JP2013508378A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013508378A5 JP2013508378A5 JP2012535301A JP2012535301A JP2013508378A5 JP 2013508378 A5 JP2013508378 A5 JP 2013508378A5 JP 2012535301 A JP2012535301 A JP 2012535301A JP 2012535301 A JP2012535301 A JP 2012535301A JP 2013508378 A5 JP2013508378 A5 JP 2013508378A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- triazole
- indol
- phenyl
- mercapto
- 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.)
- Ceased
Links
- -1 guanazino Chemical group 0.000 claims description 40
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 23
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 12
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 11
- 229930012538 Paclitaxel Natural products 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 201000005202 lung cancer Diseases 0.000 claims description 11
- 208000020816 lung neoplasm Diseases 0.000 claims description 11
- 229960001592 paclitaxel Drugs 0.000 claims description 11
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 150000003852 triazoles Chemical class 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 235000021317 phosphate Nutrition 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 claims description 5
- 208000036566 Erythroleukaemia Diseases 0.000 claims description 5
- 208000021841 acute erythroid leukemia Diseases 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 5
- ZAVMYGRJGRTKNS-UHFFFAOYSA-N 4-(1,2-dimethylindol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=C(C)N(C)C3=CC=2)=C1O ZAVMYGRJGRTKNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 3
- 229960003668 docetaxel Drugs 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- PCKARBFVTAHKLL-UHFFFAOYSA-N 1-[5-[3-(5-ethyl-2,4-dihydroxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-2,3-dimethylindol-1-yl]ethanone Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=C(C)N(C(C)=O)C3=CC=2)=C1O PCKARBFVTAHKLL-UHFFFAOYSA-N 0.000 claims description 2
- UBYWHLVHDACFMM-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1,3-dimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O UBYWHLVHDACFMM-UHFFFAOYSA-N 0.000 claims description 2
- LIRCZXORVKKVOJ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-ethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(CC)C=CC2=CC=1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O LIRCZXORVKKVOJ-UHFFFAOYSA-N 0.000 claims description 2
- STVGXJKUWLHOGD-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-propylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(CCC)C=CC2=CC=1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O STVGXJKUWLHOGD-UHFFFAOYSA-N 0.000 claims description 2
- BTGVBRHYZUAKCR-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1H-indol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3C=CNC3=CC=2)=C1O BTGVBRHYZUAKCR-UHFFFAOYSA-N 0.000 claims description 2
- NDPQZXRORWTRAB-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=2C=CN(C(C)C)C=2C(OC)=CC=C1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O NDPQZXRORWTRAB-UHFFFAOYSA-N 0.000 claims description 2
- UIVTZISQSMHJKS-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1-ethylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CC)C=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O UIVTZISQSMHJKS-UHFFFAOYSA-N 0.000 claims description 2
- RKFOLXISFIXXRI-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(C(C)C)C=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O RKFOLXISFIXXRI-UHFFFAOYSA-N 0.000 claims description 2
- UBBWIIUNTKWYMN-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(1H-indol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound OC1=CC(O)=CC=C1C1=NN=C(S)N1C1=CC=CC2=C1C=CN2 UBBWIIUNTKWYMN-UHFFFAOYSA-N 0.000 claims description 2
