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WO1981002012A1 - Nouveaux 2-amino methyl - 6 - halogenophenols, leur preparation et leurs compositions pharmaceutiques - Google Patents

Nouveaux 2-amino methyl - 6 - halogenophenols, leur preparation et leurs compositions pharmaceutiques Download PDF

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Publication number
WO1981002012A1
WO1981002012A1 PCT/CH1981/000004 CH8100004W WO8102012A1 WO 1981002012 A1 WO1981002012 A1 WO 1981002012A1 CH 8100004 W CH8100004 W CH 8100004W WO 8102012 A1 WO8102012 A1 WO 8102012A1
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WO
WIPO (PCT)
Prior art keywords
compounds
formula
methyl
mentioned above
meanings mentioned
Prior art date
Application number
PCT/CH1981/000004
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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 WO1981002012A1 publication Critical patent/WO1981002012A1/fr

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    • 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
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
    • 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
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • 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
    • 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
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Definitions

  • the invention relates to 2-aminomethyl-6-halogenophenols, their preparation and pharmaceutical supplements.
  • British Patent Application No. 2013655A describes a class of 2-aminomethyl-6-halophenols with an alkylene chain optionally substituted by alkyl between positions 3 and 4 or 4 and 5 of the phenolic ring and with an amino group which is optionally substituted by alkyl.
  • the compounds are mentioned to be used as anti-inflammatories, narcotics, antipyretics, diuretics and egg potentiators.
  • the invention relates to compounds of the formula
  • R 1 and R 2 are both either H or methyl or one of R 1 and R 2 is H and the other is methyl and both R 3 are either H or linear (C 1-4 ) alkyl or X iodine, n 1, R 1 and R 2 both H and both R 3
  • (C 1 -4 ) are alkyl, or n 2, one of R 1 and R 2 H and the other methyl or both R 1 and R 2 methyl and both R 3 are either H or (C 1 -4 ) alkyl.
  • a group of compounds is of the formula Ia,
  • R 1 , R 2 , X and n have the meanings mentioned above and both R 3 'are either H or methyl.
  • a third group of compounds is one of the formula Ib,
  • R 1 and R 2 are both H or one of R 1 and R 2 H and the other is methyl and both R 3 are either H or
  • a fourth group of compounds is one of the formula Ic,
  • R 1 , R 1 and X have the meanings mentioned above.
  • a fifth group of compounds is one of the formula I in which A, B, both R 3 and n have the meanings mentioned above and R 1 and R 2 are both methyl or one of R 1 and R 2 E and the other is methyl.
  • X is preferably Br; n is preferably 1, both R 3 are preferably methyl and at least one of R 1 and R 2 is preferably H.
  • the most preferred compounds are those in which these meanings are combined.
  • the invention also relates to a process for the preparation of the compounds according to the invention, characterized in that a) compounds of the formula I in which B
  • R 1 , R 2 , both R 3 , n and X have the meanings mentioned above, are prepared by bromination or Jcdieren a corresponding compound of formula II,
  • R 1 , R 2 , both R 3 and n have the meanings mentioned above,
  • R 1 and R 2 are H and both R 3 , n and X have the meanings mentioned above, are prepared by hydrolysis of corresponding compounds of the formula III,
  • R 1 and R 2 are H and the other is methyl, both R 3 and n have the meanings mentioned above, are prepared by reducing corresponding compounds of the formula IV,
  • R 1 and R 2 are both methyl and both R 3 and n have the meanings mentioned above, are prepared by catalytic eydrogenation of corresponding compounds of the formula V,
  • R 3 , n and X have the meanings mentioned above and a substituent X, if it has been removed by the eydrogenation, is reintroduced by bromination or iodination.
  • Process a) can be carried out in a conventional manner, as is customary for the preparation of analogous phenols.
  • the method can e.g. at temperatures between about -10 and + 50 ° C, preferably between about 0 ° and room temperature.
  • the bromination or iodination can be carried out by direct reaction with Br or C1J.
  • the bromination process is preferably carried out in a solvent which is inert under the reaction conditions, such as methylene chloride, chloroform, carbon tetrachloride or glacial acetic acid.
  • the iodination is preferably carried out with C1J.
  • the reaction can be carried out in glacial acetic acid or in water, optionally in the presence of a water-miscible solvent behaves inertly under the reaction conditions, such as dioxane.
  • the process is suitably carried out under acidic conditions.
  • Process b) can be carried out in a known manner, as is customary for the hydrolysis of analogous acylamino compounds, preferably by hydrolysis with a strong acid, such as concentrated hydrochloric acid or sulfuric acid.
  • the reaction is preferably carried out in a lower alcohol, such as ethanol, or in a water-miscible solvent, e.g. Dioxane, carried out under reflux.
  • Process c) can be carried out in a conventional manner, as is customary for the reduction of analog imino compounds, for example with complex metal hydrides, such as NaBH 4 , LiAlH 4 , diborane or borane-dimethsulphide complex, and can be carried out in a solvent which is suitable for the chosen reducing agent, such as Tetrahydrofuran, methanol, ethanol or ether, at about 0 to 70 ° C, as described in Example 2c).
  • complex metal hydrides such as NaBH 4 , LiAlH 4 , diborane or borane-dimethsulphide complex
  • Process d) can be carried out in a conventional manner for the catalytic dehydrogenation of analogous azido compounds, for example with palladium or platinum, preferably in an alcohol as solvent at about 20 to 60 ° C. and 5 to 20 atmospheric pressure, as described in Example 6c). If a halogen atom is removed by the hydrogenation, it can be reintroduced by a halogenating agent with a brominating or iodizing effect, in a manner analogous to that in process a). The isolation and purification of the reaction products can take place in a known manner.
  • the starting products of the process according to the invention can be prepared in several reaction steps, as indicated in the following reaction schemes I and II, from an indanol or a 5,6,7,8 tetrahydronaphthol of the formula IX.
  • the first substitution of compound IX takes place mainly in position 6 if an indanol is substituted, or mainly in position 3 and to a small extent in if a tetrahydronaphthol is substituted Indanol position 4 or tetrahydronaphthol position 1 instead.
  • the second substitution then takes place in the free, second ortho position of the phenol ring.
  • the main substitution is shown in Reaction Schemes I and II.
  • the starting products of the processes according to the invention can be formed by three different processes are, depending on whether the aminomethylene group in the ortho position of the phenol ring is unsubstituted or substituted by one or by two methyl groups.
  • the compounds of formula IX are known or can be prepared by known methods, e.g. as described in the examples below. Insofar as the production of a special starting product has not been described, it is known or can be produced in a known manner or in an analogous manner as described here. Free base forms of the compounds according to the invention and of the basic starting products and intermediates can be converted into acid addition salts in a known manner and vice versa. Suitable acids are hydrochloric acid, fumaric acid, oxalic acid and hydrobromic acid.
  • a solution of 10.3 g of sodium nitrite in 80 ml of water is added dropwise to 20 g of 6-amino-1,1-dimethylindan in 100 ml of water and 25 ml of concentrated sulfuric acid with stirring at 0-5 °.
  • the resulting reaction solution is then added dropwise to a boiling solution of 40 ml of concentrated sulfuric acid in 150 ml of water.
  • the title compound is separated from the reaction mixture by steam distillation and obtained by recrystallization from petroleum ether in white crystals of mp. 96-98 °.
  • the crude product described under b) is concentrated in a mixture of 80 ml of ethanol and 80 ml Hydrochloric acid boiled under reflux for 4 1/2 hours. After the ethanol has been removed in vacuo, dilute ammonia is poured onto the excess. The mixture is extracted with methylene chloride. After the organic phase has been dried and evaporated, the crude base can be converted into the crystalline hydrobromide of mp. 220-224 ° for cleaning with HBr in ethanol.
  • Example 3 6- (1-aminoethyl) -4-bromo-1,1-dimethyl-indan-5-ol (I) [Process a)]
  • Example 4 6- (1-aminoethyl) -4-iodoindan-5-oI (I) [Process a)] To a solution of 1.8 g of 6- (1-aminoethyl) indan-5-oI in 20 ml of glacial acetic acid 1.9 g of ClI are added within 10 minutes and the reaction mixture is stirred for a further 3 hours at room temperature. After the volatile constituents have been removed in vacuo, the mixture is made alkaline with aqueous dilute ammonia and extracted with methylene chloride. After the organic phase has been dried and evaporated, a brown oil remains, from which the title compound is obtained in pure form by crystallization from ethanol. Mp 119-121 ° (free base).
  • Example 5 4-Aminomethy1-6-borm-i 1,1-d imethylindan-5-ol-hydrochloride (I) [Process b)]
  • Example 5 The following compounds are prepared in succession in an analogous manner to that in Example 5: a) 1,1-diethylindan-5-ol (IX) colorless viscous oil; b) 6-bromo-1,1-diethylindan-5-ol SP 120-130 ° (at 0.1 mm Hg); c) 6-bromo-4-chloroacetylaminomethyl-1,1-diethylindan-5-ol - yellowish oil; d) 4-aminomethyl-6-bromo-1,1-diethylindan-5-ol mp 165-166 °.
  • the compounds according to the invention have a pharmacological effect and are therefore indicated as pharmaceuticals, for example for therapeutic purposes.
  • the compounds according to the invention have a salidiuretic activity, as is the case in the rat. in the standard test, described in Switzerland. Weinschrift, 93, (1963), 1232-1237.
  • salidiuretics After oral administration of 1 to 100 mg / kg of animal body weight, a salidiuretic effect is perceived.
  • the compounds are therefore indicated as salidiuretics, e.g. for the treatment of edema.
  • the compounds have an antihypertensive activity, which in the spontaneously hypertensive rat in the standard test, described in Proc. Soc.Exptl. Biol. And Med. 57 (1944) 102, can be detected.
  • an antihypertensive effect is perceived.
  • the compounds are therefore indicated as antihypertensive drugs.
  • An appropriate daily dose is between about 1 and about 150 mg and is conveniently administered two to four times a day in unit dosage forms containing about 0.25 to about 75 mg of the compounds or in a sustained release form.
  • X is bromine or iodine and n is 1 or 2
  • both R 1 and R 2 are H and both R 3 are either H or methyl
  • X is bromine or iodine and n is 1 or 2
  • both R 1 and R 2 are H and both R 3 are either H or methyl
  • They are particularly well tolerated and absorbed when given orally and show little potassium ion excretion and / or have a powerful, long-term antihypertensive effect.
  • compositions which contain a compound according to the invention in free base form or as a pharmaceutically acceptable acid addition salt, together with a pharmaceutical carrier or diluent.
  • Such compositions can be in the form of a solution or tablet, for example.
  • the preferred compounds are those of Examples 3 and 5.

