Details for Patent: 10,201,542

Which drugs does patent 10,201,542 protect, and when does it expire?

Patent 10,201,542 protects VIEKIRA PAK (COPACKAGED) and is included in one NDA.

This patent has sixteen patent family members in ten countries.

Summary for Patent: 10,201,542

Title:	Formulations of pyrimidinedione derivative compounds
Abstract:	The present disclosure relates to pharmaceutical compositions of pyrimidinedione derivative compounds and methods of preparing and uses thereof. The disclosure also relates to methods of enhancing bioavailability of pyrimidinedione derivative compounds in pharmaceutical compositions administered to a subject and methods of reducing the amount of a pyrimidinedione derivative compound in a pharmaceutical composition while achieving the same bioavailability in a subject.
Inventor(s):	Yanxia Li, Ping Gao, Yi Shi, Geoff G. Zhang, Yi Gao, Jianwei Wu
Assignee:	AbbVie Inc
Application Number:	US15/455,477
Patent Claim Types: see list of patent claims	Use; Composition; Dosage form;

Scope, claims, and US patent landscape for U.S. Patent 10,201,542 (Compound A + copovidone bioavailability-enhancing composition)

U.S. Patent 10,201,542 is a formulation-focused patent that claims a specific N-(6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide (“Compound A”, or a salt) combined with copovidone as a bioavailability-enhancing agent. The core claim set is constrained by (i) copovidone:Compound A weight ratios on a free-acid-equivalent basis, (ii) a minimum biphasic dissolution solubility threshold at 100 minutes, (iii) tablet/oral dosage constraints, and (iv) in certain dependent claims, in vivo exposure metrics (AUC24 and Cmax) and a specific precipitation inhibition test. Downstream enforceability risk is driven by whether competing products meet these numeric thresholds and whether their copovidone arrangement matches intragranular/inhibits-precipitation limitations.

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What does U.S. Patent 10,201,542 claim: compound, excipient, and numeric limitations?

Direct answer: The independent claim (Claim 1) protects a pharmaceutical composition containing Compound A (or pharmaceutically acceptable salt) plus copovidone at ≥5% by weight, with copovidone:Compound A ratio from about 4:1 to about 1:8 (free-acid equivalent basis), and with biphasic dissolution solubility of Compound A at least 20 mcg/mL at 100 minutes using a specified biphasic method profile.

Claim 1 core elements (factual “scope” checklist)

1. Active ingredient

   • Compound A: N-(6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide
   • Or pharmaceutically acceptable salt(s) of Compound A

2. Bioavailability-enhancing agent

   • Copovidone (the only named enhancer in Claim 1)

3. Quantitative thresholds

   • Copovidone is present at at least 5% by weight
   • Weight ratio on a free-acid equivalent basis:
     • copovidone : Compound A = ~4:1 to ~1:8

4. Performance/attribute limitation

   • Biphasic dissolution solubility of Compound A
   • At least 20 mcg/mL at 100 minutes (Claim 1)

5. Method context

   • “As measured by a biphasic dissolution test” (Claim 1)
   • Dependent claim supplies a specific test setup (Claim 5)

Claim 5: how the dissolution test is operationalized

Claim 5 narrows Claim 1’s dissolution test into a specific apparatus-like definition:

• 37 ± 0.2 °C
• Aqueous phase: 40 mL of 80 mM phosphate buffer
• Organic phase: 30 mL octanol This is important because generic/follow-on formulation work often shifts test conditions; infringement turns on meeting the same measured metric under the claimed test regime when that dependent claim is asserted.

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How broad is the ratio and copovidone % coverage across dependent claims?

Direct answer: Claim scope is broad in the independent claim but becomes narrow through dependent claims that carve out preferred numeric bands, dosage-mass bands, and exposure outcomes. A competitor can design around by shifting copovidone content, ratio, or dissolution solubility below the claimed thresholds, but each alternative design has to avoid the more specific dependent limitations if asserted.

Ratio bands explicitly claimed

• Claim 1: copovidone:Compound A from 4:1 to 1:8
• Claim 2: 1:1 to 1:4
• Claim 3: 1:2 to 1:3
• Claim 33: 1:1 to 1:3.5
• Claims 26–27: ratio 1:1 to 1:4 paired with specific tablet strengths

Copovidone content explicitly claimed

• Claim 1: copovidone ≥5% by weight
• Claim 13: copovidone 5% to 25% by weight
• Claim 14: copovidone 10% to 20% by weight

Practical implication for design-around

• If a follow-on tablet uses copovidone outside 5–25% or outside 10–20% (depending on which dependent claim is asserted), it can avoid dependent coverage while still potentially falling under Claim 1 if it remains ≥5% and ratio stays within Claim 1’s wide band.
• The ratio is on a free-acid equivalent weight basis, so salt selection and assay calculations are part of the legal boundary.

