# US 10,307,449 B2 · Compositions of polymeric myrcene > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,307,449 B2 - Document ID: US10307449B2 - Status: Granted - Kind: B2 - Application number: 15/486,964 - Filed: 2017-04-13 - Published: 2017-09-07 - Granted: 2019-06-04 - Earliest claimed: 2009-03-04 - Assignees: Regenera Pharma Ltd. - Applicants: Regenera Pharma Ltd. - Inventors: Zadik Hazan; Shimon Amselem - Web page: https://patentgrep.com/patent/US10307449B2 ## CPC - A61K 36/22: Anacardiaceae (Sumac family), e.g. smoketree, sumac or poison oak - A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system - A61P 3/04: Anorexiants; Antiobesity agents - A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors - A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis - A61P 9/14: Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers - A61P 11/00: Drugs for disorders of the respiratory system - A61P 17/00: Drugs for dermatological disorders - A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like - A61P 17/06: Antipsoriatics - A61P 25/00: Drugs for disorders of the nervous system - A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia - A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics - A61P 37/02: Immunomodulators - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - 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) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract Compositions and formulations comprising polymeric myrcene. More particularly, the invention relates to compositions comprising an isolated fraction of polymeric myrcene in a hydrophobic carrier and formulations which maintain the biological activity of the active polymer. ## Claims ### Claim 1 A composition consisting of an isolated fraction of mastic gum and an added pharmaceutically acceptable carrier, wherein the fraction is characterized in that it is soluble in at least one polar organic solvent and in at least one non-polar organic solvent, and wherein said fraction is substantially devoid of compounds which are soluble in said polar organic solvent but insoluble in said non-polar organic solvent, wherein the isolated fraction of mastic gum is obtained by a process comprising the steps of: (a) treating mastic gum with a polar organic solvent; (b) isolating a fraction soluble in said polar organic solvent; (c) treating the soluble fraction obtained in step (b) with a non-polar organic solvent; and (d) obtaining the isolated fraction of mastic gum by isolating a fraction soluble in said non-polar organic solvent. ### Claim 2 (depends on 1) The composition according to claim 1, wherein the mastic gum is obtained from a species of Pistacia selected from the group consisting of P. lentiscus, P. atlantica, P. palestina, P. saportae, P. terebinthus, P. vera and P. integerrima. ### Claim 3 (depends on 1) The composition according to claim 1, wherein the at least one polar organic solvent is selected from the group consisting of an alcohol, an ether, an ester, an amide, an aldehyde, a ketone, a nitrile, and combinations thereof; or wherein the polar organic solvent is selected from the group consisting of ethanol, methanol, propanol, isopropanol, 1-butanol, 2-butanol, sec-butanol, t-butanol, 1-pentanol, 2-pentanol, 3-pentanol, neopentanol, 3-methyl-1-butanol, 2-methyl-1-butanol, 3-methyl-2-butanol, 2-methyl-2-butanol, ethyleneglycol, ethyleneglycol monomethyl ether, diethyl ether, methylethyl ether, ethylpropyl ether, methylpropyl ether, 1,2-dimethoxyethane, tetrahydrofuran, dihydrofuran, furan, pyran, dihydropyran, tetrahydropyran, methyl acetate, ethyl acetate, propyl acetate, acetaldehyde, methylformate, ethylformate, ethyl propionate, methyl propionate, dichloromethane, chloroform, dimethylformamide, acetamide, dimethylacetamide, N-methylpyrrolidone, acetone, ethylmethyl ketone, diethyl ketone, acetonitrile, propionitrile, and combinations thereof; or wherein the at least one non-polar organic solvent is selected from the group consisting of acyclic or cyclic, saturated or unsaturated aliphatic hydrocarbons and aromatic hydrocarbons, each of which is optionally substituted by one or more halogens, and combinations thereof; or wherein the non-polar organic solvent is selected from the group consisting of C5-C10 alkanes, C5-C10 cycloalkanes, C6-C14 aromatic hydrocarbons and C7-C14 perfluoroalkanes, and combinations thereof; or wherein the non-polar organic solvent is selected from the group consisting of pentanes, hexanes, heptanes, octanes, nonanes, decanes, cyclopentane, cyclohexane, cycloheptane, benzene, toluene, xylene, and isomers and mixtures thereof; or wherein the non-polar organic solvent is hexane. ### Claim 4 (depends on 1) The composition according to claim 1, wherein said process further comprises the steps of: (e) optionally removing, prior to step (c) the polar organic solvent of step (b); and/or (f) optionally removing, after step (d) the non-polar organic solvent. ### Claim 5 (depends on 4) The composition according to claim 4, wherein said process further comprises the step of size fractionating the fraction obtained in step (b) or step (d); or wherein either or both of steps (e) and (f) comprise removing the solvent by a means selected from the group consisting of rotary evaporation, application of high vacuum and a combination thereof; or wherein said process further comprises repeating steps (a) to (b) and/or steps (c) to (d) for a multiplicity of cycles. ### Claim 6 (depends on 1) The composition according to claim 1, wherein the fraction is substantially devoid of terpene compounds which are soluble in said polar organic solvent and insoluble in said non-polar organic solvent. ### Claim 7 (depends on 1) The composition according to claim 1, comprising polymeric myrcene, wherein the polymeric myrcene has a number average molecular weight in the range of at least about 1,000 to about 20,000. ### Claim 8 (depends on 7) The composition according to claim 7, wherein the polymeric myrcene is selected from the group consisting of polymeric β-myrcene, polymeric α-myrcene, myrcene copolymers and combinations thereof; wherein the poly-β-myrcene is selected from the group consisting of cis-1,4-poly-β-myrcene, trans-1,4-poly-β-myrcene, 3,4-poly-β-myrcene, 1,2-poly-β-myrcene and combinations thereof. ### Claim 9 (depends on 1) The composition according to claim 1, comprising from about 0.01 to about 25% (w/w) of the isolated fraction of mastic gum, based on the total weight of the composition. ### Claim 10 (depends on 1) The composition according to claim 1, wherein the carrier is a hydrophobic carrier which is selected from the group consisting of: a) at least one oil selected from the group consisting of cottonseed oil, almond oil, canola oil, coconut oil, corn oil, grape seed oil, olive oil peanut oil, saffron oil, sesame oil, soybean oil and combinations thereof; b) at least one wax; and c) combinations thereof. ### Claim 11 (depends on 1) The composition according to claim 1, which is in a form suitable for cosmetic or dermatologic administration; or in a form suitable for administration by a route selected from the group consisting of oral, topical, parenteral, intramuscular, subcutaneous, intradermal, vaginal, rectal, intracranial, intranasal, intraocular, auricular, pulmonary intralesional, intraperitoneal, intraarterial, intracerebral, intracerebroventricular, intraosseus and intrathecal; or in a form selected from the group consisting of a capsule, a tablet, a suppository, a suspension, an ointment, a cream, a lotion, a solution, an emulsion, a film, a cement, a powder, a glue, an aerosol and a spray. ### Claim 12 (depends on 1) The composition according to claim 1, which is: a) an inclusion complex and the carrier contains at least one cyclodextrin; b) a nanoemulsion in which droplets have an average particle size of less than 800 nm; or c) a microemulsion and the carrier contains at least one non-ionic surfactant selected from the group consisting of a polyoxyl castor oil, a polyoxyethylene sorbitan fatty acid ester, a poloxamer, vitamin E, a polyoxyethylene alkyl ether, a polyoxyethylene stearates, a saturated polyglycolyzed glyceride and combinations thereof. ### Claim 13 A composition consisting of an isolated fraction of mastic gum and an added pharmaceutically acceptable carrier, wherein the fraction is characterized in that it is soluble in at least one polar organic solvent and in at least one non-polar organic solvent, and wherein said fraction is substantially devoid of compounds which are soluble in said polar organic solvent but insoluble in said non-polar organic solvent, wherein said polar organic solvent is an alcohol, wherein the carrier is an oil selected from the group consisting of cottonseed oil, almond oil, canola oil, coconut oil, corn oil, grape seed oil, olive oil peanut oil, saffron oil, sesame oil, soybean oil and combinations thereof. ### Claim 14 (depends on 13) The composition of claim 13, wherein the alcohol is selected from the group consisting of ethanol, methanol, propanol, isopropanol, 1-butanol, 2-butanol, sec-butanol, t-butanol, 1-pentanol, 2-pentanol, 3-pentanol, neopentanol, 3-methyl-1-butanol, 2-methyl-1-butanol, 3-methyl-2-butanol, 2-methyl-2-butanol. ### Claim 15 (depends on 13) The composition of claim 13, wherein the at least one non-polar organic solvent is selected from the group consisting of acyclic or cyclic, saturated or unsaturated aliphatic hydrocarbons and aromatic hydrocarbons, each of which is optionally substituted by one or more halogens, and combinations thereof; or wherein the non-polar organic solvent is selected from the group consisting of C5-C10 alkanes, C5-C10 cycloalkanes, C6-C14 aromatic hydrocarbons and C7-C14 perfluoroalkanes, and combinations thereof; or wherein the non-polar organic solvent is selected from the group consisting of pentanes, hexanes, heptanes, octanes, nonanes, decanes, cyclopentane, cyclohexane, cycloheptane, benzene, toluene, xylene, and isomers and mixtures thereof; or wherein the non-polar organic solvent is hexane. ### Claim 16 (depends on 13) The composition according to claim 13, wherein the isolated fraction is obtained by a process comprising the steps of: (a) contacting plant material with at least one alcohol, wherein the plant material is selected from the group consisting of resin, leaves, twigs, roots, flowers, seeds, buds, bark, nuts, roots and combinations thereof; (b) isolating a fraction which remains soluble in the at least one alcohol solvent (c) optionally removing said alcohol solvent; (d) treating the soluble fraction obtained in step (b) or (c) with at least one non-polar organic solvent; (e) isolating a fraction soluble in said nonpolar organic solvent; and (f) optionally removing said nonpolar organic solvent; wherein steps (a) to (c) and steps (d) to (f) are each independently optionally carried out for a number of cycles; so as to obtain an isolated fraction of mastic gum. ### Claim 17 (depends on 16) The isolated fraction according to claim 16, wherein said process further comprises the step of size fractionating the fraction obtained in step (c) or step (f); or wherein either or both of steps (c) and (f) comprise removing the solvent by a means selected from the group consisting of rotary evaporation, application of high vacuum and a combination thereof. ### Claim 18 (depends on 13) The composition according to claim 13, wherein the fraction is substantially devoid of terpene compounds which are soluble in said polar organic solvent and insoluble in said non-polar organic solvent. ### Claim 19 (depends on 13) The composition according to claim 13, wherein the fraction comprises polymeric myrcene, wherein the polymeric myrcene has a number average molecular weight in the range of at least about 1,000 to about 20,000. ### Claim 20 (depends on 13) The composition according to claim 13, comprising from about 0.01 to about 25% (w/w) of the isolated fraction of mastic gum, based on the total weight of the composition. ### Claim 21 (depends on 13) The composition according to claim 13, which is in a form suitable for cosmetic or dermatologic administration; or in a form suitable for administration by a route selected from the group consisting of oral, topical, parenteral, intramuscular, subcutaneous, intradermal, vaginal, rectal, intracranial, intranasal, intraocular, auricular, pulmonary intralesional, intraperitoneal, intraarterial, intracerebral, intracerebroventricular, intraosseus and intrathecal; or in a form selected from the group consisting of a capsule, a tablet, a suppository, a suspension, an ointment, a cream, a lotion, a solution, an emulsion, a film, a cement, a powder, a glue, an aerosol and a spray.