CN1025738C - 新肽-醛类化合物的制备方法及其组合物 - Google Patents
新肽-醛类化合物的制备方法及其组合物 Download PDFInfo
- Publication number
- CN1025738C CN1025738C CN85109736A CN85109736A CN1025738C CN 1025738 C CN1025738 C CN 1025738C CN 85109736 A CN85109736 A CN 85109736A CN 85109736 A CN85109736 A CN 85109736A CN 1025738 C CN1025738 C CN 1025738C
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- CN
- China
- Prior art keywords
- arginine
- aldehyde
- phenylalanyl
- prolyl
- carbobenzoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 41
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims abstract description 31
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- ODKSFYDXXFIFQN-UHFFFAOYSA-N Arginine Chemical group OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001711 D-phenylalanine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
- 229940024606 amino acid Drugs 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 14
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 108010016626 Dipeptides Proteins 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 239000004475 Arginine Substances 0.000 claims description 4
- 235000009697 arginine Nutrition 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 235000013372 meat Nutrition 0.000 claims description 2
- 125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 12
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- 125000000217 alkyl group Chemical group 0.000 abstract description 3
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- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 description 1
- 241001490312 Lithops pseudotruncatella Species 0.000 description 1
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- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DGGUIHNRWVRWAR-GMUIIQOCSA-N O.C(=O)(OCC1=CC=CC=C1)NC(NCCC[C@@H](NC(=O)OCC1=CC=CC=C1)C(=O)O)=N Chemical compound O.C(=O)(OCC1=CC=CC=C1)NC(NCCC[C@@H](NC(=O)OCC1=CC=CC=C1)C(=O)O)=N DGGUIHNRWVRWAR-GMUIIQOCSA-N 0.000 description 1
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- 102000001400 Tryptase Human genes 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
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- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
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- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
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- 230000002427 irreversible effect Effects 0.000 description 1
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- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000000405 phenylalanyl group Chemical group 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- 230000017854 proteolysis Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
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- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU4763/84 | 1984-12-21 | ||
| HU844763A HU192646B (en) | 1984-12-21 | 1984-12-21 | Process for preparing new n-alkyl-peptide aldehydes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN85109736A CN85109736A (zh) | 1987-03-18 |
| CN1025738C true CN1025738C (zh) | 1994-08-24 |
Family
ID=10968854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN85109736A Expired - Lifetime CN1025738C (zh) | 1984-12-21 | 1985-12-19 | 新肽-醛类化合物的制备方法及其组合物 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4703036A (enExample) |
