JP2015529235A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- -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 | ||
| PCT/EP2013/069892 WO2014048939A1 (en) | 2012-09-26 | 2013-09-25 | Cyclic ether pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018106700A Division JP2018162263A (ja) | 2012-09-26 | 2018-06-04 | 環状エーテルピラゾール−４−イル−ヘテロシクリル−カルボキサミド化合物と使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015529235A JP2015529235A (ja) | 2015-10-05 |
| JP2015529235A5 true JP2015529235A5 (enExample) | 2018-02-08 |
| JP6666147B2 JP6666147B2 (ja) | 2020-03-13 |
Family
ID=49261521
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015532459A Active JP6666147B2 (ja) | 2012-09-26 | 2013-09-25 | 環状エーテルピラゾール−４−イル−ヘテロシクリル−カルボキサミド化合物と使用方法 |
| JP2018106700A Pending JP2018162263A (ja) | 2012-09-26 | 2018-06-04 | 環状エーテルピラゾール−４−イル−ヘテロシクリル−カルボキサミド化合物と使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018106700A Pending JP2018162263A (ja) | 2012-09-26 | 2018-06-04 | 環状エーテルピラゾール−４−イル−ヘテロシクリル−カルボキサミド化合物と使用方法 |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US9328106B2 (enExample) |
| EP (1) | EP2900657B1 (enExample) |
| JP (2) | JP6666147B2 (enExample) |
| KR (1) | KR102281288B1 (enExample) |
| CN (1) | CN104640858B (enExample) |
| AU (2) | AU2013322736A1 (enExample) |
| BR (1) | BR112015006019B1 (enExample) |
| CA (1) | CA2881068C (enExample) |
| CL (1) | CL2015000530A1 (enExample) |
| CR (1) | CR20150119A (enExample) |
| DK (1) | DK2900657T3 (enExample) |
| EA (1) | EA031622B1 (enExample) |
| ES (1) | ES2791648T3 (enExample) |
| HR (1) | HRP20200681T1 (enExample) |
| HU (1) | HUE049611T2 (enExample) |
| IL (1) | IL237159A0 (enExample) |
| LT (1) | LT2900657T (enExample) |
| MX (1) | MX376762B (enExample) |
| PE (1) | PE20151375A1 (enExample) |
| PH (1) | PH12015500488B1 (enExample) |
| PL (1) | PL2900657T3 (enExample) |
| PT (1) | PT2900657T (enExample) |
| RS (1) | RS60202B1 (enExample) |
| SG (1) | SG11201502343RA (enExample) |
| SI (1) | SI2900657T1 (enExample) |
| UA (1) | UA119229C2 (enExample) |
| WO (1) | WO2014048939A1 (enExample) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG10201610936RA (en) | 2011-12-22 | 2017-02-27 | 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 |
| CN104271569B (zh) * | 2012-05-03 | 2016-08-24 | 霍夫曼-拉罗奇有限公司 | 作为lrrk2调节剂的吡唑氨基嘧啶衍生物 |
| WO2013174962A1 (en) | 2012-05-25 | 2013-11-28 | Janssen R&D Ireland | Uracyl spirooxetane nucleosides |
| CN110684067A (zh) | 2012-12-21 | 2020-01-14 | 艾丽奥斯生物制药有限公司 | 取代的核苷和核苷酸 |
| CA2897200C (en) | 2013-01-14 | 2021-07-06 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as pim kinase inhibitors |
| PE20191245A1 (es) | 2013-01-15 | 2019-09-18 | Incyte Holdings Corp | Compuestos de tiazolcarboxamidas y piridinacarboxamida utiles como inhibidores de quinasa pim |
| CN105658653A (zh) | 2013-08-23 | 2016-06-08 | 因赛特公司 | 可用作pim激酶抑制剂的呋喃并-和噻吩并-吡啶甲酰胺化合物 |
| KR20160127140A (ko) | 2014-03-18 | 2016-11-02 | 에프. 호프만-라 로슈 아게 | 옥세판-2-일-피라졸-4-일-헤테로사이클릴-카복사마이드 화합물 및 사용 방법 |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| US9822124B2 (en) | 2014-07-14 | 2017-11-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as Pim kinase inhibitors |
| SG11201707752SA (en) | 2015-04-22 | 2017-11-29 | Rigel Pharmaceuticals Inc | Pyrazole compounds and method for making and using the compounds |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| AR105967A1 (es) | 2015-09-09 | 2017-11-29 | Incyte Corp | Sales de un inhibidor de pim quinasa |
| 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 |
| WO2017059251A1 (en) | 2015-10-02 | 2017-04-06 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| US20170107216A1 (en) | 2015-10-19 | 2017-04-20 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| AU2016358100B2 (en) | 2015-11-19 | 2021-05-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| TW201726623A (zh) | 2015-12-17 | 2017-08-01 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| TWI850624B (zh) | 2015-12-22 | 2024-08-01 | 美商英塞特公司 | 作為免疫調節劑之雜環化合物 |
