DD293581A5 - PROCESS FOR THE PREPARATION OF BENZIMIDAZOLES AND THEIR USE - Google Patents

Abstract

The invention relates to processes for the preparation of benzimidazoles of the formula * in which R1 to R6 are as defined in claim 1, their 1, 3-isomer mixtures and their addition salts, which have valuable pharmaceutical properties. The new compounds are, in particular, angiotensin II antagonists. Formula (I) {Benzimidazole Preparation; pharmaceuticals; Angiotensin II antagonists}

Description

Field of application of the invention

The invention relates to processes for the preparation of benzimidazoles and their use as medicaments for the treatment of hypertension, cardiac insufficiency, ischemic peripheral circulatory disorders, myocardial ischemia, diabetic nephropathy, glaucoma of gastrointestinal disorders and bladder diseases.

Characteristic of the known state of the art

Publications which underlie the present invention as prior art are currently unknown.

Object of the invention

By the method according to the invention pharmaceutically valuable compounds are provided.

-16- 293 581 Explanation of the Essence of the Invention

It is an object of the present invention to find and prepare suitable compounds as angiotensin II antagonists.

The present invention relates to processes for the preparation of 1- and 3-isomers of benzimidazoles of the formula

R, -

and, if R | and R ₂ are each not simultaneously a hydrogen atom or not in the 4- and 7-position or in the 5- and 6-position each have the same meanings, their 1 -, 3-isomer mixtures and their addition salts, especially for the pharmaceutical application of their physiological compatible Adr'Hionssalze with inorganic or organic acids or bases.

In the above formula I means

Ri is a hydrogen, fluorine, chlorine or bromine atom,

an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxy, alkoxy, amino, alkylamino, dialkylamino or acylamino group,

an alkoxy group having 1 to 4 carbon atoms which may be substituted in the 2-, 3- or 4-position by a hydroxy, alkoxy, amino, alkylamino, dialkylamino or imidazolyl group,

a hydroxy, phenylalkoxy, acyloxy, trifluoromethylsulfonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, cycloalkylaminocarbonyloxy, cycloalkylalkylammocarbonyloxy-arylaminocarbonyloxy-aralkylaminocarbonyloxy, alkoxycarbonyloxy, cycloalkoxycarbonyloxy, cycloalkylalkoxycarbonyloxy, aryloxycarbonyloxy, aralkoxycarbonyloxy, trifluoromethyl, cyano , Nitro, alkylmercapto, alkylsulfinyl, alkylsulfonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, acylaminosulfonyl or acyl group, an amino group represented by an imidazolylalkyl, dialkylaminoalkanoyl, acyl, cycloalkoxycarbonyl, Cycloalkylalkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl or trifluoroacetyl group, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, by an alkylsulfonyl group having 1 to 4 carbon atoms, by an alkoxycarbonyl group having a total of 2 to 7 carbon atoms or by an alkoxycarbonyl group substituted by an alkoxycarbonyl group tuted

Thiazolidin-3-yl-carbonyl group G may be monosubstituted,

an alkylamino group having 1 to 6 carbon atoms, which may be substituted on the nitrogen atom by an alkyl, alkylsulfonyl or acyl group, wherein, if the acyl group represents an alkanoyl group, this may be additionally substituted by an alkoxy group, and the alkyl substituent from position 2 by a Hydroxy, alkoxy or arylamino group may be substituted,

a mono- or disubstituted by a cycloalkyl, cycloalkylalkyl, phenylalkyl or phenyl group amino group, wherein the substituents may be the same or different,

an N-alkylcycloalkylamino, N-alkylcycloalkylalkylamino, N-alkylphenylalkylamino or N-alkylphenylamino group, a pyrrolidino, piperidino or hexamethyleneimino group optionally substituted by an alkyl, cycloalkyl or phenyl group,

an N-alkoxycarbonylalkylamino, N-cycloalkoxycarbonylalkylamino, N-cycloalkylalkoxycarbonylalkylamino, N-

Aryloxycarbonyl-alkylamino or N-aralkoxycarbonyl-alkylamino group in which the alkyl group is 1 to

May contain 6 carbon atoms, an alkoxycarbonylamino, cycloalkoxycarbonylamino, cycloalkylalkoxycarbonylamino, aryloxycarbonylamino, aralkoxycarbonylamino, acylamino or alkylsulphonylamino group substituted on the nitrogen atom by a cycloalkyl, cycloalkylalkyl or aralkyl group,

a carbonyl group which is substituted by an alkyl group which is substituted in the 2- or 3-position by a hydroxy, alkanoyloxy or alkylamino group by a hydroxycarbonylalkyl, hydroxy, alkoxy, amino, cycloalkylamino, cycloalkylalkylamino, arylamino or aralkylamino group substituted by an alkylamino group substituted in the 2- or 3-position by an arylamino group or by an alkylamino group optionally substituted in the alkyl moiety by a carboxy group having 1 to 5 carbon atoms which may be additionally substituted on the nitrogen atom by an alkyl group,

an aminoacetylamino group optionally substituted by an alkoxycarbonyl group having a total of 2 to 5 carbon atoms,

an aminocarbonylamino or aminothiocurbonylamino group represented by an alkyl group of 1 to 20 carbon atoms, an alkenyl or alkynyl group of 3 to 5 carbon atoms each, a bicyclic or tricyclic alkyl group of 7 to 11 carbon atoms, a cycloalkyl, cycloalkylalkyl, Aralkyl or aryl group may be mono-, di- or trisubstituted, wherein the substituents may be the same or different and a methylene group in a cycloalkyl having 5 to 7 carbon atoms replaced by an oxygen atom and an alkyl group in the 4-, 6- or 6-position may be substituted by a hydroxy, alkanoyl or trifluoroacetyl, a Cycloalkyleniminocarbonylaminogruppe having 4 to 6 carbon atoms in Cycloalkyleniminoteil or a Morpholinocarbonylaminogruppe, both on the amino nitrogen by an alkyl group having 1 to 20 carbon atoms, by a cycloalkyl, Cycloalkylalkyl-, aralkyl or Aryl group may be substituted a phthalimino, homophthalimino, 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-carboxyphenylmethylenecarboxylylamino or 2-carboxymethylenephenylcarbonylamino group in which a carbonyl group in a phthalimino group is replaced by a methylene group and a methylene group in a homophthalimino, 2-carboxyphenylmethylencarbonylamino group or 2-carboxymethylenephenylcarbonylamino group may be substituted by one or two alkyl groups, and in addition mono- or disubstituted by the above-mentioned phenyl nuclei by alkyl or alkoxy groups, wherein the substituents may be the same or different, and simultaneously all or part

may be hydrogenated, in a 2-position by a carboxy group-substituted bicycloalkane-S-carboxylic acid amino or bicycloalkene-a-carboxylic acid amino group, a bicycloalkane ^ S-dicarboxylic imino or bicycloalkene-2,3-dicarboxylic acid in which the bicycloalkane and bicycloalkene each Containing 9 or 10 carbon atoms, substituted by 1, 2 or 3 methyl groups, and an endomethylene group substituted by an oxygen atom, a glutaric imino or S-carboxy-n-propylenecarbonyl group in which each n-propylene group is perfluorinated by one or two alkyl groups or may be substituted by a tetramethylene or pentamethylene group, or a 5,7-dioxa-1H, 3H-imidazo [1,5-c] thiazolyl group,

R ₁ denotes the meanings mentioned above for R ₁ , a 2-imidazolidin-i-yl or 3,4,5,6-tetrahydro-2 optionally substituted in the 3-position by an alkyl, cycloalkyl, cycloalkylalkyl or aralkyl group pyrimidon-1-yl group or a tetrazolyl group or

Ri and P ₂ together with 2 carbon atoms of the adjacent phenylene ring are a phenyl or 1-alkyl-3,3-dialkyl-2,3-dihydropyrrol-2-one group,

R _{3 is} a hydrogen, fluorine, chlorine or bromine atom,

an alkyl group having 1 to 6 carbon atoms in which a methylene group may be replaced by an oxygen or sulfur atom, a sulfinyl or alkylamino group, and a methyl group may be substituted by a hydroxy, alkoxy, amino, alkylamino or dialkylamino group, wherein however, the methylene group adjacent to the benzimidazole ring may not be replaced by a sulfinyl or sulfonyl group and, with simultaneous replacement of a methylene group and substitution of a methyl group, must be separated by at least 2 carbon atoms, an alkenyl or alkynyl group each having from 3 to 5 carbon atoms,

a phenylalkyl group,

a cycloalkyl or cycloalkyl-alkyl group in which the cycloalkyl portion may each contain from 5 to 7 carbon atoms, an aryl, hydroxy or imidazolylalkylamino group,

an alkylamino group having 1 to 4 carbon atoms,

an aminocarbonyl group which may be substituted by an alkyl or cycloalkyl group of 5 to 7 carbon atoms

a 5-membered heteroaromatic ring which contains an NH group, an oxygen or sulfur atom, said above-mentioned 5-membered heteroaromatic ring may additionally contain 1 to 3 N atoms, or a 6-membered heteroaromatic ring which may contain 1 or 2 nitrogen atoms, wherein the above-mentioned 5- and 6-membered heteroaromatic rings may be substituted by one or with the exception of the tetrazolyl group by two alkyl groups,

R _{4 is} an amino, phthalimino, aminomethyl, cyano, tert-butoxycarbonyl, or 1- {triphenylmethyU-tetrazolyl group, a Brönsted acid-containing group, or a group that is in vivo in a Brönsted acid-containing group can be transferred

R _{6 is} a hydrogen, fluorine, chlorine or bromine atom,

R _{6 is} a hydrogen atom or

Rs and R6, together with the two ortho-carbon atoms, form a phenyl group.

In this context, the term "a Brönsted acid-containing group" mentioned above is in particular a carboxy, aminoacetylamino, trifluoromethylcarbonylamino, trifluoromethylcarbonylaminomethyl, trifluoromethylsulfonylamino, trifluoromethylsulfonylaminomethyl or 1H-tetrazolyl group, an alkylcarbonylamino, alkylcarbonylaminomethyl, Ar / Icarbonylamino-, Arylcarbonylaminomethyl-, Aralkylcarbonylamino-, Aralkylcarbonylaminomethyl-.AIkylsulfonylaminovAlkylsulfonylaminomethyl-jArylsulfonylamino ^ Arylsulfonylaminomethyl-, Aralkylsulfonylamino-, Aralkylsulfonylaminomethyl-, Arylsulfonylaminocarbonyl- or Benzylsulfonylaminocarbonylgruppe, a Alkylsulfonylaminocarbonyl- or Perfluoralkylsulfonylanvnocarbonylgruppe each having 1 to 6 carbon atoms in the alkyl moiety,

"a group which can be converted in vivo into a Brönsted acid-containing group" with the exception of the tert-butoxycarbonyl group, an alkoxycarbonyl group having a total of 2 to 7 carbon atoms, such as the methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, n-pentoxycarbonyl or n-hexoxycarbonyl group, an aralkoxycarbonyl group such as the benzyloxycarbonyl, 1-phenylethoxycarbonyl, 2-phenylethoxycarbonyl or 3-phenylpropoxycarbonyl group or the pivaloyloxymethoxycarbonyl, phthalidylmethoxycarbonyl, ethoxycarbonyloxyethoxycarbonyl, methoxymethoxycarbonyl , Cyclohexyloxycarbonylmethoxycarbonyl or (1,3-dioxa-2-oxo-4-methyl-cyclopenten-5-yl) -methoxycarbonyl group, under "an acyl group" an alkanoyl group having 1 to 7 carbon atoms, a cycloalkylcarbonyl group having a total of 4 to 8 carbon atoms, a cycloalkylalkanoyl group having a total of 5 to 10 carbon atoms or a given optionally substituted by a fluorine, chlorine or bromine atom, an alkyl or alkoxy substituted arylcarbonyl, aralkanoyl or phenylsulfonyl group,

"an aryl group" means a phenyl group optionally substituted by a fluorine, chlorine or bromine atom, by a hydroxy, alkyl, alkoxy, phenylalkoxy or trifluoromethyl group, wherein the alkyl moiety may contain from 1 to 4 carbon atoms each, or a naphthyl group and

by "a cycloalkyl group" is meant a cycloalkyl group having from 3 to 7 carbon atoms which may be substituted by one or two alkyl groups, the alkyl and alkanoyl moieties mentioned in the definition of the moieties R) to R ₃ , unless mentioned otherwise and the above-mentioned alkyl moieties may each contain 1 to 3 carbon atoms.

The novel compounds of the above formula I have inducible properties. Thus, the compounds of formula I in which R ₄ has a Brönsted acid-containing group or a residue which can be converted into a Brönsted acid-containing group in vivo, have valuable pharmacological properties, in particular these compounds provide angiotensin II antagonists.

The remaining compounds of the formula I are valuable intermediates, since they can be converted chemically into one of the abovementioned pharmacologically active compounds of the formula I.

Another object of the present invention are thus novel drugs which are one of the above-mentioned pharmacologically active compounds of the formula I or a corresponding physiologically acceptable addition salt

and especially for the treatment of hypertension and cardiac insufficiency, for the treatment of ischemic peripheral circulatory disorders, myocarclial ischemia (angina), for the prevention of cardiac insufficiency progression after myocardial infarction, for the treatment of diabetic nephropathy, glaucoma, gastrointestinal disorders and bladder disorders.

For the meanings mentioned in the definition of the radicals R ₁ , R ₂ , Ra and R ₄ , the meaning of the hydrogen, fluorine, chlorine or bromine atom, for example, of methyl, ethyl, n-propyl, isopropyl, is given for R ₁ , n-butyl, hydroxymethyl, 2-hydroxyethyl, 2-hydroxyisopropyl, 3-hydroxypropyl, methoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxy isopropyl, 2-n-propoxy-ethyl, amino-methyl, 1-aminoethyl, 2-aminoethyl, 3-aminopropyl, methylaminomethyl, dimethylaminomethyl, ethylaminomethyl, diothylaminomethyl, N-methyl-isopropylaminomethyl- , 2-methylaminoethyl, 2-dimethylaminoethyl, 2-isopropylaminoethyl, Γϊ-diisopropylaminoethyl, 3-methylaminopropyl, 3-dimethylaminopropyl, acetaminomethyl, propionylaminomethyl, butanoylaminomethyl, pentanoylaminomethyl, benzoylaminomethyl, benzenesulfonylaminomethyl , 2-acetaminoethyl, 2-propionylaminoethyl, 2-butanoylaminoethyl, 2-benzoylaminoethyl, 3-acetaminopropyl, methoxy, ethoxy, n-propoxy, isopropoxy , n-butoxy, 2-hydroxy-ethoxy, 2-hydroxy-isopropoxy, 3-hydroxy-propoxy, 2-methoxy-ethoxy, 2-ethoxy-ethoxy, 2-methoxy-isopropoxy, 3- Methoxypropoxy, 3-n-propoxy-propoxy, 2-aminoethoxy, 2-methylamino-ethoxy, 2-dimethylamino-ethoxy, 2-ethylamino-ethoxy, 2-diethylamino-ethoxy, 2-isopropylamino -ethoxy, 3-amino-propoxy, 3-methylamino-propoxy, 3-dimethylamino-propoxy, 2- (imidazol-1-yl) -ethoxy, 2- (imidazol-2-yl) -ethoxy , 2- (imidazol-4-yl) -ethoxy, 3- (imidazol-1-yl) -propoxy, 3- (imidazol-2-yl) -propoxy, 3- (imidazol-4-yl) - propoxy, hydroxy, benzyloxy, 2-phenylethoxy, 3-phenylpropoxy, acetoxy, propionyloxy, n-butanoyloxy, n-pentanoyloxy, trifluoromethylsulfonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, isopropylaminocarbonyloxy, Dimethylaminocarbonyloxy, diethylaminocarbonyloxy, di-n-propylaminocarbonyloxy, N-methyl-ethylaminocarbonyloxy, cyclopropylaminocarbonyloxy, cyclobutylaminocarbonyloxy, cyclopentylaminocarbonyloxy, cyclohexylaminocarbonyloxy , Cycloheptylaminocarbonyloxy, cyclopropylmethylaminocarbonyloxy, cyclobutylmethylaminocarbonyloxy, cyclopentylmethylaminocarbonyloxy, cyclohexylmethylaminocarbonyloxy, cycloheptylmethylaminocarbonyloxy, (2-cyclopropylethyl) aminocarbonyloxy, (2-cyclobutylethyl) aminocarbonyloxy, (2-cyclopentylethyl) aminocarbonyloxy, (2-cyclohexylethyl ) aminocarbonyloxy, (2-cycloheptylethyl) aminocarbonyloxy, O-cyclopropylpropyD-aminocarbonyloxy, O-cyclobutylpropyD-aminocarbonyloxy, (3-cyclopentylpropyl) aminocarbonyloxy, O-cyclohexylpropyD-aminocarbonyloxy, O-cycloheptylpropyD-aminocarbonyloxy, , methoxycarbonyloxy, ethoxycarbonyloxy, n-Propoxycarbonyloxy-, isopropoxycarbonyloxy, Cyclopropoxycarbonyloxy-, Cyclobutoxycarbonyloxy-, Cyclopentoxycarbonyloxy-, Cyclohexoxycarbonyloxy-, Cycloheptoxycarbonyloxy-, Cyclopropylmethoxycarbonyloxy-, Cyclobutylmethoxycarbonyloxy-, Cyclopentylmethoxycarbonyloxy-, Cyclohexylmethoxycarbonyloxy-, Cycloheptylmethoxycarbonyloxy-, (2-cyclopropylethoxy) -c arbonyloxy, (2-cyclobutylethoxyl-carbonyloxy, (2-cyclopentylethoxy) -carbonyloxy, (2-cyclohexylethoxy) -carbonyloxy, (2-cycloheptylethoxyl-carbonyloxy, O-cyclopropylpropoxyl-carbonyloxy, O-cyclobutylpropoxyl-carbonyloxy-) , (3-cyclopentylpropoxy-1-carbonyloxy, O-cyclohexylpropoxyl-carbonyloxy, O-cycloheptylpropoxy-1-carbonyloxy, phenyloxycarbonyloxy, benzyloxycarbonyloxy, (2-phenylethoxy) -carbonyloxy, trifluoromethyl, phenylaminocarbonyloxy, benzylaminocarbonyloxy, (2- Phenylethyl) aminocarbonyloxy, cyano, nitro, methylmercapto, ethylmercapto, n-propylmercapto, isopropylmercapto, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl Isopropylsulfonyl, phenylsulfonyl, fluorophenylsulfonyl, chlorophenylsulfonyl, bromophenylsulfonyl, methylphenylsulfonyl, ethylphenylsulfonyl, isopropylphenylsulfonyl, methoxyphenylsulfonyl, ethoxyphenylsulfonyl, n-propoxyphenylsulfonyl, aminosulfonyl, methylaminosulfonic acid nonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, di-n-propylaminosulfonyl, N-methyl-ethylaminosulfonyl, phenylaminosulfonyl, fluorophenylaminosulfonyl, chlorophenylamine sulfonyl, bromophenylamine sulfonyl, methylphenylaminosulfonyl, ethylphenylaminosulfonyl -, Isopropylphenylaminsulfonyl-, Methoxyphenylaminosulfonyl-, Ethoxyphenylaminosulfonyl-, n-Propoxyphenyliiminosulfonyl-, Acetaminosulfonyl-, Propionylaminosulfonyl-, n-Butanoylaminosulfonyl-, Benzoylaminosulfonyl-, Fluorbenzoylaminosulfonyl-, Chlorbenzoylaminosulfonyl-, Brombenzoylaminsulfonyl-, Methylbenzoylaminosulfonyl-, Methoxybenzoylaminosulfonyl-, acetyl, propionyl , n-butanoyl, n-pentanoyl, n-hexanoyl, n-heptanoyl, phenylacetyl, 2-phenylpropionyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, cyclopropylmethylcarbonyl, cyclobutylmethylcarbonyl, Cyclopentylmethylcarbonyl, cyclohe xylmethylcarbonyl, cycloheptylmethylcarbonyl, (2-cyclopropylethyl) carbonyl, (2-cyclobutylethyl) carbonyl, (2-cyclopentylethyl) carbonyl, (2-cyclohexylethyl) carbonyl, (2-cycloheptylethyl) carbonyl, , O-cyclopropylpropyl-carbonyl, O-cyclobutylpropyl-carbonyl, (S-cyclopentylpropyl-carbonyl, (S-cyclohexylpropyl-carbonyl, O-cycloheptylpropyl-carbonyl, benzoyl, fluorobenzyl, chlorobenzoyl, bromobenzoyl, Methylbenzoyl, methoxybenzoyl, phenylsulfonyl, fluorophenylsulfonyl, chlorophenylsulfonyl, bromophenylsulfonyl, methylphenylsulfonyl, methoxyphenylsulfonyl, amino, 2- (imidazol-1-yl) -ethylamino, 2- (imidazol-1-yl) - isopropylamino, 3- (imidazol-1-yl) -propylamino, (imidazol-4-yl) -methylamino, 2- (imidazol-4-yl) -ethylamino, 2- (imidazol-4-yl ) -isopropylamino, 3- (imidazol-4-yl) -propylamino, acetylamino, propionylamino, n-butanylamino, isobutanoylamino, n-pentanoylamino, n-hexanoylamino, n-heptanoylamino, cyclopropylcarbonylamino, Cyclobutylcarbonylamino, cyclopentylcarbo nylamino, cyclohexylcarbonylamino, cycloheptylcarbonylamino, cyclopropylmethylcarbonylamino, cyclobutylmethylcarbonylamino, cyclopentylmethylcarbonylamino, cyclohexylmethylcarbonylamino, cycloheptylmethylcarbonylamino, (2-cyclopropylethyl) carbonylamirolo, (2-cyclobutylethyl) carbonylamino, (2-cyclopentylethyD-carbonylamino -, (2-Cyclohoxyethyl) carbonylamino, (2-cycloheptylethyl) carbonylamino, (3-cyclopropylpropyl) carbonylamino, (S-cyclobutylpropyl-carbonylamino, (S-cyclopentylpropyl) carbonylamino, (3-cyclohexylpropyl) -carbonylamino -, (S-Cycloheptylpropyl-carbonylamino, benzoylamino, fluorobenzoylamino, chlorobenzoylamino, bromobenzoylamine, methylbenzoylamino, hydroxybenzoylamino, methoxybenzoylamino, phenylacetylamino, phenylpropionylamino, naphthylcarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino) , Cyclopropyloxycarbonylamino-.Cyclobutyloxycarbonylamino, Cyclopentoxycarbonylamino, Cyclohexoxycarbonylamino, Cycloheptoxycarbo nylamino, cyclopropylmethoxycarbonylamino, cyclobutylmethoxycarbonylamino, cyclopentylmethoxycarbonylamino, cyclohexylmethoxycarbonylamino, cycloheptylmethoxycarbonylamino, (2-cyclopropylethoxy) carbonylamino, (2-cyclobutylethoxy) carbonylamino, (2-cyclopentylethoxyJ-carbonylamino, (2-cyclohexylethoxy) - carbonylamino, (2-cycloheptylethoxy) carbonylamino, (3-cyclopropylpropoxy) -carbonylamino, (S-cyclobutylpropoxyl-carbonylamino, (S-cyclopentylpropoxy) -carbonylamino,

(S-Cyclohexylpropoxyl-carbonylamino, (S-CycloheptylpropoxyJ-carbonylamino, phenoxycarbonylamino, fluorophenoxycarbonylamino, chlorphenoxycarbonylamino, bromophenoxycarbonylamino, methylphenoxycarbonylamino, hydroxyphenoxycarbonylamino, methoxyphenoxycarbonylamino, benzyloxyphenoxycarbonylamino, benzyloxycarbonylamino, (2-phenylethoxy) carbonylamino -, trifluoroacetylamino, decalinylamino, adamantylamino, methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, n-butylsulfonylamino, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, n Pentylamino, n-hexylamino, dimethylamino, diethylamino, di-n-propylamino, methyl-ethylamino, methyl-isopropylamino, methyl-n-butylamino, ethyl-n-propylamino, Nn-propylsulfonyl methylamino, methyl-n-pentylamino, ethyl-n-hexylamino, N-methylsulfonyl-methylamino, N-ethylsulfonyl-methylamino, Nn-propylsulfonyl-methylamino, N-methylsulfonyl-ethylamino, N-ethylsulfonyl-ethylamino -, N n-propylsulfonyl-ethylamino, N-methylsulfonyl-n-propylamino, N-ethylsulfonyl-n-propylamino, Nn-propylsulfonyl-n-propylamino, N-methylsulfonyl-n-butylamino, N-ethylsulfonyl-n-pentylamino, Nn-propylsulfonyl-n-hexylamino, N-acetylmethylamino, N-acetyl-ethylamino, N-acetyl-n-hexylamino, N-propionyl-methylamino, N-propionyl-ethylamino, N-propionyl-n- butylamino, Nn-butanoyl-methylamino, Nn-butanoyl-ethylamino, Nn-butanoyl-n-pentylamino, N-isobutanoyl-methylamino, N-isobutanoyl-ethylamino, N-isobutanoyl-isopropylamino, N-isobutanoyl -n-pentylamino, Nn-pentanoyl-methylamino, Nn-pentanoyl-ethylamino, Nn-pentanoyl-isopropylamino, Nn-pentanoyl-n-pentylamino, Nn-hexanoyl-methylamino, Nn-hexanoyl-ethylamino, Nn-hexanoyl-isopropylamino, Nn-hexanoyl-n-pentylamino, Nn-heptanoyl-methylamino, Nn-heptanoyl-ethylamino, Nn-heptanoyl-isopropylamino, Nn-haptanoyl-n-pentylamino, N-cyclopropylcarbonylmethylamino , N-Cyclobotylcarbonyl-methylamino, N-cyclopentylcar bonyl-methylamino, N-cyclohexylcarbonyl-methylamino, N-cycloheptylcarbonyl-methylamino, N-cyclopropylmethylcarbonyl-methylamino, N-cyclobutylmethylcarbonyl-methylamino, N-cyclobutylmethylcarbonyl-methylamino, N-cyclopentylmethylcarbonylmethylamino, N-cyclohexylmethylcarbonyl-methylamino -, N-Cyclohoptylmethylcarbonyl-methylamino, N- (2-CyclopropylethylcarbonyU-methylamino, N- (2-cyclobutylethylcarbonyl) -methylamino, N- (2-cyclopentylethylcarbonyl) -methylamino, N- (2-cyclohexyiethylcarbonyl) -methylamino N, N- (2-cycloheptylethylcarbonyl) -methylamino, N- (3-cyclopropylpropylcarbonyl) -methylamino, N-IS-cyclobutylpropylcarbonyU-methylamino, N-fS-cyclopentylpropylcarbonyl) -methylamino, NO-cyclohexylpropylcarbiyl) -methylamino- , N-lS-cycloheptylpropylcarbonyD-methylamino, N-benzoylmethylamino, N-benzoyl-ethylamino, N-benzoyl-isopropylamino, N-benzoyl-n-butylamino, N-bonozoyl-n-pentylamino, N-benzoyl -n-hexylamino, N-Rubenzoyl-methylamino, N-methylbenzoyl-ethylamino, N-methox ybenzoyl-isopropylamino, N-chlorobenzoyl-n-butylamino, N-fluorobenzoyl-n-pentylamino, N-bromobenzoyl-n-hexylamino, N-phenylacetyl-methylamino, N-phenylsulfonyl-methylamino, N- (2 -Hydroxyethyl) -methylamino, N- (2-hydroxyethyl) ethylamino, N- (2-methoxyethyl) methylamino, N- (2-methoxyethyl) ethylamino, N-hydroxyacetylmethylamino, N-hydroxyacetyl -ethylamino, N-methoxyacetyl-methylamino, N-methoxyacetyl-ethylamino, cyclopropylamino, cyclobutylannino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino, cyclohexylmethylamino, cycloheptylmethylamino, (2 Cyclopropylethyl) amino, (2-cyclobutylethyl) amino, (2-cyclopentylethyl) amino, (2-cyclohexylethyl) amino, (2-cycloheptylethyl) amino, O -cyclopropylpropyD-amino, (3 CyclopentylpropyD-amino, O-cyclohexylpropylD-amino, (3-cycloheptylpropyl) amino, benzylamino, 2-phenylethylamino, 3-phenylpropylamino, phenylamino, dicyclohexylamino, dicyclohexylm ethylamino, dibenzylamino, N-methylcyclopropylamino, N-isopropyl-cyclopropylamino, N-ethyl-cyclobutylamino, N-methyl-cyclopentylamino, N-ethylcyclohexylamino, N-fn-propyl-cycloheptylamino-N-methyl- cyclopropylmethylamino, N-isopropyl-cyclopropylmethylamino, N-ethyl-cyclobylmethylamino, N -methyl-cyclopentylmethylamino, N-ethylcyclohexylmethylamino, N- (n-propyl) -cycloheptylmethylamino, N -methyl- (2-cyclopropylethyl ) -amino, N-isopropyl- (2-cyclopropylethyl) -amino, N-ethyl- (2-cyclobutylethyl-amino, N -methyl- (2-cyclopentylethyl) -amino, N-ethyl- (2- cyclohexylethyl) amino, N- (n-propyl) - (2-cycloheptylethyl-amino, N -methyl-O-cyclopropylpropyl-amino-.N-isopropyl-O-cyclopropylpropyl-amino, N-ethyl- (3 -cyclobutylpropyD-amino, N-methyl-O-cyclopentylpropyD-amino, N-ethyl-fS-cyclohexylpropylJ-amino, N- (n-propyl) - (3-cycloheptylpropyl) amino, N-methylbenzylamino , N-ethylbenzylamino. N-isopropyl-benzylamino, N-methyl- (2-phenylethyl-amino, N-methyl-phenylamino, N- (n-propyl) -phenyl-amino, pyrrolidino, methylpyrrolidino, ethylpyrrolidino, isopropylpyrrolidino , Cyclopentylpyrrolidino, cyclohexylpyrrolidino, cycloheptylpyrrolidino, phenylpyrrolidino, piperidino, methylpiperidino, ethylpiperidino, isopropylpiperidino, cyclopentylpiperidino, cyclohexylpiperidino, cycloheptylpiperidino, phenylpiperidino, hexamethylenimine, methylhexamethylenimino, ethylhexamethylenimino, isopropylhcxamethylenimino, Cyclopentylhexamethyleneimino, cyclohexylhexamethyleneimino, cycloheptylhexamethyleneimino, phenylhexamethyleneimino, N-methoxycarbonylmethylamino, N-mothoxycarbonyl-N-ethylamino, N-methoxycarbonyl-n-pentylamino, N-methoxycarbonyl-n-hexylamino, N-ethoxycarbonyl methylamino, N-ethoxycarbonyl-ethylamino, N-cyclopropyloxycarbonyl-methylamino, N-cyclopropyloxycarbonyl-ethylamino, N-cyclopropyloxycarbonyl-n-propylamino) N-cyclobutylox / carbonyl-methylam ino, N-cyclobutyloxycarbonyl-isopropylamino, N-cyclopentyloxycarbonyl-methylamino, N-cyclopentyloxycarbonyl-ethylamino, N-cyclohexyloxycarbonyl-methylamino, N-cyclohexyloxycarbonyl-ethylamino, N-cycloheptyloxycarbonyl-methylamino, N-cyclopentylmethyloxycarbonylmethylamino, N-cyclopentylmethyloxycarbonyl-ethylari-, N-cyclohexyimethyloxycarbonyl-methylamino, N-cyclohexylmethyloxycarbonyl-ethylamino, N-cycloheptylmethyloxycarbonyl-methylamino, N-cycloheptylmethyloxycarbonyl-ethylamino, N- (2-cyclopentylethyloxy) -carbonyl-methylamino, N- (2-Cyclopentylethyloxy) carbonylethylamino, N- (2-cyclohexylethyloxy) carbonylmethylamino, N- (2-cyclohexylethyloxy) carbonylethylamino, N- (2-cycloheptylethyloxy) carbonylmethylamino, N - (2-Cycloheptylethyloxy) carbonyl-ethylamino, N-phenoxycarbonylmethylamino, N-phenoxycarbonyl-ethylamino, N-phenoxycarbonyl-isopropylamino, N-benzyloxycarbonyl-methylamino, N-benzyloxycarbonyl-ethylamino, N-benzyloxycarbonyl -isopropylamino, N- (2- Phenylethoxy) carbonyl-methylamino, N- (2-phenylethoxy-1-carbonyl-othylamino, N- (2-phenylethoxy) -carbonyl-isopropylamino, N- (3-phenylpropoxy) -carbonylmethylamino, N-fS-phenylpropoxyl carbonyl-ethylamino, NO-phenylpropoxyl-carbonyl-isopropylamino, N-methoxycarbonyl-cyclopropylamino, N-methoxycarbonyl-cyclobutylamino, N-methoxycarbonyl-cyclopentylamino, N-methoxycarbonyl-cyclohexylamino, N-methoxycarbonyl-cycloheptylamino-.N -Ethoxycarbonyl-cyclopropylamino, N-ethoxycarbonyl-cyclobutylamino, N-ethoxycarbonyl-cyclopentylamino, N-ethoxycarbonyl-cyclohexylamino, N-ethoxycarbonyl-cycloheptylamino, N-methoxycarbonyl-cyclopropylmethylamino, N-methoxycarbonylcyclobutylmethylamino, N-methoxycarbonyl cyclopentylmethylamino, N-methoxycarbonylcyclohexylmethylamino, N-methoxycarbonylcycloheptylmethylamino, N-ethoxycarbonylcyclopropylmethylamino, N-ethoxycarbonyl

cyclobutylmethylamino, N-ethoxycarbonylcyclopentylmetliylamino, N -ethoxycarbonylcyclohexylmethylamino, N -ethoxycarbonylcycloheptylmethylaniino, N-methoxycarbonyl (2-cyclopropylethyl) amino, N-methoxycarbonyl (2-cyclobutylethyl) amino, N-methoxycarbonyl- (2-cyclopentylethyl) -amino, N-methoxycarbonyl- (2-cyclohexylethyl) -amino, N-methoxycarbonyl- (2-cycloheptylethyl) -amino, N -ethoxycarbonyl- (2-cyclopropylethyl) -amino -, N-ethoxycarbonyl- (2-cyclobutylethyl) -amino, N -ethoxycarbonyl- (2-cyclopentylethyl) -amino, N -ethoxycarbonyl- (2-cyclohexylethyl) -amino, N -ethoxycarbonyl-fa-cycloheptylethyl-amino , N-methoxycarbonyl-t-cyclopropylpropyD-amino, N-methoxycarbonyl-O-cyclobutylpropyD-amino, N-methoxycarbonyl-O-cyclopentylpropyD-amino, N-methoxycarbonyl-O-cyclohexylpropyD-amino, N-methoxycarbonyl- O-cycloheptylpropyD-amino, N-ethoxycarbonyl-O-cyclopropylpropyD-amino, N -ethoxycarbonyl- (3-cyclobutylpropyD-amino, N -ethoxycarbonyl-O-cyclopentylpropyD-amino, N -ethoxycarbonyl-O-cyclohex ylpropyD-amino, N -ethoxycarbonyl-O-cycloheptylpropyD-amino, N-phenoxycarbonylcyclopropylamino, N-phenoxycarbonylcyclobutylamino, N-phenoxycarbonylcyclopentylamino, N-phenoxycarbonylcyclohexylamino, N-phenoxycarbonylcycloheptylamino, N-benzyloxycarbonyl cyclopropylamino, N-benzyloxycarbonylcyclobutylamino, N-benzyloxycarbonylcyclopentylamino, N-benzyloxycarbonylcyclohexylamino, N-benzyloxycarbonylcycloheptylamino, N- (2-phenylethoxy) carbonylcyclopropylamino, N- (2-phenylethoxy) carbonylcyclobutylamino, N- (2-phenylethoxy) carbonylcyclopentylamino, N- (2-phenylethoxy) carbonylcyclohexylamino, N- (2-phenylethoxy) carbonylcycloheptylamino, N- (3-phenylpropoxy) carbonyl-cydopropylamino ^ Np-phenylpropoxyl-carbonyl-cyclobutylamino, N- (3-phenylpropoxy) -carbonylcyclopentylamino, N-.beta.-phenylpropoxyl-carbonyl-cyclohexylamino, N-fä-phenylpropoxyl-carbonyl-cycloheptylamino, N-methylsulfonyl cyclopropylamino, N-ethylsulfonyl-cyclobuty'amino, Nn-propylsulfonyl-cyclopentyla mino, N-ethylsulfonylcyclohexylamino, N-methylsulfonylcycloheptylamino, N-phenoxycarbonylcyclopropylmethylamino, N-phenoxycarbonylcyclobutylmethylamino, N-phenoxycarbonylcyclopentylmethylamino, N-phenoxycarbonylcyclohexylmethylamino, N-phenoxycarbonylcycloheptylmethylamino, N-benzyloxycarbonylcyclopropylmethylamino, N -benzyloxycarbonylcyclobutylmethylamino, N-benzyloxycarbonylcyclopentylmethylamino, N-benzyloxycarbonylcyclohexylmethylamino, N-benzyloxycarbonylcycloheptylmethylamino, N- (2-phenylethoxycarbonyD-cyclopropylmethylamino, N- (2-phenylethoxycarbonyl) -cyclobutylmethylamino, N- (2-phenylethoxycarbonyl) -cyclopentylmethylamino, N- (2-phenylethoxycarbonyl) -cyclohexylmethylamino, N- (2-phenylethoxycarbonyl) -cycloheptylmethylamino, N-fS-phenylpropoxycarbonyD-cyclopropylmethylamino, NO-phenylpropoxycarbonyl) -cyclobutylmethylamino, N-IS-phenylpropoxycarbonylD-cyclopentylmethylamino, N- (3-phenylpropoxycarbonyl) -cyclohexylmethylamino, N-IS-phenylpropoxycarbonyD- cycloheptylmethylamino, N-methylsulfonylcyclopropylmethylamino, N-methylsulfonylcyclobutylmethylamino, N-methylsulfonylcyclopentylmethylamino, N-ethylsulfonylcyclohexylmethylamino, N-isopropylsulfonylcycloheptylmethylamino _/ N-phenoxycarbonyl- (2-cyclopropylethyl-amino-, N- Phenoxycarbonyl- (2-cyclobutylethyl) amino, N-phenoxycarbonyl- (2-cyclopentylethyl) amino, N-phenoxycarbonyl- (2-cyclohexylethyl) amino, N-phenoxyi-arbonyl- (2-cycloheptylethyl) amino N, N-Benzyloxycarbonyl- (2-cyclopropylethyl-amino, N-benzyloxycarbonyl- (2-cyclobutylethyl) -amino, N-benzyloxycarbonyl- (2-cyclopentylethyl) -amino, N-benzyloxycarbonyl- (2-cyclohexylethyl) - amino, -N-benzyloxycarbonyl- (2-cycloheptylethyl) amino, N- (2-phenylethoxycarbonyl) - (2-cyclopropylethyl) amino, N- (2-phenylethoxycarbonyl) - (2-cyclobutylethyl) amino N, N- (2-phenylethoxycarbonyl) - (2-cyclopentylethyl) amino, N- (2-phenylethoxycarbonyl) - (2-cyclohexylethyl) amino, N- (2-phenylethoxycarbonyl) - (2 -cycloheptylethyl-amino, N- (3-Phe nylpropoxycarbonyl) - (2-cyclopropylethyl) amino, N- (3-phenylpropoxycarbonyl) - (2-cyclobutylethyll-amino, N- (3-phenylpropoxycarbonyl) - (2-cyclopentylethyl) amino) , N- (3-phenylpropoxycarbonyl) - (2-cyclohexylethyl-amino, N- (3-phenylpropoxy-carbonyl) - (2-cycloheptylethyl) -amino, N-methylsulfonyl- (2-cyclopropyl-ethyl) -amino) , N-ethylsulfonyl- (2-cyclobutylethyl) -amino, N-isopropylsulfonyl- (2-cyclopentylethyl) -amino, N-methylsulfonyl- (2-cyclohexylethyl-amino, N -methylsulfonyl- (2-cycloheptylethyl) -amino -, N-Phenoxycarbonyl-lS-cyclobutylpropyD-amino, N-phenoxycarbonyl-O-cyclopentylpropyD-amino, N-phenoxycarbonyl-IS-cyclohexylpcopyD-amino, N-phenoxycarbonyl- (3-cycloheptylpropyD-amino, N-benzyloxycarbonyl -O-cyclopropylpropyD-amino, N-benzyloxycarbonyl-O-cyclobutylpropyl) -amino, N-benzyloxycarbonyl-fS-cyclopentylpropylJ-amino, N-benzyloxycarbonyl-f-cyclohexylpropyO-amino, N-benzyloxycarbonyl-IS-cycloheptylpropyD-amino- , N- (2-phenylethoxycarbonyl) - (3-cyciopropylpropyl) -amino, N- (2-Phe nylethoxycarbonyD-O-cyclobutylpropyD-amino, N- (2-phenylethoxycarbonyl) - (3-cyclopentylpropyl) -amino, N- (2-phenylethoxycarbonyD-O-cyclohexylpropyD-amino, N- (2-phenylethoxycarbonyl- (3-cyclopentylpropyl) amino) cycloheptylpropyl) amino, N- (3-phenylpropoxycarbonyD-O-cyclopropylpropyD-amino, NO-phenylpropoxycarbonyl-O-cyclobutylpropyD-amino, N- (3-phenylpropoxycarbonyO-O-cyclopentylpropyD-amino-, N- (3-phenylpropoxycarbonyl) Phenylpropoxycarbonyl) - (3-cyclohexylpropyl) amino, N- (3-phenylpropoxycarbonyD-O-cycloheptylpropyD-amino, N-methylsulfonyl-O-cyclopropylpropyD-amino, N-ethylsulfonyl- (3-cyclobutylpropyD-amino, N -lsopropylsulfonyl-O-cyclopentylpropyD-amino, N-methylsulfonyl-O-cyclohexylpropyl-D-amino, N-methylsulfonyl-1S-cycloheptylpropyl-amino, N-benzoyl-cyclopropylamino, N-benzoyl-cyclobutylamino, N-benzoylcyclopentylarpino- , N-ciocyclohexylamino, N-benzoylcycloheptylamino, N-phenylacetylcyclopropylamino, N-phenylacetyl-cyclobuV'i-imino, N-phenylacetyl-cyclopentylamino, N-phenylacetylcyclohexylamino, N- Phen ylacetylcycloheptylamino-, f ¹ · ^ honylsulfonyl-cyclopropylamino, N-phenylsulfonyl-cyclobutylamino, N-Phenylsulfonylcyclopentylamino-, M-Phonylsulfonyl-cyclohexylamino, N-phenylsulfonyl-cycloheptylamino-, N-Benzoylcyclopropylmethylamino-, N-benzoyl-cyclobutylmethylamino-, N-benzoylcyclopentylmethylamino, N-benzoylcyclohexylmethylamino, N-benzoylcycloheptylmethylamino, N-phenylacetylcyclopropylmethylamino, N-phenylacetylcyclobutylmethylamino, N-phenylacetylcyclopontylmethylamino, N-phenylacetylcyclohexylmethylamino, N-phenylacetylcycloheptylmethylamino, N-phenylsulfonylcyclopropylmethylamino, N-phenylsulfonylcyclobutylmethylamino, N-phenylsulfonylcyclopentylmethylmethylamino-N-phenylsulfonylcyclohexylmethylamino, N-phenylsulfonylcycloheptylmethylamino, N-benzoyl- (2-cyclopropylethyl) amino, N-benzoyl- (2-cyclobutylethyl) amino, N-benzoyl- (2-cyclopentylethyl-amino, N-benzoyl- (2-cyclohexylethyl) -amino, N-benzoyl- (2-cycloheptylethyl) -amino, N-phenylacetyl - (2-cy clopropylethyl) amino, N-phenylacetyl (2-cyclobutylethyl) amino, N-phenylacelyl (2-cyclopentylethyl) amino, N-phenylacetyl (2-cyclohexylethyl) amino, N-phenylacetyl ( 2-cycloheptylethyl) amino, N-phenylsulfonyl-2- (cyclobutylethyl) amino, N-phenylsulfonyl- (2-cyclopentylethyl) amino, N-phenylsulfonyl- (2-cyclohexylethyl) amino, N-phenylsulfonyl- (2-cycloheptylethyl-amino, N-benzoyl-O-cyclopropyl-propyl-D-amino, N-benzoyl-O-cyclobutyl-propyl-D-amino, N-benzoyl- (3-cyclopentyl-propyl-D-amino, N-benzoyl-F-cyclohexyl-propyl-D-amino -, N-Benzoyl-IS-cycloheptylpropyl-amino-.N-phenylacetyl- (S-cyclopropylpropyD-amino-, N-phenylacetyl-O-cycIobutylpropyD-amino-, N-phenylacetyl-O-cyclopentylpropyD-amino-, N-phenylacetyl -O-cyclohexylpropyl-amino, N-phenylacetyl-IS-cycloheptylpropyl-amino, N-phenylsulfonyl (3

cyclopropylpropyD-amino, N-phenylsulfonyl-O-cyclobutylpropyD-amino, N-phenylsulfonyl-O-cyclopentylpropyD-amino, N-phenylsulfonyl-β-cyclohexylpropyU-amino, N-phenylsulfonyl-β-cycloheptylpropyD-amino, N Acetylcyclopropylamino, N-acetylcyclobutylamino, N-acetylcyclopentylamino, N-acetylcyclohexylamino, N-acetylcycloheptylamino, N-acetylcyclopropylmethylamino-N-acetylcyclobutylmethylamino-N- acetyl-cyclopentylmethylamino-, N-acetyl-cyclohexylamino, N-acetyl-cycloheptylmethylamino-, N-acetyl- (2-cyclopropyl-ethyl) -amino, N-acetyl- (2-cyclob Jiylethyl ^l) amino, N Acetyl (2-cyclopentylethyl) amino, N-acetyl-fa-cyclohexylethyl-amino, N-acetyl-fZ-cycloheptylethyl-amino, N-acetyl (3-cyclopropylpropyl) amino, N-acetyl O-cyclobutylpropyD-amino, N-acetyl-O-cyclopentylpropyD-amino, N-acetyl-O-cyclohexylpropyl-D-amino, N-acetyl-cyclohepropyl-D-amino-N-acetylbenzylarino, N-acetyl (2-phenylethyl) amino, N-acetyl (3-phenylpropyl) amino, N-benzoylbenzylamino, N-benzoyl - (2-phenylethyl) amino, N-benzoyl- (3-phenylpropyl) amino) N -methylsulfonylbenzylamino, N -methylsulfonyl- (2-phenylethyl) amino, N -methylsulfonyl- (3-phenylpropyl ) -amino, carboxy, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl-n-butylaminocarbonyl, n-pentylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl , Cyclohexylaminocaruonyl-.Cycloheptylaminocarbonyl-, Cyclopentylmethylaminocarbonyl-, Cyclohexylmethylaminocarbonyl-, Cycloheptylmethylaminocarbonyl-, 2-Cyclohexylethylaminocarbonyl-, phenylaminocarbonyl, Fluorphenylaminocarbonyl-, Chlorphenylaminocarbonyl-, Bromphenylaminocarbonyl-, Methylphenylaminocarbonyl · Ethylphenylaminocarbonyl-, Isopropylphenylaminocarbonyl-, Methoxyphenylaminocarbonyl-, Ethoxyphenylaminocarbonyl-, Isopropoxyphenylaminocarbonyl- , n-butoxyphenylaminocarbonyl, benzylaminocarbonyl, (2-phenylethyl) aminocarbonyl, dimethylam inocarbonyl, diethylaminocarbonyl, diisopropylaminocarbonyl, N-methylethylaminocarbonyl, N-methyl-n-propylaminocarbonyl, N-methyl-n-butylaminocarbonyl, aminoacetylamino, N-methoxycarbonylaminoacetylamino, N -ethoxycarbonylaminoacetylamino, N-isopropoxycarbonyl aminoacetylamino-.aminocarbonylamino, methylaminocarbonylamino, dimethylaminocarbonylamino, N-methylaminocarbonyl-methylamino, N-imidimethylaminocarbonyD-methylamino, N-oymethylaminocarbonylethylamino, N-dimethylaminocarbonylisopropylamino, N- (dimethylaminocarbonyl) -n-pentylamino, N-methylaminocarbonyl-ethylamino, N-methylaminocarbonyl-n-pentylamino, N-methylaminocarbonyl-n-hexylamino, N-methylaminocarbonyl-n-octylamino, N-methylaminocarbonyl-n-dodecylamino, N-methylaminocarbonylcyclohexylamino, ethylaminocarbonylamino, N Ethylaminocarbonyl-methylamino-N-ethylaminocarbonyl-ethylamino, N-ethylaminocarbonyl-n-hexylamino.N-ethylaminocarbonyl-n-octylamino, N-ethylaminocarbonyl-n-dodecylamino, N-ethylaminoc arbonylcyclohexylamino, diethylaminocarbonylamino, N-idiethylaminocarbonyD-methylamino, N- (diethylaminocarbonyl) -ethylamino, N-f-diethylaminocarbonylJ-n-butylamino, N-idiethylaminocarbonyD-n-hexylamine, N-f-diethylaminocarbonyD-n-octylamino , N-diethylaminocarbonyl-n-dodecylamino, isopropylaminocarbonylamino, N-isopropylaminocarbonyl-methylamino, n-butylaminocarbonylamino, N-lr-butylaminocarbonyD-methylamino, N- (n-butylaminocarbonyl-ethylamino, N-ln-butylaminocarbonyD -isopropylamino, N-ln-butylaminocarbonylJ-n-butylamino, N-ln-butylaminocarbonyD-n-hexylamino, N-ln-butylaminocarbonyD-n-octylamino, N-ln-butylaminocarbonyD-ndodecylamino, N-tn ButylaminocarbonyD-cyclohexylamino, N-tDi-ln-ButyD-aminocarbonyD-amino, N- (di (n-butyl) -aminocarbonyU-methylamino, N-IDi-fn-butylJ-aminocarbonyl-ethylamino, N-IDi -n-n-butyl-aminocarbonyl-n-butylamino, N-idi-in-butydo-aminocarbonyD-n-hexylamino, N-idi-in-butydo-aminocarbonyD-n-octylamino, N-idi-in-butyd aminocarbonyl) -n-dode cylamino, N-in-pentylaminocarbonyD-ethylamino, N-in-hexylaminocarbonyD-ethylamino, N- (n-octylaminocarbonyl) -ethylamino, N-ln-dodecylaminocarbonylJ-ethylamino, n-hexylaminocarbonylamino, n-octylaminocarbonylamino , n-dodecylaminocarbonylamino, N-ln-hexylaminocarbonyD-n-butylamino, N-in-hexylaminocarbonyD-n-pentylamino, N- (n-hexylaminocarbonyD-n-hexylamino, N-fn-hexylaminocarbonyD-n-octylamino) , N-ln-hexylaminocarbonyD-n-dodecylamino, N-fn-octylaminocarbonyD-n-butylamino, N-fn-octylaminocarbonyD-n-pentylamino, N-ln-octylaminocarbonyD-n-hexylamino, N-fn-octylaminocarbonyD-n octylamino, N-ln-octylaminocarbonyD-n-dodecylamino, N- (n-dodecylaminocarbonyl) -J-n-butylamino, N-fn-dodecylaminocarbonyO-n-pentylamino, N-ln-dodecylaminocarbonyD-n-hexylamino, N-fn -DodecylaminocarbonyD-n-octylamino, N-ln-dodecylaminocarbonyD-n-dodecylamino, N- (n-hexylaminocarbonyl) -cyclohexylamine), N- (n-octylaminocarbonyl) -cyclohexylamino, N- (n-dodecylaminocarbonyl) - cyclohexylamino, di-fn-HexyD-am inocarbonylamino, N-tDi-fn-HexyU-aminocarbonyU-methylamino, N - ((n-hexyl) -methylaminocarbonylamino, N-cyclohexylaminocarbonyl-n-pentylamino, N -cyclohexylaminocarbonyl-n-hexylamino, N- Cyolohexylaminocarbonyl-n-octylamino-N-cyclohexylaminocarbonyl-n-dodecylamino, N-cyclohexylaminocarbonylcyclohexylamine) -, N-IEhylcyclohexylaminocarbonyl-methylamino, N-1-propylcyclohexylaminocarbonyD-methylamino, N-ln-butylcyclohexylaminocarbonyD-methylamino, adamantyl (1 l-aminocarbonylamino, 4-hydroxybutylaminocarbonylamino, B-hydroxypentylaminocarbonylamino, 6-hydroxyhexylaminocarbonylamino, allylaminocarbonylamino, but-2-enylaminocarbonylamino, pent-2-enylaminocarbonylamino, pent-3-enylaminocarbonylamino, crotylaminocarbonylamino, But-2-ynylaminocarbonylamino, pent-1-yl-aminocarbonylamino, pent-3-ynylaminocarbonylamino, tetrahydrofuran-2-yl-aminocarbonylamino _/ Tβ-tetrahydropyΓan-2-yl-aminocarbonylamino, N- (ethyl-in-pentyd-aminocarbonyD-ethylamino -, N-IMethyl-cyclopentylamine ocarbony ,; methylamino, N- (methylcyclohexylaminocarbonyD-ethylamino, cyclopropylaminocarbonylamino, N-cyclopropylaminocarbonylmeth / lamino, cyclobutylaminocarbonylamino, N-cyclobutylaminocarbonylmethylamino, cyclopentylaminocarbonylaminyl, N-cyclopentylaminocarbonylmethylamino, cyclohexylaminocarbonylamino, N -cyclohexylaminocarbonylmethylamino -, N-Cyclohexylaminocarbonyl-ethylamino, N-cyclohexylaminocarbonyl-n-propylamino, N-cyclohexylaminocarbonyl-n-butylamino, N-cyclohexylaminocarbonyl-n-pentylamino, N-cyclohexylaminocarbonyl-n-hexylamino, N-cyclohexylaminocarbonyl-n-octylamino N, N-cyclohexylaminocarbonyl-n-dodecylamino, cycloheptylaminocarbonylamino, N-cycloheptylaminocarbonyl-methylamino, cyclopentylmethylaminocarbonylamino, N-cyclopentylmethylaminocarbonylmethylamino, cyclohexylmethylaminocarbonylamino-N-cyclohexylmethylaminocarbonyl-methylamino, benzylaminocarbonylamino, (2-phenylethyl-aminocarbonylamino, Phenylaminocarbonylamino, fluorophenylaminocarbonylamino, chl orphenylaminocarbonylamino-, Bromphenylaminocarbonylamino-, Methylphenylaminocarbonylamino-, Ethylphenylaminocarbonylamino-, Isopropylphenylaminocarbonylamino-, Methoxyphenylaminocarbonylamino-, Ethoxyphenylaminocarbonylamino-, Isopropoxyphenylaminocarbonylamino-, n-Butoxyphenylaminocarbonylamino-, Aminothiocarbonylamino-, Methylaminothiocarbonylamino-, N-Methylaminocarbonylmethylamino-, N-methylaminocarbonyl-ethylamino, Ethylaminothiocarbonylamino-, N-ethylaminothiocarbonylmethylamino, N-ethylaminothiocarbonylethylamino, N-ethylaminothiocarbonyl-n-hexylanino,

Isopropylaminothiocarbonylamino, N-isopropylaminothiocarbonylmethylamino, allylaminothiocarbonyl: mino, but-2-enylaminothiocarbonylamino, pent-1-enylaminothiocarbonylamino, pent-S-enylaminothiocarbonylamino, crotylaminothiocarbonylamino, but-1-vinylaminothiocarbonylamino, pent-1-vinylaminothiocarbonylamino, pent-3-inylaminothiocarbonylamino-.Tetrahydrofuran ^ -yl ^ aminothior.arbonylamino-.Tetrahydropyran -ylaminothiocarbonylamino-.Adamantyl-dl-aminothiocarbonylamino-, Cyclopropylaminothiocarbonylamino-, N-Cyclopropylaminotliiocarbonyl-methylamino, Cyclobutylaminothiocarbonylamino-, N-Cyclobutylaminothiocarbonylmethylamino-, Cyclopentylaminothiocarbonylamino- , N-cyclopentylaminothiocarbonylmethylamino, cyclohexylaminothiocarbonylamino, N-cyclohexylaminothiocarbonylmethylamino, cycloheptylaminothiocarbonylamino, N-cycloheptylaminothiocarbonylmethylamino, cyclopentylmethylaminothiocarbonylamino, N-cyclopentylmethylaminothiocarbonylmethylamino, cyclohexylmethylaminothiocarb onylamino, N-cyclohexylmethylaminothiocarbonyl-methylamino, dimethylaminothiocarbonylamino, diethylaminothiocarbonylamino, N-Kn-HexyD-aminothiocarbonyD-amino, N-ttn-HexyD-methylaminothiocarbonyO-amino, N-t-dimethylaminothiocarbonyl) -methylamino, N-f-dimethylaminothiocarbonyD- n-pentylamino, N-f-diethylaminothiocarbonyD-methylamino, N- (diethylaminothiocarbonyD-ethylamino, N- (di- (n-hexyl) -aminothiocarbonyl) -methylamino, N- (di- (n-butyl) -aminothiocarbonyl) -n-butylamino, N-dn-hexylD-methylaminothiocarbonyD-methylamino, N- (ethyl (n-pontyl) -aminothiocarbonyD-ethylamino, N-IMethyl-cyclopentylaminothiocarbonyD-methylamino, N- (methylcyclohexylaminothiocarbonyU-ethylamino, Benzylaminothiocarbonylamino, phenylaminothiocarbonylamino, fluorophenylaminothiocarbonylamino, chlorophenylaminothiocarbonylamino, bromophenylaminothiocarbonylamino, methylphenylaminothiocarbonylamino, ethylphenylamimthiocarbonylamino, isopropylphenylaminothiocarbonylaminep, methoxyphenylaminothiocarbonylamino, Ethoxyphenylaminothiocarbonylamino, isopropoxyphenylaminothiocarbonylamino, n-butoxyphenylaminothiocarbonylamino, pyrrolidinocarbonylamino, piperidinocarbonylamino, hexamethyleneiminocarbonylamino, N-pyrrolidinocarbonylmethylamino, N-pyrrolidinocarbonylethylamino, N-pyrrolidinocarbonylisopropylamino, N-pyrrolidinocarbonyl-n-butylamino, N- Pyrrolidinocarbonyl-n-pentylamino, N-pyrrolidinocarbonyl-n-hexylamino, N-pyrrolidinocarbonyl-n-octylamino, N-pyrrolidinocarbonyl-ndodecylamino, N-pyrrolidinocarbonyl-cyclopropylamino, N-pyrrolidinocarbonyl-cyclobutylamino, N-pyrrolidinocarbonylcyclopentylamino, N Pyrrolidinocarbonylcyclohexylamino, N-pyrrolidinocarbonylcycloheptylamino, N-pyrrolidinocarbonylcyclopropylmethylamino-N-pyrrolidinocarbonylcyclobutylmethylamino, N-pyrrolidinocarbonylcyclopentylmethylamino, N-pyrrolidinocarbonylcyclohexylmethylamino, N-pyrrolidinocarbonylcycloheptylmethylamino, N-pyrrolidinocarbonyl (2-cyclopropylethyl) amino, N-pyrrolidinocarbo nyl- (2-cyclobutyl'-3-thyl) -amino, N -pyrrolidinocarbonyl- (2-cyclopentylethyl) -amino, N -pyrrolidinocarbonyl- (2-cyclohexylethyl) -amino, N -pyrrolidinocarbonyl- (2-cycloheptylethyl) -amino , N-pyrrolidinocarbonyl-IS-cyclopropylpropyD-amino, N-pyrrolidinocarbonyl-IS-cyclobutylpropylamino, N-pyrrolidinocarbonyl-O-cyclopentylpropyl-amino, N-pyrrolidinocarbonyl-O-cyclohexylpropyl-D-amino, N-pyrrolidinocarbonyl (3-cycloheptylpropyD-amino, N-pyrrolidinocarbonyl-phenylamino, N-pyrrolidinocarbonyl-benzylamino, N-piperidinocarbonyl-methylamino, N-piperidinocarbonyl-ethylamino, N-piperidinocarbonyl-isopropylamino, N-piperidinocarbonyl-n-butylamino , N-piperidinocarbonyl-n-pentylamino, N-piperidinocarbonyl-n-hexylamino, N-piperidinocarbonyl-n-octylamino, N-piperidinocarbonyl-n-dodecylamino, N-piperidinocarbonyl-cyclopropylamino, N-piperidinocarbonyl-cyclobutylamino -, N-Piperidinocarbonyl-cyclopentylamino, N-piperidinocarbonyl-cyclohexylamino, N-piperidinocarbonyl-cycloheptylamino, NP iperidinocarbonylcyclopropylmethylamino-N-piperidinocarbonylcyclobutylmethylamino, N-piperidinocarbonylcyclopentylmethylamino, N-piperidinocarbonylcyclohexylmethylamino, N-piperidinocarbonylcycloheptylmethylamino, N-piperidinocarbonyl- (2-cyclopropylethyl) amino, N-piperidinocarbonyl- (2 -cyclobutylethyl) amino, N-piperidinocarbonyl (2-cyclopentylethyl) amino, N-piperidinocarbonyl (2-cyclohexylethyl) amino, N-piperidinocarbonyl (2-cycloheptylethyl) amino, N-piperidinocarbonyl IS-cyclopropylpropyl-amino, N-piperidinocarbonyl-β-cyclobutylpropyl-amino, N-piperidinocarbonyl-fS-cyclopentylpropyl-amino, N-piperidinocarbonyl-i-cyclohexylpropyl) -amino, N-piperidinocarbonyl-O-cycloheptylpropyl-amino, N-piperidinocarbonyl-phenylamino, N-piperidinocarbonylbenzylamino, N-hexamcthyleniminocarbunyl-methylamino, N-hexamethyleneiminocarbonyl-ethylamino, N-hexamethyleneiminocarbonyl-isopropylamino, N-hexamethyleneiminocarbonyl-n-butylamino, N-hexamethyleneiminocarbonyl-n-pentylam ino, N-hexamethyleneiminocarbonyl-n-hexylamino, N-hexamethyleneiminocarbonyln-octylamino, N-hexamethyleneiminocarbonyl-n-dodecylamino, N-hexamethyleneiminocarbonyl-cyclopropylamino, N-hexamethyleneiminocarbonyl-cyclobutylamino, N-hexamethyleneiminocarbonyl-cyclopentylamino, N Hexamethyleneiminocarbonylcyclohexylamino, N-hexamethyleneiminocarbonylcycloheptylamino, N-hexamethyleneiminocarbonylcyclopropylmethylamino, N-hexamethyleneiminocarbonylcyclobutylmethylamino, N-hexamethyleneiminocarbonylcyclopentylmethylamino, N-hexamethyleneiminocarbonylcyclohexylmethylamino, N-hexamethylbenzimycarbonylcycloheptylmethylthio) _/ N- Hβxamβthylβniminocarbonyl (2-cyclopropylβthyl) · amino, N-hexamethyleneiminocarbonyl- (2-cyclobutylethyl) -amino, N-hexamethyleneiminocarbonyl- (2-cyclopentylethyl) -amino, N-hexamethyleneiminocarboxylyl- (2-cyclohexylethyl) -amino , N-hexamethyleneiminocarbonyl- (2-cycloheptylethyl) amino, N-hexamethyleneiminocarbonyl-O-cyclopropylpropyD-amino, N-hexamethylene iminocarbonyl-O-cyclobutylpropyD-amino, N-hexamethyleneiminocarbonyl- (3-cyclopentylpropyl) -amino, N-hexamethyleneiminocarbonyl-O-cyclohexylpropyD-amino, N-hexamethyleneiminocarbonyl-O-cycloheptylpropyD-amino, N-hexamethyleneiminocarbonyl-phenylamino , N-hexamethyleneiminocarbonyl-benzylamino, N-morpholinocarbonyl-methylamino, N-morpholinocarbonyl-ethylamino, N-morpholinocarbonyl-isopropylamino, N-morpholinocarbonyl-n-butylamino, N-morpholinocarbonyl-n-pentylamino, N-morpholinocarbonyl -n-hexylamino, N-morpholinocarbonyl-n-octylamino, N-morpholinocarbonyl-n-dodecylamino, N-morpholinocarbonyl-cyclopropylamino, N-morpholinocarbonyl-cyclobutylamino, N-morpholinocarbonyl-cyclopentylamino, N-morpholinocarbonyl-cyclohexylamino -, N-morpholinocarbonylcycloheptylamino, N-morpholinocarbonylcyclopropylmethylamino, N-morpholinocarbonylcyclobutylmethylamino, N-morpholinocarbonylcyclopentylmethylamino, N-morpholinocarbonylcyclohexylmethylamino, N-morpholiriocarbonylcycloheptylmeth ylamino, N-morpholinocarbonyl- (2-cyclopropylethyl-amino, N-morpholinocarbonyl- (2-cyciobutylethyl) -amino, N-morpholinocarbonyl- (2-cyclopentylethyl) -amino, N-morpholinocarbonyl- (2-cyclohexylethyl) -amino, N-morpholinocarbonyl- (2-cycloheptylethyl) amino, N-morpholinocarbonyl-O-cyclobutylpropylpropyD-amino, N-morpholinocarbonyl-O-cyclobutylpropyD-amino, N-morpholinocarbonyl-fS-cyclopentylpropyD-amino-, N-morpholinocarbonyl-fS-cyclohexylpropyD-amino, N-morpholinocarbonyl-fS-cycloheptylpropyl-amino, N-morpholinocarbonyl-phenylamino, N-morphonocarbonyl-

benzylamino, phthalimino, 5-methoxy-phthalimino, 5,6-dimethoxy-phthalimino, 6-methoxy-phthalimino, homophthalimino, -, -, - dimethyl-homophthalimino, 7-methoxy-homophthalimino, 6,7- Dimethoxy-homophthalimino, 7-Mei xyA4-dimethyl-homophthaliminov6J-dimethoxy-4,4-dimethyl-hornophthalimino, 1,2,3,6-tetrahydrophthalimino, hexahydrophthalimino, i-oxo-isoindolin-2-yl , 3,4-dimethyl-phthalimino-, 4.5 × DimethyM, 2 ₁ 3.6-tetrahydrophthalimino-, 4,5-Dimθthyl · hβxahydrophthalimino ^ 4,5-dimethyl-1-oxo-2-yl isoindoIin, 3 , 4-dinitrethoxyphthalimino ·, 4.5 · dirnethoxy · 1,2,3,6-tetrahydrophthalimino, 4,5-dimethoxy-hexahydrophthalimino, 4,5-dimethoxy-1-oxo-isoindolin-2-yl, Glutarimino, 3,3-tetramethylene glutarimino, 3,3-pentamethylene glutarimino, 2,2-dimethyl glutarimino, 3-methyl glutarimino, 3,3-dimethyl glutarimino, 3-ethyl glutarimino, hexafluoro -glutarimino, 3-ethyl-3-methyl-glutarimino, IS-cyclopentanedicarbonylimino, 2,4-dimethyl-glutarimino, 2 ₍ 4-di-n-propyl-glutarimino, Endo -bicyclol2.2.21-oct-5-ene-2,3-dicarboxylic acid imino, melhyl-5-norbornene ^ .S-dicarboxylic acid imino, Se-endo-oxo-1-AB-tetrahydro-pthalthalino-or B-no-bornin-endo ^ .S-dicarbonsäureiminogruppe,

for R 2 dio for R _{t the} meanings mentioned above or those of 1H-tetrazol-5-yl, 2-imidazolidon-1-yl, 3-methyl-2-imidazolidon-1-yl, 3-ethyl-2-imidazolidone 1-yl, 3-n-propyl-2-imidazolidone 1-yl _/ 3-isopropyl-2-imidazolidon-1-yl, 3-cyclopropyl-imidazolidin-i-yl ^ a-cyclobutyl-Z-irididazolidone i-yl, a-cyclopentyl-Z-imidazolidin-i-yl, S -cyclohexyl-imidazolidin-i-yl .s-cycloheptyl-imidazolidin-i-yl. -S-cyclopropylmethyl-imidazolidone-i -yl-.S-cyclobutylmethyl ^ - imidazolidon-1-yl, 3-cyclop-β-tylmethyl-2-imidazolidone 1-yl-3-cyclohexylmethyl-2-imϊ-diazolidon-1-yl, 3-cycloheptyl-methyl-2-imidazolidin-1-yl, 3- (2-Cyclopropylethyl) -2-imidazolidon-1-yl, S-tZ-cyclobutylethyl-1 -imidazolidin-i-yl, 3- (2-cyclopentylethyl) -2-imidazolidin-1-yl, 3 (2-Cyclohexylethyl) -2-imidazolidin-1-yl, 3- (2-cycloheptylethyl) -2-imidazolidin-i-yl, SO-cyclopropyl-propyl-D-imidazolidin-1-yl, S-β-cyclobutylpropyl -imidazolidone-i -yl, 3- (3-cyclopentylpropyl) -2-imidazolidin-1-yl, 3- (3-cyclohexylpropyl) -2-imidazo lidon-1-yl, 3- (3-cycloheptylpropyl) -2-imidazolidon-1-yl, 3-bonnyl-2-imidazolidin-1-yl, 3- (2-phenylethyl) -2-imidazolidone-1 -yl-, 3- (J-phenylpropyl) -2-imidazolidon-1-yl, 3,4,5,6-tetrahydro-2-pyrimidon-1-yl, 3-methyl-3,4,5, 6-tβ-tetrahydro-2-pyrimidone-1-yl- _/ 3-ethyl-3,4,5,6-tetrahydro-2-pyrimidon-1-yl, 3-n-propyl-3,4,5,6- tetrahydro-2-pyrimidone-i-yl, 3-isopropyl-3,4,5 _/ 6-tetrahydro-2-pyrimidon-1-yl, 3-cyclopropyl-3,4,5,6-tetrahydro-2-ol pyrimidone-1-yl, 3-cyclobutyl-3,4,5,6-tetrahydro-2-pyrimidone-1-yl, S-cyclopentyl-aA.e.e-tetrahydro-pyrimidone-i-yl, 3 -Cyclohexyl-3,4,5,6-tetrahydro-2-pyrimidone-1-yl, 3-cycloheptyl-3,4 _l 5,6-tetrahydro-2-pyrimidone-1-yl, S-cyclopropylmethyl-SAB .etetrahydro-2-pyrimidone-1-yl, 3-Cyclobutylmβthyi-3,4,5,6 · tetrahydro-2-pyrimidone-1-yl, 3-cyclopentylmethyl-3,4,5,6-tetrahydro ^ - pyrimidon-i-yl-.S-cyclohexylmethyl-SAB.e-tetrahydro -pyrimidone-i-yl-.sup.-cycloheptylmethyl-S, .beta.etetrahydro-2-pyrimidone-1-yl, 3- (2- cyclopropylethyl) -3,4,5,6-tetrahydro-2-pyrimidone-1 -yl, 3- (2-cyclobutylethyl) -3,4,5,6-tetrahydro-2-pyrimidone-i-yl, 3- (2-cyclopentylethyl) -3,4,5,6-tetrahydro 2-pyrimidone-1-yl, 3- (2-cyclohexylethyl) -3,4,5,6-tetrahydro-2-pyrimidone-1-yl, 3- (2-cycloheptylethyl) -3,4,5, 6-tetrahydro-2-pyrimidone-1-yl, SO-cyclopropylpropyl J-S, .beta.etetrahydro-2-pyrimidon-1-yl, 3- (3-cyclobutylpropyl) -3,4,5,6-tetrahydro -2-pyrimidone-1-yl, 3- (3-cyclopentylpropyl) -3,4,5,6-tetrahydro-2-pyrimidone-i-yl, S-1S-cyclohexylpropyl-SAS.e-tetrahydro ^ - pyrimidone-i-yl, 3- (3-cycloheptylpropyl) -3,4,5,6-tetrahydro-2-pyrimidon-1-yl, 3-benzyl-3,4,5,6-tetrahydro-2-yl pyrimidon-1-yl, 3- (2-phenylethyl) -3,4,5,6-tetrahydro-2-pyrimidone-1-yl or 3- (3-phenylpropyl) -3,4,5,6- tetrahydro-2-pyrimidone-1-yl group,

for R ₃ those of the hydrogen, fluorine, chlorine or bromine atom, the methyl, ethyl, n-propyl, isonropyl, η-butyl, isobutyl, tert-butyl, n-Pdntyl-, n -Hexyl, 1-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylpropyl, 1 , 1-diethylethyl, methoxymethyl, ethoxymethyl, (2-hydroxyethoxyl-methyl, 2-methoxy-ethyl, 2-ethoxy-ethyl, 3-methoxy-propyl, methylmercaptomethyl, 2-methylmercaptoethyl, S Methylmercapto-propyl, 4-methylmercaptobutyl, methylsulfinylmethyl, 2-methylsulfinylethyl, 3-methylsulfinylpropyl, 4-methylsulfinylbutyl, methylsulfonylmethyl, 2-methylsulfonylethyl, 3-methylsulfonyl-propyl, 4-methylsulfonylbutyl, 2-methylamino-ethyl, 3-vinyl-amino-propyl, 4-hydroxyethylamino-butyl, 2-dimethyl, minoethyl, 3-dimethylamino-propyl, 4-dimethylamino-butyl, 5- Dimethylamino-pentyl, 2-diethylaminoethyl, 2-di-n-propylaminoethyl, 2- (2-hydroxyethoxy) ethyl, 3- (2-hydroxyethoxy ) -propyl, 2- (2-methoxyethoxy) ethyl, 2- (2-methoxyethoxy) -isopropyl, 3- (2-methoxyethoxy) -propyl-, 2- (2-ethoxyethoxy) -ethyl, 2- (2-ethoxyethoxy) -isopropyl, 3- (2-ethoxyethoxy) -propyl, 2- (2-isopropoxyethoxy) -ethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy , 2-hydroxyethoxy, 3-hydroxypropoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-isopropoxyethoxy, 3-methoxypropoxy, 3-isopropoxypropoxv, mercapto, methylmercapto, ethylmercapto, n-propylmercapto , Isopropylmercapto, n-butylmercapto, benzyl, 2-phenylethyl, 3-phenylpropyl, allyl, n-biit-2-enyl, n-pent-2-enyl, n-prop-1-enyl , n-but-1-enyl, n-pent-1-enyl, n-but-3-enyl, n-pent-3-enyl, n-pent-4-enyl, propargyl, n-but-3-ynyl, n-pent-3-ynyl, n-pent-4-ynyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, 2-cyclopentylethyl, 2-cyclohexylethyl, 2-cycloheptylethyl, S-cyclopentylpropyl, S-cyclohexylpropyl, phenyl, hydroxyphenyl, fluorophenyl, chlorophenyl, Bromophenyl, methylphenyl, ethylphenyl, isopropylphenyl, methoxyphenyl, ethoxyphenyl, n-propoxyphenyl, n-butoxyphenyl, hydroxy, (imidazol-4-ylmethylamino, 2- (imidazol-4-ylethylamino, 3 (imidazol-4-yl) propylamino, methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, aminocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, Cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cycloheptylaminocarbonyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, pyrazolyl, 1,3-dimethylpyrazolyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl or tetrazolyl group and

R ₄ represents the carboxy, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl-tert-butoxycarbonyl, n-pentoxycarbonyl, n-hexoxycarbonyl, benzyloxycarbonyl, 1- Phenylethoxycarbonyl, 2-phenyl-ethoxycarbonyl, 3-phenyl-propoxycarbonyl, pivaloyloxymethoxycarbonyl, phthalidyloxycarbonyl, ethoxycarbonyloxyethoxycarbonyl, methoxymethoxycarbonyl, cyclohexyloxycarbonylmethoxycarbonyl, (IS-dioxa) -oxo -methyl-cyclopenten-B-yD-methoxycarbonyl , Amino, phthalimido, aminoacetylamino, methoxycarbonylaminoacetylamino, ethoxycarbonylaminoacetylamino, isopropoxycarbonylaminoacetylamino, n-butoxycarbonylaminoacetylamino, methylcarbonylamino, trifluoromethylcarbonylamino, ethylenediylcarbonylamino, n-propylcarbonylamino, isopropylcarbonylamino, cyclopentylcarbonylamino, cyclohexylcarbonylamino, cycloheptylcarbonylamino, , Phenylcarbonylamino, fluorophenylcarbonylamino, chlorophenylcarbonylamino, bromophenylcarbonylamino, methylp henylcarbonylamino, ethylphenylcarbonylamino, isopropylphenylcarbonylamino, methoxypiienylcarbonylamino, ethoxyphenylcarbonylamino, n-propoxyphenylcarbonylamino, benzylcarbonylamino, 2-phenylethylcarbonylamino, methylsulfor.ylamino, trifluoromethylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino, phenylsulfonylamino,

Fluorphenylsulfonylamino-, Chlorphenylsulfonylamino-, Bromphenylsulfonylamino-, Mothylphonylsulfonylamino-, Ethylphenylsulfonylamino · lsopropylphonylsulfonylamino-, Methoxyphenylsulfonylamino-, Ethoxyphenylsulfonylamino-, Bonzylsulfonylumino-, cyano, aminomethyl, Methylsulfonylaminomethyl-, Ethylsulfonylaminomethyl-, n-Propylsulfonylaminomethyl-, Phenylsulfonylaminomethyl-, Methylphenylsulfonylaminomethyl-, Trifluormothylsulfonylaminomothyl-, Methylsulfonylaminocarbonyl-, Ethylsulfonylaminocarbonyl-, n-Pronylsulfonyllaminocarbonyl-, Isopropylsulfonylaminocarbonyl-, n-Butylsulfonylaminocarbonyl-, Trifluormethylsulfonylaminocarbonyl-, perfluoro-n-butylsulfonylaminocarbonyl-, Phenylsulfonylaminocarbonyl-, Benzylsulfonylaminocarbonyl-, 4-Molhylphenylsulionylaminocarbonyl-, 4-Chlorphonylsulfonylaminocarbonyl-, Trifluoracetylaminoriiethyl- , IH-tetrazolyl or 1- (triphenylmethyl) -tetrazolylgruppe into consideration. Preferred compounds of general formula I are those in which R 1 is hydrogen, fluoro or chlorato, trifluoromethyl, hydroxy, benzyloxy, carboxy, cyano, amino, nitro, aminosulfonyl, mothylaminosulfonyl, Dimethylnosulfonyl, trifluoromethylsulfonyloxy or tetrazolyl group, an alkyl group having 1 to 4 carbon atoms, wherein the methyl group may additionally be substituted by a hydroxy or alkylamino group having 1 to 4 carbon atoms,

an alkoxy group having 1 to 4 carbon atoms which is substituted in the l, 3 or 4 position by a hydroxy, alkoxy, alkylamino,

Dialkylamino odor imidazolyl be substituted and dor alkyl substituent may each contain 1 to 3 carbon atoms,

an alkanoyloxy group having 1 to 4 carbon atoms or o-cycloalkylaminocarbonyloxy group having 5 to 7 carbon atoms in the cycloalkyl part,

b is an amino group represented by a benzyl, decalin, trifluoromethylcarbonyl, benzylcarbonyl, benzyloxycarbonyl, 2-ethyl-5-methylcyclohexyloxy or tert-butoxycarbonylaminoacetyl group, by an alkyl group of 1 to 5 carbon atoms, by a cycloalkyl, cycloalkylalkyl , Cycloalkoxycarbonyl, Cycloalkylcarbonyl or Cycloalkylalkanoylgruppe, wherein the

Cycloalkyl each 5 to 7 carbon atom, dor Alkyltoil 1 to 3 Kohlenstof'atomo and the Alkanoylteil 1 to

3 carbon atomo, by oino alkanoyl group having 1 to 6 carbon atoms, by an aminoalkanoyl or Dialkylaminoalkanoylgruppo, in which each of the alkyl moiety and the Alkanoylteil may contain 1 to 3 carbon atoms, by oino Alkoxycarbonylgruppo having a total of 2 to 7 carbon atoms, by an alkylsulfonyl group 1 to

Is substituted by 4 carbon atoms or by a substituted by a Alkoxycarbonylgruppo with a total of 2 to 4 carbon atoms thiazolidin-3-yl-carbonylgruppo

a Bonzylamino- or alkylamino group having 1 to 5 carbon atoms, on the nitrogen atom additionally by a benzyl or cyclohexyl group, by an alkyl group having 1 to 3 carbon atoms, in the 2- or 3-Stollung by a Alkoxygruppo having 1 to 3 carbon atoms or by oine Phenylaminogruppo may be substituted by an alkanoyl group with 1 to

5 carbon atoms, which may be substituted by an alkoxy group having 1 to 3 carbon atoms, is substituted by a cycloulkylcarbonyl group having a total of 6 to 8 carbon atoms or by an alkoxycarbonyl group having a total of 2 to 4 carbon atoms,

a carbonyl group represented by an alkyl group which is in the 2 or 3 position by a hydroxy, alkoxycarbonyl or .alpha

Alkylamino group may be substituted by an alkylamino group having 1 to 5 carbon atoms, which in the alkyl moiety

a carboxy group may be substituted by an alkylamino group, in the 2- or 3-Stollung by a

Phenylamino group is substituted by a phenyl, alkoxy, amino, benzylamino, phenylethylamino, cycloalkylamino

or cycloalkylalkylamino in which each of the alkyl portion may contain from 1 to 3 carbon atoms and the cycloalkyl portion may contain 5 to 7 carbon atoms, and additionally an alkylamino group having from 1 to 5 carbon atoms on the nitrogen atom may be substituted by an alkyl group having from 1 to 4 carbon atoms, an aminocarbonylamino or aminothiocarbonylamino group which by an alkyl group having 1 to 12 carbon atoms, by an alkenyl or alkynyl group mK in each case 3 to 5 carbon atoms, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, dl before a cycloalkyl, cycloalkylalkyl or phenylalkyl mono-, di- or may be trisubstituted, wherein the substituents may be the same or different and each of the alkyl moiety may contain from 1 to 3 carbon atoms and the cycloalkyl moiety may contain from 5 to 7 carbon atoms, and a methylene group in one

Cycloalkyl radical having 5 to 7 carbon atoms replaced by an oxygen atom and an alkyl group in the 4-, 5- or 6-position

may be substituted by a hydroxy or trifluoroacetyl group,

a Cycloalkyleniminocarbonylaminogruppe with 4 to 6 carbon atoms in Cycloalkyleniminoteil or a

Morpholinocarbonylamino group, both on the amino nitrogen by an alkyl group having 1 to 12 carbon atoms, by

a cycloalkyl, cycloalkylalkyl or phenylalkyl group in each of which the alkyl moiety may contain from 1 to 3 carbon atoms and the cycloalkyl moiety may contain from 5 to 7 carbon atoms, a phthalimino, homophthalimino, 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-

Carboxyphenylmethylencarbonylamino or 2-Carboxymethylonphenylcarbonylaminogruppe, wherein a carbonyl group in

a phthalimino group replaced by a methylene group and a methylene group in a homophthalimino, 2-

Carboxyphenylmethylencarbonylamino or 2-carboxymethylenephenylcarbonylamino group by one or two Methyl groups may be substituted, and additionally the above-mentioned Phenylkerne by methyl or Muthüxygruppen mono- or disubstituted, where the substituents may be the same or different, and at the same time completely

or partially hydrogenated, a bicycloalkane-3-carboxylic acid amino or bicycloalkene S -carboxylic acid amino group substituted in the 2-position by a carboxy group, a bicycloalkane-2,3-dicarboxylic acid amino or

Bicycloalkene-2,3-dicarboxylic acid imino group in which the bicycloalkane and bicycloalkene moieties each 9 or

Containing 10 carbon atoms, substituted by 1, 2 or 3 methyl groups, and an endomethylene group by 1

Oxygen atom may be replaced, a Glutarsäureimino- or 3-carboxy-n-propylene-carbonyl group, in each of which

perfluorinated n-propylene, may be substituted by one or two alkyl groups or by a tetramethylene or Pentamethylengruppes, or

a 5,7-dioxa-iH, 3Himidazo [1,5-c] thiazole group, a 2-imidazolidin-1-yl group optionally substituted in the 3-position by an alkyl group having 1 to 3 carbon atoms, or a 3,4, 5,6-tetrahydro-2-pyrimidone-1-yl group,

R2 is a hydrogen, fluorine or chlorine atom, a methyl, hydroxy or methoxy group, or Ri and R ₂ together with the two ortho-carbon atoms of the adjacent phenyl ring, a phenyl or

1-alkyl-3,3-dialkyl-2,3-dihydro-pyrrol-2-one group, in which the alkyl part can contain in each case 1 to 3 carbon atoms,

Ra is a hydrogen, fluorine or chlorine atom,

a hydroxy, benzyl or aminocarbonyl group,

an alkyl group having 1 to 5 carbon atoms, wherein the methyl group may be additionally substituted by a hydroxy group, by an alkoxy, alkylsulfenyl, alkylsulfinyl or alkylsulfonyl group each having 1 to 3 carbon atoms, a cycloalkyl or cycloalkylalkyl group, in which the cycloalkyl part is each 5 to 7 carbon atoms and the alkyl part 1 to

May contain 3 carbon atoms, an alkenyl or alkynyl group each having 3 to 5 carbon atoms, a phenylalkyl group having 1 to 3 carbon atoms,

an alkylamino group having 1 to 4 carbon atoms,

a pyridyl, furyl, thiazolyl or pyrazolyl group which may be substituted by one or two methyl groups,

R _{4 is} an alkoxycarbonyl having a total of 1 to 5 carbon atoms, an amino, phthalimino, aminomethyl, carboxy, cyano, Methylsulfonylaminocarbonyl-trifluoromethylsulfonylaminocarbonyl, benzenesulfonylaminocarbonyl, Trifluoromethylcarbonylaminomethyl, trifluoromethylaminomethyl, tetrazolyl or 1- (triphenylmethyl) -tetrazolyl group, R _{5 is} a hydrogen, fluorine, chlorine or bromine atom Re is a hydrogen atom or R ₅ and R ₈ together with the two ortho-substituted carbon atoms signify a phenyl group whose 1, 3, 3 Isomer mixtures and their addition salts, especially for the pharmaceutical application of their physiological

optional addition salts with inorganic or organic acids.

Particularly preferred compounds of general formula I are those in which R _{1 is} an amino group represented by a benzyl, decalin, trifluoromethylcarbonyl, benzylcarbonyl, benzyloxycarbonyl, 2-ethyl-5

methylcyclohexyloxy or tert.butoxycarbonylaminoacetyl group, by an alkyl group having 1 to 5 carbon atoms, by a cycloalkyl, cycloalkylalkyl, cycloalkoxycarbonyl, cycloalkylcarbonyl or cycloalkylalkanoyl group, wherein the

Cycloalkyl each 5 to 7 carbon atoms, the alkyl part 1 to 3 Kohienstoffatome and the Alkanoylteil 1 to 3

Carbon atoms, by an alkanoyl group having 1 to 6 carbon atoms, by an aminoalkanoyl or dialkylaminoalkanoyl group in which each of the alkyl moiety and the alkanoyl moiety may contain 1 to 3 carbon atoms, by an alkoxycarbonyl group having a total of 2 to 7 carbon atoms, by an alkylsulfonyl group having 1 is substituted by 4 to 4 carbon atoms or by a thiazolidin-3-yl-carbonyl group substituted by an alkoxycarbonyl group having a total of 2 to 4 carbon atoms,

a benzylamino or alkylamino group having 1 to 5 carbon atoms, on the nitrogen atom additionally by a benzyl or cyclohexyl group, by an alkyl group having 1 to 3 carbon atoms, in the 2- or 3-position by an alkoxy group having 1 to 3 carbon atoms or by a Phenylamino group may be substituted by an alkanoyl group having 1 to 5 carbon atoms which may be substituted by an alkoxy group having 1 to 3 carbon atoms, by a cycloalkylcarbonyl group having a total of 6 to 8 carbon atoms or by an alkoxycarbonyl group having a total of 2 to

4 carbon atoms is substituted,

an aminocarbycylamino or aminothiocarbonylamino group which is substituted by a. Alkyl group with 1 to 12

Carbon atoms, by an alkenyl or alkynyl group each having 3 to 5 carbon atoms, by a hi or

tricyclic Alkylgruppo having 7 to 11 carbon atoms, by a cycloalkyl, cycloalkylalkyl or phenylalkyl mono-, di- or may be trisubstituiert, wherein the substituents may be identical or different and each of the alkyl moiety 1 to 3 carbon atoms and the cycloalkyl part contain 5 to 7 carbon atoms can as well as a methylene group in one

Cycloalkyl radical having 5 to 7 carbon atoms replaced by an oxygen atom and an alkyl group in the 4-, 5- or 6-position

may be substituted by a hydroxy or trifluoroacetyl group,

a Cycloalkyleniminocarbonylaminogruppe with 4 to 6 carbon atoms in Cycloalkyleniminoteil or a

Morpholinocarbonylamino group, both on the amino nitrogen by an alkyl group having 1 to 12 carbon atoms, by

In each of which the alkyl moiety may contain 1 to 3 carbon atoms and the cycloalkyl moiety may contain 5 to 7 carbon atoms, a phthalimino, homophthalimino, 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-cycloalkyl, cycloalkylalkyl or phenylalkyl group may be substituted. Carboxyphenylmethylencarbonylamino or 2-carboxymethylenephenylcarbonylamino group, where a carbonyl group in a phthalimino group is replaced by a methylene group and a methylene group in a homophthalimino group, 2

Carboxyphenylmethylencarbonylamino or 2-carboxymethylenephenylcarbonylamino group by one or two Methyl groups may be substituted, and additionally the above-mentioned Phenylkerne by methyl or Mono- or disubstituted methoxy groups, wherein the substituents may be the same or different, and at the same time completely

or partially hydrogenated, a bicycloalkane-3-carboxylic acid amino or bicycloalkene S-carboxylic acid amino group substituted in the 2-position by a carboxy group, a bicycloalkane-2,3-dicarboxylic acid amino or

Bicycloalkene-2,3-dicarboxylic acid imino group in which the bicycloalkane and bicycloalkene moieties each 9 or

Containing 10 carbon atoms, substituted by 1, 2 or 3 methyl groups, and an endomethylene group by 1

Oxygen atom may be replaced, a Glutarsäureimino- or 3-carboxy-n-propylencarbonylgruppe, in each of which

perfluorinated n-propylene, may be substituted by one or two alkyl groups or by a tetramethylene or Pentamethylengruppes, or

a 5,7-oioxa-1H, 3H-imidazo (1,5-c) thlazolyl group,

R] is a hydrogen radical, a methyl or hydroxy group or R ₁ and R ₂ together with the two ortho-carbon atoms of the adjacent phenyl ring have a phenyl group, R _{3 is} an alkyl group having 3 to 5 carbon atoms, an alkenyl or alkynyl group having in each case 3 to 5 carbon atoms, R _{4 is} a carboxy, methylsulfonylaminocarbonyl, trifluoromethylsulfonylaminocarbonyl, benzenesulfonylaminocarbonyl, Trifluoromethylcarbonylaminomethyl, trifluoromethylaminomethyl or tetrazolyl group, Rs is a hydrogen atom, R _{6 is} a hydrogen atom or R ₆ and Re together with the two ortho-carbon atoms denote a phenyl group, especially those Compounds of the general formula I in which R _{1 is} an amino group represented by an alkanoyl group having 1 to β carbon atoms, by an aminoalkanoyl or Dialkylaminoalkanoylgruppe in which the alkyl moiety and the alkanoyl moiety may each contain 1 to 3 carbon atoms, by

an alkoxycarbonyl group having a total of 2 to 7 carbon atoms or substituted by a thiazolidin-3-yl-carbonyl group substituted by an alkoxycarbonyl group having a total of 2 to 4 carbon atoms,

a benzylamino or alkylamino group having 1 to 5 carbon atoms substituted on the nitrogen atom by an alkanoyl group having 1 to 5 carbon atoms which may be substituted by an alkoxy group having 1 to 3 carbon atoms by a cycloalkylcarbonyl group having a total of 6 to 8 carbon atoms or by an alkoxycarbonyl group having altogether 2 to 4

Substituted carbon atoms,

an aminocarbonylamino or aminothiocarbonylamino group represented by an alkyl group having 1 to 8 carbon atoms, by an alkenyl or alkynyl group each having 3 to 5 carbon atoms, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, by a cycloalkyl, cycloalkylalkyl or Phenylalkyl group may be mono-, di-or trisubstituted, wherein the substituents may be the same or different and each of the alkyl moiety 1 to 3 Kohlenstolffatome and the cycloalkyl part may contain 5 to 7 carbon atoms and a methylene group in one

Cycloalkyl radical having 5 to 7 carbon atoms replaced by an oxygen atom and an alkyl group in the 4-, 5- or 6-position

may be substituted by a hydroxy or trifluoroacetyl group,

a cycloalkyleneiminocarbonylamino group having 4 to 6 carbon atoms in the cycloalkyleneimine moiety or a morpholinocarbonylamino group both of which may be substituted on the amino nitrogen by an alkyl group of 1 to 8 carbon atoms, by a cycloalkyl, cycloalkylalkyl or phenylalkyl group in which each of the alkyl moiety is 1 to 3 carbon atoms and the cycloalkyl moiety 5 to 7 carbon atoms, a phthalimino, homophthalimino, 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-carboxyphenylmethylenecarbolnylamino or 2-carboxymethylenephenylcarbonylamino group, a carbonyl group in a phthalimino group being replaced by a methylene group and a methylene group in a homophthalimino group , 2-Carboxyphenylmethylencarbonylamino- or 2-carboxymethylenephenylcarbonylamino group may be substituted by one or two methyl groups, and additionally the above-mentioned phenyl nuclei by methyl or

Mono- or disubstituted methoxy groups, wherein the substituents may be the same or different, and at the same time completely

or partially hydrogenated, a bicycloalkane-3-carboxylic acid amino or bicycloalkene S-carboxylic acid amino group substituted in the 2-position, a bicycloalkane-2,3-dicarboxylic acid or bicycloalkene ^, S-dicarboxylic acid imino group in which the bicycloalkane and bicycloalkene moiety each containing 9 or 10 carbon atoms, substituted by 1, 2 or 3 methyl groups, and an endomethylene group may be replaced by an oxygen atom, a glutaric imino or 3-carboxy-n-propylenecarbonyl group, in each of which the n-propylene group is perfluorinated by or two alkyl groups or may be substituted by a tetramethylene or pentamethylene group, or

a 5,7-dioxa-1H, 3H-imidazo [1,5-c] ihiazolyl group,

R _{2 is} a hydrogen atom,

Ri and R _2, together with the two ortho-carbon atoms of the adjacent phenyl ring, have a phenyl group,

R _{3 is} an alkyl group having 3 to 5 carbon atoms, an alkenyl-containing alkynylcroup having in each case 3 to 5 carbon atoms,

R _{4 is} a carboxy or tetrazolyl group,

R _{6 is} a hydrogen atom,

Re is a hydrogen atom or

R ₅ and R 6 together with the two ortho-standing carbon atoms represent a phenyl group, their 1, 3-isomer mixtures and their addition salts, in particular for the pharmaceutical application of their physiologically acceptable addition salts with inorganic or organic acids.

According to the invention, the novel compounds of the formula I are obtained by the following processes:

a) Cyclization of a compound of the formula

in the

R ₁ and R-> are as defined above,

one of the radicals X, or Y _{1 is} a group of the formula

and the other of X ₁ or Y _{1 is} a group of the formula

_s - NH - C - R '

Represent ^J , where

R ₃ 'except for the fluorine, chlorine or bromine atom, the hydroxy, mercapto or aminocarbonyl group, which latter may be substituted by an alkyl group of 1 to 3 carbon atoms or by a cycloalkyl group of 5 to 7 carbon atoms substituted for R 2 Has ₃ meanings mentioned above,

R ₄ to R _{6 are} as defined above,

R7 is a hydrogen atom, a hydroxy group or a

Ra'CO group, wherein R ₃ 'is defined as mentioned above,

Z) and Z ₂ , which may be identical or different, optionally substituted amino groups or optionally substituted by lower alkyl groups hydroxy or mercapto groups or

Zi and Z ₂ together represent an oxygen or sulfur atom, an imino group optionally substituted by an alkyl group having 1 to 3 carbon atoms, an alkylenedioxy or alkylene dithio group each having 2 or 3 carbon atoms, but one of X) or Y, a group the formula

-N (COR, ¹ ) -

or

Z, Z. _N l / 2

- NH - C - R ₃ ¹ must represent.

The cyclization is conveniently carried out in a solvent or solvent mixture such as ethanol, isopropanol, glacial acetic acid, benzene, chlorobenzene, toluene, xylene, glycol, glycol monomethyl ether, diethylene glycol dimethylehers, sulfolane, dimethylformamide, tetralin or in an excess of that for preparing the compound of general formula II used acylating agent, for. Example, in the corresponding nitrile, anhydride, acid halide, ester or amide, for example at temperatures between 0 and 250 ⁰ C, but preferably at the boiling temperature of the reaction mixture, optionally in the presence of a condensing agent such as phosphorus oxychloride, thionyl chloride, sulfuryl chloride, sulfuric acid, p-toluenesulfonic acid , Methanesulfonic acid, hydrochloric acid, phosphoric acid, polyphosphoric acid, acetic anhydride or, if appropriate, also in the presence of a base such as potassium ethylate or potassium tert-butylate. However, the cyclization can also be carried out without a solvent and / or condensing agent. However, the reaction is carried out particularly advantageously in such a way that a compound of formula II is prepared in the reaction mixture by reduction of a corresponding o-nitro-amino compound optionally in the presence of a carboxylic acid of the formula R ₃ ¹ COOH or by acylation of a corresponding o-diamino compound. Upon termination of the reduction of the nitro group on the Hydroxylaminstufe obtained in the subsequent cyclization of the N-oxide of a compound of formula I. The resulting N-oxide is then converted by reduction into a corresponding compound of formula I.

The subsequent reduction of the resulting N-oxide of the formula I is preferably carried out in a solvent such as water, water / ethanol, methanol, glacial acetic acid, ethyl acetate or dimethylformamide with hydrogen in the presence of a hydrogenation catalyst such as Raney nickel, platinum or palladium / carbon, with metals such Iron, tin or zinc in the presence of an acid such as acetic acid, hydrochloric acid or sulfuric acid, with salts such as iron sulfate, tin dichloride or sodium dithionite, or with hydrazine in the presence of Raney nickel at temperatures between 0 and 50 ⁰ C, but preferably carried out at room temperature.

A optionally obtained 2-alkoxy compound of the formula I can then, if desired, by hydrolysis, preferably in the presence of an acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or trichloroacetic acid, in a suitable solvent such as water, water / methanol, ethanol, water / ethanol, water / Isopropanol or water / dioxane, at temperatures between -10 and 120 ⁰ C, z. B. at temperatures between 2O ⁰ C and the boiling temperature of the reaction mixture, are converted into a corresponding 2-hydroxy compound of formula I, b) for the preparation of the compounds of formula I, in the R ₃ for R ₃ initially mentioned aromatic or heteroaromatic radicals represents: reaction of a phenylenediamine of the formula

, (III)

in the

R and R _{2 are} as defined above,

one of the radicals X ₂ or Y _{2 is} a group of the formula

-NH-CH ₂

in the

R ₄ to R _{6 are} as defined above,

and the other of X ₂ or Y _{2 is} an amino group, with an aldehyde of the formula

OCH-R ₃ ", (IV)

in the

R ₃ "means the initially mentioned for R ₃ aromatic or heteroaromatic radicals. The reaction is preferably carried out in a suitable solvent such as benzene, toluene, xylene, mesitylene or

Dimethylacetamide in the presence of an oxidizing agent such as sulfur or atmospheric oxygen at temperatures between 80 and 250 ° C, preferably at the boiling temperature of the reaction mixture, performed.

A optionally obtained 2-alkoxy compound of the formula I can then, if desired, by hydrolysis, preferably in the presence of an acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or trichloroacetic acid, in a suitable solvent such as water, water / methanol, ethanol, water / ethanol, water / Isopropanol or water / dioxane, at temperatures between -10 and 120 ⁰ C, z. B. at temperatures between 20 ° C and the boiling temperature of the reaction mixture, converted into a corresponding 2-hydroxy compound of formula I.

c) For the production of compounds of formula I, in which at least one of the radicals R | represents containing _R2 and / or R3 mentioned a sulphinyl or sulphonyl residues and the |, R ₂ and / or R ₃ one of R others of the radicals R ₁ , R ₂ and / or R _{3 are} as defined above:

Oxidation of a compound of the formula

in the

R ₄ to R _{6 are} as defined above,

at least one of the radicals R /, R ₂ 'and / or R ₃ "' represents one of the radicals R 1, R ₂ and / or R ₃ mentioned above containing a sulfur atom or a sulfinyl group and the remaining radicals R 1 ', R ₂ ' and / or R ₃ "'have the meanings mentioned for Ri, R ₂ and / or R ₃ at the outset.

The oxidation is preferably carried out in a solvent or solvent mixture, ζ. As in water, water / pyridine, acetone, glacial acetic acid, dilute sulfuric acid or trifluoroacetic acid, depending on the Oxisierungsmittel used expediently at

Temperatures between -80 and 100 ° C performed. For the preparation of a sulfinyl compound of the formula 1, the oxidation

conveniently carried out with one equivalent of the oxidizing agent used, for. B. with hydrogen peroxide in glacial acetic acid, trifluoroacetic acid or formic acid at 0 to 20 ° C or in acetone at 0 to 6O ⁰ C, with a peracid such as performic acid in glacial acetic acid or trifluoroacetic acid at 0 to 50 ° C or with m-chloroperbenzoic acid in methylene chloride or chloroform at -20 to 6O ⁰ C, with sodium metaperiodate in aqueous methanol or ethanol at -15 to 25 ⁰ C, with bromine in glacial acetic acid or aqueous acetic acid, mi; N-bromo-.iuccinimide in ethanol, mitert.Butyl-hypochlorite in methanol at -80 to -30 ° C, with iodobenzodichloride in aqueous pyridine at 0 to 50 ° C, with nitric acid in glacial acetic acid at 0 to 20 ⁰ C, with chromic acid in glacial acetic acid or in acetone at 0 to 2O ⁰ C and with sulfuryl chloride in methylene chloride at -7O ⁰ C, the resulting thioether

Chlorine complex is conveniently hydrolyzed with aqueous ethanol.

For the preparation of a sulfonyl compound of the formula I, the oxidation is advantageously carried out with one or with two or more equivalents of the oxidizing agent used, for. B. with hydrogen peroxide in glacial acetic acid, trifluoroacetic acid or in formic acid at 20 to 100 ° C or in acetone at 0 to 60 ⁰ C, with a peracid such as performic acid or m-chloroperbenzoic acid in glacial acetic acid, trifluoroacetic acid, methylene chloride or chloroform at temperatures between 0 and 6O ⁰ C, with nitric acid in glacial acetic acid at 0 to 2O ⁰ C, with chromic acid or potassium permanganate in glacial acetic acid, water / sulfuric acid or in acetone at 0 to 20 ⁰ C.

d) For the preparation of a compound of the formula I in which R _{4 represents} a carboxy or amino group:

Transfer of a compound of the formula

(Vl)

in the

R ₄ to R ₃ , R ₅ and R _{6 are} as defined above and R ₄ ^{1 represents} a group convertible into a carboxy group by hydrolysis, thermolysis or hydrogenolysis or a group convertible into an amino group by hydrolysis, hydrogenolysis or transamidation.

For example, functional derivatives of the carboxy group, such as their unsubstituted or substituted amides, esters,

Thiolesters, orthoesters, iminoethers, amidines or anhydrides, the nitrile group or the tetrazolyl group by hydrolysis into a carboxy group,

Esters with tertiary alcohols, e.g. B. the tert. Butyl, by thermolysis in a carboxy group, esters with aralkanols, eg. B. the Bnnzylester, by means of hydrogenolysis in a carboxy group,

Acylamino groups, eg. As the Benzcylamino- or phthalimido, by hydrolysis in an amino group imino groups and Imino groups, z. B. the phthalimino group are converted by transamidation into an amino group.

The hydrolysis is conveniently carried out either in the presence of an acid such as hydrochloric acid, sulfuric acid, phosphoric acid, trichloroacetic acid or trifluoroacetic acid in the presence of a base such as sodium hydroxide or potassium hydroxide in a suitable solvent such as water, water / methanol, ethanol, water / ethanol, water / isopropanol or water / Dioxane at temperatures between - 10 ° C and 120 ⁰ C, z. B. at temperatures between room temperature and the boiling temperature of the reaction mixture, carried out. In the hydrolysis in the presence of an organic acid such as trichloroacetic acid or trifluoroacetic acid optionally present alcoholic hydroxyl groups can be converted simultaneously into a corresponding acyloxy group as the trifluoroacetoxy.

If R ₄ 'in a compound of the formula VI is a cyano or aminocarbonyl group, these groups may also be reacted with a nitrite, eg. As sodium nitrite, in the presence of an acid such as sulfuric acid, this is suitably used simultaneously as a solvent, be converted at temperatures between 0 and 5O ⁰ C in the carboxy group.

For example, R ₄ 'in a compound of formula VI is tert. Butyloxycarbonylgruppe, so the tert. butyl

also thermally optionally in an inert solvent such as methylene chloride, chloroform, benzene, toluene, tetrahydrofuran or dioxane and preferably in the presence of a catalytic amount of an acid such as p-toluenesulfonic acid, sulfuric acid, phosphoric acid or polyphosphoric acid, preferably at the boiling temperature of the solvent used, for. B. at temperatures between 4O ⁰ C and 100 ⁰ C, are split off.

If R ₄ 'in a compound of the formula VI is, for example, the benzyloxycarbonyl group, the benzyl group may also be hydrogenolytically reacted in the presence of a hydrogenation catalyst such as palladium / carbon in a suitable solvent, such as

Methanol, ethanol, ethanol / water, glacial acetic acid, ethyl acetate, dioxane or dimethylformamide preferably at temperatures between 0 and 5O ⁰ C, z. B. at room temperature, and a hydrogen pressure of 1 to 5 bar are split off.

In the hydrogenolysis other radicals, for. A nitro group to the amino group, a benzyloxy group to the hydroxy group, a vinylidene group to the corresponding alkylidene group or a cinnamic acid group to the corresponding phenyl-propionic acid group, mitreduziert or by hydrogen atoms, e.g. a halogen atom is replaced by a hydrogen atom.

If R ₄ 'is a phthalimino group, this group may be in the presence of a primary organic base such as methylamine, ethylamine or propylamine in a suitable solvent such as methanol, ethanol, isopropanol, dimethylformamide, methanol / dimethylformamide or methanol / water by transamidation at temperatures between 0 and 5O ⁰ C, but preferably at room temperature, particularly advantageous converted into an amino group. If R ₁ and / or R ₂ here signify one of the imino radicals mentioned in the introduction, they are simultaneously converted into a corresponding amino group.

If Ri and / or R ₂ in a compound of the formula VI have one of the imino radicals mentioned at the outset, this may furthermore be partially hydrolyzed during the reaction, ie, for example, into a 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-carboxyphenylmethylencarbonylamino or 2-carboxymethylenephenylcarbonylamino group, with one methylene group in a 2-

Carboxyphenylmethylencarbonylamino or 2-carboxymethylenephenylcarbonylamino group by one or two

In addition, the above-mentioned phenyl nuclei mono- or disubstituted by alkyl or alkoxy groups, wherein the substituents may be identical or different, and may be hydrogenated wholly or partially simultaneously, a bicycloalkane substituted in the 2-position by a carboxy group S-carboxylic acid amino or bicycloalkene-S-carboxylic acid amino group in which the bicycloalkane and bicycloalkene moiety each contain 9 or 10 carbon atoms, substituted by 1, 2 or 3 methyl groups, and an endomethylene group may be replaced by an oxygen atom, a 3-carboxy-n-propylenecarbonyl group in which the n-propylene group may be perfluorinated, substituted by one or two alkyl groups or by a tetramethylene or pentamethylene group.

e) Reaction of a benzimidazole of the formula

(VII)

in which R ₁ to R _{3 are} as defined above, with a biphenyl compound of the formula

(VIII)

in which R ₄ to Re are as defined above and Z _{3 is} a nucleophilic leaving group such as a halogen atom, for example a chlorine, bromine or iodine atom, or a substituted sulphonyloxy group, for. A methanesulfonyloxy, phenylsulfonyloxy or p-toluenesulfonyloxy group.

The reaction is conveniently carried out in a solvent or solvent mixture such as methylene chloride, diethyl ether, tetrahydrofuran, dioxane, dimethylsulfoxide or benzene optionally in the presence of an acid-binding agent such as sodium carbonate, potassium carbonate, sodium hydroxide, potassium tert-butylate, triethylamine or pyridine, the latter two being simultaneously can also be used as a solvent, preferably at temperatures between 0 and 100 ⁰ C, z. B at temperatures between room temperature and 50 ° C, carried out.

In the reaction, a mixture of the 1- and 3-isomers is preferably obtained.

f) For the preparation of a compound of the formula I in which R _{4 represents} a 1H-tetrazolyl group:

Cleavage of a protecting group from a compound of the formula

(IX)

in the Ri to R ₃ , R ₆ and R _{6 are} as defined above and R ₄ "represents a protected in 1-position by a protecting group 1 H-tetrazolyl group.

As a protective group is, for example, the triphenylmethyl, tributyltin or Triphenylzinngruppe into consideration.

The cleavage of a protective moiety used is preferably in the presence of a hydrogen halide, preferably

in the presence of hydrogen chloride, in the presence of a base such as sodium hydroxide or alcoholic ammonia in a suitable solvent such as methylene chloride, methanol, methanol / ammonia, ethanol or isopropanol at temperatures between 0 and 100 ° C, but preferably at room temperature, or even if the reaction is carried out in the presence of alcoholic ammonia, at elevated temperatures, for. B. at temperatures between 100 and 15O ⁰ C, preferably at temperatures between 120 and 140 ° C.

g) For the preparation of a compound of the formula I in which R _{4 represents} a 1H-tetrazolyl group:

Reaction of a compound of the formula

(X)

CN

in which R ₁ to R ₃ , R ₈ and R _{6 are} as defined above, with hydrazoic acid.

The reaction is preferably carried out in a solvent such as benzene, toluene or dimethylformamide at temperatures

between 80 and 130 ° C, preferably at 125 ⁰ C performed. In this case, the hydrazoic acid is particularly advantageously liberated during the reaction from an alkali azide, for example from sodium azide, in the presence of a weak acid such as ammonium chloride, h) for preparing a compound of formula I in which R ₁ and / or R _{2 represents} an aminocarbonylamino group which may be mono-, di- or trisubstituted by a bi- or tricyclic alkyl group or by an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkalkyl, aralkyl or aryl group, with a methylene group in a cycloalkyl radical having from 4 to 7 carbon atoms an oxygen atom may be replaced: reaction of a compound of the formula

RgNH

(XI)

in the

R ₂ to R o are as defined above and

R _{8 is} a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl or alkynyl group having 3 to Carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a cycloalkyl-alkyl group in which

Cycloalkyl moiety 3 to 7 carbon atoms, the Alkyiteil contain 1 to 3 carbon atoms and may be replaced by an oxygen atom in a cycloalkyl having 4 to 4 carbon atoms, a bicyclic or tricyclic alkyl group having 7 to 10 carbon atoms, an aryl or aralkyl group having 1 to 3 carbon atoms in Alkyiteil, wherein the aryl group is optionally substituted by a fluorine, chlorine or bromine atom, a hydroxy, alkyl or alkoxy group each having 1 to 4

Carbon atoms substituted phenyl group, means, with a compound of formula

N - CW -

(XII)

in the

R ₉ , which may be identical or different, have the meanings mentioned above for R a, W is an oxygen or sulfur atom,

Z _{4 is} a nucleophilic leaving group such as a chlorine or bromine atom or even if at least one of the radicals R ₃ a

Represents hydrogen atom,

Z ₄ and Rg together represent a nitrogen-carbon bond or a cycloalkyleneimino group having 4 to 6 carbon atoms or a morpholino group.

