CN100339384C - 阿齐霉素的乙醇化物，制备方法以及医药组合物 - Google Patents
阿齐霉素的乙醇化物，制备方法以及医药组合物 Download PDFInfo
- Publication number
- CN100339384C CN100339384C CNB2005100785525A CN200510078552A CN100339384C CN 100339384 C CN100339384 C CN 100339384C CN B2005100785525 A CNB2005100785525 A CN B2005100785525A CN 200510078552 A CN200510078552 A CN 200510078552A CN 100339384 C CN100339384 C CN 100339384C
- Authority
- CN
- China
- Prior art keywords
- azithromycin
- ethanolate
- weight
- ethanol
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229960004099 azithromycin Drugs 0.000 title claims abstract description 62
- 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 abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000002425 crystallisation Methods 0.000 claims abstract description 12
- 230000008025 crystallization Effects 0.000 claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- 241000894006 Bacteria Species 0.000 claims 2
- 241000251468 Actinopterygii Species 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010037075 Protozoal infections Diseases 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract 1
- 229960004756 ethanol Drugs 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930006677 Erythromycin A Natural products 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 229960003276 erythromycin Drugs 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent 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
- 238000012360 testing method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- -1 weighing scale) Chemical compound 0.000 description 1
Images
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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11029898P | 1998-11-30 | 1998-11-30 | |
| US60/110298 | 1998-11-30 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998158542A Division CN1273142C (zh) | 1998-11-30 | 1999-11-30 | 阿齐霉素的乙醇化物,制备方法以及医药组合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1737008A CN1737008A (zh) | 2006-02-22 |
| CN100339384C true CN100339384C (zh) | 2007-09-26 |
Family
ID=22332273
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100785525A Expired - Fee Related CN100339384C (zh) | 1998-11-30 | 1999-11-30 | 阿齐霉素的乙醇化物，制备方法以及医药组合物 |
| CNB998158542A Expired - Fee Related CN1273142C (zh) | 1998-11-30 | 1999-11-30 | 阿齐霉素的乙醇化物,制备方法以及医药组合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB998158542A Expired - Fee Related CN1273142C (zh) | 1998-11-30 | 1999-11-30 | 阿齐霉素的乙醇化物,制备方法以及医药组合物 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6365574B2 (enExample) |
| EP (2) | EP1484062A1 (enExample) |
| JP (1) | JP2002531409A (enExample) |
| KR (1) | KR100603226B1 (enExample) |
| CN (2) | CN100339384C (enExample) |
| AP (1) | AP1709A (enExample) |
| AT (1) | ATE279200T1 (enExample) |
| AU (1) | AU768219B2 (enExample) |
| BG (1) | BG105547A (enExample) |
| CA (1) | CA2352562A1 (enExample) |
| CZ (1) | CZ20011886A3 (enExample) |
| DE (1) | DE69921192T2 (enExample) |
| DK (1) | DK1152765T3 (enExample) |
| ES (1) | ES2229804T3 (enExample) |
| HK (1) | HK1043725B (enExample) |
| HU (1) | HUP0104241A3 (enExample) |
| IL (1) | IL143376A0 (enExample) |
| LV (1) | LV12735B (enExample) |
| NZ (1) | NZ512496A (enExample) |
| PL (1) | PL197894B1 (enExample) |
| PT (1) | PT1152765E (enExample) |
| RO (1) | RO121408B1 (enExample) |
| RU (1) | RU2240124C2 (enExample) |
| SI (1) | SI20639A (enExample) |
| WO (1) | WO2000032203A1 (enExample) |
| ZA (1) | ZA200104312B (enExample) |
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 |
