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GB1315542A - 4-phenyl-butyric acid derivatives - Google Patents

4-phenyl-butyric acid derivatives

Info

Publication number
GB1315542A
GB1315542A GB2220270A GB2220270A GB1315542A GB 1315542 A GB1315542 A GB 1315542A GB 2220270 A GB2220270 A GB 2220270A GB 2220270 A GB2220270 A GB 2220270A GB 1315542 A GB1315542 A GB 1315542A
Authority
GB
United Kingdom
Prior art keywords
group
acid
atom
hydroxyl group
general formula
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
GB2220270A
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.)
Clin Byla SA
Original Assignee
Clin Byla 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 Clin Byla SA filed Critical Clin Byla SA
Publication of GB1315542A publication Critical patent/GB1315542A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
    • 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
    • C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
    • 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
    • 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
    • C07C59/88—Unsaturated compounds containing keto groups containing halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1315542 4-Phenyl-butyric acid derivatives ETABS CLIN-BYLA 7 May 1970 [12 May 1969] 22202/70 Heading C2C Novel 4-phenyl-butyric acid derivatives of the general formula wherein R<SP>1</SP> is a chlorine atom or a nitro group, R<SP>2</SP> is an isopropyl, tertiary-butyl or cyclohexyl group, each of R<SP>3</SP> and R<SP>4</SP> is a hydrogen atom or one is a hydrogen atom and the other is a hydroxyl group or both together form an oxygen atom and R<SP>5</SP> is a hydroxyl or alkoxy group, OM where M is an equivalent of an alkali or alkaline earth metal, or NYZ where Y is a hydrogen atom or C 1-4 alkyl group and Z is defined as Y or is a tertiary amino-alkyl group or NYZ is a heterocyclic group having 5-7 ring atoms, with the proviso that when R<SP>1</SP> is a nitro group and R<SP>5</SP> is a hydroxyl group, R<SP>3</SP> and R<SP>4</SP> can only be taken together to form an oxygen atom and when R<SP>5</SP> is NYZ then R<SP>3</SP> and R<SP>4</SP> are each a hydrogen atom, and, when R<SP>5</SP> is a basic group, acid addition salts thereof are prepared (a) when R<SP>1</SP> is a chlorine atom, R<SP>3</SP> and R<SP>4</SP> together form an oxygen atom and R<SP>5</SP> is a hydroxyl group, by treatment of a 4-phenylbutyric acid of the general formula with anhydrous aluminium chloride, followed by monochlorination and decomposition with acid of the resulting complex; (b) when R<SP>1</SP> is a chlorine atom, each of R<SP>3</SP> and R<SP>4</SP> is a hydrogen atom and R<SP>5</SP> is a hydroxyl group, by Wolf- Kishner or Clemmensen reduction of the product of (a); (c) when R<SP>1</SP> is a chlorine atom, one of R<SP>3</SP> and R<SP>4</SP> is a hydrogen atom and the other is an hydroxyl group and R<SP>5</SP> is an hydroxyl group, by complex hydride reduction of the product of (a); (d) when R<SP>1</SP> is a nitro group, R<SP>3</SP> and R<SP>4</SP> together form an oxygen atom and R<SP>5</SP> is an hydroxyl group, by mononitration of a 4- phenylbutyric acid of the second general formula above; (e) when R<SP>5</SP> is an alkoxy group, by esterification of the corresponding free acid with an alkanol in the presence of a hydrogen halide; (f) when R<SP>5</SP> is NYZ, by reaction of the corresponding free acid with a thionyl halide and treatment of the resulting acid halide with ammonia or an amine of the general formula HNYZ; (g) when R<SP>5</SP> is OM, where M is an alkali metal atom, by neutralization of the corresponding free acid with an alkali metal hydroxide; (h) when R<SP>5</SP> is OM, where M is an equivalent of an alkaline earth metal, by treatment of the product of (g) with an alkaline earth metal salt; and (i) when R<SP>5</SP> is a basic group and the product is in the form of a salt, by salification of the corresponding free base with an acid. Pharmaceutical compositions having antiinflammatory and analgesic activity comprise, as active ingredient, at least one 4-phenylbutyric acid derivative of the first general formula above, together with a pharmacologically acceptable carrier, and may be administered orally, endorectally or parenterally.
GB2220270A 1969-05-12 1970-05-07 4-phenyl-butyric acid derivatives Expired GB1315542A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR6915296A FR2043467A1 (en) 1969-05-12 1969-05-12

Publications (1)

Publication Number Publication Date
GB1315542A true GB1315542A (en) 1973-05-02

Family

ID=9033892

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2220270A Expired GB1315542A (en) 1969-05-12 1970-05-07 4-phenyl-butyric acid derivatives

Country Status (10)

Country Link
JP (1) JPS4945859B1 (en)
AT (1) AT297691B (en)
BE (1) BE750233A (en)
CS (1) CS159770B2 (en)
FR (1) FR2043467A1 (en)
GB (1) GB1315542A (en)
IE (1) IE34139B1 (en)
NL (1) NL7006851A (en)
PL (1) PL73072B1 (en)
SE (1) SE379039B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0300325A3 (en) * 1987-07-20 1990-10-17 Cometec S.R.L. Compositions for promoting growth of animals
CN1050119C (en) * 1993-04-07 2000-03-08 希巴特殊化学控股公司 Alkaline earth metal salts, transition metal salts and transition metal complexes of ketocarboxylic acids as corrosion inhibitors

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2162038A1 (en) * 1970-05-05 1972-08-17 William H Rorer Ine , Fort Washington, Pa (V St A ) Process for the production of synthetic alkanoic acids and their derivatives
JPH0262858A (en) * 1988-05-09 1990-03-02 Zeria Pharmaceut Co Ltd New phenylalkanoylamine derivatives, production methods and uses

Family Cites Families (2)

* 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
GB1040735A (en) * 1964-07-23 1966-09-01 British Drug Houses Ltd 4-aryl-3-hydroxybutyric acid and esters, amides and salts thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0300325A3 (en) * 1987-07-20 1990-10-17 Cometec S.R.L. Compositions for promoting growth of animals
CN1050119C (en) * 1993-04-07 2000-03-08 希巴特殊化学控股公司 Alkaline earth metal salts, transition metal salts and transition metal complexes of ketocarboxylic acids as corrosion inhibitors

Also Published As

Publication number Publication date
JPS4945859B1 (en) 1974-12-06
NL7006851A (en) 1970-11-16
AT297691B (en) 1972-04-10
IE34139B1 (en) 1975-02-19
FR2043467A1 (en) 1971-02-19
PL73072B1 (en) 1974-08-30
SE379039B (en) 1975-09-22
BE750233A (en) 1970-10-16
CS159770B2 (en) 1975-01-31
IE34139L (en) 1970-11-12

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee