ES2177373B1 - Preparacion de azitromicina en su forma no cristalina - Google Patents
Preparacion de azitromicina en su forma no cristalinaInfo
- Publication number
- ES2177373B1 ES2177373B1 ES009902620A ES9902620A ES2177373B1 ES 2177373 B1 ES2177373 B1 ES 2177373B1 ES 009902620 A ES009902620 A ES 009902620A ES 9902620 A ES9902620 A ES 9902620A ES 2177373 B1 ES2177373 B1 ES 2177373B1
- Authority
- ES
- Spain
- Prior art keywords
- preparation
- azithromycin
- crystalline form
- dsc
- spectroscopy
- 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
- 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 abstract 2
- 229960004099 azithromycin Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 abstract 3
- 238000004566 IR spectroscopy Methods 0.000 abstract 1
- 238000002441 X-ray diffraction Methods 0.000 abstract 1
- 238000007707 calorimetry Methods 0.000 abstract 1
- 150000004683 dihydrates Chemical group 0.000 abstract 1
- 239000003120 macrolide antibiotic agent Substances 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Preparación de azitromicina en su forma no cristalina. La invención describe un procedimiento en el que el producto final se obtiene por liofilización de azitromicina en una solución de un alcohol alifático o de un éter cíclico. La invención describe métodos analíticos para diferenciar las formas no cristalina y la dihidrato cristalizada de azitromicina.
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009902620A ES2177373B1 (es) | 1999-11-26 | 1999-11-26 | Preparacion de azitromicina en su forma no cristalina |
| DE60003509T DE60003509T2 (de) | 1999-11-26 | 2000-02-23 | Herstellung von nicht-kristallinen und kristallinen Dihydratformen von Azithromycin |
| AT00500028T ATE243704T1 (de) | 1999-11-26 | 2000-02-23 | Herstellung von nicht-kristallinen und kristallinen dihydratformen von azithromycin |
| EP01204550A EP1234833B1 (en) | 1999-11-26 | 2000-02-23 | Preparation of crystalline azithromycin dihydrate. |
| EP00500028A EP1103558B1 (en) | 1999-11-26 | 2000-02-23 | Preparation of non-crystalline and crystalline dihydrate forms of azithromycin |
| DE60027919T DE60027919D1 (de) | 1999-11-26 | 2000-02-23 | Herstellung von kristalliner Dihydratform von Azithromycin |
| AT01204550T ATE325805T1 (de) | 1999-11-26 | 2000-02-23 | Herstellung von kristalliner dihydratform von azithromycin |
| US09/718,833 US6451990B1 (en) | 1999-11-26 | 2000-11-22 | Azithromycin preparation in its noncryst alline and crystalline dihydrate forms |
| TR2000/03474A TR200003474A3 (tr) | 1999-11-26 | 2000-11-23 | Azitromisinin kristalli olmayan ve kristalli dihitrat formlarinin hazirlanmasi |
| PL344101A PL195910B1 (pl) | 1999-11-26 | 2000-11-24 | Sposób wytwarzania 9-deokso-9a-aza-9a-metylo-9a-homoerytromycyny A w formie niekrystalicznej |
| CA002485433A CA2485433C (en) | 1999-11-26 | 2000-11-24 | Preparation of non-crystalline and crystalline dihydrate forms of azithromycin |
| CA002326930A CA2326930C (en) | 1999-11-26 | 2000-11-24 | Preparation of non-crystalline and crystalline dihydrate forms of azithromycin |
| JP2000359948A JP4260354B2 (ja) | 1999-11-26 | 2000-11-27 | 非結晶および結晶二水和物形態のアジスロマイシンの調製 |
| ES200202318A ES2207403B1 (es) | 1999-11-26 | 2002-10-09 | Preparacion de azitromicina en su forma dihidrato cristalina. |
| JP2008217072A JP2009007376A (ja) | 1999-11-26 | 2008-08-26 | 非結晶および結晶二水和物形態のアジスロマイシンの調製 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009902620A ES2177373B1 (es) | 1999-11-26 | 1999-11-26 | Preparacion de azitromicina en su forma no cristalina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2177373A1 ES2177373A1 (es) | 2002-12-01 |
| ES2177373B1 true ES2177373B1 (es) | 2003-11-01 |
Family
ID=8310747
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES009902620A Expired - Fee Related ES2177373B1 (es) | 1999-11-26 | 1999-11-26 | Preparacion de azitromicina en su forma no cristalina |
| ES200202318A Expired - Fee Related ES2207403B1 (es) | 1999-11-26 | 2002-10-09 | Preparacion de azitromicina en su forma dihidrato cristalina. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200202318A Expired - Fee Related ES2207403B1 (es) | 1999-11-26 | 2002-10-09 | Preparacion de azitromicina en su forma dihidrato cristalina. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6451990B1 (es) |
| EP (2) | EP1234833B1 (es) |
| JP (2) | JP4260354B2 (es) |
| AT (2) | ATE243704T1 (es) |
| CA (1) | CA2326930C (es) |
| DE (2) | DE60027919D1 (es) |
| ES (2) | ES2177373B1 (es) |
| PL (1) | PL195910B1 (es) |
| TR (1) | TR200003474A3 (es) |
Families Citing this family (32)
| 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 |
| CA2245398C (en) | 1998-08-21 | 2002-01-29 | Apotex Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
| ES2162764B1 (es) * | 2000-05-17 | 2003-04-01 | Ercros Ind Sa | Forma polimorfica del dihidrato de azitromicina, y su procedimiento deobtencion. |
| SK287814B6 (sk) * | 2000-11-27 | 2011-11-04 | Sandoz Ag | Azithromycin in the form of a monohydrate, a process for its preparation and pharmaceutical compositions comprising same |
| IN190080B (es) * | 2001-01-29 | 2003-06-07 | Alembic Ltd | |
| KR100491183B1 (ko) * | 2001-03-21 | 2005-05-25 | 한미약품 주식회사 | 아지트로마이신의 제조방법 및 이 방법에 사용되는9-데옥소-9에이-아자-9에이-호모에리트로마이신 에이의결정성 수화물 |
| EP1671978A1 (en) * | 2001-05-22 | 2006-06-21 | Pfizer Products Inc. | New Cristal Form of Azithromycin |
| SK14402003A3 (sk) | 2001-05-22 | 2004-06-08 | Pfizer Products Inc. | Kryštalické formy azitromycínu |
| US6861413B2 (en) | 2001-05-22 | 2005-03-01 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| EP1455758A1 (en) | 2001-12-21 | 2004-09-15 | Pfizer Products Inc. | Directly compressible formulations of azithromycin |
| US7452692B2 (en) | 2002-02-13 | 2008-11-18 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Method for extracting a macrolide from biomatter |
| CA2475383C (en) | 2002-02-13 | 2009-12-22 | Biogal Gyogyszergyar Rt. | Method for extracting a macrolide from biomatter |
| 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 |
| KR20050114262A (ko) * | 2003-03-31 | 2005-12-05 | 테바 기오기스제르갸르 레스즈베니타르사사그 | 마크로라이드의 결정화 및 정제 |
| WO2005010015A1 (en) | 2003-07-24 | 2005-02-03 | Teva Gyogyszergyar Reszvenytarsasag | Method of purifying macrolides |
| ES2308274T3 (es) * | 2003-12-04 | 2008-12-01 | Pfizer Products Inc. | Procedimiento para fabricar multiparticulados farmaceuticos. |
| US7384921B2 (en) * | 2004-02-20 | 2008-06-10 | Enanta Pharmaceuticals, Inc. | Polymorphic forms of 6-11 bicyclic ketolide derivatives |
| US7468428B2 (en) | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
| WO2006115494A1 (en) * | 2005-04-26 | 2006-11-02 | American Pharmaceutical Partners, Inc. | 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 |
| US7464012B2 (en) * | 2004-12-10 | 2008-12-09 | L'air Liquide, Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Simplified process simulator |
| US7582312B2 (en) * | 2004-11-15 | 2009-09-01 | Discovery Laboratories, Inc. | Methods to produce lung surfactant formulations via lyophilization and formulations and uses thereof |
| MX2007005222A (es) | 2004-12-01 | 2007-06-26 | Teva Gyogyszergyar Zartkoruen | Pimecrolimus amorfo no higroscopico y en polvo. |
| EP1904510A1 (en) * | 2005-07-14 | 2008-04-02 | Pfizer Products Incorporated | Process for forming amorphous azithromycin particles |
| AR058283A1 (es) * | 2005-12-07 | 2008-01-30 | Wyeth Corp | Metodos para la preparacion de rapamicina cristalina y para la medicion de la cristalinidad de los compuestos de rapamicina utilizando calorimetria diferencial de barrido |
| UA102128C2 (en) * | 2008-12-05 | 2013-06-10 | Х. Луннбек А/С | Nalmefene hydrochloride dihydrate |
| WO2011015219A1 (en) | 2009-08-06 | 2011-02-10 | Shifa Pharmed Industrial Group Co. | Process for the purification of azithromycin by separation from its thermal degradation products and/or isomers |
| RU2012130435A (ru) * | 2009-12-18 | 2014-01-27 | Норт-Вест Юниверсити | Композиция на основе макролида и способ его получения |
| WO2013088274A1 (en) * | 2011-12-14 | 2013-06-20 | Wockhardt Limited | Anhydrous amorphous azithromycin composition free of azithromycin dihydrate |
| CN106188177A (zh) * | 2016-07-12 | 2016-12-07 | 浙江亚太药业股份有限公司 | 一种阿奇霉素化合物的制备方法及其药物制剂 |
| CN108003109A (zh) * | 2017-12-18 | 2018-05-08 | 南开大学 | 一种大环内酯化合物的晶型及其制备方法与用途 |
Family Cites Families (9)
| 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 |
| MX12213A (es) | 1987-07-09 | 1993-05-01 | Pfizer | Metodo de preparacion de dihidrato de azitromicina cristalino |
| CA2162401C (en) | 1993-05-19 | 1998-11-03 | Bingwei V. Yang | Intermediate for azithromycin |
| ECSP951389A (es) | 1995-02-21 | 1996-05-10 | Un procedimiento de obtencion de hidrato de azitromicina | |
| ES2122905B1 (es) | 1996-07-11 | 1999-11-16 | Astur Pharma Sa | Sintesis de 11,12-hidrogenoortoborato de 9-desoxo-9a-aza-11,12-desoxi-9a-metil-9a-homoeritromicina a. un procedimiento para la preparacion de 9-desoxo-9a-aza-9a-metil-9a-homoeritromicina a dihidrato (azitromicina dihidrato). |
| PT102130A (pt) | 1998-03-13 | 1999-09-30 | Hovione Sociedade Quimica S A | Processo de preparacao de dihidrato de azitromicina |
| 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 |
-
1999
- 1999-11-26 ES ES009902620A patent/ES2177373B1/es not_active Expired - Fee Related
-
2000
- 2000-02-23 AT AT00500028T patent/ATE243704T1/de not_active IP Right Cessation
- 2000-02-23 DE DE60027919T patent/DE60027919D1/de not_active Expired - Lifetime
- 2000-02-23 AT AT01204550T patent/ATE325805T1/de not_active IP Right Cessation
- 2000-02-23 DE DE60003509T patent/DE60003509T2/de not_active Expired - Fee Related
- 2000-02-23 EP EP01204550A patent/EP1234833B1/en not_active Expired - Lifetime
- 2000-02-23 EP EP00500028A patent/EP1103558B1/en not_active Expired - Lifetime
- 2000-11-22 US US09/718,833 patent/US6451990B1/en not_active Expired - Fee Related
- 2000-11-23 TR TR2000/03474A patent/TR200003474A3/tr unknown
- 2000-11-24 PL PL344101A patent/PL195910B1/pl not_active IP Right Cessation
- 2000-11-24 CA CA002326930A patent/CA2326930C/en not_active Expired - Fee Related
- 2000-11-27 JP JP2000359948A patent/JP4260354B2/ja not_active Expired - Fee Related
-
2002
- 2002-10-09 ES ES200202318A patent/ES2207403B1/es not_active Expired - Fee Related
-
2008
- 2008-08-26 JP JP2008217072A patent/JP2009007376A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE60027919D1 (de) | 2006-06-14 |
| ATE325805T1 (de) | 2006-06-15 |
| TR200003474A2 (tr) | 2001-07-23 |
| CA2326930C (en) | 2005-03-22 |
| DE60003509D1 (de) | 2003-07-31 |
| DE60003509T2 (de) | 2004-04-15 |
| ES2207403B1 (es) | 2005-03-01 |
| US6451990B1 (en) | 2002-09-17 |
| EP1103558B1 (en) | 2003-06-25 |
| TR200003474A3 (tr) | 2001-07-23 |
| EP1234833B1 (en) | 2006-05-10 |
| ES2207403A1 (es) | 2004-05-16 |
| EP1103558A2 (en) | 2001-05-30 |
| PL195910B1 (pl) | 2007-11-30 |
| JP2001187797A (ja) | 2001-07-10 |
| ES2177373A1 (es) | 2002-12-01 |
| ATE243704T1 (de) | 2003-07-15 |
| EP1234833A2 (en) | 2002-08-28 |
| EP1103558A3 (en) | 2001-07-04 |
| EP1234833A3 (en) | 2003-03-12 |
| JP2009007376A (ja) | 2009-01-15 |
| JP4260354B2 (ja) | 2009-04-30 |
| PL344101A1 (en) | 2001-06-04 |
| CA2326930A1 (en) | 2001-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 20021201 Kind code of ref document: A1 |
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| FG2A | Definitive protection |
Ref document number: 2177373B1 Country of ref document: ES |
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| FD2A | Announcement of lapse in spain |
Effective date: 20190521 |
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Effective date: 20190604 |