Use of derivatives of cholest-4-en-3-one as medicaments, pharmaceutical compositions containing same, novel derivatives and preparation method thereof
Compound of formula I where X=O or ═N—OH group, R represents a group chosen from A=hydrogen or together with B a carbon-carbon bond, B=hydrogen, hydroxy or together with A a carbon-carbon bond, C, D, E, F=hydrogen or together with D a carbon-carbon bond, or the one of its addition salts with pharmaceutically acceptable acids, with the exception of a few compounds, as a medicament, use in particular as neuroprotectors, novel compounds of formula I and pharmaceutical compositions.
1. A pharmaceutical compound corresponding to the formula I
in which X represents an ═N—OH group,
R represents a group chosen from
A represents a hydrogen atom or together with B a carbon-carbon bond,
B represents a hydrogen atom, a hydroxy group or together with A a carbon-carbon bond,
C represents a hydrogen atom or together with D a carbon-carbon bond,
D represents a hydrogen atom or together with C a carbon-carbon bond,
E represents a hydrogen atom or together with F a carbon-carbon bond,
F represents a hydrogen atom or together with E a carbon-carbon bond,
or one of its addition salts with pharmaceutically acceptable acids,
with the exception of, cholest-4-en-3-one oxime, stigmast 4-en-3-one oxime, cholest-1-en-3-one oxime, cholestan-3-one-oxime, cholesta-4,6-dien-3-one oxime, 5α-stigmastan-3-one oxime and 5α-stigmast-22-en-3-one oxime.
2. A pharmaceutical compound according to claim 1 characterized in that in formula I, A represents together with B a carbon-carbon bond, C, D, represent a hydrogen atom, E, F represent a hydrogen atom or together a carbon-carbon bond and R has the meaning R1, or one of its addition salts with pharmaceutically acceptable acids, with the exception of cholest-4-en-3-one oxime.
3. A pharmaceutical compound according to claim 1 characterized in that in formula I, A represents together with B a carbon-carbon bond, C, D represent a hydrogen atom, E, F represent a hydrogen atom and R has the meaning R2, R3 or R4, or one of its addition salts with pharmaceutically acceptable acids.
4. A pharmaceutical compound according to claim 1 characterized in that in formula I, A represents together with B a double bond, C represents together with D a carbon-carbon bond, E, F represent a hydrogen atom and R has the meaning R1 or R6, or one of its addition salts with pharmaceutically acceptable acids.
5. A pharmaceutical compound according to claim 1 characterized in that in formula I, A represents together with B a carbon-carbon bond, C represents together with D a carbon-carbon bond, E represents together with F a carbon-carbon bond and R has the meaning R1, or one of its addition salts with pharmaceutically acceptable acids.
6. A pharmaceutical composition comprising, as active ingredient, at least one of the compounds defined in claim 1 in a pharmaceutically effective amount, as well as a pharmaceutically acceptable excipient.
7. A pharmaceutical composition comprising, as active ingredient, at least one of the compounds defined in claim 2 in a pharmaceutically effective amount, as well as a pharmaceutically acceptable excipient.
8. A pharmaceutical composition comprising, as active ingredient, at least one of the compounds defined in claim 3 in a pharmaceutically effective amount, as well as a pharmaceutically acceptable excipient.
9. A pharmaceutical composition comprising, as active ingredient, at least one of the compounds defined in claim 4 in a pharmaceutically effective amount, as well as a pharmaceutically acceptable excipient.
10. A pharmaceutical composition comprising, as active ingredient, at least one of the compounds defined in claim 5 in a pharmaceutically effective amount, as well as a pharmaceutically acceptable excipient.
11. A pharmaceutical composition comprising, as active ingredient, at least one of the compounds defined in claim 6 in a pharmaceutically effective amount, as well as a pharmaceutically acceptable excipient.
12. A medicament comprising at least one compound according to claim 1 characterized in that in formula I A represents together with B a carbon-carbon bond, C, D, represent a hydrogen atom, E, F represent a hydrogen atom or together a carbon-carbon bond and R has the meaning R1, or one of its addition salts with pharmaceutically acceptable acids.
13. A medicament comprising at least one compound according to claim 1 characterized in that in formula I, A represents together with B a carbon-carbon bond, C, D represent a hydrogen atom, E, F represent a hydrogen atom and R has the meaning R2 or R3 or R4, or one of its addition salts with pharmaceutically acceptable acids.
14. A medicament comprising at least one compound according to claim 1 characterized in that in formula I, A represents together with B a double bond, C represents together with D a carbon-carbon bond, E, F represent a hydrogen atom and R has the meaning R1 or R6, or one of its addition salts with pharmaceutically acceptable acids.
15. A medicament comprising at least one compound according to claim 1 characterized in that in formula I, A represents together with B a carbon-carbon bond, C represents together with D a carbon-carbon bond, E represents together with F a carbon-carbon bond represent a hydrogen atom and R has the meaning R1, or one of its addition salts with pharmaceutically acceptable acids.
16. A medicament comprising at least one compound according to claim 1 characterized in that in formula I, E represents together with F a carbon-carbon bond, C, D, A, B, represent a hydrogen atom and R has the meaning R1, or one of its addition salts with pharmaceutically acceptable acids.