United States Drug Patent 5,563,142: Scope and Claims Analysis

This report analyzes United States Patent 5,563,142, titled "Process for the Preparation of N-(4-hydroxyphenyl)glycinamide derivatives," focusing on its scope, claims, and the surrounding patent landscape. The patent describes a process for synthesizing specific N-(4-hydroxyphenyl)glycinamide derivatives, particularly those used as active pharmaceutical ingredients.

What is the Core Invention of Patent 5,563,142?

Patent 5,563,142 details a novel and improved process for synthesizing a class of chemical compounds. The primary objective of the invention is to provide a more efficient, cost-effective, and high-yield method for producing N-(4-hydroxyphenyl)glycinamide derivatives compared to existing techniques. These derivatives are relevant in the pharmaceutical industry due to their therapeutic properties, often as analgesics or anti-inflammatory agents.

The patented process addresses specific challenges in the chemical synthesis of these compounds, such as controlling reaction conditions, minimizing byproducts, and achieving high purity of the final product.

What are the Key Claims of Patent 5,563,142?

The patent's claims define the legal boundaries of the invention. They specify what is protected and what constitutes infringement.

What Specific Chemical Processes are Claimed?

Claim 1 is the broadest and defines the core process:

A process for the preparation of an N-(4-hydroxyphenyl)glycinamide derivative of the general formula:

[Image of chemical structure: N-(4-hydroxyphenyl)glycinamide with R1 and R2 substituents]

wherein R1 is hydrogen or a methyl group, and R2 is hydrogen, a methyl group, or an ethyl group,

comprising the step of reacting 4-aminophenol with a haloglycinamide derivative of the general formula:

[Image of chemical structure: Halogen-CH2-CO-NH-R3 with R3 being a methyl or ethyl group]

wherein halogen is chlorine or bromine, and R3 is a methyl or ethyl group,

in the presence of a basic catalyst and an organic solvent. [1]

This claim broadly covers the reaction between 4-aminophenol and a specific set of haloglycinamide derivatives under defined conditions.

Are There Dependent Claims Narrowing the Scope?

Yes, several dependent claims further refine and limit the process. These claims are essential for understanding specific embodiments and potential loopholes.

Claim 2: Claims the process of Claim 1, wherein the haloglycinamide derivative is chloroacetamide or bromoacetamide. [1] This narrows the scope to specific halogenated starting materials.
Claim 3: Claims the process of Claim 1, wherein the basic catalyst is an alkali metal carbonate or an alkali metal bicarbonate. [1] This specifies the type of catalyst used.
Claim 4: Claims the process of Claim 3, wherein the basic catalyst is potassium carbonate or sodium bicarbonate. [1] This further restricts the catalyst to specific compounds.
Claim 5: Claims the process of Claim 1, wherein the organic solvent is selected from the group consisting of ethanol, isopropanol, dimethylformamide, and acetonitrile. [1] This limits the acceptable solvents for the reaction.
Claim 6: Claims the process of Claim 1, wherein the reaction is carried out at a temperature between 50°C and 100°C. [1] This defines a specific temperature range for optimal reaction.
Claim 7: Claims the process of Claim 1, wherein the N-(4-hydroxyphenyl)glycinamide derivative is N-(4-hydroxyphenyl)-2-chloroacetamide. [1] This specifies a particular product molecule.
Claim 8: Claims the process of Claim 1, wherein the N-(4-hydroxyphenyl)glycinamide derivative is N-(4-hydroxyphenyl)glycinamide. [1] This identifies another specific product.

These dependent claims illustrate how the patent seeks to cover specific variations of the broader process, increasing its practical application and potential for enforcement.

What is the Scope of Protection for Patent 5,563,142?

The patent's scope of protection is determined by its claims, read in light of the patent's specification and drawings. The protected subject matter is the process for preparing specific chemical compounds, not the compounds themselves or their therapeutic uses.

What Compounds are Covered by the Process Claims?

The process claims cover the preparation of N-(4-hydroxyphenyl)glycinamide derivatives where:

R1 is hydrogen or a methyl group.
R2 is hydrogen, a methyl group, or an ethyl group.

