EA002817B1 - Соединения сульфоновой кислоты или сульфониламино-n-(гетероаралкил)азагетероциклиламида - Google Patents

Info

Publication number

EA002817B1

EA002817B1 EA199900542A EA199900542A EA002817B1 EA 002817 B1 EA002817 B1 EA 002817B1 EA 199900542 A EA199900542 A EA 199900542A EA 199900542 A EA199900542 A EA 199900542A EA 002817 B1 EA002817 B1 EA 002817B1

Authority

EA

Eurasian Patent Office

Prior art keywords

sulfonic acid

ylmethyl

oxopyrrolidin

amide

methoxynaphthalene

Prior art date

1996-12-13

Links

• Espacenet
• Global Dossier
• Discuss

• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title description 2
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 476
• -1 2-oxo-1,2-dihydroquinolinyl Chemical group 0.000 claims abstract description 394
• CKARHIGQRRNVFD-UHFFFAOYSA-N 7-methoxynaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(OC)=CC=C21 CKARHIGQRRNVFD-UHFFFAOYSA-N 0.000 claims abstract description 201
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims abstract description 177
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 58
• ZYDGKFWFDVZKMG-UHFFFAOYSA-N 6-chloro-1-benzothiophene-2-sulfonic acid Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)O)=CC2=C1 ZYDGKFWFDVZKMG-UHFFFAOYSA-N 0.000 claims abstract description 56
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
• 150000003839 salts Chemical class 0.000 claims abstract description 48
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 41
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims abstract description 38
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 29
• 239000001257 hydrogen Substances 0.000 claims abstract description 25
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 12
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 12
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 10
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 10
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 9
• 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims abstract description 9
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
• 125000006085 pyrrolopyridyl group Chemical group 0.000 claims abstract description 4
• 239000012453 solvate Substances 0.000 claims abstract description 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 2
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims abstract 2
• 150000001408 amides Chemical class 0.000 claims description 268
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 238000000034 method Methods 0.000 claims description 40
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
• KTVOMLQUDMNZLK-UHFFFAOYSA-N 1-benzothiophene-2-sulfonic acid Chemical compound C1=CC=C2SC(S(=O)(=O)O)=CC2=C1 KTVOMLQUDMNZLK-UHFFFAOYSA-N 0.000 claims description 33
• 108010074860 Factor Xa Proteins 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 230000000694 effects Effects 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 239000003146 anticoagulant agent Substances 0.000 claims description 22
• 150000002367 halogens Chemical group 0.000 claims description 22
• 238000002560 therapeutic procedure Methods 0.000 claims description 14
• 208000007536 Thrombosis Diseases 0.000 claims description 13
• 230000015572 biosynthetic process Effects 0.000 claims description 13
• 230000002792 vascular Effects 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• CUJKETNJIDESRG-UHFFFAOYSA-N 5-pyridin-4-ylthiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=NC=C1 CUJKETNJIDESRG-UHFFFAOYSA-N 0.000 claims description 8
• 210000001367 artery Anatomy 0.000 claims description 8
• 230000015271 coagulation Effects 0.000 claims description 8
• 238000005345 coagulation Methods 0.000 claims description 8
• 210000003462 vein Anatomy 0.000 claims description 8
• PKWPORDEAWHBJU-UHFFFAOYSA-N 5-pyridin-3-ylthiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=CN=C1 PKWPORDEAWHBJU-UHFFFAOYSA-N 0.000 claims description 7
• 208000005189 Embolism Diseases 0.000 claims description 7
• UVLKAUNUFWQFID-UHFFFAOYSA-N thieno[3,2-b]pyridine-2-sulfonic acid Chemical compound C1=CC=C2SC(S(=O)(=O)O)=CC2=N1 UVLKAUNUFWQFID-UHFFFAOYSA-N 0.000 claims description 7
• 206010053567 Coagulopathies Diseases 0.000 claims description 6
• 206010000891 acute myocardial infarction Diseases 0.000 claims description 6
• 238000007887 coronary angioplasty Methods 0.000 claims description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 230000001575 pathological effect Effects 0.000 claims description 6
• 230000002093 peripheral effect Effects 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 230000001154 acute effect Effects 0.000 claims description 5
• 201000011510 cancer Diseases 0.000 claims description 5
• 230000007774 longterm Effects 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 206010002388 Angina unstable Diseases 0.000 claims description 4
• 208000032843 Hemorrhage Diseases 0.000 claims description 4
• 206010022562 Intermittent claudication Diseases 0.000 claims description 4
• 208000010378 Pulmonary Embolism Diseases 0.000 claims description 4
• 206010040070 Septic Shock Diseases 0.000 claims description 4
• 208000001435 Thromboembolism Diseases 0.000 claims description 4
• 208000007814 Unstable Angina Diseases 0.000 claims description 4
• 208000036142 Viral infection Diseases 0.000 claims description 4
• 230000003187 abdominal effect Effects 0.000 claims description 4
• 230000002159 abnormal effect Effects 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 4
• 238000001631 haemodialysis Methods 0.000 claims description 4
• 230000000322 hemodialysis Effects 0.000 claims description 4
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 4
• 208000021156 intermittent vascular claudication Diseases 0.000 claims description 4
• 210000003141 lower extremity Anatomy 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 230000036303 septic shock Effects 0.000 claims description 4
• 238000001356 surgical procedure Methods 0.000 claims description 4
• 230000009885 systemic effect Effects 0.000 claims description 4
• 230000002537 thrombolytic effect Effects 0.000 claims description 4
• 238000002054 transplantation Methods 0.000 claims description 4
• 230000025033 vasoconstriction Effects 0.000 claims description 4
• 230000009385 viral infection Effects 0.000 claims description 4
• VOEWGXCIPLZGJE-UHFFFAOYSA-N 4-(2-chloro-6-nitrophenoxy)benzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1OC1=C(Cl)C=CC=C1[N+]([O-])=O VOEWGXCIPLZGJE-UHFFFAOYSA-N 0.000 claims description 3
• 208000015294 blood coagulation disease Diseases 0.000 claims description 3
• 210000003127 knee Anatomy 0.000 claims description 3
• 230000001052 transient effect Effects 0.000 claims description 3
• 125000005466 alkylenyl group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
• 238000007891 venous angioplasty Methods 0.000 claims 2
• 206010010904 Convulsion Diseases 0.000 claims 1
• 208000009190 disseminated intravascular coagulation Diseases 0.000 claims 1
• 230000000302 ischemic effect Effects 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• 239000002253 acid Substances 0.000 abstract description 34
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract description 14
• 125000004356 hydroxy functional group Chemical group O* 0.000 abstract description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
• 125000005945 imidazopyridyl group Chemical group 0.000 abstract description 3
• XETFBTXVGCQYBD-UHFFFAOYSA-N methanamine;2,2,2-trifluoroacetic acid Chemical compound [NH3+]C.[O-]C(=O)C(F)(F)F XETFBTXVGCQYBD-UHFFFAOYSA-N 0.000 abstract description 2
• BSXLLFUSNQCWJP-UHFFFAOYSA-N thiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CS1 BSXLLFUSNQCWJP-UHFFFAOYSA-N 0.000 abstract description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
• 125000001475 halogen functional group Chemical group 0.000 abstract 3
• IJZYUSAXPDDIKX-HNNXBMFYSA-N 6-chloro-n-[(3s)-1-(furo[3,2-b]pyridin-2-ylmethyl)-2-oxopyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide Chemical compound C1=CC=C2OC(CN3CC[C@@H](C3=O)NS(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC2=N1 IJZYUSAXPDDIKX-HNNXBMFYSA-N 0.000 abstract 2
• CVQMJHHVBFGTFG-BQAIUKQQSA-N n-[(3s)-1-[(1,6-diaminoisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=CC=C2C=C(N)C(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC2=C1N CVQMJHHVBFGTFG-BQAIUKQQSA-N 0.000 abstract 2
• VFHQLCGAUYJSRP-FERBBOLQSA-N n-[(3s)-1-[(1-aminoisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2SC(S(=O)(=O)N[C@H]3CCN(C3=O)CC3=CC=C4C=CN=C(C4=C3)N)=CC2=C1 VFHQLCGAUYJSRP-FERBBOLQSA-N 0.000 abstract 2
• RROZPQBCANKSJH-GXKRWWSZSA-N (3S)-1-[(1-aminoisoquinolin-7-yl)methyl]-3-(methylamino)pyrrolidin-2-one 7-methoxynaphthalene-2-sulfonic acid 2,2,2-trifluoroacetic acid Chemical compound CN[C@@H](CCN1CC2=CC=C(C=CN=C3N)C3=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1.OC(C(F)(F)F)=O RROZPQBCANKSJH-GXKRWWSZSA-N 0.000 abstract 1
• UVZYXTNMWPQUNE-LTCKWSDVSA-N (3S)-1-[(4-aminoquinazolin-6-yl)methyl]-3-(methylamino)pyrrolidin-2-one 7-methoxynaphthalene-2-sulfonic acid 2,2,2-trifluoroacetic acid Chemical compound CN[C@@H](CCN1CC(C=C23)=CC=C2N=CN=C3N)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1.OC(C(F)(F)F)=O UVZYXTNMWPQUNE-LTCKWSDVSA-N 0.000 abstract 1
• BNTNYSKQEQVEPH-MERQFXBCSA-N (3S)-3-amino-1-[(1,6-diaminoisoquinolin-7-yl)methyl]pyrrolidin-2-one 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1[C@@H](N)CCN1CC1=CC2=C(N)N=CC=C2C=C1N BNTNYSKQEQVEPH-MERQFXBCSA-N 0.000 abstract 1
• OTCPLQIYKUTZNU-VIFPVBQESA-N (3S)-3-amino-1-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]pyrrolidin-2-one Chemical compound O=C1[C@@H](N)CCN1CC1=CC2=C(Cl)N=CC=C2N1 OTCPLQIYKUTZNU-VIFPVBQESA-N 0.000 abstract 1
• CIBPKAOKXZTANN-UTONKHPSSA-N (3r)-3-amino-1-[(1-aminoisoquinolin-7-yl)methyl]pyrrolidin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1[C@H](N)CCN1CC1=CC=C(C=CN=C2N)C2=C1 CIBPKAOKXZTANN-UTONKHPSSA-N 0.000 abstract 1
• ZGIAFQOCODFJFG-FERBBOLQSA-N 6-chloro-n-[(3s)-1-[(1,6-diaminoisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C2SC(S(=O)(=O)N[C@H]3CCN(C3=O)CC3=CC4=C(N)N=CC=C4C=C3N)=CC2=C1 ZGIAFQOCODFJFG-FERBBOLQSA-N 0.000 abstract 1
• NILRJQHBKCPZCU-FYZYNONXSA-N 6-chloro-n-[(3s)-2-oxo-1-(1,2,3,4-tetrahydroisoquinolin-7-ylmethyl)pyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CNCC2=CC(CN3CC[C@@H](C3=O)NS(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC=C21 NILRJQHBKCPZCU-FYZYNONXSA-N 0.000 abstract 1
• CVXWDCVOOXTCIJ-INIZCTEOSA-N 6-chloro-n-[(3s)-2-oxo-1-(1h-pyrrolo[2,3-c]pyridin-2-ylmethyl)pyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide Chemical compound C1=NC=C2NC(CN3CC[C@@H](C3=O)NS(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC2=C1 CVXWDCVOOXTCIJ-INIZCTEOSA-N 0.000 abstract 1
• MOPNSDIFLDWQAX-NTISSMGPSA-N 6-chloro-n-[(3s)-2-oxo-1-(1h-pyrrolo[3,2-b]pyridin-2-ylmethyl)pyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2NC(CN3CC[C@@H](C3=O)NS(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC2=N1 MOPNSDIFLDWQAX-NTISSMGPSA-N 0.000 abstract 1