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  • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Les nouveaux composes repondent a la formule I: (FORMULE) dans laquelle A ou B represente X et l'autre: (FORMULE) formules dans lesquelles: soit X represente le brome, n = 1 ou 2, R1 et R2 representent tous les deux H ou methyl ou R1 ou R2 represente H et l'autre methyl, R3 representent tous les deux soit H ou un groupe alkyl lineaire C1-4; soit X represente l'iode, n= 1, R1 et R2 representent tous les deux H et R3 representent tous les deux un groupe alkyl C1-4 ou R1 et R2 representent tous les deux methyl ou R1 ou R2 represente H et l'autre methyl, R3 representent tous les deux soit H ou un groupe alkyl C1-4; soit n=2, R1 ou R2 represente H et l'autre methyl ou R1 et R2 representent methyl, R3 representent tous les deux soit H soit un groupe alkyl C1-4. Les composes ainsi que les sels d'acides pharmaceutiquement acceptables sont utilisables comme salidiuretiques et antihypertensifs.
PCT/CH1981/000004 1980-01-14 1981-01-13 Nouveaux 2-amino methyl - 6 - halogenophenols, leur preparation et leurs compositions pharmaceutiques WO1981002012A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH267/80 1980-01-14
CH26780 1980-01-14
CH748380 1980-10-07

Publications (1)

Publication Number Publication Date
WO1981002012A1 true WO1981002012A1 (fr) 1981-07-23

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Country Status (11)

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AU (1) AU6618081A (fr)
DE (1) DE3100592A1 (fr)
DK (1) DK13781A (fr)
FR (1) FR2473512A1 (fr)
GB (1) GB2067195A (fr)
IL (1) IL61894A0 (fr)
IT (1) IT1142256B (fr)
NL (1) NL8100078A (fr)
PT (1) PT72338B (fr)
SE (1) SE8100122L (fr)
WO (1) WO1981002012A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4583344A (en) * 1984-06-06 1986-04-22 Butler Delica M Simulated thatched roofing
GB8812342D0 (en) * 1988-05-25 1988-06-29 Ici America Inc Bicyclic compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2413358A1 (fr) * 1977-12-29 1979-07-27 Ono Pharmaceutical Co Nouveaux derives de 2-aminomethylphenol, utiles notamment comme agents anti-inflammatoires, et leur procede de preparation
WO1980000561A1 (fr) * 1978-09-06 1980-04-03 Sandoz Ag Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant
EP0020301A1 (fr) * 1979-05-28 1980-12-10 Ciba-Geigy Ag Phénols substitués basiquement, procédé pour leur préparation, préparations pharmaceutiques contenant ces composés, ainsi que leur utilisation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2413358A1 (fr) * 1977-12-29 1979-07-27 Ono Pharmaceutical Co Nouveaux derives de 2-aminomethylphenol, utiles notamment comme agents anti-inflammatoires, et leur procede de preparation
WO1980000561A1 (fr) * 1978-09-06 1980-04-03 Sandoz Ag Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant
EP0020301A1 (fr) * 1979-05-28 1980-12-10 Ciba-Geigy Ag Phénols substitués basiquement, procédé pour leur préparation, préparations pharmaceutiques contenant ces composés, ainsi que leur utilisation

Also Published As

Publication number Publication date
IT1142256B (it) 1986-10-08
PT72338A (en) 1981-02-01
GB2067195A (en) 1981-07-22
AU6618081A (en) 1981-07-23
IL61894A0 (en) 1981-02-27
DK13781A (da) 1981-07-15
SE8100122L (sv) 1981-07-15
DE3100592A1 (de) 1981-12-03
NL8100078A (nl) 1981-08-17
PT72338B (en) 1982-04-05
IT8147569A0 (it) 1981-01-14
FR2473512A1 (fr) 1981-07-17

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