US Patent 5,869,082: Scope, Claims, Expiration, and Nitroglycerin Aerosol Patent Landscape

US Patent 5,869,082 protects a metered buccal aerosol containing nitroglycerin, a C3-C8 hydrocarbon propellant, and a non-polar solvent. Its core commercial concept is a nitroglycerin spray for delivery across the oral mucosa, particularly a formulation using butane or isobutane, Miglyol, flavoring, and a metered valve.

The patent issued on February 9, 1999. Its enforceable term has expired, eliminating current US patent exclusivity from the claims. The patent remains relevant as prior art and as a technical reference for nitroglycerin lingual sprays. It does not create a current barrier to an otherwise approvable generic product.

What does US Patent 5,869,082 protect?

The patent covers three related subject-matter categories:

A composition for buccal aerosol delivery of nitroglycerin.
A method of administering nitroglycerin by spraying the oral mucosa.
A sealed aerosol container with a metered valve containing the composition.

The central claim requires all of the following:

Nitroglycerin.
A pharmacologically acceptable non-polar solvent.
A C3-C8 linear or branched hydrocarbon propellant.
The specified concentration ranges.
Use as a buccal or transmucosal aerosol composition.

The broadest formulation ranges in claim 1 are:

Component	Claimed range by weight
C3-C8 hydrocarbon propellant	50%-95%
Non-polar solvent	5%-50%
Nitroglycerin	0.1%-6.5%

The claim is composition-focused. It does not broadly cover every nitroglycerin spray, every oral nitroglycerin product, or every metered aerosol. A competing product must satisfy the individual limitations of an asserted claim, either literally or under an applicable doctrine of equivalents.

How are claims 1 through 16 structured?

Claims 1 through 4: formulation ranges

Claim 1 is the independent composition claim. Claims 2 through 4 narrow the formulation by adding flavoring and tighter concentration ranges.

Claim	Principal limitation
1	Propellant 50%-95%, solvent 5%-50%, nitroglycerin 0.1%-6.5%
2	Claim 1 plus flavoring agent at 0.05%-5%
3	Propellant 55%-85%, solvent 15%-45%, nitroglycerin 0.2%-3.0%, flavoring 0.1%-2.5%
4	Propellant 60%-80%, solvent 19%-32%, nitroglycerin 0.3%-1.5%, flavoring 1%-2%

Claim 3 and claim 4 are nested species claims. A formulation within claim 4 will generally also fall within the broader concentration ranges of claim 3 and claim 1, assuming the other limitations are met.

Claims 5 through 7: propellant limitations

Claim 5 repeats the C3-C8 hydrocarbon limitation. Claim 6 identifies specific propellants:

Propane
N-butane
Isobutane
N-pentane
Isopentane
Neopentane
Mixtures of those compounds

Claim 7 adds chemical-quality specifications for n-butane or isobutane:

Water content no higher than 0.2%.
Oxidizing agents, reducing agents, Lewis acids, and Lewis bases below 0.1%.

These limitations are important in infringement analysis because they concern raw-material quality, not only the nominal identity of the propellant. A product using butane may fall outside claim 7 if its water or reactive-impurity profile exceeds the stated thresholds, although it could still fall within claim 1 or another claim.

Claims 8 and 9: solvent limitations

Claim 8 covers:

C7-C18 linear or branched hydrocarbons.
C2-C6 alkanoyl esters of C7-C18 carboxylic acids.
Triglycerides of C7-C18 carboxylic acids.

Claim 9 narrows the solvent to Miglyol. Miglyol is a commercial medium-chain triglyceride solvent, commonly associated with caprylic and capric acid triglycerides. The claim language creates a formulation-specific pathway for products using Miglyol or a materially equivalent solvent composition.

Claim 10: flavoring

Claim 10 depends on claim 2 and identifies:

Peppermint oil.
Spearmint oil.
Citrus oil.
Fruit flavors.
Sweeteners.
Combinations of those agents.

Flavoring is not required by claim 1. It becomes relevant to claims 2 through 4, 10, and the specific formulation claims 11 through 13.

Claims 11 through 13: specific formulations

Claims 11 through 13 cover three narrow compositions:

Claim	Propellant	Miglyol	Nitroglycerin	Flavoring
11	N-butane 67%	30.75%	1.25%	1.0%
12	Isobutane 67%	30.75%	1.25%	1.0%
13	Isobutane 33.75% plus n-butane 33.75%	31.19%	0.31%	1.0%

These claims are comparatively narrow because they recite exact percentages. Minor formulation changes may avoid literal infringement, but the legal effect depends on measurement tolerances, claim construction, product specifications, and the doctrine of equivalents.

Claims 14 and 15: method of administration

Claim 14 covers administering nitroglycerin to a mammal by spraying the oral mucosa with a composition of claim 1. Claim 15 requires that the amount sprayed be predetermined.

The method claims therefore connect the formulation to:

Oral-mucosal delivery.
Nitroglycerin treatment.
A defined or controlled spray amount.

A product could avoid a method claim only if the relevant administration method, composition, or predetermined-dose limitation is absent. Because method claims are directed to conduct, their practical enforcement analysis differs from the analysis for a composition or container claim.

Claim 16: container and metered valve

Claim 16 covers a sealed aerosol spray container containing a claim 1 composition and a metered valve capable of releasing a predetermined amount.

This claim reaches the combination of:

A sealed container.
The claimed formulation.
A metered dispensing valve.
Predetermined release of the composition.

The claim does not cover an unmetered pump or a formulation sold separately without the claimed container configuration unless the product still satisfies the claim limitations.

What formulations are protected by US Patent 5,869,082?

The patent’s strongest commercial coverage is directed to butane-based nitroglycerin aerosols using a non-polar triglyceride solvent.

A product is most closely aligned with the patent where it has:

N-butane, isobutane, or a mixture of the two.
Miglyol or a qualifying medium-chain triglyceride solvent.
Nitroglycerin in the claimed range.
A flavoring agent.
A metered aerosol valve.
Buccal or lingual administration.

The following formulation would fall within the principal concentration ranges:

Ingredient	Concentration
Isobutane	67%
Miglyol	30.75%
Nitroglycerin	1.25%
Flavoring	1.0%

It would also correspond closely to the subject matter of claim 12.

The patent does not require Miglyol in claim 1. A competing manufacturer could therefore face claim 1 risk even when using a different qualifying non-polar solvent, provided the solvent and concentration meet the claim language.

How strong is the patent estate for nitroglycerin buccal aerosol products?

The estate is technically focused but commercially narrow.

Strengths of the claims

Claim 1 covers broad concentration ranges.
The claims cover both composition and dispensing-container configurations.
The patent identifies common hydrocarbon propellants used in aerosol systems.
Miglyol and specific butane formulations are claimed directly.
The method claims connect the formulation to buccal administration.

Limitations of the claims

The claims require a non-polar solvent.
The propellant must be a C3-C8 hydrocarbon.
The claimed compositions are aerosol systems rather than all oral nitroglycerin products.
Exact formulation claims may be avoided through changes in composition.
The patent does not cover sublingual tablets, transdermal patches, ointments, conventional pumps, or non-aerosol sprays unless they independently satisfy the claim language.
The patent term has expired.

The estate therefore had meaningful product-specific value during its term but no current blocking force in the United States.

When did US Patent 5,869,082 lose exclusivity?

The patent was issued on February 9, 1999, and is identified as US Patent 5,869,082. Under the applicable 20-year patent-term framework, the patent expired no later than the relevant term date calculated from its US nonprovisional filing or applicable priority structure. Public patent records identify the patent as expired. Google Patents lists US 5,869,082 as expired, and the patent is no longer a live US exclusion right.[1]

The practical consequence is:

Issue	Current position
Composition claims	Expired
Method claims	Expired
Container claim	Expired
US patent exclusivity	None
Prior-art significance	Remains
Ability to support a new Paragraph IV challenge	None, because the patent is not a current Orange Book barrier
Freedom to practice	Not established solely by expiration; other patents and regulatory obligations may apply

Expiration does not eliminate other potential rights relating to a different formulation, device, manufacturing process, trademark, trade secret, or later patent.

What is the Orange Book status of the nitroglycerin aerosol product?

Nitroglycerin lingual spray products have been approved through the FDA new drug application framework. The reference product associated with Nitrolingual Pumpspray is an FDA-approved metered lingual aerosol delivering 0.4 mg nitroglycerin per spray. The FDA labeling describes administration by spraying onto or under the tongue and identifies the product as a metered spray.[2]

The Orange Book is the FDA’s primary source for approved drug products and listed patents. It does not treat every technical patent as an active Orange Book patent, and it does not itself determine infringement or validity.[3]

For current commercial analysis:

US Patent 5,869,082 is expired.
It should not be treated as a current Orange Book exclusivity barrier.
Any listed patent associated with a nitroglycerin spray NDA must be reviewed separately by NDA, patent number, expiration date, and use code.
FDA approval of a generic or follow-on product would still require satisfaction of the applicable ANDA or other regulatory pathway.

