IP Library Granted Patent US 8,258,130
Granted Patent B2
US 8,258,130 · App. 12/570,355 · Granted Sep 4, 2012

Pyrimidine hydrazide compounds as PGDS inhibitors

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 8,258,130
App. No.
12/570,355
Granted
Sep 4, 2012
Kind
B2
Abstract

This invention is directed to a compound of formula (I): wherein R 1 , R 2 , R 3 , R 4 and L 1 are as defined herein, a pharmaceutical composition comprising the compound, and the use of the compound to treat allergic and/or inflammatory disorders, particularly disorders such as allergic rhinitis, asthma and/or chronic obstructive pulmonary disease (COPD).

Claims (455)

1. A compound of formula (I):

wherein:

R 1 is (C 1 -C 6 )-alkyl optionally substituted one or more times independently by halo, hydroxy, (C 1 -C 6 )-alkoxy, or (C 1 -C 4 )-haloalkoxy, or

(C 3 -C 6 )-cycloalkyl, aryl or heteroaryl, each of which is optionally substituted one or more times independently by halo, (C 1 -C 6 )-alkyl, hydroxy, (C 1 -C 6 )-alkoxy, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-haloalkoxy;

R 2 is hydrogen or (C 1 -C 4 )-alkyl optionally substituted one or more times by halogen;

R 3 is hydrogen, alkyl, aryl or heteroaryl,

R 4 is cycloalkyl, aryl, heterocyclyl, heteroaryl, heteroarylsulfonyl, —C(═O)—NY 1 Y 2 , —C(═S)—NY 1 Y 2 , R 5 , —C(═O)—R 5 or —C(═S)—R 5 , wherein the aryl, heteroaryl or heterocyclyl moiety is optionally substituted one or more times independently by R 6 , or

R 3 and R 4 together with the nitrogen atom to which they are attached form heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, each of which is optionally substituted one or more times independently by R 6 ;

R 5 is cycloalkyl, cycloalkenyl, aryl, heteroaryl, heterocyclyl, heterocyclenyl, or multicyclic alkaryl, each of which is optionally substituted one or more times independently by R 6 ;

L 1 is a bond, —O—, —C(═O)—, —NH—C(═O)—, or (C 1 -C 2 )-alkylene optionally substituted one or more times by halo;

R 6 is oxo, cyano, nitro, halo, hydroxy, carboxy, Y 1 Y 2 N—, Y 1 Y 2 N—C(═O)—, Y 1 Y 2 N—SO 2 —,

acyl, acyloxy, alkyl, alkenyl, alkynyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, or alkylsulfonyl, each of which is optionally substituted one or more times independently by:

acyloxy, halo, alkoxy, haloalkoxy, hydroxy, carboxy, alkoxycarbonyl,

Y 1 Y 2 N—, Y 1 Y 2 N—C(═O)—, Y 1 Y 2 N—SO 2 —,

aryl, aryloxy, aroyl, heteroaryl, heteroaryloxy, heteroaroyl, heterocyclyl, heterocyclenyl, cycloalkyl, cycloalkenyl, or multicyclic alkaryl, each of which is optionally substituted one or more times independently by alkyl, halo, haloalkyl, alkoxy, haloalkoxy, hydroxy, amino, alkylamino, dialkylamino, carboxy, or alkoxycarbonyl, or

aryl, heteroaryl, aroyl, heteroaroyl, aryloxy, heteroaryloxy, heterocyclyl, heterocyclenyl, cycloalkyl, cycloalkenyl, or multicyclic alkaryl, each of which is optionally substituted one or more times independently by alkyl, haloalkyl, halo, alkoxy, haloalkoxy, hydroxy, carboxy, alkoxycarbonyl, Y 1 Y 2 N—, or Y 1 Y 2 N—SO 2 —,

wherein the heterocyclyl, heterocyclenyl, cycloalkyl, cycloalkenyl, or multicyclic alkaryl moiety of R 6 is also optionally substituted one or more times independently by oxo;

Y 1 and Y 2 are each independently:

hydrogen, alkylsulfonyl, aroyl, heteroaroyl, or

alkyl optionally substituted one or more times independently by hydroxy, carboxy, halo, amino, alkylamino, dialkylamino, alkoxy, heterocyclyl, aryl or heteroaryl, or

Y 1 and Y 2 together with the nitrogen atom to which they are attached form heterocyclyl;

or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 , wherein R 1 is aryl or heteroaryl, each of which is optionally substituted one or more times independently by halo, (C 1 -C 6 )-alkyl, hydroxy, (C 1 -C 6 )-alkoxy, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-haloalkoxy, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1 , wherein R 1 is phenyl or five or six membered heteroaryl, each of which is optionally substituted one or more times independently by halo, (C 1 -C 6 )-alkyl, hydroxy, or (C 1 -C 6 )-alkoxy, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1 , wherein R 1 is phenyl, pyridyl, pyrimidinyl, thiazolyl, or oxadiazolyl, each of which is optionally substituted one or more times independently by halo, (C 1 -C 6 )-alkyl, hydroxy, or (C 1 -C 6 )-alkoxy, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

5. The compound according to claim 1 , wherein R 1 is phenyl, pyridyl or pyrimidinyl, each of which is optionally substituted independently at the ortho or meta position by halo, (C 1 -C 6 )-alkyl, hydroxy, or (C 1 -C 6 )-alkoxy, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

6. The compound according to claim 1 , wherein R 1 is phenyl optionally substituted independently at the ortho or meta position by halo, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

7. The compound according to claim 1 , wherein R 1 is pyridyl, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

8. The compound according to claim 1 , wherein R 2 is hydrogen, methyl or trifluoromethyl, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

9. The compound according to claim 1 , wherein R 2 is hydrogen, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

10. The compound according to claim 1 , wherein R 2 is methyl, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

11. The compound according to claim 1 , wherein L 1 is a bond, —O—, —C(═O)—, or —NH—C(═O)—, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

12. The compound according to claim 1 , wherein L 1 is a bond, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

13. The compound according to claim 1 , wherein:

R 3 and R 4 together with the nitrogen atom to which they are attached form heterocyclyl, heterocyclenyl, arylheterocyclyl, or heteroaryl, each of which is optionally substituted one or more times independently by R 6 ;

R 6 is alkoxy, hydroxyl, cycloalkyl, carboxy, cycloalkyl, halo, cyano, alkylsulfonyl, Y 1 Y 2 N—, Y 1 Y 2 N—SO 2 —,

alkyl optionally substituted one or more times independently by acyloxy, hydroxy, alkoxycarbonyl, alkoxy, carboxy, aryl, halo, alkylsulfonyl, cyano, Y 1 Y 2 N—, or Y 1 Y 2 N—C(═O)—,

acyl or aryl, each of which is optionally substituted one or more times independently by halo,

alkoxycarbonyl optionally substituted one or more times independently by aryl,

heteroaroyl optionally substituted one or more times independently by alkyl,

heterocyclyl optionally substituted one or more times by oxo, or

aryloxy optionally substituted one or more times independently by haloalkyl; and

Y 1 and Y 2 are each independently hydrogen, alkylsulfonyl, aroyl, or alkyl optionally substituted by morpholinyl, or

Y 1 and Y 2 together with the nitrogen atom to which they are attached form morpholinyl;

or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

14. The compound according to claim 1 , wherein:

R 3 and R 4 together with the nitrogen atom to which they are attached form [1,2,4]triazolyl, pyrrolyl, indolyl, pyrrolo[2,3-b]pyridyl, pyrrolo[3,2-b]pyridyl, or pyrrolo[2,3-c]pyridyl, each of which is optionally substituted one or more times independently by R 6 ;

R 6 is alkoxy, carboxy, cycloalkyl, halo, cyano, alkylsulfonyl, Y 1 Y 2 N—SO 2 —,

alkyl optionally substituted one or more times independently by Y 1 Y 2 N—C(═O)—, hydroxy, alkoxycarbonyl, alkoxy, carboxy, aryl, halo, heterocyclyl, cycloalkyl, alkylsulfonyl, cyano, heterocyclylcarbonyl,

acyl or aryl, each of which is optionally substituted one or more times independently by halo,

alkoxycarbonyl optionally substituted one or more times independently by aryl,

heteroaroyl optionally substituted one or more times independently by alkyl,

heterocyclyl optionally substituted one or more times by oxo, or

aryloxy optionally substituted one or more times independently by haloalkyl; and

Y 1 and Y 2 are each independently hydrogen, or alkyl optionally substituted by morpholinyl, or

Y 1 and Y 2 together with the nitrogen atom to which they are attached form morpholinyl;

or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

15. The compound according to claim 1 , wherein:

R 3 and R 4 together with the nitrogen atom to which they are attached form imidazolidinyl, [1,2,4]triazinanyl, piperazinyl, morpholinyl, pyrrolidinyl, 1,2,3,4-tetrahydro-pyrimidinyl, piperidinyl, oxazolidinyl, 2,3-dihydro-indolyl, octahydro-cyclopenta[c]pyrrolyl, or 3,4-dihydro-benzo[1,4]oxazine, each of which is optionally substituted one or more times independently by R 6 ;

R 6 is oxo, alkoxy, carboxy, cycloalkyl, halo, cyano, alkylsulfonyl, Y 1 Y 2 N—SO 2 —,

alkyl optionally substituted one or more times independently by hydorxy, alkoxycarbonyl, alkoxy, carboxy, aryl, halo, heterocyclyl, cycloalkyl, alkylsulfonyl, cyano, heterocyclylcarbonyl,

acyl or aryl, each of which is optionally substituted one or more times independently by halo,

alkoxycarbonyl optionally substituted one or more times independently by aryl,

heteroaroyl optionally substituted one or more times independently by alkyl,

heterocyclyl optionally substituted one or more times by oxo, or

aryloxy optionally substituted one or more times independently by haloalkyl; and

Y 1 and Y 2 are each independently hydrogen, or alkyl optionally substituted by morpholinyl, or

Y 1 and Y 2 together with the nitrogen atom to which they are attached form morpholinyl;

or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

16. The compound according to claim 1 , wherein:

R 3 and R 4 together with the nitrogen atom to which they are attached form indolyl, optionally substituted one or more times independently by R 6 ;

R 6 is Y 1 Y 2 N—SO 2 —, alkoxycarbonyl, carboxyalkyl, cyano, halo, alkylsulfonyl, alkoxy, or acyl optionally substituted one or more times independently by halo; and

Y 1 and Y 2 are each independently hydrogen, or alkyl optionally substituted by morpholinyl, or

Y 1 and Y 2 together with the nitrogen atom to which they are attached form morpholinyl;

or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

17. The compound according to claim 1 , wherein:

R 5 is phenyl, pyridyl, or benzo[1,3]dioxolyl, each of which is optionally substituted one or more times independently by R 6 ;

R 6 is Y 1 Y 2 N—SO 2 —, hydroxy, alkoxy, halo, alkyl, or haloalkyl; and

Y 1 and Y 2 are each independently hydrogen or alkyl,

or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

18. The compound according to claim 1 , which is

2-Pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)amide,

2-Pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

4-Methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-Pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-Pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

4-Methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-acetyl)-indol-1-1yl]-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-amide,

4-Methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2,3-dimethyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-chloro-2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-bromo-indol-1-yl)-amide,

3-Oxo-4-[(2-phenyl-pyrimidine-5-carbonyl)-amino]-piperazine-1-carboxylic acid benzyl ester,

2-(3-Fluorophenyl)pyrimidine-5-carboxylic acid-(3-dimethylsulfamoyl-5-fluoro-indol-1-yl)amide,

2-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid-(3-dimethylsulfamoyl-5-fluoroindol-1-yl)amide,

2-(3-Fluorophenyl)pyrimidine-5-carboxylicacid-[5-fluoro-3-(morpholine-4-sulfonyl)indol-1-yl]amide,

2-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid-[5-fluoro-3-(morpholine-4-sulfonyl) indol-1-yl]amide,

2-(3-Fluorophenyl)pyrimidine-5-carboxylic acid-[5-fluoro-3-sulfamoylindol-1-yl]amide,

2-(3-Fluorophenyl)pyrimidine-5-carboxylic acid-[5-fluoro-3-methylsulfamoyl]indol-1-yl]amide,

2-(3-Fluorophenyl)pyrimidine-5-carboxylic acid-[5-fluoro-3-(2-morpholin-4-ylethylsulfamoyl)indol-1-yl]amide,

2-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid-[5-fluoro-3-methylsulfamoyl]indol-1-yl]amide,

2-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid-{5-fluoro-[(3-tetrahydropyran-4-ylmethyl)sulfamoyl]indol-1-yl}amide,

2-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid-[5-fluoro-3-(2-morpholin-4-ylethylsulfamoyl)indol-1-yl]amide,

2-(3-Fluorophenyl)pyrimidine-5-carboxylic acid-(4-fluoroindol-1-yl)amide,

2-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid-(4-fluoroindol-1-yl)amide,

