Title of Invention	A PROCESS FOR THE MANUFACTURE OF NOVEL ARYL CYCLOALKANOL DERIVATIVES HAVING ANTI-INFLAMMATORY PROPERTIES.
Abstract	A process for the manufacture of novel arylcycloakanol derivatives having anti-inflammatory properties and having a structure as per the formula I shown in the drawings-accompanying the provisional specification, wherein R. is C--Cfi- substituted alkyl, C(0) 0-c1-CA-alkyl C(O) CH or groups Jhown in Fig. 1 to 10 of the drawings 4 accompanying the provisional specification, wherein R- is one or more of the following residues : V. Ci-C-- substituted alkyl-, hydroxy, alkoxy, -C,-C.-al'kyl-0-C,-C, alkyl, 20-C--C4 alkY1-» -0-C(0)-C1-C4alkyl, -C<0)-O-C>C4alkylf 1 4 halogens such as chloro, bromo, fludro, amino, -NH-c]-C4- alkyl, -N-t-C^-C^ alkyl )o"or groups such as -C.-C.-alkyl-FL-. wherein R, is groups^hawn In Ffgs 11 to 15 of the drawings accompanying the° ; provisional specification and X.is O, S, W-H or H-alkyl, R^ is H, C,-Q6-alkyl or.- C(O)- C.-CA-alkyl, R~ is one or more of the following resiaues :, . H, C--C,- alkyl, - C(0)-0-alkyl, OH, 0-C1-CA-aikyl, 0-C(0)-C1-Cfi alkyl or halogens such as chloro, bromo,fluoro, Rz is H» -°H» -0-C--CA- alkyl -O-C(0)-alkyl, -C(O) OH or -C(0)-0-alkyl, n*is O, 1 or 2 and 'a9 represents an ethylenic linkage or a saturated system, which comprises. (i) treating an aryllithium of the formula IV shown in the drawings accompanying the provisional specification wherein"R„ and R-are as defined above, with cyclohexanone followed by dehydration of the resulting product in the presence of an acid catalyst such as hydrochloric acid to obtain a compound of the formula V shown in the^ drawings accompanying the provisional specification, wherein JU and R3 are as defined above ; (ii} treating the compound of the formula V with a reagent such as borane tetrahydroufuran, borane-dimethylsufide, followed by oxidation of the resulting organoborane in situ with alkaline hydrogen perox'ide" to give a compound of the formula VI shown in the drawings accompanying the provisional specification wherein R- , R_ and R4 are as defined above or treating the compound of the formula V with a perncid such as m-chloroperbenzoic acid, followed by treatment of the resulting epoxide in situ with a hydride reagent such as lithium aluminium hydride to give an enantiomeric mixture of compounds of the formula VI, wherein R?, R3 and R. are as defined above and resolving the enantiomeric mixture In known manner; (iii) treating the enantiomeric compound of the formula VI with acetic anhydride and a mineral acid such as phosphoric acid or sulfucic acid and demethylating the resulting compound with a Lewis acid such as boron tribromide or a demethylating agent such as metal thiolate followed by treatment of the resulting product with a dilute alkali such as sodium hydroxide or potassium hydraoxid to obtain a compound of the formula VII shown in the drawings accompanying the provisional specification, wherein R^,, R- and R. are as defined above ; (iV) treating the compound of the formula VII with an aldehyde such as benzaldehyde in the presence of a base such as socium hydroxide or potassium hydroxide followed by hydrogenation of the resulting cholcone with'H« and pd/c to obtain the compound of the formula,!

Title of Invention

A PROCESS FOR THE MANUFACTURE OF NOVEL ARYL CYCLOALKANOL DERIVATIVES HAVING ANTI-INFLAMMATORY PROPERTIES.

Abstract

A process for the manufacture of novel arylcycloakanol derivatives having anti-inflammatory properties and having a structure as per the formula I shown in the drawings-accompanying the provisional specification, wherein R. is C--Cfi- substituted alkyl, C(0) 0-c1-CA-alkyl C(O) CH or groups Jhown in Fig. 1 to 10 of the drawings 4 accompanying the provisional specification, wherein R- is one or more of the following residues : *V. Ci-C-- substituted alkyl-, hydroxy, alkoxy, -C,-C.-al'kyl-0-C,-C, alkyl, 20-C--C4 alkY1-» -0-C(0)-C1-C4alkyl, -C<0)-O-C>C4alkylf 1 4 halogens such as chloro, bromo, fludro, amino, -NH-c]-C4- alkyl, -N-t-C^-C^ alkyl )o"or groups such as -C.-C.-alkyl-FL-. wherein R, is groups^hawn In Ffgs 11 to 15 of the drawings accompanying the° ; provisional specification and X.is O, S, W-H or H-alkyl, R^ is H, C,-Q6-alkyl or.- C(O)- C.-CA-alkyl, R~ is one or more of the following resiaues :, . H, C--C,- alkyl, - C(0)-0-alkyl, OH, 0-C1-CA-aikyl, *0-C(0)-C1-Cfi alkyl or halogens such as chloro, bromo,fluoro, Rz is H» -°H» -0-C--CA- alkyl -O-C(0)-alkyl, -C(O) OH or -C(0)-0-alkyl, n*is O, 1 or 2 and 'a9 represents an ethylenic linkage or a saturated system, which comprises. (i) treating an aryllithium of the formula IV shown in the drawings accompanying the provisional specification wherein"R„ and R-are as defined above, with cyclohexanone followed by dehydration of the resulting product in the presence of an acid catalyst such as hydrochloric acid to obtain a compound of the formula V shown in the^ drawings accompanying the provisional specification, wherein JU and R3 are as defined above ; (ii} treating the compound of the formula V with a reagent such as borane tetrahydroufuran, borane-dimethylsufide, followed by oxidation of the resulting organoborane in situ with alkaline hydrogen perox'ide" to give a compound of the formula VI shown in the drawings accompanying the provisional specification wherein R- , R_ and R4 are as defined above or treating the compound of the formula V with a perncid such as m-chloroperbenzoic acid, followed by treatment of the resulting epoxide in situ with a hydride reagent such as lithium aluminium hydride to give an enantiomeric mixture of compounds of the formula VI, wherein R?, R3 and R. are as defined above and resolving the enantiomeric mixture In known manner; (iii) treating the enantiomeric compound of the formula VI with acetic anhydride and a mineral acid such as phosphoric acid or sulfucic acid and demethylating the resulting compound with a Lewis acid such as boron tribromide or a demethylating agent such as metal thiolate followed by treatment of the resulting product with a dilute alkali such as sodium hydroxide or potassium hydraoxid to obtain a compound of the formula VII shown in the drawings accompanying the provisional specification, wherein R^,, R- and R. are as defined above ; (iV) treating the compound of the formula VII with an aldehyde such as benzaldehyde in the presence of a base such as socium hydroxide or potassium hydroxide followed by hydrogenation of the resulting cholcone with'H« and pd/c to obtain the compound of the formula,!

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Patent Number

173734

Indian Patent Application Number

194/BOM/1991

PG Journal Number

39/2012

Publication Date

28-Sep-2012

Grant Date

27-Jan-1995

Date of Filing

02-Jul-1991

Name of Patentee

HOECHST INDIA LIMITED

Applicant Address

HOCHEST HOUSE, NARIMAN POINT, 193 BACKBAY RECLAMATION, BOMBAY 400021

Inventors:

#	Inventor's Name	Inventor's Address
1	ROBERT RUDER	HOCHEST WERKE ALBERT, HOECHST AG, 6230 FRANKFURT, (M)-80, GERMANY
2	K.U.WEITHMANN	HOCHEST WERKE ALBERT, HOECHST AG, 6230 FRANKFURT, (M)-80, GERMANY
3	VILAS NARAYAN MUMBAIKAR	HOCHEST INDIA LIMITED, RESEARCH CENTRE, L B S MARG, MULUND (W), BOMBAY 400080
4	RAMCHANDRAN GANPATI NAIK	HOCHEST INDIA LIMITED, RESERCH CENTRE, L B S MARG, MULUND (W), BOMBAY 400080
5	RANGARAJAN VASUMATHY	HOCHEST INDIA LIMITED, RESEARCH CENTRE, L B S MARG, MULUND (W), BOMBAY 400080
6	AFTAB DAWOODBHAI LAKADA	HOCHEST INDIA LIMITED, RESEARCH CENTRE, L B S MARG, MULUND (W), BOMBAY 400080
7	MANDAKINI VITHALRAO SHIROLE	HOCHEST INDIA LIMITED, RESEARCH CENTRE, L B S MARG, MULUND (W), BOMBAY 400080
8	BANSI LAL	HOCHEST INDIA LIMITED, RESEARCH CENTRE, L B S MARG, MULUND (W), BOMBAY 400080
9	JURGEN BLUMBACH	HOCHEST INDIA LIMITED, RESEARCH CENTRE, L B S MARG, MULUND (W), BOMBAY 400080

PCT International Classification Number

A61K31/00

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA