IP Library Granted Patent US 9,309,243
Granted Patent B2
US 9,309,243 · App. 14/414,287 · Granted Apr 12, 2016

Imidazopyridine derivatives as modulators of TNF activity

Inventors: Jonathan Mark Bentley (Abingdon, GB); Daniel Christopher Brookings (Slough, GB); Julien Alistair Brown (Slough, GB); Thomas Paul Cain (Abingdon, GB); Praful Tulshi Chovatia (Abingdon, GB); Anne Marie Foley (Slough, GB); Ellen Olivia Gallimore (Slough, GB); Laura Jane Gleave (Abingdon, GB); Alexander Heifetz (Abingdon, GB); Helen Tracey Horsley (Slough, GB); Martin Clive Hutchings (Slough, GB); Victoria Elizabeth Jackson (Slough, GB); James Andrew Johnson (Slough, GB); Craig Johnstone (Abingdon, GB); Boris Kroeplien (Slough, GB); Fabien Claude Lecomte (Slough, GB); Deborah Leigh (Abingdon, GB); Martin Alexander Lowe (Slough, GB); James Madden (Abingdon, GB); John Robert Porter (Slough, GB); Joanna Rachel Quincey (Slough, GB); Laura Claire Reed (Abingdon, GB); James Thomas Reuberson (Slough, GB); Anthony John Richardson (Abingdon, GB); Sarah Emily Richardson (Abingdon, GB); Matthew Duncan Selby (Slough, GB); Michael Alan Shaw (Slough, GB); Zhaoning Zhu (Slough, GB)
Assignee: UCB Biopharma SPRL
C07D471/04A61K31/437A61K31/496A61K31/506A61K31/5377A61K31/541A61K31/554A61K31/5513C07D491/107C07D519/00
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Quick Facts
Patent No.
US 9,309,243
App. No.
14/414,287
Granted
Apr 12, 2016
Kind
B2
Abstract

A series of imidazo[1,2-a]pyridine derivatives of formula (I), being potent modulators of human TNFa activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

Claims (339)

1. A compound represented by formula (IIB) or a pharmaceutically acceptable salt thereof:

wherein

E represents —N(R 5 ), —CH 2 —, —CH(OH)—, —CH(OCH 3 )—, —CH(OCH 2 CO 2 H)—, —CH(NH 2 )—, —CH(NHCOCH 3 )—, —CH(CO 2 H)—, —CH(CO 2 benzyl)—, —CH(CH 3 )— or -C(CH 3 )(OH)—;

Q represents a covalent bond; or Q represents —CH 2 —, —CH(CN)—, —CH(OH)—, —CH(OCH 3 )—, —CH 2 O—,—CH 2 N(R 6 )— or —H 2 OCH 2 —;

Z represents hydrogen, halogen or trifluoromethyl; or Z represents C 1-6 alkyl, C 3-7 cycloalkyl, aryl, C 3-7 heterocycloalkyl, C 3-7 heterocycloalkenyl or heteroaryl, any of which groups is optionally substituted by one or more substituents; or Z represents —Z 1 —Z 2 or —Z 1 —C(O)—Z 2 , either of which moieties is optionally substituted by one or more halogen, cyano, nitro, C 1-6 alkyl, trifluoromethyl, oxo, hydroxy, hydroxy(C 1-6 )alkyl, C 1-6 alkoxy, difluoromethoxy, trifluoromethoxy, C 1-3 alkylenedioxy, C 1-6 alkylsulfonyl, amino, di(C 1-6 )alkylamino, di(C 1-6 )alkylamino(C 1-6 )alkyl, C 2-6 alkylcarbonylamino, C 1-6 alkyl-sulfonylamino, formyl, carboxy, C 2-6 alkoxycarbonyl, aminocarbonyl, C 1-6 alkylamino-carbonyl, di(C 1-6 )alkylaminocarbonyl, aminocarbonylamino, and hydrazinocarbonyl;

Z 1 represents a divalent radical derived from an aryl, C 3-7 heterocycloalkyl or heteroaryl group;

Z 2 represents aryl, C 3-7 heterocycloalkyl, C 3-7 heterocycloalkenyl or heteroaryl;

V represents C—R 22 or N;

R 5 and R 6 independently represent hydrogen or C 1-6 alkyl;

R 12 represents hydrogen, halogen, trifluoromethyl or C 1-6 alkyl optionally substituted with C 2-6 alkoxycarbonyl;

R 15 and R 16 independently represent hydrogen, halogen, cyano, nitro, C 1-6 alkyl, trifluoromethyl, hydroxy, C 1-6 alkoxy, difluoromethoxy, trifluoromethoxy, C 1-6 alkylthio, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, amino, C 1-6 alkylamino, di(C 1-6 )alkylamino, arylamino, C 2-6 alkylcarbonylamino, C 1-6 alkylsulfonylamino, formyl, C 2-6 alkylcarbonyl, C 3-6 cycloalkylcarbonyl, C 3-6 heterocycloalkylcarbonyl, carboxy, C 2-6 alkoxycarbonyl, aminocarbonyl, C 1-6 alkylaminocarbonyl, di(C 1-6 )alkylaminocarbonyl, aminosulfonyl, C 1-6 alkylaminosulfonyl or di(C 1-6 alkylaminosufonyl;