The reaction is preferably carried out in a solvent such as tetrahydrofuran, dioxane, ethylene chloride or benzene optionally in the presence of an acid-binding agent such as triethylamine or pyridine at temperatures between 0 and 100 ⁰ C, preferably at temperatures between 20 and 8O ⁰ C.

i) for the preparation of a compound of the formula I in which R _{4 is} a trifluoromethylcarbonylamino, trifluoromethylcarbonylaminomethyl, trifluoromethylsulphonylamino, trifluoromethylsulphonylaminomethyl or 1H-tetrazolyl group, an alkylcarbonylamino, alkylcarbonylaminomethyl, arylcarbonylamino, arylcarbonylaminomethyl, aralkylcarbonylamino, aralkylcarbonylaminomethyl, Alkylsulfonylamino, alkylsulfonylaminomethyl, arylsulfonylamino, arylsulfonylaminomethyl, aralkylsulfonylamino or aralkylsulfonylaminomethyl groups in which the alkyltiil is 1 to

May contain carbon atoms, represents: Acylation of a compound of the formula

(XlIl)

in the

R ₁ to R ₃ , R ₉ and Re are as defined above and R ₄ "'represents an amino or aminomethyl group, with a compound of the formula

HO-UR ₁₀

(XIV)

in the

R _{10 is} a trifluoromethyl group, an alkyl, aryl or aralkyl group, wherein the alkyl moiety may each contain 1 to 3 carbon atoms, and

U represents a carbonyl or sulfonyl group, or with their reactive derivatives such as their acid halides, acid esters or acid anhydrides.

Examples of reactive derivatives of a compound of the formula XIV are their esters, such as the methyl, ethyl or benzyl esters, their thioesters, such as the methylthio or ethyl thioesters, their halides, such as the acid chloride, their anhydrides

or imidazolides.

The reaction is conveniently carried out in a solvent or solvent mixture such as water, methylene chloride,

Chloroform, ether, tetrahydrofuran, dioxane or dimethylformamide with an appropriate carboxylic acid in the presence of an acid activating or dehydrating agent such as thionyl chloride, with their anhydrides such as acetic anhydride, with their esters such as ethyl acetate, with their halides such as acetyl chloride or methanesulfonyl optionally in the presence of an inorganic or tertiary organic base, such as sodium hydroxide, potassium carbonate, triethylamine or pyridine, the two latter can also serve as a solvent, at temperatures between -25 and 100 "C, but preferably at temperatures between -10 and 80 ⁰ C performed.

k) For the preparation of a compound of the formula I in which R _{4 is} an alkylsulfonylaminocarbonyl or perfluoroalkylsulfonylamino group each having 1 to 4 carbon atoms in the alkyl portion or a benzylsulfonylaminocarbonyl group:

Reaction of a reactive derivative of a carboxylic acid of the formula

(XV)

COOH

in the

Ri to Ra, R5 and R _{6 are} as defined above, with a sulfonamide of the formula

H ₂ N-SO ₂ -Rn,

(XVI)

in the

Ru represents an alkyl or perfluoroalkyl group each having 1 to 4 carbon atoms or a benzyl group, or with the same Alkali salt.

Suitable reactive derivatives of a carboxylic acid of the formula XV which can be prepared in the reaction mixture are their halides such as the chloride or bromide or their carbonic ester derivatives such as the Imiazolcarbonyloxy- or Diphenylcarbamoyloxyderivat into consideration.

The reaction is conveniently carried out in a suitable solvent such as methylene chloride, tetrahydrofuran, dioxane or dimethyl sulfoxide at temperatures between 0 and 180 ° C, preferably between room temperature and 150 ⁰ C. However, the reaction can also be carried out in the melt.

1) For the preparation of a compound of the formula I in which R _{2 is} a 2-imidazolidon-1-yl or 3,4,5,6-one which is optionally substituted in the 3-position by an alkyl, cycloalkyl, cycloalkylalkyl or aralkyl group Tetrahydro-2-pyrimidon-1-yl group represents:

Cyclization of a compound of the formula

(XVII)

Hal (CH ₂ J _n -NH-CO-N

in which R ₁ , R ₃ and R ₄ to R 9 are as defined above, Hal represents a chlorine, bromine or iodine atom and η represent the number 2 or 3, and if necessary subsequent reaction with a compound of the formula

R ₁₂ -Hal,

(XVIII)

in the

R _{12 is} an alkyl, cycloalkyl, cycloalkylalkyl or aralkyl group and

Hai represents a chlorine, bromine or iodine atom.

The cyclization and, if necessary, the subsequent alkylation is conveniently carried out in a solvent such as methanol, ethanol, benzene or dimethyl sulfoxide optionally in the presence of a phase transfer catalyst such as benzyltriethylammonium bromide in the presence of an acid-binding agent such as sodium hydroxide, sodium methoxide, sodium ethylate, sodium hydride or potassium tert-butylate at temperatures between 20 and 100 ° C, preferably at temperatures between 30 and 7O ⁰ C performed.

m) For the preparation of compounds of the general formula I in which

R _{1 represents} an amino group represented by a dialkylaminoalkanoyl, acyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl,

Aryloxycarbonyl, aralkoxycarbonyl or trifluoroacetyl group, monosubstituted by an alkylsulfonyl group having 1 to 4 carbon atoms, by an alkoxycarbonyl group having a total of 2 to 7 carbon atoms or by an alkoxycarbonyl-substituted thiazolidone-3-yl-carbonyl group,

an alkylamino group having 1 to 6 carbon atoms which may be substituted on the nitrogen atom by an alkylsulfonyl or acyl group, where, if the acyl group is an alkanoyl group, this may additionally be substituted by an alkoxy group, and the alkyl substituent from position 2 is replaced by a hydroxy group Alkoxy or arylamino group may be substituted,

an N-alkoxycarbonyl-alkylamino, N-cycloalkoxycarbonyl-alkylamino, N-cycloalkylalkoxycarbonylalkylamino, N-aryloxycarbonylalkylamino or N-aralkoxycarbonylalkylamino group in which the alkyl group may each contain 1 to 6 carbon atoms, one on the nitrogen atom alkoxycarbonylamino, cycloalkoxycarbonylamino, cycloalkylalkoxycarbonylamino, aryloxycarbonylamino, aralkoxycarbonylamino, acylamino or alkylsulfonylamino group substituted by a cycloalkyl, cycloalkylalkyl or aralkyl group, or a phthalimino, homophthalimino, 2-carboxyphenylmethylenecarbonylamino or 2-carboxyphenylcarbonylamino, 2-carboxy phenyl methylamino, 2-carboxyphenylmethylenecarbonylamino or 2-carboxymethylenephenylcarbonylamino group, wherein a carbonyl group in a phthalimino group may be replaced by a methylene group and a methylene group in a homophthalimino, 2-carboxymethylenephenylcarbonylamino group may be substituted by one or two alkyl groups, and in addition the mono- or di-substituted phenyl nuclei mono- or disubstituted by alkyl or alkoxy groups, where the substituents may be the same or different, and at the same time may be fully or partially hydrogenated, a bicycloalkane-S-carboxylic acid amino or bicycloalkene substituted in the 2-position by a carboxy group -S-carboxylic acid amino group, a bicycloalkane-2,3-dicarboximino or bicycloalkene-2,3-dicarboxylic acid imino group in which the bicycloalkane and bicycloalkene moiety each contain 9 or 10 carbon atoms, substituted by 1, 2 or 3 methylene groups, and an endomethylene group Oxygen atom may be replaced, a Glutarsäureimino- or 3-carboxy-npropylencarbonylgruppe, in each of which the n-propylene group perfluorinated by one or two alkyl groups or by a tetramethylene or pentamethylene group may be substituted, and R ₄ with the exception or amino group for R _{4 has} meanings mentioned in the beginning t: Acylation of a compound of the general formula

(XIX)

in the

R2f R3. Rs and Re are as defined above,

R4 with the exception of the amino group as defined above and

Ru is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, which may be substituted from position 2 by a hydroxy, alkoxy or arylamino group, a cycloalkyl, cycloalkylalkyl or aralkyl group, with a compound of formula

Ru-Z ₆ (XX)

in the

Ri _{4 is} a dialkylaminoalkanoyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl or trifluoroacetyl group, an alkylsulfonyl group having 1 to 4 carbon atoms, an alkoxycarbonyl group having a total of 2 to 7 carbon atoms, an alkoxycarbonyl-substituted thiazolidin-3-yl-carbonyl group or a Acyl group in which, if the acyl group represents an alkanoyl group, it may be additionally substituted by an alkoxy group, or a 2-carboxyphenylcarbonyl, 2-carboxyphenylmethyl, 2-carboxyphenylmethylenecarbonyl or 3-carboxymethylenephenylcarbonyl group, wherein a methylene group in a 2-carboxyphenylmethylenecarbonyl or 2-carboxymethylenephenylcarbonyl group may be substituted by one or two alkyl groups, and in addition mono- or disubstituted by the above-mentioned phenyl nuclei by alkyl or alkoxy group, wherein the substituents may be the same or different, and g may be partially or partially hydrogenated, a bicycloalkane-S-carbonyl or bicycloalkene-S-carbonyl group substituted in the 2-position by a carboxy group, in which the bicycloalkane and bicycloalkene moieties each contain 9 or 10 carbon atoms, by 1,2 or 3 methylene groups substituted and an endomethylene group may be replaced by an oxygen atom, a 3-carboxy-n-propylencarbonyl group in which the n-propylene group may be perfluorinated, substituted by one or two alkyl groups or by a tetramethylene or pentamethylene group, and

Z _{s represent} a nucleophilic leaving group, or with their reactive derivatives such as their acid halides, acid esters or acid anhydrides.

Suitable reactive derivatives of a compound of the formula XIX are, for example, their esters, such as the methyl, ethyl or benzyl esters, their thioesters, such as the methylthio or ethylthioester, their halides, such as the acid chloride, their anhydrides or imidazolides.

The reaction is conveniently carried out in a solvent or solvent mixture such as water, methylene chloride, chloroform, ether, tetrahydrofuran, dioxane or dimethylformamide with an appropriate carboxylic acid in the presence of an acid activating or dehydrating agent such as thionyl chloride, with their anhydrides such as acetic anhydride, with their esters such as ethyl acetate , with their halides such as acetyl chloride or methanesulfonyl chloride, optionally in the presence of an inorganic or tertiary organic base, such as sodium hydroxide, potassium carbonate, triethylamine or pyridine, the two latter also serving as a solvent

can be used, at temperatures between -25 and 100 ° C, but preferably at temperatures between -10 and 8O ⁰ C performed.

n) For the preparation of compounds of the general formula I in which at least one of the radicals R ₁ or R _{2 is} a 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-carboxyphenylrnethylenecarbonylamino or 2-carboxymethylenephenylcarbonylamino group, a methylene group being in a 2- Carboxyphenylethylenecarbonylamino or 2-carboxymethylenephenylcarbonylamino group may be substituted by one or two alkyl groups, and additionally mono- or di-substituted by alkyl or alkoxy groups, wherein the substituents may be the same or different, and at the same time be fully or partially hydrogenated, one Bicycloalkane-S-carboxylic acid amino or bicycloalkene-S-carboxylic acid amino group substituted in the 2-position by a carboxy group, in which the

Bicycloalkane and bicycloalkene moieties each containing 9 or 10 carbon atoms, substituted by 1, 2 or 3 methyl groups

and an endomethylene group may be replaced by an oxygen atom, an S-carboxy-n-propylenecarbonyl group in which the n-propylene group may be perfluorinated, substituted by one or two alkyl groups or by a tetramethylene or pentamethylene group means: partial hydrolysis of a compound of general formula

(XXI)

in the

R ₂ to Rg are as defined above and

Ris is a phthalimino or homophthalimino group wherein a carbonyl group in a phthalimino group may be replaced by a methylene group and a methylene group in a homophthalimino group may be substituted by one or two alkyl groups, and in addition mono- or disubstituted by alkyl or alkoxy groups, the above-mentioned phenyl nuclei; Substituents may be the same or different, and may be fully or partially hydrogenated at the same time, a bicycloalkane-2,3-dicarboxylic acid or Bicycloalken ^ .S-dicarboxylic acid in which the bicycloalkane and Bicycloalkenteil each contain 9 or 10 carbon atoms, by Substituted 1,2 or 3 methyl groups and an endomethylene group may be replaced by an oxygen atom, a Glutarsäureiminogruppe in the diene propylene group perfluorinated, by one or two alkyl groups or by a tetramethylene or pentamethylene group may be substituted means.

The partial hydrolysis is conveniently carried out either in the presence of an acid such as hydrochloric acid, sulfuric acid, phosphoric acid, trichloroacetic acid or trifluoroacetic acid or in the presence of a base such as sodium hydroxide or potassium hydroxide in a suitable solvent such as water, water / methanol, ethanol, water / ethanol, water / isopropanol or Water / dioxane at temperatures between - 10 ° C and 120 ⁰ C, for example at temperatures between room temperature and the boiling temperature of the reaction mixture, carried out. However, the partial hydrolysis is particularly advantageously carried out in the presence of one equivalent of an inorganic base at room temperature.

In the reactions described above, optionally present reactive groups such as hydroxyl, amino or alkylamino groups can be protected during the reaction by conventional protecting groups, which are cleaved again after the reaction.

For example, the protective radical for a hydroxy group is trimethylsilyl, acetyl, benzovl, methyl, ethyl, tert-butyl,

Benzyl or tetrahydropyranyl group and as a protective group for an amino, alkylamino or imino group, the acetyl, benzoyl, ethoxycarbonyl or benzyl group into consideration.

The optional subsequent cleavage of a protective moiety used is preferably carried out hydrolytically in an aqueous solvent, for. Example, in water, isopropanol / water, tetrahydrofuran / water or dioxane / water, in the presence of an acid such as hydrochloric acid or sulfuric acid or in the presence of an alkali metal base such as sodium hydroxide or potassium hydroxide at temperatures between 0 and 100 ° C, preferably at the boiling temperature of the reaction mixture. However, the cleavage of a benzyl radical is preferably carried out by hydrogenolysis, for. B. with hydrogen in the presence of a catalyst such as palladium / carbon in a solvent such as methanol, ethanol, ethyl acetate or glacial acetic acid optionally with the addition of an acid such as hydrochloric acid at temperatures between 0 and 5O ⁰ C, but preferably at room temperature, and a hydrogen pressure of 1 to 7 bar, but preferably from 3 to 5 bar.

If, according to the invention, a compound of the formula I in which R ₁ and / or R ₂ represent a nitro group can be converted into a corresponding amino compound of the formula I by reduction or a compound of the formula I ₁ in R ₁ and / or R _{3 2 represents} a hydroxy, amino, alkylamino, phenylalkylamino, alkylsulfonylamino or acylamino group, this can be converted by means of alkylation into a corresponding alkylated compound of the formula I or

a compound of the formula I in which R ₁ and / or R ₂ represents a benzyloxy group may be converted by debenzylation into a corresponding compound of the formula I in which R 1 and / or R _{2 is} a hydroxy group, or a compound of the formula I, in which R ₁ and / or R _{2 represents} a carboxy group, it may by means of amidation in a corresponding compound of formula I, in the R ₁ and / or R _{2 is} optionally substituted by one or two alkyl groups each having 1 to 3 carbon atoms represents substituted aminocarbonyl, be converted or a compound of formula I, in which R _t and / or R _{2 is} a carboxy group and / or R _{4 represents} a cyano group, it may by reduction into a corresponding compound of formula I, in the R ₁ and / or R _{2 represents} a hydroxymethyl group and / or R _{4 represents} an aminomethyl group, or

a compound of the formula I in which R ₁ and / or R _{2 represents} an alkoxycarbonyf group, this can be converted by hydrolysis into a corresponding compound of the formula I, in which R ₁ and / or R _{2 represents} a carboxy group, or a compound of the formula I, in which R ₁ and / or R _{2 represents} an alkoxy or phenylalkoxy group, this can by means of

Ether cleavage into a corresponding compound of formula I, in which R, and / or R _{2 represents} a hydroxy group, be converted or

a compound of formula I in which Ri and / or R _{2 represents} an aminocarbonylamino or aminothiocarbonyl group substituted by a cycloalkyl group of from 5 to 10 carbon atoms in which a methylene group in the 2-position is replaced by an oxygen atom, and additionally by a An alkyl group having 1 to 20 carbon atoms, by an alkenyl or alkynyl group each having 3 to 5 carbon atoms, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, mono- or disubstituted by a cycloalkyl, cycloalkylalkyl, aralkyl or aryl group may be prepared by reduction to a corresponding compound of the formula I in which R 1 and / or R _{2 is} an aminocarbonylamino or aminothiocarbonyl group which is protected by a 4-hydroxy-n-butyl, 5-hydroxy-n-pentyl or 6-hydroxy-n-hexyl group and additionally by an alkyl group having 1 to 20 carbon atoms, by an alkenyl or alkynyl group each having 3 to 5 carbon atoms, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, mono- or disubstituted by a cycloalkyl, cycloalkylalkyl, aralkyl or aryl group, is converted, or a compound of formula I, in the Ri and / or R _{2 represents} a phthalimino group which may be mono- or disubstituted by an alkyl or alkoxy group, wherein the substituents may be the same or different, this may be by reduction to a corresponding compound of formula I in which R, and or R _{2 represents} a 1-oxo-isoindolin-2-yl group which may be mono- or disubstituted by an alkyl or alkoxy group, where the substituents may be identical or different, are converted or

a obtained 1, 3 -soriorengemisch a compound of formula I are separated by isomer separation in its 1 and 3 isomer.

The subsequent reduction of the nitro group is preferably carried out in a solvent such as water, water / ethanol, methanol, glacial acetic acid, ethyl acetate or dimethylformamide suitably with hydrogen in the presence of a hydrogenation catalyst such as Raney nickel, platinum or palladium / carbon, with metals such as iron, tin or zinc in the presence of an acid, with salts such as iron (II) sulfate, tin dichloride, sodium sulfide, sodium hydrogen sulfite or sodium dithionite, or with hydrazine in the presence of Raney nickel at temperatures between 0 and 8O ⁰ C, but preferably at temperatures between 20 and 40 ° C. , carried out.

The subsequent alkylation is preferably carried out in a solvent or solvent mixture such as methylformamide,

Dimethylformamide. Dimethylsulfoxide, benzene, chlorobenzene, tetrahydi ofuran, benzene / tetrahydrofuran or dioxane in Presence of an alkylating agent such as methyl iodide, methyl bromide, ethyl bromide, dimethyl sulfate, benzyl chloride or

Diazomethane optionally, preferably in the presence of an acid-binding agent, for. Example, an alcoholate such as potassium tert-butoxide, an alkali metal hydroxide such as sodium or potassium hydroxide, an alkali metal carbonate such as potassium carbonate, an alkali metal such as sodium amide or an alkali metal hydride such as sodium hydride zweckmu'ßigerweise at temperatures between 0 and 150 ° C, preferably at temperatures between 0 and 5O ⁰ C performed.

The subsequent reductive amination of an amino group is carried out in a suitable solvent such as methanol, ethanol, Tetrahydrofuran, dioxane or acetonitrile in the presence of a suitable reducing agent such as a suitable complex Metal hydride, but preferably in the presence of sodium cyanoborohydride at a pH of 5 to 7, at temperatures

between 0 and 5O ⁰ C, but preferably at room temperature, performed.

The subsequent elimination of a benzyl radical is preferably carried out by hydrogenolysis, z. B. with hydrogen in the presence

a catalyst such as palladium / carbon in a solvent such as methanol, ethanol, ethyl acetate or glacial acetic acid, if necessary with the addition of an acid such as hydrochloric acid at temperatures between 0 and 50 ° C, but preferably at

Room temperature, and a hydrogen pressure of 1 to 7 bar, but preferably from 3 to 5 bar. The subsequent amidation is conveniently carried out in a solvent such as methylene chloride, chloroform, Carbon tetrachloride, ether, tetrahydrofuran, dioxane, benzene, toluene, acetonitrile or dimethylformamide, particularly advantageous

but in an excess of the amine used, for. In methanol, ethanol, n-propanol, isopropanol, ammonia,

Methylamine, ethylamine, dimethylamine or diethylamine, optionally in the presence of an acid activating agent

or a dehydrating agent, e.g. In the presence of ethyl chloroformate, thionyl chloride,

Phosphorus trichloride, phosphorus pentoxide, N, N'-dicyclohexylcarbodiimide, Ν, Ν'-dicyclohexylcarbodiimide / N-hydroxy-succinimide,

Ν, Ν'-carbonyldiimidazole or N, N'-thionyldiimidazole or triphenylphosphine / carbon tetrachloride, or one of

Amino group activating agent, e.g. Phosphorus trichloride, and optionally in the presence of an inorganic base such as Sodium carbonate or a tertiary organic base such as triethylamine or pyridine, which simultaneously as a solvent

can serve at temperatures between -25 ° C and 250 ° C, but preferably at temperatures between -10 ° C and the

Boiling temperature of the solvent used, carried out. Subsequent reduction of the carboxy group is carried out in a suitable solvent such as methanol, ethanol, ether, Tetrahydrofuran, dioxane or glacial acetic acid in the presence of catalytically excited hydrogen, z. B. of hydrogen in Presence of platinum or palladium / carbon, and optionally in the presence of an acid such as hydrochloric acid or perchloric acid

or in the presence of a metal hydride such as sodium borohydride, lithium borohydride or lithium aluminum hydride

Temperatures between 0 and 100 ⁰ C, preferably at temperatures between 20 and 80 ⁰ C performed. The subsequent hydrolysis is preferably carried out hydrolytically in an aqueous solvent, for. In water, isopropanol / Water, tetrahydrofuran / water or dioxane / water, in the presence of an acid such as hydrochloric acid or sulfuric acid or in Presence of an alkali metal base such as sodium hydroxide or potassium hydroxide at temperatures between 0 and 100 ⁰ C, preferably

at the boiling temperature of the reaction mixture.

The subsequent ether cleavage is carried out in the presence of an acid such as hydrogen chloride, hydrogen bromide, sulfuric acid, Boron trichloride, boron tribromide or aluminum chloride in a suitable solvent such as methanol, ethanol, water / Isopropanol, methylene chloride, chloroform or carbon tetrachloride at temperatures between -30 ⁰ C and the Boiling temperature of the reaction mixture performed. The subsequent reduction is preferably carried out in a solvent such as water, water / ethanol, methanol, glacial acetic acid, Essigsäureäthylester or dimethylformamide advantageously with hydrogen in the presence of a hydrogenation catalyst

as Raney nickel, platinum or palladium / carbon, or with hydrecin in the presence of Raney nickel at temperatures between 0 and 50 ° C, but preferably carried out at room temperature.

The subsequent reduction of a phthalimino group is preferably carried out in a solvent such as glacial acetic acid

nascent hydrogen, for example with zinc / glacial acetic acid, at temperatures between 80 and 12O ⁰ C, preferably at the boiling temperature of the reaction mixture, carried out.

The subsequent isomer separation is preferably carried out by chromatography using a support such as silica gel

or alumina.

Furthermore, the compounds of formula I obtained in their acid addition salts, in particular for the pharmaceutical application in their physiologically acceptable salts with inorganic or organic acids, converted. Examples of suitable acids are hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, fumaric acid, succinic acid, lactic acid, citric acid, tartaric acid or maleic acid.

In addition, the novel compounds of formula I thus obtained, if they contain a carboxy group,

if desired, then convert into their addition salts with inorganic or organic bases, in particular for the pharmaceutical application in their physiologically acceptable addition salts. As bases come here

For example, sodium hydroxide, potassium hydroxide, cyclohexylamine, ethanolamine, diethanolamine and triethanolamine into consideration.

The compounds of the formulas II to XXI used as starting materials are partially known from the literature or are obtained

according to literature methods.

Thus, for example, a compound of the formula II or III is obtained by alkylation of a corresponding o-aminonitro compound and subsequent reduction of the nitro group.

A compound of the formulas V, VI, VII, IX, X, XI, XIII, XV, XVII, XIX or XXI used as starting material is obtained by alkylation of a corresponding o-phenylenediamine or a corresponding o-amino-nitro compound and subsequent reduction of the nitro group and subsequent cyclization of an o-diaminophenyl compound thus obtained or by NH-alkylation of a corresponding 1H-benzimidazole, wherein the isomer mixture thus obtained then by conventional methods, for. B. by chromatography, can be separated.

The novel compounds of the formula I and their physiologically acceptable addition salts have valuable pharmacological properties. They are in particular angiotensin II antagonists.

For example, the compounds were

A = 4 '- [(2-n-butylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid,

B = 4 '- [(2-methoxymethylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid, C = 4' - [(2-methyl-5- and 6-butanoylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, D = 4 '- [(2-n-propyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid,

E = 4'- | (2-ethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid,

F = 4 '- [(2-methylthiomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid-silver nitrilotiacetate, G = 4' - [(2-ethylthio-benzimidazol-1-yl) -methyl-biphenyl- 2-carboxylic acid,

H = 4 '- [(2-n-butyl-5-methoxybenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid, I = 4' - [(2-n-butyl-6-methoxy-benzimidazole 1 -yl) -methyl] biphenyl-2-carboxylic acid, J = 4'-I (2-n-butyl-5,6-dimethylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, K = 4'-l (2-n-propyl-naphtho [2,3-dimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, L = 4 '- [(2-n-butyl-5,6-dimethoxy benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid, M = 4 '- [(2- (1-butyn-4-yl) benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid , N = 4 '- [(2-n-butyl-5-acetylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, O = 4' - [(2-cyclohexylmethyl-5,6-dihydroxy-) benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid, P = 4 '- [(6-aminothiocarbonylamino-2-n-butyl-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid hemihydrate, Q = 4 '- [(6-aminocarbonylamino-2-n-butyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid trifluoracetatund

R = 4'-l (2-n-butyl-5- (n-butylaminocarbonylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid semifluoroacetate

examined for their biological effects as follows:

a) Rats (male, 180-220g) are anesthetized with hexobarbital sodium (150mg / kg i.p.). After the narcosis has occurred, a tracheostomy tube is placed, the animals are despinalized and then artificially ventilated with a breathing pump. The arterial blood pressure is registered via a cannula in the carotid artery by means of a Bell & Howell pressure transducer.

Substances are administered via a cannula into the jugular vein.

Test substances are administered at three doses (10, 20 and 30 mg / kg i.v.), one substance dose per animal being tested. Three minutes after the intravenous administration of the test substance, angiotensin-II is administered intravenously in increasing doses, thus achieving a cumulative dose-response relationship for angiotensin-II in the presence of the test substances. The measuring parameter is the increase of the arterial blood pressure.

These dose-response curves are compared to standard curves for angiotensin-II without test substances. By means of a computer program, the right shifts in the dose-response curves of angiotensin II are determined by test substances and calculated according to pA ₂ values for the test substances.

The following table shows the average pA _r values of the investigated substances:

substances PAJ values A 4.40 B 5.10 C 5.30 D 5.49 e 5.25 F 5.25 G 5.10 H 5.00 I 5.17 J 5.41 K 4.90 L 5.27 M 4.97 N 4.88 O - P 5.22 Q 5.43 R 5.47

b) The inhibitory effect of the new compounds on the binding of angiotensin II to bovine adrenocortical receptor preparations was determined analogously to the method of Glossmann et al. Chem. 249, 825-834 [1974]). The incubation mixture contained aliquots of a bovine adrenal cortex membrane preparation in Tris buffer, increasing concentrations of the potential antagonist and 5OpM ¹²⁵ I-angiotensin-II. After 45 minutes, incubation was terminated by rapid filtration through glass fiber filters. The filter-bound radioactivity was determined in a γ-Coiintor with a count yield of 80%.

The table below shows the inhibitor concentration of antagonists causing 50% inhibition of specific ¹²⁵ I-angiotensin H binding:

substances ICmIuM / I] A 1.2 B 5.9 C 1.9 D 0.6 e 1.0 F 1.5 G 2.1 H 0.9 I 2.4 J 9.5 K 2.3 L 4.0 M 6.4 N 2.4 O 29.0 P 0.8 Q 0.9 R 1.0

Furthermore, in the application of the above compounds up to a dose of 30 mg / kg i.V. no toxic side effects, e.g. no negative inotropic effect and no cardiac arrhythmias are observed. The compounds are therefore well tolerated.

Because of their pharmacological properties, the novel compounds and their physiologically acceptable addition salts are suitable for the treatment of hypertension and heart failure, for the treatment of ischemic peripheral circulatory disorders, myocardial ischemia (angina), for the prevention of cardiac insufficiency progression after myocardial infarction, for the treatment of diabetic nephropathy, glaucoma, gastrointestinal diseases and bladder diseases.

The dosage required to achieve a corresponding effect is expediently from 20 to 100 mg, preferably from 30 to 70 mg, given by intravenous administration, and from 50 to 200 mg, preferably from 75 to 150 mg, by oral administration, in each case 1 to 3 times daily. For this purpose, the compounds of formula I according to the invention, optionally in combination with other active substances, together with one or more inert conventional carriers and / or diluents, for. As with corn starch, lactose, cane sugar, microcrystalline cellulose, magnesium stearate, polyvinylpyrrolidone, citric acid, tartaric acid, water, water / ethanol, water / glycerol, water / sorbitol, water / polyethylene glycol, propylene glycol, cetylstearyl alcohol, carboxymethylcellulose or fatty substances such as hard fat or their suitable mixtures, in common pharmaceutical preparations such as tablets, Dragoes, capsules, powders, suspensions or suppositories. The following examples are intended to explain the invention in more detail:

Ausführungsbelsplele Example A

4VN- (5-Benzylamino-2-n-phenyl) -pontanoylanilnomethyl / -blphenyl-2-carboxylic acid tert -butyl ester 3.9g (7.5 mmol) 4 '- / N- (5-chloro-2-nitro-phenyl) -pentanoylaminomethyl / biphenyl-2-carboxylic acid tert-butyl ester are stirred together with 3.9 ml of benzylamine for 3 hours in a 150 to 16O ⁰ C hot oil bath. After cooling the

Reaction mixture dissolves the residue in ca, 25ml methylene chloride and the substance is purified on a silica gel column

(Grain size: 0.063 to 0.2mm, eluent: cyclohexane: 5 to 10% ethyl acetate). The corresponding fractions are on

Concentrated rotary evaporator. Yield: 2.9 g (65.5% of theory), Oil, Rr value: 0.55 (silica gel: cyclohexane / ethyl acetate = 2: 1) The following compounds are obtained analogously:

4VN- (5- (N-benzyl-methylamino) -2-nitro-phenyl) pentanoylaminomethyl / biphenyl-2-carboxylic acid tert-butyl ester

Oil, R ₁ -WeM: 0.40 (silica gel: cyclohexane / ethyl acetate = 4: 1)

4 '- / N- (5-dimethylamino-2-nitro-phenyl) -pentanoylaminomethyl / biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.35 (silica gel: hexane / ethyl acetate = 4: 1) example 1

4 '- / (Benzlmldazol-1-yl) -methyl / blphenyl-2-carboxylic acid tert.butylester0.95g (8mMol) of benzimidazole are dissolved in 50ml dimethyl sulfoxide and treated with 1.0g OmMoI) potassium tert-butylate. to

Salt formation is then stirred for 30 minutes at room temperature and then sets 2.8 g (8 mmol) of 4'-bromomethyl-biphenyl-2

carboxylic acid tert-butyl ester added. After stirring for 2 hours at room temperature, the reaction is complete. Dilute with

Water to 500ml and extracted 3 times with about 100ml of ethyl acetate. The combined organic phases are with Dried magnesium sulfate and concentrated to dryness. The oily residue is passed through a silica gel column (particle size:

0.063-0.2 mm) using as eluent methylene chloride with 1% ethanol. The uniform fractions are concentrated to dryness. The residue is an oil.

Yield: 2.8 g (90.8% of theory), Rr value: 0.35 (silica gel: methylene chloride / ethanol = 19: 1)

Calc .: C 78.10 H 6.29 N 7.29

Found .: C78.18 H6.34 N7.19

The following compounds are obtained analogously:

4 '- [(2-Hydroxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.15 (silica gel: methylene chloride / ethanol = 49: 1)

4 '- [(2-n-butyl-7- (2-diethylamino-ethoxy -4-methyl-benzimidazol-l-yl)) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.55 (silica gel: methylene chloride / ethanol = 9: 1)

4 '- ((2-ethylthio-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.45 (silica gel: methylene chloride / ethanol = 49: 1)

4 '- ((2-n-Propylthiomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R f value: 0.55 (silica gel: methylene chloride / ethanol = 19: 1) 4' -I (2-methyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.60 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2-methylmercapto-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.55 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2-Methyl-5- and 6-nitro-benzimidazol-1-yD-methyllbiphenyl) -carboxylic acid tert-butyl ester

Oil, Rr value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2-Methyl-5- and 6-butanoylamino-benzimidazol-1-yD-methyl-2-butylbiphenyl-2-carboxylate

Oil, Rf value: 0.60 (silica gel: methylene chloride / ethanol = 9: 1)

4 '- [(2- (2-methyl-propyl) -benzoimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.50 (silica gel: methyl ethyl ketone / xylene = 1: 1)

^ MU Methopxyffiethyl-benzimidazole-i-yll-methyllbiphenyl ^ carboxylic acid tert-butyl ester

Oil, Rr value: 0.50 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4'| (2- (pyridyl- (2)) - benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.40 (silica gel: methylene chloride / FAhanol = 19: 1)

^ '- [(B-unde-methyl-benzimidazoM-YLJ-methyllbiphenyl ^ -carboxylic acid tert.-butyl ester

Oil, Rr value: 0.25 (silica gel: methylene chloride / ethanol = 19: 1)

4'-l (2-phenyl-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.45 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- ((2- (thiazol-4-yl) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, R ₁ -WeH: 0.30 {silica gel: methylene chloride / ethanol = 49: 1)

4 '- [(2- (3,5-dimethyl-pyrazol-1-yl) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.35 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2- (furyl) (2) - benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.40 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2-aminocarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2-isopropyl-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.50 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4 '- [(2-hydroxymethyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.35 (silica gel: methylene chloride / ethanol = 19: 1)

4'-t (2- (3-hydroxypropyl) benzimidazol-1-yl) -methyllbiphenvl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.40 (silica gel: methylene chloride / ethanol = 19: 1) 4'- [(2-Methyl-5-und6- (N- (methoxy-acetyl) -n-butylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester oil, R, value: 0.20 (Silica gel: methylene chloride / ethanol = 19: 1) 4- ^l - [(2- (1-Methylpropyl) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester

Oil, Ri value: 0.80 (silica gel, methyl ethyl ketone / xylene = 1: 1)

4'-l (2- (2-methylbutyl) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, RrWeri: 0.60 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4 '- ((2-methyl-5-und6- (N-2-methoxy-ethyl) -n-butylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, R | value: 0.25 (silica gel: methylene chloride / ethanol = 19: 1) 4 '-! (2-n-pentyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Oil, Rr value: 0.50 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4'-l (2-n-butyl-7, methoxy-4-methyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R _r value: 0.50 (silica gel: methylene chloride / Ethanol = 19: 1) 4 '- [(2-n-propylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl tester Melting point: 140-141 ° C

4'-l (2-ethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert -butyl ester Melting point: 129-13O ⁰ C

4'-l (2-ethylthiomethyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Η, value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-methylthiomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.45 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- ((2-chloro-benzimidazol-1-yl) -methyl | biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rp value: 0.55 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- ((2-n-butylthio-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert, butyl ester oil, Rr value : 0.55 (silica gel: methylene chloride / ethanol = 49: 1) 4 '- [(2- (4-methoxyphenyl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil R f value: 0.80 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4 '- [(2-n-propylthio-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester, Rr value: 0.50 (silica gel: methylene chloride / ethanol = 49: 1) 4'- | 2-n-butylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.45 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2- (4-methoxy-phenyl) -5- and 6-chloro-benzimidazol-1-yl) -methyl-biphenyl-2-one carboxylic acid tert.-butyl ester

Oil, R, value: 0.50 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4 '- ((2-n-butyl-5-and 6-acetamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.60 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1) 4 '- [(2-n-butyl-5-and 6-butanoylamino-benzimidazol-1-yl) -methyl] biphenyl 2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.80 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1) 4 '- [(2-n-butyl-5-and 6-methoxy-benzimidazol-1-yl) -methyl) biphenyl- 2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.70 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4 '- [(7-n-butoxy-2-n-butyl-4-methyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.65 (silica gel : methylene chloride / ethanol = 19: 1) 4 '- [(2- (4-hydroxyphenyl) -benzimidazole-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester melting point: 258-260 ⁰ C.

4 '- [(2- (4-n-Butoxyphenyl) benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.70 (silica gel: methyl ethyl ketone / xylene = 1 :1)

4 '- ((2-n-butyl-4-nitrobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.45 (silica gel: methylene chloride / ethanol = 19: 1 ) 4 '- [(2- (3-Pyridyl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.40 (silica gel: methyl ethyl ketone / xylene = 5: 2)

4 '- [(2- (4-Benzyloxyphenyl) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid teri-butyl ester Oil, R, value: 0.75 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4 '- [(2-n-butyl-5,6-dimethyl-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1 ) 4 '- [(2- (2,2-Dimethylpropyl) -5,6-dimethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert -butyl ester oil, R, value: 0.48 (Silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-benzyl-5,6-dimethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0, 52 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2- (2-methylbutyl) -5,6-dimethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil , Rr value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-cyclohexylmethyl) -5,6-dimethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert. butyl ester oil, Rr value: 0.52 (silica gel: methylene chloride / ethanol = 19: 1) tert-butyl 4 '- [(2-cyclohexylmethyl-5,6-dichloro-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate Oil, Rr value: 0.46 (silica gel: methylene chloride / ethanol = 19: 1) 4'- (2- (2-methylbutyl) -na phtho [2,3-dimazid-1-yl-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.57 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-n -propyl-naphthol2,3-d] imidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert. butyl ester oil, Rr value: 0.57 (silica gel: methylene chloride / ethanol = 19: 1) 4'-t (2-n-butyl-5,6-dichloro-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.45 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2-Cyclohexvlmethyl-5,6-dimethoxy-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

Oil, R, value: 0.47 (silica gel: methylene chloride / ethanol = 19: 1)

4'-l (2-n-butyl-5,6-dimethoxybenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.46 (silica gel: methylene chloride / ethanol = 19 : 1) 4 '- [(2-Cyclopentylmethyl-5,6-dimethoxybenzimidazol-1-yl) -fine] -biphenyl-2-carboxylic acid tert-butyl ester

Oil, Ri value: 0.47 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- ({2- (3-methylbutyl) -5,6-dimethoxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.47 (silica gel: methylene chloride / ethanol = 19: 1)

4'-l (2-Cyclohexyl-5,6-dimethylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R _r value: 0.50 (silica gel: methylene chloride / ethanol = 19 : 1) 4 '- [(2- (1-Butyn-4-yl) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.49 (silica gel: methylene chloride / ethanol = 19: 1)

4'-I (2-n-Butyl · 6-ethoxycabonyl-benzimidazol-1-yl) · methyllbiphenyl-2-carboxylic acid tert-butyl ester

Oil, Ri value: 0.60 (silica gel: petroleum ether / ethyl acetate = 1: 1 + 1% glacial acetic acid)

4'-l (2-cyclopentyl-5,6-dimethyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Ri value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1)

^ γγνΙρ

Oil, Rr value: 0.25 (silica gel: methylene chloride / ethanol = 50: 1)

4 '- [(2-n-butyl-5,6-dimethyl-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.28 (silica gel: methylene chloride / ethanol = 50: 1)

4'-l (2-n-butyl-5-and 6-trifluoromethylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.33 (silica gel: methylene chloride / ethanol = 50 : 1) 4 '- [(2-n-butyl-4-cyano-benzimidazol-1-yl) -methyl-1-biphenyl-2-carboxylic acid tert-butylated oil, Rr value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1) tert-butyl 4 '- [(2-n-butyl-5- and 6-n-butylaminocarbonyl-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate, Rr value: 0.30 (silica gel: methylene chloride / methanol / Acetic acid = 19: 0.8: 0.2) 4 '- [(2-n-butyl-6-carboxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.90 (silica gel: methylene chloride / methanol / acetic acid = 9: 0.8: 0.2) 4 '- ((2-n-butyl-5-carboxy-benzimidazol-1-yl) - methyl] biphenyl-2-carboxylic acid tert-butyl ester Melting point: 224-225 ° C

4 '- [(2-n-butyl-6-aminocarbonyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester melting point: 159-160 ⁰ C.

4 '- [(2-n-butyl-5-aminocarbonyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Melting point: 135-138 ° C (dec.)

Oil of tert-butyl 4 '- [(2-n-butyl-5- and 6-cyano-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate, R _r value: 0.50 (silica gel: methylene chloride / ethanol = 100 : 1) 4 '- [(2-n-Butyl-6- (1H-tetrazol-5-yl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Melting point: from 115 ° C (dec.)

4 '- [(2-n-butyl-5-und6- (1H-tetrazol-5-yl) -benzoimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester melting point: from 92 ⁰ C ( dec.)

4 '- [(2-n-Butyl-6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -methyl] -1-cyano-2-phenyl-naphthalene 4' - [(2-n-butyl -benzimidazol-1-yl) -methyl] -2-phenyl-naphthalene-1-carboxylic acid tert-butyl ester, Rr value: 0.25 (silica gel: methylene chloride / ethanol = 50: 1) 4'-1 (2-n-butyl -6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -methyl] -2-phenyl-naphthalene-1-carboxylic acid tert-butyl ester 4 '- [(2-n-butyl-6- (cis-hexahydrophthalimino) -benzimidazol-1-yl) -methyl] -4-bromo-biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.43 (silica gel: ethyl acetate / petroleum ether = 2: 1) 4 '- [(2-n Butyl-benzimidazol-1-yl) -methyl] -4-biphenyl-2-carboxylic acid tert-butyl ester Oil, Rr value: 0.35 (silica gel: methylene chloride / ethanol = 50: 1) 4 '- [(2-n Butyl-6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -methyl] -4-chloro-2-cyano-biphenyl oil, Rr value: 0.90 (silica gel: methylene chloride / ethanol = 9: 1)

Example 2 4 '- [(2-n-butyl-5 and 6-nitro-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester

a) 2-n-butyl-6-nitrobenzimidazole

11.5 g (0.075 mol) of 4-nitro-o-phenylenediamine are introduced in portions at room temperature into a mixture of 8.66 g (0.085 mol) of valeric acid and 120 ml of phosphorus oxychloride. Then it is boiled for 3 hours at reflux.

The reaction mixture is decomposed in 1.5 kg of ice-water, made alkaline with concentrated ammonia and washed three times with 500 ml Extracted vinegar. The organic phase is separated, dried with magnesium sulfate and concentrated by rotary evaporation. The oily one The residue is purified on a silica gel column (particle size: 0.063-0.2 mm, eluent: methylene chloride / 0-2% ethanol). The uniform fractions are concentrated to dryness.

Yield: 10.2 g (62.2% of theory), Melting point: 139-141 ⁰ C.

Calc .: C 60.27 H 5.98 N 19.17

Gof .: C 60.30 H 6.00 N 19.42

b) 9.5 g (43 mmol) of 2-n-butyl-6-nitro-benzimidazole are dissolved in 100 ml of dimethyl sulfoxide and treated with 5.3 g (47.6 mmol) of potassium tert-butylate. The mixture is stirred for 30 minutes and 16.6 g (47.6 mmol) of 4'-bromomethyl-biphenyl-2-carbon acid tert.butylester added. After 2 hours, the reaction mixture is mixed with about 600 ml of water and extracted 3 times with about 200 ml of ethyl acetate. The organic phase is dried with magnesium sulfate and concentrated by rotary evaporation. The crude product thus obtained is purified on a silica gel column (particle size: 0.063-0.2 mm, eluent: methylene chloride / O-1% ethanol). The uniform fractions are concentrated to dryness.

Yield: 19.9 g (95.2% of theory), oil, Ri value: 0.50 (silica gel: methylene chloride + 5% ethanol)

Calc .: C71 / 73 H6.43 N8.65

Found: C 72.00 H 6.66 N 8.80

The following compounds are obtained analogously:

Tert-butyl ester of 4'-l (2-n-butyl-4-and-7-nitro-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylate, Rr value: 0.45 and 0.47 (silica gel: Methylene chloride / ethanol = 19: 1) tert-butyl 4 '- [(2-n-butyl-5- and 6-methoxy-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylate, Rr value: 0, 55 (silica gel: methyl ethyl ketone / xylene = 1: 1) 4 '- [(2-n-butyl-5-and 6-nitro-benzimidazol-1-yl) -methyl-1-biphenyl-2-carboxylic acid tert-butyl ester oil , Rp value: 0.60 (silica gel: methyl ethyl ketone / xylene = 1: 1) 4 '- [(2-n-butyl-5- and 6-chloro-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid -tert.butylester

Oil, Rr value: 0.55 (silica gel: methyl ethyl ketone / xylene = 1: 1)

Tert-Butyl ester 4 '- [(2-n-butyl-5-and 6-acetamido-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylate oil, R _r value: 0.20 (silica gel: methyl) ethyl ketone / xylene = 1: 1) tert-butyl 4 '- [(2-n-butyl-5- and 6-butanoylamino-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylate, Rp value: 0, 80 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1)

Example 3

4 '- [(5-And-6-Amino-2-n-butyl-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid tur t.butyl ester 18.3g (37.7 mmol) 4' - [(5- and 5-yl e-nitro ^ -n-butyl-benzimidazol-i-yD-methyllbiphenyl ^ -carboxylic acid tert-butyl ester are dissolved in200ml ethanol, mixed with 10 g of Raney nickel and hydrogenated for 3 hours at 5O ⁰ C and 5 bar hydrogen pressure. Nachbeendigter hydrogen uptake is from Catalyst sucked off and evaporated.

Yield: 17.1 g (100% of theory), Oil, Rr value: 0.1 and 0.2 (silica gel: methylene chloride / ethanol = 95: 5) The following compound is prepared analogously:

4 '- ((4-and 7-amino-2-n-butyl-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.20 and 0.22 (silica gel: methylene chloride / ethanol = 50: 1)

Example 4 4 '- [(6-Amino-2-n-butyl-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid tert-butyl ester (l)

4 '- [(5-Amino-2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester (II) The isomer mixture of I and II obtained in Example 3 (17,1 g) is separated on a chromatography column filled with 1700 ml of silica gel (particle size: 0.063-0.2 mm), the first being isolated by elution with methylene chloride / ethanol = 98:21.

Yield: 7.32 g (42.8% of theory),

Oil, R _r value: 0.2 (silica gel: methylene chloride / ethanol = 95: 5). Then, with methylene chloride / ethanol = 96: 4, II is eluted.

Yield: 9.28 g (54.3% of theory), oil, Rr value: 0.1 (silica gel: methylene chloride / ethanol = 95: 5) Analogously, the following compounds were isolated in pure form from the corresponding isomer mixtures:

4'-l (4-amino-2-n-butyl-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester Yield: 86.1% of theory,

Oil, Rr value: 0.25 (silica gel: methylene chloride / ethanol = 99: 1)

4'- | (7-Amino-2-n-butyl-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester Yield: 5.0% of theory,

Oil, Rr value: 0.30 (silica gel: methylene chloride / ethanol = 99: 1) 4 '- [(7-benzyloxy-2-n-butyl-4-methylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester Yield: 90.5% of theory,

Melting point: 100-102 "C

4 '- [(4-Benzyloxy-2-n-butyl-7-methyl-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester. Yield: 1.9% of theory,

Oil, Rr value: 0.20 (alumina: cyclohexane / ethyl acetate = 4: 1)

Ex! EL5

4 '- [(2-n-butyl-6-methyl-benzimldazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

a) 2-Pentanoylamino-5-methyl-nitrobenzene 6g (0.04 mol) 2-nitro-6-methyl-aniline are dissolved in 50 ml of pyridine, cooled to 0 ° C and with stirring 5.3 g

(0.04 mol + 10%) valeryl chloride. After stirring for 1 hour at room temperature is poured into ice water and the

The crystals were filtered off with suction and dried.

Yield: 9g (96.7% of theory),

Melting point: 69-71 ⁰ C

Calc .: C 61.00 H 6.83 N 11.86

Found: C 61.21 H 6.79 N 11.72

b) 2-Pentanoylamino-S-methyl-anilene

8.5 g (0.035 mol) of 2-pentanoylamino-5-methyl-nitrobenzene are dissolved in 100 ml of methyl alcohol and hydrogenated at room temperature and 5 bar with 2 g of 10% palladium / carbon. After completion of the reaction, the catalyst is filtered off with suction and evaporated in vacuo.

Yield: 7.1 g (94.7% of theory), Melting point: 132-134 ⁰ C (methanol)

Calc .: C 69.87 H 8.80 N 13.58

Found: C69.28 H8.74 N 13.31

c) N- (2-Pentanoylamino-5-methyl-phenyl) -2-tert-butoxycarbonyl-phenyl-4'-yl-methyl-amine

2.1 g (0.01 mol) of 2-pentanoylamino-5-methyl-aniline are dissolved in 10 ml of dimethylformamide and 5 ml of N, N-diisopropylethylamine, with 3.5 g (0.01 mol of 4'-bromomethyl-biphenyl-2-carboxylic acid tert-butyl ester and heated with stirring to 12O ⁰ C. After 2 hours, the reaction is complete and the solvent is distilled off in vacuo.The resulting oily residue is dissolved in ethyl acetate, washed with water and evaporated after drying over sodium sulfate in vacuo. After column chromatography on silica gel (particle size: 0.06-0.2 mm, eluent: methylene chloride), a yellowish oil is obtained Yield: 3.8 g (80% of theory), oil, R _r value: 0.75 (silica gel: methyl ethyl ketone / xylene = 1: 1) Calc .: C 76.24 H 7.68 N 5.93

Gef .: C76.16 H7.85 N5,87

d) 4 '- [(2-n-butyl-6-methyl-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid tert-butyl ester

3.6 g (0.076 mol) of N- (2-pentanoylamino-5-methyl-phenyl) -2-tert-butoxycarbonyl-biphenyl-4'-yl-methylamine are taken up in 5 ml of diglyme and heated to reflux. After 2 hours, the reaction is complete, the reaction product is dissolved in ethyl acetate, washed with water and, after drying over sodium sulfate, evaporated in vacuo. After column chromatography on silica gel (particle size: 0.06-0.2 mm, eluent: methylene chloride + 1% ethanol), a yellowish oil is obtained.

Yield: 2.1 g (61.7% of theory), oil, R _r value: 0.6 (silica gel: methyl ethyl ketone / xyclol = 1: 2

Calc .: C 79.26 H 7.54 N 6.16

Found: C79.12 H7.46 N 6.09

The following compounds are obtained analogously:

4'- | (2-n-butyl-6-chloro-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.6 (silica gel: methyl ethyl ketone / xylene = 1 : 2) 4 '- [(2-n-Butyl-6-methoxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rp value: 0.65 (silica gel: methyl ethyl ketone / Xylene = 1: 2)

Example 6 4 '- [(2-n-butyl-5-methoxy-benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid tert-butyl ester

a) 2-pentanoyl-5-methoxy-n-n-nitrobenzene

4.2 g (0,025MoI) 2-nitro-4-methoxy-aniline are dissolved in 30 ml of pyridine, cooled to 0 ⁰ C and added under stirring with 3.3 g (0,0275MoI) valeryl chloride. After 1 hour of stirring at room temperature is poured into ice water, the crystals are filtered off and dried.

Yield: 6 g (95.2% of theory), Melting point: 74-75 ⁰ C

C ₁₂ H ₁₆ N ₂ O ₄ (252.27)

Calc .: C57,13 H6,39 N 11,11

Found: C 57.43 H 6.45 N 10.97

b) N- (2-nitro-4-methoxy-phenyl) -N-pentanoyl- (2-tert-butoxy-carbonyl-phenyl-4'-yl) -methylamine

2.5 g (0.01 mol) of 2-pentanoylamino-5-methoxy-nitrobenzene are dissolved in 30 ml of dimethylformamide, with 550 mg (0.11 mol)

Sodium hydride (50% in oil) and stirred at 80 ⁰ C for 30 minutes. Then 3.5 g (0.01 mol) of 4'-bromomethyl-biphenyl-2-carboxylic acid tert.butylester are added and stirred at 80 ° C for 2 hours. The solvent is distilled off in vacuo, the oily residue obtained is dissolved in ethyl acetate, washed with water and, after drying over sodium sulfate, evaporated in vacuo. After column chromatography (silica gel: 0.06-0.2 mm, eluent: methylene chloride) men receives a yellowish

Yield: 4.0 g (78.4% of theory), oil, R _r value: 0.8 (silica gel: methyl ethyl ketone / xylene = 1: 2) C ₃₀ H ₃₄ N ₂ O ₆ (518.61)

Calcd .: C, 69.48, H, 6.61, N, 5.40

Found: C 69.31 H 6.53 N 5.39

c) N- (2-Amino-4-methoxyphenyl) -N-pentanoyl- (2-tert-butoxycarbonyl-phenyl-4'-yl) -methylamine

3.8 g (0.007 mol) of N- (2-nitro-4-methoxyphenyl) -N-pentanoyl- (2-tert-butoxycarbonyl-biphenyl-4'-yl) -methylamine are dissolved in 100 ml of methanol and added at Room temperature and 5bar hydrogenated in the presence of 1 g of 70% palladium / carbon. After completion of the reaction, the catalyst is filtered off with suction and evaporated in vacuo.

Yield: 3.2 g (93.6% of theory), oil, Rr value: 0.5 (silica gel: methyl ethyl ketone / xylene = 1: 2) C ₃₀ H ₃₆ N ₂ O ₄ (488.63)

Calc .: C 73.74 H 7.43 N 5.73

Found: C 73.59 H 7.40 N 5.72

d) 4 '- [(2-n-butyl-5-methoxybenzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid tert -butyl ester 3g (0.006 mol) N- (2-amino-4-methoxyv -phenyl) -N-pentanoyl- (2-tert-butoxy-carbonyl-biphenyl-4'-yl) -methylamine are dissolved in 100 ml of glacial acetic acid and heated to reflux with stirring. After one hour, the solvent is distilled off and the

oil obtained was chromatographed over silica gel (particle size: 0.06-0.2 mm, eluant: mathylene chloride / ethanol = 19: 1) for further purification.

