NO324951B1 - Azitromycin og fremgangsmate for fremstilling derav - Google Patents
Azitromycin og fremgangsmate for fremstilling derav Download PDFInfo
- Publication number
- NO324951B1 NO324951B1 NO20032371A NO20032371A NO324951B1 NO 324951 B1 NO324951 B1 NO 324951B1 NO 20032371 A NO20032371 A NO 20032371A NO 20032371 A NO20032371 A NO 20032371A NO 324951 B1 NO324951 B1 NO 324951B1
- Authority
- NO
- Norway
- Prior art keywords
- azithromycin
- monohydrate
- water
- weeks
- water content
- 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 abstract description 81
- 229960004099 azithromycin Drugs 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000004682 monohydrates Chemical class 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 230000015556 catabolic process Effects 0.000 description 11
- 238000006731 degradation reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000000634 powder X-ray diffraction Methods 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 150000004683 dihydrates Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007857 degradation product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- -1 ammonia or alkali Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960000763 azithromycin anhydrous Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- SIERWFVYDSKSDJ-UHFFFAOYSA-M magnesium;hydroxide Chemical compound [OH-].[Mg+2] SIERWFVYDSKSDJ-UHFFFAOYSA-M 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000721 toxic potential Toxicity 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
- A61P31/04—Antibacterial agents
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)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25311900P | 2000-11-27 | 2000-11-27 | |
| GB0031355A GB0031355D0 (en) | 2000-12-21 | 2000-12-21 | Organic compounds |
| PCT/EP2001/013760 WO2002042315A2 (en) | 2000-11-27 | 2001-11-26 | Macrolide solvates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20032371D0 NO20032371D0 (no) | 2003-05-26 |
| NO20032371L NO20032371L (no) | 2003-07-10 |
| NO324951B1 true NO324951B1 (no) | 2008-01-14 |
Family
ID=26245472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20032371A NO324951B1 (no) | 2000-11-27 | 2003-05-26 | Azitromycin og fremgangsmate for fremstilling derav |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6949519B2 (cs) |
| EP (1) | EP1339730A2 (cs) |
| JP (1) | JP2004519430A (cs) |
| KR (1) | KR100815163B1 (cs) |
| AU (1) | AU2002221895A1 (cs) |
| BG (1) | BG66200B1 (cs) |
| CA (1) | CA2429639C (cs) |
| CZ (1) | CZ303343B6 (cs) |
| EE (1) | EE05200B1 (cs) |
| HR (1) | HRP20030430B1 (cs) |
| HU (1) | HU229488B1 (cs) |
| NO (1) | NO324951B1 (cs) |
| PL (1) | PL207076B1 (cs) |
| SK (1) | SK287814B6 (cs) |
| WO (1) | WO2002042315A2 (cs) |
Families Citing this family (17)
| 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 |
| US6861413B2 (en) | 2001-05-22 | 2005-03-01 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| JP2004530703A (ja) | 2001-05-22 | 2004-10-07 | ファイザー・プロダクツ・インク | 結晶形アジスロマイシン |
| GB0214277D0 (en) * | 2002-06-20 | 2002-07-31 | Biochemie Gmbh | Organic compounds |
| US6855813B2 (en) | 2002-07-19 | 2005-02-15 | Alembic Limited | Process for the preparation of azithromycin monohydrate |
| 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 |
| GB0224197D0 (en) * | 2002-10-17 | 2002-11-27 | Biochemie Gmbh | Organic compounds |
| EP1606299A1 (en) * | 2003-03-25 | 2005-12-21 | Teva Pharmaceutical Industries Ltd. | Degradation products of azithromycin, and methods for their identification |
| US20050101547A1 (en) * | 2003-11-06 | 2005-05-12 | Sadatrezaei Mohsen | Stabilized azithromycin composition |
| US7943585B2 (en) | 2003-12-22 | 2011-05-17 | Sandoz, Inc. | Extended release antibiotic composition |
| US7384921B2 (en) | 2004-02-20 | 2008-06-10 | Enanta Pharmaceuticals, Inc. | Polymorphic forms of 6-11 bicyclic ketolide derivatives |
| 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 |
| JP4471941B2 (ja) * | 2005-03-10 | 2010-06-02 | 山一電機株式会社 | 半導体装置用ソケット |
| US20090318375A1 (en) * | 2005-06-08 | 2009-12-24 | Hanmi Pharm Co., Ltd | Crystalline Azithromycin L-Malate Monohydrate and Pharmaceutical Composition Containing Same |
| US20120058936A1 (en) | 2009-03-13 | 2012-03-08 | Assistance Publique - Hopitaux De Paris | Compositions and methods for elimination of gram negative bacteria |
Family Cites Families (10)
| 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 |
| PT102006B (pt) * | 1997-05-19 | 2000-06-30 | Hovione Sociedade Quimica S A | Novo processo de preparacao de azitromicina |
| PT102130A (pt) * | 1998-03-13 | 1999-09-30 | Hovione Sociedade Quimica S A | Processo de preparacao de dihidrato de azitromicina |
| CA2245398C (en) * | 1998-08-21 | 2002-01-29 | Apotex Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
| JP2002531409A (ja) * | 1998-11-30 | 2002-09-24 | テバ ファーマシューティカル インダストリーズ リミティド | アジスロマイシンのエタノール付加物、その製造方法、及びその医薬製剤 |
| HRP20010956B1 (hr) * | 1999-06-29 | 2010-09-30 | Biochemie S.A. | Makrolidi |
| ES2177373B1 (es) * | 1999-11-26 | 2003-11-01 | Astur Pharma Sa | Preparacion de azitromicina en su forma no cristalina |
-
2001
- 2001-11-26 CZ CZ20031439A patent/CZ303343B6/cs not_active IP Right Cessation
- 2001-11-26 PL PL361276A patent/PL207076B1/pl unknown
- 2001-11-26 CA CA002429639A patent/CA2429639C/en not_active Expired - Fee Related
- 2001-11-26 WO PCT/EP2001/013760 patent/WO2002042315A2/en active Application Filing
- 2001-11-26 JP JP2002544448A patent/JP2004519430A/ja not_active Withdrawn
- 2001-11-26 HU HU0302099A patent/HU229488B1/hu not_active IP Right Cessation
- 2001-11-26 EE EEP200300255A patent/EE05200B1/xx not_active IP Right Cessation
- 2001-11-26 AU AU2002221895A patent/AU2002221895A1/en not_active Abandoned
- 2001-11-26 EP EP01997498A patent/EP1339730A2/en not_active Withdrawn
- 2001-11-26 SK SK635-2003A patent/SK287814B6/sk not_active IP Right Cessation
- 2001-11-26 HR HR20030430A patent/HRP20030430B1/xx not_active IP Right Cessation
- 2001-11-26 US US10/432,545 patent/US6949519B2/en not_active Expired - Fee Related
- 2001-11-26 KR KR1020037006623A patent/KR100815163B1/ko not_active Expired - Fee Related
-
2003
- 2003-05-21 BG BG107832A patent/BG66200B1/bg unknown
- 2003-05-26 NO NO20032371A patent/NO324951B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HRP20030430A2 (en) | 2005-04-30 |
| NO20032371L (no) | 2003-07-10 |
| CZ20031439A3 (cs) | 2003-10-15 |
| HUP0302099A2 (hu) | 2003-10-28 |
| EE200300255A (et) | 2003-08-15 |
| US6949519B2 (en) | 2005-09-27 |
| US20040053862A1 (en) | 2004-03-18 |
| SK6352003A3 (en) | 2003-11-04 |
| HUP0302099A3 (en) | 2009-08-28 |
| CZ303343B6 (cs) | 2012-08-08 |
| EE05200B1 (et) | 2009-08-17 |
| SK287814B6 (sk) | 2011-11-04 |
| CA2429639A1 (en) | 2002-05-30 |
| PL207076B1 (pl) | 2010-10-29 |
| KR20030055305A (ko) | 2003-07-02 |
| HRP20030430B1 (hr) | 2011-11-30 |
| HU229488B1 (hu) | 2014-01-28 |
| NO20032371D0 (no) | 2003-05-26 |
| AU2002221895A1 (en) | 2002-06-03 |
| EP1339730A2 (en) | 2003-09-03 |
| WO2002042315A3 (en) | 2002-10-31 |
| BG107832A (bg) | 2004-07-30 |
| WO2002042315A2 (en) | 2002-05-30 |
| JP2004519430A (ja) | 2004-07-02 |
| BG66200B1 (bg) | 2012-01-31 |
| KR100815163B1 (ko) | 2008-03-19 |
| PL361276A1 (en) | 2004-10-04 |
| CA2429639C (en) | 2009-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |