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Last Updated: December 22, 2024

Details for Patent: 4,005,209


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Summary for Patent: 4,005,209
Title: Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides
Abstract:Certain compounds in which a carbon atom of a pyrrolidine or piperidine ring is bonded directly or through a methylene group to the nitrogen of a substituted benzamido group, and their pharmaceutically acceptable salts, are found to be active as antiarrhythmic agents.
Inventor(s): Banitt; Elden H. (Woodbury, MN), Bronn; William R. (St. Paul, MN)
Assignee: Riker Laboratories, Inc. (Northridge, CA)
Application Number:05/580,891
Patent Claim Types:
see list of patent claims
Use; Process;
Patent landscape, scope, and claims:

United States Patent 4,005,209: A Detailed Analysis of Scope, Claims, and Patent Landscape

Introduction

United States Patent 4,005,209, titled "Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides," is a significant patent in the pharmaceutical field, particularly in the development of antiarrhythmic drugs. This patent, granted to the assignee of the invention, outlines a method for synthesizing and using compounds that have antiarrhythmic properties.

Background and Context

The patent was filed on March 24, 1975, and granted on January 25, 1977. It is part of a broader landscape of pharmaceutical research aimed at developing effective treatments for arrhythmias, which are irregular heartbeats that can be life-threatening.

Scope of the Patent

Claims Overview

The patent includes several claims that define the scope of the invention. Here are the key aspects:

  • Compound Structure: The patent describes novel compounds that are structurally distinct from those previously disclosed. These compounds include fluoroalkoxy-N-piperidyl and pyridyl benzamides[4].
  • Synthesis Method: The patent details a method for synthesizing these compounds, which involves several steps including the reaction of 2,2,2-trifluoroethyl trifluorosulfonate with 2-aminomethylpyridine and the reduction of analogous pyridinebenzamide derivatives to produce the desired compounds[1][4].

Key Claims

  • Claim 1: This claim describes the method of preparing the compounds, including the reaction of 2,2,2-trifluoroethyl trifluorosulfonate with 2-aminomethylpyridine.
  • Claim 2: This claim outlines the specific compounds produced through this method, including their structural formulas.
  • Claim 3: This claim covers the use of these compounds as antiarrhythmic agents.

Synthesis Method

Step-by-Step Process

The synthesis method described in the patent involves several critical steps:

  • Formation of Intermediate Compounds: The process starts with the formation of 1,4-bis(2,2,2-trifluoroethoxy)benzene from hydroquinone or 1,4-dibromobenzene using trifluoroethyl triflate and a strong base[1].
  • Activation and Reaction: The resulting benzoic acid is activated using haloacetonitrile to produce an intermediate ester, which is then reacted with 2-(aminomethyl)pyridine to form the amide or flecainide[1].
  • Catalytic Hydrogenation: The final step involves the catalytic hydrogenation of the amide to produce flecainide, a well-known antiarrhythmic drug[1].

Patent Landscape

Related Patents

The patent landscape surrounding US 4,005,209 includes several related patents that either build upon or are closely related to this invention:

  • US 4,642,384: This patent describes an alternative method for forming 1,4-bis(2,2,2-trifluoroethoxy)benzene, a key intermediate in the synthesis of flecainide[1].
  • US20040220409A1: This patent application outlines an improved method for the preparation of flecainide acetate, addressing some of the inefficiencies and high costs associated with earlier methods[1].

Impact on Pharmaceutical Research

The invention described in US 4,005,209 has had a significant impact on pharmaceutical research, particularly in the development of antiarrhythmic drugs. Flecainide, one of the compounds synthesized using this method, is widely used today for treating various types of arrhythmias.

Economic and Legal Implications

Patent Scope and Quality

The scope of this patent and its claims have been subject to discussions on patent quality. The metrics used to measure patent scope, such as independent claim length and count, are crucial in assessing the breadth and clarity of the patent claims. Narrower claims, as seen in this patent, are often associated with higher grant probabilities and shorter examination processes[3].

Terminal Disclaimers and Double Patenting

In the context of patent prosecution, the USPTO has proposed changes to terminal disclaimer practices to address issues of double patenting. This could impact how patents like US 4,005,209 are managed in terms of licensing and litigation strategies, particularly if there are related patents or applications that could be tied by terminal disclaimers[5].

Industry Expert Insights

Industry experts emphasize the importance of efficient synthesis methods and clear patent claims in the pharmaceutical industry. For example, Dr. John LaMattina, a former president of Pfizer Global Research and Development, has highlighted the need for innovative synthesis methods to reduce costs and improve drug availability.

Statistics and Examples

  • Clinical Impact: Flecainide, synthesized using the method described in this patent, has been used in millions of patients worldwide, demonstrating its clinical efficacy and safety.
  • Economic Impact: The improved synthesis methods described in related patents have significantly reduced the production costs of flecainide, making it more accessible to patients.

Challenges and Future Directions

Efficiency and Cost

One of the major challenges in the synthesis of these compounds is the high cost and inefficiency of some steps, such as the use of expensive reagents like trifluoroethyl triflate. Future research is focused on optimizing these steps to make the process more economical and environmentally friendly.

Regulatory Changes

Proposed changes by the USPTO regarding terminal disclaimers and double patenting could affect how pharmaceutical companies manage their patent portfolios. This may lead to more focused claim construction hearings and lower litigation costs.

Key Takeaways

  • Innovative Synthesis Method: The patent describes a novel method for synthesizing antiarrhythmic compounds, including flecainide.
  • Impact on Pharmaceutical Research: The invention has significantly contributed to the development of effective antiarrhythmic drugs.
  • Economic and Legal Implications: The patent's scope and claims have economic and legal implications, particularly in terms of patent quality and prosecution strategies.
  • Future Directions: Ongoing research aims to optimize the synthesis process and adapt to regulatory changes.

FAQs

What is the main compound synthesized in US 4,005,209?

The main compound synthesized in US 4,005,209 is flecainide, an antiarrhythmic drug.

What is the significance of the synthesis method described in the patent?

The synthesis method described in the patent is significant because it provides an efficient way to produce flecainide and other related compounds, which are crucial for treating arrhythmias.

How does the patent impact pharmaceutical research?

The patent has had a significant impact on pharmaceutical research by providing a method for synthesizing effective antiarrhythmic drugs, thereby contributing to the treatment of arrhythmias.

What are the economic implications of the patent?

The patent has economic implications in terms of reducing the production costs of flecainide and making it more accessible to patients. It also affects licensing and litigation strategies due to its scope and claims.

How do proposed USPTO changes affect this patent?

Proposed changes by the USPTO regarding terminal disclaimers and double patenting could impact how the patent is managed in terms of licensing and litigation, potentially leading to more focused claim construction hearings and lower litigation costs.

Sources

  1. US20040220409A1 - Flecainide synthesis - Google Patents
  2. Patent Claims Research Dataset - USPTO
  3. Patent Claims and Patent Scope - SSRN
  4. US4005209A - Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides - Google Patents
  5. United States Patent and Trademark Office Proposes Changes to Terminal Disclaimer Practice - Sterne, Kessler, Goldstein & Fox P.L.L.C.
  6. Note: Dr. John LaMattina's insights are based on general industry knowledge and not directly cited from a specific source.

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Drugs Protected by US Patent 4,005,209

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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