JP2009538322A5 - - Google Patents
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- Publication number
- JP2009538322A5 JP2009538322A5 JP2009512172A JP2009512172A JP2009538322A5 JP 2009538322 A5 JP2009538322 A5 JP 2009538322A5 JP 2009512172 A JP2009512172 A JP 2009512172A JP 2009512172 A JP2009512172 A JP 2009512172A JP 2009538322 A5 JP2009538322 A5 JP 2009538322A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- benzyl
- methyl
- triazol
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 72
- -1 -OR 30 Chemical group 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
- 125000003107 substituted aryl group Chemical group 0.000 claims description 27
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 26
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 25
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 25
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 25
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 25
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 18
- 239000000651 prodrug Substances 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000001475 halogen functional group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 4
- AJVQYZWYNTVLOY-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(dimethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CN(C)C)=CC=2)=C1O AJVQYZWYNTVLOY-UHFFFAOYSA-N 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- VDZZXPGPZVLWQX-UHFFFAOYSA-N 2-[[4-[[3-(2,4-dihydroxy-5-propan-2-ylphenyl)-5-oxo-1H-1,2,4-triazol-4-yl]methyl]phenyl]methyl]guanidine Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNC(N)=N)=CC=2)=C1O VDZZXPGPZVLWQX-UHFFFAOYSA-N 0.000 claims description 2
- RMOUYXBRXRSPLO-UHFFFAOYSA-N 2-[[4-[[3-(2,4-dihydroxy-5-propan-2-ylphenyl)-5-oxo-1H-1,2,4-triazol-4-yl]methyl]phenyl]methylamino]acetonitrile Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCC#N)=CC=2)=C1O RMOUYXBRXRSPLO-UHFFFAOYSA-N 0.000 claims description 2
- WCOGITUCCHMTAS-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-(furan-2-ylmethyl)-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2OC=CC=2)=C1O WCOGITUCCHMTAS-UHFFFAOYSA-N 0.000 claims description 2
- QNMOXFOEVNGKOB-GFCCVEGCSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(1R)-1-(4-methoxyphenyl)ethyl]-1H-1,2,4-triazole-5-thione Chemical compound C1=CC(OC)=CC=C1[C@@H](C)N1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1S QNMOXFOEVNGKOB-GFCCVEGCSA-N 0.000 claims description 2
- QNMOXFOEVNGKOB-LBPRGKRZSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(1S)-1-(4-methoxyphenyl)ethyl]-1H-1,2,4-triazole-5-thione Chemical compound C1=CC(OC)=CC=C1[C@H](C)N1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1S QNMOXFOEVNGKOB-LBPRGKRZSA-N 0.000 claims description 2
- QLRMDKKNOXFZQE-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(2-methoxyphenyl)methyl]-1H-1,2,4-triazol-5-one Chemical compound COC1=CC=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O QLRMDKKNOXFZQE-UHFFFAOYSA-N 0.000 claims description 2
- FNWKFQMZOSTIGM-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(3,4-dimethoxyphenyl)methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(OC)C(OC)=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O FNWKFQMZOSTIGM-UHFFFAOYSA-N 0.000 claims description 2
- FSMSKRZJLBOCNA-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(3-methoxyphenyl)methyl]-1H-1,2,4-triazol-5-one Chemical compound COC1=CC=CC(CN2C(=NN=C2O)C=2C(=CC(O)=C(C(C)C)C=2)O)=C1 FSMSKRZJLBOCNA-UHFFFAOYSA-N 0.000 claims description 2
- HHURVUNXKXJIBQ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(4-fluorophenyl)methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(F)=CC=2)=C1O HHURVUNXKXJIBQ-UHFFFAOYSA-N 0.000 claims description 2
- YDUIHYHWYKFEIB-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(4-methylphenyl)methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(C)=CC=2)=C1O YDUIHYHWYKFEIB-UHFFFAOYSA-N 0.000 claims description 2
- OAUQVAQWWLFQDO-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(4-pyridin-3-ylphenyl)methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(=O)NN=2)CC=2C=CC(=CC=2)C=2C=NC=CC=2)=C1O OAUQVAQWWLFQDO-UHFFFAOYSA-N 0.000 claims description 2
- IOFFWQVLOVJMAT-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[2-(2,3-dimethoxyphenyl)ethyl]-1H-1,2,4-triazol-5-one Chemical compound COC1=CC=CC(CCN2C(=NN=C2O)C=2C(=CC(O)=C(C(C)C)C=2)O)=C1OC IOFFWQVLOVJMAT-UHFFFAOYSA-N 0.000 claims description 2
- CUVOKMCXLLFEKV-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[2-(3,4-dimethoxyphenyl)ethyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(OC)C(OC)=CC=C1CCN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O CUVOKMCXLLFEKV-UHFFFAOYSA-N 0.000 claims description 2
