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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-
2007
- 2007-05-25 US US11/807,201 patent/US8318790B2/en not_active Expired - Fee Related
- 2007-05-25 CA CA002653222A patent/CA2653222A1/en not_active Abandoned
- 2007-05-25 JP JP2009512169A patent/JP5441690B2/ja not_active Expired - Fee Related
- 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 EP EP07809199A patent/EP2034996A2/en not_active Withdrawn
- 2007-05-25 TW TW096118677A patent/TW200804313A/zh unknown
-
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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