Yield: 2.3 g (82.1% of theory), oil, Rr value: 0.7 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1) C ₃₀ H ₃₄ N ₂ O ₃ (470.61)

Calc .: C 76.56 H 7.28 N 5.95

Found .: C 76.36 H 7.31 N 5.79

The following compounds are obtained analogously:

4 '- ((2-n-butyl-chloro-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R _r value: 0.7 (silica gel: ethyl acetate / ethanol / ammonia = 90 : 10: 1) ^ '- [(S-Amino) -n-butylbenzimidazol-i-yD-methyllbiphenylcarboxylic acid tert-butyl ester

Oil, Rf value: 0.5 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1) 4'- [(2-n-butyl-5-methyl-benzimidazol-1-yl) -methyl] biphenyl 2-carboxylic acid tert-butyl ester oil, Rr value: 0.8 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1) 4 '- ((2-n-butyl-7-cyano-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R _r value: 0.49 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-n-butyl-5,7-difluoro-benzimidazole 1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.27 (silica gel: methylene chloride / ethanol = 50: 1) 4'- (2-n-butyl-5-acetyl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Oil, R, value: 0.30 (silica gel: methylene chloride / ethanol = 50: 1) 4'-l (2-n-butyl) Tert-butyl 6-dimethylamino-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate, Rf value: 0.60 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- ((7-amino-2-n -butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R _r value: 0.30 (alumina: methylene chloride / ethanol - 99 : 1) 4 '- [(6- (N-Benzyl-methylamino) 2-n-butylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.40 (silica gel : Methylene chloride / ethanol = 19: 1) 4 '- ((2-n-butyl-5-dimethylaminosulfonyl-3-N-oxido-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester (prepared by incomplete reduction of the nitro group followed by cyclization) melting point: 59-62 ⁰ C

4'-l (7-Benzyloxy-2-n-butylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.50 (silica gel: methyl ethyl ketone / xylene = 1 : 1) 4 '- ((4-Benzyloxy-2-n-butyl-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.65 (silica gel: methyl ethyl ketone / Xylene = 1: 4) 4 '- [(2-n-butyl-7-methoxybenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.80 (silica gel: methyl ethyl ketone / xylene = 1: 1) 4 '- [(2-n-butyl-4-methoxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.70 ( Silica gel: methyl ethyl ketone / xylene = 1: 2) 4 '- [(2,5-di-n-butylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester 4' - [( 2,6-di-n-butyl-benzimidazol-1-yl) -methyl-bi-phenyl-2-carboxylic acid tert-butyl ester ^ '- ((e-benzyloxy) -n-butylbenzimidazol-i-yD-methyllbiphenylcarboxylic acid -tert.butylester

Oil, Rr value: 0.40 (silica gel: methyl ethyl ketone / xylene = 1: 2) 4 '- [(2-n-butyl-6-methylamino-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.10 (silica gel: methylene chloride / ethanol = 50: 1) 4 '- [(2-n-butyl-6-cyclohexylamino-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.20 (silica gel: ethyl acetate / petroleum ether = 60:40) 4 '- [(2-n-butyl-6- (3-cyclohexyl-piperidino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.65 (silica gel: methylene chloride / ethanol = 9: 1) 4 '- [(2-n-butyl-6-phthaliminobenzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester · Melting point: 182-184 ° C

4 '- [(2-n-butyl-6- (n-pentylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid t6rt.butylester

Oil, Rr value: 0.70 (silica gel: methyl ethyl ketone / xylene = 1: 1) 4 '- [(2,5-di-n-butyl-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.30 (silica gel: methyl ethyl ketone / xylene = 1: 4) 4'-l (2,6-di-n-butylbenzimidazol-1-yl) methyl] biphenyl-2 -carboxylic acid tert.butyl ester oil, Rf value: 0.50 (silica gel: methyl ethyl ketone / xylene = 1: 4)

Example 7

4 - [(2-n-butyl-5- (n-butylaminocarbonylamino) -benzlmldazol-1-yl) -methyl] -blphenyl-2-carboxylic acid tert -butyl ester 2.0 g (4.4 mmol) 4 '- [(5- Amino-2-n-butylbenzimidazol-1-yl) -mothyl] biphenyl-2-carboxylic acid tert-butyl ester are dissolved in 50 ml

Dissolved tetrahydrofuran and mixed with 2.0 ml of triethylamine and 2.0 ml of n-butyl isocyanate. The reaction mixture is

Boiled for 4 hours at reflux, concentrated by rotary evaporation, and the residue on a silica gel column (particle size: 0.063mm-0.2 mm,

Eluent: methylene chloride / 0-2% ethanol). The uniform fractions are concentrated to dryness. Yield: 2.1 g (86.4% of theory), Oil, Rf value: 0.45 (silica gel: methylene chloride / ethanol = 19: 1) The following compounds are obtained analogously:

4 '- ((2-n-butyl-6-phenylaminocarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Amorphous substance, Ri value: 0.30 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2-n-butyl-6-cyclohxylaminocarbonylamino-benzimidazol-1-yl) -meth>, i) biphenyl-2-carboxylic acid tert-butyl ester

Amorphous substance, R ₁ value: 0.25 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- ((2-n-Butyl-ethylaminocarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Amorphous substance, Rf value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(6-aminocarbonylamino-2-n-butyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Melting point: 210-21 TC

4'-l (2-n-butyl-6- (n-hexylaminocarbonylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Melting lane ¹ ; 142-143 ⁰ C

4 '- [(2-n-butyl-4-cyclohexylaminocarbonylamino-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

Melting point: 104-106 ° C (amorphous)

4 '- [(2-n-butyl-5-cyclohexylaminocarbonylamino-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

Melting point: 118-12O ⁰ C (amorphous)

4 '- ((2-n-butyl-7-cyclohexylaminocarbonylamino-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester

Melting point: 152-154 ⁰ C

4 '- [(6-Aminothiocarbonylamino-2-n-butyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Melting point: 175-176 ° C

4 '- [(2-n-butyl-6-cyclohexylaminothiocarbonylarr> ino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Melting point: 91-93 ° C (amorphous)

4 '- ((5-Aminothiocarbonylamίno-2-n-butyl · benzimidazol-1-yl) methyl] bίphenyl-2-carboxylic acid tert-butyl ester

Melting point: 196-197 ⁰ C

4 '- [(2-n-butyl-6-benzylaminocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert -butyl ester Melting point: 163-165 ° C ^' - [(e-Allylaminocarbonylamino) - n-butyl-benzimidazol-i-yD-methyllbiphenyl ^ -carboxylic acid tert.-butyl ester

Oil, Rp value: 0.10 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-n-butyl-6- (tetrahydropyran-2-yl-aminocarbonyl-tiino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid ethyl ester melting point: 86-88 ⁰ C (amorphous) 4 '- [(2-n-butyl-6- (tetrahydropyran-2-yl-aminocarbonylamino) -benzoimidazol-1-yl) -methyllbiphenyl -2-carboxylic acid tert.-butyl ester

Oil, Ri value: 0.20 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-n-pentylamino) -benz-imidazol-1-yl ) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R _r value: 0.30 (silica gel: methyl ethyl ketone / xylene = 5: 2) 4 '- [(2-n-butyl-6-cyclohexylaminocarbonylamino) benzimidazol-1-yl) -methyl] -2-phthalimino-biphenyl oil, Rr value: 0.45 (Kieselge: methylene chloride / ethanol = 9: 1) 4 '- [(6- (adamant-1-yl-aminocarbonylamino) -2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Melting point: 251-253 ° C 4 '- [(6- (adamant-1-yl-aminocarbonylamino) -2-n-butyl -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Melting point: 196-198 ⁰ C 4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-methylamino) -benzimidazole-1 -yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.30 (silica gel: methyl ethenyl ketone / xylene = 5: 2) 4 '- [(2-n-butyl-6- ( N- (n-butylaminocar'jonyl) -methylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester Oil, R _r Value: 0.70 (Ki silica gel: methyl ethyl ketone / xylene = 5: 2) 4'- | (2-n-butyl-5- (N-methylaminocarbonyl-n-pentylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert. butyl ester oil, Ri value: 0.45 (silica gel: methyl oleyl ketone / xylene = 1: 2 '!' - ((e-ln-butylaminocarbonylaminol) -n-butyl-benzimidazol-i-yD-methyllbiphenylcarboxylic acid isrt.butylester

Oil, Rr value: 0.7 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1) 4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-methylamino) -benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.7 (silica gel: methyl ethyl ketone / xylene = 5: 2) 4 '- [(2-n-butyl-6- (N- (n-) butylaminocarbonyl) -methylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert. butyl ester, Rf value: 0.55 (silica gel: methyl ethyl ketone = 5: 2) 4 '- [(2-n-butyl 6- (N-cyclohexylaminocarbonyl-n-pentylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylate

Oil, R _r value: 0.8 (silica gel: methyl ethyl ketone = 5: 2) 4 '- [(2-n-butyl-6- (N- (n-hexylaminocarbonyl) cyclohexylamino) benzimidazol-1-yl) methyl] biphenyl-2-carboxylate

Oil, R _r Value: 0.40 (alumina plate: ethyl acetate / petroleum ether = 3: 7) 4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonylcyclohexylamino) benzimidazol-1-yl) - methyl] biphenyl-2-carboxylate

Oil, Rp value: 0.40 (alumina: ethyl acetate / petroleum ether = 4: 1) 4 '- [(2-n-butyl-6- (N- (n-butylaminonarbonyl) -cyclohexylamino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylate

Oil, Rp value: 0.35 (silica gel: ethyl acetate / petroleum ether = 4: 1)

4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-cyclohex ^{<aminoJ-benzimidazol-i-yD-methylJbiphenyl} ^ -carboxylic acid tert.-butyl ester

Oil, Rp value: 0.45 (alumina: ethyl acetate / petroleum ether = 7: 3)

4'-l (2-n-butyl-6- (N-methylaminocarbonyl-benzyl / lamino) -b6nzimidazol-1-yl) methyl] Biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.45 (alumina: ethyl acetate / petroleum ether = 6: 4)

4 '- [(2-n-butyl-6- (N- (n-hexylaminocarbonyl) -benzyl-amino) -benzimidazole-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rp value: 0.50 (alumina: ethyl acetate / petroleum ether = 4: 6)

4 '- [(2-n-butyl · 6- (N-cyclohθxylaminocarbonyl-n-butylamϊno) -benzίmidazol-1-yl) -mβthyl | biphβnyl-2-carboxylic acid tert.butylθster

Melting point: 106-108 ° C (amorphous)

4'-l (2-n-butyl-6- (N-cyclohexylaminocarbonyl-benzylamino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.60 (silica gel: ethyl acetate / petroleum ether = 6; 4)

4 '- [(2-n-butyl-6- (N- (2-trifluormethylphenylaminocarbonyl) methylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylate

Oil, Rf value: 0.90 (silica gel: methyl ethyl ketone / xylene = 5: 2)

4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-n-hexylamino) -benzoimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

Oil, Ri value: 0.70 (silica gel: ethyl acetate / petroleum ether = 6: 4)

4 '- ((2-n-butyl-6- (N-cyclohexylaminocarbonyl-n-propylamino) -benzoimidazol-1-yl) methyl) biphenyl-2-carboxylate

Oil, Rr value: 0.50 (silica gel: ethyl acetate / petroleum ether = 6: 4)

4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-ethylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Ri value: 0.20 (silica gel: ethyl acetate / petroleum ether = 6: 4)

4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-N- (2-phenylethyl) amino) -bonzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rp value: 0.55 (silica gel: ethyl acetate / petroleum ether = 6: 4)

4'| (2-n-butyl-6- (N- (n-hexylaminocarbonyl) -N- (2-phenylethyl) amino) -benzoimidazol-1-yl-methyl] biphenyl-2-carboxylic acid tert butyl ester

Oil, R _r value: 0.20 (silica gel: ethyl acetate / petroleum ether = 7: 3)

4 '- [(2- (1-trans-butenyl) -6-cyclohexylaminocarbonylamino-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rp value: 0.20 (alumina / methylene chloride / ethanol = 50: 1)

4 '- [(2-n-butyl-6- (N- (dimethylaminocarbonyl) -n-pentylamino) -benzoimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.50 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4 '- [(2-n-butyl-6-cyclohexylaminocarbonylamino-benzimidazol-1-yl) methyl] -2- (1-triphenylmethyl-tetrazol-5-yl) biphenyl

Melting point: 183-187 ° C

4'- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl.methylthio) bβnzimidazol-1-yl) methyl] -2- (1-triphenylmethyl-tβ-trazol-b-yl) biphenyl

Melting point: 185-186 ⁰ C

4 '- ((2-n-butyl-6-cyclohexylaminocarbonyloxy-bonzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Melting point: 76-78 ° C (amorphous)

4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-N- (3-cyclohexyl-n-propyl) amino) benzimidazole-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.15 (aluminum oxide: petroleum ether / ethyl acetate = 2: 3)

4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-methylamino) -benzoimidazol-1-yl) methyl] -1-cyano-2-phenylnaphthalin4' - [(2-n-propyl-6- (N-cyclohexylaminocarbonyl-methylamino) benz-imidazol-1-yl) methyl] -2-phenylnaphthalene-1-carboxylic acid tert-butyl ester

4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-methylamino) -benzoimidazol-1-yl) methyl] -4-chloro-2-cyano-biphenyl4' - [(2-n-butyl 6- (N- (n-dodecylaminocarbonyl) methylamino) -benzimi (lazol-1-yl) methyl] biphenyl-2-curbonsäure tert.-butyl ester

Oil, Rr value: 0.40 (alumina: petroleum ether / ethyl acetate = 3: 7)

4 '- [(2-n-butyl-6- (N- (cyclohexylaminocarbonyl) n-octylamino) -benzoimidazol-1-yl) methyl | biphenyl-2-carboxylate

Oil, Rr value: 0.35 (alumina: petroleum ether / ethyl acetate = 3: 2)

4 '- (2-n-butyl-6- (N- (n-octylaminocarbonyl) methylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.35 (alumina: petroleum ether / ethyl acetate = 2: 3) Example 8

4 '- [(2-n-butyl-4-butanoylamlno-benzlmidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert. butyl ester 1.6 g (3.5 mmol) 4 '- [(4-amino-2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester are dissolved in 30 ml

Pyridine dissolved and added dropwise with stirring at room temperature 0.52 ml (6.0 mmol) butyryl chloride. After an hour will be from Distilled off solvent and the residue triturated with about 20ml diethyl ether. It sucks from the precipitate and dried

at 5O ⁰ C in vacuo.

Yield: 1.75 g (94.6% of theory), Melting point: 167-168 ° C The following compounds are obtained analogously:

4 '- [(2-n-butyl-5-acetamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rp value: 0.70 (silica gel: methylene chloride / ethanol = 9: 1)

4 '- [(2-n-butyl-5-butanoylamino-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.80 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1)

4 '- [(2-n-butyl-5-methanesulfonamino-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.75 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1)

4 '- [(2-n-butyl-6-isopropylsulfonamino-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert. butyl ester

Amorphous substance, R ₁ value: 0.55 (silica gel: methylene chloride / ethanol = 19: 1)

4 '- [(2-n-butyl-6-ethoxycarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Amorphous substance, R, value: 0.30 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-n-butyl-5- (tert-butoxycarbonylamino-acetamino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester Melting point: 101-103 ° C (amorphous) 4 '- [(2-n-Butyl-6- (N-butanoyl-methylamino) -benzimidazol-1-yl) -methyl-biphenyl 2-carboxylic acid tert-butyl ester oil, Rr value: 0.70 (Kieselgek methylene chloride / ethanol = 19: 1) 4'-l (2-n-butyl-7-butanesulfony! Amino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid ethyl ester oil, Rp value: 0.50 (silica gel: methylene chloride / ethanol = 19: 1) 4 '- [(2-n-butyl-5-propanoylamino-benzimidazol-1-yl) -methyl] biphenyl- 2-carboxylic acid ethyl ester melting point: 221-223 ⁰ C.

4 '- [(6-Äcetamino-2-n-butyl-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester melting point: 192-194 ⁰ C.

4 '- [(2-n-Butyl-6-propanoylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Melting point: 133-135 ° C

4 '- [(6-butanoylamino-2-n-butyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Melting point: 127-129 ⁰ C

Oil of tert-butyl 4 '- [(2-n-butyl-6-n-pentanoylaminobenzimidazol-1-yl) -methyllbiphenyl-2-carboxylate, R _r value: 0.6 (silica gel: methylene chloride / ethanol = 19 : 1) 4 '- [(2-n-butyl-6-dimethylaminocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.4 (silica gel: methyl ethyl ketone / Xylene = 5: 2) tert-butyl 4 '- [(2-n-butyl-6- (N- (dimethylaminocarbonyl) -methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylate

Oil, Rr value: 0.45 (silica gel: methylene chloride / ethanol = 19: 1)

Tert-butyl 4 '- [(2-n-butyl-6-phenylacetamino-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate Rr value: 0.30 (silica gel: mathylene chloride / ethanol = 50: 1). Melting point: 178 -18O ⁰ C

4'- | (2-n-Buty! -6-cyclohexylacetamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester Rr value: 0.30 (silica gel: ethyl acetate / petroleum ether = 4: 1)

Melting point: 64-66 ⁰ C (amorphous)

Tert-butyl 4 '- [(2-n-butyl-6-cyclohexylcarbonylamino-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate Rr value: 0.70 (silica gel: ethyl acetate / petroleum ether = 9: 1) Melting point: 72 -76 ⁰ C (amorphous)

4 '- ((6-Benzyloxycarbonylamino-2-n-butyl-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester Rr value: 0.80 (silica gel: ethyl acetate / petroleum ether = 9: 1). Melting point: 84 -86 ° C

4 '- [(2-n-butyl-6-cyclohexylmethylaminocarbonyl-benzimidazol-1-yl) methyl | biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.45 (silica gel: petroleum ether / ethyl acetate / ethanol = 2.5: 2.5: 0.5) 4 '- [(2-n-butyl-6-cyclohexylaminocarbonyl-benzimidazol-1-yl) - Methyl-biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.50 (silica gel: petroleum ether / ethyl acetate / ethanol = 2.5: 2.5: 0.5) 4 '- ((2-n-butyl-6-) (N-methyl-n-butylaminocarbonyl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.40 (silica gel: petroleum ether / ethyl acetate / ethanol = 6: 3: 1 + 1% glacial acetic acid) 4 '- [(2-n-butyl-5- (n-butylaminocarbonyl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.75 (silica gel : Petroleum ether / ethyl acetate = 1: 2 + 1% glacial acetic acid) 4'- | (2-n-butyl-6- (2-isopropyl-5-methyl-cyclohexyloxycarbonylamino) -benzimidazol-1-yl) -methyl] biphenyl-2 -carboxylic acid tert-butyl ester

Oil, Rr value: 0.45 (silica gel: ethyl acetate / petroleum ether = 60:40)

4 '- [(2-n-butyl-6- (N-ethoxycarbonyl-cyclohexylamino) -benzimidazol-1-yl) -methyl) -biph8-nyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.65 (silica gel: ethyl acetate / petroleum ether = 6: 4) 4'-I (2-n-butyl-6-cyclohexylacetamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester melting point: 65-66 ⁰ C (amorphous)

4 '- [(2-n-Butyl-6- (N-ethoxycarbonylbenzylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.60 (silica gel: ethyl acetate Petroleum ether = 7: 3) tert-butyl 4 '- [(2-n-butyl-6- (n-hexyloxycarbonylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate, Rf value: 0, 55 (silica gel: ethyl acetate / petroleum ether = 6: 4) 4 '- [(2-n-butyl-6- (5,7-dioxo-1H, 3H-imidazo | 1,5-c] -thiazol-6-yl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.55 (alumina: ethyl acetate / petroleum ether = 7: 3) 4 '- ((2-n-butyl-6-) (N- (n-butanoyl) -n-butylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R, value: 0.60 (silica gel: ethyl acetate / petroleum ether = 6 : 4) 4 '- [(2-n-Butyl-6- (N- (4-methoxycarbonylthiazolidin-3-yl-carbonyl) -n-butylamino) -benzimidazol-1-yl) -methyl] biphenyl-2 carboxylic acid tert-butyl ester

Oil, Rr value: 0.55 (silica gel: ethyl acetate / petroleum ether = 6: 4) 4 '- ((2-n-butyl-6- (N-cyclohexylcarbonyl-n-hexylamino) -benzimidazol-1-yl) -methyl] tert-butyl biphenyl-2-carboxylate, Rr value: 0.55 (silica gel: ethyl acetate / petroleum ether = 6: 4) 4 '- [(2-n-butyl-6- (N-cyclohexylcarbonyl-methylamino) -benzimidazole] 1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Ri value: 0.70 {silica gel: ethyl acetate / petroleum ether = 6: 4) 4 '- [(2-n-butyl-6- ( N- (n-butanoyl) -n-pentylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.60 (silica gel: methyl ethyl ketone / xylene = 1: 1) 4 '- ((2-n-butyl-6-isopropylcarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.15 (silica gel: ethyl acetate / petroleum ether = 7: 3) 4 '- [(2-n-butyl-6- (N-ethoxycarbonyl-methylamino) -benzimidazol-1-yl) -methyl ] biphenyl-2-carboxylic acid tert-butylrster oil, R, value: 0.35 (silica gel: ethyl acetate / petroleum ether = 6: 4) 4'- | (2-n-butyl-6- (N-ethoxycarbonyl-n -pentylamino) -benzoimidazol-l-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil. Rr value: 0.70 (silica gel: methyl ethyl ketone / xylene = 1: 1)

4 '- [(2-n-Butyl-6- (N- (dimethylaminocarb (' nyl) -benzylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester oil, Rp value: 0.45 ( Silica gel: ethyl acetate / strolether = 4: 1)

4'-t {2-n-butyl-6-diethylaminocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.20 (silica gel: ethyl acetate / petroleum ether = 9: 1 )

T-butyl ester of 4 '- [(2-n-butyl-6- (dimethylaminoacetamino) benzimidazol-1-yl) -methyllbiphenyl-2-carboxylate, Rr value: 0.40 (silica gel: methyl ethyl ketone / xylene = 5 : 2) tert-butyl 4 '- [(2-n-butyl-6- (2,2-dimethyl-propionylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate, Ri value: 0, 60 (silica gel: ethyl acetate / petroleum ether = 9: 1)

- '. - [(2-n-butyl-6-cyclopcntylcarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R _r value: 0.35 (silica gel: ethyl acetate / petroleum ether = 7: 3 )

4 '- [(2-n-butyl-6-cyclopropylcarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert.bulylester Melting point: 175-177 ⁰ C.

4 '- [(2-n-butyl-6-cyclohexyloxycarbonylamino-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester Melting point: 68-70 ⁰ C (amorphous)

4 '- [(2-n-butyl-6-dimethylaminocarbonylamino-benzimidazol-1-yl) -methyl) -2- (1-triphenylmethyl-tretrazol-5-yl) -biphenyl oil, Rr value: 0.75 (silica gel: Ethyl acetate / ethanol / ammonia = 90: 10: 1)

4 '- ((2-n-butyl-6-morpholinocarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester Melting point: 74-76 ⁰ C

4 '- [(2-n-butyl-6-pyrrolidinocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester 4' - [{2-n-butyl-6-dimethylaminocarbonyloxy-benzimidazole] 1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester melting point: 137-138 ⁰ C.

4 '- [(2-n-butyl-6- (N-acetyl-n-octylamino) -benzimidazol-1-yl) -me'-ethyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0, 25 (silica gel: ethyl acetate / petroleum ether = 7: 3)

Example 9

4 '- [(2-Hydroxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid _f

0.9 g (2.25 mmol) of 4 '- [(2-hydroxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester are dissolved in 10 ml of methylene chloride and admixed with 10 ml of trifluoroacetic acid. The solution is stirred for 2 hours at room temperature and then concentrated on a rotary evaporator to dryness. The oily residue is dissolved in 50 ml of methylene chloride and shaken twice with water. The organic phase is dried with magnesium sulfate and concentrated to dryness.

The crystalline residue thus obtained is triturated with a little diethyl ether, suction filtered and dried in vacuo at 5O ⁰ C.

Yield: 0.75 g (97.4% of theory),

Melting point: 303-304 ⁰ C

C ₂₁ H ₁₆ N ₂ O ₃ (344.37)

Ben: C73,24 H4,68 N8,13

Found: C 73.07 H 4.81 N 7.95

Analogously, the following compounds are obtained: 4 '- [(2,5-di-n-butyl-benzimidazol-1-yl) -methyl] biphei.vl-2-carboxylic acid Melting point: 199-201 ° C

4 '- [! 2,6-di-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Melting point: 188-19O ⁰ C

Example 10

4 '- [(2-n-butyl-6-methoxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-methoxy-benzimidazole) 1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 73.9% of theory

Oil, Rr value: 0.6 (silica gel: ethyl acetate / ethanol / ammonia = 50: 45: 5)

C ₂₆ H ₂₆ N ₂ O ₃ (414.51)

Calc .: C 75.34 H 6.23 N 6.76

Found: C 75.27 H 6.03 N 6.52

Example 11

4 '- [(2-n-butyl-4-methyl-7- (2-diethylamino-ethoxy) -benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid dihydrate Prepared analogously to Example 9 in 4Μ (2 × η-ΒΜνΙ · 4 ^ β% | -7- (2 · αϊβ% ^ ϊηο · βΜοχγ) ^ βηζϊΓΤΊία3ζοΙ-1-γΙ) · πιβ% |] ^ ρηβηνΙ-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 94.2% of theory,

Melting point: 94-96 ⁰ C

C ₃₂ H ₃₉ N ₃ Oi x H ₂ O (549.72)

Calcd .: C, 69.92, H, 7.88, N, 7.64

Found: C 69.62 H 7.60 N 7.40

Example 12

4 '- [(2-Ethylthlo-benzlmldazol-1-yl) methyl] blphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- ((2-ethylthio-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 92.9% of theory,

Melting point: 197-198 ° C

Cj ₃ H ₂₀ N ₂ O ₂ S (388.48)

Calc .: C71.11 H5.19 N7.21 S8.25

Found .: C, 71.12, H, 5.13, N, 7.23, S, 8.31

Example 13 4 '- [(2-n-Propylthlomethyl-benzl-mldazol-1-yl) -methyl] -phenyl Yl-2-carboxylic acid Prepared analogously to Example 9 from 4'- [(2-n-propylthiomethyl-benzimidazol-1-yl-methyllbiphenyl . ^ -carboxylic acid tert-butyl ester and trifluoroacetic acid yield: 96, ε% of theory, melting point: 139-141 ⁰ CC ₂₆ H ₂₄ N ₂ O ₂ S (416.54)

Calc .: C 72.09 H 5.81 N 6.73 S 7.70

Found: C, 71.82, H, 5.83, N, 6.57, S, 7.43

Example 14

4 '- [(2-Methyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid χ 0.33 HCl Prepared analogously to Example 9 from 4M (2-methyl-benzimidazoM-yl) -methyl] biphenyl-2- carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 93.2% of theory, melting point: 255-256 ⁰ CC ₂₂ H ₁₈ N ₂ O ₂ x 0.33HCl (354.54)

Calc .: C 74.53 H 5.21 N 7.90 Cl 3.32

Found: C74.60 H 5.14 N 8.16 Cl 3.40

Example 15

4 '- [(2-Methylmercaptobenzlazazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-methylmercapto-benzimidazol-1-yl) -methyl] biphenyl 2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 88.2% of theory, m.p .: 197-199 ⁰ CC ₂₂ H ₁₈ N ₂ O ₂ S (374.46)

Calcd .: C, 70.67, H, 4.84, N, 7.48, S, 8.56

Found: C, 70.30, H, 4.87, N, 7.25, S, 8.25

Example 16

Prepared analogously to Example 9 from 4 '- [(2-methyl-5- and 6-nitro-benzimidazol-i-yD-methyllbiphenyl) -carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 71.1% of theory,

Melting point: 285-288 ° C

C ₂₂ H ₁₇ N ₃ O ₄ (387.39)

Calc .: C 68.21 H 4.42 N 10.85

Found: C, 67.96, H, 4.40, N, 10.83

Example 17

4 '- [(2-Methyl-5- and 6-butanoylo-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2-methyl-5- and e -butanoylaminobenzimidazoM-YO-methyllbiphenyl -carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield 79.5% of theory, m.p .: 261-262 ⁰ CC ₂₆ H ₂₅ N ₃ O ₃ (427.50)

Calc .: C 73.05 H 5.89 N 9.83

Found: C, 72.85, H, 5.90, N, 9.80

Example 18

4 '- [(2- (2-Methylpropyl) benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2- (2-methylpropyl) benzimidazol-1-yl ) -methyl] biphenyl-2-carboxylic acid tert.butylcaster and trifluoroacetic acid.

Yield: 71.9% of theory, m.p .: 211-212 ⁰ CC ₂₆ H ₂₄ N ₂ O ₂ (384.48)

Calc .: C 78.10 H 6.29 N 7.29

Found .: C 77.95 H 6,22 N 7,15

Example 19

4 '- [(2-Methoxymethyl-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-methoxymethylbenzimidazol-1-yl) -methyl] biphenyl-2- carboxylic acid tert, butyl ester and trifluoroacetic acid.

Yield: 80.3% of theory,

Melting point: i-o-197 ° C

C ₂₃ H ₂₀ N ₂ O ₃ (372.43)

Re: C74.18 H5.41 N7.52

Found: C 73.99 H 5.39 N 7.43

Example 20

4 '- [(2- (2-pyridyl) -benzlmidazol-1-yl) -mothyl] biphenyl-2-carbons3ure

Prepared analogously to Example 9 from 4 '- [(2- (2-pyridyl) benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid. Yield: 50.0% of theory, Melting point: 262-264 ° C

C ₂₆ H ₁₉ N ₃ O ₂ (405.45)

Calc .: C77.02 H4,72 N 10,36

Found: C 77.21 H 4.58 N 10.20

Example 21

4 '- [(5-and 6-methyl-benzlmidazol-1-yl) methyl] blphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(5- and e-methyl-benzimidazol-i-methyl-methylbiphenyl] -carboxylic acid tert-butyl ester and Trifluoroacetic acid. Yield: 92.0% of theory, Melting point: 228-23O ⁰ C

C ₂₂ H ₁₈ N ₂ O ₂ (342.396)

Calc .: C77.17 H 5.30 N8 / I8

Found: C, 76.94, H, 5.23, N, 7.93

Example 22

4 '- [(2-Phenyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-phenyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid. Yield: 56.8% of theory,

Melting point: 275-277 ° CC ₂₇ H ₂₀ N ₂ O ₂ (404.47)

Calc .: C 80.18 H 4.98 N 6.93

Found: C 79.90 H 5.05 N 6.92

Example 23

4 '- [(2- (Thiazol-4-yl) -benzimidazol-1-yl) -methyl] -b-phenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-l (2- (thiazol-4-yl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 94.6% of theory, m.p .: 284 ~ 286 ° CC ₂₄ H ₁₇ N ₃ O ₂ S (411.48)

Calc .: C70.06 H4.16 N 10.21 S7.79

Gef .: C69.90 H4.29 N 9.97 S7.59

Example 24

4 '- [(2- (3,5-Dimethyl-pyrazol-1-yl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-I (2- (3, 5-Dimethyl-pyrazol-1-yl) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 87.2% of theory, melting point: 185-187 ⁰ CC ₂₆ H ₂₂ N ₄ O ₂ (422.49)

Calc .: C 73.92 H 5.25 N 13.26

Found: C, 73.86, H, 5.37, N, 13.27

Example 25

4 '- [(2- (Furyl- (2)) benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2- (furyl- (2)) benzimidazole 1 -yl) -methyllbipnenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 78.4% of theory, Melting point: 263-265 ⁰ C

C "H, _B N ₂ O ₃ (394.43)

Calc .: C76.13 H4.60 N7.10

Found: C7L 14H 4.64N 6.83

Example 26

4 '- [(2-aminocarbonylamino-benzlmidazol-1-yl) methyl] biphBnyl-2-carboxylic acid monohydrate

Prepared analogously to Example 9 from 4 '- [(2-aminocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester

and trifluoroacetic acid.

Yield: 53.3% of theory, Melting point: 214-216 ° C

C ₂₂ H ₁₈ N ₄ O ₃ x H ₂ O (404.42)

Calc .: C 65.34 H 4.98 N 13.85

Found: C 65.18 H 5.05 N 13.61

Example 27

4 '- [(2-isopropyl-benzimidazol-1-yl) -mothyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'- (2-isopropyl-benzimidazol-1-yl) -methyl) biphenyl-2- carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 80% of theory,

Melting point: 20 & -208 ° C

C ₂₄ H ₂₂ N ₂ O ₂ (370.46)

Calc .: C77.81 H5.99 N7.56

Found: C 77.55 H 5.97 N 7.43

Example 28

4 '- [(7-benzyloxy-2-n-butyl-4-niethyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid trifluoroacetate

Prepared analogously to Example 9 from 4 "-l (7-benzyloxy-2-n-butyl-4-methylbenzimidazol-1-yl-methyllbiphenylcarboxylic acid

tert.butyl ester and trifluoroacetic acid.

Yield: 85.5% of theory, m.p .: 217-219 ° C

C ₃₃ H ₃₂ N ₂ O ₃ χ CF ₃ COOH (618.66)

Re: C67.95 H5.37 N4.52

Found: C, 68.19, H, 5.56, N, 4.74

Example 29

4 '- [(2-Hydroxymethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid trifluoroacetate Prepared analogously to Example 9 from 4' - [(2-hydroxymethyl-benzimidazol-1-yl) -methyl-biphenyl-2- carboxylic acid tert-butyl ester and

Trifluoroacetic acid. Yield: 81.9% of theory,

Melting point: 188-19O ⁰ C

C ₂₂ H ₁₈ N ₂ O ₃ x CF ₃ COOH (472.42)

Calc .: C 61.02 H 4.05 N 5.93

Gef .: C61.23 H4.08 N5.91

Example 30

4 '- [(2- (3-hydroxypropyl-benzimidazol-1-yl) methyl] biphenyl-2-carbonsäur3 trifluoroacetate

Prepared analogously to Example 9 from 4 '- [(2- (3-hydroxypropyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid. Yield: 58.8% of theory, Melting point: 150-152 ° C

C ₂₄ H ₂₂ N ₂ O ₃ x CF ₃ COOH (500.47)

Calc .: C, 62.40, H, 4.63, N, 5.60

Found: C, 62.13, H, 4.70, N, 5.83

Example 31

4 '- [(2-methyl-5-und6- (N- (2-methoxy-acetyl) -n-butylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-methyl-5- and 6- (N- (2-methoxy-acetyl) -n-butylamino) -benzimidazol-1-yl)

tert-butyl methyllbiphenyl-2-carboxylate and trifluoroacetic acid.

Yield: 84.8% of theory, Melting point: 186-188 ⁰ C

C ₂₉ H ₃₁ N ₃ O ₄ (485.58)

Calc .: C 71.73 H 6.43 N 8.65

Found: C, 72.67, H, 6.68, N, 8.74

Example 32

4 '- [(2- (1-Methylpropyl) benzimidazol-1-yl) methyl] b! Phenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2- (1-methylpropyl) benzimidazol-1-yl) -methyl] biphenyl-2-tert-butyl ester and Trifluoroacetic acid. Yield: 80% of theory, Melting point: 147-148 ⁰ C

C ₂₅ H ₂₄ N ₂ O ₂ (384.48)

Calc .: C 78.10 H 6.29 N 7.29

Found .: C 77.91 H 6.23 N 7.37

Example 33

4 '- [(2- (2-methylbutyl) -benzlmldazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2- (2-methylbutyl) benzimidazol-1-yl-methyllbiphenyl] -carboxylic acid tert-butyl ester and Trifluoroacetic acid.

Yield: 60% of theory,

Melting point: 209-210 ⁰ C

Calc .: C 78.36 H 6.58 N 7.03

Gef .: C78.27 H6.51 N6.99

Example 34

4 '- [(2-Mothyl-5-and 6- (N- (2-me1hoxy-ethyl) -n-butylamino) -benzlmldazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 of 4'- [(2-Methyl-5- and 6- (N- (2-methoxy-ethyl) -n-butylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 46.5% of theory, m.p .: 102-106 "C

C ₂₉ H ₃₃ N ₃ O ₃ (471.598)

Calc .: C 73.86 H 7.05 N 8.91

Found .: C 73.60 H 7,13 N 8,85

Example 35

4 '- [(2-n-pentyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-pentyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 87% of theory,

Melting point: 181-183 ° C

C ₂₆ H ₂₆ N ₂ O ₂ (398.51)

Calc .: C 78.36 H 6.58 N 7.03

Found .: C 78.12 H 6.42 N 7.09

Example 36

4 '- [(Benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 90.9% of theory,

Melting point: 217-219 ° C

C ₂₁ H ₁₀ N ₂ O ₂ (328.37)

Calc .: C76.81 H4.91 N 8.53

Found .: C 77.03 H 5.00 N 8.42

Example 37

4 '· [(2 × n-butyl-4-methyl-7-methylthiobenzimidazole 1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-4-methyl-7 -methoxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 86.6% of theory,

Melting point: 216-218 ° C

C ₂₇ H ₂₈ N ₂ O ₃ (428.54)

Calcd .: C, 75.68, H, 6.59, N, 6.54

Found: C, 75.48, H, 6.59, N, 6.45

Example 38

4 '- [(2-n-propylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-propylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 85.2% of theory, melting point: 237-238 ° C

C ₂₄ H ₂₂ N ₂ O ₂ (370.45)

Calc .: C 77.81 H 5.39 N, 7.56

Found: C 78.08 H 5.74 N 7.37

Example 39

4 '- [(2-Ethylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2-ethylbenzimidazole) -ol-1-yl) methyllbiphenyl-2 -carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 81.6% of theory, melting point: 251-253 ° C

C ₂₃ H ₂₀ N ₂ O ₂ (356.42)

Calc .: C 77.51 H 5.66 N 7.86

Found: C 77.72 H 5.64 N 7.59

Example 40

4 '- [(2-Ethylthiomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid semitrifluoroacetate Prepared analogously to Example 9 from 4' - [(2-ethylthiomethylbenzimidazol-1-yD-methyllbiphenylcarboxylic acid] tert.butyl ester and trifluoroacetic acid.

Yield: 96.1% of theory,

Melting point: 139-141 ⁰ C

C ₂₄ H ₂₂ N ₂ O ₂ S χ Vz CF ₃ COOH (459.52)

Calc .: C65.35 H4.94 N 6.10 S 6.98

Found: C 65.24 H 5.00 N 6.18 S 6.98

Example 41

4 '- [(2-MethvlthlomethYl-bönzimldazol-1-yl) -methyUbiphonvl-2-carbonsäuro-semitrilluoracetat

Prepared analogously to Example 9 from 4 '- [(2-methylthiomethyl-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester

and trifluoroacetic acid.

Yield: 98.6% of theory,

Melting point: 147-149 ⁰ C

C ₂₃ H ₂₀ N ₂ O ₂ S x '/ 2 CF ₃ COOH (445.495)

Calc .: C, 64.71, H, 4.64, N, 6.29, S, 7.20

Found: C 64.70 H 5.04 N 6.51 S 6.91

Example 42

4 '- [(2-Chloro-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-chloro-benzimidazol-1-yl-1) -methyl] biphenyl-2- carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 84.0% of theory, Melting point: 169-171 ⁰ C

C ₂₁ H ₁₆ CIN ₂ O ₂ (362,815)

Calc .: C69.52 H4.17 N 7.72 Cl 9.77

Found: C 69.39 H 4.13 N 7.66 Cl 9.72

Example 43

4 '- [(2-n-Butylthlo-benzlmldazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4'- | (2-n-butylthio-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid.

Yield: 88.0% of theory,

Melting point: 160-162 ⁰ C

C ₂₆ H ₂₄ N ₂ O ₂ S (416.54)

Calc .: C 72.09 H 5.81 N 6.73 S 7.70

Found: C, 71.93, H, 5.75, N, 6.74, S, 7.71

Example 44

4 '- [(2-n-butyl-5-acetamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid hydrate

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-5-acetamino-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

and trifluoroacetic acid.

Yield: 71.3% of theory,

Melting point: 187-189 ⁰ C

C ₂₇ H ₂₇ N ₃ O ₃ x H ₂ O (459.54)

Calc .: C 70.56 H 6.36 N 9.14

Found: C 70.40 H 6.22 N 9.08

Example 45

4 '- [(2- (4-Mothoxyphenyl) -bGnzimldazol-1-yl) methyllbiphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2- (4-methoxyphenyl) -benzimidazol-1-yl) methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 87.5% of theory, Melting point: 283-286 ⁰ C

C ₂₈ H ₂₂ N ₂ O ₃ (434.50)

Calc .: C 77.40 H 5.10 N 6.45

Found: C 77.45 H 5.20 N 6.44

Example 46

4 '- [(2-n-Propylthio-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-t (2-n-propylthio-benzimidazol-1-yl) -methyl] biphenyl -2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 90.5% of theory, Melting point: 219-22O ⁰ C

C ₂₄ H ₂₂ N ₂ O ₂ S (402.51)

Ref .: C71.62 H5,51 N6.96 S7.97

Gef .: C71.47 H 5,51 N 6,75 S8.09

Example 47

4 '- [(2-n-butylamino-benzlmidazol-1-yl) methyl] biphenyl-2-carbonsöure-semitrifluoracetat

Prepared analogously to Example 9 from 4 '- [(2-n-butylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid.

Yield: 80.0% of theory, melting point: 247-249 ° CC ₂₅ H ₂₆ N ₃ O ₂ X 'Λ CF ₃ COOH (456.50)

Calc .: C 68.41 H 5.63 N 9.20

Found: C 68.56 H 5.84 N 9.07

Example 48

4 '- [(2- (4-methoxy-phenyl) -5-and 6-chloro-benzimidazol-1-yl) -mothyllbiphenyl-2-carboxylic acid &

Prepared Example 9 from 4'-l (2- (4-methoxy-phenyl-5- and e-chloro-benzimidazol-i-YD-methyl-biphenyl) -carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 76.3% of theory, Melting point: 234-236 ⁰ C.

C ₂₈ H ₂ IN ") ₃ (468.95)

Calc .: C71.71 H4.51 N5.97 CI7.56

Found: C71.57 H4.39 N 5.85 CI7.79

Example 49

4 '- [(2-n-butyl-5-methoxy-benzimiciazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5-methoxybenzimidazole -1-yl) -methyllbiphenyl-2-carboxylic acid tert-butylstyrene and trifluoroacetic acid.

Yield: 66.2% of theory, Melting point: 203-205 ⁰ C.

C ₂₆ H ₂₆ N ₂ O ₃ (414.51)

Calc .: C 75.34 H 6.32 N 6.76

Found: C, 75.19, H, 6.31, N, 6.61

Example 50

4 '- [(2-n-butyl-5- and 6-acetamido-benzimidazol-1-yl) -mothyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 ius 4' - [(2-n-butyl-5- and e-acetaminocarbonimidazol-i-yD-methyllbiphenyl -carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 83.7% of theory, m.p .: 117-119 "C

C ₂₇ H ₂₇ N ₃ O ₃ (441.54)

Calc .: C, 73.45, H, 6.16, N, 9.52

Found .: C 73.25 H 6.23 N 9.47

Example 51

4 '- [(2-n-butyl-5- and 6-butanoylaminobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5-) and e-butanoylaminobenzimidazole-i-yD-methyllbiphenyl -carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 80.0% of theory, Melting point: 123-127 ⁰ C.

C ₂₉ H ₃₁ N ₃ O ₃ (469.59)

Calc .: C74.18 H6.65 N8.95

Found: C 73.96 H 6.19 N 8.99

Example 52

4 '- [(6- (N-Benzyl-methylamino) -2-n-butylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(6- (N-benzyl -methylamino) -2-n-butyl-benzimidazol-1-yl) -methyl | biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 82.0% of theory, melting point: 237-238 ° C

C ₃₃ H ₃₃ N ₃ O ₂ (503.64)

Calc .: C 78.70 H 6.60 N 8.34

Found: C, 78.68, H, 6.71, N, 8.44

Example 53

4 '- [(2-n-butyl-b-chloro-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5-chlorobenzimidazole-1 -d-methyllbiphenylcarboxylic acid-tert-butyl ester and trifluoroacetic acid.

Yield: 70.6% of theory, Melting point: 191-193 ⁰ C.

C ₂₆ H ₂₃ CIN ₂ O ₂ (418.92)

Calc .: C71.68 H5.53 N6.69 CI8.46

Gef .: C71.48 H5,40 N6,53 CI8.43

Example 54

4 '- [(2-n-Butyl-5- and 6-methoxy-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5 - and e-methoxy-benzimidazol-i-yD-methyllbiphenyl ^ -carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 84.1% of theory, Melting point: 128-133 ⁰ CC ₂₆ H ₂₆ N ₂ O ₃ (414.51)

Calc .: C75.34 H 6.32 N 6.76

Found: C, 75.32, H, 6.14, N, 6.75

Example 55

4 * ((2-η-ΒυΐνΙ-7-η ^ ^ υΙοχν · 4ΓηβΙΗνΙ βηζ! (Ηί £ ΐ8ζοΙ1νΙ) Γηβ1ΙινΙ] ο1ρΗβηνΙ2ε8ΓΟοη8ΐυΓθΐΓΐ "υοΓβοβΐ

Prepared analogously to Example 9 from 4'-l (2-n-Butyl-7-n-butoxy-4-methyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butylester in methylene chloride.

Yield: 63.3% of theory, m.p .: 172-173 ⁰ CC ₃₀ H ₃₄ N ₂ O ₃ x CF ₃ COOH (584.65)

Calc .: C 65.74 H 6.03 N 4.73

Found: C 66.52 H 6.15 N 4.95

Example 56 2-n-Butyl 1 - [(2-carboxy-biphenyl-4'-yl) -methylthvl-6,7-dihydro-7,7-dimethyl-5-ethyl-5H-pyrrolo [2,3-f] -benzimidazole-6-yne monohydrate

5 g (10.3 mmol) of 6-amino-5-l (2-tert-butoxycarbonyl-biphenyl-4'-yl) -methyl] -amino-3,4-dimethyl-1-ethyl-indol-2-one and 5 ml Valeric acid is boiled for 4 hours at reflux. After cooling, it is stirred into 50 ml of saturated aqueous sodium carbonate solution. It is shaken 3 times with 30 ml of methylene chloride. The methylene chloride phase is dried with sodium sulfate and concentrated in vacuo. The crude product is washed with a silica gel column (eluent:

Ethyl acetate / ethanol / ammonia = 90: 10: 1).

Yield: 1.55 g (30.3% of theory),

Melting point: 185-187 "C

C ₃ IH ₃₃ N ₃ O ₃ X '/ 2H ₂ O (504, S4)

Calc .: C 73.81 H 6.79 N 8.33

Found: C 73.91 H 6.86 N 8.36

Example 57

4 '- [(2-n-butyl-7-hydroxy-4-methyl-benzimidazol-1-yl) -methyl] -2- (1H-tetrazol-5-yl) -blphenyl-hydrate 0.9g (1, 7mlvol) 4 '- [(2-n-butyl-7-benzyloxy-4-methyl-benzimidazol-1-yl) -methyl] -2- (1H-tetrazol-5-yl) -biphenyl dissolved in 100 ml of methanol , are hydrogenated under 5 bar hydrogen pressure in the presence of 0.9 g of 20% palladium hydroxide on carbon at room temperature. The catalyst is then filtered off with suction and the filtrate is concentrated to dryness in vacuo.

The crude product is recrystallized from acetone / ether and dried in vacuo at 50 ° C.

Yield: 0.72 g (97.3% of theory), m.p .: 231-233 ° CC ₂₆ H ₂ BN ₆ O x H ₂ O (456.56)

Calc .: C68.40 H6,18 N 18,40

Gef .: C68, S4 H6,40 N 18,55

The following compounds are obtained analogously:

4 '- [(2-n-butyl-7-hydroxy-4-methyl-benzimidazol-1-yl) methyl) -2-trifluoracetamino-biphenyl Melting point: 243-245 ⁰ C. 4' - [(2-n- butyl-7-hydroxy-4-methyl-benzimidazol-1-yl) methyl] -2-trifli; ormethansulfonaminobiphenyl melting point: 160-162 ⁰ C. 4 '- [(2-n-butyl-7-hydroxy-benzimidazol-1 -yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rf value: 0.60 (silica gel: methyl ethyl ketone / xylene = 1: 1) 4 '- [(2-n-butyl-6-hydroxybenzimidazol-1-yl) methyl] biphenyl-2- tert-butyl carboxylic acid oil, Rp value: 0.55 (silica gel: methyl ethyl ketone / xylene = 1: 1) 4 '- [(2-n-butyl-4-hydroxybenzimidazol-1-yl) methyl] tert-butyl biphenyl-2-carboxylate Melting point: 91-93 ⁰ C 4 '- [(2-n-butyl-5-hydroxybenzimidazol-1-yl) -rnyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.60 (silica gel: methyl ethyl ketone / xylene = 1: 2)

Melting point: 224-226 ° C

Example 58

4 '- [(2-n-Butyl-benzimldazol-1-yl) methyl] -2- (1 H-tetrazol-S-yl) -biph8nyl

a) 4 '- [(2-n-butyl-benzimidazol-1-yl! -methyl] -2- (1-trifluoromethyl-tetrazo-5-yl) -blphenyl!

0.87 g (5 mmol) 2-n-butyl-benzimidazo! are dissolved in 20 ml of dimethyl sulfoxide and treated while stirring with 0.61 g (5.5 mmol) of potassium tert-butylate. After 1/2 hour, 4'-bromomethyl-2-C! -Triphenylmethyl-1H-tetrazol-5-yl) -biphenyl is added and the mixture is stirred.

3 hours at room temperature. It is poured into about 50 ml of ice-water and shaken 3 times with 30 ml of ethyl acetate each. The ethyl acetate phase is extracted by shaking with 20 ml of water, dried over sodium sulfate and concentrated to dryness. The crude product is purified over a silica gel column (particle size: 0.063-0.2 mm, eluent: methylene chloride / ethanol = 100: 1).

Yield: 2.1 g {64.6% of theory), Melting point: 85-87 ⁰ C

CmH ₃₈ N ₆ (650,84)

Calc .: C81.20 H 5.88 N 12.91

Found: C, 80.97, H, 5.90, N, 12.66

b) 4 '- [¢ 2-n-butylbenzimidezol-1-yl) -methyl] -2- {1H-tetrazole-5-vl) -bubbylate

2 g OmMoI) 4 '- ((2-n-butyl-benzimidazol-1-yl) methyl] -2- (1-triphenylmethyl-tetrazol-5-yl) -biphenyl are dissolved in a mixture of 1.0 ml of methylene chloride and 10 ml of methanol are added, 10 ml of ethereal hydrochloric acid are added and the mixture is stirred at room temperature for 3 hours, evaporated to dryness in vacuo, the residue is dissolved in methanol, made alkaline with ammonia and concentrated again by rotary evaporation. 0.063-0.2 mm, eluent: methylene chloride / ethanol / ammonia = 19: 1, 0.1, purified, crystallized from ether and dried in vacuo at 50 ° C. Yield: 1.02 g (81.6% of theory) .

Melting point: 241-243 ° C

C ₂₅ H ₂₄ N ₆ (408.52)

Calc .: C 73.50 H 5.92 N 20.57

Found: C 73.34 H 5.92 N 20.47

Example 59

νν

A mixture of 3.8 g (7.1 mmol) ammonium chloride, 4.5 g (69 mmol) sodium azide, 20 ml dimethylformamide and 2.2 g (4.53 mmol) 4 '- [2-n-butyl-7-benzyloxy-4- Methyl-benzimidazol-1-yl) -methyl | -2-cyano-biphenyl is heated with stirring to 120 ° C internal temperature for 36 hours. The mixture is filtered from the sodium chloride formed and the filtrate is rotated in vacuo. The oily residue is crosslinked with 50 ml of water and under cooling with concentrated hydrochloric acid to pH 2. It is filtered from the oily crude product, this takes up in 50 ml of methylene chloride and dried over sodium sulfate. It is then purified on a silica gel column (particle size: 0.063-0.2 mm, eluent: methylene chloride / ethanol = 19: 1). The uniform fractions are concentrated to dryness in vacuo and the residue is dried at 50 ° C. Yield: 1.6 g (68% of theory), Melting point: 112-116 ⁰ CC ₃₃ H ₃₂ N ₆ O x VaH ₂ O (537.66) Calc .: C 73.73 H 6.18 N 15.63

Found: C 73.55 H 6.33 N 15.91

Example 60

4 '- [(7-Acetoxy-2-n-butyl-4-methyl-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid 0.55 g (1 mmol) of 4' - [(2-n- Butyl-7-hydroxy-4-methyl-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid trifluoroacetate are dissolved in 20 ml of pyridine. For this purpose (7 mmol) of acetyl chloride under stirring at 5 "C 0.5 ml was added dropwise. The mixture is stirred 1 hour at 5 ⁰ C and then for 2 hours at room temperature. The pyridine is distilled off on a rotary evaporator in vacuo. The Rückstano is triturated with water and filtered off with suction. After washing with water C is dried in vacuo at 5O ^0th

Yield: 0.43 g (94% of theory),

Melting point: 242-244 ⁰ C

C ₂₈ H ₂₈ N ₂ O ₄ (456.55)

Calc .: C73.66 H 6,18 N 6,14

Found: C 73.50 H 6.20 N 6.36

Example 61 4 '- [(7-n-Butoxy-2-n-butyl-4-methyl-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid trifluoroacetate

a) 4 '- [(7-n-Butoxy-2-n-butyl-4-methyl-benzimidazol-1-yl) -methyl] -blphenyl-2-cp.rbons-acid-tert-butyl ester

A mixture of 0.94 g (2 mmol) of 4 '- [(2-n-butyl-7-hydroxy-4-methyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester, 36 ml of dimethylformamide, 4 ml of water , 1.4 g (10 μmol) of potassium carbonate and 0.9 g (6.6 mmol) of n-butyl bromide are stirred at room temperature for 16 hours. It is poured onto 200 ml of ice-water and takes up the precipitated oily precipitate after decantation in methylene chloride. The methylene chloride solution is dried over sodium sulfate and concentrated in vacuo. The crude product is purified on a silica gel column (particle size: 0.065-0.2 mm, eluent: methylene chloride / ethanol = 50: 1).

Yield: 0.8 g (76% of theory),

Oil, Rf value: 0.6 (silica gel: methylene chloride / ethanol = 19: 1)

C ₃₄ H ₄₂ N ₂ O ₃ (526.7)

Calc .: C 77.53 H 8.04 N 5.32

Found: C 77.53 H 7.87 N 5.31

The following compounds are obtained analogously:

4 '- [(2-n-Butyl-7-methoxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rp value: 0.70 (silica gel: methyl ethyl ketone / xylene = 1 :1)

4 '- [(2-n-butyl-7- (2-methoxyethoxy) -4-methyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R i value: 0.35 (alumina plate: methylene chloride / ethanol = 99: 1)

b) 4 '- [(7-n-Butoxy-2-n-butyl-4-methylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid trifluoroacetate

0.8 g (1.5 mmol) of tert-butyl 4 '- [(7-n-butoxy-2-n-butyl-4-methylbenzimidazol-1-yl) -yl) -methyl) -2-carboxylate are dissolved in 15 ml of methylene chloride , mixed with 5 ml of trifluoroacetic acid and stirred for 2 hours at room temperature. It is rotated to dryness in vacuo and the residue is recrystallized from acetone. The crystals are dried in vacuo at 5O ⁰ C.

Yield: 0.45 g (51.3% of theory), Melting point: 172-174 ⁰ C.

C ₃₀ H ₃₄ N ₂ O ₃ X _CF3COOH (584.65)

Calc .: C 65.74 H 6.03 N 4.73

Gef .: C65.52 H6.15 N4.95

The following compounds are obtained analogously: 4 '- [(2-n-butyl-7- (2- (1-imidazolyl) -ethoxy) -4-methylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid bis-trifluoroacetate

Melting point: 229-231 "C

4 '- ^[(2: n-butyl-7- (2-hydroxy-ethoxy) -4-methyl-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid Melting point: 216 ⁰ C.

Example 62

4 '- [(2-n-butyl-4-hydroxy-7-methylbenzimidazole-1-vl) -methYI] -blphenY1-2-carboxylic acid Prepared analogously to Example 57 from 4' - [(4-benzyloxy-2- n-butyl-methyl-benzimidazol-1-yl-methyl-biphenylcarboxylic acid and hydrogen in methanol / dimethylformamide in the presence of 20% palladium hydroxide on carbon. Yield: 64.4% of theory, m.p .: 291-294 ⁰ CC ₂₆ H ₂₆ N ₂ O ₃ (414.51)

Calcd .: C75.34 H 6.32 N 6.76

Found: C, 75.22, H, 6.40, N, 6.64

Example 63

4 '- [(2-Ethylsulfinylmethyl-benzl-mldazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid 2.01 g (5, OmMoI) 4' - [(2-ethylthiomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid are dissolved in 25 ml of glacial acetic acid and treated with 0.51 ml of 30% hydrogen peroxide. The solution is allowed to stand for 24 hours at room temperature and then concentrated to dryness. The residue is purified over a silica gel column (particle size: 40-63 μ, eluent:

Methylene chloride / ethanol / glacial acetic acid = 50/1 / 0.15). The uniform fractions are combined, the solvents distilled off, the residue dissolved in methylene chloride and washed three times with water. The organic phase is dried with magnesium sulfate and concentrated to dryness. The crystalline residue is triturated with diethyl ether, filtered off and the crystals are dried in vacuo at 75 ⁰ C.

Yield: 1.90 g (90.9% of theory),

Melting point: 161-163 ⁰ CC ₂₄ H ₂₂ N ₂ O ₃ S (418.51)

Calc .: C 68.88 H 5.30 N 6.69 S 7.66

Found: C, 68.65, H, 5.40, N, 6.72, S, 7.64

Example 64

4 '- [(2-n-propylsulfinylmethylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 63 from 4' - [(2-n-propylthiomethylbenzimidazol-1-yl) methyllbiphenyl-2- carboxylic acid and hydrogen peroxide in glacial acetic acid.

Yield: 78.7% of theory,

Melting point: 128-130 ⁰ C

C ₂₆ H ₂₄ N ₂ O ₃ S (432.54)

Calc .: C 69.42 H 5.59 N 6.48 S 7.41

Found: C 69.57 H 5.46 N 6.04 S 7.28

Example 65

4 '- [(2-Hydroxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid 3-N-oxide Prepared analogously to Example 63 from 4' - [(2-methylmercaptobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid and hydrogen peroxide in glacial acetic acid.

Yield: 35.9% of theory, m.p .: 272-274 ⁰ CC ₂₁ H ₁₆ N ₂ O ₄ (.160.37)

Ber. C 69.99 H 4.47 N 7.77

Found .: C 70.00 H 4.85 N 7.51

Example 66

4 '- [(2-Methylsulfinylmethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 63 from 4' - [(2-methylthiomethylbenzimidazol-1-yl) -methylbiphenyl-2-carboxylic acid and hydrogen peroxide / acetic acid.

Yield: 79.2% of theory, melting point: 232-234 ° CC ₂₃ H ₂₀ N ₂ O ₃ S (404.48)

Calc .: C 68.80 H 4.98 N 6.93 S 7.93

Gef .: C68,17 H4,86 N7.04 S7.89

Example 67

4 '- [(2-Ethylsulfonylmethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid 2.01 g (5.0 mmol) 4'-t (2-ethyltiomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid are dissolved in 25 ml of formic acid and treated with 1.02 ml (1OmMoI) of 30% hydrogen peroxide. The solution will stand at room temperature for 24 hours

left and then concentrated to dryness. The residue is purified over a silica gel column (particle size: 40-63μ, eluent: methylene chloride / ethanol / glacial acetic acid = 100/1 / 0.15 to 50/1 / 0.15). The uniform fractions are combined and concentrated to dryness. The residue is dissolved in methylene chloride, washed three times with water, the organic phase dried with magnesium sulfate and concentrated to dryness. The crystalline residue is triturated with diethyl ether, filtered off with suction and dried at 75 ^° C. under reduced pressure.

Yield: 1.80 g (82.9% of theory), melting point: 158-16O ⁰ C.

C ₂₄ H ₂₂ N ₂ O ₄ S (434.51)

Ref .: C66.34 H5.10 N 6.45 S7.38

Found: 'C 66.32 H 5.05 N 6.54 S 7.27

The following compounds are obtained analogously:

4 '- [(2-n-butyl-6-methylsulfonyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid 4' - [(2-n-eutyl-6-ethylsulfonylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid 4 '- [(2-n-butyl-6-n-butylsulfonylbenzimidazol-1-yl) -rnyl] biphenyl-2-carboxylic acid

Example 68

4 '- [(2-n-propylsulfonylmethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 67 from 4' - [(2-n-propylthiomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid and

Hydrogen peroxide in formic acid.

Yield: 78.1% of theory,

Melting point: 135-137 ⁰ C

C ₁₆ H ₂₄ N ₂ O ₄ S (448.54)

Calc .: C66.95 H 5.39 N 6.25 S 7.15

Found: C 66.83 H 5.46 N 6.03 S 7.06

Example 69

^ (Z-Methylsulfonylmethyl-benzimidazole-1-methyl-1-phenylcarboxylic acid Prepared analogously to Example 67 from 4 '- [(2-methylthiomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid and hydrogen peroxide.

Yield: 80.0% of theory,

Melting point: 290-292 ⁰ C

C ₂₃ H ₂₀ N ₂ O ₄ S (420.48)

Calc .: C 65.70 H 4.79 N 6.66 S 7.62

Found: C, 65.67, H, 4.64, N, 6.88, S, 7.72

Example 70

Ethyl 4 '- [(2-n-butyl-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylate 1.2 g (7 mmol) of 2-n-butylbenzimidazole are dissolved in 25 ml of dimethylsulfoxide, with O, 8 g (7 mmol ) Potassium tert-butylate and stirred for 20 minutes at room temperature. Then 2.25 g (7 mmol) of 2-carbethoxy-biphenyl-4'-yl-methyl bromide are added and stirred until the quantitative reaction (about 1 hour) at room temperature. After pouring into 100 ml of ice water, it is extracted twice with ethyl acetate, and the combined organic extracts are dried over sodium sulfate and evaporated. The crude product obtained is passed through a silica gel column (particle size: 0.06-0.2 mm, eluent:

Methylene chloride / ethanol = 24.Ί), yield: 2.3 g (79.3% of theory),

Oil, Rr value: 0.6 (silica gel: methyl ethyl ketone / xylene = 1: 1) C ₂₇ H ₂₈ N ₂ O ₂ (412.53)

Calc .: C, 78.61, H, 6.84, N, 6.79

Found .: C78.43 H 6.76 N 7.01

The following compound is obtained analogously:

4 '- [(2-n-butyl-7-n-butylsulfonamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid ethyl ester oil, Rr value: 0.50 (silica gel: methylene chloride / ethanol = 10: 1 )

Example 71

4 '- [(2-n-Buiyl-benzimidazl-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-l (2-n-butylbenzimidazole Ί-yl-methyllbiphenyl) -carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 62.3% of theory,

Melting point: 214-215 ° C

C ₂₆ H ₂₄ N ₂ O ₂ (38 <"48)

Calc .: C 78.10 H 6.29 N 7.29

Gef .: C77.93 H6,21 N7,39

Example 72

4 '- [(6-Benzylamino-2-n-butyl-benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid 1.30 g (2.5 mmol) 4' - [(6-benzylamino-2-n-butyl) butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid ethyl ester are dissolved in 20 ml of ethanol, treated with 20 ml of 2N sodium hydroxide solution and boiled for 2 hours at reflux. After cooling to room temperature, the solution is diluted with water to 500 ml and acidified with glacial acetic acid to pH5. The thus precipitated precipitate is filtered off with suction, suspended in acetone, nocnmals suction filtered and dried in vacuum at 9O ⁰ C.

Yield: 1.10 g (89.4% of theory), Melting point: 250-251 ⁰ C

C ₃₂ H ₃₁ N ₃ O ₂ (489.62)

Calc .: C78.50 H6.38 N8.58

Found: C 78.30 H 6.49 N 8.71

The following compound is obtained analogously:

4'-I (2-n-butyl-7-cyclohexylaminocarbonylamino-benzimidazol-1-yl methyl] biphenyl-2-carboxylic acid Melting point: 278-279 ⁰ C (dec).

Example 73 4 '- [(2-n-butyl-4-methyl-7-hydroxy-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid hydrate

Prepared analogously to Example 72 from 4 '- [(2-n-butyl-4-methyl-7-hydroxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

methyl ester and 2N sodium hydroxide solution in ethanol.

Yield: 55.1% of theory, Melting point: 313-315 ⁰ C

C ₂₆ H ₂₆ N ₂ O ₃ x H ₂ O (432.52)

Calc .: C 72.20 H 6.53 N 6.43

Found: C, 72.43, H, 6.30, N, 6.34

Example 74

4 '- [(2-n-butyl-4-methyl-7-hydroxy-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid tert-butyl ester Prepared analogously to Example 57 of 4' - [(2- n-butyl-4-methyl-7-benzyloxybenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and hydrogen in the presence of palladium hydroxide on carbon in methanol.

Yield: 80.0% of theory, Melting point: 214-216 ⁰ C

C ₃₀ H ₃₄ N ₂ O ₃ (470.62)

Calc .: C 76.57 H 7.28 N 5.95

Gef .: C76.83 H7,12 N6.00

Example 75 Prepared analogously to Example 56 from 3-amino-2 - [(2-tert-butoxycarbonyl-biphenyl-4'-yl) -methyllaminotoluene and valeric acid. Yield: 28.6% of theory,

Melting point: 231-233 ° C

C ₂₆ H ₂₆ N ₂ O ₂ x H ₂ O (416.52)

Calc .: C 74.98 H 6.78 N 6.73

Gef .: C74.89 H6.52 N6,85

Example 76

4 '- [(6-Amlno-2-n-butyl-benzimldazol-1-yl) methyl] biphenyl-2-carbons8ure ditrifluoroacetate

Prepared analogously to Example 9 from 4 '- [(6-amino-2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid. Yield: 72.5% of theory, Melting point: 72-74 ⁰ C

C ₂₆ H ₂₆ N ₃ O ₂ χ 2CF ₃ COOH (627.54)

Calc .: C 55.51 H 4.34 N 6.70

Found: C 55.70 H 4.61 N 6.55

Example 77

4 '- [(5-Amino-2-n-butylbenzitnidazol-1-yl) -mothyl] biphenyl-2-carboxylic acid-ditrillo-chloro-6: ₁ Prepared analogously to Example 9 from 4'- (5-amino-2 -n-butyl-benzimidazol-1-yl-methyl-biphenyl-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 45.9% of theory, Melting point: 64-66 ⁰ C C ₂₆ H ₂₅ N ₃ O ₂ x 2 CF ₃ COOH (627.54)

Lor .: C 55.51 H 4.34 N 6.70

Found: C 55.66 H 4.42 N 6.54

Example 78

4 '- [(2 x n x butyl-5- (n · butylaminocarbonylamino) -bθnzimidazol · 1-yl) · methyl] biphenyl-2 · · carbons8ure sθmitrifluoracetat

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-5- (n-butyl-aminocarbonylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 84.2% of theory, melting point: 165-167 ° C

C ₃₀ H ₃₄ N ₄ O ₃ X '/ 2CF ₃ COOH (555.64)

Calc .: C 67.01 H 6.26 N 10.08

Found: C66.88 H, 6.51 N, 9.89

Example 79

4 '- [(2-n-butyl-6-phenylamlnocarbonylamino-benzimid8zol-1-yl) methyl] blphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-phenylaminocarbonylaminobenzimidazol-1-yl) methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 92.6% of theory,

Melting point: 281-283 ° C

C ₃₂ H ₃₀ N ₄ O ₃ (518.61)

Calc .: C74.11 H 5.83 N 10.80

Gef .:. C, 73.93, H, 5.83, N, 10.58

Example 80

4 '- [(2-n-butyl-e-r / clohexylaminocarbonylamino-benz <-imidazol-1-yl) methyl] biphenyl-2-carboxylic acid trlfluoracetat

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-cyclohexylaminocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 86.5% of theory, Melting point: 199-200 ⁰ C C ₃₂ H ₃₈ N ₄ O ₃ x CF ₃ COOH (638.68)

Calc .: C 63.94 H 5.84 N 8.77

Gef .: C64.12 H6,15 N9,01

Example 81

4 '- [(2-n-butyl-5-butanoylamlno-benzlmidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-5-butanoyl-amino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 93% of theory, Melting point: 163-165 ° C

C ₂₃ H ₃₁ N ₃ O ₃ (469.59)

Calc .: C74.18 H6.65 N8.95

Found: C74.13 H 6.67 N 8.74

Example 82

4 '- [(2- (4-hydroxyphenyl) -benzimldazol-1-yl) methyl] blphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2- {4-hydroxyphenyl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester

trifluoroacetic / methylene chloride.

Yield: 87.3% of theory,

Melting point: 251-253 ⁰ C

C ₂₇ H ₂₀ N ₂ O ₃ (420.47)

Calc .: C 77.13 H 4.79 N 6.66

Found: C, 76.98, H, 4.83, N, 6.62

Example 83

4 '- [(2- (4-n-butoxyphenyl) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2- (4-n-butoxyphenyl) benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

trifluoroacetic / methylene chloride.

Yield: 85.2% of theory,

Melting point: 246-248 ° C

C ₃ ) H ₂₈ N ₂ O ₃ (476.58)

Calc .: C, 78.13, H, 5.92, N, 5.88

Found: C, 78.33, H, 5.76, N, 5.67

Example 84

4 '- [(2-n-butyl-6-chloro-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-chlorobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and

Trifluoroacetic acid / methylene chloride.

Yield: 63.6% of theory, Melting point: 220-222 ⁰ C.

C ₂₆ H ₂₃ CIN ₂ O ₂ (418.92)

Calcd .: C, 71.68, H, 5.53, N, 6.69, Cl, 8.46

Found: C, 71.81, H, 5.64, N, 6.69, Cl, 8.39

Example 85

4 '- [(2-n-butyl-6-methyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-methylbenzimidazole-1 -yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 70.6% of theory, Melting point: 219-221 ⁰ C

C ₂₆ H ₂₆ N ₂ O ₂ (398.51)

Calc .: C 78.36 H 6.58 N 7.03

Found: C, 78.49, H, 6.53, N, 6.98

Example 86

^ U-S-n-butyl-methansulfonamlno benzimldazoM-yllrnethyllblphenyl ^ -carbonsaure

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-5-methanesulfonaminobenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 75.7% of theory, Melting point: 242-244 ⁰ C

C ₂₈ Hj ₇ N ₃ O ₄ S (477.59)

Calc .: C 65.39 H 5.70 N 8.80 S 6.71

Found: C 65.52 H 5.65 N 8.55 S 6.51

Boispiel 87

4 '- [(7-n-butanoyloxy-2-n-butyM-methyl-benzlmIdazol-1-yl) -mathyl] blphenyl-2-carboxylic acid

Prepared analogously to Example 60 from 4 '- [(2-n-butyl-7-hydroxy-4-methylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid and Butyric acid chloride in pyridine. Yield: 29.1% of theory, Melting point: 240-242 ⁰ C

C ₃₀ H ₃₂ N ₂ O ₄ (484.60)

Calc .: C 74.63 H 6.66 N 5.78

Found: C 74.20 H 6.76 N 5.87

Example 88

4 '- [(2-n-butyl-6-ethoxycarbonylamlno-benzlmldazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Beis M 9 from 4 '- [(2-n-butyl-6-ethoxycarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 88.2% of theory, Melting point: 240-242 "C

C ₂₈ H ₂₉ N ₃ O ₃ (471.55)

Calc .: C 71.32 H 6.20 N 8.91

Found: C, 71.06, H, 6.36, N, 9.04

Example 89

4 '- [(2-n-butyl-6-lsopropylsulfonamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-isopropylsulfonamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 91.5% of theory, Melting point: 155-157 ⁰ C

C ₂₈ H ₃₁ N ₃ O ₄ S (505.63)

Calc .: C 66.51 H 6.18 N 8.31 S 6.34

Found: C 66.26 H 6.33 N 8.34 S 6.43

Example SO

4 '- [(2-n-Butyl-4-nitro-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4'-l (2-n-butyl-4-nitro-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid / methylene chloride. Yield: 84.6% of theory, Melting point: 238-240 ⁰ C

C ₂₅ H ₂₃ N ₃ O ₄ (429.48)

Calc .: C 69.92 H 5.40 N 9.78

Found: C, 69.85, H, 5.43, N, 9.67

Example 91

4 '- [(2-n-butyl-4-butanoylamlno-benzlmIdazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-4-butanoylamino-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid

tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 96.1% of theory, Melting point: 270-271 ⁰ C

C ₂₉ H ₃₁ N ₃ O ₃ (469.58)

Calc .: C 74.18 H 6.65 N 8.95

Found: C 74.02 H 6.74 N 8.99

Example 92

4 '- [(2-n-butyl-4-ethylaminocarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-4-ethylaminocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl

2-carboxylic acid tert.butylesterundTrifluoressigsäure / methylene chloride.

Yield: 87.5% of theory,

Melting point: 344-346 ⁰ C (dec.) C ₂₈ H ₃₀ N ₄ O ₃ (470.57)

Calcd .: C, 71.47, H, 6.43, N, 11.91

Found .: C 71.51 H 6.29 N 11.48

Example 93

4 '- [(2- (3-Pyridyl) -benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2- (3-pyridyl) -benzimidazol-1-yl ) -methyllbiphonyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 73.3% of theory, Melting point: 24 ^ -251 ⁰ C.

C ₂₆ H ₁₉ N ₃ O ₂ (405.46)

Calc .: C 77.02 H 4.72 N 10.36

Found: C 76.85 H 4.72 N 10.15

Example 94

4 '- [{2-n-butyl-5-methylbenzimidyl-1-yl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5-methylbenzyl-benzimidazole -1-yl) -methyl) biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 58.8% of theory, m.p .: 188-19O ⁰ C (dec.) C ₂₆ H ₂₆ N ₂ O ₂ (398.51)

Calc .: C 78.36 H 6.58 N 7.03

Found: C 78.21 H 6.62 N 6.98

Example 95

4 '- [(2-n-butyl-6-dimethylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid trifluoroacetate Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-dimethylamino -benzirnidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 65.4% of theory, C ₂₇ H ₂₉ N ₃ O ₂ x CF ₃ COOH (541.58)

Ben: C 64.31 H 5.58 N 7.76

Found: C, 64.53, H, 5.66, N, 7.89

Example 96

4 '- [(2 × n-butyl-5- (tert-butoxycarbonylamino-aco-thyl) -benzimidazol-1-yl) -methyl] -biphino-2-carboxylic acid θ Prepared analogously to Example 72 from 4'-l (2-n-butyl -5- (tert-butoxycarbonylamino-acetamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid ethyl ester and 2N sodium hydroxide solution.

Yield: 16.7% of theory, m.p .: 149-151 "C

C ₃₂ H ₃₆ N ₄ O ₆ (556.66)

Calc .: C 69.05 H 6.52 N 10.06

Found .: C 69.12 H 6.32 N 9.87

Example 97 4 '- [(2-n-butyl-5,6-dimethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5 , 6-Dimathyl-benzimidazol-1-yl) -methylJbiphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 17.5% of theory, Melting point: 222-225 ⁰ C.

C ₂₇ H ₂₈ N ₂ O ₂ (412.50)

Calc .: C 78.62 H 6.84 N e, 79

Found: C 78.36 H 6.90 N 6.83

Example 98

4 '- [(2- (2,2-Dimethylpropyl) -5,6-dimethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-i (2- (2, 2-Dimethylpropyl) -5,6-dimethylbenzimidazole-1-yl-methyllbiphenyl -carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 45% of theory,

Melting point: from 115 ° C (amorphous) C ₂₈ H ₃₀ N ₂ O ₂ (426.60)

Calc .: C 78.83 H 7.09 N 6.57

Found: C 78.64 H 7.11 N 6.89

Example 99 4 '- [(2-Benzyl-5,6-dimethyl-benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-benzyl-5,6-dimethyl benzimidazol-1-yl-methyllbiphenyl-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 68% of theory,

Melting point: 252-255 ⁰ C

C ₃₀ H ₂₆ N ₂ O ₂ (446.60)

Calcd .: C, 80.69, H, 5.87, N, 6.27

Found: C, 80.94, H, 5.76, N, 5.97

Example 10C

Prepared analogously to Example 9 from 4'- | (2- (2-methylbutyl) -5,6-dimethyl-ben2imidazol-1-yl) -methyl | biphenyl-2-carboxylic acid tert.butylester and Trifluoressigsäurt in methylone chloride. Yield: 57% of theory, melting point: 211-215 ° CC ₂₈ H ₃₀ N ₂ O ₂ (426.60)

Calc .: C 78.84 H 7.09 N 6.57

Found: C, 78.67, H, 7.24, N, 6.43

Example 101

4M (2-Cyclohexylmethyl) -5,6-dimethylbenzimidazol-1-yl) -methyl] -phenyl-2-carboxylic acid Prepared analogously to Example 9 from 4 '- [(2-cyclohexylmethyl) -5,6-dimethylbenzimidazole] Tert-butyl) and trifluoroacetic acid in methylene chloride.

Yield: 31% of theory,

Melting point: 199-201 ⁰ C

C ₃₀ H ₃₂ N ₂ O, (452.60)

Calc .: C 79.61 H 7,13 N 6,19

Found .: C 79.45 H 7,17 N 6,06

Example 102

4 '- [(2-Cyclohexylmethyl-5,6-dichloro-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2-cyclohexylmethyl-5,6-dichloro-benzimidazole -1-yl) -methyllbiphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 39% of theory,

Melting point: 219-222 ⁰ C

C ₂₈ H ₂₆ CI ₂ N ₂ O ₂ (493.40)

Calc .: C 68.16 H 5.31 N 5.68 Cl 14.37

Found: C, 67.97, H, 5.29, N, 5.52, Cl, 14, 12

Example 103

4 '- [(2- (2-methylbutyl) -naphtho [2,3-dl-midazol-1-yl) -methyl] -phenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2- (2- Methylbutyl) -naphtho [2,3-d] imidazole-1-yl-methyllbiphenyl -carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 64% of theory,

Melting point: 206-208 ⁰ C

C ₃₀ H ₂₈ N ₂ O ₂ (448.60)

Calcd .: C, 80.33, H, 6.29, N, 6.25

Found: C, 80.20, H, 6.36, N, 6.24

Example 104

4 '- [(2-n-Propylnaphtho [2,3-d] imidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-propylnaphtho [2,3-d] imidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride. Yield: 85% of theory,

Melting point: 269-272 ⁰ C

C ₂₈ H ₂₄ N ₂ O ₂ (420.50)

Calcd .: C, 79.98, H, 5.75, N, 6.66

Found: C, 79.87, H, 5.68, N, 6.48

Example 105

4 '- [(2-n-butyl-5,6-dichloro-benzimidazol-1-yl) -methyl] biphenyl-2-ca: bonsäure Prepared analogously to Example 9 from 4'-I (2-n-butyl-5 , 6-dichloro-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 50% of theory,

Melting point: 237-239 ⁰ C

C ₂₆ H ₂₂ Cl ₂ N ₂ O ₂ (453.40)

Calc .: C 66.23 H 4.89 N 6.18 Cl 15.64

Found: C, 66.10 H, 4.82, N, 6.05, Cl, 15.42

Example 106

4 '- [(2-Cyslohexylmethyl-5,6-dimethoxy-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-cyclohexylmethyl-5,6-dimethoxybenzimidazole -1-yl) -methyl) biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 45% of theory,

Melting point: 245-247 ⁰ C

C ₃₀ H ₃₂ N ₂ O ₄ (484.60)

Calc .: C 74.36 H 6.66 N 5.78

Found: C 74.11 H 6.58 N 6.02

Example 107

4 '- [(2-n-butyl-5,6-dimethoxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5,6- dimethoxy-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Ausboute: 52% of theory,

Melting point: 257-259 ⁰ C

C ₂₇ H ₂₈ N ₂ O ₄ (444.50)

The .: C 72.95 H 6.35 N 6.30

Found: C 72.77 H 6.26 N 6.49

Example 108

4 '- [(2-Cyclopentylmethyl-5,6-dlmethoxybenzlmldazol-1-yl) -methyl] biphenyly-2-carboxylic acid Prepared analogously to Example 9 from 4M (2-cyclopentylmethyl-5,6-dimethoxy-benzimidazole) Tert-butyl) and trifluoroacetic acid in methylene chloride.

Yield: 47% of theory,

Melting point: 233-234 ° C

CMH ₃₀ N ₂ O ₄ (470.60)

Calc .: C 74.02 H 6.43 N 5.95

Found: C 73.90 H 6.56 N 6.18

Example 109

4 '- [(2- (3-Methylbutyl) -5,6-dlmethoxy-benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-I (2- (3-methylbutyl) -5,6-dimethoxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 39% of theory,

Melting point: 237-239 ⁰ C

C ₂₈ H ₃₀ N ₂ O ₄ (458, υΟ)

Calc .: C 73.34 H 6.59 N 6.11

Found: C 73.50 H 6.48 N 6.02

Example 110

4 '- [(2-Cyclohexyl-5,6-dimethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-cyclohexyl-5,6-dimethylbenzimidazole -1-yl) -methyl) biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 27% of theory, Melting point: 240-242 ⁰ C

C ₂₉ H ₃₀ N ₂ O ₂ (438.60)

Calc .: C 79.42 H 6.89 N 6.39

Found .: C 79.30 H 7.02 N 6.39

Example 111

4 '- [(2- (1-Butyn-4-yl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2- (1-butyne) 4-vl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 55% of theory,

Melting point: 218-221 ⁰ C

C ₂₆ H ₂₀ N ₂ O ₂ (380.50)

Calc .: C, 78.93, H, 5.30, N, 7.36

Found: C, 78.97, H, 5.24, N, 7.31

Example 112

4 '- [(2-cyclopentyl-5,6-dimethyl-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-cyclopentyl-5,6-dimethylbenzimidazole -1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 75% of theory,

Melting point: 262-265 ⁰ C

C ₂₈ H ₂₈ N ₂ O ₂ (424.50)

Calc .: C 79.22 H 6.65 N 6.60

Found: C, 78.99, H, 6.54, N, 6.67

Example 113

4 '- [(2-n-butyl-5-and 6-fluoro-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-5- and e-fluoro-benzimidazoM-yD-methyllbiphenylcarboxylic acid tert-butyl ester

and trifluoroacetic acid in methylene chloride.

Yield: 80% of theory, Melting point: 167-169 ⁰ C

C ₂₆ H ₂₃ FN ₂ O ₂ (402.50)

Calc .: C 74.61 H 5.76 N 6.96

Found: C 74.57 H 5.77 N 7.05

Example 114

4 '- [(2-n-butyl-5- and 6-benzoyl-benziniid8zol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5-benzoyl - and e-benzoyl-benzimidazol-i-yU-methyllbiphenyl ^ -carboxylic acid tert.butylester and trifluoroacetic acid in methylene chloride.

Yield: 58.5% of theory, Melting point: 180-182 ⁰ C.

C ₃₂ H ₂₈ N ₂ O ₃ (488.60)

Boron: C7C.67H 5.78N 5.73

Found: C, 78.75, H, 5.74, N, 5.63

Example 115

4 '- [(2-n-Butyl-5- and e-trifluoromethyl-benzimidazol-1-yl-methyl-1-biphenylcarboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5- and e-trifluoromethyl benzimidazole-i-yO-methyl-biphenyl-carboxylic acid tert -butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 85% of theory,

Melting point: 172-174 ° C

C ₂₆ H ₂₃ F ₃ N ₂ O ₃ (452.50)

Calc .: C 69.01 H 5.12 N 6.19

Found: C 69.10 H 5.24 N 6.11

Example 116

4 '- [(2-n-butyl-4-cyano-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2-n-butyl-4-cyano-benzimidazole -1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 72% of theory,

Melting point: 190-192 ⁰ C

C ₂₆ H ₂₃ N ₃ O ₂ (409.49)

Calc .: C 76.26 H 5.66 N 10.62

Found: C 76.01 H 5.72 N 10.51

Example 117

4 '- [(2-n-Butyl-5 and 6-n-butyl-aminocarbonylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5 - and 3-n-butylaminocarbonyl-benzimidazol-1-yl) -iriethyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 69% of theory,

Melting point: from 88 ° C (decomp.) C30H33N3O3 x Vz CF3COOH (483.60)

Calc .: C 68.88 H 6.25 N 7.77

Found: C 68.65 H 6.32 N 7.71

Example 118

4 '- [(2-n-Butyl-6-carboxy-benzimidazol-1-yl) -methyl] -b-phenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-carboxy -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 91% of theory,

Melting point: 315-32O ⁰ C (dec.) C ₂₆ H ₂₄ N ₂ O ₄ (428.50)

Calcd .: C, 72.88, H, 5.65, N, 6.54

Found: C, 72.74, H, 5.66, N, 6.55

Example 119

4 '- [(2-n-Butyl-5-carboxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-t (2-n-butyl-5-carboxy-benzimidazole -1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 63% of theory,

Melting point: 247-248 ⁰ C

C ₂₆ H ₂₄ N ₂ O ₄ (428.50)

Calcd .: C, 72.88, H, 5.65, N, 6.54

Found: C, 72.76, H, 5.52, N, 6.52

Example 120

4 '- [(2-n-butyl-6-aminocarbonyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-aminocarbonyl-benzimidazol-1-yl-methyljbiphthenyl] -carboxylic acid

tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 45% of theory,

Melting point: 243-244 ° C

C ₂₆ H ₂₆ N ₃ O ₃ X '/ 2H ₂ O (436.51)

Calc .: C 71.54 H 6.00 N 9.63

Found: C, 71.34, H, 6.16, N, 9.45

Example 121

^ (Zn-butyl-s-aminocarbonyl-benzimidazol-1-yl-methyl-biphenyl-carboxylic acid Prepared analogously to Example 9 from 4 '- [(2-n-butyl-5-aminocarbonyl-benzimidazol-1-yl) -methyl] biphenyl -2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 55% of theory,

Melting point: 227-228 ⁰ C

C ₂₆ H ₂₆ N ₃ O ₃ x V ₂ H ₂ O (436.51)

Calc .: C 71.54 H 6.00 N 9.63

Found: C, 71.42, H, 5.94, N, 9.46

Example 122

4 '- [(2-n-Butyl-5 and 6-cyano-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5 and 5-yl] Tert-Butyl 6-cyano-benzimidazol-i-yl-methyllbiphenylcarboxylate and trifluoroacetic acid in methylene chloride.

Yield: 70% of theory,

Melting point: 214-215 ⁰ C

C ₂₆ H ₂₃ N ₃ O ₂ (409.50)

Calc .: C 76.26 H 5.66 N 10.26

Found: C 76.06 H 5.44 N 10.11

Example 123

4 '- [(2-n-Butyl-5- (1H-tetrazol-5-yl) -benzlmldazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n Butyl-5- (1H-tetrazol-5-yl) -benzimidazol-1-yl-methyllbiphenyl-carboxylic acid tert -butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 66% of theory,

Melting point: 249-25O ⁰ C

C ₂₆ H ₂₄ N ₆ O ₂ (452.50)

Calc .: C 69.01 H 5.35 N 18.57

Found: C 68.92 H 5.48 N 18.78

Example 124

4 '- [(2-n-Butyl-5 and 6- (1H-tetrazol-5-yl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2 -n-butyl-5- and e -dH-tetrazol-S-yU-benzimidazoM-yO-methyllbiphenyl-1-carbonic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 55% of theory,

Melting point: from 220 ° C (decomp.)

C ₂₆ H ₂₄ N ₆ O ₂ (452.50)

Calc .: C 69.01 H 5.35 N 18.57

Gef: C68.92 H5,41 N 18,35

Example 125

4 '- [(2-n-butyl-5-dimethylaminosulfonyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Prepared analogously to Example 9 from 4' - [(2-n-butyl-5 -dimethylaminosulfonyl-3-N-oxido-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester by catalytic hydrogenation in the presence of Raney nickel and subsequent reaction with trifluoroacetic acid in methylene chloride.

Yield: 92% of theory,

Melting point: 24O-242 ° C

C ₂₇ H ₂₉ N ₃ O ₄ S (491.60)

Calc .: C 65.97 H 5.95 N 8.55 S 6.52

Found: C65.41 H6.09 N8.46 S6.60

Example 126

4 '- [(2-n-Butyl-5- and e -methoxycarbonyl-benzimidazol-1-yl-methyl] -IIH-tetrazol-1-yl-1-biphenyl (0.71g) (1, OmMoI) 4' - [(2-n Butyl-5-and e-methoxycarbonyl-benzimidazol-i-yD-methyll ^ -d-triphenylmethyl-tetrazol-S-yl) biphenyl be with 25 ml of 5% methanolic ammonia in a pressure vessel at 125-130 ⁰ C for 16 hours After cooling, the solvent is distilled off, the residue is taken up in dilute acetic acid and extracted three times with ethyl acetate, the combined ethyl acetate phases are washed with brine, dried over sodium sulfate, concentrated and the residue is purified over a silica gel column with methylene chloride / ethanol 25: 1 as eluent.

Yield: 0.34 g (73% of theory),

Melting point: 136-138 ⁰ C

C ₂₇ H ₂₆ N ₆ O ₂ (466.56)

Calc .: C 69.50 H 5.57 N 17.98

Found .: C 69.42 H 5.33 N 17.44

Example 127

4 '- [(2-n-butyl-5- and 6-n-butyl-aminocarbonyl-benzimidazol-1-vl) -methyl] -2- (1H-tetrazol-5-yl) -phenol>.' 216 mg (1.05 mmol) of dicyclohexylcarbodiimide and 141 mg (1.05 mmol) of 1-hydroxybenzotriazole hydrate are dissolved in 30 ml of acetonitrile and mixed with 452 mg (1.0 μmol) 4 '- [(2-n-butyl-5- and 6-carboxy benzimidazol-1-yl) methyl] -2- (1H-tetrazol-5-yl) -biphenyl. After 30minütiyem stirring at room temperature 146mg (2.0OmMoI) n-butylamine are added and the reaction mixture stirred for 4 hours at room temperature. The precipitated dicyclohexylurea is filtered off and the

Concentrated filtrate. The residue obtained is taken up in methylene chloride and washed once each with 5% sodium bicarbonate Solution and brine solution. After renewed concentration, the end product is obtained by chromatography

a silica gel column (eluent: methylene chloride / ethanol = 25: 1).

Yield: 95 mg (19% of theory). Melting point: 245-247 ⁰ C

C ₃₀ H ₃₃ N ₇ O (507.63)

Calc .: 071.00 H 6.50 N 19.30

Found: C 70.77 H 6.66 N 19.36

Example 128

4 '· [(2 · η · ΒϋΙνΙ · 5 · and e-aminocarbonyl-benzimidazoM-ylJ-melhylJ ^ -HH-tetrazole-S-yO-biphenyl

Prepared analogously to Example 127 from 4'-I (2-n-butyl-5-and e-carboxy-benzimidazol-1-yl-methyll ^ -d H-tetrazol-5-yl) -biphenyl. Yield: 17% of theory, Melting point: 225-227 ⁰ C

Cj ₆ H ₂₆ N ₇ O (451.62)

Calc .: C69.98 H5.54 N21.62

Found: C 69.85 H 5.30 N 21.48

Example 129

4 '- [(2-n-butyl-5 · and 6-hydroxymethyl-benzimidazol-1-yl) -methyl] 2 (1H-tetrazcl-5-yl) biphosyl-452mg (1.0OmMoI) 4' - [(2-n Butyl-5- and 6-carboxy-benzimidazol-1-yl) -methyl-2- (1H-tetrazol-5-yl) -biphenyl are dissolved in 20 ml

Dissolved tetrahydrofuran and treated with 67.0mg (1.75 mmol) of lithium aluminum hydride. The suspension is 4 hours at 4O ⁰ C.

stirred and then decomposed with 20 ml of water / ethanol (1: 1). After filtration through kieselguhr is concentrated and on

Silica gel (eluent: methylene chloride / ethanol = 9: 1 with the addition of 1% ammonia) Chromatography «. Yield: 90 mg (21% of theory), Melting point: 173-175 ⁰ C

C ₂₆ H ₂₆ N ₆ O (438.54)

Calc .: C 71.50 H 5.96 N 19.20

Gef .: C71.32 H6.06 N 19.02

The following compound is obtained analogously:

4 '- [(2-n-butyl-5-und6- (n-butylaminomethyl) -benzoimidazol-1-yl) -methyll-2- (1H-tetrazol-5-yl) biphenyl Melting point: 146-149 ⁰ C.

Example 130

4 '- [(2-rc-Butyl-5 and 6-carboxy-benzimidazol-1-yl) -methyl] -2- (1H-tetrazol-5-yl) -biphenyl2,1 g (3, OmMoI) 4' - [ (2-n-Butyl-5 and e-methoxycarbonyl-benzimidazol-i-yD-methyll ^ -d-triphenyl-methyl-tetrazol-S-yl) -biphenyl are dissolved in 100 ml of ethanol with warming, at 4O ⁰ C with 25 ml of 1N sodium hydroxide added and 60 hours at

Cleared iperatur stirred. The reaction solution is concentrated, the residue obtained is dissolved in ice-water and brought to 2N Acetic acid to pH4-5. The precipitated crude product is filtered off, washed with water until neutral and over a Silica gel column (eluent: methylene chloride '' ethanol - 9: 1 with the addition of 1% glacial acetic acid). Yield: 0.65 g (48% of theory), Melting point: 188-19O ⁰ C

C ₂₆ H ₂₄ N ₆ O ₂ (452.60)

Calc .: C 68.80 H 5.53 N 18.52

Found: C, 68.63, H, 5.34, N, 18.65

Example 131

4 '- [(2-n-butyl-7-cyano-l-benzlmidazol-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-7-cyano-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid in methylene chloride. Yield: 68% of theory, Melting point: 190-192 ⁰ C

C ₂₆ H ₂₃ N ₃ O ₄ (409.49)

Calc .: C 76.26 H 5.66 N 10.26

Found: C, 75.99 H, 5.4 'N, 10.25

Example 132

4 '- [(2-n-butyl-5,7-difluoro-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-5,7-difluorobenzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid in methylene chloride. Yield: 0.49% of theory, Melting point: from 155 ⁰ C (amoprh)

C ₂₆ H ₂₂ F ₂ N ₂ O ₂ (420.40)

Calcd .: C, 71.41, H, 5.27, N, 6.66

Found: C, 71.38, H, 5.09, N, 6.39

Example 133

4 '- [(2-n-butyl-5-acetyl-benzimidazTl-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4'-l (2-n-butyl-5-acetyl-bt; nzirr, iL'azol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid in methylene chloride.

Yield: 59.5% of theory,

Melting point: 182-184 ⁰ C

C ₂₇ H ₂₆ N ₂ O ₃ (426.50)

Ref .: C76.03 H6.14 N6.57

Found: C75.89 H 6.35 N 6.33

Example 134

4 '- [(2-cyclohexylmethyl-5,6-dihydroxy-benzimidazol-1-yl) methyl] blphenyl-2-carboxylic acid

To a suspension of 242 mg (0.5 mmol) of 4'-l (2-cyclone-methylmethyl-5,6-dimethoxy-benzimidazol-1-yl) -methyl] -biphenyl-2-

carboxylic acid in 25 ml of dichloromethane are added dropwise at -5 ° C, 0.29 ml (3 mmol) boron tribromide. When the addition is complete, the cooling bath is removed and stirred for 5 hours at room temperature. With ice-cooling, 20 ml of methanol are then added, then the reaction mixture is evaporated to dryness and the residue is suspended in 10 ml of water with stirring. The precipitated crude product is filtered off with suction, washed with additional 10 ml of water, dried and over a

Silica gel column (eluent: dichloromethane / ethanol = 9: 1) chromatographed. Yield: 51 mg (22% of theory), Melting point: amorphous

C ₂₈ H ₂₈ N ₂ O ₄ (456.50)

Calc .: C73.66 H 6,18 N 6,14

Found: C, 73.79, H, 6.31, N, 6.22

The following compounds are obtained analogously:

4'| (2-n-butyl-5-hydroxy-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid Melting point: 306-307 ⁰ C.

4 '- [(2-n-butyl-4-hydroxy-benzimidzaol-1-yl) methyl] biphenyl-2-carboxylic acid Melting point: 292-293 ⁰ C.

4 '- [(2-n-butyl-7-hydroxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid Melting point: 295-297 ⁰ C.

Example 135 4 '- [(2- (3-Methylbutyl) -5-me5hoxy-6-hydroxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid and 4' - [(2- (3-methylbutyl) - 5-hydroxy-6-methoxy-benziinldazol-1-yl) methyl] biphenyl-2-carboxylic acid

To a suspension of 600 mg (1.3 mmol) 4 '- [(2- (il-methylbutyl) -5,6-dimethoxybenzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid in 50 ml of dried dichloromethane are added 3 g of aluminum trichloride and the mixture is refluxed for 15 minutes. The solvent is then distilled off, the residue is filtered off with suction, washed with 30 ml of water and dried. After chromatography over silica gel (eluent: dichloromethane / ethanol = 9: 1), 360 mg (62% of theory) of a mixture of the isomeric products are obtained.

To separate the isomers, 230 mg of the mixture are again chromatographed over Kesel gel (eluent: Dichloromethane / ethanol = 11: 1). This gives 80 mg of 4 '- ((2- (3-methylbutyl) -5-methoxy-6-hydroxy-benzimidazol-1-yl) -

methyl] biphenyl-2-carboxylic acid (melting point: 189-192 ⁰ C) C ₂₇ H ₂₈ N ₂ O ₄ (444.50)

Calc .: C 72.95 H 6.35 N 6.30

Gef .: C72.84 H6.32 N6,19

and 30 mg of 4 '- [(2- (3-Me ^f .hylbutyl) -5-hydroxy-6-methoxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid (melting point:

C ₂₇ H ₂₈ N ₂ O ₄ (444.50)

Calc .: C72.95 H6.35 N6.30

Gef .: C73.13 H6.39 N6,41

Example 136

4 '- [(2-n-butyl-7-n-propylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid ethyl ester 2.0g (4.7moles) 4' - ((7-amino) Ethyl 2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylate are dissolved in 50 ml of ethanol and treated with 0.53 ml (7.5 mmol) of propionaldehyde and 0.5 g of 10% of palladium Charcoal added and 2 hours

Room temperature and hydrogenated 5bar hydrogen pressure. The catalyst is then filtered off with suction and the solvent in Vacuum removed. The oily residue is purified over an alumina column (neutral, activity H-III), with cyclohexane / Methylene chloride = 3: 1 and 1: 1 eluted. The appropriate fractions are combined and concentrated. Yield: 2.0 g (90.9% of theory),

Oil, Rp value: 0.50 (silica gel: methylene chloride / ethanol) = 19: 1) Analogously, the following compounds are obtained:

4 '- [(2-n-butyl-5-n-pentylaminobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Ri value: 0.45 (aluminum oxide, methylene chloride) r'- ((2-n-Butyl-6-n-pentylamino-berizimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rr value: 0.40 (silica gel: methyl ethyl ketone / xylene = 1: 1) 4'- | (2-n-Butyl-6-n-butylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rp value: 0.50 (silica gel: methyl ethyl ketone / Xylene = 1: 1) tert-butyl 4'-l (2-n-butyl-6- (2-cyclohexyl-ethyll-tiino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate, Rp value: 0, 40 (silica gel: ethyl acetate / petroleum ether = 60:40) 4 '- [(2-n-butyl-6- (cis-undtrans-decahydro-naphth-2-yl-amino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylate

Oil, Rr value: 0.65 (alumina plate: petroleum ether / ethyl acetate = 9: 1) Example 137

4 '- [(2-n-Butyl-7-n-propylamino-benzl-mldazol-1-yl) -methyl] -biphanyl-2-carboxylic acid Prepared analogous to Example 72 from 4' - [(2-n-butyl-7-n -propyl-amino-benzimidazol-1-yl) -methyl] biphenyl-2-crabonsäureethylester and 2 N sodium hydroxide solution / ethanol.

Yield: 85.7% of theory, Melting point: 262-263 ⁰ C.

C ₂₈ H ₃ IN ₃ O ₂ (441.57)

Calc .: 076.16 H 7.08 N 9.52

Found: C 76.35 H 7.26 N 9.60

Example 138

4 '- [(2-n-Butyl-5 and 6-nltro-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-5 and 5-yl] Tert-Butyl 6-nitrobenzimidazole-1-yl-methyllbiphenylcarboxylic acid and trifluoroacetic acid in methylene chloride.

Yield: 54.4% of theory, Melting point: 223-224 ⁰ C.

Cj ₅ H ₂₃ N ₃ O ₄ (429.48)

Calc .: C 69.92 H 5.60 N 9.78

Gef .: C69.81 H5.47 N9,72

Example 139

4 ^ (2-n-Butyl-7-n-butylsulfonamino-benzimidazoM-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 72 from 4 '- [(2-n-butyl-7-n-butyl-sulfonamino ethylbenzimidazol-1-yl) -methyl) -biphenyl-2-carboxylate and sodium hydroxide solution in ethanol.

Yield: 94.7% of theory,

Melting point: 225-226 ⁰ C

C ₂₉ H ₃₃ N ₃ O ₄ S (519.66)

Calc .: C 67.03 H 6.40 N 8.09 S 6.17

Found: C 66.92 H 6.63 N 8.09 S 5.91

Example 140

4 '- [(2-n-butyl-5-n-pentylamino-banzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid hemitrifluoroacetate Prepared analogously to Example 9 from 4' - [(2-n-butyl-5- n-pentylamino-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 92.3% of theory, Melting point: 155-157 ⁰ C.

C ₃₀ H ₃₅ N ₃ O ₄ x '/ 2CF ₃ COOH (526.64)

Calc .: C 70.70 H 6.79 N 7.98

Found: C, 70.84, H, 6.94, N, 8.05

Example 141

4 '- [(2-n-Butyl-6-cyclohexylaminocarbonylamino-benzimidazol-1-yl) -methyl] -2-aminobiphenyl 2g (3.2moles) 4'- (2-n-butyl-5-cyclohexylaminocarbonylamino -bonzimidazol-1-yl) -methyl] -2-phthalimino-biphenyl are dissolved in 20 ml of methanol and 10 ml of dimethylformamide and stirred for 2 hours at room temperature after addition of 20 ml of 40% methylamine solution. It is evaporated to dryness in vacuo. The remaining residue is suspended in ether and the insoluble N-methyl-phthalimide is filtered off. The filtrate is evaporated to dryness in vacuo and purified over silica gel (particle size: 0.063-0.2 mm, eluant: methylene chloride with 0.5-2% ethanol). The product obtained is suspended in ether, filtered off with suction, washed with ether and dried in vacuo.

Yield: 1.37 g (85.6% of theory), Melting point: 209-211 ⁰ C.

C ₃ iH ₃₇ N ₅ O (495.68)

Calc .: C75,12 H7,52 N 14,13

Found: C75.33 H7.57 N 14.01

The following compound is obtained analogously:

4 '- ((2-n-butyl-7-hydroxy-4-methyl-benzimidazol-1-yl) -methyl] -2-amino-biphenyl m.p .: 249-250 ° C

Example 142

4 '- [(2-n-butyl-7-hydroxy-4-methyl-benzenimidazol-1-yl) -methyl] -2-aminomethyl-biphenyl 3.3 g (7.1 mmol) 4' - [(7 Benzyloxy-2-n-butyl-4-methyl-benzimidazol-1-yl) -methyl] -2-cyano-biphenyl are dissolved in 100 ml of methanol and in the presence of 0.5 g of palladium (10% on carbon) with 5 bar of hydrogen hydrogenated at room temperature. After 3 hours, the catalyst is filtered off. The filtrate is mixed with 20 ml of 20% ammonia in methanol and hydrogenated in the presence of 0.5 g Raney nickel with 5 bar of hydrogen at 70 ° C err.eut. After 4 hours, the catalyst is filtered off with suction and the filtrate is evaporated to dryness in vacuo. The crystalline crude product is suspended in ether, filtered off, washed with ether and dried in vacuo.

Yield: 2.6 g (92.8% of theory), Melting point: 207-212 ⁰ C.

C ₂₆ H ₂₉ N ₃ O (399.53)

Calc .: C78.16 H 7.32 N 10.52

Found: C 77.97 H 7.34 N 10.51

Example 143

4 '- [(2-n-Butyl-6-cyclohexylaminocarbolnylamino-benzyl) -azol-1-yl) -methyl] -2-trifluoroacetamino-biphenyl 0.35 g (0.7 mmol) 4' - [(2- n-Butyl-6-cyclohexylaminocarbonylamino-benzimidazol-1-yl) -methyl] -2-amino-biphenyl dissolved in 15 ml of methylene chloride and 0.85 ml (6.1 mmol) of triethylamine are cooled to -60 ° C and stirred added dropwise with 0.85 ml of trifluoroacetic anhydride in 2 ml of methylene chloride. It is allowed to rise to room temperature overnight and evaporated to dryness. The residue is purified over silica gel (eluent: methylene chloride with 0.5-2% ethanol). The collected eluates are evaporated, crystallized from ether / gasoline 60-80 ° C and dried in vacuo.

Yield: 0.21 g (50% of theory), Melting point: 231-233 ⁰ CC ₃₃ H ₃₆ F ₃ N ₆ O ₂ (591.68)

Calc .: C66.99 H6,13 N 11,83

Found: C66.83 H 5.96 N 11.71

The following compounds are obtained analogously:

4 '- [(7-Benzyloxy-2-n-butyl-4-methyl-benzimidazol-1-yl) -methyl) -2-trifluoroacetamino-biphenyl Melting point: 147-149 ° C 4'-I (2-n- Butyl-7-hydroxy-4-methyl-benzimidazol-1-yl) -methyl) -2-trifluoroacetaminomethyl-biphenyl Melting point: 247-2-19 ⁰ C 4 '- [(7-Benzyloxy-2-n-butyl-4 methyl-benzimidazol-1-yl) methyl] -2-biphenyl-trifluormethansulfonamino

Oil, Rr value: 0.65 (silica gel: petroleum ether / ethyl acetate = 1: 1) 4 '- [(2-n-butyl-7-trifluoromethanesulfonyloxy-4-methylbenzimidazol-1-yl) -methylI-2-trifluoromethanesulfonaminomethyl- biphenyl melting point: 137-139 ° C.

Example 144

4 '- [(2-n-butyl-4-methoxy-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-4-methoxybenzenimidazole-1 -yl) -methyl] biphenyl-2-carboic acid tert-butyl ester and trifluoroacetic acid.

Yield: 76.5% of theory, m.p .: 179-181 ⁰ CC ₂₆ H ₂₆ N ₂ O ₃ (414.51)

Calc .: C 75.34 H 6.32 N 6.76

Found .; C 75.07 H 6.35 N 6.71

Example 145

4 '- [(2-n-Butyl-7-methoxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-7-methoxybenzimidazole-1 -yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 80% of theory, m.p .: 260-261 ° CC ₂₆ H ₂₆ N ₂ O ₃ (414.51)

Calc .: C 75.34 H 6.32 N 6.76

Found: C, 75.09, H, 6.37, N, 6.79

Example 146

4 '- [(5-Aminoacetamino-2-n-butylbenzimidazole-1-vl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(5-aminoacetamino-2-n-butylbenzimidazole -1-yl) methyl] biphen _i 'l-2-carboxylate and trifluoroacetic acid.

Yield: 40% of theory, Melting point: 230-232 ⁰ C (dec.) C ₂₇ H ₂₈ N ₄ O ₃ (456.54)

Calc .: C71.03 H6.18 N 12.27

Found: C, 70.83, H, 6.36, N, 11.98

Example 147

4 '- [(2-n-butyl-5-n-pentylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid hemi-trifluoroacetate Prepared analogously to Example 9 from 4' - ((2-n-Bu (yl -5-n-pentylamino-benzimidazol-1-yl) -methyl | biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 92.3% of theory, Melting point: 155-157 ⁰ C (dec.) C ₃₀ H ₃₅ N ₃ O ₂ x '/ 2CF ₃ COOH (526.64)

Calc .: C 70.70 H 6.79 N 7.98

Gef .: C71.04 H 7,14 N 8,05

Example 148

4 '- [(2-n-Butyl-6-ethylthio) -benzo-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid hemitrifluoroacetate Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-methyl -amino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 77.3% of theory, melting point: 197-199 ° C

C ₂₈ H ₂₇ N ₃ O ₂ x V ₂ CF ₃ COOH (470.53)

Calc .: C, 68.92, H, 5.89, N, 8.93

Found: C 68.82 H 5.80 N 8.62

Example 149

4'-t (2-n-Butyl-6- (N-butanovinylmethylamino) -benzimidazole-1-vinyl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-I (2-n-butyl -6- (N-butanoyl-methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 70.3% of theory, Melting point: 165-167 ⁰ C.

C30H33N3O3 (483.62)

Calc .: C 74.51 H 6.87 N 8.68

Gef .: C74.51 H6.89 N8.56

Example 150

4 '- [(6-Aminocarbonylamino-2-n-butyl-benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid trifluoroacetate Prepared analogously to Example 9 from 4' - [(6-aminocarbonylamino-2-n-butyl -benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 93.8% of theory, Melting point: 134-136 ⁰ C (amorphous) C ₂ CH ₂₆ N ₄ O ₃ x CF ₃ COOH (556.54)

Calc .: C60.43 H4.89 N 10.07

Found: C, 60.22, H, 4.87, N, 9.80

Example 151

4 '- [(2-n-butyl-6- (n-1-nitroaminocarbonylamino) -benzimidazol-1-yl) -methYl] biphenol-2-ocarboxylic acid trifluoroacetate Prepared analogously to Example 9 from 4' - [(2-n-butyl -6- (n-hexylaminocarbonylamino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 93.3% of theory, melting point: 138-14O ⁰ C.

C ₃₂ H ₃₈ N ₄ O ₃ x CF ₃ COOH (640.70)

Calc .: C 63.74 H 6,14 N 8,74

Found: C63.66 H6.19 N8.51

Example 152

4 '- [(2-n-butyl-4-hydroxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-4-hydroxybenzimidazole) 1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 72.5% of theory, Melting point: 292-293 ⁰ C.

C ₂₅ H ₂₄ N ₂ O ₃ (400.48)

Calc .: C 74.98 H 6.04 N 7.00

Found: C 74.85 H 6,13 N 6,91

Example 153

4 '- [(2-n-Butyl-5-cyclohexylaminocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carbonyl-trifluoroacetate Prepared analogously to Example 9 from 4' - [(2-n-butyl-5-cyclohexylaminocarbonylamino -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 81.1% of theory, Melting point: 176-177 ⁰ C (amorphous) C ₃₂ H ₃₆ N ₄ O ₃ x CF ₃ COOH (638.69)

Calc .: C 63.94 H 5.84 N 8.77

Found: C 64.04 H 6.00 N 9.05

Example 154

4 '- [(2-n-butyl-7-isopropylaminomethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid hydrate Prepared analogously to Example 9 from 4' - [(2-n-butyl-7-isopropylaminomethyl -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 53% of theory,

Melting point: 156-158 ° C

C ₂₉ H ₃₃ N ₃ O ₂ x H ₂ O (473.61)

Calc .: C 73.54 H 7.45 N 8.87

Gef .: C73.69 H7.37 N8.91

Example 155

4'-t (6-Aminothocarbonylamino-2-n-butyl-benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid hemihydrate Prepared analogously to Example 9 from 4 '- [(6-aminothiocarbonyl-amino-2-n-butyl -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 80.4% of theory, melting point: 147-149 ⁰ C.

