KR20120115290A - 트리아졸로피리딘 - Google Patents

Info

Publication number

KR20120115290A

KR20120115290A KR1020127016940A KR20127016940A KR20120115290A KR 20120115290 A KR20120115290 A KR 20120115290A KR 1020127016940 A KR1020127016940 A KR 1020127016940A KR 20127016940 A KR20127016940 A KR 20127016940A KR 20120115290 A KR20120115290 A KR 20120115290A

Authority

KR

South Korea

Prior art keywords

alkyl

alkoxy

halo

phenyl

amino

Prior art date

2009-11-30

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.)

Ceased

Links

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• 150000008523 triazolopyridines Chemical class 0.000 title description 3
• -1 triazolopyridine compound Chemical class 0.000 claims abstract description 386
• 150000001875 compounds Chemical class 0.000 claims abstract description 254
• 238000000034 method Methods 0.000 claims abstract description 85
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 55
• 238000002360 preparation method Methods 0.000 claims abstract description 52
• 238000011282 treatment Methods 0.000 claims abstract description 35
• 201000010099 disease Diseases 0.000 claims abstract description 33
• 230000002265 prevention Effects 0.000 claims abstract description 11
• 239000000203 mixture Substances 0.000 claims description 155
• 150000003839 salts Chemical class 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 57
• 125000005843 halogen group Chemical group 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 50
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 49
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
• 206010028980 Neoplasm Diseases 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 239000012453 solvate Substances 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 238000005859 coupling reaction Methods 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
• 150000001204 N-oxides Chemical class 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
• 230000024932 T cell mediated immunity Effects 0.000 claims description 16
• 230000004663 cell proliferation Effects 0.000 claims description 16
• 230000001413 cellular effect Effects 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 150000004677 hydrates Chemical class 0.000 claims description 16
• 230000028709 inflammatory response Effects 0.000 claims description 16
• 230000004083 survival effect Effects 0.000 claims description 16
• 206010027476 Metastases Diseases 0.000 claims description 14
• 230000010261 cell growth Effects 0.000 claims description 14
• 230000002074 deregulated effect Effects 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
• 150000001408 amides Chemical class 0.000 claims description 9
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000000524 functional group Chemical group 0.000 claims description 7
• 208000032839 leukemia Diseases 0.000 claims description 7
• 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 6
• 206010025323 Lymphomas Diseases 0.000 claims description 6
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 6
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 6
• 150000001502 aryl halides Chemical class 0.000 claims description 6
• 210000000481 breast Anatomy 0.000 claims description 6
• 230000008878 coupling Effects 0.000 claims description 6
• 238000010168 coupling process Methods 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 229960001592 paclitaxel Drugs 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 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 6
• 208000002699 Digestive System Neoplasms Diseases 0.000 claims description 5
• 208000009849 Female Genital Neoplasms Diseases 0.000 claims description 5
• 229930012538 Paclitaxel Natural products 0.000 claims description 5
• 239000004202 carbamide Substances 0.000 claims description 5
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 5
• 210000003734 kidney Anatomy 0.000 claims description 5
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• 230000001404 mediated effect Effects 0.000 claims description 5
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• 210000003932 urinary bladder Anatomy 0.000 claims description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 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 4
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
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• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 4
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 4
• 206010029098 Neoplasm skin Diseases 0.000 claims description 4
• 210000000038 chest Anatomy 0.000 claims description 4
• 229960002949 fluorouracil Drugs 0.000 claims description 4
• 201000005787 hematologic cancer Diseases 0.000 claims description 4
• 229960004641 rituximab Drugs 0.000 claims description 4
• 201000004477 skin sarcoma Diseases 0.000 claims description 4
• WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 3
• 108010006654 Bleomycin Proteins 0.000 claims description 3
• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 3
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 229960004630 chlorambucil Drugs 0.000 claims description 3
