JP2017505291A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017505291A5 JP2017505291A5 JP2016541077A JP2016541077A JP2017505291A5 JP 2017505291 A5 JP2017505291 A5 JP 2017505291A5 JP 2016541077 A JP2016541077 A JP 2016541077A JP 2016541077 A JP2016541077 A JP 2016541077A JP 2017505291 A5 JP2017505291 A5 JP 2017505291A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- composition
- composition according
- halogen
- 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
- 150000001875 compounds Chemical class 0.000 claims description 310
- 125000000217 alkyl group Chemical group 0.000 claims description 246
- 229910052736 halogen Inorganic materials 0.000 claims description 142
- 150000002367 halogens Chemical class 0.000 claims description 116
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 229940124597 therapeutic agent Drugs 0.000 claims description 65
- 239000003814 drug Substances 0.000 claims description 62
- 125000000623 heterocyclic group Chemical group 0.000 claims description 59
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- -1 R 1 is H Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 102000015303 Fatty Acid Synthases Human genes 0.000 claims description 22
- 108010039731 Fatty Acid Synthases Proteins 0.000 claims description 22
- 230000008482 dysregulation Effects 0.000 claims description 22
- 230000037361 pathway Effects 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims description 10
- 229960003901 dacarbazine Drugs 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 9
- 208000036142 Viral infection Diseases 0.000 claims description 8
- 208000029742 colonic neoplasm Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 230000009385 viral infection Effects 0.000 claims description 8
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
- 201000002528 pancreatic cancer Diseases 0.000 claims description 6
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
- 206010073478 Anaplastic large-cell lymphoma Diseases 0.000 claims description 4
- 208000000659 Autoimmune lymphoproliferative syndrome Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 208000012609 Cowden disease Diseases 0.000 claims description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 4
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 4
- 208000032004 Large-Cell Anaplastic Lymphoma Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
- 239000012830 cancer therapeutic Substances 0.000 claims description 3
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims description 2
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 claims description 2
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 claims description 2
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims description 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 102000015790 Asparaginase Human genes 0.000 claims description 2
- 108010024976 Asparaginase Proteins 0.000 claims description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
- 108010006654 Bleomycin Proteins 0.000 claims description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 2
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 2
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims description 2
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 claims description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 2
- 108010092160 Dactinomycin Proteins 0.000 claims description 2
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 2
- 206010016935 Follicular thyroid cancer Diseases 0.000 claims description 2
- 208000002927 Hamartoma Diseases 0.000 claims description 2
- 206010019695 Hepatic neoplasm Diseases 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims description 2
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims description 2
- 238000006029 Jeger synthesis reaction Methods 0.000 claims description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 2
- 239000002136 L01XE07 - Lapatinib Substances 0.000 claims description 2
- 206010049459 Lymphangioleiomyomatosis Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000001344 Macular Edema Diseases 0.000 claims description 2
- 206010025415 Macular oedema Diseases 0.000 claims description 2
- 229930192392 Mitomycin Natural products 0.000 claims description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 2
- 208000009905 Neurofibromatoses Diseases 0.000 claims description 2
- 229930012538 Paclitaxel Natural products 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
- 206010062106 Respiratory tract infection viral Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- YCPOZVAOBBQLRI-WDSKDSINSA-N Treosulfan Chemical compound CS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-WDSKDSINSA-N 0.000 claims description 2
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 2
- 241000700605 Viruses Species 0.000 claims description 2
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims description 2
- 208000009956 adenocarcinoma Diseases 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 229960000473 altretamine Drugs 0.000 claims description 2
- 229960003272 asparaginase Drugs 0.000 claims description 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 claims description 2
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 2
- 208000001119 benign fibrous histiocytoma Diseases 0.000 claims description 2
- 229960000997 bicalutamide Drugs 0.000 claims description 2
- 229960001561 bleomycin Drugs 0.000 claims description 2
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 2
- 229960002092 busulfan Drugs 0.000 claims description 2
- BMQGVNUXMIRLCK-OAGWZNDDSA-N cabazitaxel Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OC)C(=O)C1=CC=CC=C1 BMQGVNUXMIRLCK-OAGWZNDDSA-N 0.000 claims description 2
- 229960001573 cabazitaxel Drugs 0.000 claims description 2
- 229960004117 capecitabine Drugs 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 229960004562 carboplatin Drugs 0.000 claims description 2
- 229960005243 carmustine Drugs 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 claims description 2
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 2
- 229960004630 chlorambucil Drugs 0.000 claims description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 2
- 229960004316 cisplatin Drugs 0.000 claims description 2
- 229960004397 cyclophosphamide Drugs 0.000 claims description 2
- 229960000684 cytarabine Drugs 0.000 claims description 2
- BFSMGDJOXZAERB-UHFFFAOYSA-N dabrafenib Chemical compound S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 BFSMGDJOXZAERB-UHFFFAOYSA-N 0.000 claims description 2
- 229960000640 dactinomycin Drugs 0.000 claims description 2
- 229960004679 doxorubicin Drugs 0.000 claims description 2
- 229950009791 durvalumab Drugs 0.000 claims description 2
- 208000023965 endometrium neoplasm Diseases 0.000 claims description 2
- 229960004671 enzalutamide Drugs 0.000 claims description 2
- WXCXUHSOUPDCQV-UHFFFAOYSA-N enzalutamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1N1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S WXCXUHSOUPDCQV-UHFFFAOYSA-N 0.000 claims description 2
- 229960001904 epirubicin Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229960005420 etoposide Drugs 0.000 claims description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims description 2
- 229960000390 fludarabine Drugs 0.000 claims description 2
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims description 2
- 229960002949 fluorouracil Drugs 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 2
- 229960005277 gemcitabine Drugs 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 2
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 claims description 2
- 229960000908 idarubicin Drugs 0.000 claims description 2
- 229960001101 ifosfamide Drugs 0.000 claims description 2
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 2
- 229960004768 irinotecan Drugs 0.000 claims description 2
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 claims description 2
- 229960004891 lapatinib Drugs 0.000 claims description 2
- 208000003849 large cell carcinoma Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 208000020141 lung sclerosing hemangioma Diseases 0.000 claims description 2
- 208000002780 macular degeneration Diseases 0.000 claims description 2
- 201000010230 macular retinal edema Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 2
- 229960001924 melphalan Drugs 0.000 claims description 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 2
- 229960001428 mercaptopurine Drugs 0.000 claims description 2
- 229960000485 methotrexate Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229960004857 mitomycin Drugs 0.000 claims description 2
- 229960001156 mitoxantrone Drugs 0.000 claims description 2
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 2
- 208000025113 myeloid leukemia Diseases 0.000 claims description 2
- 201000004931 neurofibromatosis Diseases 0.000 claims description 2
- 229960003301 nivolumab Drugs 0.000 claims description 2
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims description 2
- 229960001756 oxaliplatin Drugs 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229960001592 paclitaxel Drugs 0.000 claims description 2
- 229960002621 pembrolizumab Drugs 0.000 claims description 2