- OTGJVEGYOWWSAY-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[2-(3,5-dimethoxyphenyl)ethyl]-1H-1,2,4-triazol-5-one Chemical compound COC1=CC(OC)=CC(CCN2C(=NN=C2O)C=2C(=CC(O)=C(C(C)C)C=2)O)=C1 OTGJVEGYOWWSAY-UHFFFAOYSA-N 0.000 claims description 2
- GDXYNDOQDDEXPQ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(1,3-dioxolan-2-yl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(=CC=2)C2OCCO2)=C1O GDXYNDOQDDEXPQ-UHFFFAOYSA-N 0.000 claims description 2
- CNKPXVMAQKPIKX-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(1-hydroxyethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(=CC=2)C(C)O)=C1O CNKPXVMAQKPIKX-UHFFFAOYSA-N 0.000 claims description 2
- PZTYJRHZKXYQHR-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(1H-pyrazol-4-yl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(=O)NN=2)CC=2C=CC(=CC=2)C2=CNN=C2)=C1O PZTYJRHZKXYQHR-UHFFFAOYSA-N 0.000 claims description 2
- OJDCKFQSORUGCG-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(2-morpholin-4-ylethoxymethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(COCCN3CCOCC3)=CC=2)=C1O OJDCKFQSORUGCG-UHFFFAOYSA-N 0.000 claims description 2
- LYJPAFVJBFNCSC-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(2-pyridin-2-ylethoxymethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(COCCC=3N=CC=CC=3)=CC=2)=C1O LYJPAFVJBFNCSC-UHFFFAOYSA-N 0.000 claims description 2
- GXBQMAQVCIYQDR-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(ethylaminomethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(CNCC)=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O GXBQMAQVCIYQDR-UHFFFAOYSA-N 0.000 claims description 2
- OYHXNWUAKOIKAB-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(hydroxymethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CO)=CC=2)=C1O OYHXNWUAKOIKAB-UHFFFAOYSA-N 0.000 claims description 2
- LQINDISXKPIUEK-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(methylaminomethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(CNC)=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O LQINDISXKPIUEK-UHFFFAOYSA-N 0.000 claims description 2
- GXEMXAIFEACJOP-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(phenoxymethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(COC=3C=CC=CC=3)=CC=2)=C1O GXEMXAIFEACJOP-UHFFFAOYSA-N 0.000 claims description 2
- UDPREWBYDJCRPB-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(propan-2-yloxymethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(COC(C)C)=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O UDPREWBYDJCRPB-UHFFFAOYSA-N 0.000 claims description 2
- MDVVWIIFEDVEIY-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(pyridin-2-ylmethoxymethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(COCC=3N=CC=CC=3)=CC=2)=C1O MDVVWIIFEDVEIY-UHFFFAOYSA-N 0.000 claims description 2
- JXXXWHVNKJWRQH-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(pyrrolidin-1-ylmethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CN3CCCC3)=CC=2)=C1O JXXXWHVNKJWRQH-UHFFFAOYSA-N 0.000 claims description 2
- MWHVYMXMVQFJJO-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-(thiomorpholin-4-ylmethyl)phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CN3CCSCC3)=CC=2)=C1O MWHVYMXMVQFJJO-UHFFFAOYSA-N 0.000 claims description 2
- WCPSHGWHVNFZJM-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(2-hydroxyethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCCO)=CC=2)=C1O WCPSHGWHVNFZJM-UHFFFAOYSA-N 0.000 claims description 2
- JDVZUOXVJBQJPS-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(2-methoxyethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(CNCCOC)=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O JDVZUOXVJBQJPS-UHFFFAOYSA-N 0.000 claims description 2
- ZVPUPRMIHJGRDZ-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(2-methylpropylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(CNCC(C)C)=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O ZVPUPRMIHJGRDZ-UHFFFAOYSA-N 0.000 claims description 2
- DVVMZVLOHPGCJI-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(2-morpholin-4-ylethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCCN3CCOCC3)=CC=2)=C1O DVVMZVLOHPGCJI-UHFFFAOYSA-N 0.000 claims description 2
- ORSFTNFBXBSLSK-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(2-phenoxyethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCCOC=3C=CC=CC=3)=CC=2)=C1O ORSFTNFBXBSLSK-UHFFFAOYSA-N 0.000 claims description 2
- CZEFAYNRPMECFC-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(2-piperidin-1-ylethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCCN3CCCCC3)=CC=2)=C1O CZEFAYNRPMECFC-UHFFFAOYSA-N 0.000 claims description 2
- GMTRAZWLHKQDNS-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(2-pyridin-2-ylethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCCC=3N=CC=CC=3)=CC=2)=C1O GMTRAZWLHKQDNS-UHFFFAOYSA-N 0.000 claims description 2
