ZA200303847B - Guanidine and amidine derivatives as factor XA inhibitors. - Google Patents
Guanidine and amidine derivatives as factor XA inhibitors. Download PDFInfo
- Publication number
- ZA200303847B ZA200303847B ZA200303847A ZA200303847A ZA200303847B ZA 200303847 B ZA200303847 B ZA 200303847B ZA 200303847 A ZA200303847 A ZA 200303847A ZA 200303847 A ZA200303847 A ZA 200303847A ZA 200303847 B ZA200303847 B ZA 200303847B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- another
- unsubstituted
- mono
- trisubstituted independently
- Prior art date
Links
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title description 4
- 229940123583 Factor Xa inhibitor Drugs 0.000 title description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title description 2
- 150000001409 amidines Chemical class 0.000 title description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 108010074860 Factor Xa Proteins 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 208000007536 Thrombosis Diseases 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000003146 anticoagulant agent Substances 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 230000023555 blood coagulation Effects 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 208000001435 Thromboembolism Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 238000002399 angioplasty Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 230000002537 thrombolytic effect Effects 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 206010000891 acute myocardial infarction Diseases 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 239000012634 fragment Substances 0.000 claims 8
- 125000000524 functional group Chemical group 0.000 claims 3
- 239000002243 precursor Substances 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 230000020764 fibrinolysis Effects 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- 210000003462 vein Anatomy 0.000 claims 2
- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims 1
- 206010002388 Angina unstable Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 206010053567 Coagulopathies Diseases 0.000 claims 1
- 208000005189 Embolism Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000034486 Multi-organ failure Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 208000010378 Pulmonary Embolism Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000032109 Transient ischaemic attack Diseases 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- 206010047249 Venous thrombosis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 230000003187 abdominal effect Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000007887 coronary angioplasty Methods 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 230000028709 inflammatory response Effects 0.000 claims 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 1
- 210000003127 knee Anatomy 0.000 claims 1
- 210000003141 lower extremity Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 229920005990 polystyrene resin Polymers 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 201000010875 transient cerebral ischemia Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000003130 blood coagulation factor inhibitor Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 208000032843 Hemorrhage Diseases 0.000 description 3
- 108090000190 Thrombin Proteins 0.000 description 3
- 108010000499 Thromboplastin Proteins 0.000 description 3
- 102000002262 Thromboplastin Human genes 0.000 description 3
- 208000034158 bleeding Diseases 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 229960004072 thrombin Drugs 0.000 description 3
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 206010003162 Arterial injury Diseases 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 241000282520 Papio Species 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00126750 | 2000-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200303847B true ZA200303847B (en) | 2004-04-15 |
Family
ID=8170585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200303847A ZA200303847B (en) | 2000-12-06 | 2003-05-19 | Guanidine and amidine derivatives as factor XA inhibitors. |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US20020173656A1 (et) |
| EP (1) | EP1345900B1 (et) |
| JP (1) | JP4274522B2 (et) |
| KR (1) | KR20040015036A (et) |
| CN (1) | CN1479722A (et) |
| AR (1) | AR033684A1 (et) |
| AU (2) | AU3320602A (et) |
| BR (1) | BR0115938A (et) |
| CA (1) | CA2430518C (et) |
| CZ (1) | CZ20031554A3 (et) |
| DE (1) | DE60126143T2 (et) |
| DK (1) | DK1345900T3 (et) |
| EE (1) | EE200300192A (et) |
| ES (1) | ES2278798T3 (et) |
| HR (1) | HRP20030447A2 (et) |
| HU (1) | HUP0302604A3 (et) |
| IL (2) | IL156214A0 (et) |
| MX (1) | MXPA03004848A (et) |
| NO (1) | NO20032489L (et) |
| NZ (1) | NZ526269A (et) |
| PL (1) | PL362320A1 (et) |
| PT (1) | PT1345900E (et) |
| RU (1) | RU2003120070A (et) |
| SK (1) | SK6862003A3 (et) |
| WO (1) | WO2002046159A1 (et) |
| ZA (1) | ZA200303847B (et) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004014844A2 (en) * | 2002-08-09 | 2004-02-19 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
| US7405210B2 (en) | 2003-05-21 | 2008-07-29 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase |
| US7459472B2 (en) * | 2003-08-08 | 2008-12-02 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions, and methods of use |
