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US 6,191,115 B1Granted
C-terminus modified heptapeptide LHRH analogs
AssigneeAbbott Laboratories
InventorsFortuna Haviv, Wesley J. Dwight, Charles J. Nichols, Jonathan Greer
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Abstract
The present invention relates to a class of heptapeptide analogs of LHRH. These compounds are useful in the treatment of disease conditions which are mediated by reproductive hormones, including benign prostate hyperplasia, prostate tumors, breast and ovaries tumors, cryptorchidism, hirsuitism, gastric motility disorders, dysmenorrhea, and endometriosis.
Claims13
A peptide of the formula:
- or a pharmaceutically acceptable salt or ester thereof, wherein:
- R1 is of the formula R3(C═O)—, wherein R3 is lower alkyl;
- A is an amino acyl residue selected from the group consisting of:
- 3-(2-naphthyl)-D-alanyl;
- [3-(4-chloro)]-D-phenylalanyl;
- and
- sarcosyl;
- B is an amino acyl residue selected from the group consisting of:
- 3-(1-naphthyl)-D-alanyl;
- and
- [3-(4-chloro)]-D-phenylalanyl;
- C is an amino acyl residue selected from the group consisting of:
- 3-(3-pyridyl)-D-alanyl;
- and
- 3-(1-naphthyl)-D-alanyl;
- D is seryl;
- E is an acyl group selected from the group consisting of:
- arginyl;
- (N-epsilon-nicotinyl)lysyl;
- N-methylphenylalanyl;
- [4-(3-amino-1,2,4-triazol-5-yl)]phenylalanyl;
- [4-(3-amino-1,2,4-triazol-5-yl)]-N-methylphenylalanyl;
- [4-(N-acetyl)]-N-methylphenylalanyl;
- [4-(N-nitro)]-N-methylphenylalanyl;
- [4-(N-acetyl)]-phenylalanyl;
- tyrosyl;
- N-methyltyrosyl;
- and
- 1,2,3,4-tetrahydroisoquinoline-3-carbonyl;
- F is an amino acyl residue selected from the group consisting of:
- D-arginyl;
- D-asparaginyl;
- D-citrullyl;
- D-glutamyl;
- D-homocitrullyl;
- D-2-amino-6-NG,NG-diethylguanidinohexanoyl;
- (N-epsilon-nicotinyl)-D-lysyl;
- [4-(3-amino-1,2,4-triazol-5-yl)]-D-phenylalanyl;
- [4-(N-acetyl)]-D-phenylalanyl;
- and
- D-tryptyl;
- G is an amino acyl residue selected from the group consisting of:
- cyclohexylalanyl;
- leucyl;
- and
- N-methylleucyl;
- and
- R2 is of the formula —NR4R5;
- wherein
- R4 is selected from the group consisting of:
- hydrogen;
- methyl;
- and
- ethyl;
- R5 is selected from the group consisting of:
- lower alkyl;
- and
- lower alkyl-R6;
- and
- R6 is selected from the group consisting of amino, guanidino, hydrogen, hydroxy, phenyl, morpholinyl, piperidinyl, pyrrolyl, pyridyl, pyrrolidinyl, pyrrolidinonyl and quinuclidinyl;
- and wherein the piperidinyl, pyrrolyl, pyrrolidinyl, and pyrrolidinonyl groups are optionally substituted with a methyl group.
58 more elements
Dependencies are inferred from the claim text.