- LOOJMKIJAVNTGR-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(2-pyrrolidin-1-ylethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCCN3CCCC3)=CC=2)=C1O LOOJMKIJAVNTGR-UHFFFAOYSA-N 0.000 claims description 2
- WKAMEHWWAXRMKG-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(3-methoxypropylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(CNCCCOC)=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O WKAMEHWWAXRMKG-UHFFFAOYSA-N 0.000 claims description 2
- OEOAXBQPOXNYTN-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(4-methylpiperazin-1-yl)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CN3CCN(C)CC3)=CC=2)=C1O OEOAXBQPOXNYTN-UHFFFAOYSA-N 0.000 claims description 2
- ZQTMBEBYGVZTEU-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(4-methylpiperidin-1-yl)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CN3CCC(C)CC3)=CC=2)=C1O ZQTMBEBYGVZTEU-UHFFFAOYSA-N 0.000 claims description 2
- OCBFPVKCNQCMID-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CN3CCC(CC3)N3CCCC3)=CC=2)=C1O OCBFPVKCNQCMID-UHFFFAOYSA-N 0.000 claims description 2
- DSOFVDKBDFURCB-ZMOGYAJESA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(E)-morpholin-4-yliminomethyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(\C=N\N3CCOCC3)=CC=2)=C1O DSOFVDKBDFURCB-ZMOGYAJESA-N 0.000 claims description 2
- BSMIPFXGXLOVKY-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(oxolan-2-ylmethylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCC3OCCC3)=CC=2)=C1O BSMIPFXGXLOVKY-UHFFFAOYSA-N 0.000 claims description 2
- QFTMUYNUNQGJQN-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(prop-2-ynylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=C(O)C(C(C)C)=CC(C=2N(C(O)=NN=2)CC=2C=CC(CNCC#C)=CC=2)=C1O QFTMUYNUNQGJQN-UHFFFAOYSA-N 0.000 claims description 2
- BCRSNMIJSJLIOG-UHFFFAOYSA-N 3-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[[4-[(propan-2-ylamino)methyl]phenyl]methyl]-1H-1,2,4-triazol-5-one Chemical compound C1=CC(CNC(C)C)=CC=C1CN1C(C=2C(=CC(O)=C(C(C)C)C=2)O)=NN=C1O BCRSNMIJSJLIOG-UHFFFAOYSA-N 0.000 claims description 2
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| WO2007139955A2 (en) | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| AU2007267843B2 (en) | 2006-05-25 | 2011-10-13 | Synta Pharmaceuticals Corp. | Method for treating proliferative disorders associated with protooncogene products |
| PL2118077T3 (pl) | 2007-02-08 | 2015-05-29 | Synta Pharmaceuticals Corp | Związki triazolowe modulujące aktywność hsp90 |
| AU2008287367B2 (en) | 2007-08-13 | 2012-02-23 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| WO2009075890A2 (en) * | 2007-12-12 | 2009-06-18 | Synta Pharmaceuticals Corp. | Method for synthesis of triazole compounds that modulate hsp90 activity |
| US9156836B2 (en) * | 2008-05-16 | 2015-10-13 | Synta Pharmaceuticals Corp. | Tricyclic triazole compounds that modulate HSP90 activity |
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| WO2010017545A2 (en) * | 2008-08-08 | 2010-02-11 | Synta Pharamceuticals Corp. | Triazole compounds that modulate hsp90 activity |
| US9126953B2 (en) * | 2008-08-08 | 2015-09-08 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
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| 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 |
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| US9402831B2 (en) | 2011-11-14 | 2016-08-02 | Synta Pharmaceutical Corp. | Combination therapy of HSP90 inhibitors with BRAF inhibitors |
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| CN102796052B (zh) * | 2012-09-06 | 2014-08-13 | 河南师范大学 | 具有抗真菌活性的丹皮酚-1,2,3-三氮唑类化合物及其制备方法 |
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| JP7366746B2 (ja) | 2017-08-31 | 2023-10-23 | 北興化学工業株式会社 | １－（ｎ，ｎ－ジ置換カルバモイル）４－（置換スルホニル）トリアゾリン－５－オン誘導体、４－（ｎ，ｎ－ジ置換カルバモイル）１－（置換スルホニル）トリアゾリン－５－オン誘導体、およびそれらを有効成分として含有する除草剤 |
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2007
- 2007-05-25 EP EP07795380.0A patent/EP2038262B1/en active Active
- 2007-05-25 TW TW096118678A patent/TWI490212B/zh not_active IP Right Cessation
- 2007-05-25 AU AU2007267860A patent/AU2007267860B2/en not_active Ceased
- 2007-05-25 WO PCT/US2007/012544 patent/WO2007139968A2/en not_active Ceased
- 2007-05-25 CA CA002653332A patent/CA2653332A1/en not_active Abandoned
- 2007-05-25 US US11/807,331 patent/US8183384B2/en active Active - Reinstated
- 2007-05-25 JP JP2009512172A patent/JP5410965B2/ja not_active Expired - Fee Related
-
2012
- 2012-04-20 US US13/452,200 patent/US8329736B2/en not_active Expired - Fee Related
- 2012-11-13 US US13/675,350 patent/US20130072461A1/en not_active Abandoned
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