JP2010503625A5 - - Google Patents
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- Publication number
- JP2010503625A5 JP2010503625A5 JP2009527720A JP2009527720A JP2010503625A5 JP 2010503625 A5 JP2010503625 A5 JP 2010503625A5 JP 2009527720 A JP2009527720 A JP 2009527720A JP 2009527720 A JP2009527720 A JP 2009527720A JP 2010503625 A5 JP2010503625 A5 JP 2010503625A5
- Authority
- JP
- Japan
- Prior art keywords
- ylcarbamoyl
- hydroxy
- amino
- phenylethyl
- benzimidazol
- 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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- -1 amino, amidino, aminomethylene, aminopyridinyl Chemical group 0.000 claims 98
- 150000001408 amides Chemical class 0.000 claims 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- MBAPEUGRHHCVFO-UHFFFAOYSA-N n-[3-[(2-amino-3h-benzimidazol-5-yl)amino]-1-(3-chlorophenyl)-2-hydroxy-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C=C(Cl)C=CC=1)C(O)C(=O)NC1=CC=C(N=C(N)N2)C2=C1 MBAPEUGRHHCVFO-UHFFFAOYSA-N 0.000 claims 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- JBWZIRYKBWGONS-UHFFFAOYSA-N 1-ethyl-2,3-dimethylindole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N(CC)C(C)=C(C)C2=C1 JBWZIRYKBWGONS-UHFFFAOYSA-N 0.000 claims 1
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- GSYIVQLTSZFJRV-UHFFFAOYSA-N 3-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1 GSYIVQLTSZFJRV-UHFFFAOYSA-N 0.000 claims 1
- FXLZVJIGHKRUIB-UHFFFAOYSA-N 3-amino-N-(2-amino-3H-benzimidazol-5-yl)-2-hydroxy-3-phenylpropanamide Chemical compound C=1C=C2N=C(N)NC2=CC=1NC(=O)C(O)C(N)C1=CC=CC=C1 FXLZVJIGHKRUIB-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- NEBLBCLYWNCQIH-UHFFFAOYSA-N 3-ethoxyquinoxaline-2-carboxylic acid Chemical compound C1=CC=C2N=C(C(O)=O)C(OCC)=NC2=C1 NEBLBCLYWNCQIH-UHFFFAOYSA-N 0.000 claims 1
- PMHDSACGRKBACK-UHFFFAOYSA-N 4h-thieno[3,2-b]pyrrole-5-carboxylic acid Chemical compound S1C=CC2=C1C=C(C(=O)O)N2 PMHDSACGRKBACK-UHFFFAOYSA-N 0.000 claims 1
- UZHQHNDRVITJPL-UHFFFAOYSA-N 5,6-dimethoxy-1h-indole-2-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC2=C1NC(C(O)=O)=C2 UZHQHNDRVITJPL-UHFFFAOYSA-N 0.000 claims 1
- ZVBNGIDVTPTFCL-UHFFFAOYSA-N 5-ethylthiophene-2-carboxylic acid Chemical compound CCC1=CC=C(C(O)=O)S1 ZVBNGIDVTPTFCL-UHFFFAOYSA-N 0.000 claims 1
- WGPALAIKGVKNGT-UHFFFAOYSA-N 5-ethylthiophene-3-carboxylic acid Chemical compound CCC1=CC(C(O)=O)=CS1 WGPALAIKGVKNGT-UHFFFAOYSA-N 0.000 claims 1
- YEBJVSLNUMZXRJ-UHFFFAOYSA-N 5-methoxyindole-2-carboxylic acid Chemical compound COC1=CC=C2NC(C(O)=O)=CC2=C1 YEBJVSLNUMZXRJ-UHFFFAOYSA-N 0.000 claims 1
- XNBGANWAZJWOHS-UHFFFAOYSA-N 6-methoxy-1h-indole-2-carboxylic acid Chemical compound COC1=CC=C2C=C(C(O)=O)NC2=C1 XNBGANWAZJWOHS-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000002785 azepinyl group Chemical group 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000004623 carbolinyl group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000003838 furazanyl group Chemical group 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 1
- 125000005438 isoindazolyl group Chemical group 0.000 claims 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- HBHLOJRWBTVNSR-BJKOFHAPSA-N n-[(1r,2r)-3-[(1-aminoisoquinolin-6-yl)amino]-1-(furan-2-yl)-2-hydroxy-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)N[C@@H](C=1OC=CC=1)[C@@H](O)C(=O)NC1=CC=C(C(N)=NC=C2)C2=C1 HBHLOJRWBTVNSR-BJKOFHAPSA-N 0.000 claims 1
- NKNCBARULWURJY-XZOQPEGZSA-N n-[(1s,2r)-3-[(2-amino-3h-benzimidazol-5-yl)amino]-1-(2-fluorophenyl)-2-hydroxy-3-oxopropyl]-4-propan-2-ylbenzamide Chemical compound C1=CC(C(C)C)=CC=C1C(=O)N[C@@H](C=1C(=CC=CC=1)F)[C@@H](O)C(=O)NC1=CC=C(N=C(N)N2)C2=C1 NKNCBARULWURJY-XZOQPEGZSA-N 0.000 claims 1
- DDSHPRLJCJHNPN-RBUKOAKNSA-N n-[(1s,2r)-3-[(2-amino-3h-benzimidazol-5-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]-1-methylpyrrole-2-carboxamide Chemical compound CN1C=CC=C1C(=O)N[C@@H](C=1C=CC=CC=1)[C@@H](O)C(=O)NC1=CC=C(N=C(N)N2)C2=C1 DDSHPRLJCJHNPN-RBUKOAKNSA-N 0.000 claims 1
- BJIGXSLRXOMDFV-LEWJYISDSA-N n-[(1s,2r)-3-[4-(aminomethyl)anilino]-2-hydroxy-3-oxo-1-phenylpropyl]benzamide Chemical compound C1=CC(CN)=CC=C1NC(=O)[C@H](O)[C@H](C=1C=CC=CC=1)NC(=O)C1=CC=CC=C1 BJIGXSLRXOMDFV-LEWJYISDSA-N 0.000 claims 1
- RYDUVNKDWACUOO-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-6-yl)amino]-1-(2-chlorophenyl)-2-hydroxy-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C(=CC=CC=1)Cl)C(O)C(=O)NC1=CC=C(C(N)=NC=C2)C2=C1 RYDUVNKDWACUOO-UHFFFAOYSA-N 0.000 claims 1
- PSBYACUVMCPYGG-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-6-yl)amino]-1-(2-chlorophenyl)-2-hydroxy-3-oxopropyl]-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NC(C=1C(=CC=CC=1)Cl)C(O)C(=O)NC1=CC=C(C(N)=NC=C2)C2=C1 PSBYACUVMCPYGG-UHFFFAOYSA-N 0.000 claims 1
- QZVGWVHWNPFPBV-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-6-yl)amino]-1-(3-bromophenyl)-2-hydroxy-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C=C(Br)C=CC=1)C(O)C(=O)NC1=CC=C(C(N)=NC=C2)C2=C1 QZVGWVHWNPFPBV-UHFFFAOYSA-N 0.000 claims 1
- XGZAPPILAXIYJW-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-6-yl)amino]-1-(3-bromophenyl)-2-hydroxy-3-oxopropyl]-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NC(C=1C=C(Br)C=CC=1)C(O)C(=O)NC1=CC=C(C(N)=NC=C2)C2=C1 XGZAPPILAXIYJW-UHFFFAOYSA-N 0.000 claims 1
- LNLPEXKJVBDGJP-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-6-yl)amino]-1-(4-bromophenyl)-2-hydroxy-3-oxopropyl]-4-ethylbenzamide Chemical compound C1=CC(CC)=CC=C1C(=O)NC(C=1C=CC(Br)=CC=1)C(O)C(=O)NC1=CC=C(C(N)=NC=C2)C2=C1 LNLPEXKJVBDGJP-UHFFFAOYSA-N 0.000 claims 1
- GLRLIGWNGNASCP-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-6-yl)amino]-2-hydroxy-3-oxo-1-[4-(trifluoromethyl)phenyl]propyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C=CC(=CC=1)C(F)(F)F)C(O)C(=O)NC1=CC=C(C(N)=NC=C2)C2=C1 GLRLIGWNGNASCP-UHFFFAOYSA-N 0.000 claims 1
- OVIVYWGUNOGZSR-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-6-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]-4-cyclopropylbenzamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1NC(=O)C(O)C(C=1C=CC=CC=1)NC(=O)C(C=C1)=CC=C1C1CC1 OVIVYWGUNOGZSR-UHFFFAOYSA-N 0.000 claims 1
- OMCZJDPPHMOPNR-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-6-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]benzamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1NC(=O)C(O)C(C=1C=CC=CC=1)NC(=O)C1=CC=CC=C1 OMCZJDPPHMOPNR-UHFFFAOYSA-N 0.000 claims 1
- DOAGNBRUTGGWAU-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-7-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C=CC=CC=1)C(O)C(=O)NC1=CC=C(C=CN=C2N)C2=C1 DOAGNBRUTGGWAU-UHFFFAOYSA-N 0.000 claims 1
- SQYDTBLYOUGWMS-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-7-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]-4-propan-2-ylbenzamide Chemical compound C1=CC(C(C)C)=CC=C1C(=O)NC(C=1C=CC=CC=1)C(O)C(=O)NC1=CC=C(C=CN=C2N)C2=C1 SQYDTBLYOUGWMS-UHFFFAOYSA-N 0.000 claims 1
- FCVDQEGIRQCHHX-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-7-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]-5-ethylthiophene-2-carboxamide Chemical compound S1C(CC)=CC=C1C(=O)NC(C=1C=CC=CC=1)C(O)C(=O)NC1=CC=C(C=CN=C2N)C2=C1 FCVDQEGIRQCHHX-UHFFFAOYSA-N 0.000 claims 1
- BTWBLJNOLTUPJG-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-7-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]-5-methoxy-1h-indole-2-carboxamide Chemical compound C=1C2=CC(OC)=CC=C2NC=1C(=O)NC(C(O)C(=O)NC=1C=C2C(N)=NC=CC2=CC=1)C1=CC=CC=C1 BTWBLJNOLTUPJG-UHFFFAOYSA-N 0.000 claims 1
- ZPLOCHOZGQBTKE-UHFFFAOYSA-N n-[3-[(1-aminoisoquinolin-7-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]-5-tert-butylthiophene-2-carboxamide Chemical compound S1C(C(C)(C)C)=CC=C1C(=O)NC(C=1C=CC=CC=1)C(O)C(=O)NC1=CC=C(C=CN=C2N)C2=C1 ZPLOCHOZGQBTKE-UHFFFAOYSA-N 0.000 claims 1
- DHNOUOOOSHHVHC-UHFFFAOYSA-N n-[3-[(2-amino-1,3-benzothiazol-6-yl)amino]-1-(2-chlorophenyl)-2-hydroxy-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C(=CC=CC=1)Cl)C(O)C(=O)NC1=CC=C(N=C(N)S2)C2=C1 DHNOUOOOSHHVHC-UHFFFAOYSA-N 0.000 claims 1
- NTMQSMIATALJNE-UHFFFAOYSA-N n-[3-[(2-amino-1,3-benzothiazol-6-yl)amino]-1-(3-ethoxyphenyl)-2-hydroxy-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound CCOC1=CC=CC(C(NC(=O)C=2C=CC(=CC=2)N(CC)CC)C(O)C(=O)NC=2C=C3SC(N)=NC3=CC=2)=C1 NTMQSMIATALJNE-UHFFFAOYSA-N 0.000 claims 1
- UKAYXJYCJJGLMM-UHFFFAOYSA-N n-[3-[(2-amino-1,3-benzothiazol-6-yl)amino]-1-(3-ethoxyphenyl)-2-hydroxy-3-oxopropyl]-4-propan-2-ylbenzamide Chemical compound CCOC1=CC=CC(C(NC(=O)C=2C=CC(=CC=2)C(C)C)C(O)C(=O)NC=2C=C3SC(N)=NC3=CC=2)=C1 UKAYXJYCJJGLMM-UHFFFAOYSA-N 0.000 claims 1
- GFMVOBJCVYCOCH-UHFFFAOYSA-N n-[3-[(2-amino-1,3-benzothiazol-6-yl)amino]-2-hydroxy-3-oxo-1-[4-(trifluoromethyl)phenyl]propyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C=CC(=CC=1)C(F)(F)F)C(O)C(=O)NC1=CC=C(N=C(N)S2)C2=C1 GFMVOBJCVYCOCH-UHFFFAOYSA-N 0.000 claims 1
- NQUXFDSRTUUIDV-UHFFFAOYSA-N n-[3-[(2-amino-1,3-benzothiazol-6-yl)amino]-2-hydroxy-3-oxo-1-phenylpropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C=CC=CC=1)C(O)C(=O)NC1=CC=C(N=C(N)S2)C2=C1 NQUXFDSRTUUIDV-UHFFFAOYSA-N 0.000 claims 1
- NLMJZJRDJCHRPJ-UHFFFAOYSA-N n-[3-[(2-amino-3h-benzimidazol-5-yl)amino]-1-(3,5-dimethoxyphenyl)-2-hydroxy-3-oxopropyl]-4-propan-2-ylbenzamide Chemical compound COC1=CC(OC)=CC(C(NC(=O)C=2C=CC(=CC=2)C(C)C)C(O)C(=O)NC=2C=C3NC(N)=NC3=CC=2)=C1 NLMJZJRDJCHRPJ-UHFFFAOYSA-N 0.000 claims 1
- CKIRYJVCMIPWKM-UHFFFAOYSA-N n-[3-[(2-amino-3h-benzimidazol-5-yl)amino]-1-(5-fluoro-2-methylsulfonylphenyl)-2-hydroxy-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C(=CC=C(F)C=1)S(C)(=O)=O)C(O)C(=O)NC1=CC=C(N=C(N)N2)C2=C1 CKIRYJVCMIPWKM-UHFFFAOYSA-N 0.000 claims 1
- YBSYXYJWBBWWRK-UHFFFAOYSA-N n-[3-[(2-amino-3h-benzimidazol-5-yl)amino]-2-hydroxy-1-(2-methoxyphenyl)-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C(=CC=CC=1)OC)C(O)C(=O)NC1=CC=C(NC(N)=N2)C2=C1 YBSYXYJWBBWWRK-UHFFFAOYSA-N 0.000 claims 1
- YDOJLNHVVKMASH-UHFFFAOYSA-N n-[3-[(2-amino-3h-benzimidazol-5-yl)amino]-2-hydroxy-1-(2-methylphenyl)-3-oxopropyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C(=CC=CC=1)C)C(O)C(=O)NC1=CC=C(N=C(N)N2)C2=C1 YDOJLNHVVKMASH-UHFFFAOYSA-N 0.000 claims 1
- NYNJVVKPTQUXLT-UHFFFAOYSA-N n-[3-[(2-amino-3h-benzimidazol-5-yl)amino]-2-hydroxy-3-oxo-1-[2-(trifluoromethoxy)phenyl]propyl]-4-(diethylamino)benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)NC(C=1C(=CC=CC=1)OC(F)(F)F)C(O)C(=O)NC1=CC=C(N=C(N)N2)C2=C1 NYNJVVKPTQUXLT-UHFFFAOYSA-N 0.000 claims 1
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| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| EP2049543B1 (en) * | 2006-09-07 | 2014-11-05 | Callaghan Innovation Research Limited | Acyclic amine inhibitors of 5'-methylthioadenosine phosphorylase and nucleosidase |
| WO2009132051A1 (en) | 2008-04-21 | 2009-10-29 | Signum Biosciences, Inc. | Compounds, compositions and methods for making the same |
| AU2009322342A1 (en) | 2008-12-05 | 2011-06-30 | Merck Sharp & Dohme Corp. | Morpholinone compounds as factor IXa inhibitors |
| JP2013503163A (ja) * | 2009-08-31 | 2013-01-31 | 持田製薬株式会社 | 第ＩＸａ因子阻害薬としてのモルホリノン化合物 |
| WO2015160636A1 (en) | 2014-04-16 | 2015-10-22 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| CN109627218B (zh) * | 2018-11-27 | 2022-03-29 | 深圳市龙华区中心医院 | 一种抗凝小分子化合物及其应用和包含其的药物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4238260A1 (de) | 1992-11-12 | 1994-05-19 | Basf Ag | Substituierte ortho-Ethenylphenylessigsäurederivate |
| CA2159649A1 (en) | 1993-03-29 | 1994-10-13 | Queen's University At Kingston | Anticoagulant compounds |
| TW394760B (en) * | 1993-09-07 | 2000-06-21 | Hoffmann La Roche | Novel Carboxamides, process for their preparation and pharmaceutical composition containing the same |
| FI974437A0 (fi) * | 1995-06-06 | 1997-12-05 | Pfizer | Substituoituja N-(indoli-2-karbonyyli)amideja ja johdannaisia glykogeenifosforylaasi-inhibiittoreina |
| MX9709875A (es) * | 1995-06-06 | 1998-03-31 | Pfizer | N-(indol-2-carbonil)-glicinamidas substituidas y derivados como inhibidores de glicogeno fosforilasa, composiciones que las contienen y uso de las mismas. |
