JP2004520302A5 - - Google Patents
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- Publication number
- JP2004520302A5 JP2004520302A5 JP2002550771A JP2002550771A JP2004520302A5 JP 2004520302 A5 JP2004520302 A5 JP 2004520302A5 JP 2002550771 A JP2002550771 A JP 2002550771A JP 2002550771 A JP2002550771 A JP 2002550771A JP 2004520302 A5 JP2004520302 A5 JP 2004520302A5
- Authority
- JP
- Japan
- Prior art keywords
- thiosemicarbazide
- carboxyphenyl
- hydroxy
- hydroxybenzylidene
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 150000002148 esters Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- -1 Sulfonyloxy Chemical group 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 5
- VFCALJNTDQGHMK-UHFFFAOYSA-N 3-[[[2-hydroxy-3-[3-(trifluoromethyl)phenyl]phenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C(C=CC=2)C=2C=C(C=CC=2)C(F)(F)F)O)=C1 VFCALJNTDQGHMK-UHFFFAOYSA-N 0.000 claims 4
- QIJSYAISKLCJCC-UHFFFAOYSA-N 3-[[[3-(4-chlorophenyl)-2-hydroxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C(C=CC=2)C=2C=CC(Cl)=CC=2)O)=C1 QIJSYAISKLCJCC-UHFFFAOYSA-N 0.000 claims 4
- MWCYXFDINULMKT-UHFFFAOYSA-N 4-[[[2-hydroxy-3-[3-(trifluoromethyl)phenyl]phenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC=CC(C=2C=C(C=CC=2)C(F)(F)F)=C1O MWCYXFDINULMKT-UHFFFAOYSA-N 0.000 claims 4
- ALKUTHOCHXTHGO-UHFFFAOYSA-N CC1=NN(C=2C=C(Cl)C=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 Chemical compound CC1=NN(C=2C=C(Cl)C=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 ALKUTHOCHXTHGO-UHFFFAOYSA-N 0.000 claims 4
- YHBPNJPFCBCOFR-UHFFFAOYSA-N CC1=NN(C=2C=CC(C)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 Chemical compound CC1=NN(C=2C=CC(C)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 YHBPNJPFCBCOFR-UHFFFAOYSA-N 0.000 claims 4
- WEFMDLQCHTYNBX-UHFFFAOYSA-N CC1=NN(C=2C=CC(C)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 Chemical compound CC1=NN(C=2C=CC(C)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 WEFMDLQCHTYNBX-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 4
- ZWARMPFQILFHQI-UHFFFAOYSA-N 3-[[(2-hydroxy-3-naphthalen-1-ylphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C(C=CC=2)C=2C3=CC=CC=C3C=CC=2)O)=C1 ZWARMPFQILFHQI-UHFFFAOYSA-N 0.000 claims 3
- FVLKOLRURFXGTB-UHFFFAOYSA-N 3-[[[3-(3,4-dimethylphenyl)-2-hydroxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(C=NNC(=S)NC=2C=C(C=CC=2)C(O)=O)=C1O FVLKOLRURFXGTB-UHFFFAOYSA-N 0.000 claims 3
- VALRCPIAPNZYED-UHFFFAOYSA-N 3-[[[3-(3-chlorophenyl)-2-hydroxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C(C=CC=2)C=2C=C(Cl)C=CC=2)O)=C1 VALRCPIAPNZYED-UHFFFAOYSA-N 0.000 claims 3
- WCKCUVQDZQNIGP-UHFFFAOYSA-N 4-[[(2-hydroxy-3-naphthalen-1-ylphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC=CC(C=2C3=CC=CC=C3C=CC=2)=C1O WCKCUVQDZQNIGP-UHFFFAOYSA-N 0.000 claims 3
- GBWWYDCAADZYJT-UHFFFAOYSA-N 4-[[(3-dibenzofuran-1-yl-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC=CC(C=2C=3C4=CC=CC=C4OC=3C=CC=2)=C1O GBWWYDCAADZYJT-UHFFFAOYSA-N 0.000 claims 3
