SK6862003A3 - Guanidine and amidine derivatives as factor XA inhibitors, process for the preparation thereof, pharmaceutical composition and use thereof - Google Patents
Guanidine and amidine derivatives as factor XA inhibitors, process for the preparation thereof, pharmaceutical composition and use thereof Download PDFInfo
- Publication number
- SK6862003A3 SK6862003A3 SK686-2003A SK6862003A SK6862003A3 SK 6862003 A3 SK6862003 A3 SK 6862003A3 SK 6862003 A SK6862003 A SK 6862003A SK 6862003 A3 SK6862003 A3 SK 6862003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- alkyl
- mono
- unsubstituted
- carbon atoms
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 230000008569 process Effects 0.000 title claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title description 5
- 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 1
- 150000001409 amidines Chemical class 0.000 title 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title 1
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- 125000000217 alkyl group Chemical group 0.000 claims description 130
- -1 amino, hydroxy Chemical group 0.000 claims description 111
- 125000004432 carbon atom Chemical group C* 0.000 claims description 102
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
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- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000012634 fragment Substances 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
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- 125000003277 amino group Chemical group 0.000 claims description 17
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 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 description 2
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- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 108010014806 prothrombinase complex Proteins 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 208000013223 septicemia Diseases 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WANOACLWTJGHKX-UHFFFAOYSA-N tert-butyl (ne)-n-[amino-[4-(aminomethyl)piperidin-1-yl]methylidene]carbamate Chemical compound CC(C)(C)OC(=O)NC(=N)N1CCC(CN)CC1 WANOACLWTJGHKX-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960001322 trypsin Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00126750 | 2000-12-06 | ||
| PCT/EP2001/013874 WO2002046159A1 (en) | 2000-12-06 | 2001-11-28 | Guanidine and amidine derivatives as factor xa inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK6862003A3 true SK6862003A3 (en) | 2004-02-03 |
Family
ID=8170585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK686-2003A SK6862003A3 (en) | 2000-12-06 | 2001-11-28 | Guanidine and amidine derivatives as factor XA inhibitors, process for the preparation thereof, pharmaceutical composition and use thereof |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US20020173656A1 (de) |
| EP (1) | EP1345900B1 (de) |
| JP (1) | JP4274522B2 (de) |
| KR (1) | KR20040015036A (de) |
| CN (1) | CN1479722A (de) |
| AR (1) | AR033684A1 (de) |
| AU (2) | AU3320602A (de) |
| BR (1) | BR0115938A (de) |
| CA (1) | CA2430518C (de) |
| CZ (1) | CZ20031554A3 (de) |
| DE (1) | DE60126143T2 (de) |
| DK (1) | DK1345900T3 (de) |
| EE (1) | EE200300192A (de) |
| ES (1) | ES2278798T3 (de) |
| HR (1) | HRP20030447A2 (de) |
| HU (1) | HUP0302604A3 (de) |
| IL (2) | IL156214A0 (de) |
| MX (1) | MXPA03004848A (de) |
| NO (1) | NO20032489L (de) |
| NZ (1) | NZ526269A (de) |
| PL (1) | PL362320A1 (de) |
| PT (1) | PT1345900E (de) |
| RU (1) | RU2003120070A (de) |
| SK (1) | SK6862003A3 (de) |
| WO (1) | WO2002046159A1 (de) |
| ZA (1) | ZA200303847B (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1703395A (zh) * | 2002-08-09 | 2005-11-30 | 特兰斯泰克制药公司 | 芳基和杂芳基化合物以及调节凝血的方法 |
| US7405210B2 (en) | 2003-05-21 | 2008-07-29 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase |
| US7208601B2 (en) * | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| US7501538B2 (en) | 2003-08-08 | 2009-03-10 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| WO2005014533A2 (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 |
| ATE483708T1 (de) | 2004-03-08 | 2010-10-15 | Prosidion Ltd | Pyrrolopyridin-2-carbonsäurehydrazide als inhibitoren von glykogenphosphorylase |
| ATE424821T1 (de) | 2004-12-02 | 2009-03-15 | Prosidion Ltd | Pyrrolopyridin-2-karbonsäureamide |
| 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 |
| IL272838B2 (en) | 2017-10-06 | 2023-09-01 | Forma Therapeutics Inc | Peptidase-specific ubiquitin inhibition 30 |
| SG11202011299PA (en) | 2018-05-17 | 2020-12-30 | Forma Therapeutics Inc | Fused bicyclic compounds useful as ubiquitin-specific peptidase 30 inhibitors |
| PE20211053A1 (es) | 2018-10-05 | 2021-06-07 | Forma Therapeutics Inc | Inhibicion de la proteasa 30 especifica de la ubiquitina (usp30) |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201303B (de) * | 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. |
| SK286094B6 (sk) * | 1994-04-26 | 2008-03-05 | Aventis Pharmaceuticals Inc. | Zlúčenina špecificky inhibujúca aktivitu faktora Xa, farmaceutická kompozícia s jej obsahom a jej použitie |
| 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 |
| US6417200B1 (en) * | 1997-06-26 | 2002-07-09 | Eli Lilly And Company | Antithrombotic agents |
| BR9909086A (pt) * | 1998-03-23 | 2001-09-04 | Aventis Pharm Prod Inc | Derivados de piperidinila e n-amidinopiperidinila |
| US20020016339A1 (en) * | 1998-03-23 | 2002-02-07 | Klein Scott I. | Piperididinyl and N-amidinopiperidinyl derivatives |
| EP0987274A1 (de) | 1998-09-15 | 2000-03-22 | Hoechst Marion Roussel Deutschland GmbH | Faktor VIIa Inhibitore |
| KR20020047175A (ko) * | 1999-09-17 | 2002-06-21 | 밀레니엄 파머슈티컬스 인코퍼레이티드 | Ｘａ 인자의 억제제 |
-
2001
- 2001-11-28 PL PL01362320A patent/PL362320A1/xx unknown
- 2001-11-28 DK DK01984775T patent/DK1345900T3/da active
- 2001-11-28 WO PCT/EP2001/013874 patent/WO2002046159A1/en active IP Right Grant
- 2001-11-28 MX MXPA03004848A patent/MXPA03004848A/es active IP Right Grant
- 2001-11-28 CA CA2430518A patent/CA2430518C/en not_active Expired - Fee Related
- 2001-11-28 ES ES01984775T patent/ES2278798T3/es not_active Expired - Lifetime
- 2001-11-28 DE DE60126143T patent/DE60126143T2/de not_active Expired - Lifetime
- 2001-11-28 BR BR0115938-0A patent/BR0115938A/pt not_active Application Discontinuation
- 2001-11-28 KR KR10-2003-7007612A patent/KR20040015036A/ko not_active Application Discontinuation
- 2001-11-28 AU AU3320602A patent/AU3320602A/xx active Pending
- 2001-11-28 CZ CZ20031554A patent/CZ20031554A3/cs unknown
- 2001-11-28 JP JP2002547898A patent/JP4274522B2/ja not_active Expired - Fee Related
- 2001-11-28 RU RU2003120070/04A patent/RU2003120070A/ru not_active Application Discontinuation
- 2001-11-28 NZ NZ526269A patent/NZ526269A/en unknown
- 2001-11-28 PT PT01984775T patent/PT1345900E/pt unknown
- 2001-11-28 AU AU2002233206A patent/AU2002233206B2/en not_active Ceased
- 2001-11-28 HU HU0302604A patent/HUP0302604A3/hu unknown
- 2001-11-28 IL IL15621401A patent/IL156214A0/xx unknown
- 2001-11-28 SK SK686-2003A patent/SK6862003A3/sk unknown
- 2001-11-28 CN CNA018201121A patent/CN1479722A/zh active Pending
- 2001-11-28 EP EP01984775A patent/EP1345900B1/de not_active Expired - Lifetime
- 2001-11-28 EE EEP200300192A patent/EE200300192A/xx unknown
- 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
Also Published As
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