Are there Paragraph IV challenges to US Patent 5,869,082?

A current Paragraph IV challenge to US Patent 5,869,082 would have no practical purpose because the patent has expired. Paragraph IV certifications are relevant to unexpired listed patents that an ANDA applicant asserts are invalid, unenforceable, or not infringed.[4]

The relevant historical question is whether an ANDA applicant challenged the patent before expiration. Public patent and FDA records should be distinguished from litigation databases:

The patent’s expiration prevents a current injunction based on the patent.
Any historical Paragraph IV notice would be a past procedural event.
A Paragraph IV filing does not by itself establish invalidity or non-infringement.
Litigation involving a related NDA, formulation, or later patent would not automatically determine the status of this patent.

What patent litigation affects the patent?

No current enforceable dispute can arise solely from US Patent 5,869,082 because the patent has expired. The patent may still appear in historical litigation, patent-family records, prosecution records, or product development analyses.

The principal litigation questions would have been:

Whether the accused product contained a C3-C8 hydrocarbon propellant.
Whether the solvent was a claimed non-polar solvent.
Whether the concentration ranges were satisfied.
Whether the product was intended for buccal or transmucosal administration.
Whether a metered valve released a predetermined amount.
Whether the patent claims were valid over prior aerosol and nitroglycerin formulations.

The patent’s formulation claims would have required detailed product discovery, including confidential manufacturing specifications and analytical testing. Patent infringement cannot generally be established from the product name alone.

How does this patent compare with other nitroglycerin delivery technologies?

Technology	Delivery route	Relationship to US 5,869,082
Nitroglycerin lingual aerosol	Oral mucosa	Core technology covered by the patent
Sublingual tablet	Under the tongue	Outside the patent’s aerosol limitations
Transdermal patch	Skin	Outside the patent’s aerosol and buccal limitations
Topical ointment	Skin	Outside the patent’s aerosol limitations
Intravenous nitroglycerin	Injection	Outside the patent’s composition and delivery limitations
Non-hydrocarbon oral spray	Oral mucosa	May avoid the C3-C8 hydrocarbon limitation
Non-metered oral spray	Oral mucosa	May avoid claim 16, but composition and method claims require separate analysis

The patent’s technical differentiation was the use of a liquefied hydrocarbon aerosol propellant with a non-polar solvent to deliver nitroglycerin through the oral mucosa. The claims did not monopolize the pharmacological use of nitroglycerin itself.

What generic entry risks exist for a nitroglycerin spray?

The patent-specific risk is low because the patent is expired. Current entry risks are more likely to involve regulatory, formulation, device, manufacturing, and commercial issues.

Regulatory risks

An applicant may need to establish:

Bioequivalence or comparable drug delivery, depending on the FDA pathway.
Consistent nitroglycerin dose per actuation.
Container-closure integrity.
Valve performance over the labeled number of sprays.
Stability and impurity control.
Propellant and solvent safety.
Microbiological and chemical quality.
Labeling and directions for buccal or sublingual use.

Technical risks

Nitroglycerin is sensitive to formulation and packaging conditions. Key development issues include:

Uniformity of dose per spray.
Solubility and physical stability.
Adsorption or migration into container and valve components.
Propellant purity.
Water content.
Oxidizing or reducing impurities.
Leakage and pressure stability.
Flavor and patient acceptability.
Reproducibility of spray plume and droplet size.

The limitations in claim 7 show that propellant quality was a central technical concern. Even though the claim is expired, its specifications remain relevant to formulation development and quality-by-design analysis.

Commercial risks

Market access may be constrained by:

Existing brand recognition.
Limited demand relative to broader cardiovascular medicines.
Device and filling-line requirements.
Product liability exposure.
Distribution economics.
The need to maintain stable supply of suitable hydrocarbon propellant and valve components.

No reliable public source establishes standalone revenue attributable specifically to the patent or to a single nitroglycerin spray presentation. Product-level revenue should not be inferred from broader company disclosures.

What licensing deals or patent-family rights are relevant?

US Patent 5,869,082 should be reviewed as part of its international family and ownership history. The patent was associated with Pohl-Boskamp-type nitroglycerin aerosol technology and the Nitrolingual product platform. Assignment records, foreign counterparts, and regulatory ownership may differ by jurisdiction and time.

The expiration of the US patent does not automatically terminate:

Foreign patent rights that expired on different dates.
Trademark rights in names such as Nitrolingual.
Confidential manufacturing know-how.
Device supply agreements.
Product licenses.
Later patents covering a modified formulation, valve, container, or manufacturing process.

No current US license is required to practice the expired claims. A transaction involving the branded product or manufacturing technology would still require separate review of trademarks, regulatory rights, contracts, and non-patent intellectual property.

What is the geographic coverage of the patent?

US Patent 5,869,082 provided rights only in the United States. Its territorial scope did not extend automatically to Canada, Europe, Japan, or other markets.

A global freedom-to-operate review should distinguish:

US patent 5,869,082.
Foreign family members.
National-phase patents.
Continuations or divisionals.
Later patents covering device or formulation improvements.
Regulatory exclusivities in each market.

The US patent’s expiration has no direct legal effect on a still-active foreign counterpart.

Is there biosimilar risk for this product?

No. Nitroglycerin is a small-molecule active pharmaceutical ingredient, not a biologic. Biosimilar pathways under the Public Health Service Act are therefore not the relevant regulatory route.

The competitive issue is generic or follow-on entry through an applicable FDA small-molecule pathway, not biosimilar substitution. For a metered nitroglycerin aerosol, the principal questions are formulation equivalence, delivered dose, device performance, and regulatory comparability.

Key Takeaways

US Patent 5,869,082 covers nitroglycerin buccal aerosol compositions using C3-C8 hydrocarbon propellants and non-polar solvents.
The broadest claim requires propellant at 50%-95%, solvent at 5%-50%, and nitroglycerin at 0.1%-6.5%.
Dependent claims specifically cover butane, isobutane, Miglyol, flavoring agents, metered valves, and three defined formulations.
Claims 14 and 15 cover buccal administration and predetermined spray dosing.
Claim 16 covers a sealed container with a metered valve.
The patent is expired and does not impose current US patent exclusivity.
A current Paragraph IV challenge to this patent has no practical commercial purpose.
Nitroglycerin tablets, patches, ointments, injections, and non-aerosol products are outside the patent’s core claim structure.
Current entry barriers are more likely to involve FDA approval, device performance, formulation stability, manufacturing controls, trademarks, and later patent rights.
The patent remains relevant as prior art and as a technical reference for hydrocarbon-propelled nitroglycerin sprays.

Frequently Asked Questions

Does US Patent 5,869,082 cover Nitrolingual Pumpspray?

The patent claims technology closely aligned with a metered nitroglycerin lingual aerosol using hydrocarbon propellant and a non-polar solvent. Product-specific coverage depends on the marketed formulation, device configuration, and applicable claim limitations.

Can a generic use Miglyol in a nitroglycerin oral spray?

Yes, the patent’s expiration removes this patent as a current US barrier. A generic manufacturer must still evaluate other active patents, regulatory requirements, formulation safety, and device rights.

Does the patent cover nitroglycerin sublingual tablets?

No. The claims are directed to aerosol compositions, buccal spraying methods, and a sealed metered aerosol container. A tablet does not ordinarily satisfy those aerosol limitations.

Does patent expiration permit use of the exact formulation in claim 11?

The expired patent no longer prevents use of the claimed formulation in the United States. Other intellectual property, regulatory, contractual, or product-specific restrictions must be analyzed independently.

Are nitroglycerin spray products eligible for an ANDA?

Potentially. The appropriate FDA pathway depends on the reference product, dosage form, device characteristics, formulation, and FDA product-specific requirements. Patent expiration alone does not establish ANDA approval or bioequivalence.

References

Google Patents. (n.d.). US5869082A: Nitroglycerin-containing aerosol composition. https://patents.google.com/patent/US5869082A/en
U.S. Food and Drug Administration. (n.d.). Nitrolingual Pumpspray prescribing information. DailyMed. https://dailymed.nlm.nih.gov/
U.S. Food and Drug Administration. (n.d.). Approved drug products with therapeutic equivalence evaluations. Orange Book. https://www.accessdata.fda.gov/scripts/cder/ob/
U.S. Food and Drug Administration. (2024). ANDA submissions: Content and format of an abbreviated new drug application. https://www.fda.gov/drugs/guidance-compliance-regulatory-information/guidances-drugs

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
Austria	237322	⤷ Start Trial
Australia	1969397	⤷ Start Trial
Canada	2251564	⤷ Start Trial
>Country	>Patent Number	>Estimated Expiration	>Supplementary Protection Certificate	>SPC Country	>SPC Expiration

Details for Patent: 5,869,082

Summary for Patent: 5,869,082