JP2015529235A5 - - Google Patents
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- JP2015529235A5 JP2015529235A5 JP2015532459A JP2015532459A JP2015529235A5 JP 2015529235 A5 JP2015529235 A5 JP 2015529235A5 JP 2015532459 A JP2015532459 A JP 2015532459A JP 2015532459 A JP2015532459 A JP 2015532459A JP 2015529235 A5 JP2015529235 A5 JP 2015529235A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- methyl
- carboxamide
- thiazole
- pyrazol
- 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 2,6-difluorophenyl Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 15
- 206010028980 Neoplasm Diseases 0.000 claims 11
- 201000011510 cancer Diseases 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- QYFKQWAZVKFMEO-UHFFFAOYSA-N 5-amino-n-[5-(6-amino-4,4-difluorooxepan-2-yl)-1-methylpyrazol-4-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C(F)(F)CC(N)COC1C=1N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F QYFKQWAZVKFMEO-UHFFFAOYSA-N 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- 208000025966 Neurological disease Diseases 0.000 claims 3
- 208000036142 Viral infection Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 230000007368 endocrine function Effects 0.000 claims 3
- 208000026278 immune system disease Diseases 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 230000007102 metabolic function Effects 0.000 claims 3
- 230000009385 viral infection Effects 0.000 claims 3
- PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 claims 2
- LSDYXXXNGXKTAV-ZLXOECBPSA-N 5-amino-n-[5-[(2r,7r)-5-amino-7-ethyloxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound O1[C@H](CC)CC(N)CC[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2F)F)=N1 LSDYXXXNGXKTAV-ZLXOECBPSA-N 0.000 claims 2
- GVRONTFMKDHPGJ-KTYPHDMWSA-N 5-amino-n-[5-[(5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C([C@H](F)[C@H](N)CC1)OC1C=1N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F GVRONTFMKDHPGJ-KTYPHDMWSA-N 0.000 claims 2
- 208000003200 Adenoma Diseases 0.000 claims 2
- 206010001233 Adenoma benign Diseases 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims 2
- 206010014733 Endometrial cancer Diseases 0.000 claims 2
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 2
- 208000003445 Mouth Neoplasms Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 208000009565 Pharyngeal Neoplasms Diseases 0.000 claims 2
- 206010034811 Pharyngeal cancer Diseases 0.000 claims 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 201000010881 cervical cancer Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010017758 gastric cancer Diseases 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 210000000244 kidney pelvis Anatomy 0.000 claims 2
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 102000020233 phosphotransferase Human genes 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- 201000002510 thyroid cancer Diseases 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- SCADKGSQUJNFSO-SCRDCRAPSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,5-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC(F)=CC(F)=C1F SCADKGSQUJNFSO-SCRDCRAPSA-N 0.000 claims 1
- KVYQPSVHULBNGT-LOWVWBTDSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,6-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC(F)=C1F KVYQPSVHULBNGT-LOWVWBTDSA-N 0.000 claims 1
- ZHOFPMKYJUYBTO-SCRDCRAPSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=CC(F)=C1F ZHOFPMKYJUYBTO-SCRDCRAPSA-N 0.000 claims 1
- FXQXRXUKLGCVRL-GUTXKFCHSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=CC=C1F FXQXRXUKLGCVRL-GUTXKFCHSA-N 0.000 claims 1
- NCLFDUDPYBHZOA-SNPRPXQTSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,5-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=C(N)SC(C=2C(=C(F)C=C(F)C=2)F)=N1 NCLFDUDPYBHZOA-SNPRPXQTSA-N 0.000 claims 1
- BESIACQRKWNYKW-XBFCOCLRSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,6-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=C(N)SC(C=2C(=C(F)C=CC=2F)F)=N1 BESIACQRKWNYKW-XBFCOCLRSA-N 0.000 claims 1
- OKIYRFOZQMNDOS-SNPRPXQTSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=C(N)SC(C=2C(=C(F)C=CC=2)F)=N1 OKIYRFOZQMNDOS-SNPRPXQTSA-N 0.000 claims 1
- YJIADGLOWQBVKG-KBMXLJTQSA-N 5-amino-n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=C(N)SC(C=2C(=CC=CC=2)F)=N1 YJIADGLOWQBVKG-KBMXLJTQSA-N 0.000 claims 1
- KVYQPSVHULBNGT-WZRBSPASSA-N 5-amino-n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,6-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC(F)=C1F KVYQPSVHULBNGT-WZRBSPASSA-N 0.000 claims 1
- ZHOFPMKYJUYBTO-BZPMIXESSA-N 5-amino-n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=CC(F)=C1F ZHOFPMKYJUYBTO-BZPMIXESSA-N 0.000 claims 1
- FXQXRXUKLGCVRL-NFAWXSAZSA-N 5-amino-n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=CC=C1F FXQXRXUKLGCVRL-NFAWXSAZSA-N 0.000 claims 1
- PYGKGAMKDMHKDO-BZPMIXESSA-N 5-amino-n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-[2-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=CC=CC(C(F)(F)F)=C1F PYGKGAMKDMHKDO-BZPMIXESSA-N 0.000 claims 1
- GVRONTFMKDHPGJ-RJTITELWSA-N 5-amino-n-[5-[(5s,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C([C@@H](F)[C@@H](N)CC1)OC1C=1N(C)N=CC=1NC(=O)C(=C(S1)N)N=C1C1=C(F)C=CC=C1F GVRONTFMKDHPGJ-RJTITELWSA-N 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 206010023347 Keratoacanthoma Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010023825 Laryngeal cancer Diseases 0.000 claims 1
- 206010062038 Lip neoplasm Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 206010062129 Tongue neoplasm Diseases 0.000 claims 1
- 208000008385 Urogenital Neoplasms Diseases 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 201000009036 biliary tract cancer Diseases 0.000 claims 1
- 208000020790 biliary tract neoplasm Diseases 0.000 claims 1
- 208000015322 bone marrow disease Diseases 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 125000004452 carbocyclyl group Chemical group 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 1
- 230000001886 ciliary effect Effects 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 230000003325 follicular Effects 0.000 claims 1
- 210000004907 gland Anatomy 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 208000014899 intrahepatic bile duct cancer Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000006721 lip cancer Diseases 0.000 claims 1
- 201000005249 lung adenocarcinoma Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000003747 lymphoid leukemia Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 210000000214 mouth Anatomy 0.000 claims 1
- 208000025113 myeloid leukemia Diseases 0.000 claims 1
- CYDPFSRPUFLBOV-UHFFFAOYSA-N n-(2-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound FC1=CC=CC=C1NC(=O)C1=CSC=N1 CYDPFSRPUFLBOV-UHFFFAOYSA-N 0.000 claims 1
- NPPJPSWJANUZGN-ZOWXZIJZSA-N n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,6-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=C(F)C=CC(F)=C1F NPPJPSWJANUZGN-ZOWXZIJZSA-N 0.000 claims 1
- MRDDLCBBDJHAQI-ZENOOKHLSA-N n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=CC=CC(F)=C1F MRDDLCBBDJHAQI-ZENOOKHLSA-N 0.000 claims 1
- PIBVQGPNQNIACT-ZENOOKHLSA-N n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=C(F)C=CC=C1F PIBVQGPNQNIACT-ZENOOKHLSA-N 0.000 claims 1
- JDGJVHTXRIDZOI-FCEWJHQRSA-N n-[5-[(2s,5r,6r)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-6-(2,6-difluoro-4-methoxyphenyl)-5-fluoropyridine-2-carboxamide Chemical compound FC1=CC(OC)=CC(F)=C1C1=NC(C(=O)NC2=C(N(C)N=C2)[C@H]2OC[C@H](F)[C@H](N)CC2)=CC=C1F JDGJVHTXRIDZOI-FCEWJHQRSA-N 0.000 claims 1
- VNEKRGIKAVDMQT-KCXAZCMYSA-N n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,6-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=CSC(C=2C(=C(F)C=CC=2F)F)=N1 VNEKRGIKAVDMQT-KCXAZCMYSA-N 0.000 claims 1
- LJNAHNRMZXPSTO-COXVUDFISA-N n-[5-[(2s,5r,6r)-5-amino-6-methoxyoxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C1C[C@@H](N)[C@@H](OC)CO[C@@H]1C(N(N=C1)C)=C1NC(=O)C1=CSC(C=2C(=CC=CC=2F)F)=N1 LJNAHNRMZXPSTO-COXVUDFISA-N 0.000 claims 1
- QJCFGVBELPPPLO-IOASZLSFSA-N n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,5-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=CC(F)=CC(F)=C1F QJCFGVBELPPPLO-IOASZLSFSA-N 0.000 claims 1
- NPPJPSWJANUZGN-JMSVASOKSA-N n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3,6-trifluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=C(F)C=CC(F)=C1F NPPJPSWJANUZGN-JMSVASOKSA-N 0.000 claims 1
- MRDDLCBBDJHAQI-IOASZLSFSA-N n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,3-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=CC=CC(F)=C1F MRDDLCBBDJHAQI-IOASZLSFSA-N 0.000 claims 1
- WCGMEHSXDIGVLJ-CPUCHLNUSA-N n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,4-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=CC=C(F)C=C1F WCGMEHSXDIGVLJ-CPUCHLNUSA-N 0.000 claims 1
- PIBVQGPNQNIACT-IOASZLSFSA-N n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=C(F)C=CC=C1F PIBVQGPNQNIACT-IOASZLSFSA-N 0.000 claims 1
- BHVNVQZCRDWTBP-CPUCHLNUSA-N n-[5-[(2s,5r,6s)-5-amino-6-fluorooxepan-2-yl]-1-methylpyrazol-4-yl]-2-(2-fluorophenyl)-1,3-thiazole-4-carboxamide Chemical compound C=1([C@H]2OC[C@@H](F)[C@H](N)CC2)N(C)N=CC=1NC(=O)C(N=1)=CSC=1C1=CC=CC=C1F BHVNVQZCRDWTBP-CPUCHLNUSA-N 0.000 claims 1
- 125000004322 oxepan-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108010083755 proto-oncogene proteins pim Proteins 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 208000000649 small cell carcinoma Diseases 0.000 claims 1
- 201000002314 small intestine cancer Diseases 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 201000006134 tongue cancer Diseases 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261705791P | 2012-09-26 | 2012-09-26 | |
| US61/705,791 | 2012-09-26 | ||
| US201361864882P | 2013-08-12 | 2013-08-12 | |
| US61/864,882 | 2013-08-12 | ||
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Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG10201913554YA (en) | 2011-12-22 | 2020-03-30 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| EP2844652B1 (en) * | 2012-05-03 | 2019-03-13 | Genentech, Inc. | Pyrazole aminopyrimidine derivatives as lrrk2 modulators |
| MX2014014323A (es) | 2012-05-25 | 2015-02-12 | Janssen R & D Ireland | Nucleosidos de espirooxetano de uracilo. |
| BR112015014457A2 (pt) | 2012-12-21 | 2017-11-21 | Alios Biopharma Inc | composto ou sal farmaceuticamente aceitável do mesmo e composição farmacêutica e respectivos usos e processos para melhorar ou tratar infecção de hcv, para inibir a atividade da ns5b polimerase do vírus da hepatite c e a replicação de vírus da hepatite c |
