Cycloalkane-substituted phenylacetic acid derivatives, their...

Details Cycloalkane-substituted phenylacetic acid derivatives, their... Cycloalkane-substituted phenylacetic acid derivatives, their...

C - Chemistry, Metallurgy

07

C

260/515.3, 260/4

C07C 59/86 (2006.01) C07C 69/738 (2006.01) C07C 279/14 (2006.01)

Patent

CA 1113113

ABSTRACT: 4-(2-oxo- or 2-hydroxyimino-cycloalkan-1-yl- methyl)phenylacetic acid derivatives and non-toxic pharmaceutically acceptable salts and esters thereof are useful as anti-inflammatory agents. The 2-oxo compounds may be prepared by (a) hydrolyzing and then decarboxylating the corresponding 4-(1-alkoxy- carbonyl-2-oxocycloalkan-1-ylmethyl)phenylacetic acid ester or by (b) reacting a p-halomethyl- or p-sulphonyl- oxymethyl-phenylacetic acid ester derivative with an enamine of a cycloalkanone and hydrolyzing the resulting product. The 2-hydroxyimino compounds may be prepared by (c) reacting the corresponding 2-oxo compound, which can have been produced by process (a) or process (b), with hydroxylamine or a derivative thereof or by (d) reacting a dilithium salt of a cycloalkanone oxime with a p-halomethyl- or p-sulphonyloxymethyl-phenylacetic acid ester derivative to produce the ester of the 2-hydroxy- imino compound and, if desired, hydrolyzing the resulting product. The salts and esters may be produced from the corresponding acids by conventional salification and esterification processes.

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