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US 5,629,339 AGranted
Diosmetin compounds
AssigneeAdir et Compagnie
InventorsMichel Wierzbicki, Marie-Fran.cedilla.oise Boussard, Tony Verbeuren, Marie-Odile Vallez, Emmanuel Canet, Yves Rolland
Life of this patent
Estimating the term…
Abstract
Disclosed herein are new diosmetin compounds of formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description. The said compounds are useful in the treatment of chronic venous insufficiency.
Claims22
Diosmetin compounds selected from those of formula I:
- wherein:
- R.sub.1 represents hydrogen, allyl, or 1,2-dideuteroallyl;
- R.sub.2 represents hydrogen, allyl, propargyl, 2,3-dihydroxypropyl, (2,2-dimethyl-1,3-dioxol-4-yl)methyl, or 3-acetoxy-2-hydroxypropyl;
- R.sub.3 represents hydrogen, propyl, allyl or 1,2-dideuteroallyl;
- R.sub.4 represents hydrogen, allyl, propargyl, 2,3-dihydroxypropyl, (2,2-dimethyl-1,3-dioxol-4-yl)methyl, or --COR'.sub.4, wherein R'.sub.4 represents alkyl having 1 to 5 carbon atoms inclusive in straight or branched chain or phenyl;
- R.sub.5 represents hydrogen, propyl, allyl, 1,2-dideuteroallyl, and
- R.sub.6 represents hydrogen, allyl, or propargyl, 2,3-dihydroxypropyl, (2,2- dimethyl-1,3-dioxol-4-yl)methyl, or --COR'.sub.6 wherein R'.sub.6 represents alkyl having 1 to 5 carbon atoms inclusive in straight or branched chain, or phenyl,
- with the proviso that:
- at least one of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 has a meaning other than hydrogen,
- if R.sub.1, R.sub.2 and R.sub.3 each simultaneously represent hydrogen, then R.sub.4 also represents hydrogen;
- and, when R.sub.4 is COR'.sub.4 and/or R.sub.6 is COR'.sub.6 (R'.sub.4 and R'.sub.6 being as above-defined), then at least one of R.sub.1, R.sub.2, R.sub.3, and R.sub.5 is other than hydrogen or propyl;
- and also their diastereoisomers and/or enantiomers.
9 more elements
A compound selected from the group consisting of 7-allyloxy-5-hydroxy-2-(3-allyloxy-4-methoxyphenyl)-4H-1-benzopyran-4-one,
- 5,7-dihydroxy-2-{3-[(2,3-dihydroxypropoxy)-4-methoxyphenyl}-4H-1-benzopyran -4-one,
- (R,S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-(2,3-dihydroxypropoxy)-4H-1 -benzopyran-4-one,
- 5,7-di-(2,3-dihydroxypropoxy)-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran -4-one,
- 5-hydroxy-2-(4-methoxy-3-pivaloyloxyphenyl)-7-(2,3-dihydroxypropoxy)-4H-1-b enzopyran-4-one,
- 5-allyloxy-2-(3-allyloxy-4-methoxyphenyl)-7-(2,3-dihydroxypropoxy)-4H-1-ben zopyran-4-one,
- 6-allyl-5-hydroxy-2-(2-allyl-3-hydroxy-4-methoxyphenyl)-7-(2,3-dihydroxypro poxy)-4H-1-benzopyran-4-one,
- 5-hydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-6-propyl-7-(2,3-dihydroxyp ropoxy)-4H-1-benzopyran-4-one,
- (R,S)-5-hydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-7-(2,3-dihydroxyprop oxy)-4H-1-benzopyran-4-one, in the two forms .alpha. and .beta.,
- (R)-5-hydroxy-2- (3-hydroxy-4-methoxy-2-propylphenyl)-7-(2,3-dihydroxypropoxy)-4H-1-benzopy ran-4-one,
- (S)-5-hydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-7-(2,3-dihydroxypropox y)-4H-1-benzopyran-4-one,
- (R,S)-5-hydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-7-(3-acetoxy-2-hydro xypropoxy)-4H-1-benzopyran-4-one,
- 5-hydroxy-2-[4-methoxy-2-propyl-3-(6-carboxy-3,4,5-trihydroxytetrahydropyra n-2-yloxy)phenyl]-7-(2,3-dihydroxypropoxy)-4H-1-benzopyran-4-one,
- 5-hydroxy-2-[4-methoxy-3-(2,3-dihydroxypropoxy)-phenyl]-7- (2,3-dihydroxypropoxy)-4H-1-benzopyran-4-one,
- 6,8-diallyl-5,7-dihydroxy-2-(2-allyl-3-hydroxy-4-methoxyphenyl)-4H-1-benzop yran-4-one, and
- 5,7-dihydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-6,8-dipropyl-4H-1-benz opyran-4-one.
12 more elements
Dependencies are inferred from the claim text.