Last Updated: November 8, 2026

Details for Patent: 5,439,670

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Summary for Patent: 5,439,670
Title:Medicinal aerosol formulations
Abstract:A self-propelling aerosol formulation which may be free from CFC's which comprises a medicament, 1,1,1,2-tetrafluoroethane, a surface active agent and at least one compound having a higher polarity than 1,1,1,2-tetrafluoroethane.
Inventor(s):Tarlochan S. Purewal, David J. Greenleaf
Assignee: 3M Innovative Properties Co
Application Number:US08/086,820
Patent Claim Types:
see list of patent claims
Formulation; Compound;
Patent landscape, scope, and claims:

US Drug Patent 5,439,670: Claim Scope, Expiration, Litigation and HFA Inhaler Patent Landscape

U.S. Patent No. 5,439,670 covers hydrofluoroalkane-based aerosol formulations that use 1,1,1,2-tetrafluoroethane, commonly known as HFA-134a, with a surface-active agent and a more polar co-compound. The patent is directed primarily to metered-dose inhaler formulations replacing chlorofluorocarbon propellants.

The patent’s practical exclusivity has ended. Its principal commercial value was the formulation technology used during the transition from CFC-containing inhalers to HFA inhalers. It does not create a current blocking right against ordinary HFA-134a inhalers because the patent term expired in 2012, absent an unusual term adjustment or restoration.

What does US Patent 5,439,670 protect?

The patent protects pharmaceutical aerosol formulations containing four core elements:

  1. A medicament.
  2. HFA-134a as a propellant.
  3. A surface-active agent.
  4. A compound more polar than HFA-134a under the Kauri-butanol value test.

Claims 1 and 15 are the principal independent claims. Claim 29 is a separate independent formulation claim focused on isopropyl myristate.

Independent claim Core limitation Key distinction
Claim 1 Medicament, HFA-134a, surface-active agent, more-polar compound, and less than 5% of specified alternative propellants Permits limited quantities of CHClF2, CH2F2, CF3CH3, or mixtures
Claim 15 Medicament, HFA-134a, surface-active agent, more-polar compound, and no chlorofluorocarbons CFC-free formulation
Claim 29 Medicament, HFA-134a, surface-active agent, more-polar compound, isopropyl myristate, and less than 5% of specified alternative propellants Narrows the surfactant/co-compound package to isopropyl myristate

The claims use the term “comprising.” That is legally significant. A formulation can contain additional excipients, propellants, stabilizers, cosolvents, or processing aids and still fall within the literal scope if it contains all required claim elements.

When did US 5,439,670 expire?

The patent’s statutory term expired in approximately November 2012, based on the relevant early-1990s filing and priority chronology. No current enforceable patent term is generally associated with U.S. Patent 5,439,670.

Event Date or period
Earliest priority period 1991
U.S. patent issuance August 8, 1995
Patent term framework 20 years from the applicable nonprovisional or international filing date
Estimated U.S. expiration November 2012
Current status Expired
Patent-term extension relevance No identified extension that preserves current enforceability

The patent issued before the Uruguay Round Agreements Act changed the standard U.S. patent term to 20 years from the earliest effective filing date. Accordingly, the issuance date is not the controlling expiration benchmark. Patent term adjustment, if any, would have to be confirmed in the USPTO prosecution record. The ordinary commercial conclusion remains unchanged: the patent no longer blocks launch.

How are claims 1 through 14 structured?

Claims 1 through 14 form a dependent-claim chain built on claim 1.

Claim 1: broad formulation architecture

Claim 1 requires:

  • HFA-134a;
  • less than 5% by weight of one or more specified alternative propellants;
  • a surface-active agent;
  • a higher-polarity compound; and
  • a medicament.

The claim does not require inhalation, a particular dosage strength, a specific drug, a particular canister, or a particular valve. Those limitations appear in dependent claims.

The “higher polarity” requirement is defined functionally by Kauri-butanol value rather than by a single chemical class. This gives the claim a broader conceptual reach than a claim limited only to ethanol or propylene glycol, although the specification and prosecution history would control how the term is construed in litigation.

Claims 2 and 11: ingredient lists

Claim 2 identifies permissible higher-polarity compounds, including:

  • ethanol;
  • isopropanol;
  • propylene glycol;
  • light hydrocarbons;
  • legacy propellants;
  • dimethyl ether; and
  • other listed propellant compounds.

Claim 11 identifies a long list of surface-active agents, including:

  • sorbitan esters;
  • polysorbates;
  • lecithins;
  • polyoxyethylene/polyoxypropylene block copolymers;
  • oleic acid;
  • fatty alcohols;
  • polyethylene glycol 400;
  • isopropyl myristate; and
  • vegetable oils.

These lists are limiting for the specific dependent claims, but they do not necessarily limit claim 1 to those listed substances. A formulation may infringe claim 1 with a different qualifying compound if it satisfies the functional and compositional limitations.

Claims 3 through 5: route and physical state

Claim 3 limits the formulation to oral or nasal inhalation.

Claim 4 requires medicament particles with a median particle size below 10 microns. This limitation is relevant to suspension products in which micronized drug particles are dispersed in the propellant system.

Claim 5 covers drug in solution. The patent therefore reaches both major pMDI formulation architectures:

Formulation type Relevant claim concept
Suspension pMDI Micronized drug particles, generally under 10 microns
Solution pMDI Drug dissolved in HFA-134a/co-solvent system

The distinction matters because a solution product may avoid claim 4 but can still fall within claims 1, 3, 5, 6-14, or the corresponding claim 15 chain.

What formulation concentrations and ratios are claimed?

Claims 6 through 10 and 20 through 24 define quantitative HFA-134a and co-compound ranges.

Claim limitation Scope
HFA-134a concentration At least 50% by weight
Preferred HFA-134a concentration 60% to 95% by weight
HFA-134a:higher-polarity compound ratio 1:1 to 99:1
Narrower ratio 2.33:1 to 49:1
Narrowest stated ratio 5.67:1 to 19:1

The ratio claims are nested. A formulation with an HFA-134a-to-ethanol ratio of 10:1, for example, would fall within all three ratio ranges, assuming the other elements are present.

Claim 14 and claim 28 require medicament content of 0.01% to 5% by weight. That is a broad range covering many therapeutic aerosol products, although commercial products may be characterized by dose per actuation rather than total formulation weight.

Claim 12 and claim 26 require a surface-active-agent-to-medicament weight ratio of 1:100 to 10:1. This range is unusually broad and can cover formulations with very low surfactant loading as well as formulations in which surfactant is present at a substantial multiple of the drug weight.

Which drugs are expressly covered?

Claims 13 and 27 identify the following medicaments:

  • salbutamol, also known as albuterol;
  • beclomethasone dipropionate;
  • disodium cromoglycate;
  • pirbuterol;
  • isoprenaline;
  • adrenaline;
  • rimiterol; and
  • ipratropium bromide.

The express drug list is commercially important because it maps onto bronchodilator, corticosteroid, mast-cell stabilizer, and anticholinergic inhaler products. The list does not necessarily define the full scope of claim 1 or claim 15. Those independent claims recite “a medicament” without limiting the drug to the named compounds.

A competitor using a different active ingredient could still implicate the independent claims if the formulation satisfies the remaining limitations.

What is the scope of claim 15’s CFC-free limitation?

Claim 15 requires that the formulation be free of chlorofluorocarbons. It otherwise tracks claim 1:

  • medicament;
  • HFA-134a;
  • surface-active agent; and
  • a more-polar compound.

The claim is directed to the regulatory and technical shift away from CFC propellants under the Montreal Protocol and U.S. ozone-depletion controls. The phrase “free of chlorofluorocarbons” is narrower than a general “environmentally acceptable” limitation. HFA-134a itself is a hydrofluoroalkane, not a chlorofluorocarbon.

Claims 15 through 28 largely duplicate claims 1 through 14 while adding the CFC-free limitation. For claim-chart purposes, the patent can be analyzed as two parallel claim families:

  1. A formulation family allowing less than 5% of specified alternative propellants.
  2. A CFC-free family without that exact quantitative limitation.

What does claim 29 add?

Claim 29 requires isopropyl myristate. It is independently drafted and does not depend on claim 1 by reference.

Its required elements are:

  • a medicament;
  • HFA-134a;
  • a surface-active agent;
  • a higher-polarity compound;
  • isopropyl myristate; and
  • less than 5% of specified alternative propellants.

Because claim 29 uses “comprising,” isopropyl myristate must be present, but other surfactants or excipients may also be present. The claim may cover isopropyl myristate as a co-surfactant, dispersing aid, or formulation stabilizer, depending on the specification’s disclosure and the product composition.

A product containing ethanol, oleic acid, HFA-134a, and isopropyl myristate would be a close historical claim-chart candidate. The patent’s expiration eliminates current infringement exposure, but the formulation architecture remains relevant for prior-art and freedom-to-operate analysis involving later patents.

What patent landscape surrounded HFA-134a inhalers?

The patent landscape developed around four technical problems:

Technical problem Typical patent strategy
Replacing CFC-11 and CFC-12 HFA-134a or HFA-227ea propellant systems
Suspending micronized drug Surfactants, particle engineering, valve and canister compatibility
Dissolving drug in HFA Ethanol or other polar co-solvents
Delivering consistent dose Valve metering, actuator geometry, fill volume, and manufacturing controls

U.S. Patent 5,439,670 occupies the formulation-composition segment. It is less focused on:

  • actuator design;
  • metering-valve structure;
  • canister coatings;
  • manufacturing processes;
  • particle morphology;
  • dose-counter systems; or
  • device-specific aerosol plume control.

Those adjacent rights often determined commercial freedom to operate after the basic HFA formulation patents expired.

Representative competing formulation approaches

Approach Typical ingredients Patent risk profile
HFA-134a suspension HFA-134a, micronized drug, surfactant Historically closest to claims 1 and 15
HFA-134a solution HFA-134a, ethanol, dissolved drug Potentially within claims 5 and 19
HFA-134a with oleic acid HFA-134a, drug, oleic acid, co-solvent Potentially within listed surfactant claims
HFA-134a with isopropyl myristate HFA-134a, drug, IPM, polar compound Specifically relevant to claim 29
HFA-227ea systems HFA-227ea, drug, excipients May avoid claims requiring HFA-134a, but can implicate later patents
Dry-powder inhaler Drug powder and carrier, no propellant Outside the aerosol-composition claims

The critical claim boundary is HFA-134a. A formulation using only HFA-227ea and no HFA-134a would ordinarily fall outside these claims, subject to any equivalents analysis and the actual product composition.

What is the Orange Book status of US 5,439,670?

U.S. Patent 5,439,670 is not a current Orange Book exclusivity barrier. The Orange Book lists patents submitted by sponsors for approved drug products, but the presence or absence of a patent in the Orange Book does not determine whether a formulation patent is valid or enforceable in all circumstances. The patent has expired and therefore cannot support a current Paragraph IV blocking strategy.

The relevant regulatory pathways for products using the claimed formulation technology are:

Product type Likely FDA pathway
Generic albuterol or other small-molecule pMDI ANDA under section 505(j)
Reformulated inhaler or new dosage form 505(b)(2) application
New active ingredient NDA
Biosimilar Not applicable

A biosimilar analysis is not relevant because the claimed products contain conventional small-molecule drugs, not biologic active ingredients. Regulatory competition would proceed through ANDA or 505(b)(2) pathways rather than the biosimilar pathway.

Which companies were exposed to the patent’s formulation scope?

The patent’s technical scope was relevant to companies commercializing CFC-transition inhalers, including major respiratory-product manufacturers such as:

  • GlaxoSmithKline;
  • 3M Pharmaceuticals;
  • AstraZeneca;
  • Boehringer Ingelheim;
  • Schering-Plough;
  • Teva;
  • Cipla; and
  • other manufacturers developing HFA-based metered-dose inhalers.

The patent itself does not establish that each company infringed, licensed, challenged, or settled the patent. Product-level analysis requires the formulation composition, manufacturing date, and relevant patent-family records.

Commercial products such as albuterol HFA, beclomethasone HFA, fluticasone HFA, and combination inhalers illustrate the broader market transition, but product inclusion alone does not prove coverage by U.S. Patent 5,439,670.

Were there Paragraph IV challenges or litigation?

No current Paragraph IV risk exists for U.S. Patent 5,439,670 because the patent has expired.

A historical Paragraph IV challenge would have required an ANDA applicant to certify that the patent was invalid, unenforceable, or not infringed. The statutory framework is under the Hatch-Waxman Act, 21 U.S.C. § 355(j)(2)(A)(vii)(IV). Because the patent is no longer enforceable, a later ANDA applicant would not need to use the patent as a launch-blocking litigation target.

No widely reported, currently operative settlement agreement, injunction, or exclusion order is associated with this patent. Patent-specific litigation should be checked against PACER and USPTO Patent Center records rather than inferred from litigation involving later HFA inhaler patents.

How strong was the patent estate?

Historical strength

The patent had meaningful historical value because it claimed a broad formulation combination at a time when the industry was replacing CFC propellants. Its strengths included:

  • two broad independent claim families;
  • coverage of both suspension and solution formulations;
  • broad “comprising” language;
  • numerous listed co-solvents and surfactants;
  • quantitative concentration and ratio claims; and
  • express coverage of major respiratory drugs.

Weaknesses

The main vulnerabilities were:

  • dependence on the measurable presence of HFA-134a;
  • dependence on a higher-polarity compound;
  • potential indefiniteness or construction disputes concerning Kauri-butanol value;
  • extensive prior art in aerosol formulations;
  • possible design-around using a different propellant;
  • possible use of alternative surfactants or drug-delivery formats; and
  • limited relevance to device, valve, actuator, and manufacturing patents.

The patent’s current strength is zero as an exclusionary right because it is expired. Its residual value is evidentiary: it may be cited as prior art against later claims directed to similar HFA-134a, ethanol, surfactant, or isopropyl-myristate formulations.

What generic launch scenarios exist?

Current launch scenarios are not constrained by this patent. A generic or follow-on manufacturer can generally pursue:

  1. An HFA-134a suspension inhaler with a micronized active ingredient.
  2. An HFA-134a solution inhaler using ethanol.
  3. A different HFA propellant system.
  4. A reformulated product under 505(b)(2).
  5. A device-and-formulation combination with separate patent analysis.

The remaining commercial barriers are more likely to involve:

  • FDA sameness and performance requirements;
  • aerodynamic particle-size distribution;
  • delivered-dose uniformity;
  • extractables and leachables;
  • valve and actuator compatibility;
  • container-closure integrity;
  • manufacturing reproducibility;
  • device patents;
  • formulation patents filed after 1995; and
  • regulatory exclusivity tied to a particular reference product.

Does the patent create manufacturing or geographic barriers?

No current geographic barrier exists in the United States from U.S. Patent 5,439,670. A U.S. patent has no direct exclusionary effect in Europe, Canada, Japan, China, or other jurisdictions.

International risk would depend on counterpart patents in the same family and their individual expiration dates. The formulation technology may also have been protected by national counterparts, continuation applications, or related patents directed to specific drugs, devices, or manufacturing methods.

Manufacturing processes can remain protected separately even after a composition patent expires. Relevant process questions include:

  • whether the drug is micronized before filling;
  • whether the formulation is filled by cold-fill or pressure-fill methods;
  • whether ethanol is introduced through a concentrate;
  • whether the valve is crimped under controlled pressure;
  • whether the canister has a polymer coating; and
  • whether the formulation uses a proprietary suspension-stabilization process.

Those issues are outside the literal composition scope of the claims supplied.

Key Takeaways

  • U.S. Patent 5,439,670 covers HFA-134a aerosol formulations containing a medicament, surfactant, and more-polar compound.
  • Claims 1 and 15 are the central independent claim families.
  • Claims 3 through 14 and 17 through 28 narrow the formulation by route, particle size, solution state, concentration, ratio, surfactant, drug, and drug loading.
  • Claim 29 separately targets formulations containing isopropyl myristate.
  • The patent’s term expired in approximately November 2012.
  • It is not a current Orange Book or Paragraph IV launch barrier.
  • Biosimilar risk is irrelevant because the patent covers small-molecule inhaler formulations.
  • Current freedom-to-operate risk is more likely to arise from later formulation, device, valve, actuator, manufacturing, or combination-product patents.
  • HFA-227ea, dry-powder inhalers, alternative co-solvents, and device redesigns provide potential historical design-around paths.
  • The patent remains relevant as prior art and as a technical marker in the CFC-to-HFA inhaler transition.

Frequently Asked Questions

Can an HFA-134a inhaler still infringe US 5,439,670?

The patent is expired, so an HFA-134a inhaler cannot generate current liability under that patent. The formulation may still be relevant to later, unexpired patents.

Does ethanol in an inhaler automatically trigger US 5,439,670?

No. Ethanol is one listed higher-polarity compound, but all required elements, including HFA-134a, a medicament, and a surface-active agent, must be present for literal coverage.

Is isopropyl myristate required for all claims?

No. Isopropyl myristate is specifically required by claim 29 and is listed as a surfactant in claim 11 and claim 25. It is not required by independent claims 1 or 15.

Are dry-powder inhalers covered by this patent?

Ordinary dry-powder inhalers do not contain the claimed HFA-134a propellant system and therefore fall outside the literal aerosol-composition claims.

Can later patents still block an HFA inhaler after this patent expired?

Yes. Later patents may cover a specific drug formulation, device, valve, actuator, canister coating, dose counter, manufacturing process, or combination product even though U.S. Patent 5,439,670 has expired.

References

  1. U.S. Patent No. 5,439,670, “Pharmaceutical formulations,” issued August 8, 1995, U.S. Patent and Trademark Office. Google Patents. https://patents.google.com/patent/US5439670A/en

  2. U.S. Food and Drug Administration. (2024). Approved drug products with therapeutic equivalence evaluations. https://www.fda.gov/drugs/drug-approvals-and-databases/orange-book-data-files

  3. U.S. Food and Drug Administration. (2023). Abbreviated new drug application submissions: Refuse-to-receive standards. https://www.fda.gov/drugs/guidance-compliance-regulatory-information

  4. U.S. Code, 21 U.S.C. § 355. New drugs and abbreviated applications.

  5. U.S. Patent and Trademark Office. (2024). Patent term calculator. https://www.uspto.gov/patents/laws/patent-term-calculator

  6. United Nations Environment Programme. (1987). Montreal Protocol on substances that deplete the ozone layer. https://ozone.unep.org/treaties/montreal-protocol <|endoftext|>

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Drugs Protected by US Patent 5,439,670

Applicant Tradename Generic Name Dosage NDA Approval Date TE Type RLD RS Patent No. Patent Expiration Product Substance Delist Req. Patented / Exclusive Use Submissiondate
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