IP Library Granted Patent US 8,178,573
Granted Patent B2
US 8,178,573 · App. 12/226,372 · Granted May 15, 2012

Compounds

Assignee: Glaxo Group Limited
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,178,573
App. No.
12/226,372
Granted
May 15, 2012
Kind
B2
Abstract

The present invention provides compounds of formula (I): pharmaceutical compositions comprising the compounds and the use of the compounds for the manufacture of a medicament, particularly for the treatment of inflammation and/or allergic conditions.

Claims (30)

1. A compound of formula (I):

wherein

A 1 represents 5-fluoro-2-methoxy-phenyl or 5-fluoro-2-hydroxy-phenyl;

R 1 represents —N(R 2 )C(R 3 )(R 4 )CONHR 5

R 2 represents hydrogen or methyl;

R 3 represents hydrogen and R 4 represents hydrogen, methyl or hydroxymethyl, or R 3 and R 4 each represent methyl; and

R 5 represents hydrogen or methyl;

or a physiologically functional derivative thereof.

2. A compound according to claim 1 wherein A 1 represents 5-fluoro-2-methoxy-phenyl.

3. A compound according to claim 1 wherein R 1 represents

4. A compound which is selected from the group consisting of:

1-{[3-(4-{[(2R)-4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)phenyl]carbonyl}-D-prolinamide; and

a physiologically functional derivative thereof.

5. A compound which is:

1-{[3-(4-{[(2R)-4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)phenyl]carbonyl}-D-prolinamide.

6. A compound which is:

1-{[3-(4-{[(2R)-4-[5-fluoro-2-(methyloxy)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]amino}-6-methyl-1H-indazol-1-yl)phenyl]carbonyl}-D-prolinamide or a physiologically functional derivative thereof in crystalline form.

7. A method for the treatment of a human or animal subject with an inflammatory and/or allergic condition, which method comprises administering to said human or animal subject an effective amount of a compound as claimed in claim 1 , or a physiologically functional derivative thereof.

8. A pharmaceutical composition comprising a compound as claimed in claim 1 , or a physiologically functional derivative thereof, and optionally, in admixture with one or more physiologically acceptable diluents, carriers, or mixtures thereof.

9. A pharmaceutical composition according to claim 8 which further comprises another therapeutically active agent.

10. A process for the preparation of a compound of formula (I) as claimed in claim 1 , or a physiologically functional derivative thereof, comprising:

a) coupling of a carboxylic acid of formula (II):

wherein A 1 is as defined in claim 1 with an amine HN(R 2 )C(R 3 )(R 4 )CONHR 5 or

wherein R 2 , R 3 , R 4 and R 5 are as defined in claim 1 , or

b) coupling of a carboxylic acid of formula (II):

wherein A 1 is as defined in claim 1 with an amine HN(R 2 )C(R 3 )(R 4 )CO 2 H or D- or L-proline, followed by a second coupling with R 5 —NH 2 , wherein R 2 , R 3 , R 4 and R 5 are as defined in claim 1 .

11. A compound of formula (V):

wherein P 1 is an ester protecting group.

12. A compound of formula (X):

wherein P 1 is an ester protecting group.

Assignments (2)
CHANGE OF ADDRESS Recorded Apr 16, 2025
From: GLAXO GROUP LIMITED
To: GLAXO GROUP LIMITED
Reel/Frame 071044/0904 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 25, 2008
From: BIGGADIKE, KEITH; COOPER, ANTHONY WILLIAM JAMES; HOUSE, DAVID; MCLAY, IAIN MCFARLANE; WOOLLAM, GRAHAME ROBERT
To: GLAXO GROUP LIMITED
Reel/Frame 021888/0905 →
Priority Claims (4)
GB 0607840.6 · Apr 20, 2006 · national
GB 0620382.2 · Oct 13, 2006 · national
GB 0706515.4 · Apr 3, 2007 · national
GB 0706516.2 · Apr 3, 2007 · national
Continuity (1)
Related Publication 20090111866A1 · Apr 30, 2009