NZ554405A - Method for preparing crystalline and crystal-like forms of purified lipopeptides - Google Patents
Method for preparing crystalline and crystal-like forms of purified lipopeptidesInfo
- Publication number
- NZ554405A NZ554405A NZ554405A NZ55440501A NZ554405A NZ 554405 A NZ554405 A NZ 554405A NZ 554405 A NZ554405 A NZ 554405A NZ 55440501 A NZ55440501 A NZ 55440501A NZ 554405 A NZ554405 A NZ 554405A
- Authority
- NZ
- New Zealand
- Prior art keywords
- daptomycin
- crystal
- solution
- crystalline
- crystallizing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 53
- 108010028921 Lipopeptides Proteins 0.000 title claims 2
- 108010013198 Daptomycin Proteins 0.000 claims abstract 35
- DOAKLVKFURWEDJ-QCMAZARJSA-N daptomycin Chemical compound C([C@H]1C(=O)O[C@H](C)[C@@H](C(NCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C(=O)N1)[C@H](C)CC(O)=O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CCCCCCCCC)C(=O)C1=CC=CC=C1N DOAKLVKFURWEDJ-QCMAZARJSA-N 0.000 claims abstract 35
- 229960005484 daptomycin Drugs 0.000 claims abstract 35
- 150000001768 cations Chemical class 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000011549 crystallization solution Substances 0.000 claims abstract 5
- 239000000872 buffer Substances 0.000 claims abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 10
- 239000000243 solution Substances 0.000 claims 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 238000002425 crystallisation Methods 0.000 claims 6
- 230000008025 crystallization Effects 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 230000001376 precipitating effect Effects 0.000 claims 5
- 238000001556 precipitation Methods 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 4
- 235000013772 propylene glycol Nutrition 0.000 claims 4
- 238000001914 filtration Methods 0.000 claims 3
- 238000000386 microscopy Methods 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 239000006179 pH buffering agent Substances 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 150000005846 sugar alcohols Polymers 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical group OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims 2
- 239000008000 CHES buffer Substances 0.000 claims 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims 2
- 239000007995 HEPES buffer Substances 0.000 claims 2
- 239000007987 MES buffer Substances 0.000 claims 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims 2
- MKWKNSIESPFAQN-UHFFFAOYSA-N N-cyclohexyl-2-aminoethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CCCCC1 MKWKNSIESPFAQN-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 239000006172 buffering agent Substances 0.000 claims 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims 2
- 239000001639 calcium acetate Substances 0.000 claims 2
- 229960005147 calcium acetate Drugs 0.000 claims 2
- 235000011092 calcium acetate Nutrition 0.000 claims 2
- 238000005119 centrifugation Methods 0.000 claims 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical class C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 claims 2
- 229940096405 magnesium cation Drugs 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- 229940044613 1-propanol Drugs 0.000 claims 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 238000012835 hanging drop method Methods 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 229940006486 zinc cation Drugs 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Fodder In General (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25626800P | 2000-12-18 | 2000-12-18 | |
| US27474101P | 2001-03-09 | 2001-03-09 | |
| US34052501P | 2001-12-13 | 2001-12-13 | |
| US34131501P | 2001-12-13 | 2001-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ554405A true NZ554405A (en) | 2009-04-30 |
Family
ID=27500563
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ571597A NZ571597A (en) | 2000-12-18 | 2001-12-17 | Method for preparing crystalline and crystal-like forms of purified daptomycin lipopeptides |
| NZ554405A NZ554405A (en) | 2000-12-18 | 2001-12-17 | Method for preparing crystalline and crystal-like forms of purified lipopeptides |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ571597A NZ571597A (en) | 2000-12-18 | 2001-12-17 | Method for preparing crystalline and crystal-like forms of purified daptomycin lipopeptides |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20030045484A1 (enExample) |
| EP (3) | EP1343811A4 (enExample) |
| JP (2) | JP2004525108A (enExample) |
| KR (4) | KR20090122469A (enExample) |
| CN (3) | CN1982330B (enExample) |
| AT (1) | ATE535539T1 (enExample) |
| AU (3) | AU2002246688A1 (enExample) |
| CA (1) | CA2432096A1 (enExample) |
| ES (2) | ES2377931T5 (enExample) |
| IL (3) | IL156394A0 (enExample) |
| NZ (2) | NZ571597A (enExample) |
| WO (1) | WO2002056829A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6696412B1 (en) | 2000-01-20 | 2004-02-24 | Cubist Pharmaceuticals, Inc. | High purity lipopeptides, Lipopeptide micelles and processes for preparing same |
| US20060014674A1 (en) | 2000-12-18 | 2006-01-19 | Dennis Keith | Methods for preparing purified lipopeptides |
| US20040077533A1 (en) * | 2002-05-23 | 2004-04-22 | Sayada Chalom B. | Methods and compositions for treating bacterial infections and diseases associated therewith |
| WO2003099217A2 (en) * | 2002-05-23 | 2003-12-04 | Activbiotics, Inc. | Methods of treating bacterial infections and diseases associated therewith |
| US20090149453A1 (en) * | 2002-05-23 | 2009-06-11 | Activbiotics Pharma Llc | Methods and compositions for treating bacterial infections and diseases associated therewith |
| AU2003240545A1 (en) | 2002-06-06 | 2003-12-22 | Therapeutics Corporation Genome | Use of ramoplanin to treat diseases associated with the use of antibiotics |
| JP2006515294A (ja) * | 2002-12-12 | 2006-05-25 | アクティブバイオティクス インコーポレイティッド | アテローム性動脈硬化症およびその関連疾患を治療または予防するための方法および試薬 |
| AU2003296963A1 (en) * | 2002-12-12 | 2004-07-09 | Activbiotics, Inc. | Methods and compositions for treating and preventing ear infections |
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| KR20080038224A (ko) * | 2006-07-20 | 2008-05-02 | 시코르, 인크. | 고체 멸균 유효 약리 성분의 제조 방법 |
| WO2009144739A1 (en) * | 2008-05-26 | 2009-12-03 | Biocon Limited | Amorphous daptomycin and a method of purification thereof |
| PT2398817E (pt) * | 2009-02-19 | 2015-08-28 | Xellia Pharmaceuticals Aps | Processo para purificar lipopéptidos |
| CN101830970B (zh) * | 2009-03-12 | 2012-06-27 | 成都雅途生物技术有限公司 | 一种高纯度达托霉素(Daptomycin)的纯化制备方法 |
| CN101899094B (zh) * | 2009-06-01 | 2012-11-21 | 安徽丰原发酵技术工程研究有限公司 | 一种高纯达托霉素的制备方法 |
| DK2504353T4 (da) * | 2009-11-23 | 2023-11-20 | Cubist Pharmaceuticals Llc | Lipopeptidsammensætninger og tilsvarende fremgangsmåder |
| JP2013511522A (ja) * | 2009-11-23 | 2013-04-04 | イーグル・ファーマシューティカルズ・インコーポレーテッド | ダプトマイシン製剤 |
| KR101151878B1 (ko) * | 2010-06-08 | 2012-05-31 | 미원상사주식회사 | 지방산 트리펩타이드염 및 이를 함유하는 항균 조성물 |
| CN102276696B (zh) * | 2010-06-09 | 2014-11-05 | 上海来益生物药物研究开发中心有限责任公司 | 达托霉素的纯化方法 |
| TW201309346A (zh) | 2011-01-05 | 2013-03-01 | Hospira Inc | 噴霧乾燥萬古黴素 |
| KR101034663B1 (ko) * | 2011-03-18 | 2011-05-17 | 김태욱 | 손목 피로를 저감시키는 마우스 |
| CN102206694B (zh) * | 2011-04-06 | 2013-10-16 | 山东新时代药业有限公司 | 一种含有癸酸的缓释组合物 |
| JP2014515371A (ja) * | 2011-05-26 | 2014-06-30 | キュービスト ファーマシューティカルズ， インコーポレイテッド | Ｃｂ−１８３，３１５組成物および関連する方法 |
| CN102241732B (zh) * | 2011-05-30 | 2015-01-21 | 浙江海正药业股份有限公司 | 一种脂肽化合物的纯化方法 |
| EA032840B8 (ru) * | 2011-06-22 | 2020-06-18 | Вайоми Терапеутикс Лимитед | Пролекарства на основе конъюгатов противогрибковых агентов и их применение |
| CN102875652A (zh) * | 2011-07-13 | 2013-01-16 | 北大方正集团有限公司 | 一种分离纯化达托霉素的方法 |
| WO2013012101A1 (ko) * | 2011-07-15 | 2013-01-24 | 미원상사주식회사 | 지방산 트리펩타이드염 및 이를 함유하는 항균 조성물 |
| CN102718839B (zh) * | 2012-07-05 | 2017-05-24 | 鲁南新时代生物技术有限公司 | 一种分离纯化达托霉素的方法 |
| WO2014031681A1 (en) * | 2012-08-20 | 2014-02-27 | The University Of Chicago | Inhibiting gram positive bacteria |
| CN104043104B (zh) | 2013-03-15 | 2018-07-10 | 浙江创新生物有限公司 | 含盐酸万古霉素的喷雾干粉及其工业化制备方法 |
| CN104387444B (zh) * | 2014-11-13 | 2017-12-08 | 北大医药重庆大新药业股份有限公司 | 一种达托霉素杂质rs‑2高纯度样品的制备方法 |
| US10647746B2 (en) | 2016-04-08 | 2020-05-12 | Versitech Limited | Antibacterial cyclic lipopeptides |
| US11667674B2 (en) | 2016-04-08 | 2023-06-06 | Versitech Limited | Antibacterial cyclic lipopeptides |
| CN109476704B (zh) * | 2016-04-08 | 2022-08-16 | 港大科桥有限公司 | 抗菌环脂肽 |
| IT201600127655A1 (it) | 2016-12-16 | 2018-06-16 | Gnosis Spa | Processo per la purificazione di antibiotici lipopolipeptidici |
| US10072045B1 (en) | 2017-06-26 | 2018-09-11 | Ramapo Pharmaceuticals, Inc. | Antibacterial lipopeptides and methods for their preparation and use |
| IT201800006314A1 (it) * | 2018-06-14 | 2019-12-14 | Uso di resine a scambio cationico per la purificazione di antibiotici lipopolipeptidici | |
| US12060439B2 (en) | 2018-10-25 | 2024-08-13 | Napp Pharmaceutical Group Limited | Polymorph of echinocandin antifungal agent |
| CN113271922A (zh) | 2018-12-21 | 2021-08-17 | 艾瑞克有限公司 | 新型组合物 |
| CN112979756B (zh) * | 2019-12-13 | 2023-01-03 | 浙江昌海制药有限公司 | 达托霉素的提纯方法 |
| CN113480623B (zh) * | 2021-08-09 | 2022-12-27 | 广州天赐高新材料股份有限公司 | 一种脂肽组合物及其制备方法和应用 |
| CN116726145A (zh) * | 2022-03-04 | 2023-09-12 | 海南普利制药股份有限公司 | 一种稳定的酯肽类药物组合物 |
| WO2024085235A1 (ja) * | 2022-10-20 | 2024-04-25 | 中外製薬株式会社 | 環状ペプチドの結晶の製造方法 |
| EP4631955A1 (en) * | 2022-12-28 | 2025-10-15 | Chugai Seiyaku Kabushiki Kaisha | Purification method and production method of cyclic peptide |
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