# US 4,399,125 A · Novel antagonists of the antidiuretic action of arginine vasopressin > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,399,125 A - Document ID: US4399125A - Status: Granted - Kind: A - Application number: 06/322,071 - Filed: 1981-11-16 - Granted: 1983-08-16 - Earliest claimed: 1981-03-24 - Inventors: Maurice Manning; Wilbur H. Sawyer - Web page: https://patentgrep.com/patent/US4399125A ## CPC - C07K 7/16: Oxytocins; Vasopressins; Related peptides - A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00) - Y10S 930/15: Oxytocin or vasopressin; related peptides - C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## Abstract Compounds acting as antagonists of the antidiuretic activity of arginine vasopressin are those of the formula ##STR1## wherein X is D-Phe, D-Val, D-Leu, D-Ile, D-Arg, D-norvaline, D-norleucine, D-cyclohexylalanine, D-.alpha.-aminobutyric acid, D-threonine or D-methionine and Z is D- or L-Arg. ## Claims ### Claim 1 A compound of the formula ##STR4## wherein X is D-Phe, D-Val, D-Leu, D-Ile, D-Arg, D-norvaline, D-norleucine, D-cyclohexylalanine, D-.alpha.-aminobutyric acid, D-threonine or D-methionine and Z is D- or L-Arg. ### Claim 2 (depends on 1) A compound of claim 1, wherein X is D-Phe, D-Val, D-Leu or D-Ile. ### Claim 3 (depends on 1) A compound of claim 1, wherein Z is L-Arg. ### Claim 4 (depends on 1) [1-(.beta.-Mercapto-.beta.,.beta.-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 4-valine]-arginine vasopressin, a compound of claim 1. ### Claim 5 (depends on 1) [1-(.beta.-Mercapto-.beta.,.beta.-cyclopentamethylenepropionic acid), 2-D-valine, 4-valine]-arginine vasopressin, a compound of claim 1. ### Claim 6 (depends on 1) [1-(.beta.-Mercapto-.beta.,.beta.-cyclopentamethylenepropionic acid), 2-D-leucine, 4-valine]-arginine vasopressin, a compound of claim 1. ### Claim 7 (depends on 1) [1-(.beta.-Mercapto-.beta.,.beta.-cyclopentamethylenepropionic acid), 2-D-isoleucine, 4-valine]-arginine vasopressin, a compound of claim 1. ### Claim 8 (depends on 1) [1-(.beta.-Mercapto-.beta.,.beta.-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 4-valine, 8-D-arginine] vasopressin, a compound of claim 1. ### Claim 9 (depends on 1) A method for antagonizing the in vivo response of an animal to the antidiuretic action of an antidiuretic hormone, comprising administering to the animal being treated an amount of a compound of claim 1, in admixture with a physiologically and pharmaceutically acceptable carrier, effective to antagonize the antidiuretic response to the antidiuretic hormone. ### Claim 10 (depends on 9) The method of claim 9, wherein the antiduretic hormone is arginine vasopressin. ### Claim 11 (depends on 9) The method of claim 9, wherein the compound is administered parenterally. ### Claim 12 (depends on 7) A method for antagonizing the in vivo response of an animal to the antidiuretic action of an antidiuretic hormone, comprising administering to the animal being treated an amount of the compound of claim 7, in admixture with a physiologically and pharmaceutically acceptable carrier, effective to antagonize the antidiuretic response to the antidiuretic hormone. ### Claim 13 (depends on 4) A method for antagonizing the in vivo response of an animal to the antidiuretic action of an antidiuretic hormone, comprising administering to the animal being treated an amount of the compound of claim 4, in admixture with a physiologically and pharmaceutically acceptable carrier, effective to antagonize the antidiuretic response to the antidiuretic hormone.