JP2009538321A5 - - Google Patents
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- JP2009538321A5 JP2009538321A5 JP2009512171A JP2009512171A JP2009538321A5 JP 2009538321 A5 JP2009538321 A5 JP 2009538321A5 JP 2009512171 A JP2009512171 A JP 2009512171A JP 2009512171 A JP2009512171 A JP 2009512171A JP 2009538321 A5 JP2009538321 A5 JP 2009538321A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- triazole
- hydroxy
- indol
- methyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 268
- 125000001072 heteroaryl group Chemical group 0.000 claims description 141
- 125000000623 heterocyclic group Chemical group 0.000 claims description 123
- 125000003107 substituted aryl group Chemical group 0.000 claims description 112
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 100
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 100
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 96
- -1 guanazino Chemical group 0.000 claims description 94
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 90
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 90
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 89
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 88
- 229910052757 nitrogen Inorganic materials 0.000 claims description 80
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 229940002612 prodrug Drugs 0.000 claims description 59
- 239000000651 prodrug Substances 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 59
- 239000012453 solvate Substances 0.000 claims description 58
- 125000001188 haloalkyl group Chemical group 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000002947 alkylene group Chemical group 0.000 claims description 32
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 32
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 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 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 7
- 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 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 230000014399 negative regulation of angiogenesis Effects 0.000 claims description 3
- AAUDDEVGIAWLCV-UHFFFAOYSA-N 2-(1h-1,2,4-triazol-5-ylsulfanyl)ethanol Chemical compound OCCSC=1N=CNN=1 AAUDDEVGIAWLCV-UHFFFAOYSA-N 0.000 claims description 2
- VSFBAMLPDZXWHL-UHFFFAOYSA-N 2-amino-2-[5-(1-amino-1-carboxyethyl)-2-[1-(2-aminopropanoyl)-4-(1-methylindol-5-yl)-5-oxo-1,2,4-triazol-3-yl]-4-propan-2-ylphenyl]propanoic acid;trihydrochloride Chemical compound Cl.Cl.Cl.C=1C=C2N(C)C=CC2=CC=1N1C(=O)N(C(=O)C(N)C)N=C1C1=CC(C(C)C)=C(C(C)(N)C(O)=O)C=C1C(C)(N)C(O)=O VSFBAMLPDZXWHL-UHFFFAOYSA-N 0.000 claims description 2
- KHDDWPCBVUJQED-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-methoxyphenyl)-4-naphthalen-1-yl-5-(sulfamoylamino)-1,2,4-triazole Chemical compound C1=C(O)C(OC)=CC(C=2N(C(NS(N)(=O)=O)=NN=2)C=2C3=CC=CC=C3C=CC=2)=C1O KHDDWPCBVUJQED-UHFFFAOYSA-N 0.000 claims description 2
- NIOZAKGGUFNQOF-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-methoxyphenyl)-5-(sulfamoylamino)-4-[3-(trifluoromethyl)phenyl]-1,2,4-triazole Chemical compound C1=C(O)C(OC)=CC(C=2N(C(NS(N)(=O)=O)=NN=2)C=2C=C(C=CC=2)C(F)(F)F)=C1O NIOZAKGGUFNQOF-UHFFFAOYSA-N 0.000 claims description 2
