JP2016529311A5 - - Google Patents
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- JP2016529311A5 JP2016529311A5 JP2016540386A JP2016540386A JP2016529311A5 JP 2016529311 A5 JP2016529311 A5 JP 2016529311A5 JP 2016540386 A JP2016540386 A JP 2016540386A JP 2016540386 A JP2016540386 A JP 2016540386A JP 2016529311 A5 JP2016529311 A5 JP 2016529311A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- oxo
- cycloalkyl
- propyl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 175
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 75
- 150000002367 halogens Chemical class 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 125000005843 halogen group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- -1 pyridine compound Chemical class 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- YIUSVSPYCXFTHR-UHFFFAOYSA-N 2-[2-ethoxy-5-[4-[3-[4-(2-fluorophenyl)-5-oxo-1-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-yl]propyl]phenyl]phenyl]acetic acid Chemical compound C1=C(CC(O)=O)C(OCC)=CC=C1C(C=C1)=CC=C1CCCC(N(C1=O)C=2C(=CC=CC=2)F)=NN1C1=CC=C(C(F)(F)F)C=C1 YIUSVSPYCXFTHR-UHFFFAOYSA-N 0.000 claims description 3
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- XENNSGUFERGIAR-UHFFFAOYSA-N C1=CC=C(C(=C1)N2C=NN(C2=O)C3=CC=C(C=C3)C(F)(F)F)Cl Chemical compound C1=CC=C(C(=C1)N2C=NN(C2=O)C3=CC=C(C=C3)C(F)(F)F)Cl XENNSGUFERGIAR-UHFFFAOYSA-N 0.000 claims description 3
- LDKNDIYPSQASAC-UHFFFAOYSA-N C1=CC=C(C=C1)N2C=NN(C2=O)C3=CC=C(C=C3)C(F)(F)F Chemical compound C1=CC=C(C=C1)N2C=NN(C2=O)C3=CC=C(C=C3)C(F)(F)F LDKNDIYPSQASAC-UHFFFAOYSA-N 0.000 claims description 3
- AOLVMEKBTUBAKM-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccc(cc2)C(F)(F)F)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccc(cc2)C(F)(F)F)cc1 AOLVMEKBTUBAKM-UHFFFAOYSA-N 0.000 claims description 3
- RNRVJDZNWLTZIL-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2cccc(F)c2)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2cccc(F)c2)cc1 RNRVJDZNWLTZIL-UHFFFAOYSA-N 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- KZEHHKVRXLRSMJ-UHFFFAOYSA-N FC1=C(C=C(C=C1)F)N1C(=NN(C1=O)C1=CC=C(C=C1)C(F)(F)F)CCCC1=CC=C(C=C1)C1=CC(=C(C=C1)OCC)CC(=O)O Chemical compound FC1=C(C=C(C=C1)F)N1C(=NN(C1=O)C1=CC=C(C=C1)C(F)(F)F)CCCC1=CC=C(C=C1)C1=CC(=C(C=C1)OCC)CC(=O)O KZEHHKVRXLRSMJ-UHFFFAOYSA-N 0.000 claims description 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 206010038389 Renal cancer Diseases 0.000 claims description 3
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 201000010982 kidney cancer Diseases 0.000 claims description 3
- 201000007270 liver cancer Diseases 0.000 claims description 3
- 208000014018 liver neoplasm Diseases 0.000 claims description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 230000004060 metabolic process Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- QVUBGEROTOSOJC-UHFFFAOYSA-N 4-propan-2-yl-2-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-one Chemical compound CC(C)N1C=NN(C1=O)C2=CC=C(C=C2)C(F)(F)F QVUBGEROTOSOJC-UHFFFAOYSA-N 0.000 claims description 2
- MNYYQFBWONVQBE-UHFFFAOYSA-N 4-propyl-2-[4-(trifluoromethyl)phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N(CCC)C=NN1C1=CC=C(C(F)(F)F)C=C1 MNYYQFBWONVQBE-UHFFFAOYSA-N 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
- NJECQQYHTLEGIL-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=C(C=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)F)=O)C1=CC=C(C=C1)C(F)(F)F)C)C(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=C(C=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)F)=O)C1=CC=C(C=C1)C(F)(F)F)C)C(=O)O NJECQQYHTLEGIL-UHFFFAOYSA-N 0.000 claims description 2
- UATGOEFSRWFOAS-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=C(C=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)F)=O)C1=CC=C(C=C1)C(F)(F)F)C)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=C(C=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)F)=O)C1=CC=C(C=C1)C(F)(F)F)C)CC(=O)O UATGOEFSRWFOAS-UHFFFAOYSA-N 0.000 claims description 2
- PMJJNGWFMFAJEW-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)CC)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)CC)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O PMJJNGWFMFAJEW-UHFFFAOYSA-N 0.000 claims description 2
- YHNQWDMZRVJOSA-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)F)=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)F)=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)O YHNQWDMZRVJOSA-UHFFFAOYSA-N 0.000 claims description 2
- WNZRKSQCSOZRSN-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)OC)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1=C(C=CC=C1)OC)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O WNZRKSQCSOZRSN-UHFFFAOYSA-N 0.000 claims description 2
- AZZDDOPPVYASAB-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1=NC=CC=C1)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1=NC=CC=C1)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O AZZDDOPPVYASAB-UHFFFAOYSA-N 0.000 claims description 2
- XNFBODXREMLBRJ-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1C(CCCC1)C)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1C(CCCC1)C)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O XNFBODXREMLBRJ-UHFFFAOYSA-N 0.000 claims description 2
- SKQGOHHRDDPTLU-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1CC(CCC1)C)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1CC(CCC1)C)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O SKQGOHHRDDPTLU-UHFFFAOYSA-N 0.000 claims description 2
- DTUFKZIBYVBNOE-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1CCC(CC1)C)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C1CCC(CC1)C)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O DTUFKZIBYVBNOE-UHFFFAOYSA-N 0.000 claims description 2
- FPWFNQRLZHTUKG-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1CC1=C(C=CC=C1)F)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1CC1=C(C=CC=C1)F)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O FPWFNQRLZHTUKG-UHFFFAOYSA-N 0.000 claims description 2
- KLYGHILRINOIBL-UHFFFAOYSA-N CC(C)CN1C=NN(C1=O)C2=CC=C(C=C2)C(F)(F)F Chemical compound CC(C)CN1C=NN(C1=O)C2=CC=C(C=C2)C(F)(F)F KLYGHILRINOIBL-UHFFFAOYSA-N 0.000 claims description 2
- PTDNOZGYAIQXNG-UHFFFAOYSA-N CCCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2F)cc1 Chemical compound CCCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2F)cc1 PTDNOZGYAIQXNG-UHFFFAOYSA-N 0.000 claims description 2
- YINVWPZUDREAHC-UHFFFAOYSA-N CCCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2C2CC2)cc1 Chemical compound CCCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2C2CC2)cc1 YINVWPZUDREAHC-UHFFFAOYSA-N 0.000 claims description 2
- YVKXDAJDYDLGBC-UHFFFAOYSA-N CCN1C=NN(C1=O)C2=CC=C(C=C2)C(F)(F)F Chemical compound CCN1C=NN(C1=O)C2=CC=C(C=C2)C(F)(F)F YVKXDAJDYDLGBC-UHFFFAOYSA-N 0.000 claims description 2
- ZNWNTTKJQUBCKA-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2c(F)cccc2F)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2c(F)cccc2F)cc1 ZNWNTTKJQUBCKA-UHFFFAOYSA-N 0.000 claims description 2
- ZDNWKSHBSTTYNI-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccc(cc2)C(C)(C)C)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccc(cc2)C(C)(C)C)cc1 ZDNWKSHBSTTYNI-UHFFFAOYSA-N 0.000 claims description 2
- GVOZDCQZMCBVAH-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2C(F)(F)F)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2C(F)(F)F)cc1 GVOZDCQZMCBVAH-UHFFFAOYSA-N 0.000 claims description 2
- FAPMCFBRELDXBS-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2C)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2C)cc1 FAPMCFBRELDXBS-UHFFFAOYSA-N 0.000 claims description 2
- JYYASSFNFYOHEH-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3Cl)C(F)(F)F)c(=O)n2-c2ccccc2F)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3Cl)C(F)(F)F)c(=O)n2-c2ccccc2F)cc1 JYYASSFNFYOHEH-UHFFFAOYSA-N 0.000 claims description 2
