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 |
|---|---|
| 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) |
| US7851503B2 (en) | 2002-08-14 | 2010-12-14 | Nissan Chemical Industries, Ltd. | Thrombopoetin receptor activator and process for producing the same |
| TWI324593B (en) | 2002-10-09 | 2010-05-11 | Nissan Chemical Ind Ltd | Pyrazolone compounds and thrombopoietin receptor activator |
| UA82695C2 (uk) * | 2003-06-06 | 2008-05-12 | Нисан Кемикал Индастриз, Лтд. | Гетероароматичні сполуки як активатори рецептора тромбопоетину |
| CN101386596B (zh) * | 2003-06-06 | 2011-10-26 | 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作为血小板生成素受体激活剂 |
| 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 |
| DE602005024599D1 (de) * | 2004-10-25 | 2010-12-16 | Ligand Pharm Inc | Verbindungen modulierende thrombopoietinaktivität und verfahren |
| TW200633998A (en) * | 2004-12-08 | 2006-10-01 | Nissan Chemical Ind Ltd | Substituted heterocyclic compounds and thrombopoietin receptor activators |
| WO2006062240A1 (en) * | 2004-12-08 | 2006-06-15 | Nissan Chemical Industries, Ltd. | 3-ethylidenehydrazino substituted heterocyclic compounds as thrombopoietin receptor activators |
| TW200633997A (en) * | 2004-12-08 | 2006-10-01 | Nissan Chemical Ind Ltd | Substituted heterocyclic compounds and thrombopoietin receptor activators |
| KR101215207B1 (ko) | 2004-12-14 | 2012-12-26 | 닛산 가가쿠 고교 가부시키 가이샤 | 아미드 화합물 및 트롬보포이에틴 리셉터 활성화제 |
| JP5071375B2 (ja) | 2005-07-15 | 2012-11-14 | 日産化学工業株式会社 | チオフェン化合物及びトロンボポエチンレセプター活性化剤 |
| JP5104752B2 (ja) | 2005-07-20 | 2012-12-19 | 日産化学工業株式会社 | ピラゾール化合物及びトロンボポエチンレセプター活性化剤 |
| US8026368B2 (en) | 2005-11-07 | 2011-09-27 | Nissan Chemical Industries, Ltd. | Hydrazide compounds and thrombopoietin receptor activators |
| US8093251B2 (en) | 2006-06-07 | 2012-01-10 | Nissan Chemical Industries, Ltd. | Nitrogen-containing heterocyclic compounds and thrombopoietin receptor activators |
| 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 |
| EP3023426A1 (en) | 2008-07-17 | 2016-05-25 | Critical Outcome Technologies, Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| 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 |
| EP2434894B1 (en) | 2009-05-29 | 2016-08-31 | Novartis AG | Methods of administration of thrombopoietin agonist compounds |
| EP2492262B1 (en) * | 2009-10-23 | 2016-04-20 | Nissan Chemical Industries, Ltd. | Fused heterocyclic compound and thrombopoietin receptor activator |
| WO2011120153A1 (en) | 2010-04-01 | 2011-10-06 | Critical Outcome Technologies Inc. | Compounds and method for 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 |
| WO2013086436A1 (en) | 2011-12-08 | 2013-06-13 | Fred Hutchinson Cancer Research Center | Compositions and methods for enhanced generation of hematopoietic stem/progenitor cells |
| SI2807165T1 (sl) | 2012-01-27 | 2019-08-30 | Universite De Montreal | Pirimido(4,5-B)indol derivati in njihova uporaba pri ekspanziji hematopoetskih matičnih celic |
| CA2946446C (en) | 2014-04-22 | 2020-11-03 | Universite De Montreal | Pyrido-pyrrolo-pyrimidine and pyrido-indole compounds, pharmaceutical compositions containing same and their use thereof in the expansion of hematopoietic stem cells and/or hematopoietic progenitor cells |
| SG11201703407UA (en) | 2014-10-31 | 2017-05-30 | Nissan Chemical Ind Ltd | Ligand-binding fiber and cell culture substrate using said fiber |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO1999011262A1 (en) | 1997-09-02 | 1999-03-11 | Roche Diagnostics Gmbh | Mpl-receptor ligands, process for their preparation, medicaments containing them and 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 |
| AU771460B2 (en) * | 1999-09-24 | 2004-03-25 | Smithkline Beecham Corporation | Thrombopoietin mimetics |
| JP2003513965A (ja) * | 1999-11-05 | 2003-04-15 | スミスクライン・ビーチャム・コーポレイション | セミカルバゾン誘導体およびそれらのトロンボポエチン模倣物としての使用 |
| US6720345B1 (en) * | 1999-11-05 | 2004-04-13 | Smithkline Beecham Corporation | Semicarbazone derivatives and their use as thrombopoietin mimetics |
-
2001
- 2001-12-19 JP JP2002550771A patent/JP2004520302A/ja active Pending
- 2001-12-19 AU AU2002239718A patent/AU2002239718A1/en not_active Abandoned
- 2001-12-19 EP EP01987514A patent/EP1349613A4/en not_active Withdrawn
- 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 CA CA002436288A patent/CA2436288A1/en not_active Abandoned
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