US2022378729A1PendingUtilityA1

Topical formulations of cyclooxygenase inhibitors and their use

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Assignee: SMARTECH TOPICAL INCPriority: Nov 6, 2019Filed: Nov 5, 2020Published: Dec 1, 2022
Est. expiryNov 6, 2039(~13.3 yrs left)· nominal 20-yr term from priority
Inventors:Thomas Hnat
A61K 9/0014A61K 31/165A61K 47/12A61K 47/38A61K 31/245A61K 31/167A61K 31/60A61K 31/196A61K 47/20A61K 31/416A61K 9/06A61K 47/10A61K 31/7034A61K 31/405A61K 31/192
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Claims

Abstract

A topical cyclooxygenase (COX) inhibitor formulation comprising an inhibitor of COX-1 and/or COX-2, one or more long chain monounsaturated fatty acids, long chain monounsaturated fatty alcohols, terpenes, or combinations thereof; and a solvent mixture comprising ethanol, propylene glycol, 2-(2-Ethoxyethoxy)ethanol, and optionally dimethylsulfoxide.

Claims

exact text as granted — not AI-modified
I claim: 
     
         1 . A topical cyclooxygenase (COX) inhibitor formulation, comprising
 one or more COX inhibitors that inhibit human COX-1, human COX-2, or both human COX-1 and human COX-2;   between about 1.0 and about 15.0 wt % of long chain monounsaturated fatty acids, long chain monounsaturated fatty alcohols, terpenes, or combinations thereof;   between 0 and about 5.0 wt % of a poloxamer;   between 0 and about 5.0 wt % of a pharmaceutically acceptable cellulosic excipient;   a solvent mixture comprising ethanol, propylene glycol, 2-(2-Ethoxyethoxy)ethanol, and optionally dimethylsulfoxide; and   wherein the formulation comprises about 5.0 wt % or less water.   
     
     
         2 . A topical COX inhibitor formulation according to  claim 1 , wherein the formulation comprises a COX inhibitor selected from the group consisting of Naproxen, Acetaminophen, Benzydamine, Bufexamac, Diclofenac, Etofenamate, Flufenamic acid, Ibuprofen, Indomethacin, Ketoprofen, salicylic acid, salicin, diflunisal, magnesium salicylate, and choline salicylate. 
     
     
         3 . A topical COX inhibitor formulation according to  claim 2 , wherein the one or more COX inhibitors present in the formulation consists of Diclofenac. 
     
     
         4 . A topical COX inhibitor formulation according to  claim 3 , wherein the formulation comprises between about 1.0 and about 2.5 wt % Diclofenac. 
     
     
         5 . A topical COX inhibitor formulation according to  claim 4 , wherein the formulation provides a per-cutaneous absorption of the Diclofenac of at least about 7%. 
     
     
         6 . A topical COX inhibitor formulation according to  claim 5 , wherein the formulation provides a per-cutaneous absorption of the Diclofenac of at least about 10%. 
     
     
         7 . A topical COX inhibitor formulation according to one of  claims 1 - 6 , wherein the formulation comprises about 1.0 wt % or less water. 
     
     
         8 . A topical COX inhibitor formulation according to  claim 7 , wherein the formulation is anhydrous. 
     
     
         9 . A topical COX inhibitor formulation according to one of  claims 1 - 8 , wherein the formulation comprises between about 25.0 and about 50.0 wt % ethanol, between about 2.0 and about 12.5 wt % propylene glycol, between about 0 and about 25.0 wt % dimethylsulfoxide, and between about 20.0 and about 49.9 wt % 2-(2-Ethoxyethoxy)ethanol; and wherein the solvent mixture is between about 70.0 and about 95.0 wt % of the formulation. 
     
     
         10 . A topical COX inhibitor formulation according to one of  claims 1 - 9 , wherein the formulation comprises between about 1.0 and about 10.0 wt % of a long chain monounsaturated fatty acid, a long chain monounsaturated alcohol, or mixtures thereof. 
     
     
         11 . A topical COX inhibitor formulation according to one of  claims 1 - 10 , wherein the long chain monounsaturated fatty acid, a long chain monounsaturated alcohol, or mixtures thereof present in the formulation comprises or consists of oleic acid, oleyl alcohol, or a mixture thereof. 
     
     
         12 . A topical COX inhibitor formulation according to one of  claims 1 - 11 , wherein the formulation comprises a poloxamer selected from the group consisting of poloxamer-101, -105, -105 benzoate, -108, -122, -123, -124, -181, -182, -182 dibenzoate, -183, -184, -185, -188, -212, -215, -217, -231, -234, -235, -237, -238, -282, -284, -288, -331, -333, -334, -335, -338, -401, -402, -403, and -407. 
     
     
         13 . A topical COX inhibitor formulation according to  claim 12 , wherein the formulation comprises between 0 and about 5.0 wt % of poloxamer-188. 
     
     
         14 . A topical COX inhibitor formulation according to one of  claims 1 - 11 , wherein the formulation comprises a pharmaceutically acceptable cellulosic excipient selected from the group consisting of hydroxypropylcellulose, hydroxypropyl methylcellulose, carboxymethylcellulose, methylcellulose, ethylcellulose, hydroxyethyl cellulose, hydroxyethylmethylcellulose and ethyl hydroxyethylcellulose. 
     
     
         15 . A topical COX inhibitor formulation according to  claim 14 , wherein the formulation comprises between about 1.0 and about 5.0 wt % of hydroxypropylcellulose. 
     
     
         16 . A topical COX inhibitor formulation according to  claim 1 , wherein the formulation comprises:
 between about 1.0 and about 2.5 wt % diclofenac;   between about 1.0 and about 10.0 wt % of oleic acid, oleyl alcohol, or a mixture thereof;   between 0 and about 5.0 wt % of a poloxamer;   between about 2.0 and about 5.0 wt % of hydroxypropylcellulose;   an anhydrous solvent mixture comprising ethanol, propylene glycol, dimethylsulfoxide, and 2-(2-Ethoxyethoxy)ethanol,   wherein the formulation comprises between about 25.0 and about 50.0 wt % ethanol, between about 2.0 and about 12.5 wt % propylene glycol, between about 15.0 and about 25.0 wt % dimethylsulfoxide, and between about 20.0 and about 49.9 wt % 2-(2-Ethoxyethoxy)ethanol; and wherein the solvent mixture is between about 70.0 and about 95.0 wt % of the formulation.   
     
     
         17 . A topical COX inhibitor formulation according to  claim 1 , wherein the formulation is anhydrous and comprises or consists of:
 about 2.0 wt % Diclofenac;   about 27.0 wt % ethanol;   about 8.0 wt % oleic acid, oleyl alcohol, or a mixture thereof;   about 0.5 wt % poloxamer 188;   about 11.0 wt % propylene glycol;   about 3.0 wt % hydroxypropylcellulose;   about 21.0 wt % dimethylsulfoxide; and   about 25.0 wt % 2-(2-Ethoxyethoxy)ethanol.   
     
     
         18 . A topical COX inhibitor formulation according to  claim 1 , wherein the formulation is anhydrous and comprises or consists of:
 about 2.0 wt % Diclofenac;   about 43.5% ethanol;   about 4.0 wt % oleic acid, oleyl alcohol, or a mixture thereof;   0 wt % poloxamer 188;   about 3.0 wt % propylene glycol;   about 3.0 wt % hydroxypropylcellulose;   about 20.0 wt % dimethylsulfoxide; and   about 24.5 wt % 2-(2-Ethoxyethoxy)ethanol.   
     
     
         19 . A topical COX inhibitor formulation according to  claim 1 , wherein the formulation is anhydrous and comprises or consists of:
 about 2.0 wt % Diclofenac;   about 37.5% ethanol;   about 2.0 wt % oleic acid, oleyl alcohol, or a mixture thereof;   0 wt % poloxamer 188;   about 11.0 wt % propylene glycol;   about 3.0 wt % hydroxypropylcellulose;   about 20.0 wt % dimethylsulfoxide; and   about 24.5 wt % 2-(2-Ethoxyethoxy)ethanol.   
     
     
         20 . A topical COX inhibitor formulation according to  claim 1 , wherein the formulation is anhydrous and comprises or consists of:
 about 2.0 wt % Diclofenac;   about 31.5% ethanol;   about 8.0 wt % oleic acid, oleyl alcohol, or a mixture thereof;   0 wt % poloxamer 188;   about 11.0 wt % propylene glycol;   about 3.0 wt % hydroxypropylcellulose;   about 20.0 wt % dimethylsulfoxide; and   about 24.5 wt % 2-(2-Ethoxyethoxy)ethanol.   
     
     
         21 . A method of topically treating a pain episode at a location on the human body, comprising topically applying a topical COX inhibitor formulation according to one of  claims 1 - 20  to the location. 
     
     
         22 . A method according to  claim 21 , wherein the pain episode is an acute pain episode. 
     
     
         23 . A method according to  claim 21 , wherein the pain episode is a chronic pain episode. 
     
     
         24 . A method of topically treating pain of osteoarthritis of the knee(s), comprising topically applying a topical COX inhibitor formulation according to one of  claims 1 - 20  to the knee(s). 
     
     
         25 . A method according to one of  claims 21 - 24 , wherein the COX inhibitor is diclofenac, and the topical dose of diclofenac is about 80 mg or less. 
     
     
         26 . A method according to  claim 25 , wherein the topical dose of diclofenac is about 80 mg, about 40 mg, about 30 mg, about 20 mg, or about 10 mg. 
     
     
         27 . A method according to one of  claims 21 - 26 , wherein the topical COX inhibitor formulation comprises about 2 wt % diclofenac.

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