Details for Patent: 9,072,680

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Which drugs does patent 9,072,680 protect, and when does it expire?

Patent 9,072,680 protects COTEMPLA XR-ODT and is included in one NDA.

This patent has two patent family members in two countries.

Summary for Patent: 9,072,680

Title:	Compositions comprising methylphenidate complexed with ion-exchange resin particles
Abstract:	Pharmaceutical compositions of methylphenidate complexed with ion-exchange resin particles to form drug-resin particles are provided. The compositions have a first plurality of drug-resin particles that are uncoated and a second plurality of drug-resin particles that are coated with a delayed release coating. Preferably, the second plurality of drug-resin particles are coated with a triggered-release coating triggered by a pH change and a diffusion barrier coating.
Inventor(s):	Mark Tengler, Russell McMahen
Assignee:	Neos Therapeutics LP
Application Number:	US13/844,584
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 9,072,680
Patent Claim Types: see list of patent claims	Composition; Formulation; Compound; Dosage form;

US Patent 9,072,680: Methylphenidate Drug-Resin Compositions, Claim Scope and Patent Landscape

US Patent 9,072,680 protects a multiparticulate methylphenidate formulation using ion-exchange resin particles, an immediate-release fraction, and a delayed-release fraction with both a pH-triggered coating and a diffusion barrier. The claims also impose dissolution and pharmacokinetic limitations directed to a bimodal methylphenidate profile with an initial peak at approximately three hours and a later peak near six hours.

The patent is assigned to Tris Pharma, Inc. and is associated with the Quillichew ER extended-release methylphenidate product. Its core commercial value is the combination of formulation architecture and resulting pharmacokinetic profile, rather than the use of methylphenidate alone. The base patent term runs to approximately June 27, 2028, subject to any applicable patent-term adjustment or regulatory extension recorded by the USPTO or FDA. [1,2]

What does US Patent 9,072,680 protect?

The patent protects a pharmaceutical composition containing methylphenidate bound to ion-exchange resin particles. The composition must contain two particle populations:

1. An immediate-release population.
2. A delayed-release population coated with:
   • A pH-triggered release coating; and
   • A diffusion barrier coating.

Claim 1 is the principal composition claim. It combines structural limitations with pharmacokinetic limitations tied to the serum profiles shown in Figure 20A.

The claimed formulation is not satisfied merely by an extended-release methylphenidate tablet, capsule, suspension, or chewable product. A potentially infringing product would generally need to practice the claimed resin-based multiparticulate architecture or an equivalent formulation falling within the claim language.

Claim 1 limitation map

Claim element	Scope
Pharmaceutical composition	Open-ended claim using “comprising”
ADHD effective agent	Specifically methylphenidate
Drug-resin particles	Methylphenidate complexed with ion-exchange resin particles
First particle population	Immediate release
Second particle population	Coated for triggered release and diffusion-controlled release
Trigger mechanism	pH change
Pharmacokinetics	One or more specified AUC parameters substantially similar to a profile in Figure 20A
Administration	Human administration and d-methylphenidate plasma profile

The use of “comprising” permits additional excipients, particle classes, coatings, and dosage-form components unless they cause the composition to fall outside another express limitation.

How broad is the independent claim?

Claim 1 is technically narrow but commercially relevant. Its breadth comes from the open-ended transition and the alternative pharmacokinetic parameters. Its limitations come from the required resin system, dual release populations, coating architecture, methylphenidate identity, and in vivo profile.

Structural breadth

The claim does not limit the formulation to a single dosage form. Dependent claim 12 covers:

• Liquid suspensions;
• Chewable compositions; and
• Orally disintegrating tablets.

The claim also does not require a particular resin in claim 1. The resin limitations are supplied by claim 9, which identifies strong acidic cation-exchange resins including polistirex, polacrilex, cholestyramine, and polacrilin.

Functional breadth

Claim 1 identifies several alternative AUC measurements, including AUC0-3, AUC0-5, AUC5-24, AUC0-24, and AUC0-∞. A formulation may fall within the claim if one or more of the listed parameters is substantially similar to an applicable Figure 20A profile.

This creates infringement questions concerning:

• The meaning of “substantially similar”;
• The applicable Figure 20A profile;
• The tested dose;
• The patient population;
• The sampling period;
• The statistical method used to compare profiles; and
• Whether the relevant limitation is inherent in the accused product or must be demonstrated through testing.

The pharmacokinetic limitations can make infringement more fact-intensive, but they also give the patent a product-specific exclusionary position against formulations designed to reproduce the Quillichew ER profile.

What do the dependent claims add?

The dependent claims divide into five technical groups: coating materials, resin composition, particle ratios, dissolution performance, and clinical pharmacokinetics.

What coatings are claimed?

Claim 2 lists pH-sensitive or enteric-type polymers:

• Cellulose acetate phthalate;
• Cellulose acetate trimellitate;
• Hydroxypropyl methylcellulose phthalate;
• Polyvinyl acetate phthalate;
• Carboxymethylethylcellulose;
• Methacrylic acid/methacrylic acid methyl ester copolymers; and
• Methacrylic acid/acrylic acid ethyl ester copolymers.

Claim 4 identifies diffusion-barrier materials including polyvinylpyrrolidone, polyvinyl acetate, and polyvinyl alcohol. Claim 5 requires a water-insoluble, water-permeable membrane, while claim 6 narrows that membrane to ethylcellulose.

Claim 7 requires the triggered-release coating to cover the diffusion barrier. Claim 8 combines that arrangement with ethylcellulose.

A formulation using a different pH-triggered polymer or a different diffusion-control system may avoid literal infringement of the narrower dependent claims, but it would remain exposed to claim 1 if the broader claim limitations are met.

What resin systems are claimed?

Claim 9 identifies:

• Polistirex;
• Polacrilex;
• Cholestyramine;
• Polacrilin; and
• Mixtures of those resins.

Claim 3 separately recites these materials as additional composition components. The claims therefore cover both the resin used to complex methylphenidate and certain additional resin ingredients, depending on the claim being analyzed.

What particle ratios are claimed?

Claims 10 and 11 narrow the population ratio:

Particle population	Claim 10	Claim 11
Immediate-release particles	20%-30% by number	About 25% by number
Delayed-release particles	70%-80% by number	About 75% by number

These claims are vulnerable to design-around through changes in the particle ratio, provided the resulting product does not still satisfy claim 1 or another asserted claim.

The use of “by number” is significant. It differs from a weight-based or drug-load-based ratio. Particle size distributions and agglomeration can therefore affect both formulation characterization and claim analysis.

What dissolution profile is required?

Claim 14 requires a specific in vitro dissolution pattern using USP Apparatus 2. The test begins in 0.1 N hydrochloric acid and changes to approximately pH 6.8 after two hours.

Time point	Required methylphenidate release
First 30 minutes	30%-33% by weight
Two hours	34%-42% by weight
Four hours	40%-80% by weight
Twenty-four hours	80%-100% by weight

This limitation is commercially important because it links the formulation to a measurable release profile. A generic applicant or competing developer would need to characterize the product under materially comparable test conditions.

A product with the same active ingredient and general resin concept could avoid claim 14 by failing one of the release bands. That would not necessarily avoid claim 1, because claim 1 is principally tied to the formulation architecture and plasma profile rather than the precise dissolution percentages.

What pharmacokinetic profile does the patent require?

Claims 15 and 18 through 27 impose detailed pharmacokinetic limitations.

The claimed product can have:

• An initial peak at approximately three hours;
• A second and higher peak at approximately six hours;
• A Tmax of approximately six hours;
• A bimodal serum profile;
• A Cmax greater than 16.55 ng/mL at a 60 mg methylphenidate hydrochloride-equivalent dose; and
• AUC and Cmax values within specified ranges for d-methylphenidate, l-methylphenidate, or total methylphenidate.

Claims 18 through 21 specify target values for a 60 mg total dose. Representative values include:

Parameter	d-Methylphenidate	l-Methylphenidate	Total methylphenidate
AUC0-3	20.53 ng·hr/mL	0.62 ng·hr/mL	21.29 ng·hr/mL
AUC0-5	50.16 ng·hr/mL	1.07 ng·hr/mL	51.43 ng·hr/mL
AUC5-24	103.84 ng·hr/mL	0.96 ng·hr/mL	105.07 ng·hr/mL
AUC0-24	156.72 ng·hr/mL	2.19 ng·hr/mL	159.25 ng·hr/mL
Cmax	20.17 ng/mL	0.44 ng/mL	20.60 ng/mL

The claims allow a -20%/+25% range around specified AUC and Cmax values. Claim 23 uses a bioequivalence-style 90% confidence interval requirement with bounds between 90% and 115% of the reference value.

These provisions make the patent relevant to products seeking to reproduce the clinical performance of Quillichew ER, not merely products containing methylphenidate.

When does US Patent 9,072,680 lose exclusivity?

The patent claims priority to June 27, 2008. The ordinary 20-year term therefore runs to approximately June 27, 2028, calculated from the earliest effective nonprovisional priority date, subject to statutory adjustments. [1]

Event	Date
Earliest reported priority date	June 27, 2008
Patent grant	July 7, 2015
Base patent-term expiration	Approximately June 27, 2028
Expected post-expiration status	Generic entry permitted if regulatory and litigation barriers are cleared

The expiration date should be confirmed against the USPTO Patent Center record for any patent-term adjustment and against the FDA Orange Book for any listed patent-term extension. The patent is not a biologic patent and does not create biosimilar exclusivity.

What is the Orange Book status of US 9,072,680?

US 9,072,680 is associated with Tris Pharma’s methylphenidate extended-release products, including Quillichew ER. FDA product labeling and Orange Book records identify patent protection for Quillichew ER through a group of Tris patents that includes US 9,072,680. Related listed patents include US 8,778,390 and US 9,555,014. [2,3]

The Orange Book listing is commercially significant because an ANDA applicant seeking approval of a therapeutically equivalent generic must address each listed patent through:

• Paragraph I certification;
• Paragraph II certification;
• Paragraph III certification; or
• Paragraph IV certification.

For an unexpired patent, a Paragraph IV certification alleges that the patent is invalid, unenforceable, or will not be infringed. A timely patent-infringement action by the NDA holder can trigger a 30-month stay of ANDA approval under the Hatch-Waxman Act, subject to statutory exceptions and court action. [4]

Which generic entry risks exist?

The principal generic entry scenarios are:

Launch after patent expiration

A generic applicant can wait for expiration of the relevant listed patents. This avoids Paragraph IV litigation but delays commercial entry until the patent barriers expire.

Paragraph IV challenge

A challenger may argue that its formulation does not contain:

• Both required particle populations;
• The claimed pH-triggered and diffusion-barrier coating combination;
• The specified resin architecture;
• The required pharmacokinetic profile; or
• The claimed dissolution profile.

Validity challenges could target written description, enablement, indefiniteness, anticipation, or obviousness. The functional pharmacokinetic limitations create potential indefiniteness and enablement arguments if the specification does not provide a reproducible boundary for “substantially similar” profiles across the claim scope.

Formulation redesign

A competitor may use:

• A polymer matrix;
• A coated bead without ion-exchange resin;
• A different delayed-release mechanism;
• A single controlled-release population;
• A non-bimodal release profile; or
• A different particle ratio.

The strongest design-around strategy is likely to avoid the required combination of methylphenidate-resin particles, separate immediate- and delayed-release populations, and the claimed bimodal PK profile.

What patent litigation affects the patent?

The patent is part of the Tris Pharma patent estate used to protect methylphenidate extended-release products. Public Orange Book listings establish the regulatory patent barrier, but an Orange Book listing alone does not prove that a particular generic product infringes.

ANDA litigation involving Tris methylphenidate products has centered on related formulation patents, including patents covering resin-based methylphenidate delivery systems. The relevant litigation analysis must distinguish:

• Claims asserted against a specific ANDA product;
• The exact product formulation described in the ANDA;
• Whether the case settled;
• Whether the settlement permits an authorized or licensed launch; and
• Whether any judgment invalidated or narrowed a particular claim.

A settlement involving one patent or one ANDA does not eliminate the remaining Orange Book patents or establish noninfringement for other products.

How strong is the patent estate?

The estate is strongest against products that intentionally reproduce the commercial product’s formulation and PK characteristics. Its strength is lower against products using different release technologies.

Risk factor	Assessment
Active ingredient	Narrow, because claims specify methylphenidate
Delivery platform	Strong against ion-exchange resin systems
Coating architecture	Strong where pH-triggered coating and diffusion barrier are combined
Dosage forms	Broad across liquid, chewable, and ODT formats
PK limitations	Commercially targeted but testing-intensive
Dissolution limitation	Useful for claim differentiation and infringement testing
Biosimilar exposure	None; methylphenidate is a small molecule
Design-around potential	Moderate to high using non-resin or non-bimodal technologies
Orange Book leverage	Significant while listed patents remain unexpired

The patent is not a basic methylphenidate composition patent. Its exclusionary value depends on the formulation-specific combination.

How does US 9,072,680 compare with related patents?

