JP2018505903A5 - - Google Patents
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- Publication number
- JP2018505903A5 JP2018505903A5 JP2017543931A JP2017543931A JP2018505903A5 JP 2018505903 A5 JP2018505903 A5 JP 2018505903A5 JP 2017543931 A JP2017543931 A JP 2017543931A JP 2017543931 A JP2017543931 A JP 2017543931A JP 2018505903 A5 JP2018505903 A5 JP 2018505903A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- bipyridin
- haloalkyl
- imidazo
- methyl
- 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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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 83
- 125000000217 alkyl group Chemical group 0.000 claims 69
- 229910052736 halogen Inorganic materials 0.000 claims 56
- 150000002367 halogens Chemical class 0.000 claims 56
- 125000004093 cyano group Chemical group *C#N 0.000 claims 55
- -1 6-([2,2′-bipyridin] -3-yl) imidazo [1,2-a] pyridine-3-carbonitrile 6- (6 ′-(trifluoromethyl)-[2,2′-bipyridine] -3-yl) imidazo [1,2-a] pyridine-3-carbonitrile Chemical compound 0.000 claims 44
- 229910052739 hydrogen Inorganic materials 0.000 claims 39
- 239000001257 hydrogen Substances 0.000 claims 39
- 150000002431 hydrogen Chemical class 0.000 claims 38
- 125000001188 haloalkyl group Chemical group 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 11
- 125000002619 bicyclic group Chemical group 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 208000035475 disorder Diseases 0.000 claims 9
- 229940002612 prodrug Drugs 0.000 claims 9
- 239000000651 prodrug Substances 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 150000001204 N-oxides Chemical class 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- ZMBYQTGAXZOMOO-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CC=CN2C(C(=O)N)=CN=C21 ZMBYQTGAXZOMOO-UHFFFAOYSA-N 0.000 claims 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- DGXAOSOMFMODCF-UHFFFAOYSA-N pyrido[3,2-d]pyrimidin-4-amine Chemical compound C1=CN=C2C(N)=NC=NC2=C1 DGXAOSOMFMODCF-UHFFFAOYSA-N 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 3
- DREUPRFRJOSEAM-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=CC=CN2C(C#N)=CN=C21 DREUPRFRJOSEAM-UHFFFAOYSA-N 0.000 claims 3
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- AZFAJDPMNWNYRF-UHFFFAOYSA-N 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-1h-indazole Chemical compound CC1=CC=CC(C=2C(=CC=CN=2)C=2C=C3C=NNC3=CC=2)=N1 AZFAJDPMNWNYRF-UHFFFAOYSA-N 0.000 claims 2
- QGCULEVNMWYGBD-UHFFFAOYSA-N 6-(2-pyridin-2-ylpyridin-3-yl)quinazolin-3-ium-4-amine formate Chemical compound [O-]C=O.[NH3+]c1ncnc2ccc(cc12)-c1cccnc1-c1ccccn1 QGCULEVNMWYGBD-UHFFFAOYSA-N 0.000 claims 2
- PEFYDHOUMOOYOE-UHFFFAOYSA-N 6-(2-pyridin-2-ylpyridin-3-yl)quinazolin-4-amine Chemical compound N1=C(C(=CC=C1)C=1C=C2C(=NC=NC2=CC=1)N)C1=NC=CC=C1 PEFYDHOUMOOYOE-UHFFFAOYSA-N 0.000 claims 2
- SLVTUHAQKLQPFF-UHFFFAOYSA-N 6-[2-(6-fluoropyridin-2-yl)pyridin-3-yl]quinazolin-3-ium-4-amine 2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.[NH3+]c1ncnc2ccc(cc12)-c1cccnc1-c1cccc(F)n1 SLVTUHAQKLQPFF-UHFFFAOYSA-N 0.000 claims 2
- RUNNKSXKWNXOAY-UHFFFAOYSA-N 6-[2-(6-fluoropyridin-2-yl)pyridin-3-yl]quinazolin-4-amine Chemical compound FC1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2C(=NC=NC2=CC=1)N RUNNKSXKWNXOAY-UHFFFAOYSA-N 0.000 claims 2
- ZORXRGAPSQEFGA-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)N=CN=2 ZORXRGAPSQEFGA-UHFFFAOYSA-N 0.000 claims 2