| US7208601B2 (en) * | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| CA2531796A1 (en) * | 2003-08-08 | 2005-02-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions, and methods of use |
| US8603481B2 (en) * | 2003-10-10 | 2013-12-10 | Chugai Seiyaku Kabushiki Kaisha | Therapeutic agents for solid tumors |
| DE602005023965D1 (de) | 2004-03-08 | 2010-11-18 | Prosidion Ltd | Pyrrolopyridin-2-carbonsäurehydrazide als inhibitoren von glykogenphosphorylase |
| WO2006059164A2 (en) | 2004-12-02 | 2006-06-08 | Prosidion Limited | Pyrrolopyridine-2-carboxylic acid amides |
| DE102006048300A1 (de) * | 2006-01-26 | 2007-08-02 | Hellstern, Peter, Prof. Dr.med. | Inhibitoren des Blutgerinnungsfaktors Xa zur Verwendung als Antikoagulans |
| WO2010098866A1 (en) | 2009-02-27 | 2010-09-02 | Supergen, Inc. | Cyclopentathiophene/cyclohexathiophene dna methyltransferase inhibitors |
| US8507640B2 (en) | 2010-08-19 | 2013-08-13 | International Business Machines Corporation | Methods of ring opening polymerization and catalysts therefor |
| JO3407B1 (ar) | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| MA49566A (fr) | 2017-07-11 | 2020-05-20 | Vertex Pharma | Carboxamides utilisés en tant qu'inhibiteurs des canaux sodiques |
| WO2019071073A1 (en) | 2017-10-06 | 2019-04-11 | Forma Therapeutics, Inc. | INHIBITION OF THE SPECIFIC PEPTIDASE OF UBIQUITIN |
| DK3860989T3 (da) | 2018-10-05 | 2023-05-01 | Forma Therapeutics Inc | Kondenserede pyrroliner der fungerer som inhibitorer af ubiquitin-specifik protease 30 (usp30) |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201303B (et) * | 1990-07-05 | 1993-03-01 | Hoffmann La Roche | |
| US5506134A (en) | 1990-10-22 | 1996-04-09 | Corvas International, Inc. | Hypridoma and monoclonal antibody which inhibits blood coagulation tissue factor/factor VIIa complex |
| US5833982A (en) | 1991-02-28 | 1998-11-10 | Zymogenetics, Inc. | Modified factor VII |
| US5788965A (en) | 1991-02-28 | 1998-08-04 | Novo Nordisk A/S | Modified factor VII |
| ES2103181B1 (es) * | 1994-08-01 | 1998-04-01 | Menarini Lab | Amidas naftalenicas con accion antagonista de los leucotrienos. |
| CN1181091C (zh) * | 1994-04-26 | 2004-12-22 | 西莱克泰德公司 | 因子Xa抑制剂 |
| US5792769A (en) * | 1995-09-29 | 1998-08-11 | 3-Dimensional Pharmaceuticals, Inc. | Guanidino protease inhibitors |
| GB9602166D0 (en) * | 1996-02-02 | 1996-04-03 | Zeneca Ltd | Aminoheterocyclic derivatives |
| TW542822B (en) * | 1997-01-17 | 2003-07-21 | Ajinomoto Kk | Benzamidine derivatives |
| EP1007037A4 (en) * | 1997-06-26 | 2004-10-06 | Lilly Co Eli | ANTITHROMBOTIC AGENTS |
| PL344056A1 (en) | 1998-03-23 | 2001-09-24 | Aventis Pharm Prod Inc | Piperididinyl and n-amidinopiperidinyl derivatives |
| US20020016339A1 (en) * | 1998-03-23 | 2002-02-07 | Klein Scott I. | Piperididinyl and N-amidinopiperidinyl derivatives |
| EP0987274A1 (en) | 1998-09-15 | 2000-03-22 | Hoechst Marion Roussel Deutschland GmbH | Factor VIIa Inhibitors |
| CA2385592C (en) * | 1999-09-17 | 2011-01-11 | Bing-Yan Zhu | Benzamides and related inhibitors of factor xa |
-
2001
- 2001-11-28 RU RU2003120070/04A patent/RU2003120070A/ru not_active Application Discontinuation
- 2001-11-28 KR KR10-2003-7007612A patent/KR20040015036A/ko not_active Application Discontinuation
- 2001-11-28 CA CA2430518A patent/CA2430518C/en not_active Expired - Fee Related
- 2001-11-28 AU AU3320602A patent/AU3320602A/xx active Pending
- 2001-11-28 ES ES01984775T patent/ES2278798T3/es not_active Expired - Lifetime
- 2001-11-28 WO PCT/EP2001/013874 patent/WO2002046159A1/en active IP Right Grant
- 2001-11-28 EE EEP200300192A patent/EE200300192A/et unknown
- 2001-11-28 HU HU0302604A patent/HUP0302604A3/hu unknown
- 2001-11-28 EP EP01984775A patent/EP1345900B1/en not_active Expired - Lifetime
- 2001-11-28 MX MXPA03004848A patent/MXPA03004848A/es active IP Right Grant
- 2001-11-28 IL IL15621401A patent/IL156214A0/xx unknown
- 2001-11-28 CN CNA018201121A patent/CN1479722A/zh active Pending
- 2001-11-28 PT PT01984775T patent/PT1345900E/pt unknown
- 2001-11-28 SK SK686-2003A patent/SK6862003A3/sk unknown
- 2001-11-28 NZ NZ526269A patent/NZ526269A/en unknown
- 2001-11-28 JP JP2002547898A patent/JP4274522B2/ja not_active Expired - Fee Related
- 2001-11-28 PL PL01362320A patent/PL362320A1/xx unknown
- 2001-11-28 AU AU2002233206A patent/AU2002233206B2/en not_active Ceased
- 2001-11-28 DE DE60126143T patent/DE60126143T2/de not_active Expired - Lifetime
- 2001-11-28 DK DK01984775T patent/DK1345900T3/da active
- 2001-11-28 CZ CZ20031554A patent/CZ20031554A3/cs unknown
- 2001-11-28 BR BR0115938-0A patent/BR0115938A/pt not_active Application Discontinuation
- 2001-12-04 AR ARP010105642A patent/AR033684A1/es unknown
- 2001-12-06 US US10/004,422 patent/US20020173656A1/en not_active Abandoned
-
2003
- 2003-05-19 ZA ZA200303847A patent/ZA200303847B/en unknown
- 2003-05-29 IL IL156214A patent/IL156214A/en not_active IP Right Cessation
- 2003-06-02 NO NO20032489A patent/NO20032489L/no not_active Application Discontinuation
- 2003-06-04 HR HR20030447A patent/HRP20030447A2/hr not_active Application Discontinuation
-
2004
- 2004-07-07 US US10/886,312 patent/US7435747B2/en not_active Expired - Fee Related
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