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Carboxyalkyl peptide derivatives

Assignee: GD Searle LLC
•
Filing: 1984-04-12
•
Granted: 1985-04-16
•
Expires: 2004-04-12
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Abstract

Abstract This invention encompasses novel carboxyalkyl peptide derivatives which are collagenase inhibitors.

Inventors

  • 👤 Keith G. McCullagh
  • 👤 Harry J. Wadsworth
  • 👤 Michael M. Hann

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 19:54
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/02; C07K5/022; C07K5/0222; A; A61; A61P; A61P1/00; A61P1/02; A61P29/00; A61P43/00; A61K; A61K38/00

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 71 words
A compound of the formula ##STR29## and the pharmaceutically acceptable acid addition salts thereof wherein x represents hydrogen, alkoxy or benzyloxy; y represents a radical selected from alkyl, alkylthioalkyl, ##STR30## wherein v is 2 or 3, ##STR31## wherein z represents hydrogen or nitro; W 1 and W 2 represent methyl or trifluoromethyl; and R 1 represents hydroxy or alkoxy and the stereochemistry of the carbon marked by the asterisk is R.
Claim 2
Dependent Claim 71 words
A compound of the formula ##STR29## and the pharmaceutically acceptable acid addition salts thereof wherein x represents hydrogen, alkoxy or benzyloxy; y represents a radical selected from alkyl, alkylthioalkyl, ##STR30## wherein v is 2 or 3, ##STR31## wherein z represents hydrogen or nitro; W 1 and W 2 represent methyl or trifluoromethyl; and R 1 represents hydroxy or alkoxy and the stereochemistry of the carbon marked by the asterisk is R.
Claim 3
Dependent Claim 61 words
A compound according to claim 1 having the formula ##STR32## and the pharmaceutically acceptable salts thereof wherein R 1 , R 3 , R 17 , and R 18 are as described in claim 1; and R 13 represents benzyloxy; benzyloxy substituted with 4-chloro, 2-chloro, 4-methyl, 4-nitro or 4-amino; benzylamino; phenyl or phenyl substituted with 4-chloro, 2-chloro, 4-methyl, 4-nitro or 4-amino.
Claim 4
Dependent Claim 16 words
A compound according to claim 1 which is N-[1-(R)-carboxyethyl]-L-leucyl-O-benzyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim 16 words
A compound according to claim 1 which is N[1-(R)-carboxy-3-methylthiopropyl]-L-leucyl-O-methyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim 16 words
A compound according to claim 1 which is N-[4-N-(benzyloxycarbonyl)amino-1-(R)-crboxybutyl]-L-leucyl-O-methyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim 16 words
A compound according to claim 1 which is N-[3-N-(benzyloxycarbonyl)amino-1-(R)-carboxypropyl]-L-leucyl-O-methyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim 16 words
A compound according to claim 1 which is N-[3-N-(p-nitrobenzyloxycarbonyl)amino-1-(R)-carboxypropyl]-L-leucyl-O-methyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 9
Dependent Claim 16 words
A compound according to claim 1 which is N-[3-N-(benzoyl)amino-1-(R)-carboxypropyl]-L-leucyl-O-methyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 10
Dependent Claim 16 words
A compound according to claim 1 which is N-[3-(N'-benzyl)carbamoyl-1-(R)-carboxypropyl]-L-leucyl-O-methyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 11
Dependent Claim 17 words
A compound according to claim 1 which is N-[2-(S)-N-(1-(R)-carboxyethyl amino-4,4-di-(trifluoromethyl)butanoyl]-O-methyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 12
Dependent Claim 16 words
A compound according to claim 1 which is N-[2-(S)-N-(3-N-(benzyloxycarbonyl)amino-1-(R)-carboxypropyl)amino-4,4-di-(trifluoromethyl)-butanoyl]-O-methyl-L-tyrosine N-methylamide and the pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim 154 words
A compound having the formula: ##STR33## R 1 represents hydroxy, alkoxy, aralkoxy; R 3 represents alkyl or alkyl substituted with one or two trifluoromethyl groups; R 4 represents hydrogen or alkyl; n is 1 to 4 inclusive; R 13 represents alkyl, aryl, aralkyl, aralkoxy, alkoxy, alkylamino, arylamino, aralkylamino, dailkylamino, or substituted aryl, substituted aralkyl, and substituted aralkoxy wherein the substituent on the aromatic moiety may be one or more groups selected from halogen, alkyl, hydroxy, alkoxy, aralkoxy, aralkoxyamino, aminomethyl, cyano, acylamino, dialkylamino, carboxy, sulphonamido, alkylthio, nitro and phenyl; R 17 represents substituted alkyl wherein the substituent is alkoxy, aralkoxy, alkoxycarbonylamino, aralkoxycarbonylamino, carboxyalkyl or carboxyaralkyl; or substituted aralkyl wherein the aryl substituent is one or more groups selected from alkyl, alkoxy, alkyl thio or aralkoxy; and R 18 represents amino, alkylamino, dailkylamino, substituted alkylamino wherein the substituent is amino, hydroxy, alkoxy, carboxy, carboxamido, carboxyalkyl, alkyl thio, alkylsulphinyl or alkylsulphonyl, hydroxamino, alkoxyamino, aralkylamino, alkoxy, aralkoxy, alkylaminoalkoxy.
Claim 14
Dependent Claim 154 words
A compound having the formula: ##STR33## R 1 represents hydroxy, alkoxy, aralkoxy; R 3 represents alkyl or alkyl substituted with one or two trifluoromethyl groups; R 4 represents hydrogen or alkyl; n is 1 to 4 inclusive; R 13 represents alkyl, aryl, aralkyl, aralkoxy, alkoxy, alkylamino, arylamino, aralkylamino, dailkylamino, or substituted aryl, substituted aralkyl, and substituted aralkoxy wherein the substituent on the aromatic moiety may be one or more groups selected from halogen, alkyl, hydroxy, alkoxy, aralkoxy, aralkoxyamino, aminomethyl, cyano, acylamino, dialkylamino, carboxy, sulphonamido, alkylthio, nitro and phenyl; R 17 represents substituted alkyl wherein the substituent is alkoxy, aralkoxy, alkoxycarbonylamino, aralkoxycarbonylamino, carboxyalkyl or carboxyaralkyl; or substituted aralkyl wherein the aryl substituent is one or more groups selected from alkyl, alkoxy, alkyl thio or aralkoxy; and R 18 represents amino, alkylamino, dailkylamino, substituted alkylamino wherein the substituent is amino, hydroxy, alkoxy, carboxy, carboxamido, carboxyalkyl, alkyl thio, alkylsulphinyl or alkylsulphonyl, hydroxamino, alkoxyamino, aralkylamino, alkoxy, aralkoxy, alkylaminoalkoxy.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-04-15 1988-10-15 1989-04-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-04-15 1992-10-15 1993-04-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-04-15 1996-10-15 1997-04-16 $7700.00 Window Closed / Lapsed

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