HRP20040642A2 - Processes for preparing crystalline and amorphous mupirocin calcium - Google Patents
Processes for preparing crystalline and amorphous mupirocin calcium Download PDFInfo
- Publication number
- HRP20040642A2 HRP20040642A2 HR20040642A HRP20040642A HRP20040642A2 HR P20040642 A2 HRP20040642 A2 HR P20040642A2 HR 20040642 A HR20040642 A HR 20040642A HR P20040642 A HRP20040642 A HR P20040642A HR P20040642 A2 HRP20040642 A2 HR P20040642A2
- Authority
- HR
- Croatia
- Prior art keywords
- calcium
- solution
- dihydrate
- water
- mupirocin calcium
- Prior art date
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- DDHVILIIHBIMQU-YJGQQKNPSA-L mupirocin calcium hydrate Chemical compound O.O.[Ca+2].C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1.C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC([O-])=O)OC1 DDHVILIIHBIMQU-YJGQQKNPSA-L 0.000 title claims description 191
- 229960000313 mupirocin calcium Drugs 0.000 title claims description 108
- 238000000034 method Methods 0.000 title claims description 104
- 230000008569 process Effects 0.000 title claims description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 130
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 130
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 111
- MINDHVHHQZYEEK-UHFFFAOYSA-N (E)-(2S,3R,4R,5S)-5-[(2S,3S,4S,5S)-2,3-epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-(beta)-methyl-2H-pyran-2-crotonic acid ester with 9-hydroxynonanoic acid Natural products CC(O)C(C)C1OC1CC1C(O)C(O)C(CC(C)=CC(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-UHFFFAOYSA-N 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 90
- 229960003128 mupirocin Drugs 0.000 claims description 84
- MINDHVHHQZYEEK-HBBNESRFSA-N mupirocin Chemical compound C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(=O)OCCCCCCCCC(O)=O)OC1 MINDHVHHQZYEEK-HBBNESRFSA-N 0.000 claims description 83
- 229930194369 pseudomonic acid Natural products 0.000 claims description 75
- 239000002904 solvent Substances 0.000 claims description 70
- 238000002360 preparation method Methods 0.000 claims description 58
- 150000004683 dihydrates Chemical class 0.000 claims description 42
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 33
- 229910001424 calcium ion Inorganic materials 0.000 claims description 33
- 239000012535 impurity Substances 0.000 claims description 29
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- 239000003125 aqueous solvent Substances 0.000 claims description 21
- 239000011575 calcium Substances 0.000 claims description 20
- 229910052791 calcium Inorganic materials 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 16
- 238000003556 assay Methods 0.000 claims description 16
- 150000007942 carboxylates Chemical class 0.000 claims description 16
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 15
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- 238000002844 melting Methods 0.000 claims description 14
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- 239000000292 calcium oxide Substances 0.000 claims description 10
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 10
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- 239000002253 acid Substances 0.000 claims description 9
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- GJRQTCIYDGXPES-UHFFFAOYSA-N isobutyl acetate Chemical group CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 9
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical group CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 5
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- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 3
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- 239000006187 pill Substances 0.000 description 1
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- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
- 239000000770 propane-1,2-diol alginate Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940032159 propylene carbonate Drugs 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
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- 230000000241 respiratory effect Effects 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 229960004274 stearic acid Drugs 0.000 description 1
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- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34411701P | 2001-12-28 | 2001-12-28 | |
| US34411801P | 2001-12-28 | 2001-12-28 | |
| US34818302P | 2002-01-11 | 2002-01-11 | |
| US34814202P | 2002-01-11 | 2002-01-11 | |
| US36072102P | 2002-03-01 | 2002-03-01 | |
| US36873502P | 2002-03-29 | 2002-03-29 | |
| PCT/US2002/035585 WO2003065975A2 (en) | 2001-12-28 | 2002-11-06 | Processes for preparing crystalline and amorphous mupirocin calcium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040642A2 true HRP20040642A2 (en) | 2005-10-31 |
Family
ID=27739507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040642A HRP20040642A2 (en) | 2001-12-28 | 2004-07-13 | Processes for preparing crystalline and amorphous mupirocin calcium |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US7737177B2 (xx) |
| EP (1) | EP1455769A4 (xx) |
| JP (1) | JP2005516984A (xx) |
| KR (1) | KR20040075857A (xx) |
| CN (1) | CN1625394A (xx) |
| AU (1) | AU2002365431A1 (xx) |
| CA (1) | CA2460970C (xx) |
| DE (1) | DE20220885U1 (xx) |
| HR (1) | HRP20040642A2 (xx) |
| HU (1) | HUP0600679A2 (xx) |
| IL (1) | IL162457A0 (xx) |
| MX (1) | MXPA04006391A (xx) |
| PL (1) | PL371263A1 (xx) |
| WO (1) | WO2003065975A2 (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL150907A (en) * | 2002-07-25 | 2007-07-04 | Stephan Cherkez | Process for the preparation of stable amorphous calcium pseudomonate |
| ES2339682T3 (es) * | 2004-06-01 | 2010-05-24 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Procedimiento para la preparacion de la forma amorfa de un farmaco. |
| US8158139B2 (en) * | 2004-07-12 | 2012-04-17 | Taro Pharmaceuticals North America, Inc. | Topical gel formulation comprising organophosphate insecticide and preparation thereof |
| WO2006017263A1 (en) | 2004-07-12 | 2006-02-16 | Taro Pharmaceutical Industries Ltd. | Topical gel formulation comprising organophosphate insecticide and its preparation thereof |
| WO2006109934A1 (en) * | 2005-03-28 | 2006-10-19 | Pantech Co., Ltd. | Multiple access digital communicating method in ultra-wideband radio access networks |
| US7560445B2 (en) * | 2005-07-06 | 2009-07-14 | Taro Pharmaceuticals North America, Inc. | Process for preparing malathion for pharmaceutical use |
| GB2441328A (en) | 2006-08-30 | 2008-03-05 | Alpharma Aps | A method for obtaining mupirocin calcium |
| AR099354A1 (es) | 2013-11-15 | 2016-07-20 | Akebia Therapeutics Inc | Formas sólidas de ácido {[5-(3-clorofenil)-3-hidroxipiridin-2-carbonil]amino}acético, composiciones, y sus usos |
| CN107963991A (zh) * | 2017-12-29 | 2018-04-27 | 成都百裕制药股份有限公司 | 一种无定形托伐普坦的生产方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643240A1 (de) | 1966-09-16 | 1971-06-24 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung neuer racemischer oder optisch aktiver 1-Phenoxy-2-aminoalkane |
| US3977943A (en) | 1971-06-12 | 1976-08-31 | Beecham Group Limited | Antibiotics |
| GB1395907A (en) | 1971-06-12 | 1975-05-29 | Beecham Group Ltd | Antibiotics |
| US4071536A (en) | 1971-06-12 | 1978-01-31 | Beecham Group Limited | Antibiotics |
| JPS5270083A (en) | 1975-12-04 | 1977-06-10 | Yoshitomi Pharmaceut Ind Ltd | Manufacture of an antibiotics, trans-pseudomonic acid |
| GB1577730A (en) * | 1976-10-23 | 1980-10-29 | Beecham Group Ltd | Treatment of infections with pseudomonicacid salts or esters thereof |
| GB1577545A (en) | 1977-07-27 | 1980-10-22 | Beecham Group Ltd | Treatment of swine dysenter |
| CA1103264A (en) | 1977-09-30 | 1981-06-16 | Norman H. Rogers | Purification of pseudomonic acid |
| CA1115699A (en) | 1978-05-20 | 1982-01-05 | Alan D. Curzons | Lithium pseudomonate and its preparation |
| CA1196284A (en) | 1982-05-28 | 1985-11-05 | Joshua Oduro-Yeboah | Pharmaceutical formulations |
| GB8415579D0 (en) | 1984-06-19 | 1984-07-25 | Beecham Group Plc | Compounds |
| GB8428952D0 (en) * | 1984-11-16 | 1984-12-27 | Beecham Group Plc | Formulations |
| GB8530796D0 (en) | 1985-12-13 | 1986-01-22 | Beecham Group Plc | Pharmaceutical composition |
| IE59628B1 (en) | 1986-06-26 | 1994-03-09 | Beecham Group Plc | Treatment of fungal infections |
| US5594026A (en) | 1990-12-11 | 1997-01-14 | Smithkline Beecham Group P.L.C. | Polymorphs of crystalline mupirocin |
| US5292892A (en) | 1991-05-07 | 1994-03-08 | Sankyo Company, Limited | Anti-bacterial compound and pharmaceutical compositions thereof |
| US6503881B2 (en) | 1996-08-21 | 2003-01-07 | Micrologix Biotech Inc. | Compositions and methods for treating infections using cationic peptides alone or in combination with antibiotics |
| KR20000048812A (ko) | 1996-10-01 | 2000-07-25 | 스튜어트 알. 수터, 스티븐 베네티아너, 피터 존 기딩스 | 병원성 유기체에 의한 비인두 전이증식 관련 세균 감염 치료용약제를 제조하기 위한 뮤피로신의 용도 |
| US6231875B1 (en) | 1998-03-31 | 2001-05-15 | Johnson & Johnson Consumer Companies, Inc. | Acidified composition for topical treatment of nail and skin conditions |
| DE19849924A1 (de) * | 1998-10-29 | 2000-05-04 | Degussa | Verfahren zur Abtrennung organischer Säuren aus wäßrigen Lösungen |
| TR200102234T2 (tr) | 1999-02-03 | 2002-10-21 | Biogal Gyogyszergyar Rt. | Psödomonik asit A antibiyotiğinin mikrobiyolojik yöntem ile hazırlanması için işlem |
| HUP0105286A3 (en) | 1999-02-03 | 2003-03-28 | Biogal Gyogyszergyar | Process for the isolation of pseudomonic acid a from pseudomonic acid complex-containing culture broth |
| US6335023B1 (en) | 1999-06-30 | 2002-01-01 | Ruey J. Yu | Oligosaccharide aldonic acids and their topical use |
| US6528086B2 (en) | 1999-09-28 | 2003-03-04 | Zars, Inc. | Methods and apparatus for drug delivery involving phase changing formulations |
| IL137363A (en) | 2000-07-18 | 2005-12-18 | Agis Ind 1983 Ltd | Pharmaceutical compositions containing mupirocin |
| CA2448547A1 (en) * | 2001-06-21 | 2003-01-03 | Biogal Gyogyszergyar Rt. | Metabolic controlled fermentation process for pseudomonic acid production |
| IL150907A (en) * | 2002-07-25 | 2007-07-04 | Stephan Cherkez | Process for the preparation of stable amorphous calcium pseudomonate |
-
2002
- 2002-11-06 HU HU0600679A patent/HUP0600679A2/hu unknown
- 2002-11-06 IL IL16245702A patent/IL162457A0/xx unknown
- 2002-11-06 WO PCT/US2002/035585 patent/WO2003065975A2/en active Application Filing
- 2002-11-06 US US10/289,919 patent/US7737177B2/en not_active Expired - Fee Related
- 2002-11-06 DE DE20220885U patent/DE20220885U1/de not_active Expired - Lifetime
- 2002-11-06 AU AU2002365431A patent/AU2002365431A1/en not_active Abandoned
- 2002-11-06 EP EP02805702A patent/EP1455769A4/en not_active Withdrawn
- 2002-11-06 PL PL02371263A patent/PL371263A1/xx unknown
- 2002-11-06 KR KR10-2004-7005940A patent/KR20040075857A/ko not_active Application Discontinuation
- 2002-11-06 CA CA002460970A patent/CA2460970C/en not_active Expired - Fee Related
- 2002-11-06 CN CNA02826391XA patent/CN1625394A/zh active Pending
- 2002-11-06 JP JP2003565401A patent/JP2005516984A/ja active Pending
-
2004
- 2004-06-25 MX MXPA04006391A patent/MXPA04006391A/es not_active Application Discontinuation
- 2004-07-13 HR HR20040642A patent/HRP20040642A2/hr not_active Application Discontinuation
-
2006
- 2006-07-07 US US11/483,418 patent/US20080249322A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7737177B2 (en) | 2010-06-15 |
| WO2003065975A3 (en) | 2004-02-19 |
| HUP0600679A2 (en) | 2008-06-30 |
| WO2003065975A2 (en) | 2003-08-14 |
| AU2002365431A1 (en) | 2003-09-02 |
| JP2005516984A (ja) | 2005-06-09 |
| IL162457A0 (en) | 2005-11-20 |
| CA2460970A1 (en) | 2003-08-14 |
| EP1455769A2 (en) | 2004-09-15 |
| CN1625394A (zh) | 2005-06-08 |
| US20080249322A1 (en) | 2008-10-09 |
| EP1455769A4 (en) | 2004-09-22 |
| KR20040075857A (ko) | 2004-08-30 |
| DE20220885U1 (de) | 2004-06-24 |
| US20040024052A1 (en) | 2004-02-05 |
| PL371263A1 (en) | 2005-06-13 |
| CA2460970C (en) | 2005-10-18 |
| MXPA04006391A (es) | 2004-10-04 |
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