NO310457B1 - Substituerte (sulfinsyre, sulfonsyre, sulfonylamino eller sulfinylamino)-N-[(aminoiminometyl)fenylalkyl]azaheterocyklylamidforbindelser - Google Patents
Substituerte (sulfinsyre, sulfonsyre, sulfonylamino eller sulfinylamino)-N-[(aminoiminometyl)fenylalkyl]azaheterocyklylamidforbindelser Download PDFInfo
- Publication number
- NO310457B1 NO310457B1 NO19975762A NO975762A NO310457B1 NO 310457 B1 NO310457 B1 NO 310457B1 NO 19975762 A NO19975762 A NO 19975762A NO 975762 A NO975762 A NO 975762A NO 310457 B1 NO310457 B1 NO 310457B1
- Authority
- NO
- Norway
- Prior art keywords
- aminoiminomethyl
- benzyl
- oxopyrrolidin
- sulfonic acid
- trifluoroacetate
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 663
- -1 sulfinylamino Chemical group 0.000 title claims description 177
- 125000003884 phenylalkyl group Chemical group 0.000 title claims description 6
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 235
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 107
- 150000001408 amides Chemical class 0.000 claims description 73
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 108010074860 Factor Xa Proteins 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- MRQFYDABMZCZLM-CZCBIWLKSA-N FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 Chemical compound FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 MRQFYDABMZCZLM-CZCBIWLKSA-N 0.000 claims description 6
- UMQQZKPPZYVKBT-BDQAORGHSA-N N-[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]quinoline-6-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NN=CC1=CC=CC(CN2C([C@@H](NS(=O)(=O)C=3C=C4C=CC=NC4=CC=3)CC2)=O)=C1 UMQQZKPPZYVKBT-BDQAORGHSA-N 0.000 claims description 6
- NKBSYLJRVLPKJV-FTBISJDPSA-N OC(=O)C(F)(F)F.C([C@@H](C1=O)NS(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)CN1CC1=CC=CC(C=NN)=C1 Chemical compound OC(=O)C(F)(F)F.C([C@@H](C1=O)NS(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)CN1CC1=CC=CC(C=NN)=C1 NKBSYLJRVLPKJV-FTBISJDPSA-N 0.000 claims description 6
- PSMSAULBRKZYPJ-JIDHJSLPSA-N OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N[C@@H]2C(N(CC=3C=C(C=NN)C=CC=3)CC2)=O)=C1 Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N[C@@H]2C(N(CC=3C=C(C=NN)C=CC=3)CC2)=O)=C1 PSMSAULBRKZYPJ-JIDHJSLPSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- MFBILERJKRDWIH-FGJQBABTSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=CC(=CC=C3C=C2)N)=O)C=CC1 Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=CC(=CC=C3C=C2)N)=O)C=CC1 MFBILERJKRDWIH-FGJQBABTSA-N 0.000 claims description 5
- KPSBUCMUVWEHQO-JIDHJSLPSA-N N-[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]-4-(3-methylphenyl)benzenesulfonamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N[C@@H]2C(N(CC=3C=C(C=NN)C=CC=3)CC2)=O)=C1 KPSBUCMUVWEHQO-JIDHJSLPSA-N 0.000 claims description 5
- KOSRXDWVXPMSMD-FERBBOLQSA-N N-[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]-5-pyridin-2-ylthiophene-2-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NN=CC1=CC=CC(CN2C([C@@H](NS(=O)(=O)C=3SC(=CC=3)C=3N=CC=CC=3)CC2)=O)=C1 KOSRXDWVXPMSMD-FERBBOLQSA-N 0.000 claims description 5
- 239000003146 anticoagulant agent Substances 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
- XGVKSGFXYYTXDJ-YNMZEGNTSA-N 2-[[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]-(7-methoxynaphthalen-2-yl)sulfonylamino]-N-(2-phenylethyl)acetamide 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 XGVKSGFXYYTXDJ-YNMZEGNTSA-N 0.000 claims description 4
