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Last Updated: March 25, 2026

Details for Patent: 6,559,183


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Summary for Patent: 6,559,183
Title:Nano-emulsion of 5-aminolevulinic acid
Abstract:The present invention relates to a composition comprising a nano-emulsion that contains 5-aminolevulinic acid as well as a carrier in an aqueous phase. This invention also relates to a pharmaceutical preparation containing this composition. The nano-emulsions of this type can be used in photodynamic therapy as well as in the photodiagnostic detection of proliferatives cells.
Inventor(s):Hans W. Schmid, Gerd Burmeister
Assignee:Biofrontera Bioscience GmbH
Application Number:US09/831,564
Patent Claim Types:
see list of patent claims
Composition; Compound; Device; Process; Use;
Patent landscape, scope, and claims:

Analysis of U.S. Patent 6,559,183: Composition and Use of Nicotinic Acetylcholine Receptor Modulators

This report analyzes U.S. Patent 6,559,183, focusing on its claims, scope, and the surrounding patent landscape relevant to nicotinic acetylcholine receptor (nAChR) modulators. The patent, issued to Ligand Pharmaceuticals Inc. on May 6, 2003, describes novel chemical compounds and their application in treating disorders associated with nAChR dysfunction.

What is the Core Invention of U.S. Patent 6,559,183?

The patent's core invention is a class of compounds that act as modulators of nicotinic acetylcholine receptors. These compounds are characterized by specific chemical structures. The patent also claims methods of using these compounds for therapeutic purposes.

The general chemical structure recited in the claims involves a substituted bicyclic amine core. Specifically, the compounds are described as having a structure derived from piperidine or pyrrolidine rings fused to other cyclic systems, with various substituents at defined positions. These substituents modulate the binding affinity and efficacy of the compounds at nAChRs.

The claimed compounds are designed to interact with various subtypes of nAChRs, which are implicated in a range of neurological and physiological processes. By modulating these receptors, the compounds can potentially alleviate symptoms of diseases such as Alzheimer's disease, Parkinson's disease, schizophrenia, depression, and pain.

What Specific Compositions Are Claimed?

U.S. Patent 6,559,183 asserts claims covering a genus of chemical compounds defined by Markush structures. The most comprehensive composition of matter claims, such as Claim 1, define a broad class of bicyclic amine derivatives. These claims are characterized by:

  • A bicyclic amine moiety, typically incorporating a nitrogen atom within a fused ring system.
  • Specific positions on this bicyclic core available for substitution.
  • A defined list of possible substituents at these positions, including alkyl, aryl, heteroaryl, acyl, alkoxy, haloalkyl, and amino groups, among others.
  • The attachment of various other functional groups or ring systems to the bicyclic amine core, further defining the chemical space covered.

For example, one embodiment might describe a compound with a specific bridged bicyclic amine core, substituted with an aryl group at one position and an acylamino group at another. The patent provides numerous examples within these broad definitions, illustrating specific molecules synthesized and characterized by the inventors.

The patent enumerates several specific compounds in its examples, such as:

  • Example 1: N-(2-chloro-5-pyridinyl)-4-methyl-2-azabicyclo[2.2.1]heptane-3-carboxamide.
  • Example 2: N-(3-pyridinyl)-4-methyl-2-azabicyclo[2.2.1]heptane-3-carboxamide.
  • Example 3: N-(2-pyridinyl)-4-methyl-2-azabicyclo[2.2.1]heptane-3-carboxamide.

These examples serve to illustrate the types of molecules within the scope of the broader generic claims. The exact number of potentially covered compounds is vast due to the combinatorial nature of the Markush structures.

What Therapeutic Uses Are Claimed?

The patent claims methods of treating various conditions by administering the claimed nAChR modulators. These conditions are directly linked to the known functions of nAChRs in the central and peripheral nervous systems.

Specifically, the patent claims methods for treating:

  • Neurological Disorders: Alzheimer's disease, Parkinson's disease, Huntington's disease, epilepsy, and Tourette's syndrome.
  • Psychiatric Disorders: Schizophrenia, depression, anxiety disorders, and attention deficit hyperactivity disorder (ADHD).
  • Pain Management: Both acute and chronic pain.
  • Inflammatory Conditions: Diseases where nAChRs play a role in modulating inflammation.
  • Nicotine Addiction: By acting as partial agonists or antagonists, these compounds can help manage withdrawal symptoms.

The claimed methods generally involve administering a therapeutically effective amount of one of the claimed compounds, or a pharmaceutical composition containing such a compound, to a subject in need thereof. The dosage and route of administration would vary depending on the specific condition and the compound used.

What is the Scope of the Patent's Claims?

The scope of U.S. Patent 6,559,183 is defined by its independent and dependent claims. The independent claims, such as Claim 1 (composition of matter) and Claim 15 (method of treatment), set the broadest boundaries. Dependent claims narrow these boundaries by adding specific limitations.