- UAWYHCROQVOBQD-UHFFFAOYSA-N 4-[[[3-(3,4-dimethylphenyl)-2-hydroxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(C=NNC(=S)NC=2C=CC(=CC=2)C(O)=O)=C1O UAWYHCROQVOBQD-UHFFFAOYSA-N 0.000 claims 3
- LBMNKCJYSAWRFO-UHFFFAOYSA-N 4-[[[3-(3-chlorophenyl)-2-hydroxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC=CC(C=2C=C(Cl)C=CC=2)=C1O LBMNKCJYSAWRFO-UHFFFAOYSA-N 0.000 claims 3
- WIJLTARCTKJYKH-UHFFFAOYSA-N 4-[[[3-(4-fluorophenyl)-2-hydroxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC=CC(C=2C=CC(F)=CC=2)=C1O WIJLTARCTKJYKH-UHFFFAOYSA-N 0.000 claims 3
- PYSPXZUPBGJJKO-UHFFFAOYSA-N CC1=NN(C=2C=C(C)C(C)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 Chemical compound CC1=NN(C=2C=C(C)C(C)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 PYSPXZUPBGJJKO-UHFFFAOYSA-N 0.000 claims 3
- IDSLFZRXTLXFDQ-UHFFFAOYSA-N CC1=NN(C=2C=C(C)C(C)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 Chemical compound CC1=NN(C=2C=C(C)C(C)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 IDSLFZRXTLXFDQ-UHFFFAOYSA-N 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- TWAWOIXFARPQEV-UHFFFAOYSA-N 1-naphthalen-1-yl-3-[(2,4,6-trihydroxyphenyl)methylideneamino]thiourea Chemical compound OC1=CC(O)=CC(O)=C1C=NNC(=S)NC1=CC=CC2=CC=CC=C12 TWAWOIXFARPQEV-UHFFFAOYSA-N 0.000 claims 2
- TUOFIEPMBWHMFM-UHFFFAOYSA-N 2-hydroxy-3-[[(2-phenylphenyl)carbamothioylhydrazinylidene]methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=NNC(=S)NC=2C(=CC=CC=2)C=2C=CC=CC=2)=C1O TUOFIEPMBWHMFM-UHFFFAOYSA-N 0.000 claims 2
- LQZRVCNWPMJYPJ-UHFFFAOYSA-N 3-[[(1-hydroxynaphthalen-2-yl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C3C=CC=CC3=CC=2)O)=C1 LQZRVCNWPMJYPJ-UHFFFAOYSA-N 0.000 claims 2
- NPJUJWQHRHKWFD-UHFFFAOYSA-N 3-[[(2-hydroxy-3-methylphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound CC1=CC=CC(C=NNC(=S)NC=2C=C(C=CC=2)C(O)=O)=C1O NPJUJWQHRHKWFD-UHFFFAOYSA-N 0.000 claims 2
- HISAASSZNKFWCP-UHFFFAOYSA-N 3-[[(2-hydroxy-4-phenylmethoxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=CC(OCC=3C=CC=CC=3)=CC=2)O)=C1 HISAASSZNKFWCP-UHFFFAOYSA-N 0.000 claims 2
- JVOHKSPQGGNUBU-UHFFFAOYSA-N 3-[[(2-hydroxy-4-phenylphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=CC(=CC=2)C=2C=CC=CC=2)O)=C1 JVOHKSPQGGNUBU-UHFFFAOYSA-N 0.000 claims 2
- GECNPSKMOQGWAZ-UHFFFAOYSA-N 3-[[(2-hydroxy-5-methylphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound CC1=CC=C(O)C(C=NNC(=S)NC=2C=C(C=CC=2)C(O)=O)=C1 GECNPSKMOQGWAZ-UHFFFAOYSA-N 0.000 claims 2
- QMOAVDKGYWFNAG-UHFFFAOYSA-N 3-[[(2-hydroxynaphthalen-1-yl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C3=CC=CC=C3C=CC=2O)=C1 QMOAVDKGYWFNAG-UHFFFAOYSA-N 0.000 claims 2
- GRKPGUWGRCLPRE-UHFFFAOYSA-N 3-[[(3,5-dibromo-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C(Br)C=C(Br)C=2)O)=C1 GRKPGUWGRCLPRE-UHFFFAOYSA-N 0.000 claims 2
- IODNLNAHXFGQHJ-UHFFFAOYSA-N 3-[[(3,5-dichloro-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C(Cl)C=C(Cl)C=2)O)=C1 IODNLNAHXFGQHJ-UHFFFAOYSA-N 0.000 claims 2
- ZRSHOJCPIOKLKE-UHFFFAOYSA-N 3-[[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=NNC(=S)NC=2C=C(C=CC=2)C(O)=O)=C1O ZRSHOJCPIOKLKE-UHFFFAOYSA-N 0.000 claims 2
- VJMQJWOCTBFBPN-UHFFFAOYSA-N 3-[[(3-dibenzofuran-1-yl-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C(C=CC=2)C=2C=3C4=CC=CC=C4OC=3C=CC=2)O)=C1 VJMQJWOCTBFBPN-UHFFFAOYSA-N 0.000 claims 2
- USYCRXALBNDUKJ-UHFFFAOYSA-N 3-[[(5-chloro-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=CC=C(Cl)C=2)O)=C1 USYCRXALBNDUKJ-UHFFFAOYSA-N 0.000 claims 2
- WSDQJMNLGVQDBD-UHFFFAOYSA-N 3-[[[2-hydroxy-3-(2-methylphenyl)phenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=CC(C=NNC(=S)NC=2C=C(C=CC=2)C(O)=O)=C1O WSDQJMNLGVQDBD-UHFFFAOYSA-N 0.000 claims 2
- PSFGRFWWSASYCL-UHFFFAOYSA-N 3-[[[2-hydroxy-3-(3-nitrophenyl)phenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=S)NN=CC=2C(=C(C=CC=2)C=2C=C(C=CC=2)[N+]([O-])=O)O)=C1 PSFGRFWWSASYCL-UHFFFAOYSA-N 0.000 claims 2
- VXOICBRTBCNFKN-UHFFFAOYSA-N 3-[[[3-(4-chlorophenyl)-2-methoxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC=C(C=2C=CC(Cl)=CC=2)C(OC)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 VXOICBRTBCNFKN-UHFFFAOYSA-N 0.000 claims 2
- UDQCKYBBGYUIEG-UHFFFAOYSA-N 3-[[[3-(4-fluorophenyl)-2-methoxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC=C(C=2C=CC(F)=CC=2)C(OC)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 UDQCKYBBGYUIEG-UHFFFAOYSA-N 0.000 claims 2
- LKWHYVVNESTTIU-UHFFFAOYSA-N 3-hydroxy-4-[(naphthalen-1-ylcarbamothioylhydrazinylidene)methyl]benzoic acid Chemical compound OC1=CC(C(=O)O)=CC=C1C=NNC(=S)NC1=CC=CC2=CC=CC=C12 LKWHYVVNESTTIU-UHFFFAOYSA-N 0.000 claims 2
- CQBBXJRDZBQGOR-UHFFFAOYSA-N 3-hydroxy-4-[C-methyl-N-(naphthalen-1-ylcarbamothioylamino)carbonimidoyl]benzoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=S)NN=C(C)C1=CC=C(C(O)=O)C=C1O CQBBXJRDZBQGOR-UHFFFAOYSA-N 0.000 claims 2
- LUTNFNMHDCINPH-UHFFFAOYSA-N 3-hydroxy-4-[[(2-phenylphenyl)carbamothioylhydrazinylidene]methyl]benzoic acid Chemical compound OC1=CC(C(=O)O)=CC=C1C=NNC(=S)NC1=CC=CC=C1C1=CC=CC=C1 LUTNFNMHDCINPH-UHFFFAOYSA-N 0.000 claims 2
- ZYQUZDHIWLYVGE-UHFFFAOYSA-N 3-hydroxy-4-[[(4-methylphenyl)carbamothioylhydrazinylidene]methyl]benzoic acid Chemical compound C1=CC(C)=CC=C1NC(=S)NN=CC1=CC=C(C(O)=O)C=C1O ZYQUZDHIWLYVGE-UHFFFAOYSA-N 0.000 claims 2
- VTJLRWCGVUSVLQ-UHFFFAOYSA-N 4-[[(1-hydroxynaphthalen-2-yl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC=C(C=CC=C2)C2=C1O VTJLRWCGVUSVLQ-UHFFFAOYSA-N 0.000 claims 2
- UPYSQLCTQXVZNP-UHFFFAOYSA-N 4-[[(2-hydroxy-3-methylphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound CC1=CC=CC(C=NNC(=S)NC=2C=CC(=CC=2)C(O)=O)=C1O UPYSQLCTQXVZNP-UHFFFAOYSA-N 0.000 claims 2
- YQXNVEAPRKYUKO-UHFFFAOYSA-N 4-[[(2-hydroxy-4-phenylmethoxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC(C(=C1)O)=CC=C1OCC1=CC=CC=C1 YQXNVEAPRKYUKO-UHFFFAOYSA-N 0.000 claims 2
- XMXAJWXDVMPTHI-UHFFFAOYSA-N 4-[[(2-hydroxy-4-phenylphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC=C(C=2C=CC=CC=2)C=C1O XMXAJWXDVMPTHI-UHFFFAOYSA-N 0.000 claims 2
- HNJYHRAQHTUHOF-UHFFFAOYSA-N 4-[[(2-hydroxynaphthalen-1-yl)methylideneamino]carbamothioylamino]benzenesulfonic acid Chemical compound OC1=CC=C2C=CC=CC2=C1C=NNC(=S)NC1=CC=C(S(O)(=O)=O)C=C1 HNJYHRAQHTUHOF-UHFFFAOYSA-N 0.000 claims 2
- HVQHPDYIFALHFO-UHFFFAOYSA-N 4-[[(2-hydroxynaphthalen-1-yl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=C(O)C=CC2=CC=CC=C12 HVQHPDYIFALHFO-UHFFFAOYSA-N 0.000 claims 2
- DCCGJSLGJZENLV-UHFFFAOYSA-N 4-[[(3,5-dibromo-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC(Br)=CC(Br)=C1O DCCGJSLGJZENLV-UHFFFAOYSA-N 0.000 claims 2
- OFUFMJBVLRNBKR-UHFFFAOYSA-N 4-[[(3,5-dichloro-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzenesulfonic acid Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=NNC(=S)NC1=CC=C(S(O)(=O)=O)C=C1 OFUFMJBVLRNBKR-UHFFFAOYSA-N 0.000 claims 2
- QMGQAJPXSFAAJN-UHFFFAOYSA-N 4-[[(3,5-dichloro-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC(Cl)=CC(Cl)=C1O QMGQAJPXSFAAJN-UHFFFAOYSA-N 0.000 claims 2
- AKLJHKWOWQKHGD-UHFFFAOYSA-N 4-[[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=NNC(=S)NC=2C=CC(=CC=2)C(O)=O)=C1O AKLJHKWOWQKHGD-UHFFFAOYSA-N 0.000 claims 2
- KRKLVKVKGJPTKL-UHFFFAOYSA-N 4-[[(3-chloro-2-methylphenyl)carbamothioylhydrazinylidene]methyl]-3-hydroxybenzoic acid Chemical compound CC1=C(Cl)C=CC=C1NC(=S)NN=CC1=CC=C(C(O)=O)C=C1O KRKLVKVKGJPTKL-UHFFFAOYSA-N 0.000 claims 2
- OMBHPXMNKZUCQK-UHFFFAOYSA-N 4-[[(3-chloro-4-methylphenyl)carbamothioylhydrazinylidene]methyl]-3-hydroxybenzoic acid Chemical compound C1=C(Cl)C(C)=CC=C1NC(=S)NN=CC1=CC=C(C(O)=O)C=C1O OMBHPXMNKZUCQK-UHFFFAOYSA-N 0.000 claims 2
- XXBOTESYSVDCKG-UHFFFAOYSA-N 4-[[(3-dibenzofuran-1-yl-2-methoxyphenyl)methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC=C(C=2C=3C4=CC=CC=C4OC=3C=CC=2)C(OC)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 XXBOTESYSVDCKG-UHFFFAOYSA-N 0.000 claims 2
- PLHRTNRUXYEBMB-UHFFFAOYSA-N 4-[[[2-hydroxy-3-(2-methylphenyl)phenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=CC(C=NNC(=S)NC=2C=CC(=CC=2)C(O)=O)=C1O PLHRTNRUXYEBMB-UHFFFAOYSA-N 0.000 claims 2
- ITKPBXHMSPJQOS-UHFFFAOYSA-N 4-[[[2-hydroxy-3-(3-nitrophenyl)phenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=S)NN=CC1=CC=CC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1O ITKPBXHMSPJQOS-UHFFFAOYSA-N 0.000 claims 2
- GZOZAGSXKSBOIM-UHFFFAOYSA-N 4-[[[2-methoxy-3-(4-methylphenyl)phenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC=C(C=2C=CC(C)=CC=2)C(OC)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 GZOZAGSXKSBOIM-UHFFFAOYSA-N 0.000 claims 2
- URXCYDYNDFNSPK-UHFFFAOYSA-N 4-[[[3-(4-chlorophenyl)-2-methoxyphenyl]methylideneamino]carbamothioylamino]benzoic acid Chemical compound C1=CC=C(C=2C=CC(Cl)=CC=2)C(OC)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 URXCYDYNDFNSPK-UHFFFAOYSA-N 0.000 claims 2
- QNDNPQMXJMDUFD-UHFFFAOYSA-N CC1=NN(C=2C=C(Cl)C=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 Chemical compound CC1=NN(C=2C=C(Cl)C=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 QNDNPQMXJMDUFD-UHFFFAOYSA-N 0.000 claims 2
- WCENBRDPMHYUHH-UHFFFAOYSA-N CC1=NN(C=2C=CC(Cl)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 Chemical compound CC1=NN(C=2C=CC(Cl)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 WCENBRDPMHYUHH-UHFFFAOYSA-N 0.000 claims 2
- LEMGSEFDBUTNLL-UHFFFAOYSA-N CC1=NN(C=2C=CC(Cl)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 Chemical compound CC1=NN(C=2C=CC(Cl)=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 LEMGSEFDBUTNLL-UHFFFAOYSA-N 0.000 claims 2
- SHTIKJUFDWIZFQ-UHFFFAOYSA-N CC1=NN(C=2C=CC=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 Chemical compound CC1=NN(C=2C=CC=CC=2)C(O)=C1C=NNC(=S)NC1=CC=C(C(O)=O)C=C1 SHTIKJUFDWIZFQ-UHFFFAOYSA-N 0.000 claims 2
- OXCWBKOCWCBSIW-UHFFFAOYSA-N CC1=NN(C=2C=CC=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 Chemical compound CC1=NN(C=2C=CC=CC=2)C(O)=C1C=NNC(=S)NC1=CC=CC(C(O)=O)=C1 OXCWBKOCWCBSIW-UHFFFAOYSA-N 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- DBGIPLVUWNOTCU-UHFFFAOYSA-N chembl530042 Chemical compound OC1=CC(O)=CC=C1C=NNC(=S)NC1=CC=CC2=CC=CC=C12 DBGIPLVUWNOTCU-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 206010043554 thrombocytopenia Diseases 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- VKHXYYHYCASSEP-UHFFFAOYSA-N 1-(4-chloro-2-methylphenyl)-3-[(2-hydroxy-3,5-dinitrophenyl)methylideneamino]thiourea Chemical compound CC1=CC(Cl)=CC=C1NC(=S)NN=CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O VKHXYYHYCASSEP-UHFFFAOYSA-N 0.000 claims 1
- VFTMCXMWDFLPQM-UHFFFAOYSA-N 1-[(2-hydroxy-3,5-dinitrophenyl)methylideneamino]-3-(2-methylphenyl)thiourea Chemical compound CC1=CC=CC=C1NC(=S)NN=CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O VFTMCXMWDFLPQM-UHFFFAOYSA-N 0.000 claims 1
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- FQJSETGPFVXDQM-UHFFFAOYSA-N ethyl 4-[[(3,5-dichloro-2-hydroxyphenyl)methylideneamino]carbamothioylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=S)NN=CC1=CC(Cl)=CC(Cl)=C1O FQJSETGPFVXDQM-UHFFFAOYSA-N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25662200P | 2000-12-19 | 2000-12-19 | |
| PCT/US2001/050774 WO2002049413A2 (en) | 2000-12-19 | 2001-12-19 | Thrombopoietin mimetics |
Publications (2)
| Publication Number | Publication Date |
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| JP2004520302A JP2004520302A (ja) | 2004-07-08 |
| JP2004520302A5 true JP2004520302A5 (enExample) | 2005-12-22 |
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| JP2002550771A Pending JP2004520302A (ja) | 2000-12-19 | 2001-12-19 | トロンボポエチン模倣物 |
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| EP (1) | EP1349613A4 (enExample) |
| JP (1) | JP2004520302A (enExample) |
| AU (1) | AU2002239718A1 (enExample) |
| CA (1) | CA2436288A1 (enExample) |
| WO (1) | WO2002049413A2 (enExample) |
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| CY2010012I2 (el) | 2000-05-25 | 2020-05-29 | Novartis Ag | Μιμητικα θρομβοποιητινης |
| AUPS120902A0 (en) * | 2002-03-19 | 2002-04-18 | Unisearch Limited | Iron chelators as anti-proliferative agents against tumour cells |
