WO2007015265A3 - A process for preparing 6,9-imino ether - Google Patents
A process for preparing 6,9-imino ether Download PDFInfo
- Publication number
- WO2007015265A3 WO2007015265A3 PCT/IN2006/000180 IN2006000180W WO2007015265A3 WO 2007015265 A3 WO2007015265 A3 WO 2007015265A3 IN 2006000180 W IN2006000180 W IN 2006000180W WO 2007015265 A3 WO2007015265 A3 WO 2007015265A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ether
- erythromycin
- lmino
- preparing
- imino ether
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,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-oxacyclotetradec Chemical compound 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)(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-PGYIPVOXSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 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 abstract 1
- PGNYNCTUBKSHHL-UHFFFAOYSA-N 2,3-diaminobutanedioic acid Chemical compound OC(=O)C(N)C(N)C(O)=O PGNYNCTUBKSHHL-UHFFFAOYSA-N 0.000 abstract 1
- VQEMDSRIOVZAOM-UHFFFAOYSA-N 4-(4-methylsulfonylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CSC(N)=N1 VQEMDSRIOVZAOM-UHFFFAOYSA-N 0.000 abstract 1
- 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
- 229960004924 azithromycin dihydrate Drugs 0.000 abstract 1
- 230000002051 biphasic effect Effects 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 238000006485 reductive methylation reaction Methods 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 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
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- 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
A process for preparing 6,9-lmino ether from Erythromycin thiocyanate without isolating Erythromycin base and Erythromycin oxime and Beckmann's rearrangement of erythromycin oxime is carried in the presence biphasic solvent system comprising methylene chloride and water in the presence of triethylamine along with sodium bicarbonate to obtain 87-96 % pure 6,9-lmino ether. Further the 6,9-lmino ether is hydrogenated to 9-Deoxo-9a-aza-9a-homoerythromycin A followed by reductive methylation to obtain Azithromycin dihydrate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN627MU2005 | 2005-05-24 | ||
| IN627/MUM/2005 | 2005-05-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2007015265A2 WO2007015265A2 (en) | 2007-02-08 |
| WO2007015265A3 true WO2007015265A3 (en) | 2007-12-06 |
Family
ID=37709013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2006/000180 WO2007015265A2 (en) | 2005-05-24 | 2006-05-24 | A process for preparing 6,9-imino ether |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2007015265A2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090054634A1 (en) * | 2007-08-09 | 2009-02-26 | Vinod Kumar Kansal | Process for the preparation of clarithromycin |
| WO2009156938A2 (en) * | 2008-06-24 | 2009-12-30 | Alembic Limited | A cost effective process for preparing 6,9-imino ether |
| US8106111B2 (en) | 2009-05-15 | 2012-01-31 | Eastman Chemical Company | Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions |
| CN105481913B (en) * | 2014-09-19 | 2019-01-08 | 宁夏启元药业有限公司 | A method of synthesis azithromycin |
| CN106083954B (en) * | 2016-06-22 | 2018-12-11 | 连云港笃翔化工有限公司 | A kind of preparation method of 6,9 imines ether compound of erythromycin |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994026758A1 (en) * | 1993-05-19 | 1994-11-24 | Pfizer Inc. | Intermediate for azithromycin |
| US20010047089A1 (en) * | 2000-01-04 | 2001-11-29 | Judith Aronhime | Preparation method of azithromycin dihydrate |
| WO2002044193A1 (en) * | 2000-11-30 | 2002-06-06 | Ercros Industrial, S.A. | Method for obtaining azaerythromycin |
| EP1469008A1 (en) * | 2000-03-15 | 2004-10-20 | Hanmi Pharm. Co., Ltd. | Method of preparing a non-pharmaceutical grade clarithromycin |
-
2006
- 2006-05-24 WO PCT/IN2006/000180 patent/WO2007015265A2/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994026758A1 (en) * | 1993-05-19 | 1994-11-24 | Pfizer Inc. | Intermediate for azithromycin |
| US20010047089A1 (en) * | 2000-01-04 | 2001-11-29 | Judith Aronhime | Preparation method of azithromycin dihydrate |
| EP1469008A1 (en) * | 2000-03-15 | 2004-10-20 | Hanmi Pharm. Co., Ltd. | Method of preparing a non-pharmaceutical grade clarithromycin |
| WO2002044193A1 (en) * | 2000-11-30 | 2002-06-06 | Ercros Industrial, S.A. | Method for obtaining azaerythromycin |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE CASREACT STN INTERNATIONAL, KARLSRUHE; 2003, QIN N.: "Study on the processes for preparation roxithromycin" * |
| GUANGDONG YAOXUE, vol. 13, no. 6, pages 23 - 24 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007015265A2 (en) | 2007-02-08 |
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