ES2179756A1 - Method for obtaining azaerythromycin - Google Patents
Method for obtaining azaerythromycinInfo
- Publication number
- ES2179756A1 ES2179756A1 ES200002858A ES200002858A ES2179756A1 ES 2179756 A1 ES2179756 A1 ES 2179756A1 ES 200002858 A ES200002858 A ES 200002858A ES 200002858 A ES200002858 A ES 200002858A ES 2179756 A1 ES2179756 A1 ES 2179756A1
- Authority
- ES
- Spain
- Prior art keywords
- azaerythromycin
- obtaining
- iminoether
- erythromycin
- yielding
- 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
- HRKNNHYKWGYTEN-HOQMJRDDSA-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-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)NC[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 HRKNNHYKWGYTEN-HOQMJRDDSA-N 0.000 title abstract 3
- 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 abstract 1
- 229930006677 Erythromycin A Natural products 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000005456 alcohol based solvent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229960003276 erythromycin Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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)
- 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)
Abstract
The invention relates to a method for obtaining azaerythromycin of formula (I) from 6,9-iminoether of erythromycin A, which is catalytically reduced at low pressure (less than 5 bars) after adjusting the pH with an appropriate acid and using alcohol solvents with 1-3 carbon atoms or mixtures thereof with water. High-yielding, highly-pure azaerythromycin is obtained under adequate conditions.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200002858A ES2179756B1 (en) | 2000-11-30 | 2000-11-30 | PROCEDURE FOR OBTAINING AZAERITHROMYCIN. |
| PT10256401A PT102564B (en) | 2000-11-30 | 2001-02-12 | PROCESS FOR THE PREPARATION OF AZAERITROMYCIN |
| PCT/ES2001/000452 WO2002044193A1 (en) | 2000-11-30 | 2001-11-26 | Method for obtaining azaerythromycin |
| AU2002220757A AU2002220757A1 (en) | 2000-11-30 | 2001-11-26 | Method for obtaining azaerythromycin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200002858A ES2179756B1 (en) | 2000-11-30 | 2000-11-30 | PROCEDURE FOR OBTAINING AZAERITHROMYCIN. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2179756A1 true ES2179756A1 (en) | 2003-01-16 |
| ES2179756B1 ES2179756B1 (en) | 2004-10-01 |
Family
ID=8495813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES200002858A Expired - Fee Related ES2179756B1 (en) | 2000-11-30 | 2000-11-30 | PROCEDURE FOR OBTAINING AZAERITHROMYCIN. |
Country Status (4)
| Country | Link |
|---|---|
| AU (1) | AU2002220757A1 (en) |
| ES (1) | ES2179756B1 (en) |
| PT (1) | PT102564B (en) |
| WO (1) | WO2002044193A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1304407C (en) * | 2004-09-03 | 2007-03-14 | 南京圣和药业有限公司 | Azithromycin refining process |
| WO2007029266A2 (en) * | 2005-05-24 | 2007-03-15 | Kopran Research Laboratories Ltd | A process for preparing 9-deoxo-9a-aza-9a-homoerythromycin a |
| WO2007015265A2 (en) * | 2005-05-24 | 2007-02-08 | Kopran Research Laboratories Ltd | A process for preparing 6,9-imino ether |
| WO2007017898A2 (en) * | 2005-05-24 | 2007-02-15 | Kopran Research Laboratories Ltd. | A process of recovery of pt/c catalyst in the preparation of azithromycin dihydrate |
| CN109575092B (en) * | 2018-12-19 | 2022-05-10 | 宜昌东阳光生化制药有限公司 | Synthesis method of azithromycin rearrangement impurity lactam |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328334A (en) * | 1979-04-02 | 1982-05-04 | Pliva Pharmaceutical And Chemical Works | 11-Aza-10-deoxo-10-dihydroerythromycin A and derivatives thereof as well as a process for their preparation |
| WO1994026758A1 (en) * | 1993-05-19 | 1994-11-24 | Pfizer Inc. | Intermediate for azithromycin |
| EP0879823A1 (en) * | 1997-05-19 | 1998-11-25 | Hovione Inter Ltd. | Preparation of azithromycin |
-
2000
- 2000-11-30 ES ES200002858A patent/ES2179756B1/en not_active Expired - Fee Related
-
2001
- 2001-02-12 PT PT10256401A patent/PT102564B/en not_active IP Right Cessation
- 2001-11-26 AU AU2002220757A patent/AU2002220757A1/en not_active Abandoned
- 2001-11-26 WO PCT/ES2001/000452 patent/WO2002044193A1/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328334A (en) * | 1979-04-02 | 1982-05-04 | Pliva Pharmaceutical And Chemical Works | 11-Aza-10-deoxo-10-dihydroerythromycin A and derivatives thereof as well as a process for their preparation |
| WO1994026758A1 (en) * | 1993-05-19 | 1994-11-24 | Pfizer Inc. | Intermediate for azithromycin |
| EP0879823A1 (en) * | 1997-05-19 | 1998-11-25 | Hovione Inter Ltd. | Preparation of azithromycin |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002220757A1 (en) | 2002-06-11 |
| ES2179756B1 (en) | 2004-10-01 |
| WO2002044193A1 (en) | 2002-06-06 |
| PT102564A (en) | 2002-05-31 |
| PT102564B (en) | 2004-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 20030116 Kind code of ref document: A1 |
|
| FG2A | Definitive protection |
Ref document number: 2179756B1 Country of ref document: ES |
|
| FD1A | Patent lapsed |
Effective date: 20100803 |