IP Library Granted Patent US 9,522,878
Granted Patent B2
US 9,522,878 · App. 15/084,816 · Granted Dec 20, 2016

4-methylsulfonyl-2-butenenitrile and its pharmaceutical use

Inventors: Joseph P. St. Laurent (Lakeville, MA); Gerald S. Jones (Norwood, MA); David M. Bresse (Middleboro, MA); Scott A. Goodrich (Stoughton, MA)
Assignee: Olatec Therapeutics LLC
C07C317/28C07C315/00
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Quick Facts
Patent No.
US 9,522,878
App. No.
15/084,816
Granted
Dec 20, 2016
Kind
B2
Abstract

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 4-methylsulfonyl-2-butenenitrile, in an amount effective to reduce or eliminate the symptoms of the inflammatory skin disease or disorder. Topical administration and oral administration are preferred routes of administration.

Claims (12)

1. A compound of 4-methylsulfonyl-2-butenenitrile 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 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 4-methylsulfonyl-2-butenenitrile, comprising the step of:

reacting 4-bromo-2-butenenitrile with sodium methanesulfinate.

9. The process according to claim 8 , further comprises the steps of preparing 4-bromo-2-butenenitrile by:

reacting bromine Br 2 with allyl cyanide, and

adding a basic solution.

Assignments (3)
CHANGE OF NAME Recorded Nov 7, 2023
From: OLATEC THERAPEUTICS LLC
To: OLATEC THERAPEUTICS, INC.
Reel/Frame 065489/0809 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2016
From: ST. LAURENT, JOSEPH P.; JONES, GERALD S.; BRESSE, DAVID M.; GOODRICH, SCOTT A.
To: OLATEC INDUSTRIES LLC
Reel/Frame 040258/0797 →
CHANGE OF NAME Recorded Nov 8, 2016
From: OLATEC INDUSTRIES LLC
To: OLATEC THERAPEUTICS LLC
Reel/Frame 040579/0265 →
Continuity (4)
Continuation In Part PCTUS2014058685 · Oct 1, 2014
Provisional Application 61887776 · Oct 7, 2013
Provisional Application 62142855 · Apr 3, 2015
Related Publication 20160207881A1 · Jul 21, 2016