- XBRZTHDHIMYWLN-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N XBRZTHDHIMYWLN-UHFFFAOYSA-N 0.000 claims 2
- DGFSIJYSSFFQNN-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N DGFSIJYSSFFQNN-UHFFFAOYSA-N 0.000 claims 2
- YJCOVIQCBIRRBN-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]quinazolin-3-ium-4-amine 2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.Cc1cccc(n1)-c1ncccc1-c1ccc2ncnc([NH3+])c2c1 YJCOVIQCBIRRBN-UHFFFAOYSA-N 0.000 claims 2
- XHPVHXBWWXRLEP-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]quinazolin-4-amine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=C2C(=NC=NC2=CC=1)N XHPVHXBWWXRLEP-UHFFFAOYSA-N 0.000 claims 2
- NDKQYMPVBHCEOS-UHFFFAOYSA-N 7-[2-(6-methylpyridin-2-yl)pyridin-3-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=CC=2N(C=C1)N=CN=2 NDKQYMPVBHCEOS-UHFFFAOYSA-N 0.000 claims 2
- 208000021642 Muscular disease Diseases 0.000 claims 2
- 102000004472 Myostatin Human genes 0.000 claims 2
- 108010056852 Myostatin Proteins 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 210000003205 muscle Anatomy 0.000 claims 2
- 201000006938 muscular dystrophy Diseases 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- UZKRYDHOEMBIPL-UHFFFAOYSA-N 2,2,2-trifluoro-N-[6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridin-3-yl]acetamide Chemical compound FC(C(=O)NC1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)C)(F)F UZKRYDHOEMBIPL-UHFFFAOYSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 claims 1
- WRPFUIWJWHZDCJ-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)pyridin-3-yl]quinoline Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=CC=NC2=CC=CC=C12 WRPFUIWJWHZDCJ-UHFFFAOYSA-N 0.000 claims 1
- QWIQXNOJDBEHSZ-UHFFFAOYSA-N 5-[2-(5-fluoropyridin-2-yl)pyridin-3-yl]-1H-indazole Chemical compound FC=1C=CC(=NC=1)C1=NC=CC=C1C=1C=C2C=NNC2=CC=1 QWIQXNOJDBEHSZ-UHFFFAOYSA-N 0.000 claims 1
- YCRXUCWREMOUMS-UHFFFAOYSA-N 5-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C1=NC=2N(C=C1)N=CC=2C#N YCRXUCWREMOUMS-UHFFFAOYSA-N 0.000 claims 1
- LECLRDWVJRSFSE-UHFFFAOYSA-N 5-methyl-2-pyridin-2-ylpyridine Chemical compound N1=CC(C)=CC=C1C1=CC=CC=N1 LECLRDWVJRSFSE-UHFFFAOYSA-N 0.000 claims 1
- RMHXAAARAOIMIT-UHFFFAOYSA-N 6-(2-pyridin-2-ylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N1=C(C(=CC=C1)C=1C=CC=2N(C=1)N=CN=2)C1=NC=CC=C1 RMHXAAARAOIMIT-UHFFFAOYSA-N 0.000 claims 1
- VHGGWLBXAAHMCY-UHFFFAOYSA-N 6-(2-pyridin-2-ylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound N1=C(C(=CC=C1)C=1C=CC=2N(C=1)C(=CN=2)C#N)C1=NC=CC=C1 VHGGWLBXAAHMCY-UHFFFAOYSA-N 0.000 claims 1
- GAMFQISAYKUQHQ-UHFFFAOYSA-N 6-[2-(5-fluoro-6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carboxamide Chemical compound FC=1C=CC(=NC=1C)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C(=O)N GAMFQISAYKUQHQ-UHFFFAOYSA-N 0.000 claims 1
- DDLRSTPDXCUOSI-UHFFFAOYSA-N 6-[2-(6-methoxypyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound COC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C=1)C(=CN=2)C#N DDLRSTPDXCUOSI-UHFFFAOYSA-N 0.000 claims 1
- HWKJOTIADMVNGT-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N HWKJOTIADMVNGT-UHFFFAOYSA-N 0.000 claims 1
- YCBKRCCFJLNHQE-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]pyrido[3,2-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N=CN=C(C=2N=1)N YCBKRCCFJLNHQE-UHFFFAOYSA-N 0.000 claims 1
- WVYXOAYTRDTDQJ-UHFFFAOYSA-N 6-[2-(6-methylpyridin-2-yl)pyridin-3-yl]quinazolin-3-ium-4-amine formate Chemical compound [O-]C=O.Cc1cccc(n1)-c1ncccc1-c1ccc2ncnc([NH3+])c2c1 WVYXOAYTRDTDQJ-UHFFFAOYSA-N 0.000 claims 1
- HEADPVLOZICIIU-UHFFFAOYSA-N 6-[2-(6-propan-2-ylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C(C)(C)C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(N=1)C(=CN=2)C#N HEADPVLOZICIIU-UHFFFAOYSA-N 0.000 claims 1
- RSZIJRFZWKINKF-UHFFFAOYSA-N 6-[4-(hydroxymethyl)-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound OCC1=C(C(=NC=C1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C#N RSZIJRFZWKINKF-UHFFFAOYSA-N 0.000 claims 1
- MSPZFXKELDKRLD-UHFFFAOYSA-N 6-[6-methyl-2-(6-methylpyridin-2-yl)pyridin-3-yl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound CC1=CC=C(C(=N1)C1=NC(=CC=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C#N MSPZFXKELDKRLD-UHFFFAOYSA-N 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 241000156724 Antirhea Species 0.000 claims 1
- 206010065687 Bone loss Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- RGTHFAUZIHIEQJ-UHFFFAOYSA-N FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N)F.C(N)(=O)C2=CN=C1N2C=C(C=C1)C=1C(=NC=CC1)C1=NC=C(C=C1)C(=O)O Chemical compound FC(C1=CC=CC(=N1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N)F.C(N)(=O)C2=CN=C1N2C=C(C=C1)C=1C(=NC=CC1)C1=NC=C(C=C1)C(=O)O RGTHFAUZIHIEQJ-UHFFFAOYSA-N 0.000 claims 1
- VIQUZGMJVPASJF-UHFFFAOYSA-N FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N.FC=2C=CC(=NC2C)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C#N Chemical compound FC1=CC(=NC=C1)C1=NC=CC=C1C=1C=CC=2N(C1)C(=CN2)C#N.FC=2C=CC(=NC2C)C2=NC=CC=C2C=2C=CC=1N(C2)C(=CN1)C#N VIQUZGMJVPASJF-UHFFFAOYSA-N 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000002720 Malnutrition Diseases 0.000 claims 1
- 206010028289 Muscle atrophy Diseases 0.000 claims 1
- 208000029578 Muscle disease Diseases 0.000 claims 1
- 206010049565 Muscle fatigue Diseases 0.000 claims 1
- AHIHHHDVKREJBC-UHFFFAOYSA-N N-[5-(3-cyanoimidazo[1,2-a]pyridin-6-yl)-6-(6-methylpyridin-2-yl)pyridin-3-yl]acetamide Chemical compound C(#N)C1=CN=C2N1C=C(C=C2)C=1C(=NC=C(C=1)NC(C)=O)C1=NC(=CC=C1)C AHIHHHDVKREJBC-UHFFFAOYSA-N 0.000 claims 1
- HSUXLMSGKDVTIT-UHFFFAOYSA-N N-[6-[3-(3-cyanoimidazo[1,2-a]pyridin-6-yl)pyridin-2-yl]pyridin-2-yl]acetamide Chemical compound C(#N)C1=CN=C2N1C=C(C=C2)C=1C(=NC=CC=1)C1=NC(=CC=C1)NC(C)=O HSUXLMSGKDVTIT-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000011623 Obstructive Lung disease Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 208000005770 Secondary Hyperparathyroidism Diseases 0.000 claims 1
- 208000026062 Tissue disease Diseases 0.000 claims 1
- 206010047626 Vitamin D Deficiency Diseases 0.000 claims 1
- 210000000577 adipose tissue Anatomy 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 239000003098 androgen Substances 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 230000037182 bone density Effects 0.000 claims 1
- 230000003412 degenerative effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- 230000002710 gonadal effect Effects 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
- BEHYAANJUKYBTH-UHFFFAOYSA-N imidazo[1,2-a]pyridine-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CN21 BEHYAANJUKYBTH-UHFFFAOYSA-N 0.000 claims 1
- DOGXPDFZEQXZDS-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound C1=CC=CN2C(C(=O)O)=CN=C21 DOGXPDFZEQXZDS-UHFFFAOYSA-N 0.000 claims 1
- YLXWTAXPOOYRSL-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1=CC=NN2C(C#N)=CN=C21 YLXWTAXPOOYRSL-UHFFFAOYSA-N 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 238000011866 long-term treatment Methods 0.000 claims 1
- 230000001071 malnutrition Effects 0.000 claims 1
- 235000000824 malnutrition Nutrition 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000020763 muscle atrophy Effects 0.000 claims 1
- 201000000585 muscular atrophy Diseases 0.000 claims 1
- 208000018360 neuromuscular disease Diseases 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 208000015380 nutritional deficiency disease Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims 1
- XMRIUEGHBZTNND-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC=NC2=C(C(=O)N)C=NN21 XMRIUEGHBZTNND-UHFFFAOYSA-N 0.000 claims 1
- PJESVVYWPFAJCS-UHFFFAOYSA-N pyridazine-3-carbonitrile Chemical compound N#CC1=CC=CN=N1 PJESVVYWPFAJCS-UHFFFAOYSA-N 0.000 claims 1
- 208000001076 sarcopenia Diseases 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 *c1cccnc1-c1ncccc1 Chemical compound *c1cccnc1-c1ncccc1 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562119052P | 2015-02-20 | 2015-02-20 | |
| US62/119,052 | 2015-02-20 | ||
| PCT/US2016/017938 WO2016133838A1 (en) | 2015-02-20 | 2016-02-15 | Gdf-8 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018505903A JP2018505903A (ja) | 2018-03-01 |
| JP2018505903A5 true JP2018505903A5 (enExample) | 2019-03-28 |
| JP6800158B2 JP6800158B2 (ja) | 2020-12-16 |
Family
ID=55587333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017543931A Expired - Fee Related JP6800158B2 (ja) | 2015-02-20 | 2016-02-15 | Ｇｄｆ−８阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9981944B2 (enExample) |
| EP (1) | EP3259264B1 (enExample) |
| JP (1) | JP6800158B2 (enExample) |
| CN (1) | CN107531666A (enExample) |
| AR (1) | AR103740A1 (enExample) |
| ES (1) | ES2928084T3 (enExample) |
| TW (1) | TW201643157A (enExample) |
| WO (1) | WO2016133838A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK3636649T3 (da) | 2014-01-24 | 2024-05-21 | Turning Point Therapeutics Inc | Diarylmakrocykler som modulatorer af proteinkinaser |
| EP3317285B1 (en) | 2015-07-02 | 2021-01-27 | Turning Point Therapeutics, Inc. | Chiral diaryl macrocycles as modulators of protein kinases |
| EP3319968A1 (en) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| WO2017007759A1 (en) | 2015-07-06 | 2017-01-12 | Tp Therapeutics, Inc. | Diaryl macrocycle polymorph |
| RS62639B1 (sr) | 2015-07-06 | 2021-12-31 | Alkermes Inc | Hetero-halo inhibitori histonskih deacetilaza |
| HK1255330A1 (zh) | 2015-08-26 | 2019-08-16 | 缆图药品公司 | 适用於治疗与ntrk相关的病症的化合物和组合物 |
| WO2017087778A1 (en) | 2015-11-19 | 2017-05-26 | Blueprint Medicines Corporation | Compounds and compositions useful for treating disorders related to ntrk |
| AU2018207402B2 (en) | 2017-01-11 | 2023-09-28 | Alkermes, Inc. | Bicyclic inhibitors of histone deacetylase |
| EA039417B1 (ru) | 2017-08-07 | 2022-01-25 | Родин Терапеутикс, Инк. | Бициклические ингибиторы гистондеацетилазы |
| BR112020003481B1 (pt) | 2017-08-22 | 2023-12-05 | Bayer Aktiengesellschaft | Derivados de heterocicleno, seus usos, formulação agroquímica, e métodos para controlar pragas animais e para proteger sementes ou uma planta germinativa de pragas |
| CN110066276B (zh) * | 2018-01-24 | 2020-09-18 | 上海璎黎药业有限公司 | 芳香杂环化合物、其中间体、制备方法、药物组合物和应用 |
| US11414431B2 (en) * | 2018-10-15 | 2022-08-16 | Nimbus Lakshmi, Inc. | Substituted pyrazolo[1,5-a]pyrimidines as TYK2 inhibitors |
| AR119140A1 (es) | 2019-06-13 | 2021-11-24 | Pi Industries Ltd | Compuestos heterocíclicos fusionados y su uso como agentes de control de plagas |
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| ATE322681T1 (de) | 1999-01-21 | 2006-04-15 | Metamorphix Inc | Inhibitoren für wachstumdifferenzierungsfaktor und ihre anwendungen |
| JP2001097950A (ja) * | 1999-10-01 | 2001-04-10 | Sankio Chemical Co Ltd | 新規なピリジン誘導体 |
| US7320789B2 (en) | 2001-09-26 | 2008-01-22 | Wyeth | Antibody inhibitors of GDF-8 and uses thereof |
| MXPA06007017A (es) | 2003-12-18 | 2006-08-31 | Janssen Pharmaceutica Nv | Derivados de pirido y pirimidopirimidina como agentes antiproliferativos. |
| PE20091268A1 (es) | 2007-12-19 | 2009-09-19 | Amgen Inc | Derivados heterociclicos como inhibidores de pi3 quinasa |
| FR2925902B1 (fr) | 2008-01-02 | 2011-01-07 | Sanofi Aventis | DERIVES D'IMIDAZO°1,2-a!PYRIDINE-2-CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| EP2304834A4 (en) | 2008-07-18 | 2014-03-19 | Flexel Llc | THIN, FLEXIBLE AND RECHARGEABLE ELECTROCHEMICAL ENERGY CELL AND METHOD FOR THE PRODUCTION THEREOF |
| WO2011050245A1 (en) | 2009-10-23 | 2011-04-28 | Yangbo Feng | Bicyclic heteroaryls as kinase inhibitors |
| US8575203B2 (en) | 2010-04-21 | 2013-11-05 | Boehringer Ingelheim International Gmbh | Chemical compounds |
| WO2011141848A1 (en) | 2010-05-11 | 2011-11-17 | Pfizer Inc. | Morpholine compounds as mineralocorticoid receptor antagonists |
| KR20130131293A (ko) * | 2010-07-05 | 2013-12-03 | 메르크 파텐트 게엠베하 | 키나아제 - 유도된 질환의 치료에 유용한 바이피리딜 유도체 |
| CA2852936A1 (en) | 2011-10-20 | 2013-04-25 | Glaxosmithkline Llc | Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators |
| EP2773641B1 (en) | 2011-10-31 | 2017-09-27 | Xenon Pharmaceuticals Inc. | Biaryl ether sulfonamides and their use as therapeutic agents |
| BR112014027181A2 (pt) | 2012-05-15 | 2017-06-27 | Novartis Ag | derivados de benzamida para a inibição da atividade de abl1, abl2 e bcr-abl1 |
| EP2903978B1 (en) | 2012-10-05 | 2022-12-07 | Rigel Pharmaceuticals, Inc. | Gdf-8 inhibitors |
| WO2014074657A1 (en) | 2012-11-08 | 2014-05-15 | Bristol-Myers Squibb Company | Bicyclic heterocycle substituted pyridyl compounds useful as kinase modulators |
| US9908867B2 (en) | 2013-01-08 | 2018-03-06 | Samumed, Llc | 3-(benzoimidazol-2-yl)-indazole inhibitors of the Wnt signaling pathway and therapeutic uses thereof |
| US20160280699A1 (en) | 2013-09-26 | 2016-09-29 | Bayer Pharma Aktiengesellschaft | Substituted phenylalanine derivatives |
| RS58376B1 (sr) | 2013-10-11 | 2019-04-30 | Hoffmann La Roche | Supstituisana heterociklična sulfonamidna jedinjenja korisna kao modulatori trpa1 |
| GB201321729D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| CN106536507B (zh) * | 2014-04-08 | 2020-04-07 | 里格尔药品股份有限公司 | 作为TGF-β抑制剂的2,3-二取代的吡啶化合物及其使用方法 |
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- 2016-02-15 JP JP2017543931A patent/JP6800158B2/ja not_active Expired - Fee Related
- 2016-02-15 WO PCT/US2016/017938 patent/WO2016133838A1/en not_active Ceased
- 2016-02-15 CN CN201680022627.4A patent/CN107531666A/zh active Pending
- 2016-02-15 ES ES16711043T patent/ES2928084T3/es active Active
- 2016-02-15 EP EP16711043.6A patent/EP3259264B1/en active Active
- 2016-02-19 AR ARP160100449A patent/AR103740A1/es not_active Application Discontinuation
- 2016-02-19 TW TW105104992A patent/TW201643157A/zh unknown
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