# US 11,298,365 B2 · Bioavailable solid state (17-β)-hydroxy-4-androsten-3-one esters > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,298,365 B2 - Document ID: US11298365B2 - Status: Granted - Kind: B2 - Application number: 16/849,957 - Filed: 2020-04-15 - Published: 2021-03-11 - Granted: 2022-04-12 - Earliest claimed: 2014-08-28 - Applicants: Lipocine Inc. - Inventors: Mahesh V. Patel; Nachiappan Chidambaram; Satish Kumar Nachaegari; Srinivasan Venkateshwaran; Joel Frank - Web page: https://patentgrep.com/patent/US11298365B2 ## CPC - A61K 31/568: substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone - A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration} - A61K 9/16: Agglomerates; Granulates; Microbeadlets {; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction (A61K9/20 takes precedence if the final form is a tablet; microspheres with drug-free outer coating, microcapsules A61K9/50; mixture of different granules, microcapsules, (coated) microparticles A61K9/5084; nanoparticles A61K9/51)} - A61K 39/00: Medicinal preparations containing antigens or antibodies (materials for immunoassay G01N33/53) - 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 Disclosed are bioavailable solid state (17-β)-Hydroxy-4-Androsten-3-one esters suitable for pharmaceutical uses and administration to mammals in need of (17-β)-Hydroxy-4-Androsten-3-one. ## Claims ### Claim 1 A pharmaceutical composition comprising or prepared from a crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate form having a melting point in the range of 68-75° C. fully or partially dissolved in a lipophilic surfactant. ### Claim 2 (depends on 1) The pharmaceutical composition of claim 1, comprising a crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate form having a melting point in the range of 68-75° C. ### Claim 3 (depends on 1) The pharmaceutical composition of claim 1, prepared from a crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate form having a melting point in the range of 68-75° C. ### Claim 4 (depends on 1) The pharmaceutical composition of claim 1, further comprising a pharmaceutically acceptable carrier having a hydrophilic surfactant. ### Claim 5 (depends on 1) The pharmaceutical composition of claim 1, wherein said lipophilic surfactant comprises a fatty acid. ### Claim 6 (depends on 1) The pharmaceutical composition of claim 1, wherein said lipophilic surfactant comprises a monoglyceride. ### Claim 7 (depends on 1) The pharmaceutical composition of claim 1, wherein said lipophilic surfactant comprises a diglyceride. ### Claim 8 (depends on 5) The pharmaceutical composition of claim 5, further comprising a polyethylene glycol. ### Claim 9 (depends on 6) The pharmaceutical composition of claim 6, further comprising a polyethylene glycol. ### Claim 10 (depends on 1) The pharmaceutical composition of claim 1, formulated as a capsule or tablet. ### Claim 11 (depends on 5) The pharmaceutical composition of claim 5, wherein said fatty acid comprises a diglyceride. ### Claim 12 (depends on 5) The pharmaceutical composition of claim 5, wherein the composition releases greater than 70% of the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate at 2 hours and less than 100% at 30 minutes when tested with a USP type 2 apparatus in about 1000 mL 8% Octoxynol-9 solution in water at 37° C. (±0.5) at 100 rpm. ### Claim 13 (depends on 6) The pharmaceutical composition of claim 6, wherein when tested with a USP type 2 apparatus in about 1000 mL 8% Octoxynol-9 solution in water at 37° C. (±0.5) at 100 rpm the composition releases at least 40% of the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate at 60 minutes. ### Claim 14 (depends on 7) The pharmaceutical composition of claim 7, wherein the composition releases greater than 70% of the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate at 2 hours when tested with a USP type 2 apparatus in about 1000 mL 8% Octoxynol-9 solution in water at 37° C. (±0.5) at 100 rpm. ### Claim 15 (depends on 11) The pharmaceutical composition of claim 11, wherein the composition releases less than 100% of the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate at 30 minutes when tested in a USP type 2 apparatus in about 1000 mL 8% Octoxynol-9 solution in water at 37° C. (±0.5) at 100 rpm. ### Claim 16 (depends on 7) The pharmaceutical composition of claim 7, wherein the composition releases greater than 70% of the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate at 2 hours and less than 100% at 30 minutes when tested with a USP type 2 apparatus in about 1000 mL 8% Octoxynol-9 solution in water at 37° C. (±0.5) at 100 rpm. ### Claim 17 (depends on 12) The pharmaceutical composition of claim 12, wherein the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate is present in an amount of 300 mg or more and the composition is formulated as an oral capsule for administration to humans. ### Claim 18 (depends on 13) The pharmaceutical composition of claim 13, wherein the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate is present in an amount of 300 mg or more of and the composition is formulated as an oral capsule for administration to humans. ### Claim 19 (depends on 14) The pharmaceutical composition of claim 14, wherein the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate is present in an amount of 300 mg or more of and the composition is formulated as an oral capsule for administration to humans. ### Claim 20 (depends on 15) The pharmaceutical composition of claim 15, wherein the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate is present in an amount of 300 mg or more of and the composition is formulated as an oral capsule for administration to humans. ### Claim 21 (depends on 12) The pharmaceutical composition of claim 12, wherein the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate is present in an amount of from 250 mg to about 300 mg. ### Claim 22 (depends on 13) The pharmaceutical composition of claim 13, wherein the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate is present in an amount of from 250 mg to about 300 mg. ### Claim 23 (depends on 14) The pharmaceutical composition of claim 14, wherein the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate is present in an amount of from 250 mg to about 300 mg.