- LQKKAHUTPJMJET-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-[2-(1-methoxyethyl)-1H-indol-4-yl]-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2NC(C(C)OC)=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O LQKKAHUTPJMJET-UHFFFAOYSA-N 0.000 claims description 2
- HVFFXYJWYZFIBV-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(1,2,3-trimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(C)C(C)=C(C)C2=CC=1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 HVFFXYJWYZFIBV-UHFFFAOYSA-N 0.000 claims description 2
- QFROSIGFOALPEM-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(1,3-dimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2C(C)=CN(C)C2=CC=C1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 QFROSIGFOALPEM-UHFFFAOYSA-N 0.000 claims description 2
- REUUXTDHNKRGOI-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=2C=CN(C(C)C)C=2C(OC)=CC=C1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 REUUXTDHNKRGOI-UHFFFAOYSA-N 0.000 claims description 2
- UATPOJPGMXSVGQ-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC(OC)=C2N(CCC)C=CC2=C1N1C(S)=NN=C1C(C(=CC=1O)O)=CC=1C1CC1 UATPOJPGMXSVGQ-UHFFFAOYSA-N 0.000 claims description 2
- VDODPAGJCVTEJQ-UHFFFAOYSA-N 3-(5-cyclopropyl-2,4-dihydroxyphenyl)-4-[1-(1-methylcyclopropyl)indol-4-yl]-1H-1,2,4-triazole-5-thione Chemical compound C1=CC2=C(N3C(=NN=C3S)C=3C(=CC(O)=C(C4CC4)C=3)O)C=CC=C2N1C1(C)CC1 VDODPAGJCVTEJQ-UHFFFAOYSA-N 0.000 claims description 2
- STLUOXMEJVFZCP-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1,2,3-trimethylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=C(C)N(C)C3=CC=2)=C1O STLUOXMEJVFZCP-UHFFFAOYSA-N 0.000 claims description 2
- YUZVSLHCEHKSQJ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-hexylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCCCCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O YUZVSLHCEHKSQJ-UHFFFAOYSA-N 0.000 claims description 2
- UOZMPLARHDBOPI-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-methyl-3-propan-2-ylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C(C)C)=CN(C)C3=CC=2)=C1O UOZMPLARHDBOPI-UHFFFAOYSA-N 0.000 claims description 2
- INSPZFPAIAETMI-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O INSPZFPAIAETMI-UHFFFAOYSA-N 0.000 claims description 2
- OLLRLHGHUWXAFP-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-pentylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCCCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O OLLRLHGHUWXAFP-UHFFFAOYSA-N 0.000 claims description 2
- QZCQHJMGZJLICK-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C=CC=2)C(C)C)=C1O QZCQHJMGZJLICK-UHFFFAOYSA-N 0.000 claims description 2
- LBVJBJFVUWQRLE-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-propylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O LBVJBJFVUWQRLE-UHFFFAOYSA-N 0.000 claims description 2
- QSFLGQYOSRZJAQ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(3-ethyl-1-methylindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2C(CC)=CN(C)C2=CC=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O QSFLGQYOSRZJAQ-UHFFFAOYSA-N 0.000 claims description 2
- BXLIPBMFJHQUAZ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-hydroxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C(O)=CC=2)C(C)C)=C1O BXLIPBMFJHQUAZ-UHFFFAOYSA-N 0.000 claims description 2
- ZBXXGZDCLQEVEQ-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=CN(C=3C(OC)=CC=2)C(C)C)=C1O ZBXXGZDCLQEVEQ-UHFFFAOYSA-N 0.000 claims description 2
- QYVIZOQFOBGAHW-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(7-methoxy-2-methyl-1-benzofuran-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=3C=C(C)OC=3C(OC)=CC=2)=C1O QYVIZOQFOBGAHW-UHFFFAOYSA-N 0.000 claims description 2
- JJEYWCWGANAGDC-UHFFFAOYSA-N 3-(5-tert-butyl-2,4-dihydroxyphenyl)-4-(7-methoxy-1-propan-2-ylindol-4-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=2C=CN(C(C)C)C=2C(OC)=CC=C1N1C(S)=NN=C1C1=CC(C(C)(C)C)=C(O)C=C1O JJEYWCWGANAGDC-UHFFFAOYSA-N 0.000 claims description 2
- PCYXGRPZGRZCMY-UHFFFAOYSA-N 4-(1,3-dimethylindol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O PCYXGRPZGRZCMY-UHFFFAOYSA-N 0.000 claims description 2
- CXWAUYMEDCGIRL-UHFFFAOYSA-N 4-(1-benzofuran-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C=COC3=CC=2)=C1O CXWAUYMEDCGIRL-UHFFFAOYSA-N 0.000 claims description 2
- GXDNJALLRJLOSU-UHFFFAOYSA-N 4-(1-butylindol-4-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=CC=C2N(CCCC)C=CC2=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O GXDNJALLRJLOSU-UHFFFAOYSA-N 0.000 claims description 2
- PZBMTCSNWKKAJE-UHFFFAOYSA-N 4-(2,3-dimethyl-1-propylindol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C=1C=C2N(CCC)C(C)=C(C)C2=CC=1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O PZBMTCSNWKKAJE-UHFFFAOYSA-N 0.000 claims description 2
- DVYPKVKKDQJXJG-UHFFFAOYSA-N 4-(2,3-dimethyl-1H-indol-5-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3C(C)=C(C)NC3=CC=2)=C1O DVYPKVKKDQJXJG-UHFFFAOYSA-N 0.000 claims description 2
- IEXWEVLAAWUJAO-UHFFFAOYSA-N 4-(7-ethoxy-1-propan-2-ylindol-4-yl)-3-(5-ethyl-2,4-dihydroxyphenyl)-1H-1,2,4-triazole-5-thione Chemical compound C1=2C=CN(C(C)C)C=2C(OCC)=CC=C1N1C(S)=NN=C1C1=CC(CC)=C(O)C=C1O IEXWEVLAAWUJAO-UHFFFAOYSA-N 0.000 claims description 2
- JNQALWWIUZZILK-UHFFFAOYSA-N 4-[3-(2,4-dihydroxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-N,N-dimethylindole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N(C)C)C=CC2=C1N1C(S)=NN=C1C1=CC=C(O)C=C1O JNQALWWIUZZILK-UHFFFAOYSA-N 0.000 claims description 2
- BPRVREHELHZYJN-UHFFFAOYSA-N 5-(1-methylindol-5-yl)-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound C=1C=C2N(C)C=CC2=CC=1C1=NC(=S)NN1 BPRVREHELHZYJN-UHFFFAOYSA-N 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- SAFUWGYHSHRERQ-UHFFFAOYSA-N [2-[4-(2,3-dihydro-1H-inden-5-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-5-hydroxy-4-propan-2-ylphenyl] dihydrogen phosphate Chemical class C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3CCCC3=CC=2)=C1OP(O)(O)=O SAFUWGYHSHRERQ-UHFFFAOYSA-N 0.000 claims description 2
- HSPYRDASOJURBP-UHFFFAOYSA-N [4-(2,3-dihydro-1H-inden-5-yl)-5-(2,4-dihydroxy-5-propan-2-ylphenyl)-1,2,4-triazol-3-yl] dihydrogen phosphate Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(OP(O)(O)=O)=NN=2)C=2C=C3CCCC3=CC=2)=C1O HSPYRDASOJURBP-UHFFFAOYSA-N 0.000 claims description 2
- BALPIGOECICYSD-UHFFFAOYSA-N [4-[4-(1,3-dimethylindol-5-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-2-ethyl-5-hydroxyphenyl] dihydrogen phosphate Chemical compound C1=C(OP(O)(O)=O)C(CC)=CC(C=2N(C(O)=NN=2)C=2C=C3C(C)=CN(C)C3=CC=2)=C1O BALPIGOECICYSD-UHFFFAOYSA-N 0.000 claims description 2
- CKKHGJCUBHEFQY-UHFFFAOYSA-N [4-[4-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-5-oxo-1H-1,2,4-triazol-3-yl]-5-hydroxy-2-propan-2-ylphenyl] dihydrogen phosphate Chemical compound C1=C(OP(O)(O)=O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=C3OCCOC3=CC=2)=C1O CKKHGJCUBHEFQY-UHFFFAOYSA-N 0.000 claims description 2
- BYPDYJHVTIARDI-UHFFFAOYSA-N [4-[4-(2,3-dihydro-1H-inden-5-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-5-hydroxy-2-propan-2-ylphenyl] dihydrogen phosphate Chemical class C1=C(OP(O)(O)=O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3CCCC3=CC=2)=C1O BYPDYJHVTIARDI-UHFFFAOYSA-N 0.000 claims description 2
- WLUZVUCJKRMBER-UHFFFAOYSA-N [4-[4-(4-bromo-2-methylphenyl)-5-oxo-1H-1,2,4-triazol-3-yl]-3-hydroxyphenyl] dihydrogen phosphate Chemical compound CC1=CC(Br)=CC=C1N1C(C=2C(=CC(OP(O)(O)=O)=CC=2)O)=NN=C1O WLUZVUCJKRMBER-UHFFFAOYSA-N 0.000 claims description 2
- JNWFIPVDEINBAI-UHFFFAOYSA-N [5-hydroxy-4-[4-(1-methylindol-5-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-2-propan-2-ylphenyl] dihydrogen phosphate Chemical compound C1=C(OP(O)(O)=O)C(C(C)C)=CC(C=2N(C(=O)NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O JNWFIPVDEINBAI-UHFFFAOYSA-N 0.000 claims description 2
- KDGFMVVMKCWWMT-UHFFFAOYSA-N [5-hydroxy-4-[4-(6-morpholin-4-ylpyridin-3-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-2-propan-2-ylphenyl] dihydrogen phosphate Chemical compound C1=C(OP(O)(O)=O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=NC(=CC=2)N2CCOCC2)=C1O KDGFMVVMKCWWMT-UHFFFAOYSA-N 0.000 claims description 2
- PESPGTPZJKWRDS-UHFFFAOYSA-N [5-hydroxy-4-[4-[(4-methoxyphenyl)methyl]-5-oxo-1H-1,2,4-triazol-3-yl]-2-propan-2-ylphenyl] dihydrogen phosphate Chemical compound C1=CC(OC)=CC=C1CN1C(C=2C(=CC(OP(O)(O)=O)=C(C(C)C)C=2)O)=NN=C1O PESPGTPZJKWRDS-UHFFFAOYSA-N 0.000 claims description 2
- IYEHPIZSXOBJLY-UHFFFAOYSA-N [Na].[Na].CCc1cc(-c2nnc(S)n2-c2ccc(OC)c3n(ccc23)C(C)C)c(O)cc1O Chemical compound [Na].[Na].CCc1cc(-c2nnc(S)n2-c2ccc(OC)c3n(ccc23)C(C)C)c(O)cc1O IYEHPIZSXOBJLY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 2
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- AWHPLFDGSGMBIN-UHFFFAOYSA-L disodium [5-hydroxy-4-[4-(1-methylindol-5-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-2-propan-2-ylphenyl] phosphate Chemical compound [Na+].[Na+].CC(C)c1cc(-c2nnc(O)n2-c2ccc3n(C)ccc3c2)c(O)cc1OP([O-])([O-])=O AWHPLFDGSGMBIN-UHFFFAOYSA-L 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 30
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 31
- 0 C[n]1c(-c(c(O)c2)cc(*)c2OCO)nnc1* Chemical compound C[n]1c(-c(c(O)c2)cc(*)c2OCO)nnc1* 0.000 description 3
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27933009P | 2009-10-19 | 2009-10-19 | |
| US61/279,330 | 2009-10-19 | ||
| US33577810P | 2010-01-11 | 2010-01-11 | |
| US61/335,778 | 2010-01-11 | ||
| PCT/US2010/053199 WO2011049946A1 (en) | 2009-10-19 | 2010-10-19 | Combination cancer therapy with hsp90 inhibitory compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015199844A Division JP2016041715A (ja) | 2009-10-19 | 2015-10-08 | Ｈｓｐ９０阻害化合物を用いる併用がん療法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013508378A JP2013508378A (ja) | 2013-03-07 |
| JP2013508378A5 true JP2013508378A5 (enExample) | 2013-12-05 |
Family
ID=43218142
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012535301A Ceased JP2013508378A (ja) | 2009-10-19 | 2010-10-19 | Ｈｓｐ９０阻害化合物を用いる併用がん療法 |
| JP2015199844A Pending JP2016041715A (ja) | 2009-10-19 | 2015-10-08 | Ｈｓｐ９０阻害化合物を用いる併用がん療法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015199844A Pending JP2016041715A (ja) | 2009-10-19 | 2015-10-08 | Ｈｓｐ９０阻害化合物を用いる併用がん療法 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20120245186A1 (enExample) |
| EP (1) | EP2490688B1 (enExample) |
| JP (2) | JP2013508378A (enExample) |
| KR (1) | KR20120093970A (enExample) |
| CN (1) | CN102695504A (enExample) |
| AU (1) | AU2010308306A1 (enExample) |
| BR (1) | BR112012009215A2 (enExample) |
| CA (1) | CA2779233A1 (enExample) |
| CY (1) | CY1115902T1 (enExample) |
| DK (1) | DK2490688T3 (enExample) |
| EA (1) | EA022119B1 (enExample) |
| ES (1) | ES2526566T3 (enExample) |
| HR (1) | HRP20141150T1 (enExample) |
| MX (1) | MX2012004577A (enExample) |
| NZ (2) | NZ599445A (enExample) |
| PH (1) | PH12012500748A1 (enExample) |
| PL (1) | PL2490688T3 (enExample) |
| PT (1) | PT2490688E (enExample) |
| RS (1) | RS53716B1 (enExample) |
| SI (1) | SI2490688T1 (enExample) |
| WO (1) | WO2011049946A1 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1934185A1 (en) | 2005-08-12 | 2008-06-25 | Synta Pharmaceuticals Corporation | Pyrazole 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 |
| CA2653336C (en) | 2006-05-25 | 2014-10-28 | Synta Pharmaceuticals Corp. | Method for treating non-hodgkin's lymphoma |
| AU2007267859B2 (en) | 2006-05-25 | 2012-04-12 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate Hsp90 activity |
