ES2195727A1 - Un procedimiento para la obtencion de claritromicina. - Google Patents
Un procedimiento para la obtencion de claritromicina.Info
- Publication number
- ES2195727A1 ES2195727A1 ES200101562A ES200101562A ES2195727A1 ES 2195727 A1 ES2195727 A1 ES 2195727A1 ES 200101562 A ES200101562 A ES 200101562A ES 200101562 A ES200101562 A ES 200101562A ES 2195727 A1 ES2195727 A1 ES 2195727A1
- Authority
- ES
- Spain
- Prior art keywords
- clarithromycin
- acetal
- oxime
- necessary
- reaction
- 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.)
- Granted
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 abstract 4
- 229960002626 clarithromycin Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 2
- 150000001241 acetals Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 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 compound 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 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007806 chemical reaction intermediate Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000003386 deoximation reaction Methods 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- -1 oxime hydrochloride Chemical class 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 150000004756 silanes Chemical class 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
Un procedimiento para la obtención de claritromicina. Este procedimiento está destinado a la obtención de la claritromicina; según el procedimiento se parte del clorohidrato de 9-oxima de eritromicina A, el cual se transforma en claritromicina mediante una secuencia sintética en la que inicialmente se forma un acetal de la 9-oxima. El uso del clorohidrato de oxima permite que sólo sea necesario utilizar cantidades catalíticas de sales de piridina para favorecer la reacción. Seguidamente se protegen los hidroxilos deposiciones 2'' y 4'''' con un agente sililante, se metila el hidroxilo deposición 6; todo ello sin que sea necesario el aislamiento de ningún intermedio de reacción. Finalmente la desprotección del acetal y de los silanos de 2'' y 4'''', seguida de la desoximación rinde claritromicina con alto rendimiento y de forma fácilmente aplicable industrialmente.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200101562A ES2195727B1 (es) | 2001-07-05 | 2001-07-05 | Un procedimiento para la obtencion de claritromicina. |
| US10/180,127 US6642364B2 (en) | 2001-07-05 | 2002-06-27 | Process to obtain clarithromycin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200101562A ES2195727B1 (es) | 2001-07-05 | 2001-07-05 | Un procedimiento para la obtencion de claritromicina. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2195727A1 true ES2195727A1 (es) | 2003-12-01 |
| ES2195727B1 ES2195727B1 (es) | 2005-03-01 |
Family
ID=8498293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200101562A Expired - Fee Related ES2195727B1 (es) | 2001-07-05 | 2001-07-05 | Un procedimiento para la obtencion de claritromicina. |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US6642364B2 (es) |
| ES (1) | ES2195727B1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0302466A2 (hu) * | 2000-02-29 | 2003-11-28 | Teva Pharmaceutical Industries Ltd. | Eljárások clarithromycin, clarithromycin intermedier, gyakorlatilag oximmentes clarithromycin és ezt tartalmazó gyógyszerkészítmény előállítására |
| US20050084540A1 (en) * | 2003-10-17 | 2005-04-21 | Indranil Nandi | Taste masking antibiotic composition |
| US8168228B2 (en) * | 2003-10-17 | 2012-05-01 | Sandoz Ag | Antibiotic clarithromycin micropellet compositions |
| US20050101547A1 (en) * | 2003-11-06 | 2005-05-12 | Sadatrezaei Mohsen | Stabilized azithromycin composition |
| WO2009023191A2 (en) * | 2007-08-09 | 2009-02-19 | Teva Pharmaceutical Industries Ltd. | An improved process for the preparation of clarithromycin |
| CN111747979B (zh) * | 2020-07-07 | 2021-10-08 | 新乡海滨药业有限公司 | 一种美罗培南关键中间体n-三甲基硅咪唑的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0272110A2 (en) * | 1986-12-17 | 1988-06-22 | Taisho Pharmaceutical Co. Ltd | Erythromycin a derivatives and method for the preparation of the same |
| JPH0276893A (ja) * | 1988-06-15 | 1990-03-16 | Taisho Pharmaceut Co Ltd | エリスロマイシンａ誘導体およびその製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1036084A1 (en) * | 1997-12-01 | 2000-09-20 | Abbott Laboratories | Chemical synthesis of 6-o-alkyl erythromycin c |
-
2001
- 2001-07-05 ES ES200101562A patent/ES2195727B1/es not_active Expired - Fee Related
-
2002
- 2002-06-27 US US10/180,127 patent/US6642364B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0272110A2 (en) * | 1986-12-17 | 1988-06-22 | Taisho Pharmaceutical Co. Ltd | Erythromycin a derivatives and method for the preparation of the same |
| JPH0276893A (ja) * | 1988-06-15 | 1990-03-16 | Taisho Pharmaceut Co Ltd | エリスロマイシンａ誘導体およびその製造方法 |
Non-Patent Citations (1)
| Title |
|---|
| BASE DE DATOS CA en STN, AN 113:132694 & JP 02076893 A (TAISHO PHARMACEUTICAL) 16.03.1990, resumen. * |
Also Published As
| Publication number | Publication date |
|---|---|
| US6642364B2 (en) | 2003-11-04 |
| US20030023053A1 (en) | 2003-01-30 |
| ES2195727B1 (es) | 2005-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
Ref document number: 2195727B1 Country of ref document: ES |
|
| FD1A | Patent lapsed |
Effective date: 20100315 |