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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Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1143120A (ja) * | 1997-07-28 | 1999-02-16 | Ishikawajima Harima Heavy Ind Co Ltd | 容器の後処理装置 |
| EP1817295B1 (en) | 2004-11-18 | 2012-11-07 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| CN101160291B (zh) * | 2005-03-09 | 2012-09-05 | 日本化药株式会社 | 作为hsp90抑制剂的三唑衍生物 |
| US7608635B2 (en) | 2005-08-12 | 2009-10-27 | Synta Pharmaceuticals Corp. | Pyrazole compounds that modulate HSP90 activity |
| JP5118039B2 (ja) | 2005-08-18 | 2013-01-16 | シンタ ファーマシューティカルズ コーポレーション | Ｈｓｐ９０活性を調節するトリアゾール化合物 |
| 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 |
| CA2653327A1 (en) * | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Compounds that modulate hsp90 activity and methods for identifying same |
| WO2007139955A2 (en) | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| AU2007267843B2 (en) | 2006-05-25 | 2011-10-13 | Synta Pharmaceuticals Corp. | Method for treating proliferative disorders associated with protooncogene products |
| SI2035396T1 (sl) | 2006-05-25 | 2014-08-29 | Synta Pharmaceuticals Corp. | Triazolne spojine, ki modulirajo aktivnost HSP90 |
| US8063083B2 (en) | 2006-05-25 | 2011-11-22 | Synta Pharmaceuticals Corp. | Method for treating non-Hodgkin's lymphoma |
| AU2007284537B2 (en) | 2006-08-17 | 2012-04-12 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| US20110046125A1 (en) * | 2006-10-19 | 2011-02-24 | Synta Pharmaceuticals Corp. | Method for treating infections |
| PL2118077T3 (pl) * | 2007-02-08 | 2015-05-29 | Synta Pharmaceuticals Corp | Związki triazolowe modulujące aktywność hsp90 |
| TW200904417A (en) * | 2007-02-20 | 2009-02-01 | Synta Pharmaceuticals Corp | Triazole compounds that modulate Hsp90 activity |
| WO2008112199A1 (en) * | 2007-03-12 | 2008-09-18 | Synta Pharmaceuticals Corp. | Method for inhibiting topoisomerase ii |
| AU2008287367B2 (en) | 2007-08-13 | 2012-02-23 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| WO2009075890A2 (en) * | 2007-12-12 | 2009-06-18 | Synta Pharmaceuticals Corp. | Method for synthesis of triazole compounds that modulate hsp90 activity |
| CA2714181C (en) * | 2008-02-04 | 2013-12-24 | Mercury Therapeutics, Inc. | Ampk modulators |
| US9156836B2 (en) * | 2008-05-16 | 2015-10-13 | Synta Pharmaceuticals Corp. | Tricyclic triazole compounds that modulate HSP90 activity |
| US8450500B2 (en) | 2008-06-04 | 2013-05-28 | Synta Pharmaceuticals Corp. | Pyrrole compounds that modulate HSP90 activity |
| US8648071B2 (en) | 2008-06-27 | 2014-02-11 | Synta Pharmaceuticals Corp. | Hydrazonamide compounds that modulate Hsp90 activity |
| WO2010017545A2 (en) * | 2008-08-08 | 2010-02-11 | Synta Pharamceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| US9126953B2 (en) * | 2008-08-08 | 2015-09-08 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| WO2010100127A1 (en) | 2009-03-04 | 2010-09-10 | Novartis Ag | Disubstituted imidazole derivatives as modulators of raf kinase |
| CA2764339A1 (en) * | 2009-06-05 | 2010-12-09 | Oslo University Hospital Hf | Azole derivatives as wtn pathway inhibitors |
| 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 |
| WO2011060394A1 (en) * | 2009-11-16 | 2011-05-19 | Schering Corporation | Compounds useful as chemokine receptor antagonists |
| EP2560640A1 (en) | 2010-04-19 | 2013-02-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
