Cyclopeptides and pharmaceutical preparations thereof and also processes for their manufacture
First Claim
1. A cyclic octapeptide of the formula ##STR44## in which trp represents D-Trp, andGaba(Ar) represents the residue of a γ
- -amino-butyric acid substituted in the β
-position by cyclohexyl, phenyl or naphthyl or by a phenyl or naphthyl which is substituted by halogen, nitro or phenoxy, a pharmaceutically acceptable acid addition salt and a complex thereof.
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Accused Products
Abstract
The somatostatin-analogous cyclic octapeptides according to the invention of the general formula ##STR1## in which trp represents L-Trp or D-Trp, in which the benzene ring may be substituted by a halogen atom, and
Gaba(Ar) represents the residue of a γ-aminobutyric acid substituted by a cyclic hydrocarbyl radical,
and their acid addition salts and complexes are distinguished by a strong inhibition of the insulin and glucagon secretion of the pancreas and are therefore therapeutically acceptable, preferably in the form of pharmaceutical preparations, in similar indications to those of somatostatin, especially as anti-diabetics. The compounds are manufactured by conventional processes of peptide synthesis, especially by liberation from corresponding protected intermediates after intramolecular cyclization of a corresponding linear octapeptide.
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Citations
15 Claims
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1. A cyclic octapeptide of the formula ##STR44## in which trp represents D-Trp, and
Gaba(Ar) represents the residue of a γ - -amino-butyric acid substituted in the β
-position by cyclohexyl, phenyl or naphthyl or by a phenyl or naphthyl which is substituted by halogen, nitro or phenoxy, a pharmaceutically acceptable acid addition salt and a complex thereof. - View Dependent Claims (2, 3, 4, 5, 12, 13)
- -amino-butyric acid substituted in the β
-
6. [D-Trp8 ;
- β
-cyclohexyl-Gaba12 ]-cyclosomatostatin(5-12)-octapeptide, in the form of a diastereoisomeric mixture or of an individual diastereoisomer, a pharmaceutically acceptable acid addition salt and a complex thereof. - View Dependent Claims (7)
- β
-
8. [D-Trp8 ;
- β
-(3-phenoxyphenyl)-Gaba12 ]-cyclosomatostatin(5-12)-octapeptide, in the form of a diastereoisomeric mixture or of an individual diastereoisomer, a pharmaceutically acceptable acid addition salt and a complex thereof. - View Dependent Claims (9)
- β
-
10. [D-Trp8 ;
- β
-(1-naphthyl)-Gaba12 ]-cyclosomatostatin(5-12)-octapeptide, in the form of a diastereoisomeric mixture or of an individual diastereoisomer, a pharmaceutically acceptable acid addition salt and a complex thereof. - View Dependent Claims (11)
- β
-
14. A compound of the formula ##STR45## in which trp represents [L-Trp or] D-Trp, and
Gaba(Ar) represents the residue of a γ - -amino-butyric acid substituted in the β
-position by cyclohexyl, phenyl or naphthyl, or by a phenyl or naphthyl which is substituted by halogen, nitro or phenoxy,A represents an γ
-amino-protecting group or hydrogen andB represents a hydroxyl-protecting group or hydrogen, it being possible for only one of the symbols A and B to represent hydrogen, and an acid addition salt thereof.
- -amino-butyric acid substituted in the β
- 15. A linear peptide of the formula
- space="preserve" listing-type="equation">H-Asn-Phe-Phe-trp-Lys(A)-Thr(B)-Phe-Gaba(Ar)-C (IIIb)
in which trp represents D-Trp, Gaba(Ar) represents the residue of a γ
-amino-butyric acid substituted in the β
-position by cyclohexyl, phenyl or naphthyl, or by a phenyl or naphthyl which is substituted by halogen, nitro or phenoxy,A represents an ε
-amino-protecting group or hydrogen,B represents a hydroxyl-protecting group or hydrogen, it being possible for only one of the symbols A and B to represent hydrogen, and C represents a free hydroxyl group, a hydroxyl group modified by an activating group or represents the hydrazino group --NH--NH2, and a acid addition salt thereof.
Specification