- BBXCKRLARZOVHB-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[1-(3-methoxypropanoyl)indol-5-yl]-1H-1,2,4-triazol-5-one Chemical compound C=1C=C2N(C(=O)CCOC)C=CC2=CC=1N1C(O)=NN=C1C1=CC(C(C)C)=C(O)C=C1O BBXCKRLARZOVHB-UHFFFAOYSA-N 0.000 claims description 2
- ORBJUPQOBVYLES-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-phenyl-5-(sulfamoylamino)-1,2,4-triazole Chemical compound C=1C=CC=CC=1N1C(NS(=O)(=O)N)=NN=C1C1=CC=C(O)C=C1O ORBJUPQOBVYLES-UHFFFAOYSA-N 0.000 claims description 2
- SOSYJMJCHKNCSU-UHFFFAOYSA-N 3-(3,5-dihydroxy-6-propan-2-ylpyridin-2-yl)-4-(1-methyl-2,3-dihydroindol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=NC(C=2N(C(O)=NN=2)C=2C=C3CCN(C)C3=CC=2)=C1O SOSYJMJCHKNCSU-UHFFFAOYSA-N 0.000 claims description 2
- PAMXGEALZAGFID-UHFFFAOYSA-N 3-(3,5-dihydroxy-6-propan-2-ylpyridin-2-yl)-4-(1-methylindol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=NC(C=2N(C(O)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O PAMXGEALZAGFID-UHFFFAOYSA-N 0.000 claims description 2
- QHLDJQHXGSRINY-UHFFFAOYSA-N 3-(3,5-dihydroxy-6-propan-2-ylpyridin-2-yl)-4-(2-methoxy-2,3-dihydro-1H-inden-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2CC(OC)CC2=CC=C1N1C(S)=NN=C1C1=NC(C(C)C)=C(O)C=C1O QHLDJQHXGSRINY-UHFFFAOYSA-N 0.000 claims description 2
- WHAFFLIEXRSPTP-UHFFFAOYSA-N 3-(3,5-dihydroxy-6-propan-2-ylpyridin-2-yl)-4-[2-(2-hydroxyethoxy)-2,3-dihydro-1H-inden-5-yl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=NC(C=2N(C(O)=NN=2)C=2C=C3CC(CC3=CC=2)OCCO)=C1O WHAFFLIEXRSPTP-UHFFFAOYSA-N 0.000 claims description 2
- OGDQCGPBYRKYOC-UHFFFAOYSA-N 3-(3,5-dihydroxy-6-propan-2-ylpyridin-2-yl)-4-[2-(2-methoxyethyl)-1,3-dihydroisoindol-5-yl]-1H-1,2,4-triazol-5-one Chemical compound C1=C2CN(CCOC)CC2=CC=C1N1C(O)=NN=C1C1=NC(C(C)C)=C(O)C=C1O OGDQCGPBYRKYOC-UHFFFAOYSA-N 0.000 claims description 2
- RFRXKGVENGLCGU-UHFFFAOYSA-N 3-(3,5-dihydroxy-6-propan-2-ylpyridin-2-yl)-4-[4-(dimethylamino)phenyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=NC(C=2N(C(O)=NN=2)C=2C=CC(=CC=2)N(C)C)=C1O RFRXKGVENGLCGU-UHFFFAOYSA-N 0.000 claims description 2
- CGIBJFYENYZZFQ-UHFFFAOYSA-N 3-(6-cyclopropyl-3,5-dihydroxypyridin-2-yl)-4-[[4-(dimethylamino)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(N(C)C)=CC=C1CN1C(C=2C(=CC(O)=C(C3CC3)N=2)O)=NN=C1O CGIBJFYENYZZFQ-UHFFFAOYSA-N 0.000 claims description 2
- MBKXXZHPXKWIOF-UHFFFAOYSA-N 3-(6-ethyl-3,5-dihydroxypyridin-2-yl)-4-(1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=NC(C=2N(C(S)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O MBKXXZHPXKWIOF-UHFFFAOYSA-N 0.000 claims description 2
- WSNISFAAWKKBBC-UHFFFAOYSA-N 3-(6-ethyl-3,5-dihydroxypyridin-2-yl)-4-[(4-methoxyphenyl)methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(CC)=NC(C=2N(C(O)=NN=2)CC=2C=CC(OC)=CC=2)=C1O WSNISFAAWKKBBC-UHFFFAOYSA-N 0.000 claims description 2
- SVFYBLVEVIDHLU-UHFFFAOYSA-N 3-(6-hydroxy-1,3-benzodioxol-5-yl)-4-(1-propan-2-ylbenzimidazol-4-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=CC=C2N(C(C)C)C=NC2=C1N1C(O)=NN=C1C(C(=C1)O)=CC2=C1OCO2 SVFYBLVEVIDHLU-UHFFFAOYSA-N 0.000 claims description 2
- ZHWJXIQJNAIVMH-UHFFFAOYSA-N 3-(6-hydroxy-1H-indol-5-yl)-4-(1-methylindol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C=1C=C2N(C)C=CC2=CC=1N1C(O)=NN=C1C(C(=C1)O)=CC2=C1NC=C2 ZHWJXIQJNAIVMH-UHFFFAOYSA-N 0.000 claims description 2
- PWERFEJUOOMBTM-UHFFFAOYSA-N 3-(6-hydroxy-2,2-dimethyl-1,3-benzodioxol-5-yl)-4-(4-methylphenyl)-1H-1,2,4-triazol-5-one Chemical compound C1=CC(C)=CC=C1N1C(C=2C(=CC=3OC(C)(C)OC=3C=2)O)=NN=C1O PWERFEJUOOMBTM-UHFFFAOYSA-N 0.000 claims description 2
- KVCKYJPBRSJMCQ-UHFFFAOYSA-N 3-(6-hydroxy-2,2-dimethyl-1,3-benzodioxol-5-yl)-4-(7H-purin-6-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C2OC(C)(C)OC2=CC(O)=C1C1=NN=C(O)N1C1=NC=NC2=C1N=CN2 KVCKYJPBRSJMCQ-UHFFFAOYSA-N 0.000 claims description 2
- TYRQZYJINFZUQU-UHFFFAOYSA-N 3-(6-hydroxy-2-oxo-1,3-benzodioxol-5-yl)-4-[2-(2H-tetrazol-5-yl)phenyl]-1H-1,2,4-triazol-5-one Chemical compound OC1=NN=C(C=2C(=CC=3OC(=O)OC=3C=2)O)N1C1=CC=CC=C1C1=NN=NN1 TYRQZYJINFZUQU-UHFFFAOYSA-N 0.000 claims description 2
- IRZZMEBBYBPQEG-UHFFFAOYSA-N 3-(6-hydroxy-3-methyl-1H-indol-5-yl)-4-(1-methylindazol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2N(C)N=CC2=CC(N2C(S)=NN=C2C2=C(O)C=C3NC=C(C3=C2)C)=C1 IRZZMEBBYBPQEG-UHFFFAOYSA-N 0.000 claims description 2
- HRQWCJMMSJGLAJ-UHFFFAOYSA-N 3-(6-hydroxy-3-methyl-1H-indol-5-yl)-4-(6-methoxynaphthalen-1-yl)-1H-1,2,4-triazol-5-one Chemical compound C=1C=CC2=CC(OC)=CC=C2C=1N1C(O)=NN=C1C(C(=C1)O)=CC2=C1NC=C2C HRQWCJMMSJGLAJ-UHFFFAOYSA-N 0.000 claims description 2
- BQMIWCHKHOATFT-UHFFFAOYSA-N 3-[2-hydroxy-4-(2-hydroxyethoxy)phenyl]-4-naphthalen-1-yl-1H-1,2,4-triazole-5-thione Chemical compound OC1=CC(OCCO)=CC=C1C1=NN=C(S)N1C1=CC=CC2=CC=CC=C12 BQMIWCHKHOATFT-UHFFFAOYSA-N 0.000 claims description 2
- OZASOSPCYINUQC-UHFFFAOYSA-N 3-[2-hydroxy-4-(2-methoxyethoxy)phenyl]-4-naphthalen-1-yl-1H-1,2,4-triazole-5-thione Chemical compound OC1=CC(OCCOC)=CC=C1C1=NN=C(S)N1C1=CC=CC2=CC=CC=C12 OZASOSPCYINUQC-UHFFFAOYSA-N 0.000 claims description 2
- YXBNBRSXWAXDHJ-UHFFFAOYSA-N 3-[3,5-dihydroxy-6-(2-phenylethyl)pyridin-2-yl]-4-[4-(methoxymethyl)phenyl]-1H-1,2,4-triazole-5-thione Chemical compound C1=CC(COC)=CC=C1N1C(C=2C(=CC(O)=C(CCC=3C=CC=CC=3)N=2)O)=NN=C1S YXBNBRSXWAXDHJ-UHFFFAOYSA-N 0.000 claims description 2
- HOIGNJXPVHCCND-UHFFFAOYSA-N 3-[3,5-dihydroxy-6-(2-phenylethyl)pyridin-2-yl]-4-[4-[(dimethylamino)methyl]phenyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(CN(C)C)=CC=C1N1C(C=2C(=CC(O)=C(CCC=3C=CC=CC=3)N=2)O)=NN=C1O HOIGNJXPVHCCND-UHFFFAOYSA-N 0.000 claims description 2
- NTOOVOHYWJAFSD-UHFFFAOYSA-N 3-ethyl-6-hydroxy-5-[5-oxo-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazol-3-yl]-1,3-dihydroindol-2-one Chemical compound C1=C2C(CC)C(=O)NC2=CC(O)=C1C1=NN=C(O)N1C1=CC=CC2=C1C=CN2C(C)C NTOOVOHYWJAFSD-UHFFFAOYSA-N 0.000 claims description 2
- HGBSPDZOQXZEBF-UHFFFAOYSA-N 4-(1,2-dihydroacenaphthylen-5-yl)-3-(6-hydroxy-3H-benzimidazol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1CC2=CC=CC3=C2C1=CC=C3N1C(S)=NN=C1C1=CC(N=CN2)=C2C=C1O HGBSPDZOQXZEBF-UHFFFAOYSA-N 0.000 claims description 2
- JSBXNTKXKSSXQR-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2OCOC2=CC(N2C(S)=NN=C2C2=CC=3OCOC=3C=C2O)=C1 JSBXNTKXKSSXQR-UHFFFAOYSA-N 0.000 claims description 2
- VPGZUHIHULGQID-UHFFFAOYSA-N 4-(1,3-dimethylindol-5-yl)-3-(6-hydroxy-2,2-dimethyl-1,3-benzodioxol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C2C(C)=CN(C)C2=CC=C1N1C(O)=NN=C1C(C(=C1)O)=CC2=C1OC(C)(C)O2 VPGZUHIHULGQID-UHFFFAOYSA-N 0.000 claims description 2
- COUIMJHPHSGKBK-UHFFFAOYSA-N 4-(1-acetylindol-5-yl)-3-(2,4-dihydroxy-5-propan-2-ylphenyl)-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=CN(C3=CC=2)C(C)=O)=C1O COUIMJHPHSGKBK-UHFFFAOYSA-N 0.000 claims description 2
- AKMXICSNXROPSB-UHFFFAOYSA-N 4-(1-ethyl-2-methylbenzimidazol-5-yl)-3-(6-hydroxy-2,3-dimethyl-1H-indol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(CC)C(C)=NC2=CC=1N1C(S)=NN=C1C(C(=C1)O)=CC2=C1NC(C)=C2C AKMXICSNXROPSB-UHFFFAOYSA-N 0.000 claims description 2
- UIJDDPDLQMJNMC-UHFFFAOYSA-N 4-(1-ethylindol-4-yl)-3-(6-hydroxy-1H-indol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CC)C=CC2=C1N1C(S)=NN=C1C(C(=C1)O)=CC2=C1NC=C2 UIJDDPDLQMJNMC-UHFFFAOYSA-N 0.000 claims description 2
- KJJFTIZLONURNN-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-3-(6-hydroxy-1H-indazol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound OC1=NN=C(C=2C(=CC=3NN=CC=3C=2)O)N1C1=CC=CC(Cl)=C1Cl KJJFTIZLONURNN-UHFFFAOYSA-N 0.000 claims description 2
- OEKOTGXMMYNSQV-UHFFFAOYSA-N 4-(2,3-dimethyl-1H-indol-4-yl)-3-(6-hydroxy-2,3-dimethyl-1H-indol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2C(C)=C(C)NC2=CC(O)=C1C1=NN=C(S)N1C1=CC=CC2=C1C(C)=C(C)N2 OEKOTGXMMYNSQV-UHFFFAOYSA-N 0.000 claims description 2
- ZAXGIDABLBQRJC-UHFFFAOYSA-N 4-(3-ethyl-1-methylindol-5-yl)-3-(6-hydroxy-1H-indazol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2C(CC)=CN(C)C2=CC=C1N1C(S)=NN=C1C(C(=C1)O)=CC2=C1NN=C2 ZAXGIDABLBQRJC-UHFFFAOYSA-N 0.000 claims description 2
- JRUPADJGDRBBBC-UHFFFAOYSA-N 4-[1-(cyclopropylmethyl)indol-4-yl]-3-[6-hydroxy-2-(trifluoromethyl)-3H-benzimidazol-5-yl]-1H-1,2,4-triazole-5-thione Chemical compound OC1=CC=2NC(C(F)(F)F)=NC=2C=C1C1=NN=C(S)N1C(C=1C=C2)=CC=CC=1N2CC1CC1 JRUPADJGDRBBBC-UHFFFAOYSA-N 0.000 claims description 2
- SNCPBGHPVDYWPY-UHFFFAOYSA-N 4-[3-(2,2-diethyl-6-hydroxy-1,3-benzodioxol-5-yl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-N,N-dimethylindole-1-carboxamide Chemical compound C1=C2OC(CC)(CC)OC2=CC(O)=C1C1=NN=C(S)N1C1=CC=CC2=C1C=CN2C(=O)N(C)C SNCPBGHPVDYWPY-UHFFFAOYSA-N 0.000 claims description 2
- BNKRZEINXYDTOZ-UHFFFAOYSA-N 4-[3-(2,4-dihydroxy-5-methoxyphenyl)-5-(sulfamoylamino)-1,2,4-triazol-4-yl]-1-propan-2-ylbenzimidazole Chemical compound C1=C(O)C(OC)=CC(C=2N(C(NS(N)(=O)=O)=NN=2)C=2C=3N=CN(C=3C=CC=2)C(C)C)=C1O BNKRZEINXYDTOZ-UHFFFAOYSA-N 0.000 claims description 2
- KVJNBLMKAFOHRE-UHFFFAOYSA-N 4-[3-(6-hydroxy-2-methyl-3H-benzimidazol-5-yl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]naphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N3C(S)=NN=C3C=3C=C4N=C(NC4=CC=3O)C)=CC=C(C(O)=O)C2=C1 KVJNBLMKAFOHRE-UHFFFAOYSA-N 0.000 claims description 2
- OTMRSILIQSOGDJ-UHFFFAOYSA-N 4-[4-(1-methylindol-5-yl)-5-(quinolin-6-ylamino)-1,2,4-triazol-3-yl]-6-propan-2-ylbenzene-1,3-diol Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC=3C=C4C=CC=NC4=CC=3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O OTMRSILIQSOGDJ-UHFFFAOYSA-N 0.000 claims description 2
- BAYYSWDARVOTBH-UHFFFAOYSA-N 4-[4-(1-methylindol-5-yl)-5-[3-(trifluoromethyl)anilino]-1,2,4-triazol-3-yl]-6-propan-2-ylbenzene-1,3-diol Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC=3C=C(C=CC=3)C(F)(F)F)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O BAYYSWDARVOTBH-UHFFFAOYSA-N 0.000 claims description 2
- FCCBATACBZGWEY-UHFFFAOYSA-N 4-[5-(3-aminoanilino)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-6-propan-2-ylbenzene-1,3-diol Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC=3C=C(N)C=CC=3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O FCCBATACBZGWEY-UHFFFAOYSA-N 0.000 claims description 2
- QRCDPGACVVTIQE-UHFFFAOYSA-N 4-[5-(3-methoxyanilino)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-6-propan-2-ylbenzene-1,3-diol Chemical compound COC1=CC=CC(NC=2N(C(C=3C(=CC(O)=C(C(C)C)C=3)O)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1 QRCDPGACVVTIQE-UHFFFAOYSA-N 0.000 claims description 2
- LCXPQEJQXWFKHH-UHFFFAOYSA-N 4-[5-(benzylamino)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-6-propan-2-ylbenzene-1,3-diol Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NCC=3C=CC=CC=3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O LCXPQEJQXWFKHH-UHFFFAOYSA-N 0.000 claims description 2
- HMFFWDSYKQETMG-UHFFFAOYSA-N 4-[5-(methylamino)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-6-propan-2-ylbenzene-1,3-diol Chemical compound C=1C=C2N(C)C=CC2=CC=1N1C(NC)=NN=C1C1=CC(C(C)C)=C(O)C=C1O HMFFWDSYKQETMG-UHFFFAOYSA-N 0.000 claims description 2
- VKSRNPRPIUGCGY-UHFFFAOYSA-N 4-[5-amino-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-6-propan-2-ylbenzene-1,3-diol Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(N)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O VKSRNPRPIUGCGY-UHFFFAOYSA-N 0.000 claims description 2
- OPMWGJZUMRXMFK-UHFFFAOYSA-N 4-[5-amino-4-(1-propan-2-ylindol-4-yl)-1,2,4-triazol-3-yl]-6-ethylbenzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(C=2N(C(N)=NN=2)C=2C=3C=CN(C=3C=CC=2)C(C)C)=C1O OPMWGJZUMRXMFK-UHFFFAOYSA-N 0.000 claims description 2
- KNBGHGVEYZRZFS-UHFFFAOYSA-N 4-[5-amino-4-(3-methoxyphenyl)-1,2,4-triazol-3-yl]-6-ethylbenzene-1,3-diol Chemical compound C1=C(O)C(CC)=CC(C=2N(C(N)=NN=2)C=2C=C(OC)C=CC=2)=C1O KNBGHGVEYZRZFS-UHFFFAOYSA-N 0.000 claims description 2
- JSUQKARSXROANH-UHFFFAOYSA-N 4-[5-anilino-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-6-propan-2-ylbenzene-1,3-diol Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC=3C=CC=CC=3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O JSUQKARSXROANH-UHFFFAOYSA-N 0.000 claims description 2
- GNDCQBSRGVQFKP-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-2-propanoyl-1,2,4-triazol-3-one Chemical compound C=1C=C2N(C)C=CC2=CC=1N1C(=O)N(C(=O)CC)N=C1C1=CC(C(C)C)=C(O)C=C1O GNDCQBSRGVQFKP-UHFFFAOYSA-N 0.000 claims description 2
- GJJSVNQUWUNRAI-UHFFFAOYSA-N 5-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]-6-hydroxy-3-methyl-1H-benzimidazol-2-one Chemical compound O1CCOC2=C1C=CC=C2N1C(S)=NN=C1C1=C(O)C=C(NC(N2C)=O)C2=C1 GJJSVNQUWUNRAI-UHFFFAOYSA-N 0.000 claims description 2
- YUWJOFPBGRYMCX-UHFFFAOYSA-N 5-[4-(3,5-dimethylphenyl)-5-oxo-1H-1,2,4-triazol-3-yl]-6-hydroxy-1,3-dihydroindol-2-one Chemical compound CC1=CC(C)=CC(N2C(=NN=C2O)C=2C(=CC=3NC(=O)CC=3C=2)O)=C1 YUWJOFPBGRYMCX-UHFFFAOYSA-N 0.000 claims description 2
- HDCNCXIWHYIKRE-UHFFFAOYSA-N 5-hydroxy-2-oxo-6-[4-phenyl-5-(sulfamoylamino)-1,2,4-triazol-3-yl]-1,3-dihydrobenzimidazole Chemical compound NS(=O)(=O)NC1=NN=C(C=2C(=CC=3NC(=O)NC=3C=2)O)N1C1=CC=CC=C1 HDCNCXIWHYIKRE-UHFFFAOYSA-N 0.000 claims description 2
- MBIGPUABGRFHBJ-UHFFFAOYSA-N 5-hydroxy-6-[4-(1-propan-2-ylindol-4-yl)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]-1,3-benzodioxol-2-one Chemical compound C1=CC=C2N(C(C)C)C=CC2=C1N1C(S)=NN=C1C(C(=C1)O)=CC2=C1OC(=O)O2 MBIGPUABGRFHBJ-UHFFFAOYSA-N 0.000 claims description 2
- IDHIUDDIQPUNDF-UHFFFAOYSA-N 5-hydroxy-6-[4-(4-methoxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]-1,3-benzodioxol-2-one Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC=3OC(=O)OC=3C=2)O)=NN=C1S IDHIUDDIQPUNDF-UHFFFAOYSA-N 0.000 claims description 2
- QHKWYHNSPZDOLM-UHFFFAOYSA-N 6-[4-(1,3-benzothiazol-4-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-7-hydroxy-3-methyl-1H-quinolin-2-one Chemical compound OC=1C=C2NC(=O)C(C)=CC2=CC=1C1=NN=C(O)N1C1=CC=CC2=C1N=CS2 QHKWYHNSPZDOLM-UHFFFAOYSA-N 0.000 claims description 2
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- VAVYPWKORADOHY-UHFFFAOYSA-N 6-hydroxy-5-[4-(7-methoxy-2-methyl-1-benzofuran-4-yl)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]-3-methyl-1H-benzimidazol-2-one Chemical compound C1=2C=C(C)OC=2C(OC)=CC=C1N1C(S)=NN=C1C(C(=C1)O)=CC2=C1NC(=O)N2C VAVYPWKORADOHY-UHFFFAOYSA-N 0.000 claims description 2
- CMIXNIKEZNHRBS-UHFFFAOYSA-N 6-hydroxy-5-[4-(7-methoxy-2-methyl-1-benzofuran-4-yl)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]-3-propan-2-yl-1H-benzimidazol-2-one Chemical compound C1=2C=C(C)OC=2C(OC)=CC=C1N1C(S)=NN=C1C(C(=C1)O)=CC2=C1NC(=O)N2C(C)C CMIXNIKEZNHRBS-UHFFFAOYSA-N 0.000 claims description 2
- MMRTYOAEQFKPBM-UHFFFAOYSA-N 6-hydroxy-5-[4-[1-(2-methoxyethyl)indol-4-yl]-5-sulfanylidene-1H-1,2,4-triazol-3-yl]-3,3-dimethyl-1H-indol-2-one Chemical compound C1=CC=C2N(CCOC)C=CC2=C1N1C(S)=NN=C1C(C(=C1)O)=CC2=C1NC(=O)C2(C)C MMRTYOAEQFKPBM-UHFFFAOYSA-N 0.000 claims description 2
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- XSTRJZWUFDUINV-UHFFFAOYSA-N CCC1=CC(=C(C=C1C2=CC=CC=C2C(=O)O)C3=CC=CC=C3C(=O)O)C4=NN=C(N4C5=CC=CC6=CC=CC=C65)S Chemical compound CCC1=CC(=C(C=C1C2=CC=CC=C2C(=O)O)C3=CC=CC=C3C(=O)O)C4=NN=C(N4C5=CC=CC6=CC=CC=C65)S XSTRJZWUFDUINV-UHFFFAOYSA-N 0.000 claims description 2
- WNLWNONQVGQDQI-UHFFFAOYSA-N Cl.Cl.Cl.C1=C(C(N)C(O)=O)C(C(C)C)=CC(C=2N(C(=O)N(C(=O)CN)N=2)C=2C=C3C=CN(C)C3=CC=2)=C1C(N)C(O)=O Chemical compound Cl.Cl.Cl.C1=C(C(N)C(O)=O)C(C(C)C)=CC(C=2N(C(=O)N(C(=O)CN)N=2)C=2C=C3C=CN(C)C3=CC=2)=C1C(N)C(O)=O WNLWNONQVGQDQI-UHFFFAOYSA-N 0.000 claims description 2
- VKUZBTZUKJXEOQ-UHFFFAOYSA-N Cl.Cl.Cl.NC(C(=O)N1N=C(N(C1=O)C=1C=C2C=CN(C2=CC1)C)C1=C(C=C(C(=C1)C(C)C)C(C(=O)O)(CC1=CC=CC=C1)N)C(C(=O)O)(CC1=CC=CC=C1)N)CC1=CC=CC=C1 Chemical compound Cl.Cl.Cl.NC(C(=O)N1N=C(N(C1=O)C=1C=C2C=CN(C2=CC1)C)C1=C(C=C(C(=C1)C(C)C)C(C(=O)O)(CC1=CC=CC=C1)N)C(C(=O)O)(CC1=CC=CC=C1)N)CC1=CC=CC=C1 VKUZBTZUKJXEOQ-UHFFFAOYSA-N 0.000 claims description 2
- PCDAEHQBNBRWOS-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-2,2,2-trifluoroacetamide Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC(=O)C(F)(F)F)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O PCDAEHQBNBRWOS-UHFFFAOYSA-N 0.000 claims description 2
- JTNSKWLRTDCTIN-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-2-methoxyacetamide Chemical compound C=1C=C2N(C)C=CC2=CC=1N1C(NC(=O)COC)=NN=C1C1=CC(C(C)C)=C(O)C=C1O JTNSKWLRTDCTIN-UHFFFAOYSA-N 0.000 claims description 2
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- XFQUQJHLRBIMIY-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-2-phenylacetamide Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC(=O)CC=3C=CC=CC=3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O XFQUQJHLRBIMIY-UHFFFAOYSA-N 0.000 claims description 2
- VUTVILJHSCSIII-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-3,4-difluorobenzamide Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC(=O)C=3C=C(F)C(F)=CC=3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O VUTVILJHSCSIII-UHFFFAOYSA-N 0.000 claims description 2
- JUUHKWUKGLKMCZ-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC(=O)C3=NOC(C)=C3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O JUUHKWUKGLKMCZ-UHFFFAOYSA-N 0.000 claims description 2
- NQYVUOUNGQDZAU-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]acetamide Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC(C)=O)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O NQYVUOUNGQDZAU-UHFFFAOYSA-N 0.000 claims description 2
- WVGCXBMZAJAXQN-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]benzamide Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC(=O)C=3C=CC=CC=3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O WVGCXBMZAJAXQN-UHFFFAOYSA-N 0.000 claims description 2
- QHMQQZQPQNXECY-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]butanamide Chemical compound C=1C=C2N(C)C=CC2=CC=1N1C(NC(=O)CCC)=NN=C1C1=CC(C(C)C)=C(O)C=C1O QHMQQZQPQNXECY-UHFFFAOYSA-N 0.000 claims description 2
- GLDWMOZRBCZKFE-UHFFFAOYSA-N N-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindol-5-yl)-1,2,4-triazol-3-yl]furan-2-carboxamide Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC(=O)C=3OC=CC=3)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O GLDWMOZRBCZKFE-UHFFFAOYSA-N 0.000 claims description 2
- BFVOZELYTXHXQK-UHFFFAOYSA-N S-[[5-(2,4-dihydroxyphenyl)-4-naphthalen-1-yl-1,2,4-triazol-3-yl]] N,N-dimethylcarbamothioate Chemical compound C=1C=CC2=CC=CC=C2C=1N1C(SC(=O)N(C)C)=NN=C1C1=CC=C(O)C=C1O BFVOZELYTXHXQK-UHFFFAOYSA-N 0.000 claims description 2
- HTECKPBLFTUPFO-UHFFFAOYSA-N [1-(dimethylcarbamoyl)-5-[5-(dimethylcarbamoylsulfanyl)-4-(1-ethylindol-4-yl)-1,2,4-triazol-3-yl]indol-6-yl] n,n-dimethylcarbamate Chemical compound C1=CC=C2N(CC)C=CC2=C1N1C(SC(=O)N(C)C)=NN=C1C(C(=C1)OC(=O)N(C)C)=CC2=C1N(C(=O)N(C)C)C=C2 HTECKPBLFTUPFO-UHFFFAOYSA-N 0.000 claims description 2
- MFDWIAJXIVRXGI-UHFFFAOYSA-N [2,6-diethyl-3-[5-(ethylcarbamoylsulfanyl)-4-naphthalen-1-yl-1,2,4-triazol-3-yl]phenyl] carbamate Chemical compound C=1C=CC2=CC=CC=C2C=1N1C(SC(=O)NCC)=NN=C1C1=CC=C(CC)C(OC(N)=O)=C1CC MFDWIAJXIVRXGI-UHFFFAOYSA-N 0.000 claims description 2
- JZVIEINBFWBPDJ-UHFFFAOYSA-N [2-chloro-5-hydroxy-4-(4-quinolin-5-yl-5-sulfanylidene-1H-1,2,4-triazol-3-yl)phenyl] N,N-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=C(Cl)C=C(C2=NN=C(S)N2C2=C3C=CC=NC3=CC=C2)C(O)=C1 JZVIEINBFWBPDJ-UHFFFAOYSA-N 0.000 claims description 2
- RROJYLNOPDVWGW-UHFFFAOYSA-N [2-ethyl-5-hydroxy-4-(4-naphthalen-2-yl-5-oxo-1H-1,2,4-triazol-3-yl)phenyl] N,N-dimethylcarbamate Chemical compound OC1=C(C=C(C(=C1)OC(N(C)C)=O)CC)C1=NN=C(N1C1=CC2=CC=CC=C2C=C1)O RROJYLNOPDVWGW-UHFFFAOYSA-N 0.000 claims description 2
- SDVIYNIGUBTNGS-UHFFFAOYSA-N [2-ethyl-5-hydroxy-4-[4-(1-methylbenzimidazol-4-yl)-5-oxo-1H-1,2,4-triazol-3-yl]phenyl] 2-methylpropanoate Chemical compound C1=C(OC(=O)C(C)C)C(CC)=CC(C=2N(C(O)=NN=2)C=2C=3N=CN(C)C=3C=CC=2)=C1O SDVIYNIGUBTNGS-UHFFFAOYSA-N 0.000 claims description 2
- ZQQYPBLEMMVSOG-UHFFFAOYSA-N [3-(2-methylpropanoyloxy)-4-[5-(2-methylpropanoylsulfanyl)-4-naphthalen-1-yl-1,2,4-triazol-3-yl]phenyl] 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC(OC(=O)C(C)C)=CC=C1C1=NN=C(SC(=O)C(C)C)N1C1=CC=CC2=CC=CC=C12 ZQQYPBLEMMVSOG-UHFFFAOYSA-N 0.000 claims description 2
- YZNCRIMHGZLBBC-UHFFFAOYSA-N [3-(dimethylcarbamoyloxy)-4-[5-(dimethylcarbamoylsulfanyl)-4-naphthalen-1-yl-1,2,4-triazol-3-yl]phenyl] n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC(OC(=O)N(C)C)=CC=C1C1=NN=C(SC(=O)N(C)C)N1C1=CC=CC2=CC=CC=C12 YZNCRIMHGZLBBC-UHFFFAOYSA-N 0.000 claims description 2
- YSSCRUWTJXLQAN-UHFFFAOYSA-N [3-(dimethylcarbamoyloxy)-4-[5-(dimethylcarbamoylsulfanyl)-4-quinolin-5-yl-1,2,4-triazol-3-yl]phenyl] n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC(OC(=O)N(C)C)=CC=C1C1=NN=C(SC(=O)N(C)C)N1C1=CC=CC2=NC=CC=C12 YSSCRUWTJXLQAN-UHFFFAOYSA-N 0.000 claims description 2
- BBBPKYYDQYCYBX-UHFFFAOYSA-N [3-acetyloxy-4-(4-naphthalen-1-yl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)phenyl] acetate Chemical compound CC(=O)OC1=CC(OC(=O)C)=CC=C1C1=NN=C(S)N1C1=CC=CC2=CC=CC=C12 BBBPKYYDQYCYBX-UHFFFAOYSA-N 0.000 claims description 2
- HFSPRTPMZQPXSA-UHFFFAOYSA-N [3-acetyloxy-4-(5-acetylsulfanyl-4-naphthalen-1-yl-1,2,4-triazol-3-yl)phenyl] acetate Chemical compound CC(=O)OC1=CC(OC(=O)C)=CC=C1C1=NN=C(SC(C)=O)N1C1=CC=CC2=CC=CC=C12 HFSPRTPMZQPXSA-UHFFFAOYSA-N 0.000 claims description 2
- TZHUUTFRTLZTTD-UHFFFAOYSA-N [4-(2,3-difluorophenyl)-5-(2,4-dihydroxy-5-methoxyphenyl)-1,2,4-triazol-3-yl]urea Chemical compound C1=C(O)C(OC)=CC(C=2N(C(NC(N)=O)=NN=2)C=2C(=C(F)C=CC=2)F)=C1O TZHUUTFRTLZTTD-UHFFFAOYSA-N 0.000 claims description 2
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| PCT/US2007/012543 WO2007139967A2 (en) | 2006-05-25 | 2007-05-25 | Triazole compounds that modulate hsp90 activity |
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| JP2009538321A JP2009538321A (ja) | 2009-11-05 |
| JP2009538321A5 true JP2009538321A5 (https=) | 2010-07-08 |
| JP5441691B2 JP5441691B2 (ja) | 2014-03-12 |
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| JP (1) | JP5441691B2 (https=) |
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