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US 7,612,213 B2Granted
Compound having antitumor activity and process for producing the same
AssigneeRiken
InventorsHiroyuki Osada, Hideaki Kakeya, Yujiro Hayashi
Life of this patent
Estimating the term…
Abstract
A compound represented by the general formula (I): (I) wherein R represents linear, branched, or cyclic alkyl or aryl; a process for producing the compound; and an antitumor agent containing the compound as an active ingredient.
Claims8
A compound represented by the following general formula (I)
- wherein R in the general formula (I) is a tert-butyl group.
A process for producing a compound represented by the following general formula (I):
- wherein R represents a linear, branched, or cyclic alkyl having 2 or more carbon atoms or an aryl group comprising:
- (1) reacting tetrahydropyran-2-ol with (ethoxycarbonylethylidene) triphenylphospholane;
- (2) protecting a free hydroxyl group of the reaction product from (1);
- (3) transforming a hydroxymethyl group of the reaction product from (2) into a formyl group;
- (4) reacting the reaction product from (3) with phosphonoacetic acid ester represented by the following general formula (A):
- wherein R and X each represent a linear, branched, or cyclic alkyl or aryl group;
- (5) reacting the reaction product from (4) with a base and acetaldehyde;
- (6) formally dehydrating the reaction product from (5);
- (7) deblocking a protecting group of the reaction product from (6);
- (8) oxidizing the reaction product from (7);
- (9) reacting the reaction product from (8) with phosphonopropionic acid methyl ester represented by the following general formula (B):
- wherein X is defined as in (4) above;
- (10) reacting the reaction product from (9) with acetonitrile in the presence of a base;
- (11) reacting the reaction product from (10) with propanal represented by the following general formula (C):
- wherein Y represents a hydroxyl protecting group;
- (12) epoxidizing the reaction product from (11);
- (13) deblocking a protecting group of the reaction product from (12);
- (14) dehydrating a cyano group from the reaction product from (13);
- and
- (15) lactamizing the reaction product from (14).
17 more elements
A compound represented by the following general formula (III):
- wherein R represents a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group or n-hexyl group and Y represents a tert-butyldiphenylsilyl group, a tert-butyldimethylsilyl group, a triethylsilyl group, a group, a dimethylethylsilyl group, a teterahydropyranyl group, an ethoxyethyl group, a methoxymethyl group or a benzyl group.
A process for producing a compound represented by the following general formula (III):
- wherein R represents a linear, branched, or cyclic alkyl or aryl group and Y represents a hydroxyl protecting group, comprising
- reacting a compound represented by the following general formula (IV):
- wherein R and Y are defined as above for (III),
- with a peroxide that steroselectively epoxidizes the compound (IV).
1 more element
Dependencies are inferred from the claim text.