JP2009538320A5 - - Google Patents
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- JP2009538320A5 JP2009538320A5 JP2009512169A JP2009512169A JP2009538320A5 JP 2009538320 A5 JP2009538320 A5 JP 2009538320A5 JP 2009512169 A JP2009512169 A JP 2009512169A JP 2009512169 A JP2009512169 A JP 2009512169A JP 2009538320 A5 JP2009538320 A5 JP 2009538320A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- triazol
- diol
- hydroxy
- 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.)
- Granted
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- -1 guanazino Chemical group 0.000 claims description 340
- 150000001875 compounds Chemical class 0.000 claims description 294
- 125000001072 heteroaryl group Chemical group 0.000 claims description 107
- 125000000623 heterocyclic group Chemical group 0.000 claims description 102
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 90
- 229910052757 nitrogen Inorganic materials 0.000 claims description 86
- 125000003107 substituted aryl group Chemical group 0.000 claims description 86
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 84
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 81
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 78
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 78
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 78
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 78
- 125000001188 haloalkyl group Chemical group 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 31
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
- 229940002612 prodrug Drugs 0.000 claims description 30
- 239000000651 prodrug Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000012453 solvate Substances 0.000 claims description 30
- 241000124008 Mammalia Species 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 229960001755 resorcinol Drugs 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 210000004027 cell Anatomy 0.000 claims description 6
- 230000015556 catabolic process Effects 0.000 claims description 5
- 238000006731 degradation reaction Methods 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000001939 inductive effect Effects 0.000 claims description 5
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 claims description 4
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims description 4
- 101001016865 Homo sapiens Heat shock protein HSP 90-alpha Proteins 0.000 claims description 4
- 101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 claims description 4
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 claims description 4
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 claims description 4
- 102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 claims description 4
- 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 4
- 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 4
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 4
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 4
- LYZLSQLEAHGMQA-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindazol-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=NN(C)C3=CC=2)=C1O LYZLSQLEAHGMQA-UHFFFAOYSA-N 0.000 claims description 3
- AHXQIXWOSLLMNU-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylindazol-6-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3N(C)N=CC3=CC=2)=C1O AHXQIXWOSLLMNU-UHFFFAOYSA-N 0.000 claims description 3
- IKBGRYOHMRPODX-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-methylindazol-6-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C2=CC3=NN(C)C=C3C=C2)=C1O IKBGRYOHMRPODX-UHFFFAOYSA-N 0.000 claims description 3
- JJGWYOSOCCDKJU-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[1-methyl-2-(trifluoromethyl)benzimidazol-5-yl]-1H-1,2,4-triazole-5-thione Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(S)=NN=2)C=2C=C3N=C(N(C)C3=CC=2)C(F)(F)F)=C1O JJGWYOSOCCDKJU-UHFFFAOYSA-N 0.000 claims description 3
- NDJPGJFQGHQYDJ-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-(5,6,7,8-tetrahydronaphthalen-1-yl)-1H-1,2,4-triazole-5-thione Chemical compound OC1=CC(O)=CC=C1C1=NN=C(S)N1C1=CC=CC2=C1CCCC2 NDJPGJFQGHQYDJ-UHFFFAOYSA-N 0.000 claims description 3
- PLZZEEUELXPBRR-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-4-isoquinolin-5-yl-1H-1,2,4-triazole-5-thione Chemical compound OC1=CC(O)=CC=C1C1=NN=C(S)N1C1=CC=CC2=CN=CC=C12 PLZZEEUELXPBRR-UHFFFAOYSA-N 0.000 claims description 3
- MJOVNZNBOYZUES-UHFFFAOYSA-N 3-(5-ethyl-2,4-dihydroxyphenyl)-4-(1-methyl-2,3-dihydroindol-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=C3CCN(C)C3=CC=2)=C1O MJOVNZNBOYZUES-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- AFKBFFIARXHSKJ-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-(2,4-dihydroxy-5-propan-2-ylphenyl)-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=C3OCOC3=CC=2)=C1O AFKBFFIARXHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- MHSMEFZGWDQCLQ-UHFFFAOYSA-N 4-(2,3-dihydro-1H-inden-5-yl)-3-(2,4-dihydroxy-5-propan-2-ylphenyl)-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=C3CCCC3=CC=2)=C1O MHSMEFZGWDQCLQ-UHFFFAOYSA-N 0.000 claims description 3
- QUMCEVYUCICCPO-UHFFFAOYSA-N 5-[3-(5-ethyl-2,4-dihydroxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3NC(=O)NC3=CC=2)=C1O QUMCEVYUCICCPO-UHFFFAOYSA-N 0.000 claims description 3
- ADDLVFDOBGWGMK-UHFFFAOYSA-N 5-[3-(5-ethyl-2,4-dihydroxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-1,3-dihydroindol-2-one Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3CC(=O)NC3=CC=2)=C1O ADDLVFDOBGWGMK-UHFFFAOYSA-N 0.000 claims description 3
- VIJCSJWVEITRBE-UHFFFAOYSA-N 6-[3-(5-ethyl-2,4-dihydroxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-3-methyl-1,3-benzothiazol-2-one Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3SC(=O)N(C)C3=CC=2)=C1O VIJCSJWVEITRBE-UHFFFAOYSA-N 0.000 claims description 3
- AVUJFTYWVXBGRV-UHFFFAOYSA-N 6-[3-(5-ethyl-2,4-dihydroxyphenyl)-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-3H-1,3-benzothiazol-2-one Chemical compound C1=C(O)C(CC)=CC(C=2N(C(S)=NN=2)C=2C=C3SC(=O)NC3=CC=2)=C1O AVUJFTYWVXBGRV-UHFFFAOYSA-N 0.000 claims description 3
- 208000028564 B-cell non-Hodgkin lymphoma Diseases 0.000 claims description 3
- RANGGRFKXIPVTL-UHFFFAOYSA-N OC1=CC(O)=CC=C1C1=NN=C(S)N1C1=CC=CC2=NC=CC=C12 Chemical compound OC1=CC(O)=CC=C1C1=NN=C(S)N1C1=CC=CC2=NC=CC=C12 RANGGRFKXIPVTL-UHFFFAOYSA-N 0.000 claims description 3
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 3
- VQRUPYILIOUPSA-UHFFFAOYSA-N [5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(3-methylquinolin-5-yl)-1,2,4-triazol-3-yl]carbamic acid Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(NC(O)=O)=NN=2)C=2C3=CC(C)=CN=C3C=CC=2)=C1O VQRUPYILIOUPSA-UHFFFAOYSA-N 0.000 claims description 3
- IDKYLRUSKCDRNJ-UHFFFAOYSA-N [5-(5-ethyl-2,4-dihydroxyphenyl)-4-quinolin-5-yl-1,2,4-triazol-3-yl]urea Chemical compound C1=C(O)C(CC)=CC(C=2N(C(NC(N)=O)=NN=2)C=2C3=CC=CN=C3C=CC=2)=C1O IDKYLRUSKCDRNJ-UHFFFAOYSA-N 0.000 claims description 3
- 230000017531 blood circulation Effects 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 210000000987 immune system Anatomy 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- BOLSCKSQXHRCIU-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-phenylphenyl)-4-naphthalen-1-yl-1H-1,2,4-triazole-5-thione Chemical compound C1=C(C=2N(C(S)=NN=2)C=2C3=CC=CC=C3C=CC=2)C(O)=CC(O)=C1C1=CC=CC=C1 BOLSCKSQXHRCIU-UHFFFAOYSA-N 0.000 claims description 2
- ARZFHEBGTJGCBN-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methyl-2,3-dihydroindol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3CCN(C)C3=CC=2)=C1O ARZFHEBGTJGCBN-UHFFFAOYSA-N 0.000 claims description 2
- FGOBJTIASHBAOW-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(1-methylsulfonyl-2,3-dihydroindol-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(=O)NN=2)C=2C=C3CCN(C3=CC=2)S(C)(=O)=O)=C1O FGOBJTIASHBAOW-UHFFFAOYSA-N 0.000 claims description 2
- CHUJYSWTCNNZKD-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-ethoxy-2,3-dihydro-1H-inden-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2CC(OCC)CC2=CC=C1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O CHUJYSWTCNNZKD-UHFFFAOYSA-N 0.000 claims description 2
- TWCMQDJOBJQALD-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-ethyl-1,3-dihydroisoindol-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2CN(CC)CC2=CC=C1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O TWCMQDJOBJQALD-UHFFFAOYSA-N 0.000 claims description 2
- QOVKQTBLQIWWAQ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-hydroxy-2,3-dihydro-1H-inden-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3CC(O)CC3=CC=2)=C1O QOVKQTBLQIWWAQ-UHFFFAOYSA-N 0.000 claims description 2
- IYSOWEVTQCOKRS-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-methoxy-2,3-dihydro-1H-inden-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C2CC(OC)CC2=CC=C1N1C(O)=NN=C1C1=CC(C(C)C)=C(O)C=C1O IYSOWEVTQCOKRS-UHFFFAOYSA-N 0.000 claims description 2
- ABFCXDBXYPECGQ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-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=CC(C(C)C)=C(O)C=C1O ABFCXDBXYPECGQ-UHFFFAOYSA-N 0.000 claims description 2
- UPAAMKCFKSXWLK-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-methyl-1,3-dihydroisoindol-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=C3CN(C)CC3=CC=2)=C1O UPAAMKCFKSXWLK-UHFFFAOYSA-N 0.000 claims description 2
- UFPBXKVQPASGBJ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-morpholin-4-yl-2,3-dihydro-1H-inden-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(=O)NN=2)C=2C=C3CC(CC3=CC=2)N2CCOCC2)=C1O UFPBXKVQPASGBJ-UHFFFAOYSA-N 0.000 claims description 2
- DEQQATIVSBOTAT-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-morpholin-4-yl-2,3-dihydro-1H-inden-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=C3CC(CC3=CC=2)N2CCOCC2)=C1O DEQQATIVSBOTAT-UHFFFAOYSA-N 0.000 claims description 2
- PRILXIAAFGTMKG-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-propoxy-2,3-dihydro-1H-inden-5-yl)-1H-1,2,4-triazole-5-thione Chemical compound C1=C2CC(OCCC)CC2=CC=C1N1C(S)=NN=C1C1=CC(C(C)C)=C(O)C=C1O PRILXIAAFGTMKG-UHFFFAOYSA-N 0.000 claims description 2
- ZDHCZQOEHBYDIJ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-pyrrolidin-1-yl-2,3-dihydro-1H-inden-5-yl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3CC(CC3=CC=2)N2CCCC2)=C1O ZDHCZQOEHBYDIJ-UHFFFAOYSA-N 0.000 claims description 2
- CICMDMLKPGNUGX-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(2-pyrrolidin-1-yl-2,3-dihydro-1H-inden-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=C3CC(CC3=CC=2)N2CCCC2)=C1O CICMDMLKPGNUGX-UHFFFAOYSA-N 0.000 claims description 2
- MPKZDZVKZJKDCW-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(5,6,7,8-tetrahydronaphthalen-1-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=3CCCCC=3C=CC=2)=C1O MPKZDZVKZJKDCW-UHFFFAOYSA-N 0.000 claims description 2
- ABTDREDRXWKWLD-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-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=CC(C(C)C)=C(O)C=C1O ABTDREDRXWKWLD-UHFFFAOYSA-N 0.000 claims description 2
- ZWUZGNVPEOCDPY-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[2-(dimethylamino)-2,3-dihydro-1H-inden-5-yl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)C=2C=C3CC(CC3=CC=2)N(C)C)=C1O ZWUZGNVPEOCDPY-UHFFFAOYSA-N 0.000 claims description 2
- FTZLWLNIJKDHKV-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[2-(dimethylamino)-2,3-dihydro-1H-inden-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=C3CC(CC3=CC=2)N(C)C)=C1O FTZLWLNIJKDHKV-UHFFFAOYSA-N 0.000 claims description 2
- KBUMFPWDZWEKDW-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[2-(ethoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-1H-1,2,4-triazol-5-one Chemical compound C1=C2CC(OCOCC)CC2=CC=C1N1C(O)=NN=C1C1=CC(C(C)C)=C(O)C=C1O KBUMFPWDZWEKDW-UHFFFAOYSA-N 0.000 claims description 2
- FSLCQIJCGLFKFD-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[2-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-1H-1,2,4-triazol-5-one Chemical compound C1=C2CC(OCOC)CC2=CC=C1N1C(O)=NN=C1C1=CC(C(C)C)=C(O)C=C1O FSLCQIJCGLFKFD-UHFFFAOYSA-N 0.000 claims description 2
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| 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 |
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| WO2007140002A2 (en) | 2006-05-25 | 2007-12-06 | 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 |
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| CA2677481C (en) * | 2007-02-08 | 2015-07-07 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
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| WO2009023211A1 (en) | 2007-08-13 | 2009-02-19 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
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| 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 |
| PT2328893E (pt) * | 2008-08-08 | 2013-06-27 | Synta Pharmaceuticals Corp | Compostos de triazol que modulam a actividade da hsp90 |
| TW201011003A (en) | 2008-08-08 | 2010-03-16 | Synta Pharmaceuticals Corp | Triazole compounds that modulate HSP90 activity |
| BRPI1010882A2 (pt) * | 2009-06-08 | 2019-09-24 | California Capital Equity Llc | derivados de triazina e suas aplicações terapêuticas. |
| 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 |
| WO2011060328A1 (en) * | 2009-11-13 | 2011-05-19 | Infinity Pharmaceuticals, Inc. | Compositions, kits, and methods for identification, assessment, prevention, and therapy of cancer |
| US9205086B2 (en) | 2010-04-19 | 2015-12-08 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a Hsp90 inhibitory compounds and a EGFR inhibitor |
| JP2014520808A (ja) | 2011-07-07 | 2014-08-25 | シンタ ファーマシューティカルズ コーポレーション | Ｈｓｐ９０阻害化合物を用いた癌の治療 |
| CN104081203B (zh) | 2011-07-08 | 2018-07-31 | 索隆-基特林癌症研究协会 | 标记的hsp90抑制剂的用途 |
| 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 |
| EP2776025A1 (en) | 2011-11-02 | 2014-09-17 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with platinum-containing agents |
| EP2780010A1 (en) | 2011-11-14 | 2014-09-24 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
| AU2013266086B2 (en) | 2012-05-25 | 2018-03-01 | Berg Llc | Methods of treating a metabolic syndrome by modulating heat shock protein (HSP) 90-beta |
| CN102977012B (zh) * | 2012-12-20 | 2015-06-03 | 江苏弘和药物研发有限公司 | 4-溴吡啶-2-甲酸甲酯的合成方法 |
| WO2014099503A1 (en) | 2012-12-20 | 2014-06-26 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| JP2016529311A (ja) | 2013-09-06 | 2016-09-23 | インセプション ２、 インコーポレイテッド | トリアゾロン化合物類及びそれらの使用 |
| WO2015066053A2 (en) * | 2013-10-28 | 2015-05-07 | Synta Pharmaceuticals Corp. | Targeted therapeutics |
| JP6783224B2 (ja) | 2014-04-04 | 2020-11-11 | デル マー ファーマシューティカルズ | 肺の非小細胞癌腫及び卵巣癌を処置するためのジアンヒドロガラクチトール及びその類縁体又は誘導体の使用 |
| WO2015188198A2 (en) | 2014-06-06 | 2015-12-10 | Berg Llc | Methods of treating a metabolic syndrome by modulating heat shock protein (hsp) 90-beta |
| NZ737004A (en) | 2015-05-20 | 2022-10-28 | Amgen Inc | Triazole agonists of the apj receptor |
| EP3452466B1 (en) | 2016-05-03 | 2020-08-12 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| EP3541803B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| MA46827A (fr) | 2016-11-16 | 2019-09-25 | Amgen Inc | Composés de triazole à substitution cycloalkyle en tant qu'agonistes du récepteur apj |
| EP3541810B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole phenyl compounds as agonists of the apj receptor |
| WO2018097945A1 (en) | 2016-11-16 | 2018-05-31 | Amgen Inc. | Heteroaryl-substituted triazoles as apj receptor agonists |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| US11191762B2 (en) | 2016-11-16 | 2021-12-07 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the APJ Receptor |
| 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 |
| EP3704122B1 (en) | 2017-11-03 | 2021-09-01 | Amgen Inc. | Fused triazole agonists of the apj receptor |
| MA52487A (fr) | 2018-05-01 | 2021-03-10 | Amgen Inc | Pyrimidinones substituées en tant qu'agonistes du récepteur apj |
| BR112020026450A2 (pt) * | 2018-06-29 | 2021-03-23 | F. Hoffmann-La Roche Ag | Compostos de fórmula i |
| CN113121505B (zh) * | 2021-03-02 | 2023-03-07 | 中国人民解放军海军军医大学 | 一种具有抗真菌与抗肿瘤双重作用的三唑酮类化合物及应用 |
| CN114539098B (zh) * | 2022-02-26 | 2024-05-24 | 青岛大学 | 一种双功能hdac6抑制剂、合成方法及应用 |
Family Cites Families (59)
| 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 |
| US4624995A (en) | 1985-04-09 | 1986-11-25 | Minnesota Mining And Manufacturing Company | Triazolinethione-containing polymer |
| US4740568A (en) | 1985-04-09 | 1988-04-26 | 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 |
| CZ283018B6 (cs) | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| AU669160B2 (en) | 1992-03-13 | 1996-05-30 | Merck Sharp & Dohme Limited | Imidazole, triazole and tetrazole derivatives |
| TW218017B (enExample) | 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 |
| 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 |
