US 2015/0086615 A1 · STEROL DERIVATIVES AND USE THEREOF FOR TREATING DISEASES INVOLVING TRANSFORMED ASTROCYTE CELLS OR FOR TREATING MALIGNANT HAEMOPATHIES

Abstract

Novel sterol derivatives, the preparation method thereof, pharmaceutical compositions containing them and use thereof for treating diseases involving transformed astrocyte cells or for treating malignant haemopathies. The treatment of glioblastoma multiforme, as well as of other cancers, such as lymphomas, neuroblastomas and melanomas is also described.

Claims23

Dependent claims

1-22. (canceled)

Compound of formula (I) having a 7beta-hydroxycholesterol basic structure

in which
A represents
an —(R1)n— group in which R1 is an amino acid residue bound by its
C-terminal end and n=1 or 2, each R1 being identical or different, in which the
N-terminal end of said amino acid can be substituted with a —C(O)—R2 group in which R2 is a mono- or polycyclic C6-C14 arylalkyl group or a mono- or polycyclic C5-C14 heteroarylalkyl group that can comprise one or more heteroatoms, which may be identical or different, which is unsubstituted or substituted with at least one linear or branched C1-C4 alkyl group;
a mono- or polycyclic C6-C14 arylalkyloxy group or a mono- or polycyclic C5-C14 heteroarylalkyloxy group that can comprise one or more heteroatoms, which may be identical or different, which are unsubstituted or substituted with at least one linear or branched C1-C4 alkyl group, or
a —C(O)—NH—R4 or —C(S)—NH—R4 group in which R4 is hydrogen;
a C1-C12 alkyl group, linear or branched, unsubstituted or substituted with at least one group selected from OR, NHR and SR, where R represents hydrogen, a linear C1-C12 alkyl or an unsubstituted C6-C14 aryl;
a C6-C14 aryl group, unsubstituted or substituted with at least one linear or branched C1-C6 alkyl or at least one group selected from OR, NHR and SR, as defined above;
an acyl group;
a formyl group;
a sulphonyl group;
a sulphinyl group;
or else R4 represents an allyl group or a sugar residue;
a —C(O)—OR5 group in which R5 is a C1-C12 alkyl, linear or branched, unsubstituted or substituted with at least one group selected from OR, NHR and SR, as defined above;
a —C(O)—R6 group in which R6 is a saturated C5-C14 heterocycle comprising 1 or 2 heteroatoms, unsubstituted or substituted with at least one linear or branched C1-C6 alkyl or at least one group selected from OR, NHR and SR, as defined above;
or a linear or branched C1-C12 alkyl group unsubstituted or substituted with a group selected from OR, NHR and SR, as defined above;
a C6-C14 aryl group or a C5-C14 heteroaryl group, which are unsubstituted or substituted with at least one linear or branched C1-C6 alkyl or with at least one group selected from OR, NHR and SR, as defined above;
or else a sugar residue.
B represents a —C(O)—R7 group in which R7 is hydrogen;
a C1-C12, preferably C1-C6, alkyl, linear or branched, unsubstituted or substituted with at least one group selected from OR, NHR and SR, as defined above;
a C6-C14 aryl group, unsubstituted or substituted with at least one linear or branched C1-C6 alkyl or at least one group selected from OR, NHR and SR, as defined above;
or R7 represents OR8, in which R8 is a linear or branched, C1-C12, preferably C1-C6, alkyl,
provided that:
when B is —C(O)—R7 and A is —C(O)—R6, then R6 and R7 are not simultaneously methyl, propyl or an unsubstituted phenyl group;
when B is —C(O)—R7 where R7 is OR8 and R8 is ethyl, then A is different from —C(O)—OR5 where R5 is ethyl.

23 more elements

Dependencies are inferred from the claim text.

Facts

Application

14/399,336Filed 7 May 2013

Priority

FR 12305518.810 May 2012

Published

26 Mar 2015

Term ends

Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07J 9/005
Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g.…:…
A61K 31/575
Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids: substituted in position 17 beta by a chain…
A61K 31/58
Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids: containing heterocyclic rings, e.g. danazol,…
A61P 35/00
Antineoplastic agents

Abstract

Claims23

Dependent claims

1-22. (canceled)

Compound of formula (I) having a 7beta-hydroxycholesterol basic structure

in which
A represents
an —(R1)n— group in which R1 is an amino acid residue bound by its
C-terminal end and n=1 or 2, each R1 being identical or different, in which the
N-terminal end of said amino acid can be substituted with a —C(O)—R2 group in which R2 is a mono- or polycyclic C6-C14 arylalkyl group or a mono- or polycyclic C5-C14 heteroarylalkyl group that can comprise one or more heteroatoms, which may be identical or different, which is unsubstituted or substituted with at least one linear or branched C1-C4 alkyl group;
a mono- or polycyclic C6-C14 arylalkyloxy group or a mono- or polycyclic C5-C14 heteroarylalkyloxy group that can comprise one or more heteroatoms, which may be identical or different, which are unsubstituted or substituted with at least one linear or branched C1-C4 alkyl group, or
a —C(O)—NH—R4 or —C(S)—NH—R4 group in which R4 is hydrogen;
a C1-C12 alkyl group, linear or branched, unsubstituted or substituted with at least one group selected from OR, NHR and SR, where R represents hydrogen, a linear C1-C12 alkyl or an unsubstituted C6-C14 aryl;
a C6-C14 aryl group, unsubstituted or substituted with at least one linear or branched C1-C6 alkyl or at least one group selected from OR, NHR and SR, as defined above;
an acyl group;
a formyl group;
a sulphonyl group;
a sulphinyl group;
or else R4 represents an allyl group or a sugar residue;
a —C(O)—OR5 group in which R5 is a C1-C12 alkyl, linear or branched, unsubstituted or substituted with at least one group selected from OR, NHR and SR, as defined above;
a —C(O)—R6 group in which R6 is a saturated C5-C14 heterocycle comprising 1 or 2 heteroatoms, unsubstituted or substituted with at least one linear or branched C1-C6 alkyl or at least one group selected from OR, NHR and SR, as defined above;
or a linear or branched C1-C12 alkyl group unsubstituted or substituted with a group selected from OR, NHR and SR, as defined above;
a C6-C14 aryl group or a C5-C14 heteroaryl group, which are unsubstituted or substituted with at least one linear or branched C1-C6 alkyl or with at least one group selected from OR, NHR and SR, as defined above;
or else a sugar residue.
B represents a —C(O)—R7 group in which R7 is hydrogen;
a C1-C12, preferably C1-C6, alkyl, linear or branched, unsubstituted or substituted with at least one group selected from OR, NHR and SR, as defined above;
a C6-C14 aryl group, unsubstituted or substituted with at least one linear or branched C1-C6 alkyl or at least one group selected from OR, NHR and SR, as defined above;
or R7 represents OR8, in which R8 is a linear or branched, C1-C12, preferably C1-C6, alkyl,
provided that:
when B is —C(O)—R7 and A is —C(O)—R6, then R6 and R7 are not simultaneously methyl, propyl or an unsubstituted phenyl group;
when B is —C(O)—R7 where R7 is OR8 and R8 is ethyl, then A is different from —C(O)—OR5 where R5 is ethyl.

23 more elements

Dependencies are inferred from the claim text.

Sterol derivatives and use thereof for treating diseases involving transformed astrocyte cells or for treating malignant haemopathies

Life of this patent

Abstract

Claims23

Sterol derivatives and use thereof for treating diseases involving transformed astrocyte cells or for treating malignant haemopathies

Life of this patent

Abstract

Claims23