# US 6,228,383 B1 · Use of fatty acid esters as bioadhesive substances > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 6,228,383 B1 - Document ID: US6228383B1 - Status: Granted - Kind: B1 - Application number: 08/462,222 - Filed: 1995-06-05 - Granted: 2001-05-08 - Earliest claimed: 1994-03-03 - Assignees: GS Development AB - Inventors: Jens Hansen; Lise Sylvest Nielsen; Tomas Norling - Web page: https://patentgrep.com/patent/US6228383B1 ## CPC - A61K 9/5078: {with drug-free core} - A61K 9/1274: Non-vesicle bilayer structures, e.g. liquid crystals, tubules, cubic phases or cochleates; Sponge phases - A61K 9/5015: {Organic compounds, e.g. fats, sugars} - A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract Use of fatty acid esters as bioadhesive substances. The fatty acid esters have molecular weights below about 1000 dalton and the fatty acid component of the fatty acid ester is a saturated or unsaturated fatty acid having a total number of carbon atoms of from C8 to C22. Particularly suitable fatty acid esters for use according to the invention are fatty acid esters which are selected from the group consisting of fatty acid esters of polyhydric alcohols, fatty acid esters of hydroxycarboxylic acids, fatty acid esters of monosaccharides, fatty acid esters of glycerylphosphate derivatives, fatty acid esters of glycerylsulfate derivative, and mixtures thereof. Excellent bioadhesive properties have been observed for fatty acid esters are glyceryl monooleate, glyceryl monolinoleate or glyceryl monolinolenate. Methods are described for administering an active or protective substance to undamaged or damaged skin or mucosa of an animal such as a human by combining the active or protective substance with a bioadhesive fatty acid ester. The mucosa may be the oral, aural, nasal, lung, gastrointestinal, vaginal, or rectal mucosa. The administration may also be to body cavities such as the oral cavity, e.g. via buccal administration. ## Claims ### Claim 1 A method of using fatty acid esters as bioadhesive substances for administering substances selected from the group consisting of active substances, protective substances, and mixtures thereof, the method comprising applying a bioadhesive composition to a portion of an animal or human body selected from the group consisting of oral, nasal, rectal, aural and vaginal mucosa, said bioadhesive composition comprising at least one substance selected from the group consisting of active substances, protective substances, and mixtures thereof, and at least 6% w/w, calculated on the composition, of at least one bioadhesive substance selected from the group consisting of fatty acid esters and mixtures of fatty acid esters. ### Claim 2 (depends on 1) A method according to claim 1, wherein the composition is applied to a mucosal site of the animal or human body at which it is subject to at least one of mechanical clearance or fluid clearance influence. ### Claim 3 (depends on 1) A method according to claim 1, wherein said bioadhesive composition is applied to one of a damaged or inflamed mucosa of the animal or human body. ### Claim 4 (depends on 1) A method according to claim 1, wherein the fatty acid component of the fatty acid ester is a fatty acid selected from the group consisting of a saturated and unsaturated fatty acid having a total number of carbon atoms of from C8 to C22. ### Claim 5 (depends on 4) A method according to claim 4, wherein the fatty acid component of said fatty acid ester is a saturated fatty acid moiety selected from the group consisting of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid. ### Claim 6 (depends on 4) A method according to claim 4, wherein the fatty acid component of said fatty acid ester is an unsaturated fatty acid moiety selected from the group consisting of palmitoleic acid, oleic acid, linoleic acid, linolenic acid, and arachidonic acid. ### Claim 7 (depends on 1) A method according to claim 1, wherein the fatty acid ester is selected from the group consisting of fatty acid esters of polyhydric alcohols, fatty acid esters of hydroxycarboxylic acids, fatty acid