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Novel decapeptides, intermediates therefor, and compositions and methods employing said decapeptides
| Details |
Inventors: Coy, David H.; Kastin, Abba J.;
Assignee:
Primary Examiner: Phillips; Delbert R.
Assistant Examiner:
Attorney, Agent or Firm: Niblack; Joyce R.
Novel decapeptides having the following amino acid sequence: H-Tyr-X-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Y wherein: X is a chiral residue of a D-amino acid selected from the group consisting of D-alanine, D-leucine, D-isoleucine, D-valine, D-phenylalanine, D-tyrosine, D-tryptophan, D-serine, D-threonine, D-methionine, D-glutamic acid, D-glutamine, D-proline D-aspartic acid, D-asparagine, D-lysine, D-arginine and D-histidine; and Y is selected from the group consisting of hydroxy, amino, loweralkylamino, diloweralkylamino and lower alkoxy; and the pharmaceutically acceptable salts thereof; intermediates useful in making the novel compounds; and pharmaceutical compositions and methods employing the novel compounds. |
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DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS The compounds of this invention are decapeptides represented by formula I and having the following amino acid sequence: H-Tyr-X-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Y (I) wherein: X is a chiral residue of a D-amino acid selected from the group consisting of D-alanine, D-leucine, D-isoleucine, D-valine, D-phenylalanine, D-tyrosine, D-tryptophan, D-serine, D-threonine, D-methionine, D-glutamic acid, D-glutamine, D-aspartic acid, D-proline, D-asparagine, D-lysine, D-arginine and D-histidine; and Y is selected from the group consisting of hydroxy, amino, aminoloweralkyl, aminodiloweralkyl, or lower alkoxy; and the pharmaceutically acceptable salts thereof.
All chiral amino acid residues identified herein are in the natural or L-configuration unless otherwise specified.
In keeping with standard peptide nomenclature, abbreviations for chiral amino acid residues have been used herein as follows:
______________________________________
Tyr
L-tyrosine Ile
L-isoleucine
D-Tyr
D-tyrosine
D-Ile
D-isoleucine
Gly
glycine
Leu
L-leucine
Phe
L-phenylalanine
D-Leu
D-leucine
D-Phe
D-phenylalanine
Thr
L-threonine
Met
L-methionine
D-Thr
D-threonine
D-Met
D-methionine
Val
L-valine
Ala
L-alanine
D-Val
D-valine
D-Ala
D-alanine
Pro
L-proline
Ser
L-serine
D-Pro
D-proline
D-Ser
D-serine
Gln
L-glutamine
Lys
L-lysine
D-Gln
D-glutamine
D-Lys
D-lysine
Glu
L-glutamic acid
Asn
L-asparagine
D-Glu
D-glutamic acid
D-Asn
D-asparagine
Trp
L-tryptophan
His
L-histidine
D-Trp
D-tryptophan
D-His
D-histidine
D-Asp
D-aspartic acid
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The term "pharmaceutically acceptable salts," as used herein, refers to the non-toxic alkali metal, alkaline earth metal and ammonium salts commonly used in the pharmaceutical industry including the sodium, potassium, lithium, calcium, magnesium, barium and ammonium salts which are prepared by methods well known in the art
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