Novel methylenedioxy phenolic compounds and their use to treat disease
AssigneesInvasc Therapeutics, Inc., The Ohio State University Research Foundation
InventorsSAMPATH PARTHASARATHY, SANJAY RAJAGOPALAN, DESIKAN RAJAGOPAL
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Abstract
Pharmaceutical compounds and compositions are provided which are methylenedioxy phenolic compounds and their derivatives, along with methods of making them and methods of using them for therapeutic purposes. The compounds and compositions are advantageous in that they can be used to treat or prevent cardiovascular disease, vascular disease and/or inflammatory disease, as well as Type I and Type II Diabetes and Dyslipidemia patients at risk for hypertension, stroke, cardiovascular and renal disease.
Claims20
A compound having the formula:
- wherein
- R1 is acetyl, ethyl ester, propyl ester, butyl ester, hydrogen, lipoyl, dihydrolipoyl, ferulyl, or isomeric-ferulyl;
- R2 is absent or is O2N, hydroxyl, methoxy, ethoxy, branched alkyl of 1 to 8 carbons, acetyl, lipoyl, dihydrolipoyl, ferulyl, a heterocycle selected from the group consisting of imidazole, quinaline, isoquinaline, thiazolidinedione, pyrrolidone and piperidine, carboxyl, methyl ester, ethyl ester, an aliphatic amide of 1 to 3 carbons, an alicyclic amide selected from the group consisting of pyrrolidone and piperidine, an aromatic amide selected from the group consisting of aniline and substituted aniline, amine, an alkylated amine of 1 to 3 carbons, an amide functional group via lipoic acid or dihydrolipoic acid, an aromatic acid selected from the group consisting of ferulic acid and cinnamic acid, a heterocyclic amide derived from proline, substituted proline, or pipecolinic acid, or a halogen;
- and
- R3 is absent or is a linear alkyl group of 1 to 3 carbons, a branched chain alkyl group of 3 to 5 carbons, an alkyl group having a functional group of a free carboxylic acid, ester or amide, free hydroxyl derivatives or alkylated ether derivatives, an alkyl group of 1 to 3 carbons having a functional group selected from amine and alkylated amine, an aliphatic amide, an aromatic amide or a heterocyclic amide selected from the group consisting of imidazole, quinoline, isoquinoline, thiozoline, and piperazine, or a halogenated group;
- except wherein the compound is not 3,4-methylenedioxy phenyl acetate (INV-73);
- 3,4-methylenedioxy-6-nitrophenol (INV-74), or 3,4-methylenedioxy-6-nitrophenyl acetate (INV-75).
A method of treating or preventing cardiovascular disease, vascular disease, inflammatory disease, and Type I and Type II diabetes and dyslipidemia patients at risk for hypertension, stroke, cardiovascular and renal disease in a patient comprising administering to the patient an effective amount of a compound having the formula:
- wherein
- R1 is acetyl, ethyl ester, propyl ester, butyl ester, hydrogen, lipoyl, dihydrolipoyl, ferulyl, or isomeric-ferulyl;
- R2 is absent or is O2N, hydroxyl, methoxy, ethoxy, branched alkyl of 1 to 8 carbons, acetyl, lipoyl, dihydrolipoyl, ferulyl, a heterocycle selected from the group consisting of imidazole, quinaline, isoquinaline, thiazolidinedione, pyrrolidone and piperidine, carboxyl, methyl ester, ethyl ester, an aliphatic amide of 1 to 3 carbons, an alicyclic amide selected from the group consisting of pyrrolidone and piperidine, an aromatic amide selected from the group consisting of aniline and substituted aniline, amine, an alkylated amine of 1 to 3 carbons, an amide functional group via lipoic acid or dihydrolipoic acid, an aromatic acid selected from the group consisting of ferulic acid and cinnamic acid, a heterocyclic amide derived from proline, substituted proline, or pipecolinic acid, or a halogen;
- and
- R3 is absent or is a linear alkyl group of 1 to 3 carbons, a branched chain alkyl group of 3 to 5 carbons, an alkyl group having a functional group of a free carboxylic acid, ester or amide, free hydroxyl derivatives or alkylated ether derivatives, an alkyl group of 1 to 3 carbons having a functional group selected from amine and alkylated amine, an aliphatic amide, an aromatic amide or a heterocyclic amide selected from the group consisting of imidazole, quinoline, isoquinoline, thiozoline, and piperazine, or a halogenated group.
Dependencies are inferred from the claim text.