CA2674389A1 - Rho kinase inhibitors - Google Patents
Rho kinase inhibitors Download PDFInfo
- Publication number
- CA2674389A1 CA2674389A1 CA002674389A CA2674389A CA2674389A1 CA 2674389 A1 CA2674389 A1 CA 2674389A1 CA 002674389 A CA002674389 A CA 002674389A CA 2674389 A CA2674389 A CA 2674389A CA 2674389 A1 CA2674389 A1 CA 2674389A1
- Authority
- CA
- Canada
- Prior art keywords
- benzamide
- benzyl
- tetrahydro
- ylcarbamoyl
- dimethoxy
- 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.)
- Abandoned
Links
- 239000003590 rho kinase inhibitor Substances 0.000 title description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 108010041788 rho-Associated Kinases Proteins 0.000 claims abstract description 17
- 102000000568 rho-Associated Kinases Human genes 0.000 claims abstract description 17
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 12
- 208000010228 Erectile Dysfunction Diseases 0.000 claims abstract description 8
- 201000001881 impotence Diseases 0.000 claims abstract description 8
- 208000017169 kidney disease Diseases 0.000 claims abstract description 8
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 7
- 208000006673 asthma Diseases 0.000 claims abstract description 7
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 201000011510 cancer Diseases 0.000 claims abstract description 6
- -1 4-methyl-1-piperazinyl ring Chemical group 0.000 claims description 187
- 150000001875 compounds Chemical class 0.000 claims description 151
- 238000000034 method Methods 0.000 claims description 126
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 206010020772 Hypertension Diseases 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 208000006011 Stroke Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- AOTJVGQNGQYEAY-UHFFFAOYSA-N 3,4-dimethoxy-n-[[3-(1,2,3,4-tetrahydroisoquinolin-7-ylcarbamoyl)phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CNCCC3=CC=2)=C1 AOTJVGQNGQYEAY-UHFFFAOYSA-N 0.000 claims description 7
- QDAQEKNRPXBKCO-NRFANRHFSA-N 3,4-dimethoxy-n-[[3-[[(6s)-6-morpholin-4-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](CCC=3N=2)N2CCOCC2)=C1 QDAQEKNRPXBKCO-NRFANRHFSA-N 0.000 claims description 7
- MCIPSMFHIWYOIN-UHFFFAOYSA-N 3-[[(4-cyanophenyl)carbamoylamino]methyl]-n-(1,2,3,4-tetrahydroisoquinolin-7-yl)benzamide Chemical compound C=1C=CC(C(=O)NC=2C=C3CNCCC3=CC=2)=CC=1CNC(=O)NC1=CC=C(C#N)C=C1 MCIPSMFHIWYOIN-UHFFFAOYSA-N 0.000 claims description 7
- 206010019280 Heart failures Diseases 0.000 claims description 7
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 7
- VUAKQQXGRWHENF-MRXNPFEDSA-N n-[[3-[[(6r)-6-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-3-chloro-4-methoxybenzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](N)CCC=3N=2)=C1 VUAKQQXGRWHENF-MRXNPFEDSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 7
- ZMYOSCXCQCZDAA-FQEVSTJZSA-N 3,4-dimethoxy-n-[[3-[[(6s)-6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]benzamide Chemical compound C([C@@H](CC=1S2)NCCC)CC=1N=C2NC(=O)C(C=1)=CC=CC=1CNC(=O)C1=CC=C(OC)C(OC)=C1 ZMYOSCXCQCZDAA-FQEVSTJZSA-N 0.000 claims description 6
- SCIFUGGHOXNSJC-UHFFFAOYSA-N 3-[[(4-carbamoylphenyl)carbamoylamino]methyl]-n-(1,2,3,4-tetrahydroisoquinolin-7-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC(=O)NCC1=CC=CC(C(=O)NC=2C=C3CNCCC3=CC=2)=C1 SCIFUGGHOXNSJC-UHFFFAOYSA-N 0.000 claims description 6
- LCJBYZGNYPVZSS-UHFFFAOYSA-N 3-[[(4-cyanophenyl)carbamoylamino]methyl]-n-[4-(dimethylamino)butyl]benzamide Chemical compound CN(C)CCCCNC(=O)C1=CC=CC(CNC(=O)NC=2C=CC(=CC=2)C#N)=C1 LCJBYZGNYPVZSS-UHFFFAOYSA-N 0.000 claims description 6
- VRXYOJOPGLAOQW-IBGZPJMESA-N 3-chloro-4-methoxy-n-[[3-[[(6s)-6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]benzamide Chemical compound C([C@@H](CC=1S2)NCCC)CC=1N=C2NC(=O)C(C=1)=CC=CC=1CNC(=O)C1=CC=C(OC)C(Cl)=C1 VRXYOJOPGLAOQW-IBGZPJMESA-N 0.000 claims description 6
- WWKGSLZIGCEEEZ-FQEVSTJZSA-N 3-chloro-4-methoxy-n-[[3-[[(6s)-6-morpholin-4-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](CCC=3N=2)N2CCOCC2)=C1 WWKGSLZIGCEEEZ-FQEVSTJZSA-N 0.000 claims description 6
- ARCOISRMIVSDHR-GOSISDBHSA-N 3-chloro-n-[[3-[[(6r)-6-(dimethylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-4-methoxybenzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@@H](CCC=3N=2)N(C)C)=C1 ARCOISRMIVSDHR-GOSISDBHSA-N 0.000 claims description 6
- ARCOISRMIVSDHR-SFHVURJKSA-N 3-chloro-n-[[3-[[(6s)-6-(dimethylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-4-methoxybenzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](CCC=3N=2)N(C)C)=C1 ARCOISRMIVSDHR-SFHVURJKSA-N 0.000 claims description 6
- 208000001286 intracranial vasospasm Diseases 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- MDBFMZNSFPEUHN-HXUWFJFHSA-N n-[[3-[[(6r)-6-(dimethylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-4-methoxy-3-methylbenzamide Chemical compound C1=C(C)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@@H](CCC=3N=2)N(C)C)=C1 MDBFMZNSFPEUHN-HXUWFJFHSA-N 0.000 claims description 6
- MDBFMZNSFPEUHN-FQEVSTJZSA-N n-[[3-[[(6s)-6-(dimethylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-4-methoxy-3-methylbenzamide Chemical compound C1=C(C)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](CCC=3N=2)N(C)C)=C1 MDBFMZNSFPEUHN-FQEVSTJZSA-N 0.000 claims description 6
- WDMKCBKSWLBWPX-KRWDZBQOSA-N n-[[3-[[(6s)-6-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@@H](N)CCC=3N=2)=C1 WDMKCBKSWLBWPX-KRWDZBQOSA-N 0.000 claims description 6
- WVKXLPYVWVUFQT-UHFFFAOYSA-N 2-bromo-4,5-dimethoxy-n-[[3-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC(Br)=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CN(C)CCC3=CC=2)=C1 WVKXLPYVWVUFQT-UHFFFAOYSA-N 0.000 claims description 5
- VGQMQYBEZDGNSS-UHFFFAOYSA-N 2-methyl-3,4-dihydro-1h-isoquinoline-7-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2CN(C)CCC2=C1 VGQMQYBEZDGNSS-UHFFFAOYSA-N 0.000 claims description 5
- XAAZBMINIBYRPX-UHFFFAOYSA-N 3,4-dimethoxy-n-[[3-(2-piperidin-3-ylethylcarbamoyl)phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NCCC2CNCCC2)=C1 XAAZBMINIBYRPX-UHFFFAOYSA-N 0.000 claims description 5
- HSKITMMIPIGXTH-UHFFFAOYSA-N 3,4-dimethoxy-n-[[3-(4,5,6,7-tetrahydro-[1,3]thiazolo[5,4-c]pyridin-2-ylcarbamoyl)phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3CNCCC=3N=2)=C1 HSKITMMIPIGXTH-UHFFFAOYSA-N 0.000 claims description 5
- BPSAUZOYNCGXMG-UHFFFAOYSA-N 3,4-dimethoxy-n-[[3-[(2-morpholin-4-yl-2,3-dihydro-1h-inden-5-yl)carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CC(CC3=CC=2)N2CCOCC2)=C1 BPSAUZOYNCGXMG-UHFFFAOYSA-N 0.000 claims description 5
- FDNORQUIWSIWKF-UHFFFAOYSA-N 3,4-dimethoxy-n-[[3-[(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3CN(C)CCC=3N=2)=C1 FDNORQUIWSIWKF-UHFFFAOYSA-N 0.000 claims description 5
- AQYDBKYCZFZNAF-UHFFFAOYSA-N 3,4-dimethoxy-n-[[3-[2-(1-methylpiperidin-3-yl)ethylcarbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NCCC2CN(C)CCC2)=C1 AQYDBKYCZFZNAF-UHFFFAOYSA-N 0.000 claims description 5
- QDAQEKNRPXBKCO-OAQYLSRUSA-N 3,4-dimethoxy-n-[[3-[[(6r)-6-morpholin-4-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@@H](CCC=3N=2)N2CCOCC2)=C1 QDAQEKNRPXBKCO-OAQYLSRUSA-N 0.000 claims description 5
- CXIAHIQUZUIHBM-UHFFFAOYSA-N 3-[[(3-ethynylphenyl)carbamoylamino]methyl]-n-(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)benzamide Chemical compound S1C=2CN(C)CCC=2N=C1NC(=O)C(C=1)=CC=CC=1CNC(=O)NC1=CC=CC(C#C)=C1 CXIAHIQUZUIHBM-UHFFFAOYSA-N 0.000 claims description 5
- DDXSWRNQMBOYNX-UHFFFAOYSA-N 3-[[(4-cyanophenyl)carbamoylamino]methyl]-n-(2-piperidin-3-ylethyl)benzamide Chemical compound C=1C=C(C#N)C=CC=1NC(=O)NCC(C=1)=CC=CC=1C(=O)NCCC1CCCNC1 DDXSWRNQMBOYNX-UHFFFAOYSA-N 0.000 claims description 5
- QVFKAXVIOVRQEX-UHFFFAOYSA-N 4-methoxy-3-methyl-n-[[3-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(C)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CN(C)CCC3=CC=2)=C1 QVFKAXVIOVRQEX-UHFFFAOYSA-N 0.000 claims description 5
- CBVODQKZOOSINP-NRFANRHFSA-N 4-methoxy-3-methyl-n-[[3-[[(6s)-6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]benzamide Chemical compound C([C@@H](CC=1S2)NCCC)CC=1N=C2NC(=O)C(C=1)=CC=CC=1CNC(=O)C1=CC=C(OC)C(C)=C1 CBVODQKZOOSINP-NRFANRHFSA-N 0.000 claims description 5
- SSYXZESTUAIROQ-QFIPXVFZSA-N 4-methoxy-3-methyl-n-[[3-[[(6s)-6-morpholin-4-yl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(C)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](CCC=3N=2)N2CCOCC2)=C1 SSYXZESTUAIROQ-QFIPXVFZSA-N 0.000 claims description 5
- 206010002383 Angina Pectoris Diseases 0.000 claims description 5
- 206010003225 Arteriospasm coronary Diseases 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000003890 Coronary Vasospasm Diseases 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 201000011634 coronary artery vasospasm Diseases 0.000 claims description 5
- 208000028867 ischemia Diseases 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- RGUHTIWGUPVADN-UHFFFAOYSA-N n-[3-[[(3,4-dimethoxybenzoyl)amino]methyl]phenyl]-2-methyl-3,4-dihydro-1h-isoquinoline-6-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(NC(=O)C=2C=C3CCN(C)CC3=CC=2)=C1 RGUHTIWGUPVADN-UHFFFAOYSA-N 0.000 claims description 5
- OQXFACQMBUZLKB-UHFFFAOYSA-N n-[3-[[(3,4-dimethoxybenzoyl)amino]methyl]phenyl]-4,5,6,7-tetrahydro-[1,3]thiazolo[5,4-c]pyridine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(NC(=O)C=2SC=3CNCCC=3N=2)=C1 OQXFACQMBUZLKB-UHFFFAOYSA-N 0.000 claims description 5
- YGNSENLWUQWPRG-UHFFFAOYSA-N n-[3-[[(4-cyanophenyl)carbamoylamino]methyl]phenyl]-2-methyl-3,4-dihydro-1h-isoquinoline-7-carboxamide Chemical compound C1=C2CN(C)CCC2=CC=C1C(=O)NC(C=1)=CC=CC=1CNC(=O)NC1=CC=C(C#N)C=C1 YGNSENLWUQWPRG-UHFFFAOYSA-N 0.000 claims description 5
- FARBCDMPQBPCIY-UHFFFAOYSA-N n-[[3-[(2-benzyl-3,4-dihydro-1h-isoquinolin-7-yl)carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CN(CC=4C=CC=CC=4)CCC3=CC=2)=C1 FARBCDMPQBPCIY-UHFFFAOYSA-N 0.000 claims description 5
- GKBAYDIXMMANQN-LJQANCHMSA-N n-[[3-[[(6r)-6-(dimethylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@@H](CCC=3N=2)N(C)C)=C1 GKBAYDIXMMANQN-LJQANCHMSA-N 0.000 claims description 5
- COKNHADRCGAEMW-VWLOTQADSA-N n-[[3-[[(6s)-6-(1,3-dihydroisoindol-2-yl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](CCC=3N=2)N2CC3=CC=CC=C3C2)=C1 COKNHADRCGAEMW-VWLOTQADSA-N 0.000 claims description 5
- GKBAYDIXMMANQN-IBGZPJMESA-N n-[[3-[[(6s)-6-(dimethylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](CCC=3N=2)N(C)C)=C1 GKBAYDIXMMANQN-IBGZPJMESA-N 0.000 claims description 5
- XSCPPIVJZTUFDL-SANMLTNESA-N n-[[3-[[(6s)-6-[benzyl(propyl)amino]-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-3-chloro-4-methoxybenzamide Chemical compound CCCN([C@@H]1CC=2SC(NC(=O)C=3C=C(CNC(=O)C=4C=C(Cl)C(OC)=CC=4)C=CC=3)=NC=2CC1)CC1=CC=CC=C1 XSCPPIVJZTUFDL-SANMLTNESA-N 0.000 claims description 5
- VUAKQQXGRWHENF-INIZCTEOSA-N n-[[3-[[(6s)-6-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-3-chloro-4-methoxybenzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@@H](N)CCC=3N=2)=C1 VUAKQQXGRWHENF-INIZCTEOSA-N 0.000 claims description 5
- WPLZNVHCFPVSDT-UHFFFAOYSA-N n-[[3-[[2-(2-cyanoethyl)-3,4-dihydro-1h-isoquinolin-7-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CN(CCC#N)CCC3=CC=2)=C1 WPLZNVHCFPVSDT-UHFFFAOYSA-N 0.000 claims description 5
- QVWADFSTTCAAMY-UHFFFAOYSA-N n-[[3-[[2-[(3-fluorophenyl)methyl]-3,4-dihydro-1h-isoquinolin-7-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CN(CC=4C=C(F)C=CC=4)CCC3=CC=2)=C1 QVWADFSTTCAAMY-UHFFFAOYSA-N 0.000 claims description 5
- CJLDEBMSVPBFQY-UHFFFAOYSA-N n-[[3-[[5-[(dimethylamino)methyl]-1,3-thiazol-2-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC(CN(C)C)=CN=2)=C1 CJLDEBMSVPBFQY-UHFFFAOYSA-N 0.000 claims description 5
- MMCAPCFOJJDVNO-UHFFFAOYSA-N n-benzyl-3,4-dimethoxy-n-[[3-[(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-2-yl)carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N(CC=1C=C(C=CC=1)C(=O)NC=1SC=2CN(C)CCC=2N=1)CC1=CC=CC=C1 MMCAPCFOJJDVNO-UHFFFAOYSA-N 0.000 claims description 5
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 5
- JXDIHMPDMUCOTI-UHFFFAOYSA-N 1-methyl-n-[[3-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)carbamoyl]phenyl]methyl]-6-oxopyridine-3-carboxamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C(C=1)=CC=CC=1CNC(=O)C=1C=CC(=O)N(C)C=1 JXDIHMPDMUCOTI-UHFFFAOYSA-N 0.000 claims description 4
- VUBLTFWGVBUVGZ-UHFFFAOYSA-N 2,4,5-trimethoxy-n-[[3-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(OC)C(OC)=CC(OC)=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CN(C)CCC3=CC=2)=C1 VUBLTFWGVBUVGZ-UHFFFAOYSA-N 0.000 claims description 4
- MKNYDQXDYYRFSG-UHFFFAOYSA-N 2-hydroxy-3,4-dimethoxy-n-[[3-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)carbamoyl]phenyl]methyl]benzamide Chemical compound OC1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C3CN(C)CCC3=CC=2)=C1 MKNYDQXDYYRFSG-UHFFFAOYSA-N 0.000 claims description 4
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- IVVANNSYKVZGPX-UHFFFAOYSA-N 3-[[(3,4-dimethoxyphenyl)carbamoylamino]methyl]-n-(1,2,3,4-tetrahydroisoquinolin-6-yl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)NCC1=CC=CC(C(=O)NC=2C=C3CCNCC3=CC=2)=C1 IVVANNSYKVZGPX-UHFFFAOYSA-N 0.000 claims description 2
- VBWXDGZYWJFRCV-UHFFFAOYSA-N 3-[[(3-carbamoylphenyl)carbamoylamino]methyl]-n-[4-[(dimethylamino)methyl]phenyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)NC=2C=C(C=CC=2)C(N)=O)=C1 VBWXDGZYWJFRCV-UHFFFAOYSA-N 0.000 claims description 2
- ANYOJLMYGDPTHX-UHFFFAOYSA-N 3-[[(3-cyanophenyl)carbamoylamino]methyl]-n-[4-[(dimethylamino)methyl]phenyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)NC=2C=C(C=CC=2)C#N)=C1 ANYOJLMYGDPTHX-UHFFFAOYSA-N 0.000 claims description 2
- MSMWPPBCSAITML-UHFFFAOYSA-N 3-[[(4-acetylphenyl)carbamoylamino]methyl]-n-[4-[(dimethylamino)methyl]phenyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)NC=2C=CC(=CC=2)C(C)=O)=C1 MSMWPPBCSAITML-UHFFFAOYSA-N 0.000 claims description 2
- RZNZSTXLRMIFPT-UHFFFAOYSA-N 3-[[(4-carbamoylphenyl)carbamoylamino]methyl]-n-[4-[(dimethylamino)methyl]phenyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)NC=2C=CC(=CC=2)C(N)=O)=C1 RZNZSTXLRMIFPT-UHFFFAOYSA-N 0.000 claims description 2
- AOMLHURUTKIYJI-UHFFFAOYSA-N 3-[[(4-chlorophenyl)carbamoylamino]methyl]-n-[4-[(dimethylamino)methyl]phenyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)NC=2C=CC(Cl)=CC=2)=C1 AOMLHURUTKIYJI-UHFFFAOYSA-N 0.000 claims description 2
- RXEBZMMATZDNTI-UHFFFAOYSA-N 3-[[(4-cyanobenzoyl)amino]methyl]-n-[4-[(dimethylamino)methyl]phenyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)C=2C=CC(=CC=2)C#N)=C1 RXEBZMMATZDNTI-UHFFFAOYSA-N 0.000 claims description 2
- AZWXKWPFYCFFOQ-UHFFFAOYSA-N 3-[[(4-cyanophenyl)carbamoylamino]methyl]-n-(1,2,3,4-tetrahydroisoquinolin-6-yl)benzamide Chemical compound C=1C=CC(C(=O)NC=2C=C3CCNCC3=CC=2)=CC=1CNC(=O)NC1=CC=C(C#N)C=C1 AZWXKWPFYCFFOQ-UHFFFAOYSA-N 0.000 claims description 2
- MBWBQWVICWBWLB-UHFFFAOYSA-N 3-[[(4-cyanophenyl)carbamoylamino]methyl]-n-[3-[(dimethylamino)methyl]phenyl]benzamide Chemical compound CN(C)CC1=CC=CC(NC(=O)C=2C=C(CNC(=O)NC=3C=CC(=CC=3)C#N)C=CC=2)=C1 MBWBQWVICWBWLB-UHFFFAOYSA-N 0.000 claims description 2
- BXCQIDVVQQYTNJ-UHFFFAOYSA-N 3-[[(4-cyanophenyl)carbamoylamino]methyl]-n-[4-[(dimethylamino)methyl]phenyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)NC=2C=CC(=CC=2)C#N)=C1 BXCQIDVVQQYTNJ-UHFFFAOYSA-N 0.000 claims description 2
- CLHFYZQTYYWLHB-UHFFFAOYSA-N 3-chloro-4-methoxy-n-[[3-[[4-(2-pyrrolidin-1-ylethyl)phenyl]carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CCN3CCCC3)=CC=2)=C1 CLHFYZQTYYWLHB-UHFFFAOYSA-N 0.000 claims description 2
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- JSLIEZKRKUGNEF-UHFFFAOYSA-N 4-methoxy-3-methyl-n-[[3-[[4-(2-pyrrolidin-1-ylethyl)phenyl]carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C(C)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CCN3CCCC3)=CC=2)=C1 JSLIEZKRKUGNEF-UHFFFAOYSA-N 0.000 claims description 2
- VYVXFNZKVUMLOE-UHFFFAOYSA-N 4-n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]benzene-1,4-dicarboxamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)C=2C=CC(=CC=2)C(N)=O)=C1 VYVXFNZKVUMLOE-UHFFFAOYSA-N 0.000 claims description 2
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- QUZCCVXIHCIHPV-UHFFFAOYSA-N n-[3-[3-(4-cyanoanilino)-3-oxopropyl]phenyl]-3-piperidin-3-ylpropanamide;n-[3-[3-(3,4-dimethoxyanilino)-3-oxopropyl]phenyl]-3-piperidin-3-ylpropanamide Chemical compound C=1C=CC(CCC(=O)NC=2C=CC(=CC=2)C#N)=CC=1NC(=O)CCC1CCCNC1.C1=C(OC)C(OC)=CC=C1NC(=O)CCC1=CC=CC(NC(=O)CCC2CNCCC2)=C1 QUZCCVXIHCIHPV-UHFFFAOYSA-N 0.000 claims description 2
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- SFLBZARATFKMJY-UHFFFAOYSA-N n-[4-(aminomethyl)phenyl]-3-[[(4-cyanophenyl)carbamoylamino]methyl]benzamide Chemical compound C1=CC(CN)=CC=C1NC(=O)C1=CC=CC(CNC(=O)NC=2C=CC(=CC=2)C#N)=C1 SFLBZARATFKMJY-UHFFFAOYSA-N 0.000 claims description 2
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- BFIRBXUGLIZKLJ-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]phenyl]-3-[[(4-methoxybenzoyl)amino]methyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 BFIRBXUGLIZKLJ-UHFFFAOYSA-N 0.000 claims description 2
