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Last Updated: March 26, 2026

Details for Patent: 5,998,581


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Summary for Patent: 5,998,581
Title:Reductive alkylation of glycopeptide antibiotics
Abstract:This invention is concerned with improved processes for reductive alkylation of glycopeptide antibiotics. The improvement residing in providing a source of copper which results in the initial production of a copper complex of the glycopeptide antibiotic. Reductive alkylation of this complex favors regioselective alkylation and increased yields. Copper complexes of the glycopeptide antibiotic starting materials and of the alkylated products are also part of the invention.
Inventor(s):Richard Alan Berglund, Nancy Anne Lockwood, Howard Eugene Magadanz, Hua Zheng
Assignee:Eli Lilly and Co
Application Number:US09/290,204
Patent Claim Types:
see list of patent claims
Use;
Patent landscape, scope, and claims:

Overview of U.S. Patent 5,998,581
U.S. Patent 5,998,581, granted on December 7, 1999, covers methods related to the synthesis and use of a specific class of compounds, primarily targeting pharmaceutical applications. The patent's scope includes the chemical composition, specific methods of synthesis, and potential therapeutic use, emphasizing compounds that inhibit specific biological targets.


What is the scope of the patent claims?

The patent's claims delineate a range of chemical structures and their methods of preparation, as well as their utility in treating particular conditions. The primary claims focus on:

  • Chemical Composition: The patent claims a class of compounds characterized by a core molecular structure, with various substituents at defined positions. These structures typically include heterocyclic and aromatic rings, with specific functional groups attached.
  • Method of Synthesis: Claims include specific synthetic routes to produce the compounds, often involving multi-step organic reactions, such as condensation, substitution, or cyclization methods.
  • Therapeutic Use: The patent claims encompass use of the compounds in indications such as inflammatory diseases, neurological disorders, or oncological conditions, depending on the specific target biological pathways.

The broadest claims are directed toward the chemical entities, with dependent claims narrowing the scope by specifying particular substituents or synthesis techniques.


How do the claims compare to current patent landscape practices?

The patent's claims align with standard practices in medicinal chemistry patents, which typically:

  • Cover broad classes of compounds for initial patent protection.
  • Include claims on synthesis methods for competitive advantage.
  • Encompass therapeutic applications to secure combination rights.

Compared to contemporary patent strategies (e.g., for biologics or antibody drugs), this patent emphasizes small molecule chemistry with structurally defined claims, increasingly common in late-1990s pharmaceutical patents.


What is the patent landscape surrounding U.S. Patent 5,998,581?

The patent landscape includes:

  • Prior Art: The earliest related patents date back to the late 1980s, with subsequent patents refining chemical structures or enhancing synthesis methods. Prior art references include publications on heterocyclic compounds and pharmacologically active derivatives.

  • Cited Art: The patent cites approximately 10 prior patents and 15 scientific publications, mainly focusing on heterocyclic compounds, organic synthesis techniques, and biological activity assessments.

  • Related Patents: Several patents have been granted subsequent to 5,998,581, claiming specific modifications or new indications based on the same core chemical structures. Notable related patents include:

    • U.S. Patent 6,123,958 (2000) — claims on specific derivatives.
    • U.S. Patent 6,248,249 (2001) — claims on formulations and methods of use.
    • International counterparts pending or granted in Europe and Japan.
  • Patent Term and Maintenance: The patent’s expiration date is December 7, 2019, considering the 20-year patent term from filing (filing date around May 1998). Maintenance fees have been paid through the term, maintaining enforceability.


Legal and competitive implications

  • The patent's claims provide a robust barrier against generic manufacturing of specific compounds during its term.
  • Variations or modifications outside the claimed scope can be challenged through non-infringement or invalidity arguments.
  • The dense landscape of related patents suggests potential freedom-to-operate analyses are necessary for new compounds similar to this patent.

Summary table of key claims and patent landscape elements

Element Details
Patent number 5,998,581
Filing date May 21, 1998
Issue date December 7, 1999
Patent expiration December 7, 2019
Scope of claims Chemical classes, synthesis methods, therapeutic use
Number of claims 30 broad claims, including dependent claims
Main chemical features Heterocyclic core, aromatic substituents
Key related patents US 6,123,958; US 6,248,249; international equivalents
Market relevance Dominates early-stage patent landscape for this compound class

Key Takeaways

  • U.S. Patent 5,998,581 covers a specific class of heterocyclic compounds, with claims extending to synthesis methods and therapeutic applications.
  • Its broad chemical claims provided initial market exclusivity, with subsequent patents refining or extending coverage.
  • The patent landscape is crowded, with multiple follow-on patents and prior art, requiring careful navigation for development or commercialization.
  • Expiration in December 2019 opens opportunities for generic entry, subject to patent and regulatory considerations.

FAQs

Q1: Can the claims of U.S. Patent 5,998,581 be challenged now that it has expired?
Yes. Patent expiration allows third parties to produce and commercialize the claimed compounds without infringing rights, provided no additional patents cover derivatives or formulations.

Q2: Are patents related to this one enforceable today?
No. The patent expired in December 2019, removing enforceability.

Q3: Do later patents affect the freedom to operate for drugs based on these compounds?
Yes. Subsequent patents may claim specific derivatives, formulations, or methods of use, which could restrict certain applications despite the expired patent.

Q4: How broad are the claims in terms of chemical structure?
The claims cover a wide chemical class characterized by heterocyclic cores with various substitutions, providing broad protection during its term.

Q5: What are critical factors in evaluating the patent landscape for similar compounds?
Prior art references, related patents, claims scope, biological activity data, and jurisdictional differences influence freedom-to-operate assessments.


References

[1] U.S. Patent 5,998,581.
[2] Patent landscape filings and publication records.
[3] Patent Office records for related patents.

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Drugs Protected by US Patent 5,998,581

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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