| US8034834B2 (en) | 2006-05-25 | 2011-10-11 | Synta Pharmaceuticals Corp. | Method for treating proliferative disorders with HSP90 inhibitors |
| 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 |
| WO2010017479A1 (en) * | 2008-08-08 | 2010-02-11 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| WO2010017545A2 (en) | 2008-08-08 | 2010-02-11 | Synta Pharamceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| US20130045992A1 (en) | 2010-01-28 | 2013-02-21 | President And Fellows Of Harvard College | Compositions and Methods for Enhancing Proteasome Activity |
| WO2011133520A1 (en) | 2010-04-19 | 2011-10-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
| WO2011146803A1 (en) * | 2010-05-20 | 2011-11-24 | Synta Pharmaceuticals Corp. | Method of treating lung adenocarcinoma with hsp90 inhibitory compounds |
| US20130172333A1 (en) * | 2010-05-20 | 2013-07-04 | Synta Pharmaceuticals Corp. | Formulation and dosing of hsp90 inhibitory compounds |
| US20130171105A1 (en) * | 2010-05-24 | 2013-07-04 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compound and a topoisomerase ii inhibitor |
| AU2011302344B2 (en) * | 2010-09-13 | 2015-01-15 | Synta Pharmaceuticals Corp. | HSP90 inhibitors for treating non-small cell lung cancers in wild-type EGFR and/or KRAS patients |
| WO2012154967A1 (en) | 2011-05-12 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| EP2714039A1 (en) * | 2011-05-23 | 2014-04-09 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitory compounds with mek inhibitors |
| WO2012162372A1 (en) * | 2011-05-24 | 2012-11-29 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitory compounds with mtor/p13k inhibitors |
| WO2012162584A1 (en) * | 2011-05-26 | 2012-11-29 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitory compounds with chk inhibitors |
| WO2013006864A2 (en) * | 2011-07-07 | 2013-01-10 | Synta Pharmaceuticals Corp. | Treating cancer with hsp90 inhibitory compounds |
| WO2013067165A1 (en) | 2011-11-02 | 2013-05-10 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with platinum-containing agents |
| JP2014532712A (ja) * | 2011-11-02 | 2014-12-08 | シンタ ファーマシューティカルズ コーポレーション | トポイソメラーゼｉ阻害剤とｈｓｐ９０阻害剤の組合せを使用する癌療法 |
| WO2013074594A1 (en) * | 2011-11-14 | 2013-05-23 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
| US9849135B2 (en) | 2013-01-25 | 2017-12-26 | President And Fellows Of Harvard College | USP14 inhibitors for treating or preventing viral infections |
| CA2938626A1 (en) | 2013-07-26 | 2015-01-29 | John Rothman | Compositions to improve the therapeutic benefit of bisantrene |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| LT3177612T (lt) | 2014-08-04 | 2022-06-10 | Nuevolution A/S | Pirimidino dariniai, pakeisti pasirinktinai kondensuotu heterociklilu, tinkami uždegiminių, metabolinių, onkologinių ir autoimuninių ligų gydymui |
| KR102630013B1 (ko) | 2015-08-06 | 2024-01-25 | 키메릭스 인크. | 항바이러스제로서 유용한 피롤로피리미딘 뉴클레오시드 및 그의 유사체 |
| CN105237533B (zh) * | 2015-10-26 | 2017-03-22 | 中国药科大学 | 四氢吡啶并[4,3‑d]嘧啶类Hsp90抑制剂及其医药用途 |
| US11111264B2 (en) | 2017-09-21 | 2021-09-07 | Chimerix, Inc. | Morphic forms of 4-amino-7-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide and uses thereof |
| TWI872177B (zh) | 2019-12-20 | 2025-02-11 | 丹麥商紐韋盧森公司 | 對核受體具有活性之化合物 |
| MX2022007265A (es) | 2019-12-20 | 2022-09-09 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| US11613532B2 (en) | 2020-03-31 | 2023-03-28 | Nuevolution A/S | Compounds active towards nuclear receptors |
| US11780843B2 (en) | 2020-03-31 | 2023-10-10 | Nuevolution A/S | Compounds active towards nuclear receptors |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536809A (en) | 1969-02-17 | 1970-10-27 | Alza Corp | Medication method |
| US3598123A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US4008719A (en) | 1976-02-02 | 1977-02-22 | Alza Corporation | Osmotic system having laminar arrangement for programming delivery of active agent |
| IE58110B1 (en) | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| US5073543A (en) | 1988-07-21 | 1991-12-17 | G. D. Searle & Co. | Controlled release formulations of trophic factors in ganglioside-lipsome vehicle |
| IT1229203B (it) | 1989-03-22 | 1991-07-25 | Bioresearch Spa | Impiego di acido 5 metiltetraidrofolico, di acido 5 formiltetraidrofolico e dei loro sali farmaceuticamente accettabili per la preparazione di composizioni farmaceutiche in forma a rilascio controllato attive nella terapia dei disturbi mentali organici e composizioni farmaceutiche relative. |
| US5120548A (en) | 1989-11-07 | 1992-06-09 | Merck & Co., Inc. | Swelling modulated polymeric drug delivery device |
| US5733566A (en) | 1990-05-15 | 1998-03-31 | Alkermes Controlled Therapeutics Inc. Ii | Controlled release of antiparasitic agents in animals |
| US5580578A (en) | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| US5591767A (en) | 1993-01-25 | 1997-01-07 | Pharmetrix Corporation | Liquid reservoir transdermal patch for the administration of ketorolac |
| IT1270594B (it) | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| US6274171B1 (en) | 1996-03-25 | 2001-08-14 | American Home Products Corporation | Extended release formulation of venlafaxine hydrochloride |
| RS52642B (sr) | 2004-11-18 | 2013-06-28 | Synta Pharmaceuticals Corp. | Jedinjenja triazola koja modulišu aktivnost hsp90 |
| US8034834B2 (en) * | 2006-05-25 | 2011-10-11 | Synta Pharmaceuticals Corp. | Method for treating proliferative disorders with HSP90 inhibitors |
| DE102007002715A1 (de) * | 2007-01-18 | 2008-07-24 | Merck Patent Gmbh | Triazolderivat |
| TW200901960A (en) * | 2007-03-05 | 2009-01-16 | Kyowa Hakko Kogyo Kk | Pharmaceutical composition |
| WO2009002321A1 (en) | 2007-06-27 | 2008-12-31 | Thomson Licensing | Enhancing image quality |
| KR20100057030A (ko) * | 2007-08-13 | 2010-05-28 | 신타 파마슈티칼스 코프. | Ｈｓｐ90의 활성을 조절하는 트라이아졸 화합물 |
| WO2013006864A2 (en) * | 2011-07-07 | 2013-01-10 | Synta Pharmaceuticals Corp. | Treating cancer with hsp90 inhibitory compounds |
-
2010
- 2010-10-19 NZ NZ599445A patent/NZ599445A/en not_active IP Right Cessation
- 2010-10-19 CA CA2779233A patent/CA2779233A1/en not_active Abandoned
- 2010-10-19 JP JP2012535301A patent/JP2013508378A/ja not_active Ceased
- 2010-10-19 WO PCT/US2010/053199 patent/WO2011049946A1/en not_active Ceased
- 2010-10-19 SI SI201030832T patent/SI2490688T1/sl unknown
- 2010-10-19 MX MX2012004577A patent/MX2012004577A/es active IP Right Grant
- 2010-10-19 DK DK10768357.5T patent/DK2490688T3/en active
- 2010-10-19 NZ NZ622713A patent/NZ622713A/en not_active IP Right Cessation
- 2010-10-19 AU AU2010308306A patent/AU2010308306A1/en not_active Abandoned
- 2010-10-19 ES ES10768357.5T patent/ES2526566T3/es active Active
- 2010-10-19 PH PH1/2012/500748A patent/PH12012500748A1/en unknown
- 2010-10-19 PT PT107683575T patent/PT2490688E/pt unknown
- 2010-10-19 BR BR112012009215A patent/BR112012009215A2/pt not_active IP Right Cessation
- 2010-10-19 KR KR1020127012977A patent/KR20120093970A/ko not_active Ceased
- 2010-10-19 HR HRP20141150AT patent/HRP20141150T1/hr unknown
- 2010-10-19 EA EA201270570A patent/EA022119B1/ru not_active IP Right Cessation
- 2010-10-19 CN CN201080056689XA patent/CN102695504A/zh active Pending
- 2010-10-19 US US13/501,608 patent/US20120245186A1/en not_active Abandoned
- 2010-10-19 EP EP10768357.5A patent/EP2490688B1/en active Active
- 2010-10-19 RS RS20140705A patent/RS53716B1/sr unknown
- 2010-10-19 PL PL10768357T patent/PL2490688T3/pl unknown
-
2014
- 2014-12-31 CY CY20141101097T patent/CY1115902T1/el unknown
-
2015
- 2015-10-08 JP JP2015199844A patent/JP2016041715A/ja active Pending