Novel antihistaminic piperidine derivatives and intermediates for the preparation thereof

• US 20030022919A1
• Filed: 06/12/2002
• Published: 01/30/2003
• Est. Priority Date: 07/02/1998
• Status: Active Grant

• Current Assignee: Chattem Incorporated (Sanofi )
• Original Assignee: Aventis Pharmaceuticals Incorporated (Sanofi )
• Inventors: Brown, Paul W., Ayers, Timothy A.
• Granted Patent: US 6,683,094 B2
• Time in Patent Office: Days
• US Class Current: 514/317
• CPC Class Codes: C07D 211/22 by oxygen atoms

Abstract

This invention relates to novel piperidine derivatives of formula (I) and a process for the preparation thereof.

wherein

R₁ is H or C₁-C₆alkyl wherein the C₁-C₆alkyl moiety is straight or branched;

R₂ is —COOH or —COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; or stereoisomers or pharmaceutically acceptable acid addition salt thereof.

Claims

1. A compound of the formula

2. The compound of claim 1 wherein R₁ is methyl and R₂ is COOCH₂CH₃.

17. A method of treating a patient suffering from a histamine-mediated allergic disorder comprising administering daily to said patient an effective antiallergic amount of a compound of claim 1.

18. A pharmaceutical composition in unit dosage form comprising an effective antiallergic amount of a compound of claim 1 in admixture with a pharmaceutically acceptable carrier.

11. A process for preparing a compound of the formula

12. A process according to claim 11 wherein the suitable selective reducing agent is lithium tri-tert-butoxyaluminohydride.

13. A process according to claim 11 wherein the process is catalytic.

14. A process according to claim 11 wherein the suitable selective reducing agent is a suitable silane in combination with a suitable titanocene-based catalyst.

15. A process according to claim 14 wherein the suitable silane is polymethylhydrosiloxane and the suitable titanocene-based catalyst is “

Cp₂TiH”

.

16. A process according to claim 11 wherein the reduction is asymmetric.