SI20743A - Novi trombinski inhibitorji - Google Patents
Novi trombinski inhibitorji Download PDFInfo
- Publication number
- SI20743A SI20743A SI200000326A SI200000326A SI20743A SI 20743 A SI20743 A SI 20743A SI 200000326 A SI200000326 A SI 200000326A SI 200000326 A SI200000326 A SI 200000326A SI 20743 A SI20743 A SI 20743A
- Authority
- SI
- Slovenia
- Prior art keywords
- formula
- alkyl
- compound
- same meaning
- compounds
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 8
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 8
- 108090000190 Thrombin Proteins 0.000 claims description 7
- 229960004072 thrombin Drugs 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 102000009123 Fibrin Human genes 0.000 claims description 3
- 108010073385 Fibrin Proteins 0.000 claims description 3
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 229950003499 fibrin Drugs 0.000 claims description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
- 229910004373 HOAc Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000011946 reduction process Methods 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- DBGRZURIIFFWFO-UHFFFAOYSA-N tert-butyl hydrazinecarbonyl carbonate Chemical compound CC(C)(C)OC(=O)OC(=O)NN DBGRZURIIFFWFO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 229940122388 Thrombin inhibitor Drugs 0.000 description 5
- ROLZYTOAMYXLMF-UHFFFAOYSA-N amino(benzyl)carbamic acid Chemical class OC(=O)N(N)CC1=CC=CC=C1 ROLZYTOAMYXLMF-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000003868 thrombin inhibitor Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 108010022999 Serine Proteases Proteins 0.000 description 3
- 102000012479 Serine Proteases Human genes 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- -1 benzyl R 11 Chemical compound 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000014508 negative regulation of coagulation Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- MVTHUEOHHHQQKY-QMMMGPOBSA-N (2s)-2-(diaminomethylideneamino)-3-phenylpropanoic acid Chemical class NC(N)=N[C@H](C(O)=O)CC1=CC=CC=C1 MVTHUEOHHHQQKY-QMMMGPOBSA-N 0.000 description 1
- WVNVBGHCMUXODA-LURJTMIESA-N (2s)-2-[amino(pyridin-2-yl)amino]propanoic acid Chemical class OC(=O)[C@H](C)N(N)C1=CC=CC=N1 WVNVBGHCMUXODA-LURJTMIESA-N 0.000 description 1
- BYDKEYCXCIVOOV-JTSKRJEESA-N 2-[[(2s)-4-[[(3s)-1-carbamimidoylpiperidin-3-yl]methylamino]-2-(naphthalen-2-ylsulfonylamino)-4-oxobutanoyl]-cyclopropylamino]acetic acid Chemical compound C1N(C(=N)N)CCC[C@H]1CNC(=O)C[C@@H](C(=O)N(CC(O)=O)C1CC1)NS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 BYDKEYCXCIVOOV-JTSKRJEESA-N 0.000 description 1
- GLPDBPGNFRRABU-UHFFFAOYSA-N 2-methylbenzenecarboximidamide Chemical compound CC1=CC=CC=C1C(N)=N GLPDBPGNFRRABU-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical group CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 206010062506 Heparin-induced thrombocytopenia Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- NTUPOKHATNSWCY-JYJNAYRXSA-N Phe-Pro-Arg Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)C1=CC=CC=C1 NTUPOKHATNSWCY-JYJNAYRXSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 101000712605 Theromyzon tessulatum Theromin Proteins 0.000 description 1
- 208000001435 Thromboembolism Diseases 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- KYJGWEQIDCBJRT-UHFFFAOYSA-N [3-[[(4-methylpiperidine-1-carbonyl)-(naphthalen-2-ylsulfonylamino)amino]methyl]benzenecarboximidoyl]azanium;chloride Chemical compound [Cl-].C1CC(C)CCN1C(=O)N(NS(=O)(=O)C=1C=C2C=CC=CC2=CC=1)CC1=CC=CC(C([NH3+])=N)=C1 KYJGWEQIDCBJRT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000011360 adjunctive therapy Methods 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 238000013130 cardiovascular surgery Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 208000009190 disseminated intravascular coagulation Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 230000020764 fibrinolysis Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- UMHCOLAWOWTRTA-UHFFFAOYSA-N n-[(3-cyanophenyl)methyl]-4-methyl-n'-naphthalen-2-ylsulfonylpiperidine-1-carbohydrazide Chemical compound C1CC(C)CCN1C(=O)N(NS(=O)(=O)C=1C=C2C=CC=CC2=CC=1)CC1=CC=CC(C#N)=C1 UMHCOLAWOWTRTA-UHFFFAOYSA-N 0.000 description 1
- MXYXTVOCANUZHW-UHFFFAOYSA-N n-[(3-cyanophenyl)methyl]-4-methylpiperidine-1-carbohydrazide Chemical compound C1CC(C)CCN1C(=O)N(N)CC1=CC=CC(C#N)=C1 MXYXTVOCANUZHW-UHFFFAOYSA-N 0.000 description 1
- 229950005835 napsagatran Drugs 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- QUUYRYYUKNNNNS-UHFFFAOYSA-N piperidine-1-carboximidamide Chemical compound NC(=N)N1CCCCC1 QUUYRYYUKNNNNS-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000013037 reversible inhibitor Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- C07C311/49—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200000326A SI20743A (sl) | 2000-12-22 | 2000-12-22 | Novi trombinski inhibitorji |
| US10/433,358 US7285547B2 (en) | 2000-12-22 | 2001-12-20 | Amidinophenylalanine derivatives as thrombin inhibitors |
| ES01272199T ES2240345T3 (es) | 2000-12-22 | 2001-12-20 | Derivados de amidinofenilalanina como inhibidores de trombina. |
| AT01272199T ATE291016T1 (de) | 2000-12-22 | 2001-12-20 | Amidinophenylalaninderivate als thrombininhibitoren |
| DE60109498T DE60109498T2 (de) | 2000-12-22 | 2001-12-20 | Amidinophenylalaninderivate als thrombininhibitoren |
| PCT/IB2001/002600 WO2002051824A1 (en) | 2000-12-22 | 2001-12-20 | Amidinophenylalanine derivatives as thrombin inhibitors |
| DK01272199T DK1355894T3 (da) | 2000-12-22 | 2001-12-20 | Amidinophenylalaninderivater som thrombininhibitorer |
| EP01272199A EP1355894B1 (en) | 2000-12-22 | 2001-12-20 | Amidinophenylalanine derivatives as thrombin inhibitors |
| PT01272199T PT1355894E (pt) | 2000-12-22 | 2001-12-20 | Derivados de amidinofenilalanina como inibidores de trombina |
| JP2002552919A JP4390453B2 (ja) | 2000-12-22 | 2001-12-20 | トロンビン阻害物質としてのアミジノフェニルアラニン誘導体 |
| US11/854,532 US20080004256A1 (en) | 2000-12-22 | 2007-09-12 | Amidinophenylalanine Derivatives as Thrombin Inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200000326A SI20743A (sl) | 2000-12-22 | 2000-12-22 | Novi trombinski inhibitorji |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI20743A true SI20743A (sl) | 2002-06-30 |
Family
ID=20432799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI200000326A SI20743A (sl) | 2000-12-22 | 2000-12-22 | Novi trombinski inhibitorji |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7285547B2 (enExample) |
| EP (1) | EP1355894B1 (enExample) |
| JP (1) | JP4390453B2 (enExample) |
| AT (1) | ATE291016T1 (enExample) |
| DE (1) | DE60109498T2 (enExample) |
| DK (1) | DK1355894T3 (enExample) |
| ES (1) | ES2240345T3 (enExample) |
| PT (1) | PT1355894E (enExample) |
| SI (1) | SI20743A (enExample) |
| WO (1) | WO2002051824A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0523539D0 (en) * | 2005-11-18 | 2005-12-28 | Lek Tovarna Farmacevtskih | New use of organic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9322976D0 (en) * | 1993-11-08 | 1994-01-05 | Pfizer Ltd | Therapeutic agents |
-
2000
- 2000-12-22 SI SI200000326A patent/SI20743A/sl not_active IP Right Cessation
-
2001
- 2001-12-20 AT AT01272199T patent/ATE291016T1/de active
- 2001-12-20 ES ES01272199T patent/ES2240345T3/es not_active Expired - Lifetime
- 2001-12-20 DE DE60109498T patent/DE60109498T2/de not_active Expired - Lifetime
- 2001-12-20 WO PCT/IB2001/002600 patent/WO2002051824A1/en not_active Ceased
- 2001-12-20 US US10/433,358 patent/US7285547B2/en not_active Expired - Fee Related
- 2001-12-20 JP JP2002552919A patent/JP4390453B2/ja not_active Expired - Fee Related
- 2001-12-20 PT PT01272199T patent/PT1355894E/pt unknown
- 2001-12-20 DK DK01272199T patent/DK1355894T3/da active
- 2001-12-20 EP EP01272199A patent/EP1355894B1/en not_active Expired - Lifetime
-
2007
- 2007-09-12 US US11/854,532 patent/US20080004256A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002051824A1 (en) | 2002-07-04 |
| PT1355894E (pt) | 2005-08-31 |
| US20080004256A1 (en) | 2008-01-03 |
| DK1355894T3 (da) | 2005-07-11 |
| DE60109498T2 (de) | 2006-04-13 |
| ES2240345T3 (es) | 2005-10-16 |
| EP1355894B1 (en) | 2005-03-16 |
| EP1355894A1 (en) | 2003-10-29 |
| JP4390453B2 (ja) | 2009-12-24 |
| DE60109498D1 (en) | 2005-04-21 |
| ATE291016T1 (de) | 2005-04-15 |
| JP2004516317A (ja) | 2004-06-03 |
| US7285547B2 (en) | 2007-10-23 |
| US20040048851A1 (en) | 2004-03-11 |
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