# US 10,245,273 B2 · Oral pharmaceutical products and methods of use combining testosterone esters with hypolipidemic agents

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- Number: US 10,245,273 B2
- Document ID: US10245273B2
- Status: Granted
- Kind: B2
- Application number: 15/107,492
- Filed: 2014-12-24
- Published: 2016-11-03
- Granted: 2019-04-02
- Earliest claimed: 2013-12-26
- Assignees: Clarus Therapeutics, Inc.
- Applicants: Clarus Therapeutics, Inc.
- Inventors: Wael Salameh; Panayiotis Constantinides
- Web page: https://patentgrep.com/patent/US10245273B2

## 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 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 9/20: Pills, tablets, {discs, rods (A61K9/0004, A61K9/0007, A61K9/0056, A61K9/0065 take precedence; for reconstitution of a drink A61K9/0095)}
- A61K 9/2009: {Inorganic compounds}
- A61K 9/48: Preparations in capsules, e.g. of gelatin, of chocolate {(A61K9/0004 takes precedence; bite capsules A61K9/0056)}
- A61K 9/485: {Inorganic compounds}
- A61K 9/4858: {Organic compounds}
- A61K 31/192: having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid {(cannabinoids A61K31/658)}
- A61K 31/195: having an amino group
- A61K 31/216: of acids having aromatic rings, e.g. benactizyne, clofibrate
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 5/26: Androgens
- A61K 9/143: {with inorganic compounds}
- 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

Pharmaceutical products comprising a hypolipidemic agent and a testosterone ester such as testosterone undecanoate are provided. Methods of safely treating a testosterone deficiency or its symptoms with the inventive pharmaceutical products are also provided.

## Claims

### Claim 1

A oral pharmaceutical composition comprising:
a. a hypolipidemic agent that is a peroxisome proliferator activating receptor (PPAR) agonist; and
b. 18 to 22 percent by weight of solubilized testosterone undecanoate, solubilized in a carrier comprising
i. 15 to 17 percent by weight of hydrophilic surfactant;
ii. 50 to 55 percent by weight of lipophilic surfactant; and
iii. 10-15 percent by weight of a mixture of borage oil and peppermint oil.

### Claim 2 (depends on 1)

The pharmaceutical product of claim 1, wherein said PPAR agonist is a pan-PPAR agonist.

### Claim 3 (depends on 1)

The pharmaceutical product of claim 1, wherein said PPAR agonist is a selective PPARδ agonist.

### Claim 4 (depends on 1)

The pharmaceutical product of claim 1, wherein said PPAR agonist is a selective PPARα agonist.

### Claim 5 (depends on 4)

The pharmaceutical product of claim 4, wherein said selective PPARα agonist is selected from: bezafibrate, ciprofibrate, clofibrate, fenofibrate, and gemfibrozil.

### Claim 6 (depends on 1)

The pharmaceutical product of claim 1, wherein said hypolipidemic agent and said testosterone ester are combined in the same pharmaceutical composition.

### Claim 7 (depends on 6)

The pharmaceutical product of claim 6 wherein said pharmaceutical composition is a liquid- or semi-solid filled capsule, a powder-filled capsule, or a tablet.

### Claim 8 (depends on 1)

A method of treating testosterone deficiency or its symptoms comprising orally administering to an individual suffering from testosterone deficiency or its symptoms an effective amount of a pharmaceutical product of claim 1.

### Claim 9 (depends on 8)

The method of claim 8 in which said one or more pharmaceutical compositions are administered once daily.

### Claim 10 (depends on 8)

The method of claim 8 in which said one or more pharmaceutical compositions are administered twice daily.

### Claim 11 (depends on 8)

The method of claim 8 which gives rise to a testosterone Cmax value in said individual falling in the range of about 900 to 1100 ng/dL.