Use of 3-deoxyanthocyanidins for treating occular diseases

Patent metadata

Field	Value
Publication number	US-10513503-B2
Application number	US-201615577173-A
Country	US
Kind code	B2
Filing date	May 27, 2016
Priority date	May 27, 2015
Publication date	Dec 24, 2019
Grant date	Dec 24, 2019

Abstract

Disclosed is a method for the treatment, prevention and/or stabilisation of ARMD, Stargardt disease, pigmentary retinopathy and/or diabetic retinopathy, including the application of a 3-deoxyanthocyanidin of formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and X − are as defined, with the condition that at least one of R 1 , R 2 , R 3 , R 4 or R 5 is a hydroxyl and at least one of R 8 , R 9 , R 10 or R 11 is a hydroxyl.

First claim

The invention claimed is:

1. A method for treating and/or stabilising AMD, Stargardt disease, pigmentary retinopathy and/or diabetic retinopathy, comprising the administration to a patient in need thereof of an effective amount of a compound of Formula I

wherein
R 1 , R 2 , R 3 , R 4 and R 5 each independently is a group selected from hydrogen, halo, hydroxyl, alkoxy, aryloxy, heteroaryloxy, acyloxy, alkyl, aryl, aralkyl, alkylaryl, alkenyl, nitro, nitrile, amino, with the condition that at least one of R 1 , R 2 , R 3 , R 4 or R 5 is a hydroxyl;
R 6 is hydrogen;
R 7 is a group selected from hydrogen, halo, hydroxyl, alkoxy, aryloxy, heteroaryloxy, acyloxy, alkyl, aryl, aralkyl, alkylaryl, alkenyl, nitro, nitrile, amino;
R 8 , R 9 , R 10 and R 11 each independently is a group selected from hydrogen, halo, hydroxyl, alkoxy, aryloxy, heteroaryloxy, acyloxy, alkyl, aryl, aralkyl, alkylaryl, alkenyl, nitro, nitrile, amino, with the condition that at least one of R 8 , R 9 , R 10 or R 11 is a hydroxyl; and
X − is an anion selected from: anion derived from a mineral acid; anion derived from an organic acid; or an anion derived from a sulphate or sulphonate group.

2. The method according to claim 1 , wherein the anion derived from a mineral acid is selected from a bromide, chloride, borotetrafluoride and perchloride anion; and wherein the anion derived from an organic acid is selected from an acetate, borate, citrate, tartrate, bisulphate, sulphate and phosphate anion.

3. The method according to claim 1 , wherein the compound is of Formula Ia

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 8 , R 10 and X − are such as defined in claim 1 .

4. The method according to claim 1 , wherein:
R 1 , R 2 , R 3 , R 4 and R 5 each independently is a group selected from hydrogen, hydroxyl and alkoxy, with the condition that at least one of R 1 , R 2 , R 3 , R 4 or R 5 is a hydroxyl; and
R 8 and R 10 each independently is a group selected from hydrogen, hydroxyl and alkoxy, with the condition that at least one of R 8 or R 10 is a hydroxyl.

5. The method according to claim 1 , wherein the compound is of Formula Ib

wherein R 1 , R 2 , R 3 , R 8 and X − are such as defined in claim 1 .

6. The method according to claim 1 , wherein R 8 is a hydrogen atom.

7. The method according to claim 1 , wherein the compound is selected from:
2′,7-dihydroxy-4′-methoxy-flavylium chloride;
2′,3′,7-trihydroxy-4′-methoxy-flavylium chloride;
3′,7-dihydroxy-4′-methoxy-flavylium chloride;
4′,5,7-trihydroxy-flavylium chloride;
3′,5,7-trihydroxy-4′-methoxy-flavylium chloride;
3′,4′,5′,5,7-pentadroxy-flavylium chloride; and
3′,4′,5,7-tetrahydroxy-flavylium chloride.

Assignees

• Biophytis
• Univ Pierre Et Marie Curie—Paris 6 Upmc
• Centre Nat Rech Scient
• Inst Nat Sante Rech Med
• Univ Sorbonne

Inventors

• Fontaine Valerie
• Lafont Rene
• Sahel Jose-Alain
• Veillet Stanislas

Classifications

• A61P27/02

  Ophthalmic agents · CPC title

• A61P27/00

  Drugs for disorders of the senses · CPC title

• C07D311/60 Primary

  with aryl radicals attached in position 2 · CPC title

• A61K31/352 Primary

  condensed with carbocyclic rings, e.g. methantheline  {(cannabinoids A61K31/658)} · CPC title