Details for Patent: 8,709,392

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Which drugs does patent 8,709,392 protect, and when does it expire?

Patent 8,709,392 protects DIFFERIN and is included in one NDA.

This patent has seventeen patent family members in twelve countries.

Summary for Patent: 8,709,392

Title:	Cosmetic/dermatological compositions comprising naphthoic acid compounds and polyurethane polymers
Abstract:	Cosmetic/dermatological compositions for topical application and useful for the treatment, e.g., of acne, contain, formulated into a physiologically acceptable medium, at least one naphthoic acid compound and at least one polyurethane polymer or derivative thereof, the at least one naphthoic acid compound being dispersed therein.
Inventor(s):	Claire Mallard, Eve Ferrara
Assignee:	Galderma Research and Development SNC
Application Number:	US13/889,163
Patent Claim Types: see list of patent claims	Use; Composition; Dosage form;

US Patent 8,709,392: Claim Scope, Adapalene Formulation Coverage, and Patent Landscape

US Patent 8,709,392 protects topical compositions that combine an undissolved naphthoic acid compound, principally adapalene, with a polyurethane polymer that reduces irritation. The patent also covers manufacturing processes and acne-treatment methods using those compositions. Its strongest commercial relevance is to adapalene formulations containing a specified polyurethane anti-irritant, particularly polyolprepolymer type 2.

The claims do not cover every adapalene product. They require a specific combination of active ingredient, physical state, polyurethane component, therapeutic or cosmetic vehicle, and absence of saw palmetto extract. A product containing adapalene alone, or adapalene dissolved rather than dispersed in undissolved form, falls outside the literal scope of independent claim 1.

What does US Patent 8,709,392 protect?

The patent has three principal claim groups:

Claim group	Claims	Protected subject matter
Composition claims	1-21, 29-30	Topical cosmetic, dermatological, or medicament compositions
Manufacturing claims	22-24	Processes for dispersing the naphthoic acid compound and incorporating polyurethane
Treatment claims	25-28	Treatment of acne, acne-prone skin, seborrhea, photodamage, and aging

The broadest composition claim is claim 1. It requires all of the following:

1. A topically applicable, stable cosmetic or dermatological composition.
2. At least one naphthoic acid compound.
3. The naphthoic acid compound dispersed in undissolved form.
4. At least one polyurethane polymer.
5. The polyurethane polymer present in an amount sufficient to reduce irritation.
6. A physiologically acceptable topical medium.
7. No extract of saw palmetto berries.

The claim is therefore a combination claim. The patent does not claim the naphthoic acid compound, adapalene, or polyurethane polymer in isolation.

Which active ingredients fall within the patent?

Claim 2 defines a broad naphthoic acid structure using substituent R groups that include hydrogen, hydroxyl, C1-C4 alkyl, C1-C10 alkoxy, and cycloaliphatic radicals.

Claim 4 narrows the compounds to four substituted 6-phenyl-2-naphthoic acids:

• 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid
• 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthoic acid
• 6-[3-(1-adamantyl)-4-decyloxyphenyl]-2-naphthoic acid
• 6-[3-(1-adamantyl)-4-hexyloxyphenyl]-2-naphthoic acid

The first compound is adapalene. Claims 5-7 focus specifically on adapalene at concentrations of approximately 0.1% and 0.3%.

Claim	Active-ingredient limitation
1	At least one naphthoic acid compound
2	Compound within the defined structural formula
3	Naphthoic acid compound at 0.001%-10% by weight
4	Four specified substituted naphthoic acids
5	Adapalene
6	Approximately 0.1% adapalene
7	Approximately 0.3% adapalene
8	Naphthoic acid compound is the only active principle

The 0.1% and 0.3% concentrations correspond to commercially important adapalene strengths. The concentration limitations in claims 6 and 7 are narrow, but they become commercially significant when combined with the polyurethane and undissolved-dispersion requirements.

How does the undissolved-dispersion limitation affect infringement?

The phrase "dispersed in undissolved form" is central to claim 1. It distinguishes the claimed formulation from a composition in which the naphthoic acid compound is fully solubilized.

A formulation may contain the same active ingredient and the same polyurethane but avoid literal infringement if the active ingredient is dissolved. That distinction creates a formulation-design pathway for competitors, although the practical value depends on whether the product can remain stable, therapeutically effective, and non-irritating after changing the active's physical state.

The claim also requires a polyurethane amount "sufficient to decrease the irritant effect." This functional limitation is potentially enforceable, but it introduces evidentiary issues. An infringement case would likely examine:

• The identity and concentration of the polyurethane.
• Particle size and solid-state form of the active.
• Comparative irritation testing.
• Product composition and manufacturing records.
• Whether the polyurethane performs the claimed anti-irritant function.
• Whether the product's formulation and use produce the claimed technical effect.

A product containing a polyurethane for viscosity, film formation, or texture control could still fall within the claim if the polymer also satisfies the anti-irritant limitation.

What polyurethane polymers are protected?

Claims 9-12 narrow the polyurethane component. Claim 9 identifies:

• Polyolprepolymer of type 2
• Polyolprepolymer of type 14
• Polyolprepolymer of type 15
• Mixtures of those polymers

Claim 10 selects polyolprepolymer type 2. Claim 11 sets a broad polyurethane concentration range of 0.5%-20% by weight. Claim 12 identifies approximately 1%, 3%, 7%, and 10%.

Limitation	Scope
Broad polyurethane range	0.5%-20%
Express preferred concentrations	About 1%, 3%, 7%, or 10%
Named polymer classes	Polyolprepolymer types 2, 14, and 15
Preferred polymer	Polyolprepolymer type 2

The polyurethane limitation is commercially important because ordinary polymers, carbomers, acrylates, silicones, or conventional emulsifiers do not automatically satisfy claims 9-12. A competitor using a different anti-irritant polymer may avoid the narrower claims, subject to the scope of independent claim 1 and equivalents analysis.

What formulations are protected?

Claims 13-20 cover multiple dosage-form and vehicle configurations. The patent reaches:

• Aqueous dispersions
• Aqueous-alcoholic dispersions
• Oily dispersions
• Lotions
• Aqueous gels
• Anhydrous or lipophilic gels
• Creams
• Cream-gels
• Pomades
• Emulsions
• Microemulsions
• Microcapsules
• Microparticles
• Ionic or nonionic vesicular dispersions

Claim 14 narrows the composition to a gel. Claims 15-17 cover creams, lotions, and cream-gels. Claim 18 gives a detailed aqueous-gel formulation. Claim 19 covers cream, lotion, and cream-gel compositions with a fatty phase and emollient. Claim 20 narrows the formulation to a lotion with approximately 0.1% naphthoic acid compound and 3% polyurethane.

Representative claim 18 formulation

The claimed gel may contain:

Component	Claimed amount
Naphthoic acid compound	0.1%-0.3%
Polyurethane polymer	1%-10%
Gelling agent	0.1%-3%
Chelating agent	0.01%-1.5%
Wetting agent	1%-10%
Preservative	0.01%-3%

Representative claim 20 lotion

The lotion may contain:

Component	Claimed amount
Naphthoic acid compound	About 0.1%
Polyurethane polymer	About 3%
Gelling or suspending agent	About 0.2%
Chelating agent	About 0.1%
Wetting agent	2%-6%
Emollient	0.1%-20%
Fatty phase	About 7%
Preservatives	1%-1.5%
Emulsifiers	4%-6%

The detailed formulation claims are valuable against products that reproduce a commercial formulation architecture. They are less useful against products that use the same active and anti-irritant concept but materially change excipient classes or concentrations.

What manufacturing steps are protected?

Claims 22-24 protect a process in which the naphthoic acid compound is mixed into a vehicle and remains undissolved. The process includes:

1. Combining the active with water, wetting agents, chelating agents, gelling agents, and optional emulsifiers or emollients.
2. Stirring until the active is fully dispersed in undissolved form.
3. Separately preparing a fatty phase when an emulsion is required.
4. Combining the fatty and aqueous phases.
5. Adjusting pH with a gelling-agent neutralizer.
6. Adding the polyurethane during the aqueous phase, fatty phase, or neutralization stage, depending on its hydrophilic or lipophilic character.
7. Heating selected phases to approximately 60 degrees Celsius.
8. Cooling, homogenizing, and packaging the final product.

Claim 24 provides a process sequence with particular operating conditions, including a target pH of 5.5 +/- 0.5 and staged heating. A generic manufacturer could infringe a process claim even if the final product is difficult to analyze, provided the patented process is used.

The process claims are most relevant in discovery involving batch records, master manufacturing instructions, formulation-development reports, and supplier specifications.

What medical uses are protected?

Claims 25-28 cover treatment methods for acne and related conditions. Claim 25 lists multiple acne subtypes, including:

• Common acne
• Comedonic acne
• Papulopustular acne
• Papulocomedonic acne
• Nodulocystic acne
• Acne conglobata
• Neonatal acne
• Occupational acne
• Senile acne
• Solar acne
• Medication-related acne

Claim 27 extends the claimed uses to:

• Acne-prone skin
• Greasy skin or hair
• Protection against harmful sunlight effects
• Physiologically greasy skin
• Light-induced aging
• Chronological aging

Claims 26 and 28 narrow the method to common acne and acne generally.

The treatment claims require administration of a composition satisfying claim 1. Use of adapalene alone does not meet the claim unless the administered formulation also contains the claimed polyurethane and undissolved active.

When does US Patent 8,709,392 lose exclusivity?

The patent issued on April 29, 2014. Its exact expiration date depends on the earliest effective nonprovisional filing date, any patent-term adjustment, terminal disclaimer, and applicable patent-term history. The issue date alone does not establish the expiration date.

The patent's remaining enforceability should be checked against:

• The USPTO Patent Center prosecution record.
• The patent face page for priority and term data.
• Any terminal disclaimer.
• Patent-term adjustment.
• Maintenance-fee status.
• Assignment and ownership records.

Patent-term rules generally provide a 20-year term measured from the earliest effective nonprovisional filing date, subject to statutory adjustments under 35 U.S.C. § 154. A priority filing date does not necessarily control the expiration calculation unless the relevant application chain makes it legally effective for term purposes (35 U.S.C. § 154; USPTO, n.d.-a).

What is the Orange Book status of US Patent 8,709,392?

The claims are drafted to cosmetic and dermatological compositions, processes, and treatment methods. The patent is not, by its claim language alone, an Orange Book-listed patent.

Orange Book listing depends on an approved new drug application and the sponsor's submission of patent information for that approved product. FDA listing is product-specific, not a general declaration that every claim covering an active ingredient is enforceable against every product (FDA, 2024).

The patent's adapalene relevance should therefore be separated from Orange Book status:

Issue	Assessment
Claims adapalene formulations	Yes
Claims adapalene as a molecule	No
Claims topical dosage forms	Yes
Claims a manufacturing process	Yes
Automatically Orange Book listed	No
Creates an automatic Paragraph IV basis	No
Could be relevant to an ANDA product	Yes, if the ANDA product practices the claims

For an ANDA, a Paragraph IV certification would be relevant only if the patent is listed for the reference product and the applicant certifies that the patent is invalid, unenforceable, or will not be infringed. A nonlisted patent can still create litigation risk, but it does not create the same statutory ANDA notice and 30-month-stay framework.

What Paragraph IV and generic-entry risks exist?

The principal generic-entry risks are formulation-specific rather than molecule-specific.

Higher-risk products

A generic or follow-on product presents higher risk if it has:

• Adapalene at 0.1% or 0.3%.
• Undissolved adapalene particles.
• Polyolprepolymer type 2, 14, or 15.
• Polyurethane at approximately 1%, 3%, 7%, or 10%.
• A gel, cream, lotion, or cream-gel vehicle.
• A formulation substantially matching the claimed excipient ranges.
• Manufacturing records showing the claimed dispersion and staged processing steps.

Lower-risk design pathways

Risk may be reduced by:

• Using a non-polyurethane anti-irritant.
• Eliminating the polyurethane entirely.
• Solubilizing the active, if stability and performance permit.
• Using a materially different dosage form.
• Changing the process so that the claimed sequence is not practiced.
• Using a different active concentration where the asserted claim requires a specified concentration.

These are not automatic noninfringement conclusions. Claim 1 is broader than claims 5-7 and 9-12, and doctrine-of-equivalents arguments could affect a design-around analysis.

How strong is the patent estate?

US 8,709,392 has moderate formulation-patent strength and weaker molecule-level exclusivity.

Estate characteristic	Strength
Active ingredient exclusivity	Low
Combination-formulation coverage	Moderate to high
Physical-state limitation	Moderate
Polyurethane-specific coverage	High for named polymers
Broad dosage-form coverage	Moderate
Process coverage	Moderate
Treatment-method coverage	Moderate
Generic substitution risk	Significant
Biosimilar risk	Not applicable

The patent is a small-molecule topical formulation patent, not a biologic patent. Biosimilar provisions under the Biologics Price Competition and Innovation Act do not apply. Competitive risk comes from generic topical products, OTC switches, alternative excipients, and noninfringing formulations rather than biosimilar development.

Which companies are likely to face the patent?

The commercial exposure is concentrated among companies marketing or developing topical adapalene products, including branded dermatology companies, generic pharmaceutical manufacturers, contract developers, and private-label topical manufacturers.

The highest-risk products would be adapalene gels, creams, lotions, or cream-gels that use the named polyolprepolymer materials. Products using adapalene without the claimed polyurethane architecture present a materially different risk profile.

No conclusion regarding a specific company's infringement or litigation position follows from the claims alone. That requires comparison of the accused product's complete composition, manufacturing process, labeling, and regulatory filing.

What licensing and litigation issues matter?

The claims indicate a formulation technology that could be licensed separately from adapalene molecule rights. A licensing diligence review should examine:

• Ownership and assignment history.
• Related continuation and divisional applications.
• Foreign counterparts.
• Terminal disclaimers.
• Maintenance-fee payments.
• Any license recorded with the USPTO.
• Litigation involving the patent or related family.
• Settlement agreements restricting generic launch.
• Product-specific patent listings.

The supplied claim set does not establish a licensing transaction, Paragraph IV settlement, consent judgment, or active infringement case. Those issues must be determined from USPTO, PACER, FDA, and assignment records rather than inferred from the claims.

How does this patent compare with core adapalene patents?

US 8,709,392 should be distinguished from patents claiming adapalene itself or broad therapeutic use of adapalene.

Patent category	Typical protection	Relevance of US 8,709,392
Compound patent	Adapalene molecule and analogs	Separate
Broad dermatological-use patent	Use of retinoid compounds	Separate
Combination patent	Adapalene plus another active	Usually separate
Formulation patent	Adapalene in a defined vehicle	Directly relevant
Process patent	Dispersion, emulsification, or manufacture	Directly relevant
Method-of-treatment patent	Acne or keratinization disorders	Directly relevant

The patent's value increases where the commercial product depends on polyurethane-mediated irritation reduction. It decreases where manufacturers can achieve acceptable tolerability using different polymers, surfactants, particle engineering, encapsulation, or vehicle systems.

Key Takeaways

• US 8,709,392 is a combination patent covering naphthoic acid compounds, principally adapalene, with polyurethane anti-irritants.
• The active must be dispersed in undissolved form under claim 1.
• Polyolprepolymer types 2, 14, and 15 receive specific protection, with type 2 preferred.
• Claims cover gels, creams, lotions, cream-gels, emulsions, microdispersions, and related topical vehicles.
• The patent includes composition, manufacturing-process, and acne-treatment claims.
• It does not claim adapalene alone and does not automatically block every adapalene generic.
• Orange Book listing cannot be inferred from the patent and depends on an approved-product listing.
• The principal design-around routes are a non-polyurethane anti-irritant, a materially different vehicle, or a dissolved rather than undissolved active.
• Biosimilar risk is irrelevant because adapalene is a small molecule.
• Exact expiration, maintenance status, family scope, licensing, and litigation require the patent's prosecution and public-record history.

FAQs

Does US 8,709,392 cover Differin gel?

It may be relevant to a Differin-type adapalene gel only if the product contains the claimed polyurethane and the adapalene is dispersed in undissolved form. The patent does not cover every adapalene gel automatically.

Can a generic avoid the patent by using carbomer instead of polyurethane?

A carbomer-only formulation may avoid the polyurethane limitation, but the full formulation and any process claim must be evaluated. The substitution is not a guaranteed noninfringement result.

Does the saw palmetto limitation narrow the patent significantly?

Yes. Claim 1 requires the composition to be devoid of saw palmetto berry extract. A composition containing that extract may fall outside the literal scope of claim 1, subject to the structure of the asserted claim and any separate related claims.

Are claims 25-28 treatment claims or product claims?

Claims 25-28 are method-of-treatment claims. They require administering a composition that meets the composition limitations incorporated from claim 1.

Is this a biologic patent subject to biosimilar litigation?

No. The patent concerns topical small-molecule naphthoic acid compounds, including adapalene. Generic-drug and formulation litigation frameworks are more relevant than biosimilar procedures.

References

Food and Drug Administration. (2024). Approved drug products with therapeutic equivalence evaluations. U.S. Department of Health and Human Services.

United States Patent and Trademark Office. (2014). U.S. Patent No. 8,709,392: Topically applicable compositions comprising a naphthoic acid compound and a polyurethane polymer. U.S. Department of Commerce.

United States Patent and Trademark Office. (n.d.-a). 35 U.S.C. § 154: Contents and term of patent; provisional rights. U.S. Department of Commerce.

United States Patent and Trademark Office. (n.d.-b). Manual of Patent Examining Procedure, Chapter 2700: Patent term. U.S. Department of Commerce.

Drugs Protected by US Patent 8,709,392

Applicant	Tradename	Generic Name	Dosage	NDA	Approval Date	TE	Type	RLD	RS	Patent No.	Patent Expiration	Product	Substance	Delist Req.	Patented / Exclusive Use	Submissiondate
Galderma Labs Lp	DIFFERIN	adapalene	LOTION;TOPICAL	022502-001	Mar 17, 2010		DISCN	Yes	No			Y			TREATMENT OF ACNE

International Family Members for US Patent 8,709,392

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
Argentina	057866
Australia	2006290364
Brazil	PI0617045
Canada	2622468
China	101262862