esters of monosaccharides, fatty acid esters of glycerylphosphate derivatives, fatty acid esters of glycerylsulfate derivatives, and mixtures thereof. ### Claim 8 (depends on 7) A method according to claim 7, wherein the polyhydric alcohol is selected from the group consisting of glycerol, 1,2-propanediol, 1,3-propanediol, diacylgalactosylglycerol, diacyldigalactosylglycerol, erythritol, xylitol, adonitol, arabitol, mannitol, and sorbitol. ### Claim 9 (depends on 7) A method according to claim 7, wherein the fatty acid ester is selected from the group consisting of glycerylmonooleate, glycerylmonolinoleate, glycerolmonolinolenate, and mixtures thereof. ### Claim 10 (depends on 7) A method according to claim 7, wherein the hydroxycarboxylic acid is selected from the group consisting of malic acid, tartaric acid, citric acid, and lactic acid. ### Claim 11 (depends on 7) A method according to claim 7, wherein the fatty acid ester is a fatty acid monoester of citric acid. ### Claim 12 (depends on 7) A method according to claim 7, wherein the monosaccharide is selected from the group consisting of glucose, mannose, fructose, threose, gulose, arabinose, ribose, erythrose, lyxose, galactose, sorbose, altrose, tallose, idose, rhamnose, and allose. ### Claim 13 (depends on 7) A method according to claim 7, wherein the fatty acid ester is a fatty acid monoester of a monosaccharide selected from the group consisting of sorbose, galactose, ribose, and rhamnose. ### Claim 14 (depends on 7) A method according to claim 7, wherein the glycerylphosphate derivative is a phospholipid selected from the group consisting of phospatidic acid, phosphatidylserine, phosphatidylethanolamine, phosphatidylcholine, phosphatidylglycerol, phosphatidylinositole, and diphosphatidylglycerol. ### Claim 15 (depends on 7) A method according to claim 7, wherein the fatty acid ester is a fatty acid ester of a glycerylphosphate derivative or a glycerylsulfate derivative, and the fatty acid component is selected from the group consisting of lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and behenic acid. ### Claim 16 (depends on 7) A method according to claim 7, wherein the fatty acid ester is selected form the group consisting of dioleoyl phosphatidylcholin, dilauroyl phosphatidylcholin, dimyristoyl phosphatidylcholin, dipalmitoyl phosphatidylcholin, distearoyl phosphatidylcholin, dibehenoyl phosphatidylcholin, dimyristoyl phosphatidylethanolamine, dipalmitoyl phosphatidylethanolamine, dioleoyl phosphatidylglycerol, dilauroyl phosphatidylglycerol, dimyristoyl phosphatidylglycerol, dipalmitoyl phosphatidylglycerol, distearoyl phosphatidylglycerol, dipalmitoyl phosphatidic acid and mixtures thereof. ### Claim 17 (depends on 1) A method according to claim 1, wherein said fatty acid ester or mixture of fatty acid esters forms a fluid crystalline phase when contacted with an aqueous medium. ### Claim 18 (depends on 1) A method according to claim 1, wherein the composition is adapted for use as one of a pharmaceutical, cosmetic, veterinary, or agrochemical composition. ### Claim 19 (depends on 1) A method according to claim 1, wherein said fatty acid ester or mixture of fatty acid esters is present in a concentration of at least about 15% w/w, calculated on the composition. ### Claim 20 (depends on 1) A method according to claim 1, wherein said fatty acid ester or mixture of fatty acid esters is present in a concentration of at the most 95% w/w, calculated on the composition. ### Claim 21 (depends on 1) A method according to claim 1, wherein said fatty acid ester or mixture of fatty acid esters is present in a concentration of at the most 80% w/w, calculated on the composition. ### Claim 22 (depends on 1) A method according to claim 1, wherein contact of the composition with an aqueous medium results in formation of a fluid crystalline phase. ### Claim 23 (depends on 1) A method according to claim 1, wherein the composition further comprises a pharmaceutically acceptable excipient. ### Claim 24 (depends on 1) A method according to claim 1, wherein the composition is in the form of a spray.