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WO1980000561A1 - Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant - Google Patents

Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant Download PDF

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Publication number
WO1980000561A1
WO1980000561A1 PCT/CH1979/000113 CH7900113W WO8000561A1 WO 1980000561 A1 WO1980000561 A1 WO 1980000561A1 CH 7900113 W CH7900113 W CH 7900113W WO 8000561 A1 WO8000561 A1 WO 8000561A1
Authority
WO
WIPO (PCT)
Prior art keywords
halogen
alkyl
atomic number
compounds
formula
Prior art date
Application number
PCT/CH1979/000113
Other languages
German (de)
English (en)
Inventor
H Ott
Original Assignee
Sandoz Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sandoz Ag filed Critical Sandoz Ag
Publication of WO1980000561A1 publication Critical patent/WO1980000561A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones

Definitions

  • the invention relates to ⁇ -alkyl-o-oxybenzylamine derivatives, their preparation and medicinal compositions containing them.
  • oxy residue can e.g. Hydroxy or acyloxy mean.
  • the invention relates in particular to the new compounds of the formula I,
  • R 1 denotes alkyl with 1-4 carbon atoms
  • R 2 to R 4 independently of one another are hydrogen or alkyl having 1-4 carbon atoms and either Z is hydrogen or alkyl having 1-7 carbon atoms and W is halogen with an atomic number from 17 to 53, or Z is halogen with an atomic number from 17 to 53 and
  • W represents hydrogen or alkyl of 1-7 carbon atoms, or Z and W represent halogen with an atomic number from 9 to 53, with the restriction that they do not both represent fluorine, and their O- and / or N-acyl derivatives.
  • N-acyl derivatives are only suitable if in form
  • O- and / or N-acyl derivatives of the compounds of formula I are those derivatives in which the hydroxy and / or amino group is present in acylated form.
  • the compounds of formula I are preferred over their derivatives. Of the derivatives, preference is given to those which are acylated only on the nitrogen atom.
  • R 1 , R 2 , R 3 and / or R4 are alkyl, they preferably contain 1-2, in particular 1 carbon atom (s) They are preferably straight-chain. If Z or W represents alkyl, it preferably contains 3-5, in particular 3 or 4, carbon atoms. It is preferably branched in the ⁇ -position to the phenyl ring carbon atom, such as in isopropyl or tert-butyl. Halogen is preferably bromine or iodine, especially bromine.
  • R 3 is preferably hydrogen. If it means alkyl, it is preferably identical to R 1 .
  • R 2 and / or R4 are preferably hydrogen. If R 2 and R 4 are alkyl, they are preferably identical. If R 2 and / or R 4 are alkyl, R 3 is preferably hydrogen.
  • Z is preferably alkyl or halogen, especially alkyl.
  • W preferably represents halogen or alkyl, especially halogen.
  • a group of compounds of the formula I consists of the compounds of the formula Ipa
  • R 1 and R 2 have the above meaning and Z pa alkyl having 1-7 carbon atoms and
  • W pa is halogen with an atomic number from 17 to 53.
  • Another group of compounds of the formula I consists of the compounds of the formula Ipb,
  • R 1 and R 2 have the above meaning and Z pb is halogen with an atomic number from 17 to 53 and W pb is alkyl with 1-7 carbon atoms.
  • Another group of compounds of the formula I consists of the compounds of the formula Ipc,
  • R 1 and R 2 have the above meaning and Z pc halogen with an atomic number from 9 to 53 and W pc halogen with an atomic number from 17 to 53.
  • Another group of compounds of the formula I consists of the compounds of the formula Ipd,
  • R 1 and R 2 have the above meaning, means alkyl with 1-4 carbon atoms and either Z pd alkyl with 1-7 carbon atoms and W pd halogen with an atomic number from 17 to 53, or Z pd for halogen with an atomic number from 17 to 53 and W pd represent alkyl with 1-7 carbon atoms, or Z pd halogen with an atomic number from 9 to 53 and W pd HHaeogen with an atomic number from 17 to
  • the compounds according to the invention are obtained analogously to known methods, e.g. by appropriately chlorinating, brominating or iodinating corresponding ⁇ -alkyl-o-oxybenzylamine derivatives which are substituted in the phenyl ring by at most one halogen atom.
  • R 1 to R 4 have the above meaning and possessing s' atoms of hydrogen or alkyl with 1-7 carbon and W 'is either Z is hydrogen, or Z' is hydrogen and
  • W ' is alkyl with 1-7 carbon atoms or Z' is halogen with an atomic number from 9 to 53 and W 'is hydrogen, or Z' is hydrogen and
  • Z and W are halogen with an atomic number from 17 to 53 and are different, one of Z 'and W' is halogen with an atomic number of 17 to 53 and B) if Z or W is fluorine, correspondingly Z 'or W 'represents fluorine, or its O- and / or N-acyl derivatives, suitably chlorinated, brominated or iodinated.
  • the halogenation process according to the invention can be carried out analogously to known methods for the production of analog o-oxy-halobenzylamines by mono- or dihalogenation.
  • the reaction temperature is about -10 ° to about + 50 ° C, preferably about 0 ° C to room temperature.
  • Chlorination or bromination can e.g. be carried out by direct reaction with chlorine gas or bromine.
  • a catalyst such as iron or iron (III) chloride is expediently used.
  • the reaction is preferably carried out in an inert solvent such as methylene chloride, chloroform, carbon tetrachloride or acetic acid.
  • the iodination can e.g. done with iodine chloride.
  • the implementation is e.g. carried out in water, preferably using an additional hydrophilic solvent such as dioxane. Acidic conditions are expediently used.
  • Z 'and W' are hydrogen, a mixture of compounds can be formed which is known, e.g. can be separated by chromatography or fractional crystallization.
  • the compounds according to the invention can be isolated and purified from the reaction mixture in a known manner.
  • the compounds according to the invention can be in free form or in salt form. Salts can be prepared in a known manner from the compounds in free form win and vice versa. Acid addition salts can be obtained with acids such as maleic, fumaric, tartaric and hydrochloric acid. If the oxy radical is a hydroxyl group, salts with strong bases, such as sodium hydroxide, can be obtained.
  • R 1 and R 3 are different, the carbon atom which bears these substituents is asymmetrically substituted.
  • These compounds can therefore be in racemic or optically active form.
  • the compounds in optically active form can be obtained in a known manner, for example starting from the corresponding racemates, by known Auftrennermeth, such as fractional crystallization of the corresponding diastereoisomeric salts with optically active acids, for example tartaric acid, malic acid or mandelic acid.
  • the starting compounds can be obtained analogously to known methods.
  • O- and / or N-acyl derivatives of the compounds of formula II are obtained e.g. by 0- and / or N-acylation of corresponding compounds of the formula II, if necessary selectively.
  • R 3I represents alkyl with 1-4 carbon atoms and either Z ' , hydrogen, fluorine or alkyl with 1-7 carbon atoms and W''mean hydrogen, or Z''for hydrogen and
  • W '' represent alkyl with 1-7 carbon atoms or fluorine.
  • the starting product is obtained as follows:
  • the starting product is obtained as follows:
  • the starting product is obtained as follows:
  • the compounds according to the invention in free form or in the form of their physiologically tolerable salts are distinguished by interesting pharmacodynamic properties. They can be used as a remedy.
  • They have salidiuretic properties. Due to their salidiuretic effect, they can be used as salidiuretics, for example for the treatment of edema and hypertension.
  • the doses to be used naturally vary depending on the type of substance, the administration and the condition to be treated. However, generally satisfactory results are obtained with a daily dose of about 1 to about 50 mg; if necessary, this dose can be administered in 2 to 4 portions or as a slow-release form.
  • the partial doses contain about 0.25 to about 20 mg of the compounds according to the invention in addition to solid or liquid carrier substances.
  • the compounds according to the invention in free form or in the form of their physiologically tolerable salts can be administered alone or in a suitable dosage form become.
  • the dosage forms for example a solution or a tablet, can be prepared analogously to known methods.
  • the invention therefore relates to medicinal products which contain the compounds according to the invention, and to the preparation of these medicinal products in a manner known per se.
  • the auxiliaries and carriers customary in pharmacy can be used for their production.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Les nouveaux derives de l'(Alpha)-alcoyle-o-oxy-benzylamine, qui presentent dans le cycle phenylique comme substituants un ou au plus deux atomes d'halogene d'un nombre d'ordre dans le systeme periodique de 17 a 53, le ou les atomes d'halogene se trouvant en position meta par rapport au reste amino-alcoyle, possedent des proprietes salidiuretiques et antihypertensives. On les obtient par exemple par chloruration, bromuration ou ioduration.
PCT/CH1979/000113 1978-09-06 1979-08-27 Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant WO1980000561A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH937078 1978-09-06
CH9370/78 1978-09-06
CH437779 1979-05-10
CH437579 1979-05-10
CH557679 1979-06-14