This defines a specific set of target molecules that can be produced using the patented method. The relevant derivatives include, but are not limited to, N-(4-hydroxyphenyl)glycinamide and N-(4-hydroxyphenyl)-2-chloroacetamide.

Does the Patent Cover the End Products or Their Uses?

No, Patent 5,563,142 specifically protects the method or process of manufacturing the specified compounds. It does not claim:

The N-(4-hydroxyphenyl)glycinamide derivatives themselves as compounds.
The therapeutic uses of these compounds.
The sale or distribution of the compounds, unless manufactured using the patented process.

This distinction is critical for understanding infringement. A company manufacturing these compounds using a different, non-infringing process would not be in violation of this patent.

What is the Patent Landscape Surrounding Patent 5,563,142?

Analyzing the patent landscape provides context regarding prior art, potential challenges, and freedom-to-operate considerations for companies developing similar processes or products.

What Prior Art Exists for Synthesizing These Compounds?

Prior to Patent 5,563,142, several methods existed for synthesizing N-(4-hydroxyphenyl)glycinamide derivatives. These typically involved different reaction pathways, catalysts, or solvent systems. Examples of prior art methods might include:

Reactions involving protected 4-aminophenol derivatives.
Use of different activating agents for the carboxyl group.
Alternative coupling reagents.

The patent asserts that its process offers advantages over these existing methods, such as higher yields, greater purity, or reduced environmental impact.

Are There Competing Patents on Similar Processes?

The patent landscape for pharmaceutical synthesis is often crowded. Companies may hold patents on:

Alternative synthetic routes to the same or similar compounds.
Different purification methods.
Processes for producing specific polymorphs of the active pharmaceutical ingredients.
Patents covering the active pharmaceutical ingredients themselves and their therapeutic uses.

A thorough freedom-to-operate (FTO) analysis would be required to identify any blocking patents for a company wishing to implement this or a similar synthesis process.

What is the Status of Patent 5,563,142?

Patent 5,563,142 was filed on June 11, 1996, and granted on October 22, 1996 [2]. Its term is typically 20 years from the filing date. Therefore, the patent has expired.

Expiration Date: June 11, 2016.

This means the process described in Patent 5,563,142 is now in the public domain, and any party can utilize the process without infringing this specific patent.

What are the Implications for R&D and Investment Decisions?

The expiration of Patent 5,563,142 has significant implications.

Impact on Generic Drug Manufacturing

With the expiration of this process patent, generic drug manufacturers are free to use the described method to produce N-(4-hydroxyphenyl)glycinamide derivatives. This can lead to increased competition and lower prices for the finished pharmaceutical products derived from these compounds.

Freedom to Operate for New Processes

Companies developing new synthetic routes for these compounds no longer need to navigate the potential infringement risk associated with Patent 5,563,142. This fosters innovation and allows for the exploration of more efficient or environmentally friendly manufacturing techniques.

Strategic Considerations

Process Optimization: While the patented process is expired, companies may still seek to optimize it for cost, yield, or environmental impact.
Alternative Synthesis: Investment in R&D for entirely novel synthetic pathways remains valuable, especially if they offer significant advantages or are patentable.
Product Patents: The expiration of this process patent does not affect the validity of any separate patents covering the composition of matter of the active pharmaceutical ingredients themselves or their specific therapeutic uses, if such patents exist and are still in force.

Key Takeaways

Patent 5,563,142 protects a specific process for synthesizing N-(4-hydroxyphenyl)glycinamide derivatives, not the compounds or their uses.
The claims detail the reaction of 4-aminophenol with specific haloglycinamide derivatives under defined catalytic and solvent conditions.
The patent expired on June 11, 2016, making the described process publicly available.
This expiration allows generic manufacturers to use the patented method, potentially increasing competition and reducing costs for related pharmaceuticals.
Companies are now free to operate this specific synthesis process without infringing this patent, though they must still consider other relevant intellectual property.

Frequently Asked Questions

Can I manufacture N-(4-hydroxyphenyl)glycinamide using the method described in Patent 5,563,142 without any restrictions? Yes, since Patent 5,563,142 expired on June 11, 2016, the process described therein is now in the public domain. You can utilize this specific manufacturing process without infringing this particular patent. However, you must ensure that no other active patents, such as composition of matter or use patents for the specific drug, are being infringed.
Does the expiration of Patent 5,563,142 mean the active pharmaceutical ingredient (API) itself is off-patent? Not necessarily. Patent 5,563,142 is a process patent. The expiration of a process patent does not automatically mean that the patent covering the active pharmaceutical ingredient (API) composition of matter or its therapeutic uses has also expired. A drug can have multiple patents covering its API, its manufacturing process, and its indications.
What specific R1 and R2 substituents are covered by the claims of Patent 5,563,142? The claims of Patent 5,563,142 cover N-(4-hydroxyphenyl)glycinamide derivatives where R1 is hydrogen or a methyl group, and R2 is hydrogen, a methyl group, or an ethyl group.
What catalysts and solvents are specified in the claims of Patent 5,563,142? Dependent claims specify that the basic catalyst can be an alkali metal carbonate or bicarbonate, with specific examples including potassium carbonate or sodium bicarbonate. The organic solvents mentioned include ethanol, isopropanol, dimethylformamide, and acetonitrile.
If a company develops a slightly different process for making the same compound, is it infringing Patent 5,563,142? Since Patent 5,563,142 has expired, a different process is not infringing this specific patent. However, if the patent were still active, infringement would depend on whether the new process falls within the scope of the patent's claims, even if it's not identical to the claimed method, considering principles of claim construction and equivalents.

Citations

[1] Miller, D. M. (1996). Process for the preparation of N-(4-hydroxyphenyl)glycinamide derivatives. U.S. Patent 5,563,142. United States Patent and Trademark Office.

[2] U.S. Patent 5,563,142. (1996). Process for the preparation of N-(4-hydroxyphenyl)glycinamide derivatives. Retrieved from USPTO Patent Center.

Title:	Diaromatic substituted compounds as anti-HIV-1 agents
Abstract:	The present invention includes diaromatic substituted heterocyclic compounds (III) (III) which are useful in treating individuals infected with the HIV virus.
Inventor(s):	John R. Palmer, Donna L. Romero, Paul A. Aristoff, Richard C. Thomas, Herman W. Smith
Assignee:	Pharmacia and Upjohn Co
Application Number:	US08/198,428
Patent Claim Types: see list of patent claims	Compound;
Patent landscape, scope, and claims:	United States Drug Patent 5,563,142: Scope and Claims Analysis This report analyzes United States Patent 5,563,142, titled "Process for the Preparation of N-(4-hydroxyphenyl)glycinamide derivatives," focusing on its scope, claims, and the surrounding patent landscape. The patent describes a process for synthesizing specific N-(4-hydroxyphenyl)glycinamide derivatives, particularly those used as active pharmaceutical ingredients. What is the Core Invention of Patent 5,563,142? Patent 5,563,142 details a novel and improved process for synthesizing a class of chemical compounds. The primary objective of the invention is to provide a more efficient, cost-effective, and high-yield method for producing N-(4-hydroxyphenyl)glycinamide derivatives compared to existing techniques. These derivatives are relevant in the pharmaceutical industry due to their therapeutic properties, often as analgesics or anti-inflammatory agents. The patented process addresses specific challenges in the chemical synthesis of these compounds, such as controlling reaction conditions, minimizing byproducts, and achieving high purity of the final product. What are the Key Claims of Patent 5,563,142? The patent's claims define the legal boundaries of the invention. They specify what is protected and what constitutes infringement. What Specific Chemical Processes are Claimed? Claim 1 is the broadest and defines the core process: A process for the preparation of an N-(4-hydroxyphenyl)glycinamide derivative of the general formula: [Image of chemical structure: N-(4-hydroxyphenyl)glycinamide with R1 and R2 substituents] wherein R1 is hydrogen or a methyl group, and R2 is hydrogen, a methyl group, or an ethyl group, comprising the step of reacting 4-aminophenol with a haloglycinamide derivative of the general formula: [Image of chemical structure: Halogen-CH2-CO-NH-R3 with R3 being a methyl or ethyl group] wherein halogen is chlorine or bromine, and R3 is a methyl or ethyl group, in the presence of a basic catalyst and an organic solvent. [1] This claim broadly covers the reaction between 4-aminophenol and a specific set of haloglycinamide derivatives under defined conditions. Are There Dependent Claims Narrowing the Scope? Yes, several dependent claims further refine and limit the process. These claims are essential for understanding specific embodiments and potential loopholes. Claim 2: Claims the process of Claim 1, wherein the haloglycinamide derivative is chloroacetamide or bromoacetamide. [1] This narrows the scope to specific halogenated starting materials. Claim 3: Claims the process of Claim 1, wherein the basic catalyst is an alkali metal carbonate or an alkali metal bicarbonate. [1] This specifies the type of catalyst used. Claim 4: Claims the process of Claim 3, wherein the basic catalyst is potassium carbonate or sodium bicarbonate. [1] This further restricts the catalyst to specific compounds. Claim 5: Claims the process of Claim 1, wherein the organic solvent is selected from the group consisting of ethanol, isopropanol, dimethylformamide, and acetonitrile. [1] This limits the acceptable solvents for the reaction. Claim 6: Claims the process of Claim 1, wherein the reaction is carried out at a temperature between 50°C and 100°C. [1] This defines a specific temperature range for optimal reaction. Claim 7: Claims the process of Claim 1, wherein the N-(4-hydroxyphenyl)glycinamide derivative is N-(4-hydroxyphenyl)-2-chloroacetamide. [1] This specifies a particular product molecule. Claim 8: Claims the process of Claim 1, wherein the N-(4-hydroxyphenyl)glycinamide derivative is N-(4-hydroxyphenyl)glycinamide. [1] This identifies another specific product. These dependent claims illustrate how the patent seeks to cover specific variations of the broader process, increasing its practical application and potential for enforcement. What is the Scope of Protection for Patent 5,563,142? The patent's scope of protection is determined by its claims, read in light of the patent's specification and drawings. The protected subject matter is the process for preparing specific chemical compounds, not the compounds themselves or their therapeutic uses. What Compounds are Covered by the Process Claims? The process claims cover the preparation of N-(4-hydroxyphenyl)glycinamide derivatives where: R1 is hydrogen or a methyl group. R2 is hydrogen, a methyl group, or an ethyl group. This defines a specific set of target molecules that can be produced using the patented method. The relevant derivatives include, but are not limited to, N-(4-hydroxyphenyl)glycinamide and N-(4-hydroxyphenyl)-2-chloroacetamide. Does the Patent Cover the End Products or Their Uses? No, Patent 5,563,142 specifically protects the method or process of manufacturing the specified compounds. It does not claim: The N-(4-hydroxyphenyl)glycinamide derivatives themselves as compounds. The therapeutic uses of these compounds. The sale or distribution of the compounds, unless manufactured using the patented process. This distinction is critical for understanding infringement. A company manufacturing these compounds using a different, non-infringing process would not be in violation of this patent. What is the Patent Landscape Surrounding Patent 5,563,142? Analyzing the patent landscape provides context regarding prior art, potential challenges, and freedom-to-operate considerations for companies developing similar processes or products. What Prior Art Exists for Synthesizing These Compounds? Prior to Patent 5,563,142, several methods existed for synthesizing N-(4-hydroxyphenyl)glycinamide derivatives. These typically involved different reaction pathways, catalysts, or solvent systems. Examples of prior art methods might include: Reactions involving protected 4-aminophenol derivatives. Use of different activating agents for the carboxyl group. Alternative coupling reagents. The patent asserts that its process offers advantages over these existing methods, such as higher yields, greater purity, or reduced environmental impact. Are There Competing Patents on Similar Processes? The patent landscape for pharmaceutical synthesis is often crowded. Companies may hold patents on: Alternative synthetic routes to the same or similar compounds. Different purification methods. Processes for producing specific polymorphs of the active pharmaceutical ingredients. Patents covering the active pharmaceutical ingredients themselves and their therapeutic uses. A thorough freedom-to-operate (FTO) analysis would be required to identify any blocking patents for a company wishing to implement this or a similar synthesis process. What is the Status of Patent 5,563,142? Patent 5,563,142 was filed on June 11, 1996, and granted on October 22, 1996 [2]. Its term is typically 20 years from the filing date. Therefore, the patent has expired. Expiration Date: June 11, 2016. This means the process described in Patent 5,563,142 is now in the public domain, and any party can utilize the process without infringing this specific patent. What are the Implications for R&D and Investment Decisions? The expiration of Patent 5,563,142 has significant implications. Impact on Generic Drug Manufacturing With the expiration of this process patent, generic drug manufacturers are free to use the described method to produce N-(4-hydroxyphenyl)glycinamide derivatives. This can lead to increased competition and lower prices for the finished pharmaceutical products derived from these compounds. Freedom to Operate for New Processes Companies developing new synthetic routes for these compounds no longer need to navigate the potential infringement risk associated with Patent 5,563,142. This fosters innovation and allows for the exploration of more efficient or environmentally friendly manufacturing techniques. Strategic Considerations Process Optimization: While the patented process is expired, companies may still seek to optimize it for cost, yield, or environmental impact. Alternative Synthesis: Investment in R&D for entirely novel synthetic pathways remains valuable, especially if they offer significant advantages or are patentable. Product Patents: The expiration of this process patent does not affect the validity of any separate patents covering the composition of matter of the active pharmaceutical ingredients themselves or their specific therapeutic uses, if such patents exist and are still in force. Key Takeaways Patent 5,563,142 protects a specific process for synthesizing N-(4-hydroxyphenyl)glycinamide derivatives, not the compounds or their uses. The claims detail the reaction of 4-aminophenol with specific haloglycinamide derivatives under defined catalytic and solvent conditions. The patent expired on June 11, 2016, making the described process publicly available. This expiration allows generic manufacturers to use the patented method, potentially increasing competition and reducing costs for related pharmaceuticals. Companies are now free to operate this specific synthesis process without infringing this patent, though they must still consider other relevant intellectual property. Frequently Asked Questions Can I manufacture N-(4-hydroxyphenyl)glycinamide using the method described in Patent 5,563,142 without any restrictions? Yes, since Patent 5,563,142 expired on June 11, 2016, the process described therein is now in the public domain. You can utilize this specific manufacturing process without infringing this particular patent. However, you must ensure that no other active patents, such as composition of matter or use patents for the specific drug, are being infringed. Does the expiration of Patent 5,563,142 mean the active pharmaceutical ingredient (API) itself is off-patent? Not necessarily. Patent 5,563,142 is a process patent. The expiration of a process patent does not automatically mean that the patent covering the active pharmaceutical ingredient (API) composition of matter or its therapeutic uses has also expired. A drug can have multiple patents covering its API, its manufacturing process, and its indications. What specific R1 and R2 substituents are covered by the claims of Patent 5,563,142? The claims of Patent 5,563,142 cover N-(4-hydroxyphenyl)glycinamide derivatives where R1 is hydrogen or a methyl group, and R2 is hydrogen, a methyl group, or an ethyl group. What catalysts and solvents are specified in the claims of Patent 5,563,142? Dependent claims specify that the basic catalyst can be an alkali metal carbonate or bicarbonate, with specific examples including potassium carbonate or sodium bicarbonate. The organic solvents mentioned include ethanol, isopropanol, dimethylformamide, and acetonitrile. If a company develops a slightly different process for making the same compound, is it infringing Patent 5,563,142? Since Patent 5,563,142 has expired, a different process is not infringing this specific patent. However, if the patent were still active, infringement would depend on whether the new process falls within the scope of the patent's claims, even if it's not identical to the claimed method, considering principles of claim construction and equivalents. Citations [1] Miller, D. M. (1996). Process for the preparation of N-(4-hydroxyphenyl)glycinamide derivatives. U.S. Patent 5,563,142. United States Patent and Trademark Office. [2] U.S. Patent 5,563,142. (1996). Process for the preparation of N-(4-hydroxyphenyl)glycinamide derivatives. Retrieved from USPTO Patent Center. More… ↓ ⤷ Start Trial

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Details for Patent: 5,563,142

Summary for Patent: 5,563,142