| US6583090B1 (en) | 1998-03-09 | 2003-06-24 | Basf Aktiengesellschaft | Hetaryl-substituted benzyl phenyl ethers, method for the production thereof, and their use for combating harmful fungi and animal pests |
| 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 |
| WO2002066447A1 (en) * | 2001-02-21 | 2002-08-29 | Ono Pharmaceutical Co., Ltd. | 4h-1,2,4-triazole-3(2h)-thione deratives as sphingomyelinase inhibitors |
| 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 |
| ATE438630T1 (de) | 2001-11-28 | 2009-08-15 | Ipsen Pharma | 5-sulfanyl-4h-1,2,4-triazolderivate und deren verwendung zur behandlung von somatostatine vermittelten krankheiten |
| 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 |
| MXPA06011046A (es) | 2004-03-26 | 2007-03-21 | Amphora Discovery Corp | Ciertos compuestos basados en triazol, composiciones, y usos de los mismos. |
| ME01498B (me) * | 2004-11-18 | 2014-04-20 | Synta Pharmaceuticals Corp | Jedinjenja triazola koja modulišu aktivnost hsp90 |
| 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 |
| 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 |
| US8629285B2 (en) | 2005-08-18 | 2014-01-14 | Synta Pharmaceuticals Corp. | Imidazole compounds that modulate HSP90 activity |
| EP1928846B1 (en) * | 2005-08-18 | 2014-06-04 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| DE102006023337A1 (de) * | 2006-05-18 | 2007-11-22 | Merck Patent Gmbh | Triazolderivate II |
| WO2007139955A2 (en) | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| EP2038262B1 (en) | 2006-05-25 | 2014-11-12 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| AU2007267859B2 (en) | 2006-05-25 | 2012-04-12 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate Hsp90 activity |
| WO2007140002A2 (en) | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Method for treating non-hodgkin's lymphoma |
| TW200806637A (en) | 2006-05-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Synthesis of triazole compounds that modulate HSP90 activity |
| EP2034995A2 (en) | 2006-05-25 | 2009-03-18 | Synta Pharmaceuticals Corporation | Method for treating proliferative disorders associated with protooncogene products |
| US20080027047A1 (en) | 2006-05-25 | 2008-01-31 | Weiwen Ying | Compounds that modulate HSP90 activity and methods for identifying same |
| US8188075B2 (en) | 2006-08-17 | 2012-05-29 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| US20110046125A1 (en) | 2006-10-19 | 2011-02-24 | Synta Pharmaceuticals Corp. | Method for treating infections |
| US20100280032A1 (en) | 2006-10-26 | 2010-11-04 | Synta Pharmaceuticals Corp. | Method for treating inflammatory disorders |
| CA2677481C (en) | 2007-02-08 | 2015-07-07 | 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 |
| 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 |
| WO2009023211A1 (en) | 2007-08-13 | 2009-02-19 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| WO2009139916A1 (en) | 2008-05-16 | 2009-11-19 | 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 |
| TW201011003A (en) | 2008-08-08 | 2010-03-16 | Synta Pharmaceuticals Corp | Triazole compounds that modulate HSP90 activity |
| PT2328893E (pt) | 2008-08-08 | 2013-06-27 | Synta Pharmaceuticals Corp | Compostos de triazol que modulam a actividade da hsp90 |
| WO2012037072A1 (en) | 2010-09-13 | 2012-03-22 | Synta Pharmaceuticals Corporation | Hsp90 inhibitors for treating non-small cell lung cancers in wild-type egfr and/or kras patients |
-
2007
- 2007-05-25 WO PCT/US2007/012524 patent/WO2007139955A2/en not_active Ceased
- 2007-05-25 AU AU2007267847A patent/AU2007267847B2/en not_active Ceased
- 2007-05-25 CA CA002653222A patent/CA2653222A1/en not_active Abandoned
- 2007-05-25 US US11/807,201 patent/US8318790B2/en not_active Expired - Fee Related
- 2007-05-25 EP EP07809199A patent/EP2034996A2/en not_active Withdrawn
- 2007-05-25 TW TW096118677A patent/TW200804313A/zh unknown
- 2007-05-25 JP JP2009512169A patent/JP5441690B2/ja not_active Expired - Fee Related
-
2012
- 2012-01-13 US US13/350,296 patent/US8927548B2/en active Active
-
2014
- 2014-12-31 US US14/587,531 patent/US20150183771A1/en not_active Abandoned
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