AU735598B2 - Crystal form 0 of clarithromycin - Google Patents
Crystal form 0 of clarithromycin Download PDFInfo
- Publication number
- AU735598B2 AU735598B2 AU55326/98A AU5532698A AU735598B2 AU 735598 B2 AU735598 B2 AU 735598B2 AU 55326/98 A AU55326/98 A AU 55326/98A AU 5532698 A AU5532698 A AU 5532698A AU 735598 B2 AU735598 B2 AU 735598B2
- Authority
- AU
- Australia
- Prior art keywords
- methylerythromycin
- solvate
- complex
- prepared
- bacterial infections
- 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
Links
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 title claims description 94
- 229960002626 clarithromycin Drugs 0.000 title claims description 35
- 239000013078 crystal Substances 0.000 title claims description 14
- 239000012453 solvate Substances 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 229920002125 Sokalan® Polymers 0.000 claims description 31
- 229960001631 carbomer Drugs 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- MWBJRTBANFUBOX-SQYJNGITSA-N (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/O)/[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MWBJRTBANFUBOX-SQYJNGITSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 14
- 208000035143 Bacterial infection Diseases 0.000 claims description 13
- 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 claims description 13
- 229930006677 Erythromycin A Natural products 0.000 claims description 13
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 13
- 229960003276 erythromycin Drugs 0.000 claims description 13
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 11
- 229940011051 isopropyl acetate Drugs 0.000 claims description 11
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- YBZRLMLGUBIIDN-UHFFFAOYSA-N Spicamycin Chemical compound O1C(C(O)CO)C(NC(=O)CNC(=O)CCCCCCCCCCCCC(C)C)C(O)C(O)C1NC1=NC=NC2=C1NC=N2 YBZRLMLGUBIIDN-UHFFFAOYSA-N 0.000 claims description 8
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- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 6
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- KYTWXIARANQMCA-RWJQBGPGSA-N (3r,4s,5s,6r,7r,9r,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2 Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=NO)[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 KYTWXIARANQMCA-RWJQBGPGSA-N 0.000 claims 2
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 claims 2
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- -1 6-O-methylerythromycin A oxime Chemical class 0.000 description 5
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/785,623 US5945405A (en) | 1997-01-17 | 1997-01-17 | Crystal form O of clarithromycin |
| US08/785623 | 1997-01-17 | ||
| PCT/US1997/023607 WO1998031699A1 (en) | 1997-01-17 | 1997-12-19 | Crystal form 0 of clarithromycin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5532698A AU5532698A (en) | 1998-08-07 |
| AU735598B2 true AU735598B2 (en) | 2001-07-12 |
Family
ID=25136084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU55326/98A Expired AU735598B2 (en) | 1997-01-17 | 1997-12-19 | Crystal form 0 of clarithromycin |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5945405A (enExample) |
| EP (1) | EP1077988A1 (enExample) |
| JP (3) | JP4058114B2 (enExample) |
| KR (1) | KR100567149B1 (enExample) |
| CN (1) | CN1174991C (enExample) |
| AR (3) | AR011077A1 (enExample) |
| AU (1) | AU735598B2 (enExample) |
| BR (1) | BR9714287A (enExample) |
| CA (4) | CA2387356C (enExample) |
| CZ (1) | CZ297433B6 (enExample) |
| DE (1) | DE97951771T1 (enExample) |
| ES (1) | ES2173058T1 (enExample) |
| IL (1) | IL130255A0 (enExample) |
| NZ (1) | NZ336073A (enExample) |
| TR (1) | TR199901578T2 (enExample) |
| TW (1) | TW574224B (enExample) |
| WO (1) | WO1998031699A1 (enExample) |
| ZA (1) | ZA98116B (enExample) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5945405A (en) * | 1997-01-17 | 1999-08-31 | Abbott Laboratories | Crystal form O of clarithromycin |
| KR100377159B1 (ko) * | 1998-09-09 | 2003-08-19 | 한미약품공업 주식회사 | 잔류 용매가 없는 클라리스로마이신의 결정형 2의 제조 방법 |
| GB9827355D0 (en) * | 1998-12-11 | 1999-02-03 | Biochemie Sa | Organic compounds |
| KR100322313B1 (ko) * | 1999-10-21 | 2002-02-06 | 민경윤 | 클라리스로마이신 결정형 2의 제조방법 및 이에 사용되는 클라리스로마이신 포르메이트 |
| US6627743B1 (en) | 1999-12-03 | 2003-09-30 | Abbott Laboratories | 6-O-methylerythromycin A crystal form III |
| CN1666991A (zh) * | 1999-12-16 | 2005-09-14 | 特瓦制药工业有限公司 | 克拉霉素多晶型物的制备方法和新的多晶型物ⅳ |
| FR2802534B1 (fr) * | 1999-12-20 | 2002-02-01 | Merial Sas | Procede pour preparer et isoler la 9-deoxo-9 (z)- hydroxyiminoerythromycine a |
| CN1450903A (zh) | 2000-01-11 | 2003-10-22 | 特瓦制药工业有限公司 | 克拉霉素多晶型物的制备方法 |
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| US6565882B2 (en) | 2000-02-24 | 2003-05-20 | Advancis Pharmaceutical Corp | Antibiotic composition with inhibitor |
| CA2401571A1 (en) * | 2000-02-29 | 2001-09-07 | Ilya Avrutov | Processes for preparing clarithromycin and clarithromycin intermediate, essentially oxime-free clarithromycin, and pharmaceutical composition comprising the same |
| DE60122791T2 (de) * | 2000-03-15 | 2007-10-04 | Hanmi Pharm. Co., Ltd. | Verfahren zur Herstellung von Clarythromycin mit nicht pharmazeutischer Qualität |
| KR100367981B1 (ko) * | 2000-11-23 | 2003-01-14 | 한미약품공업 주식회사 | 클라리스로마이신 결정형 2의 제조 방법 및 이 방법에사용되는 결정성 클라리스로마이신 메실레이트 삼수화물 |
| AU6381201A (en) * | 2000-03-28 | 2001-10-08 | Biochemie Gmbh | Granulated particles with masked taste |
| US8980290B2 (en) | 2000-08-03 | 2015-03-17 | Antares Pharma Ipl Ag | Transdermal compositions for anticholinergic agents |
| US20040198706A1 (en) * | 2003-03-11 | 2004-10-07 | Carrara Dario Norberto R. | Methods and formulations for transdermal or transmucosal application of active agents |
| US20070225379A1 (en) * | 2001-08-03 | 2007-09-27 | Carrara Dario Norberto R | Transdermal delivery of systemically active central nervous system drugs |
| US7198801B2 (en) * | 2000-08-03 | 2007-04-03 | Antares Pharma Ipl Ag | Formulations for transdermal or transmucosal application |
| ATE485837T1 (de) * | 2000-08-03 | 2010-11-15 | Antares Pharma Ipl Ag | Zusammensetzung zur transdermalen und/oder transmukosalen verabreichung von wirkstoffen, die ausreichende therapeutische spiegel garantiert |
| US20020068078A1 (en) | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
| US6541014B2 (en) | 2000-10-13 | 2003-04-01 | Advancis Pharmaceutical Corp. | Antiviral product, use and formulation thereof |
| KR100408848B1 (ko) * | 2001-03-12 | 2003-12-06 | 주식회사 씨트리 | 클래리스로마이신의 정제방법 |
| RU2217160C2 (ru) * | 2001-04-20 | 2003-11-27 | Челябинская государственная медицинская академия | Способ местного лечения урогенитального хламидиоза у женщин |
| JP2004537566A (ja) * | 2001-08-01 | 2004-12-16 | ブリストル−マイヤーズ スクイブ カンパニー | 味マスキング組成物 |
| TW200302830A (en) * | 2002-01-11 | 2003-08-16 | Chugai Pharmaceutical Co Ltd | Anhydrate/hydrate of an erythromycin derivative and processes for preparing said anhydrate/hydrate |
| CN100427498C (zh) * | 2003-03-02 | 2008-10-22 | 王凌峰 | 克拉霉素a型结晶 |
| US20040185092A1 (en) * | 2003-03-18 | 2004-09-23 | Yih Ming Hsiao | Pharmaceutical preparations of omeprazole and/or clarithromycin for oral use |
| JP2006528185A (ja) | 2003-07-21 | 2006-12-14 | アドバンシス ファーマスーティカル コーポレイション | 抗生物質製剤、その使用法及び作成方法 |
| EP1648415A4 (en) | 2003-07-21 | 2011-11-16 | Middlebrook Pharmaceuticals Inc | ANTIBIOTIC PRODUCT, ITS USE AND FORMULATION |
| WO2005009368A2 (en) | 2003-07-21 | 2005-02-03 | Advancis Pharmaceutical Corporation | Antibiotic product, use and formulation thereof |
| CA2535177A1 (en) | 2003-08-11 | 2005-02-24 | Advancis Pharmaceutical Corporation | Robust pellet |
| CA2535398C (en) | 2003-08-12 | 2013-11-12 | Advancis Pharmaceuticals Corporation | Antibiotic product, use and formulation thereof |
| WO2005023184A2 (en) * | 2003-08-29 | 2005-03-17 | Advancis Pharmaceuticals Corporation | Antibiotic product, use and formulation thereof |
| AU2004273830B2 (en) | 2003-09-15 | 2011-03-24 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| PL1670433T3 (pl) | 2003-10-10 | 2013-03-29 | Ferring Bv | Przezskórna formulacja farmaceutyczna do zmniejszania pozostałości na skórze |
| EP1771158A4 (en) | 2004-07-02 | 2008-03-12 | Advancis Pharmaceutical Corp | TABLET FOR PULSE DISTRIBUTION |
| US20060111560A1 (en) * | 2004-11-01 | 2006-05-25 | Glenmark Pharmaceuticals Limited | Process for the preparation of crystalline form II of clarithromycin |
| US8067399B2 (en) * | 2005-05-27 | 2011-11-29 | Antares Pharma Ipl Ag | Method and apparatus for transdermal or transmucosal application of testosterone |
| CA2614412A1 (en) * | 2005-07-07 | 2007-01-18 | Elan Pharma International, Limited | Nanoparticulate clarithromycin formulations |
| WO2007036951A2 (en) * | 2005-08-31 | 2007-04-05 | Alembic Limited | Process to obtain 6-o-methylerythromycin a (clarithromycin)_form ii |
| US8778924B2 (en) | 2006-12-04 | 2014-07-15 | Shionogi Inc. | Modified release amoxicillin products |
| US8357394B2 (en) | 2005-12-08 | 2013-01-22 | Shionogi Inc. | Compositions and methods for improved efficacy of penicillin-type antibiotics |
| CN101426475A (zh) | 2006-04-21 | 2009-05-06 | 安塔雷斯制药Ipl股份公司 | 使用用于经皮或经粘膜应用的制剂治疗热潮红的方法 |
| US8299052B2 (en) | 2006-05-05 | 2012-10-30 | Shionogi Inc. | Pharmaceutical compositions and methods for improved bacterial eradication |
| WO2008067991A2 (en) * | 2006-12-08 | 2008-06-12 | Antares Pharma Ipl Ag | Skin-friendly drug complexes for transdermal administration |
| DE102007016367A1 (de) | 2007-04-03 | 2008-10-09 | Grünenthal GmbH | Polymorph von Clarithromycin (Form V) |
| WO2009023191A2 (en) * | 2007-08-09 | 2009-02-19 | Teva Pharmaceutical Industries Ltd. | An improved process for the preparation of clarithromycin |
| EP2030613A1 (en) | 2007-08-17 | 2009-03-04 | Abbott GmbH & Co. KG | Preparation of compositions with essentially noncrystalline embedded macrolide antibiotics |
| US9119769B2 (en) | 2011-12-30 | 2015-09-01 | The Curators Of The University Of Missouri | Method for transforming pharmaceutical crystal forms |
| CN103087130B (zh) * | 2013-02-06 | 2015-12-23 | 浙江国邦药业有限公司 | 一种克拉霉素晶型转换方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5782400A (en) | 1980-11-12 | 1982-05-22 | Taisho Pharmaceut Co Ltd | Erythromycin derivative |
| US4331803A (en) * | 1980-06-04 | 1982-05-25 | Taisho Pharmaceutical Co., Ltd. | Novel erythromycin compounds |
| JPS60214796A (ja) | 1984-04-06 | 1985-10-28 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシン類の製法 |
| JPS61103890A (ja) | 1984-10-26 | 1986-05-22 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシンａ誘導体 |
| US4670549A (en) | 1985-03-18 | 1987-06-02 | Taisho Pharmaceutical Co., Ltd. | Method for selective methylation of erythromycin a derivatives |
| DE3782994T2 (de) * | 1986-09-18 | 1993-04-08 | Taisho Pharma Co Ltd | Erythromycin-a-derivate und verfahren zu ihrer herstellung. |
| JPH0755958B2 (ja) * | 1986-10-03 | 1995-06-14 | 大正製薬株式会社 | エリスロマイシンａ誘導体の製造方法 |
| KR960000434B1 (ko) * | 1986-12-17 | 1996-01-06 | 다이쇼 세이야꾸 가부시끼가이샤 | 에리스로마이신 a유도체 및 그의 제조 방법 |
| JP2526951B2 (ja) * | 1986-12-17 | 1996-08-21 | 大正製薬株式会社 | エリスロマイシンａ誘導体およびその製造方法 |
| US4808411A (en) * | 1987-06-05 | 1989-02-28 | Abbott Laboratories | Antibiotic-polymer compositions |
| JP2751385B2 (ja) * | 1988-05-19 | 1998-05-18 | 大正製薬株式会社 | エリスロマイシンａオキシム及びその塩の製造方法 |
| US5556839A (en) * | 1991-04-29 | 1996-09-17 | Eli Lilly And Company | Form II Dirithromycin |
| US5872229A (en) | 1995-11-21 | 1999-02-16 | Abbott Laboratories | Process for 6-O-alkylation of erythromycin derivatives |
| US5837829A (en) | 1996-04-02 | 1998-11-17 | Abbott Laboratories | 9-oximesilyl erythromycin a derivatives |
| US5719272A (en) | 1996-04-02 | 1998-02-17 | Abbott Laboratories | 2'-protected 3'-dimethylamine, 9-etheroxime erythromycin A derivatives |
| CA2261732C (en) * | 1996-07-29 | 2001-07-24 | Abbott Laboratories | Preparation of crystal form ii of clarithromycin |
| US5858986A (en) * | 1996-07-29 | 1999-01-12 | Abbott Laboratories | Crystal form I of clarithromycin |
| US5945405A (en) * | 1997-01-17 | 1999-08-31 | Abbott Laboratories | Crystal form O of clarithromycin |
-
1997
- 1997-01-17 US US08/785,623 patent/US5945405A/en not_active Expired - Lifetime
- 1997-12-19 TR TR1999/01578T patent/TR199901578T2/xx unknown
- 1997-12-19 CA CA002387356A patent/CA2387356C/en not_active Expired - Lifetime
- 1997-12-19 CA CA002277274A patent/CA2277274C/en not_active Expired - Lifetime
- 1997-12-19 JP JP53437298A patent/JP4058114B2/ja not_active Expired - Lifetime
- 1997-12-19 ES ES97951771T patent/ES2173058T1/es active Pending
- 1997-12-19 KR KR1019997006446A patent/KR100567149B1/ko not_active Expired - Fee Related
- 1997-12-19 CN CNB971814325A patent/CN1174991C/zh not_active Expired - Fee Related
- 1997-12-19 NZ NZ336073A patent/NZ336073A/xx not_active IP Right Cessation
- 1997-12-19 EP EP97951771A patent/EP1077988A1/en not_active Withdrawn
- 1997-12-19 CA CA002387361A patent/CA2387361C/en not_active Expired - Lifetime
- 1997-12-19 DE DE0001077988T patent/DE97951771T1/de active Pending
- 1997-12-19 IL IL13025597A patent/IL130255A0/xx not_active IP Right Cessation
- 1997-12-19 WO PCT/US1997/023607 patent/WO1998031699A1/en not_active Ceased
- 1997-12-19 BR BR9714287-5A patent/BR9714287A/pt not_active Application Discontinuation
- 1997-12-19 CZ CZ0242699A patent/CZ297433B6/cs not_active IP Right Cessation
- 1997-12-19 AU AU55326/98A patent/AU735598B2/en not_active Expired
- 1997-12-19 CA CA002419499A patent/CA2419499A1/en not_active Abandoned
- 1997-12-30 TW TW86119997A patent/TW574224B/zh not_active IP Right Cessation
-
1998
- 1998-01-07 ZA ZA98116A patent/ZA98116B/xx unknown
- 1998-01-16 AR ARP980100207A patent/AR011077A1/es not_active Application Discontinuation
-
2003
- 2003-04-24 AR ARP030101427A patent/AR039666A2/es not_active Application Discontinuation
- 2003-04-24 AR ARP030101428A patent/AR039667A2/es not_active Application Discontinuation
- 2003-09-03 JP JP2003311358A patent/JP2004075689A/ja not_active Withdrawn
-
2008
- 2008-12-24 JP JP2008327022A patent/JP5190350B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CZ297433B6 (cs) | 2006-12-13 |
| JP2004075689A (ja) | 2004-03-11 |
| US5945405A (en) | 1999-08-31 |
| BR9714287A (pt) | 2000-04-18 |
| AU5532698A (en) | 1998-08-07 |
| CN1244869A (zh) | 2000-02-16 |
| JP2000509725A (ja) | 2000-08-02 |
| AR039666A2 (es) | 2005-03-02 |
| DE97951771T1 (de) | 2004-07-08 |
| CA2387361A1 (en) | 1998-07-23 |
| CA2387356C (en) | 2003-05-27 |
| CA2419499A1 (en) | 1998-07-23 |
| WO1998031699A1 (en) | 1998-07-23 |
| EP1077988A1 (en) | 2001-02-28 |
| CA2277274C (en) | 2003-05-27 |
| AR011077A1 (es) | 2000-08-02 |
| CN1174991C (zh) | 2004-11-10 |
| KR100567149B1 (ko) | 2006-04-04 |
| NZ336073A (en) | 2001-01-26 |
| TW574224B (en) | 2004-02-01 |
| CA2277274A1 (en) | 1998-07-23 |
| KR20000070220A (ko) | 2000-11-25 |
| JP5190350B2 (ja) | 2013-04-24 |
| JP2009137975A (ja) | 2009-06-25 |
| CA2387361C (en) | 2003-05-27 |
| ES2173058T1 (es) | 2002-10-16 |
| IL130255A0 (en) | 2000-06-01 |
| AR039667A2 (es) | 2005-03-02 |
| CA2387356A1 (en) | 1998-07-23 |
| ZA98116B (en) | 1998-07-08 |
| TR199901578T2 (xx) | 1999-09-21 |
| CZ242699A3 (cs) | 1999-11-17 |
| JP4058114B2 (ja) | 2008-03-05 |
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| FGA | Letters patent sealed or granted (standard patent) |