NO318372B1 - Azasykloheksapeptidforbindelser, antimikrobielt preparat og anvendelse av disse forbindelser ved fremstilling av et farmasoytisk preparat. - Google Patents
Azasykloheksapeptidforbindelser, antimikrobielt preparat og anvendelse av disse forbindelser ved fremstilling av et farmasoytisk preparat. Download PDFInfo
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- NO318372B1 NO318372B1 NO19953648A NO953648A NO318372B1 NO 318372 B1 NO318372 B1 NO 318372B1 NO 19953648 A NO19953648 A NO 19953648A NO 953648 A NO953648 A NO 953648A NO 318372 B1 NO318372 B1 NO 318372B1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/08—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis for Pneumocystis carinii
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Chemical Vapour Deposition (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/032,847 US5378804A (en) | 1993-03-16 | 1993-03-16 | Aza cyclohexapeptide compounds |
| PCT/US1994/002580 WO1994021677A1 (en) | 1993-03-16 | 1994-03-10 | Aza cyclohexapeptide compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO953648D0 NO953648D0 (no) | 1995-09-15 |
| NO953648L NO953648L (no) | 1995-11-15 |
| NO318372B1 true NO318372B1 (no) | 2005-03-14 |
Family
ID=21867140
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19953648A NO318372B1 (no) | 1993-03-16 | 1995-09-15 | Azasykloheksapeptidforbindelser, antimikrobielt preparat og anvendelse av disse forbindelser ved fremstilling av et farmasoytisk preparat. |
| NO2005020C NO2005020I2 (no) | 1993-03-16 | 2005-09-13 | Caspofungin, eventuelt i form av et farmasoeytisk akseptabelt salt saerlig caspofungiacetat |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2005020C NO2005020I2 (no) | 1993-03-16 | 2005-09-13 | Caspofungin, eventuelt i form av et farmasoeytisk akseptabelt salt saerlig caspofungiacetat |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US5378804A (cs) |
| EP (1) | EP0620232B1 (cs) |
| JP (1) | JP2568474B2 (cs) |
| KR (1) | KR100329693B1 (cs) |
| CN (1) | CN1098274C (cs) |
| AT (1) | ATE186736T1 (cs) |
| AU (1) | AU668804B2 (cs) |
| BG (1) | BG63047B1 (cs) |
| BR (2) | BR9406009A (cs) |
| CA (1) | CA2118757C (cs) |
| CZ (1) | CZ286235B6 (cs) |
| DE (2) | DE69421639T2 (cs) |
| DK (1) | DK0620232T3 (cs) |
| ES (1) | ES2139043T3 (cs) |
| FI (1) | FI109542B (cs) |
| GR (1) | GR3031872T3 (cs) |
| HK (1) | HK1008674A1 (cs) |
| HR (1) | HRP940161B1 (cs) |
| HU (2) | HU217614B (cs) |
| IL (1) | IL108892A (cs) |
| LU (1) | LU90875I2 (cs) |
| LV (1) | LV12574B (cs) |
| NL (1) | NL300076I2 (cs) |
| NO (2) | NO318372B1 (cs) |
| NZ (1) | NZ263360A (cs) |
| PL (1) | PL179261B1 (cs) |
| RO (1) | RO113246B1 (cs) |
| RU (1) | RU2122548C1 (cs) |
| SI (1) | SI9420013B (cs) |
| SK (1) | SK282527B6 (cs) |
| UA (1) | UA59329C2 (cs) |
| WO (1) | WO1994021677A1 (cs) |
| ZA (1) | ZA941807B (cs) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5874403A (en) * | 1992-10-15 | 1999-02-23 | Merck & Co., Inc. | Amino acid conjugates of cyclohexapeptidyl amines |
| US5378804A (en) * | 1993-03-16 | 1995-01-03 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| US5948753A (en) * | 1993-05-04 | 1999-09-07 | Merck & Co., Inc. | Cyclohexapeptidyl propanolamine compounds |
| EP0779895B1 (en) * | 1994-08-23 | 1999-11-17 | Merck & Co. Inc. | An improved process for preparing side chain derivatives of cyclohexapeptidyl lipopeptides |
| EP0781141B1 (en) * | 1994-09-16 | 2002-09-04 | Merck & Co. Inc. | Aza cyclohexapeptide compounds |
| US5514651A (en) * | 1994-09-16 | 1996-05-07 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| US5516757A (en) * | 1994-09-16 | 1996-05-14 | Merck & Co., Inc. | Semi-synthetic lipopeptides, compositions containing said lipopeptides, and methods of use |
| US5516756A (en) * | 1994-10-31 | 1996-05-14 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| WO1996022784A1 (en) * | 1995-01-26 | 1996-08-01 | Merck & Co., Inc. | Novel antifungal cyclohexapeptides |
| US5552521A (en) * | 1995-02-10 | 1996-09-03 | Merck & Co., Inc. | Process for preparing certain aza cyclohexapeptides |
| WO1997017365A1 (en) * | 1995-11-09 | 1997-05-15 | Merck & Co., Inc. | Cyclohexapeptidyl bisamine compound, compositions containing said compound and methods of use |
| US5952300A (en) * | 1996-04-19 | 1999-09-14 | Merck & Co., Inc. | Antifungal compositions |
| AR006598A1 (es) * | 1996-04-19 | 1999-09-08 | Merck Sharp & Dohme | "composiciones anti-fungosas, su uso en la manufactura de medicamentos y un procedimiento para su preparación" |
| HRP970318B1 (en) * | 1996-06-14 | 2002-06-30 | Merck & Co Inc | A process for preparing certain aza cyclohexapeptides |
| DK0925070T3 (da) * | 1996-09-12 | 2003-12-01 | Merck & Co Inc | Antifungal kombinationsterapi |
| USRE38984E1 (en) * | 1996-09-12 | 2006-02-14 | Merck & Co., Inc. | Antifungal combination therapy |
| US5854212A (en) * | 1996-10-23 | 1998-12-29 | Merck & Co., Inc. | Cyclohexapeptidyl bisamine compound, compositions containing said compound and methods of use |
| US5936062A (en) * | 1997-06-12 | 1999-08-10 | Merck & Co., Inc. | Process for preparing certain aza cyclohexapeptides |
| EP1204677B1 (en) * | 1999-07-27 | 2008-12-03 | Aventis Pharma Deutschland GmbH | Cyclohexapeptide compounds, process for their production and their use as a pharmaceutical |
| AR035808A1 (es) * | 2001-04-12 | 2004-07-14 | Merck & Co Inc | Proceso de deshidratacion capaz de minimizar la epimerizacion de un grupo hidroxilo por ciertas equinocandinas |
| IL163666A0 (en) | 2002-02-22 | 2005-12-18 | New River Pharmaceuticals Inc | Active agent delivery systems and methods for protecting and administering active agents |
| US7214768B2 (en) * | 2002-04-08 | 2007-05-08 | Merck & Co., Inc. | Echinocandin process |
| ES2298821T3 (es) | 2003-07-22 | 2008-05-16 | Theravance, Inc. | Utilizacion de un agente antifungico de equinocandina en combinacion con un agente antibacteriano glicopeptidico. |
| CA2557333A1 (en) * | 2004-02-24 | 2005-09-01 | Commonwealth Scientific And Industrial Research Organisation | Antifungal peptides |
| EP1785432A1 (en) | 2005-11-15 | 2007-05-16 | Sandoz AG | Process and intermediates for the synthesis of caspofungin. |
| CA2657817C (en) | 2006-07-26 | 2016-05-31 | Sandoz Ag | Caspofungin formulations |
| TW200826957A (en) * | 2006-10-16 | 2008-07-01 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Purification processes for echinocandin-type compounds |
| JP5537425B2 (ja) * | 2007-06-26 | 2014-07-02 | メルク・シャープ・アンド・ドーム・コーポレーション | 凍結乾燥抗真菌組成物 |
| US20090075870A1 (en) * | 2007-09-17 | 2009-03-19 | Protia, Llc | Deuterium-enriched caspofungin |
| US20090291996A1 (en) * | 2008-05-21 | 2009-11-26 | Ferenc Korodi | Caspofungin free of caspofungin Co |
| US8048853B2 (en) * | 2008-06-13 | 2011-11-01 | Xellia Pharmaceuticals Aps | Process for preparing pharmaceutical compound and intermediates thereof |
| US20090324635A1 (en) * | 2008-06-25 | 2009-12-31 | Ferenc Korodi | Caspofungin free of caspofungin impurity A |
| WO2010008493A2 (en) * | 2008-06-25 | 2010-01-21 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Processes for preparing high purity aza cyclohexapeptides |
| WO2010064219A1 (en) | 2008-12-04 | 2010-06-10 | Ranbaxy Laboratories Limited | Process for the preparation of a novel intermediate for caspofungin |
| TW201024322A (en) * | 2008-12-31 | 2010-07-01 | Chunghwa Chemical Synthesis & Biotech Co Ltd | Preparation method for nitrogen containing heterocyclic hexapeptide with high conversion rate |
| WO2010108637A1 (en) | 2009-03-27 | 2010-09-30 | Axellia Pharmaceuticals Aps | Crystalline compound |
| CN101602795B (zh) * | 2009-07-20 | 2011-12-21 | 中国人民解放军第二军医大学 | 环六脂肽胺类抗真菌化合物及其盐类和制备方法 |
| US20120190815A1 (en) * | 2009-08-06 | 2012-07-26 | Tianhui Xu | Azacyclohexapeptide or its pharmaceutical acceptable salt, preparing method and use thereof |
| US8751760B2 (en) * | 2009-10-01 | 2014-06-10 | Dell Products L.P. | Systems and methods for power state transitioning in an information handling system |
| CN101792486A (zh) * | 2010-04-12 | 2010-08-04 | 浙江海正药业股份有限公司 | 一种合成醋酸卡泊芬净的方法 |
| CN102219832B (zh) | 2010-04-15 | 2013-08-21 | 上海天伟生物制药有限公司 | 一种氮杂环六肽或其盐的纯化方法 |
| RU2013114993A (ru) | 2010-09-20 | 2014-10-27 | Кселлия Фармасьютикалз Апс | Композиция каспофунгина |
| CA2813330A1 (en) * | 2010-09-29 | 2012-04-05 | Shanghai Techwell Biopharmaceutical Co., Ltd. | Process for purifying cyclolipopeptide compounds or the salts thereof |
| US8877777B2 (en) * | 2010-09-30 | 2014-11-04 | Shanghai Techwell Biopharmaceutical Co., Ltd. | Process for purifying cyclolipopeptide compounds or the salts thereof |
| CN102367268B (zh) | 2010-11-10 | 2013-11-06 | 上海天伟生物制药有限公司 | 一种卡泊芬净类似物及其用途 |
| CN102367267B (zh) | 2010-11-10 | 2013-09-04 | 上海天伟生物制药有限公司 | 一种卡泊芬净的制备方法 |
| CN102367269B (zh) | 2010-11-10 | 2013-11-06 | 上海天伟生物制药有限公司 | 一种卡泊芬净类似物及其制备方法和用途 |
| KR101331984B1 (ko) | 2010-12-09 | 2013-11-25 | 종근당바이오 주식회사 | 카스포펀진 제조방법 및 그의 신규 중간체 |
| WO2012093293A1 (en) * | 2011-01-03 | 2012-07-12 | Biocon Limited | Process for preparation of caspofungin acetate and intermediates |
| CN102618606B (zh) * | 2011-01-30 | 2014-09-10 | 浙江海正药业股份有限公司 | 一种棘白菌素生物转化方法 |
| HUE036778T2 (hu) | 2011-03-03 | 2018-07-30 | Cidara Therapeutics Inc | Gombaellenes szerek és alkalmazásuk |
| CN102746384B (zh) | 2011-04-22 | 2016-01-20 | 上海天伟生物制药有限公司 | 一种高纯度的卡泊芬净或其盐及其制备方法和用途 |
| WO2012146099A1 (zh) | 2011-04-28 | 2012-11-01 | 上海源力生物技术有限公司 | 用于合成卡帕芬净的中间体及其制备方法 |
| DK3677252T3 (da) | 2012-03-19 | 2023-10-02 | Cidara Therapeutics Inc | Doseringsregimer for echinocandin-klasse forbindelser |
| WO2014081443A1 (en) * | 2012-11-20 | 2014-05-30 | Fresenius Kabi Usa, Llc | Caspofungin acetate formulations |
| CN105481952B (zh) * | 2014-12-24 | 2020-12-29 | 上海天伟生物制药有限公司 | 一种含氮杂环六肽前体的组合物及其制备方法和用途 |
| WO2017034961A1 (en) | 2015-08-21 | 2017-03-02 | Trilogy Therapeutics, Inc. | Methods of treating lung infection with caspofungin |
| US10369188B2 (en) | 2016-01-08 | 2019-08-06 | Cidara Therapeutics, Inc. | Methods for preventing and treating pneumocystis infections |
| EP4268896A3 (en) | 2016-03-16 | 2024-01-03 | Cidara Therapeutics, Inc. | Dosing regimens for treatment of fungal infections |
| WO2017185030A1 (en) * | 2016-04-22 | 2017-10-26 | Fresenius Kabi Usa, Llc | Caspofungin formulation with low impurities |
| JP2020529973A (ja) | 2017-07-12 | 2020-10-15 | シダラ セラピューティクス インコーポレーテッド | 真菌感染症の処置のための組成物及び方法 |
| WO2019157453A1 (en) | 2018-02-12 | 2019-08-15 | Trilogy Therapeutics, Inc. | Caspofungin compositions for inhalation |
| EP3620462A1 (en) | 2018-09-04 | 2020-03-11 | Xellia Pharmaceuticals ApS | Process for the preparation of caspofungin |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2704030A1 (de) * | 1976-02-12 | 1977-08-18 | Sandoz Ag | Neue organische verbindungen, ihre herstellung und verwendung |
| BE851310A (fr) * | 1976-02-12 | 1977-08-10 | Sandoz Sa | Nouveaux derives de la tetrahydro-equinocandine b |
| DE2742435A1 (de) * | 1976-09-28 | 1978-04-06 | Sandoz Ag | Aminoalkylaether der peptide tetrahydro- sl 7810/f-ii, s 31794/f-1, aculeacin a und tetrahydroechinocandin b, ihre verwendung und herstellung |
| US4293489A (en) * | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of A-30912A nucleus |
| US4293485A (en) * | 1979-12-13 | 1981-10-06 | Eli Lilly And Company | Derivatives of S31794/F-1 nucleus |
| GB2065130A (en) * | 1979-12-13 | 1981-06-24 | Lilly Co Eli | Recovery process for a-30912 antibiotics |
| US4320053A (en) * | 1979-12-13 | 1982-03-16 | Eli Lilly And Company | Derivatives of A-30912D nucleus |
| US4287120A (en) * | 1979-12-13 | 1981-09-01 | Eli Lilly And Company | Derivatives of S31794/F-1 nucleus |
| DE3030554A1 (de) * | 1980-08-13 | 1982-03-25 | Chemische Werke Hüls AG, 4370 Marl | Einbrennlacke |
| US4931352A (en) * | 1987-10-07 | 1990-06-05 | Merck & Co., Inc. | Antifungal fermentation product |
| US5166135A (en) * | 1988-09-12 | 1992-11-24 | Merck & Company, Inc. | Method for the control of pneumocystis carinii |
| DK173802B1 (da) * | 1988-09-12 | 2001-11-05 | Merck & Co Inc | Præparat til behandling af Pneumocystis carinii infeksioner og anvendelse af et cyclohexapeptid til fremstilling af et lægemiddel mod Pneumocystis carinii infektioner |
| US5202309A (en) * | 1989-06-30 | 1993-04-13 | Merck & Co., Inc. | Antibiotic cyclopeptide fermentation product |
| IL94862A (en) * | 1989-06-30 | 1994-10-07 | Merck & Co Inc | History of Echinocandin Antifungal Antibiotics, Its Production and Pharmaceutical Preparations Containing It |
| US5021341A (en) * | 1990-03-12 | 1991-06-04 | Merck & Co., Inc. | Antibiotic agent produced by the cultivation of Zalerion microorganism in the presence of mannitol |
| US5194377A (en) * | 1989-06-30 | 1993-03-16 | Merck & Co., Inc. | Antibiotic agent |
| GB8925593D0 (en) * | 1989-11-13 | 1990-01-04 | Fujisawa Pharmaceutical Co | Fr901379 substance and preparation thereof |
| US5159059A (en) * | 1990-05-29 | 1992-10-27 | Merck & Co., Inc. | Process for reduction of certain cyclohexapeptide compounds |
| IL122315A (en) * | 1992-03-19 | 2002-03-10 | Lilly Co Eli | Cyclic peptides and antifungal pharmaceutical compositions containing them |
| US5378804A (en) * | 1993-03-16 | 1995-01-03 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| US5516757A (en) * | 1994-09-16 | 1996-05-14 | Merck & Co., Inc. | Semi-synthetic lipopeptides, compositions containing said lipopeptides, and methods of use |
| US5516756A (en) * | 1994-10-31 | 1996-05-14 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
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