IE33611L - ß-PHENYL FATTY ACID COMPOUNDS - Google Patents

Abstract

1,260,875. Beta-phenyl-fatty acid derivatives. CIBA-GEIGY A.G. 24 Oct., 1969 [25 Oct., 1968; 23 May, 1969; 23 Sept., 1969], No. 52230/69. Heading C2C. Novel compounds I in which X is free, esterified or amidated carboxyl; A is a free or substituted OH group or together with B forms a bond; B is H, aliphatic hydrocarbyl, with A forms a bond or with R 2 forms a divalent aliphatic hydrocarbon residue; R 1 is H or aliphatic hydrocarbyl; R 2 is as R 1 or with B forms a divalent aliphatic hydrocarbon residue; Ph is phenylene optionally substituted by alkyl, halo, CF 3 , amino or nitro and R is cycloaliphatic hydrocarbyl which may be substituted are prepared by: (1) reacting R-Ph-COR 1 in the presence of Zn with Hal-C(B)(R 2 )-X 0 where X 0 is esterified carboxyl; (2) decarboxylating (3) isomerizing R-Ph-C(=R 1 <SP>1</SP>)-CHR 2 -X where R 1 <SP>1</SP> is a divalent residue of aliphatic character in which the free valencies emanate from the same carbon atom; or (4) converting the CN group in to X and where necessary in (1)-(4) conventionally modifying the products to give other compounds I. Novel compounds II are prepared by (1) splitting off the residues Y<SP>11</SP> in (one Y<SP>11</SP> is H, the other a free or reactively esterified OH) or (2) isomerizing a compound R-Ph-C(R 1 ) = C(R 2 )-X followed in either (1) or (2) by conventional modification as necessary. Intermediates isolated are 2-[p-(1<SP>1</SP>-hydroxy-1<SP>1</SP>- cyclohexyl)-phenyl]-2-methyl-1,3-dioxolan, prepared by reaction of 2-(p-bromo-phenyl)-2- methyl-1,3-dioxolan with cyclohexanone; p- (1-cyclohexenyl)-acetophenone, prepared by the action of conc. HCl in the first-named intermediate; 2-(m-bromophenyl)-2-methyl-1,3-dioxolan, prepared from ethylene glycol and m-bromoacetophenone; 2-[m-(1<SP>1</SP>-hydroxy-1<SP>1</SP>-cyclohexyl)- phenyl]-2-methyl-1,3-dioxolan, prepared similarly to the first-named intermediate; m-(1-cyclohexenyl)-acetophenone, prepared by action of cone. HCl on the last-named intermediate; 2-[p- (1<SP>1</SP> - hydroxy - 1<SP>1</SP> - cycloheptyl) - phenyl] - 2- methyl-1,3-dioxolan and p-(-cycloheptenyl)-acetophenone, prepared similarly to the first- and second-named intermediates; 2-[p-(1<SP>1</SP>-hydroxy- 1<SP>1</SP>-cyclopentyl)-phenyl]-2-methyl-1,3-dioxolan and p-(1-cyclopentenyl)acetophenone, prepared similarly to the first- and second-named intermediates; 2-[p-(4-methoxy-1-hydroxy-cyclohexyl)-phenyl]-2-methy.-1,3-dioxolan and p-(4-methoxy-1- cyclohexenyl)-acetophenone, prepared similarly to the first- and second-named intermediates; 2-[p-(2 - methyl- 1 - hydroxy - cyclohexyl) - phenyl]- 2-methyl-1,3-dioxolan, prepared similarly to the first-named intermediate; a mixture of p-(6- methyl-1-cycloheexnyl)- and p-(2-methyl-1-cyclohexenyl)-acetophenone, prepared by reaction of the last-named intermediate with 2NHCl; pcyclohexyl-benzoic acid amide, prepared from the acid chloride by reaction with NH 3 ; p-cyclohexylbenzonitrile, prepared by reaction of the lastnamed intermediate with POCl 3 ; p-cyclohexylbenzaldehyde, prepared from the last-named intermediate by reaction with HCl gas in the presence of SnCl 4 ; and p-cycloheryl-benzylidenemalonic acid, prepared from the last-named intermediate by reaction with diethyl malonate, followed by hydrolysis. Pharmaceutical compositions comprise a compound I or II together with a suitable carrier and have analgesic and anti-inflammatory activity when administered, enterally, parenterally or topically. [GB1260875A]