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Last Updated: January 3, 2025

Details for Patent: 4,089,969


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Summary for Patent: 4,089,969
Title: 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof
Abstract:Novel 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid compounds represented by the formula ##STR1## and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein R is hydrogen or a lower alkyl group containing from 1 to 4 carbon atoms and R.sup.1 is hydrogen, a lower alkyl group having from 1 to 4 carbon atoms, a lower alkoxy group of 1 to 4 carbon atoms, chloro, fluoro or bromo, the R.sup.1 substitution being at the ortho, meta or para positions of the aroyl group and process for the production of such compounds; 5-p-toluoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid is representative of the class. These compounds, as the racemic mixture or the (1)-isomer, are useful as anti-inflammatory, analgesic and antipyretic agents and as smooth muscle relaxants.
Inventor(s): Muchowski; Joseph M. (Mexico City, MX), Kluge; Arthur F. (Los Altos, CA)
Assignee: Syntex (U.S.A.) Inc. (Palo Alto, CA)
Application Number:05/771,286
Patent Claim Types:
see list of patent claims
Compound; Use; Composition; Delivery;
Patent landscape, scope, and claims:

Detailed Analysis of the Scope and Claims of United States Patent 4,089,969

Introduction

United States Patent 4,089,969, titled "5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof," is a significant patent in the field of pharmaceuticals. This patent, issued on May 16, 1978, covers novel compounds and their production processes, which have been utilized in various medical applications.

Background and Context

The patent is part of a broader category of pharmaceutical inventions that focus on the development of new compounds with therapeutic properties. The specific compounds described in this patent are 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids, which exhibit anti-inflammatory, analgesic, and anti-pyretic activities[4].

Scope of the Patent

Chemical Compounds

The patent describes novel 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids, including their individual (l)-acid isomers and (d)-acid isomers, as well as their pharmaceutically acceptable esters and salts. These compounds are represented by a specific formula where R and R1 can vary, allowing for a range of derivatives[4].

Production Process

The patent outlines a detailed process for the production of these compounds. This includes the synthesis of key intermediates through selective esterification and decarboxylation reactions. The process involves treating the carboxylic acid group with lower aliphatic alcohols in the presence of hydrogen chloride, followed by heating to achieve decarboxylation[4].

Claims

The patent includes several claims that define the scope of protection:

Compound Claims

  • Claims cover the novel 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and their isomers.
  • Specific claims are made for the pharmaceutically acceptable esters and salts of these compounds[4].

Process Claims

  • Claims are made for the method of producing these compounds, including the steps of selective esterification and decarboxylation.
  • The process claims cover the conditions and reagents used in the synthesis, such as the use of lower aliphatic alcohols and the temperature range for decarboxylation[4].

Patent Landscape

Related Patents and Extensions

The patent has been referenced in various contexts, including patent term extensions. For instance, patents related to pharmaceutical products often undergo term extensions due to regulatory reviews by the FDA, as outlined in 35 U.S.C. 156(e)(1)[2].

Industry Applications

The compounds described in this patent have been used in human therapy as analgesics and anti-inflammatory agents. For example, ketorolac, a compound related to the ones described in this patent, is used in therapeutic compositions for intranasal administration[1].

Competitive Landscape

The patent landscape in the pharmaceutical sector is highly competitive, with numerous patents covering various aspects of drug discovery and development. Patent analytics tools are often used to track and analyze the claims and scope of patents to identify gaps and opportunities in intellectual property protection[3].

Impact and Utilization

Therapeutic Uses

The compounds and processes described in this patent have significant therapeutic applications. They are used to elicit physiological responses such as anti-inflammatory, analgesic, or anti-pyretic activities, making them valuable in medical treatments[4].

Commercial Significance

The commercial significance of this patent lies in its contribution to the development of new pharmaceutical products. Companies like Roxro Pharma, Inc., which have been associated with related patents, benefit from the intellectual property protection provided by such patents[1].

Legal Status and Maintenance

The patent has expired, as indicated by its legal status. However, understanding the history and maintenance of such patents is crucial for companies to navigate the patent landscape effectively. This includes tracking payment histories and any extensions or amendments made during the patent's lifetime[1].

Conclusion

United States Patent 4,089,969 is a pivotal patent in the pharmaceutical industry, covering novel compounds and their production processes. Its scope includes specific chemical compounds and their therapeutic applications, as well as detailed process claims. Understanding this patent's claims and the broader patent landscape is essential for companies involved in drug development and intellectual property management.

Key Takeaways

  • Novel Compounds: The patent covers 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and their derivatives.
  • Production Process: Detailed steps for the synthesis of these compounds, including selective esterification and decarboxylation.
  • Therapeutic Applications: The compounds exhibit anti-inflammatory, analgesic, and anti-pyretic activities.
  • Patent Landscape: Part of a competitive landscape with related patents and extensions.
  • Commercial Significance: Contributes to the development of new pharmaceutical products and provides intellectual property protection.

FAQs

What are the main compounds covered by this patent?

The main compounds are 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids, including their isomers and pharmaceutically acceptable esters and salts[4].

What is the production process outlined in the patent?

The process involves selective esterification with lower aliphatic alcohols and decarboxylation at elevated temperatures[4].

What are the therapeutic applications of these compounds?

The compounds exhibit anti-inflammatory, analgesic, and anti-pyretic activities, making them useful in medical treatments[4].

Is the patent still active?

No, the patent has expired. It was issued on May 16, 1978, and has since reached the end of its term[1].

How does this patent fit into the broader patent landscape?

It is part of a competitive landscape in the pharmaceutical sector, with related patents and extensions often being tracked and analyzed using patent analytics tools[3].

Cited Sources

  1. Canadian Patents Database: Therapeutic compositions for intranasal administration of ketorolac.
  2. United States Patent and Trademark Office: Extension Under 35 U.S.C. 156(e)(1).
  3. SLWIP: Patent Analytics.
  4. Google Patents: 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof.

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Drugs Protected by US Patent 4,089,969

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

International Family Members for US Patent 4,089,969

Country Patent Number Estimated Expiration Supplementary Protection Certificate SPC Country SPC Expiration
Argentina 224997 ⤷  Subscribe
Austria 363465 ⤷  Subscribe
Austria 364844 ⤷  Subscribe
Austria 369003 ⤷  Subscribe
Austria A402479 ⤷  Subscribe
Austria A509077 ⤷  Subscribe
>Country >Patent Number >Estimated Expiration >Supplementary Protection Certificate >SPC Country >SPC Expiration

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