Details for Patent: 11,642,355

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Which drugs does patent 11,642,355 protect, and when does it expire?

Patent 11,642,355 protects AZMIRO and is included in one NDA.

Summary for Patent: 11,642,355

Title:	Pharmaceutical compositions of testosterone
Abstract:	The present invention provides stable pharmaceutical compositions, comprising a pharmaceutically effective amount of testosterone or a pharmaceutically acceptable ester thereof, a pharmaceutically acceptable oil vehicle, and a stabilizing amount of benzyl alcohol, for example, about 1% to 3% weight/volume of benzyl alcohol. The present invention also provides a process for stabilizing testosterone-containing pharmaceutical compositions by ageing them at a temperature of about 20° C. to about 60° C. for at least 48 hours, e.g., prior to secondary packing and labeling. These compositions were stable over the shelf life of the product, without exhibiting crystal formation, even upon storing at temperatures of about 2° C. to about 8° C. Other aspects of the invention relate to methods for making such pharmaceutical compositions, as well as methods of using such pharmaceutical compositions for hormone replacement therapy, e.g., in a male patient having a condition associated with symptoms of deficiency or absence of endogenous testosterone.
Inventor(s):	Umangi K. SONI, Prem Prakash SINGH, Hanimi Reddy BAPATU, Praveen Kumar Subbappa, Ajay Kumar Singh
Assignee:	Azurity Pharmaceuticals Inc
Application Number:	US17/696,319
Patent Claim Types: see list of patent claims	Composition;

United States Drug Patent 11,642,355: Claim Scope, Validity Risks, and Testosterone Cypionate Patent Landscape

U.S. Patent No. 11,642,355 covers a narrow injectable testosterone cypionate formulation and related pre-filled syringe. The asserted combination is approximately 200 mg/mL testosterone cypionate, 15-30 mg/mL benzyl alcohol, benzyl benzoate, and cottonseed oil. The claims also require sterilization, intramuscular suitability, and defined resistance to crystal formation during storage.

The patent’s commercial scope depends on whether a competing product uses the claimed excipient combination and benzyl alcohol concentration. A conventional testosterone cypionate injection may avoid infringement if it uses a different oil, lacks benzyl alcohol, falls outside the claimed concentration range, or cannot satisfy the claimed stability limitations. The patent does not broadly cover testosterone cypionate as an active ingredient, all injectable testosterone products, or every 200 mg/mL formulation.

What does U.S. Patent 11,642,355 protect?

The patent protects three related subject-matter categories:

Claim group	Protected subject matter	Principal additional limitation
Claim 1 and claims 4-7	Injectable pharmaceutical composition	No crystal formation for six months at approximately 10°C to 15°C
Claim 2 and claims 8-11	Pre-filled syringe containing the composition	Same formulation and stability requirements
Claim 3 and claims 12-15	Injectable pharmaceutical composition subjected to pre-aging	At least 48 hours at approximately 20°C to 60°C before storage at 2°C to 8°C without crystal formation

The independent claims require a closed ingredient set:

1. About 200 mg/mL testosterone cypionate.
2. About 15 mg/mL to 30 mg/mL benzyl alcohol.
3. Benzyl benzoate.
4. Cottonseed oil.

The composition must also be sterilized and suitable for intramuscular injection. The claims are therefore formulation claims, not claims to the testosterone cypionate molecule or to a therapeutic method of administering testosterone.

How broad is the formulation claim?

The formulation claim is narrow because it uses “consisting of.” In patent claim construction, that language generally excludes additional unrecited ingredients that materially alter the claimed composition, subject to the interpretation of the intrinsic record and possible doctrine-of-equivalents arguments.[1]

The claim has several cumulative limitations:

• Testosterone cypionate must be present at approximately 200 mg/mL.
• Benzyl alcohol must be within approximately 15-30 mg/mL.
• Benzyl benzoate must be present.
• Cottonseed oil must be present.
• The product must be sterile.
• The product must be suitable for intramuscular injection.
• The specified crystal-formation result must be met.

A product with 10 mg/mL benzyl alcohol would generally fall outside the literal 15-30 mg/mL range. A product with 35 mg/mL may also fall outside the range. The treatment of “about” depends on the specification, prosecution history, technical meaning, and evidence regarding formulation tolerances.

The concentration-dependent claims add commercial clarity but limited breadth. Claims 4-7 expressly identify approximately 15, 20, 25, and 30 mg/mL benzyl alcohol. Claims 8-11 and 12-15 repeat those concentrations for the syringe and pre-aged composition categories.

What do the dependent claims add?

Claims 4-7 depend from claim 1 and narrow the benzyl alcohol concentration. Claims 8-11 depend from claim 2 and apply the same concentration points to the pre-filled syringe. Claims 12-15 depend from claim 3 and apply them to the pre-aged composition.

These claims create fallback positions if the broader 15-30 mg/mL range is challenged. Their practical value depends on whether the patent specification supports each concentration as a distinct technical embodiment and whether the prior art discloses the same formulation and stability performance.

The phrase “comprising consisting of” in several supplied claim formulations is internally awkward. The issued patent’s official claim text, rather than an informal transcription, controls the legal analysis. If the issued claims use “comprising” and “consisting of” in different locations, the distinction may affect whether unlisted excipients are permitted.

What stability limitation must an accused product satisfy?

Claim 1 requires that the composition “does not exhibit crystal formation for 6 months” when stored at approximately 10°C to 15°C. Claim 3 requires the same result after pre-aging and subsequent storage at approximately 2°C to 8°C.

These are performance limitations, not merely ingredient limitations. A formulation containing the claimed ingredients may still avoid literal infringement if it fails the stated stability requirement. Conversely, the patent owner would likely need a reproducible testing protocol to establish infringement.

Important technical questions include:

• What qualifies as a crystal?
• Is visual inspection sufficient, or is polarized-light microscopy required?
• What container and fill volume are used?
• Does the six-month period begin after sterilization, filling, or release?
• Are the storage temperatures controlled continuously?
• Does the claim require testing of the accused commercial product or can formulation data establish infringement?

The claim language does not, by itself, define these testing parameters. The specification, prosecution history, and expert evidence would determine how the limitation is applied.

What does claim 3 add through pre-aging?

Claim 3 covers a composition that has been aged in containers for at least 48 hours at approximately 20°C to 60°C before refrigerated storage at approximately 2°C to 8°C. The composition must then avoid crystal formation for six months.

This claim is materially narrower than claim 1. A competing manufacturer could potentially avoid claim 3 by using:

• No intentional pre-aging step.
• Pre-aging for less than 48 hours.
• A temperature below 20°C or above 60°C.
• A different container or processing sequence.
• A formulation that does not satisfy the claimed low-temperature stability result.

The claim may create manufacturing-process risk even where the final formulation is identical. Evidence could include batch records, stability protocols, standard operating procedures, deviation reports, and manufacturing validation documents.

Does the patent cover testosterone cypionate generic products?

It may cover some generic products, but not all testosterone cypionate injections.

A generic product is exposed when its approved composition and manufacturing process contain the claimed combination. The highest-risk profile is a sterile 200 mg/mL testosterone cypionate injection using cottonseed oil, benzyl benzoate, and benzyl alcohol within the claimed range.

Lower-risk profiles include products using:

• A different vegetable oil or synthetic oil.
• No benzyl alcohol.
• Benzyl alcohol below or above the claimed range.
• A different testosterone ester.
• A different concentration of testosterone cypionate.
• A formulation lacking the claimed six-month crystal-resistance result.
• A pre-filled syringe that does not contain the claimed liquid composition.

Product-by-process exposure under claim 3 requires particular attention. A manufacturer may have a formulation that meets the composition limitations but still avoid claim 3 if it did not perform the claimed aging step. The legal treatment of process limitations in product claims depends on claim construction and the governing infringement facts.

What prior art creates validity risk?

The claimed ingredients are individually conventional in oil-based injectable testosterone products. Testosterone cypionate injections have historically used cottonseed oil and benzyl benzoate as formulation components. Benzyl alcohol is also a known preservative or co-solvent in injectable products, depending on the formulation and dosage presentation.[2]

The likely validity dispute is therefore not whether each ingredient was known separately. The central questions are whether a single prior-art reference disclosed:

• Approximately 200 mg/mL testosterone cypionate.
• Benzyl alcohol at 15-30 mg/mL.
• Benzyl benzoate.
• Cottonseed oil.
• Sterile intramuscular use.
• The claimed crystal-free stability period and temperature conditions.

For obviousness, the analysis would examine whether a skilled formulator would have selected the claimed benzyl alcohol range and expected the claimed reduction in crystal formation. Experimental data showing an unexpected stability advantage could support validity. Routine optimization, overlapping ranges, or prior examples identifying the same excipient concentrations could weaken the patent.

Relevant prior-art sources would include:

• Earlier testosterone cypionate injection labels.
• Published patent applications involving oil-based testosterone formulations.
• Formulation-development reports.
• FDA submissions and product specifications.
• Scientific literature on testosterone cypionate solubility and crystallization.

The existing commercial product landscape is particularly relevant because formulation patents can face anticipation or obviousness arguments based on long-marketed reference products. The exact prior-art record must be determined from the patent’s cited references and prosecution history.[1]

What is the Orange Book status of U.S. Patent 11,642,355?

The patent’s Orange Book significance cannot be inferred from the patent number or claim language alone. Orange Book listing requires an approved drug product, an NDA holder, and a patent submission accepted by FDA under applicable listing standards.[3]

A formulation patent may be listed if it claims the drug substance, drug product, or an approved method of use in a manner recognized by FDA regulations. A patent that covers only a manufacturing process generally has a different listing analysis. The relevant questions are:

• Whether the patent is listed against an approved testosterone cypionate NDA.
• Which NDA and product presentation are identified.
• Whether the listing covers a vial, ampule, or pre-filled syringe.
• Whether an FDA-recognized expiration date appears.
• Whether the patent has been delisted or disputed.

The patent should not be treated as an Orange Book barrier unless the current FDA Orange Book records confirm a listing.

When does U.S. Patent 11,642,355 lose exclusivity?

A patent normally expires 20 years after the earliest effective nonprovisional U.S. filing date, subject to patent-term adjustment, patent-term extension, terminal disclaimers, and other statutory adjustments.[4]

The grant date alone does not establish the expiration date. Patent No. 11,642,355 issued on May 9, 2023, but its enforceable term depends on its priority and filing chain. A continuation may have the same effective priority date as an earlier application, while a terminal disclaimer may tie its expiration to another patent.

The controlling sources are:

• The front page of the issued patent.
• The continuity and priority statements.
• USPTO Patent Center.
• The patent-term-adjustment calculation.
• Any terminal disclaimer.
• Any FDA patent-term extension record.

No reliable launch date should be calculated without those records.

Are Paragraph IV challenges likely?

A Paragraph IV certification is relevant if the patent is listed in the Orange Book for the reference product and a generic applicant seeks approval before patent expiration.[5] The potential grounds would include:

1. Noninfringement: The proposed product lacks one or more required ingredients or falls outside the benzyl alcohol range.
2. Invalidity: The claims are anticipated or obvious in light of prior testosterone cypionate formulations.
3. Indefiniteness: Terms such as “about,” “does not exhibit crystal formation,” or “suitable for intramuscular injection” may be challenged if the intrinsic record does not provide workable boundaries.
4. Written description or enablement: The challenger may argue that the full 15-30 mg/mL range or all claimed storage conditions is not adequately supported.
5. Lack of patent listing eligibility: The patent may not properly claim the approved drug product.

A Paragraph IV notice would generally trigger the statutory litigation framework and could impose a 30-month stay of approval under the Hatch-Waxman Act, subject to the statute and litigation events.[5] No particular generic challenger or settlement should be assumed without a verified FDA filing or court docket.

Which companies face the greatest commercial exposure?

The highest exposure would fall on manufacturers marketing or developing 200 mg/mL testosterone cypionate injections with the same excipient architecture. Exposure is lower for companies using different vehicles or dosage presentations.

Product strategy	Relative exposure
200 mg/mL, cottonseed oil, benzyl benzoate, 15-30 mg/mL benzyl alcohol	High
Same formulation in a pre-filled syringe	High under claim 2
Same ingredients but benzyl alcohol outside the range	Lower
Same active ingredient in a different oil vehicle	Lower
Testosterone cypionate at a different concentration	Lower
Testosterone enanthate or another testosterone ester	Generally outside these claims
Same formulation with documented 48-hour pre-aging and refrigerated stability	Highest under claim 3

Revenue exposure depends on the sales of the affected product and the availability of non-infringing formulation changes. Because the patent is directed to a specific formulation, design-around options may be more practical than for a composition-of-matter patent, but reformulation could require FDA supplements, stability work, manufacturing validation, and new commercial packaging.

How strong is the patent estate?

Based on the supplied claims, U.S. Patent 11,642,355 is a focused formulation patent with potential commercial relevance but limited product-category breadth.

Its strengths are:

• A defined excipient combination.
• Multiple concentration-specific fallback claims.
• A stability result tied to crystal formation.
• Coverage of both bulk injectable composition and pre-filled syringe presentation.
• A separate pre-aging embodiment directed to manufacturing practice.

Its vulnerabilities are:

• Conventionality of the individual ingredients.
• Potentially broad “about” ranges.
• Dependence on a crystal-formation test that may require detailed proof.
• Possible prior-art overlap with existing testosterone cypionate injections.
• Limited protection against different oils, concentrations, or delivery formats.
• Potential uncertainty over whether the patent is listed in the Orange Book.

The patent is stronger against an exact-copy formulation than against a redesigned product. The pre-filled syringe claims may increase packaging and presentation exposure, but they do not independently protect every syringe containing testosterone cypionate.

What litigation and settlement issues should be monitored?

The relevant litigation indicators are:

• A Paragraph IV notice involving an NDA to which the patent is listed.
• A Hatch-Waxman complaint filed within the statutory period.
• Claim-construction disputes over “about,” crystal formation, and pre-aging.
• Inter partes review or post-grant validity proceedings.
• Declaratory-judgment actions by generic or specialty pharmaceutical companies.
• Settlement agreements providing a licensed entry date.
• FDA records showing patent delisting or an amended expiration date.

A settlement could permit an earlier generic launch without invalidating the patent. Its commercial effect would depend on the agreed entry date, authorized-generic rights, supply terms, and restrictions on alternative formulations.

Key Takeaways

• U.S. Patent 11,642,355 is directed to a specific testosterone cypionate injectable formulation, not testosterone cypionate generally.
• The core formulation requires approximately 200 mg/mL testosterone cypionate, 15-30 mg/mL benzyl alcohol, benzyl benzoate, and cottonseed oil.
• Claims 1 and 2 require six-month resistance to crystal formation at approximately 10°C to 15°C.
• Claim 3 adds at least 48 hours of pre-aging at approximately 20°C to 60°C before refrigerated storage.
• The concentration-specific claims provide fallback protection at approximately 15, 20, 25, and 30 mg/mL benzyl alcohol.
• Exact-copy products face the greatest infringement risk.
• Products using different oils, benzyl alcohol concentrations, testosterone concentrations, or formulation architectures may offer design-around paths.
• Orange Book status, patent expiration, Paragraph IV activity, litigation, and settlements must be confirmed from current FDA and USPTO records.
• The principal validity risks are prior-art overlap, obviousness based on formulation optimization, and proof of the crystal-formation limitation.

FAQs

Does U.S. Patent 11,642,355 cover Depo-Testosterone?

It may create risk for a product with the claimed composition, but the patent does not automatically cover every product sold under the Depo-Testosterone name. The product’s current formulation, concentration, packaging, stability data, and patent records must be compared claim by claim.

Can a generic avoid the patent by changing only the benzyl alcohol level?

Potentially. A formulation below 15 mg/mL or above 30 mg/mL may avoid literal infringement, but the meaning of “about” and possible doctrine-of-equivalents arguments must be evaluated.

Does the patent cover testosterone cypionate in a pre-filled syringe regardless of formulation?

No. Claim 2 is limited to a pre-filled syringe containing the specified testosterone cypionate composition and satisfying the sterilization, intramuscular-use, and crystal-stability requirements.

Is claim 3 a method-of-manufacturing claim?

Claim 3 is drafted as a composition claim with a historical or process-related limitation requiring that the composition “has been aged” under specified conditions. Its infringement treatment depends on how the claim is construed and whether the accused product can be shown to have undergone the required aging.

Can a company launch before patent expiration if its product is not Orange Book-listed?

Orange Book listing affects Hatch-Waxman certification and stay procedures. It does not eliminate ordinary patent infringement risk. A company may still face infringement litigation under the patent even if the patent is not listed against the relevant NDA.

References

1. United States Patent and Trademark Office. (2023). U.S. Patent No. 11,642,355.
2. U.S. Food and Drug Administration. (n.d.). Testosterone cypionate injection prescribing information.
3. U.S. Food and Drug Administration. (n.d.). Approved drug products with therapeutic equivalence evaluations.
4. United States Code, 35 U.S.C. §§ 154, 156.
5. United States Code, 21 U.S.C. § 355(j).

Drugs Protected by US Patent 11,642,355

Applicant	Tradename	Generic Name	Dosage	NDA	Approval Date	TE	Type	RLD	RS	Patent No.	Patent Expiration	Product	Substance	Delist Req.	Patented / Exclusive Use	Submissiondate
Azurity	AZMIRO	testosterone cypionate	SOLUTION;INTRAMUSCULAR	216318-001	Jun 2, 2022		DISCN	Yes	No	11,642,355		Y