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What solubility/in vitro dissolution thresholds matter for infringement?

Direct answer: The patent uses a numeric biphasic dissolution solubility threshold (Claim 1: ≥20 mcg/mL at 100 min), and a dependent claim increases it (Claim 4: ≥30 mcg/mL). These thresholds are anchored to the biphasic dissolution test conditions in Claim 5 when that dependent claim is used.

Numeric dissolution claims

• Claim 1: solubility ≥ 20 mcg/mL at 100 minutes
• Claim 4: solubility ≥ 30 mcg/mL at 100 minutes
• Claim 5: test conditions (temperature, phases, volumes)

How this tends to play out legally

In enforcement against formulation products:

• Plaintiff will typically run the claimed biphasic dissolution test to demonstrate that the accused tablet reaches or exceeds the solubility thresholds.
• Defense often attacks assay/test replication (but here the claims define key parameters via Claim 5, reducing ambiguity).

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What solid-state and salt limitations are claimed for Compound A?

Direct answer: The claims escalate from “pharmaceutically acceptable salt” to a specific sodium salt and then a specific polymorph/solid-state “pattern B crystalline monosodium salt” and a monohydrate designation (Claims 6–9). That is a narrow carve-in that can be targeted by solids-focused design-around.

Salt coverage

• Claim 6: pharmaceutical composition comprises a salt of Compound A
• Claim 7: the salt is a sodium salt
• Claim 8: sodium salt is a pattern B crystalline monosodium salt
• Claim 9: pattern B monosodium salt is a monohydrate

Practical implication

• If a competitor uses a different salt form (e.g., potassium, calcium, or a different polymorphic form of sodium salt), it can reduce exposure to Claims 7–9.
• Claim 1 still includes “pharmaceutically acceptable salt,” so salts other than the claimed pattern B monohydrate may still fall under Claim 1 unless a court construes a narrower scope based on specification linkage (not provided here).

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What tablet weight and in vivo exposure metrics are claimed?

Direct answer: The patent includes multiple dependent claims restricting oral dosage form weight, tablet mass, and single-dose exposure metrics (AUC24 and Cmax). These are high-leverage limitations because they require demonstrating specific pharmacokinetic performance of the accused product in humans.

Tablet/oral dosage constraints

• Claim 16: oral dosage form
• Claim 17: oral dosage form weight < 1500 mg
• Claim 18: tablet
• Claim 19: tablet weight 500 mg to 900 mg
• Claim 10–12: amount of Compound A (free-acid equivalent) ranging:
  • Claim 10: 200 mg to 300 mg
  • Claim 11: about 250 mg
  • Claim 12: at least about 20% by weight

Specific dose bands for Compound A

• Claims 22–25: oral dosage form weight <1500 mg with Compound A content:

  • Claim 22: about 225–275 mg
  • Claim 23: about 240–260 mg
  • Claim 24: about 240–260 mg
  • Claim 25: about 245–255 mg

• Claims 26–27: same dose band (240–260 or 245–255) paired with ratio 1:1 to 1:4

Pharmacokinetic performance limitations

• Claim 20: average AUC24 ≥ 4500 ng·hr/mL
• Claim 21: average AUC24 ≥ 5000 ng·hr/mL and average Cmax < 1200 ng/mL

Practical implication for infringement analysis

• A product can practice the composition elements but still fall outside Claims 20–21 if its PK profile does not satisfy those numeric exposure constraints.
• A competitor seeking design-around often adjusts formulation to change Cmax and exposure dynamics even if dissolution solubility remains similar.

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What “precipitation inhibition” limitation is claimed, and why it matters?

Direct answer: Claim 15 adds a functional limitation: copovidone inhibits precipitation of Compound A, and defines a specific controlled test protocol for determining inhibition relative to a control without copovidone. This can be asserted as a composition quality attribute tied to the claimed enhancer.

Claim 15: precipitation inhibition method

The claim defines a process:

1. Prepare test solution with Compound A (or salt) + copovidone
2. Prepare control solution identical except no copovidone
3. Maintain both under same conditions for the test period
4. Determine extent of precipitation inhibition in test vs control at end of test

Infringement leverage

• If a defendant can show equivalent or greater precipitation in the presence of copovidone or uses a copovidone grade/process that does not inhibit precipitation under the protocol, it weakens Claim 15 coverage.
• But even if Claim 15 fails, Claim 1 may still succeed if Claim 1’s biphasic dissolution solubility threshold is met.

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How does the patent claim therapeutic use and method claims (hepatitis C)?

Direct answer: The patent contains method-of-use claims that administer the claimed composition for treating hepatitis C. Those method claims typically become a licensing and litigation focal point because they link formulation scope to clinical claims while staying dependent on composition infringement.

Method-of-use claims

• Claim 28: treating hepatitis C by administering the composition of Claim 1
• Claim 29: method further includes one or more additional therapeutic agents

Practical implication

• Even if a competitor uses the same composition but in a different therapeutic context, enforcement could face a use-specific evidentiary burden.
• If a competitor positions a product for hepatitis C, the method claims create direct infringement theories tied to actual prescribing/labeling and real-world administration.

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What manufacturing and formulation-process claims exist?

Direct answer: The patent includes a preparation method claim and functional manufacturing-related claims focused on blending and tabletability. These can expand leverage beyond final dosage form.

Preparation and functional manufacturing claims

• Claim 30: method of preparing composition by blending Compound A/salt and copovidone
• Claim 31: method enhancing bioavailability by preparing a composition according to Claim 1 and administering
• Claim 32: method improving tabletability where the tablet has improved tensile strength versus similar tablets not containing the bioavailability agent
• Claim 34: copovidone present as an intragranular component

Implication for process-based infringement

• If a defendant’s manufacturing uses different sequencing, granulation, or placement (e.g., extragranular coating vs intragranular), Claim 34 can be avoided.
• Tensile strength and “improved compared to similar tablet not containing copovidone” in Claim 32 create an evidentiary contest, but it is a valuable angle for plaintiffs during accused-product characterization.

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Who is likely covered by these claims: what product designs fall inside vs outside?

Direct answer: Coverage is strongest for oral tablets where Compound A is combined with copovidone at ≥5% and within the copovidone:Compound A ratio band, and where biphasic dissolution solubility meets ≥20 mcg/mL at 100 minutes. Coverage weakens if (i) solubility falls below threshold, (ii) copovidone content/ratio falls outside asserted bands, (iii) salt form is not within the claimed sodium pattern B monohydrate chain of dependent limitations, or (iv) PK metrics AUC24/Cmax do not match Claims 20–21.

Inside the claim estate (high-confidence “likely infringing” design pattern)

• Tablet containing Compound A (or acceptable salt)
• Copovidone present ≥5% w/w (often 10–20% in embodiments)
• Copovidone:Compound A ratio within 1:1 to 1:4 band if using stronger dependent coverage
• Biphasic dissolution solubility ≥20 mcg/mL (and ideally ≥30 mcg/mL)
• If pursuing dependent claim coverage: intragranular copovidone and precipitation inhibition demonstrated in the defined protocol

Outside or reduced-risk design patterns

• Reduce copovidone below 5% w/w
• Shift ratio outside asserted bands for dependent claims (but still within Claim 1 may remain risky)
• Use different salt form and avoid sodium pattern B monohydrate (Claims 7–9)
• Adjust formulation so biphasic dissolution solubility is <20 mcg/mL at 100 minutes
• Adjust PK profile so AUC24 <4500 or Cmax ≥1200 to avoid Claims 20–21

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What patent landscape issues arise around U.S. Patent 10,201,542: composition-of-matter vs formulation-and-performance?

Direct answer: The patent is not broad in the way “compound itself” patents are. It is a composition plus performance claim that uses a known-excipient concept (copovidone) paired with a specific poorly soluble active and specific dissolution/PK outcomes. The landscape consequence is that infringement fights often pivot to (i) whether the accused composition hits dissolution/PK thresholds and (ii) whether the excipient role is captured by the defined functional limitations (precipitation inhibition; intragranular placement).

Claim architecture that tends to narrow scope

• Composition claims are tightly tied to:
  • numeric dissolution solubility metric
  • numeric excipient ratio bands
  • salt selection (in dependent claims)
  • tablet weight bands (in dependent claims)
  • human PK exposure metrics (in dependent claims)
• Method claims largely track composition infringement:
  • treating hepatitis C is administered via the Claim 1 composition

Typical “design-around” pressure points

• Copovidone ratio and amount
• Dissolution test adherence (and achieving ≥20 or ≥30 mcg/mL)
• Salt form and hydrate/polymorph selection
• Intragranular placement and precipitation inhibition properties

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How many separate claim “buckets” exist in this patent, and which are likely to be asserted?

Direct answer: The claims group into at least five independent “buckets” that plaintiffs can mix and match:

1. Core composition (Claim 1 + ratio/copovidone %)
2. In vitro dissolution enhancements (Claims 4–5)
3. Salt form and crystalline specificity (Claims 6–9)
4. Tablet and human PK performance (Claims 10–12 and 17–21, 22–27)
5. Functional and process/formulation mechanics (Claims 15, 30–32, 34)

Assertion pattern likely in litigation

• Most enforcement starts with Claim 1 plus the dissolution test limitations (Claim 4/5).
• If the accused product is close on those, plaintiffs add dependent claims for stronger barriers:
  • PK outcome claims (20–21) if human data are available
  • intragranular copovidone (34) and precipitation inhibition (15) if formulation characterization supports it

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Which competing generic or follow-on risks exist for tablets with copovidone-based solubility enhancement?

Direct answer: Any follow-on hepatitis C tablet containing Compound A plus copovidone in ≥5% w/w and meeting the claimed biphasic dissolution metric is within the principal infringement zone. The risk increases if the product uses similar dosing (200–300 mg range; particularly 240–260 mg) and similar formulation architecture (intragranular copovidone).

Risk matrix for an accused product (conceptual, claim-driven)

• High risk if:
  • copovidone ≥5% and ratio within 4:1 to 1:8, and biphasic solubility ≥20 mcg/mL at 100 min
• Additional risk if:
  • solubility ≥30 mcg/mL and test conditions align with Claim 5
• Tier 3 risk if:
  • salt is sodium pattern B monohydrate and tablets match mass/dose bands
• Tier 4 risk if:
  • human PK matches AUC24 ≥4500 and Cmax <1200 and tablet mass/strength constraints align
• Cross-cutting risk if:
  • copovidone inhibits precipitation under Claim 15 protocol and is intragranular (Claim 34)

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What about US regulatory and Orange Book status: what can be inferred from the claim set?

Direct answer: The patent claims are consistent with a formulation enhancer and solid-state performance barrier that would typically appear in an Orange Book “patent” listing for a specific NDA/ANDA product tied to oral tablets. However, no Orange Book listing, NDA number, or listed patent reference for U.S. Patent 10,201,542 is provided in the input, so no definitive status or listed expiration timeline can be stated here.

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Key Takeaways

• U.S. Patent 10,201,542 protects a specific composition: Compound A (or pharmaceutically acceptable salt) + copovidone with ≥5% w/w copovidone and a copovidone:Compound A ratio from about 4:1 to 1:8.
• The composition’s enforceability hinges on biphasic dissolution solubility: ≥20 mcg/mL at 100 minutes (and ≥30 mcg/mL in a dependent claim), measured under defined biphasic conditions in Claim 5.
• The estate adds layered dependent barriers: specific sodium pattern B monohydrate salt (Claims 7–9), tablet dose/weight bands, and human PK constraints (AUC24 and Cmax) in Claims 20–21.
• Process/formulation characteristics expand scope via precipitation inhibition (Claim 15), tabletability via tensile strength (Claim 32), and intragranular copovidone (Claim 34).
• The method-of-use claims for hepatitis C (Claims 28–29) are tethered to administering the Claim 1 composition.

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FAQs

1. Does U.S. Patent 10,201,542 cover tablets without copovidone?
   No. Claim 1 and all identified dependent enhancer-related limitations are tied to copovidone as the bioavailability enhancing agent.

2. Can a product avoid infringement by using a different copovidone amount but keeping the same dissolution profile?
   It can avoid some dependent claims, but Claim 1 still requires ≥5% by weight and the claimed ratio range plus the dissolution solubility threshold.

3. Are the precipitation inhibition and intragranular placement limitations required to be met for Claim 1 infringement?
   No. Those are dependent, function/formulation-specific limitations tied to separate claims (Claim 15 and Claim 34).

4. Do the AUC24 and Cmax limitations apply to all asserted compositions?
   They are in dependent claims (Claims 20–21), so they apply only if those dependent claims are asserted and the accused product matches the prerequisite tablet composition/dose constraints.

5. What is the most direct design-around lever for this patent?
   The most direct is failing the claimed biphasic dissolution solubility threshold at the specified time and conditions, while also moving copovidone content/ratio outside target dependent bands.

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References

1. U.S. Patent 10,201,542, Claims 1–34 (provided in prompt).

Drugs Protected by US Patent 10,201,542

Applicant	Tradename	Generic Name	Dosage	NDA	Approval Date	TE	Type	RLD	RS	Patent No.	Patent Expiration	Product	Substance	Delist Req.	Patented / Exclusive Use	Submissiondate
Abbvie	VIEKIRA PAK (COPACKAGED)	dasabuvir sodium; ombitasvir, paritaprevir, ritonavir	TABLET;ORAL	206619-001	Dec 19, 2014		DISCN	Yes	No	10,201,542		Y			TREATMENT OF HCV INFECTION USING DASABUVIR

International Family Members for US Patent 10,201,542

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
Australia	2013330993
Brazil	112015008927
Canada	2888883
China	104853752