IP Library › Granted Patent US 10,696,693

Granted Patent B2

US 10,696,693 · App. 15/527,908 · Granted Jun 30, 2020

Fused imidazole derivatives as TGF-beta inhibitors

Inventors: Rajinder Singh (Belmont, CA); Todd Kinsella (Redwood City, CA); Jiaxin Yu (Foster City, CA); Marina Gelman (San Francisco, CA); Ihab S. Darwish (San Carlos, CA)

Assignee: Rigel Pharmaceuticals, Inc.

C07D519/00 A61K31/416 A61K31/4188 A61K31/428 A61K31/437 A61K31/4365 A61K31/4709 A61K31/498 A61K31/517 A61K31/519 A61K31/5377 A61K45/06 A61P19/02 C07D487/04 C07D498/04

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Quick Facts

Patent No.: US 10,696,693
App. No.: 15/527,908
Granted: Jun 30, 2020
Kind: B2

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Abstract

Disclosed are imidazole compounds, as well as pharmaceutical compositions and methods of use thereof. One embodiment is a compound having the structure Formula (I) and pharmaceutically acceptable salts, prodrugs and N-oxides thereof (and solvates and hydrates thereof), wherein A, Z, X, R 1 , R 2 m, p and a are as described herein. In certain embodiments, a compound disclosed herein inhibits TGF-β, and can be used to treat disease by blocking TGF-β signaling.

Claims (426)

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

or a pharmaceutically acceptable salt, or solvate or hydrate thereof,

wherein bond α is a single or double bond;

X is CH 2 , —CH(R x )—, or —N(R a )—;

wherein R a is hydrogen, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C(O)OR, —C(O)NR 2 , —C(O)R, —S(O)R, —S(O) 2 R, —S(O)OR, —S(O) 2 OR, —S(O)NR 2 , —S(O) 2 NR 2 , —OC(O)R, —OC(O)OR, —OC(O)NR 2 , —N(R)C(O)R, —N(R)C(O)OR, —N(R)C(O)NR 2 , —N(R)S(O)R or —N(R)S(O) 2 R, and

wherein when X is —CH(R x )—, p≥1, and R x combines with an R 1 group bound to the carbon adjacent to X to form a 5- or 6-membered heterocyclyl with an annular —N(R a )—;

m is 1 or 2;

A is phenyl, optionally substituted with one to five R 2 groups, wherein

each R 2 is independently halogen, —C 1 -C 6 alkyl, —C 1 -C 6 haloalkyl, —C 1 -C 6 alkoxy, C 3-8 Cak(C 0-6 alkyl), Hca(C 0-6 alkyl), Ar(C 0-6 alkyl), Het(C 0-6 alkyl), —O—(C 0 -C 6 alkyl)-Ar, —O—(C 0 -C 6 alkyl)-Het, —O—(C 0 -C 6 alkyl)-Cak, —O—(C 0 -C 6 alkyl)-Hca, —NO 2 or —CN, wherein the Ar, Het, Cak, Hca, alkyl, and haloalkyl are optionally substituted with 1, 2, 3, or 4 groups that are each independently halogen, cyano, nitro, —OR, —SR, —NR 2 , —C(O)OR, —C(O)NR 2 , —C(O)R, —S(O)R, —S(O) 2 R, —S(O)OR, —S(O) 2 OR, —S(O)NR 2 , —S(O) 2 NR 2 , —OC(O)R, —OC(O)OR, —OC(O)NR 2 , —N(R)C(O)R, —N(R)C(O)OR, —N(R)C(O)NR 2 , —N(R)S(O)R, —N(R)S(O) 2 R, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;

Z is a fused bicyclic ring of the formula,

wherein

Z is optionally substituted by one or two —R Z groups that are each independently C 3-8 Cak(C 0-6 alkyl), Hca(C 0-6 alkyl), Ar(C 0-6 alkyl), Het(C 0-6 alkyl), halogen, cyano, C 1-6 alkyl, C 1-6 haloalkyl, —C 1 -C 6 alkoxy, —OR, —SR, —NR 2 , —C(O)R, —C(O)OR, —C(O)NR 2 , —S(O) 2 NR 2 , —S(O) 2 R, —OC(O)R, —N(R)C(O)R, —OC(O)OR, —OC(O)NR 2 , —N(R)C(O)OR, —N(R)C(O)NR 2 , —N(R)S(O) 2 R, —OP(O)(OR) 2 , —CH 2 —OP(O)(OR), —O—C 1-6 alkyl-OR, —O—C 1-6 alkyl-SR, —O—C 1-6 alkyl-NR 2 , —O—C 1-6 alkyl-Hca, wherein each Ar, Het, Cak, Hca, alkyl, and haloalkyl group is optionally substituted by one or two —R Z2 groups;

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

each optionally substituted as described above,

each R 1 is independently hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —C 1 -C 6 alkoxy, C 3 -Cak(C 0-6 alkyl), Hca(C 0-6 alkyl), Ar(C 0-6 alkyl), Het(C 0-6 alkyl), —O—(C 0 -C 6 alkyl)-Ar, —O—(C 0 -C 6 alkyl)-Het, —O—(C 0 -C 6 alkyl)-Cak, —O—(C 0 -C 6 alkyl)-Hca, —C(O)OR, —NO 2 or —CN, wherein the Ar, Het, Cak, Hca, alkyl, and haloalkyl are optionally substituted with 1, 2, 3, or 4 groups that are each independently halogen, cyano, nitro, —OR, —SR, —NR 2 , —C(O)OR, —C(O)NR 2 , —C(O)R, —S(O)R, —S(O) 2 R, —S(O)OR, —S(O) 2 OR, —S(O)NR 2 , —S(O) 2 NR 2 , —OC(O)R, —OC(O)OR, —OC(O)NR 2 , —N(R)C(O)R, —N(R)C(O)OR, —N(R)C(O)NR 2 , —N(R)S(O)R, —N(R)S(O) 2 R, C 1 -C 6 alkyl, —C 1 -C 6 alkoxy or C 1 -C 6 haloalkyl;

or, when α is a single bond, two R 1 groups taken together, when attached to the same carbon atom, form a spirocycle, wherein the spirocycle is C 3 -C 8 Cak, or C 3 -C 8 Hca, and the Cak and Hca are optionally substituted with 1, 2, 3, or 4 groups which are each independently halogen, cyano, nitro, —OR, —SR, —NR 2 , —C(O)OR, —C(O)NR 2 , —C(O)R, —S(O)R, —S(O) 2 R, —S(O)OR, —S(O) 2 OR, —S(O)NR 2 , —S(O) 2 NR 2 , —OC(O)R, —OC(O)OR, —OC(O)NR 2 , —N(R)C(O)R, —N(R)C(O)OR, —N(R)C(O)NR 2 , —N(R)S(O)R, —N(R)S(O) 2 R, C 1 -C 6 alkyl, —C 1 -C 6 alkoxy, or C 1 -C 6 haloalkyl;

p is 0, 1, 2, 3, 4, 5 or 6;

each R 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;

wherein “Cak” represents cycloalkyl and “Hca” represents heterocycloalkyl;

provided that

the compound is not

1-isopropylsulfonyl-2-amino-6-(2-(phenyl)-imidazo[1,2-a]pyridin-3-yl) benzimidazole dimethanesulfonate,

1-isopropylsulfonyl-2-amino-6-(8-(methyl)-2-(phenyl)-imidazo[1,2-a]pyridin-3-yl)-benzimidazole dimethanesulfonate,

1-isopropylsulfonyl-2-amino-6-(2-(phenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-benzimidazole dimethanesulfonate,

1-isopropylsulfonyl-2-amino-6-(2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole-3-yl)benzimidazole methanesulfonate, or

1-isopropylsulfonyl-2-amino-6-(2-(phenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-3-yl)-benzimidazole.

2. The compound of claim 1 , wherein the compound has the structure

3. A compound that is:

6-(2-(m-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3-(trifluoromethyl)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3-chlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridin

6-(2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,3,4-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(3,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine

3-isopropyl-6-(2-(2,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridine

3-isopropyl-6-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridine

3-isopropyl-6-(2-(2,3,4-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridine

6-(2-(4-chloro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-chloro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2,3-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,3-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(4-chloro-2-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-chloro-2-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(4-methoxy-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-methoxy-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(4,5-difluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

3-(trifluoromethyl)-6-(2-(3,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridine

3-(trifluoromethyl)-6-(2-(2,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridine

3-(trifluoromethyl)-6-(2-(2,3,4-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridine

6-(2-(3-chloro-4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(3-chloro-4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2,4-difluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,4-difluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(3-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(4-fluoro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-fluoro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3,4-difluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,4-difluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,4-difluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2,5-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,5-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2-chloro-4,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2-chloro-4,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3-chloro-4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(2-(4,5-difluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(2-(3,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

6-(2-(4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(5-chloro-4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(5-chloro-4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(5-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(5-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(3-chloro-4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile

6-(2-(2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(4-fluoro-2,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-fluoro-2,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2-chloro-4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2-chloro-4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

2-fluoro-N-(3-(3-(imidazo[1,2-a]pyridin-6-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-2-yl)phenyl)benzenesulfonamide

3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclopentane-1,6′-pyrrolo[1,2-a]imidazole]

2′-(4-fluorophenyl)-3′-(imidazo[1,2-a]pyridin-6-yl)-5′H,7′H-spiro[cyclopentane-1,6′-pyrrolo[1,2-a]imidazole]

6-(2-(4-fluoro-2,3-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-fluoro-2,3-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

(3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazol]-4-yl)methanol

3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]-4-carboxylic acid

ethyl 3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]-4-carboxylate

3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-N-methyl-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]-4-carboxamide

3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-N,N-dimethyl-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]-4-carboxamide

3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]-4-carboxamide

6-(2-(3-chloro-2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(5-chloro-2-fluoro)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(5-chloro-2-fluoro)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

(3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazol]-4-yl)methyl methanesulfonate

3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-(azidomethyl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]

1-(3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazol]-4-yl)-N-methylmethanamine

1-(3′-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazol]-4-yl)-N,N-dimethylmethanamine

benzyl 3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-(4-fluorophenyl)-5,5a,6,7,9,9a-hexahydro-8H-imidazo[1′,2′: 1,2]pyrrolo[3,4-c]pyridine-8-carboxylate

3-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-(4-fluorophenyl)-8-methyl-5a,6,7,8,9,9a-hexahydro-5H-imidazo[1′,2′: 1,2]pyrrolo[3,4-c]pyridine

6-(2-(5-chloro-2-methyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(5-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,5-dichlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2,5-dichlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

6-(2-(5-chloro-2,4-difluoro)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(2-(2-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

2-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)thieno[3,2-c]pyridine

2-(2-(2,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)thieno[3,2-c]pyridine

2-(2-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)thieno[3,2-c]pyridine

2-(2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)thieno[3,2-c]pyridine

2-(2-(5-chloro-2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)thieno[3,2-c]pyridine

6-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)benzo[d]thiazole

1-(5-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-1-yl)ethan-1-one

6-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine

6-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)quinoxaline

6-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)quinoline

6-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)imidazo[1,2-a]pyridine

1-(5-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-1-yl)ethan-1-one

6-(6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)quinoline

6-(6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)quinoxaline

2-(6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)thieno[3,2-c]pyridine

6-(6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)quinazolin-4-amine

1-(5-(3-(2-methoxyethoxy)quinoxalin-6-yl)-6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-1-yl)ethan-1-one

2-(2-methoxyethoxy)-7-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)quinoxaline

2-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)thieno[3,2-c]pyridine

2-(2-methoxyethoxy)-7-(2-(2,3,5-trifluorophenyl)-5,6-dihydro-7λ 2 -imidazo[3,2-a]imidazol-3-yl)quinoxaline

5-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazole-2-carboxylic acid

5-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1-acetyl-6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazole-2-carboxylic acid

N,N-dimethyl-2-((7-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)quinoxalin-2-yl)oxy)ethan-1-amine

(5-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-2-yl)methanol

4-(2-((7-(6-(2,4,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl)quinoxalin-2-yl)oxy)ethyl)morpholine

(5-(quinolin-6-yl)-6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-2-yl)methanol

(5-(quinoxalin-6-yl)-6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazol-2-yl)methanol

5-(quinoxalin-6-yl)-6-(2,3,5-trifluorophenyl)-2,3-dihydro-1H-imidazo[1,2-a]imidazole-2-carboxylic acid

6-(4-fluorophenyl)-5-(1H-indazol-5-yl)imidazo[2,1-b]oxazole

5-(benzo[d]thiazol-6-yl)-6-(4-fluorophenyl)imidazo[2,1-b]oxazole

6-(4-fluorophenyl)-5-(1H-indazol-6-yl)imidazo[2,1-b]oxazole

6-(4-fluorophenyl)-5-(imidazo[1,2-a]pyridin-6-yl)imidazo[2,1-b]oxazole

6-(4-fluorophenyl)-5-(quinoxalin-6-yl)imidazo[2,1-b]oxazole

6-(3,4-difluorophenyl)imidazo[2,1-b]oxazole

6-(3,4-difluorophenyl)-5-iodoimidazo[2,1-b]oxazole

6-(3,4-difluorophenyl)-5-(1H-indazol-5-yl)imidazo[2,1-b]oxazole

6-(3,4-difluorophenyl)-5-(1H-indazol-6-yl)imidazo[2,1-b]oxazole

5-(benzo[d]thiazol-6-yl)-6-(3,4-difluorophenyl)imidazo[2,1-b]oxazole

6-(3,4-difluorophenyl)-5-(quinoxalin-6-yl)imidazo[2,1-b]oxazole

6-(3,4-difluorophenyl)-5-(imidazo[1,2-a]pyridin-6-yl)imidazo[2,1-b]oxazole

5-iodo-6-(m-tolyl)imidazo[2,1-b]oxazole

6-(m-tolyl)-5-(1H-indazol-5-yl)imidazo[2,1-b]oxazole

6-(m-tolyl)-5-(1H-indazol-6-yl)imidazo[2,1-b]oxazole

5-(benzo[d]thiazol-6-yl)-6-(m-tolyl)imidazo[2,1-b]oxazole

5-(quinoxalin-6-yl)-6-(m-tolyl)imidazo[2,1-b]oxazole

6-(m-tolyl)-5-(imidazo[1,2-a]pyridin-6-yl)imidazo[2,1-b]oxazole

5-(quinolin-6-yl)-6-(m-tolyl)imidazo[2,1-b]oxazole

5-(quinolin-6-yl)-6-(3,4-difluorophenyl)imidazo[2,1-b]oxazole

5-(quinolin-6-yl)-6-(4-fluorophenyl)imidazo[2,1-b]oxazole

6-(2,4,5-trifluorophenyl)-5-(1H-indazol-6-yl)imidazo[2,1-b]oxazole

6-(2,4,5-trifluorophenyl)-5-(imidazo[1,2-a]pyridin-6-yl)imidazo[2,1-b]oxazole

5-(quinoxalin-6-yl)-6-(2,4,5-trifluorophenyl)imidazo[2,1-b]oxazole

5-(quinolin-6-yl)-6-(2,4,5-trifluorophenyl)imidazo[2,1-b]oxazole

5-(benzo[d]thiazol-6-yl)-6-(2,4,5-trifluorophenyl)imidazo[2,1-b]oxazole

6-(2,4,5-trifluorophenyl)-5-(1H-indazol-5-yl)imidazo[2,1-b]oxazole

5-bromo-6-(2-fluoro-4-methylphenyl)imidazo[2,1-b]oxazole

6-(2,4-difluorophenyl)-5-(1H-indazol-5-yl)imidazo[2,1-b]oxazole

6-(2,4-difluorophenyl)-5-(1H-indazol-6-yl)imidazo[2,1-b]oxazole

5-(benzo[d]thiazol-6-yl)-6-(2,4-difluorophenyl)imidazo[2,1-b]oxazole

6-(2,4-difluorophenyl)-5-(quinoxalin-6-yl)imidazo[2,1-b]oxazole

5-(quinolin-6-yl)-6-(2,4-difluorophenyl)imidazo[2,1-b]oxazole

6-(2,4-difluorophenyl)-5-(imidazo[1,2-a]pyridin-6-yl)imidazo[2,1-b]oxazole

6-(2,3,4-trifluorophenyl)-5-(1H-indazol-5-yl)imidazo[2,1-b]oxazole

5-(benzo[d]thiazol-6-yl)-6-(2,3,4-trifluorophenyl)imidazo[2,1-b]oxazole

5-(quinolin-6-yl)-6-(2,3,4-trifluorophenyl)imidazo[2,1-b]oxazole

5-(imidazo[1,2-a]pyridin-6-yl)-6-(2,3,4-trifluorophenyl)imidazo[2,1-b]oxazole

5-(quinoxalin-6-yl)-6-(2,3,4-trifluorophenyl)imidazo[2,1-b]oxazole

6-(2-(2,3,5-trifluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-3-yl)quinoline

6-(2-(2,3,5-trifluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine

2-(2-methoxyethoxy)-7-(2-(2,3,5-trifluorophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-3-yl)quinoxaline

5-(2-(m-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(m-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(m-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

5-(2-(m-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-benzo[d]imidazole

5-(2-(4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

5-(2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(m-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(3-(trifluoromethyl)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-(trifluoromethyl)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-(trifluoromethyl)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3-(trifluoromethyl)phenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(3-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(3-chlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-chlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-chlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3-chlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(3,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2,4-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2,4,5-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,4,5-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2,4,5-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(2,4,5-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

5-(2-(2,3,6-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,3,6-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

3-(benzo[d][1,3]dioxol-5-yl)-2-(3-fluorophenyl)-6,7-dihydro-5H-pyrrolol[1,2-a]imidazole

6-(2-(2,3,4-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(2,3,4-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,3,4-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3,4,5-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(3,4,5-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3,4,5-tifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

5-(2-(3,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(3,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

5-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(4-chloro-2,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(4-chloro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-chloro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-chloro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(4-chloro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(3,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(2,3-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,3-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2,3-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2,3-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(4-chloro-2-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-chloro-2-fluoro-5-methylpheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-chloro-2-fluoro-5-methylpheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(4-chloro-2-fluoro-5-methylpheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(4-methoxy-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-methoxy-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-methoxy-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(4-methoxy-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(3,4-difluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3,4-difluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3,4-difluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(3,4-difluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(3-chloro-4-fluoropheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-chloro-4-fluoropheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3-chloro-4-fluoropheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(3-chloro-4-fluoropheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(2,4-difluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,4-difluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2,4-difluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2,4-difluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(3-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(3-chloro-4-fluoro-5-methylpheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(3-chloro-4-fluoro-5-methylpheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(3-chloro-4-fluoro-5-methylpheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(4-fluoro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-fluoro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-fluoro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(4-fluoro-3,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(2,4-difluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,4-difluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2,4-difluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2,4-difluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(2,5-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2,5-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2,5-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2,5-difluoro-4-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(2-chloro-4,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2-chloro-4,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2-chloro-4,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2-chloro-4,5-difluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

5-(2-(4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(5-chloro-4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(5-chloro-4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(5-chloro-4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(5-chloro-4-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(5-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(5-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(5-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(5-fluoro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(o-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(o-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(o-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(o-tolyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(4-fluoro-2,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-fluoro-2,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-fluoro-2,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(4-fluoro-2,5-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(2-chloro-4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2-chloro-4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2-chloro-4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2-chloro-4-fluoro-3-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

5-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

N-(3-(3-(1H-indazol-5-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-2-yl)phenyl)-2-fluorobenzenesulfonamide

6-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2-chloro-4-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

2′-(4-fluorophenyl)-3′-(1H-indazol-5-yl)-5′H,7′H-spiro[cyclopentane-1,6′-pyrrolo[1,2-a]imidazole]

6-(2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclopentane-1,6′-pyrrolo[1,2-a]imidazol]-3′-yl)benzo[d]thiazole

2′-(4-fluorophenyl)-3′-(quinoxalin-6-yl)-5′H,7′H-spiro[cyclopentane-1,6′-pyrrolo[1,2-a]imidazole]

2′-(4-fluorophenyl)-3′-(quinolin-6-yl)-5′H,7′H-spiro[cyclopentane-1,6′-pyrrolo[1,2-a]imidazole]

5-(2-(4-fluoro-2,3-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1H-indazole

6-(2-(4-fluoro-2,3-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-fluoro-2,3-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(4-fluoro-2,3-dimethylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

3′-(benzo[d]thiazol-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]-4-carboxylic acid

Ethyl 2′-(4-fluorophenyl)-3′-(quinoxalin-6-yl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]-4-carboxylate

2′-(4-fluorophenyl)-3′-(quinoxalin-6-yl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazole]-4-carboxylic acid

(3′-(benzo[d]thiazol-6-yl)-2′-(4-fluorophenyl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazol]-4-yl)methanol

(2′-(4-fluorophenyl)-3′-(quinoxalin-6-yl)-5′H,7′H-spiro[cyclohexane-1,6′-pyrrolo[1,2-a]imidazol]-4-yl)methanol

6-(2-(5-chloro-2-fluoropheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(5-chloro-2-fluoropheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(5-chloro-2-fluoropheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(5-chloro-2-methylpheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(4-methyl-3-(3-(quinoxalin-6-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-2-yl)phenyl)quinoxaline

6-(2-(5-chloro-2-methylpheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2,5-dichlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinazolin-4-amine

6-(2-(2,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinazolin-4-amine

6-(2-(5-chloro-2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinazolin-4-amine

6-(2-(3-chloro-4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinazolin-4-amine

6-(2-(2,5-dichloropheny)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(2,5-dichlorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(5-chloro-2-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

2-(2-methoxyethoxy)-7-(2-(2,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

7-(2-(5-chloro-2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-2-(2-methoxyethoxy)quinoxaline

7-(2-(3-chloro-4-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-2-(2-methoxyethoxy)quinoxaline

6-(2-(2-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(2-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

7-(2-(2-fluoro-5-methylphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-2-(2-methoxyethoxy)quinoxaline

2-(1H-imidazol-1-yl)-7-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

7-(2-(5-chloro-2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-2-(1H-imidazol-1-yl)quinoxaline

N,N-dimethyl-2-((7-(2-(2,3,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxalin-2-yl)oxy)ethan-1-amine

N,N-dimethyl-2-((7-(2-(2,4,5-trifluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxalin-2-yl)oxy)ethan-1-amine

2-((7-(2-(5-chloro-2-fluorophenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxalin-2-yl)oxy)-N,N-dimethylethan-1-amine

6-(2-(6-methylpyridin-2-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

5-(2-(pyridin-2-yl)-3a,4,5,6-tetrahydrocyclopenta[b]pyrrol-3-yl)-1H-indazole

6-(2-(pyridin-2-yl)-3a,4,5,6-tetrahydrocyclopenta[b]pyrrol-3-yl)-1H-indazole

6-(2-(pyridin-2-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)benzo[d]thiazole

6-(2-(pyridin-2-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoxaline

6-(2-(pyridin-2-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)quinoline

6-(2-(pyridin-2-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)imidazo[1,2-a]pyridine

or a pharmaceutically acceptable salt, or solvate or hydrate thereof.

4. The compound of claim 1 , wherein the compound has the structure,

5. The compound of claim 1 , wherein the compound has the structure,

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

7. A method for treating rheumatoid arthritis in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound of formula (I):

or a pharmaceutically acceptable salt, or solvate or hydrate thereof,

wherein

bond α is a single or double bond;

X is —CH 2 —, —CH(R x )—, —N(R a )— or —O—,

wherein when X is —CH(R x )—, p≥1, and R x combines with an R 1 group bound to the carbon adjacent to X to form a 5- or 6-membered heterocyclyl with an annular —N(R a )—;

m is 1 or 2;

A is phenyl or pyridyl, each optionally substituted with one to five R 2 groups, wherein

Z is

a fused bicyclic ring of the formula,

wherein

ring A is Ar or 5- or 6-membered Het,

ring B is 5- or 6-membered Het,

wherein

each R 1 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, —C 1 -C 6 alkoxy, C 3-8 Cak(C 0-6 alkyl), Hca(C 0-6 alkyl), Ar(C 0-6 alkyl), Het(C 0-6 alkyl), —O—(C 0 -C 6 alkyl)-Ar, —O—(C 0 -C 6 alkyl)-Het, —O—(C 0 -C 6 alkyl)-Cak, —O—(C 0 -C 6 alkyl)-Hca, —C(O)OR, —NO 2 or —CN, wherein the Ar, Het, Cak, Hca, alkyl, and haloalkyl are optionally substituted with 1, 2, 3, or 4 groups that are each independently halogen, cyano, nitro, —OR, —SR, —NR 2 , —C(O)OR, —C(O)NR 2 , —C(O)R, —S(O)R, —S(O) 2 R, —S(O)OR, —S(O) 2 OR, —S(O)NR 2 , —S(O) 2 NR 2 , —OC(O)R, —OC(O)OR, —OC(O)NR 2 , —N(R)C(O)R, —N(R)C(O)OR, —N(R)C(O)NR 2 , —N(R)S(O)R, —N(R)S(O) 2 R, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;

or, when α is a single bond, two R 2 groups taken together, when attached to the same carbon atom, form a spirocycle, wherein the spirocycle is C 3 -C 8 Cak, or C 3 -C 8 Hca, and the Cak and Hca are optionally substituted with 1, 2, 3, or 4 groups which are each independently halogen, cyano, nitro, —OR, —SR, —NR 2 , —C(O)OR, —C(O)NR 2 , —C(O)R, —S(O)R, —S(O) 2 R, —S(O)OR, —S(O) 2 OR, —S(O)NR 2 , —S(O) 2 NR 2 , —OC(O)R, —OC(O)OR, —OC(O)NR 2 , —N(R)C(O)R, —N(R)C(O)OR, —N(R)C(O)NR 2 , —N(R)S(O)R, —N(R)S(O) 2 R, C 1 -C 6 alkyl, —C 1 -C 6 alkoxy or C 1 -C 6 haloalkyl;

p is 0, 1, 2, 3, 4, 5 or 6; and

and wherein Cak is cycloalkyl and Hca is heterocycloalkyl.

8. A pharmaceutical composition comprising a pharmaceutically acceptable diluent, carrier, or excipient and a compound according to claim 4 .

9. A pharmaceutical composition comprising a pharmaceutically acceptable diluent, carrier, or excipient and a compound according to claim 5 .

Assignments (4)

SECURITY INTEREST Recorded May 8, 2026

From: RIGEL PHARMACEUTICALS, INC.

To: MIDCAP FUNDING IV TRUST

Reel/Frame 075576/0880 →

SECURITY INTEREST Recorded Aug 25, 2022

From: RIGEL PHARMACEUTICALS, INC.

To: MIDCAP FINANCIAL TRUST