JP2013526613A5 - - Google Patents
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- JP2013526613A5 JP2013526613A5 JP2013512197A JP2013512197A JP2013526613A5 JP 2013526613 A5 JP2013526613 A5 JP 2013526613A5 JP 2013512197 A JP2013512197 A JP 2013512197A JP 2013512197 A JP2013512197 A JP 2013512197A JP 2013526613 A5 JP2013526613 A5 JP 2013526613A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- chloro
- methyl
- cancer
- administered
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 claims description 53
- 206010028980 Neoplasm Diseases 0.000 claims description 35
- 201000011510 cancer Diseases 0.000 claims description 33
- ZLOLCGXDJBXQCN-UHFFFAOYSA-N 5-[[4-[(2,3-dimethylindazol-6-yl)methylamino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.C1=CC2=C(C)N(C)N=C2C=C1CNC(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 ZLOLCGXDJBXQCN-UHFFFAOYSA-N 0.000 claims description 23
- -1 chloro-1-methyl-1H-pyrazol-5-yl Chemical group 0.000 claims description 22
- 206010006187 Breast cancer Diseases 0.000 claims description 21
- 208000026310 Breast neoplasm Diseases 0.000 claims description 21
- 206010033128 Ovarian cancer Diseases 0.000 claims description 21
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 21
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 21
- 206010060862 Prostate cancer Diseases 0.000 claims description 21
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 21
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 21
- 201000002528 pancreatic cancer Diseases 0.000 claims description 21
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 21
- CUIHSIWYWATEQL-UHFFFAOYSA-N pazopanib Chemical compound C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CUIHSIWYWATEQL-UHFFFAOYSA-N 0.000 claims description 18
- YFQJOPFTGMHYNV-YDALLXLXSA-N n-[(2s)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide;hydrochloride Chemical compound Cl.CN1N=CC(Cl)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=C1 YFQJOPFTGMHYNV-YDALLXLXSA-N 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 13
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 108010011536 PTEN Phosphohydrolase Proteins 0.000 claims description 3
- 102000014160 PTEN Phosphohydrolase Human genes 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 238000012423 maintenance Methods 0.000 claims 2
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 1
- YNSCKPCDFIDINW-UHFFFAOYSA-N 3-[[2-[[1-[2-(dimethylamino)acetyl]-6-methoxy-4,4-dimethyl-2,3-dihydroquinolin-7-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound COC1=CC(C(CCN2C(=O)CN(C)C)(C)C)=C2C=C1NC(N=C1NC=CC1=1)=NC=1NC=1C=CSC=1C(N)=O YNSCKPCDFIDINW-UHFFFAOYSA-N 0.000 claims 1
- 108091007960 PI3Ks Proteins 0.000 claims 1
- 238000000034 method Methods 0.000 description 53
- AFJRDFWMXUECEW-LBPRGKRZSA-N N-[(2S)-1-amino-3-(3-fluorophenyl)propan-2-yl]-5-chloro-4-(4-chloro-2-methyl-3-pyrazolyl)-2-thiophenecarboxamide Chemical compound CN1N=CC(Cl)=C1C1=C(Cl)SC(C(=O)N[C@H](CN)CC=2C=C(F)C=CC=2)=C1 AFJRDFWMXUECEW-LBPRGKRZSA-N 0.000 description 12
- RHMRHGLMZBCOKT-UHFFFAOYSA-N 2-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.CC1=CC=CC=C1S(N)(=O)=O RHMRHGLMZBCOKT-UHFFFAOYSA-N 0.000 description 10
- 208000032839 leukemia Diseases 0.000 description 8
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 6
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 6
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 5
- 101150029707 ERBB2 gene Proteins 0.000 description 4
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 101000605639 Homo sapiens Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Proteins 0.000 description 4
- 208000008839 Kidney Neoplasms Diseases 0.000 description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 4
- 208000034578 Multiple myelomas Diseases 0.000 description 4
- 102100038332 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Human genes 0.000 description 4
- 206010035226 Plasma cell myeloma Diseases 0.000 description 4
- 108091008611 Protein Kinase B Proteins 0.000 description 4
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 4
- 206010038389 Renal cancer Diseases 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 description 4
- 201000010982 kidney cancer Diseases 0.000 description 4
- 201000005202 lung cancer Diseases 0.000 description 4
- 208000020816 lung neoplasm Diseases 0.000 description 4
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 2
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
- 206010005003 Bladder cancer Diseases 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 2
- 208000011691 Burkitt lymphomas Diseases 0.000 description 2
- WDVGKIUWNWZVSV-MPQZCIACSA-N C/C(/C=N)=C(\c1c(C)[s]c(C(N/C(/CN)=C/c2cc(F)ccc2)=O)c1)/N(C)C Chemical compound C/C(/C=N)=C(\c1c(C)[s]c(C(N/C(/CN)=C/c2cc(F)ccc2)=O)c1)/N(C)C WDVGKIUWNWZVSV-MPQZCIACSA-N 0.000 description 2
- QPNRLWAITMLQNQ-MKVJVEEPSA-O C/C(/C=[NH2+])=C(\c1c(C)[s]c(CN[C@@H](Cc2cc(F)ccc2)CN)c1)/NC Chemical compound C/C(/C=[NH2+])=C(\c1c(C)[s]c(CN[C@@H](Cc2cc(F)ccc2)CN)c1)/NC QPNRLWAITMLQNQ-MKVJVEEPSA-O 0.000 description 2
- 206010008342 Cervix carcinoma Diseases 0.000 description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- 208000012609 Cowden disease Diseases 0.000 description 2
- 201000002847 Cowden syndrome Diseases 0.000 description 2
- 206010014733 Endometrial cancer Diseases 0.000 description 2
- 206010014759 Endometrial neoplasm Diseases 0.000 description 2
- 206010014967 Ependymoma Diseases 0.000 description 2
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 2
- 208000036566 Erythroleukaemia Diseases 0.000 description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 2
- 208000006168 Ewing Sarcoma Diseases 0.000 description 2
- 208000002966 Giant Cell Tumor of Bone Diseases 0.000 description 2
- 208000032612 Glial tumor Diseases 0.000 description 2
- 206010018338 Glioma Diseases 0.000 description 2
- 208000017604 Hodgkin disease Diseases 0.000 description 2
- 208000021519 Hodgkin lymphoma Diseases 0.000 description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 2
- 208000005726 Inflammatory Breast Neoplasms Diseases 0.000 description 2
- 206010021980 Inflammatory carcinoma of the breast Diseases 0.000 description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 208000035490 Megakaryoblastic Acute Leukemia Diseases 0.000 description 2
- 206010027406 Mesothelioma Diseases 0.000 description 2
- 208000003445 Mouth Neoplasms Diseases 0.000 description 2
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 2
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 description 2
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 2
- 206010029260 Neuroblastoma Diseases 0.000 description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 2
- 208000007452 Plasmacytoma Diseases 0.000 description 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 description 2
- 206010061934 Salivary gland cancer Diseases 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 description 2
- 208000000389 T-cell leukemia Diseases 0.000 description 2
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 description 2
- 206010042971 T-cell lymphoma Diseases 0.000 description 2
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 description 2
- 206010057644 Testis cancer Diseases 0.000 description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
- 206010047741 Vulval cancer Diseases 0.000 description 2
- 208000004354 Vulvar Neoplasms Diseases 0.000 description 2
- 208000008383 Wilms tumor Diseases 0.000 description 2
- 208000021841 acute erythroid leukemia Diseases 0.000 description 2
- 208000037833 acute lymphoblastic T-cell leukemia Diseases 0.000 description 2
- 208000013593 acute megakaryoblastic leukemia Diseases 0.000 description 2
- 208000020700 acute megakaryocytic leukemia Diseases 0.000 description 2
