JP2010500993A5 - - Google Patents
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- Publication number
- JP2010500993A5 JP2010500993A5 JP2009524665A JP2009524665A JP2010500993A5 JP 2010500993 A5 JP2010500993 A5 JP 2010500993A5 JP 2009524665 A JP2009524665 A JP 2009524665A JP 2009524665 A JP2009524665 A JP 2009524665A JP 2010500993 A5 JP2010500993 A5 JP 2010500993A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- triazole
- mercapto
- phenyl
- dihydroxy
- 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
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- -1 guanazino Chemical group 0.000 claims description 156
- 125000001072 heteroaryl group Chemical group 0.000 claims description 84
- 125000000623 heterocyclic group Chemical group 0.000 claims description 70
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 68
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 62
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 56
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 56
- 125000003107 substituted aryl group Chemical group 0.000 claims description 56
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 53
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 125000001188 haloalkyl group Chemical group 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000001475 halogen functional group Chemical group 0.000 claims description 36
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 230000017531 blood circulation Effects 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- ZAVMYGRJGRTKNS-UHFFFAOYSA-N 4-(1,2-dimethylindol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=C(C)N(C)C3=CC=2)=C1O ZAVMYGRJGRTKNS-UHFFFAOYSA-N 0.000 claims description 6
- RHAYKNNJVHVROS-UHFFFAOYSA-N 4-[5-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C=3OCCOC=3C=CC=2)=C(S)N=N1 RHAYKNNJVHVROS-UHFFFAOYSA-N 0.000 claims description 6
- QDVZGIRSUDZLCA-UHFFFAOYSA-N 4-[5-(2,6-dimethylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC=CC(C)=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O QDVZGIRSUDZLCA-UHFFFAOYSA-N 0.000 claims description 6
- GPNWYLMMEXOXCR-UHFFFAOYSA-N 4-[5-(5-methoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=CC=C2C(OC)=CC=CC2=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O GPNWYLMMEXOXCR-UHFFFAOYSA-N 0.000 claims description 6
- LDFCAQGPDVBWHQ-UHFFFAOYSA-N 4-ethyl-6-[5-(1-ethylbenzimidazol-4-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C=3N=CN(CC)C=3C=CC=2)=C1O LDFCAQGPDVBWHQ-UHFFFAOYSA-N 0.000 claims description 6
- PCWPLZYTBMDRLQ-UHFFFAOYSA-N 5-amino-2-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)phenol Chemical compound OC1=CC(N)=CC=C1N1C(C=2C3=CC=CC=C3C=CC=2)=C(S)N=N1 PCWPLZYTBMDRLQ-UHFFFAOYSA-N 0.000 claims description 6
- PJSPUHPGJHMUDP-UHFFFAOYSA-N 5-methoxy-2-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)phenol Chemical compound OC1=CC(OC)=CC=C1N1C(C=2C3=CC=CC=C3C=CC=2)=C(S)N=N1 PJSPUHPGJHMUDP-UHFFFAOYSA-N 0.000 claims description 6
- XJNHHOSTXIXKSG-UHFFFAOYSA-N n-[3-hydroxy-4-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)phenyl]acetamide Chemical compound OC1=CC(NC(=O)C)=CC=C1N1C(C=2C3=CC=CC=C3C=CC=2)=C(S)N=N1 XJNHHOSTXIXKSG-UHFFFAOYSA-N 0.000 claims description 6
- DTXOCJGLLMAFBX-UHFFFAOYSA-N oxo-[[1-[2-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]ethoxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCCOCN1C=CC(=C[NH+]=O)C=C1 DTXOCJGLLMAFBX-UHFFFAOYSA-N 0.000 claims description 6
- 230000033115 angiogenesis Effects 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 230000001603 reducing effect Effects 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- SYTBMCIDAYQZAC-UHFFFAOYSA-N 1-(2,4-dihydroxy-5-methoxyphenyl)-4-(sulfamoylamino)-5-[3-(trifluoromethyl)phenyl]triazole Chemical compound C1=C(O)C(OC)=CC(N2C(=C(NS(N)(=O)=O)N=N2)C=2C=C(C=CC=2)C(F)(F)F)=C1O SYTBMCIDAYQZAC-UHFFFAOYSA-N 0.000 claims description 3
- ZBQGGNRZZXNKRJ-UHFFFAOYSA-N 1-(2,4-dihydroxy-5-methoxyphenyl)-5-naphthalen-1-yl-4-(sulfamoylamino)triazole Chemical compound C1=C(O)C(OC)=CC(N2C(=C(NS(N)(=O)=O)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O ZBQGGNRZZXNKRJ-UHFFFAOYSA-N 0.000 claims description 3
- FNIXUOSHBLGHJQ-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-5-phenyl-4-(sulfamoylamino)triazole Chemical compound NS(=O)(=O)NC=1N=NN(C=2C(=CC(O)=CC=2)O)C=1C1=CC=CC=C1 FNIXUOSHBLGHJQ-UHFFFAOYSA-N 0.000 claims description 3
- RYQIKRMARWEKEE-UHFFFAOYSA-N 1-(2-hydroxy-5-propan-2-ylphenyl)-5-naphthalen-1-yltriazol-4-ol Chemical compound CC(C)C1=CC=C(O)C(N2C(=C(O)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1 RYQIKRMARWEKEE-UHFFFAOYSA-N 0.000 claims description 3
- XDVUMDGLIFBVKT-UHFFFAOYSA-N 1-(5-ethoxy-2-hydroxyphenyl)-5-naphthalen-1-yltriazol-4-ol Chemical compound CCOC1=CC=C(O)C(N2C(=C(O)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1 XDVUMDGLIFBVKT-UHFFFAOYSA-N 0.000 claims description 3
- PCKARBFVTAHKLL-UHFFFAOYSA-N 1-[5-[3-(5-ethyl-2,4-dihydroxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-2,3-dimethylindol-1-yl]ethanone Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=C(C)N(C(C)=O)C3=CC=2)=C1O PCKARBFVTAHKLL-UHFFFAOYSA-N 0.000 claims description 3
- CDZAJNIMEUBWQV-UHFFFAOYSA-N 1-ethyl-3-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)-2h-pyridine-4,6-diol Chemical compound C1=C(O)N(CC)CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O CDZAJNIMEUBWQV-UHFFFAOYSA-N 0.000 claims description 3
- OJGHDSTXSCTGQW-UHFFFAOYSA-N 1-methyl-3-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)-2h-pyridine-4,6-diol Chemical compound C1=C(O)N(C)CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O OJGHDSTXSCTGQW-UHFFFAOYSA-N 0.000 claims description 3
- YKUMZHGVARQMOZ-UHFFFAOYSA-N 2,5-dimethyl-4-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound CC1=CC(O)=C(C)C(O)=C1N1C(C=2C3=CC=CC=C3C=CC=2)=C(S)N=N1 YKUMZHGVARQMOZ-UHFFFAOYSA-N 0.000 claims description 3
- FBZZGYMSYBBAKH-UHFFFAOYSA-N 2-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)phenol Chemical compound OC1=CC=CC=C1N1C(C=2C3=CC=CC=C3C=CC=2)=C(S)N=N1 FBZZGYMSYBBAKH-UHFFFAOYSA-N 0.000 claims description 3
- GXECTKAVRLKCRG-UHFFFAOYSA-N 2-(hydroxymethyl)-5-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,4-diol Chemical compound C1=C(O)C(CO)=CC(O)=C1N1C(C=2C3=CC=CC=C3C=CC=2)=C(S)N=N1 GXECTKAVRLKCRG-UHFFFAOYSA-N 0.000 claims description 3
- BRGRHLDKJMLGSH-UHFFFAOYSA-N 2-[8-[3-(5-ethyl-2,4-dihydroxyphenyl)-5-sulfanyltriazol-4-yl]naphthalen-2-yl]oxyacetic acid Chemical compound C1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C3=CC(OCC(O)=O)=CC=C3C=CC=2)=C1O BRGRHLDKJMLGSH-UHFFFAOYSA-N 0.000 claims description 3
- VODMUHBBWURJBK-UHFFFAOYSA-N 2-chloro-4-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound OC1=C(Cl)C(O)=CC=C1N1C(C=2C3=CC=CC=C3C=CC=2)=C(S)N=N1 VODMUHBBWURJBK-UHFFFAOYSA-N 0.000 claims description 3
- DMERZNBHHPJRBH-UHFFFAOYSA-N 2-chloro-4-ethyl-6-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)benzene-1,3-diol Chemical compound ClC1=C(O)C(CC)=CC(N2C(=C(S)N=N2)C=2C3=CC=CC=C3C=CC=2)=C1O DMERZNBHHPJRBH-UHFFFAOYSA-N 0.000 claims description 3
- MXKIFFBZWXCSSS-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1,3-dimethylindol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O MXKIFFBZWXCSSS-UHFFFAOYSA-N 0.000 claims description 3
- UBYWHLVHDACFMM-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1,3-dimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O UBYWHLVHDACFMM-UHFFFAOYSA-N 0.000 claims description 3
- LIRCZXORVKKVOJ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-ethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(CC)C=CC2=CC=1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O LIRCZXORVKKVOJ-UHFFFAOYSA-N 0.000 claims description 3
- AWBAVFLOUGHJRJ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=3C=CN(C=3C=CC=2)C(C)C)=C1O AWBAVFLOUGHJRJ-UHFFFAOYSA-N 0.000 claims description 3
- STVGXJKUWLHOGD-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-propylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(CCC)C=CC2=CC=1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O STVGXJKUWLHOGD-UHFFFAOYSA-N 0.000 claims description 3
- BTGVBRHYZUAKCR-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1H-indol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3C=CNC3=CC=2)=C1O BTGVBRHYZUAKCR-UHFFFAOYSA-N 0.000 claims description 3
- NDPQZXRORWTRAB-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=2C=CN(C(C)C)C=2C(OC)=CC=C1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O NDPQZXRORWTRAB-UHFFFAOYSA-N 0.000 claims description 3
- UIVTZISQSMHJKS-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1-ethylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CC)C=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O UIVTZISQSMHJKS-UHFFFAOYSA-N 0.000 claims description 3
- RKFOLXISFIXXRI-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(C(C)C)C=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O RKFOLXISFIXXRI-UHFFFAOYSA-N 0.000 claims description 3
- UBBWIIUNTKWYMN-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1H-indol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound OC1=CC(O)=CC=C1C1=NN=C(S)N1C1=CC=CC2=C1C=CN2 UBBWIIUNTKWYMN-UHFFFAOYSA-N 0.000 claims description 3
- LQKKAHUTPJMJET-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-[2-(1-methoxyethyl)-1H-indol-4-yl]-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2NC(C(C)OC)=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O LQKKAHUTPJMJET-UHFFFAOYSA-N 0.000 claims description 3
- HVFFXYJWYZFIBV-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(1,2,3-trimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(C)C(C)=C(C)C2=CC=1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 HVFFXYJWYZFIBV-UHFFFAOYSA-N 0.000 claims description 3
- QFROSIGFOALPEM-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(1,3-dimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2C(C)=CN(C)C2=CC=C1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 QFROSIGFOALPEM-UHFFFAOYSA-N 0.000 claims description 3
- CXYAPZNVLMXJNT-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(C)C=CC2=CC=1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 CXYAPZNVLMXJNT-UHFFFAOYSA-N 0.000 claims description 3
- REUUXTDHNKRGOI-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=2C=CN(C(C)C)C=2C(OC)=CC=C1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 REUUXTDHNKRGOI-UHFFFAOYSA-N 0.000 claims description 3
- UATPOJPGMXSVGQ-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC(OC)=C2N(CCC)C=CC2=C1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 UATPOJPGMXSVGQ-UHFFFAOYSA-N 0.000 claims description 3
- STLUOXMEJVFZCP-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1,2,3-trimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=C(C)N(C)C3=CC=2)=C1O STLUOXMEJVFZCP-UHFFFAOYSA-N 0.000 claims description 3
- YUZVSLHCEHKSQJ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-hexylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCCCCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O YUZVSLHCEHKSQJ-UHFFFAOYSA-N 0.000 claims description 3
- INSPZFPAIAETMI-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O INSPZFPAIAETMI-UHFFFAOYSA-N 0.000 claims description 3
- OLLRLHGHUWXAFP-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-pentylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCCCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O OLLRLHGHUWXAFP-UHFFFAOYSA-N 0.000 claims description 3
- QZCQHJMGZJLICK-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C=CC=2)C(C)C)=C1O QZCQHJMGZJLICK-UHFFFAOYSA-N 0.000 claims description 3
- LBVJBJFVUWQRLE-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-propylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O LBVJBJFVUWQRLE-UHFFFAOYSA-N 0.000 claims description 3
- QSFLGQYOSRZJAQ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(3-ethyl-1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2C(CC)=CN(C)C2=CC=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O QSFLGQYOSRZJAQ-UHFFFAOYSA-N 0.000 claims description 3
- BXLIPBMFJHQUAZ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-hydroxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C(O)=CC=2)C(C)C)=C1O BXLIPBMFJHQUAZ-UHFFFAOYSA-N 0.000 claims description 3
- ZBXXGZDCLQEVEQ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C(OC)=CC=2)C(C)C)=C1O ZBXXGZDCLQEVEQ-UHFFFAOYSA-N 0.000 claims description 3
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- BORCHZNOBITQAC-UHFFFAOYSA-N 4-[5-(4-chloronaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1N1C(C=2C3=CC=CC=C3C(Cl)=CC=2)=C(S)N=N1 BORCHZNOBITQAC-UHFFFAOYSA-N 0.000 claims 1
- FPSHBUWKMHVLCF-UHFFFAOYSA-N [1-(2,4-dihydroxy-5-propan-2-ylphenyl)-5-(3-methylquinolin-5-yl)triazol-4-yl]carbamic acid Chemical compound C1=C(O)C(C(C)C)=CC(N2C(=C(NC(O)=O)N=N2)C=2C3=CC(C)=CN=C3C=CC=2)=C1O FPSHBUWKMHVLCF-UHFFFAOYSA-N 0.000 claims 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 description 105
- 229940002612 prodrug Drugs 0.000 description 15
- 239000000651 prodrug Substances 0.000 description 15
- 239000012453 solvate Substances 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 12
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- FMRNAECAMZWTOH-UHFFFAOYSA-N 4-(1-ethylbenzimidazol-4-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3N=CN(CC)C=3C=CC=2)=C1O FMRNAECAMZWTOH-UHFFFAOYSA-N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
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- 101001016865 Homo sapiens Heat shock protein HSP 90-alpha Proteins 0.000 description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
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- AHXQIXWOSLLMNU-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindazol-6-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3N(C)N=CC3=CC=2)=C1O AHXQIXWOSLLMNU-UHFFFAOYSA-N 0.000 description 2
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- JJGWYOSOCCDKJU-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[1-methyl-2-(trifluoromethyl)benzimidazol-5-yl]-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3N=C(N(C)C3=CC=2)C(F)(F)F)=C1O JJGWYOSOCCDKJU-UHFFFAOYSA-N 0.000 description 2
- FODKQXTYMMCSPC-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-ethyl-2-methylbenzimidazol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3N=C(C)N(CC)C3=CC=2)=C1O FODKQXTYMMCSPC-UHFFFAOYSA-N 0.000 description 2
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- NZZXFHSCKWJAQF-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(3-ethyl-2-methylbenzimidazol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3N(CC)C(C)=NC3=CC=2)=C1O NZZXFHSCKWJAQF-UHFFFAOYSA-N 0.000 description 2
- QYVIZOQFOBGAHW-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-methoxy-2-methyl-1-benzofuran-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=C(C)OC=3C(OC)=CC=2)=C1O QYVIZOQFOBGAHW-UHFFFAOYSA-N 0.000 description 2
- CXWAUYMEDCGIRL-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=COC3=CC=2)=C1O CXWAUYMEDCGIRL-UHFFFAOYSA-N 0.000 description 2
- UATJXGDPDCSCQW-UHFFFAOYSA-N 4-[5-(4-fluoro-2-methylphenyl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound CC1=CC(F)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O UATJXGDPDCSCQW-UHFFFAOYSA-N 0.000 description 2
- PQMIPBAOVWAVPP-UHFFFAOYSA-N 4-[5-(4-propoxynaphthalen-1-yl)-4-sulfanyltriazol-1-yl]benzene-1,3-diol Chemical compound C12=CC=CC=C2C(OCCC)=CC=C1C1=C(S)N=NN1C1=CC=C(O)C=C1O PQMIPBAOVWAVPP-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C)CC1=*=*=**1=*=**#C Chemical compound CC(C)CC1=*=*=**1=*=**#C 0.000 description 2