| RU2013128448A (ru) | 2010-12-08 | 2015-01-20 | Осло Юниверсити Хоспитал Хф | Производные триазола в качестве ингибиторов сигнального пути wnt |
| AU2012204650A1 (en) * | 2011-01-07 | 2013-08-01 | Taiho Pharmaceutical Co., Ltd. | Novel indole or indazole derivative or salt thereof |
| CA2840986A1 (en) | 2011-07-07 | 2013-01-10 | Synta Pharmaceuticals Corp. | Treating cancer with hsp90 inhibitory compounds |
| JP2014534228A (ja) | 2011-11-02 | 2014-12-18 | シンタ ファーマシューティカルズ コーポレーション | 白金含有剤とｈｓｐ９０阻害剤の組合せ療法 |
| CA2853799A1 (en) | 2011-11-02 | 2013-05-10 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of hsp90 inhibitors with topoisomerase i inhibitors |
| US9402831B2 (en) | 2011-11-14 | 2016-08-02 | Synta Pharmaceutical Corp. | Combination therapy of HSP90 inhibitors with BRAF inhibitors |
| WO2013148857A1 (en) * | 2012-03-28 | 2013-10-03 | Synta Pharmaceuticals Corp. | Triazole derivatives as hsp90 inhibitors |
| CN103664910B (zh) * | 2012-09-14 | 2017-07-04 | 南京大学 | 含1，4‑苯并二噁烷的1，2，4‑三氮唑类衍生物及其制法与其抗菌活性 |
| US20140256776A1 (en) * | 2013-03-06 | 2014-09-11 | C & C Biopharma, Llc | Treatment of cancer and other conditions using a transcription factor modulator |
| JO3377B1 (ar) * | 2013-03-11 | 2019-03-13 | Takeda Pharmaceuticals Co | مشتقات بيريدينيل وبيريدينيل مندمج |
| WO2015066053A2 (en) * | 2013-10-28 | 2015-05-07 | Synta Pharmaceuticals Corp. | Targeted therapeutics |
| EP3626707A1 (en) * | 2014-01-13 | 2020-03-25 | The General Hospital Corporation | Heteroaryl disulfide compounds as allosteric effectors for increasing the oxygen-binding affinity of hemoglobin |
| HUE050317T2 (hu) * | 2015-05-20 | 2020-11-30 | Amgen Inc | APJ receptor triazol agonistái |
| US9988369B2 (en) | 2016-05-03 | 2018-06-05 | Amgen Inc. | Heterocyclic triazole 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 |
| US10736883B2 (en) | 2016-11-16 | 2020-08-11 | Amgen Inc. | Triazole furan 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 |
| WO2018093577A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Cycloalkyl substituted triazole 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 |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| US20180236199A1 (en) * | 2017-02-23 | 2018-08-23 | Kyle J. Lussier | Nasal Cannula |
| US10767164B2 (en) | 2017-03-30 | 2020-09-08 | The Research Foundation For The State University Of New York | Microenvironments for self-assembly of islet organoids from stem cells differentiation |
| MA50509A (fr) | 2017-11-03 | 2021-06-02 | Amgen Inc | Agonistes de triazole fusionnés du récepteur apj |
| GB201801226D0 (en) * | 2018-01-25 | 2018-03-14 | Redx Pharma Plc | Modulators of Rho-associated protein kinase |
| US11807624B2 (en) | 2018-05-01 | 2023-11-07 | Amgen Inc. | Substituted pyrimidinones as agonists of the APJ receptor |
| JP2025533648A (ja) * | 2022-10-06 | 2025-10-07 | レグラニオン、エルエルシー | 化膿性汗腺炎を治療するための方法および組成物 |
| CN115754090B (zh) * | 2022-12-15 | 2023-08-29 | 华夏生生药业(北京)有限公司 | 一种lc-ms检测氟康唑相关杂质的方法 |
| WO2024223907A1 (en) * | 2023-04-26 | 2024-10-31 | Universitat De Barcelona | 1,2,4-triazole-3-thione inhibitors of trex2 for use in the treatment of psoriasis, atopic dermatitis or ichthyosis |
| WO2026032382A1 (zh) * | 2024-08-09 | 2026-02-12 | 普罗思特(南京)生物科技有限公司 | 取代的1,2,4-三唑衍生物及其应用 |
Family Cites Families (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB928919A (en) * | 1960-08-16 | 1963-06-19 | Bellon Labor Sa Roger | Triazole derivatives and a process for their preparation |
| US4269846A (en) * | 1979-10-29 | 1981-05-26 | Usv Pharmaceutical Corporation | Heterocyclic compounds useful as anti-allergy agents |
| JPS5910574A (ja) | 1982-07-07 | 1984-01-20 | Fujisawa Pharmaceut Co Ltd | トリアゾ−ル誘導体およびその製造法 |
| FR2546887B1 (fr) | 1983-05-30 | 1985-08-30 | Paris 7 Universite | Procede de preparation de dihydro-2,4 triazol-1,2,4 thiones-3 disubstituees en positions 4 et 5 et nouveaux composes pouvant etre prepares par ce procede |
| US4740568A (en) * | 1985-04-09 | 1988-04-26 | Minnesota Mining And Manufacturing Company | Triazolinethione-containing polymer |
| US4624995A (en) * | 1985-04-09 | 1986-11-25 | Minnesota Mining And Manufacturing Company | Triazolinethione-containing polymer |
| US5436252A (en) * | 1986-12-19 | 1995-07-25 | Merrell Dow Pharmaceuticals Inc. | 5-aryl-3H-1,2,4-triazol-3-ones and their use in the treatment of neurodegenerative disorders |
| US5006650A (en) * | 1987-02-11 | 1991-04-09 | The Upjohn Company | Novel N-1 substituted beta-lactams as antibiotics |
| DE3729070A1 (de) * | 1987-09-01 | 1989-03-09 | Bayer Ag | Substituierte triazolinone |
| US5869609A (en) * | 1990-12-12 | 1999-02-09 | Zymogenetics, Inc. | G protein coupled glutamate receptors |
| CZ283018B6 (cs) * | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| ATE205202T1 (de) * | 1992-03-13 | 2001-09-15 | Merck Sharp & Dohme | Imidazol-, triazol- und tetrazolderivate |
| TW218017B (https=) * | 1992-04-28 | 1993-12-21 | Takeda Pharm Industry Co Ltd | |
| DE4222771A1 (de) * | 1992-07-10 | 1994-01-13 | Bayer Ag | Heterocyclyltriazolinone |
| DE4303376A1 (de) * | 1993-02-05 | 1994-08-11 | Bayer Ag | Substituierte Triazolinone |
| DE4303676A1 (de) * | 1993-02-09 | 1994-08-11 | Bayer Ag | 1-Aryltriazolin(thi)one |
| US5538988A (en) * | 1994-04-26 | 1996-07-23 | Martinez; Gregory R. | Benzocycloalkylazolethione derivatives |
| US5489598A (en) * | 1994-06-08 | 1996-02-06 | Warner-Lambert Company | Cytoprotection utilizing aryltriazol-3-thiones |
| JP3372365B2 (ja) * | 1994-08-19 | 2003-02-04 | 富士写真フイルム株式会社 | ハロゲン化銀写真感光材料およびそれを用いた画像形成方法 |
| DE19521162A1 (de) * | 1995-06-09 | 1996-12-12 | Bayer Ag | N-Aryl-1,2,4-triazolin-5-one |
| TW467902B (en) | 1996-07-31 | 2001-12-11 | Bristol Myers Squibb Co | Diphenyl heterocycles as potassium channel modulators |
| JP2001504121A (ja) * | 1996-11-12 | 2001-03-27 | セプラコール，インク． | ２ｒ，４ｓ，ｒ，ｓ―および２ｓ，４ｒ，ｒ，ｓ―ヒドロキシイトラコナゾール―およびヒドロキシサパーコナゾール誘導体 |
| JP3788676B2 (ja) * | 1997-11-11 | 2006-06-21 | 富士写真フイルム株式会社 | 有機エレクトロルミネツセンス素子材料およびそれを使用した有機エレクトロルミネツセンス素子 |
| JP2002506060A (ja) * | 1998-03-09 | 2002-02-26 | ビーエーエスエフ アクチェンゲゼルシャフト | ヘテロアリール置換ベンジルフェニルエーテル、その製造方法、並びに有害菌類及び有害動物防除用としての使用法 |
| JP2000284412A (ja) | 1999-03-30 | 2000-10-13 | Fuji Photo Film Co Ltd | 熱現像写真材料 |
| US6492406B1 (en) * | 1999-05-21 | 2002-12-10 | Astrazeneca Ab | Pharmaceutically active compounds |
| JP4102124B2 (ja) | 2001-08-01 | 2008-06-18 | 富士フイルム株式会社 | ハロゲン化銀乳剤およびハロゲン化銀写真感光材料 |
| ATE374753T1 (de) | 2001-12-21 | 2007-10-15 | Vernalis Cambridge Ltd | 3-(2,4)dihydroxyphenyl-4-phenylpyrazole und deren medizinische verwendung |
| GB0315111D0 (en) * | 2003-06-27 | 2003-07-30 | Cancer Rec Tech Ltd | Substituted 5-membered ring compounds and their use |
| JP2005084612A (ja) * | 2003-09-11 | 2005-03-31 | Fuji Photo Film Co Ltd | ハロゲン化銀乳剤、ハロゲン化銀感光材料、および熱現像感光材料 |
| WO2005044194A2 (en) | 2003-10-28 | 2005-05-19 | Pharmacia Corporation | TREATMENT OR PREVENTION OF NEOPLASIA BY USE OF AN Hsp90 INHIBITOR |
| CA2560954A1 (en) * | 2004-03-26 | 2005-10-20 | Amphora Discovery Corporation | Certain triazole-based compounds, compositions, and uses thereof |
| EP1817295B1 (en) * | 2004-11-18 | 2012-11-07 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| DE102005007304A1 (de) * | 2005-02-17 | 2006-08-24 | Merck Patent Gmbh | Triazolderivate |
| CN101160291B (zh) | 2005-03-09 | 2012-09-05 | 日本化药株式会社 | 作为hsp90抑制剂的三唑衍生物 |
| US7608635B2 (en) | 2005-08-12 | 2009-10-27 | Synta Pharmaceuticals Corp. | Pyrazole compounds that modulate HSP90 activity |
| JP5118039B2 (ja) * | 2005-08-18 | 2013-01-16 | シンタ ファーマシューティカルズ コーポレーション | Ｈｓｐ９０活性を調節するトリアゾール化合物 |
| WO2007021877A1 (en) | 2005-08-18 | 2007-02-22 | Synta Pharmaceuticals Corp. | Imidazole 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 |
| CA2653327A1 (en) | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Compounds that modulate hsp90 activity and methods for identifying same |
| WO2007139952A2 (en) | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Method for the preparation of triazole compounds with hsp90 modulating activity |
| SI2035396T1 (sl) | 2006-05-25 | 2014-08-29 | Synta Pharmaceuticals Corp. | Triazolne spojine, ki modulirajo aktivnost HSP90 |
| WO2007139955A2 (en) | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| US8063083B2 (en) | 2006-05-25 | 2011-11-22 | Synta Pharmaceuticals Corp. | Method for treating non-Hodgkin's lymphoma |
| EP2038262B1 (en) | 2006-05-25 | 2014-11-12 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| AU2007284537B2 (en) * | 2006-08-17 | 2012-04-12 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| US20110046125A1 (en) | 2006-10-19 | 2011-02-24 | Synta Pharmaceuticals Corp. | Method for treating infections |
| WO2008057246A2 (en) | 2006-10-26 | 2008-05-15 | Synta Pharmaceuticals Corp. | Method for treating inflammatory disorders |
| PL2118077T3 (pl) | 2007-02-08 | 2015-05-29 | Synta Pharmaceuticals Corp | Związki triazolowe modulujące aktywność hsp90 |
| WO2008112199A1 (en) | 2007-03-12 | 2008-09-18 | Synta Pharmaceuticals Corp. | Method for inhibiting topoisomerase ii |
| EP2155694B1 (en) | 2007-03-27 | 2012-01-04 | Synta Pharmaceuticals Corp. | Triazinone and diazinone derivatives useful as hsp90 inhibitors |
| WO2008153730A2 (en) | 2007-05-25 | 2008-12-18 | Synta Pharmaceuticals Corp. | Method for treating proliferative disorders associated with mutations in c-met |
| AU2008287367B2 (en) | 2007-08-13 | 2012-02-23 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| US9156836B2 (en) | 2008-05-16 | 2015-10-13 | Synta Pharmaceuticals Corp. | Tricyclic triazole compounds that modulate HSP90 activity |
| US8450500B2 (en) | 2008-06-04 | 2013-05-28 | Synta Pharmaceuticals Corp. | Pyrrole compounds that modulate HSP90 activity |
| US8648071B2 (en) | 2008-06-27 | 2014-02-11 | Synta Pharmaceuticals Corp. | Hydrazonamide compounds that modulate Hsp90 activity |
| WO2010017545A2 (en) | 2008-08-08 | 2010-02-11 | Synta Pharamceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| US9126953B2 (en) | 2008-08-08 | 2015-09-08 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| EP2490688B1 (en) | 2009-10-19 | 2014-10-08 | Synta Pharmaceuticals Corp. | Combination cancer therapy with hsp90 inhibitory compounds |
| 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 |
| EP2560640A1 (en) | 2010-04-19 | 2013-02-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
| WO2011146801A1 (en) | 2010-05-20 | 2011-11-24 | Synta Pharmaceuticals Corp. | Formulation and dosing of hsp90 inhibitory compounds |
| EP2575810A1 (en) | 2010-05-24 | 2013-04-10 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compound and a topoisomerase ii inhibitor |
| US20130225870A1 (en) | 2010-08-25 | 2013-08-29 | Synta Pharmaceuticals Corp. | Method of synthesizing substituted 2-alkyl phenols |
| CN103269701A (zh) | 2010-09-13 | 2013-08-28 | 辛塔医药品有限公司 | 用于治疗野生型egfr和/或kras患者的非小细胞肺癌的hsp90抑制剂 |
| CA2817564A1 (en) | 2010-11-18 | 2012-05-24 | Ronald K. Blackman | Preselection of subjects for therapeutic treatment based on hypoxic status |
| JP2014503500A (ja) | 2010-11-18 | 2014-02-13 | シンタ ファーマスーティカルズ コーポレーション | 低酸素状態に基づく酸素感受性薬剤による治療に適した被験体の事前選択 |
| US20140005145A1 (en) | 2010-12-08 | 2014-01-02 | Synta Pharmaceuticals Corp. | Combination breast cancer therapy with hsp90 inhibitory compounds |
| US20130331357A1 (en) | 2011-01-11 | 2013-12-12 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitory compounds with proteasome inhibitors |
| WO2012116061A1 (en) | 2011-02-23 | 2012-08-30 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitory compounds with radiotherapy |
| AU2012243289A1 (en) | 2011-02-24 | 2013-08-29 | Synta Pharmaceuticals Corp. | Prostate cancer therapy with Hsp90 inhibitory compounds |
| WO2012116247A1 (en) | 2011-02-25 | 2012-08-30 | Synta Pharmaceuticals Corp. | Hsp90 inhibitory compounds in treating jak/stat signaling-mediated cancers |
| WO2012155063A1 (en) | 2011-05-11 | 2012-11-15 | Synta Pharmaceuticals Corp. | Treating cancer with an hsp90 inhibitory compound |
| WO2012162293A1 (en) | 2011-05-23 | 2012-11-29 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitory compounds with mek inhibitors |
| EP2714038A1 (en) | 2011-05-24 | 2014-04-09 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitory compounds with mtor/pi3k inhibitors |
| WO2012162584A1 (en) | 2011-05-26 | 2012-11-29 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitory compounds with chk inhibitors |
| CA2840986A1 (en) | 2011-07-07 | 2013-01-10 | Synta Pharmaceuticals Corp. | Treating cancer with hsp90 inhibitory compounds |
| US20140296176A1 (en) | 2011-08-19 | 2014-10-02 | Synta Pharmaceuticals Corp. | Combination cancer therapy with an hsp90 inhibitor and an antimetabolite |
| US8628752B2 (en) | 2011-10-28 | 2014-01-14 | Synta Pharmaceuticals Corp. | Methods of identifying HSP90 inhibitors with less ocular toxicity |
| JP2014534228A (ja) | 2011-11-02 | 2014-12-18 | シンタ ファーマシューティカルズ コーポレーション | 白金含有剤とｈｓｐ９０阻害剤の組合せ療法 |
| CA2853799A1 (en) | 2011-11-02 | 2013-05-10 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of hsp90 inhibitors with topoisomerase i inhibitors |
| US9402831B2 (en) | 2011-11-14 | 2016-08-02 | Synta Pharmaceutical Corp. | Combination therapy of HSP90 inhibitors with BRAF inhibitors |
| WO2013148857A1 (en) | 2012-03-28 | 2013-10-03 | Synta Pharmaceuticals Corp. | Triazole derivatives as hsp90 inhibitors |
-
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- 2007-05-25 PL PL07795379T patent/PL2035396T3/pl unknown
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2013
- 2013-04-05 US US13/857,665 patent/US8835464B2/en active Active
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2014
- 2014-08-29 US US14/473,366 patent/US9006277B2/en active Active
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2015
- 2015-04-13 US US14/685,178 patent/US9206162B2/en active Active
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