SK160697A3 - Substituted derivatives of (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino)-n- -[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds - Google Patents
Substituted derivatives of (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino)-n- -[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds Download PDFInfo
- Publication number
- SK160697A3 SK160697A3 SK1606-97A SK160697A SK160697A3 SK 160697 A3 SK160697 A3 SK 160697A3 SK 160697 A SK160697 A SK 160697A SK 160697 A3 SK160697 A3 SK 160697A3
- Authority
- SK
- Slovakia
- Prior art keywords
- trifluoroacetic acid
- oxopyrrolidin
- acid salt
- aminoiminomethyl
- benzyl
- Prior art date
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- -1 sulfinylamino Chemical group 0.000 title claims description 585
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title description 2
- 125000003884 phenylalkyl group Chemical group 0.000 title 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 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 claims abstract description 613
- 230000000694 effects Effects 0.000 claims abstract description 8
- 230000004962 physiological condition Effects 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 816
- 229910052739 hydrogen Inorganic materials 0.000 claims description 197
- 238000000034 method Methods 0.000 claims description 152
- 229910052799 carbon Inorganic materials 0.000 claims description 136
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 96
- 229910052757 nitrogen Inorganic materials 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 83
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 82
- 239000002253 acid Substances 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
- 150000002431 hydrogen Chemical group 0.000 claims description 43
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 8
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 claims description 7
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 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 6
- 239000003146 anticoagulant agent Substances 0.000 claims description 6
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- JLTUANWNGKWRQO-UHFFFAOYSA-N 5-chloro-3-methyl-1-benzothiophene-2-sulfonyl chloride Chemical group C1=C(Cl)C=C2C(C)=C(S(Cl)(=O)=O)SC2=C1 JLTUANWNGKWRQO-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 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
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 230000002792 vascular Effects 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 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
- HKCOOJZUUOHZDF-SFHVURJKSA-N 5-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide Chemical compound C([C@@H](C1=O)NS(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)CN1CC1=CC=C(C(N)=N)S1 HKCOOJZUUOHZDF-SFHVURJKSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 206010000891 acute myocardial infarction Diseases 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 210000003127 knee Anatomy 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- QSELGEUCFNFITD-UHFFFAOYSA-N thiophene-2-carboximidamide Chemical compound NC(=N)C1=CC=CS1 QSELGEUCFNFITD-UHFFFAOYSA-N 0.000 claims description 3
- 210000005166 vasculature Anatomy 0.000 claims description 3
- 210000003462 vein Anatomy 0.000 claims description 3
- WEPXLRANFJEOFZ-UHFFFAOYSA-N 2,3,4-trifluorobenzoic acid Chemical class OC(=O)C1=CC=C(F)C(F)=C1F WEPXLRANFJEOFZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- QYBYIJVOSNTBCB-NRFANRHFSA-N 3-amino-5-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]benzenecarboximidamide Chemical compound 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 QYBYIJVOSNTBCB-NRFANRHFSA-N 0.000 claims description 2
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
- 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 claims description 2
- YRDOJWMRCBPRCU-RMRYJAPISA-N 4-[[(3s)-3-[(6-aminonaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide;dihydrochloride Chemical compound Cl.Cl.S1C(C(=N)N)=CC(CN2C([C@@H](NS(=O)(=O)C=3C=C4C=CC(N)=CC4=CC=3)CC2)=O)=C1 YRDOJWMRCBPRCU-RMRYJAPISA-N 0.000 claims description 2
- UPAPPWMUBINJHX-IBGZPJMESA-N 4-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]methyl]pyridine-2-carboximidamide Chemical compound C([C@@H](C1=O)NS(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)CN1CC1=CC=NC(C(N)=N)=C1 UPAPPWMUBINJHX-IBGZPJMESA-N 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- MOJHPDSIDALHOG-IBGZPJMESA-N C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N[C@@H]1C(=O)N(CC=2C(=CC=C(C=2)C(N)=N)N)CC1 Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N[C@@H]1C(=O)N(CC=2C(=CC=C(C=2)C(N)=N)N)CC1 MOJHPDSIDALHOG-IBGZPJMESA-N 0.000 claims description 2
- AIYQGDIDZBAGCM-MHZLTWQESA-N 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)CC1=CC=CC=C1 Chemical compound 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)CC1=CC=CC=C1 AIYQGDIDZBAGCM-MHZLTWQESA-N 0.000 claims description 2
- 206010053567 Coagulopathies Diseases 0.000 claims description 2
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- 210000005249 arterial vasculature Anatomy 0.000 claims description 2
- 210000001367 artery Anatomy 0.000 claims description 2
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
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- 150000004677 hydrates Chemical class 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 230000002035 prolonged effect Effects 0.000 claims description 2
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- 239000012453 solvate Substances 0.000 claims description 2
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- 230000002537 thrombolytic effect Effects 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims 2
- WOHFPZCMATXVRV-DEOSSOPVSA-N 4-[[(3s)-3-[(7-aminonaphthalen-2-yl)sulfonyl-benzylamino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide Chemical compound S1C(C(=N)N)=CC(CN2C([C@@H](N(CC=3C=CC=CC=3)S(=O)(=O)C=3C=C4C=C(N)C=CC4=CC=3)CC2)=O)=C1 WOHFPZCMATXVRV-DEOSSOPVSA-N 0.000 claims 1
- YQYYTNCSSDRJHZ-IBGZPJMESA-N 4-[[(3s)-3-[(7-methoxynaphthalen-2-yl)sulfonyl-methylamino]-2-oxopyrrolidin-1-yl]methyl]thiophene-2-carboximidamide Chemical compound C([C@@H](C1=O)N(C)S(=O)(=O)C=2C=CC3=CC=C(C=C3C=2)OC)CN1CC1=CSC(C(N)=N)=C1 YQYYTNCSSDRJHZ-IBGZPJMESA-N 0.000 claims 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical class OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims 1
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- 206010022562 Intermittent claudication Diseases 0.000 claims 1
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- 230000001575 pathological effect Effects 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- JKCKRNYECSTMLV-UHFFFAOYSA-N thiophene-3-carboximidamide Chemical compound NC(=N)C=1C=CSC=1 JKCKRNYECSTMLV-UHFFFAOYSA-N 0.000 claims 1
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- BWMPXGBHGZIGFJ-PPHPATTJSA-N 3-[[(3s)-3-amino-2,5-dioxopyrrolidin-1-yl]methyl]benzonitrile;hydrochloride Chemical compound Cl.O=C1[C@@H](N)CC(=O)N1CC1=CC=CC(C#N)=C1 BWMPXGBHGZIGFJ-PPHPATTJSA-N 0.000 description 2
- FTODNVYPDPSLQM-ZOWNYOTGSA-N 3-[[(3s)-3-amino-2-oxoazepan-1-yl]methyl]benzonitrile;hydrochloride Chemical compound Cl.O=C1[C@@H](N)CCCCN1CC1=CC=CC(C#N)=C1 FTODNVYPDPSLQM-ZOWNYOTGSA-N 0.000 description 2
- BDAQHLRPAUPBNA-UHFFFAOYSA-N 3-fluoro-4-phenylbenzenesulfonyl chloride Chemical compound FC1=CC(S(Cl)(=O)=O)=CC=C1C1=CC=CC=C1 BDAQHLRPAUPBNA-UHFFFAOYSA-N 0.000 description 2
- XLFSJIGVCSPHDH-UHFFFAOYSA-N 4-(1-methylimidazol-2-yl)benzenesulfonyl chloride Chemical compound CN1C=CN=C1C1=CC=C(S(Cl)(=O)=O)C=C1 XLFSJIGVCSPHDH-UHFFFAOYSA-N 0.000 description 2
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- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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)
- 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 (1)
| Publication Number | Publication Date |
|---|---|
| SK160697A3 true SK160697A3 (en) | 1998-11-04 |
Family
ID=23910281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1606-97A SK160697A3 (en) | 1995-06-07 | 1996-06-07 | Substituted derivatives of (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) |
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| 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 |
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| DE69833036T2 (de) | 1997-09-30 | 2006-06-22 | Daiichi Pharmaceutical Co., Ltd. | Sulfonylderivate |
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| 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 |
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| 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 |
| EP1150979A1 (en) * | 1999-02-09 | 2001-11-07 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines as protease inhibitors |
| DE19909237A1 (de) * | 1999-03-03 | 2000-09-07 | Merck Patent Gmbh | Pyrazol-3-on-derivate |
| US6794412B1 (en) * | 1999-03-11 | 2004-09-21 | Bristol-Myers Squibb Pharma Company | Treatment of thrombosis by combined use of a factor Xa inhibitor and aspirin |
| US6586617B1 (en) * | 1999-04-28 | 2003-07-01 | Sumitomo Chemical Takeda Agro Company, Limited | Sulfonamide derivatives |
| JP2001026506A (ja) * | 1999-04-28 | 2001-01-30 | Takeda Chem Ind Ltd | スルホンアミド誘導体 |
| AU5566300A (en) | 1999-06-22 | 2001-01-09 | Takeda Chemical Industries Ltd. | Acylhydrazine derivatives, process for preparing the same and use thereof |
| EP1208097B1 (en) * | 1999-07-28 | 2009-02-18 | Aventis Pharmaceuticals Inc. | Substituted oxoazaheterocyclyl compounds |
| US6544981B2 (en) | 2000-06-09 | 2003-04-08 | Bristol-Myers Squibb Company | Lactam inhibitors of factor Xa and method |
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| CN1756756A (zh) * | 2003-03-07 | 2006-04-05 | 先灵公司 | 取代的2-吖丁啶酮化合物、其制剂及其治疗高胆甾醇血症的用途 |
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| AU2004249671A1 (en) | 2003-05-20 | 2004-12-29 | Genentech, Inc. | Benzofuran inhibitors of factor VIIa |
| WO2004113278A2 (en) | 2003-05-20 | 2004-12-29 | Genentech, Inc. | Acylsulfamide inhibitors of factor viia |
| EP1680406A1 (en) * | 2003-10-29 | 2006-07-19 | Elan Pharmaceuticals, 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 |
| ATE517085T1 (de) * | 2004-11-23 | 2011-08-15 | Astrazeneca Ab | Zur behandlung von atemwegserkrankungen geeignete phenoxyessigsäurederivate |
| AU2006244206A1 (en) | 2005-05-10 | 2006-11-16 | Vertex Pharmaceuticals Incorporated | Bicyclic derivatives as modulators of ion channels |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4121947A1 (de) * | 1991-07-03 | 1993-01-07 | Basf Ag | 2-(3-(4-amidino-phenyl))-propionsaeurederivate, ihre herstellung und verwendung |
| AU2869092A (en) * | 1991-10-11 | 1993-05-03 | 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 (en) * | 1993-09-21 | 1995-03-30 | Yamanouchi Pharmaceutical Co., Ltd. | N-(3-pyrrolidinyl)benzamide derivative |
| 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 CN CN96194489A patent/CN1190395A/zh active Pending
- 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
-
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 |
|---|---|
| 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 |
| AP799A (en) | 2000-01-19 |
| 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 |
| JPH11507368A (ja) | 1999-06-29 |
| NO310457B1 (no) | 2001-07-09 |
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