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US 6,686,503 B2Granted
Methods for the synthesis of highly substituted 2,4-dioxopiperidine libraries
AssigneeOrtho-McNeil Pharmaceutical, Inc.
InventorsWenying Chai, William V. Murray
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Abstract
The invention relates to methods of synthesizing libraries of diverse and complex highly substituted 2,4-dioxopiperidine compounds of the general formula: 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.
Claims12
A compound selected from those of the formula:
- wherein:
- is a solid support;
- R1 is selected from the group consisting of a standard natural amino acid side chain, CH3, CFI(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 COOalkyl, CN, COloweralkyl, COaralkyl wherein said aralkyl is benzyl or substituted benzyl, and COaryl;
- where aryl is phenyl, substituted phenyl, thienyl, furyl or naphthyl.
8 more elements
A compound selected from those of the formula:
- wherein:
- R1 is selected from the group consisting of a standard natural amino acid side chain, CH3, CH(CH3)CH2CH2 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 COOalkyl, CN COloweralkyl, COaralkyl wherein said aralkyl is benzyl or substituted benzyl, and COaryl;
- where aryl is phenyl, substituted phenyl, thienyl, furyl or naphthyl.
7 more elements
Dependencies are inferred from the claim text.