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 4
- LFIBSJAAXWZLOV-FERBBOLQSA-N 5-chloro-N-[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]-3-methyl-1-benzothiophene-2-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@H](C1=O)NS(=O)(=O)C2=C(C3=CC(Cl)=CC=C3S2)C)CN1CC1=CC=CC(C=NN)=C1 LFIBSJAAXWZLOV-FERBBOLQSA-N 0.000 claims description 4
- FLFRAFPLANTDFS-BDQAORGHSA-N 8-chloro-N-[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]-7-methoxynaphthalene-2-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@H](C1=O)NS(=O)(=O)C=2C=CC3=CC=C(C(=C3C=2)Cl)OC)CN1CC1=CC=CC(C=NN)=C1 FLFRAFPLANTDFS-BDQAORGHSA-N 0.000 claims description 4
- OPPOFRGNBFHSFF-ARIINYJRSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCCC=2C=NC=CC2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCCC=2C=NC=CC2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 OPPOFRGNBFHSFF-ARIINYJRSA-N 0.000 claims description 4
- MPTFFWXYVITTCJ-UQIIZPHYSA-N FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCC)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 Chemical compound FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCC)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 MPTFFWXYVITTCJ-UQIIZPHYSA-N 0.000 claims description 4
- UBYDCDMXHCFYEO-YNMZEGNTSA-N FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC=C(C=C3C=C2)OC)=O)C=CC1 Chemical compound FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC=C(C=C3C=C2)OC)=O)C=CC1 UBYDCDMXHCFYEO-YNMZEGNTSA-N 0.000 claims description 4
- KISOLBMUZFDONM-UCRKPPETSA-N FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCCCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 Chemical compound FC(C(=O)O)(F)F.NN=CC=1C=C(CN2C([C@H](CC2)N(CC(=O)NCCCC2=CC=CC=C2)S(=O)(=O)C2=CC3=CC(=CC=C3C=C2)OC)=O)C=CC1 KISOLBMUZFDONM-UCRKPPETSA-N 0.000 claims description 4
- 241000562429 Jamides Species 0.000 claims description 4
- CBTIAQXKRXXQOQ-JIDHJSLPSA-N N-[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxoazepan-3-yl]-7-methoxynaphthalene-2-sulfonamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C([C@@H](C1=O)NS(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)CCCN1CC1=CC=CC(C=NN)=C1 CBTIAQXKRXXQOQ-JIDHJSLPSA-N 0.000 claims description 4
- HYUZUJGWAXJHHJ-BQAIUKQQSA-N N-[(3S)-1-[(3-methanehydrazonoylphenyl)methyl]-2-oxopyrrolidin-3-yl]-4-phenylbenzenesulfonamide 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NN=CC1=CC=CC(CN2C([C@@H](NS(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)CC2)=O)=C1 HYUZUJGWAXJHHJ-BQAIUKQQSA-N 0.000 claims description 4
- GWDCVMIEISJHES-FTBISJDPSA-N OC(=O)C(F)(F)F.C([C@@H](C1=O)NS(=O)(=O)C2=CC3=CC=C(C=C3C=C2)OC)CN1CC1=CC=CC(C=NN)=C1 Chemical compound OC(=O)C(F)(F)F.C([C@@H](C1=O)NS(=O)(=O)C2=CC3=CC=C(C=C3C=C2)OC)CN1CC1=CC=CC(C=NN)=C1 GWDCVMIEISJHES-FTBISJDPSA-N 0.000 claims description 4
- GOWSSNKUORTWFJ-GTVPGWBMSA-N OC(=O)C(F)(F)F.NN=CC1=CC=CC(CN2C([C@@H](NS(=O)(=O)C3(C=CC=CC3)C=3C=[N+]([O-])C=CC=3)CC2)=O)=C1 Chemical compound OC(=O)C(F)(F)F.NN=CC1=CC=CC(CN2C([C@@H](NS(=O)(=O)C3(C=CC=CC3)C=3C=[N+]([O-])C=CC=3)CC2)=O)=C1 GOWSSNKUORTWFJ-GTVPGWBMSA-N 0.000 claims description 4
- SNKPSXCJWCTAMZ-BDQAORGHSA-N OC(=O)C(F)(F)F.NN=CC1=CC=CC(CN2C([C@@H](NS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)CC2)=O)=C1 Chemical compound OC(=O)C(F)(F)F.NN=CC1=CC=CC(CN2C([C@@H](NS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)CC2)=O)=C1 SNKPSXCJWCTAMZ-BDQAORGHSA-N 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- YFVJOHQIZCJFGM-UHFFFAOYSA-N methyl 2-[4-methanehydrazonoyl-2-[[3-[(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]phenoxy]acetate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC(=O)COC1=CC=C(C=NN)C=C1CN1C(=O)C(NS(=O)(=O)C=2C=C3C=C(OC)C=CC3=CC=2)CC1 YFVJOHQIZCJFGM-UHFFFAOYSA-N 0.000 claims description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940080818 propionamide Drugs 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- DCBBASNUFIWQRY-UHFFFAOYSA-N 2-[4-methanehydrazonoyl-2-[[3-[(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]phenoxy]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=CC(OC)=CC=C2C=CC=1S(=O)(=O)NC(C1=O)CCN1CC1=CC(C=NN)=CC=C1OCC(O)=O DCBBASNUFIWQRY-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- LBRJUBLMIYOGNN-FERBBOLQSA-N 3-[[(3s)-2-oxo-3-(2-phenylethenylsulfonylamino)pyrrolidin-1-yl]methyl]benzenecarboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=N)C1=CC=CC(CN2C([C@@H](NS(=O)(=O)C=CC=3C=CC=CC=3)CC2)=O)=C1 LBRJUBLMIYOGNN-FERBBOLQSA-N 0.000 claims description 3
- KKPUHYNHYFSGJU-FERBBOLQSA-N 3-[[(3s)-2-oxo-3-(2-phenylethylsulfonylamino)pyrrolidin-1-yl]methyl]benzenecarboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=N)C1=CC=CC(CN2C([C@@H](NS(=O)(=O)CCC=3C=CC=CC=3)CC2)=O)=C1 KKPUHYNHYFSGJU-FERBBOLQSA-N 0.000 claims description 3
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
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- XBCAHQUVHHVHHL-UHFFFAOYSA-N naphthalen-2-ylmethanamine Chemical compound C1=CC=CC2=CC(CN)=CC=C21 XBCAHQUVHHVHHL-UHFFFAOYSA-N 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000010101 prophylactic anticoagulation Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 108010014806 prothrombinase complex Proteins 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- XELRMPRLCPFTBH-UHFFFAOYSA-N quinazoline-2,4-diamine Chemical compound C1=CC=CC2=NC(N)=NC(N)=C21 XELRMPRLCPFTBH-UHFFFAOYSA-N 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-M sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- KATWGOIXXDLFBD-UHFFFAOYSA-M sodium;6-methoxynaphthalene-2-sulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C=CC2=CC(OC)=CC=C21 KATWGOIXXDLFBD-UHFFFAOYSA-M 0.000 description 1
- ICTBAYJGWSLZKL-UHFFFAOYSA-M sodium;6-phenylmethoxynaphthalene-2-sulfonate Chemical compound [Na+].C1=CC2=CC(S(=O)(=O)[O-])=CC=C2C=C1OCC1=CC=CC=C1 ICTBAYJGWSLZKL-UHFFFAOYSA-M 0.000 description 1
- OYZSUNZAHSNSJF-UHFFFAOYSA-M sodium;7-ethoxynaphthalene-2-sulfonate Chemical compound [Na+].C1=CC(S([O-])(=O)=O)=CC2=CC(OCC)=CC=C21 OYZSUNZAHSNSJF-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PZYLFTPEOMFQFJ-UHFFFAOYSA-N tert-butyl 3-(bromomethyl)pyrazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CC(CBr)=N1 PZYLFTPEOMFQFJ-UHFFFAOYSA-N 0.000 description 1
- CMIBWIAICVBURI-UHFFFAOYSA-N tert-butyl 3-aminopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)C1 CMIBWIAICVBURI-UHFFFAOYSA-N 0.000 description 1
- NXWNLOCSIIRTNL-INIZCTEOSA-N tert-butyl n-[(3s)-1-[(3-cyanophenyl)methyl]-2-oxoazepan-3-yl]carbamate Chemical compound O=C1[C@@H](NC(=O)OC(C)(C)C)CCCCN1CC1=CC=CC(C#N)=C1 NXWNLOCSIIRTNL-INIZCTEOSA-N 0.000 description 1
- NJMSEXDHKYVLKY-YFKPBYRVSA-N tert-butyl n-[(3s)-2-oxoazetidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CNC1=O NJMSEXDHKYVLKY-YFKPBYRVSA-N 0.000 description 1
- KEVGTZZWRJSZFQ-UHFFFAOYSA-N tert-butyl n-[1-[(5-cyanothiophen-3-yl)methyl]-2-oxopyrrolidin-3-yl]carbamate Chemical compound O=C1C(NC(=O)OC(C)(C)C)CCN1CC1=CSC(C#N)=C1 KEVGTZZWRJSZFQ-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- NLJDBTZLVTWXRG-UHFFFAOYSA-N tert-butylazanium;iodide Chemical compound [I-].CC(C)(C)[NH3+] NLJDBTZLVTWXRG-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/481,024 US5612353A (en) | 1995-06-07 | 1995-06-07 | Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) N-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds |
PCT/US1996/009816 WO1996040679A1 (en) | 1995-06-07 | 1996-06-07 | Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) n-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
NO975762D0 NO975762D0 (no) | 1997-12-08 |
NO975762L NO975762L (no) | 1998-02-06 |
NO310457B1 true NO310457B1 (no) | 2001-07-09 |
Family
ID=23910281
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19975762A NO310457B1 (no) | 1995-06-07 | 1997-12-08 | Substituerte (sulfinsyre, sulfonsyre, sulfonylamino eller sulfinylamino)-N-[(aminoiminometyl)fenylalkyl]azaheterocyklylamidforbindelser |
Country Status (21)
Country | Link |
---|---|
US (1) | US5612353A (hu) |
EP (1) | EP0853618B1 (hu) |
JP (1) | JP4312829B2 (hu) |
KR (1) | KR100291711B1 (hu) |
CN (1) | CN1190395A (hu) |
AP (1) | AP799A (hu) |
AT (1) | ATE520655T1 (hu) |
AU (1) | AU714319B2 (hu) |
BG (1) | BG63628B1 (hu) |
BR (1) | BR9608405A (hu) |
CA (1) | CA2223403C (hu) |
CZ (1) | CZ385397A3 (hu) |
EA (1) | EA000700B1 (hu) |
HU (1) | HUP9801882A3 (hu) |
MX (1) | MX9709977A (hu) |
NO (1) | NO310457B1 (hu) |
OA (1) | OA10752A (hu) |
PL (1) | PL323780A1 (hu) |
SI (1) | SI9620093A (hu) |
SK (1) | SK160697A3 (hu) |
WO (1) | WO1996040679A1 (hu) |
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US20060287254A1 (en) * | 2001-01-26 | 2006-12-21 | Schering Corporation | Use of substituted azetidinone compounds for the treatment of sitosterolemia |
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JP2004518688A (ja) | 2001-01-30 | 2004-06-24 | ブリストル−マイヤーズ スクイブ カンパニー | ファクターXa阻害剤のスルホンアミドラクタムおよびその方法 |
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US7053080B2 (en) * | 2001-09-21 | 2006-05-30 | Schering Corporation | Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors |
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DE10302500A1 (de) | 2003-01-23 | 2004-07-29 | Merck Patent Gmbh | Carbonsäureamidderivate |
ES2318274T3 (es) * | 2003-03-07 | 2009-05-01 | Schering Corporation | Compuestos de azetidinona sustituida, formulaciones y uso de los mismos para el tratamiento de hipercolesterolemia. |
ATE406364T1 (de) * | 2003-03-07 | 2008-09-15 | Schering Corp | Substituierte azetidinon-derivate, deren pharmazeutische formulierungen und deren verwendung zur behandlung von hypercholesterolemia |
US7459442B2 (en) * | 2003-03-07 | 2008-12-02 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
AU2004249671A1 (en) | 2003-05-20 | 2004-12-29 | Genentech, Inc. | Benzofuran inhibitors of factor VIIa |
JP2007505160A (ja) | 2003-05-20 | 2007-03-08 | ジェネンテック・インコーポレーテッド | 第VIIa因子のアシルスルファミド阻害剤 |
NZ547528A (en) * | 2003-10-29 | 2008-11-28 | Elan Pharm Inc | N-substituted benzene sulfonamides |
EP1533298A1 (en) | 2003-11-21 | 2005-05-25 | Newron Pharmaceuticals S.p.A. | 3-aminopyrrolidone derivatives |
TWI396686B (zh) | 2004-05-21 | 2013-05-21 | Takeda Pharmaceutical | 環狀醯胺衍生物、以及其製品和用法 |
JP5208510B2 (ja) * | 2004-11-23 | 2013-06-12 | アストラゼネカ・アクチエボラーグ | 呼吸器疾患の処置に有用なフェノキシ酢酸誘導体 |
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WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
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DE4121947A1 (de) * | 1991-07-03 | 1993-01-07 | Basf Ag | 2-(3-(4-amidino-phenyl))-propionsaeurederivate, ihre herstellung und verwendung |
WO1993007141A1 (en) * | 1991-10-11 | 1993-04-15 | Smithkline Beecham Corporation | Heterocyclic 3-phenylpyrrolidin-2-ones, their preparation and use for the manufacture of a medicament for inhibiting tumor necrosis factor production |
JPH05201971A (ja) * | 1992-01-28 | 1993-08-10 | Hokuriku Seiyaku Co Ltd | 環状アミン含有ベンゼンスルホンアミド誘導体 |
US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
WO1995008533A1 (fr) * | 1993-09-21 | 1995-03-30 | Yamanouchi Pharmaceutical Co., Ltd. | Derive de n-(3-pyrrolidinyl)benzamide |
FR2714378B1 (fr) * | 1993-12-24 | 1996-03-15 | Sanofi Sa | Dérivés de l'indol-2-one substitués en 3 par un groupe azoté, leur préparation, les compositions pharmaceutiques en contenant. |
-
1995
- 1995-06-07 US US08/481,024 patent/US5612353A/en not_active Expired - Lifetime
-
1996
- 1996-06-07 WO PCT/US1996/009816 patent/WO1996040679A1/en not_active Application Discontinuation
- 1996-06-07 AP APAP/P/1997/001144A patent/AP799A/en active
- 1996-06-07 EP EP96919298A patent/EP0853618B1/en not_active Expired - Lifetime
- 1996-06-07 HU HU9801882A patent/HUP9801882A3/hu unknown
- 1996-06-07 CN CN96194489A patent/CN1190395A/zh active Pending
- 1996-06-07 AU AU61669/96A patent/AU714319B2/en not_active Ceased
- 1996-06-07 EA EA199800043A patent/EA000700B1/ru not_active IP Right Cessation
- 1996-06-07 BR BR9608405A patent/BR9608405A/pt not_active Application Discontinuation
- 1996-06-07 AT AT96919298T patent/ATE520655T1/de not_active IP Right Cessation
- 1996-06-07 CZ CZ973853A patent/CZ385397A3/cs unknown
- 1996-06-07 PL PL96323780A patent/PL323780A1/xx unknown
- 1996-06-07 SK SK1606-97A patent/SK160697A3/sk unknown
- 1996-06-07 KR KR1019970708866A patent/KR100291711B1/ko not_active IP Right Cessation
- 1996-06-07 SI SI9620093A patent/SI9620093A/sl unknown
- 1996-06-07 CA CA002223403A patent/CA2223403C/en not_active Expired - Fee Related
- 1996-06-07 JP JP50202997A patent/JP4312829B2/ja not_active Expired - Fee Related
-
1997
- 1997-12-03 OA OA70149A patent/OA10752A/en unknown
- 1997-12-08 NO NO19975762A patent/NO310457B1/no unknown
- 1997-12-08 MX MX9709977A patent/MX9709977A/es not_active IP Right Cessation
-
1998
- 1998-01-06 BG BG102162A patent/BG63628B1/bg unknown
Also Published As
Publication number | Publication date |
---|---|
KR19990022386A (ko) | 1999-03-25 |
NO975762D0 (no) | 1997-12-08 |
HUP9801882A3 (en) | 1999-01-28 |
CZ385397A3 (cs) | 1999-05-12 |
KR100291711B1 (ko) | 2001-09-17 |
NO975762L (no) | 1998-02-06 |
SK160697A3 (en) | 1998-11-04 |
EA199800043A1 (ru) | 1998-08-27 |
JP4312829B2 (ja) | 2009-08-12 |
BG102162A (en) | 1998-09-30 |
CA2223403A1 (en) | 1996-12-19 |
CN1190395A (zh) | 1998-08-12 |
AU6166996A (en) | 1996-12-30 |
AU714319B2 (en) | 2000-01-06 |
PL323780A1 (en) | 1998-04-27 |
MX9709977A (es) | 1998-07-31 |
HUP9801882A2 (hu) | 1998-12-28 |
AP799A (en) | 2000-01-19 |
SI9620093A (sl) | 1999-02-28 |
EP0853618A1 (en) | 1998-07-22 |
WO1996040679A1 (en) | 1996-12-19 |
US5612353A (en) | 1997-03-18 |
EP0853618B1 (en) | 2011-08-17 |
OA10752A (en) | 2001-07-04 |
EA000700B1 (ru) | 2000-02-28 |
JPH11507368A (ja) | 1999-06-29 |
AP9701144A0 (en) | 1998-01-31 |
BR9608405A (pt) | 1999-08-24 |
BG63628B1 (bg) | 2002-07-31 |
ATE520655T1 (de) | 2011-09-15 |
EP0853618A4 (en) | 2000-03-15 |
CA2223403C (en) | 2002-04-23 |
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