EP0253190A2
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EP
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Partially retro-inverted tuftsin analogues, method for the preparation thereof and pharmaceutical compositions containing them
Assignee: Sclavo SpA
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Filing: 1987-06-29
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Granted: —
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Expires: 2007-06-29
Abstract
Abstract New partially retro-inverted tuftsin analogues of general formula I wherein R represents the side-chain of the amino acids threonine, methionine or leucine R¹ represents the side-chain of the amino acids lysine or arginine R² is hydrogen or a metabolically labile acyl group, all the asymmetric carbon atoms are either of the S- or R-configuration, or, alternatively, the first, third, and fourth asymmetric carbons, starting from the N-terminal residue, are of the S-configuration while the second one is of the R- or (R,S)-configuration, and the corresponding pharmacologically acceptable salts, esters and amides. The new compounds which share the same pharmacological properties of tuftsin, are much more stable toward the enzymatic degradation than the parent molecule.
Inventors
- 👤 Antonio Silvio Verdini
- 👤 Fabio Bonelli
- 👤 Antonello Pessi
- 👤 Franco Cardinali
- 👤 Diana Boraschi
- 👤 Stefano Censini
- 👤 Romano Di Trapani
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-30 16:40
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/02; C07K5/0212; A; A61; A61P; A61P31/00; A61P31/04; A61P35/00; A61P37/00; A61P37/02; A61P37/04; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; C07C323/00
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
52 words
1) A compound of general formula I wherein R represents the side-chain of the amino acids threonine, methionine or leucine, R¹ represents the side-chain of the amino acids lysine or arginine, and R² is a hydrogen atom or a metabolically labile acyl group, and the corresponding pharmacologically acceptable salts, esters and amides.
Claim 2
Dependent Claim
52 words
1) A compound of general formula I wherein R represents the side-chain of the amino acids threonine, methionine or leucine, R¹ represents the side-chain of the amino acids lysine or arginine, and R² is a hydrogen atom or a metabolically labile acyl group, and the corresponding pharmacologically acceptable salts, esters and amides.
Claim 3
Dependent Claim
11 words
2) A compound as in claim 1 wherein R² is hydrogen.
Claim 4
Dependent Claim
17 words
3) A compound as in claim 2 wherein R¹ represents the side-chain of the amino acid lysine.
Claim 5
Dependent Claim
17 words
4) A compound as in claim 3 wherein R represents the side-chain of the amino acid threonine.
Claim 6
Dependent Claim
12 words
5) A compound as in claim 4 which is the {2-[N-(1-amino-2-hydroxypropyl)carbamyl]-6-amino} hexanoyl-prolyl-arginine.
Claim 7
Dependent Claim
163 words
6) A process for preparing a compound of claim 1 which consists of condensing a malonic acid derivative of formula II wherein R 1ʹ is the side-chain of the amino acids lysine or arginine wherein the amino or guanidino group is suitably protected, P is an easily removable carboxyl protecting group Pʹ is an easily removable guanidino protecting group with an amide of formula III wherein Rʹ represents the side-chain of the amino acids threonine, methionine or leucine wherein the functional groups, if any, are suitably protected, in the presence of a suitable coupling agent, reacting the thus obtained compound of formula IV wherein Rʹ, R 1ʹ , P, and Pʹ are as defined above, with (1,1-bis-trifluoroacetoxy)iodobenzene to convert the terminal amido group in primary amino, acylating, if desired, the terminal amino function with a metabolically labile acyl group, removing the protecting groups and, if desired, converting the thus obtained compound of formula I into the corresponding pharmacologically acceptable salts, esters and amides.
Claim 8
Dependent Claim
131 words
7) A process for preparing a compound of claim 2 which consists in condensing a malonic acid derivative of formula II wherein R 1ʹ is the side-chain of the amino acids lysine or arginine wherein the amino or guanidino group is suitably protected, P is an easily removable carboxyl protecting group Pʹ is an easily removable guanidino protecting group with an amide of formula III wherein Rʹ represents the side-chain of the amino acids threonine, methionine and leucine wherein the functional groups, if any, are suitably protected, in the presence of a suitable coupling agent, removing the protecting groups, reacting the thus obtained compound with (1,1-bis-trifluoroacetoxy)- iodobenzene and, if desired, converting the thus obtained compound of formula I wherein R² is hydrogen into the corresponding pharmacologically acceptable salts, esters and amides.
Claim 9
Dependent Claim
29 words
8) A pharmaceutical composition comprising an immunostimulating effective amount of the peptides of claims 1, 2, 3, 4 or 5 alone or in combination With a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
32 words
9) A compound of general formula IV wherein Rʹ, R 1ʹ , P, and Pʹ are as defined in claim 6 and the corresponding derivatives wherein the protecting groups have been removed.
Claim 11
Dependent Claim
9 words
10) A compound of claim 9 which is {2-[N-(1-carbamyl-2-hydroxy-propyl)carbamyl]-6-amino}hexanoyl-L-prolyl-L-arginine.
References Cited (Backward Citations)
No citation records indexed.
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