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| | 1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride Basic information |
| Product Name: | 1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride | | Synonyms: | R50547;LIVOSTIN;[3s-[1(cis),3α,4β]]-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic acid;4-Piperidinecarboxylic acid, 1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-, monohydrochloride, [3S-[1(cis),3a,4b]]-;4-Piperidinecarboxylic acid, 1-[cis-4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-, monohydrochloride, (3S,4R)- (9CI);Levophta, Levostin, R50547, [3S-[1(cis),3α,4β]]-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic acid;LEVOPHTA;LEVOCABASTINE HCL | | CAS: | 79547-78-7 | | MF: | C26H30ClFN2O2 | | MW: | 456.99 | | EINECS: | 209-062-5 | | Product Categories: | Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 79547-78-7.mol |  |
| | 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 | | Major Application | pharmaceutical (small molecule) | | InChIKey | OICFWWJHIMKBCD-VALQNVSPSA-N | | SMILES | Cl[H].C[C@@H]1CN(CC[C@]1(C(O)=O)c2ccccc2)[C@@H]3CC[C@@](CC3)(C#N)c4ccc(F)cc4 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 2933399090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 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 Preparation Products And Raw materials |
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