US 5,399,487 AGranted

6-peptidylamino-1-naphthalenesulfonamides useful as fluorogenic proteolytic enzyme substrates

AssigneeHaematologic Technologies, Inc.

InventorsSaulius Butenas, Jeffrey H. Lawson, Kenneth G. Mann

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Abstract

The present invention encompasses compounds of formula I: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof; wherein R.sub.1 is hydrogen, lower alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, or phenylalkyl; R.sub.2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, cycloalkylalkyl, or phenylalkyl; or NR.sub.1 R.sub.2 forms a nitrogen heterocycle; and R.sub.3 is hydrogen, an amino acid or a peptide residue. These compounds may be employed as substrates in assays for determining proteolytic enzyme activity or as enzyme inhibitors. The invention also encompasses methods for determining proteolytic enzyme activity using the compounds of formula I.

Claims38

Dependent claims

A compound of the formula:

##STR28## and the pharmaceutically acceptable non-toxic salts thereof;
wherein R.sub.1 is hydrogen, straight or branched chain lower alkyl having 1-6 carbon atoms, straight or branched chain alkenyl having 2-8 carbon atoms, straight or branched chain alkynyl having 2-8 carbon atoms, cycloalkyl having 3-7 carbon atoms, alkylcycloalkyl where the alkyl portion has 1-6 carbon atoms, cycloalkylalkyl where the alkyl portion has 1-6 carbon atoms, or phenylalkyl where the alkyl portion is straight or branched chain alkyl having 1-6 carbon atoms, or a group of the formula ##STR29## wherein R.sub.5 represents an amino acid side chain and R.sub.4 is hydroxy, an amino acid or a peptide residue;
R.sub.2 is hydrogen, straight or branched chain lower alkyl having 1-6 carbon atoms, straight or branched chain alkenyl having 2-8 carbon atoms, straight or branched chain alkynyl having 2-8 carbon atoms, cycloalkyl having 3-7 carbon atoms, alkylcycloalkyl where the alkyl portion has 1-6 carbon atoms, cycloalkylalkyl where the alkyl portion has 1-6 carbon atoms, or phenylalkyl where the alkyl portion is straight or branched chain alkyl having 1-6 carbon atoms, or a group of the formula ##STR30## wherein R.sub.5 represents an amino acid side chain and R.sub.4 is hydroxy, an amino acid or a peptide residue;
or
NR.sub.1 R.sub.2 forms a nitrogen heterocycle;
and
R.sub.3 is an amino acid or a peptide residue.

4 more elements

Dependencies are inferred from the claim text.