Compounds for treating inflammation and pain
View Patent ↗The present invention is directed to a compound of 2-N halo-4-methylsulfonyl-butyric acid, such as 2-N chloro-4-methylsulfonyl-butyric acid, or a pharmaceutically acceptable salt or solvate thereof. The present invention is also directed to a pharmaceutical composition comprises the compound and a pharmaceutically acceptable carrier. The present invention is further directed to a method for treating inflammation or inflammatory-related disorders, bacterial infection, pain, or skin conditions, by administering 2-N halo-4-methylsulfonyl-butyric acid to a subject in need thereof.
1. A compound of 2-N halo-4-methylsulfonyl-butyric acid or a pharmaceutically acceptable salt or solvate thereof;
where X═F, Cl, or Br.
2. The compound of claim 1 , wherein X═Cl.
3. A pharmaceutical composition comprises the compound of claim 1 and a pharmaceutically acceptable carrier.
4. The pharmaceutical composition according to claim 3 , wherein the pharmaceutically acceptable carrier comprises lauryl lactate in an amount of 5-15% (w/w).
5. The pharmaceutical composition according to claim 3 , which is in a form of a gel and the compound is in an amount of about 0.03-0.3% (w/w).
6. A method for preparing the compound of claim 1 , comprising the steps of:
(a) mixing methionine, a water-immiscible organic solvent, and a halogenating agent, and reacting at a temperature between 0-30° C.;
(b) removing the aqueous phase; and
(c) obtaining the compound in the organic solvent.
7. The method according to claim 6 , wherein said water-immiscible organic solvent is ethyl acetate, hexane, heptane, methylene chloride, mineral oil, or a fatty acid ester.
8. The method according to claim 6 , wherein said halogenating agent is hypochlorite.
9. The method according to claim 6 , wherein the methionine is D-methionine, L-methionine, or a mixture thereof.
10. A method for preparing the compound of claim 2 , comprising the steps of:
(a) mixing methionine, ethyl acetate, and an aqueous hypochlorite solution and reacting at a temperature between 0-30° C.;
(b) removing the aqueous phase;
(c) obtaining the compound in ethyl acetate;
(d) adding a lactate ester solvent or a fatty acid ester solvent to the ethyl acetate solution and mixing;
(e) removing the ethyl acetate solvent; and
(f) obtaining the compound in the lactate ester solvent or in the fatty acid ester solvent.
11. The method according to claim 10 , wherein said lactate ester solvent is lauryl lactate, myristyl lactate, or cetyl lactate.
12. The method according to claim 10 , wherein said fatty acid ester solvent is isopropyl myristate.
13. A method of treating inflammation, comprising the steps of:
identifying a subject suffering from inflammation, and
topically administering to the subject the compound of claim 1 , in an amount effective to treat inflammation.
14. The method according to claim 13 , wherein said method reduces or alleviates the symptoms of localized manifestations of inflammation characterized by acute or chronic swelling, pain, or redness.
15. The method according to claim 13 , wherein said inflammation is inflammation of joints or soft tissues.
16. A method of treating pain, comprising the steps of:
identifying a subject suffering from pain, and
topically administering to the subject the compound of claim 1 , in an amount effective to treat pain.
17. The method according to claim 16 , wherein said pain is pain derived from rheumatoid arthritis, pain derived from osteoarthritis, joint pain, muscle pain, tendon pain, or burn pain.