JP2011527675A5 - - Google Patents
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- Publication number
- JP2011527675A5 JP2011527675A5 JP2011517424A JP2011517424A JP2011527675A5 JP 2011527675 A5 JP2011527675 A5 JP 2011527675A5 JP 2011517424 A JP2011517424 A JP 2011517424A JP 2011517424 A JP2011517424 A JP 2011517424A JP 2011527675 A5 JP2011527675 A5 JP 2011527675A5
- Authority
- JP
- Japan
- Prior art keywords
- alkoxy
- optionally substituted
- independently selected
- hydroxy
- aryl
- 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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- 125000003545 alkoxy group Chemical group 0.000 claims description 327
- 125000003118 aryl group Chemical group 0.000 claims description 320
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 306
- 125000001424 substituent group Chemical group 0.000 claims description 266
- 229910052736 halogen Inorganic materials 0.000 claims description 256
- 150000002367 halogens Chemical group 0.000 claims description 253
- 125000000217 alkyl group Chemical group 0.000 claims description 233
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 208
- 125000001072 heteroaryl group Chemical group 0.000 claims description 181
- 229910052739 hydrogen Inorganic materials 0.000 claims description 166
- 239000001257 hydrogen Substances 0.000 claims description 166
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 102
- 125000000623 heterocyclic group Chemical group 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 74
- 125000001931 aliphatic group Chemical group 0.000 claims description 64
- -1 heteroaliphatic Chemical group 0.000 claims description 60
- 229910052760 oxygen Inorganic materials 0.000 claims description 60
- 229910052717 sulfur Inorganic materials 0.000 claims description 60
- 125000002723 alicyclic group Chemical group 0.000 claims description 57
- 125000005842 heteroatom Chemical group 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000002619 bicyclic group Chemical group 0.000 claims description 48
- 150000002431 hydrogen Chemical group 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 210000000056 organ Anatomy 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 35
- 206010016654 Fibrosis Diseases 0.000 claims description 35
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 28
- 230000004761 fibrosis Effects 0.000 claims description 27
- 101150065749 Churc1 gene Proteins 0.000 claims description 26
- 102100038239 Protein Churchill Human genes 0.000 claims description 26
- 208000027418 Wounds and injury Diseases 0.000 claims description 25
- 206010063837 Reperfusion injury Diseases 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 230000000302 ischemic effect Effects 0.000 claims description 24
- 239000007909 solid dosage form Substances 0.000 claims description 24
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 24
- 229920002554 vinyl polymer Polymers 0.000 claims description 24
- 208000031225 myocardial ischemia Diseases 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 22
- 239000000651 prodrug Substances 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 230000006378 damage Effects 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 208000014674 injury Diseases 0.000 claims description 17
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 16
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 16
- 230000001684 chronic effect Effects 0.000 claims description 16
- 206010012601 diabetes mellitus Diseases 0.000 claims description 16
- 201000006370 kidney failure Diseases 0.000 claims description 16
- 201000006938 muscular dystrophy Diseases 0.000 claims description 16
- 206010061481 Renal injury Diseases 0.000 claims description 15
- 208000028867 ischemia Diseases 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 12
- 239000000872 buffer Substances 0.000 claims description 12
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 12
- 210000004185 liver Anatomy 0.000 claims description 12
- 229940068886 polyethylene glycol 300 Drugs 0.000 claims description 12
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 12
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 12
- 229920000053 polysorbate 80 Polymers 0.000 claims description 12
