US Patent 10,696,684: Oxycodone Free Base With Low-14-Hydroxycodeinone After HCl Conversion

What does the patent claim?

US Drug Patent 10,696,684 claims compositions of oxycodone free base combined with the minor impurity precursor 8α,14-dihydroxy-7,8-dihydrocodeinone, with a defined performance outcome when the mixture is treated with hydrochloric acid (HCl) to form oxycodone hydrochloride. The core claim limitation is control of the impurity “14-hydroxycodeinone” formed during conversion, expressed as ppm thresholds and, in some dependent claims, an HPLC ratio threshold for the precursor relative to product.

Claim 1 (independent) sets the mechanism and the key quality spec

Claim 1:

Composition: oxycodone free base + 8α,14-dihydroxy-7,8-dihydrocodeinone
Conversion step: react with HCl to form an oxycodone hydrochloride composition
Reaction conditions: conditions are “capable of converting” the 8α,14-dihydroxy-7,8-dihydrocodeinone to 14-hydroxycodeinone
Outcome limit: the amount of 14-hydroxycodeinone in the resulting oxycodone hydrochloride is < 100 ppm

This is a product-by-process-informed product spec: the pre-conversion mixture is defined, and the post-conversion impurity in the salt is the enforceable boundary.

Dependent impurity controls tighten the spec

Claim 2: 14-hydroxycodeinone < 25 ppm after conversion
Claim 3: 14-hydroxycodeinone < 10 ppm after conversion

Salt forms are expressly claimed

The patent includes acid addition salt compositions made from the low-conversion compositions:

Claims 4-6: salts made from the Claim 1 free base composition
- Claim 5: HCl salt
- Claim 6: sulfuric acid salt
Claims 7-9: salts made from the Claim 2 free base composition
- Claim 8: HCl salt
- Claim 9: sulfuric acid salt

HPLC ratio limits further narrow the precursor-to-product relationship

Claim 10 (independent quality metric): after reacting with HCl, the ratio of 8α,14-dihydroxy-7,8-dihydrocodeinone to oxycodone hydrochloride is 0.04% or less (HPLC)

Claims 11-17 mirror Claim 1 structure while adding alternate combinations of:

explicit ratio limits,
and inclusion of 14-hydroxycodeinone as a present component in the mixture (claims 12 and 17),
with the same impurity ceiling for 14-hydroxycodeinone.

Claim set mapping (what is covered vs what is not)

Claim group	What is defined	What must be controlled	Main enforceable metric
1 (independent)	oxycodone free base + 8α,14-dihydroxy-7,8-dihydrocodeinone	impurity formation after HCl conversion	14-hydroxycodeinone < 100 ppm in oxycodone HCl
2-3 (dependent)	same core composition	impurity formation after HCl conversion	<25 ppm and <10 ppm
4-9 (dependent)	acid addition salts from claim compositions	relies on the underlying free base spec	salt form + underlying conversion impurity compliance
10-11 (dependent)	same composition with additional HPLC constraint	precursor presence relative to product	8α,14-dihydroxy-7,8-dihydrocodeinone:oxycodone HCl ≤ 0.04%
12,17 (dependent)	compositions additionally containing 14-hydroxycodeinone	already-present impurity level (not only formed impurity)	14-hydroxycodeinone < 25 ppm
16 (dependent)	composition without explicit HCl outcome phrasing	HPLC ratio metric at ≤ 0.04%	8α,14-dihydroxy-7,8-dihydrocodeinone:oxycodone ≤ 0.04%

What is the scope of coverage in plain technical terms?

The claim scope centers on a tightly defined impurity-management problem:

Starting point: oxycodone free base is intentionally formulated (or at least commercially supplied) with the impurity precursor 8α,14-dihydroxy-7,8-dihydrocodeinone.
Conversion event: under reaction conditions “capable” of converting that precursor, the mixture is reacted with HCl to produce oxycodone hydrochloride.
Outcome: the product must contain very low levels of 14-hydroxycodeinone, expressed as ppm thresholds and/or ratios measured by HPLC.

The critical claim hook: “conditions capable of converting”

The phrase “under reaction conditions capable of converting” expands risk beyond scenarios where conversion is complete or measured in the claims as a fixed stoichiometry. It means that if the conversion conditions inherently allow formation, the claim is still evaluated based on the measured impurity in the resulting salt.

The critical enforceable measuring methods

14-hydroxycodeinone: measured in oxycodone hydrochloride composition by a ppm threshold (claims 1-3, 12, 17)
Precursor to product ratio: assessed by HPLC (claims 10, 11, 16)

What falls within scope vs outside scope?

Likely within scope (by literal reading)

Commercial or lab-prepared oxycodone free base compositions containing 8α,14-dihydroxy-7,8-dihydrocodeinone
Any conversion to oxycodone hydrochloride using HCl under conditions that can convert the precursor, where the resulting 14-hydroxycodeinone is below the claimed ppm ceilings
Salt conversion steps that create:
- oxycodone hydrochloride or sulfate (depending on which dependent claim is asserted)
Formulations where the precursor-to-product HPLC ratio is ≤ 0.04%

Likely outside scope (by literal reading)

Conversions using acids other than hydrochloric acid for claims that require the HCl conversion step (claims 1-3, 10-12, 16-17 require HCl in the conversion narrative)
Situations where the resulting 14-hydroxycodeinone exceeds <100 ppm, <25 ppm, or <10 ppm, depending on which claim target is asserted
If a product is prepared without including 8α,14-dihydroxy-7,8-dihydrocodeinone in the defined oxycodone free base composition, the literal composition limitation is not met (though indirect infringement theories could be argued in practice, the claims as provided are composition-based and conversion-outcome based)

How broad are the claims, and where are the sharp edges?

Breadth drivers

The independent claim (Claim 1) sets a relatively high impurity ceiling: <100 ppm.
The composition allows the precursor to be present; the differentiation is the impurity formation control after conversion.
Salt forms are included, so enforcement can extend to marketed salts if the underlying compliance is met.

Narrowing drivers

Dependent claims ladder down to <25 ppm and <10 ppm, creating a tiered landscape:
- A competitor could “design around” by aiming at thresholds above 25 ppm (to avoid claims 2-3) while still remaining at or below 100 ppm (to potentially avoid or invite claim 1 disputes depending on actual measured values).
Claim 10-style ratios (≤0.04%) can be a second design constraint:
- Even if ppm is controlled, failing the HPLC ratio could avoid some claim subsets.

Practical “design-around” pressure points

The enforceable pressure is not only “make oxycodone hydrochloride” but “make oxycodone hydrochloride with extremely low 14-hydroxycodeinone produced from a specific precursor.” That creates a process-quality barrier:

impurity control in input free base,
control over conversion conditions and/or impurity transformation kinetics,
validated analytical methods to demonstrate HPLC ratios and ppm impurity levels.

Patent landscape: what this claim set implies for competitive freedom to operate

Because you provided only the claim text (not the complete bibliographic record, prosecution history, related family members, expiration dates, or cited references), a full landscape map across the US portfolio cannot be completed from the supplied data alone. Still, the claim structure indicates how the patent is likely positioned in the market:

This patent targets a “salt conversion impurity formation” niche

The claims are drafted around a specific chemical transformation:

8α,14-dihydroxy-7,8-dihydrocodeinone → 14-hydroxycodeinone during HCl conversion to the salt.

This narrows the relevant competitive set to players that:

manufacture oxycodone free base with measurable levels of that precursor impurity, and
convert it to oxycodone hydrochloride in a way that produces detectable 14-hydroxycodeinone.

Two-layer infringement surface

Impurity outcome surface: meet ppm thresholds after HCl conversion
Analytical ratio surface: meet HPLC ratio ≤ 0.04% in certain claim versions

As a result, competitor risk is not only about chemistry. It also depends on:

product specs,
conversion validation,
and analytical reporting that aligns with the claim measurement framing.

Claim-by-claim scope checkpoints for FTO screening

Use the following checkpoints to assess whether a competitor’s product or manufacturing route is likely to land inside the literal claim boundaries you supplied:

Checkpoint A: Composition

Does the oxycodone free base composition include 8α,14-dihydroxy-7,8-dihydrocodeinone?

Checkpoint B: Conversion

Does the route involve reacting that composition with HCl to form oxycodone hydrochloride?

Checkpoint C: Conversion-capable conditions

Are the reaction conditions “capable of converting” the precursor into 14-hydroxycodeinone?

Checkpoint D: Outcome

What is the measured 14-hydroxycodeinone level in the resulting oxycodone hydrochloride?
- Compare to <100 ppm, <25 ppm, <10 ppm
For ratio claims: what is the HPLC ratio of
- precursor to oxycodone hydrochloride (≤0.04%), or
- precursor to oxycodone (≤0.04%) depending on the claim variant?

Checkpoint E: Salt identity

Is the commercial product the HCl salt or sulfate (matching claims 5-6, 8-9)?

Key Takeaways

US 10,696,684 claims oxycodone free base formulations containing 8α,14-dihydroxy-7,8-dihydrocodeinone where HCl conversion to oxycodone hydrochloride yields 14-hydroxycodeinone below defined ppm thresholds.
The enforcement lever is measurable: 14-hydroxycodeinone <100 ppm (Claim 1), tightened to <25 ppm (Claim 2) and <10 ppm (Claim 3), plus additional HPLC ratio limits (≤0.04%) in Claims 10, 11, and 16.
Salt scope covers oxycodone hydrochloride and sulfuric acid salts via dependent claim sets.
Competitive risk concentrates on manufacturers who cannot eliminate the precursor impurity in the free base yet must control the salt-conversion impurity outcome at extremely low levels.

FAQs

1) What is the single most important number in the claims?

100 ppm is the ceiling in the independent Claim 1 for 14-hydroxycodeinone in the resulting oxycodone hydrochloride (with narrower dependent claims at 25 ppm and 10 ppm).

2) Is hydrochloride formation required for all claims?

Not for every dependent salt claim, but the core asserted conversion mechanism in the claim set you provided explicitly uses HCl to form oxycodone hydrochloride for the impurity-outcome limitation (notably Claims 1-3 and ratio claims like Claim 10).

3) What does “conditions capable of converting” mean for infringement analysis?

It does not require that conversion be total; it focuses on whether the conditions used are capable of converting 8α,14-dihydroxy-7,8-dihydrocodeinone to 14-hydroxycodeinone, then infringement hinges on the measured 14-hydroxycodeinone level in the salt.

4) Does the patent require 14-hydroxycodeinone to be present before conversion?

No. Claim 1 and its main dependent set focus on the amount present in the oxycodone hydrochloride composition after conversion. Claims 12 and 17 additionally require compositions that further comprise 14-hydroxycodeinone with a ppm limit.

5) What analytic methods are explicitly called out?

The claims you provided explicitly require HPLC for the ratio metrics:

8α,14-dihydroxy-7,8-dihydrocodeinone to oxycodone hydrochloride ≤ 0.04% (Claims 10 and 11)
8α,14-dihydroxy-7,8-dihydrocodeinone to oxycodone ≤ 0.04% (Claim 16)

References

[1] US Drug Patent 10,696,684 (claims as provided in the prompt).

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
African Regional IP Organization (ARIPO)	2232	⤷ Start Trial
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Details for Patent: 10,696,684

Summary for Patent: 10,696,684