- 230000000241 respiratory effect Effects 0.000 claims description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 2
- 201000009484 sclerosing hemangioma Diseases 0.000 claims description 2
- 208000000649 small cell carcinoma Diseases 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 229940081616 tafinlar Drugs 0.000 claims description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 2
- 229960001196 thiotepa Drugs 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims description 2
- 229960003087 tioguanine Drugs 0.000 claims description 2
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960000303 topotecan Drugs 0.000 claims description 2
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 2
- 229960003181 treosulfan Drugs 0.000 claims description 2
- 210000000689 upper leg Anatomy 0.000 claims description 2
- GPXBXXGIAQBQNI-UHFFFAOYSA-N vemurafenib Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(Cl)=CC=2)=C1F GPXBXXGIAQBQNI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003048 vinblastine Drugs 0.000 claims description 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 2
- 229960004528 vincristine Drugs 0.000 claims description 2
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 2
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 2
- 229960004355 vindesine Drugs 0.000 claims description 2
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 claims description 2
- 229940034727 zelboraf Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 183
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 4
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 204
- 125000000753 cycloalkyl group Chemical group 0.000 description 46
- 0 *C1(*)CN(*)C1 Chemical compound *C1(*)CN(*)C1 0.000 description 20
- 239000003443 antiviral agent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361919235P | 2013-12-20 | 2013-12-20 | |
| US61/919,235 | 2013-12-20 | ||
| PCT/US2014/071617 WO2015095767A1 (en) | 2013-12-20 | 2014-12-19 | Heterocyclic modulators of lipid synthesis and combinations thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017505291A JP2017505291A (ja) | 2017-02-16 |
| JP2017505291A5 true JP2017505291A5 (enExample) | 2018-02-08 |
| JP6820097B2 JP6820097B2 (ja) | 2021-01-27 |
Family
ID=52302407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016541077A Active JP6820097B2 (ja) | 2013-12-20 | 2014-12-19 | 脂質合成の複素環式モジュレータ及びその組み合わせ |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10226449B2 (enExample) |
| EP (1) | EP3083583B1 (enExample) |
| JP (1) | JP6820097B2 (enExample) |
| KR (1) | KR20160100329A (enExample) |
| CN (1) | CN106061963B (enExample) |
| AU (1) | AU2014368945C1 (enExample) |
| CA (1) | CA2934251C (enExample) |
| ES (1) | ES2841137T3 (enExample) |
| WO (1) | WO2015095767A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170119786A1 (en) | 2011-03-08 | 2017-05-04 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| JP6109934B2 (ja) | 2012-07-03 | 2017-04-05 | 3−ブイ・バイオサイエンシーズ・インコーポレイテッド3−V Biosciences,Inc. | 脂質合成の複素環モジュレーター |
| JP6691909B2 (ja) * | 2014-08-15 | 2020-05-13 | サギメット バイオサイエンシーズ インコーポレイテッド | 薬物耐性癌の治療で用いるための脂肪酸シンターゼ阻害剤 |
| CA2979696A1 (en) | 2015-03-19 | 2016-09-22 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| UY36629A (es) | 2015-04-17 | 2016-11-30 | Abbvie Inc | Indazolonas como moduladores de la señalización de tnf |
| CA3043308A1 (en) * | 2016-11-11 | 2018-05-17 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| AU2018209164B2 (en) | 2017-01-17 | 2021-11-04 | Heparegenix Gmbh | Protein kinase inhibitors for promoting liver regeneration or reducing or preventing hepatocyte death |
| CN107163043A (zh) * | 2017-06-16 | 2017-09-15 | 上海毕得医药科技有限公司 | 一种吡唑并[1,5‑a]吡啶‑3‑羧酸酯衍生物的合成方法 |
| WO2019101511A1 (en) | 2017-11-23 | 2019-05-31 | Basf Se | Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi |
| CN109956973B (zh) * | 2017-12-25 | 2020-11-03 | 上海启甄环境科技有限公司 | 一种放射性同位素碳-14标记毒氟磷的合成方法 |
| CN109503575B (zh) * | 2018-12-20 | 2021-01-29 | 温州大学 | 无催化剂N-N偶联反应合成[1,2,3]三氮唑[1,5-a]吡啶类化合物的方法 |
| CN111592495A (zh) * | 2020-07-06 | 2020-08-28 | 上海启讯医药科技有限公司 | 一种2-正丁基-4-氯-5甲酰基咪唑的制备方法 |
| GB202213166D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
| CN116482278B (zh) * | 2023-05-06 | 2024-02-09 | 广州清瑞生物科技有限责任公司 | 一种用于检测阿昔洛韦的对照品的制备方法 |
| CN119080742A (zh) * | 2023-06-05 | 2024-12-06 | 甘莱制药有限公司 | 脂质合成的杂环调节剂的工业化制备 |
| WO2025080818A1 (en) * | 2023-10-10 | 2025-04-17 | Sagimet Biosciences Inc. | Combinations of fasn inhibitors and glp-1 agonists for liver diseases |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3625214A (en) | 1970-05-18 | 1971-12-07 | Alza Corp | Drug-delivery device |
| US4906474A (en) | 1983-03-22 | 1990-03-06 | Massachusetts Institute Of Technology | Bioerodible polyanhydrides for controlled drug delivery |
| US4789734A (en) | 1985-08-06 | 1988-12-06 | La Jolla Cancer Research Foundation | Vitronectin specific cell receptor derived from mammalian mesenchymal tissue |
| CH671155A5 (enExample) | 1986-08-18 | 1989-08-15 | Clinical Technologies Ass | |
| US5811128A (en) | 1986-10-24 | 1998-09-22 | Southern Research Institute | Method for oral or rectal delivery of microencapsulated vaccines and compositions therefor |
| US5075109A (en) | 1986-10-24 | 1991-12-24 | Southern Research Institute | Method of potentiating an immune response |
| US4897268A (en) | 1987-08-03 | 1990-01-30 | Southern Research Institute | Drug delivery system and method of making the same |
| JPH08505625A (ja) | 1993-01-11 | 1996-06-18 | ダナ−ファーバー キャンサー インスティチュート | 細胞毒性tリンパ球応答の誘導 |
| AU2004215428B2 (en) | 2003-02-26 | 2009-08-27 | Sugen LLC | Aminoheteroaryl compounds as protein kinase inhibitors |
| AU2006319247B2 (en) | 2005-12-01 | 2010-03-11 | F. Hoffmann-La Roche Ag | Heteroaryl substituted piperidine derivatives as L-CPT1 inhibitors |
| JP2010502731A (ja) | 2006-09-05 | 2010-01-28 | バイパー サイエンシズ,インコーポレイティド | Parp阻害剤による脂肪酸合成の阻害、及びその治療方法 |
| WO2008059214A1 (en) * | 2006-11-13 | 2008-05-22 | Astrazeneca Ab | Bisamlde derivatives and use thereof as fatty acid synthase inhibitors |
| TW200833663A (en) | 2006-12-21 | 2008-08-16 | Astrazeneca Ab | Therapeutic agents |
| TW200831092A (en) | 2006-12-21 | 2008-08-01 | Astrazeneca Ab | Therapeutic agents |
| WO2008075077A1 (en) | 2006-12-21 | 2008-06-26 | Astrazeneca Ab | Piperidine derivatives for the treatment of obesity |
| ES2524883T3 (es) | 2008-03-18 | 2014-12-15 | Merck Sharp & Dohme Corp. | 4-Hidroxipirimidina-5-carboxamidas sustituidas |
| US20110118262A1 (en) | 2008-07-08 | 2011-05-19 | Boehringer Ingelheim International Gmbh | Pyrrolidinyl and Piperidinyl Compounds Useful as NHE-1 Inhibitiors |
| JO3041B1 (ar) | 2008-07-25 | 2016-09-05 | Galapagos Nv | مركبات جديدة مفيدة لمعالجة الأمراض التنكسية والالتهابية |
| US8324250B2 (en) | 2009-03-19 | 2012-12-04 | Hoffmann-La Roche Inc. | Piperidine derivatives as NK3 receptor antagonists |
| WO2011102864A2 (en) | 2009-11-19 | 2011-08-25 | University Of Pittsburgh -- Of The Commonwealth System Of Higher Education | On-demand nanoelectronics platform |
| US8633183B2 (en) | 2010-01-26 | 2014-01-21 | Boehringer Ingelheim International Gmbh | 5-alkynyl-pyrimidines |
| US8871790B2 (en) * | 2011-03-08 | 2014-10-28 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| HUE032459T2 (en) | 2011-03-08 | 2017-09-28 | 3-V Biosciences Inc | Heterocyclic modulators of lipid synthesis |
| US8604016B2 (en) * | 2011-11-21 | 2013-12-10 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| JP6109934B2 (ja) * | 2012-07-03 | 2017-04-05 | 3−ブイ・バイオサイエンシーズ・インコーポレイテッド3−V Biosciences,Inc. | 脂質合成の複素環モジュレーター |
-
2014
- 2014-12-19 ES ES14825066T patent/ES2841137T3/es active Active
- 2014-12-19 CA CA2934251A patent/CA2934251C/en active Active
- 2014-12-19 AU AU2014368945A patent/AU2014368945C1/en active Active
- 2014-12-19 US US15/106,539 patent/US10226449B2/en active Active
- 2014-12-19 CN CN201480075661.9A patent/CN106061963B/zh active Active
- 2014-12-19 KR KR1020167018773A patent/KR20160100329A/ko not_active Ceased
- 2014-12-19 JP JP2016541077A patent/JP6820097B2/ja active Active
- 2014-12-19 EP EP14825066.5A patent/EP3083583B1/en active Active
- 2014-12-19 WO PCT/US2014/071617 patent/WO2015095767A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017505291A5 (enExample) | ||
| JP2015522036A5 (enExample) | ||
| JP2018508547A5 (enExample) | ||
| JP2016517417A5 (enExample) | ||
| JP2011525171A5 (enExample) | ||
| JP2015535277A5 (enExample) | ||
| JP2019500387A5 (enExample) | ||
| JP2014520898A5 (enExample) | ||
| RU2016127634A (ru) | Гетероциклические модуляторы синтеза липидов для применения против рака и вирусных инфекций | |
| JP2013544860A5 (enExample) | ||
| JP2016525135A5 (enExample) | ||
| JP2010536887A5 (enExample) | ||
| JP2018516917A5 (enExample) | ||
| JP2014508811A5 (enExample) | ||
| JP2003531103A5 (enExample) | ||
| JP2016530259A5 (enExample) | ||
| RU2009132512A (ru) | Аналоги 2-5а и способы их применения | |
| JP2012530713A5 (enExample) | ||
| JP2021500394A5 (enExample) | ||
| JP2013537203A5 (enExample) | ||
| JP2019505529A5 (enExample) | ||
| AR094262A1 (es) | Compuestos antivirales para el tratamiento de la hepatitis c | |
| JP2010518128A5 (enExample) | ||
| JP2009504772A5 (enExample) | ||
| JP2008503591A5 (enExample) |