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Details for Patent: 4,529,595

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Details for Patent: 4,529,595

Title: GRF Analogs
Abstract:Human pancreatic GRF analogs which are extremely potent in stimulating the release of pituitary GH in mammals and which have the formula: H-R-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-R.sub.15 -Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-R.sub.27 -Ser-Arg-Gln-Gln-Gly-Glu-Ser-Asn-Gln-Glu-Arg-Gly-Ala-Y wherein R is selected from the D- and L-isomers of Tyr, Phe and His, R.sub.15 is Gly or D-Ala, R.sub.27 is selected from the group consisting of the D- and L-isomers of Ala, Nle, Ile, Leu, Met and Val, and Y signifies the carboxyl moiety of the amino acid residue at the C-terminal and is the radical --COOR.sub.1,--CR.sub.1 O,--CONHNHR.sub.1,--CON(R.sub.1)(R.sub.2) or --CH.sub.2 OR.sub.1, with R.sub.1 and R.sub.2 being lower alkyl or hydrogen, provided that when R is Tyr, R.sub.27 is other than Met. Phe may be substituted for Tyr in the 10-position, and D-Ala may be substituted for Gly in the 28-position. These peptides or biologically active fragments thereof, which will generally extend from the N-terminal to the vicinity of a residue between positions 27 and 32, as well as nontoxic salts of any of the foregoing, may be administered therapeutically to animals, including humans, and may be used diagnostically.
Inventor(s): Rivier; Jean E. F. (LaJolla, CA), Vale, Jr.; Wylie W. (LaJolla, CA)
Assignee: The Salk Institute for Biological Studies (San Diego, CA)
Filing Date:Jan 13, 1983
Application Number:06/457,862
Claims:1. A synthetic peptide having the formula: H-R-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Al a-Arg-Lys-Leu-Leu-Gln-Asp-Ile-R.sub.27 -Ser-Arg-Gln-Gln-Gly-Glu-Ser-Asn-Gln-Glu-Arg-Gly-Ala-Y wherein R is selected from the D- and L-isomers of Tyr, Phe and His, R.sub.27 is selected from the group consisting of the D- and L-isomers of Ala, Nle, Ile, Leu, Met and Val and Y signifies the carboxyl moiety of the amino acid residue at the C-terminal and is the radical --COOR.sub.1, --CR.sub.1 O, --CONHNHR.sub.1, --CON(R.sub.1 )(R.sub.2) or --CH.sub.2 OR.sub.1, with R.sub.1 and R.sub.2 being lower alkyl or hydrogen, wherein D-Ala can be substituted for Gly in the 15-position or for Ser in the 28-position, and wherein Phe can be substituted for Tyr in the 10-position, provided however that when R is Tyr, R.sub.27 is other than Met; or a biologically active fragment thereof extending from R at the N-terminus to a residue in any of positions 27 through 39 as its C-terminus; or a nontoxic salt of the foregoing.

2. A synthetic peptide having the formula of claim 1 wherein R is His.

3. A synthetic peptide having the formula of claim 2 wherein Y is CONH.sub.2.

4. A synthetic peptide having the formula of claim 3 wherein R.sub.27 is Nle.

5. A synthetic peptide having the formula of claim 4 having only residues 1 through 32.

6. A synthetic peptide having the formula of claim 1 wherein R.sub.27 is Nle.

7. A synthetic peptide having the formula of claim 6 wherein D-Ala is substituted for Ser in the 28-position.

8. A synthetic peptide having the formula of claim 6 having only residues 1 through 32.

9. A synthetic peptide having the formula of claim 1 wherein R is D-Tyr.

10. A synthetic peptide having the formula of claim 9 wherein R.sub.27 is Nle.

11. A synthetic peptide having the formula of claim 1 wherein R.sub.27 is Val.

12. A synthetic peptide having the formula of claim 1 wherein R.sub.27 is Ile.

13. A synthetic peptide having the formula of claim 1 wherein Phe is substituted for Tyr in the 10-position.

14. A composition for stimulating the release of GH in an animal comprising an effective amount of the peptide of claim 1 or a nontoxic salt thereof, and a veterinarily or pharmaceutically acceptable liquid or solid carrier therefor.

15. A method of stimulating the release of growth hormone in an animal, which comprises administering to said animal an effective amount of a composition as defined in claim 14.

16. A method in accordance with claim 15 wherein said administering is carried out either orally, intravenously, subcutaneously, intramuscularly or intranasally.

17. A method of stimulating the release of GH in a mammal by administering an effective amount of a compound having the formula: H-R-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Al a-Arg-Lys-Leu-Leu-Gln-Asp-Ile-R.sub.27 -Ser-Arg-Gln-Gln-Gly-Glu-Ser-Asn-Gln-Glu-Arg-Gly-Ala-Y wherein R is selected from the D- and L-isomers of Tyr, Phe and His, R.sub.27 is selected from the group consisting of the D- and L-isomers of Ala, Nle, Ile, Leu, Met and Val and Y signifies the carboxyl moiety of the amino acid residue at the C-terminal and is the radical --COOR.sub.1, --CR.sub.1 O, --CONHNHR.sub.1, --CON(R.sub.1)(R.sub.2) or --CH.sub.2 OR.sub.1, with R.sub.1 and R.sub.2 being lower alkyl or hydrogen, wherein D-Ala can be substituted for Gly in the 15-position or for Ser in the 28-position, and wherein Phe can be substituted for Tyr in the 10-position, provided however that when R is Tyr, R.sub.27 is other than Met; or a biologically active fragment thereof extending from R at the N-terminus to a residue in any of positions 27 through 39 as its C-terminus; or a nontoxic salt of the foregoing.

18. A composition for stimulating the release of GH in an animal comprising an effective amount of a peptide or a nontoxic salt thereof having the sequence: R-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-R.sub.10 -Arg-Lys-Val-Leu-R.sub.15 -Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-R.sub.27 ; wherein R is selected from the D- and L-isomers of Tyr, Phe and His, R.sub.10 is Tyr or Phe, R.sub.15 is Gly or D-Ala, and R.sub.27 is selected from the group consisting of the D- and L-isomers of Ala, Nle, Ile, Leu, Met and Val; provided however that when R is Tyr, R.sub.27 is other than Met; and a veterinarily or pharmaceutically acceptable liquid or solid carrier therefor.

19. A composition for stimulating the release of growth hormone in an animal as defined in claim 18 having the sequence: R-Ala-Asp-Ala-Ile-Phe-Thr-Asn-Ser-R.sub.10 -Arg-Lys-Val-Leu-R.sub.15 -Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-R.sub.27 -R.sub.28 -Arg-Gln-Gln-Gly.

20. A composition as defined in claim 19 wherein R.sub.27 is Nle.
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