| CA2245398C (en) | 1998-08-21 | 2002-01-29 | Apotex Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
| HK1043725B (en) * | 1998-11-30 | 2005-05-06 | Teva Pharmaceutical Industries Ltd. | Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions thereof |
| JP2004519430A (ja) * | 2000-11-27 | 2004-07-02 | バイオケミ・エセ・ア | マクロライドの溶媒和物 |
| 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 |
| KR100431431B1 (ko) * | 2001-04-25 | 2004-05-14 | 한미약품 주식회사 | 아지트로마이신 수화물의 1,2-프로필렌글리콜 내포화합물,그의 제조방법 및 그의 약학적 조성물 |
| HUP0400446A2 (hu) * | 2001-05-22 | 2004-09-28 | Pfizer Products Inc. | Azitromicin kristályformái |
| US6861413B2 (en) * | 2001-05-22 | 2005-03-01 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| EP1671978A1 (en) * | 2001-05-22 | 2006-06-21 | Pfizer Products Inc. | New Cristal Form of Azithromycin |
| EP1541134A3 (en) * | 2001-10-18 | 2007-06-06 | Teva Pharmaceutical Industries Limited | Stabilized azithromycin compositions |
| EP1446010B1 (en) | 2001-10-18 | 2009-04-15 | Teva Pharmaceutical Industries Ltd. | Stabilized azithromycin compositions |
| US20080149521A9 (en) * | 2001-10-18 | 2008-06-26 | Michael Pesachovich | Methods of stabilizing azithromycin |
| IL161259A0 (en) * | 2001-12-21 | 2004-09-27 | Pfizer Prod Inc | Methods for wet granulating azithromycin |
| WO2003053416A1 (en) * | 2001-12-21 | 2003-07-03 | Pfizer Products Inc. | Directly compressible formulations of azithromycin |
| PL372394A1 (en) * | 2002-02-01 | 2005-07-25 | Pfizer Products Inc. | Dry granulated formulations of azithromycin |
| 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 |
| 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 |
| JP2007513147A (ja) * | 2003-12-04 | 2007-05-24 | ファイザー・プロダクツ・インク | 押し出し機を使用して、好ましくはポロキサマーとグリセリドを含有する多粒子結晶性医薬組成物を製造するための噴霧凝結方法 |
| CA2547597A1 (en) * | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Multiparticulate compositions with improved stability |
| DE602004014805D1 (de) * | 2003-12-04 | 2008-08-14 | Pfizer Prod Inc | Verfahren zur herstellung von pharmazeutischen multiteilchenförmigen produkten |
| CN1889933A (zh) * | 2003-12-04 | 2007-01-03 | 辉瑞产品公司 | 由基于液体的工艺制备的阿奇霉素多颗粒剂型 |
| WO2005053652A1 (en) | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Multiparticulate crystalline drug compositions containing a poloxamer and a glyceride |
| US7943585B2 (en) | 2003-12-22 | 2011-05-17 | Sandoz, Inc. | Extended release antibiotic composition |
| US20060116336A1 (en) * | 2004-03-17 | 2006-06-01 | American Pharmaceutical Partners, Inc. | Lyophilized azithromycin formulation |
| US7468428B2 (en) * | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
| US7683162B2 (en) * | 2004-08-30 | 2010-03-23 | Taro Pharmaceutical Industries Limited | Process of preparing a crystalline azithromycin monohydrate |
| CA2591744A1 (en) * | 2004-12-21 | 2006-06-29 | Pfizer Products Inc. | 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 |
| US9433516B2 (en) * | 2007-04-17 | 2016-09-06 | Micell Technologies, Inc. | Stents having controlled elution |
| JP2012520268A (ja) | 2009-03-13 | 2012-09-06 | ダ・ボルテラ | グラム陰性細菌の除去のための組成物及び方法 |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU43006B (en) | 1981-03-06 | 1989-02-28 | Pliva Pharm & Chem Works | Process for preparing n-methyl-11-aza-10-deoxo-10-dihydro erythromycin 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 |
| CA2245398C (en) * | 1998-08-21 | 2002-01-29 | Apotex Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
| HK1043725B (en) * | 1998-11-30 | 2005-05-06 | 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 |
| HUP0400446A2 (hu) * | 2001-05-22 | 2004-09-28 | Pfizer Products Inc. | Azitromicin kristályformái |
-
1999
- 1999-11-30 HK HK02102775.5A patent/HK1043725B/en not_active IP Right Cessation
- 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 CA CA002352562A patent/CA2352562A1/en not_active Abandoned
- 1999-11-30 NZ NZ512496A patent/NZ512496A/xx unknown
- 1999-11-30 DE DE69921192T patent/DE69921192T2/de not_active Expired - Fee Related
- 1999-11-30 RO ROA200100573A patent/RO121408B1/ro unknown
- 1999-11-30 WO PCT/US1999/028368 patent/WO2000032203A1/en not_active Ceased
- 1999-11-30 RU RU2001118035/15A patent/RU2240124C2/ru not_active IP Right Cessation
- 1999-11-30 KR KR1020017006669A patent/KR100603226B1/ko not_active Expired - Fee Related
- 1999-11-30 DK DK99965069T patent/DK1152765T3/da active
- 1999-11-30 EP EP04014455A patent/EP1484062A1/en not_active Withdrawn
- 1999-11-30 PT PT99965069T patent/PT1152765E/pt unknown
- 1999-11-30 ES ES99965069T patent/ES2229804T3/es not_active Expired - Lifetime
- 1999-11-30 CN CNB998158542A patent/CN1273142C/zh not_active Expired - Fee Related
- 1999-11-30 EP EP99965069A patent/EP1152765B1/en not_active Expired - Lifetime
- 1999-11-30 AP APAP/P/2001/002183A patent/AP1709A/en active
- 1999-11-30 PL PL347971A patent/PL197894B1/pl not_active IP Right Cessation
- 1999-11-30 IL IL14337699A patent/IL143376A0/xx unknown
- 1999-11-30 US US09/451,738 patent/US6365574B2/en not_active Expired - Lifetime
- 1999-11-30 AT AT99965069T patent/ATE279200T1/de not_active IP Right Cessation
- 1999-11-30 HU HU0104241A patent/HUP0104241A3/hu unknown
- 1999-11-30 JP JP2000584898A patent/JP2002531409A/ja active Pending
- 1999-11-30 SI SI9920086A patent/SI20639A/sl not_active IP Right Cessation
- 1999-11-30 CZ CZ20011886A patent/CZ20011886A3/cs unknown
-
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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100339384C (zh) | 阿齐霉素的乙醇化物，制备方法以及医药组合物 | |
| WO2000032203A9 (en) | Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions thereof | |
| EP2578596A1 (en) | Levocarrimycin, pharmaceutical compositions, preparation methods and uses thereof | |
| RU2478643C2 (ru) | Макроциклические полиморфы, композиции, содержащие такие полиморфы, и способы их применения и получения | |
| RU2647236C1 (ru) | Левоизовалерилспирамицин ii, препараты, способ приготовления и употребления | |
| CN111812250A (zh) | 一种水产品中药物残留的快速检测方法 | |
| WO2022007629A1 (zh) | 乌帕替尼的晶型及其制备方法和用途 | |
| CN119060111A (zh) | 一种高品质乳糖酸红霉素的制备方法 | |
| FI75173B (fi) | Foerfarande foer framstaellning av nya cytostatiskt verkande antracyklinderivat. | |
| MXPA04009009A (es) | Pseudopolimorfos isoestructurales de 9-desoxo-9a-aza-9a-metil-9a-homoeritromicina a. | |
| WO1996019489A1 (en) | Compounds | |
| CN102382007B (zh) | 一种盐酸多西环素化合物及其制法 | |
| CN110204470A (zh) | 一种艾地骨化醇的新的结晶形式及其制备方法和应用 | |
| CN116143647A (zh) | 双氯芬酸二乙胺的新晶型及其制备方法 | |
| CN113149857B (zh) | 一种酰胺类化合物及其制备方法和用途 | |
| CN114315897B (zh) | 一种磷酸特地唑胺新晶体及其制备方法 | |
| HUT54298A (en) | Process for producing pharmaceutical compositions containing p(2-)5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphtyl(-propenyl)-phenol active for the immunsysthem | |
| CN107266518B (zh) | 一种糠酸莫米松晶型及其制备方法 | |
| CN116178138A (zh) | 一种忍冬藤提取物的制备方法与应用 | |
| CN120535429A (zh) | 一种米洛巴林-富马酸晶型及其制备方法 | |
| CN108586556A (zh) | 一种喷司他丁的新晶型及其制备方法和用途 | |
| CN1896063A (zh) | 一种更稳定的高熔点阿立哌唑新晶型及其制备方法 | |
| CN101775005A (zh) | 盐酸卡屈沙星i型结晶及其制备方法 | |
| SI8612050A8 (sl) | Nova nehigroskopična oblika n,n-dimetil-1-1-(4-klorofenil) ciklobutil -3-metilbutilamin klorhidrata |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |