IP Library › Granted Patent US 10,179,804

Granted Patent B2

US 10,179,804 · App. 15/214,845 · Granted Jan 15, 2019

Melanocortin receptor-specific peptides

Inventors: Yi-qun Shi (East Brunswick, NJ); Shubh D. Sharma (Cranbury, NJ); John H. Dodd (Spring Mills, PA); Wei Yang (Edison, NJ)

Assignee: Palatin Technologies, Inc.

C07K7/64 C07K5/1024 C07K7/56 C07K14/685 A61K38/00 A61K38/12

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Quick Facts

Patent No.: US 10,179,804
App. No.: 15/214,845
Granted: Jan 15, 2019
Kind: B2

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Abstract

Melanocortin receptor-specific cyclic peptides of the formula where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and z are as defined in the specification, compositions and formulations including the peptides of the foregoing formula, and methods of preventing, ameliorating or treating melanocortin receptor-mediated diseases, indications, conditions and syndromes.

Claims (160)

1. A cyclic peptide selected from the group consisting of:

Ac-Arg-cyclo(Asp-His-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Lys-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Ser-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Ser-D-Phe-Lys-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Ala-D-Phe-Cit-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-His-D-Phe-Lys-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Lys-D-Phe-Lys-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Ala-D-Phe-Lys-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Ala-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Phe-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Tyr-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Leu-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Nle-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Thr(Bzl)-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Hyp(Bzl)-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Val-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Aic-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Pro(4R-Bzl)-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-His-D-Nal 1-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Nle-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Ala-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Ser-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-His-D-Phe-Ala-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-His-D-Phe-Nle-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-His-D-Phe-Val-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-His-D-Phe-Ser-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Aib-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Arg-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Asp-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Glu-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Gln-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Gly-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Ile-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Thr-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Trp-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Val-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Met-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Arg-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Asp-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-His-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Leu-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Lys-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Thr-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Trp-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Thr(Bzl)-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-D-Cha-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Phe(2-C(═O)—NH 2 )-D-Phe-Arg-Trp-Lys)-NH 2 ,

Ac-Arg-cyclo(Asp-Phe-(3-(C(═O)—NH 2 ))-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Phe(4-(C(═O)—NH 2 ))-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-H is-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-Ala-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-H is-D-Phe-Cit-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-Hyp(Bzl)-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-Pro(Bn)-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-Asn-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-Gln-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-Orn-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-Dap-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-His-D-(alpha-Me)Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-His-(alpha-Me)-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Dap-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Sar-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Glu-His-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Asp-H is-D-Phe-Met(O 2 )-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-His-D-Phe-Gln-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Orn-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-His-D-Phe-D-Nle-Trp-Lys)-NH 2

Ac-D-Arg-cyclo(Asp-His-D-Phe-Arg-Trp-Lys)-NH 2

Ac-D-Arg-cyclo(Asp-Ala-D-Phe-Arg-Trp-Lys)-NH 2

Ac-D-Arg-cyclo(Asp-Gln-D-Phe-Arg-Trp-Lys)-NH 2

Ac-D-Arg-cyclo(Asp-Pro(4R-Bzl)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Arg-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Glu-Gln-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Orn-His-D-Phe-Arg-Trp-Glu)-NH 2

Ac-Arg-cyclo(Asp-Arg-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Met-(O 2 )-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Gln-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Hyp-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Pro(4R-NH 2 )-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Glu-Gln-D-Phe-Arg-Trp-Orn)-OH

Ac-Arg-cyclo(Glu-His-D-Phe-Arg-Trp-Orn)-OH

Ac-Arg-cyclo(Orn-Gln-D-Phe-Arg-Trp-Glu)-OH

Ac-Arg-cyclo(Orn-H is-D-Phe-Arg-Trp-Glu)-OH

Ac-D-Arg-cyclo(Glu-His-D-Phe-Arg-Trp-Orn)-OH

Ac-D-Arg-cyclo(Glu-Gln-D-Phe-Arg-Trp-Orn)-OH

Ac-D-Arg-cyclo(Glu-Dab-D-Phe-Arg-Trp-Orn)-OH

Ac-Arg-cyclo(Glu-Arg-D-Phe-Arg-Trp-Orn)-OH

Ac-Arg-cyclo(Glu-Lys-D-Phe-Arg-Trp-Orn)-OH

Ac-Arg-cyclo(Glu-Orn-D-Phe-Arg-Trp-Orn)-OH

Ac-Arg-cyclo(Glu-Asn-D-Phe-Arg-Trp-Orn)-OH

Ac-Arg-cyclo(Glu-Cit-D-Phe-Arg-Trp-Orn)-OH

Ac-Arg-cyclo(Asp-Dab(Acetyl)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Dab(Glycly)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Thr-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Lys-His-D-Phe-Arg-Trp-Asp)-NH 2

Ac-Arg-cyclo(Asp-Phe(4-(C(═O)—NH 2 ))-D-Phe-Arg-Trp-Lys)-OH

Ac-D-Arg-cyclo(Orn-His-D-Phe-Arg-Trp-Glu)-NH 2

Arg-cyclo(Orn-His-D-Phe-Arg-Trp-Glu)-NH 2

Ac-Arg-cyclo(Glu-Met(O 2 )-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Glu-Hyp-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Glu-Arg-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Glu-Lys-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Glu-Orn-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Glu-Cit-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Asp-Gln-D-Phe-Arg-Trp-Lys)-NH-cyclopropyl

Ac-Arg-cyclo(Glu-Gln-D-Phe-Arg-Trp-Orn)-NH-Et

Ac-Arg-cyclo(Glu-Gln-D-Phe-Arg-Trp-Orn)-NH-cyclopropyl

Ac-Arg-cyclo(Glu-His-D-Phe-Arg-Trp-Orn)-NH-Et

Ac-Arg-cyclo(Glu-His-D-Phe-Arg-Trp-Orn)-NH-cyclopropyl

Ac-Arg-cyclo(Glu-Met(═O)-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Glu-Pro(4R-NH 2 )-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Asp-Thr(Bzl)-D-Phe-Arg-Trp-Lys)-OH

Ac-Arg-cyclo(Asp-Dab(Acetyl)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-His-D-Phe-Cit-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Lys-D-Phe-Cit-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Ser-D-Phe-Cit-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Dap(betaPro)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Orn-Dab-D-Phe-Arg-Trp-Glu)-NH 2

Ac-Arg-cyclo(Orn-Ala-D-Phe-Arg-Trp-Glu)-NH 2

Ac-Arg-cyclo(Lys-Dab-D-Phe-Arg-Trp-Asp)-NH 2

Ac-Arg-cyclo(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH-cyclopropyl

Ac-Arg-cyclo(Asp-Pro(4R-2-Cl-Bzl)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Pro(4R-3-Cl-Bzl)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Asp-Pro(4R-4-Cl-Bzl)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(hGlu-His-D-Phe-Arg-Trp-Dab)-NH 2

Ac-Arg-cyclo(hGlu-Dab-D-Phe-Arg-Trp-Dab)-NH 2

Ac-Arg-cyclo(Dab-H is-D-Phe-Arg-Trp-hGlu)-NH 2

Ac-Arg-cyclo(Dab-Dab-D-Phe-Arg-Trp-hGlu)-NH 2

Ac-Arg-cyclo(Orn-Dab-D-Phe-Arg-Trp-Glu)-OH

Ac-Arg-cyclo(Lys-Dab-D-Phe-Arg-Trp-Asp)-OH

Ac-Lys-cyclo(Orn-His-D-Phe-Arg-Trp-Glu)-NH 2

Ac-D-Lys-cyclo(Orn-His-D-Phe-Arg-Trp-Glu)-NH 2

Arg-cyclo(Asp-Ser(Bzl)-D-Phe-Arg-Trp-Lys)-OH

Ac-Lys-cyclo(Asp-His-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Dab-Dab-D-Phe-Arg-Trp-hGlu)-OH

Cyclohexanoyl-Arg-cyclo(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH 2

Cyclopentylacetyl-Arg-cyclo(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH 2

Cyclohexylacetyl-Arg-cyclo(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH 2

Phenylacetyl-Arg-cyclo(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Cit-cyclo(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Gln-cyclo(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Glu-Dab(Acetyl)-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(hGlu-Dab-D-Phe-Arg-Trp-Dab)-OH

Ac-Arg-cyclo(hGlu-Met(O 2 )-D-Phe-Arg-Trp-Dab)-NH 2

Ac-Arg-cyclo(hGlu-Hyp-D-Phe-Arg-Trp-Dab)-NH 2

Ac-Arg-cyclo(hGlu-Gln-D-Phe-Arg-Trp-Dab)-NH 2

Ac-Arg-cyclo(Asp-Orn(Acetyl)-D-Phe-Arg-Trp-Lys)-NH 2

Ac-Arg-cyclo(Glu-Orn(Acetyl)-D-Phe-Arg-Trp-Orn)-NH 2

Ac-Arg-cyclo(Orn-Gln-D-Phe-Arg-Trp-Glu)-NH 2

Ac-Arg-cyclo(Lys-Gln-D-Phe-Arg-Trp-Asp)-NH 2

Ac-D-Arg-cyclo(Orn-Gln-D-Phe-Arg-Trp-Glu)-NH 2

Arg-cyclo(Orn-Asn-D-Phe-Arg-Trp-Glu)-NH 2

Ac-Orn-cyclo(Orn-Asn-D-Phe-Arg-Trp-Glu)-NH 2

Ac-Arg-cyclo(Dab-Gln-D-Phe-Arg-Trp-hGlu)-NH 2

Ac-Arg-cyclo(Lys-Asn-D-Phe-Arg-Nal 2-Asp)-NH 2 ,

or a pharmaceutically acceptable salt of any of the foregoing.

2. A pharmaceutical composition comprising a cyclic peptide or pharmaceutically acceptable salt thereof of claim 1 and a pharmaceutically acceptable carrier.

3. A method for treatment of a melanocortin receptor-mediated disease, indication, condition or syndrome in a human or non-human mammal, comprising the step of administering the pharmaceutical composition of claim 2 .

4. A method for treating a condition responsive to changes in melanocortin receptor function in a human or non-human mammal, comprising the step of administering the pharmaceutical composition of claim 2 .

Continuity (5)

Continuation 14328995 · Jul 11, 2014

Division 13311824 · Dec 6, 2011

Continuation In Part PCTUS2010037589 · Jun 7, 2010

Provisional Application 61184929 · Jun 8, 2009

Related Publication 20160318977A1 · Nov 3, 2016