Method of using of dihydro-resveratrol or its stilbenoid derivatives and/or chemical variants as antimicrobial agents

Patent metadata

Field	Value
Publication number	US-10351500-B2
Application number	US-201816030854-A
Country	US
Kind code	B2
Filing date	Jul 9, 2018
Priority date	Jun 16, 2015
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

The present invention relates to a composition for preventing or reducing microbial growth, particularly the growth of dermatophytic fungi, and/or aciduric and acidogenic gram-positive bacteria. More particularly, it relates to the use of trans-3,5,4′-trihydroxybibenzyl, also known as dihydro-resveratrol, or its dihydrostilbene derivatives and/or chemical variants as an anti-microbial agent. The present invention further relates to the management of dermatophytosis often caused by dermatophytic fungi and the management of dental caries often mediated by aciduric and acidogenic gram-positive Streptococci. The present invention therefore has applications in preventing, alleviating and/or treating dermatophytosis and dental caries.

First claim

The invention claimed is:

1. An anti-microbial agent comprising compound of formula (3):

wherein
R 2 , R 4 , and R 8 are selected from —OR 11 , —OCH 2 R 11 , —OC(O)R 11 , —OCH 2 C(O)OR 11 or —OC(O)CH 2 R 11 ;
R 1 , R 3 , R 5 , R 6 , R 7 , R 9 and R 10 are each independently selected from hydrogen, halogen, trifluoromethyl, —OR 11 and —OC(O)R 11 ; or R 2 and R 3 , or R 7 and R 8 are taken together with the carbon atoms to which they are attached to form a cyclic group;
R 11 is hydrogen, hydrocarbyl or heterocyclyl which is optionally substituted with 1, 2, 3, 4 or 5 R 12 ;
R 12 is selected from halogen, trifluoromethyl, cyano, nitro, oxo, —OR 13 , —C(O)R 14 , —C(O)N(R 13 )R 14 , —C(O)OR 13 , —OC(O)R 14 , —S(O) 2 R 13 , —S(O) 2 N(R 13 )R 14 ; or —N(R 13 )R 14 ;
R 13 and R 14 are each independently hydrogen, or selected from hydrocarbyl or heterocyclyl which is optionally substituted with 1, 2, 3, 4 or 5 substituents independently selected from halogen, cyano, amino, hydroxy, C 1-6 alkyl or C 1-6 alkoxy;
or an enantiomer thereof;
or a pharmaceutically acceptable salt or prodrug thereof;

or a mixture, derivative and/or chemical variants thereof.

2. The anti-microbial agent according to claim 1 , wherein the compound further comprises compounds of formulae:

3. The anti-microbial agent according to claim 1 , wherein the compound further comprises compound of Formula (I):

wherein R is jointly OC(═O)R′; R′ is an alkenyl.

4. A method for prevention, alleviation, and/or treatment of dermatophytosis comprising applying the anti-microbial agent according to claim 1 to a subject in need thereof.

5. A method for prevention, alleviation, and/or treatment of dental caries comprising applying the anti-microbial agent according to claim 1 to a subject in need thereof.

6. A method for preventing or reducing the growth of micro-organisms comprising applying the anti-microbial agent according to claim 1 to where the micro-organisms are found.

7. The method according to claim 6 , wherein said micro-organisms comprise dermatophytic fungi and/or aciduric and acidogenic gram-positive bacteria.

8. The method according to claim 7 , wherein said dermatophytic fungi comprise Trichophyton rubrum and Trichophyton mentagraphytes.

9. The method according to claim 7 , wherein said aciduric and acidogenic gram-positive bacteria comprise Streptococcus mutans and Streptococcus sobrinus.

10. The method according to claim 8 , wherein said micro-organisms are found in Tinea pedis of a subject being applied with said anti-microbial agent.

11. The method according to claim 9 , wherein said micro-organisms are found in oral cavity of a subject being applied with said anti-microbial agent.

12. The method according to claim 4 , wherein said anti-microbial agent is formulated as topical fungicidal or fungistatic gel, lotion, cream, emulsion, paste, solution or moist spray.

13. The method according to claim 5 wherein said anti-microbial agent is formulated as toothpaste, oral gel, toothbrush sanitizer, mouthwash or chewing gum.

14. The method according to claim 4 , wherein said anti-microbial agent is of a concentration ranging from 25 μM to 100 μM.

15. The method according to claim 5 , wherein said anti-microbial agent is of a concentration ranging from 25 μM to 100 μM.

16. The method according to claim 8 , wherein said anti-microbial agent is of a concentration ranging from 25 μM to 100 μM.

17. The method according to claim 9 , wherein said anti-microbial agent is of a concentration ranging from 25 μM to 100 μM.

Assignees

• Univ Hong Kong Baptist Univ

Inventors

• Zhang Hongjie
• Tsang Siu Wai

Classifications

• A61K31/05

  Phenols {(cannabinoids A61K31/658)} · CPC title

• C07C69/34

  Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom · CPC title

• C07C69/78

  Benzoic acid esters · CPC title

• C07C69/30

  esterified with trihydroxylic compounds (fats, oils C11B, C11C) · CPC title

• C07C43/23 Primary

  containing hydroxy or O-metal groups · CPC title