| MY142390A (en) | 2002-05-22 | 2010-11-30 | Glaxosmithkline Llc | 3' - [(2z)-[1-(3,4-dimethylphenyl)-1,5- dihydro-3- methyl-5-0xo-4h-pyrazol-4- ylidene]hydrazino]-2' -hydroxy -[1,1' -biphenyl]-3-carboxylic acid bis-(monoethanolamine) |
| JP4412173B2 (ja) | 2002-08-14 | 2010-02-10 | 日産化学工業株式会社 | トロンボポエチンレセプター活性化剤ならびにそれらの製造方法 |
| TWI324593B (en) * | 2002-10-09 | 2010-05-11 | Nissan Chemical Ind Ltd | Pyrazolone compounds and thrombopoietin receptor activator |
| CN100443472C (zh) * | 2003-06-06 | 2008-12-17 | 日产化学工业株式会社 | 3-亚烷基肼基取代的杂芳基化合物以及含有其的药物 |
| UA82695C2 (uk) * | 2003-06-06 | 2008-05-12 | Нисан Кемикал Индастриз, Лтд. | Гетероароматичні сполуки як активатори рецептора тромбопоетину |
| TW200526638A (en) | 2003-10-22 | 2005-08-16 | Smithkline Beecham Corp | 2-(3,4-dimethylphenyl)-4-{[2-hydroxy-3'-(1H-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one choline |
| JP4716672B2 (ja) * | 2004-05-19 | 2011-07-06 | 大塚製薬株式会社 | 巨核球産生誘導剤 |
| WO2005118551A2 (en) * | 2004-05-28 | 2005-12-15 | Ligand Pharmaceuticals Inc. | Thrombopoietin activity modulating compounds and methods |
| WO2006047344A1 (en) * | 2004-10-25 | 2006-05-04 | Ligand Pharmaceuticals, Inc. | Thrombopoietin activity modulating compounds and methods |
| TW200633997A (en) * | 2004-12-08 | 2006-10-01 | Nissan Chemical Ind Ltd | Substituted heterocyclic compounds and thrombopoietin receptor activators |
| CA2588979C (en) * | 2004-12-08 | 2013-01-22 | Nissan Chemical Industries, Ltd. | 3-ethylidenehydrazino substituted heterocyclic compounds as thrombopoietin receptor activators |
| TW200633998A (en) * | 2004-12-08 | 2006-10-01 | Nissan Chemical Ind Ltd | Substituted heterocyclic compounds and thrombopoietin receptor activators |
| AU2005314788B2 (en) * | 2004-12-14 | 2011-09-22 | Nissan Chemical Industries, Ltd. | Amide compound and thrombopoietin receptor activator |
| NZ563202A (en) | 2005-07-15 | 2011-02-25 | Nissan Chemical Ind Ltd | Thiophene compounds and thrombopoietin receptor activators |
| EP1904488B1 (en) | 2005-07-20 | 2013-03-06 | Nissan Chemical Industries, Ltd. | Pyrazole compounds and thrombopoietin receptor activators |
| KR101350099B1 (ko) | 2005-11-07 | 2014-01-09 | 닛산 가가쿠 고교 가부시키 가이샤 | 하이드라지드 화합물 및 트롬보포이에틴 리셉터 활성화제 |
| WO2007142308A1 (ja) | 2006-06-07 | 2007-12-13 | Nissan Chemical Industries, Ltd. | 含窒素ヘテロ環化合物及びトロンボポエチンレセプター活性化剤 |
| US8138191B2 (en) | 2007-01-11 | 2012-03-20 | Critical Outcome Technologies Inc. | Inhibitor compounds and cancer treatment methods |
| ECSP077628A (es) | 2007-05-03 | 2008-12-30 | Smithkline Beechman Corp | Nueva composición farmacéutica |
| US8466151B2 (en) | 2007-12-26 | 2013-06-18 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| PE20100362A1 (es) | 2008-10-30 | 2010-05-27 | Irm Llc | Derivados de purina que expanden las celulas madre hematopoyeticas |
| US8680150B2 (en) * | 2009-05-28 | 2014-03-25 | Ligand Pharmaceuticals, Inc. | Small molecule hematopoietic growth factor mimetic compounds that activate hematopoietic growth factor receptors |