R 21 represents hydrogen, halogen, halo(C 1-6 )alkyl, cyano, C 1-6 alkyl, trifluoro-methyl, C 2-6 alkenyl, C 2-6 alkynyl, hydroxy, hydroxy(C 1-6 )alkyl, C 1-6 alkoxy,(C 1-6 )alkoxy-(C 1-6 )alkyl, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, carboxy(C 3-7 )cycloalkyloxy, C 1-6 alkylthio, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, amino, amino-(C 1-6 )alkyl, C 1-6 alkylamino, di(C 1-6 )alkylamino, (C 1-6 )alkoxy(C 1-6 )alkylamino, N-[(C 1-6 ) -alkyl]-N-[hydroxy(C 1-6 )alkyl]amino, C 2-6 alkylcarbonylamino, (C 2-6 )alkylcarbonylamino-(C 1-6 )alkyl, C 2-6 alkoxycarbonylamino, N-[(C 1-6 )alkyl]-N-[carboxy(C 1-6 )alkyl]amino, carboxy(C 3-7 )cycloalkylamino, carboxy(C 3-7 )cycloalkyl(C 1-6 )alkylamino, C 1-6 alkyl-sulphonylamino, C 1-6 alkylsulphonylamino(C 1-6 )alkyl, formyl, C 2-6 alkylcarbonyl, (C 2-6 )alkylcarbonyloxy(C 1-6 )alkyl, carboxy, carboxy(C 1-6 )alkyl, C 2-6 alkoxycarbonyl, morpholinyl(C 1-6 )alkoxycarbonyl, C 2-6 alkoxycarbonyl(C 1-6 )alkyl, C 2-6 alkoxycarbonyl-methylidenyl, aminocarbonyl, C 1-6 alkylaminocarbonyl, di(C 1-6 )alkylaminocarbonyl, aminosulphonyl, C 1-6 alkylaminosulphonyl or di(C 1-6 )alkylaminosulphonyl; or R 21 represents (C 3-7 )cycloalkyl, (C 3-7 )cycloalkyl(C 1-6 )alkyl, (C 4-7 )cycloalkenyl, (C 4-9 )bicycloalkyl, (C 3-7 )heterocycloalkyl, (C 3-7 )heterocycloalkenyl, (C 4-9 )heterobicycloalkyl or (C 4-9 )spiroheterocycloalkyl, any of which groups is optionally substituted by one, two or three substituents independently selected from C 1-6 alkyl, oxo, carboxy, carboxy(C 1-6 )alkyl, C 2-6 alkoxycarbonyl, tetrazolyl, tetrazolyl(C 1-6 )alkyl, halogen, halo(C 1-6 )alkyl, cyano, nitro(C 1-6 )alkyl, trifluoromethyl, hydroxy, hydroxy(C 1-6 )alkyl, C 1-6 alkoxy, C 1-6 alkylsulphonyl, amino, (C 2-6 )alkylcarbonylamino(C 1-6 )alkyl, formyl, morpholinyl(C 1-6 )alkoxycarbonyl, C 2-6 alkoxycarbonylmethylidenyl, hydroxyoxadiazolyl, C 1-6 alkoxyaminocarbonyl, C 1-6 alkylsulphonylaminocarbonyl, aminosulphonyl and C 2-6 alkylcarbonylaminosulphonyl;

R 22 represents hydrogen, halogen or C 1-6 alkyl; and

R 23 represents hydrogen, C 1-6 alkyl, trifluoromethyl or C 1-6 alkoxy.

2. The compound as claimed in claim 1 or a pharmaceutically acceptable salt thereof wherein R 21 represents hydroxy(C 1-6 )alkyl.

3. The compound as claimed in claim 1 represented by formula (IIC), (IID), (IIE), (IIF), (IIG), (IIH), (IIJ), (IIK) or (IIL) or a pharmaceutically acceptable salt thereof:

wherein

T represents —CH 2 — or —CH 2 CH 2 —;

U represents C(O) or S(O) 2 ;

W represents O, S, S(O), S(O) 2 , N(R 31 ) or C(R 32 )(R 33 );

-M-represents —CH 2 — or —CH 2 CH 2 —;

R 31 represents hydrogen, cyano(C 1-6 )alkyl, C 1-6 alkyl, trifluoromethyl, trifluoroethyl, C 1-6 alkylsulphonyl, (C 1-6 )alkylsulphonyl(C 1-6 )alkyl, formyl, C 2-6 alkylcarbonyl, carboxy, carboxy(C 1-6 )alkyl, C 2-6 alkoxycarbonyl, C 2-6 alkoxycarbonyl(C 1-6 )alkyl, aminocarbonyl, C 1-6 alkylamino-carbonyl, di(C 1-6 )alkylaminocarbonyl, aminosulphonyl, (C 1-6 )alkylaminosulphonyl, di(C 1-6 )alkyalaminosulphonyl or tetrazolyl(C 1-6 )alkyl;

R 32 represents hydrogen, halogen, cyano, hydroxy, hydroxy(C 1-6 )alkyl, C 1-6 alkylsulphonyl, formyl, carboxy, carboxy (C 1-6 )alkyl, C 2-6 alkylcarbonyl, C 2-6 alkoxycarbonyl, (C 1-6 )alkyl, aminosulphonyl, (C 1-6 )alkoxyaminocarbonyl,(C 1-6 )alkyl-sulphonylaminocarbonyl, (C 2-6 )alkylcarbonlaminosulphonyl, hydroxyoxadiazolyl or tetrazolyl;

R 33 represents hydrogen, halogen, C 1-6 alkyl, trifluoromethyl, hydroxy, hydroxy-(C 1-6 )alkyl, C 1-6 alkoxy, amino or carboxy;

R 34 represents hydrogen, halogen, halo(C 1-6 )alkyl, hydroxy, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkylsulphinyl, C 1-6 alkylsulphonyl, amino, C 1-6 alkylamino, di(C 1-6 )alkylamino, (C 2-6 )alkylcarbonylamino, (C 2-6 )alkylcarbonylamino(C 1-6 )alkyl, (C 1-6 )alkylsulphonylamino, or (C 1-6 )alkylsulphonylamino(C 1-6 )alkyl.

4. The compound as claimed in claim 3 or a pharmaceutically acceptable salt thereof, wherein R 34 represents hydrogen or hydroxy.

5. The compound as claimed in claim 1 or a pharmaceutically acceptable salt thereof, wherein R 15 represents difluoromethoxy.

6. A compound according to claim 1 that is,

N-(2,5-Dichlorophenyl)-6-(6-methoxypyridin-3-yl)-2-methylimidazo[1,2-a]pyridin-3-amine,

3-[2-(Difluoromethoxy)benzyl]-6-(6-methoxy-5-methylpyridin-3-yl)-2-methyl -imidazo[1,2-a]pyridine,

5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}-3-methyl-pyridin-2(1H)-one,

3-[2-(Difluoromethoxy)benzyl]-2-methyl-6-[6-(piperazin-1-yl)pyridin-3-yl]imidazo[1,2-a]pyridine,

3-[2-(Difluoromethoxy)benzyl]-6-(6-methoxypyridin-3-yl)-2-methylimidazo[1,2-a]-pyridine,

{3-[2-(Difluoromethoxy)benzyl]-6-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridin-2-yl}-methanol,

3-[2-(Difluoromethoxy)benzyl]-2-methyl-6-[2-(piperazin-1-yl)pyrimidin-5-yl]-imidazo[1,2-a]pyridine,

4-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)piperazin-2-one,

3-[2-(Difluoromethoxy)benzyl]-6-[2-(1,1-dioxidothiomorpholin-4-yl)pyrimidin -5-yl]-2-methylimidazo[1,2-a]pyridine,

5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyridin-2(1H)-one,

4-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)-morpholine,

5-{3-[2(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}-2-methoxy-4-methylpyridine,

5{3[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin 6-yl}-4-methyl-pyridin-2(1H)-one,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)piperidine-4-carboxylic acid,

4-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)morpholine,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-1,4-diazepan-5-one,

5-(5{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-1,2,5-thiadiazepan-1,1-dioxide,

4-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methyl-7-(trifluoromethyl)imidazo[1,2-a]-pyridin-6-yl}pyrimidin-2-yl)piperazin-2-one,

4-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methyl-7-(trifluoromethyl)imidazo[1,2-a]-pyridin-6-yl}pyrimidin-2-yl)morpholine,

5-{3-[2(Difluoromethoxy)benzyl]-2-methyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl}-2-(piperazin-1yl),pyrimidine,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methyl-7-(trifluoromethyl)imidazo[1,2-a]-pyridin-6-yl}pyridin-2-yl)piperazine,

4-(5-{3-[2-(Difluoromethoxy)benzyl]-2,7-dimethylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)piperazin-2-one,

4-(5-{3-[2-(Difluoromethoxy)benzyl]-2,7-dimethylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)morpholine,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2,7-dimethylimidazo[1,2-a]pyridin-6-yl}pyridin-2-yl)piperazine,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-7-fluoro-2-(methoxymethyl)imidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)piperidine-4-carboxylic acid,

5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-2-oxa-5-azabicyclo[2.2.1]heptane,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-methylpiperidine-3-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3-methylpiperidine-3-carboxylic acid hydrochloride,

Ethyl 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclohex-3-ene-1-carboxylate,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]cyclohex-3-ene-1-carboxylic acid,

trans-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-]pyridin-6-yl)pyrimidin-2-yl]cyclohexane-1-carboxylic acid,

cis-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]cyclohexane-1-carboxylic acid,

Methyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-4 -methylpiperidine-4-carboxylic acid,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid,

Ethyl 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo [3.1.0]hexane -6-carboxylate,

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo [1,2-]pyridin-6-yl)-pyrimidin-2-yl]-3-azabicyclo [3.1.0 ]hexane-6-carboxylic acid,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]piperidine-4-carboxylic acid,

2-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo [1 ,2-a]pyridin-6-yl)-pyrimidin-2-yl]-2-azaspiro [3.3 ]heptane -6-carboxylic acid,

5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)-2-[4-(1H-tetrazol-5-ylmethyl)piperazin-1-yl]pyrimidine formate,

5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)-2-[4-(1H-tetrazol-5-yl)piperidin-1-yl]pyrimidine,

(3R)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]pyrrolidine-3-carboxylic acid,

2-{4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperazin-1-yl}propanoic acid,

(3S)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]pyrrolidine-3-carboxylic acid,

(1R,2S)-2-{[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]amino}cyclopentane-1-carboxylic acid,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2,7-dimethylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]morpholine-2-carboxylic acid,

(3S)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-3-carboxylic acid,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid,

(1R,3S)-3-{[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]amino}cyclopentane-1-carboxylic acid,

Ammonium (3R)-1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-3-carboxylate,

Ammonium 1-({[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo [1 ,2-a]pyridin-6-yl)pyrimidin-2-yl]amino}methyl)cyclopropane-1-carboxylate,

