ES8402252A1 - 4-Para-bi:phenylyl 4-oxo 2-methyl butyric acid prepn. - by condensn. of 4-bromo:acetyl-bi:phenyl with di:ethyl methyl-malonate carbanion, saponification and decarboxylation - Google Patents

4-Para-bi:phenylyl 4-oxo 2-methyl butyric acid prepn. - by condensn. of 4-bromo:acetyl-bi:phenyl with di:ethyl methyl-malonate carbanion, saponification and decarboxylation

Info

Publication number
ES8402252A1
ES8402252A1 ES521154A ES521154A ES8402252A1 ES 8402252 A1 ES8402252 A1 ES 8402252A1 ES 521154 A ES521154 A ES 521154A ES 521154 A ES521154 A ES 521154A ES 8402252 A1 ES8402252 A1 ES 8402252A1
Authority
ES
Spain
Prior art keywords
methyl
oxo
carbanion
butyric acid
condensn
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
ES521154A
Other languages
Spanish (es)
Other versions
ES521154A0 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pierre Fabre SA
Original Assignee
Pierre Fabre SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pierre Fabre SA filed Critical Pierre Fabre SA
Publication of ES521154A0 publication Critical patent/ES521154A0/en
Publication of ES8402252A1 publication Critical patent/ES8402252A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The prepn. of 4-para-biphenylyl-4-oxo -2-methyl-butyric acid ((I) or Metbufene) is by (a) condensn. of 4-bromacetylbiphenyl (II) with diethyl-methyl malonate carbanion (III) in an organic solvent (b) saponification of the obtd. diester (IV) to give 4-p-bephenyl-4-oxo -2-methyl-2-carboxy-butyric acid (V), which is decarboxylated to yield (I). (II) and (III) carbanion are used in stoichiometric amts. and the condensation effected in hexamethyl-phosphorotriamide (HMPT). The carbanion of (III) is pref. obtd. by treatment with sodium hydride in HMPT. (IV) is saponified with NaOH and (V) decarboxylated by heating in acid medium in decatin. (I) is known medicament, normally prepd. by acylation of biphenyl with itaconic anhydride and reduction of the methylenic double bond.
ES521154A 1982-04-05 1983-03-30 4-Para-bi:phenylyl 4-oxo 2-methyl butyric acid prepn. - by condensn. of 4-bromo:acetyl-bi:phenyl with di:ethyl methyl-malonate carbanion, saponification and decarboxylation Expired ES8402252A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8206021A FR2524463A1 (en) 1982-04-05 1982-04-05 4-Para-bi:phenylyl 4-oxo 2-methyl butyric acid prepn. - by condensn. of 4-bromo:acetyl-bi:phenyl with di:ethyl methyl-malonate carbanion, saponification and decarboxylation

Publications (2)

Publication Number Publication Date
ES521154A0 ES521154A0 (en) 1984-01-16
ES8402252A1 true ES8402252A1 (en) 1984-01-16

Family

ID=9272837

Family Applications (1)

Application Number Title Priority Date Filing Date
ES521154A Expired ES8402252A1 (en) 1982-04-05 1983-03-30 4-Para-bi:phenylyl 4-oxo 2-methyl butyric acid prepn. - by condensn. of 4-bromo:acetyl-bi:phenyl with di:ethyl methyl-malonate carbanion, saponification and decarboxylation

Country Status (2)

Country Link
ES (1) ES8402252A1 (en)
FR (1) FR2524463A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU719396B2 (en) * 1996-02-19 2000-05-11 Japan Tobacco Inc. Therapeutic agent for diabetes
EP0927156A1 (en) * 1996-09-04 1999-07-07 Warner-Lambert Company Biphenyl butyric acids and their derivatives as inhibitors of matrix metalloproteinases

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1091403A (en) * 1964-01-24 1967-11-15 Boots Pure Drug Co Ltd Therapeutically active phenylalkane derivatives

Also Published As

Publication number Publication date
ES521154A0 (en) 1984-01-16
FR2524463B1 (en) 1984-05-11
FR2524463A1 (en) 1983-10-07

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19971001