Multi-functionalized polysaccharide compounds and use thereof for targeting the cation-independent mannose 6-phosphate receptor

A compound having the general formula (I):

• in which:
• n is an integer ranging from 1 to 3,
• represents a single bond or a double bond,
• each of the P1 represents, independently of one another, H, or an acid-labile, base-labile, hydrogen-labile, photo-labile or halogen-labile protecting group, in particular chosen from (CH3)3Si—;
• tBuMe2Si—;
• C6H5CH2—;
• 4-CH3OC6H5CH2—;
• o-NO2C6H5CH2—;
• CH3CO—;
• C6H5CO— or CF3CO—;
• X represents:
• when is a single bond:
• the phosphonate group:
• the fluorophosphonate group:
• the difluorophosphonate group:
• the carboxylate group:
• the malonate group:
• when is a double bond:
• the phosphonate group:
• the carboxylate group:
• with Z representing, independently of one another, H;
• a C1-5 alkyl;
• CF3CH2—;
• C6H5CH2—;
• C6H5—;
• (CH3)3Si—;
• an alkali metal chosen from Na, Li or K;
• an ammonium NH4;
• A represents a divalent radical chosen from —O—, —S—, —NH—, —CH2—;
• L represents:
• —H;
• —NH2;
• —(CH2)n1—CH═CH2 or —(CH2)n1—C≡CH with n1 representing an integer ranging from 0 to 4, then in each of these cases, L1 is absent,
• a substituted or unsubstituted, linear or branched, saturated divalent hydrocarbon-based radical having from 1 to 30 carbon atoms, a substituted or unsubstituted, linear or branched, unsaturated divalent hydrocarbon-based radical having from 2 to 30 carbon atoms,
• a saturated or unsaturated divalent hydrocarbon-based radical as defined above, in which one or more —CH2—, —CH═CH— and/or —C≡C— groups of the saturated or unsaturated hydrocarbon-based radical is (are) replaced, independently of one another, with an —O— group;
• —NH— group;
• —NR1— group with R1 representing a C1-C5 alkyl;
• —S— group;
• —CO—NH— group;
• —NH—CO—O— group;
• —O—N═CH— group;
• —CO—NH—N═CH— group;
• a substituted or unsubstituted, saturated or unsaturated, cyclic or heterocyclic system;
• L1 represents:
• —(CH2)n1—CH═CH2;
• —(CH2)n1—C≡CH;
• —(CH2)n1—N3;
• —(CH2)n1—SH;
• —(CH2)n1—NH2;
• —(CH2)n1—N═C═O;
• —(CH2)n1—N═C═S;
• —(CH2)n1—NHR1;
• —(CH2)n1—NR1R2;
• —(CH2)n1-A1-NH2;
• —(CH2)n1-A1-NHR1;
• —(CH2)n1-A1-NR1R2;
• —(CH2)n1—NHCO—CH2Hal;
• —(CH2)n1—COZ1;
• —(CH2)n1-A1COZ1;
• —(CH2)n1—O—N═CH2;
• —(CH2)n1—CO—NH—N═CH2;
• —(CH2)n1—H;
• a substituted or unsubstituted, saturated or unsaturated, cyclic or heterocyclic system;
• a halogen chosen from F, Cl, Br or I;
• with
• n1 as defined above,
• R1 and R2 representing, independently of one another, a C1-C5 alkyl,
• A1 representing —O—, —NH—,
• Hal representing Cl, Br or I;
• Z1 representing —OH, —OR1, —NHR1, —NH—NH2, —NH—NHR1, —NH—NR1R2, with R1 and R2 as defined above, a halogen chosen from F, Cl, Br or I.