Pharmaceutical active ingredient and use thereof, in particular for the prevention and treatment of metabolic disorders in humans and animals

Patent metadata

Field	Value
Publication number	US-2020009101-A1
Application number	US-201816486381-A
Country	US
Kind code	A1
Filing date	Feb 13, 2018
Priority date	Feb 16, 2017
Publication date	Jan 9, 2020
Grant date	—

Abstract

The invention relates to an active pharmaceutical ingredient consisting exclusively of the combination of (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-)dihydroxyphenyl)-2-propenoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid and of methyl (2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H -pyran-5-carboxylate for use as a drug or veterinary product, particularly in the prevention and/or treatment of pathological disorders of carbohydrate and/or lipid metabolism.

First claim

1 . A pharmaceutical active ingredient consisting of:
of the (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)-4)-2-propenoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid, and of the methyl (2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate, for use as a drug or veterinary product.

2 . The pharmaceutical active ingredient for use according to claim 1 , in the prevention and/or treatment of at least one disease selected from among type 2 diabetes, non-alcoholic fatty liver diseases, cardiovascular pathologies, dyslipidemia, obesity and metabolic syndrome.

3 . The pharmaceutical active ingredient for use according to claim 2 , characterized in that the cardiovascular pathologies are selected from among coronary heart disease, cerebrovascular diseases, peripheral arterial diseases and deep vein thromboses.

4 . The pharmaceutical active ingredient for use according to claim 2 , characterized in that the non-alcoholic fatty liver disease is non-alcoholic fatty liver disease.

5 . The pharmaceutical active ingredient for use according to claim 1 , characterized in that the ratio of (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid over methyl(2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate by weight is between 1/40 and 1/1.

6 . The pharmaceutical active ingredient for use according to claim 1 , characterized in that the molecules of (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid and of (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid, and of methyl (2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate are natural or synthetic molecules by a chemical and/or biotechnological process.

7 . The pharmaceutical active ingredient for use according to claim 1 , characterized in that it is in liquid form.

8 . The pharmaceutical active ingredient for use according to claim 1 orally, enterally, parenterally or subcutaneously.

9 . The pharmaceutical active ingredient for use according to claim 1 in a pharmaceutical composition.

10 . The pharmaceutical composition comprising an active pharmaceutical ingredient according to claim 1 , characterized in that it is in the form of tablets, capsules, gel capsules, powder, sachets, ampoules, solution for dropper or injectable solution.

11 . The pharmaceutical composition for use according to claim 10 , characterized in that it comprises between 0.5 and 100% of the pharmaceutical active ingredient by weight of dry matter.

12 . A method for preventing and/or treating at least one disease selected from among type 2 diabetes, non-alcoholic fatty liver diseases, cardiovascular pathologies, dyslipidemia, obesity and metabolic syndrome, wherein the method comprises administering to a mammal in need of the prevention and/or treatment a drug or veterinary product comprising the pharmaceutical active ingredient of claim 1 .

13 . The method of claim 12 , characterized in that the cardiovascular pathologies are selected from among coronary heart disease, cerebrovascular diseases, peripheral arterial diseases and deep vein thromboses.

14 . The method of claim 12 , characterized in that the non-alcoholic fatty liver disease is non-alcoholic fatty liver disease.

15 . The method of claim 12 , wherein the pharmaceutical active ingredient has the ratio of (1S,3R,4R,5 R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid over methyl(2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate by weight between 1/40 and 1/1.

16 . The method of claim 12 , wherein the pharmaceutical active ingredient is further characterized in that the molecules of (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-4,5-trihydroxycyclohexanecarboxylic acid and of (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid, and of methyl (2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-(β-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-5-carboxylate are natural or synthetic molecules by a chemical and/or biotechnological process.

17 . The method of claim 12 , wherein the drug or veterinary product is administered orally, enterally, parenterally or subcutaneously.

18 . The method of claim 12 , wherein the drug or veterinary product is a pharmaceutical composition.

19 . The method of claim 12 , wherein the drug or veterinary product is in the form of tablets, capsules, gel capsules, powder, sachets, ampoules, solution for dropper or injectable solution.

20 . The method of claim 12 , wherein the drug or veterinary product comprises between 0.5 and 100% of the pharmaceutical active ingredient by weight of dry matter.

Assignees

• Valbiotis
• Univ Clermont Auvergne
• Univ La Rochelle
• Centre Nat Rech Scient

Inventors

• Peltier Sebastien
• Chavanelle Vivien
• Le Joubioux Florian
• Sirvent Pascal
• Maugard Thierry

Classifications

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P3/06

  Antihyperlipidemics · CPC title

• A61P3/04

  Anorexiants; Antiobesity agents · CPC title

• A61P3/00

  Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00) · CPC title