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US 8,524,694 B2Granted
Aminoalkylsterol compounds with antitumoral and neuroprotective activity
AssigneeInstitut National De La Sante Et De La Recherche Medicale (Inserm)
InventorsMarc Poirot, Philippe De Medina, Sandrine Poirot
Life of this patent
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Abstract
Sterol derivatives of formula (I) and a method for the production of the compounds, a medicament using one of the compounds and a pharmaceutical composition comprising the medicament.
Claims18
A sterol-based compound, corresponding to formula (I)
- wherein:
- T1 and T2 represent, independently, H or CH3 with CH3 in the α and/or β position;
- T4 represents H, CH3 or C2H5;
- T3 represents H or a β CH3;
- the bond between carbons 5 and 6 is a single bond and the bond between carbons 7 and 8 is a single or a double bond;
- Z is in position 5 and represents OH;
- and
- R is in position 6 or 7, on a carbon not bearing a double bond, and represents a substituent of formula -Q0-Q1 wherein:
- -Q0- represents the radical of formula (II):
- —X—(CH2)no[Y1—(CH2)n1]p1[Y2—(CH2)n2]p2[Y3—(CH2)n3]p3[Y4—(CH2)n4]p4[Y5—(CH2)n5]p5— (II)
- in which formula (II):
- p1, p2, p3, p4 and p5 are integers independently equal to 0 or 1,
- n0, n1, n2, n3, n4 and n5 are independent integers such that:
- 1≦n0≦4
- 0≦n1,n2,n3,n4,n5≦4
- —X— represents —S—, —O—, —CH2—, —NR3—, in which R3 is H or a C1-C4 alkyl radical, or a heterocycle
- —Y1—, —Y2—, —Y3—, —Y4— and —Y5— represent, independently of each other, —S—, —O—, —CH2— or —NR3—, in which R3 has the meaning given above;
- -Q1 represents an indole nucleus, a morpholine or thiomorpholine nucleus attached via its nitrogen atom, a heterocycle
- in which R1 represents H, COCH3, or a C1-C4 alkyl radical, or Q1 represents
- in which R1 has the meanings given above and R2 represents H or a C1-C4 alkyl radical, or R1 and R2 together constitute a piperidine, pyridine or piperazine ring optionally substituted with a C2-C4 alkyl radical, or constitute a pyrrole or pyrrolidine heterocycle comprising a nitrogen atom and 4 carbon atoms, with the proviso that:
- if —X-=—NH— and
- at least one of the numbers p1, p2, p3, p4 and p5 is other than 0;
- and
- if —X—=—CH2—, n0=1 and all the numbers p1, p2, p3, p4 and p5 are zero, Q2 is other than —NH2.
21 more elements
A sterol-based compound corresponding to formula (I):
- wherein:
- (i) T4 represents CH3 or C2H5;
- and
- the bond C7-C8 is a single bond, Z represents OH in position 5, T1=T2=T3=H, and R is in position 6 and represents:
- or
- (ii) T4 represents H, CH3 or C2H5;
- and
- the bond C7-C8 is a single bond, Z represents OH in position 5, T1=T2=T3=H, and R is in position 6 and represents:
5 more elements
A sterol-based compound selected from the group consisting of:
- cholestane-3β,5α diol-6β-N—[N,N′-bis(3-aminopropyl)butane-1,4-diamine];
- cholest-7-ene-3β,5α diol-6β-N—[N,N′-bis(3-aminopropyl)butane-1,4-diamine];
- cholestane-3β,5α diol-6β-N-({1H-imidazol-4-yl}ethyl)acetamide;
- cholestane-3β,5α diol-6β-(3-aminopropylacetamide);
- cholestane-3β,5α diol-6β-(4-aminobutylyl-1-acetamide);
- cholestane-3β,5α-diol-6β-(6-aminohexylacetamide);
- cholestene-7-3β,5α diol-6β-(3-aminopropylacetamide);
- cholest-7-ene-3β,5α diol-6β-(4-aminobutylyl-1-acetamide);
- cholestene-7-3β,5α diol-6β-(6-aminohexylacetamide);
- sitostane-3β,5α diol-6β-(3-aminopropylacetamide);
- campestane-3β,5α diol-6β-(3-aminopropylacetamide);
- campestane-3β,5α diol-6β-(4-aminobutyl-1-acetamide);
- sitostane-3β,5α diol-6β-(6-aminohexylacetamide);
- campestane-3β,5α diol-6β-(6-aminohexylacetamide);
- sitostane-3β,5α diol-6β-N—[N,N′-bis(aminopropyl)butane-1,4-diamine];
- and
- campestane-3β,5α diol-6β-N—[N,N′-bis(aminopropyl)butane-1,4-diamine].
14 more elements
Dependencies are inferred from the claim text.