Phosphinolactone derivatives and pharmaceutical uses thereof
AssigneesInstitut National De La Sante Et De La Recherche Medicale (Inserm), Ecole Pratique Des Hautes Etudes, Ecole Nationale Superieure De Chimie De Montpellier, Centre National De La Recherche Scientifique, Universite De Montpellier
InventorsTangui Maurice, Jean-Noël Volle, David Virieux, Jean-Luc Pirat, Coralie Laborde
Life of this patent
Estimating the term…
Abstract
A compound of following formula (I): where: X is O or S; A is an aromatic (hetero)cycle having 5 to 10 atoms selected from among carbon and nitrogen atoms, optionally being substituted; R′ is H or (C1-C6)alkyl group; R1, R2, R3, R4 and R5, the same or different, are selected from the group formed by: H, (C1-C6)alkyl groups and (C6-C10)aryl groups. The compound is for the treatment of neurodegenerative diseases.
Claims15
A method of treating a neurodegenerative disease, comprising administering to a subject in need thereof an effective a compound of following formula (I):
- where:
- X is O or S;
- A is selected from the group formed by:
- (C6-C10) aryl groups,
- heteroaryl groups having 5 to 10 atoms, and
- heterocycloalkyls having 5 to 10 atoms,
- said aryl, heteroaryl and heterocycloalkyl groups optionally being substituted by at least one substituent selected from the group formed by halogen atoms, ORa, SRa, NO2, NRaRb, N(Ra)COORc, R′a and OR′a;
- Ra and Rb, the same or different, being H or (C1-C6) alkyl group;
- Rc being a —(C1-C6) alkylene-(C6-C10) aryl radical, in particular a —CH2— (C6-C10) aryl radical;
- R′a being selected from the groups CF3, CHF2 and CH2F
- R′ is H or (C1-C6)alkyl group;
- R1, R2, R3, R4 and R5, the same or different, are selected from the group formed by:
- H,
- (C1-C6)alkyl groups, and
- (C6-C10) aryl groups,
- R1 and R2, together with their carrier carbon atom, able to form a spiran ring having 3 to 6 carbon atoms, and/or
- R3 and R4, together with their carrier carbon atom, able to form a spiran ring having 3 to 6 carbon atoms.
Compound of following formula (I-1):
- where:
- R′1, R′2 and R′3, the same or different, are (C1-C6) alkyl groups or (C6-C10)aryl groups, R′1, R′2 and R′3 preferably being methyl groups;
- R4 and R5, the same or different, are selected from the group formed by:
- H,
- (C1-C6)alkyl groups, and
- (C6-C10) aryl groups,
- R′1 and R′2, together with their carrier carbon atom, able to form a spiran ring having 3 to 6 carbon atoms, and/or
- R′3 and R4, together with their carrier carbon atom, able to form a spiran ring having 3 to 6 carbon atoms;
- is selected from the group formed by:
- (C6-C10) aryl groups,
- heteroaryl groups having 5 to 10 atoms, and
- heterocycloalkyls having 5 to 10 atoms,
- said aryl, heteroaryl and heterocycloalkyl groups optionally being substituted by at least one substituent selected from the group formed by halogen atoms, ORa, SRa, NO2, NRaRb, N(Ra)COORc, R′a and OR′a;
- Ra and Rb, the same or different, being H or (C1-C6) alkyl group;
- Rc being a —(C1-C6) alkylene-(C6-C10) aryl radical, in particular a —CH2— (C6-C10) aryl radical;
- R′a being selected from among the groups CF3, CHF2 and CH2F;
- and, when R′1═R′2═R′3=Me, R4=Me or H and R5═H, A differs from the following groups:
Compound of following formula (1-2):
- where:
- A is selected from the group formed by:
- (C6-C10) aryl groups,
- heteroaryl groups having 5 to 10 atoms, and,
- heterocycloalkyls having 5 to 10 atoms,
- said aryl, heteroaryl and heterocycloalkyl groups optionally being substituted by at least one substituent selected from the group formed by halogen atoms, ORa, SRa, NO2, NRaRb, N(Ra)COORc, R′a and OR′a;
- Ra and Rb, the same or different, being H or (C1-C6) alkyl group;
- Rc being a —(C1-C6) alkylene-(C6-C10) aryl radical, in particular a —CH2— (C6-C10) aryl radical;
- R′a being selected from the groups CF3, CHF2 and CH2F;
- R′ is H or (C1-C6)alkyl group;
- R1, R2, R3, R4 and R5, the same or different, are selected from the group formed by:
- H,
- (C1-C6)alky groups, and
- (C6-C10) aryl groups,
- R1 and R2, together with their carrier carbon atom, able to form a spiran ring having 3 to 6 carbon atoms, and/or
- R3 and R4, together with their carrier carbon atom, able to form a spiran ring having 3 to 6 carbon atoms.
Compound of following formula (1-3):
- where:
- X is O or S;
- A is selected from the group formed by:
- (C6-C10) aryl groups,
- heteroaryl groups having 5 to 10 atoms, and
- heterocycloalkyls having 5 to 10 atoms,
- said aryl, heteroaryl and heterocycloalkyl groups optionally being substituted by at least one substituent selected from the group formed by halogen atoms, ORa, SRa, NO2, NRaRb, N(Ra)COORc, R′a and OR′a;
- Ra and Rb, the same or different, being H or (C1-C6) alkyl group;
- Rc being a —(C1-C6) alkylene-(C6-C10) aryl radical, in particular a —CH2— (C6-C10) aryl radical;
- R′a being selected from the groups CF3, CHF2 and CH2F;
- R″ is a (C1-C6) alkyl group;
- R1, R2, R3, R4 and R5, the same or different, are selected from the group formed by:
- H,
- (C1-C6)alky groups, and
- (C6-C10) aryl groups,
- R1 and R2, together with their carrier carbon atom, able to form a spiran ring having 3 to 6 carbon atoms, and/or
- R3 and R4, together with their carrier carbon atom, able to form a spiran ring having 3 to 6 carbon atoms.
Dependencies are inferred from the claim text.