| EP (1) | EP0185390B1 (enExample) |
| JP (1) | JPH0680078B2 (enExample) |
| CN (1) | CN1025738C (enExample) |
| AR (1) | AR241710A1 (enExample) |
| AT (1) | ATE68002T1 (enExample) |
| AU (1) | AU585561B2 (enExample) |
| CA (1) | CA1261547A (enExample) |
| DE (1) | DE3584281D1 (enExample) |
| DK (1) | DK171403B1 (enExample) |
| ES (1) | ES8708237A1 (enExample) |
| FI (1) | FI85980C (enExample) |
| GR (1) | GR853121B (enExample) |
| HU (1) | HU192646B (enExample) |
| IL (1) | IL77416A (enExample) |
| PT (1) | PT81746B (enExample) |
| SU (1) | SU1384203A3 (enExample) |
| ZA (1) | ZA859756B (enExample) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH075634B2 (ja) * | 1987-10-30 | 1995-01-25 | 日東紡績株式会社 | トリペプチド類及びこれを含有する抗プラスミン剤 |
| GB2244994B (en) * | 1990-06-12 | 1994-01-19 | Richter Gedeon Vegyeszet | Improved process for the preparation of tripeptide aldehydes |
| IL99527A (en) * | 1990-09-28 | 1997-08-14 | Lilly Co Eli | Tripeptide antithrombotic agents |
| US5430023A (en) * | 1990-09-28 | 1995-07-04 | Eli Lilly And Company | Tripeptide antithrombotic agents |
| EP0503203A1 (en) * | 1991-03-15 | 1992-09-16 | Merrell Dow Pharmaceuticals Inc. | Novel thrombin inhibitors |
| US5391705A (en) * | 1991-03-15 | 1995-02-21 | Merrell Dow Pharmaceuticals Inc. | Polyfluorinated tripeptide thrombin inhibitors |
| CA2071621C (en) * | 1991-06-19 | 1996-08-06 | Ahihiko Hosoda | Aldehyde derivatives |
| CA2075154A1 (en) * | 1991-08-06 | 1993-02-07 | Neelakantan Balasubramanian | Peptide aldehydes as antithrombotic agents |
| US5252566A (en) * | 1991-11-12 | 1993-10-12 | Eli Lilly And Company | Antithrombotic agents |
| US5416093A (en) * | 1991-11-12 | 1995-05-16 | Eli Lilly And Company | Antithrombotic agents |
| CZ333492A3 (en) * | 1991-11-12 | 1993-09-15 | Lilly Co Eli | Dipeptide of l-azetidine-2-carboxylic acids and l-argininaldehyde, process of its preparation and pharmaceutical preparation in which said dipeptide is comprised |
| JPH08501057A (ja) * | 1992-03-04 | 1996-02-06 | ヂョヂセルクタトー インテーゼット カーエフテー | 新規な抗凝結因子ペプチド誘導体及びそれを含有する製薬学的組成物及びその製造方法 |
| IL108031A0 (en) * | 1992-12-22 | 1994-04-12 | Procter & Gamble | Difluoro pentapeptide derivatives and pharmaceutical compositions containing them |
| US5455229A (en) * | 1992-12-23 | 1995-10-03 | Eli Lilly And Company | Method for minimizing and containing ischemic and reperfusion injury |
| US5672582A (en) * | 1993-04-30 | 1997-09-30 | Merck & Co., Inc. | Thrombin inhibitors |
| AU670381B2 (en) * | 1993-04-30 | 1996-07-11 | Merck & Co., Inc. | Thrombin inhibitors |
| SE9301916D0 (sv) * | 1993-06-03 | 1993-06-03 | Ab Astra | New peptides derivatives |
| US6984627B1 (en) | 1993-06-03 | 2006-01-10 | Astrazeneca Ab | Peptide derivatives |
| US5783563A (en) * | 1993-06-03 | 1998-07-21 | Astra Aktiebolag | Method for treatment or prophylaxis of venous thrombosis |
| US5484772A (en) * | 1994-03-04 | 1996-01-16 | Eli Lilly And Company | Antithrombotic agents |
| US5602101A (en) * | 1994-03-04 | 1997-02-11 | Eli Lilly And Company | Antithrombotic agents |
| US5707966A (en) * | 1994-03-04 | 1998-01-13 | Eli Lilly And Company | Antithrombotic agents |
| US5439888A (en) * | 1994-03-04 | 1995-08-08 | Eli Lilly And Company | Antithrombotic agents |
| US5885967A (en) * | 1994-03-04 | 1999-03-23 | Eli Lilly And Company | Antithrombotic agents |
| US5488037A (en) * | 1994-03-04 | 1996-01-30 | Eli Lilly And Company | Antithrombotic agents |
| US5436229A (en) * | 1994-03-04 | 1995-07-25 | Eli Lilly And Company | Bisulfite adducts of arginine aldehydes |
| US5726159A (en) * | 1994-03-04 | 1998-03-10 | Eli Lilly And Company | Antithrombotic agents |
| CA2143533A1 (en) * | 1994-03-04 | 1995-09-05 | Kenneth D. Kurz | Antithrombotic agents |
| US5705487A (en) * | 1994-03-04 | 1998-01-06 | Eli Lilly And Company | Antithrombotic agents |
| ZA951618B (en) * | 1994-03-04 | 1996-08-27 | Lilly Co Eli | Antithrombotic agents |
| DE4421052A1 (de) * | 1994-06-17 | 1995-12-21 | Basf Ag | Neue Thrombininhibitoren, ihre Herstellung und Verwendung |
| DE69525641T2 (de) * | 1994-06-17 | 2002-10-17 | Corvas International, Inc. | Verfahren zur herstellung von peptidyl-argininaldehyden |
| US5514777A (en) * | 1994-06-17 | 1996-05-07 | Corvas International, Inc. | Methods of synthesis of peptidyl argininals |
| SE9404196D0 (sv) * | 1994-12-02 | 1994-12-02 | Astra Ab | New antithrombotic formulation |
| US5696231A (en) * | 1994-12-21 | 1997-12-09 | Corvas International, Inc. | N-substituted glycine derivatives as enzyme inhibitors |
| US6025472A (en) * | 1994-12-21 | 2000-02-15 | Corvas International, Inc. | N-substituted glycine derivatives as enzyme inhibitors |
| CZ245797A3 (cs) * | 1995-02-17 | 1998-06-17 | Basf Aktiengesellschaft | Derivát amidinu dipeptidu jako inhibitor thrombinu |
| US5914319A (en) * | 1995-02-27 | 1999-06-22 | Eli Lilly And Company | Antithrombotic agents |
| US5710130A (en) * | 1995-02-27 | 1998-01-20 | Eli Lilly And Company | Antithrombotic agents |
| SA96170106A (ar) | 1995-07-06 | 2005-12-03 | أسترا أكتيبولاج | مشتقات حامض أميني جديدة |
| US6069232A (en) * | 1995-10-02 | 2000-05-30 | Hoechst Marion Roussel, Inc. | Polyfluoroalkyl tryptophan tripeptide thrombin inhibitors |
| TWI238827B (en) * | 1995-12-21 | 2005-09-01 | Astrazeneca Ab | Prodrugs of thrombin inhibitors |
| DE19549118C2 (de) * | 1995-12-29 | 2000-07-13 | Thomas W Stief | Hämostaseaktivierungs-Inhibitor und Verfahren zum Hemmen der Hämostaseaktivierung in Blut oder anderen biologischen Flüssigkeiten |
| DE19605039A1 (de) | 1996-02-12 | 1997-08-14 | Hoechst Ag | Verfahren zur Herstellung von Oligopeptid-Aldehyden |
| US5739354A (en) * | 1996-03-26 | 1998-04-14 | Hoechst Marion Roussel, Inc. | Process for the preparation of N-methyl-D-phenylalanyl-N- 1- 3- (aminoiminomethyl)amino!propyl!-3,3-difluoro-2-oxohexyl!-L-prolinamide |
| HU222199B1 (hu) * | 1996-06-05 | 2003-05-28 | Gyógyszerkutató Intézet Kft. | Véralvadásgátló hatású peptid-aldehid-származékok és a vegyületeket tartalmazó gyógyszerkészítmények |
| HU224315B1 (hu) * | 1996-06-05 | 2005-07-28 | Gyógyszerkutató Intézet Kft. | Véralvadásgátló hatású peptidil-arginin-aldehid-származékok és a vegyületeket tartalmazó gyógyszerkészítmények |
| SE9602263D0 (sv) | 1996-06-07 | 1996-06-07 | Astra Ab | New amino acid derivatives |
| SE9602646D0 (sv) | 1996-07-04 | 1996-07-04 | Astra Ab | Pharmaceutically-useful compounds |
| US6162783A (en) * | 1996-09-24 | 2000-12-19 | The Procter & Gamble Company | Liquid detergents containing proteolytic enzyme and protease inhibitors |
| US6165966A (en) * | 1996-09-24 | 2000-12-26 | The Procter & Gamble Company | Liquid detergents containing proteolytic enzyme and protease inhibitors |
| JP2000506932A (ja) | 1996-09-24 | 2000-06-06 | ザ、プロクター、エンド、ギャンブル、カンパニー | タンパク質分解酵素およびプロテアーゼインヒビターを含有した液体洗濯洗剤組成物 |
| US5798377A (en) * | 1996-10-21 | 1998-08-25 | Merck & Co., Inc. | Thrombin inhibitors |
| AR013084A1 (es) | 1997-06-19 | 2000-12-13 | Astrazeneca Ab | Derivados de amidino utiles como inhibidores de la trombina, composicion farmaceutica, utilizacion de dichos compuestos para la preparacion demedicamentos y proceso para la preparacion de los compuestos mencionados |
| SE9704543D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Ab | New compounds |
| KR100689923B1 (ko) | 1998-01-26 | 2007-03-09 | 애보트 게엠베하 운트 콤파니 카게 | 트롬빈 억제제 |
| SE9804313D0 (sv) | 1998-12-14 | 1998-12-14 | Astra Ab | New compounds |
| CN1170842C (zh) | 1999-01-13 | 2004-10-13 | 阿斯特拉曾尼卡有限公司 | 新的脒基苄基胺衍生物及其作为凝血酶抑制剂的用途 |
| KR20020004971A (ko) * | 1999-03-16 | 2002-01-16 | 이경하 | 치환 프로린 유도체 및 이들을 함유하고 있는 의약 조성물 |
| SE0001803D0 (sv) | 2000-05-16 | 2000-05-16 | Astrazeneca Ab | New compounds i |
| US6433186B1 (en) | 2000-08-16 | 2002-08-13 | Astrazeneca Ab | Amidino derivatives and their use as thormbin inhibitors |
| US7129233B2 (en) | 2000-12-01 | 2006-10-31 | Astrazeneca Ab | Mandelic acid derivatives and their use as thrombin inhibitors |
| AR035216A1 (es) | 2000-12-01 | 2004-05-05 | Astrazeneca Ab | Derivados de acido mandelico ,derivados farmaceuticamente aceptables, uso de estos derivados para la fabricacion de medicamentos, metodos de tratamiento ,procesos para la preparacion de estos derivados, y compuestos intermediarios |
| US6528503B2 (en) | 2000-12-18 | 2003-03-04 | Merck & Co., Inc. | Thrombin inhibitors |
| WO2002050056A1 (en) | 2000-12-18 | 2002-06-27 | Merck & Co., Inc. | Benzylamine derivatives and their use as thrombin inhibitors |
| JP2005504003A (ja) | 2001-02-09 | 2005-02-10 | メルク エンド カムパニー インコーポレーテッド | トロンビン阻害剤 |
| AR034517A1 (es) * | 2001-06-21 | 2004-02-25 | Astrazeneca Ab | Formulacion farmaceutica |
| NZ531315A (en) * | 2001-08-21 | 2005-08-26 | Ivax Drug Res Inst Ltd | Peptide arginals and methods for treating disseminated intravascular coagulation (DIC) |
| US7084134B2 (en) * | 2002-05-02 | 2006-08-01 | Merk & Co., Inc. | Thrombin inhibitors |
| SE0201659D0 (sv) | 2002-05-31 | 2002-05-31 | Astrazeneca Ab | Modified release pharmaceutical formulation |
| SE0201661D0 (sv) | 2002-05-31 | 2002-05-31 | Astrazeneca Ab | New salts |
| US7781424B2 (en) * | 2003-05-27 | 2010-08-24 | Astrazeneca Ab | Modified release pharmaceutical formulation |
| US7795205B2 (en) | 2004-04-12 | 2010-09-14 | Canyon Pharmaceuticals, Inc. | Methods for effecting regression of tumor mass and size in a metastasized pancreatic tumor |
| TW200827336A (en) | 2006-12-06 | 2008-07-01 | Astrazeneca Ab | New crystalline forms |
| WO2009068926A1 (en) | 2007-11-30 | 2009-06-04 | University Of Debrecen | Use of urokinase type plasminogen activator inhibitors for the treatment of corneal disorders |
| US9085750B2 (en) | 2011-07-01 | 2015-07-21 | Novozymes A/S | Stabilized subtilisin composition |
| US20170121646A1 (en) | 2014-07-03 | 2017-05-04 | Novozymes A/S | Improved Stabilization of Non-Protease Enzyme |
| CN107469379B (zh) * | 2016-06-07 | 2020-03-06 | 中国科学院大连化学物理研究所 | 一种样品中残留水溶性有机溶剂的去除方法 |
| MX2021015894A (es) | 2019-07-01 | 2022-02-03 | Basf Se | Peptidos acetales para estabilizar enzimas. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU177098B (en) * | 1979-01-04 | 1981-07-28 | Gyogyszerkutato Intezet | Process for producing new peptidyl-n-carboxy-l-arginin-a |
| CA1161431A (en) * | 1979-05-11 | 1984-01-31 | Lars G. Svendsen | Tripeptide derivatives |
| HU184368B (en) * | 1981-01-13 | 1984-08-28 | Gyogyszerkutato Intezet | Process for preparing d-phenyl-alanyl-l-propyl-l-arginine-ald ehyde-shulphate |
| US4434096A (en) * | 1981-06-30 | 1984-02-28 | E. I. Du Pont De Nemours And Company | Substrates for the quantitative determination of proteolytic enzymes |
| US4448717A (en) * | 1982-11-12 | 1984-05-15 | Eli Lilly And Company | Pharmacologically active peptides |
| DE3244030A1 (de) * | 1982-11-27 | 1984-05-30 | Behringwerke Ag, 3550 Marburg | Chromogene verbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| CA1267499A (en) * | 1983-07-12 | 1990-04-03 | Cedric H. Hassall | Peptide amides and aldehydes |
-
1984
- 1984-12-21 HU HU844763A patent/HU192646B/hu unknown
-
1985
- 1985-12-19 CN CN85109736A patent/CN1025738C/zh not_active Expired - Lifetime
- 1985-12-20 GR GR853121A patent/GR853121B/el not_active IP Right Cessation
- 1985-12-20 JP JP60285851A patent/JPH0680078B2/ja not_active Expired - Fee Related
- 1985-12-20 FI FI855118A patent/FI85980C/fi not_active IP Right Cessation
- 1985-12-20 CA CA000498306A patent/CA1261547A/en not_active Expired
- 1985-12-20 AR AR85302660A patent/AR241710A1/es active
- 1985-12-20 US US06/811,937 patent/US4703036A/en not_active Expired - Lifetime
- 1985-12-20 SU SU3992296A patent/SU1384203A3/ru active
- 1985-12-20 AU AU51553/85A patent/AU585561B2/en not_active Ceased
- 1985-12-20 DK DK596385A patent/DK171403B1/da not_active IP Right Cessation
- 1985-12-20 IL IL77416A patent/IL77416A/xx active IP Right Grant
- 1985-12-20 ES ES550296A patent/ES8708237A1/es not_active Expired
- 1985-12-20 PT PT81746A patent/PT81746B/pt not_active IP Right Cessation
- 1985-12-20 ZA ZA859756A patent/ZA859756B/xx unknown
- 1985-12-23 AT AT85116383T patent/ATE68002T1/de not_active IP Right Cessation
- 1985-12-23 EP EP85116383A patent/EP0185390B1/de not_active Expired - Lifetime
- 1985-12-23 DE DE8585116383T patent/DE3584281D1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1261547A (en) | 1989-09-26 |
| PT81746A (en) | 1986-01-01 |
| DK171403B1 (da) | 1996-10-14 |
| DE3584281D1 (de) | 1991-11-07 |
| ZA859756B (en) | 1986-09-24 |
| CN85109736A (zh) | 1987-03-18 |
| ES8708237A1 (es) | 1987-10-01 |
| ATE68002T1 (de) | 1991-10-15 |
| DK596385A (da) | 1986-06-22 |
| HU192646B (en) | 1987-06-29 |
| JPH0680078B2 (ja) | 1994-10-12 |
| AR241710A1 (es) | 1992-11-30 |
| FI855118L (fi) | 1986-06-22 |
| AU5155385A (en) | 1986-06-26 |
| HUT38954A (en) | 1986-07-28 |
| PT81746B (pt) | 1987-11-11 |
| DK596385D0 (da) | 1985-12-20 |
| US4703036A (en) | 1987-10-27 |
| JPS61152699A (ja) | 1986-07-11 |
| FI85980B (fi) | 1992-03-13 |
| FI855118A0 (fi) | 1985-12-20 |
| EP0185390A2 (de) | 1986-06-25 |
| FI85980C (fi) | 1992-06-25 |
| GR853121B (enExample) | 1986-04-22 |
| EP0185390B1 (de) | 1991-10-02 |
| ES550296A0 (es) | 1987-10-01 |
| EP0185390A3 (en) | 1988-09-07 |
| SU1384203A3 (ru) | 1988-03-23 |
| IL77416A (en) | 1990-04-29 |
| AU585561B2 (en) | 1989-06-22 |
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