- OCDZHXBZSVPCLL-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]phenyl]-3-[[(4-methoxyphenyl)carbamoylamino]methyl]benzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 OCDZHXBZSVPCLL-UHFFFAOYSA-N 0.000 claims description 2
- HKDVENGCVKSWHN-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]phenyl]-3-[[(4-methylsulfanylbenzoyl)amino]methyl]benzamide Chemical compound C1=CC(SC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 HKDVENGCVKSWHN-UHFFFAOYSA-N 0.000 claims description 2
- YWCUAPIFVOPZEI-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]phenyl]-3-[[[3-(trifluoromethyl)benzoyl]amino]methyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1 YWCUAPIFVOPZEI-UHFFFAOYSA-N 0.000 claims description 2
- XIAWNXZYZQNYEO-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]phenyl]-3-[[[4-(trifluoromethoxy)benzoyl]amino]methyl]benzamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)C=2C=CC(OC(F)(F)F)=CC=2)=C1 XIAWNXZYZQNYEO-UHFFFAOYSA-N 0.000 claims description 2
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- AHJYPRHNOXXVRT-KRWDZBQOSA-N n-[[3-[[(6s)-2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)N[C@@H]2CC=3SC(N)=NC=3CC2)=C1 AHJYPRHNOXXVRT-KRWDZBQOSA-N 0.000 claims description 2
- GPEMGGFDBKPUNW-UHFFFAOYSA-N n-[[3-[[3-(aminomethyl)phenyl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=C(CN)C=CC=2)=C1 GPEMGGFDBKPUNW-UHFFFAOYSA-N 0.000 claims description 2
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- BQZWAEKWKGMNHA-UHFFFAOYSA-N n-[[3-[[4-(dimethylamino)cyclohexyl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC2CCC(CC2)N(C)C)=C1 BQZWAEKWKGMNHA-UHFFFAOYSA-N 0.000 claims description 2
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- ONERQDONRMNOLJ-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C=C(C=CC=2)C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 ONERQDONRMNOLJ-UHFFFAOYSA-N 0.000 claims description 2
- MMRPIWYTUYGTFQ-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 MMRPIWYTUYGTFQ-UHFFFAOYSA-N 0.000 claims description 2
- ZNMZMLILKIXZHP-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]-3,5-dimethoxybenzamide Chemical compound COC1=CC(OC)=CC(C(=O)NCC=2C=C(C=CC=2)C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 ZNMZMLILKIXZHP-UHFFFAOYSA-N 0.000 claims description 2
- NDUNRHQNNNHQFV-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]-3-fluoro-4-methoxybenzamide Chemical compound C1=C(F)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 NDUNRHQNNNHQFV-UHFFFAOYSA-N 0.000 claims description 2
- ZAAATGOITDPPKG-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]-4-methoxy-3,5-dimethylbenzamide Chemical compound C1=C(C)C(OC)=C(C)C=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 ZAAATGOITDPPKG-UHFFFAOYSA-N 0.000 claims description 2
- SFICHRQXHBPAGM-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]-4-methoxy-3-(methoxymethyl)benzamide Chemical compound C1=C(OC)C(COC)=CC(C(=O)NCC=2C=C(C=CC=2)C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 SFICHRQXHBPAGM-UHFFFAOYSA-N 0.000 claims description 2
- JHAMKJGGGMLIGX-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]-4-methoxy-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 JHAMKJGGGMLIGX-UHFFFAOYSA-N 0.000 claims description 2
- ZHYPMHNQQRIWRP-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]-4-methoxy-3-methylbenzamide Chemical compound C1=C(C)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2C=CC(CN(C)C)=CC=2)=C1 ZHYPMHNQQRIWRP-UHFFFAOYSA-N 0.000 claims description 2
- PWFHHGIUVHLZME-UHFFFAOYSA-N n-[[3-[[4-[(dimethylamino)methyl]phenyl]carbamoyl]phenyl]methyl]quinoline-6-carboxamide Chemical compound C1=CC(CN(C)C)=CC=C1NC(=O)C1=CC=CC(CNC(=O)C=2C=C3C=CC=NC3=CC=2)=C1 PWFHHGIUVHLZME-UHFFFAOYSA-N 0.000 claims description 2
- PAYRKVARELJZIS-UHFFFAOYSA-N n-[[3-[[4-[2-(dimethylamino)ethyl]-1,3-thiazol-2-yl]carbamoyl]phenyl]methyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=C(CCN(C)C)N=2)=C1 PAYRKVARELJZIS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
- KBELWXQYQJTLLV-GOSISDBHSA-N n-[[3-[[(6r)-6-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-4-methoxy-3-methylbenzamide Chemical compound C1=C(C)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@H](N)CCC=3N=2)=C1 KBELWXQYQJTLLV-GOSISDBHSA-N 0.000 claims 3
- KBELWXQYQJTLLV-SFHVURJKSA-N n-[[3-[[(6s)-6-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]carbamoyl]phenyl]methyl]-4-methoxy-3-methylbenzamide Chemical compound C1=C(C)C(OC)=CC=C1C(=O)NCC1=CC=CC(C(=O)NC=2SC=3C[C@@H](N)CCC=3N=2)=C1 KBELWXQYQJTLLV-SFHVURJKSA-N 0.000 claims 3
- RHNAQSUNHOXWMV-UHFFFAOYSA-N 2-cyano-4-methyl-n-[[3-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)carbamoyl]phenyl]methyl]benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C(C=1)=CC=CC=1CNC(=O)C1=CC=C(C)C=C1C#N RHNAQSUNHOXWMV-UHFFFAOYSA-N 0.000 claims 2
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| JPWO2010024258A1 (ja) * | 2008-08-29 | 2012-01-26 | 塩野義製薬株式会社 | Pi3k阻害活性を有する縮環アゾール誘導体 |
| US20120225862A1 (en) * | 2009-07-21 | 2012-09-06 | Auckland Univservices Limited | Heteroaryl benzamides, compositions and methods of use |
| US9126978B2 (en) | 2009-11-17 | 2015-09-08 | The Regents Of The University Of Michigan | 1,4-benzodiazepine-2,5-diones and related compounds with therapeutic properties |
| US8835444B2 (en) * | 2010-02-02 | 2014-09-16 | Novartis Ag | Cyclohexyl amide derivatives as CRF receptor antagonists |
| US9079880B2 (en) * | 2010-07-07 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| US8697911B2 (en) | 2010-07-07 | 2014-04-15 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| WO2012054367A1 (en) | 2010-10-19 | 2012-04-26 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| AR083855A1 (es) * | 2010-11-15 | 2013-03-27 | Abbott Lab | Inhibidores de nampt y rock |
| US9029370B2 (en) * | 2011-06-10 | 2015-05-12 | Hoffmann-La Roche Inc. | Substituted benzamide derivatives |
| WO2013057944A1 (ja) | 2011-10-19 | 2013-04-25 | 興和株式会社 | 新規なスピロインドリン化合物、及びそれを含有する医薬 |
| CN104011026B (zh) | 2011-12-20 | 2016-07-20 | 拜耳知识产权股份有限公司 | 杀虫用芳酰胺 |
| AU2013318206B2 (en) | 2012-09-20 | 2018-07-26 | Temple University - Of The Commonwealth System Of Higher Education | Substituted alkyl diaryl derivatives, methods of preparation and uses |
| JP6488239B2 (ja) | 2013-01-18 | 2019-03-20 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | Rock阻害剤としてのフタラジノンおよびイソキノリノン |
| WO2014177699A1 (en) * | 2013-05-03 | 2014-11-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Rhoa (rock) inhibitors for the treatment of enflammatory bowel disease |
| US9902702B2 (en) | 2014-07-15 | 2018-02-27 | Bristol-Myers Squibb Company | Spirocycloheptanes as inhibitors of rock |
