JP2008540595A5 - - Google Patents
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- Publication number
- JP2008540595A5 JP2008540595A5 JP2008511622A JP2008511622A JP2008540595A5 JP 2008540595 A5 JP2008540595 A5 JP 2008540595A5 JP 2008511622 A JP2008511622 A JP 2008511622A JP 2008511622 A JP2008511622 A JP 2008511622A JP 2008540595 A5 JP2008540595 A5 JP 2008540595A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazol
- benzylidene
- phenyl
- group
- piperazin
- 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 2,5-disubstituted thiazol-4-one Chemical class 0.000 claims 112
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 20
- 125000002950 monocyclic group Chemical group 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 18
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 18
- 229910052801 chlorine Inorganic materials 0.000 claims 17
- 229920006395 saturated elastomer Polymers 0.000 claims 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 15
- 229910052794 bromium Inorganic materials 0.000 claims 14
- 239000000460 chlorine Substances 0.000 claims 14
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 12
- 125000004076 pyridyl group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000002098 pyridazinyl group Chemical group 0.000 claims 11
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000001931 aliphatic group Chemical group 0.000 claims 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 8
- 125000001624 naphthyl group Chemical group 0.000 claims 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 229910052740 iodine Inorganic materials 0.000 claims 7
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 229910052751 metal Inorganic materials 0.000 claims 6
- 239000002184 metal Substances 0.000 claims 6
- 229910052987 metal hydride Inorganic materials 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 239000012429 reaction media Substances 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 3
- 229910000105 potassium hydride Inorganic materials 0.000 claims 3
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000012312 sodium hydride Substances 0.000 claims 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- WTKDAOBOUKOOJJ-UHFFFAOYSA-N 2-morpholin-4-yl-5-[[4-(trifluoromethyl)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C=C1C(=O)N=C(N2CCOCC2)S1 WTKDAOBOUKOOJJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- YKKQRGBWSSRCED-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound C1=CC(O)=CC=C1C=C1C(=O)N=C(N2CCOCC2)S1 YKKQRGBWSSRCED-UHFFFAOYSA-N 0.000 claims 2
- BERNZRBKZLKWTM-UHFFFAOYSA-N 5-[(4-tert-butylphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C=C1C(=O)N=C(N2CCOCC2)S1 BERNZRBKZLKWTM-UHFFFAOYSA-N 0.000 claims 2
- OHOSRFPWXKVSDP-UHFFFAOYSA-N 5-[3-(4-methoxyphenyl)but-2-enylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound C1=CC(OC)=CC=C1C(C)=CC=C1C(=O)N=C(N2CCOCC2)S1 OHOSRFPWXKVSDP-UHFFFAOYSA-N 0.000 claims 2
- YEMNNZXQUHAYGV-UHFFFAOYSA-N 5-[3-(4-tert-butylphenyl)but-2-enylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound C=1C=C(C(C)(C)C)C=CC=1C(C)=CC=C(C(N=1)=O)SC=1N1CCOCC1 YEMNNZXQUHAYGV-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- BBOPZMIUSLVPJX-JLHYYAGUSA-N (5e)-5-[(4-methylphenyl)methylidene]-2-pyrrolidin-1-yl-1,3-thiazol-4-one Chemical compound C1=CC(C)=CC=C1\C=C\1C(=O)N=C(N2CCCC2)S/1 BBOPZMIUSLVPJX-JLHYYAGUSA-N 0.000 claims 1
- OOMSONMXRODLHX-UVTDQMKNSA-N (5z)-2-morpholin-4-yl-5-[(3,4,5-trimethoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound COC1=C(OC)C(OC)=CC(\C=C/2C(N=C(S\2)N2CCOCC2)=O)=C1 OOMSONMXRODLHX-UVTDQMKNSA-N 0.000 claims 1
- PYMZXMIPXYOMGP-XFXZXTDPSA-N (5z)-5-[(2-hydroxyphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound OC1=CC=CC=C1\C=C/1C(=O)N=C(N2CCOCC2)S\1 PYMZXMIPXYOMGP-XFXZXTDPSA-N 0.000 claims 1
- VWAWKRNOYSHZSA-RAXLEYEMSA-N (5z)-5-[(2-methoxyphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound COC1=CC=CC=C1\C=C/1C(=O)N=C(N2CCOCC2)S\1 VWAWKRNOYSHZSA-RAXLEYEMSA-N 0.000 claims 1
- RJMUQCUOEKPBKD-UVTDQMKNSA-N (5z)-5-[(3,4-dimethoxyphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound C1=C(OC)C(OC)=CC=C1\C=C/1C(=O)N=C(N2CCOCC2)S\1 RJMUQCUOEKPBKD-UVTDQMKNSA-N 0.000 claims 1
- JREKHXBULNREND-RAXLEYEMSA-N (5z)-5-[(4-chlorophenyl)methylidene]-2-piperidin-1-yl-1,3-thiazol-4-one Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(=O)N=C(N2CCCCC2)S\1 JREKHXBULNREND-RAXLEYEMSA-N 0.000 claims 1
- KUIFSWAFSKZRSU-LCYFTJDESA-N (5z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound C1=C(O)C(OC)=CC(\C=C/2C(N=C(S\2)N2CCOCC2)=O)=C1 KUIFSWAFSKZRSU-LCYFTJDESA-N 0.000 claims 1
- UKGZFYRVZKIRSP-KAMYIIQDSA-N (5z)-5-[[4-(dimethylamino)phenyl]methylidene]-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound C1=CC(N(C)C)=CC=C1\C=C/1C(=O)N=C(N2CCOCC2)S\1 UKGZFYRVZKIRSP-KAMYIIQDSA-N 0.000 claims 1
- RXOOHGDIEIAHRA-BENRWUELSA-N (5z)-5-benzylidene-2-morpholin-4-yl-1,3-thiazol-4-one Chemical compound O=C1N=C(N2CCOCC2)S\C1=C/C1=CC=CC=C1 RXOOHGDIEIAHRA-BENRWUELSA-N 0.000 claims 1
- VMBXNIKUJJZUOA-UHFFFAOYSA-N 1-[4-oxo-5-[[4-(trifluoromethyl)phenyl]methylidene]-1,3-thiazol-2-yl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1C=C1C(=O)N=C(NC(=O)NC=2C(=CC=CC=2)C(F)(F)F)S1 VMBXNIKUJJZUOA-UHFFFAOYSA-N 0.000 claims 1
- AFWJHNNBKHVDNE-UHFFFAOYSA-N 1-[4-oxo-5-[[4-(trifluoromethyl)phenyl]methylidene]-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC(S1)=NC(=O)C1=CC1=CC=C(C(F)(F)F)C=C1 AFWJHNNBKHVDNE-UHFFFAOYSA-N 0.000 claims 1
- AOHINRKSHNCSMX-UHFFFAOYSA-N 1-[5-[(4-methylphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]-3-[2-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C)=CC=C1C=C1C(=O)N=C(NC(=O)NC=2C(=CC=CC=2)C(F)(F)F)S1 AOHINRKSHNCSMX-UHFFFAOYSA-N 0.000 claims 1
- LCTHWENQRPECBE-UHFFFAOYSA-N 1-[5-[(4-methylphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C)=CC=C1C=C1C(=O)N=C(NC(=O)NC=2C=CC(=CC=2)C(F)(F)F)S1 LCTHWENQRPECBE-UHFFFAOYSA-N 0.000 claims 1
- SRRVXELRMUCVPF-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethylamino)-5-(naphthalen-1-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1=CC=C2C(C=C3SC(NCC=4C=C5OCOC5=CC=4)=NC3=O)=CC=CC2=C1 SRRVXELRMUCVPF-UHFFFAOYSA-N 0.000 claims 1
- KGMXAYSVXOVUJX-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethylamino)-5-[[4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C=C1C(=O)N=C(NCC=2C=C3OCOC3=CC=2)S1 KGMXAYSVXOVUJX-UHFFFAOYSA-N 0.000 claims 1
- YYHQFNWWBUUDQD-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethylamino)-5-[[4-(trifluoromethyl)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C=C1C(=O)N=C(NCC=2C=C3OCOC3=CC=2)S1 YYHQFNWWBUUDQD-UHFFFAOYSA-N 0.000 claims 1
- ZNDKIVHPQCXQJE-UHFFFAOYSA-N 2-(2,3-dihydroindol-1-yl)-5-[(4-methylphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C)=CC=C1C=C1C(=O)N=C(N2C3=CC=CC=C3CC2)S1 ZNDKIVHPQCXQJE-UHFFFAOYSA-N 0.000 claims 1
- PSRCOPIOXOGTJC-UHFFFAOYSA-N 2-(2,3-dihydroindol-1-yl)-5-[[4-(trifluoromethyl)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C=C1C(=O)N=C(N2C3=CC=CC=C3CC2)S1 PSRCOPIOXOGTJC-UHFFFAOYSA-N 0.000 claims 1
- ZMZXKEFAKVKPTI-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-(naphthalen-1-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C3=CC=CC=C3C=CC=2)C(=O)N=C1N(CC1)CCN1CC1=CC=CC=C1 ZMZXKEFAKVKPTI-UHFFFAOYSA-N 0.000 claims 1
- IAYVFWWWUXJBHX-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-(naphthalen-2-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3C=CC=CC3=CC=2)C(=O)N=C1N(CC1)CCN1CC1=CC=CC=C1 IAYVFWWWUXJBHX-UHFFFAOYSA-N 0.000 claims 1
- KYAGKVWJHKMNKV-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-(quinolin-3-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3C=CC=CC3=NC=2)C(=O)N=C1N(CC1)CCN1CC1=CC=CC=C1 KYAGKVWJHKMNKV-UHFFFAOYSA-N 0.000 claims 1
- KYENUZOHPDQMEO-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-[(3-phenoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound O=C1N=C(N2CCN(CC=3C=CC=CC=3)CC2)SC1=CC(C=1)=CC=CC=1OC1=CC=CC=C1 KYENUZOHPDQMEO-UHFFFAOYSA-N 0.000 claims 1
- HBQKYULPFINXJD-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-[(4-methylphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C)=CC=C1C=C1C(=O)N=C(N2CCN(CC=3C=CC=CC=3)CC2)S1 HBQKYULPFINXJD-UHFFFAOYSA-N 0.000 claims 1
- TVIQEXYEBGLMSW-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-[(4-propan-2-ylphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C(C)C)=CC=C1C=C1C(=O)N=C(N2CCN(CC=3C=CC=CC=3)CC2)S1 TVIQEXYEBGLMSW-UHFFFAOYSA-N 0.000 claims 1
- JLXKGKRSTOJRHI-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-[(4-tert-butylphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C=C1C(=O)N=C(N2CCN(CC=3C=CC=CC=3)CC2)S1 JLXKGKRSTOJRHI-UHFFFAOYSA-N 0.000 claims 1
- TYGJEHXRRCWSDD-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-[(6-methoxynaphthalen-2-yl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C=C(C(N=1)=O)SC=1N(CC1)CCN1CC1=CC=CC=C1 TYGJEHXRRCWSDD-UHFFFAOYSA-N 0.000 claims 1
- DEDSBZDZQRVHJR-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-[[4-(pentafluoro-$l^{6}-sulfanyl)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(S(F)(F)(F)(F)F)=CC=C1C=C1C(=O)N=C(N2CCN(CC=3C=CC=CC=3)CC2)S1 DEDSBZDZQRVHJR-UHFFFAOYSA-N 0.000 claims 1
- IQYAEDSKNVGNDD-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-[[4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C=C1C(=O)N=C(N2CCN(CC=3C=CC=CC=3)CC2)S1 IQYAEDSKNVGNDD-UHFFFAOYSA-N 0.000 claims 1
- ZXCIXDZAYYZIRZ-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-5-[[4-(trifluoromethyl)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C=C1C(=O)N=C(N2CCN(CC=3C=CC=CC=3)CC2)S1 ZXCIXDZAYYZIRZ-UHFFFAOYSA-N 0.000 claims 1
