Sulfamide and bis-sulfamide amino acid derivatives as inhibitors of proteolytic enzymes

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Issue Date
2002-12-17
Embargo End Date
Authors
Groutas, William C.
Advisor
Citation

Groutas, William C., inventor. Wichita State University, assignee. Sulfamide and bis-sulfamide amino acid derivatives as inhibitors of proteolytic enzymes. United States patent US 6,495,358. 2002, Dec.17.

Abstract

Compounds of the general formula I are provided: ##STR1## and pharmaceutically acceptable salts thereof, wherein, Z is a chemical species or R.sub.i capable of binding at a primary specificity site of a protease; Y is a chemical species reactive to a specific class of protease; each of R.sub.2, R.sub.3, R.sub.5 and R.sub.7 is independently selected from the group consisting hydrogen, alkyls, aryls, substituted aryls, alkylaryls and arylalkyls; R.sub.4 and R.sub.6 are independently selected from the group consisting of: (a) H, alkyl, aryl, arylalkyl, alkylaryl, substituted derivatives thereof, and R.sub.i ; (b) --C(O)OH and derivatives thereof, said derivatives selected from the group consisting of --C(O)OQ, --C(O)NR.sub.Y R.sub.Z, --C(O)[NHCHR.sub.i(q) C(O)].sub.q OQ, and --C(O)[NHCHR.sub.i(q) C(O)].sub.q NR.sub.Y R.sub.Z ; and (c) --CHR.sub.i NH.sub.2 and derivatives thereof, said derivatives selected from the group consisting of --CHR.sub.i NHW, --CHR.sub.i NHC(O)OQ, --CHR.sub.i NHC(O)R, --CHR.sub.i NHC(O)NR.sub.Y R.sub.Z, --CHR.sub.i NHC(O)[NHCHR.sub.i(q) C(O)].sub.q OQ, --CHR.sub.i NHSO.sub.2 R, and --CHR.sub.i NH[C(O)CHR.sub.i(r) NH].sub.r W, where q and r independently are integers from 1 to 10 inclusive; J is a carboxyl protecting group; G is an amino protecting group; Q is H, R or J; W is H, R or G; each R.sub.i is independently selected from naturally or non-naturally occurring amino acid side chains; R is alkyl, aryl, substituted aryl, alkylaryl, arylalkyl, or heterocyclic radical; and each R.sub.Y and R.sub.Z is independently H, alkyl, aryl, substituted aryl, alkylaryl, arylalkyl, or heterocyclic radical.

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Description
WSU inventor: William C. Groutas, Dept. of Chemistry, College of Liberal Arts and Sciences
Appl. No.: 09/552,554 filed Apr 19, 2000. Patent No.: U.S. 6,495,358 granted Dec 17, 2002.
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