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EP0212617B1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Process for producing 4-biphenylylacetic acid

Assignee: Pfizer Japan Inc
•
Filing: 1986-08-19
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Granted: 1989-01-11
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Expires: 2006-08-19
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Abstract

No abstract record available.

Inventors

  • 👤 Osamu Shimada
  • 👤 Sakae Aoyagi
  • 👤 Yunosuke Nagase

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-09 03:48
CPC Classifications
C; C07; C07C; C07C61/00; C07C61/12; C07C61/125; C07C61/13; C07D; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07C51/00; C07C51/347; C07C51/377; C07C51/38; C07C57/00; C07C57/30; C07C57/38; C07D233/00; C07D233/96; C07D263/00; C07D263/02; C07D263/30; C07D263/34; C07D263/36; C07D263/42

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 250 words
A process for producing 4-biphenylylacetic acid or its salt represented by the following formula I wherein M represents an alkali metal or a hydrogen atom, which comprises either (a) reacting 4-biphenylylaldehyde represented by the following formula II with an N-acylglycine represented by the following formula III wherein R represents a substituted or unsubstituted phenyl or lower alkyl group, in the presence of a base to convert 4-biphenylylaldehyde into an azlactone compound represented by the following formula V wherein R is as defined above, heating the resulting azlactone compound of formula V, and if desired, neutralizing it to form an alpha-keto acid represented by the following formula VII wherein M is as defined above, and thereafter decarboxylating the alpha-keto acid ; or (b) reacting 4-biphenylylaldehyde of the following formula II with a lactam compound represented by the following formula IV wherein R' represents a hydrogen atom, a lower alkyl group or a carboxy-lower alkyl group, X represents an oxygen or sulfur atom, and Y represents a sulfur atom or -NH-, in the presence of a base to form a condensate represented by the following formula VI wherein R 1 , X and Y are as defined above, heating the resulting condensate of formula VI in the presence of an alkali base, and if desired, neutralizing it to form a derivative represented by the following formula VIII wherein M and Y are as defined above, and treating the derivative of formula VIII with a peroxide in the presence of an aqueous base.
Claim 2
Dependent Claim 250 words
A process for producing 4-biphenylylacetic acid or its salt represented by the following formula I wherein M represents an alkali metal or a hydrogen atom, which comprises either (a) reacting 4-biphenylylaldehyde represented by the following formula II with an N-acylglycine represented by the following formula III wherein R represents a substituted or unsubstituted phenyl or lower alkyl group, in the presence of a base to convert 4-biphenylylaldehyde into an azlactone compound represented by the following formula V wherein R is as defined above, heating the resulting azlactone compound of formula V, and if desired, neutralizing it to form an alpha-keto acid represented by the following formula VII wherein M is as defined above, and thereafter decarboxylating the alpha-keto acid ; or (b) reacting 4-biphenylylaldehyde of the following formula II with a lactam compound represented by the following formula IV wherein R' represents a hydrogen atom, a lower alkyl group or a carboxy-lower alkyl group, X represents an oxygen or sulfur atom, and Y represents a sulfur atom or -NH-, in the presence of a base to form a condensate represented by the following formula VI wherein R 1 , X and Y are as defined above, heating the resulting condensate of formula VI in the presence of an alkali base, and if desired, neutralizing it to form a derivative represented by the following formula VIII wherein M and Y are as defined above, and treating the derivative of formula VIII with a peroxide in the presence of an aqueous base.
Claim 3
Dependent Claim 32 words
The process of claim 1 wherein the process variant (a) is carried out in a single reactor without isolating the azlactone compound of formula V and the alpha-keto compound of formula VII.
Claim 4
Dependent Claim 32 words
The process of claim 2 wherein in a single reactor, the 4-biphenylylaldehyde of formula II and the N-acylglycine of formula III are heat-treated in the presence of a base, followed by decarboxylation.
Claim 5
Dependent Claim 19 words
The process of claim 1 wherein the decarboxylation is carried out by treatment with a peroxide under basic conditions.
Claim 6
Dependent Claim 23 words
An azlactone compound which is represented by the following formula V wherein R represents an unsubstituted or substituted phenyl or lower alkyl group.
Claim 7
Dependent Claim 23 words
An azlactone compound which is represented by the following formula V wherein R represents an unsubstituted or substituted phenyl or lower alkyl group.
Claim 8
Dependent Claim 32 words
The process of claim 1 wherein the process variant (b) is carried out in a single reactor without isolating the condensate represented by formula VI and the derivative represented by formula VIII.
Claim 9
Dependent Claim 36 words
The process of claim 6 whereirr in a single reactor, 4-biphenylylaldehyde of formula II and the lactam compound of formula IV are heat-treated in the presence of a base, and then treated in an aqueous solvent.
Claim 10
Dependent Claim 38 words
A compound represented by the following formula VI wherein R' represents a hydrogen atom, a lower alkyl group or a carboxy-lower alkyl group, X represents an oxygen or sulfur atom, and Y represents a sulfur atom or -NH-.
Claim 11
Dependent Claim 38 words
A compound represented by the following formula VI wherein R' represents a hydrogen atom, a lower alkyl group or a carboxy-lower alkyl group, X represents an oxygen or sulfur atom, and Y represents a sulfur atom or -NH-.

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