- 229940068968 polysorbate 80 Drugs 0.000 claims description 12
- 210000004204 blood vessel Anatomy 0.000 claims description 10
- 238000001727 in vivo Methods 0.000 claims description 10
- 210000003734 kidney Anatomy 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 238000002054 transplantation Methods 0.000 claims description 10
- 206010052428 Wound Diseases 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 210000000013 bile duct Anatomy 0.000 claims description 9
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 8
- 208000007848 Alcoholism Diseases 0.000 claims description 8
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 8
- 208000015163 Biliary Tract disease Diseases 0.000 claims description 8
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 8
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 8
- 208000018565 Hemochromatosis Diseases 0.000 claims description 8
- 208000027761 Hepatic autoimmune disease Diseases 0.000 claims description 8
- 208000005331 Hepatitis D Diseases 0.000 claims description 8
- 208000002972 Hepatolenticular Degeneration Diseases 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 8
- 208000018839 Wilson disease Diseases 0.000 claims description 8
- 210000004556 brain Anatomy 0.000 claims description 8
- 206010008118 cerebral infarction Diseases 0.000 claims description 8
- 230000007882 cirrhosis Effects 0.000 claims description 8
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical group P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 claims description 8
- 210000002216 heart Anatomy 0.000 claims description 8
- 208000029570 hepatitis D virus infection Diseases 0.000 claims description 8
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 8
- 208000017169 kidney disease Diseases 0.000 claims description 8
- 210000004072 lung Anatomy 0.000 claims description 8
- 230000002107 myocardial effect Effects 0.000 claims description 8
- 208000010125 myocardial infarction Diseases 0.000 claims description 8
- 238000010606 normalization Methods 0.000 claims description 8
- 230000010412 perfusion Effects 0.000 claims description 8
- 239000002953 phosphate buffered saline Substances 0.000 claims description 8
- 230000002685 pulmonary effect Effects 0.000 claims description 8
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 8
- 239000004575 stone Substances 0.000 claims description 8
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims description 7
- 206010053648 Vascular occlusion Diseases 0.000 claims description 7
- 230000033115 angiogenesis Effects 0.000 claims description 7
- 208000002672 hepatitis B Diseases 0.000 claims description 7
- 208000016245 inborn errors of metabolism Diseases 0.000 claims description 7
- 208000015978 inherited metabolic disease Diseases 0.000 claims description 7
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims description 7
- 208000010157 sclerosing cholangitis Diseases 0.000 claims description 7
- 208000021331 vascular occlusion disease Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 208000005176 Hepatitis C Diseases 0.000 claims description 5
- 230000035876 healing Effects 0.000 claims description 5
- 208000037806 kidney injury Diseases 0.000 claims description 5
- 208000019423 liver disease Diseases 0.000 claims description 5
- 201000002793 renal fibrosis Diseases 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 4
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 4
- 206010056328 Hepatic ischaemia Diseases 0.000 claims description 4
- 229930195725 Mannitol Natural products 0.000 claims description 4
- 229920000881 Modified starch Polymers 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 claims description 4
- 229930003427 Vitamin E Natural products 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000002872 contrast media Substances 0.000 claims description 4
- 230000003176 fibrotic effect Effects 0.000 claims description 4
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 4
- 235000012208 gluconic acid Nutrition 0.000 claims description 4
- 239000000174 gluconic acid Substances 0.000 claims description 4
- 229950006191 gluconic acid Drugs 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- 229940099563 lactobionic acid Drugs 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 4
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 4
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 4
- 229940046009 vitamin E Drugs 0.000 claims description 4
- 235000019165 vitamin E Nutrition 0.000 claims description 4
- 239000011709 vitamin E Substances 0.000 claims description 4
- VWESQMOYFHDJMO-SNAWJCMRSA-N (6-chloropyridin-3-yl)-[3-[(e)-2-thiophen-2-ylethenyl]pyrazol-1-yl]methanone Chemical compound C1=NC(Cl)=CC=C1C(=O)N1N=C(\C=C\C=2SC=CC=2)C=C1 VWESQMOYFHDJMO-SNAWJCMRSA-N 0.000 claims description 2
- ROAIMWPBGVEJLH-SOFGYWHQSA-N (6-morpholin-4-ylpyridin-3-yl)-[3-[(e)-2-phenylethenyl]pyrazol-1-yl]methanone Chemical compound C1=CC(\C=C\C=2C=CC=CC=2)=NN1C(=O)C(C=N1)=CC=C1N1CCOCC1 ROAIMWPBGVEJLH-SOFGYWHQSA-N 0.000 claims description 2
- ACMPNFSQDDTAIB-SNAWJCMRSA-N 1,3-benzodioxol-5-yl-[3-[(e)-2-(furan-2-yl)ethenyl]pyrazol-1-yl]methanone Chemical compound C=1C=C2OCOC2=CC=1C(=O)N(N=1)C=CC=1\C=C\C1=CC=CO1 ACMPNFSQDDTAIB-SNAWJCMRSA-N 0.000 claims description 2
- ADAKSJMCFLSJDL-SNAWJCMRSA-N 1,3-benzodioxol-5-yl-[3-[(e)-2-thiophen-2-ylethenyl]pyrazol-1-yl]methanone Chemical compound C=1C=C2OCOC2=CC=1C(=O)N(N=1)C=CC=1\C=C\C1=CC=CS1 ADAKSJMCFLSJDL-SNAWJCMRSA-N 0.000 claims description 2
- PBSKHGYZCGLRMW-SNAWJCMRSA-N 1-[4-[3-[(e)-2-thiophen-2-ylethenyl]pyrazole-1-carbonyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C(=O)N1N=C(\C=C\C=2SC=CC=2)C=C1 PBSKHGYZCGLRMW-SNAWJCMRSA-N 0.000 claims description 2
- PVFHXSKBMLKNOI-BQYQJAHWSA-N 2-(4-chlorophenyl)-1-[3-[(e)-2-thiophen-2-ylethenyl]pyrazol-1-yl]ethanone Chemical compound C1=CC(Cl)=CC=C1CC(=O)N1N=C(\C=C\C=2SC=CC=2)C=C1 PVFHXSKBMLKNOI-BQYQJAHWSA-N 0.000 claims description 2
- HWLXDCWWKCZSLC-JXMROGBWSA-N 2-(4-methoxyphenyl)-1-[3-[(e)-2-phenylethenyl]pyrazol-1-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)N1N=C(\C=C\C=2C=CC=CC=2)C=C1 HWLXDCWWKCZSLC-JXMROGBWSA-N 0.000 claims description 2
- SCDNPHPQYKUMQW-AATRIKPKSA-N 2-[(E)-2-(1H-pyrazol-5-yl)ethenyl]-1H-indole Chemical compound C=1C2=CC=CC=C2NC=1\C=C\C=1C=CNN=1 SCDNPHPQYKUMQW-AATRIKPKSA-N 0.000 claims description 2
- SCDNPHPQYKUMQW-WAYWQWQTSA-N 2-[(Z)-2-(1H-pyrazol-5-yl)ethenyl]-1H-indole Chemical compound C=1C2=CC=CC=C2NC=1/C=C\C=1C=CNN=1 SCDNPHPQYKUMQW-WAYWQWQTSA-N 0.000 claims description 2
- OAHIEMNLLAWRLZ-VOTSOKGWSA-N 3-[3-[(E)-2-(1H-pyrrol-2-yl)ethenyl]pyrazol-1-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2N=C(\C=C\C=3NC=CC=3)C=C2)=C1 OAHIEMNLLAWRLZ-VOTSOKGWSA-N 0.000 claims description 2
- NQDNQIKHDMEMDL-SNAWJCMRSA-N 3-[3-[(E)-2-(1H-pyrrol-3-yl)ethenyl]pyrazole-1-carbonyl]benzonitrile Chemical compound C1=CC(\C=C\C2=CNC=C2)=NN1C(=O)C1=CC=CC(C#N)=C1 NQDNQIKHDMEMDL-SNAWJCMRSA-N 0.000 claims description 2
- LVOFZXYKYGTEMU-SNAWJCMRSA-N 3-[3-[(e)-2-(furan-3-yl)ethenyl]pyrazole-1-carbonyl]benzonitrile Chemical compound C1=CC(\C=C\C2=COC=C2)=NN1C(=O)C1=CC=CC(C#N)=C1 LVOFZXYKYGTEMU-SNAWJCMRSA-N 0.000 claims description 2
- LIQIDBDGLKJLBP-VOTSOKGWSA-N 3-[3-[(e)-2-thiophen-2-ylethenyl]pyrazole-1-carbonyl]benzonitrile Chemical compound C1=CC(\C=C\C=2SC=CC=2)=NN1C(=O)C1=CC=CC(C#N)=C1 LIQIDBDGLKJLBP-VOTSOKGWSA-N 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- ZIEVRTDKRHVCJQ-BQYQJAHWSA-N 4-[3-[(e)-2-thiophen-2-ylethenyl]pyrazole-1-carbonyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)N1N=C(\C=C\C=2SC=CC=2)C=C1 ZIEVRTDKRHVCJQ-BQYQJAHWSA-N 0.000 claims description 2
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- QNQPCKJLSXTOPS-UPHRSURJSA-N 5-[(Z)-2-(1H-pyrrol-3-yl)ethenyl]-1H-pyrazole Chemical compound C1=CNC=C1/C=C\C=1C=CNN=1 QNQPCKJLSXTOPS-UPHRSURJSA-N 0.000 claims description 2
- WTLCERBYPIMJNW-SNAWJCMRSA-N 5-[(e)-2-(2,6-dichlorophenyl)ethenyl]-1h-pyrazole Chemical compound ClC1=CC=CC(Cl)=C1\C=C\C1=CC=NN1 WTLCERBYPIMJNW-SNAWJCMRSA-N 0.000 claims description 2
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- FSONDHSXOHJMCO-DJWKRKHSSA-N 5-[(z)-2-(4-methoxyphenyl)ethenyl]-1h-pyrazole Chemical compound C1=CC(OC)=CC=C1\C=C/C1=NNC=C1 FSONDHSXOHJMCO-DJWKRKHSSA-N 0.000 claims description 2
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- SVGZNMNPBUUXQL-UPHRSURJSA-N 5-[(z)-2-thiophen-3-ylethenyl]-1h-pyrazole Chemical compound C1=CSC=C1/C=C\C=1C=CNN=1 SVGZNMNPBUUXQL-UPHRSURJSA-N 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 2
- TZTVBBLETXICAZ-FLIBITNWSA-N N1(N=CC=C1)\C=C/C1=CC=C(N(C)C)C=C1 Chemical compound N1(N=CC=C1)\C=C/C1=CC=C(N(C)C)C=C1 TZTVBBLETXICAZ-FLIBITNWSA-N 0.000 claims description 2
- 241000750042 Vini Species 0.000 claims description 2
- MRKQFTGFBWZIIP-VOTSOKGWSA-N [3-[(e)-2-(2,6-dichlorophenyl)ethenyl]pyrazol-1-yl]-thiophen-2-ylmethanone Chemical compound ClC1=CC=CC(Cl)=C1\C=C\C1=NN(C(=O)C=2SC=CC=2)C=C1 MRKQFTGFBWZIIP-VOTSOKGWSA-N 0.000 claims description 2
- QXVFVWIMRPHTFC-VOTSOKGWSA-N [3-[(e)-2-(furan-2-yl)ethenyl]pyrazol-1-yl]-(1-methylpyrrol-2-yl)methanone Chemical compound CN1C=CC=C1C(=O)N1N=C(\C=C\C=2OC=CC=2)C=C1 QXVFVWIMRPHTFC-VOTSOKGWSA-N 0.000 claims description 2
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| RU2639876C2 (ru) | 2010-03-30 | 2017-12-25 | Версеон Корпорейшн | Мультизамещенные ароматические соединения в качестве ингибиторов тромбина |
| 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 |
| MX373964B (es) | 2013-03-15 | 2020-07-13 | Verseon Corp | Compuestos aromaticos multisustituidos como inhibidores de serina proteasa. |
| US9951025B2 (en) | 2013-03-15 | 2018-04-24 | Verseon Corporation | Halogenopyrazoles as inhibitors of thrombin |
| US10189810B2 (en) | 2014-09-17 | 2019-01-29 | Verseon Corporation | Pyrazolyl-substituted pyridone compounds as serine protease inhibitors |
| SI3261639T1 (sl) | 2015-02-27 | 2023-01-31 | Verseon International Corporation | Substituirane pirazolne spojine kot zaviralci serinskih proteaz |
| JP6830158B2 (ja) * | 2016-12-22 | 2021-02-17 | 諾貝兒寶貝股▲ふん▼有限公司Ｎｏｒｂｅｌ Ｂａｂｙ Ｃｏ．， Ｌｔｄ． | 肝損傷を予防または治療する医薬組成物の調製における（２ｒ，４ｒ）−１，２，４−トリヒドロキシヘプタデカ−１６−インの応用 |
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| US6610726B2 (en) * | 2001-06-29 | 2003-08-26 | North Shore-Long Island Jewish Research Institute | Compositions and agents for modulating cellular proliferation and angiogenesis |
| US6589997B2 (en) * | 2001-06-29 | 2003-07-08 | North Shore-Long Island Jewish Health System | Small-molecule modulators of hepatocyte growth factor/scatter factor activities |
| US20030073692A1 (en) * | 2001-08-07 | 2003-04-17 | Pharmacia & Upjohn S.P.A. | Amino-phthalazinone derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions containing them |
| CN101172104B (zh) * | 2002-02-22 | 2013-04-03 | 默沙东公司 | 抗肿瘤剂,特别是替莫唑胺的药物制剂,其制备方法和用途 |
| AU2002313690A1 (en) | 2002-07-19 | 2004-02-09 | Targacept, Inc. | Five-membered heteroaromatic olefinic azacyclic compounds, pharmaceutical compositions containing them and their use as inhibitors of ncotinic cholinergic receptors |
| US7192976B2 (en) * | 2002-12-21 | 2007-03-20 | Angion Biomedica Corporation | Small molecule modulators of hepatocyte growth factor (scatter factor) activity |
| FR2868519B1 (fr) * | 2004-03-30 | 2006-06-16 | Christian Muller | Generateur thermique a materiau magneto-calorique et procede de generation de thermies |
| GB0419072D0 (en) * | 2004-08-26 | 2004-09-29 | Kudos Pharm Ltd | Phthalazinone derivatives |
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| US20110230407A1 (en) * | 2005-03-14 | 2011-09-22 | Alexander Yuzhakov | Hepatocyte growth factor pathway activators in demyelinating diseases and central nervous system trauma |
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| CA2678248C (en) * | 2007-03-08 | 2016-06-28 | Janssen Pharmaceutica Nv | Quinolinone derivatives as parp and tank inhibitors |
| WO2009064422A2 (en) | 2007-11-13 | 2009-05-22 | Angion Biomedica Corp. | Hepatocyte growth factor pathway activators in fibrotic connective tissue diseases |
| 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 |
| US20110098304A1 (en) * | 2008-10-22 | 2011-04-28 | Bijoy Panicker | Small molecule inhibitors of PARP activity |
| US20120190668A1 (en) | 2009-08-12 | 2012-07-26 | Oehlen Lambertus J W M | Enhancement of cellular transplantation using small moleucle modulators of hepatocyte growth factor (scatter factor) activity |
| 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 |
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2011
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2014
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2017
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