| PL2434894T3 (pl) | 2009-05-29 | 2017-04-28 | Novartis Ag | Sposoby podawania związków będących agonistami trombopoetyny |
| EP2492262B1 (en) * | 2009-10-23 | 2016-04-20 | Nissan Chemical Industries, Ltd. | Fused heterocyclic compound and thrombopoietin receptor activator |
| EP3235818A3 (en) | 2010-04-01 | 2018-03-14 | Critical Outcome Technologies, Inc. | Compounds for the treatment of hiv |
| UA109287C2 (uk) * | 2010-11-02 | 2015-08-10 | Солі органічного аміну похідних амінобензойної кислоти і спосіб їх одержання | |
| WO2012102937A2 (en) | 2011-01-25 | 2012-08-02 | Irm Llc | Compounds that expand hematopoietic stem cells |
| EP2788476B1 (en) | 2011-12-08 | 2019-05-22 | Fred Hutchinson Cancer Research Center | Compositions and methods for enhanced generation of hematopoietic stem/progenitor cells |
| RS59002B1 (sr) | 2012-01-27 | 2019-08-30 | Univ Montreal | Pirimido[4,5-b]indol derivati i njihova primena u ekspanziji hematopoetskih matičnih ćelija |
| WO2015161373A1 (en) | 2014-04-22 | 2015-10-29 | Université de Montréal | Compounds and use thereof in the expansion of hematopoietic stem cells and/or hematopoietic progenitor cells |
| WO2016068270A1 (ja) | 2014-10-31 | 2016-05-06 | 日産化学工業株式会社 | リガンド結合繊維及び当該繊維を用いた細胞培養基材 |
Family Cites Families (9)
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| DE290184C (enExample) * | ||||
| DE286580C (enExample) * | ||||
| EP0433526A1 (de) * | 1989-12-19 | 1991-06-26 | Richter, Peter, Prof. Dr.sc.nat. | Mittel zur Behandlung von Herz-Kreislauf-Erkrankungen, insbesondere von Arrythmien |
| US5376451A (en) * | 1990-06-29 | 1994-12-27 | Minnesota Mining And Manufacturing Company | Yellow color-formers |
| AU9265698A (en) | 1997-09-02 | 1999-03-22 | Boehringer Mannheim Gmbh | Mpl-receptor ligands, process for their preparation, medicaments containing themand their use for the treatment and prevention of thrombocytopaenia and anaemia |
| EP1133291B1 (en) | 1998-11-17 | 2006-01-11 | Smithkline Beecham Corporation | Cyclic polyamines for treating thrombocytopenia |
| WO2001021180A1 (en) * | 1999-09-24 | 2001-03-29 | Smithkline Beecham Corporation | Thrombopoietin mimetics |
| US6720345B1 (en) * | 1999-11-05 | 2004-04-13 | Smithkline Beecham Corporation | Semicarbazone derivatives and their use as thrombopoietin mimetics |
| EP1228051A1 (en) | 1999-11-05 | 2002-08-07 | SmithKline Beecham Corporation | Semicarbazone derivatives and their use as thrombopoietin mimetics |
-
2001
- 2001-12-19 US US10/451,300 patent/US7241783B2/en not_active Expired - Fee Related
- 2001-12-19 WO PCT/US2001/050774 patent/WO2002049413A2/en not_active Ceased
- 2001-12-19 EP EP01987514A patent/EP1349613A4/en not_active Withdrawn
- 2001-12-19 JP JP2002550771A patent/JP2004520302A/ja active Pending
- 2001-12-19 CA CA002436288A patent/CA2436288A1/en not_active Abandoned
- 2001-12-19 AU AU2002239718A patent/AU2002239718A1/en not_active Abandoned
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