Publications (1)

Publication Number Publication Date
WO1980000561A1 true WO1980000561A1 (fr) 1980-04-03

Family

ID=27428769

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH1979/000113 WO1980000561A1 (fr) 1978-09-06 1979-08-27 Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant

Country Status (14)

Country Link
AU (1) AU5056579A (fr)
DE (1) DE2934508A1 (fr)
DK (1) DK362379A (fr)
ES (1) ES483865A1 (fr)
FI (1) FI792676A (fr)
FR (1) FR2435461A1 (fr)
GB (1) GB2029830A (fr)
IL (1) IL58169A0 (fr)
NL (1) NL7906557A (fr)
PT (1) PT70142A (fr)
SE (1) SE7907185L (fr)
SU (1) SU895283A3 (fr)
WO (1) WO1980000561A1 (fr)
YU (1) YU215279A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1981002012A1 (fr) * 1980-01-14 1981-07-23 Sandoz Ag Nouveaux 2-amino methyl - 6 - halogenophenols, leur preparation et leurs compositions pharmaceutiques

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2792046B2 (ja) * 1987-10-09 1998-08-27 住友化学工業株式会社 光学活性なアミン−ホウ素系化合物、それを有効成分とする不斉還元剤ならびにそれを用いる光学活性化合物の製造方法
US5231227A (en) * 1987-10-09 1993-07-27 Sumitomo Chemical Company, Limited Optically active hydroxybenzylamine derivative and process for producing said compound

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1493949A1 (de) * 1962-05-30 1969-07-10 Merck Ag E Verfahren zur Herstellung von primaeren Aminen
FR2119066A1 (fr) * 1970-12-23 1972-08-04 Merck & Co Inc
FR2203639A1 (fr) * 1972-10-23 1974-05-17 Thomae Gmbh Dr K
FR2212145A1 (fr) * 1973-01-02 1974-07-26 Gerot Pharmazeutika

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1493949A1 (de) * 1962-05-30 1969-07-10 Merck Ag E Verfahren zur Herstellung von primaeren Aminen
FR2119066A1 (fr) * 1970-12-23 1972-08-04 Merck & Co Inc
FR2203639A1 (fr) * 1972-10-23 1974-05-17 Thomae Gmbh Dr K
FR2212145A1 (fr) * 1973-01-02 1974-07-26 Gerot Pharmazeutika

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1981002012A1 (fr) * 1980-01-14 1981-07-23 Sandoz Ag Nouveaux 2-amino methyl - 6 - halogenophenols, leur preparation et leurs compositions pharmaceutiques

Also Published As

Publication number Publication date
DK362379A (da) 1980-03-07
DE2934508A1 (de) 1980-03-20
GB2029830A (en) 1980-03-26
SU895283A3 (ru) 1981-12-30
PT70142A (fr) 1979-10-01
AU5056579A (en) 1980-03-13
ES483865A1 (es) 1980-04-16
SE7907185L (sv) 1980-03-07
IL58169A0 (en) 1979-12-30
FR2435461A1 (fr) 1980-04-04
FI792676A (fi) 1980-03-07
YU215279A (en) 1983-04-30
NL7906557A (nl) 1980-03-10

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