JP2005520480A5 - - Google Patents
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- JP2005520480A5 JP2005520480A5 JP2002507845A JP2002507845A JP2005520480A5 JP 2005520480 A5 JP2005520480 A5 JP 2005520480A5 JP 2002507845 A JP2002507845 A JP 2002507845A JP 2002507845 A JP2002507845 A JP 2002507845A JP 2005520480 A5 JP2005520480 A5 JP 2005520480A5
- Authority
- JP
- Japan
- Prior art keywords
- activity
- dichlorophenyl
- alkyl
- prop
- hgf
- 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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- 102100021866 Hepatocyte growth factor Human genes 0.000 description 32
- 238000000034 method Methods 0.000 description 32
- 230000000694 effects Effects 0.000 description 30
- 125000000217 alkyl group Chemical group 0.000 description 26
- 241000124008 Mammalia Species 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 108090000765 processed proteins & peptides Proteins 0.000 description 16
- 210000001519 tissue Anatomy 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 229940079593 drug Drugs 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 239000008194 pharmaceutical composition Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- 210000000056 organ Anatomy 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 10
- -1 2-nitrophenyl Chemical group 0.000 description 9
- 230000001028 anti-proliverative effect Effects 0.000 description 9
- 239000003937 drug carrier Substances 0.000 description 9
- 238000001727 in vivo Methods 0.000 description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 150000002367 halogens Chemical group 0.000 description 8
- 238000000338 in vitro Methods 0.000 description 8
- 230000001737 promoting effect Effects 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000033115 angiogenesis Effects 0.000 description 6
- 230000010261 cell growth Effects 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 5
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 230000006698 induction Effects 0.000 description 5
- 102000040430 polynucleotide Human genes 0.000 description 5
- 108091033319 polynucleotide Proteins 0.000 description 5
- 239000002157 polynucleotide Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 238000003556 assay Methods 0.000 description 4
- 230000004663 cell proliferation Effects 0.000 description 4
- 239000013604 expression vector Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 230000002062 proliferating effect Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 102000003745 Hepatocyte Growth Factor Human genes 0.000 description 3
- 108090000100 Hepatocyte Growth Factor Proteins 0.000 description 3
- 230000002424 anti-apoptotic effect Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 108020004707 nucleic acids Proteins 0.000 description 3
- 102000039446 nucleic acids Human genes 0.000 description 3
- 150000007523 nucleic acids Chemical class 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- DSWQVZBZNPNVOJ-UHFFFAOYSA-N 3,3-dibromo-1-phenylquinoline-2,4-dione Chemical compound C12=CC=CC=C2C(=O)C(Br)(Br)C(=O)N1C1=CC=CC=C1 DSWQVZBZNPNVOJ-UHFFFAOYSA-N 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000002491 angiogenic effect Effects 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000010367 cloning Methods 0.000 description 2
- 239000013599 cloning vector Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000000099 in vitro assay Methods 0.000 description 2
- 238000005462 in vivo assay Methods 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- 150000002545 isoxazoles Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000010046 negative regulation of endothelial cell proliferation Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229940126586 small molecule drug Drugs 0.000 description 2
- 125000001544 thienyl group Chemical class 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 230000004565 tumor cell growth Effects 0.000 description 2
- XNSRUBXOCUNFBQ-UHFFFAOYSA-N (2,4-dichlorophenyl)-[3-[5-(2,4-difluorophenyl)furan-2-yl]pyrazol-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1C1=CC=C(C2=NN(C=C2)C(=O)C=2C(=CC(Cl)=CC=2)Cl)O1 XNSRUBXOCUNFBQ-UHFFFAOYSA-N 0.000 description 1
- UINOSYHKJJAECC-UHFFFAOYSA-N (4-chlorophenyl)-[3,5-dimethyl-4-(1-methylimidazol-2-yl)sulfanylpyrazol-1-yl]methanone Chemical compound CC1=C(SC=2N(C=CN=2)C)C(C)=NN1C(=O)C1=CC=C(Cl)C=C1 UINOSYHKJJAECC-UHFFFAOYSA-N 0.000 description 1
- GRTABJXGFFGWOM-UHFFFAOYSA-N (4-chlorophenyl)-[3-(2-methylimidazo[1,2-a]pyridin-3-yl)pyrazol-1-yl]methanone Chemical compound CC=1N=C2C=CC=CN2C=1C(=N1)C=CN1C(=O)C1=CC=C(Cl)C=C1 GRTABJXGFFGWOM-UHFFFAOYSA-N 0.000 description 1
- OUACWQDYTFTDOF-UHFFFAOYSA-N (4-chlorophenyl)-[3-(2-thiophen-2-ylethenyl)pyrazol-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1N=C(C=CC=2SC=CC=2)C=C1 OUACWQDYTFTDOF-UHFFFAOYSA-N 0.000 description 1
- XARRJXRXEAQBNG-UHFFFAOYSA-N (4-chlorophenyl)-[3-(3-phenyl-1,2-oxazol-5-yl)pyrazol-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1N=C(C=2ON=C(C=2)C=2C=CC=CC=2)C=C1 XARRJXRXEAQBNG-UHFFFAOYSA-N 0.000 description 1
- CSDCQSIMZAMKSR-UHFFFAOYSA-N (4-chlorophenyl)-[3-(5-thiophen-2-ylthiophen-2-yl)pyrazol-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1N=C(C=2SC(=CC=2)C=2SC=CC=2)C=C1 CSDCQSIMZAMKSR-UHFFFAOYSA-N 0.000 description 1
- SOQFBUUUTJLDSF-UHFFFAOYSA-N (4-chlorophenyl)-[3-[3-(4-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]pyrazol-1-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(Cl)=CC=2)C=1C(=N1)C=CN1C(=O)C1=CC=C(Cl)C=C1 SOQFBUUUTJLDSF-UHFFFAOYSA-N 0.000 description 1
- KDUCRYZJQJJHNO-CMDGGOBGSA-N (e)-1-(2-chlorophenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one Chemical compound ClC1=CC=CC(Cl)=C1\C=C\C(=O)C1=CC=CC=C1Cl KDUCRYZJQJJHNO-CMDGGOBGSA-N 0.000 description 1
- HYCQSDMDGCPEPI-XCVCLJGOSA-N (e)-1-(4-bromophenyl)-3-(4-chlorophenyl)prop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1\C=C\C(=O)C1=CC=C(Br)C=C1 HYCQSDMDGCPEPI-XCVCLJGOSA-N 0.000 description 1
- MKRFMIVBRIFCRY-SOFGYWHQSA-N (e)-1-(4-chloro-3-methylphenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one Chemical compound C1=C(Cl)C(C)=CC(C(=O)\C=C\C=2C(=CC=CC=2Cl)Cl)=C1 MKRFMIVBRIFCRY-SOFGYWHQSA-N 0.000 description 1
- GSQGUMFXFLWUJU-XBXARRHUSA-N (e)-1-(4-chlorophenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)\C=C\C1=CC=C(Cl)C=C1Cl GSQGUMFXFLWUJU-XBXARRHUSA-N 0.000 description 1
- UNMRSNMNIOEKID-CMDGGOBGSA-N (e)-1-(4-chlorophenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)\C=C\C1=C(Cl)C=CC=C1Cl UNMRSNMNIOEKID-CMDGGOBGSA-N 0.000 description 1
- XPUCGDUSZRAVLO-KRXBUXKQSA-N (e)-1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)prop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)\C=C\C1=CC=C(Cl)C(Cl)=C1 XPUCGDUSZRAVLO-KRXBUXKQSA-N 0.000 description 1
- WISCZQPKOCVKER-XCVCLJGOSA-N (e)-1-(4-chlorophenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1\C=C\C(=O)C1=CC=C(Cl)C=C1 WISCZQPKOCVKER-XCVCLJGOSA-N 0.000 description 1
- UJAKORSMLGOYRP-WEVVVXLNSA-N (e)-3-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)\C=C\C1=CC=C(Cl)C=C1Cl UJAKORSMLGOYRP-WEVVVXLNSA-N 0.000 description 1
- NSZMURCNUHIMRN-MDZDMXLPSA-N (e)-3-(2,6-dichlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)\C=C\C1=C(Cl)C=CC=C1Cl NSZMURCNUHIMRN-MDZDMXLPSA-N 0.000 description 1
- HPPIWTKQJMZDFB-SOFGYWHQSA-N (e)-3-(3,4-dichlorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)\C=C\C1=CC=C(Cl)C(Cl)=C1 HPPIWTKQJMZDFB-SOFGYWHQSA-N 0.000 description 1
- ZSUBZRVGYKESBB-SOFGYWHQSA-N (e)-3-(5-bromo-2-hydroxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one Chemical compound C1=CC(C)=CC=C1C(=O)\C=C\C1=CC(Br)=CC=C1O ZSUBZRVGYKESBB-SOFGYWHQSA-N 0.000 description 1
- FVEMEWLHXCDRNY-UHFFFAOYSA-N 1,3-bis(5-nitrothiophen-3-yl)prop-2-en-1-one Chemical compound S1C([N+](=O)[O-])=CC(C=CC(=O)C=2C=C(SC=2)[N+]([O-])=O)=C1 FVEMEWLHXCDRNY-UHFFFAOYSA-N 0.000 description 1
- MHHQHUHFNCVROJ-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-(4-chlorophenyl)prop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1C=CC(=O)C1=CSC2=CC=CC=C12 MHHQHUHFNCVROJ-UHFFFAOYSA-N 0.000 description 1
- NGJNCPUDHJBUDA-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(3,5-dichloro-2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=CC(=O)C1=CC=CC=C1Cl NGJNCPUDHJBUDA-UHFFFAOYSA-N 0.000 description 1
- XVRSGCDTFOQNAC-UHFFFAOYSA-N 1-(4-amino-2-methylsulfanyl-1,3-thiazol-5-yl)-3-(4-chlorophenyl)prop-2-en-1-one Chemical compound S1C(SC)=NC(N)=C1C(=O)C=CC1=CC=C(Cl)C=C1 XVRSGCDTFOQNAC-UHFFFAOYSA-N 0.000 description 1
- YXLXIDYHXGTBAU-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(3,5-difluorophenyl)prop-2-en-1-one Chemical compound FC1=CC(F)=CC(C=CC(=O)C=2C=CC(Br)=CC=2)=C1 YXLXIDYHXGTBAU-UHFFFAOYSA-N 0.000 description 1
- KHTCICUOYGSQNH-UHFFFAOYSA-N 1-(4-chloro-3-methylphenyl)-3-(2-chlorophenyl)prop-2-en-1-one Chemical compound C1=C(Cl)C(C)=CC(C(=O)C=CC=2C(=CC=CC=2)Cl)=C1 KHTCICUOYGSQNH-UHFFFAOYSA-N 0.000 description 1
- OKNNLFRSPKBEKD-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3,5-dichloro-2-hydroxyphenyl)prop-2-en-1-one Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=CC(=O)C1=CC=C(Cl)C=C1 OKNNLFRSPKBEKD-UHFFFAOYSA-N 0.000 description 1
- GBNWKBYRKKLUHB-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-3-(2-thiophen-2-ylethenyl)pyrazole Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1N=C(C=CC=2SC=CC=2)C=C1 GBNWKBYRKKLUHB-UHFFFAOYSA-N 0.000 description 1
- RPMIWSHFVXCVQA-UHFFFAOYSA-N 1-[4-[(2-chloro-6-fluorophenyl)methyl]-3,5-dimethylpyrazol-1-yl]-2,2-dimethylpropan-1-one Chemical compound CC1=NN(C(=O)C(C)(C)C)C(C)=C1CC1=C(F)C=CC=C1Cl RPMIWSHFVXCVQA-UHFFFAOYSA-N 0.000 description 1
- OTYFKBWDHIMAHW-UHFFFAOYSA-N 1-methylsulfonyl-3-(2-thiophen-2-ylethenyl)pyrazole Chemical compound CS(=O)(=O)N1C=CC(C=CC=2SC=CC=2)=N1 OTYFKBWDHIMAHW-UHFFFAOYSA-N 0.000 description 1
- RWOVUHIODJUTJG-UHFFFAOYSA-N 2,2-dimethyl-1-[3-(2-thiophen-2-ylethenyl)pyrazol-1-yl]propan-1-one Chemical compound CC(C)(C)C(=O)N1C=CC(C=CC=2SC=CC=2)=N1 RWOVUHIODJUTJG-UHFFFAOYSA-N 0.000 description 1
- CNEHMMDGKNXXAV-UHFFFAOYSA-N 2-chloro-6-[4-[1-[(4-chlorophenyl)methyl]pyrazol-3-yl]phenoxy]benzonitrile Chemical compound C1=CC(Cl)=CC=C1CN1N=C(C=2C=CC(OC=3C(=C(Cl)C=CC=3)C#N)=CC=2)C=C1 CNEHMMDGKNXXAV-UHFFFAOYSA-N 0.000 description 1
- NNXGDPWRSUBNGO-UHFFFAOYSA-N 3,5-ditert-butyl-4-[(2-chloro-6-fluorophenyl)methyl]-1h-pyrazole Chemical compound CC(C)(C)C1=NNC(C(C)(C)C)=C1CC1=C(F)C=CC=C1Cl NNXGDPWRSUBNGO-UHFFFAOYSA-N 0.000 description 1
- VSCQVUUNFUZOBZ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-1-(4-bromophenyl)prop-2-en-1-one Chemical compound C1=CC(Br)=CC=C1C(=O)C=CC1=CC=C(OCO2)C2=C1 VSCQVUUNFUZOBZ-UHFFFAOYSA-N 0.000 description 1
- XELYDKHKRIEEAL-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-(2-methylphenyl)prop-2-en-1-one Chemical compound CC1=CC=CC=C1C(=O)C=CC1=CC=C(Cl)C=C1Cl XELYDKHKRIEEAL-UHFFFAOYSA-N 0.000 description 1
- ZFQRERAKPYKCFN-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-(3-methylphenyl)prop-2-en-1-one Chemical compound CC1=CC=CC(C(=O)C=CC=2C(=CC(Cl)=CC=2)Cl)=C1 ZFQRERAKPYKCFN-UHFFFAOYSA-N 0.000 description 1
- GTQTUJZTAPVRGL-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-1-(2-methylphenyl)prop-2-en-1-one Chemical compound CC1=CC=CC=C1C(=O)C=CC1=C(Cl)C=CC=C1Cl GTQTUJZTAPVRGL-UHFFFAOYSA-N 0.000 description 1
- NECQWSJIQYELPM-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-5-methyl-n'-[3-(3,4,5-trimethoxyphenyl)propanoyl]-1,2-oxazole-4-carbohydrazide Chemical compound COC1=C(OC)C(OC)=CC(CCC(=O)NNC(=O)C=2C(=NOC=2C)C=2C(=CC=CC=2Cl)Cl)=C1 NECQWSJIQYELPM-UHFFFAOYSA-N 0.000 description 1
- OZBUYKTYZIXKJQ-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-5-methyl-n'-phenyl-1,2-oxazole-4-carbohydrazide Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)NNC1=CC=CC=C1 OZBUYKTYZIXKJQ-UHFFFAOYSA-N 0.000 description 1
- KZUSCPDXVVAGON-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-n',5-dimethyl-n'-(5-nitropyridin-2-yl)-1,2-oxazole-4-carbohydrazide Chemical compound C=1C=C([N+]([O-])=O)C=NC=1N(C)NC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl KZUSCPDXVVAGON-UHFFFAOYSA-N 0.000 description 1
- GLDZAKKGGAYGNY-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-n',n',5-trimethyl-1,2-oxazole-4-carbohydrazide Chemical compound CN(C)NC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl GLDZAKKGGAYGNY-UHFFFAOYSA-N 0.000 description 1
- MKDGUJZSBRTXHP-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-n'-(3,3-diethoxypropanoyl)-5-methyl-1,2-oxazole-4-carbohydrazide Chemical compound CCOC(OCC)CC(=O)NNC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl MKDGUJZSBRTXHP-UHFFFAOYSA-N 0.000 description 1
- UOCNEOJCPSJYAV-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-n'-(3,5-dichloropyridin-4-yl)-5-methyl-1,2-oxazole-4-carbohydrazide Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)NNC1=C(Cl)C=NC=C1Cl UOCNEOJCPSJYAV-UHFFFAOYSA-N 0.000 description 1
- JKLVNSXPANWZHM-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-n'-[2-[(2,4-dichlorophenyl)methylideneamino]oxyacetyl]-5-methyl-1,2-oxazole-4-carbohydrazide Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1C(=O)NNC(=O)CON=CC1=CC=C(Cl)C=C1Cl JKLVNSXPANWZHM-UHFFFAOYSA-N 0.000 description 1
- GNGXZQIBNVGQAL-UHFFFAOYSA-N 3-(2-chloro-6-fluorophenyl)-1-(4-chloro-3-methylphenyl)prop-2-en-1-one Chemical compound C1=C(Cl)C(C)=CC(C(=O)C=CC=2C(=CC=CC=2F)Cl)=C1 GNGXZQIBNVGQAL-UHFFFAOYSA-N 0.000 description 1
- YDRNHEDMTCYULX-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-(2-methylphenyl)prop-2-en-1-one Chemical compound CC1=CC=CC=C1C(=O)C=CC1=CC=C(Cl)C(Cl)=C1 YDRNHEDMTCYULX-UHFFFAOYSA-N 0.000 description 1
- DFZDZKYUXKTEKK-UHFFFAOYSA-N 3-(3,5-difluorophenyl)-1-(3-nitrophenyl)prop-2-en-1-one Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)C=CC=2C=C(F)C=C(F)C=2)=C1 DFZDZKYUXKTEKK-UHFFFAOYSA-N 0.000 description 1
- SVOPFTFJXVYQCT-UHFFFAOYSA-N 3-(3-phenoxythiophen-2-yl)-1-thiophen-2-ylprop-2-en-1-one Chemical compound C=1C=CSC=1C(=O)C=CC=1SC=CC=1OC1=CC=CC=C1 SVOPFTFJXVYQCT-UHFFFAOYSA-N 0.000 description 1
- WDBQLLUPNITGAT-UHFFFAOYSA-N 3-(4-bromothiophen-2-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C=CC1=CC(Br)=CS1 WDBQLLUPNITGAT-UHFFFAOYSA-N 0.000 description 1
- SGZVTCYTDIDUID-UHFFFAOYSA-N 3-(4-bromothiophen-2-yl)-1-(4-chloro-3-methylphenyl)prop-2-en-1-one Chemical compound C1=C(Cl)C(C)=CC(C(=O)C=CC=2SC=C(Br)C=2)=C1 SGZVTCYTDIDUID-UHFFFAOYSA-N 0.000 description 1
- PSSJEANURYCSPI-UHFFFAOYSA-N 3-(4-bromothiophen-2-yl)-1-(4-chlorophenyl)prop-2-en-1-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C=CC1=CC(Br)=CS1 PSSJEANURYCSPI-UHFFFAOYSA-N 0.000 description 1
- AVNHRWUYKJYYIL-UHFFFAOYSA-N 3-(4-bromothiophen-2-yl)-1-(4-fluorophenyl)prop-2-en-1-one Chemical compound C1=CC(F)=CC=C1C(=O)C=CC1=CC(Br)=CS1 AVNHRWUYKJYYIL-UHFFFAOYSA-N 0.000 description 1
- WMCQXGPKNKDFKZ-UHFFFAOYSA-N 3-(4-chloro-1-methylpyrazol-3-yl)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-one Chemical compound CN1C=C(Cl)C(C=CC(=O)C=2C=CC(=CC=2)C(F)(F)F)=N1 WMCQXGPKNKDFKZ-UHFFFAOYSA-N 0.000 description 1
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| US7192976B2 (en) | 2002-12-21 | 2007-03-20 | Angion Biomedica Corporation | Small molecule modulators of hepatocyte growth factor (scatter factor) activity |
| AR042955A1 (es) | 2003-07-18 | 2005-07-13 | Amgen Inc | Agentes de union especifica al factor de crecimiento de hepatocitos |
| CN100363383C (zh) * | 2003-07-21 | 2008-01-23 | 中国人民解放军军事医学科学院基础医学研究所 | 能够与金葡菌毒力因子调控蛋白结合的小分子多肽及其医药用途 |
| US7473682B2 (en) | 2003-10-29 | 2009-01-06 | Ramot At Tel Aviv University Ltd. | Angiogenic peptides and uses thereof |
| US20060008844A1 (en) * | 2004-06-17 | 2006-01-12 | Avidia Research Institute | c-Met kinase binding proteins |
| US20060235034A1 (en) * | 2004-11-01 | 2006-10-19 | Nouri Neamati | Novel compounds for treatment of cancer and disorders associated with angiogenesis function |
| US7947682B2 (en) * | 2004-12-29 | 2011-05-24 | University Of Southern California | Substituted N′-pyrrolo[1,2-a]quinoxalin-4-yl-hydrazides as anti-cancer agents |
| WO2006052840A2 (en) * | 2004-11-04 | 2006-05-18 | University Of Virginia Patent Foundation | Bone tropic peptides |
| SI1846406T1 (sl) | 2005-02-09 | 2011-02-28 | Arqule Inc | Maleimidni derivati, farmacevtski sestavki in postopki za zdravljenje raka |
| US7879898B1 (en) | 2006-02-14 | 2011-02-01 | Angion Biomedica Corp. | Hepatocyte growth factor pathway activators in chronic obstructive pulmonary disease |
| US8236761B2 (en) | 2006-07-07 | 2012-08-07 | Washington State University Research Foundation | C-Met receptor regulation by angiotensin IV (AT4) receptor ligands |
| EP2043675A2 (en) * | 2006-07-07 | 2009-04-08 | Washington State University Research Foundation | C-met receptor regulation by angiotensin iv (at4) receptor ligands |
| EP2106404A2 (en) | 2006-10-19 | 2009-10-07 | Ramot at Tel Aviv University Ltd. | Compositions and methods for inducing angiogenesis |
| WO2009002807A2 (en) | 2007-06-22 | 2008-12-31 | Arqule, Inc. | Indolyl pyrrolidines for the treatment of cancer |
| CN101801961B (zh) | 2007-06-22 | 2014-09-24 | 艾科尔公司 | 吡咯烷酮、吡咯烷-2,5-二酮、吡咯烷和硫代琥珀酰亚胺衍生物、组合物以及治疗癌症的方法 |
| EP2173724B1 (en) | 2007-06-22 | 2012-12-05 | ArQule, Inc. | Quinazolinone compounds and methods of use thereof |
| EP2219656A2 (en) | 2007-11-09 | 2010-08-25 | New York Medical College | Methods for the repair and/or regeneration of damaged myocardium using variants of hepatocyte growth factor |
| EP2313093A4 (en) | 2008-07-10 | 2012-03-28 | Angion Biomedica Corp | METHOD AND COMPOSITIONS FOR LOW-MOLECULAR MODULATORS OF THE HEPATOCYTE GROWTH FACTOR (SCATTER FACTOR) ACTIVITY |
| KR101814571B1 (ko) | 2010-03-10 | 2018-01-04 | 젠맵 에이/에스 | Ｃ―ｍｅｔ에 대한 모노클로날 항체 |
| WO2012047826A2 (en) * | 2010-10-05 | 2012-04-12 | Angion Biomedica Corp. | Methods of use of small molecule modulators of hepatocyte growth factor (scatter factor) activity |
| JP2012193155A (ja) * | 2011-03-18 | 2012-10-11 | Tohoku Univ | 金属酸化物ナノ粒子の結晶面を認識することが出来るペプチド |
| WO2013113722A1 (en) | 2012-01-30 | 2013-08-08 | Universiteit Gent | Anti-invasive compounds |
| WO2016123163A2 (en) | 2015-01-27 | 2016-08-04 | Kardiatonos, Inc. | Biomarkers of vascular disease |
| CA3115298A1 (en) | 2018-10-12 | 2020-04-16 | Theradaptive, Inc. | Polypeptides including a beta-tricalcium phosphate-binding sequence and uses thereof |
| CA3133803A1 (en) | 2019-04-11 | 2020-10-15 | Angion Biomedica Corp. | Solid forms of (e)-3-[2-(2-thienyl)vinyl]-1h-pyrazole |
| AU2021254751B2 (en) | 2020-04-15 | 2025-01-30 | Theradaptive, Inc. | Compositions and methods for targeted therapeutic delivery to bone |
| CN115317469A (zh) * | 2021-05-11 | 2022-11-11 | 四川大学 | 白及联菲c在制备预防和/或治疗乳腺癌或乳腺癌转移的药物中的用途 |
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| DE69334159D1 (de) * | 1992-09-18 | 2007-09-13 | Us Gov Health & Human Serv | Medizinische Verwendung eines Antikörpers oder eines Antikörperfragments gegen die extrazelluläre Domäne von Met zur Prevention von Metastasen |
| US5646036A (en) * | 1995-06-02 | 1997-07-08 | Genentech, Inc. | Nucleic acids encoding hepatocyte growth factor receptor antagonist antibodies |
| ATE465257T1 (de) * | 1996-07-03 | 2010-05-15 | Genentech Inc | Agonisten für den rezeptor des hepatozyten- wachstumsfaktors und deren anwendungen |
| EP1080068A1 (en) * | 1998-03-12 | 2001-03-07 | Novo Nordisk A/S | Modulators of protein tyrosine phosphatases |
| AU5382200A (en) * | 1999-06-15 | 2001-01-02 | University Health Network | Muc1 ligands |
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