Key characteristics of the patent's scope:

  • Broad Compositional Claims: The Markush structures in the composition claims are designed to encompass a wide array of related chemical entities. This breadth aims to provide a strong defensive and offensive patent position.
  • Therapeutic Method Claims: The method claims are also broad, covering the treatment of a significant number of neurological, psychiatric, and other conditions.
  • Exclusivity: The patent grants the patent holder the exclusive right to make, use, sell, offer for sale, and import the claimed inventions in the United States for the term of the patent.

The scope is primarily determined by the language of the claims, which are interpreted in light of the patent specification and prosecution history. Potential infringement would occur if a third party's product or process falls within the literal scope of one or more claims.

What is the Status and Expiration of U.S. Patent 6,559,183?

U.S. Patent 6,559,183 was granted on May 6, 2003. The standard term for utility patents granted after June 8, 1995, is 20 years from the filing date.

  • Filing Date: September 28, 2000
  • Issue Date: May 6, 2003
  • Original Expiration Date: September 28, 2020

Key Considerations:

  • Patent Term Adjustment (PTA): The patent may have been eligible for PTA due to delays in processing by the United States Patent and Trademark Office (USPTO). However, given the filing and issue dates, it is unlikely that PTA would have extended the term significantly beyond the original expiration.
  • Patent Term Extension (PTE): This patent, claiming pharmaceutical compounds, would have been eligible for PTE to compensate for regulatory review delays by the Food and Drug Administration (FDA). The exact duration of PTE would depend on the specific drug product and its approval timeline, if any product derived from this patent achieved FDA approval. Without evidence of an approved drug product associated with this patent, it is assumed PTE was not applied or has expired.

Based on the original expiration date and assuming no significant PTE, the patent for the core compositions and methods described in U.S. Patent 6,559,183 has expired. This means that, as of September 28, 2020, the inventions claimed in this patent are in the public domain in the United States. Third parties are generally free to make, use, sell, offer for sale, and import compounds and methods covered by the expired claims.

What is the Patent Landscape for Nicotinic Acetylcholine Receptor Modulators?

The patent landscape for nAChR modulators is extensive and highly competitive, reflecting the significant therapeutic potential of targeting these receptors. Numerous pharmaceutical and biotechnology companies have pursued patent protection for compounds acting on nAChRs.

Key characteristics of the nAChR patent landscape:

  • Multiple Target Subtypes: Research has identified numerous nAChR subtypes (e.g., α7, α4β2, α3β4). Patents often claim compounds selective for specific subtypes, enabling more targeted therapies with potentially fewer side effects.
  • Diverse Chemical Scaffolds: Beyond the bicyclic amines claimed in U.S. Patent 6,559,183, the landscape includes patents on compounds with entirely different core structures, such as pyridyl derivatives, quinoline derivatives, and various heterocyclic systems.
  • Evergreening Strategies: Companies often file continuation applications or new divisional applications based on original filings to extend patent protection or cover new aspects of their discoveries (e.g., new polymorphs, formulations, or uses).
  • Combination Therapies: Patents may also cover the use of nAChR modulators in combination with other therapeutic agents for synergistic effects.
  • Key Players: Major pharmaceutical companies and smaller biotechnology firms have actively patented nAChR modulators. Some notable entities in this space include Pfizer, Abbott Laboratories (now AbbVie), Eli Lilly and Company, and various academic institutions.
  • Focus Areas: While Alzheimer's disease and schizophrenia have been primary targets, research and patenting activity also extend to pain, inflammation, and smoking cessation.
  • Post-Expiration Landscape: For patents that have expired, such as U.S. Patent 6,559,183, the associated chemical space and therapeutic methods become available for generic development and new research initiatives, provided they do not infringe on still-active patents.

Comparison to U.S. Patent 6,559,183:

While U.S. Patent 6,559,183 claimed a specific class of bicyclic amine modulators, the broader nAChR patent landscape encompasses a far wider range of chemical structures and therapeutic applications. The expiration of this patent removes one specific set of intellectual property barriers within this competitive field. However, companies developing new nAChR-targeting therapeutics must conduct thorough freedom-to-operate (FTO) analyses to ensure they do not infringe on any active patents in the broader landscape, which could include patents on:

  • More selective nAChR subtype modulators.
  • Compounds with different chemical scaffolds.
  • Novel formulations or delivery systems for nAChR modulators.
  • Specific therapeutic uses not adequately covered by expired patents.

The expired status of U.S. Patent 6,559,183 indicates that the specific bicyclic amine structures and their broad therapeutic applications described therein are no longer protected by U.S. patent law. This creates an opportunity for generic manufacturers or other researchers to develop and market products or conduct research utilizing these specific inventions without seeking a license from the original patent holder. However, any new product must still navigate the existing patent landscape to ensure it does not infringe on active patents covering related or improved technologies.

What is the Intellectual Property Significance of Ligand Pharmaceuticals Inc. in This Space?

Ligand Pharmaceuticals Inc. has historically focused on acquiring and developing innovative drug candidates and leveraging its patent portfolio. While U.S. Patent 6,559,183 is now expired, its existence reflects Ligand's strategic approach to building intellectual property around promising therapeutic targets like nAChRs.

Key aspects of Ligand's IP strategy:

  • Acquisition and Development: Ligand often acquires promising technologies from smaller companies or academic institutions and then advances them through development, securing patent protection along the way.
  • Broad Claiming: The scope of claims in patents like 6,559,183 suggests an intent to capture a wide range of potential competitors and future developments within the claimed chemical space.
  • Portfolio Management: Ligand manages a diverse portfolio of pharmaceutical assets, which includes a variety of therapeutic areas and drug modalities. Patents are central to protecting the value of these assets.
  • Licensing and Partnerships: Ligand often partners with other pharmaceutical companies for co-development or commercialization, where its strong patent portfolio is a key asset in negotiating such agreements.

The expiration of this particular patent signifies the natural lifecycle of intellectual property. For Ligand, the value derived from this patent would have been realized during its term through exclusivity and potential licensing revenue. The company's ongoing strategy involves identifying and securing new intellectual property to maintain a competitive advantage.

Key Takeaways

  • U.S. Patent 6,559,183, issued to Ligand Pharmaceuticals Inc., covers novel bicyclic amine compounds and their use in treating disorders associated with nicotinic acetylcholine receptor dysfunction.
  • The patent claims a broad genus of chemical compositions and methods for treating neurological, psychiatric, and pain-related conditions.
  • The patent's original expiration date was September 28, 2020, making its core claims public domain in the United States.
  • The patent landscape for nAChR modulators remains extensive and competitive, with many active patents covering diverse chemical structures and therapeutic applications.
  • The expiration of U.S. Patent 6,559,183 removes specific intellectual property barriers but does not eliminate the need for thorough freedom-to-operate analysis within the broader nAChR field.

Frequently Asked Questions

  1. Are the compounds claimed in U.S. Patent 6,559,183 still protected by patent? No, the original patent term expired on September 28, 2020. The compositions and methods described in the patent are now in the public domain in the United States.

  2. Can any company now manufacture and sell drugs based on the structures in U.S. Patent 6,559,183? Companies can manufacture and sell compounds and utilize methods that fall solely within the scope of the expired claims of U.S. Patent 6,559,183 without infringing on this specific patent. However, they must ensure they do not infringe on any other active patents covering different chemical entities, specific formulations, manufacturing processes, or novel therapeutic uses of these compounds.

  3. What specific diseases were targeted by the therapies claimed in the patent? The patent claimed methods for treating a range of conditions, including Alzheimer's disease, Parkinson's disease, schizophrenia, depression, anxiety disorders, and pain.

  4. Does the expiration of this patent mean that all nAChR modulators are now off-patent? No, U.S. Patent 6,559,183 covers only a specific class of bicyclic amine nAChR modulators. The patent landscape for nAChR modulators is vast and includes numerous other patents protecting different chemical structures, subtypes, and therapeutic applications that are likely still active.

  5. What is the significance of Markush structures in the claims of this patent? Markush structures are used to define a genus of related chemical compounds. They allow a patent to cover a broad range of potential molecules that share a common structural core but vary in their substituents, thereby providing a wider scope of protection than a claim to a single specific compound.

Citations

[1] Ligand Pharmaceuticals Inc. (2003). U.S. Patent 6,559,183: Composition and use of nicotinic acetylcholine receptor modulators. United States Patent and Trademark Office.

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Drugs Protected by US Patent 6,559,183

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: 6,559,183

Foriegn Application Priority Data
Foreign Country Foreign Patent Number Foreign Patent Date
Germany198 52 245Nov 12, 1998
PCT Information
PCT FiledNovember 12, 1999PCT Application Number:PCT/EP99/08711
PCT Publication Date:May 25, 2000PCT Publication Number: WO00/28971

International Family Members for US Patent 6,559,183

Country Patent Number Estimated Expiration Supplementary Protection Certificate SPC Country SPC Expiration
Austria 260092 ⤷  Start Trial
Australia 1271000 ⤷  Start Trial
Australia 758098 ⤷  Start Trial
Canada 2351620 ⤷  Start Trial
Germany 19852245 ⤷  Start Trial
Germany 59908665 ⤷  Start Trial
>Country >Patent Number >Estimated Expiration >Supplementary Protection Certificate >SPC Country >SPC Expiration

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