C ₂₆ H ₂₈ N ₄ O ₂ S χ V ₂ H ₂ O (467.58)

Calcd .: C66.80 H 5.81 N 6.85

Found: C 66.92 H 5.91 N 6.66

Example 156

4 '- [(2-n-butyl-6-cvclohexylaminothlocarbonylamino-benzlmidazol-1-yl) methyl] blphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-cyclohexylaminothiocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 88.2% of theory,

Melting point: 223-225 ⁰ C (dec.)

C ₃₂ H ₃₆ N ₄ O ₂ S (540.72)

Calc .: C71.08 H6.71 N 10.36 S5.93

Found: C, 70.95, H, 6.77, N, 10.53, S, 6.23

Example 157

4 '- [(2-n-butyl-6-hydroxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-hydroxybenzimidazole-1 yl) -methyl) biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 76.5% of theory, m.p .: 264-266 ° C

C ₂₆ H ₂₄ N ₂ O ₃ (400.48)

Calc .: C 74.98 H 6.04 N 7.00

Found: C 75.06 H 5.95 N 6.98

Example 158

4 '- [(2-n-Butvl-7- (2-methoxy-ethoxy) -4-methyl-benzlmidazol-1-yl) methyl] blphenyl-2-carbons8ure

Prepared analogously to Example 9 from 4'-l (2-n-butyl-7- (2-methoxy-ethoxy) -4-methylbenzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 63.6% of theory, Melting point: 205-207 ⁰ C

C ₂₈ H ₃₂ N ₂ O ₄ (472.58)

Calc .: C 73.71 H 6.82 N 5.93

Found: C, 73.48, H, 6.64, N, 6.15

Example 159

4 '- [(2-n-butyl-6-trifluoroacetylamino-benzimldazol-1-yl) methyl] blphenyl-2 - <: arbon acid

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-6-trifluoroacetylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

tert.butyl ester and trifluoroacetic acid.

Yield: 69.6% of theory, Melting point: 84-86 ⁰ C

C ₂₇ H ₂₄ N ₃ O ₃ F ₃ (495.50)

Calc .: C, 65.45, H, 4.88, N, 8.48

Found: C 65.20 H 5.06 N 8.64

Example 160

4 '- acid [(2-n-Butyl-4-cyclohexylamlnocarbonylamino-benzlmldazol-1-yl) methyl] blphenyl-2-carboxylic "

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-4-cyclohexylaminocarbonylamino-benzimidazol-1-yl) -methyl) biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 94.4% of theory,

Melting point: 242-244 ° C (decomp.)

C ₃₂ H ₃₈ N ₄ O ₃ (524.66)

Calc .: C 73.26 H 6.92 N 10.68

Found: C, 72.42, H, 6.93, N, 10.77

Example 161

4 '- [(6-Allylamnocarbonylamino-2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid trifluoroacetate Prepared analogously to Example 9 from 4'- | (6-allylaminocarbonylamino-2-n-butyl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 96% of theory,

Melting point: 90-92 ° C

C ₂₉ H ₃₀ N ₄ O ₃ X _CF3COOH (596.61)

Calc .: C 62.41 H 5.24 N 9.39

Gef .: C62.20 H5,17 N9.13

Example 162

4 '- [(e-Benzylamlnocarbonylamlno-2-n-butyl-benzlmldazol-1-yl) methyl] Biphenyl-2-c "rbonsSure

Prepared analogously to Example 9 from 4 '- [(6-benzylaminocarbonylamino-2-n-butyl-benzimidazol-1-yl) -methyl) biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 79.4% of theory, Melting point: 244-245 ⁰ C.

C ₃ JH ₃₂ N ₄ O ₃ (532.64)

Calc .: C 74.41 H 6.06 N 10.52

Found: C74.32 H6.09 N 10.31

Example 163

4 '- [(2-n-Butyl-6- (N-mothylamino-carbonyl-n-pentylamino) -benzlmldazol-1-vl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [{2-n Butyl-6- (N-methylaminocarbonyl-n-pentylamino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 54% of theory,

Melting point: 149-152 ° C

C ₃ JH ₃₈ N ₄ O ₃ (526.68)

Calc .: C, 72.98, H, 7.27, N, 10.64

Found: C 72.95 H 7.27 N 10.73

Example 164

4 '- [(5-Aminothiocarbonylamino-2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid hydrochloride Prepared analogously to Example 9 from 4'- (5-aminothiocarbonylamino-2-n-butyl benzimidazole-1-yl-methyl-biphenyl-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 66.6% of theory, melting point: 150-152 ⁰ C.

C ₂₈ H ₂₇ N ₄ O ₂ SCI (495.04)

Calc .: C 63.08 H 5.49 N 11.31 S 6.46

Found: C, 62.83, H, 5.76, N, 11.15, S, 6.22

Example 165

4 '- [(2-n-butyl-5-formylamlno-benzimidazol-1-yl) -methvl] blphenvl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-5-formylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.

butyl ester and trifluoroacetic acid.

Yield: 64.6% of theory, melting point: 229-23O ⁰ C.

C ₂₆ H ₂₆ N ₃ O ₃ (427.51)

Calc .: C 73.05 H 5.89 N 9.83

Found: C73.31 H6.11 N9.58

Example 166

4 '· [(2 · n · butyl · 5- (N-propanoyl · methylthioamino) benzimidazol · 1-yl) · methyl] blphenyl · 2 · carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl -5- (N-propanoyl-methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 77.8% of theory, Melting point: 178-18O ⁰ C

C ₂₉ H ₃₁ N ₃ O ₃ (469.59)

Calc .: C74.18 H6.65 N8.95

Gef .: C73.93 H6,70 N9.07

Example 167

4 '* [(2n-butyl-β- (N-methyl-aminocarbonyl-methylthylamino) -benzimidazol-1-yl) methyl] -bl-phenyl-2-carboxylicbenzone Prepared analogously to Example 9 from 4' - [(2-n-butyl -6- (N-methylaminocarbonyl-methylamino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 85.7% of theory, Melting point: 163-165 ⁰ C

C ₂₈ H ₃₀ N ₄ O ₃ (470.58)

Calcd .: C71.46 H 6.42 N 11.91

Found: C71.33 H6.64 N 11.74

Example 168

4 '- [(2-n-butyl-6- (N- (n-butylamino-carbonyl) -methylamino) -benzimidazol-1-yl) -methyl] -blphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2 -n-butyl-6- (N- (n-butylaminocarbonyl) -methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 90% of theory,

Melting point: 145-147 ° C

C ₃ H _3e N ₄ O ₃ (512,65)

Calc .: C72.64 H7.08 N 10.93

Found: C 72.90 H 7,16 N 10,69

Example 169

4 '- [(2-n-butyl-S- (N-methyl-aminocarbonyl-n-pentylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n- Butyl 5- (N -methylaminocarbonyl-n-pentylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 75% of theory,

Melting point: 240-242 ⁰ C

C ₃₂ H ₃₈ N ₄ O ₃ (526.69)

Calc .: C72.97 H 7.27 N 10.64

Found: C72 / 78 H7.23 N 10.66

Example 170

4 '- [(2-n-Butyl-6- (N-propanoylmethvlamine) -benzimidazole-1-vl) -methYl] -phenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-l (2-n-butyl -6- (N-propanoyl-methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 53.7% of theory,

Melting point: 152-154 ⁰ C

C ₂₉ H ₃₁ N ₃ O ₃ (469.59)

Calc .: C 74.16 H 6.66 N 8.95

Found: C 73.96 H 6.53 N 8.97

Example 171

Prepared analogously to Example 9 from 4 '- [(6-acetamino-2-n-butylbenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 87% of theory, Melting point: 252-254 ⁰ C

C ₂₇ H ₂₇ N ₃ O ₃ (441.53)

Calc .: C, 73.45, H, 6.16, N, 9.52

Found .: C 73.28 H 5.95 N 9.39

Example 172 A'-W-n-Butvl-e-proplonylamlno-benzimldazol-i-yO-methvUbtphenyl-a-carboxylic acid

Prepared analogously to Example 9 from 4Μ (2-η-ΒυΐνΙ · 6φΓορϊοηνΐ3Γηϊηο ^ θηζΪΓΐΐϊα3ζοΙ-1-γΙ) butyl ester and trifluoroacetic acid.

Yield: 90% of theory,

Melting point: 269-271 ⁰ C

C ₂₈ H ₂₈ N ₃ O ₃ (455.56)

Calc .: C 73.82 H 6.42 N 9.22

Gef .: C73.99 H6,42 N9,18

Example 173

^ • [(en-Butanoylamino) - n -butylbenzimidomethyl-3-D-methyl-1-phenylcarboxylic acid Prepared analogously to Example 9 from 4 '- [(6-n-butanoylamino-2-n-butylbenzimidazol-1-yl) methyl] bihenyl-2-carboxylic acid tert. butyl tester and trifluoroacetic acid.

Yield: 79.1% of theory, melting point: 253-255 ⁰ C.

C ₂₉ H ₃₁ N ₃ O ₃ (469.58)

Calc .: C74.18 H 6.66 N 8.96

Found: C 73.99 H 6.65 N 8.87

Example 174

A '^ - n-Butyl-e-ln-butylaminocarbonylamino-benzimidazol-i-O-methyllblphenylcarboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6- (n-butylaminocarbonylamino) -benzimidazole] 1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 69.2% of theory, Melting point: 239-242 ⁰ C.

C ₃₀ H ₃₄ N ₄ O ₃ (498.62)

Calc .: C 72.27 H 6.87 N 11.24

Found: C, 71.92, H, 6.86, N, 10.93

Example 175

4 '- [(2-n-Butyl-6- (N-cyclohexylamino-carbonyl-methylamino) -benzlmldozol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl -6- (N-cyclohexylaminocarbonyl-methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 80% of theory,

Melting point: 215-217 "C

C ₃₃ H ₃₈ N ₄ O ₃ (538.69)

Calc .: C73.58 H7.11 N 10.40

Found: C73.52 H7 / I9 N 10.54

Example 176

A'-LtZ-n-Butyl-e-tN-ldimethylaminocarbonyl-methylamino-benzimidazol-i-yD-methyl-phenylcarboxylic acid Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (N- (dimethylaminocarbonyl ) methylamino) -benzoimidazol-1-yl) methyl] bip ^s, enyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 66% of theory,

Melting point: 224-226 ⁰ C

C ₂₈ H ₃₂ N ₄ O ₃ (484.60)

Bee: C, 71.88, H, 6.66, N, 11.56

Gef .: C71.61 H6.92 N 11.27

Example 177

4 '- [(2-n-Butyl-6-n-pentanoylamino-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-) N-pentanoylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 74.5% of theory, melting point: 253-255 ⁰ C.

C30H33N3O3 (483.61)

Boron: C 74.57 H 6.88 N 8.70

Found .: C 74.23 H 7.08 N 8.63

Example 178

4 '· [(2-n-butyl-6 · (N (dlmethylamino-carbonyl) -amino) -benzimidazol-1-yl) -methyl] -phenyl-2 · -carboxylic acid trifluoroacetate

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (N- (dimethylaminocarbonyl) -amino) -benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 83.1% of theory,

Melting point: 198-200 ⁰ C

C ₂₈ H ₃₀ N ₄ O ₃ x CF ₃ COOH (584.60)

Calcd .: C, 61.63, H, 5.34, N, 9.58

Found: C 61.62 H 5.50 N 9.68

Example 179

4 '- [(2-n-butyl-6- (N- (n-butylamlnocarbonvl) -methylamlno) -banzimldazol-1-yl) methyl] biphenyl-2-carbon3äure trifluoroacetate

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (N- (n-butylaminocarbonyl) -methylamino) -benzimidazol-1-yl)

methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 70% of theory, Melting point: 152-154 ° C C ₃₁ H ₃₆ N ₄ O ₃ x CF ₃ COOH (626.68)

Calc .: C 63.25 H 5.95 N 8.94

Found: C6H, 18H, 6.07N, 9.03

Example 180 4 '· [(2 × π-butyl-6 × (JJcyclohexylaminocarbonyln-pβntyίamino) -benzimidazole 1-yl) θmethyl] biphθnyl × 2-carboxylic acid Hergestellt Prepared analogously to Example 9 from 4' - [(2-n Butyl-6- (N-cyclohexylaminocarbonyl-n-pentylamino) -benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 46.7% of theory, Melting point: 134-137 ⁰ C.

C ₃₇ H ₄₆ N ₄ O ₃ (594.80)

Calc .: C 74.72 H 7.79 N 9.42

Found .: C 74.52 H 7.85 N 9.34

Example 181

4 '× [(2 × n-butyl-β × (N × acetyl-methylamino) -benzimidazole × 1-yl) -methyl] -brifluoro-2 ×: tert-butylcarboxylate 4,5 g (9 mmol) 4' - [ (2-n-Butyl-6-acetylamino-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester are dissolved in 50 ml of dimethylformamide and mixed with 0.48 g (9 mmol + 10%) sodium hydride suspension in oil (50 %). The reaction mixture is stirred for 30 minutes at 80 ° C, cooled to room temperature and treated with 1.5 g of methyl iodide (9 mmol + 20%). After the reaction is evaporated in vacuo, aufgenommon in ethyl acetate and washed with water. The organic phase is dried over sodium sulfate and evaporated in vacuo to give an oily residue.

After purification over a silica gel column (particle size: 0.02-0.5 mm, eluent: methylene chloride / ethanol = 49: 1.24: 1), a yellowish oil is obtained.

Yield: 3.7 g (80.4% of theory), oil, R _r value: 0.75 (silica gel: methylene chloride / ethanol = 19: 1) C ₃₂ H ₃₇ N ₃ O ₃ (O 11.66)

Calc .: C 75.12 H 7.29 N 8.21

Found .: C 74.99 H 7,32 N 8,22

The following compounds are prepared analogously:

4 '- [(2-n-butyl-5- (N-propionyl-methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, R (value: 0.80 ( Silica gel: Essiges'ar / ethanol / ammonia = 90: 10: 1) 4 '- [(2-n-butyl-6- (N-propionyl-methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2 <; arbon acid butyl ester

Oil, Rr value: 0.65 (silica gel: methylene chloride / ethanol = 19: 1) Example 182

4 '- [(2-n-Butyl-e- (tetrahydropyran-2-yl-aminocarbonyiylamino) benzimidazol-1-yl) -methyl] blonphonyl-2-carboxylic acid Prepared analogously to Example 7 of 4' - ((6 -Amino-2-n-butylbenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid and tetrahydropyran-2-yl isocyanate.

Yield: 35.7% of theory, Melting point: 172-174 ⁰ C

C ₃ IH ₃₄ N ₄ O ₄ (562.64)

Ben: C 70,70 H 6,51 N 10,64

Found: C70.59 H6.77 N 10.88

Example 183

4 '- [(2-n-Butyl-6-phenyl-acetamido-benzimidazole-1-vl) -methyl] -bliphenyl-2-carboxylic acid-lieml-trifluoroacetate Prepared analogously to Example 9 from 4'- | (2-n-butyl-6-phenylacetamino) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid.

Yield: 29.2% of theory, Melting point: 273-275 ° C (dec.) C ₃₃ H ₃₁ N ₃ O ₃ x 0,5CF ₃ COOH (574.64) Calc .: C71.07 H5.53 N7. 31

Gef .: C71.01 H5.60 N7.11

Example 184

4 '- [(2-n-butyl-6- (N- (n-hexylaminocarbonyl) -cyclohexylamlno) -benzlmidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4'- | (2-n-butyl-6- (N- (n-hexylaminocarbonyl) -cyclohexylamino) -benzimidazol-1-yl) -methyll ·

biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 97.1% of theory, Melting point: 196-197 ⁰ C

C ₃₈ H ₄₈ N ₄ O ₃ (608.82)

Ben: C 74.97 H 7.95 N 9.20

Gef .: C74.75 H7.92 N9.19

Example * i85

V - ^ - n-Butyl-e-cyclohexylcarbonylamlno-benzimlHazol-i-yO-methyllblphenyl ^ -carbonsSure

Prepared analogously to Example 9 from 4Μ (2-η-ΒυΙγΙ · 6 · ϋνο ^ βχγΙ · θ3 ^ οηνΐ8πιϊπο ^ βηζΐιτιϊα8ζοΙ-1-νΙ) -ΓηβΐηγΙ] ΜρηβηνΙ-2

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 68.4% of theory, Melting point: 298-300 ⁰ C (dec.)

C ₃₂ H ₃₅ N ₃ O ₄ (509.65)

3rd: C 75.41 H 6.92 N 8.24

Found .: C 75.38 H 6.78 N 8.11

Example 186

44 (6-benzyloxycarbonylamino-2-n-butyl-benzlmidazol-1-yl) methyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(6-benzyloxycarbonylamino-2-n-butyl-benzimidazol-1-yl) -metl, yl-biphenyl-2-carboxylic acid

tert.butyl ester and trifluoroacetic acid.

Yield: 64.9% of theory, Melting point: 238-24O ⁰ C (decomp.)

Calc .: C 74.28 H 5.86 N 7.87

Found .: C 74.14 H 5.97 N 7.72

Example 187

4 '- [(2-n-butyl-6- (2-cyclohexyl-ethylamlno) -benzlmidazol-1-yl) methyl] blphenyl-2-carbonized sure

Prepared analogously to Example 98υ84Μ (2-η-ΒυΙνΙ · 6- (2-ογο ^ βχνΝθ ^ ν ^ ϊηο) ^ βηζϊη ^ 8ζοΙ-1-νΙ) -ι

tert.butyl ester and trifluoroacetic acid.

Yield: 66.6% of theory, Melting point: 217-219 ⁰ C

C ₃₃ H ₃₉ N ₃ O ₂ (509.69)

Calc .: C 77.77 H 7.71 N 8.24

Found: C 77.57 H 7.56 N 8.23

Example 188

4 '· [(2 · n · · butyl 6-cyclohθxylmθthylamlnocarbonyl bθnzimldazol · · 1 · yl) · mθthyl] biphenyl · 2 · carbons8urθ

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-cyclohexylmethylaminocarbonyl-benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 80.4% of theory, Melting point: 239-241 "C

C ₃₃ H ₃₇ N ₃ O ₃ (523.67)

Calc .: C 75.69 H 7.12 N 8.02

Found: C 75.53 H 6.94 N 7.97

Example 189

4 '- [(2-n-butyl-6-cyclohexylamlnocarbonyI-benzimidazol-1-yl) methyl] blphenyl-2-carbons8ure

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-cyclohexylaminocarbonyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

tert.butyl ester and trifluoroacetic acid.

Yield: 89.2% of theory, Melting point: 305-308 ⁰ C (dec.) C32H35N3O3 (509.65)

Calc .: C 75.42 H 6.92 N 8.24

Found .: C 75.31 H 7.03 N 8.11

Example 190

4 '- [(2-n-butyl-6- (N-methyl-N-butyluminocarbonvl) -benzimldazol-1-yl) methyl] blphenyl-2-carbonsfiure

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (N-methyl-n-butylaminocarbonyl) -benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 94.5% of theory, Melting point: 176-178 ⁰ C

C ₃₁ H ₃₅ N ₃ O ₃ (497.64)

Re: C74.82 H7.09 N8.44

Found: C74.98 H7.21 N8.50

Example 191

4 '- [(2-n-Butyl-6-ethoxycarbonyl-benzimidazol-1-yl) -rriethyl] -blphenyl-2-carboniaure Prepared analogously to Example 9 from 4' - ((2-n-butyl-6-ethoxycarbonyl-benzimidazole -l-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 59.7% of theory,

Melting point: 219-220 ° C

Cj ₈ H ₂₈ N ₂ O ₄ (456.54)

Calc .: C73.66 H6.18 N6.14

Found: C 73.49 H 6,13 N 5,94

Example 192

4 '- [(2-n-butyl-5-n-butYlamlnocarbonyl-benzlmld'Jzol-1-yl) methyl] blphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-5-n-butylaminocarbonyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

tert-butyl ester and trifluoroacetic acid.

Yield: 48.9% of theory, Melting point: 209-210 ° C

C ₃₀ H ₃₃ N ₃ O ₃ (483.61)

Calc .: C 74.51 H 6.88 N 8.69

Found .: C 74.54 H 6.79 N 8.79

Example 193

4 '- [(2-n-butyl-6- (3-cyclohexyl-piperidino) -benzlmldazol-1-yl) -mothyl] biphenyl-2-carboxylic acid-sesquitrifluoracetat

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (3-cyclohexyl-piperidino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid

tert.butyl ester and trifluoroacetic acid.

Yield: 85.0% of theory, Melting point: 155-157 ⁰ C C ₃ SH ₄₃ N ₃ O ₂ x 1.5CF ₃ COOH (720.80)

Calcd .: C 64.99 H 6.22 N 5.83

Found: C 64.88 H 6.41 N 5.95

Example 194

4 '- [(2-n-butyl-6- (cls-undtran $ -decahydronaphth-2-yl-amlno) -benzlmldazol-1-yl) methyl] blphenyl-2-Cerbon "iuredlhydrochlorld

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-e- (cis- and trans-decahydronaphth) -yl-amino-1-benzimidazoM-y-methyl-1-one)

Biphenyl-2-carb - ιε-acid tert-butyl ester and trifluoroacetic acid.

Yield: 24.0 ^C A Her theory, Melting point, yy! 32 "C

C ₃₆ H ₄ IN ₃ O ₂ X 2HCl (608.65)

Calc .: C 69.07 H 7.12 N 6.90

Found: C 68.98 H 7.23 N 6.97

Example 195

4 '[(2n-butyl-β-cyclohexylaminobenzlmldazol-1-yl) methylsulfuryl-2-carboxylic acid-β-β-quitl-fluoroacetate

Prepared analogously to Example 9 from 4'-l (2-n-butyl-6-cyclohexylamino-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid

tert.butyl ester and trifluoroacetic acid.

Yield: 99.0% of theory, Melting point: 64-66 ⁰ C (amorphous) C ₃ IH ₃₅ N ₃ O ₂ x 1,5CF ₃ COOH (652.68)

Calc .: C 62.57 H 5.64 N 6.44

Gef .: C62.68 H5.81 N6.25

semitrlfluoracetat

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (2-isopropyl-5-methylcyclohexyloxycorbonylamino) benzimidazol-1-yl)

methyllbiphenyl-a-carboxylic acid tert.butvlesterundTrifluoressigsöure.

Yield: 94.1% of theory, Melting point: 149-151 ⁰ C C ₃₈ H ₄₃ N ₃ O ₄ x 0,5CF ₃ COOH (638.77)

Ber .:. C 69.57 H 6.86 N 6.58

Found: C 69.39 H 6.91 N 6.56

Example 197

4M (2-n-butyl-6-cyclohexylacetamlno-benzfmidazoM-yl) -rnethyl] bfphenyl-2-carbonsfiure

Prepared analogously to Example 9 from 4M (2-n-butyl-6-cyclohexylacetamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

tert-butyl ester and trifluoroacetic acid.

Example 198

4 '- [(2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amld960mg (2.5 mmol) 4' · [(2-η-ΒυΙγΙββζΐζΐηιαζζοΙ -1-γΙ) -πιβΙΙινΙ | ^ ρηβηγΙ · 2 · 08ΐΐοη33υΓβ are dissolved in 25 ml of methylene chloride, treated with 2 ml of thionyl chloride and heated for one hour under reflux. The solvent is then distilled off and evaporated twice after the addition of methylene chloride. The residue is treated with 390 mg (2.5 mmol) of benzenesulfonamide are added anda hour at 14O ⁰ C heated. After cooling, the resulting oil is taken up in ethyl acetate / sodium chloride solution and extracted 3 times with ethyl acetate. The combined ethyl acetate phases are dried over sodium sulphate, concentrated and the crude product obtained is purified on a silica gel column with methylon chloride / ethanol as eluent.

Yield: 0.15 g (11% of theory), Melting point: 131-132 ⁰ C

C31H29N3O3S {523,65)

Calcd .: C, 71.11, H, 5.58, N, 8.02

Found .: C 70.96 H 5.49 N 8.21

The following compounds are obtained analogously:

4 '- [(2-n-Butyl-8-methoxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4' - [(2-Methoxymethyl-benzimidazol-1-yl ) -methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-pentyl-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4' -I (2-n-butyl-4-methyl-7-methoxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-propyl-benzimidazole -1-yl) -methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4'- | (2-n-butyl-5-acetamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid (N-methanesulfonyl) -amid4 '- [(2-n-butyl-5-chloro-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4' - [(2-n -butyl-5-butylaminocarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-butyl-6-phenylaminocarbonyiainino-benzimidazol-1-yl) - methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-butyl-6-cyclohexylaminocarbonylamino-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid ( N-methanesulfonyl) -amid4 '- [(2-n-butyl-5-butanoylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4' - [(2-n- butyl-6-chloro-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-butyl-5-methanesulfonamino-benzimidazol-1-yl) methyl ] biphenyN2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-butyl-6-ethoxycarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4'- [(2-n-butyl-6-isopropylsulfonamino-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid {N-methanesulfonyl) -amid4 '- [(2-n-butyl-4-butanoylamino-benzimidazole 1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-butyl-6-dimethylamino-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid ( N-methanesulfonyl) -amid4 '- ((2-n-butyl-5,6-dimethoxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-mothansulfonyl) -amid4' - [(2- (1-Butyn-4-yl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-methanesulfonyl) -amide 4 '- [(2-n-butyl-5 and e-trifluoromethylbenzimi dazol-i-yll-methyllbiphenyl ^ -carboxylic acid IN-methansulfonyD-amid4 '- [(2-n-butyl-5-and 6-n-butylaminocarbcnyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid ( N-methanesulfonyl) -amid4 '- [(2-n-butyl-5-dimethylaminosulfonyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4' - [(2-n- butyl-7-cyano-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-butyl-6-cyclohexylaminocarbonyl-benzimidazol-1-yl) methyl ] biphene, '- 2-carboxylic acid- (N-methanesulfonyl) amide 4' - [(2-n-butyl-6 * (N-methyl-n-butylaminocarbonyl) -benzine-1-azl-1-yl) -methyl] -biphinyl-2-carboxylic acid - (^ '· methanεulfoπyl) -

4 '- [(2-n-butyl-6-cyclohexylcarbonylamino-benzimidazol-1-yl) -mothyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4' - [(2-n-butyl-6- ( N-cyclohexylaminocarbonyl-n-pentylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-catbonsäure- (N-methansulfonyD-amide

4 '- [(6-n-butanoylamino-2-n-butyl-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4' - [(2-n-butyl-6-propionylamino -benzimidazole-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-butyl-5- (N-methylaminocarbonyl-n-pentylamino) -benzoimidazol-1-yl ) -methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) amide

4 '- [(2-n-butyl-6- (N- (n-butylaminocarbonyl) methylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) amide

4 '- ({2-n-Butyl-5- (N-propanoyl-methylamino) -benzoimidazol-1-yl) methyl) biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amiQ4'- | (2-n -butyl-5-formylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) -amid4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-n-pentylamino) -benzimidazole-1-yl) methyl) biphenyl-2-carboxylic acid- (N-methansulfonyD-amide

4 '- [(6-Aminothiocarbonylamino-2-n-butyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-methanesulfonyl) amide

4 '- [(2-n-butyl-7-methoxy-benz ^! Midazol-1-yl) -methyl) biphenyl-2-carboxylic acid (N-methanesulfonyl) -amide 4' - [(2-n-butyl) 6-cyclohexylmetliylaminocarbonyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-methanesulfonyl) -amide 4 '- [(2-n-butyl-6-methoxy-benzimidazol-1-yl) -methyl-biphenyl- 2-Carboxylic acid (N-tri (luoromethanesulfonyl) -amide) 4 '- [(2-Methoxymethyl-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amide 4' - [(2-n -Pentyi-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amide

'!' - ^ - n-butyl ^ methyl-y-methoxy-benzimidazol-i-yD-methyllbiphenyl ^ -carboxylic acid IN-trifluormethansulfonyD-amid4'-f (2-n-propyl-benzimidazol-1-yl) - methyl) biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amide

4 '- [(2-n-butyl-5-acetamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-tri (luormethansulfonyl) -amid4' - ({2-n-butyl-5 -chloro-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4 '- [(2-n-butyl-5-butylaminocarbonylamino-bonzimidazol-1-yl) methyl] biphenyl 2-carboxylic acid (N-trifluoromethanesulfonyl) -

4 '- [(2-n-butyl-6-phenylaminocarbonylamino-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid (N-trifluoromethanesulfonyl) -amide 4' - [(2-n-butyl-6-) cyclohexylaminocarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amide

4W (2-n-butyl-5-butanoylamino-benzimidazoM-yl) methyl] biphenyl-2-carbonsaure- (N-trifluoromethanesulfonyl) -amide

4'-l (2-n-butyl-6-chloro-benzimidazol-1-yl) -methyljbiphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4 '- [(2-n-butyl-5-methansulfcnamino-benzimidazole -1-yl) -methyl] biphenyl-2-carboxylic acid- (N-trjfluormethansulfonyl) -amid4 '- [(2-n-butyl-6-ethoxycarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid (N-triiluormethansulfonyl) -amid4 '- [(2-n-butyl-6-isopropylsulfonamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4' - [(2-n Butyl-4-butanoylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-trifluoromethanesulfonyl) -amide 4 '- [(2-n-butyl-6-dimethylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amide

4'-i (2-n-butyl × _{5/6-dimethoxy-benzimidazol-1-yl)} -mβthyl] biphenyl-2-carbonsäurβ- (N · triΠuormβthansulfonyl) -amid4 '- [{2- (1-butyne 4-yl) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluormothansulfonyl) -amid4 '- [(2-n-butyl-5-and 6-trifluoromethyl-benzimidazol-1-yl) - methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4 '- [(2-n-butyl-5-and 6-n-butylaminocarbonyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N -trifluormethansulfonyl) -

4 '- [(2-n-butyl-5-dimethylaminosulfonyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-trifluoromethanesulfonyl) -amide 4' - [(2-n-butyl-7-) cyano-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4'- | {2-n-butyl-6-cyclohexylaminocarbonyl-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid - (N-trifluoromethanesulfonyl) -amid4 '- [(2-n-butyl-6- (N-methyl-n-butylaminocarbonyl) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) amide

4 '- [(2-n-butyl-6-cyclohexylcarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4' - ((2-n-butyl-6- ( N-cyclohexylaminocarbonyl-n-pentylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluormethansulfonyD-amide

4 '- ((s-Butanoylarnino-2-n-butyl-benimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-tri (luormethansulfonyl) -amid4' - [(2-n-Butyl-e propionylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4 '- [(2-n-butyl-5- (N-methylaminocarbonyl-n-pentylamino) -benzimidazole-1 -yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amide

4 '- [(2-n-butyl-6- (N- (n-butylaminocarbonyl) methylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluonnethansulfonyD-amide

4 '- ((2-n-Butyl-5- (N-propanoyl-methylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -

4 '- [(2-n-butyl-5-formylamino-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4' - [(2-n-butyl-6- ( N-methylaminocarbonyl-n-pentylamino) -benzoimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amide

4 '- [(6-Aminothiocarbonylamino-2-n-butyl-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid- (N-1rifluormethansulfonyl) -amid4' - [(2-n-butyl-7-methoxy-benzimidazole -1-yl) -methyl) biphenyl-2-carboxylic acid- (N-trifluoromethanesulfonyl) -amid4 '- [(2-n-butyl-6-cyclohexylmethylaminocarbonyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid (N-trifluoromethanesulfonyl) -amide

4 '- [(2-n-butyl-6-methoxy-benzimidazol-1-yl) methyl) biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4' - [(2-Methoxymethyl-benzimidazol-1-yl ) -methyl] biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4 '- [(2-n-pentyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amide

4'-j (2-n-butyl-4-methyl-7-methoxy-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4 '- [(2-n-propyl -benzimidazole-1-yl) methyl) biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4 '- [{2-n-butyl-S-acetamino-benzimidazol-1-yl) methyl] biphenyl-2- carboxylic acid- (N-benzenesulfonyl) -amid4 '- [(2-n-butyl-5-chloro-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4' - ((2 -n-butyl-5-butylaminocarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4 '- ((2-n-butyl-6-phenylaminocarbonylamino-benzimidazol-1-yl ) -methyl] biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4 '- [(2-n-butyl-6-cyclohexylaminocarbonylamino-benzimidazol-1-yl) methyl | biphenyl-2-carboxylic acid- (N-benzenesulfonyl ) -amido 4 '- [(2-n-butyl-5-butanoylaminobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-b8nzolsulfonyl) -amide 4' - [(2-n-butyl) 6-chloro-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4 '- [(2-n-butyl-5-methanesulfonarsino-benzimidazol-1-yl) -me ethyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4 '- [(2-n-butyl-6-ethoxycarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amid4 '- ((2-n-butyl-6-isopropylsulfonamino-benzimidazol-1-yl) -me (hyl | biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4' - [(2-n-butyl 4-butanoylamino-benzimidazol-1-yl) -m6thyl | biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amid4 '- [(2-n-butyl-6-dimethylamino-benzimidazol-l-yl) methyl) biphenyl -2-carboxylic acid (N-benzenesulfonyl) -amid4 '- [(2-n-butyl-5, e-dimethoxy-benzimidazol-1-yl) methyl] biphenyl-2-carbonsSure- (N-benzenesulfonyl) -amid4 '- [(2- (1-Butyn-4-yl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -arr'!

4 '- [(2-n-butyl-5- and 6-trifluoromethyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide

4 '- [(2-n-Bu: New York Convention ^l-yl-5 6-n-butylaminocarbonyl-benzimida2ol-1-yl) methyl | biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amide

4 - [(2-n-Butyl-5-dimethylarninosulfonyl-benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid- (N-benzenesulfonyl) -arnid

4 '- [(2-n-Butyl-7v ^{(yano-benzimidazol-1-yl)} methyl) biphenyl-2-carbor _l ääure- (N-benzenesulfonyl) -amide

4 '- [(2-n-butyl-6-cy <: lohexylaminocarbonyl-benzimidazol-1-yl) methyl] biphenyl-2-carbonsöure- {N-benzenesulfonyl) -amide

4'-i (2-n-butyl-6- (N-roethyl-n-butylaminocarbonyl) -ben2imidQzol-1-yr; -methyllbiphenyl-2-carboxylic acid- (N-benzolsulfonyO-amide

4 '- [(2-n-butyl-6-cyclo (exylcarbonylamino-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amide

4 '- ((2-n-butyl-6- (N-cyclohexylaminocarbonyl-n-pentylamino) -benzoimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid- (N-benzolsulfonyD-amide

4 '- [(6-n-Butanoylamino-2-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4'-l (2-n-butyl) 6-propionylamino-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4 '- [(2-n-butyl-5- (N-methylaminocarbonyl-n-pentylamino) -benzimidazole-1 -yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4 '- [(2-n-butyl-e- (N- (n-butylaminocarbonyl) -methylamino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid- (N · benzenesulfonyl) -amide

4'- | (2-n-butyl-5- (N-propanoyl-methylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4'-l (2-n- Butyl-5-formylaminobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-n-pentylamino) -b6nzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid- (N-benzenesulfonyl) -amide

4 '- [(6-Aminothiocarbonylamino-2-n-butyl-benzimidazol-1-yD-methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4' - [(2-n-butyl-7-methoxy -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (N-benzenesulfonyl) -amide 4 '- [(2-n-butyl-6-cyclohexylmethylaminocarbonyl-benzimidazol-1-yl) -methyl] biphenyl-2 -carboxylic acid (N-benzenesulfonyl) -amide

Example 199

4 '- [(2-n-butyl-e-formylamino-benzimidazol-1-yl) -methYl] -blphenyl-2-carboxylic acid EX, 7% trifluoroalic acid Prepared analogously to Example 9 from 4'-1 (2-n-butyl-6-formylamino) benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 84.0% of _theory:

Melting point: 110-112 ⁰ C (amorphous) C33H37N3O3 X 0.75 CF ₃ COOH (513.02)

Ben: C 64.38 H 5.06 N 8.19

Found: C 64.70 H 5.25 N 7.91

Example 200

4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-cyclohexylamino) -benzlmidazol-1-yl) -muthyl] blphenyl-2-carbonsäuresemitrifluoracetat

Prepared analogously to Example 9 from tert-butyl 4 '- [(2-n-butyl-6- (N-cyclohexyl-> -minocarbonylcyclohexylamino) benzimidazol-1-yl) -methyllbiphenyl-2-carboxylate and trifluoroacetic acid.

Yield: 91.9% of theory, Melting point: 130-132 ⁰ C (amorphous) C ₃₈ hwn ₄ O ₃ χ 0.5 CF ₃ COOH (663.82)

Calc .: C 70.57 H 7.06 N 8.44

Found .: C 70.48 H 7,13 N 8,60

Belsple! 201

4 '- [(2-n-butyl-6- (N- (n-butylaminocarbonyl) cyc ohexylamino) -benzoimidazol-1-yl!) Methyl] b phenyl-2-carboxylic acid!

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (N- (n-butylaminocarbonyl) -cyclohexylamino) -benzimidazol-1-yl)

tert-butyl methyllbiphenyl-2-carboxylate and trifluoroacetic acid.

Yield: 85.7% of theory, Melting point: 227-228 ⁰ C

C ₃₆ H ₄₄ N ₄ O ₃ (580.77)

Calc .: C, 74.45, H, 7.64, N, 9.65

Gef .: C74.32 H7,70 N9,50

Example 202

4 '- [(2-n-Butyl-6- (N-methylaminocarbonylcyclohexylamino) -benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl -6- (N-methylaminocarbonylcyclohexylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 88.3% of theory, m.p .: 204-206T

C ₃₃ H ₃₈ N ₄ C (538.69)

Calc .: C73.58 H 7.11 N 10.40

Found: C 73.65 H 6.99 N 10.49

Example 203

4 '- [(2-n-Butyl-6- (N-3-thoxycarbonylcyclohexylamino) -b-2-imidazol-1-yl) -methyl] -blphenyl-2-carbonyl acid Prepared analogously to Example 9 from 4' - [(2-n-butyl) 6- (N-ethoxycarbonyl-cyclohexylamino) -benzoimidazol-1-yl) -2- -methyllbiphenyl

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 89.0% of theory, melting point: 239-24O ⁰ CC ₃₄ H ₃₉ N ₃ O ₄ (553.70)

Calc .: C 73.75 H 7.10 N 7.59

Found .: C 73.76 H 7.25 N 7.68

Example 204

^ • [U-n-butyl-B-cyclohexylacetamino-indulmldazol-i-y-d-mothylbliphenylcarboxylic acid x 0.7 trifluorosulfuric acid

Prepared analogously to Example 9 from 'r -is-n-butyl-e-cyclohexylacotamino-benzimidazol-i-yl) -methyl] biphenyl-r: -carboxylic acid

tert.butyl ester and trifluoroacetic acid.

Yield: 97.5% of theory, Melting point: 117-119'C CjjHjjNjOj x 0.7 CF ₃ COOH (603.49)

3rd: C 68.46 H 6.30 N 6.96

Found: C 68.80 H 6.60 N 6.73

Example 205

4 '· [(2 · n · butyl · 6 · phthalimnone · bonzlmldazol · 1 · yl) · mothyl · blphθnvl · 2 · carboxylic acid semidrug acetate

Prepared analogously to Example 9 from 4'- | (2-n-butyl-6-phthalimino-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester

and trifluorosulfonic acid in molylonyl chloride.

Yield: 85.5% of the Thoorie, Melting point: 181-183 ⁰ C

C ₃₃ H ₂₇ N ₃ O ₄ x 0.5 CF ₃ COOH (586.61)

Calc .: C69.62 H4.73 N 7.16

Found: C 69.70 H 4.81 N 7.31

Example 206

Prepared analogously to Example 198 from 4'- | (2-n-butyl-1,4-benzimidazol-1-yl) -methyl | biphenyl-2-carbonic acid and thionyl chloride / methanesulfonamide.

Yield: 32.4% of theory, Melting point: 127-129 ⁰ C.

C ₂ JH ₂₇ N ₃ O ₃ S (461.50)

Calc .: C67.67 H5,90 N9,10 S6,92

Found: C 67.52 H 6.10 N 9.07 S 6.87

Example 207

4 '- [(2-l1.butyl-.beta. ((5-trifluoroac-β-methyl-pentyl) -amino-carbonyl. -Nano) benzimidazole. 1-yl). M-butyl] -blphenyl. 2-carboxylic acid semi-trifluoroacetate semi-hydrate 1.92g (3, 3 mmol) 4 '- [(2-n-butyl-theta-trifluoropyran-2-yl-aminocarbonylamino) -benzimidazol-1-yl) -methyl) -biphothyl-2-carboxylic acid tert-butyl ester are dissolved in 100 ml of ethanol and treated with 1 , 9g Raney nickel spiked. The reaction solution is then hydrogenated for 4 hours at 120 ⁰ C and 10Obar hydrogen. The catalyst is then filtered off with suction and the solvent in

Vacuum distilled off. The oily residue is purified on a column (silica gel, particle size: 0.063-0.2 mm), using Methylene chloride and increasing parts of 2-5% ethanol is eluted. After spinning in the appropriate fractions,

Dissolve the resulting oil in a mixture of 10 ml of methylene chloride and 10 ml of trifluoroacetic acid and leave the solution for 15 hours at room temperature. The solvent is then removed by rotary evaporation, the residue is dissolved in about 50 ml of ethyl acetate and the organic phase is washed 3 times with about 50 ml of water. The organic solution is dried with about 20 g of magnesium sulfate, filtered off and concentrated by rotary evaporation. The product thus obtained is dried at 5O ⁰ C in vacuo.

Yield: 1.5 g (66.0% of theory), Melting point: 80-82 ° C (amorphous)

Calc .: C 59.13 H 5.33 N 8.11

Found: C 59.22 H 5.52 N 7.95

Example 208

4 '- [(2-n-butyl-e- (N-ethoxycarbonyl-benzylamlno) -benzlmldazol-1-yl) methyl] blphonyl-2-carbons8ure

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-6- (N-ethoxycarbonyl-benzylamino) -benzimidazol-1-yl) -methyl) biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 86.4% of theory, Melting point: 218-220 ° C

C ₃₆ H ₃₆ N ₃ O ₄ (561.68)

Calc .: C 74.84 H 6.28 N 7.48

Found: C74.57 H 6.14 N 7.59

Example 209

4 '- [(2 · n · butyl · 6 · {N · mθthylamiΓιocarbonyl · benzylamino) benzimidazole 1 · yl) · methylthyl] blphenyl · 2 · cβrbonslure

Prepared as described in Example 9 from 4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-benzylamino) -benzimidazol-1-yl] -methyl] -biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

233

From ieute: 83.3% of theory, Point of view: 247-249 ⁰ C

C ₃₄ H ₃₄ N ₄ O ₃ (546.67)

Calc .: C74.70 H6.27 N 10.25

Found: C 74.95 H 6.37 N 10,12

Example 210

ννρν

Prepared analogously to Example 9 cus 4 '- [(2-n-butyl-6- (n-hexyloxycarbonylamino) -benzimidazol-1-yl-methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluorossigsoluro. Yield: 89.5% of Theory, Melting Point: 243-244 ⁰ CC ₃₂ H ₃₇ N ₃ O ₄ (527.66)

Calc .: C, 72.84, H, 7.07, N, 7.96

Gef .: C72.65 H7.15 N 7.98

Example 211

^ • [(Z-n-butyl-e-lN-ln-hexvlamlnocarbonvD-benzylaminol-benzlmldazoM-yD-methyUblphenvl ^ -carbonsSure

Prepared analogously to Example 9 from 4 '× | (2 × n-butyl-6 × (N × (n × hoxylaminocarbonyl) -benzylamino) -benzamidamido-1-yl) -methyl] biphenyl

2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 69.2% of theory, Melting point: 186-187 "C

C _n H ₄₄ N ₄ O ₃ (616.80)

Re: C75.94 K7.19 N9.08

Found .: C 75.85 H 7,24 N 9,14

Example 212

Prepared from 4 '- ((2-n-butyl-6- (n-pentylamino) benzimidazol-1-yl) methyllbiphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid / methylene chloride Theory, Melting Point: 108-113 ⁰ CC ₃₀ H ₃₅ N ₃ O ₂ (169.62)

Calc .: C 76.73 H, 7.51 N, 8.94

Gef .: C76.56 H7.40 N8.91

Example 213

4 '- [(2-n-butyl-e- (S, 7-dloxo-1H, 3H-imldazo [1,5-c] thiazole-e-vl) -benzlmldazol-1-yl) methyl] blphenyl- 2-carboxylic acid

Prepared analogously to Example 9 from 4'- | (2-η · ΒυΐνΙ · 6 · (5,7 · οίοχο-1Η, 3Η · ίΓηία8ζο [1,5-ο1ΐΗίβζοΙ · 6 · νΙ) · οθηζίΓηί08ζοΙ-1-γΙ) ·

Methyllbiphenyl ^ -carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 95.1% of theory, Melting point: 229-23O ⁰ C

CmH ₂₁ N ₄ O ₄ S (540.64)

Bar .: C 66.65 H 5.22 N 10.36 S 5.93

Found: C66.42 H5.29 N 10.15 S6.01

Example 214 4 '* [(2n-butyl-β ((5xhydroxy-n-p-octyl) -aminocarbonylamino) -benzimidazole-1-yl) -methyl] -phenyl-2-carboxur-monohydrate Prepared analogously to Example 72 of 4M (2-n-Butyl-6 - ((5-hydroxy-n-penty!) - aminocarbonylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid ethyl ester and 2η NaOH / ethanol.

Yield: 50.0% of theory, Melting point: 158-160 ⁰ C

C ₃₁ H ₃₈ N ₄ O ₄ x H ₂ O (546.67)

Re: C68.11 H7.01 N 10.25

Found: C 68.01 H 6.90 N 10.30

Example 215

4 '· [(2 · n · β · · butyl ((5 · hydroxy · n · pentyl) -amlnocarbonylamino) · · benzimldazol-1 yl) methyl] blphenyl · 2 · carboxylic acid-ethylester7,5g (13,5mMol) 4 '- [(2n-butyl-6- (tetrahydropyran-2-yl-aminocarbonylamino) -benzimidazol-1-yl) -methyl] biphonyl-2-carboxylic acid ethyl ester are dissolved in 250 ml of ethanol and treated with 7.5 g of Raney® Nickel added. The solution is then hydrogenated for 2 hours at 12O ⁰ C and lOObar hydrogen in an autoclave. Then it is aspirated from the catalyst and distilled from

Solvent in a vacuum. The resulting oily product is purified over a column (silica gel, particle size: 0.063-0.2 mm),

being eluted with ethyl acetate / petroleum ether (9/1) and with Essigosler / ethanol (99/1). The appropriate fractions concentrated werdenim vacuum and dried in a vacuum oven at 5O ⁰ C.

Yield: 2.6 g (34.7% of theory), Oil, R ₁ : 0.50 (silica / ethyl = 9: 1) Example 216

4 '- [(2-n-butyl-8- (N- (n-butanoyl) -N-butylamino) -benzlmldazol-1-yl) methyl] blphenyl-2-carbons8ure

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (N- (n-butanoyl) -n-butylamino) -benzimidazo-1-yl) -methyl] biphenyl-2-

o-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 90.6% of theory, m.p .: 234-235 ° C

C ₃₃ H ₃₉ N ₃ O ₃ (525.69)

Calc .: C, 75.40, H, 7.48, N, 7.99

Get: C 75.55 H 7.49 N 8.02

Example 217

4 '· [(2 · n · butyl · 6 · (N · (4 · mθthoxycarbonyl · thlazolidln-3 · yl · carbonyl) · n · butylamino) · benzimidazol-1 · yl) · methyl) blphθnyl 2-carboxylic acid

Prepared analogously to Example 9 from 4M (2-n-butyl-6- (N- (4-methoxycarbonylthiazolidin-3-yl-carbonyl) -n-butylamino) -

benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 92.6% of theory, m.p .: 86-88 ° C (amorphous) C ₃₅ H ₄₀ N ₄ O ₆ (628.79)

Re: C66.86 H6.41 N8.91 S5.10

Found: C 66.68 H 6.40 N 8.50 S 5.41

Example 218

4 '× [(2 × n-butyl-6 × (N × cyclohexylaminocarbonyl-n-butylamino) -benzenedazole × 1 × yl) -methyl] -phenyl-2 × carboxylic acid Hergestellt Prepared analogously to Example 9 from 4' - [(2 N-butyl-6- (N-cyclohexylaminocarbonyl-n-butylamino) benzimidazoM-yl) -methyl | biphenyl-2-carboxylic acid tert -butyl ester and tri (1-chloroacetic acid.

Yield: 96.8% of theory, m.p .: 106-108 ° C (amorphous) C ₃₄ H ₄₄ N ₄ O ₃ (580.77)

Calc .: C, 74.45, H, 7.64, N, 9.65

Found: C 74.54 H 7.65 N 9.50

Example 219

4 '· [(2 · n · butyl 6 · (N cyclohxylaminocarhonyl · bθnzylanlino) · bβnzimidazole · 1 yl) methyl] biphθnyl · 2 · carbonsiurθ Prepared analogously to Example 1! 9aus4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-benzylamino) -benzimidazoM-yl) methyl) biphenyl-2-carboxylic acid tert-butyl ester.

Yield: 95.0% of theory, Melting point: 203-204 ⁰ C.

C ₃₉ H ₄₂ N ₄ O ₃ (614.79)

Calc .: C76.19 H 6,89 N 9,11

Found: C, 75.93, H, 7.04, N, 9.34

Example 220

4 '· [(2-n · butyl · 6 · (N · (2-trifluoromethyl-3-pyramido-methyl) -methylamino) -benzimidazol · 1-yl) -methyl] -biphino-2-carboic acid Prepared analogously to Example 9 from 4'-1 (2 -n-butyl-6- (N- (2-tri (-luoromethylphenylaminocarbonyl) -methylamino) -benzimidazol-1-yl) -methyl-biphenyl -carboxylic acid-tert-butyl ester and trifluoroacetic acid / methylene chloride.

Ausbuete: 72.2% of theory, Melting point: 142-144 ⁰ C.

O ₃₄ H ₃ IF ₃ N ₄ O ₃ x CF ₃ COOH (714.67)

3rd: C 60.52 H 4.51 N 7.84

Found: C 60.53 H 4.48 N 6.03

Example 221

4 '- [(2-n-Butyl! -6- (N-cyclohexylamino-carbonyl-n-hexylamino) -benzimidazol-1-yl) -methyl] -blphanyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2- n-butyl 6- (N -cyclohexylaminocarbonyl-n-hexylamino) -benzimidazol-1-yl) -methyl-biphenylcarboxylic acid tertiary-butyl ester and trifluoroacetic acid.

Yield: 94.1% of theory, melting point: 177-178 ⁰ C.

C ₃₈ H ₄₈ N ₄ O ₃ (608.82)

Calc .: C 74.97 H 7.95 N 9.20

Found: C 74.75 H 8.04 N 9.09

Example 222

4 '× [(2 × n-butyl-6- (N × cycloethyl / 1-carbonyl-n-hexylamino) benzimidazole-1-yl) -methyl] -biphosil-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2 -n-butyl-6 (N-cyclohexylcarbonyl-n-hexylamino) -benzimidazoM -yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 92.8% of theory, Melting point: 195-197 ⁰ C.

Calc .: C 76.86 H 7.98 N 7.08

Found .: C 76.66 H 7.94 N 7.16

Example 223

4 'x l (2 x n x butyl x 6 x (N x cyclohexylamino carbonyl x n x propyl ammonium) x n thiazol · 1 x yl) xθthyl] blphθnyl x 2 x carbons xurθ Prepared analogously to Example 9 from 4'-Ι (2 x η -ΒυΙνΙ · 6 · (Ν · ονοΙοΙιβχνΐ8Γϊ) ϊηοο8 ^ οηνΙ · methyllbiphenyl-2-carboxylic acid tert, butyl ester and trifluoroacetic acid.

Yield: 93.5% of theory, Melting point: 180-182 ⁰ C.

C ₃₆ HwN ₄ O ₃ (566.74)

Calc .: C 74.18 H 7.47 N 9.89

Qef .: C73.98 H, 7.54 N, 10.05

Example 224

4'-t (2-n-Butyl 6- (N-cyclohexylcarbonyl-methyl-amino) -imida- zol · 1-yl) -methylthiphosphinol · 2-carboxylic acid · sβ-dihydrate Prepared analogously to Example 9 from 4W (2-n-butyl-6- (N -cyclohexylcarbonyl-methylamino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert.butyl ester and trifluorossacetic acid.

Yield: 93.8% of theory, Melting point: 230-231 ⁰ C.

C ₃₃ H ₃₇ N ₃ O ₃ x 0.5 H ₂ O (532.68)

Re: C74.41 H7.19 N7.89

Found .: C 74.59 H 7,14 N 7,70

Example 225

4 '· [(2 · n · butyl 6 · (^ J · cyclohexylamlnocarbonyl etylamino) · propynyldazol · 1 · yl) · methyl] blphθnyl · 2 · carboxylic acid Hergestellt Prepared analogously to Example 9 from 4' - [(2-n-butyl-6 - (N-cyclohexylaminocarbonyl-ethylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 95.5% of theory,

Melting point: 185-186 ° C

C34H40N4O3 (552.72)

Calc .: C 73.89 H 7.29 N 10.14

Gef .: C73.79 H7.13 N 10,11

Example 226

4 '- [(2-n-Butyl-6- (N- (n-butanoyl) -n-pentylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 in 4Μ (2- η-ΒυΐνΙ · 6 · (Ν- (η ^ υΐ3ηονΙ) · πφβηΐν ^ ΐηο) ^ βηζίη ^ 8ζοΙ-1-γΙ) -πΐθΙΙινΙ] ΝρΙιβΓψΐ-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 77.8% of theory, Melting point: 206-208 ⁰ C.

CmH ₄₁ N ₃ O ₃ (539.72)

Ber .; C 75.66 H 7.66 N 7.79

Found: C 75.54 H 7.47 N 7.67

Example 227

4 '- [(2-n-butyl-6-fsopropylcarbonylamino-benzimidazol-1-yl) methyl] blphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4'-l (2-n-butyl-6-isopropylcarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid

tert.butyl ester and trifluoroacetic acid.

Yield: 73.3% of theory, Melting point: 273-275 ⁰ C.

C ₂₉ H ₃ IN ₃ O ₃ (469.58)

Calc .: C 74.18 H 6.65 N 8.95

Found: C, 73.93, H, 6.66, N, 8.84

Example 228

4 '· [(2-n-Butyl-6- (N-ethoxycarbonyl-methylamino) -benzimidazole-1-yl) -methylthylbiphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6 (N-ethoxycarbonyl-methylamino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 91.8% of theory,

Melting point: 190-192 ⁰ C

C ₂₉ H ₃₁ N ₃ O ₄ (485.58)

Calc .: C71.73 H 6.43 N 8.65

Found: C 71.60 H 6.40 N 8.69

Example 229

4 '- [(2-n-Butyl-6- (N-ethoxycarbonyl-n-pentylamino) -benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-I (2-n -butyl-6- (N-ethoxycarbonyl-n-pentyl-amino) -benzoimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert.butylesterundTrifluoressigsäure / methylene chloride.

Yield: 86.9% of theory, melting point: 201-203 ° C

C ₃₃ H ₃₉ N ₃ O ₄ (541.69)

Calc .: C 73.17 H 7.26 N 7.76

Found: C, 72.97, H, 6.98, N, 7.69

Example 230

4 '- [(2-n-Butyl-6- (N- (dlmethylaminocarbonyl) -bonzylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n Butyl-6- (N- (dimethylaminocarbonyl) -benzylamino) -benzimidazol-1-yl) -methyl-] -phenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 75.3% of theory, Melting point: 202-203 ⁰ C.

C ₃₆ H ₃₆ N ₄ O ₃ (560.69)

Calc .: C 74.98 H 6.47 N 9.99

Found: C, 74.89, H, 6.24, N, 10.02

Example 231

Prepared analogously to Example 9 from 4 '- [(2,5-di-n-butyl-ben2imidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 82.6% of theory, Melting point: 199-201 ⁰ C.

C ₂₉ H ₃₂ N ₂ O ₂ (440.58)

Calc .: C 79.06 H 7.32 N 6.36

Found: C 78.87 H 7.29 N 6.58

Example 232

4 '- [(2-n-Butyl-6- (N-CYChexylamino-N-carbonyl-N- (2-phylmethyl) -amino) -benzlmld8zol-1-vl) -methyl] -phenylene-2-carboxylic acid Prepared analogously to Example 9 of 4'. - [(2-n-Butyl-6- (N-cyclohexylaminocarbonyl-N- (2-phenylethyl) -amino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 70.0% of theory, melting point: 168-170 ⁰ C.

C ₄₀ H ₄₄ N ₄ O ₃ (628.81)

Re: C76.40 H7.05 N8.91

Found .: C 76.31 H 7.26 N 8.79

Example 233

4 '- [(2-n-butyl-6-diethylaminocarbonylaminobenzititiazol · 1-yl) .methyl] blpholyl.-2-carboxylic acid semirtrifluoroacetic acid Prepared analogously to Example 9 from 4' - ((2-n-butyl-6-diethyl -aminocarbonylaminobenzimidazol-1-yl) -rnethyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid Yield: 79.4% of theory, m.p .: 235-237 ° C

C ₃₀ H ₃₄ N ₄ O ₃ X 0.5 CF ₃ COOH (555.64)

Calc .: C 67.01 H 6.26 N 10.08

Found: C66.99 H 6.02 N 10.12

Example 234

4 '- [(2-n-butyl-6-dimethylaminoacetamino-bonimidazol-1-yl) -methyl] -biphyln-2-carboxylic acid-d-trifluoroacetate Prepared analogously to Example 9 from 4' - [(2-n-chloro-6- ( dimethyl-aminoacetamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert.butylesterundTrifluoressigsäure / methylene chloride.

Yield: 75.5% of theory, melting point: 218-22O ⁰ C.

C ₂₈ H ₃₂ N ₄ O ₃ x 2 CF ₃ COOH (712.65)

Calcd .: C 55.61 H 4.81 N, 7.86

Found: C 55.61 H, 5.05 N, 8.19

Example 235

4 '- [(2-n-butyl-6 * (2,2-dimethyl-propionylamino) benzίmίdazol-1-yl) methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl -6- (2,2-dimethyl-propionylamino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 67.5% of theory, Melting point: 326-327 ⁰ C.

C ₃₀ H ₃₃ N ₃ O ₃ (483.61)

Calc .: C 74.51 H 6.88 N 8.69

Found .: C 74.32 H 7.06 N 8.58

Example 236

4 '- [(2-n-Butyl-6 - (! M- (n-hexylaminocarbonyl) -N- (2-plienyl-ethyl) -amino) -benzlmldazot-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously Example 9 of 4 '- [(2-n-Butyl-6- (Nl (n-Hoxycarbonyl) -N- (2-phenylethyl) -arnino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert butyl ester and trifluoroacetic acid.

Yield: 66.7% of theory, melting point: 176-177 ° C

C ₄₀ H ₄₆ N ₄ O ₃ (630.83)

Calc .: C76.16 H7.35 N8.88

Found: C, 75.97, H, 7.44, N, 8.98

Example 237

4 '- [(2,6-Di-n-butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2,6-di-n-butyl-benzimidazole -1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid / methylene chloride.

Yield: 75.9% of theory, melting points: 188-190 ° C

C ₂₉ H ₃₂ N ₂ O ₂ (440.59)

Calc .: C 79.06 H 7.32 N 6.36

Found .: C 78.96 H 7.36 N 6.18

Example 238

^ • [(Z-n-butyl-e-cyclopentylcarbonvlamino-benzimidazol-i-yll-methyllbiphenyl-Z-carboxylic acid-semihydrate

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-6-cyclopentylcarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 72.2% of theory, Melting point: 272-274 ⁰ C

C ₃₁ H ₃₃ N ₃ O ₃ χ 0.5 H ₂ O (504.63)

Calc .: C 73.79 H 6.79 N 8.33

Found .: C 74.00 H 6.91 N 8.25

Example 239

4 '- [(2 * n-butyl-6-cyclopropyl' *) -rbonylaminobenzimidazole-1-yl) -methyl] -biphenyl-2-carbonylurea · hydrate

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6-cyclopropylcarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 91.7% of theory,

Melting point: 275-277 ° C

C ₂₉ H ₂₉ N ₃ O ₃ x 0.5H ₂ O (47f, 57)

Calc .: C 73.09 H 6.34 N 8.82

Found: C 72.97 H 6.50 N 8.52

Example 240 4 '- [(2-n-Butyl-6- (1-oxo-isoindolln-2-yl) -benzimidazol-1-yl) -mothyl] -blphenyl-2-carboxylic acid trifluoroacetate 1.6g (3 mmol) 4 '- [(2-n-Butyl-6-phthalimino-benzimidazol-1-yl) -ethyl-biphenyl-2-carboxylic acid trifluoroacetate are dissolved in 30 ml

Glacial acetic acid added under reflux with 1.6 g zinc dust. After each hour, 2 times 1.6g of zinc dust are added and one Cooked at reflux. It is sucked off by the excess zinc and the filtrate is evaporated to dryness. The crude product

is purified over a silica gel column (particle size: 0.063-0.2 mm) with ethyl acetate / ethanol / ammonia (90: 10: 0.1 to 80:20:01) and crystallized from ether.

Yield: 0.45 g (64.1% of theory),

Melting point: 214-216 ⁰ C C ₃₃ H ₂₉ N ₃ O ₃ x CF ₃ COOH (629.64)

Calc .: C 66.76 H 4.80 N 6.67

Found: C 66.62 H 5.08 N 6.69

Example 241 4 '· [(2 · (1-trans-butenyl) 6-dimethylaminocarbonylamino-bθnzί-mimidazol-1-yl) -methyl} blpholyl-2-carboxylic acid trifluoroacetate

a) 4 '- [2- (1-Bromobutyl) -6-phthaliminobenzimidazol-1-yl) -niethyl] -blphenyl-2-carboxylic acid tertiary butyne

10.3 g (17.6 mmol) of 4 '- [(2-n-butyl-6-phthaliminobenzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester, carbon tetrachloride and 3.1 g (17, 5 mmol) of N-bromosuccinimide are irradiated for 3 hours while stirring with a mercury immersion lamp. In this case, the internal temperature rises to 5O ⁰ C. It is then filtered from the precipitated greasy product, the residue dissolved in methylene chloride and extracted by shaking with water. The organic phase is dried over sodium sulfate and concentrated by rotary evaporation. The crude product is purified over a silica gel column (particle size: 0.063-0.2 mm) ethyl acetate / petroleum ether (1: 4). Yield: 4.5 g (33.4% of theory)

b) tert-butyl 4M2- (1-trans-butenyl) -6H-halo-imino-benzimidazolyl-methyl-2-phenylphenyl-2-carboxylate

10.8 g (16.25 mmol) of 4 '- [2- (1-bromobutyl) -6-phthaliminobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester, 110 ml of dimethylformamide and 5.1 ml (5.2 g = 34.1 mmol) ie-Diazabicyclolö ^ .Olundec ^ -en are stirred overnight at room temperature. It is pre-diluted with 200 ml of ether and extracted with 2N hydrochloric acid and water. The combined acidic phase is extracted by shaking with ethyl acetate. The ethyl acetate phase is dried over sodium sulfate and purified by rotary evaporation over a silica gel column (particle size: 0.063-0.2 mm) with ethyl acetate / petroleum ether (20:80 to 30:70). Evaporation of the appropriate fractions crystallizes the product. It is filtered off with suction and washed with ether.

Yield: 2.30 g (24.2% of theory), Melting point: 232-234 ⁰ C.

C ₃₇ H ₃₃ N ₃ O ₄ (583.69)

Calc .: C76.14 H5,70 N7.20

Found: C, 75.92, H, 5.69, N, 7.34

c) 4 '- [6-Amino- (2- (1-trans-butenyl) -benzimidazol-1-yl) -methyl] -phenyl-2-carboxylic acid tert-butyl ester

2.3 g (3.94 mmol) of tert-butyl 4 '- [(2- (1-trans-butenyl) -6-phthaliminobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylate, 80 ml of ethanol and 25 ml of 40 % aqueous methylamine are stirred for 3 hours at room temperature. It is heated for a few hours on the steam bath, cooled and rotated. The residue is slurried in acetone, cooled and filtered from undissolved N-methylphthalimide. The filtrate is evaporated to dryness. Yield: 1.78 g (100% of theory), Melting point: 174-176 ⁰ C.

d) 4 '- [(2- (1-trans-butenyl) -6-dimethylaminocarbonyl-quimobenzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester Prepared analogously to Example 8 of 4' - [6 Amino (2- (1-trans-butenyl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert -butyl ester and dimethylcarbamoyl chloride.

Yield: 82.8% of theory,

Oil, Rr value: 0.35 (silica gel, methylene chloride / ethanol = 19: 1)

e) 4 '- [(2- (1-Trans-butenyl) -6-dimethylaminocarbonylamino-benzyl-1-yl) -methyl] biphenyl-2-carboxylic acid trifluoroacetate Prepared analogously to Example 9 from 4'-t (2 - (1-Trans-Butenyl) -6-dimethylaminocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 66.6% of theory, Melting point: 221-223 ° C C ₂₈ H ₂₈ N ₄ O ₃ x CF ₃ COOH x 0.5 H ₂ O (591.59)

Calc .: C 60.90 H 5.11 N 9.47

Found: C, 60.83, H, 4.96, N, 9.53

The following compounds are obtained analogously to Example 241c:

4 '- [(6-Amino-2-n-butyl-benzimidazol-1-yl) -methyl] -2-trifluoromethanesulfonamino-biphenyl oil, Rr value: 0.30 (silica gel: ethyl acetate / ethanol / ammonia = 90: 10: 1) 4 '- [(6-amino-2-n-butyl-benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid melting point: 235-237 ⁰ C.

Example 242

4 '- [(2- (1-trans-butenyl) -6-cyclohexylaminocarbonylaniino-benzimldazol-1-yl) methyl] biphenyl-2-carboxylic acid trifluoi. Prepared analogously to Example 241 from tert-butyl 4 '- [(2- (1-trans-butonyl) -6-cyclohexylaminocarbonylaninobenzimidazol-1-yl) -methyl] biphenyme-2-carboxylate and trifluoroacetic acid in methylene chloride.

Yield: 93.7% of theory, melting point: 171-173 ⁰ C.

C ₃₂ H ₃₄ N ₄ O ₃ χ CF ₃ COOH (636.67)

Calc .: C, 64.14, H, 5.54, N, 8.80

Gef .: C 64.00 H 5.49 N 8.97

Example 243

4 '- [(2-n-Butyl-6- (cis-hexahydrophthalimino) -benziniidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid tert -butyl ester 1.8g (4 mmol) 4' - [(6-amino Tert-butyl 2-n-butyl-benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate _/ 30 ml of glacial acetic acid and 1.85 g (1.2 mmol) of cis-cyclohexane-1,2-dicarboxylic anhydride are stirred for 1 hour with stirring Reflux cooked. The reaction mixture is evaporated to dryness. The residue is washed neutral in methylene chloride, dissolved with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated by rotary evaporation. The crude product is purified over a silica gel column (particle size: 0.063-0.2 mm) with ethyl acetate / petroleum ether (10:90, 20:80 and 30:70).

Yield: 1.5 g (64.1% of theory), C ₃₇ H ₄₁ N ₃ O ₄ (591.80)

Calc .: C75.10 H 6.98 N, 7.10

Found: C 74.92 H 7.10 N 6.99

The following compounds are obtained analogously:

4'-l (2-n-butyl-6- (4,5-dimethyl-1,2,3,6-tetrahydrophthalimino) -benzoimidazol-1-yl) methyl] biphenyl-2 - <: arbon acid tert. butyl ester

Oil, Rf value: 0.30 (silica gel: ethyl acetate / petroleum ether = 1: 1)

4 '- [(2-n-Butyl-6- (3,4-dimethoxy-phthalimino) benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Melting point: 238-239 ⁰ C

4 '- ((2-n-butyl-6- (cis-hexahydrophthalimino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.45 (silica gel: ethyl acetate / petroleum ether = 4: 1)

4 '- [(2-n-butyl-6- (cis-hexahydro-phthalimino) benzimidazol-1-yl) methyl) -2- (1-triphenylmethyl-tetrazol-5-yl) biphenyl

Oil, Rr value: 0.55 (silica gel: ethyl acetate / petroleum ether / ammonia = 80: 20: 1)

4 '- [(2-n-butyl-6- (endo-bicycloI2.2,2] oct-5-en-2,3-dicarbonsäureimino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert. butyl ester

Melting point: 180-182.5 ° C

4 '- [(2-n-butyl-6- (cis-hexahydrophthalimino) -benzimida2ol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester

Oil, Rr value: 0.43 (silica gel: ethyl acetate / petroleum ether = 2: 1)

4 '· [(2-n-butyl-6- (methyl 5-norbornene-2,3-dicarboxylic acid-amino) -benzenedazol-1-yl) -methyl] -biphenyl-2-carboxylic acid tert-butyl ester

4 '- [(2-n-butyl-6- (trans-hexahydro-phthalimino) benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid tert-butyl ester melting point: 168-170 ⁰ C.

4 '- [(2-n-butyl-6- (3,6-endoxo-1,2,3,6-tetrahydro-phthalimino) benzimidazol-1-yl) methyl) biphenyl-2-carboxylate

4 '- [(2-n-butyl-6- (cis-5-norbornene-endo-2,3-dicarbonsäureimino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylate

Melting point: 179-18O ⁰ C

4 '- [(2-n-Butyl-5- (N-cyclohexylaminocarbonyl-methylamino) -benzoimidazol-1-yl) methyl] -2- (1-triphenylmethyl-tetrazol-5-yl) biphenyl

Oil, Rr value: 0.45 (silica gel: ethyl acetate / petroleum ether / ammonia = 90: 10: 1)

4 '- [(2-n-Butyl-5- (cis-hexahydrophthalimino) -benzoimidazol-1-yl) -methylJ-2- (1-triphenylmethyl-tetrazol-5-yl) biphenyl

Oil, Rr value: 0.35 (silica gel: ethyl acetate / petroleum ether = 4: 1)

Example 244

A '- ^ - n-Butyl-e-lcis-hexahydrophthaliminol-benzimidazole-i-vD-methyllbphenyl-α-carboxylic acid trifluoroacetate Prepared analogously to Example 9 from 4' - [(2-n-butyl-6- (cis-hexahydrophthalimino ) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride. Yield: 58.8% of theory,

Melting point: 27O ⁰ C (decomp.) C ₃₃ H ₃₃ N ₃ O ₄ x CF ₃ COOH (649.68)

Calc .: C, 64.71, H, 5.28, N, 6.47

Found: C64.76 H 5.41 N 6.65

Example 245

4 '· [(2-n-butyl-6- (4,5 · dlmethyl) -1,2,3,6-t-thrahydrophthalimino) -boι-zlmldazole * 1 * yl) * methyl] blpholyl * 2-carboxylic acid hydrate

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (4,5-dimethyl-1,2,3,6-tetrahydrophthalimino) benzimidazol-1-yl)

methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 30% of theory,

Melting point: 219-221 ⁰ C

C ₃ SH ₃ SN ₃ O ₄ x H ₂ O (579.69)

Calc .: C 72.52 H 6.43 N 7.23

Found: C, 72.66, H, 6.49, N, 7.43

Example 246

4 '- [(2-n-Butvl-6- (3.4-dimethoxy-phthallmlno) -benzoimidazol-1-Y)) - methyl] biphenyl-2-carboxylic acid-dlhydrat

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (3,4-dimethoxy-phthalimino) -benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 24.3% of theory, Melting point: 206-208 ° C

C ₃₆ H ₃₁ N ₃ O ₆ x 2 H ₂ O (625.68)

Calc .: C 67.19 H 5.64 N 6.72

Found: C 67.22 H 5.84 N 6.97

Example 247

4 '- [(2 x n-butyl · 6 · (N · (dimθthylamlnocarbonyl) · n-pontylamiι ^λ .o) · · benzlιnldazol 1 yl) methyl] blphθnyl-2 · carbons8ure-trifluoracθtat

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (N- (dimethylaminocarbonyl) -n-pentylamino) -benzimidazol-1-yU]

methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 81.8% of theory, Melting point: 174-176 ⁰ C C33H40N4O3 χ CF ₃ COOH (654.73)

Calc .: C64.21 H 6,31 N 8,55

Found .: C, 64.38, H, 6.28, N, 8.64

Example 248

4 '- [(2-n-Butyl-6- (N- (4-phenylamino-n-butyl) -n-piperylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 4 '- ((2-n-Butyl-6- (N- (4-phenylamino-n-butyl) -n-pentylamino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid in methylene chloride.

Example 249

4 '- [(2-n-butyl-6-cyclohexylaminocarbonylamino-ben2imidazol-1-yl) methyl] -2- (1H-tetrazol-5-yl) -blphenyl

Prepared analogously to Example 58 from 4 '- [(6-amino-2-n-butylbenzimidazol-1-yl) methyl-2- (1H-tetrazol-5-yl) -hiphenyl and Cyclohoxylisocyanate in methylene chloride. Yield: 55.1% of theory Melting point: 232-234 ° C

C ₃₂ H ₃₈ N ₈ O (548.69)

Calc .: C 70.05 H 6.61 N 20.42

Found: C 69.86 H 6.66 N 20.25

Example 250

4 '- [(2-n-butyl-6-dimethyl-aminoaminocarbonylamino) -biolazolidazole-1-yl) -methyl] -2- (1H-tetrazol-5-yl) -blpholyl

Prepared analogously to Example 58b from 4'- [(2-n-butyl-6-dimethylaminoaininocarbonylaminobenzimidazol-1-yl) methyl] -2 (1

triphenylmethyl-tetrazol-5-yl) -biphenyl and hydrochloric acid in ether / methanol / methylene chloride.

Yield: 69.8% of theory, Melting point: 239-241 ⁰ C

C ₂₈ H ₃₀ N ₈ O (494.60)

Calcd .: C 67.99 H 6.11 N 22.65

Found: C 67.85 H 6.08 N 22.55

Example 251

4 '· [(2-n-Butyl · 6- (N - (- cyclohexylamlnoarninocarbonyl · nlβthylamlno) -benzlmidazol-1-yl) methyl] -2- (1 H-5 × tθtrazol yl) -blphβnylhydrat

Prepared analogously to Example 58b from 4'- | (2-n-butyl-6- (N-cyclohexylaminoaminocarbonyl-methylamino) -benzimidazol-1-yl) -

methyl) -2- (1-triphenylmethyl-tetrazol-5-yl) -biphenyl and hydrochloric acid in methylene chloride / ether / methanol.

Yield: 97.5% of theory, melting point: 163-165 ⁰ C.

C ₃₃ H ₃₈ N ₈ O x H ₂ O (580.73)

Bar .: C 68.25 H 6.94 N 19.30

Found .: C 68.43 H 6.90 N 19.15

Example 252

4 '- [(2-n-Butyl-6-cyclohexylamino-aminocarbonylamino-boiuimidazol-1-yl) -methyl] -2-trifluoromethanesulfonamino-bliphenyl Prepared analogously to Example 7 from 4' - [(6-amino-2-n-butylbenzimidazoM) yl) -methyl] -2-trifluoromethanesulfonaminobiphenyl and cyclohexyl isocyanate.

Yield: 90.9% of theory, melting point: 163-165 ⁰ C.

C ₃₂ H ₃₆ F ₃ N ₆ O ₃ S (627.73)

Re: C61.23 H5.78 N 11.15

Found: C61.12 H 5.67 N 11.29

Example 253

4 '- [(2-n-Butyl-6-cyclohexylaminocarbonyloxy-benziniidazol-1-yl) -methyl] b! Phenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'- (2-n-butyl-6-cyclohexylaminocarbonyloxy -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and tifluoroacetic acid in methylene chloride.

Yield: 80.0% of theory, melting point: 218-219 ° C

C ₃₂ H ₃₅ N ₃ O ₄ (525.65)

Calc .: C 73.12 H 6.71 N 7.99

Found: C, 73.04, H, 6.84, N, 7.92

Example 254 4 '- [(2-n-Butyl-6-cyclohexyloxycarbonylamino-benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-1 (2-n-butyl-6-cyclohexyloxycarbonylamino -benzimidazol-1-yl) -ethyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 90.9% of theory, melting point: 238-240 ° C

C ₃₂ H ₃₅ N ₃ O ₄ (525.65)

Calc .: C73.12 H 6.71 N 7.99

Found .: C73.18 H6.74 N8.11

Example 255

4 '- [(2-n-butyl-6-morpholinocarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-morpholinocarbonylamino-benzimidazole -1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 85.0% of theory, Melting point: 278-279 ⁰ C.

C ₃₀ H ₃₂ N ₄ O ₄ (512.61)

Calc .: C 70.29 H 6.29 N 10.93

Found .: C 70.28 H 6.28 N 11.00

Example 256

4 '- [(2-n-butyl-6-pyrrolidinocarbonylaminobenzimidazole-1-yl) -methyl] -phenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-pyrrolidinocarbonylaminobenzimidazole -1 -yl-methyl-biphenyl-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Example 257

4 '- [(2-n-butyl 6 * (N-methylaminocarbonyl) IM- (3-cyclohexyl-n-propyl) amino) -benzenimidazol-1-yl) methyl] biphosyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-N- (3-cyclohexyl-n-propyl) -amino) -benzimidazol-1-yl) -methyl] biphenyl-2 carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 84.8% of theory, melting point: 215-216 ⁰ C.

C ₃₆ H ₄₄ N ₄ O ₃ (580.72)

Calc .: C, 74.45, H, 7.64, N, 9.65

Found .: C 74.52 N 7.75 N 9.76

Example 258

4 '- [(2-n-butylbenzimidazol-1-yl) methyl] -2-phenylnaphthalene-3-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-benzimidazol-1-yl) -methyl] -2-phenylnaphthalene-3-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 57% of theory,

Melting point: sinters at 100 ° C. ₂₉ H ₂₆ N ₂ O ₂ (434.54)

Calcd .: C, 80.34, H, 5.81, N, 6.46

Found: C80.63 H 5.89 N 6.28

Example 259

4 '- [(2-n-butylbenzimidazol-1-yl) methyl] -1-phenylnaphthalene-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butylbenzimidazol-1-yl) -methyl] -1-phenylnaphthalene-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 42.5% of theory,

Melting point: 218-22O ⁰ CC ₂₉ H ₂₆ N ₂ O ₂ (434.54)

Ben: C 80.34 H 5.81 N 6.46

Found: C, 80.18, H, 6.01, N, 6.55

Example 260

Prepared as in Example 59 from 4 '- [(2-n-butyl (cis-hexahydro-phthalimino-benzimidazol-1-yl) -methyl] -1-cyano-2-phenylnaphthalene and ammonium chloride / sodium azide.

Example 261

4 '- [(2-n-Propyl-6- (N-cyclohexylaminocarbonylmethylamino) benzimidazol-1-yl) -niethyl] -1- (1H-tetrazol-5-yl) 2-phenylnaphthalene Prepared analogously to Example 59 4 '- [(2-n-Propyl-6- (N-cyclohexylaminocarbonyl-methylamino) -benzimidazol-1-yl) -methyl] -1-cyano-2-phenylnaphthalene and ammonium chloride / sodium azide.

Example 262

4 '- [(2-n-propyl-6- (N-cyclohexylamino-carbonyl-methylamino) -benzimidazol-1-yl) -methyl] -2-phenyl-naphthalene-1-carboxylic acid Prepared analogously to Example 9 from 4' - [(2- n-Propyl-6- (N-cyclohexylaminocarbonyl-methylamino) -benzimidazol-1-yl) -methyl] -2-phenyl-naphthalene-1-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 73.0% of theory,

Melting point: 193-195 ° C

C ₃₆ H ₃₈ N ₄ O ₃ (574.70)

Ben: C 75.28 H 6.67 N 9.75

Found .: C75.10 H 6.71 N 9.72

Example 263

4 '- [(2-n-butyl-benzimidazol-1-yl) -methyl] -2-phenyl-naphthalene-1-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butylbenzimidazol-1-yl) -methyl] -2-phenylnaphthalene-1-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 89.0% of theory, m.p .: 228-23O ⁰ CC ₂₉ H ₂₆ N ₂ O ₂ (434.61)

Calc .: C80.16 K6.03 N6.45

Found: C 80.11 H 6.00 N 6.30

Example 264

4 '- [(2-n-butyl-6- (cis-hexahydro-phthalimino) benzimidazol-1-yl) methyl] -2-phenylnaphthalln-1-carboxylic acid

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -methyl] -2-phenylnaphthalene

1-carboxylic acid tert.butyl ester and trifluoroacetic acid. Yield: 37.0% of theory, m.p .: 215-218 ⁰ CC ₃₆ H ₃₃ N ₃ O ₄ (571.65)

Calcd .: C, 75.63, H, 5.82, N, 7.35

Found: C, 75.47, H, 5.63, N, 7.11

Example 265

4 '- [(2-n-Butyl-6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -methyl] -4-bromo-biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [( Tert-butyl 2-n-butyl-6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -metliyl] -4-bromo-biphenyl-2-carboxylate and trifluoroacetic acid.

Yield: 63.0% of theory, m.p .: 198-200 ° CC ₃₃ H ₃₂ BrN ₃ O ₄ (614.56)

Calc .: C 64.50 H 5.25 N 6.84 Br 13.00

Found: C 64.38 H 5.22 N 6.73 Br 13.05

Example 266

4 '- [(2-n-butyl-benzimidazol-1-yl) -methyl] -4-bromo-phenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2-n-butyl-benzimidazol-1 - yl) -methyl] -4-bromo-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Yield: 88% of theory,

Melting point: 209-211 ° C

C ₂₆ H ₂₃ BrN ₂ O ₂ (463.39)

Calc .: C64.80 H 5.00 N 6.05 Br 17.25

Found: C 64.68 H 5.14 N 5.97 Br 17.26

Example 267

4 '- [(2-n-butyl-benzimidazol-1-yl) -methyl] -5-chloro-phenyl-2-carboxylic acid Prepared analogously to Example 9 in 4Μ (2-η ·ΒανΙβηζϊηιία8ζοΙ-1-νΙ) ίτιβ% Ι | · 5 <ηΙθΓ-ΜρπβηνΙ-2-03 ^ οη53υΓβ-1βΓΐ ^ υ (νΙβ8ΐβΓ and trifluoroacetic acid.

Yield: 74% of theory,

Melting point: 188-19O ⁰ C

C ₂₆ H ₂₃ CIN ₂ O ₂ (418.91)

Ben: C 71.67 H 5.53 N 6.69

Found: C, 71.49, H, 5.52, N, 6.66

Example 268

4 '- [(2-n-butyl-6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -methyl] -4-chloro-2- (1H-tetrazol-5-yl) -biphenyl Prepared analogously Example 59 from 4 '- [(2-n-butyl-6- (cis-hexahydru-phthalimino) -benzimidazol-1-yl) -methyl-M-chloro-cyano-biphenyl and ammonium chloride / sodium azide.

Yield: 25.0% of theory,

Melting point:> 125 ° C

C ₃₃ H ₃₂ CIN ₇ O ₂ (594.11)

Calc .: C 66.71 H 5.43 N 16.50 Cl 5.87

Found: C66.54 H5.63 N 16.35 CI5.91

Example 269

4 '- [(2-n-Butyl-6- (N-cyclohexylamino-carbonyl-methylamino) -benzimidazol-1-yl) -methyl] -4-chloro-2- (1H-tetrazol-5-yl) -biphenyl analogously to Example 59 from 4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-methylamino) -benzimidazol-1-yl) -methyl] -4-chloro-2-cyano-biphenyl and ammonium chloride / sodium azide.

Example 270

4 '- [(2-n-Butyl-6- (N- (n-dodecylaminocarbonyl) -methylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid trifluoroacetate Prepared analogously to Example 9 of 4'-I (2-n-butyl-6- (N- (n-dodecylaminocarbonyl) methylamino) -benzoimidazol-1-yl) -methylJ-biphenyl ^ -carboxylic acid tert.butylesterinTrifluoressigsäure / methylene chloride.

Yield: 85.7% of theory, m.p .: 61-62 ° C (amorphous) C ₃₉ H ₆₂ N ₄ O ₃ x CF ₃ COOH (738.89)

Calc .: C 66.65 H 7.23 N 7.58

Found: C, 66.68, H, 7.47, N, 7.83

Example 271

4 '- [(2-n-Butyl-6- (N- (cyclohexylaminocarbonyl) -n-octylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 72 from 4' - [(2 -n-butyl-6- (N- (cyclohexylaminocarbonyl) -n-octylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid ethyl ester in ethanol / 2N sodium hydroxide.

Yield: 94.9% of theory, melting point: 151-152 ⁰ C.

C ₄₀ H ₆₂ N ₄ O ₃ (636.88)

Calc .: C, 75.44, H, 8.23, N, 8.80

Found: C, 75.63, H, 8.37, N, 8.92

Example 272

4 '- [(2-n-Butyl-6- (N- (n-octylamino-carbonyl) -methylamino) -benzlmldazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 of 4' - ((2 -n-Butyl-6- (N- (n-octylaminocarbonyl) -methylamino) -benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid tert-butyl ester in trifluoroacetic acid / methylene chloride.

Yield: 87.5% of theory, melting point: 169-17O ⁰ C.

C35H44N4O3 (568.76)

Calc .: C 73.91 H 7.80 N 9.85

Found: C 73.98 H 7.95 N 9.78

Example 273

4 '- [(2-n-butyl-6- (cis-hexahydro-phthalomino) -bithiazolazid-1-yl) .methyl] .2 * (1H.totarzol .5-yl) bipholinyl Prepared analogously to Example 58 in FIG. I (2-n-butyl-6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -methyl] -2- (1-triphenylmethyl-tetrazol-5-yl) -biphenyl and hydrochloric acid in ether / methanol / methylene chloride.

Yield: 47.6% of theory, m.p .: 147-149 ° C

C ₃₃ H ₃₃ N ₇ O ₂ (559.67)

Calc .: C 70.82 H 5.94 N 17.52

Gef .: C70.61 H6.12 N 17.63

Example 274

4 '- [(2-n-butyl-6- (endo-bicyclo [2.2.2] oct-5-en-2,3-dlcarbonsäurelmlno) -benzlmidazol-1-yl) methyl] biphenyl-2-carbonsäuretrlfluoracetat

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-6- (endobicyclo [2.2,2-oct-5-en-2,3-dicarboximino) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 88.6% of theory, m.p .: 161-163 ° C

C ₃₅ H ₃₃ N ₃ O ₄ x CF ₃ COOH (673.69)

Calcd .: C 65.96 H 5.08 N 6.23

Found: C 65.72 H 4.99 N 6.11

Example 275

4 '- [(2-n-Butyl-6- (methyl-5-norbornene-2,3-dicarboxylic acidiniino) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid (mixture of isomers)

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (methyl-5-norbornene-2,3-dicarboximino) -benzimidazol-1-yl) -methy!] Biphenyl-2-carboxylic acid tert. butyl ester (mixture of isomers) and trifluoroacetic acid in methylene chloride.

Example 276

4 '- [(2-n-Butyl-6- (trans-hexahydro-phthalimino) -benzlmldazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid dihydrate Prepared analogously to Example 9 from 4' - [(2-n Butyl-6- (transhexahydro-phthalimino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 60.7% of theory, Melting point: 188-190 ⁰ C (dec.) C ₃₃ H ₃₃ N ₃ O ₄ x 2 H ₂ O (571.67)

Calc .: C 69.33 H 6.52 N 7.35

Gof .: C 69.48 H 6.40 N 7.57

Example 277

4 '- [(2-n-Butyl-6- (3,6-endoxo-1 _l 2,3,6-tetrahydro-phthalimino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 of 4'- | (2-n-butyl-6- (3,6-endoxo-1,2,3,6-tetrahydro-phthalimino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Example 278

4 '- [(2-n-butyl-6- (cis-5-norbornene-endo-2,3-dicarbonsäureimlno) -benzimldazol-1-yl) methyl] biphenyl-2-carbonsäuremonohydrat

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (cis-5-norbornene-endo-2,3-dicarboxylic acid imino) benzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester and Trifluoroacetic acid in methylene chloride.

Yield: 22.1% of theory, m.p .: 263-265 ° C

C ₃₄ H ₃ ) N ₃ O ₄ x H ₂ O (563.65)

Calc .: C, 72.44, H, 5.90, N, 7.45

Found .: C 72.28 H 5.81 N 7.46

Example 279

4 '- [(2-n-Butyl 6 (2-carboxycyclohexylcarbonylamino) -bithium-azazol-1-yl) -methyl] -phenyl-2-carboxylic acid 0.6 g (1.5 mmol) 4' - [(6-amino-2-) n-Butyl-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid are dissolved with warming in 150 ml of methylene chloride and cooled to room temperature. After addition of 240 mg (1.55 mmol) of cis-cyclohexane-1,2-dicarboxylic anhydride is stirred for 5 hours at room temperature. The crystallized reaction product is filtered off, washed with methylene chloride and dried in a vacuum oven at 50 ⁰ C.

Yield: 0.58 g (69.8% of theory), Melting point: 186-188 ^C C

C ₃₃ H ₃₆ N ₃ O ₆ (553.66)

Calc .: C71.59 H6.37 N7.59

Found: C, 71.42, H, 6.56, N, 5.56

Example 280

4 '- [(2-n-Butyl-6- (2-carboxy-cyclohexylcarbonylamino) -benzimidazol-1-yl) -methyl] -4-bromo-biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [( Tert-butyl 2-n-butyl-6- (cis-hexahydrophthalimino) -benzimidazol-1-yl) -methyl] -4-bromo-biphenyl-2-carboxylate and trifluoroacetic acid in methylene chloride.

Yield: 88% of theory

Melting point: from 145 ° C (decomp.) C ₃₃ H ₃₄ BrN ₃ O ₆ (632.58)

Calcd .: C, 62.66, H, 5.42 Br, 12.63, N, 6.64

Found: C62.50 H5.33 Br12.78 N6.43

Example 281

4 '- [(2-n-Butyl-6- (3-carboxy-cis-5-norbornene-endo-2-carbonylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 of FIG '- [(2-n-Butyl-6- (cis-5-norbornene-endo-2,3-dicarboxylic acidimino) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert -butyl ester and trifluoroacetic acid in methylene chloride ,

Yield: 17.1% of theory, melting point: 199-201 ° C

C ₃₄ H ₃₃ N ₃ O ₆ (563.66)

Calc .: C, 72.44, H, 5.90, N, 7.45

Found: C, 72.26, H, 5.82, N, 7.44

Example 282 Prepared analogously to Example 9 from 4'-1 (2-n-butyl-6-dimethylaminocarbonyloxy-benzimidazol-1-yl) -methyl) biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield; 81.9% of theory, Melting point: 241-242 ⁰ C.

C ₂₈ H ₂₉ N ₃ O ₄ (471.56)

Calc .: C 71.32 H 6.20 N 8.91

Gef .: C71.15 H6,28 N8.89

Example 283

4 '- [(2 * n-Butyl-6- (N-acetyl-n-octylamino) -benzimidazol-1-yl) -methyl] blpholyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n Butyl-6- (N-acetyl-n-octylamino) -benzimidazol-1-yl) -methyl-bipheny! -2-carboxylic acid tert -butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 77.2% of theory, Melting point: 192-193 ⁰ C.

C ₃₆ H ₁₃ N ₃ O ₃ (533.74)

Calc .: C, 75.92, H, 7.83, N, 7.59

Found: C 75.75 H 8.03 N 7.45

Example 284

4 '- [(2-n-Butyl-6- (2-phenylethylaminocarbonyl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert -butyl ester 484 mg (1 mmol) 4' - [(2-n Butyl-6-carboxy-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester are dissolved in 10 ml of absolute tetrahydrofuran and cooled to -2O ⁰ C with stirring and dry ice / isopropanol cooling. At this temperature, 101 mg (1 mmol) of N-methylmorpholine are added. It is then cooled to -30 ⁰ C and a solution of 136mg (1 mmol) of isobutyl chloroformate, dissolved in 5 ml of absolute tetrahydrofuran, added dropwise slowly. For complete formation of the mixed anhydride for one hour at -4O ⁰ C is stirred. At -4O ⁰ C is added dropwise 134mg (1.1 mmol) of 2-phenylethylamine, dissolved in 2ml of absolute tetrahydrofuran, slowly added. Thereafter, the temperature is allowed to rise slowly to room temperature and stirred for 16 hours at room temperature. The solvent is distilled off, the residual viscous oil is taken up in saturated brine acetic acid and extracted a total of 3 times with ethyl acetate. The ethyl acetate phases are dried over sodium sulfate and concentrated. The viscous oil is dissolved in methylene chloride and purified on a silica gel column (eluent: methylene chloride / ethanol = 50: 1 and 25: 1).

Yield: bO5mg (86% of theory), oil, Rr value: 0.5 silica gel: ethanol / methylene chloride = 1:19) C ₃₈ H ₄₁ N ₃ O ₃ (587.80)

Calc .: C 77.65 H 7.03 N, 7.15

Gef. C 77.58 H 7.24 N 7.34

The following compounds are obtained analogously:

4 '- [(2-n-Butyl-6- (2-phenylamino-ethylaminocarbonyl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester oil, Rp value: 0.45 (silica gel: ethanol / Methylene chloride = 1:19) tert-butyl 4 '- [(2-n-butyl-6- (5-carboxy-n-pentylaminocarbonyl) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylate. Melting point: 166- 167 ° C

Example 285

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (2-phenylethylaminocarbonyl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 19.7% of theory, Melting point: 208-210 ⁰ C.

C ₃₄ H ₃₃ N ₃ O ₃ (531.65)

Calc .: C 76.81 H 6.26 N 7.90

Found: C76.69 H6.48 N7.92

Example 286

4 '- [(2-n-Butyl! -6- (2-phenylaminoethylaminocarbonyl) -benzlmidazol-1-yl) -methyl] biphenyl-2-carboxylic acid X 1.5HCl Prepared analogously to Example 9 of 4' - [(2-n- Eutyl-6- (2-phenylaminoethylaminocarbonyl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert -butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 30% of theory,

Melting point: 240-242 ⁰ C

C ₃₄ H ₃₄ N ₄ O ₃ χ 1.5HCl (601.36)

Calc .: C67.91 H 5.95 N 9.32

Found: C, 67.88, H, 5.93, N, 9.15

Example 287

4 '- [(2-n-Butyl-6- (5-carboxy-n-pentylamino-carbonyl) benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - ((2-n Butyl-6- (5-carboxy-n-pentylaminocarbonyl) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 37.4% of theory, melting point: from 116 ° C. (dec.) C ₃₇ H ₃₅ N ₃ O ₆ (541.70)

Ben: C 70.96 H 6,51 N 7,76

Found: C, 70.84, H, 6.42, N, 7.85

Example 288 Prepared analogously to Example 72 from 4 '- [(2-n-butyl-6- (2-carboxy-propionyl) -bonzimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid

methyl ester and caustic soda / methanol.

Example 289

4 '- [(2-n-butyl-6-homo-thallomino-ben2-imidazoM-yl) -niethyl] -blphenyl-2-carboxylic acid tert -butyl ester 1.5 g (3.3 mmol) 4 ^l - ((6-amino-2 -n-butylbenzimidazol-1-yl) -niethyl) biphenyl-2-carboxylic acid tert -butyl ester and 0.6g (3,63mMcl)

Homophthalic anhydride are refluxed in 20 ml of pyridine for 20 hours. Subsequently, the solvent is in

Vacuum removed and the residue on a silica gel (particle size: 0.063-0.2mm, eluent, methylene chloride / ethanol = 100: 2,100: 3 and 100: 5).

Yield: 15.2% dor theory, Melting point: 109-112 ⁰ C.

C ₃₈ H ₃₇ N ₃ O ₄ (599.73)

Ber .: C7G, 10 H6.22 N7.01

Found: C 75.90 H 6.28 N 6.90

The following compounds are obtained analogously:

4 '- [(2-n-Butyl-6- (3,3-tetramethylene-glutarimino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert -butyl ester 4' - [(2-n- Butyl-6- (3,3-pentamethylene-glutarimino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester 4 '- ((2-n-butyl-6- (7-methoxy-homophthalimino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester 4 '- [(2-n-butyl-6- (4,4-dimethyl-7-methoxy-homophthalimino) -benzimidazole-1 yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester 4 '- [(2-n-butyl-6- (6,7-dimethoxy-homophthalimino) -benzimidazol-1-yl) -methyl] biphenyl-2- tert-butyl carboxylic acid 4'-l (2-n-butyl-6- (6,7-dimethoxy-4,4-dimethyl-homophthalimino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester

4'- | (2-n-butyl-6-glutariminobenziinidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert-butyl ester 4 '- [(2 * n-butyl-6- (3-methylglutarimino) benzimidazol-1-yl) m-butyl] biphenyl 2-carboic acid tert-butyl ester 4'-l (2-n-butyl-6- (3,3-dimethyl-glutarimino) -benzimidazol-1-yl) -methyl] Biphenyl-2-carboxylic acid tert-butyl ester 4 '- [(2-n-butyl-6- (3-ethyl-3-methyl-glutarimino) -benzimidazol-1-yl) -methyl-biphenyl-2-carboxylic acid tert-butyl ester 4 '- [(2-n-Butyl-6- (cis-hexahydrophthalimino) -benzimidazol-1-yl) -methyl) -2- (1-triphenylmethyltetrazol-5-yl) biphenyl 4' - [(2- n-butyl-6- (4,4-dimethyl-homophthalimino) -benzoimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid tert-butyl ester

^ '- ^ - n-Butyl-e-iS-methyl-hexahydrophthaliminoJ-benzimidazol-i-YLJ-methyllbiphenyl ^ -carboxylic acid tert.-butyl ester

Oil, Rp value: 0.75 (silica gel, ethyl acetate / petroleum ether = 4: 1)

Example 290

4 '- [(2-n-Butyl-6-homophthalimino-benzimidazol-1-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n-butyl-6-homophthaliminobenzimidazole -1-yl) -methyl] biphenyl-2-carboxylic acid tert.butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 79% of theory,

Melting point: 171-173 ⁰ C

C ₃₄ H ₂₉ N ₃ O ₄ (543.62)

Calc .: C 75.12 H 5.38 N 7.73

Found .: C 74.95 H 5.18 N 7.64

Example 291

4 '- [(2-n-butyl-6- (4,4-dlmethyl-homophthallmino) -benzoimidazol-1-yl) methyl] biphenyl-2-carbonsäuro monohydrate

Prepared analogously to Example 9 from 4 '- [(2-n-3-butyl-6- (4,4-dimethyl-homophthalimino) -benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 77.4% of theory, Melting point: 299-301 ⁰ C.

C ₃₆ H ₃₃ N ₃ O ₄ x H ₂ O (589.69)

Calc .: C 73.33 H 5.98 N 7.13

Found: C 73.60 H 6,14 N 7,33

Example 292

4 '- [(2-n-Butyl-6- (3,3-tetramethylene-glutarimino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'- (2-n -Bjtyl-6- (3,3-tetramethylene-glutarimino) -benzoimidazol-1-yl) methyl) biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 40.0% of theory, m.p .: 191-194 ° C

C ₃₄ H ₃₆ N ₃ O ₄ (549.64)

Calc .: C 74.29 H 6.42 N 7.65

Found .: C 74.08 H 6.31 N 7.52

Example 293 Prepared analogously to Example 9 from 4M (2-n-butyl-6- (3,3-pontamothylon-glutarimino) -benzimidazol-1-yl) -methyl) biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid In methylene chloride

Yield: 31.0% of theory, Melting point: 182-185 ⁰ C C35H37N3O4 (563.67)

Boron: C 74.57 H 6.62 N 7.46

Found .: C, 74.43, H, 6.52, N, 7.32

Example 294

4 '- [{2-n-Butyl-6- (cis-hexahydrodphthalene) -bonzlmldazol-1-yl) -mothyl] -5-chloro-2- (1H-tetrazol-5-yl) -blphenyl Prepared analogously Example 59 from 4 '- [(2-n-butyl-6- (cis-hexahydro-phthalimino) -benzimidazol-1-yl) -methyl) -5-chloro-2-cyanobiphenyl and sodium azide / ammonium chloride.

Yield: 22.0% of theory, Melting point: from 135 ⁰ C (sintered)

C ₃₃ H ₃₂ CIN ₇ O ₂ (594.10)

Calc .: C 66.71 H 5.43 N 16.50 Cl 5.97

Found: C66.51 H5.39 N 16.77 Cl 5.92

Example 295

4 '× [(2 × n-butyl-6 × (N-cyclo-hexylamino-carbonylamino] -benzimidazole × 1 × yl) -methyl] × 5 × chloro-2 × (1H-tetrazol-5-yl) × blphOnyl Prepared analogously to Example 59 4M (2-n-butyl-6- (N-cyclohexylaminocarbonylamino) -benzimidazol-1-yl) -methyl-5-chloro-2-cyano-biphenyl and sodium azide / ammonium chloride.

Example 296

4 '- [(2-n-Butyl-6- (7-methoxy-homophthalimino) -benzimidazoM-yl) -methyl] -bliphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' · | (2-n · butyl · 6) - (7-mothoxy-homophthalimino) -benzimidazol-1-yl) -methyl] biphenyl · 2-carboxylic acid tert-butyl ester and trifluoroacetic acid.

Example 297

4 '- [(2-n-butyl-6- (4,4-dimethyl-7-methoxy-homophthalimino) -bβnzlmldazol-1-yl) -methyl] -biphonyl-2-carboxylic acid. Prepared analogously to Example 9 from 4' - [( 2-n-Butyl-6- (4,4-dimethyl-7-methoxy-homophthalimino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert -butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 60.1% of theory, melting point: 104-105 ⁰ CC ₃₇ H ₃₅ N ₃ O ₆ (601.70)

Calc .: C, 73.86, H, 5.86, N, 6.98

Found: C 73.92 H 6.04 N 7.11

Example 298

4 '· [(2 · n · butyl · 6 (6,7 dimethoxy · homophthalimino) · bθnzimidazol-1-yl) · mθthyl] blphθnvl-2 · carboic acid

Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (6,7-dimethoxy-homophthalimino) -benzimidazol-1-yl) -methyl] biphenyl-2-

carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Example 299

4 '- [(2-n-butyl-6- _(6> 7-dimethoxy-4,4-dlmethyl-homophthallmi.io) -benzlmidazol-1-yl) methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4 '- [(2-n-Butyl-6- (6,7-dimethoxy) -dimethyl-homophthaliminol-benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert -butyl ester and trifluoroacetic acid in methylene chloride.

Example 300

4 '- [(2-n-Butyl-6- (3,3-pentamethylene-glutarimino) -benzlmldaiol-1-yl) -methyl] -2- (1H-tetra-ol-5-yl) -blonphonyl Prepared analogously to Example 59 from 4 '- [(2-n-butyl-6- (3,3-pentamethylene-glutarimino) -benzimidazol-1-yl) -ethyl) -2-cyanobiphenyl and sodium azide / ammonium chloride.

Yield: 29.0% of theory, melting point: from 140 ° C. (sintered) C ₃₅ H ₃₇ N ₇ O ₂ (587.70)

Calc .: C 71.52 ^ H 6.35 N 16.68

Found: C71.37 H6.20 N 16.71

Example 301

4 '- [(2-n-Butyl-6- (3,3-tetramethylene-glutarimino) -benzimidazol-1-yl) -methyl] -2- (1H-tetrazol-5-yl) -biphenyl Prepared analogously to Example 59 from 4 '- [(2-n-butyl-6- (3,3-tetramethylene-glutarimino) -benzimidazol-1-yl) -meyl] -2-cyano-biphenyl and sodium azide / ammonium chloride.

Yield: 31.0% of theory, melting point: from 166 ° C. (sintering) C ₃₄ H ₃₅ N ₇ O ₂ (573.68)

Calc .: C71.18 H6,15 N 17,09

Gef .: C71.10 H6,22 N 17,20

Example 302

4 [(2ηΒυΙνΙ6 (3,3ΐΘίΓΗιηθΙΙ) νΙθη9ΐΙη) ν) ν] (ν) ρν

Prepared analogously to Example 59 from 4 '- [(2-n-butyl-6- (3,3-tetramethylene-glutarimino) -benzimidazol-1-yl) -methylJ-4-chloro-2-cyano-

biphenyl and sodium azicl / ammonium chloride.

Example 303 4 '- [(2-n-Butyl-6-glutarolminobenzimlzinc-1-yl-1-yl) -methyl] biphenyl-2-coreacanoic acid Prepared analogously to Example 9 from 4M (2-n-butyl-6-glutarimino-benzimidazole) 1-yl) -methyl | biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 82.0% of theory, melting point:> 220 ° C

C ₃₀ H ₂₉ N ₃ O ₄ (495.56)

Calc .: C 72.71 H 5.90 N 8.48

Found: C 72.56 H 5.79 N 8.22

Example 304

4 '- [(2-n-Butyl-6-glutarimino-benzimidazol-1-yl) -methyl] -2- (1H-tetrazol-5-yl) -biphenyl Prepared analogously to Example 59 from 4'-l (2- n-butyl-6-glutarimino-benzimidazol-1-yl) -methyl] -2-cyano-biphenyl and sodium azide / ammonium chloride.

Yield: 47.0% of theory,

Melting point: from 139 ° C (sintering)

C ₃₀ H ₂₉ N ₇ O ₂ (519.59)

Calc .: C 69.34 H 5.62 N 18.87

Gef .: C69.30 H5.52 N 18.69

Example 305

^ - [(Zn-Butyl-e-IS-methyl-glutarininol-benzimidazole-Vyll-methyl-biphenylcarboxylic acid Prepared analogously to Example 9 from 4 '- [(2-n-butyl-6- (3-methylglutarimino) -benzimidazole] Tert-butyl) and trifluoroacetic acid in methylene chloride.

Yield: 39.0% of theory, melting point:> 220 ° C

C ₃₁ H ₃₁ N ₃ O ₁ (509.58)

Calc .: C73.06 H6,13 N8,25

Found: C, 72.91, H, 5.88, N, 8.02

Example 306

4 '- [(2-n-Butyl-G- (3-methyl-glutarimino) -benzimidazol-1-vl) -methyl] -2- (1H-tetrazol-5-yl) -biphenyl Prepared analogously to Example 59 of FIG. 4 '- [(2-n-Butyl-6- (3-methyl-glutarimino) -benzimidazol-1-yl) -methyl] -2-cyano-biphenyl and sodium azide / ammonium chloride.

Yield: 28.0% of theory, Melting point: from 157 C (sinter) C ₃ IH ₃₁ N ₇ O ₂ (533.61)

Calc .: C69.77 H 5.86 N 18.38

Found .: C 69.69 H 5.81 N 18.16

Example 307

4 '[(2-n-butyl-6- (3-methyl-glutarimino) benzimidazol-1-yl) -methyl] 4-chloro-2 (1H-tetrazol-5-yl) -biphidine Prepared analogously to Example 59 from 4 '- ((2-n-butyl-6- (3-methyl-glutarimino) -benzimidazol-1-yl) -methyl) -4-chloro-2-cyanobiphenyl and sodium azide / ammonium chloride.

Example 308

4 '- [(2-n-Butyl-6- (3,3-dimethyl-glutarimino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4' - [(2-n Butyl-6- (3,3-dimethyl-glutarimino) -benzimidazol-1-yl) -methyl) biphenyl-2-carboxylic acid tert -butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 41.0% of theory,

Melting point:> 22O ° C

C ₃₂ H ₃₃ N ₃ O ₄ (523.61)

Calc .: C 73.40 H 6.35 N 8.03

Found .: C 73.29 H 6.21 N 7.91

Example 309

4 '- [(2 · n · Buty! · 6 · (3,3-dimethylglutarimino) · benzimidazol-1 · yl) -methyl} -2 · (1H-tetrazole · 5 · yl) · biphenyl Prepared analogously to Example 59 4 '- [(2-n-Butyl-6- (3,3-dimethyl-glutarimino) -benzimidazo-1-yl) -methyl-2-cyano-biphenyl and sodium azide / ammonium chloride.

Yield: 29.0% of theory,

Melting point: from 151 "C (sintering)

C ₃₂ H ₃₃ N ₇ O ₂ (547.64)

Calc .: C70.18 H6.07 N 17.91

Found: C, 69.91, H, 5.98, N, 17.85

Example 310

4 '[(2 * n-butyl-6 * (3-ethyl-3-methyl-glutarimino) -benzenesimidazol-1-yl) -ethyl] biphenyl-2-carboxylic acid

Prepared analogously to Example 9 from 4 '- ((2-n-butyl-6- (3-ethyl-3-methyl-glutarimino) -benzirnidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 38.0% of theory, melting point:> 22O ⁰ C.

C ₃₃ H ₃₅ N ₃ O ₄ (537.63)

Calc .: C 73.72 H 6.56 N 7.82

Gef .:. C 73.55 H 6.41 N 7.76

Example 311

Prepared analogously to Example 59 from 4'- [(2-n-butyl-6- (3-ethyl-3-methyl-glutarimino) -benzimidazol-1-yl) -methyl] -2-cyano-biphenyl and sodium azide / ammonium chloride.

Yield: 26.0% of theory, Melting point: from 138 ⁰ C (sinter) C ₃₃ H ₃₅ N ₇ O ₂ (561.67)

Calc .: C 70.56 H 6.28 N 17.46

Found: C 70.47 H 6.02 N 17.33

Example 312

4 '- [(2-n-butyl-6- (3-ethyl-3-methyl-glutarimino) -benzoimidazol-1-yl) methyl] -4-chloro-2- (1H-tetrazol-5-yl) -biphenyl Prepared analogously to Example 59 from 4 '- [(2-n-butyl-6- (3-ethyl-3-methyl-glutarirr, ino) -benzimidazol-1-ylmethyl-M-chloro-cyano-biphenyl and sodium azide / ammonium chloride ,

Example 313

4 '- [(2-n-Butyl-5- (N-cyclohexylaminocarbonyl-methyl-amino) -benzimidazol-1-yl) -methyl] -2- (1H-tetrazol-5-yl) -biphenyl Prepared analogously to Example 58b from FIG. 4 '- [(2-n-Butyl-5- (N-cyclohexylaminocarbonyl-methylamino) -benzimidazol-1-yl) -methyl] -2- (1-triphenylmethyl-tetrazol-5-yl) -biphenyl and hydrochloric acid in methylene chloride / ether / methanol. Yield: 76.2% of theory, melting point: 150-152 ⁰ C.

