1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride

Levocabastine hydrochloride is a new, highly potent and specific histamine HI-receptor antagonist without anticholinergic or antiserotonergic side effects. It is reported to have both a fast onset and long duration of action. Indications are the treatment of allergic conjunctivitis and allergic rhinitis.

White or almost white powder.

Janssen (Johnson & Johnson) (U.S.A.)

A histamine H1 receptor antagonist used in allergic conjunctivitis.

ChEBI: Livostin (TN) is a member of piperidines.

4-Cyano-4-(4-fluorophenyl)-heptanedioic acid diethyl ester is obtained by addition of ethyl acrylate to the anion from p-fluorophenylacetonitrile. By base catalyzed cyclization of these diester (sodium methoxide, 60°C, xylene) is synthesized an intermediate that after decarboethoxylation gives 1-(4- fluorophenyl)-4-oxycyclohexanecarbonitrile. By condensation of 3-methyl-5- phenylpiperidine-4-carboxylic acid benzyl ester and 1-(4-fluorophenyl)-4- oxycyclohexanecarbonitrile under reductive hydrogenation conditions (palladium-on-charcoal catalyst, 50°C, in ethanol) is prepared benzyl ester 4- piperidinecarboxylic acid, 1-(4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl- 4-phenyl-, (3S-(1(cis),3α,4β))-. The benzyl protecting group is then removed by hydrogenation method and 4-piperidinecarboxylic acid, 1-(4-cyano-4-(4- fluorophenyl)cyclohexyl)-3-methyl-4-phenyl-, (3S-(1(cis),3α,4β))- obtained is transformed into 4-piperidinecarboxylic acid, 1-(4-cyano-4-(4-fluorophenyl) cyclohexyl)-3-methyl-4-phenyl-, hydrochloride, (3S-(1(cis), 3α,4β))- (Levocabastine hydrochloride)

Livostin (Novartis).

Antihistaminic