Patent DE-3661922-D1 (DE)
Title: Coupling compounds, process for their preparation and their use as mediators in the development of the effects of interferons
Inventor: LEBLEU BERNARD RES LE JARDIN A
IPC: A61K31/70
Filed: 1986-05-29
Granted: 1989-03-02
Abstract: For the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE 1. Coupling compounds represented by the formula (I) defined below : see diagramm : EP0203870,P77,F1  in which : - Y and T, identical or different, represent independently of one another O, S, Se or NH ; - Z and W, identical or different, represent independently of one another O, S, or NH ; - A represents adenine or one of its derivatives, particularly those of the formula :  see diagramm : EP0203870,P77,F2  - SIGMA is a whole number equal to n-1, n being a whole number greater than or equal to 3 ; - m is a whole number greater than or equal to 0 and preferably greater than or equal to 2 ; - X is a whole number greater than or equal to 1, preferably comprised from 2 to 10 ; - Pr is a polypeptide chain comprising at least 5 amino acids, and the nitrogen atom belonging to the ring : see diagramm : EP0203870,P77,F3  belonging also to the end of a lateral sequence of the polypeptide Pr and/or belonging to a group see diagramm : EP0203870,P77,F4  coming from a COOH group modified by hydrazine. For the Contracting State : AT 1. Process for preparing coupling compounds of formula (I) :  see diagramm : EP0203870,P85,F1 in which : - Y and T, identical or different, represent independently of one another O, S, Se or NH ; - Z and W, identical or different, represent independently of one another O, S, or NH ; - A represents adenine or one of its derivatives, particularly those of the formula :  see diagramm : EP0203870,P85,F2  - SIGMA is a whole number equal to n-1, n being a whole number greater than or equal to 3 ; - m is a whole number greater than or equal to 0 and preferably greater than or equal to 2 ; - X is a whole number greater than or equal to 1, preferably comprised from 2 to 10 ; - Pr is a polypeptide chain comprising at least 5 amino acids, and the nitrogen atom belonging to the ring :  see diagramm : EP0203870,P85,F3  belonging also to the end of a lateral sequence of the polypeptide Pr and/or belonging to a group  see diagramm : EP0203870,P85,F4  coming from a COOH group modified by hydrazine characterized in that it comprises : - the oxidation of the starting compound of the following formula (Ibis) : see diagramm : EP0203870,P86,F5  in which Y, Z, T, W, A, m, SIGMA have the above mentioned meanings ; to introduce two aldehyde functions on to the carbons at the 2' and 3' positions of the last nucleoside unit and to obtain the compound of the following formula (Iter) :  see diagramm : EP0203870,P86,F6  - the reductive alkylation of the compound (Iter) by a polypeptide Pr-NH2  whose chain comprises at particularly NH2 , this reaction taking place between the aldehyde functions of the compound (Iter) with the NH2  group of the polypeptide to obtain the compound of formula (I) :  see diagramm : EP0203870,P86,F7  - the fractionation between the coupling compounds according to the invention and the uncoupled products particularly by molecular filtration.