US2020046731A1PendingUtilityA1

Bioavailable solid state (17- β)-hydroxy-4-androsten-3-one esters

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Assignee: LIPOCINE INCPriority: Aug 28, 2014Filed: Feb 12, 2019Published: Feb 13, 2020
Est. expiryAug 28, 2034(~8.1 yrs left)· nominal 20-yr term from priority
Inventors:Mahesh V. PatelNachiappan ChidambaramSatish Kumar NachaegariSrinivasan VenkateshwaranJoel Frank
A61K 9/0053A61K 31/568A61K 9/16A61K 39/00
75
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Claims

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

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate suitable for administration to human subject in need of (17-β)-Hydroxy-4-Androsten-3-one. 
     
     
         2 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , wherein at least 0.001% of the (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate dissolves in 8% Triton X100 containing aqueous solution in 30 minutes. 
     
     
         3 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , wherein the solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate has an apparent solubility in a lipid additive of at least about 5 mg/g to at least about 100 mg/g. 
     
     
         4 . The solid state of  claim 3 , wherein the lipid additive is a fatty acid or fatty acid glyceride. 
     
     
         5 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , which is crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate. 
     
     
         6 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , which is a crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate having 50% or less by total weight of (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of amorphous (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate. 
     
     
         7 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 5 , which is a solvate or a pseudopolymorph or a polymorph. 
     
     
         8 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , which is a crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate form having a powder x-ray diffraction spectra substantially the same as that shown in  FIG. 6 . 
     
     
         9 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , which is (17-3)-3-Oxoandrost-4-en-17-yl tridecanoate having a melting point in the range of 50° C. to 150° C. as determined by differential scanning calorimetry. 
     
     
         10 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , having a melting point as determined by differential scanning calorimetry characteristic of a single crystal form of (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate. 
     
     
         11 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , which is amorphous (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate. 
     
     
         12 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , wherein 20% more (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate is released using USP type 2 apparatus in about 1000 mL 8% Triton X100 solution in water, at 30 minutes than an equivalent amount of solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate that dissolves less than 0.001% in 8% Triton X100 containing aqueous solution in 30 minutes. 
     
     
         13 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , which is amorphous (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate having 50% or less by total weight of crystalline solid (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate. 
     
     
         14 . The solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1 , having a mean particle diameter or D 50  suitable for the manufacture of a pharmaceutical composition or an unit dosage form. 
     
     
         15 . A composition for administration to a human subject in need (17-β3)-Hydroxy-4-Androsten-3-one therapy, the composition comprising or made from: a) the solid state of (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate of  claim 1  and b) a pharmaceutically acceptable carrier, wherein upon oral administration of the solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate to the human subject, at least about 1% of the (17-β)-Hydroxy-4-Androsten-3-one equivalent dose is bioavailable (17-β)-Hydroxy-4-Androsten-3-one to the human subject. 
     
     
         16 . A pharmaceutical composition, comprising or prepared from a solid state pharmaceutical ingredient comprising a solid state (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate and a pharmaceutically acceptable carrier. 
     
     
         17 . The pharmaceutical composition of  claim 16 , comprising or prepared from crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate having 50% or less by total weight of non-crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate. 
     
     
         18 . The pharmaceutical composition of  claim 16 , comprising amorphous (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate substantially free of crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate. 
     
     
         19 . The pharmaceutical composition of  claim 16 , having greater than 10% w/w of (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate. 
     
     
         20 . The pharmaceutical composition of  claim 16 , prepared from crystalline (17-β)-3-Oxoandrost-4-en-17-yl tridecanoate.

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