JP2017500364A5 - - Google Patents
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- JP2017500364A5 JP2017500364A5 JP2016542969A JP2016542969A JP2017500364A5 JP 2017500364 A5 JP2017500364 A5 JP 2017500364A5 JP 2016542969 A JP2016542969 A JP 2016542969A JP 2016542969 A JP2016542969 A JP 2016542969A JP 2017500364 A5 JP2017500364 A5 JP 2017500364A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazol
- benzo
- amine
- triazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 1-hydroxymethylpropyl Chemical group 0.000 claims description 588
- 150000001875 compounds Chemical class 0.000 claims description 85
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 22
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 230000003463 hyperproliferative effect Effects 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 208000008035 Back Pain Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 201000003068 rheumatic fever Diseases 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 201000002510 thyroid cancer Diseases 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 3
- XNEKZHJLYPYEDG-FQEVSTJZSA-N (2R)-2-(4-chloro-3-fluorophenyl)-2-[5-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]benzotriazol-1-yl]ethanol Chemical compound ClC1=C(C=C(C=C1)[C@H](CO)N1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F XNEKZHJLYPYEDG-FQEVSTJZSA-N 0.000 claims description 2
- YEFNKKDOWBFTTN-OAHLLOKOSA-N (2R)-3-[[4-[1-[(3-fluoro-4-methoxyphenyl)methyl]benzotriazol-5-yl]pyrimidin-2-yl]amino]propane-1,2-diol Chemical compound FC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NC[C@H](CO)O)C=CC=1OC YEFNKKDOWBFTTN-OAHLLOKOSA-N 0.000 claims description 2
- RVUUULZWVYEJQP-HXUWFJFHSA-N (2S)-2-(3-fluoro-4-methoxyphenyl)-2-[5-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]benzotriazol-1-yl]ethanol Chemical compound FC=1C=C(C=CC=1OC)[C@@H](CO)N1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C RVUUULZWVYEJQP-HXUWFJFHSA-N 0.000 claims description 2
- XNEKZHJLYPYEDG-HXUWFJFHSA-N (2S)-2-(4-chloro-3-fluorophenyl)-2-[5-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]benzotriazol-1-yl]ethanol Chemical compound ClC1=C(C=C(C=C1)[C@@H](CO)N1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F XNEKZHJLYPYEDG-HXUWFJFHSA-N 0.000 claims description 2
- WDIUOJIBIYQMOP-ZDUSSCGKSA-N (2S)-2-[[4-[1-[(3-fluoro-4-methoxyphenyl)methyl]benzotriazol-5-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound FC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)N[C@H](CO)C)C=CC=1OC WDIUOJIBIYQMOP-ZDUSSCGKSA-N 0.000 claims description 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- WEUQDDHRMRKJFE-UHFFFAOYSA-N 1-[[4-[1-[(3-fluoro-4-methoxyphenyl)methyl]benzotriazol-5-yl]pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound FC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NCC(C)(O)C)C=CC=1OC WEUQDDHRMRKJFE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- NYWWLAGHUMTSBB-UHFFFAOYSA-N 2-methoxy-1-oxidopyridin-1-ium Chemical compound COC1=CC=CC=[N+]1[O-] NYWWLAGHUMTSBB-UHFFFAOYSA-N 0.000 claims description 2
- STDJZPGBULTFDY-UHFFFAOYSA-N 2-methyl-1-[5-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]benzotriazol-1-yl]propan-2-ol Chemical compound CC(CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)O STDJZPGBULTFDY-UHFFFAOYSA-N 0.000 claims description 2
- CYKNJZXYPCRKLB-UHFFFAOYSA-N 3-[[4-[1-[(3-fluoro-4-methoxyphenyl)methyl]benzotriazol-5-yl]pyrimidin-2-yl]amino]-2,2-dimethylpropan-1-ol Chemical compound FC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NCC(CO)(C)C)C=CC=1OC CYKNJZXYPCRKLB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- RDKGKKJJOWUXDF-UHFFFAOYSA-N 4-[1-(2,2-difluoroethyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC(CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F RDKGKKJJOWUXDF-UHFFFAOYSA-N 0.000 claims description 2
- HCHMWZLELDYETC-UHFFFAOYSA-N 4-[1-(2,2-difluoropropyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC(CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)F HCHMWZLELDYETC-UHFFFAOYSA-N 0.000 claims description 2
- VQGLNWPGWZQMQI-UHFFFAOYSA-N 4-[1-(2-ethylbutyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical class CCC(CC)CN1N=NC2=CC(=CC=C12)C1=CC=NC(NC2=CC=NN2C)=N1 VQGLNWPGWZQMQI-UHFFFAOYSA-N 0.000 claims description 2
- BSLOZWRSVSMZKZ-UHFFFAOYSA-N 4-[1-(2-methoxy-2-methylpropyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC(CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)C BSLOZWRSVSMZKZ-UHFFFAOYSA-N 0.000 claims description 2
- RJBWQPWJJXUJRG-UHFFFAOYSA-N 4-[1-(2-methylbutyl)benzotriazol-5-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical class CN1N=CC(=C1)NC1=NC=CC(=N1)C1=CC2=C(N(N=N2)CC(CC)C)C=C1 RJBWQPWJJXUJRG-UHFFFAOYSA-N 0.000 claims description 2
- DQFORPABSRBOKI-UHFFFAOYSA-N 4-[1-(2-methylbutyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical class CN1N=CC=C1NC1=NC=CC(=N1)C1=CC2=C(N(N=N2)CC(CC)C)C=C1 DQFORPABSRBOKI-UHFFFAOYSA-N 0.000 claims description 2
- ZFXUMILMBOIHCX-UHFFFAOYSA-N 4-[1-(2-methylpropyl)benzotriazol-5-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C(C(C)C)N1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C ZFXUMILMBOIHCX-UHFFFAOYSA-N 0.000 claims description 2
- LUAXHBSGWJGLEK-UHFFFAOYSA-N 4-[1-(2-methylpropyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C(C)C)N1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C LUAXHBSGWJGLEK-UHFFFAOYSA-N 0.000 claims description 2
- NLPLKXWLYFWCFF-UHFFFAOYSA-N 4-[1-(2-methylpropyl)benzotriazol-5-yl]-N-(2-methyltriazol-4-yl)pyrimidin-2-amine Chemical compound C(C(C)C)N1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=NN(N=C1)C NLPLKXWLYFWCFF-UHFFFAOYSA-N 0.000 claims description 2
- VBFQZUJOKZAWJD-UHFFFAOYSA-N 4-[1-(3-methoxy-2,2-dimethylpropyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COCC(CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)C VBFQZUJOKZAWJD-UHFFFAOYSA-N 0.000 claims description 2
- JPMKSZAMMJUAAC-UHFFFAOYSA-N 4-[1-(4,4-difluorocyclohexyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1(CCC(CC1)N1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F JPMKSZAMMJUAAC-UHFFFAOYSA-N 0.000 claims description 2
- KNCFAJZUWNSXEV-UHFFFAOYSA-N 4-[1-(5-chloro-2,3-dihydro-1H-inden-1-yl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C2CCC(C2=CC=1)N1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C KNCFAJZUWNSXEV-UHFFFAOYSA-N 0.000 claims description 2
- MTIOMNMMKZGIHG-UHFFFAOYSA-N 4-[1-(azetidin-3-ylmethyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound N1CC(C1)CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C MTIOMNMMKZGIHG-UHFFFAOYSA-N 0.000 claims description 2
- NGJRZAMQKFBJJH-UHFFFAOYSA-N 4-[1-(cyclopentylmethyl)benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CCCC1)CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C NGJRZAMQKFBJJH-UHFFFAOYSA-N 0.000 claims description 2
- UWEAQDARDSPZGN-UHFFFAOYSA-N 4-[1-[(1-methylazetidin-3-yl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC2=C(N(N=N2)CC2CN(C2)C)C=C1 UWEAQDARDSPZGN-UHFFFAOYSA-N 0.000 claims description 2
- OHEXIZIOIZJBPW-UHFFFAOYSA-N 4-[1-[(1-methylcyclobutyl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC2=C(N(N=N2)CC2(CCC2)C)C=C1 OHEXIZIOIZJBPW-UHFFFAOYSA-N 0.000 claims description 2
- UOUKLFVLAVBJBH-UHFFFAOYSA-N 4-[1-[(2,3-difluorophenyl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=C1F UOUKLFVLAVBJBH-UHFFFAOYSA-N 0.000 claims description 2
- DJJBBROQSIXUBK-UHFFFAOYSA-N 4-[1-[(2,4-difluorophenyl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC(=C1)F DJJBBROQSIXUBK-UHFFFAOYSA-N 0.000 claims description 2
- YMBKGBVKSHWGLY-UHFFFAOYSA-N 4-[1-[(2-chloropyridin-3-yl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=NC=CC=C1CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YMBKGBVKSHWGLY-UHFFFAOYSA-N 0.000 claims description 2
- PHCMAIABBYAIMF-UHFFFAOYSA-N 4-[1-[(2-methoxypyridin-3-yl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound COC1=NC=CC=C1CN1N=NC2=C1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C PHCMAIABBYAIMF-UHFFFAOYSA-N 0.000 claims description 2
- RNANUNHHDRQTEK-UHFFFAOYSA-N 4-[1-[(2-methoxypyridin-3-yl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=NC=CC=C1CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C RNANUNHHDRQTEK-UHFFFAOYSA-N 0.000 claims description 2
- WUHIAFOOFWMCNG-UHFFFAOYSA-N 4-[1-[(3,3-difluorocyclobutyl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1(CC(C1)CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F WUHIAFOOFWMCNG-UHFFFAOYSA-N 0.000 claims description 2
- ZNESWAPZNLENAL-UHFFFAOYSA-N 4-[1-[(3,5-difluoropyridin-2-yl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C(=NC=C(C=1)F)CN1N=NC2=C1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C ZNESWAPZNLENAL-UHFFFAOYSA-N 0.000 claims description 2
- GJIYHDRAQJLQGF-UHFFFAOYSA-N 4-[1-[(3-chloro-4-fluorophenyl)methyl]benzotriazol-5-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1F GJIYHDRAQJLQGF-UHFFFAOYSA-N 0.000 claims description 2
- UMSARLKOIDUXPC-UHFFFAOYSA-N 4-[1-[(3-fluoro-4-methoxyphenyl)methyl]benzotriazol-5-yl]-N-(1,3,5-trimethylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NC=2C(=NN(C=2C)C)C)C=CC=1OC UMSARLKOIDUXPC-UHFFFAOYSA-N 0.000 claims description 2
- WLFAUFCRGUTCCE-UHFFFAOYSA-N 4-[1-[(3-fluoro-4-methoxyphenyl)methyl]benzotriazol-5-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=CC=1OC WLFAUFCRGUTCCE-UHFFFAOYSA-N 0.000 claims description 2
- ATAAWMQTBNHXAP-UHFFFAOYSA-N 4-[1-[(3-fluoro-4-methoxyphenyl)methyl]benzotriazol-5-yl]-N-(1-methyltetrazol-5-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NC2=NN=NN2C)C=CC=1OC ATAAWMQTBNHXAP-UHFFFAOYSA-N 0.000 claims description 2
- CFBHLEQUNLBURB-UHFFFAOYSA-N 4-[1-[(3-fluoro-4-methoxyphenyl)methyl]benzotriazol-5-yl]-N-(2-methyl-1-morpholin-4-ylpropan-2-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CN2N=NC3=C2C=CC(=C3)C2=NC(=NC=C2)NC(CN2CCOCC2)(C)C)C=CC=1OC CFBHLEQUNLBURB-UHFFFAOYSA-N 0.000 claims description 2
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| DK2820009T3 (en) * | 2012-03-01 | 2018-04-16 | Array Biopharma Inc | Serine / threonine kinase inhibitors |
| JP2015533151A (ja) | 2012-10-16 | 2015-11-19 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | セリン／スレオニンキナーゼ阻害剤 |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| MY176049A (en) | 2013-12-06 | 2020-07-22 | Genentech Inc | Serine/threonine kinase inhibitors |
| EP3089980B1 (en) | 2013-12-30 | 2018-01-31 | Array Biopharma, Inc. | Serine/threonine kinase inhibitors |
| EP3089788B1 (en) | 2013-12-30 | 2018-10-24 | Genentech, Inc. | Serine/threonine kinase inhibitors |
| JP6877423B2 (ja) | 2015-11-09 | 2021-05-26 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | がんの処置において有用なジヒドロイミダゾピラジノン誘導体 |
| CN109072311A (zh) | 2016-04-15 | 2018-12-21 | 豪夫迈·罗氏有限公司 | 用于癌症的诊断和治疗方法 |
| US10658802B2 (en) | 2016-06-24 | 2020-05-19 | Gyrus Acmi, Inc. | Gravity plug and connector |
| AU2018294054B2 (en) * | 2017-06-30 | 2022-05-26 | Beijing Tide Pharmaceutical Co., Ltd. | Rho-associated protein kinase inhibitor, pharmaceutical composition comprising same, and preparation method and use thereof |
| US11859252B2 (en) | 2017-09-08 | 2024-01-02 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| WO2019158579A1 (en) | 2018-02-13 | 2019-08-22 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| MA52360B1 (fr) | 2018-04-26 | 2025-05-30 | Pfizer Inc. | Dérivés de 2-amino-pyridine ou de 2-amino-pyrimidine utilisés en tant qu'inhibiteurs de kinases dépendantes des cyclines |
| US20220213119A1 (en) | 2019-03-28 | 2022-07-07 | Jiangsu Hengrui Medicine Ca, Lid. | Thienoheterocyclic derivative, preparation method therefor and medical use thereof |
| KR20210146956A (ko) | 2019-03-29 | 2021-12-06 | 지앙수 헨그루이 메디슨 컴퍼니 리미티드 | 피롤로헤테로고리형 유도체, 이의 제조 방법, 및 의약에서 이의 응용 |
| WO2020238776A1 (zh) | 2019-05-24 | 2020-12-03 | 江苏恒瑞医药股份有限公司 | 取代的稠合双环类衍生物、其制备方法及其在医药上的应用 |
| CN110627775A (zh) * | 2019-10-24 | 2019-12-31 | 嘉兴特科罗生物科技有限公司 | 一种小分子化合物 |
| AU2021354821A1 (en) | 2020-09-29 | 2023-06-08 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Crystal form of pyrrolo heterocyclic derivative and preparation method therefor |
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| GB2379016A (en) * | 2001-07-27 | 2003-02-26 | Hewlett Packard Co | Portable apparatus monitoring reaction of user to music |
| DE102008037790A1 (de) | 2008-08-14 | 2010-02-18 | Merck Patent Gmbh | Bicyclische Triazolderivate |
| WO2010141360A1 (en) * | 2009-06-05 | 2010-12-09 | Merck Sharp & Dohme Corp. | Biaryl benzotriazole derivatives |
| JP6085866B2 (ja) | 2011-02-28 | 2017-03-01 | アレイ バイオファーマ、インコーポレイテッド | セリン／トレオニンキナーゼインヒビター |
| JP6097289B2 (ja) | 2011-08-04 | 2017-03-15 | アレイ バイオファーマ、インコーポレイテッド | セリン／スレオニンキナーゼインヒビターとしてのキナゾリン化合物 |
| DK2820009T3 (en) * | 2012-03-01 | 2018-04-16 | Array Biopharma Inc | Serine / threonine kinase inhibitors |
| CA2882750A1 (en) | 2012-08-27 | 2014-03-06 | Jim Blake | Serine/threonine kinase inhibitors for the treatment of hyperproliferative|diseases |
| MY176049A (en) | 2013-12-06 | 2020-07-22 | Genentech Inc | Serine/threonine kinase inhibitors |
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| EP3089980B1 (en) | 2013-12-30 | 2018-01-31 | Array Biopharma, Inc. | Serine/threonine kinase inhibitors |
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