C ₃₃ H ₃₈ N ₈ O (562.72)

Calcd .: C70.44 H6.80 N 19.91

Found: C70.32 H7.05 N 19.76

Example 314

4 '- [(2-n-Butyl-6- (5-methyl-hexahydrophthalimino) -bonzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid Prepared analogously to Example 9 from 4'-l (2-n-butyl -6- (5-methylhexahydrophthalimino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid tert-butyl ester and trifluoroacetic acid in methylene chloride.

Yield: 37% of theory,

Melting point: 143-146 "C

C ₃₃ H ₃₆ N ₃ O ₄ (549.67)

Calc .: C 74.29 H 6.42 N 7.62

Found: C, 74.47, H, 6.67, N, 7.55

Example 315

4 '- [(2-n-Butyl-5- (cis-hexahydrophthalimino) -benzimidazol-1-yl) -methyl] -2- (1H-tetrazol-5-yl) biphenyl Prepared as in Example 58 from 4' - [( 2-n-Butyl-5- (cis-hexahydrophthalimino) -benzimidazol-1-yl) -methyl-2- (1-triphenylmethyl-tetrazol-5-yl) -biphenyl and hydrochloric acid / ethanol.

Yield: 59.5% of theory, melting point: 230-232 ° C

C ₃₃ H ₃₃ N ₇ O ₂ (559.67)

Calc .: C70.82 H5.94 N 17,52

Found: C70.64 H6.10 N 17.72

Example 316

4 '- [(2-n-butyl-5- (2-carboxymethyl-propionyl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid 0.25H ₂ O Prepared analogously to Example 72 of 4' - [( Methyl 2-n-butyl-5- (2-carboxymethyl-propionyl) -sznzimidazol-1-yl) -methyl] biphenyl-2-carboxylate and sodium hydroxide / ethanol.

Yield: 25% of theory,

Melting point: 223-225 ° C

C ₃₀ H ₃₀ N ₂ O ₆ x 0.25 H ₂ O (503.08)

Calc .: C71.62 H6.11 N5.56

Gef .: C71.56 H6.14 N5.58

In the following pharmaceutical application examples, the active substance used may be any suitable compound of the formula I, e.g. the compounds of the preceding examples:

Example I Ampoules containing 50mg of active ingredient per 5ml Active ingredient 50 mg

KH ₂ PO ₄ 2 mg

Na ₂ HPO ₄ x 2 H ₂ O 50 mg

NaCl 12 mg

Water for injections ad 5 ml

production:

In a part of the water the buffer substances and the isotonan are dissolved. The active ingredient is added and filled with water to the nominal volume after complete dissolution.

Example Il

Ampoules containing 100mg of active ingredient per 5ml

Active ingredient 100 mg

Methylglucamine 35 mg

Glykofurol 1000 mg

Polyethylene glycol polypropylene

Glycol block polymer 250 mg

Water for injections ad 5 ml production:

Methylglycamine is dissolved in one part of the water and the active ingredient is dissolved with stirring and heating. After addition of the solvent is made up to the nominal volume with water.

Example III 50.0 mg Tablets containing 50 mg of active ingredient 70.0 mg active substance 40.0 mg calcium phosphate 35.0 mg lactose 3.5 mg corn starch 1.5 mg polyvinylpyrrolidone magnesium stearate

200.0 mg

production:

The active ingredient, CaHPO ₄ , lactose and corn starch are evenly moistened with an aqueous PVP solution. The mass is passed through a 2 mm sieve, dried in a circulating air drying oven at 50 ° C. and sieved again, and after admixing the lubricant, the granules are pressed on a tableting machine.

Example IV 50.0 mg Dragees containing 50 mg of active ingredient 25.0 mg active substance 60.0 mg lysine 34.0 mg lactose 10.0 mg corn starch 1.0 mg gelatin magnesium stearate

180.0 mg

production:

The active ingredient is mixed with the excipients and moistened with an aqueous gelatin solution. After sieving and drying, the granules are mixed with magnesium stearate and crushed into cores.

The cores thus produced are coated by known methods with a shell. The coating suspension or solution

Dye can be added.

Example V 100.0 mg Dragees, containing 100mg of active ingredient 50.0 mg active substance 86.0 mg lysine 50.0 mg lactose 2.8 mg corn starch 60.0 mg polyvinylpyrrolidone 1.2 mg Microcrystalline cellulose magnesium stearate

350.0 mg

production:

The active ingredient is mixed with the excipients and moistened with an aqueous PVP solution. The moist mass is passed through a 1.5 mm sieve and dried at 45 ° C. After drying, sieved again and the magnesium stearate is mixed in. This mixture is pressed into cores.

The cores thus produced are coated by known methods with a shell. Dyes may be added to the coating suspension or solution.

Example Vl 250.0 mg Capsules containing 250mg active ingredient 68.5 mg active substance 1.5 mg corn starch 320.0 mg magnesium stearate

production:

Active ingredient and corn starch are mixed and moistened with water. The moist mass is sieved and dried. The dry granules are sieved and mixed with magnesium stearate. The final mixture is filled into hard gelatin capsules size.

Example VII

Oral suspension containing 50 mg of active ingredient per 5 ml

Active ingredient 50.0 mg

Hydroxyethyl cellulose 50.0 mg

Sorbic acid 5.0 mg

Sorbitol 70% 600.0 mg

Glycerol 200.0 mg

Aroma 15.0 mg

Water ad 5.0 ml

production:

Distilled water is heated to 70 ° C. Herein, hydroxyethyl cellulose is dissolved with stirring. By adding sorbitol solution and glycerol is cooled to room temperature. At room temperature, sorbic acid, flavor and active ingredient are added. To vent the suspension is evacuated with stirring. One dose = 50mg is included in 5.0ml.

Example VIII

Suppositories containing 100mg active substance 100.0 mg

Adepssolidus 1 600.0 mg

1700.0 mg

production:

The hard fat is melted. At 4O ⁰ C the ground active substance is homogeneously dispersed in the melt. It is cooled to 38 ° C and poured into slightly pre-cooled suppository molds.

Claims (8)

-1- 293 581 Claims: R _{1 is} a hydrogen, fluorine, chlorine or bromine atom, an alkyl group having 1 to 4 carbon atoms which may be substituted by a hydroxy, alkoxy, amino, alkylamino, dialkylamino or acylamino group, an alkoxy group having 1 to 4 carbon atoms in the 2-, 3- or 4-position may be substituted by a hydroxy, alkoxy, amino, alkylamino, dialkylamino or imidazolyl group, a hydroxy, phenylalkoxy, acyloxy, trifluoromethylsulfonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, cycloalkylaminocarbonyloxy, cycloalkylalkylaminocarbonyloxy, arylaminocarbonyloxy, Aralkylaminocarbonyloxy, alkoxycarbonyloxy, cycloalkoxycarbonyloxy, cycloalkylalkoxycarbonyloxy-j-aryloxycarbonyloxy, aralkoxycarbonyloxy, trifluoromethyl, cyano, nitro, alkylmercapto, alkylsulfinyl, alkylsulfonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, Acv laminosulfonyl or acyl group, an amine group represented by an imidazolylalkyl, dialkylaminoalkanoyl, acyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl or tert-butylacetyl group, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, by an alkylsulfonyl group having 1 to 4 carbon atoms, may be monosubstituted by an alkoxycarbonyl group having a total of 2 to 7 carbon atoms or by an alkoxycarbonyl-substituted thiazolidin-3-yl-carbonyl group, an alkylamino group having 1 to 6 carbon atoms on the nitrogen atom by an alkyl, alkylsulfonyl or acyl group when the acyl group> pe represents an alkanoyl group, it may be additionally substituted by an alkoxy group, and the alkyl substituent from position 2 may be substituted by a hydroxy, alkoxy or arylamino group can a mono- or disubstituted by a cycloalkyl, cycloalkylalkyl, phenylalkyl or phenyl group amino group, wherein the substituents may be the same or different, an N-alkyl-cycloalkylamino, N-alkyl-cycloalkylalkylamino, N-alkyl-phenylalkylamino or N-Aikyl- phenylamino, an optionally substituted by an alkyl, cycloalkyl or phenyl substituted pyrrolidino, piperidino or Hexametl.yleniminogruppe, an N-alkoxycarbonyl-alkylamino, N-cycloalkoxycarbonyl-alkylamino, N-cycloalkylalkoxycarbonyl-alkylamino, N-aryloxycarbonyl-alkylamino or N-aralkoxycarbonyl-alkylamino group in which the alkyl group may each contain 1 to 6 carbon atoms, one on the nitrogen atom alkoxycarbonylamino, cycloalkoxycarbonylamino, cycloalkylalkoxycarbonylamino, aryloxycarbonylamino, aralkoxycarbonylamino, acylamino or alkylsulphonylamino group substituted by a cycloalkyl, cycloalkylalkyl or aralkyl group, a carbonyl group represented by an alkyl group which is in the 2- or 3-position by a hydroxy, Alkanoyloxy or alkylamino group, by a hydroxycarbonylalkyl, hydroxy, alkoxy, amino, cycloalkylamino, cycloalkylalkylamino, arylamino or aralkylamino group, by an alkylamino group substituted in the 2- or 3-position by an arylamino group or by an optionally in the alkyl moiety substituted by a carboxy group alkylamino mi t is 1 to 5 carbon atoms, each additionally on the nitrogen atom by an alkyl group substituted, an optionally represented by an alkoxycarbonyl group having a total of 2 to 5 carbon atoms substituted aminoacetylamino group, an aminocarbonylamino or aminothiocarbonylamino group which is represented by an alkyl group having 1 to 20 carbon atoms, by an alkenyl or alkynyl group having 3 to υ carbon atoms, by a bicyclic or acyclic alkyl group having 7 to 11 carbon atoms, by a cycloalkyl, cycloalkylalkyl, Aralkyl or aryl group may be mono-, di- or trisubstituted, where the substituents may be the same or different and a methylene group in a cycloalkyl having 5 to 7 carbon atoms replaced by an oxygen atom and an alkyl group in 4-, 5- or 6-position may be substituted by a hydroxy, alkanoyl or trifluoroacetyl group, a cycloalkyleneiminocarbonylamino group having 4 to 6 carbon atoms in the cycloalkyleneimine portion or a morpholinocarbonylamino group both of which may be substituted on the amino nitrogen by an alkyl group of 1 to 20 carbon atoms, by a cycloalkyl, cycloalkylalkyl, aralkyl or aryl group, a phthalimino, homophthalimino, 2-Carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-carboxyphenylmethylenecarbonylamino or 2-carboxymethylenephenylcarbonylamino group wherein a carbonyl group in a phthalimino group is replaced by a methylene group and a methylene group in a homophthalimino, 2-carboxyphenylmethylenecarbonylamino or 2-carboxymethylenephenylcarbonylamino group by one or two alkyl groups In addition, the above-mentioned phenyl nuclei mono- or disubstituted by alkyl or alkoxy groups, wherein the substituents may be the same or different, and may be fully or partially hydrogenated at the same time, in a 2-position by a carboxy substituted Bicycloalkan-S -carbonsäureamino- or bicycloalkene-S-carboxamino group, a bicyloalkane-2,3-dicarboximino or bicycloalkene-2,3-dicarboxylic acid in which the bicycloalkane and bicycloalkene each contain 9 or 10 carbon atoms, by 1, 2 od it may be substituted 3 methyl groups and an endomethylene group may be replaced by an oxygen atom, a Glutarsäureimino- or 3-carboxy-n-propylencarbonyl group in which each of the n-propylene perfluorinated by one or two alkyl groups or by a tetramethylene or pentamethylene group may be substituted or a 5,7-dioxa-1H, 3H-imidazo [1,5-c] thiazolyl group, R ₂ denotes the meanings mentioned above for R ₁ , a 2-imidazolidon-1-yl or 3,4,5,6-tetrahydro-2 optionally substituted in the 3-position by an alkyl, cycloalkyl, cycloalkylalkyl or aralkyl group pyrimidon-1-yl group or a tetrazolyl group or Ri and R ₂ together with k carbon atoms of the adjacent phenyl ring is a phenyl or 1-alkyl-3,3-dialkyl-2,3-dihydro-pyrrol-2-one group, R _{3 is} a hydrogen, fluorine, chlorine or bromine atom, an alkyl group having 1 to 6 carbon atoms in which a methylene group may be replaced by an oxygen or sulfur atom, a sulfinyl, sulfonyl or alkylamino group and a methyl group may be substituted by a hydroxy, alkoxy, amino, alkylamino or dialkylamino group, however, the methylene group adjacent to the benzimidazole ring may not be replaced by a sulfinyl or sulfonyl group and, with simultaneous replacement of a methylene group and substitution of a methyl group, these must be separated by at least 2 carbon atoms, an alkenyl or alkynyl group each having 3 to 5 carbon atoms, a phenylalkyl group, a cycloalkyl or cycloalkyl-alkyl group in which the cycloalkyl moiety may contain from 5 to 7 carbon atoms each, an aryl, hydroxy or imidazolylalkylamino group, an alkylamino group having 1 to 4 carbon atoms, an aminocarbonyl group which may be substituted by an alkyl or cycloalkyl group having 5 to 7 carbon atoms, a 5-membered heteroaromatic ring containing an NH group, an oxygen or sulfur atom, said above-mentioned 5-membered heteroaromatic ring may additionally contain 1 to 3 N atoms, or a 6-membered heteroaromatic ring which may contain 1 or 2 nitrogen atoms, wherein the above-mentioned 5- and 6-membered heterocyclic rings may be substituted by one or with the exception of the tetrazolyl group by two alkyl groups, R _{4 is} an amino, phthalimino, aminomethyl, cyano, tert-butoxycarbonyl, or 1- (triphenylmethyl) -tetrazolyl group, a Brönsted acid-containing group, or a residue which is in vivo incorporated into a Brönsted acid Group can be converted, R _{5 is} a hydrogen, fluorine, chlorine or bromine atom, R _{6 is} a hydrogen atom or R ₅ and R ₆ together with the two ortho-carbon atoms denote a phenyl group, whereby, unless otherwise stated, among the acyl group mentioned in the definition of the radicals R ₁ to R ₆ , an alkanoyl group having 1 to 7 carbon atoms, a Cycloalkylcarbonylgruppe having a total of 4 to 8 carbon atoms, a Cycloalkylalkanoylgruppe having a total of 5 to 10 carbon atoms or optionally by a fluorine, chlorine or Bromine atom, an alkyl or alkoxy substituted arylcarbonyl, aralkanoyl or phenylsulfonyl group, below the aryl group, a phenyl group optionally substituted by a fluorine, chlorine or bromine atom, by a hydroxy, alkyl, alkoxy, phenylalkoxy or trifluoromethyl group, wherein the alkyl portion may each contain 1 to 4 carbon atoms, or a naphthyl group, below the cycloalkyl group a cycloalkyl group having 3 to 7 carbon atoms which may be substituted by one or two alkyl groups, and among the other alkyl and alkanoyl groups mentioned in the definition of radicals R ₁ to R _{6 are} each alkyl or alkanoyl groups having 1 to 3 carbon atoms, their 1, 3-isomer mixtures and their addition salts with inorganic or organic acids or bases and optionally a pharmaceutical composition, characterized in that a) a compound of the formula (II) in the R ₁ and R ₂ are defined as mentioned above, one of the radicals X ₁ or Y _{1 is} a group of the formula R // v \ // vV -NR ₇ -CH ₂ and the other of X ₁ or Y _{1 is} one of the formula - NH - C - R ,. ' represent, wherein R ₃ 'except for the fluorine, chlorine or bromine atom, the hydroxy, mercapto or aminocarbonyl group, which latter may be substituted by an alkyl group of 1 to 3 carbon atoms or by a cycloalkyl group of 5 to 7 carbon atoms substituted for R 2 _{3 has} at least the meanings mentioned above, R ₄ to R ₆ are defined as mentioned above, R _{7 is} a hydrogen atom, a hydroxy group or an R ₃ 'CO group, wherein R ₃ ' as above mentioned is defined Z ₁ and Z ₂ , which may be identical or different, optionally substituted amino groups or optionally substituted by lower alkyl groups hydroxy or mercapto groups or Z ₁ and Z ₂ together form an oxygen or sulfur atom, an optionally substituted by an alkyl group having 1 to 3 carbon atoms imino group, an alkylenedioxy or Alkylenedithio group having in each case 2 od9r 3 carbon atoms, but where one of the radicals X ₁ or Y _{1 is} a group of the formula -N (COR _3. ¹ ) -CH ₂ or - NH - ^N C - R ₃ , ¹ must represent is cyclized or b) for the preparation of the compounds of the formula I in which R _{3 represents} the aromatic or heteroaromatic radicals mentioned above for R ₃ , a phenylenediamine of the formula in the R ₁ and R ₂ are defined as mentioned above, one of the radicals X2 or Y2 is a group of the formula -NH-CH ^R 4 in the R ₄ to R ₆ are defined as mentioned above, and the other of X ₂ or Y _{2 is} an amino group, with an aldehyde of the formula OCH-R3 " in the R ₃ "is the above-mentioned aromatic or heteroaromatic radicals for R _3, is reacted in the presence of an oxidizing agent, or c) for preparing compounds of the formula I in which at least one of the radicals R _1, R ₂ and / or R ₃ represents one of the containing for R _1, R ₂ and / or R ₃ mentioned above, a sulfinyl or sulfonyl radicals and the rest of the radicals R ₁ , R ₂ and / or R ₃ defined as mentioned above are, a compound of the formula in the R4 to Re are defined as mentioned above, '"represents one of the R _1, R ₂ and / or R ₃ mentioned above, a sulfur atom or a sulfinyl group-containing residues, and the remainder of radicals R _1' is at least one of the radicals R ₁ ', R _2' and / or R _3, R ₂ 'and / or R ₃ '"which have the meanings mentioned above for R ₁ , R ₂ and / or R ₃ , is oxidized or d) for the preparation of a compound of the formula I in which R _{4 is} a carboxy or amino group
represents a compound of the formula (Vl) in the R ₁ to R ₃ , R ₅ and Re are defined as mentioned above and R ₄ 'represents a group convertible to a carboxy or amino group, is converted into a corresponding carboxy or amino compound, or e) a benzimidazole of the formula R- (VII) in the R ₁ to R ₃ are defined as mentioned above, with a biphenyl compound of the formula (VIII) in the R4 to R6 are defined as mentioned above and Z _{3 is} a nucleophilic leaving group such as Halogen atom, e.g. A chlorine, bromine or iodine atom, or a substituted sulphonyloxy group, e.g. B. a methanesulfonyloxy, phenylsulfonyloxy or p-toluenesulfonyloxy group will or f) for preparing a compound of formula I ₁ in which R 4 represents a 1 H-tetrazolyl group Protective residue of a compound of the formula (IX) in the R ₁ to R ₃ , R ₅ and R ₆ are defined as mentioned above and R ₄ "is a 1-position by a protecting group is protected 1 H-tetrazolyl group, cleaved or g) for the preparation of a compound of the formula I in which R _{4 represents} a 1H-tetrazolyl group, a Compound of the formula (X) CN in the R ₁ to R ₃ , R ₅ and R ₆ are defined as mentioned above, is reacted with hydrazoic acid or h) for the preparation of a compound of the formula I in which R ₁ and / or R ₂ represent an aminocarbonylamino group denoted by a bi- or tricyclic alkyl group or by an alkyl, alkenyl, alkyryl, cycloalkyl, cycloalkylalkyl, aralkyl or aryl group may be mono-, di- or trisubstituted, wherein a methylene group in a cycloalkyl radical having 4 to 7 carbon atoms may be replaced by an oxygen atom, a compound of the formula • -CC * ⁴ in the R ₂ to R ₆ are defined as mentioned above and R _{8 is} a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl or alkynyl group each having 3 to 5 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a cycloalkyl-alkyl group in which the cycloalkyl part has 3 to 7 carbon atoms, the alkyl part 1 to Contain 3 carbon atoms and in a cycloalkyl part having 4 to 7 carbon atoms, a methylene group may be replaced by an oxygen atom, a bicyclic or tricyclic alkyl group having 7 to 10 carbon atoms, an aryl or aralkyl group having 1 to 3 carbon atoms in the alkyl part, wherein the aryl group is a optionally represented by a fluorine, chlorine or bromine atom, a hydroxy, alkyl or alkoxy group each having 1 to 4 carbon atoms substituted phenyl group, means with a compound of formula N-CW-Z, in the R ₉ , which may be identical or different, have the meanings mentioned above for R ₈ , W is an oxygen or sulfur atom, Z _{4 is} a nucleophilic leaving group such as a chlorine or bromine atom or else when at least one of the radicals R _{9 represents} a hydrogen atom, Z ₄ and R ₉ together represent a nitrogen-carbon bond or a Cycioalkyleniminogruppe with up to 6 carbon atoms or a morpholino group is reacted or i) for the preparation of a compound of the formula I in which R _{4 is} a trifluoromethylcarbonylamino, trifluoromethylcarbonylaminomethyltrifluoromethylsulfonylamino, trifluoromethylsulfonylaminomethyl or 1H-tetrazolyl group, an alkylcarbonylamino, alkylcarbonylaminomethyl, arylcarbonylamino, arylcarbonylaminomethyl, aralkylcarbonylamino, aralkylcarbonylaminomethyl, alkylsulfonylamino, Alkylsulfonylaminomethyl, arylsulfonylamino, Arylsulfonylaminomethyl-, Aralkylsulfonylamino- or Aralkylsulfonylaminomethylgruppe in which the alkyl moiety may each contain 1 to 3 carbon atoms, represents a compound of formula (XIII) in the Ri to R3, R ₅ and R ₆ are defined as mentioned above and R ₄ '"represents an amino or aminomethyl group, with a compound of formula HO-U-R in the R _{10 is} a THF luormethylgruppe, an alkyl, aryl or aralkyl group, wherein the alkyl moiety may each contain 1 to 3 carbon atoms, and U represents a carbonyl or sulfonyl group; or is acylated with their reactive derivatives such as their acid halides, acid esters or acid anhydrides, or k) for the preparation of a compound of the formula I in which R _{4 is} an alkylsulfonylaminocarbonyl or perfluoroalkylsulfonylamino group each having 1 to 4 carbon atoms in the alkyl moiety or a benzylsulfonylaminocarbonyl group, a reactive derivative of a carboxylic acid of the formula (XV) COOH in the R ₁ to R ₃ , R ₅ and R ₆ are defined as mentioned above, with a sulfonamide of the formula H ₂ N-SO ₂ -R _n (XVI) in the R _{11 represents} an alkyl or perfluoroalkyl group each having 1 to 4 carbon atoms or a benzyl group, or is reacted with its alkali metal salt, or I) for the preparation of a compound of the formula I in which R _{2 is} a 2-imidazolidin-1-yl or 3,4,5,6-tetrahydro optionally substituted in the 3-position by an alkyl, cycloalkyl, cycloalkylalkyl or aralkyl group Represents -2-pyrimidon-1-yl group, a compound of the formula (XVII) Hal (CHg) _n -NH-CO-N in the R ₁ , R ₃ and R ₄ to R _{6 are} as defined above, Hai represents a chlorine, bromine or iodine atom and η is the number 2 or 3, cyclized and, if desired, an NH compound thus obtained with a compound of the formula R ₁₂ -HaI (XVIII) in the Rn represents an alkyl, cycloalkyl, cycloalkylalkyl or aralkyl group and Hal represents a chlorine, bromine or iodine atom, is alkylated or m) for the preparation of compounds of general formula I ₁ in the R _1, an amino group represented by a dialkylaminoalkanoyl, acyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, aryloxycarbonyl-.Aralkoxycarbonyl or trifluoroacetyl group, by an alkylsulfonyl group having 1 to 4 carbon atoms an alkoxycarbonyl group having 2 to 7 carbon atoms in total or monosubstituted by an alkoxycarbonyl-substituted thiazolidin-3-ylcarbonyl group, an alkylamino group having 1 to 6 carbon atoms, which may be substituted on the nitrogen atom by an alkylsulfonyl or acyl group, where, if the acyl group represents an alkanoyl group, this may additionally be substituted by an alkoxy group, and the alkyl substituent from position 2 by a hydroxy, Alkoxy or Arylaminogruppe be substituted an N-alkoxycarbonylalkylamino, N-cycloalkoxycarbonylalkylamino, N-cycloalkylalkoxycarbonylalkylamino, N-aryloxycarbonylalkylamino or N-aralkoxycarbonylalkylamino group in which the alkyl group may each contain 1 to 6 carbon atoms, one on the nitrogen atom by one Cycloalkyl, cycloalkylalkyl or aralkyl group-substituted alkoxycarbonylamino, cycloalkoxycarbonylamino, cycloalkylalkoxycarbonylamino, aryloxycarbonylamino, aralkoxycarbonylamino, acylamino or alkylsulfonylamino group, or a phthalimino, homophthalimio, 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-carboxyphenylmethylenecarbonylamino or 2-carboxymethylenephenylcarbonylamino group wherein a carbonyl group in a phthalimino group is replaced by a methylene group and a methylene group in a homophthalimino, 2-carboxyphenylmethylenecarbonylamino or 2 -Carboxymethylenphenylcarbonylaminogruppe may be substituted by one or two alkyl groups, and additionally the above-mentioned phenyl nuclei mono- or disubstituted by alkyl or alkoxy groups, wherein the substituents may be identical or different, and may be hydrogenated wholly or partly simultaneously, one in 2-position a carboxy group-substituted bicycloalkane-S-carboxylic acid amino or bicycloalkene S-carboxy-amino group, a bicycloalkane ^^ dicarboxylic acid amino or bicycloalkene ^^ dicarboxylic acid imino group in which the bicycloalkane or bicycloalkene moiety each contains 9 or 10 carbon nstoffatome containing substituted by 1, 2 or 3 methyl groups and an endomethylene group may be replaced by an oxygen atom, a Glutarsäureimino- or 3-carboxy-n-propylencarbonylgruppe in which each of the n-propylene perfluorinated, by one or two alkyl groups or by a Tetramethylene or pentamethylene group may be substituted, and R _4, with the exception of the amino group has the meanings mentioned above for R ₄ , a compound of the formula (XIX) in the R2 'R3' Rs and R ₆ are defined as above, R _{4 is} other than the amino group as defined in any one of claims 1 to 6 and R _{13 is} a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may be substituted from position 2 by a hydroxy, alkoxy or arylamino group, a cycloalkyl , Cycloalkylalkyl or aralkyl group, with a compound of the formula R14-Z5 (XX) in the R _{14 is} a dialkylaminoalkanoyhcycloalkoxycarbonyl, cycloalkylalkoxycarbonyl-aryloxycarbonyl, aralkoxycarbonyl or trifluoroacetyl group, an alkylsulfonyl group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 7 carbon atoms in total, an alkoxycarbonyl-substituted thiazolidin-3-yl-carbonyl group or an acyl group, in which, if the acyl group represents an alkanoyl group, may additionally be substituted by an alkoxy group, or a 2-carboxyphenylcarbonyl, 2-carboxyphenylmethyl, 2-carboxyphenylmethylenecarbonyl or 2-carboxymethylenephenylcarbonyl group, a methylene group being present in a 2-carboxyphenylmethylencarbonyl or 2-carboxy Carboxymethylenphenylcarbonylgruppe may be substituted by one or two alkyl groups, and additionally mono- or disubstituted by the above-mentioned phenyl nuclei by alkyl or alkoxy groups, wherein the substituents may be the same or different, and at the same time completely o which may be partially hydrogenated, a bicycloalkane-S-carbonyl or bicycloalkene-3-carbonyl group substituted in the 2-position by a carboxy group, in which the bicycloalkane and bicycloalkene moieties each have 9 or 10 carbon atoms substituted by 1,2 or 3 methylene groups and an endomethylene group may be replaced by an oxygen atom, an S-carboxy-n-propylencarbonyl group in which the n-propylene perfluorinated by one or two alkyl groups or by a tetramethylone or Penamethylengruppe may be substituted, and Z _{5 represents} a nucleophilic leaving group, or is acylated with their reactive derivatives such as their acid halides, acid esters or acid anhydrides, or n) for the preparation of compounds of general formula I in which at least one of Ri or R _{2 is} a 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-carboxyethylstyrene-carbonylamino-odθr 2-carboxymethylstorylnylcarbonylamino group _/ wherein a methylene group in a 2-carboxyphenylmethylenecarbonylamino or 2-carboxymethylenephenylcarbonylamino group may be substituted by one or two alkyl groups, and in addition mono- or disubstituted the abovementioned phenyl nuclei by alkyl or alkoxy groups, where the substituents may be identical or different, and at the same time be fully or partially hydrogenated, a Positioned by a carboxy group-substituted bicycloalkane-S-carboxylic acid amino or bicycloalkene-S-carboxamino group in which the bicycloalkane and bicycloalkene each contain 9 or 10 carbon atoms substituted by 1, 2, or 3 methyl groups and an endomethylene group by an acid may be substituted, a 3-carboxy-n-propylencarbonyl group in which the n-propylene group perfluorinated by one or two alkyl groups or by a tetramethylene or pentamethylene group may be substituted, means a compound of the general formula (XXI) in the R ₂ to R ₆ are defined as mentioned above and R _{15 is} a phthalimino or homophthalimino group wherein a carbonyl group in a phthalimino group may be replaced by a methylene group and a methylene group in a homophthalimino group may be substituted by one or two alkyl groups, and in addition mono- or disubstituted by alkyl or alkoxy groups, the above-mentioned phenyl nucleus wherein the substituents may be the same or different, and may be fully or partially hydrogenated at the same time, a bicycloalkane-2,3-dicarboximino or bicycloalkene-2,3-dicarboxylic acid imino group in which the bicycloalkane and bicycloalkene moieties each contain 9 or 10 carbon atoms Substituted 1,2, or 3 methyl groups and an endomethylene group may be replaced by an oxygen atom, a Glutarsäureiminogruppe in which the n-propylene group perfluorinated by one or two alkyl groups or by a tetramethylene or pentamethylene group may be substituted, partially hydro is lysed and if necessary, a protective moiety used during the reactions a) to n) to protect reactive groups is split off and / or if desired, subsequently a compound of the formula I in which R 1 and / or R _{2 represent} a nitro group is converted by means of reduction into a corresponding amino compound of the formula I or a compound of the formula I in which R 1 and / or R _{2 is} a hydroxy, amino, alkylamino, phenylalkylamino, alkylsulfonylamino or acylamino group is converted by means of alkylation into a corresponding alkylated compound of the formula I or a compound of the formula I compound of the formula I in which R ₁ and / or R _{2 represents} a benzyloxy group is converted by means of debenzylation into a corresponding compound of the formula I, in which R ₁ and / or R _{2 represents} a hydroxy group, or a compound of formula I in which R ₁ and / or R _{2 represents} a carboxy group, by amidation in a corresponding compound of formula I ₁ in the R ₁ and / or R _{2 is} optionally substituted by one or two alkyl groups, each with 1 represents up to 3 carbon atoms substituted aminocarbonyl group, is converted or a compound of the formula I in which R ₁ and / or R _{2 represent} a carboxy group and / or R ₄ represents a cyano group, by reduction into a corresponding compound of the formula I, in which R ₁ and / or R _{2 is} a hydroxymethyl group and / or R _{4 is} a Represents aminomethyl group, is converted or a compound of the formula I in which R ₁ and / or R ₂ represent an alkoxycarbonyl group is converted by hydrolysis into a corresponding compound of the formula I, in which R ₁ and / or R _{2 represents} a carboxy group, or a compound of the formula I in which R ₁ and / or R _{2 is} an alkoxy or phenylalkoxy group is converted by means of ether cleavage into a corresponding compound of the formula I in which R ₁ and / or R _{2 is} a hydroxy group; a compound of the formula I thus obtained in which R ₁ and / or R _{2 is} an aminocarbonylamino or aminothiocarbonyl group which is substituted by a cycloalkyl group having 5 to 10 carbon atoms in which a methylene group in the 2-position is replaced by an oxygen atom and additionally by an alkyl group having 1 to 20 carbon atoms, by an alkenyl or alkynyl group each having 3 to 5 carbon atoms, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, by a cycloalkyl, cycloalkylalkyl, aralkyl or aryl group mono - or can be disubstituted, by reduction into a corresponding compound of formula I, in the Ri and / or R ₂ an aminocarbonylamino ode r represents aminothiocarbonyl group which is substituted by a 4-hydroxy-n-butyl, 5-hydroxy-n-pentyl or 6-hydroxy-n-hexyl group and additionally by an alkyl group having 1 to 20 carbon atoms, by an alkenyl or Alkynyl group each having 3 to 5 carbon atoms, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, mono- or disubstituted by a cycloalkyl, cycloalkylalkyl, aralkyl or aryl group, is, is converted or a compound of formula I in which R ₁ and / or R _{2 is} a phthalimino group which may be mono- or disubstituted by an alkyl or alkoxy group, where the substituents may be the same or different, by reduction to a corresponding compound of the formula I in which R ₁ and / or R _{2 represents} a 1-oxo-isoindolin-2-yl group which may be mono- or disubstituted by an alkyl or alkoxy group, where the substituents may be the same or different , is converted or a thus obtained 1-, 3-isomeric mixture of a compound of formula I is separated by isomer separation in its 1- and 3-isomer, or a compound of the formula I thus obtained is converted into its addition salt, in particular for pharmaceutical use in its physiologically tolerated salt with an inorganic or organic acid or BaOe, and optionally by non-chemical means a compound of the formula I in one or more inert substances and / or diluent is incorporated. Process according to claim 1, characterized in that benzimidazoles of the formula I are prepared in which R ₁ to R ₃ , R ₅ and Re are as defined in claim 1 and R _{4 is} a carboxy, aminoacetylamino, trifluoromethylcarbonylamino, trifluoromethylcarbonylaminomethyl-, Trifluormethylsulfonylamino-, Trifluormethylsulfonylaminometliyl- or IH-tetrazolyl group, a alkylcarbonylamino, Alkylcarbonylaminomethyl-, arylcarbonylamino, Arylcarbonylaminomethyl, Aralkylcarbonylamino-, Aralkylcarbonylaminomethyl-, alkylsulfonylamino, Alkylsulfonylaminomethyl-, arylsulfonylamino, Arylsulfonylaminomethyl-, Aralkylsulfonylamino-, Aralkylsulfonylaminomethyl-, Arylsulfonylaminocarbonyl- or Benzylsulfonylaminocarbonykjruppe , an alkylsulfonylaminocarbonyl or perfluoroalkylsulfonylaminocarbonyl group each having 1 to 6 carbon atoms in the alkyl part, an alkoxycarbonyl group having a total of 2 to 7 carbon atoms, an aralkoxycarbonyl group, a pivaloyloxymethoxycarbonyl, phthalide ylmethoxycarbonyl, ethoxycarbonyloxyethoxycarbonyl, methoxymethoxycarbonyl, cyclohexyloxycarbonylmethoxycarbonyl or (1,3-dioxa-2-oxo-4-methyl-cyclopenten-5-yl) -methoxycarbonyl group, their 1,3-isomer mixtures and their addition salts with inorganic or organic acids or bases. Process according to Claim 1, characterized in that benzimidazoles of the formula I are prepared in which R _{1 is} a hydrogen, fluorine or chlorine atom, a trifluoromethyl, hydroxyl, benzyloxy, carboxy, cyano, amino, nitro , Aminosulfonyl, methylaminosulfonyl, dimethylaminosulfonyl, trifluoromethylsulfonyloxy or tetrazolyl group, an alkyl group having 1 to 4 carbon atoms, wherein the methyl group may be additionally substituted by a hydroxy or alkylamino group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms which are in the 2-, 3- or 4-position by a hydroxy , Alkoxy, alkylamino, dialkylamino or imidazoyl group and the alkyl substituent may each contain 1 to 3 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a cycloalkylaniinocarbonyloxy group having 5 to 7 carbon atoms in the cycloalkyl part, an amino group represented by a benzyl , Decalin, trifluoromethylcarbonyl, benzylcarbonyl, benzyloxycarbonyl, 2-ethyl-5-methylcyclohexyloxy or tert-butoxycarbonylaminoacetyl group, by an alkyl group having 1 to 5 carbon atoms, by a cycloalkyl, cycloalkylalkyl, cycloalkoxycarbonyl, cyrloalkylcarbonyl or cycloalkylalkanoyl group wherein the cycloalkyl moiety each has 5 to 7 carbon atoms, the alky 1 to 3 carbon atoms and the alkanoyl part 1 to 3 carbon atoms and the cycloalkyl part may contain 5 to 7 carbon atoms, a phthalimino, homophthalimino, 2-Carboxyphenylcarbonylamino-, 2-Carboxyphenylmethylamino-, 2-Carboxyphenylmethylencarbonylamino- or 2-Carboxymethylenphenylcarbonylaminogruppe, wherein a carbonyl group in a phthalimino group replaced by a methylene group and a Methylene group in a homophthalimino, 2-carboxyphenylmethylencarbonylamino or 2-carboxymethylenephenylcarbonylamino group may be substituted by one or two methyl groups, and in addition mono- or di-substituted by methyl or methoxy groups, wherein the substituents may be the same or different, and simultaneously wholly or partially hydrogenated, a bicycloalkane-S-carboxylic acid amino or bicycloalkene-3-carboxylic acid amino group substituted in the 2-position by a carboxy group, a bicycloalkane-2,3-dicarboxylic acid or bicycloalkene-2,3-dicarboxylic acid acidimino group in which the bicycloalkane and bicycloalkene moiety each contain 9 or 10 carbon atoms, may be substituted by 1, 2 or 3 methyl groups, and an endomethylene group may be replaced by an oxygen atom, a glutaric imino or 3-carboxy-n-propylenecarbonyl group, in each of which perfluorinated n-propylene, may be substituted by one or two alkyl groups or by a tetramethylene or pentamethylene group, or
a 5,7-dioxa-1H, 3H-imidazo [1,5-c] thiazolyl group,
R _{2 is} a hydrogen atom, a methyl or hydroxy group or R ₁ and R ₂ together with the two ortho-standing carbon atoms of the adjacent phenyl ring is a phenyl group,
R _{3 is} an alkyl group having 3 to 5 carbon atoms, an alkenyl or alkynyl group having in each case 3 to 5 carbon atoms, R _{4 is} a carboxy, methylsulfonylaminocarbonyl, trifluoromethylsulfonylaminocarbonyl, benzenesulfonylaminocarbonyhtrifluoromethylcarbonylaminomethyl, trifluoromethylaminomethyl or tetrazolyl group, R _{5 is} a hydrogen atom, R _{6 is} a hydrogen atom or R ₅ and R ₆ together with the two ortho-standing carbon atoms represent a phenyl group, their 1-, 3-isomer mixtures and their addition salts with inorganic or organic acids or bases. Process according to claim 1, characterized in that benzimidazoles of the formula I are prepared in which R _{1 is} an amino group represented by an alkanoyl group having 1 to 6 carbon atoms, by an aminoalkanoyl or dialkylaminoalkanoyl group in which the alkyl moiety and the alkanonyl moiety! each containing 1 to 3 carbon atoms, is substituted by an alkoxycarbonyl group having a total of 2 to 7 carbon atoms or by a by an alkoxycarbonyl group having a total of 2 to 4 carbon atoms substituted thiazolidin-3-yl-carbonyl group, a benzylamino or alkylamino group with 1 to 5 carbon atoms, which may be substituted on the nitrogen atom by an alkanoyl group of 1 to 5 carbon atoms substituted by an alkoxy group of 1 to 3 carbon atoms, by a cycloalkylcarbonyl group in total 3 carbon atoms may be substituted by a Cycloalkylcarbonylgruppe having a total of 6 to 8 carbon atoms or by a Alkoxycarbonylgruppe with a total of 2 to 3 carbon atoms, by an alkanoyl group having 1 to 6 carbon atoms, by an aminoalkanoyl or dialkylaminoalkanoyl group in which each of the alkyl moiety and the alkanoyl moiety may contain 1 to 3 carbon atoms, by an alkoxycarbonyl group having a total of 2 to 7 carbon atoms, by an alkylsulfonyl group 1 to 4 '- [(2-n-butyl-6-cyclo-pentylcarbonylamino-benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, its 1,3-isomer mixtures and their addition salts with inorganic or organic acids or bases. 4 '- [(2-n-butyl-6- (N- (n-hexylaminocarbonyl) -N- (2-phenyl-ethyl) -amino) -benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid and 4 '- [(2-n-butyl-7-hydroxy-4-methylbenzimidazol-1-yl) methyl] -2- (1H-tetrazol-5-yl) -biphenyl, 4'-I (2- n-Butyl-6- (cis-hexahydrophthalimino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6- (N- (dimethylaminocarbonyl) -benzylamino) - benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid, 4'-i (2-n-butyl-6- (N- (n-butylaminocarbonyl) methylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6-cyclohexylcarbonylamino-benz imidazol-1-yl) methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-n ^ entylamino) -benzoimidazol-1-yl) methyl) biphenyl-2-carboxylic acid, 4 '- [(2-n-Butyl-6 - ((5-hydroxy-n-pentyl) -aminocarbonylamino) -benzoimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-n-hexylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic ^r e, 4 '- [(2-n-butyl-6- (N- (dimethylaminocarbonyl) -amino) -benzimidazol-1-yl) -rnethyl] biphenyl-2-carboxylic acid, 4'-i (2-n-butyl-6- (N-ethoxycarbonyl-benzylamino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-Butyl-6- (n-butylaminocarbonylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, 4' - [(6-n-butanoylamino-2-n-butyl -benzimidazole-1-yl) methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6-n-pentanoylamino-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid, 4' - [(2-n-butyl-6-propionylamino-benzimidazole] 1-yl) -methyl] -biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6-isopropylcarbonylamino-benzimidazol-1-yl) -methyl] -biphenyl-2-carboxylic acid, 4' - [( 2-n-butyl-6- (tetrahydropyran-2-yl-aminocarbonylamino) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-Butyl-6- (1-oxo-isoindolin-2-yl) -benzimidazol-1-yl) -methyl] biphenyl-2-carboxylic acid, 4' - [(2-n-butyl 6- (N-cyclohexylaminocarbonyl-benzylamino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid 4 '- [(2-n-butyl-6- (N-methylaminocarbonyl-benzylamino) -benzimidazol-1-yl) methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6- (N-cyclohexy aminocarbonyl-n-pentylamino) -benzoimidazol-1-yl!) Methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-methylamino) -benzoimidazol-1-yl) -methyljbiphenyl-2-carboxylic acid, carboxylic acid, 4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-n-propylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-ethylamino) -benzoimidazol-1-yl) -methyllbiphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6- (N-cyclohexylaminocarbonyl-n-butylamino) -benzoimidazol-1-yl) methyl] biphenyl-2-carboxylic acid, 4 '- [(2-n-butyl-6- (N- (n-hexylaminocarbonyl) -benzyl-amino) -benzimidazole-1-yl) methyl] biphenyl-2-carboxylic acid, 4 carbon atoms is substituted, an aminocarbonylamino or aminothiocarbonylamino group represented by an alkyl group having 1 to 8 carbon atoms, by an alkenyl-alkynyl group having 3 to 3 carbon atoms each 4. The method according to claim 1, characterized in that benzimidazoles of the formula I are prepared, in the R _{1 is} an amino group represented by a benzyl, decalin, trifluoromethylcarbonyl, Benzylcarbonyi-, Benzyloxycarbonyl-, 2-ethyl-5-methylcyclohexyloxy - orertert. Butoxycarbonylaminoacetylgruppe, by an alkyl group having 1 to 5 carbon atoms, by a cycloalkyl, Cycloaikylalkyl-, Cycloalkoxycarbonyl-, Cycloalkylcarbonyl-, or Cycloalkylalkanoylgruppe, wherein the Cycloalkylteil each 5 to 7 carbon atoms, the alkyl moiety 1 to 3 carbon atoms and the Alkonylteil 1 i? is3 carbon atoms, by an alkanoyl group having 1 to 6 carbon atoms, by an aminoalkanoyl or dialkylamino.oalkanoyl group in which each of the alkyl moiety and the alkanoyl moiety may contain 1 to 3 carbon atoms, by an alkoxycarbonyl group having a total of 2 to 7 carbon atoms, by an alkylsulfonyl group Is substituted by 1 to 4 carbon atoms or by a by an alkoxycarbonyl group having a total of 2 to 4 carbon atoms substituted thiazolidin-3-yl-carbonyl group, a benzylamino or alkylamino group having 1 to 5 carbon atoms, additionally on the nitrogen atom by a benzyl or Cyclohexylgr uppe, by an alkyl group having 1 to 3 carbon atoms which may be substituted in 2 or 3 position by an alkoxy group having 1 to 3 carbon atoms or by a phenylamino group, by an alkanoyl group having 1 to 5 carbon atoms represented by an alkoxy group having 1 to 3 Carbon atoms substituted by a cycloalkylcarbonyl group having a total of 6 to 8 carbon atoms or by an alkoxycarbonyl group having a total of 2 to 4 carbon atoms, an aminocarbonylamino or aminothiocarbonylamino group represented by an alkyl group having 1 to 12 carbon atoms, by an alkenyl or alkynyl group, respectively 3 to 4 carbon atoms is substituted, a carbonyl group represented by an alkyl group which may be substituted in the 2- or 3-position by a hydroxy, alkoxycarbonyl or alkylamino group by an alkylamino group having 1 to 5 carbon atoms which may be substituted by a carboxy group in the alkyl portion Alkylamino group which is substituted in the 2- or 3-position by a phenylamino group, by a phenyl, alkoxy, amino, benzylamino, phenylethylamino, Cycloalkylamino- or Cycloalkylalkylamino-, in which in each case the alkyl moiety 1 to 3 carbon atoms and the Cycloalkylteil may contain 5 to 7 carbon atoms and in addition an alkylamino group having 1 to 5 carbon atoms on the nitrogen atom may be substituted by an alkyl group having 1 to 4 carbon atoms, is substituted, an aminocarbonylamino or aminothiocarbonylamino group represented by an alkyl group having 1 to 12 carbon atoms, by an alkenyl or alkynyl group having 3 to 4 carbon atoms or substituted by an alkoxycarbonyl group having a total of 2 to 4 carbon atoms substituted thiazolidin-3-yl-carbonyl group, a benzylamino or alkylamino group having 1 to 5 carbon atoms, on the nitrogen atom additionally by a benzyl or cyclohexyl group, by an alkyl group having 1 to 3 carbon atoms which may be substituted in the 2- or 3-position by an alkoxy group having 1 to 3 carbon atoms or by a phenylamino group, by an alkanoyl group having 1 to 5 carbon atoms represented by an alkoxy group having 1 to 3 carbon atoms 5 carbon atoms, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, mono-, di- or trisubstituted by a cycloalkyl, cycloalkylalkyl or phenylalkyl group, wherein the substituents may be the same or different and each of the alkyl moiety 1 to 3 Carbon atoms and the cycloalkyl part may contain 5 to 7 carbon atoms and a Methylene group in a cycloalkyl radical having 5 to 7 carbon atoms replaced by an oxygen atom and an alkyl group in the 4-, 5- or 6-position may be substituted by a hydroxy or trifluoroacetyl group, a cycloalkyleneiminocarbonylamino group having 4 to 8 carbon atoms in the cycloalkyleneimine moiety or a morpholinocarbonylamino group both of which may be substituted on the amino nitrogen by an alkyl group of 1 to 8 carbon atoms, by a cycloalkyl, cycloalkylalkyl or phenylalkyl group in which each of the alll moiety is 1 to 3 carbon atoms and the cycloalkyl part may contain 5 to 7 carbon atoms, a phthalimino, homophthalimino, 2-carboxyphenylcarbonylamino, 2-carboxyphenylmethylamino, 2-carboxyphenylmethylencarbonylamino or 2-carboxymethylenephenylcarbonylamino group, wherein a carbonyl group in a phthalimino group is replaced by a methylene group and a methylene group in one Homophthalimino, 2-Ca boxyphenylmethylencarbonylamino or 2-carboxymethylenephenylcarbonylamino group may be substituted by one or two methyl groups, and additionally the above-mentioned phenyl nuclei mono- or by mono- or methoxy groups disubstituted, where the substituents may be identical or different, and at the same time hydrogenated in whole or in part, a bicycloalkane-S-carboxylic acid amino or bicycloalkene-3-carboxylic acid amino group substituted in the 2-position by a carboxy group, a bicycloalkane.RTM. dicarboxylic acid or bicycloalkene-2,3-dicarboxylic acid imino group in which the bicycloalkane and bicycloalkene moiety each contain 9 or 10 carbon atoms, may be substituted by 1, 2 or 3 methyl groups, and an endomethylene group may be replaced by an oxygen atom, a glutaric imino or 3-carboxy in each of which the n-propylene group may be perfluorinated, substituted by one or two alkyl groups, or by a tetramethylene or pentamethylene group, or n-propylenecarbonyl group a 5,7-dioxa-1H, 3H-imidazo [1,5-c] thiazolyl group,
R _{2 is} a hydrogen atom, R ₁ and R ₂ together with the two ortho-carbon atoms of the adjacent phenyl ring have a phenyl group, R _{3 is} an alkyl group having 3 to 5 carbon atoms, an alkenyl or alkynyl group having in each case 3 to 5 carbon atoms,
R _{4 is} a carboxy or tetrazolyl group,
R _{5 is} a hydrogen atom,
R _{6 is} a hydrogen atom or R ₅ and R ₆ together with the two ortho-standing carbon atoms represent a phenyl group, their 1-, 3-isomer mixtures and their addition salts with inorganic or organic acids or bases. 5 carbon atoms, by a bicyclic or acyclic alkyl group having 7 to 11 carbon atoms, by a cycloalkyl, cycloalkylalkyl or phenylalkyl group mono-, di- or may be trisubstituted, wherein the substituents may be the same or different and each of the alkyl part 1 to 3 Carbon atoms and the cycloalkyl part may contain 5 to 7 carbon atoms and a methylene group in a cycloalkyl group having 5 to 7 carbon atoms replaced by an oxygen atom and an alkyl group in 4-, 5- or 6-position may be substituted by a hydroxy or Trif luoracetylgruppe a cycloalkyleneiminocarbonylamino group having 4 to 6 carbon atoms in the cycloalkyleneimine moiety or a morpholinocarbonylamino group both of which may be substituted on the amino nitrogen by an alkyl group having 1 to 12 carbon atoms, by a cycloalkyl, cycloalkylalkyl or phenylalkyl group in which each of the alkyl moieties 1 to 5 carbon atoms, by a bi- or tricyclic alkyl group having 7 to 11 carbon atoms, by a cycloalkyl, cycloalkylalkyl or phenylalkyl group may be mono-, di- or trisubstituted, wherein the substituents may be the same or different and each of the alkyl moiety 1 to 3 carbon atoms and the cycloalkyl moiety may contain 5 to 7 carbon atoms and a methylene group in a cycloalkyl moiety of 5 to 7 carbon atoms may be replaced by an oxygen atom and an alkyl group in the 4-, 5- or 6-position may be substituted by a hydroxy or trifluoroacetyl group, a cycloalkyloniminocarbonylamino group having 4 to 6 carbon atoms in the cycloalkyleneimine part or a morpholinocarbonylamino group both of which may be substituted on the amino nitrogen by an alkyl group having 1 to 12 carbon atoms, by a cycloalkyl, cycloalkylalkyl or phenylalkyl group in which each of the alkyl part has 1 to 3 carbon atoms and the Cycloalkyl part may contain 5 to 7 carbon atoms, a phthalimi-, Homophthalimino-, 2-Carboxyphenylcarbonylamino-, 2-Carboxyphenylmethylamino-, 2-Carboxyphenylmethylencarbonylamino- or 2-Carboxymethylenphenylcarbonylaminogruppe, wherein a carbonyl group in a phthalimino group replaced by a methylene group and a methylene group in a homophthalimino -, 2-Carboxyphenylmethylencarbonylamino- or 2-carboxymethylenephenylcarbonylamino group may be substituted by one or two methyl groups, and additionally the above-mentioned phenyl nuclei mono- or by mono- or methoxy groups disubstituted, wherein the substituents are the same or different may, and may be fully or partially hydrogenated at the same time, a bicycloalkane-S-carboxylic acid amino or bicycloalkene-3-carboxylic acid amino group substituted in the 2-position, a bicycloalkane ^ S-dicarboxylic acid triIPPO or bicycloalkene-2,3-dicarboxylic acid imino group, in wherein the bicycloalkane and bicycloalkene moieties each contain 9 or 10 carbon atoms, may be substituted by 1, 2 or 3 methyl groups, and an endomethylene group may be replaced by an oxygen atom, a glutaric imino or 3-carboxy-n-propylenecarbonyl group, in each of which the n-propylene group perfluorinated, may be substituted by one or two alkyl groups or by biproTetramethylene or pentamethylene group, or a 5,7-dioxa-1H, 3H-imidazo [1,5-c] thiazolyl group, a 2-imidazolidin-1-yl group optionally substituted in the 3-position by an alkyl group having 1 to 3 carbon atoms, or a SASjö tetrahydro ^ -pyrimidone-i-yl group, R _{2 is} a hydrogen, fluorine or chlorine atom, a methyl, hydroxy or methoxy group, or R ₁ and R ₂ together with the two ortho-standing carbon atoms of the adjacent phenyl ring is a phenyl or 1-alkyl-3,3-dialkyl 2,3-dihydro-pyrrol-2-one group in which the alkyl moiety may contain 1 to 3 carbon atoms each,
R _{3 is} a hydrogen, fluorine or chlorine atom,
a hydroxy, benzyl or aminocarbonyl group, an alkyl group having 1 to 5 carbon atoms, wherein the methyl group may be additionally substituted by a hydroxy group, by an alkoxy, alkylsulfenyl, alkylsulfinyl or alkylsulfonyl group each having 1 to 3 carbon atoms, a cycloalkyl or cycloalkylalkyl group in which the cycoalkyl part each of 5 to 7 carbon atoms and the alkyl portion may contain 1 to 3 carbon atoms, an alkenyl or alkynyl group each having 3 to 5 carbon atoms, a phenylalkyl group having 1 to 3 carbon atoms, an alkylamino group having 1 to 4 carbon atoms, a pyridyl, furyl, thiazolyl or pyrazolyl group which may be substituted by one or two methyl groups, R _{4 is} an alkoxycarbonyl having a total of 1 to 5 carbon atoms, an amino, phthalimino, aminomethyl, Cyrboxy, cyano, methylsulfonylaminocarbonyl, trifluoromethylsulfonylaminocarbonyl, benzenesulfonylaminocarbonyl, trifluoromethylcarbonylaminomothyl, trifluoromethylaminomethyl, tetrazolyl or 1- (triphenylmethyl) -tetrazolylgruppe,
R _{5 is} a hydrogen, fluorine, chlorine or bromine atom, R _{6 represents} a hydrogen atom or R ₅ and R ₆ together with the two ortho-standing carbon atoms represent a phenyl group, their 1, 3-isomer mixtures and their addition salts with inorganic or organic acids or bases. 6. The method according to claim 1, characterized in that the following benzimidazoles of the formula I are prepared: 6 to 8 carbon atoms or by an alkoxycarbonyl group with a total of 2 to 7. The method according to claim 1, characterized in that physiologically acceptable addition salts of the compounds according to at least one of claims 1 to 6 are prepared with inorganic or organic acids or bases. 8. Use of a compound according to at least one of claims 1 to 7, characterized in that it is for the manufacture of a medicament for the treatment of hypertension, heart failure, ischemic peripheral circulatory disorders, myocardial ischemia (angina), for the prevention of heart failure progression after Myocardial infarction, is useful for the treatment of diabetic nephropathy, glaucoma, gastrointestinal disorders and bladder disorders.