IP Library › Patent Application 10544360
Patent Application
App. No. 10/544,360

2,3'-bipyridines derivatives as selective cox-2 inhibitors

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Quick Facts
Patent No.
US None
App. No.
10/544,360
Abstract

The present invention relates to 2,3′-bipyridines of formula (I), processes for their preparation, pharmaceutical compositions containing them, and their medical uses.

Claims (26)

1 . A compound of formula (I):

wherein the compound of formula (I) is in the form of any of the two different enantiomers;

or a pharmaceutically acceptable salt thereof; or a N-oxide thereof; or a mixture thereof of any such compounds in any ratio.

2 . A compound according to claim 1 which is in the form of the free base.

3 . A compound according to claim 1 , chosen from:

(R) 5-chloro-6′-methyl-3-[4-(methylsulfinyl)phenyl]-2,3′-bipyridine; and

(S) 5-chloro-6′-methyl-3-[4-(methylsulfinyl)phenyl]-2,3′-bipyridine.

4 . (canceled)

5 . A process for the preparation of a compound as claimed in claim 1 , comprising:

reacting a compound of formula (II)

with an oxidizing agent to produce a compound of formula (I), and

optionally converting the compound of formula (I) into a pharmaceutically acceptable salt or into a N-oxide.

6 . A process according to claim 5 , wherein the oxidizing agent is chosen from:

(a) sodium metaperiodate; and

(b) a mixture of titanium tetraisopropoxide, t-butyl hydroperoxide and either the (R,R) or the (S,S) form of diethyl tartrate.

7 . A process according to claim 6 , wherein the reaction takes place in at least one chlorinated solvent or in a mixture of at least one chlorinated solvent and at least one C 1 -C 4 alcohol.

8 . A process according to claim 7 , wherein the at least one chlorinated solvent is chosen from 1,2-dichloroethane, methylene chloride, chloroform, and mixtures thereof.

9 . A pharmaceutical composition comprising at least one compound according to claim 1 and at least one pharmaceutically acceptable diluent or carrier.

10 . A medicament comprising at least one compound according to claim 1 .

11 . A pharmaceutical composition comprising at least one compound according to claim 3 and at least one pharmaceutically acceptable diluent or carrier.

12 . A method for treating a subject afflicted with pathological condition or disease susceptible to amelioration by inhibition of the enzyme cyclooxygenase-2 (COX-2), comprising administering to the subject an effective amount of a compound according to claim 1 .

13 . A method according to claim 12 , wherein the pathological condition or disease is chosen from pain, fever, inflammation, prostanoid-induced smooth muscle contraction, colorectal cancer, and neurodegenerative diseases.

14 . A method for treating a subject afflicted with a pathological condition or disease susceptible of amelioration by inhibition of the enzyme cyclooxygenase-2 (COX-2), comprising administering to said subject an effective amount of a composition according to claim 11 .

15 . A method according to claim 14 , wherein the pathological condition or disease is chosen from pain, fever, inflammation, prostanoid-induced smooth muscle contraction, colorectal cancer, and neurodegenerative diseases.

16 . A compound according to claim 1 , wherein the pharmaceutically acceptable salt is a quaternary ammonium salt.

17 . A compound according to claim 16 , wherein the quaternary ammonium nitrogen is bound to a C 1 -C 6 alkyl group.

Assignments (2)
CHANGE OF NAME Recorded Jan 22, 2007
From: ALMIRALL PRODESFARMA S.A.
To: LABORATORIOS ALMIRALL, S.A.
Reel/Frame 018786/0571 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2006
From: CATURLA JAVALOYES, JUAN FRANCISCO; WARRELLOW, GRAHAM
To: ALMIRALL PRODESFARMA SA
Reel/Frame 017447/0570 →