Ethyl 2-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]propanoate,

Ammonium (2S)-1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo-[1,2---a]pyridin-6-yl)pyrimidin-2-yl]piperidine-2-carboxylate,

(2S)-2-{N-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-N-(methyl)amino}propanoic acid,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]azetidine-3-carboxylic acid,

(1S,3R)-3-{[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo [1,2-a ]-pyridin-6-yl)pyrimidin-2-yl]amino}cyclopentane-1-carboxylic acid,

Ammonium (2R)-1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo-[1,2-a ]pyridin-6-yl)pyrimidin-2-yl]piperidine-2-carboxylate,

(2S)-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]morpholine-2-carboxylic acid,

3-{[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2-methylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]oxy}cyclobutane-1-carboxylic acid,

Ammonium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a ]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylate,

Ammonium 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-1,4-oxazepane-7-carboxylate,

2-[(2R)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]pyrrolidin-2-yl]acetic acid,

5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2-methylimidazo[1,2-a]pyridin-6-yl)-2-[3-(2H-1,2,3,4-tetrazol-5-yl)azetidin-1-yl]pyrimidine,

Ammonium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylate,

5-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2-methylimidazo [1,2-a ]pyridin-6-y1)-pyrimidin-2-yl]-5-azaspiro[2.4]heptane-1-carboxylic acid,

5-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2-methylimidazo [1,2---a]pyridin-6-y1)-pyrimidin-2-yl]-5-azaspiro[2.3]hexane-1-carboxylic acid,

Ammonium (2R)-4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]morpholine-2-carboxylate,

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3,6-diazabicyclo[3.2.2]nonan-7-one,

Ammonium (1R,5S,6r)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo-[1,2-a]pyridin-6-yl)pyridin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylate,

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-6-carboxylic acid,

2-[(2S)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]pyrrolidin-2-yl]acetic acid,

N-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyridin-2-yl]methanesulfonamide,

Ammonium 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl }-2-methylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-methylpyrrolidine-3-carboxylic,

2-[(2R)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2-methylimidazo [1,2-a]-pyridin-6-yl)-pyrimidin-2-yl]-piperidin-2-yl]acetic acid,

5-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]2-oxa-5-azabicyclo[2.2.1]heptane-1carboxtlic acid,

Ammonium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo [4.1.0]heptane-1-carboxylate,

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl }-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3-azabicyclo[3.1.1]heptane-6-carboxylic acid,

2-[(2S)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidin-2-yl]acetic acid,

Potassium 5-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-1-methyl-5-azaspiro[2.3]hexane-1-carboxylate,

Potassium 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

(1R,5S,6r)-3-[5-(3-{1-[2-(Difluoromethoxy)phenyl]ethyl}-2,7-dimethylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid,

Ethyl 2-{1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidin-4-yl}acetate,

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-5-methyl-3-azabicyclo[3.1.0]hexane-1-carboxylate,

Potassium 2-{1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]piperidin-4-yl}acetate,

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-6-carboxylate (Enantiomer A),

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-6-carboxylate (Enantiomer B),

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-1-carboxylate (Enantiomer A),

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo [4.1.0]heptane-1-carboxylate (Enantiomer B),

Potassium 2-{4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]morpholin-3-yl}acetate,

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyridin-2-yl]-3-azabicyclo [4.1.0]heptane-6-carboxylate (Enantiomer A),

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyridin-2-yl]-3-azabicyclo [4.1.0]heptane-6-carboxylate (Enantiomer B),

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyridin-2-yl]-3-azabicyclo [4.1.0]heptane-1-carboxylate (Enantiomer A),

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyridin-2-yl]-3-azabicyclo [4.1.0]heptane-1-carboxylate (Enantiomer B),

Potassium 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]azepane-4-carboxylate,

5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-2-(piperidin-1-yl)pyridine,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-3-fluoropyridin-2-yl]-4-methylpiperidine-4-carboxylic acid,

2-{4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]piperidin-1-yl}acetic acid,

Ethyl (1R,5S,6r)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]-pyridin-6-yl)pyrimidin-2-yl]bicyclo [3.1.0]hexane-6-carboxylate,

Ammonium (1R,5S,6r)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl]bicyclo [3.1.0]hexane-6-carboxylate,

Potassium 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-2-methylmorpholine-2-carboxylate,

(1R,4R)-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]cyclohexane-1-carboxylic acid,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyridin-2-yl]cyclohex-3-ene-1-carboxylic acid,

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (Enantiomer A),

Potassium 1-[3-chloro-5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]-4-methylpiperidine-4-carboxylate,

Potassium 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-methylcyclohexane-1-carboxylate (unknown isomer),

Potassium 4-{[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]methyl}cyclohexane-1-carboxylic acid,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]bicyclo[4.1.0]heptane-1-carboxylic acid,

Potassium 6-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]bicyclo[4.1.0]heptane-3-carboxylate,

Ammonium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]cyclopentane-1-carboxylate,

Ethyl 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-2-methylcyclohexane-1-carboxylate,

(1r,4r)-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2,7-dimethylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]cyclohexane-1-carboxylic acid,

Potassium 2-{4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo-[1 ,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclohexyl}acetate,

Potassium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclopentane-1-carboxylate,

6-[2-(4-Carboxy-3-methylcyclohexyl)pyrimidin-5-yl]-3-{[2-(difluoromethoxy)phenyl]-methyl}-7-ethoxy-2-methylimidazo[1,2-a]pyridin-1-ium formate,

Ammonium 5-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl]bicyclo[2.2.2]octane-2-carboxylate,

Potassium 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-methylcyclohexane-1-carboxylate,

Ethyl (1R,5S,6r)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]bicyclo[3.1.0]hexane-6-carboxylate,

Potassium (1R,5S,6r)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]bicyclo[3.1.0]hexane-6-carboxylate,

(1R,4R)-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-1-methylcyclohexane-1-carboxylic acid,

Potassium 3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]bicyclo [4.1.0]heptane-7-carboxylate,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-2-methylcyclohexane-1-carboxylic acid (Isomers A),

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-2-methylcyclohexane-1-carboxylic acid (Isomers B),

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-2-methylcyclohexane-1-carboxylic acid (Isomers C),

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-2-methylcyclohexane-1-carboxylic acid (Isomers D),

Potassium (1R,5S,6S)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo [1,2-a]pyridin-6-yl)pyridin-2-yl]bicyclo[3.1.0]hexane-6-carboxylate,

(4s)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-6-hydroxy-4-methyl-2-oxabicyclo[2.2.2]octan-3-one,

Potassium 7-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-oxa-7-azabicyclo[3.3.1]nonane-9-carboxylate,

Potassium 5-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-2-carboxylate,

8-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-2-methyl-2,4,8-triazaspiro[4.5]decane-1,3-dione,

Ethyl 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]cyclohex-3-ene-1-carboxylate,

Ethyl 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]cyclohexanecarboxylate,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclohexanecarboxylic acid (cis isomer),

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclohexanecarboxylic acid (trans isomer),

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-4-(trifluoromethyl)pyrimidin-2-yl]-1,4-diazepan-5-one,

(3S)-{4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]morpholin-3-yl}methanol,

(3R)-{445-[3-[[2-(Difluoromethoxy)phenyl]methyl]-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl]pyrimidin-2-yl]morpholin-3-yl}methanol,

(3R)-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]morpholine-3-carboxylic acid,

(3S)-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]morpholine-3-carboxylic acid,

2-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]propan-2-ol,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-(hydroxymethyl)piperidine-4-carboxylate,

Sodium 1-[5-[3-[[2-(difluoromethoxy)phenyl]methyl]-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl]pyrimidin-2-yl]-4-(hydroxymethyl)piperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo [1,2-a]pyridin-6-yl]pyrimidin-2-yl]-4-(methoxycarbonyl)piperidine-4-carboxylic acid,

Ethyl 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-1-carboxylate,

Sodium 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-1-carboxylate,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-(hydroxymethyl)piperidine-4-carboxylate,

Sodium 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-(hydroxymethyl)piperidine-4-carboxylate,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-(trifluoromethyl)piperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-4-(trifluoromethyl)piperidine-4-carboxylic acid,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-fluoropiperidine-4-carboxylate,

Sodium 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl]pyrimidin-2-yl]-4-fluoropiperidine-4-carboxylate,

Methyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methoxypiperidine-4-carboxylate,

Sodium 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methoxypiperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-fluoropiperidine-4-carboxylic acid,

Methyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-4-ethylpiperidine-4-carboxylic acid,

Methyl (1R,5S)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl}-3-azabicyclo [3.2.1]octane-8-carboxylate,

Methyl (1R,5S)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-(methoxy-methyl)imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.2.1]octane-8-carboxylate,

(1R,5S)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.2.1]octane-8-carboxylic acid,

Methyl (1R,5S,8s)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo[1,2-a 9 -pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.2.1]octane-8-carboxylic,

(1R,5S,8s)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.2.1]octane-8-carboxylic acid,

(1R,5S,8e)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.2.1]octane-8-carboxylic acid,

Methyl (1R,6S or 1S, 6R)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-6-carboxylate,

(1R,6S or 1S, 6R)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-6-carboxylic acid,

Methyl (1S,5S or 1R,5R)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo [1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylate,

(1S,5S or 1R,5R)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo [3.1.0]hexane-1-carboxylic acid,

Methyl (1R or 1S)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylate,

(1R,5R or 1S,5S)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-5-carboxylic acid,

Methyl (1S,6R or 1R,6S)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-6-carboxylate (Enantiomer B),

(1S,6R or 1R,6S)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-6-carboxylic acid (Enantiomer B),

(1R,6S or 1S6R)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[4.1.0]heptane-1-carboxylic acid,

Ethyl (1S,3R and 1R,3S)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclohexanecarboxylate (racemic cis isomer),

Ethyl (1S,3R and 1R,3S)-3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclohexanecarboxylate (racemic trans isomers),

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo [1,2-a]pyridin-6-yl)-pyrimidin-2-yl]cyclohexanecarboxylic acid,

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl) -pyrimidin-2-yl]cyclohexanecarboxylic acid (racemic trans diastereomer),

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl) -pyrimidin-2-yl]cyclohexanecarboxylic acid (racemic cis diastereomer),

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-3-methylpiperidine-3-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-methylpiperidine-3-carboxylic acid,

Ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl](hydroxy)methyl}-2-methylimidazo[1,2-a]-pyridin-6-yl]pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl](hydroxy)methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid,

Sodium 4-amino-1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-4-carboxylate,

8-[5-[3-[[2-(Difluoromethoxy)phenyl]methyl]-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl]pyrimidin-2-yl]-8-azabicyclo [3.2.1]octan-3-one,

Ethyl 2-{8-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-8-azabicyclo [3.2.1 ]octan-3-ylidene }acetate,

2-(Morpholin-4-yl)ethyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-6-[2-(morpholin-4-yl)pyrimidin-5-yl]-imidazo [1,2-a]pyridin-2-yl)methanol,

4-[5-(3-{[2-(Difluoromethoxy)phenyl](hydroxy)methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperazin-2-one,

4-[5-(3-{(S or R)-[2-(Difluoromethoxy)phenyl](hydroxy)methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperazin-2-one (Enantiomer A),

4-[5-(3-{(R or S)-[2-(Difluoromethoxy)phenyl](hydroxy)methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperazin-2-one (Enantiomer B),

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-4-methoxypyrimidin-2-yl]-1,4-diazepan-5-one,

Methyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-4-methoxypyrimidin-2-yl]piperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-4-methoxypyrimidin-2-yl]piperidine-4-carboxylic acid,

Methyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-(methoxymethyl)-imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-(methoxymethyl)imidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid,

Methyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-isopropylpiperidine-4-carboxylate,

Methyl 1-[5-(3-{1-[2-(difluoromethoxy)phenyl]ethyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-4-hydroxypiperidine-4-carboxylic acid,

4-[5-(7-Chloro-3-{[2-(difluoromethoxy)phenyl]-methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]piperazin-2-one,

4-[5-(7-Chloro-3-{[2-(difluoromethoxy)phenyl]-methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]morpholine,

7-Chloro-3-{[2-(difluoromethoxy)phenyl]methyl}-2-methyl-6-{2-[4-(methylsulfonyl)piperazin-1-yl]-pyrimidin-5-yl}imidazo[1,2-a]pyridine,

1-[5-(7-Chloro-3-{[2-(difluoromethoxy)phenyl]-methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]piperidine-4-carboxylic acid,

7-Chloro-3-{[2-(difluoromethoxy)phenyl]methyl}-6-(6-methoxypyridin-3-yl)-2-methylimidazo[1,2-a]-pyridine,

3-[2-(Difluoromethoxy)benzyl]-7-fluoro-2-(methoxymethyl)-6-{2-[4-(methylsulfonyl)-piperazin-1-yl]pyrimidin-5-yl}imidazo[1,2-a]pyridine,

3-{3-[(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-6-(6-methoxypyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl)methoxy]phenyl}oxazolidin-2-one,

3-{3-[(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-6-(6-oxo-1H-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl)methoxy]phenyl}oxazolidin-2-one,

5-(3-[2-(Difluoromethoxy)benzyl]-7-fluoro-2-{[3-(2-oxo-1,3-oxazolidin-3-yl)phenoxy]-methyl}imidazo[1,2-a]pyridin-6-yl)pyridine-2-carboxylic acid,

2-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-6-[2-(morpholin-4-yl)pyrimidin-5-yl]imidazo[1,2-a]pyridin-2-yl)acetonitrile,

{1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methypiperidin-4-yl}methanol,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carbaldehyde,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-4-sulfonamide,

3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methyl-6-{2-[4-(methylsulfonyl)-piperidin-1-yl]pyrimidin-5-yl}imidazo [1,2-a]pyridine,

N-({1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]piperidin-4-yl}sulfonyl)acetamide,

5-{1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl]pyrimidin-2-yl]piperidin-4-yl]-1,3,4-oxadiazol-2-ol,

{1-[5-(3-{1-[2-(Difluoromethoxy)phenyl]ethyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidin-4-yl}methanol,

tert-Butyl 4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-{[3-(2-oxo-oxazolidin-3-yl)phenoxy]methyl}imidazo[1,2-a ]pyridin-6-yl)pyrimidin-2-yl]piperazine-1-carboxylate,

3-{3-[(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-6-[2-(piperazin-1-yl)pyrimidin-5-yl]imidazo[1,2-a ]pyridin-2-yl)methoxy]phenyl}oxazolidin-2-one hydrochloride,

Butyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

Methyl 4-[5-[3-[[2-(difluoromethoxy)phenyl]methyl]-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl]pyrimidin-2-yl]-1-methylcyclohexanecarboxylate (cis isomer),

Methyl 4-[5-[5[3-[[2-(difluoromethoxy)phenyl]methyl]-7-fluoro-2-methylimidazo[1,2- ]pyridin-6-yl]pyrimidin-2-yl]-1-methylcyclohexanecarboxylate (trans isomer),

cis-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-1-methylcyclohexanecarboxylic acid,

(8-anti)-3-(5-{3-[2-(Difluoromethoxy)benzyl]-7-fluoro-2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-3-azabicyclo[3.2.1]octane-8-carboxylic acid meglumine salt,

(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-6-[6-(methylsulfonyl)pyridin-3-yl]-imidazo[1,2-a]pyridin-2-yl)methanol,

3-[2-(Difluoromethoxy)benzyl]-2-methyl-6-[2-(methylsulfanyl)pyrimidin-5-yl]imidazo-[1,2-a]pyridine,

3-[2-(Difluoromethoxy)benzyl]-2-methyl-6-[2-(methylsulfonyl)pyrimidin-5-yl]imidazo-[1,2-a]pyridine,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl}-pyrimidin-2-yl)-4-methylpiperidine-4-carbonitrile,

5-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)tetrahydro-2H-[1,2,5]thiadiazolo[2,3-a]pyrazin-3(3aH)-one 1,1-dioxide,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-N-methoxypiperidine-4-carboxamide,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-2-methyl-1,4-diazepan-5-one,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-7-methyl-1,4-diazepan-5-one,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-N-(methylsulfonyl)piperidine-4-carboxamide,

3-[2-(Difluoromethoxy)benzyl]-7-fluoro-2-(methoxymethyl)-6-{2-[4-(2H-tetrazol-5-yl)-piperidin-1-yl]pyrimidin-5-yl}imidazo[1,2-a]pyridine, sodium salt,

3-[2-(Difluoromethoxy)benzyl]-2-methyl-6-{2-[(1R,5S)-3-oxa-8-azabicyclo[3.2.1 ]oct-8-yl]pyrimidin-5-yl}imidazo[1,2-a]pyridine,

3-[2-(Difluoromethoxy)benzyl]-2-methyl-6-{2-[4-(2H-tetrazol-5-yl)piperidin-1-yl]-pyrimidin-5-yl}imidazo[1,2-a]pyridine,

3-[2-(Difluoromethoxy)benzyl]-6-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyrimidin-5-yl}-2-methylimidazo[1,2-a]pyridine,

Ethyl 1-(5-{3- [2-(difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}-pyrimidin-2-yl)pyrrolidine-3-carboxylate,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)pyrrolidine-3-carboxylic acid,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)azetidine-3-carboxylic acid,

Ethyl 1-[5-(3-{1-[2-(difluoromethoxy)phenyl]ethyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

1-[5-(3-{1-[2-(Difluoromethoxy)phenyl]ethyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylic acid,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidin-4-one,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidin-4-ol,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-(trifluoromethyl)piperidin-4-ol,

(3R)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-3-carboxylic acid,

3(S)-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-3-carboxylic acid,

Methyl 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]piperidine-4-carboxylate,

Sodium 1-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]piperidine-4-carboxylate,

(2R)-4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-(methoxymethyl)imidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl]morpholine-2-carboxylic acid,

2(S)-4-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}7-fluoro-2-(methoxymethyl) imidazo-[1,2-a]pyridin-6-yl)pyrimidin-2-yl]morpholine-2-carboxylic acid,

(1R,5S)-3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane -6-carboxylic acid,

1-[5-(3-{[2-(Difluoromethoxy)phenyl](hydroxy)methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-4-carboxylic acid,

Ethyl 1-[5-(7-chloro-3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine -4-carboxylate,

Sodium 1-[5-(7-chloro-3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine -4-carboxylate,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-(nitromethyl)piperidin-4-ol,

Ethyl 1-[5-(3-{(amino)[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

Sodium 1-[5-(3-{(amino)[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-4-methylpiperidine-4-carboxylate,

1-[5-(3-{(Amino)[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-1,4-diazepan-5-one,

N-([2-(Difluoromethoxy)phenyl]{2-methyl-6-[2-(morpholin-4-yl)pyrimidin-5-yl]imidazo-[1,2-a]pyridin-3-yl}methyl)acetamide,

2-([2-(Difluoromethoxy)phenyl]{2-methyl-6-[2-(morpholin-4-yl)pyrimidin-5-yl]imidazo-[1,2-a]pyridin-3-yl}methoxy)acetic acid,

1-[5-(3-{1[2-(Difluoromethoxy)phenyl]ethyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-1,4-diazepan-5-one,

Methyl 1-[5-(3-{1-[2-(difluoromethoxy)phenyl]ethyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]piperidine-4-carboxylate,

1-[5-(3-{1-[2-(Difluoromethoxy)phenyl]ethyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]piperidine-4-carboxylic acid,

4-[5-(3-{[2-(Difluoromethoxy)phenyl](methoxy)methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]morpholine,

Benzyl 2-[2-(difluoromethoxy)phenyl]-2-{2-methyl-6-[2-(5-oxo-1,4-diazepan-1-yl)-pyrimidin-5-yl]imidazo[1,2-a]pyridin-3-yl}acetate,

2-[2-(Difluoromethoxy)phenyl]-2-{2-methyl-6-[2-(5-oxo-1,4-diazepan-1-yl)pyrimidin-5-yl]imidazo[1,2-a]pyridin-3-yl}acetic acid,

1[2-(Difluoromethoxy)phenyl]-1-{2-methyl-6[6-(piperazin-1-yl)pyridin-3-yl]imidazo-[1,2-a]pyridin-3-yl}ethanol,

2-(Difluoromethoxy)phenyl]{2-methyl-6-[6-(piperazin-1-yl)pyridin-3-yl]imidazo[1,2-a]-pyridin-3-yl}methanol,

4-[5-[3-[1-[2-(Difluoromethoxy)phenyl]ethyl]-2-methylimidazo[1,2-a]pyridin-6-yl]pyrimidin-2-yl]morpholine,

2-[5-(3-{[2-(Difluoromethoxy)phenyl](hydroxy)methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]propan-2-ol,

2-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyridin-2-yl]propan-2-ol,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyridin-2-yl]oxan-4-ol,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]oxan-4-ol,

tert-Butyl 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-hydroxyazetidine-1-carboxylate,

2-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]propan-2-ol,

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]oxetan-3-ol,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-1-methylpiperidin-4-ol,

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]azetidin-3-ol formic acid salt,

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-1-methylazetidin-3-ol formic acid salt,

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclobutan-1-ol,

4-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-4-hydroxycyclohexane-1-carboxylic acid,

2-(5-{3-[(1R or 1S)-1-[2-(Difluoromethoxy)phenyl]ethyl]-2-methylimidazo[1,2-a]-pyridin-6-yl}pyrimidin-2-yl)propan-2-ol (Enantiomers A),

2-(5-{3-[(1R or 1S)-1-[2-(Difluoromethoxy)phenyl]ethyl]-2-methylimidazo[1,2a]-pyridin-6-yl}pyrimidin-2-yl)propan-2-ol (Enantiomers B),

5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-2-(2-fluoropropan-2-yl)pyrimidine,

5-(3-{[2-(Difluoromethoxy)phenyl]methyl}7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-2 [1-(fluoromethyl)cyclopropyl]pyrimidine,

2-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]propan-2-yl acetate,

5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-2-(3-fluorooxetan-3-yl)pyrimidine,

2-[5-[3-[1-[2-(Difluoromethoxy)phenyl]ethyl]-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl]pyrimidin-2-yl]propan-2-ol (Enantiomers A),

2-[5-[3-[1-[2-(Difluoromethoxy)phenyl]ethyl]-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl]pyrimidin-2-yl]propan-2-ol (Enantiomers B),

N-({1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]cyclopropyl}methyl)acetamide,

2-[5-(3-{[2-(Difluoromethoxy)-5-fluorophenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]propan-2-ol,

5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6-yl)-2-(4-fluorooxan-4-yl)pyrimidine

3-[5(3-{[2-(Difluoromethoxy)phenyl]methyl}-7-fluoro-2-methylimidazo[1,2-a]pyridin-6yl)pyrimidin-2-yl]oxolan-3-ol,

3-[2-(Difluoromethoxy)benzyl]-6-[2-(4,4-difluoropiperidin-1yl)pyrimidin-5-yl]-2-methylimidazol]1,2-a]pyridine,

4-(5-{3-[2-(Difluoromethoxy)benzyl]-2-methylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)piperazine-2-carboxylic acid,

1-(5-{3-[2-(Difluoromethoxy)benzyl]-2,7-dimethylimidazo[1,2-a]pyridin-6-yl}pyrimidin-2-yl)-4-hydroxypiperidine-4-carboxylic acid,

1-[5-(3-{(1S or 1R)-1-[2-(Difluoromethoxy)phenyl]ethyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-1,4-diazepan-5-one (Enantiomer A),

1-[5-(3-{(1R or 1S)-1-[2-(Difluoromethoxy)phenyl]ethyl}-2-methylimidazo[1,2-a]-pyridin-6-yl)pyrimidin-2-yl]-1,4-diazepan-5-one (Enantiomer B),

Methyl 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (Enantiomer A),

Methyl 3-[5-(3-{[2-(difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (Enantiomer B),

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylic acid (Enantiomer A),

3-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3-azabicyclo[3.1.0]hexane-1-carboxylic acid (Enantiomer B),

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3-methylpiperidine-3-carboxylic acid (Enantiomer A),

1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3-methylpiperidine-3-carboxylic acid (Enantiomer B),

cis-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)-pyrimidin-2-yl]-3-methylpiperidine-4-carboxylic acid (Racemic), or

trans-1-[5-(3-{[2-(Difluoromethoxy)phenyl]methyl}-2-methylimidazo[1,2-a]pyridin-6-yl)pyrimidin-2-yl]-3-methylpiperidine-4-carboxylic acid (Racemic),

or a pharmaceutically acceptable salt thereof.

7. The pharmaceutical composition comprising a compound of formula (IIA) according to claim 1 or a pharmaceutically acceptable salt thereof, in association with a pharmaceutically acceptable carrier.

8. The pharmaceutical composition as claimed in claim 7 further comprising an additional pharmaceutically active ingredient.

9. The compound as claimed in claim 1 or a pharmaceurically acceptable salt thereof, wherein E represents —CH 2 — or —CH(CH 3 )—.

10. The compound as claimed in claim 1 or a pharmaceutically acceptable salt thereof, wherein R 12 represents hydrogen or fluoro.

11. The compound as claimed in claim 2 wherein R 21 is 2-hydroxyprop-2-yl.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2015
From: BENTLEY, JONATHAN MARK; BROOKINGS, DANIEL CHRISTOPHER; BROWN, JULIEN ALISTAIR; CAIN, THOMAS PAUL; CHOVATIA, PRAFUL TULSHI; FOLEY, ANNE MARIE; GALLIMORE, ELLEN OLIVIA; GLEAVE, LAURA JANE; HEIFETZ, ALEXANDER; HORSLEY, HELEN TRACEY; HUTCHINGS, MARTIN CLIVE; JACKSON, VICTORIA ELIZABETH; JOHNSON, JAMES ANDREW; JOHNSTONE, CRAIG; KROEPLIEN, BORIS; LECOMTE, FABIEN CLAUDE; LEIGH, DEBORAH; LOWE, MARTIN ALEXANDER; MADDEN, JAMES; PORTER, JOHN ROBERT; QUINCEY, JOANNA RACHEL; REED, LAURA CLAIRE; REUBERSON, JAMES THOMAS; RICHARDSON, ANTHONY JOHN; RICHARDSON, SARAH EMILY; SELBY, MATTHEW DUNCAN; SHAW, MICHAEL ALAN; ZHU, ZHAONING
To: UCB BIOPHARMA SPRL
Reel/Frame 035216/0056 →
Priority Claims (2)
GB 1212512.6 · Jul 13, 2012 · national
GB 1221920.0 · Dec 5, 2012 · national
Continuity (1)
Related Publication 20150203486A1 · Jul 23, 2015