| TW201808950A (zh) | 2016-05-06 | 2018-03-16 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| DK3472167T3 (da) | 2016-06-20 | 2022-09-05 | Incyte Corp | Heterocykliske forbindelser som immunomodulatorer |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3504198B1 (en) | 2016-08-29 | 2023-01-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| EP3558973B1 (en) | 2016-12-22 | 2021-09-15 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| IL295660A (en) | 2016-12-22 | 2022-10-01 | Incyte Corp | Benzooxazole derivatives as immunomodulators |
| ES2929193T3 (es) | 2016-12-22 | 2022-11-25 | Incyte Corp | Derivados de tetrahidro imidazo[4,5-c]piridina como inductores de la internalización de PD-L1 |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| TWI903299B (zh) | 2018-03-08 | 2025-11-01 | 美商英塞特公司 | 作為PI3K-γ抑制劑之胺基吡嗪二醇化合物 |
| RS64055B1 (sr) | 2018-03-30 | 2023-04-28 | Incyte Corp | Heterociklična jedinjenja kao imunomodulatori |
| EP4219492B1 (en) | 2018-05-11 | 2024-11-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | 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 |
| AU2020335903A1 (en) | 2019-08-30 | 2022-03-24 | Rigel Pharmaceuticals, Inc. | Pyrazole compounds, formulations thereof, and a method for using the compounds and/or formulations |
| 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 |
| CA3154131A1 (en) | 2019-09-13 | 2021-03-18 | Origenis Gmbh | 1,4-dihydrobenzo[d]pyrazolo[3,4-f][1,3]diazepine derivatives and related compounds as lrrk2, nuak1 and/or tyk2 kinase modulators for the treatment of e.g. autoimmune disease |
| EP4037773A1 (en) | 2019-09-30 | 2022-08-10 | Incyte Corporation | Pyrido[3,2-d]pyrimidine compounds as immunomodulators |
| BR112022009031A2 (pt) | 2019-11-11 | 2022-10-11 | Incyte Corp | Sais e formas cristalinas de um inibidor de pd-1/pd-l1 |
| CN115087655A (zh) | 2019-12-20 | 2022-09-20 | 辉瑞公司 | 苯并咪唑衍生物 |
| 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 |
| EP4240739A1 (en) | 2020-11-06 | 2023-09-13 | Incyte Corporation | Process for making a pd-1/pd-l1 inhibitor and salts and crystalline forms thereof |
| US11760756B2 (en) | 2020-11-06 | 2023-09-19 | Incyte Corporation | Crystalline form of a PD-1/PD-L1 inhibitor |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| 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 |
| TW202346291A (zh) | 2022-03-23 | 2023-12-01 | 美商雷傑製藥公司 | 作為ｉｒａｋ抑制劑的嘧啶—２—基—吡唑化合物 |
| WO2023202563A1 (en) * | 2022-04-18 | 2023-10-26 | Newbay Technology Development Co., Ltd. | Akt inhibitor in combination with pim kinase inhibitor |
| WO2024082724A1 (en) * | 2022-10-17 | 2024-04-25 | 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 |
| CN100528329C (zh) | 2001-07-12 | 2009-08-19 | 里艾克沙有限公司 | 微囊包封的催化剂,它们的制备方法和使用方法 |
| DE602006021205D1 (de) | 2005-10-07 | 2011-05-19 | Exelixis Inc | Azetidine als mek-inhibitoren bei der behandlung proliferativer erkrankungen |
| UY30183A1 (es) | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
| PE20080928A1 (es) * | 2006-10-31 | 2008-08-15 | Schering Corp | Derivados de anilinopiperazina como inhibidores de proteina quinasa |
| ES2431163T3 (es) * | 2007-03-01 | 2013-11-25 | Novartis Ag | Inhibidores de PIM quinasa y métodos para su uso |
| JP5591714B2 (ja) | 2007-12-12 | 2014-09-17 | マサチューセッツ インスティテュート オブ テクノロジー | 遷移金属触媒によるクロスカップリングのためのリガンド、およびその使用方法 |
| UY31679A1 (es) | 2008-03-03 | 2009-09-30 | Inhibidores de cinasa pim y metodos para su uso | |
| BRPI0914305B8 (pt) * | 2008-06-19 | 2021-05-25 | Xcovery Holding Co Llc | compostos de piridazina carboxamida substituída como compostos inibidores da quinase, uso dos compostos e uso de uma composição compreendendo os compostos |
| CN104311480A (zh) | 2008-09-02 | 2015-01-28 | 诺华股份有限公司 | 作为激酶抑制剂的吡啶甲酰胺衍生物 |
| JP5546636B2 (ja) | 2009-09-28 | 2014-07-09 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | ベンゾキセピンｐｉ３ｋ阻害剤化合物及び使用方法 |
| JP2012254939A (ja) * | 2009-10-07 | 2012-12-27 | Astellas Pharma Inc | オキサゾール化合物 |
| SG184475A1 (en) * | 2010-04-07 | 2012-11-29 | Hoffmann La Roche | Pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use |
| JP2013530199A (ja) * | 2010-07-06 | 2013-07-25 | ノバルティス アーゲー | キナーゼ阻害剤として有用な環状エーテル化合物 |
| UY33930A (es) | 2011-03-04 | 2012-10-31 | Novartis Ag | Inhibidores novedosos de quinasas |
| US8614206B2 (en) | 2011-09-27 | 2013-12-24 | F. Hoffmann-La Roche Ag | Pyrazol-4-yl-heterocyclyl-carboxamide compounds and methods of use |
-
2013
- 2013-09-25 JP JP2015532459A patent/JP6666147B2/ja active Active
- 2013-09-25 PT PT137704417T patent/PT2900657T/pt unknown
- 2013-09-25 DK DK13770441.7T patent/DK2900657T3/da active
- 2013-09-25 HR HRP20200681TT patent/HRP20200681T1/hr unknown
- 2013-09-25 CN CN201380048262.9A patent/CN104640858B/zh active Active
- 2013-09-25 LT LTEP13770441.7T patent/LT2900657T/lt unknown
- 2013-09-25 US US14/036,160 patent/US9328106B2/en active Active
- 2013-09-25 PE PE2015000409A patent/PE20151375A1/es unknown
- 2013-09-25 WO PCT/EP2013/069892 patent/WO2014048939A1/en not_active Ceased
- 2013-09-25 KR KR1020157007625A patent/KR102281288B1/ko active Active
- 2013-09-25 CA CA2881068A patent/CA2881068C/en active Active
- 2013-09-25 UA UAA201503792A patent/UA119229C2/uk unknown
- 2013-09-25 ES ES13770441T patent/ES2791648T3/es active Active
- 2013-09-25 MX MX2015003513A patent/MX376762B/es active IP Right Grant
- 2013-09-25 BR BR112015006019-6A patent/BR112015006019B1/pt active IP Right Grant
- 2013-09-25 RS RS20200475A patent/RS60202B1/sr unknown
- 2013-09-25 EA EA201590624A patent/EA031622B1/ru not_active IP Right Cessation
- 2013-09-25 EP EP13770441.7A patent/EP2900657B1/en active Active
- 2013-09-25 SG SG11201502343RA patent/SG11201502343RA/en unknown
- 2013-09-25 AU AU2013322736A patent/AU2013322736A1/en not_active Abandoned
- 2013-09-25 PL PL13770441T patent/PL2900657T3/pl unknown
- 2013-09-25 SI SI201331721T patent/SI2900657T1/sl unknown
- 2013-09-25 HU HUE13770441A patent/HUE049611T2/hu unknown
-
2015
- 2015-02-09 IL IL237159A patent/IL237159A0/en active IP Right Grant
- 2015-03-04 CL CL2015000530A patent/CL2015000530A1/es unknown
- 2015-03-06 CR CR20150119A patent/CR20150119A/es unknown
- 2015-03-06 PH PH12015500488A patent/PH12015500488B1/en unknown
-
2016
- 2016-03-30 US US15/085,164 patent/US9931323B2/en active Active
-
2018
- 2018-01-29 AU AU2018200648A patent/AU2018200648B2/en active Active
- 2018-06-04 JP JP2018106700A patent/JP2018162263A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2015529235A5 (enExample) | ||
| HRP20200681T1 (hr) | Ciklički eter pirazol-4-il-heterociklil-karboksamidni spojevi i postupci njihove upotrebe | |
| RU2016101548A (ru) | Соединения амидов гетероарилпиридона и азапиридона | |
| RU2017118165A (ru) | Ингибиторы энхансера гомолога 2 zestes | |
| JP2017532360A5 (enExample) | ||
| JP2019031560A5 (enExample) | ||
| JP2019527718A5 (enExample) | ||
| JP2021502387A5 (enExample) | ||
| RU2018138828A (ru) | Уменьшение массы опухоли путем введения ccr1 антагонистов в комбинации с pd-1 ингибиторами или pd-l1 ингибиторами | |
| JP2016513660A5 (enExample) | ||
| JP2013510123A5 (enExample) | ||
| JP2016520131A5 (enExample) | ||
| RU2015154275A (ru) | Комбинации антитела против pd-l1 и ингибитора mek и/или ингибитора braf | |
| JP2013056930A5 (enExample) | ||
| JP2016523974A5 (enExample) | ||
| JP2009513703A5 (enExample) | ||
| JP2015514808A5 (enExample) | ||
| JP2014139226A5 (enExample) | ||
| JP2009541223A5 (enExample) | ||
| HRP20220990T1 (hr) | 3-supstituirane propionske kiseline kao inhibitori alfa v integrina | |
| HRP20171696T1 (hr) | 3,4-dihidroizokinolin-2(1h)-ilni spojevi | |
| ES2917526T3 (es) | Compuestos de aminonaptoquinona y composición farmacéutica para bloquear el sistema ubiquitinación-proteasoma en enfermedades | |
| JP2017517538A5 (enExample) | ||
| JP2018515525A5 (enExample) | ||
| JP2018516994A5 (enExample) |