Last Updated: September 24, 2026

Details for Patent: 4,690,825


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Summary for Patent: 4,690,825
Title:Method for delivering an active ingredient by controlled time release utilizing a novel delivery vehicle which can be prepared by a process utilizing the active ingredient as a porogen
Abstract:Delivery vehicles comprised of a polymeric bead having a network of pores with an active ingredient held within the network are provided for use in a method to provide controlled release of the active ingredient. The network of pores is substantially non-collapsible upon removal of the active ingredient and the delivery vehicles are polymerized by a process in which the active ingredient also comprises the porogen during formation of the network of pores.
Inventor(s):Richard Won
Assignee: Heron Therapeutics LLC
Application Number:US06/784,382
Patent Claim Types:
see list of patent claims
Use; Composition; Process; Delivery;
Patent landscape, scope, and claims:

# U.S. Patent 4,690,825: Claim Scope, Expiration, Patent Landscape, and Generic-Entry Risk

U.S. Patent 4,690,825 covers porous cross-linked polymer beads that retain an active ingredient in a substantially non-collapsible pore network, together with methods for making and using those beads for controlled release. The patent issued on September 1, 1987, and, under the pre-Uruguay Round patent-term rule, its 17-year term ran to approximately September 1, 2004. It is therefore expired and cannot presently block manufacture, sale, or use in the United States.[1][2]

The patent is a platform-technology patent, not a drug-specific patent. Its claims focus on particle structure, polymer chemistry, porogen retention, particle size, loading, manufacturing conditions, and release mechanisms. The principal commercial relevance is historical or technical: it may remain useful as prior art against later patents claiming similar porous polymer microspheres, controlled-release beads, or mineral-oil delivery systems.

What does U.S. Patent 4,690,825 cover?

The patent claims three connected subject-matter categories:

Claim category Independent claims Core subject
Composition of matter 1, 28, 51 Porous polymeric bead containing an active ingredient
Manufacturing process 8, 34, 60 Suspension polymerization of monomer droplets in a porogen
Delivery method 16, 40, 68 Mixing the delivery vehicle with a medium, applying it to a surface, and releasing the ingredient

The broadest recurring limitation is a porous polymeric bead with:

  1. A network of pores;
  2. An active ingredient held within the pores; and
  3. Pores that are “substantially non-collapsible” after removal of the active ingredient.

The claims also repeatedly recite particle diameters of approximately 10 to 100 microns, cross-linking density above approximately 10%, and active-ingredient loading between approximately 5% and 60% by weight.

The claim set is drafted as a layered platform. The broad claims are followed by narrower claims directed to specific monomer systems, mineral oil, particle size, release mechanisms, and manufacturing steps.

How many independent claims does Patent 4,690,825 contain?

Patent 4,690,825 contains eight independent claims based on the claim text provided:

  • Claim 1: composition
  • Claim 8: manufacturing process
  • Claim 16: delivery method
  • Claim 28: styrene-divinylbenzene composition
  • Claim 34: styrene-divinylbenzene manufacturing process
  • Claim 40: styrene-divinylbenzene delivery method
  • Claim 51: composition defined by a substantially complete release test
  • Claim 60: manufacturing process incorporating the release test

Claim 68 is also drafted as an independent delivery-method claim, bringing the total to nine independent claims if claim dependency and punctuation are assessed according to the supplied text.

The independent claims divide into two principal families:

  • Claims 1, 8, and 16: general porous-bead technology.
  • Claims 28, 34, and 40: styrene-divinylbenzene technology.
  • Claims 51, 60, and 68: technology defined partly by a release-performance requirement.

What polymer systems are protected?

The claims identify three principal polymer systems.

Polymer system Claims expressly covering it Technical significance
Styrene-divinylbenzene 14, 28-50, 53, 61, 68-80 Cross-linked aromatic polymer bead
Vinyl stearate-divinylbenzene 2, 10, 27, 53, 61, 64, 69 Hydrophobic bead system
Methyl methacrylate and ethylene glycol dimethacrylate 2, 10, 27, 53, 64, 69 Cross-linked methacrylate bead system

The claims also refer to “styrene and divinylbenzene” as a comonomer pair and require an initiator soluble in the monomer system in certain embodiments. The process claims therefore reach beyond the finished bead and cover specific suspension-polymerization approaches.

The principal structural distinction is the use of cross-linking to maintain pore geometry after removal of the porogen or loaded active ingredient. A non-cross-linked or weakly cross-linked polymer particle may fall outside the claims if it lacks the required substantially non-collapsible pore network.

What limitations define the strongest claim scope?

The strongest practical limitations are the following:

Porous polymeric bead

The claims require a bead rather than an arbitrary porous polymer article. A formulation using a porous film, capsule, fiber, granule, or monolithic matrix would require a close analysis of whether it satisfies the “bead” limitation.

Non-collapsible pore network

This is the central structural limitation. The pore network must remain substantially non-collapsible when the active ingredient is removed. A product with pores formed only by temporary solvent extraction and substantial pore collapse may present a non-infringement position.

Active ingredient retained in the pores

The claims require the active ingredient to be held within the pore network. A coating or surface-adsorbed ingredient that does not reside within the internal pore structure may fall outside the literal claim language.

Cross-linking

Several dependent claims require calculated cross-linking density above approximately 10%. This limitation narrows the claims but also identifies the technology’s principal engineering mechanism. A competing product with a different pore-stabilization mechanism could avoid those dependent claims while still requiring analysis under broader claims 1, 8, 16, 28, 34, 40, 51, 60, or 68.

Particle size

The 10-to-100-micron range is a dependent limitation. Products outside that range are not automatically outside the patent because the independent claims do not uniformly require that size range.

Release mechanism

Claims 22-25 and 46-49 recite pressure release, diffusion, volatilization, and gradual continuous release. These claims are narrower than the underlying composition claims. A product using another release mechanism may avoid these specific dependent claims but could still implicate an independent composition claim if the bead structure is present.

What does the process claim cover?

The process claims generally require:

  1. Dissolving one or more monomers in an inert porogen;
  2. Suspending that solution in an incompatible phase;
  3. Agitating the mixture to create droplets;
  4. Activating the monomer or monomers to polymerize the droplets;
  5. Forming porous beads with the porogen retained in the pore network;
  6. Separating the beads from the incompatible phase;
  7. Removing impurities; and
  8. Retaining the porogen as the active ingredient.

This is a suspension-polymerization process. A manufacturer using a materially different process, such as emulsion polymerization, microfluidic droplet generation, phase separation, spray drying, templating, or post-polymerization pore formation, would need to determine whether all required process steps are present.

The process claims are narrower than a pure product claim because infringement requires performance of the claimed steps. They may nevertheless have been commercially important when manufacturing methods were less standardized and process evidence was available from batch records, technical specifications, or reverse engineering.

What is the significance of the mineral-oil claims?

Mineral oil appears as both:

  • An inert porogen used during bead formation; and
  • The active ingredient retained for subsequent release.

Claims 5, 11, 19, 31, 35, 43, 54, 56, 63, 70, and 73 specifically recite mineral oil.

This creates a narrow but commercially recognizable subfamily. A formulation containing mineral oil in cross-linked porous beads may satisfy several dependent claims if the remaining structural and process limitations are met. Mineral oil is not itself a drug active ingredient in the conventional pharmaceutical sense. The patent’s “active ingredient” terminology is broad enough to encompass carriers, agents, cosmetic ingredients, volatile materials, and other releasable substances.

Claim 26 and claim 50 expressly recognize an active ingredient comprising a carrier and an agent. That language supports applications in which the bead carries another substance rather than acting as a conventional oral pharmaceutical dosage form.

What is the scope of the release-test claims?

Claims 51-80 add a functional release requirement. The composition must have a calculated cross-linking density and active-ingredient concentration such that substantially all of the active ingredient is released when the bead is placed in a solvent in which the active ingredient is soluble and the bead is wetted.

Claim 52 narrows the requirement to release within approximately five minutes under moderate agitation.

These claims are potentially useful for distinguishing a controlled-release bead from a permanently loaded absorbent particle. They also create proof issues. A party assessing infringement would need to determine:

  • The solvent used for testing;
  • Whether the solvent is one in which the active ingredient is soluble;
  • What constitutes “sufficient length of time”;
  • What “substantially all” means;
  • What constitutes moderate agitation;
  • How calculated cross-linking density is determined; and
  • Whether the bead is adequately wetted before measuring release.

The performance-based language may also create validity and construction issues if the specification does not provide sufficiently objective test protocols. Those issues depend on the patent specification, prosecution history, expert testimony, and applicable claim-construction law.

When did U.S. Patent 4,690,825 lose exclusivity?

The patent issued September 1, 1987. Because it was granted before June 8, 1995, its term was generally 17 years from issuance rather than 20 years from the earliest effective U.S. nonprovisional filing date.[2]

Event Date or period
U.S. patent issue September 1, 1987
Standard patent term 17 years from issue
Approximate expiration September 1, 2004
Current enforceability Expired
Current Paragraph IV relevance None for this expired patent
Current Orange Book listing None identified from the claim subject matter

Any terminal disclaimer, patent-term adjustment, reissue, or unusual maintenance-fee event would need to be checked against the official USPTO file. Those mechanisms ordinarily do not extend a pre-1995 patent beyond the governing statutory term absent a specific statutory basis.

What is the Orange Book status of Patent 4,690,825?

Patent 4,690,825 is not a conventional Orange Book drug patent. Its claims do not identify:

  • A specific FDA-approved active pharmaceutical ingredient;
  • A specific approved dosage form;
  • A drug product strength;
  • A labeled therapeutic indication; or
  • A pharmaceutical composition tied to an approved New Drug Application.

The FDA Orange Book lists patents submitted for approved drug products under the Hatch-Waxman framework. A broad controlled-release bead platform patent of this type would not ordinarily appear as an Orange Book-listed patent unless it had been submitted for a particular approved drug product and accepted by FDA under the applicable listing rules.[3]

There is therefore no meaningful Orange Book or Paragraph IV challenge pathway directed specifically to Patent 4,690,825 today. Any generic applicant could not receive a current patent-term barrier from this expired patent.

What FDA exclusivity applies?

No FDA regulatory exclusivity can be inferred from Patent 4,690,825. Patent protection and FDA exclusivity are separate rights.

The patent does not itself establish:

  • New chemical entity exclusivity;
  • New clinical investigation exclusivity;
  • Orphan-drug exclusivity;
  • Pediatric exclusivity;
  • 3-year formulation or indication exclusivity; or
  • Biologic reference-product exclusivity.

The claims could have been used in a drug-delivery product, topical product, cosmetic product, agricultural product, or industrial release system. Regulatory exclusivity would depend on the product and regulatory submission, not on the patent’s generic delivery-vehicle claims.

Which companies are challenging Patent 4,690,825?

There is no current Paragraph IV challenger landscape for this patent because its term expired approximately two decades ago. A Paragraph IV certification is relevant to an unexpired patent listed for an approved drug product. Patent 4,690,825 does not present that current litigation profile.

Historical competitive activity is more likely to have occurred through:

  • Alternative porous polymer bead systems;
  • Different cross-linkers;
  • Different porogens;
  • Non-bead controlled-release matrices;
  • Liposomes, microparticles, and microcapsules;
  • Topical and transdermal delivery systems; and
  • Later patents claiming particular active ingredients or formulations.

Those later rights must be analyzed independently. Expiration of Patent 4,690,825 does not eliminate later patents covering a specific drug, particle coating, manufacturing process, excipient combination, or approved formulation.

How strong is the patent estate for this technology?

As a current enforcement estate, it is weak because the patent is expired. As prior art, it is potentially significant.

Factor Assessment
Current U.S. exclusionary power None after expiration
Breadth of original platform claims Broad across porous polymer beads
Product-claim reach Potentially substantial where all structural limitations are met
Process-claim reach Moderate, dependent on process evidence
Mineral-oil subclaims Narrow and technically specific
Release-test claims Narrower, with proof and construction issues
Orange Book relevance None apparent
Biosimilar relevance None
Generic-entry barrier None
Prior-art significance Potentially material for later bead and controlled-release patents

The strongest historical claims were likely the composition claims directed to the porous bead itself because they did not require proof of a particular manufacturing route. The process claims could be avoided by changing the manufacturing pathway. The method claims required application of the delivery vehicle to a surface and release of the active ingredient, which narrowed their relevance to particular commercial uses.

What patent landscape surrounds the claimed technology?

The relevant landscape has five technical clusters:

Cross-linked porous polymer beads

These patents typically claim bead composition, pore volume, pore size, cross-link density, particle diameter, and loading capacity.

Microcapsules and microparticles

Microcapsule patents often claim a discrete shell surrounding a core, which differs structurally from a bead containing a connected internal pore network.

Controlled-release pharmaceutical particles

Later pharmaceutical patents may claim a particular active ingredient, polymer blend, coating, dissolution profile, or dosage form. Those claims can remain enforceable even though Patent 4,690,825 has expired.

Topical and cosmetic delivery systems

The surface-application claims in Patent 4,690,825 make topical, cosmetic, fragrance, pesticide, and coating uses relevant. Later products may use polymer particles to release emollients, fragrances, preservatives, sunscreens, or active agents.

Manufacturing and scale-up patents

Later rights may focus on droplet-size control, surfactants, initiators, solvent extraction, residual monomer removal, sterilization, and pharmaceutical-grade manufacturing. These process patents are more likely to create current freedom-to-operate issues than Patent 4,690,825 itself.

What generic launch risks remain?

Patent 4,690,825 creates no current generic-launch risk because it is expired. The relevant risks are second-generation rights.

A generic or follow-on manufacturer using porous polymer beads should assess:

  • Patents covering the specific active pharmaceutical ingredient;
  • Patents covering the approved release profile;
  • Formulation patents covering polymer, porogen, coating, or excipient combinations;
  • Method-of-use patents for the indication;
  • Manufacturing patents for bead formation or loading;
  • Particle-size and pore-structure patents;
  • Regulatory exclusivity associated with the reference product; and
  • Trade-secret restrictions concerning manufacturing parameters.

A product can be free of Patent 4,690,825 yet infringe a later patent claiming a particular drug-loaded porous particle or controlled-release dosage form.

Key Takeaways

  • U.S. Patent 4,690,825 covers porous cross-linked polymer beads containing releasable active ingredients.
  • Its principal limitations are a non-collapsible pore network, retained active ingredient, polymeric bead structure, and specified manufacturing or release characteristics.
  • The named polymer systems include styrene-divinylbenzene, vinyl stearate-divinylbenzene, and methyl methacrylate-based cross-linked polymers.
  • Mineral oil is a recurring porogen and active-ingredient embodiment.
  • The patent issued September 1, 1987, and its standard term expired approximately September 1, 2004.
  • It does not create a current Orange Book, Paragraph IV, biosimilar, or generic-entry barrier.
  • Its principal present value is as prior art against later porous-bead, controlled-release, topical-delivery, and manufacturing patents.
  • Current freedom-to-operate analysis should focus on later patents tied to the particular drug, formulation, release profile, and manufacturing process.

FAQs About U.S. Patent 4,690,825

Can an expired patent still affect a new controlled-release formulation?

Yes. The expired patent cannot be enforced, but it can be cited as prior art against later patent applications. It may also help establish that certain bead structures or release concepts were publicly disclosed before later filings.

Does the patent cover all polymeric microspheres?

No. The claims require a porous polymeric bead with an internal pore network holding the active ingredient. Nonporous microspheres, shell-core microcapsules, liposomes, and matrices lacking the claimed structure are not automatically covered.

Does use of mineral oil create infringement risk today?

No infringement risk arises from this patent because the patent is expired. Mineral-oil formulations may still implicate later patents covering a specific particle architecture, cosmetic formulation, pharmaceutical use, or manufacturing method.

Are the 10-to-100-micron particle limits present in every claim?

No. The particle-size range appears in dependent claims. It narrows those claims but does not apply uniformly to the independent claims.

Does the patent cover oral drug-delivery products?

The claim language is broad enough to encompass delivery applications, but the asserted method claims expressly require mixing the vehicle with a medium and applying the mixture to a surface. The patent does not expressly claim a conventional oral tablet, capsule, or specific FDA-approved drug product.

References

  1. United States Patent and Trademark Office. (1987). U.S. Patent No. 4,690,825, Controlled release delivery vehicle. https://patents.google.com/patent/US4690825A/en
  2. 35 U.S.C. § 154. Patent term provisions for patents issued under the pre-June 8, 1995 term regime. https://uscode.house.gov/view.xhtml?req=granuleid:USC-prelim-title35-section154
  3. U.S. Food and Drug Administration. (2023). Approved drug products with therapeutic equivalence evaluations, commonly known as the Orange Book. https://www.fda.gov/drugs/drug-approvals-and-databases/orange-book-data-files-technical-information

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Drugs Protected by US Patent 4,690,825

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

International Family Members for US Patent 4,690,825

Country Patent Number Estimated Expiration Supplementary Protection Certificate SPC Country SPC Expiration
Austria 68965 ⤷  Start Trial
Australia 591264 ⤷  Start Trial
Australia 7132287 ⤷  Start Trial
Germany 3774266 ⤷  Start Trial
European Patent Office 0285694 ⤷  Start Trial
>Country >Patent Number >Estimated Expiration >Supplementary Protection Certificate >SPC Country >SPC Expiration

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