Back to results
US 2001/0041345 A1Published application
Methods for the synthesis of highly substituted 2,4-dioxopiperidine libraries
AssigneeOrtho-McNeil Pharmaceutical, Inc.
InventorsWenying Chai, William V. Murray
Life of this patent
Estimating the term…
Abstract
The invention relates to methods of synthesizing libraries of diverse and complex highly substituted 2,4-dioxopiperidine compounds of the general formula: 1 wherein R1, R2 and R3 are as herein described, novel intermediates useful for synthesizing such 2,4-dioxopiperidine compounds and methods for identifying and isolating the compounds.
Claims25
A method of synthesizing highly substituted 2,4-dioxopiperidine compounds having the general Formula I:
- 33
- wherein:
- R1 is selected from the group consisting of a standard natural amino acid side chain, CH3, CH(CH3)CH2CH3 and CH2Phenyl;
- R2 is selected from the group consisting of alkyl, substituted alkyl, aralkyl, phenyl and substituted aryl;
- R3 is selected from the group consisting of COalkyl, CN, COloweralkyl, COaralkyl, COaryl, COfuryl and COthienyl;
- which method comprises,
- (a) preparing a compound of the formula:
- 34
- wherein R1-R3 are as described above, on a solid resin support;
- (b) cleaving the compound from the solid resin support and methylating to yield an intermediate methyl ester compound of the formula:
- 35
- and,
- (c) condensing the intermediate methyl ester compound to provide the substituted 2,4-dioxopiperidine compounds of Formula I.
10 more elements
A compound selected from those of the formula:
- 38
- wherein:
- R1 is selected from the group consisting of a standard natural amino acid side chain, CH3, CH(CH3)CH2CH3 and CH2Ph;
- R2 is selected from the group consisting of alkyl, aralkyl, phenyl and substituted phenyl;
- where the substituents on the substituted phenyl group are selected from lower alkyl, halo, alkoxy, nitrile, cyano, alkoxycarbonyl, aryloxycarbonyl, nitro, furyl and substituted furyl;
- where the substituents on the substituted furyl group are selected from alkyl, halo, alkoxy, alkoxycarbonyl, nitrile, aryloxycarbonyl, nitro, thienyl and substituted thienyl;
- where the substituents on the substituted thienyl group are selected from lower alkyl, halo, alkoxy, nitrile, alkoxycarbonyl, aryloxycarbonyl, naphthyl and substituted naphthyl;
- where the substituents on the substituted naphthyl group are selected from lower alkyl, halo, alkoxy, nitrile, alkoxycarbonyl and aryloxycarbonyl;
- and,
- R3 is selected from the group consisting of COalkyl, CN, COloweralkyl, COaralkyl(benzyl and substituted benzyl) and COaryl;
- where aryl is phenyl, substituted phenyl, thienyl, furyl and naphthyl.
8 more elements
Dependencies are inferred from the claim text.