JP5441691B2 - Hsp90活性を調節するトリアゾール化合物 - Google Patents
Hsp90活性を調節するトリアゾール化合物 Download PDFInfo
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- JP5441691B2 JP5441691B2 JP2009512171A JP2009512171A JP5441691B2 JP 5441691 B2 JP5441691 B2 JP 5441691B2 JP 2009512171 A JP2009512171 A JP 2009512171A JP 2009512171 A JP2009512171 A JP 2009512171A JP 5441691 B2 JP5441691 B2 JP 5441691B2
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- Prior art keywords
- optionally substituted
- indol
- hydroxy
- methyl
- triazole
- Prior art date
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- -1 Triazole compounds Chemical class 0.000 title claims description 203
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 title description 50
- 230000000694 effects Effects 0.000 title description 45
- 101710113864 Heat shock protein 90 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 332
- 125000001072 heteroaryl group Chemical group 0.000 claims description 198
- 125000000623 heterocyclic group Chemical group 0.000 claims description 170
- 125000003107 substituted aryl group Chemical group 0.000 claims description 139
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 134
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 131
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 123
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 121
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 114
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 113
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 111
- 229910052757 nitrogen Inorganic materials 0.000 claims description 106
- 206010028980 Neoplasm Diseases 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- 125000001188 haloalkyl group Chemical group 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 71
- 201000011510 cancer Diseases 0.000 claims description 69
- 239000012453 solvate Substances 0.000 claims description 69
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 241000124008 Mammalia Species 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 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 14
- 230000033115 angiogenesis Effects 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 11
- 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 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 8
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 208000026278 immune system disease Diseases 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 208000035473 Communicable disease Diseases 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- WHIIXSCFGRHQCJ-UHFFFAOYSA-N [5-(2,4-dihydroxy-5-methoxyphenyl)-4-(8-methoxyquinolin-5-yl)-1,2,4-triazol-3-yl] carbamate Chemical compound C1=C(O)C(OC)=CC(C=2N(C(OC(N)=O)=NN=2)C=2C3=CC=CN=C3C(OC)=CC=2)=C1O WHIIXSCFGRHQCJ-UHFFFAOYSA-N 0.000 claims description 3
- HVWSHSGHPASERA-UHFFFAOYSA-N [5-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-methylindol-4-yl)-1,2,4-triazol-3-yl] carbamate Chemical compound C1=C(O)C(CC)=CC(C=2N(C(OC(N)=O)=NN=2)C=2C=3C=CN(C)C=3C=CC=2)=C1O HVWSHSGHPASERA-UHFFFAOYSA-N 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 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
- 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
- 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
- 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
- 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
- QHSGVPOUPDPSJM-UHFFFAOYSA-N 3-(6-hydroxy-2,3-dimethyl-1H-indol-5-yl)-4-(4-propyl-2,3-dihydro-1,4-benzoxazin-6-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2N(CCC)CCOC2=CC=C1N1C(S)=NN=C1C(C(=C1)O)=CC2=C1NC(C)=C2C QHSGVPOUPDPSJM-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
- 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
- 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
- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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| US60/808,253 | 2006-05-25 | ||
| 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 JP2009538321A5 (https=) | 2010-07-08 |
| JP5441691B2 true JP5441691B2 (ja) | 2014-03-12 |
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| JPH1143120A (ja) * | 1997-07-28 | 1999-02-16 | Ishikawajima Harima Heavy Ind Co Ltd | 容器の後処理装置 |
| WO2006055760A1 (en) * | 2004-11-18 | 2006-05-26 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| US8399464B2 (en) * | 2005-03-09 | 2013-03-19 | Nippon Kayaku Kabushiki Kaisha | HSP90 inhibitor |
| 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 |
| 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 |
| 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 |
| EP2026797A2 (en) | 2006-05-25 | 2009-02-25 | Synta Pharmaceuticals Corporation | Method for treating non-hodgkin's lymphoma |
| WO2008021364A2 (en) * | 2006-08-17 | 2008-02-21 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| 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 |
| TW200904417A (en) * | 2007-02-20 | 2009-02-01 | Synta Pharmaceuticals Corp | Triazole compounds that modulate Hsp90 activity |
| US8993608B2 (en) * | 2007-03-12 | 2015-03-31 | Synta Pharmaceuticals Corp. | Method for inhibiting topoisomerase II |
| CN101801983B (zh) | 2007-08-13 | 2014-01-29 | 辛塔制药公司 | 调控hsp90活性的三唑化合物 |
| WO2009075890A2 (en) * | 2007-12-12 | 2009-06-18 | Synta Pharmaceuticals Corp. | Method for synthesis of triazole compounds that modulate hsp90 activity |
| MX2010008376A (es) | 2008-02-04 | 2011-02-22 | Mercury Therapeutics Inc | Moduladores ampk. |
| 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 |
| WO2010100127A1 (en) | 2009-03-04 | 2010-09-10 | Novartis Ag | Disubstituted imidazole derivatives as modulators of raf kinase |
| WO2010139966A1 (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 |
| 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 |
| JP2013544874A (ja) | 2010-12-08 | 2013-12-19 | オスロ ユニヴァーシティー ホスピタル エイチエフ | Wntシグナル伝達経路阻害薬としてのトリアゾール誘導体 |
| TW201309672A (zh) * | 2011-01-07 | 2013-03-01 | Taiho Pharmaceutical Co Ltd | 新穎吲哚、吲唑衍生物或其鹽 |
| 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 |
| EP2831061A1 (en) * | 2012-03-28 | 2015-02-04 | Synta Pharmaceuticals Corp. | Triazole derivatives as hsp90 inhibitors |
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