| WO2016028971A1 (en) | 2014-08-21 | 2016-02-25 | Bristol-Myers Squibb Company | Tied-back benzamide derivatives as potent rock inhibitors |
| JP6883173B2 (ja) | 2015-05-12 | 2021-06-09 | ヘモストッド エスエー | 改善された血小板産生のための薬理学的特徴およびマイクロ流体特徴の組み合わせ |
| KR20180011843A (ko) | 2015-06-11 | 2018-02-02 | 바실리어 파마슈티카 인터내셔널 리미티드 | 유출-펌프 억제제 및 이의 치료적 용도 |
| CN105195114B (zh) * | 2015-10-29 | 2017-08-25 | 重庆郑博生物科技有限公司 | 脓毒症多种致病因子的吸附材料及其制备方法和用途 |
| TWI730032B (zh) | 2016-01-13 | 2021-06-11 | 美商必治妥美雅史谷比公司 | 作為rock抑制劑之螺庚烷水楊酸醯胺及相關化合物 |
| US10787450B2 (en) | 2016-07-07 | 2020-09-29 | Bristol-Myers Squibb Company | Spiro-fused cyclic ureas as inhibitors of rock |
| CN108203433B (zh) * | 2016-12-16 | 2020-07-03 | 成都先导药物开发股份有限公司 | 一种rock抑制剂及其应用 |
| KR102644889B1 (ko) | 2017-07-12 | 2024-03-06 | 브리스톨-마이어스 스큅 컴퍼니 | Rock 억제제로서의 스피로헵타닐 히단토인 |
| TW201908293A (zh) | 2017-07-12 | 2019-03-01 | 美商必治妥美雅史谷比公司 | 作為rock抑制劑之5員及雙環雜環醯胺 |
| US11306081B2 (en) | 2017-07-12 | 2022-04-19 | Bristol-Myers Squibb Company | Phenylacetamides as inhibitors of rock |
| US11299488B2 (en) | 2017-07-12 | 2022-04-12 | Bristol-Myers Squibb Company | Five membered-aminoheterocycle and 5,6-or 6,6-membered bicyclic aminoheterocyclic inhibitors of rock for the treatment of heart failure |
| WO2020047229A1 (en) | 2018-08-29 | 2020-03-05 | University Of Massachusetts | Inhibition of protein kinases to treat friedreich ataxia |
| WO2023091565A1 (en) * | 2021-11-17 | 2023-05-25 | The University Of North Carolina At Chapel Hill | Nsd2-targeted chemical degraders and compositions and methods of use thereof |
| WO2024076155A1 (ko) * | 2022-10-04 | 2024-04-11 | 노보렉스 주식회사 | Yeats 도메인 억제제로서 신규한 화합물 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20000065219A (ko) * | 1996-05-20 | 2000-11-06 | 마르크 젠너 | 티엔에프 저해제 및 피디이-4 저해제로서의 퀴놀린 카르복사미드 |
| JPH11139969A (ja) * | 1997-08-07 | 1999-05-25 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
| JPH11130751A (ja) * | 1997-10-30 | 1999-05-18 | Yoshitomi Pharmaceut Ind Ltd | アミド化合物およびそれらの酸付加塩の標識化合物 |
| US7217722B2 (en) * | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| WO2002100833A1 (en) * | 2001-06-12 | 2002-12-19 | Sumitomo Pharmaceuticals Company, Limited | Rho KINASE INHIBITORS |
| DE10357510A1 (de) * | 2003-12-09 | 2005-07-07 | Bayer Healthcare Ag | Heteroarylsubstituierte Benzole |
| JP2007519754A (ja) * | 2004-01-30 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | 化合物 |
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- 2008-01-02 US US12/521,817 patent/US8093266B2/en active Active
- 2008-01-02 AR ARP080100007A patent/AR064726A1/es unknown
- 2008-01-02 CA CA002674389A patent/CA2674389A1/en not_active Abandoned
- 2008-01-02 EP EP08727346.2A patent/EP2114869B1/en not_active Not-in-force
- 2008-01-02 TW TW097100054A patent/TW200843770A/zh unknown
- 2008-01-02 JP JP2009544958A patent/JP5258790B2/ja not_active Expired - Fee Related
- 2008-01-02 WO PCT/US2008/050014 patent/WO2008086047A1/en not_active Ceased
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| AR064726A1 (es) | 2009-04-22 |
| JP2010514842A (ja) | 2010-05-06 |
| EP2114869A1 (en) | 2009-11-11 |
| WO2008086047A1 (en) | 2008-07-17 |
| CL2007003874A1 (es) | 2008-05-16 |
| JP5258790B2 (ja) | 2013-08-07 |
| US20100041645A1 (en) | 2010-02-18 |
| EP2114869B1 (en) | 2014-07-23 |
| US8093266B2 (en) | 2012-01-10 |
| TW200843770A (en) | 2008-11-16 |
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