| ES2649156T3 (es) | 2013-01-14 | 2018-01-10 | Incyte Holdings Corporation | Compuestos bicíclicos de carboxamida aromática útiles como inhibidores de quinasas Pim |
| PE20191245A1 (es) | 2013-01-15 | 2019-09-18 | Incyte Holdings Corp | Compuestos de tiazolcarboxamidas y piridinacarboxamida utiles como inhibidores de quinasa pim |
| EA201690458A1 (ru) | 2013-08-23 | 2016-07-29 | Инсайт Корпорейшн | Фуро- и тиенопиридинкарбоксамиды, используемые в качестве ингибиторов pim-киназы |
| EP3119775B1 (en) | 2014-03-18 | 2019-11-06 | F. Hoffmann-La Roche AG | Oxepan-2-yl-pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use |
| US9822124B2 (en) | 2014-07-14 | 2017-11-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as Pim kinase inhibitors |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| LT3286181T (lt) * | 2015-04-22 | 2021-04-26 | Rigel Pharmaceuticals, Inc. | Pirazolo junginiai ir junginių gamybos bei naudojimo būdas |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| TWI734699B (zh) | 2015-09-09 | 2021-08-01 | 美商英塞特公司 | Ｐｉｍ激酶抑制劑之鹽 |
| CN105254624B (zh) * | 2015-09-18 | 2019-08-09 | 上海吉铠医药科技有限公司 | 异噻唑衍生物pim激酶抑制剂及其制备方法与在制药中的应用 |
| US9920032B2 (en) | 2015-10-02 | 2018-03-20 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG10202004618TA (en) | 2015-11-19 | 2020-06-29 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| MA44075A (fr) | 2015-12-17 | 2021-05-19 | Incyte Corp | Dérivés de n-phényl-pyridine-2-carboxamide et leur utilisation en tant que modulateurs des interactions protéine/protéine pd-1/pd-l1 |
| AU2016379372A1 (en) | 2015-12-22 | 2018-08-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| HUE060256T2 (hu) | 2016-06-20 | 2023-02-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018044783A1 (en) | 2016-08-29 | 2018-03-08 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| LT3558990T (lt) | 2016-12-22 | 2022-12-27 | Incyte Corporation | Tetrahidroimidazo[4,5-c]piridino dariniai kaip pd-l1 internalizavimo induktoriai |
| US20180179202A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| JP7101678B2 (ja) | 2016-12-22 | 2022-07-15 | インサイト・コーポレイション | 免疫調節剤としての複素環式化合物 |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| SMT202500157T1 (it) | 2018-03-30 | 2025-05-12 | Incyte Corp | Composti eterociclici come immunomodulatori |
| HUE061503T2 (hu) | 2018-05-11 | 2023-07-28 | Incyte Corp | Tetrahidro-imidazo[4,5-C]piridin-származékok mint PD-L1 immunmodulátorok |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| JP7665593B2 (ja) | 2019-08-09 | 2025-04-21 | インサイト・コーポレイション | Ｐｄ－１／ｐｄ－ｌ１阻害剤の塩 |
| PE20220970A1 (es) | 2019-08-30 | 2022-06-10 | Rigel Pharmaceuticals Inc | Compuestos de pirazol, formulaciones de los mismos y un metodo para usar los compuestos y/o formulaciones |
| TWI856177B (zh) * | 2019-09-11 | 2024-09-21 | 瑞士商赫孚孟拉羅股份公司 | 藥劑之製備方法 |
| JP2022548581A (ja) | 2019-09-13 | 2022-11-21 | オリゲニス ゲーエムベーハー | 例えば自己免疫疾患の処置のための、ＬＲＲＫ２、ＮＵＡＫ１および／またはＴＹＫ２キナーゼモジュレータとしての１，４－ジヒドロベンゾ［ｄ］ピラゾロ［３，４－ｆ］［１，３］ジアゼピン誘導体および関連する化合物 |
| PE20221038A1 (es) | 2019-09-30 | 2022-06-17 | Incyte Corp | Compuestos de pirido[3,2-d] pirimidina como inmunomoduladores |
| CA3160131A1 (en) | 2019-11-11 | 2021-05-20 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| EP4077316A1 (en) | 2019-12-20 | 2022-10-26 | Pfizer Inc. | Benzimidazole derivatives |
| EP3967307A1 (en) * | 2020-09-15 | 2022-03-16 | Instytut Hematologii I Transfuzologii | Use of pim kinase inhibitors to augment the efficacy of anti-cd20 antibody-based therapies in hematologic malignancies and non-malignant conditions |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之結晶形式 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| CR20230230A (es) | 2020-11-06 | 2023-07-27 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pdl1 y sales y formas cristalinas del mismo |
| CN112852960A (zh) * | 2020-12-09 | 2021-05-28 | 浙江省肿瘤医院 | 一种甲状腺乳头状癌生物标记物及其应用 |
| CN112625030A (zh) * | 2020-12-25 | 2021-04-09 | 杭州澳赛诺生物科技有限公司 | 一种一锅法合成n-保护3-溴代吡唑的合成方法 |
| US12357623B2 (en) | 2021-03-03 | 2025-07-15 | Rigel Pharmaceuticals, Inc. | Method for treating a disease or condition using a pyrazole compound or formulation thereof |
| IL315677A (en) | 2022-03-23 | 2024-11-01 | Rigel Pharmaceuticals Inc | Pyrimid-2-yl-pyrazole compounds as irak inhibitors |
| WO2023202563A1 (en) * | 2022-04-18 | 2023-10-26 | Newbay Technology Development Co., Ltd. | Akt inhibitor in combination with pim kinase inhibitor |
| EP4604953A1 (en) * | 2022-10-17 | 2025-08-27 | Ningbo Newbay Technology Development Co., Ltd | Pim kinase inhibitor in combination with kras inhibitor |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| CA1327358C (en) * | 1987-11-17 | 1994-03-01 | Morio Fujiu | Fluoro cytidine derivatives |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| US5831108A (en) | 1995-08-03 | 1998-11-03 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
| JPH1153696A (ja) | 1997-07-31 | 1999-02-26 | Toyota Motor Corp | カーブ路警報装置 |
| US7223879B2 (en) | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US6395916B1 (en) | 1998-07-10 | 2002-05-28 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| US6307087B1 (en) | 1998-07-10 | 2001-10-23 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| KR20040024564A (ko) | 2001-07-12 | 2004-03-20 | 아베시아 리미티드 | 마이크로캡슐화된 촉매, 이의 제조 방법 및 이의 사용 방법 |
| SI1934174T1 (sl) | 2005-10-07 | 2011-08-31 | Exelixis Inc | Inhibitorji MEK in postopki za njihovo uporabo |
| UY30183A1 (es) | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
| EP2078004B1 (en) * | 2006-10-31 | 2015-02-25 | Merck Sharp & Dohme Corp. | 2-aminothiazole-4-carboxylic amides as protein kinase inhibitors |
| CA2679659C (en) * | 2007-03-01 | 2016-01-19 | Novartis Ag | Pim kinase inhibitors and methods of their use |
| CN101952298B (zh) | 2007-12-12 | 2015-06-17 | 麻省理工学院 | 用于过渡金属催化的交联偶合反应的配体及其使用方法 |
| PE20091577A1 (es) | 2008-03-03 | 2009-11-05 | Novartis Ag | Inhibidores de cinasa pim y metodos para su uso |
| JP5670325B2 (ja) | 2008-06-19 | 2015-02-18 | エックスカバリー ホールディング カンパニー エルエルシー | キナーゼ阻害化合物としての置換されたピリダジンカルボキサミド化合物 |
| PL2344474T3 (pl) | 2008-09-02 | 2016-03-31 | Novartis Ag | Pochodne pikolinamidu jako inhibitory kinaz |
| US8263633B2 (en) | 2009-09-28 | 2012-09-11 | F. Hoffman-La Roche Ag | Benzoxepin PI3K inhibitor compounds and methods of use |
| JP2012254939A (ja) * | 2009-10-07 | 2012-12-27 | Astellas Pharma Inc | オキサゾール化合物 |
| JP6161537B2 (ja) * | 2010-04-07 | 2017-07-12 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | ピラゾール−４−イル−ヘテロシクリル−カルボキサミド化合物及び使用の方法 |
| US20130109682A1 (en) * | 2010-07-06 | 2013-05-02 | Novartis Ag | Cyclic ether compounds useful as kinase inhibitors |
| UY33930A (es) | 2011-03-04 | 2012-10-31 | Novartis Ag | Inhibidores novedosos de quinasas |
| EP2760857A1 (en) | 2011-09-27 | 2014-08-06 | F.Hoffmann-La Roche Ag | Pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use |
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