HU192646B - Process for preparing new n-alkyl-peptide aldehydes - Google Patents
Process for preparing new n-alkyl-peptide aldehydes Download PDFInfo
- Publication number
- HU192646B HU192646B HU844763A HU476384A HU192646B HU 192646 B HU192646 B HU 192646B HU 844763 A HU844763 A HU 844763A HU 476384 A HU476384 A HU 476384A HU 192646 B HU192646 B HU 192646B
- Authority
- HU
- Hungary
- Prior art keywords
- benzyloxycarbonyl
- proline
- xxx
- arginine
- mol
- Prior art date
Links
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- -1 aldehyde salt Chemical class 0.000 claims description 41
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000007711 Peperomia pellucida Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- NHVHYFAWHCJELN-UHFFFAOYSA-N benzene;n,n-dimethylformamide Chemical compound CN(C)C=O.C1=CC=CC=C1 NHVHYFAWHCJELN-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LYEWJUQTCPOXLM-UHFFFAOYSA-N ethyl acetate;2-pyridin-2-ylacetic acid Chemical compound CCOC(C)=O.OC(=O)CC1=CC=CC=N1 LYEWJUQTCPOXLM-UHFFFAOYSA-N 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU844763A HU192646B (en) | 1984-12-21 | 1984-12-21 | Process for preparing new n-alkyl-peptide aldehydes |
| CN85109736A 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 |
| ZA859756A ZA859756B (en) | 1984-12-21 | 1985-12-20 | Peptide-aldehydes,process for the preparation thereof and pharmaceutical compositions containing the same |
| GR853121A GR853121B (en, 2012) | 1984-12-21 | 1985-12-20 | |
| AU51553/85A AU585561B2 (en) | 1984-12-21 | 1985-12-20 | New peptide-aldehydes, process for the preparation thereof and pharmaceutical compositions containing the same |
| FI855118A FI85980C (fi) | 1984-12-21 | 1985-12-20 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara peptidaldehyder. |
| ES550296A ES8708237A1 (es) | 1984-12-21 | 1985-12-20 | Procedimiento para la preparacion de nuevos aldehidos pep- tidos |
| US06/811,937 US4703036A (en) | 1984-12-21 | 1985-12-20 | Peptide-aldehydes, process for the preparation thereof and pharmaceutical compositions containing the same |
| JP60285851A JPH0680078B2 (ja) | 1984-12-21 | 1985-12-20 | ペプチド‐アルデヒド誘導体 |
| SU3992296A SU1384203A3 (ru) | 1984-12-21 | 1985-12-20 | Способ получени сульфатов пептидил-аргининальдегидов |
| DK596385A DK171403B1 (da) | 1984-12-21 | 1985-12-20 | Peptidaldehyder og farmaceutiske præparater indeholdende sådanne forbindelser, samt fremgangsmåder til fremstilling heraf |
| PT81746A PT81746B (pt) | 1984-12-21 | 1985-12-20 | Processo para a preparacao de peptido-aldeidos e de composicoes farmaceuticas que os contem |
| IL77416A IL77416A (en) | 1984-12-21 | 1985-12-20 | N-alkylated tripeptide aldehyde sulfates,their preparation and pharmaceutical compositions containing them |
| AR85302660A AR241710A1 (es) | 1984-12-21 | 1985-12-20 | Procedimiento para la preparacion de derivados de peptido-aldehidos |
| CA000498306A CA1261547A (en) | 1984-12-21 | 1985-12-20 | Peptide-aldehydes, process for the preparation thereof and pharmaceutical compositions containing the same |
| DE8585116383T DE3584281D1 (de) | 1984-12-21 | 1985-12-23 | Tripeptidyl-argininaldehyde, verfahren zu ihrer herstellung und diese enthaltende arzneimittel sowie n-(monoalkyl)- und n,n-di-(alkyl)-xxx-l-prolin-dipeptide. |
| EP85116383A EP0185390B1 (de) | 1984-12-21 | 1985-12-23 | Tripeptidyl-argininaldehyde, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel sowie N-(Monoalkyl)- und N,N-Di-(alkyl)-Xxx-L-prolin-Dipeptide |
| AT85116383T ATE68002T1 (de) | 1984-12-21 | 1985-12-23 | Tripeptidyl-argininaldehyde, verfahren zu ihrer herstellung und diese enthaltende arzneimittel sowie n-(monoalkyl)- und n,n-di-(alkyl)-xxx-lprolin-dipeptide. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU844763A HU192646B (en) | 1984-12-21 | 1984-12-21 | Process for preparing new n-alkyl-peptide aldehydes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT38954A HUT38954A (en) | 1986-07-28 |
| HU192646B true HU192646B (en) | 1987-06-29 |
Family
ID=10968854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU844763A HU192646B (en) | 1984-12-21 | 1984-12-21 | Process for preparing new n-alkyl-peptide aldehydes |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4703036A (en, 2012) |
| EP (1) | EP0185390B1 (en, 2012) |
| JP (1) | JPH0680078B2 (en, 2012) |
| CN (1) | CN1025738C (en, 2012) |
| AR (1) | AR241710A1 (en, 2012) |
| AT (1) | ATE68002T1 (en, 2012) |
| AU (1) | AU585561B2 (en, 2012) |
| CA (1) | CA1261547A (en, 2012) |
| DE (1) | DE3584281D1 (en, 2012) |
| DK (1) | DK171403B1 (en, 2012) |
| ES (1) | ES8708237A1 (en, 2012) |
| FI (1) | FI85980C (en, 2012) |
| GR (1) | GR853121B (en, 2012) |
| HU (1) | HU192646B (en, 2012) |
| IL (1) | IL77416A (en, 2012) |
| PT (1) | PT81746B (en, 2012) |
| SU (1) | SU1384203A3 (en, 2012) |
| ZA (1) | ZA859756B (en, 2012) |
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 |
| ZA928581B (en) * | 1991-11-12 | 1994-05-06 | Lilly Co Eli | Antithrombotic agents |
| US5416093A (en) * | 1991-11-12 | 1995-05-16 | Eli Lilly And Company | Antithrombotic agents |
| AU663169B2 (en) * | 1992-03-04 | 1995-09-28 | Gyogyszerkutato Intezet Kft | New anticoagulant peptide derivatives and pharmaceutical compositions containing the same as well as a process for the preparation thereof |
| 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 |
| ATE227581T1 (de) * | 1993-04-30 | 2002-11-15 | Merck & Co Inc | Thrombin-inhibitoren |
| SE9301916D0 (sv) * | 1993-06-03 | 1993-06-03 | Ab Astra | New peptides derivatives |
| US5783563A (en) * | 1993-06-03 | 1998-07-21 | Astra Aktiebolag | Method for treatment or prophylaxis of venous thrombosis |
| US6984627B1 (en) | 1993-06-03 | 2006-01-10 | Astrazeneca Ab | Peptide derivatives |
| US5726159A (en) * | 1994-03-04 | 1998-03-10 | Eli Lilly And Company | Antithrombotic agents |
| ZA951618B (en) * | 1994-03-04 | 1996-08-27 | Lilly Co Eli | Antithrombotic agents |
| US5436229A (en) * | 1994-03-04 | 1995-07-25 | Eli Lilly And Company | Bisulfite adducts of arginine aldehydes |
| US5439888A (en) * | 1994-03-04 | 1995-08-08 | Eli Lilly And Company | Antithrombotic agents |
| US5488037A (en) * | 1994-03-04 | 1996-01-30 | Eli Lilly And Company | Antithrombotic agents |
| US5885967A (en) * | 1994-03-04 | 1999-03-23 | Eli Lilly And Company | Antithrombotic agents |
| US5602101A (en) * | 1994-03-04 | 1997-02-11 | Eli Lilly And Company | Antithrombotic agents |
| US5484772A (en) * | 1994-03-04 | 1996-01-16 | 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 |
| US5707966A (en) * | 1994-03-04 | 1998-01-13 | Eli Lilly And Company | Antithrombotic agents |
| AU701503B2 (en) * | 1994-06-17 | 1999-01-28 | Corvas International, Inc. | Methods of synthesis of peptidyl argininals |
| DE4421052A1 (de) * | 1994-06-17 | 1995-12-21 | Basf Ag | Neue Thrombininhibitoren, ihre Herstellung und Verwendung |
| 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 |
| US6025472A (en) * | 1994-12-21 | 2000-02-15 | Corvas International, Inc. | N-substituted glycine derivatives as enzyme inhibitors |
| US5696231A (en) * | 1994-12-21 | 1997-12-09 | Corvas International, Inc. | N-substituted glycine derivatives as enzyme inhibitors |
| AU708001B2 (en) * | 1995-02-17 | 1999-07-29 | Abbott Gmbh & Co. Kg | Novel thrombin inhibitors |
| 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 |
| AR005245A1 (es) | 1995-12-21 | 1999-04-28 | Astrazeneca Ab | Prodrogas de inhibidores de trombina, una formulación farmaceutica que las comprende, el uso de dichas prodrogas para la manufactura de un medicamento y un procedimiento para su preparacion |
| 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 |
| HU224315B1 (hu) * | 1996-06-05 | 2005-07-28 | Gyógyszerkutató Intézet Kft. | Véralvadásgátló hatású peptidil-arginin-aldehid-származékok és a vegyületeket tartalmazó gyógyszerkészítmények |
| HU222199B1 (hu) * | 1996-06-05 | 2003-05-28 | Gyógyszerkutató Intézet Kft. | Véralvadásgátló hatású peptid-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 |
| US6165966A (en) * | 1996-09-24 | 2000-12-26 | The Procter & Gamble Company | Liquid detergents containing proteolytic enzyme and protease inhibitors |
| JP2000506931A (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とプロテアーゼインヒビターを含有した液体洗剤 |
| BR9712114A (pt) | 1996-09-24 | 1999-08-31 | Procter & Gamble | Composições detergente líquidas para lavanderia contendo enzima proteolítica e inibidores de protease. |
| 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 |
| WO1999037668A1 (de) | 1998-01-26 | 1999-07-29 | Basf Aktiengesellschaft | Thrombininhibitoren |
| SE9804313D0 (sv) | 1998-12-14 | 1998-12-14 | Astra Ab | New compounds |
| JP2002535250A (ja) | 1999-01-13 | 2002-10-22 | アストラゼネカ アクチボラグ | 新規アミジノベンジルアミン誘導体およびトロンビン阻害物質としてのそれらの使用 |
| AU3192500A (en) * | 1999-03-16 | 2000-10-04 | C & C Research Laboratories | Substituted proline derivatives and medicinal compositions containing the same |
| 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 |
| 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 |
| US7129233B2 (en) | 2000-12-01 | 2006-10-31 | Astrazeneca Ab | Mandelic acid derivatives and their use as thrombin inhibitors |
| WO2002050056A1 (en) | 2000-12-18 | 2002-06-27 | Merck & Co., Inc. | Benzylamine derivatives and their use as thrombin inhibitors |
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| AR034517A1 (es) * | 2001-06-21 | 2004-02-25 | Astrazeneca Ab | Formulacion farmaceutica |
| CZ2004265A3 (cs) * | 2001-08-21 | 2004-08-18 | Ivaxáinstituteáforádrugáresearchźáltd | Peptidové arginaly a způsoby léčby diseminované intravaskulární koagulace |
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| 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 |
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| ES2539504T3 (es) | 2011-07-01 | 2015-07-01 | Novozymes A/S | Composición de subtilisina estabilizada |
| 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 JP JP60285851A patent/JPH0680078B2/ja not_active Expired - Fee Related
- 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 GR GR853121A patent/GR853121B/el not_active IP Right Cessation
- 1985-12-20 ES ES550296A patent/ES8708237A1/es not_active Expired
- 1985-12-20 DK DK596385A patent/DK171403B1/da not_active IP Right Cessation
- 1985-12-20 ZA ZA859756A patent/ZA859756B/xx unknown
- 1985-12-20 CA CA000498306A patent/CA1261547A/en not_active Expired
- 1985-12-20 PT PT81746A patent/PT81746B/pt not_active IP Right Cessation
- 1985-12-20 FI FI855118A patent/FI85980C/fi not_active IP Right Cessation
- 1985-12-20 IL IL77416A patent/IL77416A/xx active IP Right Grant
- 1985-12-20 SU SU3992296A patent/SU1384203A3/ru active
- 1985-12-20 AU AU51553/85A patent/AU585561B2/en not_active Ceased
- 1985-12-23 DE DE8585116383T patent/DE3584281D1/de not_active Expired - Lifetime
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| DK596385D0 (da) | 1985-12-20 |
| EP0185390B1 (de) | 1991-10-02 |
| AU5155385A (en) | 1986-06-26 |
| DE3584281D1 (de) | 1991-11-07 |
| AU585561B2 (en) | 1989-06-22 |
| AR241710A1 (es) | 1992-11-30 |
| DK596385A (da) | 1986-06-22 |
| DK171403B1 (da) | 1996-10-14 |
| CN85109736A (zh) | 1987-03-18 |
| PT81746B (pt) | 1987-11-11 |
| EP0185390A2 (de) | 1986-06-25 |
| HUT38954A (en) | 1986-07-28 |
| FI855118A0 (fi) | 1985-12-20 |
| JPH0680078B2 (ja) | 1994-10-12 |
| FI855118L (fi) | 1986-06-22 |
| FI85980C (fi) | 1992-06-25 |
| GR853121B (en, 2012) | 1986-04-22 |
| ES550296A0 (es) | 1987-10-01 |
| PT81746A (en) | 1986-01-01 |
| US4703036A (en) | 1987-10-27 |
| ZA859756B (en) | 1986-09-24 |
| IL77416A (en) | 1990-04-29 |
| CA1261547A (en) | 1989-09-26 |
| FI85980B (fi) | 1992-03-13 |
| ES8708237A1 (es) | 1987-10-01 |
| ATE68002T1 (de) | 1991-10-15 |
| JPS61152699A (ja) | 1986-07-11 |
| SU1384203A3 (ru) | 1988-03-23 |
| CN1025738C (zh) | 1994-08-24 |
| EP0185390A3 (en) | 1988-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |