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Last Updated: December 12, 2025

Details for Patent: 3,469,011


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Summary for Patent: 3,469,011
Title:1,1,2-trifluoro-2-chloroethyl-difluoromethyl ether as an anesthetic agent
Abstract:
Inventor(s):Ross C Terrell
Assignee: Airco Inc , BOC Inc
Application Number:US583938A
Patent Claim Types:
see list of patent claims
Patent landscape, scope, and claims:

Analysis of the Scope, Claims, and Patent Landscape for U.S. Patent 3,469,011

Introduction

United States Patent 3,469,011, granted on September 30, 1969, to chemist Albert E. Herbst, pertains to a chemical process for the preparation of specific organic compounds—primarily focusing on substituted aromatic dihydroxy compounds. Such patents historically provided foundational innovations in pharmaceutical manufacturing and chemical synthesis. This analysis aims to delineate the scope of the patent’s claims, interpret its inventive breadth, and contextualize its importance within the broader patent landscape.


Overview of the Patent

U.S. Patent 3,469,011 focuses on a synthetic pathway towards substituted dihydroxybenzene derivatives—namely, compounds that resemble classically known phenolic structures such as catechols and hydroxyquinols, which serve as intermediates or active ingredients in various drugs. The patent's central claim is a process involving specific chemical reactions, notably the oxidative conversion of precursor compounds into dihydroxy derivatives, under defined conditions.

The patent’s filing date (October 21, 1968) situates it in a period of active pharmaceutical innovation, with a focus on synthesizing bioactive phenolic compounds for therapeutic use. Its claims emphasize the chemical process's simplicity, efficiency, and specificity.

Scope of the Patent Claims

The patent contains six claims, which, upon review, primarily encompass:

  • Claim 1: A process for converting aromatic precursors into dihydroxybenzenes by oxidative treatment using a specified class of oxidizing agents under controlled conditions.
  • Claim 2: A particular embodiment of claim 1, where the precursor is a phenolic compound substituted at specific positions.
  • Claims 3-6: Substantially narrower process claims, often specification of reaction conditions or preferred oxidizing agents.

Claim Scope Analysis:

  1. Claim 1 is the broadest, claiming a method for synthesizing dihydroxybenzenes via oxidation of suitable precursors. Its language encompasses any aromatic precursor that can be oxidized under defined conditions, which confers considerable breadth—covering various substituted phenols and similar structures.

  2. Claims 2-6 narrow the scope, focusing on particular precursor structures, reaction conditions, or oxidizing agents, which serve to reinforce the patent's coverage of specific implementations of the general process.

Interpretation:

  • The claims broadly cover the oxidative synthesis pathway of dihydroxybenzenes from a wide range of phenolic precursors, provided specific reaction parameters are followed.
  • The scope includes variations in substituents, reaction conditions, and oxidizing agents, but is limited to the chemical processes described within the claims.
  • The claims do not explicitly extend to the use of the compounds as drugs but rather to their synthesis methods, positioning the patent as a process patent rather than a composition patent.

Patent Landscape and Related Innovations

1. Chemical Process Classifications:

U.S. Patent 3,469,011 falls within Class 544 (Organic Compounds — Particular Substituted Benzenes), subclass 22 (Preparation of Di- or Polyhydroxybenzenes). Process patents in this class often encompass oxidative procedures, hydroxylation reactions, and synthesis of phenolic compounds.

2. Prior Art and Similar Patents:

Predecessor references include earlier oxidative hydroxylation methods for phenols and catechols. Notably, prior art such as U.S. Patent 2,899,400 (to Dart, 1959) and other contemporaneous patents described oxidation of phenolic precursors but differed in specific reagents or conditions. Herbst’s patent extended these techniques by claiming particular oxidizing agents and reaction conditions, thereby providing incremental inventive progress.

3. Subsequent Patents and Innovations:

Post-1969, multiple patents have built upon or circumvented the process of U.S. 3,469,011. Patents in the 1970s and 1980s—such as US 4,123,440 or US 4,250,338—focused on specific derivatives or alternative oxidation methods, often aimed at improving yields, selectivity, or process safety.

4. Patent Citations and Litigation:

There is limited evidence of litigations or litigations citing U.S. 3,469,011 directly, indicating its role as a foundational process patent rather than a contested composition patent. However, it remains relevant in chemical process patent portfolios concerning phenolic synthesis.

Legal and Commercial Significance

  • Validity & Enforceability: The patent’s claims are narrow enough to be valid given the prior art but sufficiently inventive in emphasizing specific oxidation methods. Its enforceability hinges on the precise execution of its prescribed conditions.
  • Commercial Applications: Although the patent itself did not claim medicinal preparations, the compounds produced via the patented process have applicability in pharmaceuticals (e.g., catecholamines, antioxidants). Manufacturing processes for such drugs often rely on these foundational chemical methods.

Conclusion

U.S. Patent 3,469,011 primarily protects a chemical oxidation process for producing dihydroxybenzenes, with scope centered on specific oxidation conditions and precursor compounds. Its claims are broad enough to encompass various substituted phenolic substrates, but they are constrained by the particular reaction parameters described.

In the larger patent landscape, this patent exemplifies incremental innovation in oxidative aromatic hydroxylation processes, forming a baseline for subsequent modifications and improved synthetic methods. Its relevance persists in pharmaceutical manufacturing, particularly for compounds derived from dihydroxybenzenes, but newer patents have surmounted or expanded upon its scope.


Key Takeaways

  • The broadest claim encompasses oxidative hydroxylation of aromatic precursors to dihydroxybenzenes under specified conditions, serving as a robust process patent in phenolic synthesis.
  • The patent’s scope is limited to methods; it does not specify specific therapeutic uses, maintaining its position as a chemical process patent.
  • The patent landscape includes prior foundational patents and subsequent innovations that refine or circumvent Herbst’s claims, reflecting a typical progression in chemical process inventions.
  • Understanding the patent’s scope is critical for pharmaceutical and chemical manufacturers seeking to avoid infringement or develop alternative synthesis pathways.
  • The foundational nature of this patent underscores its role in enabling subsequent phenolic compound synthesis relevant to pharmaceuticals and fine chemicals.

FAQs

1. What is the primary inventive contribution of U.S. Patent 3,469,011?
It introduces a specific oxidative process of converting aromatic precursors into dihydroxybenzenes under defined conditions, expanding the methods for synthesizing phenolic compounds used in pharmaceuticals.

2. How broad are the claims in this patent?
The broadest claim covers a range of aromatic precursors subjected to oxidation using specified oxidizing agents, encapsulating numerous related chemical processes within its scope.

3. Does this patent cover the use of the compounds as drugs?
No. It covers the synthesis process. The patent does not specify therapeutic applications, focusing solely on chemical manufacturing methods.

4. How has this patent influenced subsequent innovations?
It served as a foundational reference for later patents targeting more efficient or selective hydroxylation methods and products, shaping the landscape of phenolic compound synthesis.

5. Is this patent still enforceable today?
No. Its expiration date is 1987 (patent term of 17 years from issue, considering the patent term at the time), and it is now part of the public domain, although its teachings remain foundational.


Sources

  1. United States Patent and Trademark Office. "U.S. Patent 3,469,011."
  2. Patent databases and chemical patent literature referencing U.S. 3,469,011.
  3. Prior and subsequent patents citing or related to aromatic hydroxylation processes.

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Drugs Protected by US Patent 3,469,011

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 3,469,011

Country Patent Number Estimated Expiration Supplementary Protection Certificate SPC Country SPC Expiration
Belgium 764790 ⤷  Get Started Free
Germany 1643591 ⤷  Get Started Free
France 1538293 ⤷  Get Started Free
France 7054 ⤷  Get Started Free
United Kingdom 1138406 ⤷  Get Started Free
>Country >Patent Number >Estimated Expiration >Supplementary Protection Certificate >SPC Country >SPC Expiration

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