AP799A - Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) N-[(aminoiminomethyl) phenylalkyl]-azaheterocyclylamide compounds. - Google Patents
Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) N-[(aminoiminomethyl) phenylalkyl]-azaheterocyclylamide compounds. Download PDFInfo
- Publication number
- AP799A AP799A APAP/P/1997/001144A AP9701144A AP799A AP 799 A AP799 A AP 799A AP 9701144 A AP9701144 A AP 9701144A AP 799 A AP799 A AP 799A
- Authority
- AP
- ARIPO
- Prior art keywords
- oxopyrrolidin
- aminoiminomethyl
- benzyl
- trifiuoroacetate
- amide
- Prior art date
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- -1 sulfinylamino Chemical group 0.000 title description 66
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title description 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 title description 2
- 125000003884 phenylalkyl group Chemical group 0.000 title 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 37
- 108010074860 Factor Xa Proteins 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 5
- 239000003112 inhibitor Substances 0.000 abstract description 5
- 238000011282 treatment Methods 0.000 abstract description 3
- 230000001668 ameliorated effect Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 230000004962 physiological condition Effects 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 52
- 125000000217 alkyl group Chemical group 0.000 description 35
- 229910052739 hydrogen Inorganic materials 0.000 description 25
- 239000001257 hydrogen Substances 0.000 description 25
- 125000003710 aryl alkyl group Chemical group 0.000 description 20
- 150000002431 hydrogen Chemical group 0.000 description 20
- 150000001408 amides Chemical class 0.000 description 19
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 13
- 125000004475 heteroaralkyl group Chemical group 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 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 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 239000003146 anticoagulant agent Substances 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- HPUKOXOQHIMLHG-MERQFXBCSA-N N[C@@H](CCN1CC2=CC(C=NN)=CC=C2)C1=O.OC(C(F)(F)F)=O Chemical compound N[C@@H](CCN1CC2=CC(C=NN)=CC=C2)C1=O.OC(C(F)(F)F)=O HPUKOXOQHIMLHG-MERQFXBCSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 229940127219 anticoagulant drug Drugs 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 206010051055 Deep vein thrombosis Diseases 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 125000005239 aroylamino group Chemical group 0.000 description 3
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 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 description 2
- GXWGRQOMOLFZDN-UHFFFAOYSA-N 5-chloro-3-methyl-1-benzothiophene-2-sulfonic acid Chemical compound C1=C(Cl)C=C2C(C)=C(S(O)(=O)=O)SC2=C1 GXWGRQOMOLFZDN-UHFFFAOYSA-N 0.000 description 2
- FOIKGWJGRNNGQP-UHFFFAOYSA-N 6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(OC)=CC=C21 FOIKGWJGRNNGQP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 206010000891 acute myocardial infarction Diseases 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229960004072 thrombin Drugs 0.000 description 2
- 230000001732 thrombotic effect Effects 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 210000005166 vasculature Anatomy 0.000 description 2
- HZKJAZKMSIAJRR-UHFFFAOYSA-N 1-(6-methoxypyridin-2-yl)cyclohexa-2,4-diene-1-sulfonic acid Chemical compound COC1=CC=CC(C2(C=CC=CC2)S(O)(=O)=O)=N1 HZKJAZKMSIAJRR-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- SVDZWRPQYYCMGG-UHFFFAOYSA-N 2,4-diaminoquinazoline-6-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=NC(N)=NC(N)=C21 SVDZWRPQYYCMGG-UHFFFAOYSA-N 0.000 description 1
- IXOFKWNMYWVYPS-JMAPEOGHSA-N 2-[[(3s)-1-[(2-carbamimidoylpyridin-4-yl)methyl]-2-oxopyrrolidin-3-yl]-(7-methoxynaphthalen-2-yl)sulfonylamino]-n-(2-phenylethyl)acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=CC(OC)=CC=C2C=CC=1S(=O)(=O)N([C@@H]1C(N(CC=2C=C(N=CC=2)C(N)=N)CC1)=O)CC(=O)NCCC1=CC=CC=C1 IXOFKWNMYWVYPS-JMAPEOGHSA-N 0.000 description 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- PYLYBGPDWHXOMR-SFHVURJKSA-N 3-[[(3S)-2-oxo-3-(2-phenylethenylsulfonylamino)pyrrolidin-1-yl]methyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(CN2C([C@@H](NS(=O)(=O)C=CC=3C=CC=CC=3)CC2)=O)=C1 PYLYBGPDWHXOMR-SFHVURJKSA-N 0.000 description 1
- OIUQBFUDCXVJLM-IBGZPJMESA-N 3-[[(3s)-3-[[4-(1-methylimidazol-2-yl)phenyl]sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]benzenecarboximidamide Chemical compound CN1C=CN=C1C1=CC=C(S(=O)(=O)N[C@@H]2C(N(CC=3C=C(C=CC=3)C(N)=N)CC2)=O)C=C1 OIUQBFUDCXVJLM-IBGZPJMESA-N 0.000 description 1
- SRVMTFXBPLBKQW-FGJQBABTSA-N 3-amino-5-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]benzenecarboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.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(N)=CC(C(N)=N)=C1 SRVMTFXBPLBKQW-FGJQBABTSA-N 0.000 description 1
- FPQOCCYRCZNLEJ-UHFFFAOYSA-N 3-fluoro-4-phenylbenzenesulfonic acid Chemical compound FC1=CC(S(=O)(=O)O)=CC=C1C1=CC=CC=C1 FPQOCCYRCZNLEJ-UHFFFAOYSA-N 0.000 description 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 1
- ADAKMYBJTQFVMB-UHFFFAOYSA-N 4-(3-methylphenyl)benzenesulfonic acid Chemical compound CC1=CC=CC(C=2C=CC(=CC=2)S(O)(=O)=O)=C1 ADAKMYBJTQFVMB-UHFFFAOYSA-N 0.000 description 1
- PRQNUELZKQBHRX-KRWDZBQOSA-N 4-[[(3S)-3-[methylsulfonyl(3-phenylpropyl)amino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide Chemical compound CS(=O)(=O)N([C@@H]1C(N(CC=2C=C(SC=2)C(N)=N)CC1)=O)CCCC1=CC=CC=C1 PRQNUELZKQBHRX-KRWDZBQOSA-N 0.000 description 1
- KTHHXNVRFKTMND-RSAXXLAASA-N 4-[[(3s)-3-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]pyridine-2-carboximidamide;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=NC(C(N)=N)=C1 KTHHXNVRFKTMND-RSAXXLAASA-N 0.000 description 1
- VUMVOECAGYRLJH-UQIIZPHYSA-N 4-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonyl-(thiophen-3-ylmethyl)amino]-2-oxopyrrolidin-1-yl]methyl]pyridine-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=CC(OC)=CC=C2C=CC=1S(=O)(=O)N([C@@H]1C(N(CC=2C=C(N=CC=2)C(N)=N)CC1)=O)CC=1C=CSC=1 VUMVOECAGYRLJH-UQIIZPHYSA-N 0.000 description 1
- DKFBSNLAEFJLHM-BQAIUKQQSA-N 4-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonyl-(thiophen-3-ylmethyl)amino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C2=CC(OC)=CC=C2C=CC=1S(=O)(=O)N([C@@H]1C(N(CC=2C=C(SC=2)C(N)=N)CC1)=O)CC=1C=CSC=1 DKFBSNLAEFJLHM-BQAIUKQQSA-N 0.000 description 1
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- SRRQGYUGZWLNCN-LMOVPXPDSA-N 4-[[(3s)-3-[[4-(2-chloro-6-nitrophenoxy)phenyl]sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.S1C(C(=N)N)=CC(CN2C([C@@H](NS(=O)(=O)C=3C=CC(OC=4C(=CC=CC=4Cl)[N+]([O-])=O)=CC=3)CC2)=O)=C1 SRRQGYUGZWLNCN-LMOVPXPDSA-N 0.000 description 1
- OZVHTTBCBZLULV-VWLOTQADSA-N 4-[[(3s)-3-[benzyl-(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide Chemical compound C=1C2=CC(OC)=CC=C2C=CC=1S(=O)(=O)N([C@@H]1C(N(CC=2C=C(SC=2)C(N)=N)CC1)=O)CC1=CC=CC=C1 OZVHTTBCBZLULV-VWLOTQADSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- NUYLILFFMSAMHM-UHFFFAOYSA-N 4-pyridin-3-ylbenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=CN=C1 NUYLILFFMSAMHM-UHFFFAOYSA-N 0.000 description 1
- LRKJKHNZRCAUSV-UHFFFAOYSA-N 4-pyridin-4-ylbenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1C1=CC=NC=C1 LRKJKHNZRCAUSV-UHFFFAOYSA-N 0.000 description 1
- KKFJNRXJRRYNRJ-VWLOTQADSA-N 5-[[(3s)-3-[benzyl-(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide Chemical compound C=1C2=CC(OC)=CC=C2C=CC=1S(=O)(=O)N([C@@H]1C(N(CC=2SC(=CC=2)C(N)=N)CC1)=O)CC1=CC=CC=C1 KKFJNRXJRRYNRJ-VWLOTQADSA-N 0.000 description 1
- RRELHGZMPGGKMS-UHFFFAOYSA-N 5-chloro-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(Cl)C(OC)=CC=C21 RRELHGZMPGGKMS-UHFFFAOYSA-N 0.000 description 1
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- OKAUOXITMZTUOJ-UHFFFAOYSA-N 7-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OKAUOXITMZTUOJ-UHFFFAOYSA-N 0.000 description 1
