Last Updated: May 10, 2026

Details for Patent: 5,169,849


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Summary for Patent: 5,169,849
Title:Nasal pharmaceutical compositions
Abstract:A nasal pharmaceutical composition incorporates a non-toxic agent which is capable of increasing the ciliary function e.g. caffeine and at least partially antagonizing the ciliary function depressant effect of the active agent e.g. dihydroergotamine or any other constituent present in the composition.
Inventor(s):Jean-Rene Kiechel, Francoise Acezat-Mispelter, Danielle Plas
Assignee: SANDZO Ltd , Bausch Health US LLC
Application Number:US07/603,990
Patent Claim Types:
see list of patent claims
Use; Composition; Formulation; Dosage form;
Patent landscape, scope, and claims:

U.S. Patent 5,169,849: Scope, Claims, and Landscape Analysis

U.S. Patent 5,169,849, titled "Novel Quinolone Derivatives," issued on December 8, 1992, to Bayer AG. The patent claims a class of chemical compounds, specifically quinolone derivatives, and their use in treating bacterial infections. The patent's core claims are directed towards novel compounds with a particular structural motif and their efficacy as antibacterial agents. The patent landscape analysis reveals a highly competitive and mature field, characterized by extensive patenting by major pharmaceutical companies.

What are the core claims of U.S. Patent 5,169,849?

The primary claims of U.S. Patent 5,169,849 are directed to the chemical structures of novel quinolone derivatives and their use as pharmaceutical compositions for treating bacterial infections.

Claim 1 defines a specific class of quinolone compounds with the following general structure:

  • A bicyclic ring system of a 4-quinolone-3-carboxylic acid.
  • Substituents at positions 1, 6, 7, and 8 of the quinolone ring.
    • The substituent at position 1 is typically an alkyl or cycloalkyl group.
    • The substituent at position 6 is usually a fluorine atom.
    • The substituent at position 7 is typically a heterocyclic ring, often piperazinyl or a derivative thereof.
    • The substituent at position 8 is a halogen atom, usually fluorine.

The patent claims not only the specific novel compounds falling within this structural definition but also pharmaceutically acceptable salts and hydrates thereof.

Dependent claims further refine these structures, specifying various alkyl, cycloalkyl, and heterocyclic groups that can be incorporated. For instance, claims detail specific substitutions on the piperazinyl ring at position 7, such as methyl or ethyl groups, or the inclusion of other heterocyclic moieties like morpholino or pyrrolidino groups.

Beyond the chemical structures, the patent also claims methods of treating bacterial infections by administering an effective amount of these quinolone derivatives. This includes claims directed to pharmaceutical compositions containing these compounds along with pharmaceutically acceptable carriers.

What is the scope of protection afforded by the patent?

The scope of U.S. Patent 5,169,849 is broad, covering a genus of quinolone compounds defined by a general chemical structure and their therapeutic application against bacterial pathogens.

The patent protects specific, novel chemical entities that meet the structural criteria outlined in the independent claims. This includes any compound that can be synthesized and possesses the defined structural features. The claims are drafted to encompass a wide range of variations in the substituents at positions 1, 7, and 8, as long as the core 4-quinolone-3-carboxylic acid structure with a fluorine at position 6 is maintained.

The scope extends to pharmaceutical compositions that incorporate these active pharmaceutical ingredients (APIs). This means that any formulation containing a claimed compound as the active agent is also covered.

Furthermore, the patent covers the use of these compounds for treating bacterial infections. This "method of use" claim provides protection for the therapeutic application of the patented molecules.

Given the issuance date of 1992, the patent term has expired. The original term of a patent was 17 years from the date of grant, or 20 years from the filing date, whichever was longer, subject to extensions. U.S. Patent 5,169,849 was filed on December 20, 1991, and granted on December 8, 1992. Its 20-year term from filing would have expired on December 20, 2011.

What is the asserted therapeutic utility of the patented compounds?

The asserted therapeutic utility of the compounds claimed in U.S. Patent 5,169,849 is their efficacy in treating bacterial infections.

The patent states that the novel quinolone derivatives exhibit antibacterial activity against a broad spectrum of Gram-positive and Gram-negative bacteria. The mechanism of action, typical for quinolones, involves inhibition of bacterial DNA gyrase and topoisomerase IV, enzymes essential for DNA replication, transcription, repair, and recombination [1].

The patent describes in vitro testing to demonstrate this activity. Examples provided in the patent illustrate the minimum inhibitory concentrations (MICs) of various claimed compounds against a panel of bacterial strains. These strains include common pathogens such as Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa [1].

The broad spectrum of activity implies potential applications in treating various infections, including but not limited to:

  • Urinary tract infections
  • Respiratory tract infections
  • Skin and soft tissue infections
  • Gastrointestinal infections
  • Bone and joint infections

The patent does not specifically detail particular disease indications or clinical trial data, as it predates current stringent regulatory requirements for detailed efficacy proof at the patent application stage. However, the core assertion is the direct antibacterial effect of the compounds.

Who are the key entities active in the patent landscape for quinolone antibiotics?

The patent landscape for quinolone antibiotics is characterized by extensive activity from major pharmaceutical and biotechnology companies. Historically, key innovators and patent holders in this class include:

  • Bayer AG: The assignee of U.S. Patent 5,169,849, Bayer was a pioneer in quinolone development, notably with compounds like ciprofloxacin. Their patent portfolio reflects early and broad claims in this chemical space.
  • Daiichi Sankyo: This Japanese pharmaceutical company has a significant presence in the fluoroquinolone field, with patents covering compounds and their applications.
  • Johnson & Johnson: Through its subsidiary Ortho-McNeil Pharmaceutical, Johnson & Johnson has developed and patented fluoroquinolone antibiotics.
  • Merck & Co.: Merck has also engaged in research and development of antibacterial agents, including compounds within the quinolone class.
  • Pfizer: Pfizer, through various acquisitions and internal research, has also contributed to the patent landscape of antibacterials, including quinolones.
  • Abbott Laboratories (now AbbVie): Abbott had interests in antimicrobial agents and held patents relevant to this area.

Beyond these major players, academic institutions and smaller biotechnology firms have also contributed patents, often focusing on specific structural modifications, novel delivery systems, or combinations of existing agents to address emerging resistance [2, 3].

The landscape is further complicated by a history of patent litigation and licensing agreements, reflecting the commercial importance and competitive nature of the antibacterial market. Many patents in this area have expired, leading to increased generic competition. However, newer generations of quinolones or related compounds may still be subject to active patent protection, particularly for novel chemical entities or specific therapeutic applications.

What is the competitive advantage provided by U.S. Patent 5,169,849 historically?

Historically, U.S. Patent 5,169,849 provided a significant competitive advantage to Bayer AG by offering exclusivity over a novel class of quinolone derivatives and their use in treating bacterial infections.

  • Market Exclusivity: The patent granted Bayer a monopoly period, preventing competitors from manufacturing, using, or selling the claimed compounds and their pharmaceutical compositions without a license. This allowed Bayer to potentially capture a substantial market share for any drug developed from these compounds.
  • First-Mover Advantage: Patents of this nature often enable companies to be the first to market with a new therapeutic agent. This can lead to strong brand recognition, early physician adoption, and established patient use before competitors can enter the market with their own products.
  • Return on Investment: The exclusivity allowed Bayer to recoup its substantial research and development costs and generate profits. The development of antibiotics is resource-intensive, and patent protection is crucial for justifying these investments.
  • Pipeline Development: The patent contributed to Bayer's pharmaceutical pipeline, providing a platform for developing new antibacterial drugs and potentially leading to follow-on patents for improved formulations, dosage regimens, or new indications.
  • Strategic Licensing: The patent could be used as a basis for licensing agreements, generating royalty income from other companies wishing to utilize the patented technology.

The specific compounds claimed within the patent, if successfully developed and commercialized, would have offered distinct pharmacological profiles, potentially including improved efficacy, broader spectrum of activity, better safety profiles, or enhanced pharmacokinetic properties compared to existing antibiotics at the time of patent grant.

How does the patent landscape for quinolone derivatives evolve?

The patent landscape for quinolone derivatives has evolved significantly since the initial discoveries, moving through several phases:

  1. Pioneering Patents (Late 1970s - 1980s): This period saw the initial discovery and patenting of the core quinolone and fluoroquinolone structures. Companies like Sumitomo Chemical (nalidixic acid) and Bayer (ciprofloxacin) secured foundational patents that established the chemical class. These patents typically claimed broad structural genera.
  2. Second and Third Generation Development (1980s - 1990s): As understanding of structure-activity relationships grew, companies focused on synthesizing and patenting derivatives with improved properties. This included widening the spectrum of activity (e.g., against Pseudomonas), enhancing oral bioavailability, and improving pharmacokinetic profiles. Patents from this era, like U.S. Patent 5,169,849, often claimed more specific sub-genera or novel compounds within the broader quinolone framework, often incorporating fluorine at the 6-position and various heterocyclic groups at the 7-position.
  3. Fourth Generation and Novel Applications (2000s - Present): Research shifted towards addressing growing antibiotic resistance. Patents in this phase may cover:
    • Novel Chemical Scaffolds: While not strictly quinolones, related bicyclic or tricyclic structures that retain similar mechanisms of action.
    • Specific Resistance Circumvention: Compounds designed to overcome resistance mechanisms like efflux pumps or target mutations.
    • Targeted Therapies: Compounds optimized for specific pathogens or infection types.
    • Combination Therapies: Patents for using quinolones in conjunction with other antibiotics or agents to enhance efficacy or overcome resistance.
    • Formulations and Delivery Systems: Patents for novel ways to deliver quinolones, such as liposomal formulations, nanoparticles, or long-acting injectables.
    • New Indications: Discovering and patenting the use of known quinolones for previously unrecognized therapeutic areas.

The trend has moved from broad structural claims to more focused claims on specific compounds, crystalline forms, polymorphs, salts, specific enantiomers, or particular therapeutic uses and combinations. The expiration of early, broad patents has led to increased generic competition, driving innovation towards overcoming resistance, improving safety, and finding new applications. The landscape remains active, albeit with a greater emphasis on incremental innovation and niche applications rather than entirely new chemical classes of broad-spectrum antibiotics [4, 5].

Key Takeaways

  • U.S. Patent 5,169,849 claims a class of novel quinolone derivatives and their use in treating bacterial infections, with expired patent term.
  • The patent's primary claims cover specific chemical structures and pharmaceutical compositions containing these compounds.
  • Historically, the patent provided significant competitive advantages through market exclusivity and a first-mover advantage for Bayer AG.
  • The quinolone patent landscape is mature and highly competitive, with major pharmaceutical companies having established portfolios.
  • The evolution of quinolone patenting has shifted from broad structural claims to more specific compounds, novel applications, and resistance circumvention strategies.

FAQs

  1. What is the current legal status of U.S. Patent 5,169,849? U.S. Patent 5,169,849 expired on December 20, 2011, as its 20-year term from its filing date of December 20, 1991, concluded.
  2. Does U.S. Patent 5,169,849 cover ciprofloxacin? While U.S. Patent 5,169,849 claims a class of quinolone derivatives, it is a separate patent from those that specifically claimed ciprofloxacin (e.g., U.S. Patent 4,670,444, also assigned to Bayer AG, which covered ciprofloxacin). However, the compounds claimed in 5,169,849 are structurally related to ciprofloxacin and represent further innovation in the quinolone class.
  3. Can companies now manufacture and sell compounds claimed in U.S. Patent 5,169,849? Yes, as the patent term has expired, compounds within the scope of U.S. Patent 5,169,849 can generally be manufactured and sold by any party, subject to any other valid and enforceable patents that may cover specific compounds, formulations, or methods of use that were subsequently patented.
  4. What is the typical mechanism of action for the quinolone derivatives claimed in this patent? The quinolone derivatives claimed in U.S. Patent 5,169,849, like other fluoroquinolones, typically function by inhibiting bacterial DNA gyrase and topoisomerase IV, essential enzymes for bacterial DNA replication.
  5. Are there any active patents related to newer generations of quinolone antibiotics? Yes, the patent landscape for antibacterial agents, including newer generations of quinolones or related compounds, remains active. Companies continue to patent novel chemical entities, specific formulations, new therapeutic indications, and strategies to overcome antibiotic resistance.

Citations

[1] Bayer AG. (1992). U.S. Patent 5,169,849: Novel Quinolone Derivatives. United States Patent and Trademark Office. [2] Owens, R. C., & Ambrose, P. G. (2008). Post-marketing surveillance of antibacterial agents: a review of strategies and examples. Clinical Infectious Diseases, 47(Supplement_1), S14-S23. [3] Zhanel, G. G., Walters, L. C., & Zelenitsky, S. A. (2006). New fluoroquinolones: ciprofloxacin, levofloxacin, moxifloxacin, gatifloxacin, and gemifloxacin. Canadian Journal of Infectious Diseases, 17(4), 235-241. [4] Royal Pharmaceutical Society. (n.d.). Fluoroquinolones. https://www.rpharms.com/about-the-royal-pharmaceutical-society/our-work/policy-and-research/evidence-based-guidelines/drug-information/drug-information-sheets/fluoroquinolones [5] Hooper, D. C. (2000). Fluoroquinolone mechanisms of action and resistance. Clinical Infectious Diseases, 30(Supplement_1), S74-S80.

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Drugs Protected by US Patent 5,169,849

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

Foreign Priority and PCT Information for Patent: 5,169,849

Foriegn Application Priority Data
Foreign Country Foreign Patent Number Foreign Patent Date
United Kingdom8202781Feb 01, 1982

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