- YFRTUEOFVNEUII-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)-5-[(4-methylphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1CN(CC)CCN1C(S1)=NC(=O)C1=CC1=CC=C(C)C=C1 YFRTUEOFVNEUII-UHFFFAOYSA-N 0.000 claims 1
- OQTQGNHTWYLFCZ-UHFFFAOYSA-N 2-(4-hydroxy-3-methoxyphenyl)-5-[(4-methylphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(O)C(OC)=CC(C=2SC(C(=O)N=2)=CC=2C=CC(C)=CC=2)=C1 OQTQGNHTWYLFCZ-UHFFFAOYSA-N 0.000 claims 1
- ZLEBATFFHPARQF-UHFFFAOYSA-N 2-(4-phenylpiperazin-1-yl)-5-(quinolin-3-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3C=CC=CC3=NC=2)C(=O)N=C1N(CC1)CCN1C1=CC=CC=C1 ZLEBATFFHPARQF-UHFFFAOYSA-N 0.000 claims 1
- STQDYYRUIUPXIT-UHFFFAOYSA-N 2-(4-phenylpiperazin-1-yl)-5-[[2-(trifluoromethyl)phenyl]methylidene]-1,3-thiazol-4-one Chemical compound FC(F)(F)C1=CC=CC=C1C=C1C(=O)N=C(N2CCN(CC2)C=2C=CC=CC=2)S1 STQDYYRUIUPXIT-UHFFFAOYSA-N 0.000 claims 1
- PXUHDIYJZSYMDZ-UHFFFAOYSA-N 2-(4-tert-butylanilino)-5-[(4-methylphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(C)=CC=C1C=C1C(=O)N=C(NC=2C=CC(=CC=2)C(C)(C)C)S1 PXUHDIYJZSYMDZ-UHFFFAOYSA-N 0.000 claims 1
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| PCT/EP2006/004666 WO2006122777A2 (de) | 2005-05-20 | 2006-05-17 | Verwendung von 2,5-disubstituierten thiazol-4-on-derivaten in arzneimitteln |
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| DE102007040336A1 (de) * | 2007-08-27 | 2009-03-05 | Johann Wolfgang Goethe-Universität Frankfurt am Main | Neue Inhibitoren der 5-Lipoxygenase und deren Verwendungen |
| CL2009000294A1 (es) * | 2008-02-08 | 2009-10-23 | Shlorion Pharma Inc | Compuestos derivados de heterociclos aril metilideno; composicion farmaceutica que los comprende; y uso en el tratamiento del dolor neuropatico e inflamacion. |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| WO2011092290A1 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| CN107249583B (zh) | 2015-02-09 | 2021-05-07 | 国立大学法人冈山大学 | 乳酸脱氢酶抑制剂以及含有该抑制剂的抗癫痫剂 |
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| HUP0104204A3 (en) * | 1998-11-03 | 2002-06-28 | Glaxo Group Ltd | Pyrazolopyridine derivatives as cox-2 inhibitors, process for their preparation and pharmaceutical compositions thereof |
| WO2003057166A2 (en) * | 2002-01-07 | 2003-07-17 | Pharmacia Corporation | Treatment of pain, inflammation, and inflammation-related disorders with a combination of a cyclooxygenase-2 selective inhibitor and aspirin |
| US7265138B2 (en) * | 2003-02-10 | 2007-09-04 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| US20090156644A1 (en) * | 2005-07-21 | 2009-06-18 | Jacob Westman | Use of thiazole derivatives and analogues in the treatment of cancer |
-
2005
- 2005-05-20 DE DE102005024012A patent/DE102005024012A1/de not_active Withdrawn
-
2006
- 2006-05-17 PL PL06753682T patent/PL1890695T3/pl unknown
- 2006-05-17 EP EP06753682A patent/EP1890695B1/de not_active Not-in-force
- 2006-05-17 JP JP2008511622A patent/JP5421589B2/ja not_active Expired - Fee Related
- 2006-05-17 ES ES06753682T patent/ES2402200T3/es active Active
- 2006-05-17 WO PCT/EP2006/004666 patent/WO2006122777A2/de not_active Ceased
- 2006-05-17 CA CA002609002A patent/CA2609002A1/en not_active Abandoned
- 2006-05-17 US US11/915,156 patent/US20090215758A1/en not_active Abandoned
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