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US 2004/0171635 A1Published application
Novel tropane esters and methods for producing and using them
OwnerNicholas J. Archer, Anita H. Lewininventors
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Abstract
This invention relates to novel primary diol tropane esters and related compounds, including methods for making and using those compounds. The compounds of this invention are those of formula (I), (II) or (III): 1 wherein A, B and R1 are as defined herein. These compounds may be used as therapeutic and prophylactic agents against diseases such as immunoregulatory disorders, neuromuscular disorders, joint disorders, connective tissue disorders, circulatory disorders and pain.
Claims29
A compound of the following formulae:
- 6
- wherein A and B are independently in the α- or β configuration;
- and
- wherein A is —CO—O—CR2—(CR3)n—X;
- B is selected from the group consisting of —O—CO—R4 and O—R5;
- R1 is selected from the group consisting of H, aryl, arylalkyl, branched or unbranched alkyl, alkenyl and alkynyl, —CO-alkyl, —CO-aryl, and —CO-arylalkyl;
- R2 is selected from the group consisting of H and branched or unbranched alkyl, alkenyl and alkynyl;
- each R3 may be the same or different and is independently selected from the group consisting of H and branched or unbranched alkyl, alkenyl and alkynyl
- R4 is selected from the group consisting of H, branched or unbranched alkyl, alkenyl and alkynyl, aryl and arylalkyl;
- R5 is selected from the group consisting of H, branched or unbranched alkyl, alkenyl and alkynyl, aryl and arylalkyl;
- X is selected from the group consisting of OH, SH, amino and halogen;
- n is an integer selected from 0, 1, 2, 3, 4, 5 and 6;
- and pharmaceutically acceptable esters and salts thereof.
10 more elements
A compound of formula (I), (II) or (III):
- 7
- wherein A is —CO—O—CR2—(CR3)n—X;
- B is selected from the group consisting of —O—CO—R4 and —O—R5;
- R1 is selected from the group consisting of H, aryl, arylalkyl, branched or unbranched alkyl, alkenyl and alkynyl, —CO-alkyl, —CO-aryl, and —CO-arylalkyl;
- R2 is selected from the group consisting of H and branched or unbranched alkyl, alkenyl and alkynyl;
- each R3 may be the same or different and is independently selected from the group consisting of H and branched or unbranched alkyl, alkenyl and alkynyl
- R4 is selected from the group consisting of H, branched or unbranched alkyl, alkenyl and alkynyl, aryl and arylalkyl;
- R5 is selected from the group consisting of H, branched or unbranched alkyl, alkenyl and alkynyl, aryl and arylalkyl;
- X is selected from the group consisting of OH, SH, amino and halogen;
- n is an integer selected from 0, 1, 2, 3, 4, 5 and 6;
- and pharmaceutically acceptable esters and salts thereof.
8 more elements
A method for producing a primary diol tropane ester, comprising the steps of
- (a) contacting an appropriately substituted tropane and 1,1′-carbonyldiimidazole to produce an activated tropane ester;
- (b) contacting the activated tropane ester with an excess of primary diol to form a reaction mixture;
- and
- (c) maintaining the reaction mixture at a temperature and for a sufficient time for the activated tropane ester to react with the primary diol to form the corresponding primary diol tropane ester.
1 more element
Dependencies are inferred from the claim text.