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

storage temp. 

2-8°C

solubility 

DMSO: ~10 mg/mL, soluble

form 

solid

color 

white

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2933399090

MSDS

• Language:English Provider:SigmaAldrich

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

Description

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.

Chemical Properties

White or almost white powder.

Originator

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

Uses

A histamine H1 receptor antagonist used in allergic conjunctivitis.

Definition

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

Manufacturing Process

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)

brand name

Livostin (Novartis).

Therapeutic Function

Antihistaminic

1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride(79547-78-7)Related Product Information

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