IP Library Granted Patent US 9,445,995
Granted Patent B2
US 9,445,995 · App. 14/604,985 · Granted Sep 20, 2016

Proliposomal testosterone formulations

Inventors: Guru V. Betageri (Chino Hills, CA); Ramachandran Thirucote (Atherton, CA); Veeran Gowda Kadajji (North Hollywood, CA)
Assignees: WESTERN UNIVERSITY OF HEALTH SCIENCES; TESORX PHARMA, LLC
A61K9/1277A61K9/10A61K9/127A61K9/145A61K9/19A61K9/2013A61K9/2846A61K9/4858A61K9/4891A61K31/568A61K31/575
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Quick Facts
Patent No.
US 9,445,995
App. No.
14/604,985
Granted
Sep 20, 2016
Kind
B2
Abstract

Novel testosterone formulations are disclosed where testosterone is incorporated into a phospholipid/cholesterol system to produce a proliposomal powder dispersion. The proliposomal powder dispersions of the invention may be formulated with phamarceutically acceptable excipients to form pharmaceutical compositions. Enterically coated oral dosage forms are disclosed as are methods of treatment for testosterone replacement therapy.

Claims (20)

1. A method of preparing a proliposomal powder dispersion, wherein the powder dispersion consists essentially of native testosterone, cholesterol, and at least one phospholipid, the method comprising:

(a) dissolving native testosterone in a water miscible solvent until the solution is clear;

(b) obtaining a dispersion of native testosterone, phospholipid and cholesterol by adding a phospholipid to the clear solution of native testosterone and water miscible solvent, and subsequently adding cholesterol to the mixture of the solution of native testosterone and water miscible solvent and phospholipid to obtain a dispersion of testosterone, phospholipid and cholesterol, wherein the native testosterone and cholesterol are added in a weight ratio (native testosterone):(cholesterol) ranging from 1.0:0.05 to 1.0:0.30, and the phospholipid is added such native testosterone, cholesterol and phospholipid are present in a weight ratio of (native testosterone): ((cholesterol)+(phospholipid)) ranging from 1:0:1.0 and 1.0:2.5; and

(c) removing the water miscible solvent by evaporation until a dry powder is obtained.

2. The method of preparing a powder dispersion according to claim 1 , wherein the weight ratio of native (testosterone):(cholesterol) ranges from 1.0:0.08 to 1.0: to 0.012, and the weight ratio of native (testosterone):((cholesterol)+(phospholipid)) ranges from 1.0:1.0 to 1.0:1.2.

3. The method of preparing a powder dispersion according to claim 1 , wherein the phospholipid is selected from distearoyl phosphatidylcholine, dipalmitoyl phosphatidylcholine, dimyristoyl phosphatidylcholine, egg phosphatidylcholine, soy phosphatidylcholine, dimyrsityl phosphatidyl glycerol sodium, 1,2-dimyristoyl-phosphatidic acid, dipalmitoylphosphatidylglycerol, dipalmitoyl phosphate, 1,2-distearoyl-sn-glycero-3-phospho-rac-glycerol, 1,2-distearoyl-sn-glycero-3-phosphatidic acid, phosphatidylserine and sphingomyelin.

4. The method of preparing a powder dispersion according to claim 3 , wherein the phospholipid is distearoyl phosphatidylcholine.

5. The method of preparing a powder dispersion according to claim 1 , wherein the dry powder is further passed through a number 60 sieve.

6. The method of preparing a powder dispersion according to claim 1 , wherein the amount of testosterone added is from 100 to 260 mg.

7. A method of preparing an oral dosage form consisting essentially of native testosterone, cholesterol and at least one phospholipid, the method comprising:

(a) dissolving native testosterone in a water miscible solvent until the solution is clear;

(b) obtaining a dispersion of native testosterone, phospholipid and cholesterol by adding a phospholipid to the clear solution of native testosterone and water miscible solvent, and subsequently adding cholesterol to the mixture of the solution of native testosterone and water miscible solvent and phospholipid to obtain dispersion of native testosterone, phospholipid and cholesterol, wherein the native testosterone and cholesterol are added in a weight ratio (native testosterone): (cholesterol) ranging from 1.0:0.08 to 1.0:0.012, wherein the weight ratio of (native testosterone): ((cholesterol)+(phospholipid)) ranges from 1:0:1.0 and 1.0:1.2; and wherein the dry powder and the microcrystalline cellulose are present in a weight ratio ranging from 1:0.5 to 1:2,

(c) removing the water miscible solvent by evaporation until a dry powder is obtained;

(d) passing the dry powder through a number 60 sieve;

(e) blending the sieved dry powder with microcrystalline cellulose; and

(f) filling capsules with the blended mixture of dry powder and microcrystalline cellulose to form the oral dosage form.

8. The method of preparing an oral dosage form according to claim 7 , wherein the dry powder and the microcrystalline cellulose are present in a weight ratio ranging from 1:0.5 to 1:1.

9. The method of preparing an oral dosage form according to claim 7 , wherein the phospholipid is distearoyl phosphatidylcholine.

10. The method of preparing an oral dosage form according to claim 7 , wherein the capsule is coated with a delayed release coating.

11. The method of preparing an oral dosage form according to claim 7 , wherein the amount of native testosterone added is from 100 to 260 mg.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2015
From: BETAGERI, GURU V.; KADAJJI, VEERAN GOWDA
To: WESTERN UNIVERSITY OF HEALTH SCIENCES
Reel/Frame 035403/0549 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2015
From: THIRUCOTE, RAMACHANDRAN
To: TESORX PHARMA, LLC
Reel/Frame 035403/0605 →
Continuity (4)
Continuation 14149227 · Jan 7, 2014
Continuation PCTUS2013040325 · May 9, 2013
Provisional Application 61644996 · May 9, 2012
Related Publication 20150157572A1 · Jun 11, 2015