US6022965A
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Method for isomerising the 10-methyl radical of erythromycin derivatives
Assignee: Aventis Pharma SA
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Filing: 1997-05-13
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Granted: 2000-02-08
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Expires: 2017-05-13
Abstract
Abstract An isomerization method wherein a compound of formula ##STR1## wherein X and y together form a 3-oxo radical, or X is a hydrogen atom and Y is either a radical a ##STR2## where R 2 is OH or O-acyl, or an O-alkyl or NH 2 radical; R 1 is a hydrogen atom or a methyl radical; Z is hydrogen or an acyl radical; and R is a hydrogen atom, an NH 2 radical or a (CH 2 ) n Ar, NH(CH 2 ) n Ar or N═CH(CH 2 ) n Ar radical, in the form of a 10α isomer or a mixture of 10α and 10β isomers, is exposed to a basic agent to give the corresponding compound of formula I in which the 10-methyl radical is in the β position.
Inventors
- 👤 Yannick Benedetti
- 👤 Jacques Lagouardat
- 👤 Jacques Scholl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:18
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08; A; A61; A61K; A61K31/00; A61K31/70
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
180 words
An isomerization process for the preparation of a compound of the formula ##STR9## with the 10-methyl in the beta position wherein R 1 is hydrogen or methyl, R 2 is selected from the group consisting of --OH, acyloxy of organic carboxylic acid of 2 to 20 carbon atoms, alkoxy of 2 to 20 carbon atoms and --NH 2 , X and Y form ═0 or X is hydrogen and Y is ##STR10## Z' is hydrogen or acyl of an organic carboxylic acid of 2 to 20 carbon atoms and R is selected from the group consisting of hydrogen, --NH 2 , --(CH 2 ) n --Ar, --NH--(CH 2 ) n --Ar and --N═CH--(CH 2 ) n --Ar, N is an integer from 1 to 6 and Ar is optionally substituted aryl or heteroaryl comprising reacting a compound of the formula ##STR11## in the 10α-isomer or a mixture of 10α- and 10β-isomers wherein Z is hydrogen or acyl of an organic carboxylic acid of 2 to 20 carbon atoms with a basic agent to obtain the 10β-methyl isomer of formula I.
Claim 2
Dependent Claim
180 words
An isomerization process for the preparation of a compound of the formula ##STR9## with the 10-methyl in the beta position wherein R 1 is hydrogen or methyl, R 2 is selected from the group consisting of --OH, acyloxy of organic carboxylic acid of 2 to 20 carbon atoms, alkoxy of 2 to 20 carbon atoms and --NH 2 , X and Y form ═0 or X is hydrogen and Y is ##STR10## Z' is hydrogen or acyl of an organic carboxylic acid of 2 to 20 carbon atoms and R is selected from the group consisting of hydrogen, --NH 2 , --(CH 2 ) n --Ar, --NH--(CH 2 ) n --Ar and --N═CH--(CH 2 ) n --Ar, N is an integer from 1 to 6 and Ar is optionally substituted aryl or heteroaryl comprising reacting a compound of the formula ##STR11## in the 10α-isomer or a mixture of 10α- and 10β-isomers wherein Z is hydrogen or acyl of an organic carboxylic acid of 2 to 20 carbon atoms with a basic agent to obtain the 10β-methyl isomer of formula I.
Claim 3
Dependent Claim
11 words
The process of claim 1 wherein Z and Z' are hydrogen.
Claim 4
Dependent Claim
12 words
The process of claim 1 wherein the basic agent is potassium hydroxide.
Claim 5
Dependent Claim
32 words
The process of claim 1 wherein the basic agent is selected from the group consisting of tetrabutylammonium hydroxide or bromide, an alkali metal carbonate sodium hydroxide, (1,8-diazabicyclo[5-4-0]undec7-ene), tripotassium phosphate and sodium methylate.
Claim 6
Dependent Claim
48 words
The process of claim 1 wherein the operation is carried out in a solvent selected from the group consisting of tetrahydrofuran, 1-methyl-2-pyrrolidinone in aqueous solution, methylene chloride and an alcohol and Z' is hydrogen or an acyl of an organic carboxylic acid of 2 to 20 carbon atoms.
Claim 7
Dependent Claim
12 words
The process of claim 5 wherein the solvent is a methanolic solution.
Claim 8
Dependent Claim
11 words
The process of claim 1 wherein R is NH 2 .
Claim 9
Dependent Claim
10 words
The process of claim 1 wherein R 1 is methyl.
Claim 10
Dependent Claim
11 words
The process of claim 1 wherein X and Y are ═0.
Claim 11
Dependent Claim
11 words
The process of claim 1 wherein Z and Z' are hydrogen.
References Cited (Backward Citations)
EP0676409A1
Cited
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