US Patent 8,044,046: Scope, Claims, Expiration, and Olodaterol Patent Landscape

US Patent 8,044,046 protects the use of five R-configured beta-2 adrenergic agonists for treating chronic obstructive pulmonary disease. Claim 1 covers olodaterol, the active ingredient in Striverdi Respimat and one component of Stiolto Respimat. The claims are method-of-treatment claims, not broad composition-of-matter claims. Their commercial value is concentrated in claim 1 because claims 2 through 5 recite closely related compounds that are not established FDA-approved products.

The patent issued on October 25, 2011. Public patent records associate it with Boehringer Ingelheim and report a September 24, 2023 expiration date, subject to any applicable patent-term adjustment or extension recorded in the official patent and Orange Book records. The patent does not create biologic exclusivity, and biosimilar law is not relevant because olodaterol is a chemically synthesized small molecule.

What does US Patent 8,044,046 cover?

US Patent 8,044,046 covers a method for treating COPD by administering one of five specifically identified R-configured benzo[1,4]oxazin-3-one derivatives, or an acid-addition salt, together with a pharmaceutically acceptable excipient or carrier.[1]

The patent does not claim:

Every beta-2 agonist used for COPD.
Every olodaterol formulation.
Every route of administering olodaterol.
The racemic form of the claimed compounds as such.
A broad genus defined by substituent variables.
A device-independent composition claim covering all products containing olodaterol.

The claims require the following elements:

A COPD treatment method.
Administration of a therapeutically effective amount.
One of five specified R-configured chemical entities or an acid-addition salt.
A pharmaceutically acceptable excipient or carrier.

The claims do not specify a dose, dosing interval, inhaler device, particle size, propellant, solvent, capsule, or particular disease severity.

What compounds are claimed by US 8,044,046?

The five claims recite individual chemical compounds rather than a Markush formula.

Claim	Principal substituent on the tert-butyl-like aryl group	Commercial relevance
1	4-Methoxyphenyl	Olodaterol
2	2,4-Difluorophenyl	No established FDA-approved product identified
3	3,5-Difluorophenyl	No established FDA-approved product identified
4	4-Ethoxyphenyl	No established FDA-approved product identified
5	4-Fluorophenyl	No established FDA-approved product identified

Claim 1 recites the compound generally known as olodaterol, marketed in the United States as olodaterol hydrochloride in the Respimat inhalation system.[2]

How does the R-configuration limit the claims?

The claims are stereochemically restricted. They require the R-configured compounds identified in the claim language. A product containing only the S-enantiomer would not literally satisfy the compound limitation. A racemate presents a more complex infringement question because it contains the R-enantiomer but is not necessarily the same claimed chemical entity.

The stereochemical limitation narrows literal claim scope but may increase the importance of:

Enantiomeric purity specifications.
Chiral separation methods.
Salt selection.
Analytical methods distinguishing the R- and S-enantiomers.
Manufacturing records showing the stereochemical composition of an active ingredient.

How strong are the claims in US Patent 8,044,046?

The claims have moderate scope and potentially strong product-specific enforcement value for olodaterol COPD products. Their principal strength comes from chemical specificity and the direct connection between the claimed use and the approved indication.

Strengths

The claims are relatively strong against a product that:

Contains olodaterol or olodaterol hydrochloride.
Is indicated or labeled for COPD.
Is administered with conventional pharmaceutical excipients or carriers.
Uses the R-configured compound in an inhaled product.

The claims also avoid dependence on a specific inhaler platform. A competing olodaterol COPD product could face method-claim exposure even if it used a different device, formulation vehicle, or dosing schedule.

Limitations

The claims are narrower than composition-of-matter claims. They may not reach:

A product containing olodaterol that is not used to treat COPD.
A product used solely for asthma if the COPD limitation is absent.
A manufacturing process that produces olodaterol.
A formulation containing olodaterol but lacking a COPD treatment use.
A device claim directed to the Respimat inhaler.
A competing product containing a structurally different beta-2 agonist.

The requirement for an excipient or carrier is also relevant. In an inhaled pharmaceutical product, this limitation is normally easy to satisfy because the product will ordinarily include a carrier, solvent, propellant substitute, or other formulation component. In practice, the COPD-use limitation is likely to be more important than the excipient limitation.

What is the FDA status of olodaterol?

The FDA approved olodaterol hydrochloride under NDA 203108 on July 31, 2014. The approved product is Striverdi Respimat, a long-acting beta-2 adrenergic agonist for the long-term, once-daily maintenance treatment of airflow obstruction in patients with COPD.[2]

Olodaterol is also combined with tiotropium in Stiolto Respimat, approved under a separate NDA. The combination product does not convert US 8,044,046 into a broad combination-product patent. The patent remains focused on the claimed olodaterol compounds and their use in COPD treatment.

FDA milestone	Date
NDA 203108 approval for Striverdi Respimat	July 31, 2014
Active ingredient	Olodaterol hydrochloride
Therapeutic class	Long-acting beta-2 adrenergic agonist
Primary indication	Maintenance treatment of COPD
Delivery system	Respimat inhalation spray

What is the Orange Book status of US 8,044,046?

US 8,044,046 was associated with olodaterol-related FDA regulatory protection and is the key patent relevant to the claimed COPD use of olodaterol. Orange Book status must be evaluated by product and NDA because the listing of a patent for Striverdi Respimat does not automatically establish the same listing for every olodaterol-containing product.[3]

The patent is a method-of-use patent. Under the Hatch-Waxman framework, a method-of-use patent can support a Paragraph IV certification if an ANDA applicant contests validity, enforceability, or infringement. A generic applicant may also attempt a section viii statement, omitting a patented indication, where the FDA-approved labeling and patent scope allow a non-infringing carve-out.[4]

Can a generic applicant use a section viii carve-out?

Potentially, but the result depends on the Orange Book-listed use code and the proposed labeling.

A section viii strategy is more viable when:

The generic label omits the patented COPD indication.
The product has a non-patented indication.
The patent does not cover the drug as a composition.
The proposed label does not encourage the patented use.

For olodaterol, the commercial product’s principal clinical purpose is COPD maintenance treatment. That fact can make a clean use-code carve-out difficult if the approved generic product would have no meaningful non-infringing indication.

When does olodaterol lose exclusivity?

Olodaterol had FDA five-year new chemical entity exclusivity beginning with the July 31, 2014 approval of Striverdi Respimat. NCE exclusivity generally prevented submission of an ANDA referencing the drug for four years and prevented approval for five years, absent a qualifying Paragraph IV challenge.[4]

The reported patent expiration date for US 8,044,046 is September 24, 2023. The relevant exclusivity timeline is:

Protection	Date or period
FDA approval of Striverdi Respimat	July 31, 2014
Four-year NCE ANDA submission restriction	Through July 30, 2018
Five-year NCE approval restriction	Through July 30, 2019
Reported US 8,044,046 expiration	September 24, 2023

Patent expiration and FDA regulatory exclusivity are separate. The 2023 patent date did not necessarily represent the end of every possible patent protecting an olodaterol product. Later patents may cover formulations, inhaler components, combinations, dosing regimens, or manufacturing processes.

What formulation patents protect olodaterol products?

US 8,044,046 does not claim a specific formulation. It requires a pharmaceutically acceptable excipient or carrier but does not define the carrier in detail.

Relevant formulation and product-development barriers for olodaterol inhalation products can include:

Aqueous inhalation solutions.
Concentration and pH ranges.
Preservative systems.
Osmolality and stability controls.
Container closure systems.
Metering and spray characteristics.
Cartridge and inhaler compatibility.
Device resistance and aerosol plume properties.
Combination formulations containing olodaterol and tiotropium.

These issues can create separate patent positions even after a method patent expires. They may also affect FDA approval independently of patent infringement. An ANDA applicant must demonstrate pharmaceutical equivalence and bioequivalence, or satisfy the applicable requirements for a complex inhalation product. Inhaled products can present greater development complexity than conventional oral generics because device performance and aerodynamic delivery may be material to approval.[5]

Does US 8,044,046 protect the Respimat device?

No. The claim language supplied is directed to treatment methods. It does not claim the Respimat inhaler, cartridge, nozzle, metering system, or device geometry.

A separate device or formulation patent could apply to the Respimat platform. Such patents would need to be assessed independently from US 8,044,046.

Are claims 2 through 5 commercially important?

Claims 2 through 5 expand the patent beyond olodaterol, but their commercial significance appears lower because the claims recite analogues rather than the FDA-approved olodaterol active ingredient.

Their strategic value is concentrated in:

Follow-on discovery programs.
Backup compound development.
Research-use restrictions.
Potential patent thickets around related beta-2 agonists.
Patentability support for stereochemically defined analogues.
Freedom-to-operate analysis for preclinical candidates.

A company developing one of these four analogues for COPD could face literal claim exposure if it administers the claimed R-configured compound with an excipient or carrier. A structurally related but non-identical compound would not literally infringe the compound limitation, although the doctrine of equivalents could become relevant depending on the differences and prosecution history.

Which companies are challenging olodaterol exclusivity?

The supplied patent and core FDA approval records do not identify a reported Paragraph IV challenger, settlement agreement, or license directed specifically to US 8,044,046.

The competitive challenge is more likely to arise through:

Generic olodaterol inhalation products.
Generic or authorized-generic Respimat-compatible products.
Combination products containing tiotropium and olodaterol.
Competing long-acting bronchodilators.
New inhaled products using different beta-2 agonists.

An ANDA applicant challenging the patent would face two principal routes:

Paragraph IV certification, asserting that the patent is invalid, unenforceable, or not infringed.
Section viii statement, omitting the patented COPD use if the labeling and use-code structure permit it.

A Paragraph IV notice could trigger a Hatch-Waxman infringement action and a statutory stay of FDA approval for up to 30 months, subject to the statutory exceptions and litigation outcome.[4]

What patent litigation affects US 8,044,046?

No reported final invalidity judgment or enforceability decision concerning US 8,044,046 is established by the sources cited here. The principal litigation risks are conventional for an Orange Book-listed method patent:

Lack of written description or enablement.
Obviousness based on earlier beta-2 agonist disclosures.
Failure to prove infringement of the COPD-use limitation.
Label-based inducement disputes.
Claim construction of “therapeutically effective amount.”
Claim construction of “acid addition salt.”
The effect of a section viii labeling carve-out.
Patent-term and Orange Book listing disputes.

The patent’s chemical specificity supports validity against broad prior-art attacks, but the COPD treatment concept and beta-2 agonist pharmacology could provide an obviousness target if prior art disclosed the same compounds or closely related compounds for respiratory disease.

How does olodaterol compare with competing COPD drugs?

Olodaterol competes with other long-acting bronchodilators, including long-acting beta-2 agonists, long-acting muscarinic antagonists, and fixed-dose combinations.

Product or class	Active ingredient	Main patent-risk profile
Striverdi Respimat	Olodaterol	Olodaterol use, formulation, device, and product patents
Stiolto Respimat	Olodaterol/tiotropium	Combination, formulation, device, and component patents
Spiriva	Tiotropium	Composition, formulation, device, and method patents
Arcapta Neohaler	Indacaterol	Composition, formulation, and inhaler patents
Anoro Ellipta	Umeclidinium/vilanterol	Combination and Ellipta device/formulation patents
Bevespi Aerosphere	Glycopyrrolate/formoterol	Combination, formulation, and Aerosphere device patents
Trelegy Ellipta	Fluticasone furoate/umeclidinium/vilanterol	Combination, formulation, and device patents

US 8,044,046 is narrower than a composition patent covering olodaterol itself. Its competitive importance depends on whether a generic can market olodaterol for a non-COPD use, carve out the patented indication, or prevail in Paragraph IV litigation.

What generic entry risks exist for olodaterol?

The principal generic-entry scenarios are:

Scenario 1: Launch after patent expiry

This is the lowest litigation-risk pathway if no later unexpired patent blocks approval or commercial launch. The applicant would still need to satisfy FDA requirements for the inhalation product and delivery device.

Scenario 2: Paragraph IV challenge

An applicant could challenge US 8,044,046 before expiration. The risk would include a district-court action, a potential 30-month stay, and exposure to damages or an injunction if the patent survived.

Scenario 3: Section viii carve-out

A carve-out could avoid infringement if the generic label omits the patented COPD use. The commercial value of this route is limited if COPD is the principal or only viable indication for olodaterol.

Scenario 4: Alternative formulation or device

A different formulation or inhaler may avoid separate formulation or device claims, but it would not necessarily avoid a method claim if the product still administers olodaterol for COPD.

Scenario 5: Combination-product entry

A generic tiotropium-olodaterol product could face a broader patent estate than a single-agent olodaterol product, including combination-specific claims and Respimat-related intellectual property.

What manufacturing and geographic IP barriers apply?

US 8,044,046 is directed to use in the United States. It does not, by itself, establish protection in Europe, Japan, China, or other jurisdictions. Geographic coverage must be assessed through the corresponding international and national patent family members.

Manufacturing risks may arise from separate patents covering:

Synthesis of the R-enantiomer.
Chiral resolution.
Intermediate compounds.
Salt formation.
Crystalline forms.
Inhalation-solution preparation.
Sterility and stability processes.
Cartridge filling.
Device assembly.

The patent’s claim language does not contain a manufacturing-process limitation. A manufacturer therefore cannot assume that a non-infringing synthesis avoids infringement if the resulting product is later administered in a claimed COPD treatment method.

Key Takeaways

US 8,044,046 is a COPD method-of-treatment patent.
Claim 1 covers olodaterol, marketed as Striverdi Respimat and used in Stiolto Respimat.
Claims 2 through 5 cover four related R-configured analogues with limited established commercial relevance.
The patent does not claim olodaterol as a composition, a specific inhaler, or a defined formulation.
The reported patent expiration date is September 24, 2023.
FDA NCE exclusivity for Striverdi Respimat began July 31, 2014 and generally ended in 2019.
A generic applicant could consider Paragraph IV or a section viii carve-out.
Biosimilar risk does not apply because olodaterol is a small-molecule drug.
Later formulation, device, combination, and manufacturing patents may create residual entry barriers after expiration of US 8,044,046.
The commercial importance of the patent is concentrated in claim 1.

FAQs About US Patent 8,044,046

Does US 8,044,046 cover olodaterol hydrochloride?

Yes. Claim 1 covers the olodaterol free compound and acid-addition salts, which include pharmaceutically acceptable salt forms such as olodaterol hydrochloride when used in the claimed COPD treatment.

Is US 8,044,046 a composition-of-matter patent?

No. The supplied claims are method claims. They require administration of a specified compound for COPD treatment with a pharmaceutically acceptable excipient or carrier.

Can a generic sell olodaterol after the patent expires?

Potentially. The applicant must still address any later unexpired patents, FDA requirements for the inhalation product, and intellectual property covering formulations, combinations, manufacturing, or the delivery device.

Does the patent cover asthma treatment?

The claims expressly recite COPD treatment. Use of the claimed compounds solely for asthma would not satisfy the express COPD limitation, although labeling, marketing conduct, and induced-infringement facts would control a particular case.

Are the four non-olodaterol compounds FDA-approved COPD drugs?

No established FDA-approved commercial COPD product corresponds to the four analogues recited in claims 2 through 5.

References

United States Patent No. 8,044,046, “Methods for the treatment of chronic obstructive pulmonary disease,” issued October 25, 2011. United States Patent and Trademark Office. https://patents.google.com/patent/US8044046
U.S. Food and Drug Administration. (2014). Striverdi Respimat (olodaterol hydrochloride) inhalation spray: Prescribing information. NDA 203108. https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf
U.S. Food and Drug Administration. (2024). Approved drug products with therapeutic equivalence evaluations: Orange Book. https://www.fda.gov/drugs/drug-approvals-and-databases/approved-drug-products-therapeutic-equivalence-evaluations-orange-book
Federal Food, Drug, and Cosmetic Act, 21 U.S.C. § 355(j), including Paragraph IV certification and section viii statement provisions.
U.S. Food and Drug Administration. (2020). Product-specific guidance for olodaterol hydrochloride inhalation spray. https://www.fda.gov/drugs/drug-development-guidance/product-specific-guidances-generic-drug-development

Foriegn Application Priority Data
Foreign Country	Foreign Patent Number	Foreign Patent Date
Germany	102 53 282	Nov 15, 2002

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
European Patent Office	1562603	⤷ Start Trial	C300650	Netherlands	⤷ Start Trial
European Patent Office	1562603	⤷ Start Trial	PA2014012	Lithuania	⤷ Start Trial
European Patent Office	1562603	⤷ Start Trial	92433	Luxembourg	⤷ Start Trial
European Patent Office	1562603	⤷ Start Trial	CR 2014 00014	Denmark	⤷ Start Trial
>Country	>Patent Number	>Estimated Expiration	>Supplementary Protection Certificate	>SPC Country	>SPC Expiration

Details for Patent: 8,044,046

Summary for Patent: 8,044,046