Antithrombotic azacycloalkylalkanoyl peptides and pseudopeptides
AssigneeAventis Pharmaceuticals Products Inc.
InventorsScott I. Klein, Bruce F. Molino
Life of this patent
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Abstract
The present invention relates to azacycloalkylalkanoyl peptides and pseudopeptides which inhibit platelet aggregation and thrombus formation thereby being useful in the prevention and treatment of thrombosis associated with disease states such as myocardial infarction, stroke, peripheral arterial disease, and disseminated intravascular coagulation, to methods for the prevention or treatment of thrombosis in a mammal in need of such therapy comprising the administration of a therapeutically effective amount of such compounds, and to pharmaceutical compositions comprising such compounds.
Claims6
A compound which is an intermediate in the synthesis of an antithrombotic pseudopeptide, having the formula:
- wherein:
- B is alkyl, cycloalkyl, cycloalkylalkyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, aralkyl, alkylaryl or alkylaralkyl;
- F′ is selected from the group consisting of —H, alkyl, hydroxymethyl, 1-hydroxyethyl, mercaptomethyl, 2-methylthioethyl, carboxymethyl, 2-carboxyethyl, aminocarbonylmethyl, 2-aminocarbonylethyl, 4-aminobutyl, 3-aminopropyl, 3-guanidinopropyl, indol-3-ylmethyl, imidazol-3-ylmethyl, cycloalkyl, cycloalkylalkyl, cyclohexylcyclohexylmethyl, 1,2,3,4-tetrahydronaphth-5-ylmethyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, substituted aryl, aralkyl, substituted aralkyl, heterocyclyl, and substituted heterocyclyl, heterocyclylalkyl, substituted heterocyclylalkyl, wherein heterocyclyl is pyridyl, pyrimidyl or pyrrolidyl;
- G′ is alkyl, cycloalkyl, cycloalkylalkyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, substituted aryl, aralkyl, substituted aralkyl, heterocyclyl, substituted heterocyclyl, heterocyclyl-alkyl and substituted heterocyclylalkyl, wherein heterocyclyl is pyridyl, pyrimidyl or pyrrolidyl,
- p is 1 to 4, and
- P2 is a carboxylic acid protecting group and P3 is an amino protecting group.
A compound which is an intermediate in the synthesis of an antithrombotic pseudopeptide, having the formula:
- wherein:
- B is alkyl, cycloalkyl, cycloalkylalkyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, aralkyl, alkylaryl or alkylaralkyl;
- F′ is selected from the group consisting of —H, alkyl, hydroxymethyl, 1-hydroxyethyl, mercaptomethyl, 2-methylthioethyl, carboxymethyl, 2-carboxyethyl, aminocarbonylmethyl, 2-aminocarbonylethyl, 4-aminobutyl, 3-aminopropyl, 3-guanidinopropyl, indol-3-ylmethyl, imidazol-3-ylmethyl, cycloalkyl, cycloalkylalkyl, cyclohexylcyclohexylmethyl, 1,2,3,4-tetrahydronaphth-5-ylmethyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, substituted aryl, aralkyl, substituted aralkyl, heterocyclyl, and substituted heterocyclyl, heterocyclylalkyl, substituted heterocyclylalkyl, wherein heterocyclyl is pyridyl, pyrimidyl or pyrrolidyl;
- G′ is alkyl, cycloalkyl, cycloalkylalkyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, substituted aryl, aralkyl, substituted aralkyl, heterocyclyl, substituted heterocyclyl, heterocyclylalkyl, substituted heterocyclylalkyl, and NR1R2, wherein heterocyclyl is pyridyl, pyrimidyl, or pyrrolidyl, and wherein R1 and R2 are independently —H, alkyl, cycloalkyl, cycloalkylalkyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, aralkyl, alkylaryl, or alkylaralkyl,
- p is 1 to 4, and P2 is a carboxylic acid protecting group conventionally used in peptide synthesis.
Dependencies are inferred from the claim text.