IP Library Granted Patent US 8,338,451
Granted Patent B2
US 8,338,451 · App. 12/881,815 · Granted Dec 25, 2012

Polysubstituted derivatives of 2-heteroaryl-6-phenylimidazo[1,2-

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Quick Facts
Patent No.
US 8,338,451
App. No.
12/881,815
Granted
Dec 25, 2012
Kind
B2
Abstract

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

Claims (214)

1. A compound of formula (I):

wherein:

R 1 represents:

a heteroaryl or heterocyclic group, wherein this group is 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, oxo, (C 1 -C 10 )thioalkyl, —S(O)(C 1 -C 10 )alkyl, -S(O) 2 (C 1 -C 10 -alkyl), hydroxyl, 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 and 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 R1 is linked to the imidazo[1,2-a]pyridine by an aromatic carbon;

X represents from 1 to 4 substituents, which may be identical to or different from one another, chosen from hydrogen, a halogen, (C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, NRaRb, nitro, and cyano, wherein the (C 1 -C 10 )alkyl group 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 may be 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 2 and X can form, together with the carbon atoms which bear them, a carbon-based ring containing from 5 to 7 carbon atoms;

R 4 represents:

a hydrogen atom;

a (C 1 -C 10 )alkyl group, optionally substituted by 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 an acid addition salt thereof.

2. The compound of formula (I) according to claim 1 , wherein:

R 1 represents an isoxazolyl, pyridinyl, thiazolyl, quinolinyl, benzo[1,3]dioxolyl, indolyl, 1,2,3,4-tetrahydroquinolinyl, benzofuranyl, dihydrobenzofuranyl, dihydrobenzoxazolyl, furyl, thienyl, pyrrolo[2,3-b]pyridinyl, pyrimidinyl, benzothiazolyl, benzothiophenyl, benzimidazolyl, indazolyl, benzisoxazolyl, isoquinolinyl or pyrazolyl group;

wherein these groups are optionally substituted with one or more atoms or groups chosen, independently of one another, from halogen, (C 1 -C 10 )alkyl, oxo, NRaRb, (C 1 -C 10 )alkoxy, aryl and CONRaRb; and

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

or an acid addition salt thereof.

3. The compound of formula (I) according to claim 1 , wherein X represents 1 or 2 hydrogen or halogen atoms;

or an acid addition salt thereof.

4. The compound of formula (I) according to claim 1 , wherein R represents, at position 3, 5, 7 or 8 of the imidazo[1,2-a]pyridine, a hydrogen atom or a (C 1 -C 10 )alkyl group;

or an acid addition salt thereof.

5. The compound of formula (I) according to claim 1 , wherein R 2 and R 3 represent, independently of one another, a hydrogen atom or a (C 1 -C 10 )alkyl group;

or an acid addition salt thereof.

6. The compound of formula (I) according to claim 1 , wherein:

R 4 represents a hydrogen atom, or a (C 1 -C 10 )alkyl group optionally substituted with an Rf group; and

Rf represents a (C 1 -C 10 )alkoxy group;

or an acid addition salt thereof.

7. The compound of formula (I) according to claim 1 , wherein:

the group

is at position 2, 3 or 4 of the phenyl which bears it;

or an acid addition salt thereof.

8. The compound of formula (I) according to claim 1 , wherein:

R 1 represents an isoxazolyl, pyridinyl, thiazolyl, quinolinyl, benzo[1,3]dioxolyl, indolyl, 1,2,3,4-tetrahydroquinolinyl, benzofuranyl, dihydrobenzofuranyl, dihydrobenzoxazolyl, furyl, thienyl, pyrrolo[2,3-b]pyridinyl, pyrimidinyl, benzothiazolyl, benzothiophenyl, benzimidazolyl, indazolyl, benzisoxazolyl, isoquinolinyl or pyrazolyl group;

wherein these groups are optionally substituted with one or more atoms or groups chosen, independently of one another, from halogen, (C 1 -C 10 )alkyl, oxo, NRaRb, (C 1 -C 10 )alkoxy, aryl and CONRaRb;

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

X represents 1 or 2 hydrogen or halogen atoms;

R represents, at position 3, 5, 7 or 8 of the imidazo[1,2-a]pyridine, a hydrogen atom or a (C 1 -C 10 )alkyl group;

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

R 4 represents a hydrogen atom, or a (C 1 -C 10 )alkyl group optionally substituted with an Rf group; and

Rf represents a (C 1 -C 10 )alkoxy group;

or an acid addition salt thereof.

9. The compound of formula (I) according to claim 1 , wherein:

R 1 represents an isoxazolyl, pyridinyl, thiazolyl, quinolinyl, benzo[1,3]dioxolyl, indolyl, 1,2,3,4-tetrahydroquinolinyl, benzofuranyl, dihydrobenzofuranyl, dihydrobenzoxazolyl, furyl, thienyl, pyrrolo[2,3-b]pyridinyl, pyrimidinyl, benzothiazolyl, benzothiophenyl, benzimidazolyl, indazolyl, benzisoxazolyl, isoquinolinyl or pyrazolyl group;

wherein these groups are optionally substituted with one or more atoms or groups chosen, independently of one another, from halogen, (C 1 -C 10 )alkyl, oxo, NRaRb, (C 1 -C 10 )alkoxy, aryl and CONRaRb;

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

X represents 1 or 2 hydrogen or halogen atoms;

R represents, at position 3, 5, 7 or 8 of the imidazo[1,2-a]pyridine, a hydrogen atom or a (C 1 -C 10 )alkyl group;

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

R 4 represents a hydrogen atom, or a (C 1 -C 10 )alkyl group optionally substituted with an Rf group;

Rf represents a (C 1 -C 10 )alkoxy group; and

the group

being at position 2, 3 or 4 of the phenyl which bears it;

or an acid addition salt thereof.

10. The compound of formula (I)according to claim 1 wherein:

R 1 represents an isoxazolyl, pyridinyl, thiazolyl, quinolinyl, benzo[1,3]dioxolyl, indolyl, 1,2,3,4-tetrahydroquinolinyl, benzofuranyl, dihydrobenzofuranyl, dihydrobenzoxazolyl, furyl, thienyl or pyrrolo[2,3-b]pyridinyl group, wherein these groups are optionally substituted with one or more atoms or groups chosen, independently of one another, from halogen, (C 1 -C 10 )alkyl, oxo, NRaRb and aryl;

X represents a hydrogen;

R represents a hydrogen or a (C 1 -C 10 )alkyl group;

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

R 4 represents a hydrogen atom or a (C 1 -C 10 )alkyl group, this group being optionally substituted with an Rf group;

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

Rf represents a (C 1 -C 10 )alkoxy group;

or an acid addition salt thereof.

11. A compound selected from the group consisting of:

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

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

6-(3-tert-butoxymethylphenyl)-2-(pyridin-3-yl)imidazo[1,2-a]pyridine hydrochloride (1:2);

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

[3-[2-(quinolin-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl]methanol and the hydrochloride thereof;

{3-[2-(1,3-benzodioxol-5-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

[3-[2-(pyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl]methanol and the hydrochloride thereof;

{3-[2-[(1H-indol5-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

6-[6-(3-hydroxymethylphenyl)imidazo[1,2-a]pyridin-2-yl]-3,4-dihydro-1H-quinolin-2-one and the hydrochloride thereof;

2-(5-bromo-2,3-dihydrobenzofuran-7-yl)-6-(3-tert-butoxymethylphenyl)imidazo[1,2-a]pyridine;

6-[6-(3-hydroxymethylphenyl)imidazo[1,2-a]pyridin-2-yl]-3H-benzoxazol-2-one and the hydrochloride thereof;

[2-(2-furan-3-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol hydrochloride (1:1);

{3-[2-(5-bromo-2,3-dihydrobenzofuran-7-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{3-[2-(5-chlorothien-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

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

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

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

{3-[2-(1H-indol-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

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

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

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

[3-[2-(benzofuran-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl]methanol;

[3-[2-(benzofuran-3-yl)imidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

[4-[2-(benzofuran-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl]methanol;

[3-[2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl]methanol;

[4-[2-(pyridin-2-yl]imidazo[1,2-a]pyridin-6-yl]phenyl]methanol;

[3-[2-(thien-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl]methanol;

2-(benzofuran-2-yl)-6[3-(2-methoxyethoxymethyl)phenyl]imidazo[1,2-a]pyridine;

6-[3-(2-methoxyethoxymethyl)phenyl]-2-(thien-2-yl)imidazo[1,2-a]pyridine and the oxalate thereof;

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

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

{3-[2-(1H-indol-3-yl)-3-methylimidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

{3-[2-(1H-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

{3-[2-(2-ethoxypyrimidin-5-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

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

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

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

[3-(2-benzo[b]thiophen-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol and the hydrochloride thereof;

[3-(2-benzo[b]thiophen-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol and the hydrochloride thereof;

3-(2-benzo[b]thiophen-3-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol and the hydrochloride thereof;

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

{3-[2-(2,3-dihydrobenzofuran-5-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

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

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

{3-[2-(3-chlorothien-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2-fluoro-6-[2-(5-methylisoxazol-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

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

2-[3-(3-methyl-2-thien-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-thien-3-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

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

2-[3-(2-benzofuran-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-thien-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-benzofuran-3-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-benzothiazol-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-benzo[b]thienyl-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

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

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

2-[3-(2-furan-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-benzofuran-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-benzo[b]thienyl-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-thiazol-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

{2-fluoro-6-[2-(1H-indazol-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

2- {3-[2-(1H-indazol-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}propan-2-ol and the hydrochloride thereof;

{2,6-difluoro-3-[2-(1H-indazol-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol and the hydrochloride thereof;

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

[2-fluoro-6-(2-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

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

[2-(2-benzothiazol-2-ylimidazo[1,2-a]pyridin-6-yl)-6-fluorophenyl]methanol;

[2-(2-benzo [b]thiophen-2-ylimidazo[1,2-a]pyridin-6-yl)-6-fluorophenyl]methanol;

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

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

[2-(2-benzo [b]thienyl-5-ylimidazo[1,2-a]pyridin-6-yl)-6-fluorophenyl]methanol;

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

[2,6-difluoro-3-(3-methyl-2-thien-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

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

[2,6-difluoro-3-(2-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

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

[3-(2-benzofuran-2-ylimidazo[1,2-a]pyridin-6-yl)-2,6-difluorophenyl]methanol;

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

[3-(2-benzofuran-3-ylimidazo[1,2-a]pyridin-6-yl)-2,6-difluorophenyl]methanol;

[3-(2-benzothiazol-2-ylimidazo[1,2-a]pyridin-6-yl)-2,6-difluorophenyl]methanol;

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

6-(3-methoxymethylphenyl)-2-(1-methyl-1H-indol-6-yl)imidazo[1,2-a]pyridine and the hydrochloride thereof;

2-(1H-indol-6-yl)-6-(3-methoxymethylphenyl)imidazo[1,2-a]pyridine and the hydrochloride thereof;

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

[2-fluoro-6-(3-methyl-2-thienyl-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

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

[2-(2-benzofuran-2-ylimidazo[1,2-a]pyridin-6-yl)-6-fluorophenyl]methanol;

[2-(2-benzofuran-3-ylimidazo[1,2-a]pyridin-6-yl)-6-fluorophenyl]methanol;

{2-fluoro-6-[2-(1-methyl-1H-benzimidazol-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

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

[3-(2-benzo [b]thienyl-2-ylimidazo[1,2-a]pyridin-6-yl)-2,6-difluorophenyl]methanol;

{2,6-difluoro-3-[2-(1-methyl-1H-benzimidazol-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

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

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

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

[3-(2-benzo [b]thienyl-5-ylimidazo[1,2-a]pyridin-6-yl)-2,6-difluorophenyl]methanol;

2-(1H-indol-6-yl)-6-[3-[2-(methoxyethyl)oxymethyl]phenyl]imidazo[1,2-a]pyridine;

2-[3-(2-benzo[d]isoxazol-3-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

[2-(2-benzo[d]isoxazol-3-ylimidazo[1,2-a]pyridin-6-yl)-6-fluorophenyl]methanol;

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

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

2-{3-[2-(2-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}propan-2-ol;

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

2-{3-[2-(1-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}propan-2-ol;

2-[3-(2-quinolin-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

2-[3-(2-isoquinolin-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

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

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

2-[3-(2-quinolin-3-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol;

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

{2-fluoro-6-[2-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2-fluoro-6-[2-(3-fluoropyridin-4-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

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

[2-fluoro-6-(2-pyrimidin-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

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

{2-fluoro-6-[2-(1H-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2-fluoro-6-[2-(2-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2-fluoro-6-[2-(4-methylthien-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2-fluoro-6-[2-(1-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

[2-fluoro-6-(2-quinolin-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

[2-fluoro-6-(2-isoquinolin-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

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

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

{2,6-difluoro-3-[2-(1H-indol-5-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2,6-difluoro-3-[2-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2,6-difluoro-3-[2-(4-methylthien-2-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2,6-difluoro-3-[2-(1H-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2,6-difluoro-3-[2-(2-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2,6-difluoro-3-[2-(4-methylthien-3-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

{2,6-difluoro-3-[2-(1-methyl-1H-indol-5-yl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol;

[2,6-difluoro-3-(2-quinolin-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

[2,6-difluoro-3-(2-isoquinolin-5-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol;

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

(2,6-difluoro-3-{2-[1-(3-methylbutyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyridin-6-yl}phenyl)methanol; and

N-tert-butyl-5-[6-(2,4-difluoro-3-hydroxymethylphenyl)imidazo [1,2-a]pyridin-2-yl]nicotinamide.

12. A pharmaceutical composition comprising a compound of formula (I) according to claim 1 , or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.

13. A pharmaceutical composition comprising a compound of formula (I) according to claim 11 , or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.

14. A compound selected from the group consisting of:

Assignments (2)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 8, 2011
From: DE PERETTI, DANIELLE; EVANNO, YANNICK; LARDENOIS, PATRICK; MACHNIK, DAVID; RAKOTOARISOA, NATHALIE; ALMARIO GARCIA, ANTONIO
To: SANOFI-AVENTIS
Reel/Frame 025915/0618 →