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 3
• 229960004316 cisplatin Drugs 0.000 claims description 3
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 3
• 229960004397 cyclophosphamide Drugs 0.000 claims description 3
• 229960000684 cytarabine Drugs 0.000 claims description 3
• 229960003668 docetaxel Drugs 0.000 claims description 3
• 229960005420 etoposide Drugs 0.000 claims description 3
• 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 3
• 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 3
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 3
• 229960001101 ifosfamide Drugs 0.000 claims description 3
• 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 3
• 229960001924 melphalan Drugs 0.000 claims description 3
• 229960000485 methotrexate Drugs 0.000 claims description 3
• 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 3
• 229960001156 mitoxantrone Drugs 0.000 claims description 3
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims description 3
• 229960000624 procarbazine Drugs 0.000 claims description 3
• MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims description 3
• 229960003087 tioguanine Drugs 0.000 claims description 3
• 229960003048 vinblastine Drugs 0.000 claims description 3
• 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 3
• 229960004528 vincristine Drugs 0.000 claims description 3
• 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 3
• FBSMWGUBAZFGFU-UHFFFAOYSA-N 1-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-3-phenylurea Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)NC=4C=CC=CC=4)C=CC=3)C=CC2=N1 FBSMWGUBAZFGFU-UHFFFAOYSA-N 0.000 claims description 2
• BYOWPAFNUFYUGB-UHFFFAOYSA-N 1-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)NC=4C=NC=CC=4)C=CC=3)C=CC2=N1 BYOWPAFNUFYUGB-UHFFFAOYSA-N 0.000 claims description 2
• GMSHWFIJJKGZLZ-UHFFFAOYSA-N 1-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-3-pyridin-4-ylurea Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)NC=4C=CN=CC=4)C=CC=3)C=CC2=N1 GMSHWFIJJKGZLZ-UHFFFAOYSA-N 0.000 claims description 2
• IYKHSNHPHQJOJT-UHFFFAOYSA-N 1-[4-[2-(2-cyanoanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-3-phenylurea Chemical compound C=1C=C(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)C=CC=1NC(=O)NC1=CC=CC=C1 IYKHSNHPHQJOJT-UHFFFAOYSA-N 0.000 claims description 2
• WCUJJQNTRQICDW-UHFFFAOYSA-N 1-cyclopropyl-3-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]urea Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)NC4CC4)C=CC=3)C=CC2=N1 WCUJJQNTRQICDW-UHFFFAOYSA-N 0.000 claims description 2
• VJYWUMCIEQFWOZ-UHFFFAOYSA-N 2-[[6-[3-(4-methylpiperazine-1-carbonyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino]benzonitrile Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)=C1 VJYWUMCIEQFWOZ-UHFFFAOYSA-N 0.000 claims description 2
• GINCZLFUPXTESW-UHFFFAOYSA-N 3-[2-(2-cyanoanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-n-cyclopentylbenzamide Chemical compound C=1C=CC(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)=CC=1C(=O)NC1CCCC1 GINCZLFUPXTESW-UHFFFAOYSA-N 0.000 claims description 2
• KGCRBQXVXUNBQF-UHFFFAOYSA-N 3-[2-(2-cyanoanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-n-cyclopropylbenzamide Chemical compound C=1C=CC(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)=CC=1C(=O)NC1CC1 KGCRBQXVXUNBQF-UHFFFAOYSA-N 0.000 claims description 2
• JLQWZDIDJPSXDW-UHFFFAOYSA-N 3-[2-(2-cyanoanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]-n-phenylbenzamide Chemical compound C=1C=CC(C2=CN3N=C(NC=4C(=CC=CC=4)C#N)N=C3C=C2)=CC=1C(=O)NC1=CC=CC=C1 JLQWZDIDJPSXDW-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 2
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-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
• 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
• 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
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 2
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• UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims description 2
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• MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 claims description 2
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• FABUFPQFXZVHFB-CFWQTKTJSA-N ixabepilone Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C)C(=O)C(C)(C)[C@H](O)CC(=O)N1)O)C)=C\C1=CSC(C)=N1 FABUFPQFXZVHFB-CFWQTKTJSA-N 0.000 claims description 2
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• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• WJOFMPVOYLCLSY-UHFFFAOYSA-N n-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-2-phenylacetamide Chemical compound COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)CC=4C=CC=CC=4)C=CC=3)C=CC2=N1 WJOFMPVOYLCLSY-UHFFFAOYSA-N 0.000 claims description 2
• VDAJUIKUYIEJFL-UHFFFAOYSA-N n-[3-[2-(2-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyridin-6-yl]phenyl]-4-methylpiperazine-1-carboxamide Chemical class COC1=CC=CC=C1NC1=NN2C=C(C=3C=C(NC(=O)N4CCN(C)CC4)C=CC=3)C=CC2=N1 VDAJUIKUYIEJFL-UHFFFAOYSA-N 0.000 claims description 2
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