Patent IE-34139-L (IE)
Title: 4-phenyl-butyric acid derivatives
IPC: C07C235/78
Filed: 1970-05-08
Abstract: 1315542 4-Phenyl-butyric acid derivatives ETABS CLIN-BYLA 7 May 1970 [12 May 1969] 22202/70 Heading C2C Novel 4-phenyl-butyric acid derivatives of the general formula wherein R<SP>1</SP> is a chlorine atom or a nitro group, R<SP>2</SP> is an isopropyl, tertiary-butyl or cyclohexyl group, each of R<SP>3</SP> and R<SP>4</SP> is a hydrogen atom or one is a hydrogen atom and the other is a hydroxyl group or both together form an oxygen atom and R<SP>5</SP> is a hydroxyl or alkoxy group, OM where M is an equivalent of an alkali or alkaline earth metal, or NYZ where Y is a hydrogen atom or C 1-4 alkyl group and Z is defined as Y or is a tertiary amino-alkyl group or NYZ is a heterocyclic group having 5-7 ring atoms, with the proviso that when R<SP>1</SP> is a nitro group and R<SP>5</SP> is a hydroxyl group, R<SP>3</SP> and R<SP>4</SP> can only be taken together to form an oxygen atom and when R<SP>5</SP> is NYZ then R<SP>3</SP> and R<SP>4</SP> are each a hydrogen atom, and, when R<SP>5</SP> is a basic group, acid addition salts thereof are prepared (a) when R<SP>1</SP> is a chlorine atom, R<SP>3</SP> and R<SP>4</SP> together form an oxygen atom and R<SP>5</SP> is a hydroxyl group, by treatment of a 4-phenylbutyric acid of the general formula with anhydrous aluminium chloride, followed by monochlorination and decomposition with acid of the resulting complex; (b) when R<SP>1</SP> is a chlorine atom, each of R<SP>3</SP> and R<SP>4</SP> is a hydrogen atom and R<SP>5</SP> is a hydroxyl group, by Wolf- Kishner or Clemmensen reduction of the product of (a); (c) when R<SP>1</SP> is a chlorine atom, one of R<SP>3</SP> and R<SP>4</SP> is a hydrogen atom and the other is an hydroxyl group and R<SP>5</SP> is an hydroxyl group, by complex hydride reduction of the product of (a); (d) when R<SP>1</SP> is a nitro group, R<SP>3</SP> and R<SP>4</SP> together form an oxygen atom and R<SP>5</SP> is an hydroxyl group, by mononitration of a 4- phenylbutyric acid of the second general formula above; (e) when R<SP>5</SP> is an alkoxy group, by esterification of the corresponding free acid with an alkanol in the presence of a hydrogen halide; (f) when R<SP>5</SP> is NYZ, by reaction of the corresponding free acid with a thionyl halide and treatment of the resulting acid halide with ammonia or an amine of the general formula HNYZ; (g) when R<SP>5</SP> is OM, where M is an alkali metal atom, by neutralization of the corresponding free acid with an alkali metal hydroxide; (h) when R<SP>5</SP> is OM, where M is an equivalent of an alkaline earth metal, by treatment of the product of (g) with an alkaline earth metal salt; and (i) when R<SP>5</SP> is a basic group and the product is in the form of a salt, by salification of the corresponding free base with an acid. Pharmaceutical compositions having antiinflammatory and analgesic activity comprise, as active ingredient, at least one 4-phenylbutyric acid derivative of the first general formula above, together with a pharmacologically acceptable carrier, and may be administered orally, endorectally or parenterally.
[GB1315542A]