US Patent 5,482,934: Ciclesonide Claims, Patent Scope, Expiration, and Generic Risk

US Patent 5,482,934 covers a class of stereochemically defined corticosteroid acetal compounds, including ciclesonide and related fluorinated analogues. Its principal protection reaches the active compound, the 22-position stereoisomers, pharmaceutical compositions, anti-inflammatory uses, topical administration, and selected hydrogenated or fluorinated substituent variants. The patent issued on January 9, 1996, and its original 17-year US patent term ended on January 9, 2013, absent a separately listed extension. The patent is therefore no longer a live US barrier to an ANDA or 505(b)(2) product. [1][2]

What drug does US Patent 5,482,934 protect?

The patent is associated with ciclesonide, an inhaled corticosteroid marketed in the United States as Alvesco. The compound identified in claim 8 is the ciclesonide active ingredient:

[11β,16α(R,S)]-16,17-[cyclohexylmethylene)bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)pregna-1,4-diene-3,20-dione.

Ciclesonide is a nonhalogenated corticosteroid prodrug. It contains:

A pregnadiene corticosteroid nucleus.
A 16α,17-acetal formed with a cyclohexylmethylene group.
An 11β-hydroxyl group.
A 21-isobutyrate ester.
A stereogenic acetal carbon at position 22.
R and S forms, as well as mixtures of those forms.

The marketed drug is generally described as ciclesonide, including the stereochemical mixture covered by claim 8. Ciclesonide is converted in the lung to desisobutyryl ciclesonide, the pharmacologically active metabolite. [3]

What are the core claims of US 5,482,934?

The claims divide into four categories: chemical compounds, stereochemical species, pharmaceutical compositions, and therapeutic methods.

Claim group	Claims	Subject matter
Broad compound genus	1	Formula-defined corticosteroids with cyclohexyl at R1 and specified R2 substituents
22S stereoisomer	2	The (22S)-epimer of claim 1
22R stereoisomer	3	The (22R)-epimer of claim 1
Anti-inflammatory drug	4	A drug containing a claim 1 compound
Treatment method	5	Administering an effective anti-inflammatory amount
Pharmaceutical composition	6	Active compound plus a pharmaceutically acceptable carrier
Topical treatment	7	Topical administration for inflammatory conditions
Ciclesonide species	8	The R/S ciclesonide compound identified by its chemical name
Ciclesonide R epimer	9	R-epimer of claim 8
Ciclesonide S epimer	10	S-epimer of claim 8
Hydrogenated substituent variant	11	Claim 1 where X1 and X2 are hydrogen
Fluorinated substituent variant	12	Claim 1 where X1 and X2 are fluorine

Claim 1 is the principal genus claim. Claims 2 and 3 separately protect each configuration at the position-22 stereocenter. Claim 8 narrows the genus to the ciclesonide structure. Claims 9 and 10 separately identify the two ciclesonide epimers.

How broad is claim 1?

Claim 1 has both structural and stereochemical limitations.

The compound must have:

The formula shown in the patent.
A cyclohexyl R1 substituent.
One of the listed R2 groups.
Hydrogen or fluorine at X1 and X2, subject to the alternatives shown in the patent formula.
Either the R epimer, the S epimer, or a mixture at the carbon designated position 22.

The claim is broader than ciclesonide because it covers a genus of related steroidal compounds. It is narrower than a claim directed to all corticosteroid acetals because it requires the specified cyclohexyl group, R2 alternatives, and X1/X2 definitions.

The formula graphics are legally material. The text supplied for claims 1 and 11 omits the chemical structures represented by the image placeholders. Those omitted structures determine the exact R2 scope and prevent a reliable reconstruction of every genus member from the text alone. The explicit ciclesonide claims, however, can be analyzed from the chemical name supplied in claim 8.

What stereochemistry does the patent cover?

The patent directly covers both configurations at position 22.

Claim 2: 22S epimer

Claim 2 narrows claim 1 to the (22S) configuration. A product containing only that stereoisomer would fall within claim 2 if it also meets the structural limitations of claim 1.

Claim 3: 22R epimer

Claim 3 covers the corresponding (22R) configuration.

Claim 1 and stereoisomeric mixtures

Claim 1 expressly covers:

The R epimer.
The S epimer.
A stereoisomeric mixture of the R and S epimers.

That wording is commercially significant. A product does not avoid the compound claim merely because it contains both epimers. A racemic or non-resolved mixture can remain within the literal scope of claim 1.

Claims 9 and 10 apply the same approach specifically to the ciclesonide structure identified in claim 8.

What formulations are protected by US Patent 5,482,934?

Claim 6 protects a pharmaceutical composition containing an effective amount of a claim 1 compound with a pharmaceutically acceptable carrier. The claim does not require a specific dosage form, device, propellant, excipient, concentration, or route.

Potentially covered dosage forms include:

Inhalation products.
Topical preparations.
Nasal formulations.
Dermatological preparations.
Oral or parenteral compositions, if otherwise pharmaceutically appropriate.

Claim 4 is framed as an anti-inflammatory drug containing the compound. Claim 6 is a conventional composition claim. Claim 7 separately requires topical administration.

The patent does not, based on the supplied claims, require:

A metered-dose inhaler.
A specific hydrofluoroalkane propellant.
A particular particle-size distribution.
A specific suspension or solution formulation.
A specific inhaler actuator.
A defined ciclesonide concentration.
A particular dosing schedule.

Those limitations may appear in the specification or in other patent families, but they are not present in the supplied claims.

What method-of-use claims does the patent contain?

Claims 5 and 7 are method claims.

Claim 5 covers administering an anti-inflammatory effective amount to treat inflammatory conditions. Claim 7 is narrower because it requires topical administration.

The claims are not limited to asthma or allergic rhinitis. On their face, they cover inflammatory conditions generally, subject to the compound and effective-dose limitations. The specification and prosecution history would be relevant to determining whether the phrase "inflammatory conditions" received a narrower construction.

For ciclesonide products, the commercial respiratory indications are more specific than the literal claim language. Alvesco is approved for maintenance treatment of asthma in patients 12 years of age and older. It is not approved as a rescue inhaler for acute bronchospasm. [3]

When did US Patent 5,482,934 lose exclusivity?

The patent issued January 9, 1996. Because the application predates the Uruguay Round Agreements Act transition, the applicable baseline term is generally 17 years from issue rather than 20 years from the earliest effective filing date. On that basis, the original term ended January 9, 2013. [1][4]

Event	Date
US Patent 5,482,934 issued	January 9, 1996
Baseline 17-year expiration	January 9, 2013
Current status	Expired
Current Paragraph IV relevance	None for this expired patent

A patent expiration date is separate from FDA regulatory exclusivity. FDA approval of Alvesco occurred in 2006, but approval did not revive or extend the patent after its statutory term ended. Any pediatric or regulatory exclusivity would have been temporary and would not create a current patent right. [2][3]

What is the Orange Book status of ciclesonide?

Ciclesonide is listed in FDA-approved drug products under the Alvesco NDA. The Orange Book is the controlling source for current FDA-listed patents, pediatric exclusivity, and therapeutic-equivalence information. [2]

US Patent 5,482,934 is an expired composition and method patent. It should not be treated as a current Orange Book patent obstacle to an abbreviated application. A current applicant must still evaluate any later-listed patents covering:

Inhalation suspension or solution characteristics.
Device components.
Dose-counter mechanisms.
Manufacturing processes.
Particle engineering.
Formulation stability.
Specific methods of treatment.
New combinations or delivery systems.

The supplied claim set does not establish that any such later patent exists or remains enforceable.

Are there Paragraph IV challenges to US Patent 5,482,934?

A Paragraph IV certification is used when an ANDA applicant asserts that a listed patent is invalid, unenforceable, or will not be infringed. Because Patent 5,482,934 has expired, a current applicant would not need to mount a Paragraph IV challenge against it. The relevant certification would generally be that the patent has expired or is otherwise no longer a bar to approval.

Historical Paragraph IV activity cannot be inferred from the claims alone. FDA Orange Book records and court filings would be required to establish the identity of any challenger, notice-letter date, litigation complaint, or settlement terms. The expired status of the patent is nevertheless clear from the patent’s term.

What patent litigation affects ciclesonide?

The supplied patent claims do not identify litigation. Patent 5,482,934 should be separated from later disputes involving:

Alvesco formulation technology.
Inhaler devices.
Generic equivalence.
Manufacturing processes.
Regulatory exclusivity.
Other ciclesonide patent families.

No litigation conclusion should be attributed to Patent 5,482,934 solely from the claim language. A court’s infringement analysis would also depend on the patent file history, product composition, assay evidence, and claim construction.

How strong is the patent estate for ciclesonide?

The patent was strong at the compound level during its enforceable term because it combined several barriers:

A defined steroid core.
A cyclohexylmethylene acetal.
A 21-isobutyrate ester.
Position-22 stereochemical coverage.
R/S mixture coverage.
Composition claims.
Anti-inflammatory treatment claims.
Topical-use claims.

Its strongest commercial claim was claim 8, which directly identified the ciclesonide compound. Claims 9 and 10 reduced the risk that a stereochemically resolved product could avoid the specific compound claim.

The estate is weak as a current exclusivity barrier because the patent has expired. Its historical value was concentrated in the active pharmaceutical ingredient. The supplied claims do not provide durable protection for a modern inhaler device, formulation platform, or manufacturing process.

How does ciclesonide patent protection compare with generic entry risk?

Issue	Impact on ciclesonide
Active ingredient patent	Patent 5,482,934 expired
Biosimilar pathway	Not applicable; ciclesonide is a small molecule
Likely FDA pathway	ANDA or, in some cases, 505(b)(2)
Stereochemical design-around	Limited value because claim 1 covers R, S, and mixtures
Formulation design-around	Potentially material if later patents exist
Device design-around	Potentially material for inhaler products
API manufacturing	Process patents may create separate risk
Current compound-level exclusivity	None under Patent 5,482,934

Ciclesonide is not a biologic, so a biosimilar application under the Public Health Service Act is not the relevant pathway. A generic inhaled product would face pharmaceutical-equivalence, bioequivalence, device, performance, and product-quality requirements rather than biosimilar interchangeability requirements. [3][5]

What licensing deals are associated with the patent?

The claim text does not establish ownership transfers, licenses, sublicenses, or commercialization agreements. Ciclesonide was developed and commercialized through companies associated with the Altana and Nycomed businesses, with later US commercialization by Covis Pharma. Those corporate relationships should not be treated as proof of a license under Patent 5,482,934.

A patent assignment is different from a commercial license. USPTO assignment records can establish recorded ownership changes, but they do not necessarily disclose private license terms, royalty rates, field restrictions, or settlement covenants. [1]

What generic launch scenarios exist for ciclesonide?

The principal launch scenarios are:

Direct ANDA entry after patent expiry. Patent 5,482,934 does not block approval on its own.
Formulation or device-based entry. A generic applicant may need to design around later patents or pursue certifications against them.
505(b)(2) entry. This route may be relevant for a materially different formulation, delivery system, or indication.
Authorized-generic or licensed entry. Commercial access may depend on agreements unrelated to the expired compound patent.
Delayed entry from technical complexity. Inhaled corticosteroid products can face development and regulatory barriers even when compound patents have expired.

The main remaining risk is therefore regulatory and technical, not infringement of Patent 5,482,934.

Key Takeaways

US Patent 5,482,934 covers ciclesonide and related steroidal acetal compounds.
Claim 1 covers R, S, and mixed stereochemical forms at position 22.
Claims 8-10 specifically cover ciclesonide and its two epimers.
Claims 4-7 add drug, composition, systemic treatment, and topical-use protection.
Claims 11 and 12 cover hydrogenated and fluorinated variants defined by X1 and X2.
The patent issued January 9, 1996, and its baseline term ended January 9, 2013.
The patent is expired and is not a current Paragraph IV barrier.
Ciclesonide is a small molecule, so biosimilar analysis does not apply.
Current generic risk depends on later formulation, device, process, and regulatory issues rather than this expired compound patent.

FAQs About US Patent 5,482,934 and Ciclesonide

Is ciclesonide still patent protected in the United States?

Patent 5,482,934 no longer provides active US compound protection. Later formulation, device, process, or use patents must be evaluated separately.

Can a generic company sell ciclesonide after Patent 5,482,934 expires?

Expiration removes the compound-patent barrier, but FDA approval, pharmaceutical equivalence, inhaler performance, formulation requirements, and any later patents remain relevant.

Does changing the R/S ratio avoid the ciclesonide patent?

Not during the patent term. Claim 1 covers either epimer and stereoisomeric mixtures, while claims 9 and 10 separately cover the R and S ciclesonide epimers.

Is ciclesonide eligible for a biosimilar application?

No. Ciclesonide is a chemically synthesized small molecule. A generic inhalation product would normally use an ANDA or, depending on the product, a 505(b)(2) application.

Does Patent 5,482,934 protect the Alvesco inhaler device?

The supplied claims do not recite an inhaler, actuator, propellant, dose counter, or device architecture. Any device protection would need to arise from separate patent claims.

References

United States Patent and Trademark Office. (1996). US Patent No. 5,482,934.
U.S. Food and Drug Administration. (n.d.). Approved drug products with therapeutic equivalence evaluations: Orange Book.
U.S. Food and Drug Administration. (2017). Alvesco (ciclesonide) inhalation aerosol prescribing information.
United States Code, 35 U.S.C. §§ 154, 156.
U.S. Food and Drug Administration. (2024). Abbreviated new drug application process.

Country	Patent Number	Estimated Expiration	Supplementary Protection Certificate	SPC Country	SPC Expiration
Austria	402930	⤷ Start Trial
Austria	A176991	⤷ Start Trial
Australia	649472	⤷ Start Trial
Australia	8368691	⤷ Start Trial
Belgium	1005876	⤷ Start Trial
Brazil	1100860	⤷ Start Trial
Canada	2050812	⤷ Start Trial
>Country	>Patent Number	>Estimated Expiration	>Supplementary Protection Certificate	>SPC Country	>SPC Expiration

Details for Patent: 5,482,934

Summary for Patent: 5,482,934