Novel stabilized activated derivatives of carbamic acid, their process of preparation and their use for the preparation of ureas

Compounds of formula (VIII bis)

• wherein:
• I) the total number of atoms forming the cycle is greater than six;
• II) “n” is a whole number greater than or equal to 1;
• III) “i” is a whole number varying from 2 to n+1;
• IV) R1 represents:
• hydrogen, a (C1-C20) alkyl group, substituted or not, an aryl group, whose cyclic structure contains 5 to 20 carbon atoms;
• V) Ri represents:
• hydrogen, the protected or unprotected side chain of an amino acid selected from natural and synthetic amino acids, a (C1-C20) alkyl group, substituted or not, an aryl group, whose cyclic structure contains 5 to 20 carbon atoms, an ORa, NH2, OH, —COORa, —CONHRa, —CONH2, —CH2COORa, —CH2CONHRa, —CH2CONH2 group,
• Ra representing an allyl, benzyl, t-butyl, fluorenylmethyl, alkyl group having 1 to 20 carbon atoms, or an aryl group whose cyclic structure contains 5 to 20 carbon atoms;
• VI) Rn+2 represents:
• hydrogen, a (C1-C20) alkyl group, substituted or not, an aryl group, whose cyclic structure contains 5 to 20 carbon atoms,
• VII) optionally groups R1 and Ri can form a cycle;
• VIII) Y is or contains:
• a (C1-C20) alkyl group, substituted or not,
• an aryl group,
• a pseudopeptide,
• or forms with N of group NW′ an amino acid residue or a chain of amino acid residues comprising 1 to 10 residues, the acid function of the amino acid residue or of the chain of amino acid residues being fixed on the group NR1;
• IX) W′is or contains:
• hydrogen,
• a (C1-C20) alkyl group, substituted or not,
• an aryl group, whose cyclic structure contains 5 to 20 carbon atoms,

Compounds of formula (VII)

• wherein:
• I) “n” is a whole number greater than or equal to 1,
• II) “i” is a whole number varying from 2 to n+1,
• III) Y is or contains:
• a pseudopeptide,
• an amino acid residue or a chain of amino acids comprising 1 to 10 residues,
• a GP group which can be:
• a protective group selected from the groups consisting of:
• oxycarbonyl,
• acyl,
• GP along with R1 and the N then are bonded to form a phthalimido group of formula:
• a biotinyle group having the following formula:
• IV) R1 represents:
• hydrogen, a (C1-C20) alkyl group, substituted or not, an aryl group, whose cyclic structure contains 5 to 20 carbon atoms,
• V) Ri represents:
• hydrogen, halogen, a protected or unprotected side chain of an amino acid selected from natural and synthetic amino acids, a (C1-C20) alkyl group, substituted or not, an aryl group, whose cyclic structure contains 5 to 20 carbon atoms, an ORa, NH2, OH, —COORa, —CONHRa, —CONH2, —CH2COORa, —CH2CONHRa, —CH2CONH2 group,
• Ra representing an allyl, benzyl, t-butyl, fluorenylmethyl, alkyl group having 1 to 20 carbon atoms, or an aryl group whose cyclic structure contains 5 to 20 carbon atoms,
• VI) W and W′ are or contain:
• hydrogen,
• a pseudopeptide,
• an amino acid residue or a chain of amino acid residues comprising 1 to 10 residues;
• VII) optionally R1 and Ri can also form a cycle;
• provided that the compounds of the following formulas are excluded:
• and provided that the compound of formula (VII) is different from the analogs of the peptide Tyr-Gly-Gly-Phe-Leu-OH, containing one or several derivatives as defined below mimicking the side chain of amino acids present in the peptide and permitting the introduction of one or several urea linkages, wherein the compound of formula (VII) is different from the following compounds:
• wherein R represents hydroxybenzyl, a hydrogen atom, a benzyl group, or an isobutyl group,
• and provided that the compound of formula (VII) is different from: