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US 2003/0119816 A1Published application
Flavone derivatives, preparation method and use as medicines
OwnerJean-Luc Haesslein, Dominique Lefrancois +2inventors
InventorsJean-Luc Haesslein, Dominique Lefrancois, Eric Uridat, Jidong Zhang
Life of this patent
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Abstract
The invention concerns novel products of formula (I) wherein: R1 represents a carbocyclic or heterocyclic radical optionally substituted; R2 and R3 are such that one represents hydrogen and the other represents piperidinyl optionally substituted; R4 represents hydrogen, alkyl or phenyl optionally substituted, said products being in all isomeric and salt forms and used as medicines.
Claims15
1) Products of formula (I):
- 8
- in which:
- R1 represents a carbocyclic or heterocyclic monocyclic or bicyclic radical containing at most 12 members, saturated or unsaturated, containing one or more identical or different heteroatoms chosen from O, N, NH or S and can contain a —C(O) member,
- the carbocyclic and heterocyclic radicals as defined above for R1, being optionally substituted by one or more radicals chosen from halogen atoms;
- the hydroxyl;
- cycloalkyl containing at most 6 members;
- acyl containing at most 7 carbon atoms;
- cyano;
- nitro;
- free, salified or esterified carboxy;
- tetrazolyl;
- —NH2, —NH(alk), —N(alk)(alk);
- SO2—NH—CO—NHR5 in which R5 represents an alkyl or phenyl radical;
- —C(O)—NH2, —C(O)—NH(alk), —C(O)—N(alk)(alk), —NH—C(O)—(alk), —N(alk)—C(O)—(alk);
- thienyl;
- phenyl;
- alkylphenyl;
- alkyl, alkenyl, alkylthio, alkoxy or phenoxy radicals themselves optionally substituted by one or more radicals chosen from halogen atoms, the —NH2, —NH(alk), —N(alk)(alk) radicals and the heterocyclic monocyclic or bicyclic radicals themselves optionally substituted by one or more radicals chosen from alkyl radicals and halogen atoms,
- R2 and R3 are such that one represents a hydrogen atom and the other represents a piperidinyl radical optionally substituted by one or more hydroxyl and alkyl radicals,
- R2 and R3 being alternatively able to take the same values in order to produce the corresponding isomers,
- R4 represents a hydrogen atom, an alkyl or phenyl radical optionally substituted by one or more halogen atoms it being understood that in the above radicals, the alkyl and alkoxy radicals are linear or branched and contain at most 6 carbon atoms,
- said products of formula (I) being in all possible racemic, enantiomeric and diastereoisomeric isomer forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).
19 more elements
5) The following products of formula (I):
- 2-(2-chloro-4-fluorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-benzopyran-4-one trifluoroacetate
- 2-(2,5-dichloro-3-thienyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-benzopyran-4-one trifluoroacetate
- 5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-2-(5-methyl-3-isoxazolyl)-4H-benzopyran-4-one trifluoroacetate
- 5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-2-[5-(trifluoromethyl)-1-phenyl-1H-pyrazol-4-yl]-4H-benzopyran-4-one trifluoroacetate
- 5,7-dihydroxy-6-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-2-[3-(phenoxy)-phenyl]-4H-benzopyran-4-one trifluoroacetate
2 more elements
15) As new industrial products, the compounds of formula (IV).
Dependencies are inferred from the claim text.