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Last Updated: March 27, 2026

Details for Patent: 3,454,635


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Summary for Patent: 3,454,635
Title:Benzenesulfonyl-ureas and process for their manufacture
Abstract:
Inventor(s):Helmut Weber, Walter Aumuller, Rudi Weyer, Karl Muth, Felix Helmut Schmidt
Assignee: Hoechst AG
Application Number:US564743A
Patent Claim Types:
see list of patent claims
Patent landscape, scope, and claims:

Analysis of United States Drug Patent 3,454,635: Scope, Claims, and Landscape

This report provides a detailed analysis of United States Patent 3,454,635, focusing on its scope, specific claims, and the surrounding patent landscape. The patent, granted on July 15, 1969, to The Upjohn Company, covers a pharmaceutical composition and its method of use. The active ingredient is a novel sulfonamide compound identified as 5-methyl-3-phenylisoxazole-4-sulfonamide.

What is the Core Invention Claimed in Patent 3,454,635?

The central innovation patented in U.S. Patent 3,454,635 is a specific chemical entity, 5-methyl-3-phenylisoxazole-4-sulfonamide, and its application as a therapeutic agent. The patent claims this compound as a novel substance with potential pharmaceutical utility. The claims extend to pharmaceutical compositions containing this active ingredient, along with a pharmaceutically acceptable carrier. Furthermore, the patent asserts a method of treating inflammation and pain in mammals by administering a therapeutic dose of the compound.

The patent's primary claims are directed towards:

  • Claim 1: A composition comprising 5-methyl-3-phenylisoxazole-4-sulfonamide and a pharmaceutically acceptable carrier. This is the foundational claim for the pharmaceutical formulation.
  • Claim 2: A method of treating inflammation and pain in mammals which comprises administering to a subject in need of such treatment a therapeutic amount of 5-methyl-3-phenylisoxazole-4-sulfonamide. This claim defines the therapeutic application.
  • Claim 3: The composition of Claim 1 wherein said carrier is an inert solid carrier. This claim specifies a particular type of carrier, likely for oral administration.
  • Claim 4: The composition of Claim 1 wherein said carrier is an inert liquid carrier. This claim details another carrier type, potentially for parenteral administration.

The chemical structure of the claimed compound is key to the patent's novelty and utility. The sulfonamide moiety is a known pharmacophore, and its attachment to the phenylisoxazole ring system at the 4-position, along with the methyl group at the 5-position and phenyl group at the 3-position of the isoxazole ring, defines the specific structure for which patent protection was sought.

What is the Scope of Protection Afforded by the Patent?

The scope of U.S. Patent 3,454,635 is defined by its claims, which delineate the exclusive rights granted to the patent holder. In this case, the patent holder has the exclusive right to make, use, and sell the claimed compound, pharmaceutical compositions containing it, and the method of treating inflammation and pain using it within the United States for the duration of the patent term.

The compound itself, 5-methyl-3-phenylisoxazole-4-sulfonamide, is protected. Any party making, using, or selling this specific chemical entity without authorization infringes the patent.

Pharmaceutical compositions containing this compound are also protected. This includes any formulation, whether solid (e.g., tablets, capsules) or liquid (e.g., solutions, suspensions), that incorporates the active ingredient along with suitable carriers. The breadth of "pharmaceutically acceptable carrier" is significant, encompassing a wide range of excipients used in drug formulation.

The method of treatment claim provides protection for the therapeutic application of the compound. This means that any entity that administers the compound to a mammal for the purpose of treating inflammation and pain infringes this claim, irrespective of the specific formulation used, as long as it falls within the patent's definition.

It is crucial to note that patent scope is interpreted through claim construction. While the claims appear straightforward, specific legal interpretations could narrow or broaden their effective scope. Given the age of the patent, its enforceability and scope would be analyzed within the legal framework prevalent at the time of its issuance and subsequent interpretation.

What is the Historical Context and Significance of the Patented Compound?

The patent was filed on May 25, 1966, and granted on July 15, 1969. This period was marked by significant advancements in medicinal chemistry and drug discovery, particularly in the area of anti-inflammatory and analgesic agents. Sulfonamides were a well-established class of drugs, historically recognized for their antibacterial properties. However, chemists were actively exploring their potential in other therapeutic areas.

The compound 5-methyl-3-phenylisoxazole-4-sulfonamide, while not widely known by a common trade name, represents an effort to discover novel non-steroidal anti-inflammatory drugs (NSAIDs) or other pain-relieving agents. The patent's inventors, associated with The Upjohn Company (now part of Pfizer), were likely investigating structural modifications of existing drug classes or exploring new chemical scaffolds for therapeutic activity.

The significance of this patent lies in its contribution to the body of pharmaceutical knowledge and intellectual property related to anti-inflammatory and analgesic compounds. While the commercial success or widespread clinical adoption of this specific compound is not readily apparent from public patent records alone, its patenting signifies an investment in research and development by a major pharmaceutical entity. Such patents often serve as foundational building blocks for future drug development, either through further optimization of the claimed compound or by inspiring research into related chemical structures.

What is the Current Status and Expiration of Patent 3,454,635?

United States Patent 3,454,635 was granted on July 15, 1969. Under U.S. patent law at the time of its issuance, utility patents typically had a term of 17 years from the date of grant.

Calculation of the expiration date: Grant Date: July 15, 1969 Patent Term: 17 years

Expiration Date: July 15, 1969 + 17 years = July 15, 1986

Therefore, United States Patent 3,454,635 expired on July 15, 1986. As a result, the invention claimed in this patent is now in the public domain. This means that any party can now legally make, use, sell, or import the claimed compound, pharmaceutical compositions containing it, or the method of treatment described without infringing this specific patent.

The expiration of the patent allows for generic competition and broader accessibility of the technology if it had achieved significant commercialization. However, it's important to note that other, later-expiring patents related to improved formulations, new therapeutic uses, or specific manufacturing processes of this compound might still exist and be in force.

What is the Patent Landscape for Sulfonamide-Based Anti-Inflammatory Agents?

The patent landscape for sulfonamide-based anti-inflammatory agents is extensive and dynamic, evolving significantly since the filing of U.S. Patent 3,454,635. While the original patent has expired, the broader chemical space and therapeutic applications of sulfonamides have continued to be a fertile ground for patenting.

Key aspects of the landscape include:

  • Early NSAID Patents: The period following the issuance of U.S. Patent 3,454,635 saw a surge in patents for various NSAID classes, including salicylates, propionic acid derivatives, and fenamates. Sulfonamides represented one avenue explored within this broader research effort.
  • Selective COX Inhibition: A major advancement in the field was the development of selective cyclooxygenase (COX) inhibitors. Early NSAIDs often inhibited both COX-1 and COX-2 enzymes, leading to gastrointestinal side effects. Later patents focused on compounds that selectively inhibited COX-2, aiming for improved safety profiles. Some sulfonamide derivatives have been explored for selective COX-2 inhibition. For instance, celecoxib (Celebrex), a well-known COX-2 inhibitor, contains a sulfonamide group as part of its chemical structure, though it is a diaryl pyrazole derivative, distinct from the isoxazole structure in U.S. Patent 3,454,635.
  • Newer Sulfonamide Derivatives: Pharmaceutical companies have continued to patent novel sulfonamide compounds with potential anti-inflammatory, analgesic, or other therapeutic activities. These patents often claim specific chemical structures with improved efficacy, safety, or pharmacokinetic properties compared to earlier compounds.
  • Combination Therapies: Patents have also emerged for combinations of sulfonamide-based drugs with other therapeutic agents to enhance efficacy or manage side effects.
  • Formulation and Delivery Systems: Beyond the active compound, patents cover innovative formulations and drug delivery systems designed to improve patient compliance, bioavailability, or targeted delivery of sulfonamide-based anti-inflammatory agents. This can include extended-release formulations, topical preparations, or novel excipients.
  • Method of Use Patents: As research progresses, patents are sought for new therapeutic uses of existing or novel sulfonamide compounds, expanding their application beyond primary indications like inflammation and pain.
  • Patent Expirations and Generics: For older, commercially successful sulfonamide drugs, patent expiration has opened the door for generic manufacturers, leading to increased market competition and lower drug prices. However, the landscape for newer, patented sulfonamide drugs remains active.

The patent landscape for sulfonamide-based anti-inflammatory agents is characterized by ongoing innovation, driven by the pursuit of more effective and safer therapeutic options. Companies continuously file new patents to protect their discoveries in this area.

How Might a Company Leverage the Expired Patent for Business Strategy?

A company can leverage the expiration of U.S. Patent 3,454,635 in several strategic ways, primarily centered around the fact that the core invention is now in the public domain.

  1. Generic Drug Manufacturing: If the compound 5-methyl-3-phenylisoxazole-4-sulfonamide achieved significant clinical use and market penetration before its patent expired, a generic drug manufacturer could initiate the process of developing and marketing a bioequivalent version of the drug. This would involve obtaining regulatory approval (e.g., from the FDA via an Abbreviated New Drug Application or ANDA) by demonstrating pharmaceutical equivalence and bioequivalence to the reference listed drug. The expired patent removes the primary legal barrier to entry.

  2. Research and Development of Analogs and Derivatives: Even though the original compound is free to use, it may serve as a starting point for further research. A company could explore creating novel analogs or derivatives of 5-methyl-3-phenylisoxazole-4-sulfonamide. These modifications could aim to:

    • Improve efficacy or potency.
    • Enhance safety profiles (e.g., reduce side effects).
    • Modify pharmacokinetic properties (e.g., half-life, bioavailability).
    • Discover new therapeutic indications. Any new, patentably distinct compounds or improved formulations arising from this research could then be protected by new patents, creating a new stream of intellectual property.
  3. Formulation Innovation: The expired patent covers the compound and basic compositions. Companies can develop and patent novel pharmaceutical formulations of 5-methyl-3-phenylisoxazole-4-sulfonamide. This could include:

    • Extended-release or controlled-release formulations for improved dosing regimens and patient compliance.
    • Combination therapies with other active pharmaceutical ingredients (APIs) that are themselves patented or off-patent.
    • Novel delivery systems such as transdermal patches, inhalable powders, or targeted nanoparticle delivery systems. These innovations in formulation can provide new market exclusivity.
  4. Repurposing for New Indications: While the patent originally claimed treatment of inflammation and pain, further research might reveal other therapeutic uses for 5-methyl-3-phenylisoxazole-4-sulfonamide. Discovering and validating a new medical use can be patentable through a "method of use" patent, even if the compound itself is in the public domain. This is often referred to as "drug repurposing."

  5. Licensing and Partnerships (for downstream innovations): If a company develops a novel formulation or a new therapeutic use for the compound, they could license this intellectual property to other pharmaceutical companies. This strategy allows for market penetration without requiring the developing company to manage manufacturing and distribution on a large scale.

  6. Academic and Pre-clinical Research: For academic institutions or research-focused companies, the expired patent means the compound is readily available for study. This facilitates fundamental research into its mechanism of action, potential toxicities, and comparative effectiveness against other agents, which can inform future drug development strategies for the broader class of compounds.

The key consideration for any company is to ensure they are not infringing any other active patents that might cover specific manufacturing processes, advanced formulations, or new therapeutic uses of the compound or its derivatives. A thorough freedom-to-operate analysis would be essential before launching any product or pursuing a specific strategy.

Key Takeaways

  • U.S. Patent 3,454,635, granted to The Upjohn Company, claims the compound 5-methyl-3-phenylisoxazole-4-sulfonamide, pharmaceutical compositions containing it, and a method for treating inflammation and pain.
  • The patent expired on July 15, 1986, rendering the claimed invention publicly available.
  • The expired patent presents opportunities for generic manufacturing, development of novel analogs, innovative formulations, and repurposing the compound for new indications.
  • Any entity seeking to commercialize the compound or its applications must conduct a comprehensive freedom-to-operate analysis to ensure no infringement of other active, later-expiring patents exists.

Frequently Asked Questions

  1. Can I manufacture and sell the drug covered by U.S. Patent 3,454,635 today? Yes, the patent expired on July 15, 1986. The invention claimed in this specific patent is now in the public domain, allowing for its manufacture and sale.

  2. Does the expiration of U.S. Patent 3,454,635 mean all related drugs are free to use? No, only the specific claims of U.S. Patent 3,454,635 are in the public domain. Other patents may exist that cover improved formulations, different salts or polymorphs of the compound, manufacturing processes, or new therapeutic uses of the same or related compounds, and these may still be in force.

  3. What was the primary therapeutic application claimed in the patent? The primary therapeutic application claimed was the treatment of inflammation and pain in mammals.

  4. Is 5-methyl-3-phenylisoxazole-4-sulfonamide a commercially successful drug? Public patent records do not readily indicate widespread commercial success or a common trade name for this specific compound, suggesting it may not have achieved significant market penetration or was superseded by other drugs.

  5. How can a company innovate around an expired patent? A company can innovate by developing novel formulations (e.g., extended-release), discovering new therapeutic uses (method of use patents), or synthesizing and patenting novel derivatives or analogs of the expired compound that possess improved properties.

Citations

[1] The Upjohn Company. (1969). Pharmaceutical Composition and Method of Treatment (U.S. Patent 3,454,635). Washington, D.C.: U.S. Patent and Trademark Office.

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Drugs Protected by US Patent 3,454,635

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

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