ES8604251A1 - A PROCEDURE FOR THE PREPARATION OF N-METHYL-11-AZA-10-DEOXO-10-DIHYDROERITHROMYCIN A - Google Patents
A PROCEDURE FOR THE PREPARATION OF N-METHYL-11-AZA-10-DEOXO-10-DIHYDROERITHROMYCIN AInfo
- Publication number
- ES8604251A1 ES8604251A1 ES544878A ES544878A ES8604251A1 ES 8604251 A1 ES8604251 A1 ES 8604251A1 ES 544878 A ES544878 A ES 544878A ES 544878 A ES544878 A ES 544878A ES 8604251 A1 ES8604251 A1 ES 8604251A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- give
- compound
- new
- deoxo
- 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
Links
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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Cpds. of formula (I) and their acid-addn. salts are new. (m and n are 0; X is Me; and R2 and R3 are H, 2-3C alkanoyl or 3-ethoxycarbonylpropionyl). - Intermediates of formula (I) are new when R2 and R3 are H; m is 1; and either X is OH and n is 0 or X is Me and n is 1. - (I) are broad-spectrum antibacterials effective on oral admin. Dose is 1-200 mg/kg daily. Also used for sterilisation purposes e.g. sick-room utensils; and as industrial antimicrobials e.g. in water treatment, slime control, paint and wood preservation. (0/0) EPAB- EP-101186 B A process for making a compound having formula (I) which comprises the steps of (a) oxidising a compound having formula (II) with hydrogen peroxide in a reaction-inert solvent to give a compound of formula (III), (b) alkylating the product of formula (II) with methyl iodide in a reaction-inert solvent in the presence of an acid acceptor to give a compound of formula (IV) wherein n is 0 or 1 and (c) reducing the product of formula (III) in a reaction-inert solvent with hydrogen in the presence of a noble metal catalyst. - (11pp) USAB- US4474768 A N-Methyl 11-aza 10-deoxo 10-dihydro erythromycin A derivs. of formula (I) and their pharmaceutically acceptable acid addn. salts are new. R2 and R3 are H, 2-3C alkanoyl or 3-carbethoxypropionyl. m is O, X is CH3. - The intermediates of formula (I; m is 1, X is OH) and (I; m is 1, X is (O)n, where n is 0 or 1) are also new. Cpds. (I) may be prepd. from 11-aza 10-deoxo 10-dihydro erythromycin A by treating with H2O2 in CH3OH to give (I; m=1, X=OH). This is treated with an alkylating agent to give (I; m=1, X=(O)n), which is catalytically reduced, e.g. using Raney Ni, to give (I).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/441,981 US4474768A (en) | 1982-07-19 | 1982-11-15 | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES544878A0 ES544878A0 (en) | 1986-01-16 |
| ES8604251A1 true ES8604251A1 (en) | 1986-01-16 |
Family
ID=23755074
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES527250A Expired ES8602838A1 (en) | 1982-11-15 | 1983-11-14 | A PROCEDURE FOR THE PREPARATION OF THE DERIVATIVE OF 11-AZA-10-DESOXO-10-DIHIDROERITROMICINA A |
| ES544878A Expired ES8604251A1 (en) | 1982-11-15 | 1985-07-04 | A PROCEDURE FOR THE PREPARATION OF N-METHYL-11-AZA-10-DEOXO-10-DIHYDROERITHROMYCIN A |
| ES544877A Expired ES8604250A1 (en) | 1982-11-15 | 1985-07-04 | A PROCEDURE FOR THE PREPARATION OF THE N-METHYLATE DERIVATIVE OF AN 11-AZA-10-DESOXO-10-DIHIDROERITROMICINA A |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES527250A Expired ES8602838A1 (en) | 1982-11-15 | 1983-11-14 | A PROCEDURE FOR THE PREPARATION OF THE DERIVATIVE OF 11-AZA-10-DESOXO-10-DIHIDROERITROMICINA A |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES544877A Expired ES8604250A1 (en) | 1982-11-15 | 1985-07-04 | A PROCEDURE FOR THE PREPARATION OF THE N-METHYLATE DERIVATIVE OF AN 11-AZA-10-DESOXO-10-DIHIDROERITROMICINA A |
Country Status (9)
| Country | Link |
|---|---|
| KR (1) | KR850000963B1 (en) |
| CS (1) | CS241533B2 (en) |
| DD (1) | DD215787A5 (en) |
| EG (1) | EG16882A (en) |
| ES (3) | ES8602838A1 (en) |
| GR (1) | GR77556B (en) |
| PL (1) | PL141924B1 (en) |
| SU (1) | SU1274626A3 (en) |
| YU (2) | YU42885B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5527780A (en) * | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| CN110655544A (en) * | 2018-06-28 | 2020-01-07 | 洛阳惠中兽药有限公司 | Method for separating, preparing and purifying gamithromycin related substances |
-
1983
- 1983-07-26 GR GR72035A patent/GR77556B/el unknown
- 1983-08-03 CS CS835758A patent/CS241533B2/en unknown
- 1983-08-19 PL PL1983243473A patent/PL141924B1/en unknown
- 1983-08-19 DD DD83254089A patent/DD215787A5/en not_active IP Right Cessation
- 1983-08-20 KR KR1019830003895A patent/KR850000963B1/en not_active Expired
- 1983-08-22 SU SU833635803A patent/SU1274626A3/en active
- 1983-10-14 YU YU2075/83A patent/YU42885B/en unknown
- 1983-11-14 ES ES527250A patent/ES8602838A1/en not_active Expired
- 1983-11-15 EG EG716/83A patent/EG16882A/en active
-
1985
- 1985-07-04 ES ES544878A patent/ES8604251A1/en not_active Expired
- 1985-07-04 ES ES544877A patent/ES8604250A1/en not_active Expired
- 1985-08-21 YU YU1332/85A patent/YU44519B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD215787A5 (en) | 1984-11-21 |
| PL243473A1 (en) | 1984-07-30 |
| ES527250A0 (en) | 1985-12-01 |
| ES544877A0 (en) | 1986-01-16 |
| SU1274626A3 (en) | 1986-11-30 |
| CS241533B2 (en) | 1986-03-13 |
| ES544878A0 (en) | 1986-01-16 |
| ES8602838A1 (en) | 1985-12-01 |
| YU133285A (en) | 1986-02-28 |
| PL141924B1 (en) | 1987-09-30 |
| ES8604250A1 (en) | 1986-01-16 |
| GR77556B (en) | 1984-09-24 |
| YU207583A (en) | 1985-12-31 |
| EG16882A (en) | 1989-06-30 |
| KR850000963B1 (en) | 1985-07-02 |
| KR840006671A (en) | 1984-12-01 |
| YU42885B (en) | 1988-12-31 |
| YU44519B (en) | 1990-08-31 |
| CS575883A2 (en) | 1985-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 20051017 |