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US 7,605,258 B2Granted
Processes for the synthesis of individual isomers of mono-peg CCI-779
AssigneeWyeth
InventorJerauld Stanley Skotnicki
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Abstract
Processes for preparing individual diastereomers of mono-pegylated rapamycin 42 ester with 3-hydroxy-2-(hydroxymethyl)-2-methylpropionic acid (CCI-779) are provided.
Claims25
A process for preparing an individual isomer of mono-pegylated rapamycin 42 ester with 3-hydroxy-2-(hydroxymethyl)-2-methylpropionic acid (CCI-779), said process comprising:
- (a) reacting
- with HY—(CH2CH2O)nCH3,
- wherein:
- X is a leaving group,
- Y is S or O,
- R is a protecting group, and
- n is an integer from 5 to 450;
- (b) protecting the alcohol group of the product of (a);
- (c) deprotecting the acid group of the product of (b);
- (d) resolving the isomers of (c) using a chiral amine or a chiral alcohol;
- (e) reacting one resolved isomer of (d) with rapamycin;
- and
- (f) deprotecting the product of (e).
10 more elements
A process for preparing an individual isomer of mono-pegylated rapamycin 42 ester with 3-hydroxy-2-(hydroxymethyl)-2-methylpropionic acid (CCI-779), said process comprising:
- (a) resolving the isomers of
- using a chiral amine or a chiral alcohol, wherein X is a leaving group and R is a protecting group;
- (b) protecting the alcohol group of an isomer product of (a);
- (c) deprotecting the acid group of an isomer product of (b);
- (d) reacting the product of (c) with rapamycin;
- (e) reacting the product of (d) with HY—(CH2CH2O)nCH3,
- wherein:
- Y is S or O, and
- n is an integer from 5 to 450;
- and
- (f) deprotecting the product of (e).
8 more elements
Dependencies are inferred from the claim text.