ZA200104312B - Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions thereof. - Google Patents
Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions thereof. Download PDFInfo
- Publication number
- ZA200104312B ZA200104312B ZA200104312A ZA200104312A ZA200104312B ZA 200104312 B ZA200104312 B ZA 200104312B ZA 200104312 A ZA200104312 A ZA 200104312A ZA 200104312 A ZA200104312 A ZA 200104312A ZA 200104312 B ZA200104312 B ZA 200104312B
- Authority
- ZA
- South Africa
- Prior art keywords
- azithromycin
- ethanolate
- ethanol
- water
- suspension
- Prior art date
Links
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 title claims description 43
- 229960004099 azithromycin Drugs 0.000 title claims description 42
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000000725 suspension Substances 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- HQUPLSLYZHKKQT-WVVFQGGUSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-o Chemical compound O.O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 HQUPLSLYZHKKQT-WVVFQGGUSA-N 0.000 description 3
- 229960003256 azithromycin monohydrate Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 102000017914 EDNRA Human genes 0.000 description 1
- 101150062404 EDNRA gene Proteins 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- 229930006677 Erythromycin A Natural products 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11029898P | 1998-11-30 | 1998-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104312B true ZA200104312B (en) | 2001-11-28 |
Family
ID=22332273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104312A ZA200104312B (en) | 1998-11-30 | 2001-05-25 | Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions thereof. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6365574B2 (https=) |
| EP (2) | EP1152765B1 (https=) |
| JP (1) | JP2002531409A (https=) |
| KR (1) | KR100603226B1 (https=) |
| CN (2) | CN100339384C (https=) |
| AP (1) | AP1709A (https=) |
| AT (1) | ATE279200T1 (https=) |
| AU (1) | AU768219B2 (https=) |
| BG (1) | BG105547A (https=) |
| CA (1) | CA2352562A1 (https=) |
| CZ (1) | CZ20011886A3 (https=) |
| DE (1) | DE69921192T2 (https=) |
| DK (1) | DK1152765T3 (https=) |
| ES (1) | ES2229804T3 (https=) |
| HK (1) | HK1043725B (https=) |
| HU (1) | HUP0104241A3 (https=) |
| IL (1) | IL143376A0 (https=) |
| LV (1) | LV12735B (https=) |
| NZ (1) | NZ512496A (https=) |
| PL (1) | PL197894B1 (https=) |
| PT (1) | PT1152765E (https=) |
| RO (1) | RO121408B1 (https=) |
| RU (1) | RU2240124C2 (https=) |
| SI (1) | SI20639A (https=) |
| WO (1) | WO2000032203A1 (https=) |
| ZA (1) | ZA200104312B (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20020231A2 (en) * | 2002-03-18 | 2003-12-31 | Pliva D D | ISOSTRUCTURAL PSEUDOPOLYMORPHS OF 9-DEOXO-9a-AZA-9a-METHYL-9a-HOMOERYTHROMYCIN A |
| TW546302B (en) * | 1998-05-08 | 2003-08-11 | Biochemie Sa | Improvements in macrolide production |
| US6245903B1 (en) | 1998-08-21 | 2001-06-12 | Apotex, Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
| AU768219B2 (en) * | 1998-11-30 | 2003-12-04 | Teva Pharmaceutical Industries Ltd. | Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions thereof |
| CN100341886C (zh) * | 2000-11-27 | 2007-10-10 | 桑多斯股份公司 | 大环内酯类化合物的溶剂化物 |
| EE05200B1 (et) * | 2000-11-27 | 2009-08-17 | Biochemie S.A. | Asitromtsiin monohdraadina, selle valmistamismeetod ja selle kasutamine ravimkoostises |
| KR100431431B1 (ko) * | 2001-04-25 | 2004-05-14 | 한미약품 주식회사 | 아지트로마이신 수화물의 1,2-프로필렌글리콜 내포화합물,그의 제조방법 및 그의 약학적 조성물 |
| DK1390377T3 (da) * | 2001-05-22 | 2006-06-19 | Pfizer Prod Inc | Ny krystalform af azithromycin |
| EP1652851A1 (en) | 2001-05-22 | 2006-05-03 | Pfizer Products Inc. | New crystal form of Azithromycin |
| US6861413B2 (en) * | 2001-05-22 | 2005-03-01 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| EP1541134A3 (en) * | 2001-10-18 | 2007-06-06 | Teva Pharmaceutical Industries Limited | Stabilized azithromycin compositions |
| US20080149521A9 (en) * | 2001-10-18 | 2008-06-26 | Michael Pesachovich | Methods of stabilizing azithromycin |
| EP1446010B1 (en) * | 2001-10-18 | 2009-04-15 | Teva Pharmaceutical Industries Ltd. | Stabilized azithromycin compositions |
| PL371259A1 (pl) * | 2001-12-21 | 2005-06-13 | Pfizer Products Inc. | Bezpośrednio sprasowywalne preparaty azytromycyny |
| AU2002353316A1 (en) * | 2001-12-21 | 2003-07-09 | Pfizer Products Inc. | Methods for wet granulating azithromycin |
| BR0307331A (pt) * | 2002-02-01 | 2004-12-07 | Pfizer Prod Inc | Formulações granuladas a seco de azitromicina |
| HRP20020614A2 (en) | 2002-07-22 | 2004-06-30 | PLIVA-ISTRAŽIVAČKI INSTITUT d.o.o. | Rhombic pseudopolymorph of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin a |
| US20050013835A1 (en) * | 2003-07-15 | 2005-01-20 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| US20050101547A1 (en) * | 2003-11-06 | 2005-05-12 | Sadatrezaei Mohsen | Stabilized azithromycin composition |
| BRPI0416534A (pt) * | 2003-12-04 | 2007-01-09 | Pfizer Prod Inc | composições multiparticuladas com estabilidade melhorada |
| WO2005053639A2 (en) * | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Controlled release multiparticulates formed with dissolution enhancers |
| US6984403B2 (en) * | 2003-12-04 | 2006-01-10 | Pfizer Inc. | Azithromycin dosage forms with reduced side effects |
| ATE399536T1 (de) * | 2003-12-04 | 2008-07-15 | Pfizer Prod Inc | Verfahren zur herstellung von pharmazeutischen multiteilchenförmigen produkten |
| EP1694304A2 (en) * | 2003-12-04 | 2006-08-30 | Pfizer Products Inc. | Azithromycin multiparticulate dosage forms by liquid-based processes |
| WO2005053652A1 (en) | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Multiparticulate crystalline drug compositions containing a poloxamer and a glyceride |
| CA2549225A1 (en) * | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Spray-congeal process using an extruder for preparing multiparticulate crystalline drug compositions containing preferably a poloxamer and a glyceride |
| US7943585B2 (en) | 2003-12-22 | 2011-05-17 | Sandoz, Inc. | Extended release antibiotic composition |
| US7468428B2 (en) * | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
| US20060116336A1 (en) * | 2004-03-17 | 2006-06-01 | American Pharmaceutical Partners, Inc. | Lyophilized azithromycin formulation |
| US7683162B2 (en) * | 2004-08-30 | 2010-03-23 | Taro Pharmaceutical Industries Limited | Process of preparing a crystalline azithromycin monohydrate |
| US20100048498A1 (en) * | 2004-12-21 | 2010-02-25 | Johnson Barbara A | Stable non-dihydrate azithromycin oral suspensions |
| US20060198895A1 (en) * | 2005-03-07 | 2006-09-07 | Kotliar Eleonora M | Azithromycin powder for oral suspension compositions |
| US20090318375A1 (en) * | 2005-06-08 | 2009-12-24 | Hanmi Pharm Co., Ltd | Crystalline Azithromycin L-Malate Monohydrate and Pharmaceutical Composition Containing Same |
| CA2754604A1 (en) | 2009-03-13 | 2010-09-16 | Da Volterra | Compositions and methods for elimination of gram-negative bacteria |
| WO2010121187A2 (en) * | 2009-04-17 | 2010-10-21 | Micell Techologies, Inc. | Stents having controlled elution |
| WO2013088274A1 (en) | 2011-12-14 | 2013-06-20 | Wockhardt Limited | Anhydrous amorphous azithromycin composition free of azithromycin dihydrate |
| CN103983730B (zh) * | 2014-06-11 | 2015-09-30 | 北京市药品检验所 | 阿奇霉素或其制剂中的杂质检查方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI8110592A8 (en) | 1981-03-06 | 1996-06-30 | Pliva Pharm & Chem Works | Process for preparing of n-methyl-11-aza-10-deoxo-10-dihydroerythromycine a and derivatives thereof |
| US4474768A (en) * | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| RO107257B1 (ro) * | 1987-07-09 | 1993-10-30 | Pfizer | Procedeu de obtinere a unui dihidrat de azitromicina, cristalin |
| WO1989002271A1 (en) * | 1987-09-10 | 1989-03-23 | Pfizer | Azithromycin and derivatives as antiprotozoal agents |
| CN1093370A (zh) * | 1993-12-10 | 1994-10-12 | 北京市集才药物研究所 | 一种新的阿齐红霉素结晶及其制备方法 |
| CN1161971A (zh) * | 1997-01-03 | 1997-10-15 | 石家庄制药集团有限公司 | 一种阿齐霉素结晶及其制备方法 |
| US6245903B1 (en) * | 1998-08-21 | 2001-06-12 | Apotex, Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
| AU768219B2 (en) * | 1998-11-30 | 2003-12-04 | Teva Pharmaceutical Industries Ltd. | Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions thereof |
| KR100491183B1 (ko) * | 2001-03-21 | 2005-05-25 | 한미약품 주식회사 | 아지트로마이신의 제조방법 및 이 방법에 사용되는9-데옥소-9에이-아자-9에이-호모에리트로마이신 에이의결정성 수화물 |
| DK1390377T3 (da) * | 2001-05-22 | 2006-06-19 | Pfizer Prod Inc | Ny krystalform af azithromycin |
-
1999
- 1999-11-30 AU AU31065/00A patent/AU768219B2/en not_active Ceased
- 1999-11-30 CN CNB2005100785525A patent/CN100339384C/zh not_active Expired - Fee Related
- 1999-11-30 HK HK02102775.5A patent/HK1043725B/en not_active IP Right Cessation
- 1999-11-30 DK DK99965069T patent/DK1152765T3/da active
- 1999-11-30 RO ROA200100573A patent/RO121408B1/ro unknown
- 1999-11-30 JP JP2000584898A patent/JP2002531409A/ja active Pending
- 1999-11-30 NZ NZ512496A patent/NZ512496A/xx unknown
- 1999-11-30 AP APAP/P/2001/002183A patent/AP1709A/en active
- 1999-11-30 EP EP99965069A patent/EP1152765B1/en not_active Expired - Lifetime
- 1999-11-30 DE DE69921192T patent/DE69921192T2/de not_active Expired - Fee Related
- 1999-11-30 CN CNB998158542A patent/CN1273142C/zh not_active Expired - Fee Related
- 1999-11-30 US US09/451,738 patent/US6365574B2/en not_active Expired - Lifetime
- 1999-11-30 SI SI9920086A patent/SI20639A/sl not_active IP Right Cessation
- 1999-11-30 IL IL14337699A patent/IL143376A0/xx unknown
- 1999-11-30 AT AT99965069T patent/ATE279200T1/de not_active IP Right Cessation
- 1999-11-30 KR KR1020017006669A patent/KR100603226B1/ko not_active Expired - Fee Related
- 1999-11-30 ES ES99965069T patent/ES2229804T3/es not_active Expired - Lifetime
- 1999-11-30 EP EP04014455A patent/EP1484062A1/en not_active Withdrawn
- 1999-11-30 PT PT99965069T patent/PT1152765E/pt unknown
- 1999-11-30 HU HU0104241A patent/HUP0104241A3/hu unknown
- 1999-11-30 WO PCT/US1999/028368 patent/WO2000032203A1/en not_active Ceased
- 1999-11-30 CZ CZ20011886A patent/CZ20011886A3/cs unknown
- 1999-11-30 PL PL347971A patent/PL197894B1/pl not_active IP Right Cessation
- 1999-11-30 CA CA002352562A patent/CA2352562A1/en not_active Abandoned
- 1999-11-30 RU RU2001118035/15A patent/RU2240124C2/ru not_active IP Right Cessation
-
2001
- 2001-05-25 ZA ZA200104312A patent/ZA200104312B/en unknown
- 2001-05-29 BG BG105547A patent/BG105547A/xx unknown
- 2001-06-22 LV LVP-01-79A patent/LV12735B/en unknown
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