Antifungal compounds derived from lavender oil

Patent metadata

Field	Value
Publication number	US-2020071284-A1
Application number	US-201816122271-A
Country	US
Kind code	A1
Filing date	Sep 5, 2018
Priority date	Sep 5, 2018
Publication date	Mar 5, 2020
Grant date	—

Abstract

Epoxides and hydroperoxide compounds having antifungal activities derived from the oxidation linalyl acetate, a major component of lavender oil, are disclosed. Also, disclosed are pharmaceutical composition and methods of treating and protecting a subject from fungal infection.

First claim

1 - 20 . (canceled)

21 : A pharmaceutical composition, comprising:
two epoxide compounds, and at least one adjuvant and/or excipient selected from the group consisting of benzyl alcohol, propylene glycol, polyethylene glycol, a vegetable oil, a fatty acid, a synthetic fatty ester, a surfactant, and a sugar, wherein the epoxide compounds consist of the compounds of formula 3 and 4:

wherein each of the compounds of formula 3 and 4 are present in the pharmaceutical composition in an equal amount in the range of 0.1%-20% by weight of the total weight of the pharmaceutical composition.

22 : The pharmaceutical composition of claim 21 further comprising:
at least one compound selected from the group consisting of linalyl acetate, the hydroperoxide compound of formula 5, and the hydroperoxide compound of formula 6:

wherein the compound is present in the pharmaceutical composition in an amount in the range of 0.1-20% by weight of the total weight of the pharmaceutical composition.

23 : The pharmaceutical composition of claim 21 , further comprising:
water and/or a buffer.

24 : The pharmaceutical composition of claim 23 , wherein the buffer is selected from the group consisting of a phosphate buffer, a citrate buffer, an acetate buffer, a borate buffer, and a carbonate/bicarbonate buffer.

25 : The pharmaceutical composition of claim 21 , further comprising:
one or more antiviral drugs.

26 : The pharmaceutical composition of claim 25 , wherein the antiviral drug is one or more antiviral agents selected from the group consisting of ketoconazole, fluconazole, isavuconazole, itraconazole, posaconazole, posaconazole, voriconazole, anidulafungin, caspofungin, and micafungin.

27 : The pharmaceutical composition of claim 21 , further comprising:
one or more antibiotic compounds.

28 : The pharmaceutical composition of claim 27 , wherein the antibiotic compound is one or more antibiotics selected from the group consisting of Vancomycin, Ceftobiprole, Ceftaroline, Clindamycin, Dalbavancin, Daptomycin, Fusidic acid, Linezolid, Mupirocin, Oritavancin, Tedizolid, Telavancin, Tigecyclin, Aminoglycosides, Carbapenems, Ceftazidime, Cefepime, Ceftobiprole, Ceftolozane/tazobactam, a fluoroquinolone, Piperacillin/tazobactam, Ticarcillin/clavulanic acid, Linezolid, Streptogramins, Tigecycline, and Daptomycin.

29 : The pharmaceutical composition of claim 21 which is formulated for immediate release.

30 : The pharmaceutical composition of claim 21 which is formulated for controlled release.

31 : The pharmaceutical composition of claim 21 which is formulated as a solid for oral administration.

32 : The pharmaceutical composition of claim 21 which is formulated as a liquid for oral administration.

33 : The pharmaceutical composition of claim 21 which is formulated as a liquid for parenteral administration.

34 : The pharmaceutical composition of claim 21 which is formulated for topical administration.

35 : A method of treating a subject having a fungal infection, comprising:
administering to the subject an antifungal effective amount of the pharmaceutical composition of claim 21 .

36 : A method of treating a subject having a fungal infection, comprising:
administering to the subject an antifungal effective amount of the pharmaceutical composition of claim 22 .

37 : The method of claim 35 , wherein the subject is a mammal.

38 : The method of claim 35 , wherein the subject is a human.

Assignees

• Univ King Abdulaziz

Inventors

• Khayyat Suzan

Classifications

• A61P31/10 Primary

  Antimycotics · CPC title

• C07D303/16

  by esterified hydroxyl radicals · CPC title

• C07D301/12 Primary

  with hydrogen peroxide or inorganic peroxides or peracids · CPC title

• C07C409/04

  the carbon atom being acyclic · CPC title

• C07C407/00

  Preparation of peroxy compounds · CPC title