2-(Pyridin-2-yl)-pyrimidine-5-carboxylic acid-(4-fluoroindol-1-yl)amide,

2-(Pyridin-2-yl)-4-methylpyrimidine-5-carboxylic acid-(4-fluoroindol-1-yl)amide,

2-Phenyl-pyrimidine-5-carboxylic acid [6-(4-fluoro-phenyl)-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl]-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4] riazine-4-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid[5-fluoro-3-(2-hydroxy-2-methyl-propyl)-indol-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [5-fluoro-3-(2-hydroxy-2-methyl-propyl)-indol-1-yl]-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid [5-fluoro-3-(2-hydroxy-2-methyl-propyl)-indol-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-cyano-5-fluoro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [5-fluoro-3-(1H-tetrazol-5-yl)-indol-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid [1,2,4]triazol-4-ylamide,

2-phenyl-pyrimidine-5-carboxylic acid piperidin-1-ylamide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-(2-fluoro-phenyl)-hydrazide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-ethyl-N′-tolyl-hydrazide,

2-Phenyl-pyrimidine-5-carboxylic acid (3-oxo-morpholin-4-yl)-amide,

2-(5-Methyl-[1,2,4]oxadiazol-3-yl)-pyrimidine-5-carboxylic acid morpholin-4-ylamide,

2-Benzoyl-pyrimidine-5-carboxylic acid morpholin-4-ylamide,

2-Benzoyl-pyrimidine-5-carboxylic acid [4-(2-hydroxy-ethyl)-piperazin-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-methyl-N′-[5-trifluoromethyl-pyridin-2-yl]-hydrazide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-methyl-N′-[4-trifluoromethyl-pyridin-2-yl]-hydrazide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-pyridin-2-yl-hydrazide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-(2-chloro-phenyl)-hydrazide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-(2-oxo-piperidin-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-cyclohexyl-N′-methyl-hydrazide,

2-Phenyoxy-pyrimidine-5-carboxylic acid N′-morpholin-4-yl-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (2,6-dimethyl-3-oxo-2,5-dihydro-3H-1,2,4-triazine-4-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (6-tert-butyl-3-oxo-2,5-dihydro-3H-1,2,4-triazine-4-yl)-amide,

2-Pyridin-2-yl-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-1,2,4-triazine-4-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (6-tert-butyl-3-oxo-2,5-dihydro-3H-1,2,4-triazine-4-yl)-amide,

3-{2,4-Dioxo-3-[(2-pheyl-pyrimidine-5-carbonyl)-amino]-1,2,3,4-tetrahydro-pyrimidin-5-yl}-propionic acid methyl ester,

3-{2,4-Dioxo-3-[(2-pheyl-pyrimidine-5-carbonyl)-amino]-1,2,3,4-tetrahydro-pyrimidin-5-yl}-propionic acid,

2-Phenyl-pyrimidine-5-carboxylic acid (4-methyl-piperazin-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid morpholin-4-ylamide,

2-Phenyl-pyrimidine-5-carboxylic acid [4-(2-hydroxy-ethyl)-piperazin-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid ((s)-2-methoxymethyl)-pyrrolidin-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid ((R)-2-methoxymethyl)-pyrrolidin-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (5-bromo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (3-isopropyl-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid pyrrol-1-ylamide,

2-Phenyl-pyrimidine-5-carboxylic acid (5-morpholin-4-ylmethyl-2-oxo-oxazolidin-3-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (4-cyclopentyl-piperazin-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (2-oxo-oxazolidin-3-yl)-amide,

4-Methyl-2-phenyl-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazine-4-yl)-amide,

[N′-(2-Phenyl-pyrimidine-5-carbonyl)-hydrazino]-acetic acid ethyl ester,

2-[N′-(2-Phenyl-pyrimidine-5-carbonyl)-hydrazino]-acetamide,

4-[3-(4-Morpholino)propyl]-1-(2-phenyl-pyrimidine-5-carbonyl)-3-thiosemicarbazide,

2-Phenyl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide,

{4-[2-Phenyl-pyrimidine-5-carbonyl]-amino]-piperazin-1-yl}-acetic acid methyl ester,

2-Phenyl-pyrimidine-5-carboxylic acid (4-cyanomethyl-piperazin-1-yl)-amide,

Acetic acid 2-{4-[(2-phenyl-pyrimidine-5-carbonyl)-amino]-piperazin-1-yl}-ethyl ester,

2-Phenyl-pyrimidine-5-carboxylic acid (4-acetyl-piperazin-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid [4-(2-oxo-tetrahydro-furan-3-yl)-piperazin-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid [4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid [4-(2-methoxy-ethyl)-piperazin-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid [4-(2-morpholin-4-yl-2-oxo-ethyl)-piperazin-1-yl]-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid piperadin-1-yl-amide,

2-Phenyl-pyrimidine-5-carboxylic acid piperadin-1-yl-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (hexahydro-cyclopenta[c]pyrrol-2-yl)-amide,

4-Methyl-2-phenyl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid pyrrolidin-1-yl-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (2,6-dimethyl-piperadin-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (4-cyclopentyl-piperazin-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (2-methyl-2,3-dihydro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (2-methyl-2,3-dihydro-indol-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-methyl-N′-pyridin-2-yl-hydrazide,

2-Phenyl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide,

2-Pyridin-2-yl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide,

2-Pyridin-2-yl-pyrimidine-5-carboxylic acid indol-1-yl-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid indol-1-yl-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2-methyl-2,3-dihydro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid indol-1-ylamide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid indol-1-ylamide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (6-methanesulfonyl-indol-1-yl)-amide,

2-Pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide,

2-Pyridin-3-yl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide,

2-Pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide,

2-Pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridine-1-ylamide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid pyrrolo[2,3-c]pyridin-1-ylamide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-c]pyridin-1-ylamide,

4-Methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide,

4-Methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-cyano-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (4-cyano-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [4-(1H-tetrazol-5-yl)-indol-1-yl]-amide,

1-{[2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carbonyl]-amino}-1H-indol-4-carboxylic acid methyl ester,

1-{[2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carbonyl]-amino}-1H-indol-4-carboxylic acid,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-cyanomethyl-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methoxy-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [3-(1H-tetrazol-5-ylmethyl)-indol-1-yl]-amide,

2-(2-Phenyl-pyrimidine-5-carbonyl)-1-hydrazinecarboxamide,

2-(2-Phenyl-pyrimidine-5-carbonyl)-1-hydrazine-1-carbothioamide,

2-Phenyl-pyrimidine-5-carboxylic acid (2,4-dioxo-imidazolidin-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]riazine-4-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-phenyl-hydrazide,

Pyridine-2-carboxylic acid N′-(2-phenyl-pyrimidine-5-carbonyl)-hydrazide,

4-[N′-(2-Phenyl-pyrimidine-5-carbonyl)-hydrazino]-benzenesulfonamide,

3-Hydroxy-benzoic acid N′-(2-phenyl-pyrimidine-5-carbonyl)-hydrazide,

Benzo[1,3]dioxo-5-carboxylic acid N′-(phenyl-pyrimidine-5-carbonyl)-hydrazide,

3,4-Dimethoxy-benzoic acid N′-(phenyl-pyrimidine-5-carbonyl)-hydrazide,

2-Phenyl-pyrimidine-5-carboxylic acid N′-methyl-N′-phenyl-hydrazide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-indol-1-yl)-amide,

2-(3-Methoxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazine-4-yl)-amide,

2-(2-Methoxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazine-4-yl)-amide,

2-(4-Methoxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazine-4-yl)-amide,

2-(3-Hydroxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazine-4-yl)-amide,

2-(2-Hydroxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazine-4-yl)-amide,

2-(4-Hydroxy-phenyl)-pyrimidine-5-carboxylic acid (6-methyl-3-oxo-2,5-dihydro-3H-[1,2,4]triazine-4-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-Thiazol-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

[2,2′]Bipyrimidinyl-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylicacid(3chloro-5-fluoro-indol-1-yl)-amide,

5-Fluoro-1-{[2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carbonyl]-amino}-1H-indole-3-carboxylic acid amide,

2-{5-Fluoro-1-[(4-methyl-2-pyridin-2-yl-pyrimidine-5-carbonyl)-amino]-1H-indol-3-yl}-2-methyl-propionic acid,

2-(5-Fluoro-1-{[2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carbonyl]-amino}-1H-indol-3-yl)-2-methyl-propionic acid,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [5-fluoro-3-(3-hydroxy-3-methyl-butyl)-indol-1-yl]-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid [5-fluoro-3-(3-hydroxy-3-methyl-butyl)-indol-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [5-fluoro-3-(2-pyridin-3-yl-ethyl)-indol-1-yl]-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-formyl-indol-1-yl)-amide,

5-Fluoro-1-[(4-methyl-2-pyridin-2-yl-pyrimidine-5-carbonyl)-amino]-1H-indole-3-carboxylic acid,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-hydroxymethyl-indol-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [5-fluoro-3-(3-hydroxy-3-methyl-butyl)-indol-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [5-fluoro-3-(3-hydroxy-3-methyl-butyl)-indol-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-indol-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-indol-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-ethyl-5-trifluoromethyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethoxy-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (6-trifluoromethyl-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (6-trifluoromethyl-indol-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (6-trifluoromethyl-indol-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (6-trifluoromethyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid N′,N′-diphenyl-hydrazide

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (7-fluoro-3-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methanesulfonyl-3-methyl-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-ethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-ethyl-pyrrolo[2,3-c] pyridin-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-5-trifluoromethyl-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo [2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-nitro-indol-1-yl)-amide,

2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-amino-indol-1-yl)-amide,

2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [5-(dimethanesulfonyl)-amino-indol-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-benzoylamino-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid [5-fluoro-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-indol-1-yl]-amide,

2-Pyridin-2-yl-4-trifluoromethyl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (6-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (6-fluoro-2,3-dihydro-1,4-benzoxazin-4-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (2-cyclopropyl-5-fluoro-indol-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (2-cyclopropyl-5-fluoro-indol-1-yl)-amide,

2-Pyrimidin-2-yl-4-methyl-pyrimidine-5-carboxylic acid (5-methoxyl-indol-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-(1-oxy-pyridin-2-yl)-pyrimidin-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-(3-Difluoromethyl-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide, or

2-(3-Trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

19. The compound according to claim 1 , which is:

2-Phenyl-pyrimidine-5-carboxylic acid (4-benzyl-piperazin-1-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid piperazin-1-ylamide,

2-Phenyl-pyrimidine-5-carboxylic acid (4-methanesulfonyl-piperazin-1-yl)-amide,

2-(2-Methyl-thiazol-4-yl)-pyrimidine-5-carboxylic acid morpholin-4-ylamide,

2-Phenyl-pyrimidine-5-carboxylic acid [4-(1-methyl-1H-imidazole-2-carbonyl)-piperazin-1-yl]-amide,

2-Phenyl-pyrimidine-5-carboxylic acid [4-(1-methyl-1H-imidazole-4-carbonyl)-piperazin-1-yl]-amide,

4-[(2-Phenyl-pyrimidine-5-carbonyl)-amino]-piperazine-1-carboxylic acid tert-butyl ester,

2-Phenyl-pyrimidine-5-carboxylic acid [4-(4-trifluoromethyl-phenoxy)-piperidin-1-yl]-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid [4-(4-trifluoromethyl-phenoxy)-piperidin-1-yl]-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid morpholin-4-ylamide,

2-Phenyl-pyrimidine-5-carboxylic acid indol-1-ylamide,

2-Phenyl-pyrimidine-5-carboxylic acid (4-methoxy-piperidin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (6-fluoro-2,3-dihydro-benzo[1,4]oxazin-4-yl)-amide,

2-Phenyl-pyrimidine-5-carboxylic acid (6-fluoro-2,3-dihydro-benzo[1,4]oxazin-4-yl)-amide,

1-{[2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carbonyl]-amino}-3-(2-morpholin-4-yl-ethyl)-1H-indole-6-carboxylic acid methyl ester,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [5-fluoro-3-(tetrahydro-pyran-4-yl)-indol-1-yl]-amide,

N-methyl-N-(5-fluoro)-indol-3-ylsulfonyl N′-[2-(3-fluoro)-phenyl-pyrimidine-5-carbonyl]-hydrazide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid [5-fluoro-3-(tetrahydro-pyran-4-yl)-indol-1-yl]-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-c]pyridin-1-ylamide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-c]pyridin-1-ylamide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-c]pyridin-1-ylamide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid pyrrolo[2,3-c]pyridin-1-ylamide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid pyrrolo[3,2-c]pyridin-1-ylamide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-c]pyridin-1-ylamide,

4-Methyl-2-(4-chloro -thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-c]pyridin-1-ylamide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-isopropyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-chloro-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-(4-Methyl-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2-methyl-3-oxo-2,3-dihydro-indazol-1-yl)amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid(5-fluoro-indol-1-yl)amide)amide,

6-(4-Chloro-thiazol-2-yl)-2-methyl-N-pyrrolo[2,3-c]pyridin-1-yl-nicotinamide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid(5-methyl-4-oxo-4,5-dihydro-pyrrolo[3,2-c]pyridin-1-yl)amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (5-difluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-b]pyridin-1-yl]-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[3,2-b]pyridin-1-yl]-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[2,3-c]pyridin-1-yl]-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[2,3-c]pyridin-1-yl]-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[2,3-b]pyridin-1-yl]-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[2,3-b]pyridin-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (5-difluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-b]pyridin-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[3,2-b]pyridin-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[2,3-c]pyridin-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[2,3-c]pyridin-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[2,3-b]pyridin-1-yl]-amide,

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[2,3-b]pyridin-1-yl]-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid (5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid (5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-2-(4-methyl-thiazol-2-yl)-pyrimidine-5-carboxylic acid (3-difluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-b]pyridin-1-yl]-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[3,2-b]pyridin-1-yl]-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[2,3-c]pyridin-1-yl]-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[2,3-c]pyridin-1-yl]-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[2,3-b]pyridin-1-yl]-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[2,3-b]pyridin-1-yl]-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (5-difluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-trifluoromethyl-pyrrolo [3,2-b]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-difluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo [3,2-b]pyridin-1-yl]-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo [3,2-b]pyridin-1-yl]-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-trifluoromethyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-difluoromethyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [3-2,2-difluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-difluoromethyl-pyrrolo [2,3-c]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo [2,3-c]pyridin-1-yl]-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo [2,3-c]pyridin-1-yl]-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (3-difluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo [2,3-b]pyridin-1-yl]-amide,

4-Methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo [2,3-b]pyridin-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-trifluoro methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-difluorom ethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-trifluoro methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-trifluoro methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-trifluoro methyl-pyrrolo[2,3-c]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-trifluoromethyl-pyrrolo[2,3-b]pyridin-1-yl)-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2-difluoro-ethyl)-pyrrolo[3,2-b]pyridin-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-b]pyridin-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[3,2-c]pyridin-1-yl]-amide,

2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid [3-(2,2,2-trifluoro-ethyl)-pyrrolo[2,3-c]pyridin-1-yl]-amide,

4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-difluoromethyl-indol-1-yl)-amide,

2-(4-Chloro-thiazol-2-yl)-4-methyl-pyrimidine-5-carboxylic acid (3-difluoromethyl-indol-1-yl)-amide, or

4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-difluoromethyl-indol-1-yl)-amide,

or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

20. A pharmaceutical composition comprising the compound according to claim 1 , or an N-oxide thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

21. A method for treating an allergic or inflammatory disorder, selected from the group consisting of allergic rhinitis, asthma and chronic obstructive pulmonary disease, in a patient in need thereof, comprising administering to the patient a pharmaceutically effective amount of the compound according to claim 1 , or an N-oxide thereof, or a pharmaceutically acceptable salt thereof.

22. The method according to claim 21 , wherein the allergic or inflammatory disorder is allergic rhinitis.

23. The method according to claim 21 , wherein the allergic or inflammatory disorder is asthma.

24. The method according to claim 21 , wherein the allergic or inflammatory disorder is chronic obstructive pulmonary disease.

Assignments (4)
CHANGE OF NAME Recorded Aug 2, 2011
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 026686/0522 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 13, 2010
From: VANDEUSEN, CHRISTOPHER
To: SANOFI-AVENTIS
Reel/Frame 024226/0075 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 13, 2010
From: ALDOUS, SUZANNE C.; FENNIE, MICHAEL WALTER; JIANG, JOHN ZIQI; JOHN, STANLY; MU, LAN; PEDGRIFT, BRIAN; PRIBISH, JAMES RAYMOND; RAUCKMAN, BARBARA SEAVEY; SABOL, JEFFREY STEPHEN; STOKLOSA, GRZEGORZ T.; THURAIRATNAM, SUKANTHINI
To: SANOFI-AVENTIS U.S. LLC
Reel/Frame 024226/0111 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 13, 2010
From: SANOFI-AVENTIS U.S. LLC
To: SANOFI-AVENTIS
Reel/Frame 024226/0132 →