- LTBDTMUWZOTWTQ-UHFFFAOYSA-N [1-(5-ethyl-2,4-dihydroxyphenyl)-5-(1-methylindol-4-yl)triazol-4-yl] carbamate Chemical compound C1=C(O)C(CC)=CC(N2C(=C(OC(N)=O)N=N2)C=2C=3C=CN(C)C=3C=CC=2)=C1O LTBDTMUWZOTWTQ-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 210000003000 inclusion body Anatomy 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- AKVDFVRIPGIRTJ-UHFFFAOYSA-N 5-(methoxymethoxy)-2-(5-naphthalen-1-yl-4-sulfanyltriazol-1-yl)phenol Chemical compound OC1=C(C=CC(=C1)OCOC)N1N=NC(=C1C1=CC=CC2=CC=CC=C12)S AKVDFVRIPGIRTJ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003527 eukaryotic cell Anatomy 0.000 description 1
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| PCT/US2007/017996 WO2008021364A2 (en) | 2006-08-17 | 2007-08-14 | Triazole compounds that modulate hsp90 activity |
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| JP2010500993A JP2010500993A (ja) | 2010-01-14 |
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| WO2006055760A1 (en) | 2004-11-18 | 2006-05-26 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| JP5178515B2 (ja) | 2005-08-12 | 2013-04-10 | シンタ ファーマシューティカルズ コーポレーション | Ｈｓｐ９０活性を調節するピラゾール化合物 |
| WO2007094819A2 (en) | 2005-08-18 | 2007-08-23 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| US20070250391A1 (en) * | 2006-04-05 | 2007-10-25 | Prade Hendrik D | Merchandising system and method for food and non-food items for a meal kit |
| AU2007267843B2 (en) | 2006-05-25 | 2011-10-13 | Synta Pharmaceuticals Corp. | Method for treating proliferative disorders associated with protooncogene products |
| WO2007139960A2 (en) * | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Compounds that modulate hsp90 activity and methods for identifying same |
| EP2035396B1 (en) * | 2006-05-25 | 2014-05-14 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| CA2653222A1 (en) | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| EP2026797A2 (en) | 2006-05-25 | 2009-02-25 | Synta Pharmaceuticals Corporation | Method for treating non-hodgkin's lymphoma |
| US20110046125A1 (en) * | 2006-10-19 | 2011-02-24 | Synta Pharmaceuticals Corp. | Method for treating infections |
| US8299107B2 (en) * | 2007-02-08 | 2012-10-30 | Synta Pharmaceuticals Corporation | Triazole compounds that modulate HSP90 activity |
| WO2008153730A2 (en) * | 2007-05-25 | 2008-12-18 | Synta Pharmaceuticals Corp. | Method for treating proliferative disorders associated with mutations in c-met |
| LT5623B (lt) | 2008-04-30 | 2010-01-25 | Biotechnologijos Institutas, , | 5-aril-4-(5-pakeistieji 2,4-dihidroksifenil)-1,2,3-tiadiazolai kaip hsp90 šaperono slopikliai ir tarpiniai junginiai jiems gauti |
| US9156836B2 (en) * | 2008-05-16 | 2015-10-13 | Synta Pharmaceuticals Corp. | Tricyclic triazole compounds that modulate HSP90 activity |
| WO2009148599A1 (en) | 2008-06-04 | 2009-12-10 | Synta Pharmaceuticals Corp. | Pyrrole compunds that modulate hsp90 activity |
| US8648071B2 (en) | 2008-06-27 | 2014-02-11 | Synta Pharmaceuticals Corp. | Hydrazonamide compounds that modulate Hsp90 activity |
| ES2415234T3 (es) * | 2008-08-08 | 2013-07-24 | Synta Pharmaceuticals Corp. | Compuestos de triazol que modulan la actividad Hsp90 |
| US8106083B2 (en) | 2008-08-08 | 2012-01-31 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| AR077405A1 (es) | 2009-07-10 | 2011-08-24 | Sanofi Aventis | Derivados del indol inhibidores de hsp90, composiciones que los contienen y utilizacion de los mismos para el tratamiento del cancer |
| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
| EP2560641A2 (en) * | 2010-04-19 | 2013-02-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a vegf inhibitor |
| US9205086B2 (en) | 2010-04-19 | 2015-12-08 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a Hsp90 inhibitory compounds and a EGFR inhibitor |
| JP2014520808A (ja) | 2011-07-07 | 2014-08-25 | シンタ ファーマシューティカルズ コーポレーション | Ｈｓｐ９０阻害化合物を用いた癌の治療 |
| AU2012332424A1 (en) | 2011-11-02 | 2014-06-05 | Synta Pharmaceuticals Corp. | Combination therapy of Hsp90 inhibitors with platinum-containing agents |
| EP2773345A1 (en) | 2011-11-02 | 2014-09-10 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of hsp90 inhibitors with topoisomerase i inhibitors |
| WO2013074594A1 (en) | 2011-11-14 | 2013-05-23 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
| WO2013177241A1 (en) | 2012-05-22 | 2013-11-28 | Trustees Of Dartmouth College | Method for synthesizing cycloalkanyl(b}indoles, cycloalkanyl(b) benzofurans, cycloalkanyl(b)benzothiophenes, compounds and methods of use |
| JP6280546B2 (ja) | 2012-06-26 | 2018-02-14 | デル マー ファーマシューティカルズ | ジアンヒドロガラクチトール、ジアセチルジアンヒドロガラクチトール、ジブロモズルシトール、又はこれらの類似体若しくは誘導体を用いた、遺伝子多型又はａｈｉ１の調節不全若しくは変異を有する患者におけるチロシンキナーゼインヒビター抵抗性悪性腫瘍を処置するための方法 |
| EP2983674A4 (en) | 2013-04-08 | 2017-05-10 | Dennis M. Brown | Therapeutic benefit of suboptimally administered chemical compounds |
| DK3300500T3 (da) | 2015-05-20 | 2020-05-18 | Amgen Inc | Triazolagonister af apj-receptoren |
| WO2017192485A1 (en) | 2016-05-03 | 2017-11-09 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| US11020395B2 (en) | 2016-11-16 | 2021-06-01 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the APJ receptor |
| EP3541803B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| WO2018093579A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole phenyl compounds as agonists of the apj receptor |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| WO2018093576A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| US11149040B2 (en) | 2017-11-03 | 2021-10-19 | Amgen Inc. | Fused triazole agonists of the APJ receptor |
| WO2019213006A1 (en) | 2018-05-01 | 2019-11-07 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
| ES2974634T3 (es) | 2018-12-21 | 2024-06-28 | Celgene Corp | Inhibidores de tienopiridinas de RIPK2 |
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| WO2004089367A1 (en) * | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | Pharmaceutical use of substituted 1,2,4-triazoles |
| GB0315111D0 (en) | 2003-06-27 | 2003-07-30 | Cancer Rec Tech Ltd | Substituted 5-membered ring compounds and their use |
| US20060235034A1 (en) * | 2004-11-01 | 2006-10-19 | Nouri Neamati | Novel compounds for treatment of cancer and disorders associated with angiogenesis function |
| WO2006055760A1 (en) | 2004-11-18 | 2006-05-26 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| DE102005007304A1 (de) * | 2005-02-17 | 2006-08-24 | Merck Patent Gmbh | Triazolderivate |
| RU2007137133A (ru) * | 2005-03-09 | 2009-04-20 | Ниппон Каяку Кабусики Кайся (Jp) | Новый ингибитор hsp90 |
| WO2007094819A2 (en) | 2005-08-18 | 2007-08-23 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| DE102006023337A1 (de) * | 2006-05-18 | 2007-11-22 | Merck Patent Gmbh | Triazolderivate II |
| AU2007267843B2 (en) * | 2006-05-25 | 2011-10-13 | Synta Pharmaceuticals Corp. | Method for treating proliferative disorders associated with protooncogene products |
| EP2026797A2 (en) * | 2006-05-25 | 2009-02-25 | Synta Pharmaceuticals Corporation | Method for treating non-hodgkin's lymphoma |
| TW200806637A (en) * | 2006-05-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Synthesis of triazole compounds that modulate HSP90 activity |
| WO2007139960A2 (en) * | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Compounds that modulate hsp90 activity and methods for identifying same |
| EP2035396B1 (en) * | 2006-05-25 | 2014-05-14 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| CA2653222A1 (en) * | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
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- 2007-08-14 JP JP2009524665A patent/JP5480623B2/ja not_active Expired - Fee Related
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- 2007-08-14 US US12/310,150 patent/US8188075B2/en active Active
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