| CZ298827B6 (cs) * | 1997-12-24 | 2008-02-20 | Sanofi - Aventis Deutschland GmbH | Deriváty indolu jako inhibitory faktoru Xa, zpusob jejich prípravy a farmaceutická kompozice, kteráje obsahuje |
| US6451832B2 (en) * | 1999-12-23 | 2002-09-17 | Boehringer Ingelheim Pharma Kg | Benzimidazoles with antithrombotic activity |
| CO5271699A1 (es) * | 2000-01-24 | 2003-04-30 | Pfizer Prod Inc | Procedimiento para el tratamiento de cardiomiopatia utilizando inhibidores de la glucogeno fosforilasa |
| JP4666440B2 (ja) * | 2000-06-30 | 2011-04-06 | 生化学工業株式会社 | アミノアルコール誘導体 |
| US6642252B2 (en) | 2000-11-07 | 2003-11-04 | Bristol-Myers Squibb Company | Acid derivatives useful as serine protease inhibitors |
| US7122559B2 (en) | 2003-02-11 | 2006-10-17 | Bristol-Myers Squibb Company | Phenylglycine derivatives useful as serine protease inhibitors |
| US7056932B2 (en) | 2003-12-19 | 2006-06-06 | Hoffman-La Roche Inc. | Heterocyclyl substituted 1-alkoxy acetic acid amides |
| US8211919B2 (en) * | 2005-09-02 | 2012-07-03 | Astellas Pharma Inc. | Amide derivatives as rock inhibitors |
| WO2007029587A1 (ja) * | 2005-09-05 | 2007-03-15 | Dainippon Sumitomo Pharma Co., Ltd. | βセクレターゼ阻害剤 |
-
2007
- 2007-08-31 NZ NZ575603A patent/NZ575603A/en not_active IP Right Cessation
- 2007-08-31 CN CN2007800341822A patent/CN101516834B/zh not_active Expired - Fee Related
- 2007-08-31 SG SG2011058724A patent/SG174080A1/en unknown
- 2007-08-31 EP EP07802031.0A patent/EP2069289B1/de active Active
- 2007-08-31 BR BRPI0716991-4A2A patent/BRPI0716991A2/pt not_active IP Right Cessation
- 2007-08-31 AU AU2007297013A patent/AU2007297013B2/en not_active Ceased
- 2007-08-31 JP JP2009527720A patent/JP5249226B2/ja not_active Expired - Fee Related
- 2007-08-31 CA CA002663544A patent/CA2663544A1/en not_active Abandoned
- 2007-08-31 RU RU2009113602/04A patent/RU2446157C2/ru not_active IP Right Cessation
- 2007-08-31 WO PCT/EP2007/007613 patent/WO2008031509A1/de not_active Ceased
- 2007-08-31 KR KR1020097005160A patent/KR20090050081A/ko not_active Ceased
- 2007-08-31 MY MYPI20090791 patent/MY150745A/en unknown
- 2007-08-31 MX MX2009002047A patent/MX2009002047A/es active IP Right Grant
- 2007-09-11 UY UY30585A patent/UY30585A1/es not_active Application Discontinuation
- 2007-09-11 AR ARP070104012A patent/AR063708A1/es not_active Application Discontinuation
- 2007-09-11 TW TW096133788A patent/TWI394570B/zh not_active IP Right Cessation
- 2007-09-12 CL CL200702652A patent/CL2007002652A1/es unknown
-
2009
- 2009-02-03 ZA ZA200900807A patent/ZA200900807B/xx unknown
- 2009-03-06 MA MA31700A patent/MA30707B1/fr unknown
- 2009-03-09 IL IL197504A patent/IL197504A/en not_active IP Right Cessation
- 2009-03-09 US US12/400,189 patent/US8097758B2/en not_active Expired - Fee Related
- 2009-03-16 NO NO20091110A patent/NO20091110L/no not_active Application Discontinuation
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