Compounds, use thereof as medicaments, and method of preparation thereof

1. A pharmaceutical composition, comprising a pharmaceutically acceptable vehicle and 0.1 to 1% by weight of a compound of the following formula (VI) as an active ingredient:

in which:

n represents an integer from 1 to 12,q and q′ represent, independently of one another, integers from 0 to 2,

p and p′ represent, independently of one another, integers from 0 to 4,

B and B′ represent, independently of one another, an oxygen atom or a CH 2 group,

R and R′ represent, independently of one another, a halogen selected from chlorine, bromine, iodine or fluorine atoms, or a linear or branched alkyl group with 1 to 3 carbon atoms,

R′″ represents a hydrogen or a group protecting the amine function selected from the groups Boc, Fmoc, Bn, Z,

if A and A′ represent, independently of one another, a CH 2 group, then m and m′ represent, independently of one another, integers from 1 to 8, and

if A and A′ represent, independently of one another, an NH group or an NR″ group, in which R″ is a linear or branched alkyl group with 1 to 3 carbon atoms, then m and m′ represent, independently of one another, integers from 2 to 8, or

a physiologically acceptable acid salt derived from a compound of formula (VI) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH),

the compounds of the following formulae being excluded:

2. The pharmaceutical composition according to claim 1 , wherein the compound is of the following formula (I):

in which:

n represents an integer from 1 to 12,

q and q′ represent, independently of one another, integers from 0 to 2,

p and p′ represent, independently of one another, integers from 0 to 4,

B and B′ represent, independently of one another, an oxygen atom or a CH 2 group,

R and R′ are, independently of one another, a halogen selected from chlorine, bromine, iodine or fluorine atoms, or a linear or branched alkyl group with 1 to 3 carbon atoms,

if A and A′ represent, independently of one another, a CH 2 group, then m and m′ represent, independently of one another, integers from 1 to 8,and

if A and A′ represent, independently of one another, an NH group or an NR″ group, in which R″ is a linear or branched alkyl group with 1 to 3 carbon atoms, then m and m′ represent, independently of one another, integers from 2 to 8,

or a physiologically acceptable acid salt derived from a compound of formula (I) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH),

the compounds of the following formulae being excluded:

3. The pharmaceutical composition according to claim 1 , wherein the compound is of the following formula (II):

in which A, A′, B, B′, R, R′, m, m′, n, p, p′ are as defined above, or

a physiologically acceptable acid salt derived from a compound of formula (II) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH).

4. The pharmaceutical composition according to claim 1 , wherein the compound is of the following formula (III):

in which A, B, R, m, n, p are as defined above, or

a physiologically acceptable acid salt derived from a compound of formula (III) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH).

5. The pharmaceutical composition according to claim 1 , wherein the compound is of the following formula (IV):

in which n represents 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12,or

a physiologically acceptable acid salt derived from a compound of formula (IV), or

a compound of the following formula 6:

a physiologically acceptable acid salt derived from a compound of formula (6) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH).

6. The pharmaceutical composition according to claim 1 , wherein,

m is different from m′, and/or

p is different from p′, and/or

R is different from R′, and/or

A is different from A′, and/or

B is different from B′.

7. The pharmaceutical composition according to claim 1 , wherein the active ingredient is a compound according to formula (II):

in which A, A′, B, B′, R, R′, m, m′, n, p, p′ are as defined above, for which the sum (m+m′+n) is less than or equal to 10,or

a physiologically acceptable acid salt derived from a compound of formula (II) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH), or

a compound according to formula (III):

in which A, B, R, m, n, p are as defined above, for which the sum (2m+n) is less than or equal to 10,or a physiologically acceptable acid salt derived from a compound of formula (III) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH),

said pharmaceutical composition being formulated in aqueous solution.

8. The pharmaceutical composition according to claim 1 , wherein the active ingredient is a compound according to formula (II):

in which A, A′, B, B′, R, R′, m, m′, n, p, p′ are as defined above, for which the sum (m+m′+n) is greater than 10,or

a physiologically acceptable acid salt derived from a compound of formula (II) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH), or

a compound according to formula (III):

in which A, B, R, m, n, p are as defined above, for which the sum (2m+n) is less than or equal to 10,or

a physiologically acceptable acid salt derived from a compound of formula (III) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH),

said pharmaceutical composition being formulated in aqueous-alcoholic solution.

9. The pharmaceutical composition according to claim 1 , wherein the composition is configured to be administered topically.

10. A method for preparing a compound of formula (Ia), comprising:

a) cleaving protecting groups Y of a compound of the following formula (X′):

in which:

n represents an integer from 1 to 12,

m and m′ represent, independently of one another, integers from 2 to 8,

q and q′ represent, independently of one another, integers from 0 to 2,

p and p′ represent, independently of one another, integers from 0 to 4,

A and A′ represent, independently of one another, an NH group or an NR″ group, in which R″ is a linear or branched alkyl group with 1 to 3 carbon atoms,

B and B′ represent, independently of one another, an oxygen atom or a CH 2 group,

R and R′ represent, independently of one another, a halogen selected from chlorine, bromine, iodine or fluorine atoms, or a linear or branched alkyl group with 1 to 3 carbon atoms,

Y represents a group protecting the amines Boc or Fmoc,

to obtain:

a compound of the following formula (XI′):

in which:

n represents an integer from 1 to 12,

m and m′ represent, independently of one another, integers from 2 to 8,

q and q′ represent, independently of one another, integers from 0 to 2,

p and p′ represent, independently of one another, integers from 0 to 4,

A and A′ represent, independently of one another, an NH group or an NR″ group, in which R″ is a linear or branched alkyl group with 1 to 3 carbon atoms,

B and B′ represent, independently of one another, an oxygen atom or a CH 2 group,

R and R′ represent, independently of one another, a halogen selected from chlorine, bromine, iodine or fluorine atoms, or a linear or branched alkyl group with 1 to 3 carbon atoms, or

an acid salt derived from a compound of formula (XI′) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH);

b) reacting the compound of formula (XI′) formed during stage a) with a compound of the following formula (XII):

in which GP represents a leaving group selected from —SR, -NTf or

 and Y represents a group protecting the amines Boc or Fmoc,

to obtain a compound of the following formula (XIII′):

in which:

n represents an integer from 1 to 12,

m and m′ represent, independently of one another, integers from 2 to 8,

q and q′ represent, independently of one another, integers from 0 to 2,

p and p′ represent, independently of one another, integers from 0 to 4,

A and A′ represent, independently of one another, an NH group or an NR″ group, in which R″ is a linear or branched alkyl group with 1 to 3 carbon atoms,

B and B′ represent, independently of one another, an oxygen atom or a CH 2 group,

R and R′ represent, independently of one another, a halogen selected from chlorine, bromine, iodine or fluorine atoms, or a linear or branched alkyl group with 1 to 3 carbon atoms, and

Y represents a group protecting the amines Boc or Fmoc; and

c) deprotecting the amine functions of the compound of formula (XIII′) obtained in stage b) to obtain a compound of the following formula (Ia):

in which:

n represents an integer from 1 to 12,

m and m′ represent, independently of one another, integers from 2 to 8,

q and q′ represent, independently of one another, integers from 0 to 2,

p and p′ represent, independently of one another, integers from 0 to 4,

A and A′ represent, independently of one another, an NH group or an NR″ group, in which R″ is a linear or branched alkyl group with 1 to 3 carbon atoms,

B and B′ represent, independently of one another, an oxygen atom or a CH 2 group,

R and R′ are, independently of one another, a halogen selected from chlorine, bromine, iodine or fluorine atoms, or a linear or branched alkyl group with 1 to 3 carbon atoms, or

an acid salt derived from a compound of formula (Ia) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH).

11. The method according to claim 10 , wherein the compound prepared is according to formula (IV), the method comprising:

a) cleaving the groups Y of a compound of the following formula (XX):

in which n represents 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12,

and Y represents a group protecting the amines Boc or Fmoc,

to obtain:

a compound of the following formula (XXI):

in which n represents 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12,or

an acid salt derived from a compound of formula (XXI) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH);

b) reacting the compound of formula (XXI) formed during stage a) with a compound of the following formula (XII):

in which GP represents a leaving group selected from —SR, -NTf or

 and Y represents a group protecting the amines Boc or Fmoc,

to obtain a compound of formula (XXII):

in which n represents 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12,and Y represents a group protecting the amines Boc or Fmoc, and

c) deprotecting the amine functions of the compound of formula (XXII) obtained in stage b) to obtain a compound of formula (IV):

in which n represents 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12,or

an acid salt derived from a compound of formula (IV) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH).

12. A pharmaceutical composition, configured to be administered topically, comprising as an active ingredient at least one compound, in a range of 0.1 to 1% by weight, of the following formula (VI):

in which:

n represents an integer from 1 to 12,

q and q′ represent, independently of one another, integers from 0 to 2,

p and p′ represent, independently of one another, integers from 0 to 4,

B and B′ represent, independently of one another, an oxygen atom or a CH 2 group,

R and R′ represent, independently of one another, a halogen selected from chlorine, bromine, iodine or fluorine atoms, or a linear or branched alkyl group with 1 to 3 carbon atoms,

R′″ represents a hydrogen or a group protecting the amine function selected from the groups Boc, Fmoc, Bn, Z,

if A and A′ represent, independently of one another, a CH 2 group, then m and m′ represent, independently of one another, integers from 1 to 8,and

if A and A′ represent, independently of one another, an NH group or an NR″ group, in which R″ is a linear or branched alkyl group with 1 to 3 carbon atoms, then m and m′ represent, independently of one another, integers from 2 to 8,or

a physiologically acceptable acid salt derived from a compound of formula (VI) selected from a hydrochloride, a formate, a trifluoroacetate or an oxalate (HOOCCOOH),

the compounds of the following formulae being excluded:

13. The pharmaceutical composition according to claim 12 , wherein the at least one compound is selected from the group consisting of: