3, 4-bis-benzylsulfonylbutyronitrile and its pharmaceutical use
The present invention is directed to a method of treating an inflammatory skin disease or disorder, such as dermatitis, psoriasis, acne, or rosacea. The method comprises administering to the subject 3, 4-bis-benzylsulfonylbutyronitrile in an amount effective to reduce or eliminate the symptoms of the inflammatory skin disease or disorder. Topical administration and oral administration are preferred route of administration.
1. A compound of 3, 4-bis-benzylsulfonylbutyronitrile or a pharmaceutically acceptable salt thereof.
2. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and the compound of claim 1 , or a pharmaceutically acceptable salt thereof.
3. The pharmaceutical composition according to claim 1 , wherein the compound has at least 90% (w/w) purity, and the composition is in a topical form of gels, creams, lotions, ointments, solutions, suspensions, sprays, or patches.
4. The pharmaceutical composition according to claim 3 , wherein the pharmaceutically acceptable carrier is an emollient selected from the group consisting of: lauryl lactate, diethylene glycol monoethyl ether, caprylic/capric triglyceride, octisalate, silicone fluid, squalene, and sunflower oil.
5. The pharmaceutical composition according to claim 2 , wherein the pharmaceutically acceptable carrier is a permeation enhancer selected from the group consisting of lactate esters and diethylene glycol monoethyl ether.
6. The pharmaceutical composition according to claim 5 , further comprising acrylates/C10-30 alkyl and tris(2-hydroxyethyl)amine.
7. The pharmaceutical composition according to claim 2 , wherein the compound has at least 90% (w/w) purity, and the composition is in an oral form of tablets, capsules, granules, powders, or syrups.
8. A process for preparing the compound of claim 1 , comprising the steps of:
(a) reacting benzyl mercaptan with 4-bromo-2-butenenitrile in a basic condition to produce 3,4-bis-benzylthiobutyronitrile, and
(b) oxidizing 3,4-bis-benzylthiobutyronitrile with peroxide to produce 3,4-bis-benzylsulfonylbutyronitrile.
9. The process according to claim 8 , further comprising a step of reacting bromine Br 2 with allyl cyanide in a basic condition to prepare 4-bromo-2-butenenitrile.