• GHJCYBFDKTZELP-KRWDZBQOSA-N 6-chloro-n-[(3s)-2-oxo-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)pyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide Chemical compound N1=CC=C2NC(CN3CC[C@@H](C3=O)NS(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC2=C1 GHJCYBFDKTZELP-KRWDZBQOSA-N 0.000 abstract 1
• WFPXVTGXHWCEQC-JIDHJSLPSA-N 7-methoxy-n-[(3s)-1-[(6-methoxyisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=CC=C2C=C(OC)C(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC2=C1 WFPXVTGXHWCEQC-JIDHJSLPSA-N 0.000 abstract 1
• GNSUPVVLHBGDAU-QHCPKHFHSA-N 7-methoxy-n-[(3s)-2-oxo-1-[(2-oxo-1h-quinolin-6-yl)methyl]pyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound N1=C(O)C=CC2=CC(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC=C21 GNSUPVVLHBGDAU-QHCPKHFHSA-N 0.000 abstract 1
• VARXSWARIPTRNM-BDQAORGHSA-N 7-methoxy-n-[(3s)-2-oxo-1-[(7-oxo-6h-thieno[2,3-c]pyridin-3-yl)methyl]pyrrolidin-3-yl]naphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CNC(=O)C2=C1C(CN1CC[C@@H](C1=O)NS(=O)(=O)C=1C=CC3=CC=C(C=C3C=1)OC)=CS2 VARXSWARIPTRNM-BDQAORGHSA-N 0.000 abstract 1
• GRZHOJRWTBYXAL-UHFFFAOYSA-N 7-methoxy-n-[2-oxo-1-[(1-oxo-2h-isoquinolin-7-yl)methyl]pyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound C1=CN=C(O)C2=CC(CN3CCC(C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC=C21 GRZHOJRWTBYXAL-UHFFFAOYSA-N 0.000 abstract 1
• RROZPQBCANKSJH-UHFFFAOYSA-N CNC(CCN1CC2=CC=C(C=CN=C3N)C3=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1.OC(C(F)(F)F)=O Chemical compound CNC(CCN1CC2=CC=C(C=CN=C3N)C3=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1.OC(C(F)(F)F)=O RROZPQBCANKSJH-UHFFFAOYSA-N 0.000 abstract 1
• DRNPKIQESPNKGA-GXKRWWSZSA-N CN[C@@H](CCN1CC2=C(C=CC(N)=N3)C3=CC=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1.OC(C(F)(F)F)=O Chemical compound CN[C@@H](CCN1CC2=C(C=CC(N)=N3)C3=CC=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1.OC(C(F)(F)F)=O DRNPKIQESPNKGA-GXKRWWSZSA-N 0.000 abstract 1
• ZCCRHCDYAANSFJ-ZOWNYOTGSA-N CN[C@@H](CCN1CC2=C(C=CC(N3)=O)C3=CC=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1 Chemical compound CN[C@@H](CCN1CC2=C(C=CC(N3)=O)C3=CC=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1 ZCCRHCDYAANSFJ-ZOWNYOTGSA-N 0.000 abstract 1
• QRLWSPQPIGZLRE-YDALLXLXSA-N CN[C@@H](CCN1CC2=CC=C(C=CC(O)=N3)C3=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1 Chemical compound CN[C@@H](CCN1CC2=CC=C(C=CC(O)=N3)C3=C2)C1=O.COC1=CC=C(C=CC(S(O)(=O)=O)=C2)C2=C1 QRLWSPQPIGZLRE-YDALLXLXSA-N 0.000 abstract 1
• PQWZYILSDOWAHR-UHFFFAOYSA-N FC(C(=O)O)(F)F.OC1=NC=CC2=C1C(=CS2)CN2C(C(CC2)NS(=O)(=O)C2=CC1=CC(=CC=C1C=C2)OC)=O Chemical compound FC(C(=O)O)(F)F.OC1=NC=CC2=C1C(=CS2)CN2C(C(CC2)NS(=O)(=O)C2=CC1=CC(=CC=C1C=C2)OC)=O PQWZYILSDOWAHR-UHFFFAOYSA-N 0.000 abstract 1
• 150000001204 N-oxides Chemical class 0.000 abstract 1
• XQYHQVFBDDWDCG-GNAFDRTKSA-N n-[(3r)-1-[(1-aminoisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CN=C(N)C2=CC(CN3CC[C@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC=C21 XQYHQVFBDDWDCG-GNAFDRTKSA-N 0.000 abstract 1
• MGBXCZRURZLLGG-BOXHHOBZSA-N n-[(3s)-1-(3h-benzimidazol-5-ylmethyl)-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C2NC=NC2=CC(CN2CC[C@@H](C2=O)NS(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)=C1 MGBXCZRURZLLGG-BOXHHOBZSA-N 0.000 abstract 1
• TUWQORIPUKBVMN-FYZYNONXSA-N n-[(3s)-1-(3h-imidazo[4,5-c]pyridin-2-ylmethyl)-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=CC=C2NC(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=NC2=C1 TUWQORIPUKBVMN-FYZYNONXSA-N 0.000 abstract 1
• ZZZUISYRHBESAT-FTBISJDPSA-N n-[(3s)-1-[(1-amino-6-methoxyisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-4-(2-chloro-6-nitrophenoxy)benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N([C@H]1CCN(C1=O)CC1=CC2=C(N)N=CC=C2C=C1OC)S(=O)(=O)C(C=C1)=CC=C1OC1=C(Cl)C=CC=C1[N+]([O-])=O ZZZUISYRHBESAT-FTBISJDPSA-N 0.000 abstract 1
• HZBSKFFTPFUHBU-BQAIUKQQSA-N n-[(3s)-1-[(1-amino-6-methoxyisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;hydrochloride Chemical compound Cl.N1=CC=C2C=C(OC)C(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC2=C1N HZBSKFFTPFUHBU-BQAIUKQQSA-N 0.000 abstract 1
• QXZJWEUMMUCXEH-FERBBOLQSA-N n-[(3s)-1-[(1-aminoisoquinolin-6-yl)methyl]-2-oxopyrrolidin-3-yl]-6-chloro-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C2SC(S(=O)(=O)N[C@H]3CCN(C3=O)CC=3C=C4C=CN=C(C4=CC=3)N)=CC2=C1 QXZJWEUMMUCXEH-FERBBOLQSA-N 0.000 abstract 1
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• CDIMXWPYBBXLPZ-FYZYNONXSA-N n-[(3s)-1-[(1-aminoisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-5-pyridin-4-ylthiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N([C@H]1CCN(C1=O)CC1=CC=C2C=CN=C(C2=C1)N)S(=O)(=O)C(S1)=CC=C1C1=CC=NC=C1 CDIMXWPYBBXLPZ-FYZYNONXSA-N 0.000 abstract 1
• WNQJRFJOLDUOFH-FERBBOLQSA-N n-[(3s)-1-[(1-aminoisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-6-chloro-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C2SC(S(=O)(=O)N[C@H]3CCN(C3=O)CC3=CC=C4C=CN=C(C4=C3)N)=CC2=C1 WNQJRFJOLDUOFH-FERBBOLQSA-N 0.000 abstract 1
• XQYHQVFBDDWDCG-BQAIUKQQSA-N n-[(3s)-1-[(1-aminoisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CN=C(N)C2=CC(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC=C21 XQYHQVFBDDWDCG-BQAIUKQQSA-N 0.000 abstract 1
• DTFIQFNBTJDSPN-BQAIUKQQSA-N n-[(3s)-1-[(2-aminoquinolin-5-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC1=CC=C2C(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC=CC2=N1 DTFIQFNBTJDSPN-BQAIUKQQSA-N 0.000 abstract 1
• QTMHKYIZBVUMKD-QHCPKHFHSA-N n-[(3s)-1-[(2-aminoquinolin-6-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide Chemical compound N1=C(N)C=CC2=CC(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC=C21 QTMHKYIZBVUMKD-QHCPKHFHSA-N 0.000 abstract 1
• QFZAMTBGXXFFQX-LMOVPXPDSA-N n-[(3s)-1-[(2-aminoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2SC(S(=O)(=O)N[C@H]3CCN(C3=O)CC=3C=CC4=CC=C(N=C4C=3)N)=CC2=C1 QFZAMTBGXXFFQX-LMOVPXPDSA-N 0.000 abstract 1
• SEYWMQRAUGNBSI-LMOVPXPDSA-N n-[(3s)-1-[(2-aminoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-6-chloro-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C2SC(S(=O)(=O)N[C@H]3CCN(C3=O)CC=3C=CC4=CC=C(N=C4C=3)N)=CC2=C1 SEYWMQRAUGNBSI-LMOVPXPDSA-N 0.000 abstract 1
• MMPKCFIXJKMLPC-FTBISJDPSA-N n-[(3s)-1-[(2-aminoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(N)=NC2=CC(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC=C21 MMPKCFIXJKMLPC-FTBISJDPSA-N 0.000 abstract 1
• KHZHBQZHEIZBHY-FYZYNONXSA-N n-[(3s)-1-[(4-aminoquinolin-6-yl)methyl]-2-oxopyrrolidin-3-yl]-1-benzothiophene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2SC(S(=O)(=O)N[C@H]3CCN(C3=O)CC3=CC=C4N=CC=C(C4=C3)N)=CC2=C1 KHZHBQZHEIZBHY-FYZYNONXSA-N 0.000 abstract 1
• CEPIVQSUYSIUSV-FYZYNONXSA-N n-[(3s)-1-[(4-aminothieno[2,3-d]pyrimidin-6-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=CN=C2SC(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC2=C1N CEPIVQSUYSIUSV-FYZYNONXSA-N 0.000 abstract 1
• SMPKINISDMQAPG-BDQAORGHSA-N n-[(3s)-1-[(7-aminothieno[2,3-c]pyridin-3-yl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=CC=C2C(CN3CC[C@@H](C3=O)NS(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CSC2=C1N SMPKINISDMQAPG-BDQAORGHSA-N 0.000 abstract 1
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