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- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 208000021156 intermittent vascular claudication Diseases 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
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- 238000012423 maintenance Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical group COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 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
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- PLUQFBYKHVFHMZ-UHFFFAOYSA-N quinoline-6-sulfonic acid Chemical compound N1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 PLUQFBYKHVFHMZ-UHFFFAOYSA-N 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- QSELGEUCFNFITD-UHFFFAOYSA-N thiophene-2-carboximidamide Chemical compound NC(=N)C1=CC=CS1 QSELGEUCFNFITD-UHFFFAOYSA-N 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000009385 viral infection Effects 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
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- 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)
- Pyrrole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (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 (2)
| Publication Number | Publication Date |
|---|---|
| AP9701144A0 AP9701144A0 (en) | 1998-01-31 |
| AP799A true AP799A (en) | 2000-01-19 |
Family
ID=23910281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1997/001144A AP799A (en) | 1995-06-07 | 1996-06-07 | Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) N-[(aminoiminomethyl) phenylalkyl]-azaheterocyclylamide compounds. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5612353A (enExample) |
| EP (1) | EP0853618B1 (enExample) |
| JP (1) | JP4312829B2 (enExample) |
| KR (1) | KR100291711B1 (enExample) |
| CN (1) | CN1190395A (enExample) |
| AP (1) | AP799A (enExample) |
| AT (1) | ATE520655T1 (enExample) |
| AU (1) | AU714319B2 (enExample) |
| BG (1) | BG63628B1 (enExample) |
| BR (1) | BR9608405A (enExample) |
| CA (1) | CA2223403C (enExample) |
| CZ (1) | CZ385397A3 (enExample) |
| EA (1) | EA000700B1 (enExample) |
| HU (1) | HUP9801882A3 (enExample) |
| MX (1) | MX9709977A (enExample) |
| NO (1) | NO310457B1 (enExample) |
| OA (1) | OA10752A (enExample) |
| PL (1) | PL323780A1 (enExample) |
| SI (1) | SI9620093A (enExample) |
| SK (1) | SK160697A3 (enExample) |
| WO (1) | WO1996040679A1 (enExample) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6034093A (en) * | 1995-06-07 | 2000-03-07 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted sulfonic acid N-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds |
| US5731315A (en) * | 1995-06-07 | 1998-03-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted sulfonic acid n- (aminoiminomethyl)phenylalkyl!-azaheterocyclamide compounds |
| US5958918A (en) * | 1995-06-07 | 1999-09-28 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino) N- (aminominomethyl)phenylalkyl!-azaheterocyclylamide compounds |
| US6080767A (en) * | 1996-01-02 | 2000-06-27 | Aventis Pharmaceuticals Products Inc. | Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides |
| US6057342A (en) * | 1996-08-16 | 2000-05-02 | Dupont Pharmaceutical Co. | Amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof |
| CN1244798A (zh) * | 1996-12-13 | 2000-02-16 | 罗纳·布朗克罗尔药制品有限公司 | 磺酸或磺酰氨基n-(杂芳烷基)-氮杂环酰胺化合物 |
| US6602864B1 (en) * | 1996-12-13 | 2003-08-05 | Aventis Pharma Deutschland Gmbh | Sulfonic acid or sulfonylamino N-(heteroaralkyl)-azaheterocyclylamide compounds |
| EP0986551B1 (en) | 1997-05-30 | 2006-08-02 | Takeda Pharmaceutical Company Limited | Sulfonamide derivatives, their production and use |
| ZA985247B (en) * | 1997-06-19 | 1999-12-17 | Du Pont Merck Pharma | Guanidine mimics as factor Xa inhibitors. |
| DE69833036T2 (de) | 1997-09-30 | 2006-06-22 | Daiichi Pharmaceutical Co., Ltd. | Sulfonylderivate |
| US6271237B1 (en) | 1997-12-22 | 2001-08-07 | Dupont Pharmaceuticals Company | Nitrogen containing heteromatics with ortho-substituted P1s as factor Xa inhabitors |
| CA2314401A1 (en) * | 1997-12-22 | 1999-07-01 | Du Pont Pharmaceuticals Company | Nitrogen containing heteroaromatics with ortho-substituted p1's as factor xa inhibitors |
| UA59433C2 (uk) * | 1998-01-27 | 2003-09-15 | Авентіс Фармасьютікалс Продактс Інк. | ЗАМІЩЕНІ ОКСОАЗАГЕТЕРОЦИКЛІЧНІ ІНГІБІТОРИ ФАКТОРА Хa ТА ПРОМІЖНІ СПОЛУКИ ДЛЯ ЇХ ОТРИМАННЯ |
| CN1290254A (zh) | 1998-02-05 | 2001-04-04 | 武田药品工业株式会社 | 氨磺酰衍生物及其制备和用途 |
| US6291514B1 (en) | 1998-02-09 | 2001-09-18 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines, preparation thereof, and use thereof as protease inhibitors |
| WO1999040088A1 (en) * | 1998-02-09 | 1999-08-12 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines as protease inhibitors, in particular as urokinase inhibitors |
| AU5196399A (en) * | 1998-08-11 | 2000-03-06 | Daiichi Pharmaceutical Co., Ltd. | Novel sulfonyl derivatives |
| DE19839499A1 (de) * | 1998-08-29 | 2000-03-02 | Merck Patent Gmbh | 2-Oxo-2H-chinolinderivate |
| WO2000032590A1 (en) * | 1998-11-25 | 2000-06-08 | Aventis Pharmaceuticals Products Inc. | SUBSTITUTED OXOAZAHETEROCYCLYL FACTOR Xa INHIBITORS |
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- 1996-06-07 SK SK1606-97A patent/SK160697A3/sk unknown
- 1996-06-07 AT AT96919298T patent/ATE520655T1/de not_active IP Right Cessation
- 1996-06-07 AU AU61669/96A patent/AU714319B2/en not_active Ceased
- 1996-06-07 SI SI9620093A patent/SI9620093A/sl unknown
- 1996-06-07 EP EP96919298A patent/EP0853618B1/en not_active Expired - Lifetime
- 1996-06-07 AP APAP/P/1997/001144A patent/AP799A/en active
- 1996-06-07 WO PCT/US1996/009816 patent/WO1996040679A1/en not_active Ceased
- 1996-06-07 BR BR9608405A patent/BR9608405A/pt not_active Application Discontinuation
- 1996-06-07 PL PL96323780A patent/PL323780A1/xx unknown
- 1996-06-07 HU HU9801882A patent/HUP9801882A3/hu unknown
- 1996-06-07 EA EA199800043A patent/EA000700B1/ru not_active IP Right Cessation
- 1996-06-07 CA CA002223403A patent/CA2223403C/en not_active Expired - Fee Related
- 1996-06-07 KR KR1019970708866A patent/KR100291711B1/ko not_active Expired - Fee Related
- 1996-06-07 CZ CZ973853A patent/CZ385397A3/cs unknown
- 1996-06-07 JP JP50202997A patent/JP4312829B2/ja not_active Expired - Fee Related
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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
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1998
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| DE4121947A1 (de) * | 1991-07-03 | 1993-01-07 | Basf Ag | 2-(3-(4-amidino-phenyl))-propionsaeurederivate, ihre herstellung und verwendung |
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Also Published As
| Publication number | Publication date |
|---|---|
| ATE520655T1 (de) | 2011-09-15 |
| NO975762L (no) | 1998-02-06 |
| CN1190395A (zh) | 1998-08-12 |
| EP0853618B1 (en) | 2011-08-17 |
| HUP9801882A2 (hu) | 1998-12-28 |
| EA000700B1 (ru) | 2000-02-28 |
| OA10752A (en) | 2001-07-04 |
| KR100291711B1 (ko) | 2001-09-17 |
| AU6166996A (en) | 1996-12-30 |
| EP0853618A4 (en) | 2000-03-15 |
| HUP9801882A3 (en) | 1999-01-28 |
| WO1996040679A1 (en) | 1996-12-19 |
| US5612353A (en) | 1997-03-18 |
| BR9608405A (pt) | 1999-08-24 |
| BG63628B1 (bg) | 2002-07-31 |
| EP0853618A1 (en) | 1998-07-22 |
| PL323780A1 (en) | 1998-04-27 |
| CA2223403C (en) | 2002-04-23 |
| BG102162A (en) | 1998-09-30 |
| CA2223403A1 (en) | 1996-12-19 |
| NO975762D0 (no) | 1997-12-08 |
| AP9701144A0 (en) | 1998-01-31 |
| MX9709977A (es) | 1998-07-31 |
| JP4312829B2 (ja) | 2009-08-12 |
| EA199800043A1 (ru) | 1998-08-27 |
| CZ385397A3 (cs) | 1999-05-12 |
| SI9620093A (sl) | 1999-02-28 |
| AU714319B2 (en) | 2000-01-06 |
| KR19990022386A (ko) | 1999-03-25 |
| SK160697A3 (en) | 1998-11-04 |
| JPH11507368A (ja) | 1999-06-29 |
| NO310457B1 (no) | 2001-07-09 |
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