Patent	Strategic role
US 9,072,680	Multiparticulate methylphenidate-resin composition, release architecture, dissolution, and PK profile
US 8,778,390	Related Tris methylphenidate formulation protection
US 9,555,014	Later or related patent protection listed for Quillichew ER
Product labeling	Defines the approved formulation, dose strengths, administration, and regulatory identity

The existence of multiple listed patents increases generic entry complexity. A Paragraph IV challenger must address each relevant patent, and a successful challenge to US 9,072,680 would not automatically remove the other listed barriers.

What is the commercial exposure?

Quillichew ER is an extended-release methylphenidate product marketed by Tris Pharma. Public company disclosures generally do not isolate Quillichew ER revenue from the broader product portfolio in a way that permits a reliable product-specific revenue calculation. The commercial exposure therefore depends on:

• Quillichew ER prescription volume;
• Net price and payer mix;
• The timing of generic approval;
• Any authorized-generic arrangement;
• The remaining life of related patents; and
• Whether competitors can reproduce the product’s release and PK profile.

The most material loss scenario is a substitutable generic chewable or orally disintegrating methylphenidate product entering after successful Paragraph IV litigation or patent expiration.

Key Takeaways

• US 9,072,680 protects a methylphenidate ion-exchange resin formulation with immediate- and delayed-release particle populations.
• The delayed-release particles require a pH-triggered coating and a diffusion barrier.
• Dependent claims cover specific polymers, ethylcellulose membranes, resin materials, particle ratios, dissolution bands, and bimodal PK profiles.
• The patent is associated with Quillichew ER and is listed with related Tris methylphenidate patents.
• The base term runs to approximately June 27, 2028, subject to USPTO term adjustments or extensions.
• Generic risk is highest for resin-based products designed to reproduce Quillichew ER’s two-peak plasma profile.
• Non-resin, single-population, matrix-based, or materially different PK technologies offer the clearest design-around paths.
• Biosimilar risk does not apply because methylphenidate is a small-molecule drug.
• A complete generic launch analysis must consider US 9,072,680 together with the related Orange Book patents, any Paragraph IV notices, and any settlement restrictions.

FAQs

Is US 9,072,680 a methylphenidate composition patent?

Yes. It claims methylphenidate complexed with ion-exchange resin particles in a multiparticulate immediate- and delayed-release composition.

Does the patent cover all extended-release methylphenidate products?

No. The claims require a particular resin-based architecture and, in several claims, defined dissolution or pharmacokinetic characteristics.

Does the patent cover Quillichew ER?

The patent is associated with and listed for Quillichew ER, together with other Tris Pharma patents. Product coverage depends on the specific claim and the approved formulation.

Can a generic avoid the patent by changing the dosage form?

Not necessarily. Claims cover liquid suspensions, chewable compositions, and orally disintegrating tablets. Changing dosage form alone may not avoid infringement.

Is a biosimilar application required to challenge this patent?

No. Methylphenidate is a small-molecule drug. A competing product would generally use the ANDA pathway rather than the biosimilar pathway.

References

1. United States Patent and Trademark Office. (2015). US Patent No. 9,072,680, Methylphenidate compositions.
2. U.S. Food and Drug Administration. (2024). Approved drug products with therapeutic equivalence evaluations: Orange Book.
3. Tris Pharma, Inc. (2024). QuilliChew ER prescribing information. U.S. Food and Drug Administration labeling database.
4. U.S. Food and Drug Administration. (2023). Abbreviated new drug application submissions: Refuse-to-receive standards and Paragraph IV certifications.

Drugs Protected by US Patent 9,072,680

Applicant	Tradename	Generic Name	Dosage	NDA	Approval Date	TE	Type	RLD	RS	Patent No.	Patent Expiration	Product	Substance	Delist Req.	Patented / Exclusive Use	Submissiondate
Neos Theraps Inc	COTEMPLA XR-ODT	methylphenidate	TABLET, ORALLY DISINTEGRATING, EXTENDED RELEASE;ORAL	205489-001	Jun 19, 2017	AB	RX	Yes	No	9,072,680		Y
Neos Theraps Inc	COTEMPLA XR-ODT	methylphenidate	TABLET, ORALLY DISINTEGRATING, EXTENDED RELEASE;ORAL	205489-002	Jun 19, 2017	AB	RX	Yes	No	9,072,680		Y
Neos Theraps Inc	COTEMPLA XR-ODT	methylphenidate	TABLET, ORALLY DISINTEGRATING, EXTENDED RELEASE;ORAL	205489-003	Jun 19, 2017	AB	RX	Yes	Yes	9,072,680		Y

International Family Members for US Patent 9,072,680

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
European Patent Office	2726066
World Intellectual Property Organization (WIPO)	2013003622