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1. (WO1991006543) GnRH ANALOGS
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1991/006543 International Application No.: PCT/US1990/006309
Publication Date: 16.05.1991 International Filing Date: 30.10.1990
Chapter 2 Demand Filed: 23.05.1991
IPC:
A61K 38/00 (2006.01) ,C07C 279/24 (2006.01) ,C07C 279/28 (2006.01) ,C07C 313/30 (2006.01) ,C07D 249/14 (2006.01) ,C07K 7/02 (2006.01) ,C07K 7/23 (2006.01)
A HUMAN NECESSITIES
61
MEDICAL OR VETERINARY SCIENCE; HYGIENE
K
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
38
Medicinal preparations containing peptides
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
279
Derivatives of guanidine, i.e. compounds containing the group the singly-bound nitrogen atoms not being part of nitro or nitroso groups
20
containing any of the groups X being a hetero atom, Y being any atom, e.g. acylguanidines
24
Y being a hetero atom
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
279
Derivatives of guanidine, i.e. compounds containing the group the singly-bound nitrogen atoms not being part of nitro or nitroso groups
28
having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
313
Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
08
Sulfenic acids; Derivatives thereof
18
Sulfenamides
26
Compounds containing any of the groups X being a hetero atom, Y being any atom
30
Y being a hetero atom
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
249
Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
02
not condensed with other rings
08
1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
10
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
14
Nitrogen atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
K
PEPTIDES
7
Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
02
Linear peptides containing at least one abnormal peptide link
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
K
PEPTIDES
7
Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
04
Linear peptides containing only normal peptide links
23
Luteinising hormone-releasing hormone (LHRH); Related peptides
Applicants:
THE SALK INSTITUTE FOR BIOLOGICAL STUDIES [US/US]; 10010 North Torrey Pines Road La Jolla, CA 92037, US
Inventors:
HOEGER, Carl, A.; US
RIVIER, Jean, Edouard, Frederic; US
THEOBALD, Paula, Guess; US
PORTER, John, S.; US
RIVIER, Catherine, Laure; US
VALE, Wylie, Walker, Jr.; US
Agent:
WATT, Phillip, H. ; Fitch, Even, Tabin & Flannery Room 900 135 South LaSalle Street Chicago, IL 60603, US
Priority Data:
428,82730.10.1989US
545,23927.06.1990US
Title (EN) GnRH ANALOGS
(FR) ANALOGUES DE GnRH
Abstract:
(EN) Peptides which include unnatural amino acids and which either inhibit or promote the secretion of gonadotropins by the pituitary gland and inhibit the release of steroids by the gonads. Administration of an effective amount of such peptides that are GnRH antagonists prevents ovulation of female mammalian eggs and/or the release of steroids by the gonads. The antagonists may be used to treat steroid-dependent tumors, such as prostatic and mammary tumors. The peptides are analogs of the decapeptide GnRH wherein there is at least one residue of an unnatural amino acid in the 3-position, the 5-position, the 6-position and/or the 8-position. Such unnatural amino acids are useful in the synthesis of peptides and have the formula U*: where n is an integer from 1 to 6; Y is N-CN, N-CONHR9, S, O or CH-NO2; R9 is H, Ac, lower alkyl, aromatic or heterocyclic; X is NH, O, S, M1(CHq)pM2 or M1-(CH2)p'-M2(CH2)p''-M3, where M1 is NR10, O, S or CHR3 wherein R3 is methyl, ethyl, propyl, phenyl, pyridinyl, pyrimidinyl or purinyl; q is 1 or 2; p, p' and p'' are integers between 0 and 6; R10 is H, lower alkyl or the like, and M2 and M3 are M1, COOH, CONH2, COOR3 or CN; R1 is H, alkyl, modified alkyl, alkenyl, alkynyl, aryl or a direct bond to X; R2 is R1, OH, NH2, NHR1, or heterocycle.
(FR) Peptides comprenant des acides aminés non naturels et soit inhibant soit favorisant la secrétion de gonadotropines par la glande pituitaire et inhibant la libération de stéroïdes par les gonades. L'administration d'une dose efficace desdits peptides, lesquels sont des antagonistes de GnRH, empêchent l'ovulation d'÷ufs de mammifères femelles et/ou la libération de stéroïdes par les gonades. On peut utiliser les antagonistes afin traiter les tumeurs dépendantes de stéroïdes telles que des tumeurs prostatiques et mammaires. Les peptides sont des analogues du décapeptide GnRH, dans lequel se trouve au moins un résidu d'un acide aminé non naturel dans la position 3, la position 5, la position 6 et/ou la position 8. Lesdits acides aminés non naturels sont utiles dans la synthèse de peptide et ont la formule U*, dans laquelle n représente un nombre entier compris entre 1 et 6; Y représente N-CN, N-CONHR9, S, O, ou CH-NO2; R9 représente H, Ac, alkyle inférieur, aromatique ou hétérocyclique; X représente NH, O, S, M1(CHq)pM2 ou M1-(CH2)p'-M2(CH2)p''-M3, où M1 représente NR10, O, S ou CHR3 dans laquelle R3 représente méthyle, éthyle, propyle, phényle, pyridinyle, pyrimidinyle ou purinyle; q représente 1 ou 2; p, p' et p'' représentent des nombres entiers compris entre 0 et 6; R10 représente H, alkyle inférieur ou analogue et M2 ainsi que M3 représentent M1, COOH, CONH2, COOR3 ou CN; R1 représente H, alkyle, alkyle modifié, alcényle, alkynyle, aryle ou une liaison directe à X; R2 représente R1, OH, NH2, NHR1 ou un hétérocycle.
Designated States: AU, CA, JP, KR
European Patent Office (AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LU, NL, SE)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
EP0500695CA2066184KR1019920702351AU1990067392