IP Library Granted Patent US 8,598,166
Granted Patent B2
US 8,598,166 · App. 13/291,660 · Granted Dec 3, 2013

Polysubstituted derivatives of 6-heteroarylimidazo[1,2-a]pyridines, and preparation and therapeutic use thereof

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Quick Facts
Patent No.
US 8,598,166
App. No.
13/291,660
Granted
Dec 3, 2013
Kind
B2
Abstract

Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , Het and X are as defined in the disclosure, or an acid addition salt thereof, and the therapeutic use and process of synthesis thereof.

Claims (202)

1. A method for modulating NOT receptors comprising administering to a patient in need thereof an effective amount of a compound of formula (I):

wherein:

R 1 represents:

a phenyl or naphthyl group, a heteroaryl group or a heterocyclic group, wherein these groups are optionally substituted with one or more atoms or groups chosen, independently of one another, from the following atoms or groups: halogen, (C 1 -C 10 )alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, halo(C 1 -C 10 )alkoxy, (C 1 -C 10 )thioalkyl, —S(O)(C 1 -C 10 )alkyl, —S(O) 2 (C 1 -C 10 )-alkyl), hydroxyl, oxo, cyano, nitro, hydroxy(C 1 -C 10 )alkylene, NRaRb(C 1 -C 10 )alkylene, (C 1 -C 10 )alkoxy(C 1 -C 10 )alkyleneoxy, NRaRb, CONRaRb, SO 2 NRaRb, NRcCORd, OC(O)NRaRb, OCO(C 1 -C 10 )alkyl, NRcC(O)ORe, NRcSO 2 Re, aryl(C 1 -C 10 )alkylene, monocyclic heteroaryl and aryl, wherein the monocyclic heteroaryl or aryl are optionally substituted with one or more substituents chosen from a halogen and a (C 1 -C 10 )alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, halo(C 1 -C 10 )alkoxy, NRaRb, hydroxyl, oxo, nitro, cyano or OCO(C 1 -C 10 )alkyl group, and R 1 is linked to the imidazo[1,2-a]pyridine by an aromatic carbon;

Het represents a monocyclic heteroaryl group containing from 5 to 6 atoms, including from 1 to 3 heteroatoms chosen from N, O and S;

X represents from 1 to 3 substituents, which are identical to or different from one another, chosen from a hydrogen, a halogen, (C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, NRaRb, nitro and cyano, wherein the (C 1 -C 10 )alkyl is optionally substituted with one or more groups chosen from a halogen, (C 1 -C 10 )alkoxy, (C 1 -C 10 )haloalkoxy, NRaRb and hydroxyl;

R represents, at position 3, 5, 7 or 8 of the imidazo[1,2-a]pyridine, from 1 to 4 substituents, which are identical to or different from one another, chosen from a hydrogen, a halogen, (C 1 -C 10 )alkyl, halo(C 1 -C 10 )alkyl and (C 1 -C 10 )alkoxy;

R 2 and R 3 represent, independently of one another,

a hydrogen atom,

a (C 1 -C 10 )alkyl group, optionally substituted with an Rf group; or

an aryl group, optionally substituted with one or more substituents chosen from a halogen and a (C 1 -C 10 )alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, halo(C 1 -C 10 )alkoxy, NRaRb, hydroxyl, nitro or cyano group;

R 4 represents:

a hydrogen atom,

a (C 1 -C 10 )alkyl group, optionally substituted with an Rf group; or

an aryl group, optionally substituted with one or more substituents chosen from a halogen and a (C 1 -C 10 )alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, halo(C 1 -C 10 )alkoxy, NRaRb, hydroxyl, nitro, cyano, (C 1 -C 10 )alkyl(CO)—, CONRaRb, NRcCORd, OC(O)NRaRb, OCO(C 1 -C 10 )alkyl, NRcC(O)ORe or aryl group, wherein the aryl is optionally substituted with one or more substituents chosen from a halogen and a (C 1 -C 10 )alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, halo(C 1 -C 10 )alkoxy, NRaRb, hydroxyl, nitro or cyano group;

Ra and Rb represent, independently of one another, a hydrogen atom or a (C 1 -C 10 )alkyl, aryl(C 1 -C 10 )alkylene or aryl group;

or Ra and Rb form, together with the nitrogen atom which bears them, an azetidine, pyrrolidine, piperidine, azepine, morpholine, thiomorpholine, piperazine or homopiperazine group, this group being optionally substituted with a (C 1 -C 10 )alkyl, aryl or aryl (C 1 -C 10 )alkylene group;

Rc and Rd represent, independently of one another, a hydrogen atom or a (C 1 -C 10 )alkyl, aryl(C 1 -C 10 )alkylene or aryl group;

or Rc and Rd together form a (C 2 -C 5 )alkylene group;

Re represents a (C 1 -C 10 )alkyl, aryl (C 1 -C 10 )alkylene or aryl group;

or Rc and Re together form a (C 2 -C 5 )alkylene group; and

Rf represents a halogen atom or a (C 1 -C 10 )alkoxy, halo(C 1 -C 10 )alkoxy, hydroxyl, cyano, NRaRb, C(O)NRaRb, NRcCORd, OC(O)NRaRb, OCO(C 1 -C 10 )alkyl, NRcCOORe, SO 2 NRaRb, NRcSO 2 Re, aryl(C 1 -C 10 )alkylene or aryl group, wherein the aryl is optionally substituted with one or more substituents chosen from a halogen and a (C 1 -C 10 )alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, halo(C 1 -C 10 )alkoxy, NRaRb, hydroxyl, nitro, cyano or OCO(C 1 -C 10 )alkyl group;

or a pharmaceutically acceptable salt thereof.

2. The method according to claim 1 , wherein, for the compound of formula (I) or pharmaceutically acceptable salt thereof:

R 1 represents a phenyl, furyl, quinolinyl, indolyl, pyrrolopyridinyl, pyridinyl, isoquinolinyl, thienyl, benzofuranyl, benzothiazolyl, benzothienyl, dihydrobenzofuranyl, thiazolyl, pyrazolyl, isoxazolyl, benzimidazolyl or indazolyl group, wherein these groups are optionally substituted with one or more groups or atoms chosen, independently of one another, from halogen, (C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, CONRaRb, NRaRb, (C 1 -C 10 )thioalkyl, —S(O) 2 (C 1 -C 10 -alkyl), halo(C 1 -C 10 )alkyl, hydroxy(C 1 -C 10 )alkylene, NRaRb(C 1 -C 10 )alkylene, NRcCORd, SO 2 NRaRb, cyano and nitro;

Ra and Rb represent, independently of one another, a hydrogen atom or a (C 1 -C 10 )alkyl group; and

Rc and Rd represent, independently of one another, a hydrogen atom or a (C 1 -C 10 )alkyl group.

3. The method according to claim 1 , wherein, for the compound of formula (I) or pharmaceutically acceptable salt thereof:

X represents from 1 to 3 substituents, which are identical to or different from one another, chosen from a hydrogen, a halogen and (C 1 -C 10 )alkyl groups.

4. The method according to claim 1 , wherein, for the compound of formula (I) or pharmaceutically acceptable salt thereof:

R represents, at position 3, 5, 7 or 8 of the imidazo[1,2-a]pyridine, from 1 to 4 substituents, which are identical to or different from one another, chosen from hydrogen and (C 1 -C 10 )alkyl.

5. The method according to claim 1 , wherein, for the compound of formula (I) or pharmaceutically acceptable salt thereof:

R 2 and R 3 represent, independently of one another, a hydrogen atom or a (C 1 -C 10 )alkyl group.

6. The method according to claim 1 , wherein, for the compound of formula (I) or pharmaceutically acceptable salt thereof:

R 4 represents a hydrogen atom or a (C 1 -C 10 )alkyl group.

7. The method according to claim 1 , wherein, for the compound of formula (I) or pharmaceutically acceptable salt thereof:

R represents, at position 3 of the imidazo[1,2-a]pyridine, 1 hydrogen atom or 1 methyl group.

8. The method according to claim 1 , wherein, for the compound of formula (I) or pharmaceutically acceptable salt thereof:

R 1 represents a phenyl, furyl or quinolinyl group, wherein these groups are optionally substituted with one or more atoms or groups chosen, independently of one another, from halogen and (C 1 -C 10 )alkyl;

Het represents a furyl group, a thienyl group, a pyridinyl group or a thiazolyl group;

X represents a hydrogen;

R is a hydrogen;

R 2 and R 3 represent, independently of one another, a hydrogen atom; and

R 4 represents a hydrogen atom.

9. The method according to claim 1 , wherein, for compound of formula (I) is selected from the group consisting of:

{5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{4-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl}methanol;

{5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]pyridin-3-yl}methanol;

{4-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{6-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]pyridin-2-yl}methanol;

{5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]thien-3-yl}methanol;

{2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-5-yl}methanol;

{2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-4-yl}methanol;

{4-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

[2-(2-Furan-3-ylimidazo[1,2-a]pyridin-6-yl)pyridin-4-yl]methanol and the hydrochloride thereof;

[5-(2-Quinolin-3-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol and the hydrochloride thereof;

[4-(2-p-Tolylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

[2-(2-Quinolin-3-ylimidazo[1,2-a]pyridin-6-yl)pyridin-4-yl]methanol and the hydrochloride thereof;

[4-(2-Quinolin-3-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol and the hydrochloride thereof;

{4-[2-(1H-Indol-5-yl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{5-[2-(1H-Indol-5-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol and the hydrochloride thereof;

[4-(2-Phenylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol and the hydrochloride thereof;

{4-[2-(1H-Pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol and the hydrochloride thereof;

{4-[2-(3-Methoxyphenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol and the hydrochloride thereof;

{2-[2-(1H-Pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl}methanol and the hydrochloride thereof;

[2-(2-Phenylimidazo[1,2-a]pyridin-6-yl)pyridin-4-yl]methanol;

[5-(2-p-Tolylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

[5-(2-Phenylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

{5-[2-(3-Methoxyphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(2,4-Difluorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-3-yl}methanol;

2-(4-Chlorophenyl)-6-(4-methoxymethyl-furan-2-yl)imidazo[1,2-a]pyridine;

{5-[2-(4-Hydroxymethylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

4-[6-(5-Hydroxymethylfuran-2-yl)imidazo[1,2-a]pyridin-2-yl]-N,N-dimethylbenzamide;

{5-[2-(1H-Indol-6-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(2-Methoxypyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

[5-(2-Quinolin-5-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

{5-[2-(4-Morpholin-4-ylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

[5-(2-Isoquinolin-5-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

(5-{2-[4-(1-Pyrrolidin-1-ylethyl)phenyl]imidazo[1,2-a]pyridin-6-yl}furan-2-yl)methanol;

4-[6-(5-Hydroxymethylthien-3-yl)imidazo[1,2-a]pyridin-2-yl]-N,N-dimethylbenzamide;

{4-[2-(2-Methoxypyridin-3-yl)imidazo[1,2-a]pyridin-6-yl}thien-2-yl]methanol;

[4-(2-Isoquinolin-5-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

N-{3-[6-(5-Hydroxymethylthien-3-yl)imidazo[1,2-a]pyridin-2-yl]phenyl}isobutyramide;

(4-{2-[4-(1-Pyrrolidin-1-ylethyl)phenyl]imidazo[1,2-a]pyridin-6-yl}thien-2-yl)methanol;

{4-[2-(4-Dimethylaminomethylphenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

2-Fluoro-4-[6-(5-hydroxymethylthien-3-yl)imidazo[1,2-a]pyridin-2-yl]-N,N-dimethylbenzamide;

{4-[2-(3-Aminophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

N-tert-Butyl-5-[6-(5-hydroxymethylthien-3-yl)imidazo[1,2-a]pyridin-2-yl]nicotinamide;

[5-(3-Methyl-2-phenylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

[5-(3-Methyl-2-thien-2-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

{5-[2-(3-Chlorophenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(4-Pyrrolidin-1-ylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

3-[6-(5-Hydroxymethylfuran-2-yl)imidazo[1,2-a]pyridin-2-yl]benzonitrile;

[5-(2-Benzofuran-2-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

[5-(2-Benzothiazol-2-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

[5-(2-Benzo[b]thien-2-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

{4-[2-(4-Nitrophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

[4-(2-Thien-3-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

{4-[2-(4-Methylthiophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{4-[2-(5-Chlorothien-2-yl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{4-[2-(4-Methylsulphonylphenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

[4-(2-Benzo[b]thien-2-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

[4-(2-Benzo[b]thien-5-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

[4-(3-Methyl-2-phenylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

[4-(3-Methyl-2-thien-2-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

{4-[2-(4-Methoxyphenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(4-Pyrrolidin-1-ylphenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(2-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(4-Methylsulphonylphenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

[4-(2-Benzofuran-2-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

[4-(2-Benzo[b]thien-2-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

[4-(2-Furan-2-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

[4-(2-Benzo[b]thien-5-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

{4-[2-(4-Pyrrolidin-1-ylphenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

1-{4-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}ethanol;

2-{4-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}propan-2-ol;

{5-[2-(4-Methoxyphenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(4-Trifluoromethylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl-methanol;

{5-[2-(4-Methoxyphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(4-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(3,4-Difluorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

[5-(2-Thien-3-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

{5-[2-(5-Chlorothien-2-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(2-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(3-Bromophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(4-Chloro-3-methylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{5-[2-(4-Methylsulphonylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

[5-(2-Thien-2-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

[5-(2-Benzofuran-3-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

{5-[2-(2,3-Dihydrobenzofuran-5-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

[5-(2-Furan-2-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

[5-(2-Benzofuran-5-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

[5-(2-Thiazol-2-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol;

{5-[2-(4-Methylthiophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

{4-[2-(4-Chlorophenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

[4-(3-Methyl-2-thien-2-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

{4-[2-(3-Chlorophenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{4-[2-(2,4-Difluorophenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{4-[2-(4-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{4-[2-(3,4-Difluorophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

3-[6-(5-Hydroxymethylthien-3-yl)imidazo[1,2-a]pyridin-2-yl]benzonitrile;

{4-[2-(2-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{4-[2-(3-Bromophenyl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

[4-(2-Benzofuran-2-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

[4-(2-Thien-2-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

[4-(2-Benzofuran-3-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

{4-[2-(1-Methyl-1H-benzimidazol-2-yl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

{4-[2-(2,3-Dihydrobenzofuran-5-yl)imidazo[1,2-a]pyridin-6-yl]thien-2-yl}methanol;

[4-(2-Furan-2-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

[4-(2-Benzofuran-5-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

[4-(2-Thiazol-2-ylimidazo[1,2-a]pyridin-6-yl)thien-2-yl]methanol;

{4-[2-(4-Chlorophenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(3-Chlorophenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(4-Trifluoromethylphenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(4-Fluorophenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(3,4-Difluorophenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

[4-(2-Thien-3-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

[4-(2-Pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

{4-[2-(5-Chlorothien-2-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(3-Bromophenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(4-Chloro-3-methylphenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

[4-(2-Thien-2-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

[4-(2-Benzofuran-3-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

{4-[2-(2,3-Dihydrobenzofuran-5-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

[4-(2-Benzofuran-5-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

[4-(2-Thiazol-2-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

{5-[2-(3-Hydroxymethylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol;

N-{3-[6-(5-Hydroxymethylfuran-2-yl)imidazo[1,2-a]pyridin-2-yl]phenyl}isobutyramide;

2-Fluoro-4-[6-(5-hydroxymethylfuran-2-yl)imidazo[1,2-a]pyridin-2-yl]-N,N-dimethylbenzamide;

2-{4-[2-(1H-Indol-6-yl)imidazo[1,2-a]pyridin-6-yl]thien-2-ylpropan-2-ol;

N-{3-[6-(2-Hydroxymethylthiazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl}acetamide;

{4-[2-(4-Hydroxymethylphenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(3-Hydroxymethylphenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(1H-Indol-5-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(4-Methylthien-2-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(1H-Indol-4-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(2-Fluoropyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

3-[6-(2-Hydroxymethylthiazol-4-yl)imidazo[1,2-a]pyridin-2-yl]-N,N-dimethylbenzamide;

{4-[2-(1H-Indol-6-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(2-Methoxypyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

4-[6-(2-Hydroxymethylthiazol-4-yl)imidazo[1,2-a]pyridin-2-yl]-N-methylbenzamide;

{4-[2-(4-Methylthien-3-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

{4-[2-(1-Methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

[4-(2-Quinolin-5-ylimidazo[1,2-a]pyridin-6-yl)-thiazol-2-yl]methanol;

N-{4-[6-(2-Hydroxymethylthiazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl}acetamide;

{4-[2-(4-Morpholin-4-ylphenyl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

[4-(2-Isoquinolin-5-ylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl]methanol;

N-{3-[6-(2-Hydroxymethyl-thiazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl}isobutyramide;

3-[6-(2-Hydroxymethylthiazol-4-yl)imidazo[1,2-a]pyridin-2-yl]-N,N-dimethylbenzenesulphonamide;

{4-[2-(2,6-Difluoropyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]thiazol-2-yl}methanol;

(4-{2-[1-(3-Methylbutyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyridin-6-yl}thiazol-2-yl)methanol;

2-{4-[2-(1H-Indol-6-yl)imidazo[1,2-a]pyridin-6-yl]-1H-pyrazol-3-yl}propan-2-ol;

2-{5-Fluoro-2-[2-(1H-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl}propan-2-ol;

2-{2-[2-(1H-Indol-6-yl)imidazo[1,2-a]pyridin-6-yl}pyridin-4-yl]propan-2-ol;

2-{2-[2-(1H-Indazol-3-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl}propan-2-ol;

2-{2-[2-(5-Methylisoxazol-3-yl)imidazo[1,2-a]pyridin-6-yl}pyridin-4-yl]propan-2-ol;

{5-[2-(1H-Indol-6-yl)imidazo[1,2-a]pyridin-6-yl]-methyl-1H-imidazol-2-yl}methanol; and

2-{5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}propan-2-ol;

or a pharmaceutically acceptable salt thereof.

Assignments (2)
CHANGE OF NAME Recorded Aug 13, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028775/0284 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2012
From: DE PERETTI, DANIELLE; EVANNO, YANNICK; MACHNIK, DAVID; RAKOTOARISOA, NATHALIE
To: SANOFI-AVENTIS
Reel/Frame 028751/0959 →