- 201000011143 bone giant cell tumor Diseases 0.000 description 2
- 201000010881 cervical cancer Diseases 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 201000004101 esophageal cancer Diseases 0.000 description 2
- 201000003444 follicular lymphoma Diseases 0.000 description 2
- 206010017758 gastric cancer Diseases 0.000 description 2
- 208000005017 glioblastoma Diseases 0.000 description 2
- 201000009277 hairy cell leukemia Diseases 0.000 description 2
- 201000010536 head and neck cancer Diseases 0.000 description 2
- 208000014829 head and neck neoplasm Diseases 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 2
- 201000004653 inflammatory breast carcinoma Diseases 0.000 description 2
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 201000001441 melanoma Diseases 0.000 description 2
- 201000008026 nephroblastoma Diseases 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 201000008968 osteosarcoma Diseases 0.000 description 2
- 230000002018 overexpression Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 2
- 201000011549 stomach cancer Diseases 0.000 description 2
- 201000003120 testicular cancer Diseases 0.000 description 2
- 201000002510 thyroid cancer Diseases 0.000 description 2
- 206010044412 transitional cell carcinoma Diseases 0.000 description 2
- 201000005112 urinary bladder cancer Diseases 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- 201000005102 vulva cancer Diseases 0.000 description 2
- RGJSVKAUQGSGDN-UHFFFAOYSA-N 4-(4-chloro-2-methylpyrazol-3-yl)thiophene-2-carboxamide;hydrochloride Chemical compound Cl.CN1N=CC(Cl)=C1C1=CSC(C(N)=O)=C1 RGJSVKAUQGSGDN-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1c(ccc(N(C)c2ccnc(Nc3ccc(C)c(S(*)(=O)=O)c3)n2)c2)c2n[n]1C Chemical compound Cc1c(ccc(N(C)c2ccnc(Nc3ccc(C)c(S(*)(=O)=O)c3)n2)c2)c2n[n]1C 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34838510P | 2010-05-26 | 2010-05-26 | |
| US61/348,385 | 2010-05-26 | ||
| PCT/US2011/037881 WO2011150044A1 (en) | 2010-05-26 | 2011-05-25 | Combination |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016084877A Division JP2016193903A (ja) | 2010-05-26 | 2016-04-21 | 組合せ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013526613A JP2013526613A (ja) | 2013-06-24 |
| JP2013526613A5 true JP2013526613A5 (https=) | 2014-07-17 |
Family
ID=45004353
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013512197A Withdrawn JP2013526613A (ja) | 2010-05-26 | 2011-05-25 | 組合せ |
| JP2016084877A Pending JP2016193903A (ja) | 2010-05-26 | 2016-04-21 | 組合せ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016084877A Pending JP2016193903A (ja) | 2010-05-26 | 2016-04-21 | 組合せ |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US20130237554A1 (https=) |
| EP (1) | EP2575460A4 (https=) |
| JP (2) | JP2013526613A (https=) |
| WO (1) | WO2011150044A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104736154A (zh) * | 2012-10-22 | 2015-06-24 | 葛兰素史克公司 | 组合 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0116452A (pt) * | 2000-12-21 | 2003-09-30 | Glaxo Group Ltd | Composto, composição farmacêutica, uso de um composto |
| UY30892A1 (es) * | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
| WO2010045309A1 (en) * | 2008-10-16 | 2010-04-22 | Glaxosmithkline Llc | Inhibitors of akt activity |
| CN102405047B (zh) * | 2009-01-30 | 2014-07-09 | 葛兰素史密斯克莱有限责任公司 | 结晶型的n-{(1s)-2-氨基-1-[(3-氟苯基)甲基]乙基}-5-氯-4-(4-氯-1-甲基-1h-吡唑-5-基)-2-噻吩甲酰胺盐酸盐 |
-
2011
- 2011-05-25 US US13/699,103 patent/US20130237554A1/en not_active Abandoned
- 2011-05-25 EP EP11787314.1A patent/EP2575460A4/en not_active Withdrawn
- 2011-05-25 JP JP2013512197A patent/JP2013526613A/ja not_active Withdrawn
- 2011-05-25 WO PCT/US2011/037881 patent/WO2011150044A1/en not_active Ceased
-
2014
- 2014-12-10 US US14/565,691 patent/US20150094283A1/en not_active Abandoned
-
2016
- 2016-04-21 JP JP2016084877A patent/JP2016193903A/ja active Pending
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