Granted Patent B2

US 9,981,944 · App. 15/043,729 · Granted May 29, 2018

Inventors: Pingyu Ding (Foster City, CA); Marina Gelman (San Francisco, CA); Todd Kinsella (Redwood City, CA); Rajinder Singh (Belmont, CA); Somasekhar Bhamidipati (Foster City, CA); Upender Velaparthi (Cheshire, CT); Robert M. Borzilleri (New Hope, PA); Hasibur Rahaman (Bangalore, IN); Jayakumar Sankara Warrier (Bangalore, IN)

Assignees: RIGEL PHARMACEUTICALS, INC; BRISTOL-MYERS SQUIBB COMPANY

C07D401/14C07B59/002C07C53/06C07C53/18C07D471/04C07D487/04C07B2200/05

Abstract

Claims (207)

1. A compound having the structure of formula)(I°):

or a pharmaceutically acceptable salt, prodrug, or N-oxide thereof, or a solvate or hydrate thereof,

wherein

n is 1, 2, 3 or 4;

R 1 is hydrogen, halogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 3-8 cycloalkenyl, heterocyclyl, aryl, heteroaryl, —R a , or —C 1-6 alkyl-R a , wherein R a is —OR S1 , —SR S1 , —NR S1 R S1 , —C(O)R S1 , —C(O)OR S1 , —C(O)NR S1 R S1 , —S(O) 2 NR S1 R S1 , —OC(O)R S1 , —N(R S1 )C(O)R S1 , —OC(O)OR S1 , —O(CH 2 ) m C(O)NR S1 R S1 , —N(R S1 )C(O)OR S1 , —N(R)C(O)NR S1 R S1 , —N(R S1 )S(O) 2 NR S1 R S1 , or —N(R S1 )S(O) 2 R S1 ;

wherein m is 0, 1, 2 or 3; and

wherein each R S1 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —(C 0 -C 6 alkyl)-Ar, —(C 0 -C 6 alkyl)-Het, —(C 0 -C 6 alkyl)-Cak, or —(C 0 -C 6 alkyl)-Hca, wherein Ar, Het, Cak, Hca, alkyl, and haloalkyl are optionally substituted with C 1 -C 6 alkyl, halogen, C 1 -C 6 haloalkyl or cyano;

p is 1, 2, 3 or 4;

R 2 is hydrogen, halogen, cyano, nitro, C 1-6 alkyl, C 1-6 haloalkyl, C 3-8 cycloalkyl, C 3-8 cycloalkenyl, heterocyclyl, aryl, heteroaryl, —R b , or —C 1-6 alkyl-R b , wherein R b is —OR S4 , —SR S4 ; —NR S4 R S4 , —C(O)R S4 , —C(O)OR S4 , —C(O)NR S4 R S4 , —S(O) 2 NR S4 R S4 , —OC(O)R S4 , —N(R S4 )C(O)R S4 , —OC(O)OR S4 , —O(CH 2 ) q C(O)NR S4 R S4 , —N(R S4 )C(O)OR S4 , —N(R)C(O)NR S4 R S4 , —N(R S4 )S(O) 2 NR S4 R S4 or —N(R S4 )S(O) 2 R S4 ;

wherein q is 0, 1, 2 or 3; and

wherein each R S4 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —(C 0 -C 6 alkyl)-Ar, —(C 0 -C 6 alkyl)-Het, —(C 0 -C 6 alkyl)-Cak, or —(C 0 -C 6 alkyl)-Hca, wherein Ar, Het, Cak, Hca, alkyl, and haloalkyl are optionally substituted with C 1 -C 6 alkyl, halogen, C 1 -C 6 haloalkyl or cyano;

Z is

a fused bicyclic ring of the formula,

 wherein

ring A is Ar or 6-membered Het,

ring B is 5- or 6-membered Het,

wherein

Z is optionally substituted by one or two —R Z groups that are each independently halogen, cyano, C 1-6 alkyl, C 1-6 haloalkyl, —C 1 -C 6 alkoxy, —OR S2 , —SR S2 , —NR S2 2 , —C(O)R S2 , —C(O)OR S2 , —C(O)NR S2 2 , —S(O) 2 NR S2 2 , —S(O) 2 R S2 , —OC(O)R S2 , —N(R S2 )C(O)R S2 , —OC(O)OR S2 , —OC(O)NR S2 2 , —N(R S2 )C(O)OR S2 , —N(R S2 )C(O)NR S2 2 , —N(R S2 )S(O) 2 R S2 , —OP(O)(OR S2 ) 2 or —CH 2 —OP(O)(OR S2 ), wherein each alkyl, haloalkyl and alkoxy is optionally substituted by one or two —R Z2 groups;

wherein each R S2 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl-O—C 1 -C 6 alkyl, —(C 0 -C 6 alkyl)-Ar, —(C 0 -C 6 alkyl)-Het, —(C 0 -C 6 alkyl)-Cak, or —(C 0 -C 6 alkyl)-Hca, wherein Ar, Het, Cak, Hca, alkyl, and haloalkyl are optionally substituted with C 1 -C 6 alkyl, halogen, C 1 -C 6 haloalkyl or cyano; and

each —R Z2 is independently halogen, cyano, C 1-6 alkyl, C 1-6 haloalkyl, —C 1 -C 6 alkoxy, —OR S3 , —SR S3 , —NR S3 2 , —C(O)R S3 , —C(O)OR S3 , —C(O)NR S3 2 , —S(O) 2 NR S3 2 , —S(O) 2 R S3 , —OC(O)R S3 , —N(R S3 )C(O)R S3 , —OC(O)OR S3 , —OC(O)NR S3 2 , —N(R S3 )C(O)OR S3 , —N(R S3 )C(O)NR S3 2 , —N(R S3 )S(O) 2 R S3 , —OP(O)(OR S3 ) 2 or —CH 2 —OP(O)(OR S3 ); and

 wherein each R S3 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —(C 0 -C 6 alkyl)-Ar, —(C 0 -C 6 alkyl)-Het, —(C 0 -C 6 alkyl)-Cak, or —(C 0 -C 6 alkyl)-Hca, wherein Ar, Het, Cak, Hca, alkyl, and haloalkyl are optionally substituted with C 1 -C 6 alkyl, halogen, C 1 -C 6 haloalkyl or cyano.

2. The compound of claim 1 , wherein

Z is

wherein Z is optionally substituted by one or two —R Z groups.

3. The compound of claim 1 , wherein

Z is

4. The compound of claim 1 , wherein n is 1 or 2 and each R 1 is independently halogen, C 1-6 alkyl, C 1-6 haloalkyl, or C 3-8 cycloalkyl.

5. The compound of claim 1 , wherein the compound has the structure of one of Formulae (Ia)-(Ih):

6. A compound according to claim 1 that is:

6-(6′-methyl-[2,2′-bipyridin]-3-yl)quinazolin-4-amine;

6-(6′-methyl-[2,2′-bipyridin]-3-yl)quinazolin-4-aminium 2,2,2-trifluoroacetate;

6-(6′-methyl-[2,2′-bipyridin]-3-yl)quinazolin-4-aminium formate;

6-(6′-Methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile;

6-(6′-Methyl-[2,2′-bipyridin]-3-yl)-[1,2,4]triazolo[1,5-a]pyridine;

7-(6′-Methyl-[2,2′-bipyridin]-3-yl)-[1,2,4]triazolo[1,5-a]pyridine;

6-(6′-Methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide;

6-([2,2′-Bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile;

6-([2,2′-Bipyridin]-3-yl)-[1,2,4]triazolo[1,5-a]pyridine;

6-([2,2′-Bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide;

6-(6′-methyl-[2,2′-bipyridin]-3-yl)pyrido[3,2-d]pyrimidin-4-amine;

6-(6′-fluoro-[2,2′-bipyridin]-3-yl)quinazolin-4-amine;

6-(6′-fluoro-[2,2′-bipyridin]-3-yl)quinazolin-4-aminium 2,2,2-trifluoroacetate;

6-([2,2′-bipyridin]-3-yl)quinazolin-4-amine;

6-([2,2′-bipyridin]-3-yl)quinazolin-4-aminium formate;

or a pharmaceutically acceptable salt, prodrug, or N-oxide thereof, or a solvate or hydrate thereof.

7. A compound according to claim 1 having the structure of formula (II):

or a pharmaceutically acceptable salt, prodrug or N-oxide thereof, or solvate or hydrate thereof,

wherein

R 1 is hydrogen, halogen, cyano, nitro, C 1-6 alkyl or C 1-6 haloalkyl;

Z is

a fused bicyclic ring of the formula,

 wherein

ring A is Ar or 6-membered Het,

ring B is 5- or 6-membered Het,

wherein

Z is optionally substituted by one or two —R Z groups that are each independently halogen, cyano, C 1-6 alkyl, C 1-6 haloalkyl, —C 1 -C 6 alkoxy, —OR S2 , —SR S2 , —NR S2 2 , —C(O)R S2 , —C(O)OR S2 , —C(O)NR S2 2 , —S(O) 2 NR S2 2 , —S(O) 2 R S2 , —OC(O)R S2 , —N(R S2 )C(O)R S2 , —OC(O)OR S2 , —OC(O)NR S2 2 , —N(R S2 )C(O)OR S2 , —N(R S2 )C(O)NR S2 2 , —NR S2 )S(O) 2 R S2 , —OP(O)(OR S2 ) 2 or —CH 2 —OP(O)(OR S2 );

wherein each R S2 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —(C 0 -C 6 alkyl)-Ar, —(C 0 -C 6 alkyl)-Het, —(C 0 -C 6 alkyl)-Cak, or —(C 0 -C 6 alkyl)-Hca, wherein Ar, Het, Cak, Hca, alkyl, and haloalkyl are optionally substituted with C 1 -C 6 alkyl, halogen, C 1 -C 6 haloalkyl or cyano;

provided that the compound is not 5-(6′-methyl-[2,2′-bipyridin]-3-yl)-1H-indazole.

8. The compound of claim 7 , wherein

Z is

wherein Z is optionally substituted by one or two —R Z groups.

9. The compound of claim 7 , wherein

Z is

wherein Z is optionally substituted by one or two —R Z groups.

10. The compound of claim 7 , wherein R 1 is hydrogen or methyl.

11. The compound of claim 7 , wherein the compound has the structure of Formulae (IIa)-(IIh):

12. The compound according to claim 1 that is

6-(6′-methyl-[2,2′-bipyridin]-3-yl)quinazolin-4-amine;

6-(6′-methyl-[2,2′-bipyridin]-3-yl)quinazolin-4-aminium 2,2,2-trifluoroacetate;

6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile;

6-(6′-Methyl-[2,2′-bipyridin]-3-yl)-[1,2,4]triazolo[1,5-a]pyridine;

7-(6′-Methyl-[2,2′-bipyridin]-3-yl)-[1,2,4]triazolo[1,5-a]pyridine;

6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide;

6-([2,2′-Bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide;

6-(6′-fluoro-[2,2′-bipyridin]-3-yl)quinazolin-4-amine;

6-(6′-fluoro-[2,2′-bipyridin]-3-yl)quinazolin-4-aminium 2,2,2-trifluoroacetate;

6-([2,2′-bipyridin]-3-yl)quinazolin-4-amine;

6-([2,2′-bipyridin]-3-yl)quinazolin-4-aminium formate;

or a pharmaceutically acceptable salt, prodrug, or N-oxide thereof, or a solvate or hydrate thereof.

13. A pharmaceutical composition comprising a compound or pharmaceutically acceptable salt according to claim 1 and a pharmaceutically acceptable carrier, excipient, or diluent.

14. A method for inhibiting GDF-8 in a cell comprising contacting the cell with an effective amount of a compound according to claim 1 .

15. A method for increasing muscle mass in a mammal in need thereof comprising administering a therapeutically effective amount of a compound according to claim 1 .

16. A method for increasing muscle strength in a mammal in need thereof comprising administering a therapeutically effective amount of a compound according to claim 1 .

17. A method for increasing trabecular bone density in a patient in need thereof, comprising administering a therapeutically effective amount of a compound according to claim 1 .

18. The compound of claim 1 , wherein the compound has the structure of one of Formulae (Ii)-(Im), (IIi)-(IIk), and (III):

19. The compound according to claim 1 that is

6-([2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(4′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-methoxy-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(5′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(5′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(4′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-(difluoromethyl)-5′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-(difluoromethyl)-5′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide methyl 3′-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-[2,2′-bipyridine]-5-carboxylate

methyl 3′-(3-carbamoylimidazo[1,2-a]pyridin-6-yl)-[2,2′-bipyridine]-5-carboxylate

3′-(3-carbamoylimidazo[1,2-a]pyridin-6-yl)-[2,2′-bipyridine]-5-carboxylic acid

6-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-ethyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-isopropyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-isopropyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-methoxy-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-cyclopropyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-cyclopropyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-(benzyloxy)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-([2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-acetyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-6-(6′-(2-hydroxypropan-2-yl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(4′,6′-dimethyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

N-(3′-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-[2,2′-bipyridin]-6-yl)methanesulfonamide

N-(3′-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-[2,2′-bipyridin]-6-yl)acetamide

6-(6′-chloro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine

6-(6′-(difluoromethyl)-5′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine

6-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carbonitrile

6-(6′-methoxy-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carbonitrile

6-(6′-methoxy-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

6-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

6-(5′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carbonitrile

6-(5′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

6-(5′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carbonitrile

6-(5′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

6-(6′-methyl-[2, 2′-bipyridin]-3-yl) imidazo[1,2-b]pyridazine-3-carbonitrile

6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

6-(4′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carbonitrile

6-(4′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carbonitrile

6-(6′-isopropyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carbonitrile

6-(6′-isopropyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

6-(6′-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carbonitrile

2,2,2-trifluoro-N-(6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridin-3-yl)acetamide

6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

N-(2,2-difluoroethyl)-6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-methyl-[2,2′-bipyridin]-3-yl)-N-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyridine-3-carboxamide

N-(2-methoxyethyl)-6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

N—( 2 H 3 )methyl-6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide

methyl-6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxylic acid

6-(6′-methyl-[2,2′-bipyridin]-3-yl)-N-(oxetan-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

N-cyclopropyl-6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-b]pyridazine-3-carboxamide

N-(6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridin-2-yl)acetamide

N-(6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridin-2-yl)acetamide

6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-2-carboxamide

6-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-2-carboxamide

6-(6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-2-carboxamide

6-(5-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(5-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-(difluoromethyl)-5-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-(difluoromethyl)-5-fluoro-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(5,5′-difluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6,6′-dimethyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6,6′-dimethyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-(difluoromethyl)-6-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6′-methyl-6-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(6′-methyl-6-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide methyl 3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-6′-methyl-[2,2′-bipyridine]-4-carboxylate

6-(4-(hydroxymethyl)-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(4-(difluoromethyl)-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(4-(difluoromethyl)-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(6-acetamido-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

N-(3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-6′-methyl-[2,2′-bipyridin]-5-yl)acetamide

6-(5-acetamido-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(5-amino-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(5-amino-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

N-(3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-6′-methyl-[2,2′-bipyridin]-4-yl)acetamide

6-(4-amino-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(4-acetamido-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)pyrido[3,2-d]pyrimidin-4-amine

6-(5′-fluoro-[2,2′-bipyridin]-3-yl)pyrido[3,2-d]pyrimidin-4-amine

6-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)pyrido[3,2-d]pyrimidin-4-amine

6-(6′-cyclopropyl-[2,2′-bipyridin]-3-yl)pyrido[3,2-d]pyrimidin-4-amine

6-(6′-ethyl-[2,2′-bipyridin]-3-yl)quinazolin-4-amine

6-(6′-isopropyl-[2,2′-bipyridin]-3-yl)quinazolin-4-amine

6-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)quinazolin-4-amine

6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)imidazo[1,2-a]pyridine-2-carboxamide

6-(6′-isopropyl-[2,2′-bipyridin]-3-yl)quinazolin-4-amine

6-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)quinoxaline

6-(6′-methyl-[2,2′-bipyridin]-3-yl)quinoxaline

6-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)quinoxaline

5-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)-1H-indazole

5-(5′-fluoro-[2,2′-bipyridin]-3-yl)-1H-indazole

5-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)-1H-indazole

3-(difluoromethyl)-5-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)-1H-indazole

5-(6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

5-(6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

5-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

5-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile ethyl 5-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

5-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)pyrazolo[1, 5-a]pyrimidine-3-carboxylic acid

N-methyl-5-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

N-cyclopropyl-5-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

N-methyl-5-(6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

N-cyclopropyl-5-(6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

5-(6′-methyl-[2,2′-bipyridin]-3-yl)-N-(oxetan-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide ethyl 5-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

5-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

N-cyclopropyl-5-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

5-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)-N-(oxetan-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide ethyl 5-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

5-(6′-(difluoromethyl)-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

5-(6′-(trifluoromethyl)-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine

5-(5′-fluoro-6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine

5-(6′-methyl-[2,2′-bipyridin]-3-yl)pyrazolo[1,5-a]pyrimidine

or a pharmaceutically acceptable salt, prodrug, or N-oxide thereof, or a solvate or hydrate thereof.

Assignments (9)

Continuity (2)