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- JUIMPRHBFTZNNF-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccccc3F)c(=O)n2-c2ccc(cc2)C(F)(F)F)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccccc3F)c(=O)n2-c2ccc(cc2)C(F)(F)F)cc1 JUIMPRHBFTZNNF-UHFFFAOYSA-N 0.000 claims description 2
- HBPHOKINZBKNPZ-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1cccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2F)c1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1cccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2F)c1 HBPHOKINZBKNPZ-UHFFFAOYSA-N 0.000 claims description 2
- ZRNRJWHAYPIKHX-UHFFFAOYSA-N COc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2C2CC2)cc1 Chemical compound COc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2C2CC2)cc1 ZRNRJWHAYPIKHX-UHFFFAOYSA-N 0.000 claims description 2
- GTICRFCPWZJBJF-UHFFFAOYSA-N COc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2Cc2ccccc2F)cc1 Chemical compound COc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2Cc2ccccc2F)cc1 GTICRFCPWZJBJF-UHFFFAOYSA-N 0.000 claims description 2
- 230000003247 decreasing effect Effects 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 241000711549 Hepacivirus C Species 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
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- KXHPLSHTOABRTL-UHFFFAOYSA-N C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C=1C=NC=CC=1)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC=C(C=C1)CCCC1=NN(C(N1C=1C=NC=CC=1)=O)C1=CC=C(C=C1)C(F)(F)F)CC(=O)O KXHPLSHTOABRTL-UHFFFAOYSA-N 0.000 description 1
- DCYYUFVXDNUMPU-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2C2CCCCC2)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CCCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2C2CCCCC2)cc1 DCYYUFVXDNUMPU-UHFFFAOYSA-N 0.000 description 1
- HLGXVKJEZYZGHX-UHFFFAOYSA-N CCOc1ccc(cc1CC(O)=O)-c1ccc(CNCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2F)cc1 Chemical compound CCOc1ccc(cc1CC(O)=O)-c1ccc(CNCc2nn(-c3ccc(cc3)C(F)(F)F)c(=O)n2-c2ccccc2F)cc1 HLGXVKJEZYZGHX-UHFFFAOYSA-N 0.000 description 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361874956P | 2013-09-06 | 2013-09-06 | |
| US61/874,956 | 2013-09-06 | ||
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| EP2616071A2 (en) | 2010-09-17 | 2013-07-24 | GlaxoSmithKline Intellectual Property Development Limited | Fatty acid synthase inhibitors |
| JP5847533B2 (ja) | 2010-10-19 | 2016-01-27 | 田辺三菱製薬株式会社 | 新規甲状腺ホルモンβ受容体作動薬 |
| WO2012058531A2 (en) | 2010-10-29 | 2012-05-03 | North Carolina State University | Modulation of response regulators by imidazole derivatives |
| WO2013134562A1 (en) * | 2012-03-09 | 2013-09-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| MX376108B (es) * | 2012-12-20 | 2025-03-07 | Tempest Therapeutics Inc | Compuestos de triazolona y usos de los mismos. |
-
2014
- 2014-09-04 KR KR1020167008627A patent/KR20160048988A/ko not_active Withdrawn
- 2014-09-04 JP JP2016540386A patent/JP2016529311A/ja active Pending
- 2014-09-04 US US14/916,860 patent/US9776976B2/en not_active Expired - Fee Related
- 2014-09-04 EA EA201690230A patent/EA201690230A1/ru unknown
- 2014-09-04 MX MX2016002795A patent/MX2016002795A/es unknown
- 2014-09-04 AU AU2014315151A patent/AU2014315151A1/en not_active Abandoned
- 2014-09-04 WO PCT/US2014/054108 patent/WO2015035059A1/en not_active Ceased
- 2014-09-04 CA CA2921420A patent/CA2921420A1/en not_active Abandoned
- 2014-09-04 CN CN201480048882.7A patent/CN105579440A/zh active Pending
- 2014-09-04 SG SG11201601066VA patent/SG11201601066VA/en unknown
- 2014-09-04 EP EP14842357.7A patent/EP3041826A4/en not_active Withdrawn
- 2014-09-04 PE PE2016000323A patent/PE20160880A1/es not_active Application Discontinuation
-
2016
- 2016-03-02 IL IL244383A patent/IL244383A0/en unknown
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