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IE34139B1 - 4-phenyl-butric acid derivatives - Google Patents

4-phenyl-butric acid derivatives

Info

Publication number
IE34139B1
IE34139B1 IE599/70A IE59970A IE34139B1 IE 34139 B1 IE34139 B1 IE 34139B1 IE 599/70 A IE599/70 A IE 599/70A IE 59970 A IE59970 A IE 59970A IE 34139 B1 IE34139 B1 IE 34139B1
Authority
IE
Ireland
Prior art keywords
group
acid
atom
hydroxyl group
general formula
Prior art date
Application number
IE599/70A
Other versions
IE34139L (en
Original Assignee
Clin Byla Ets
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 Ets filed Critical Clin Byla Ets
Publication of IE34139L publication Critical patent/IE34139L/en
Publication of IE34139B1 publication Critical patent/IE34139B1/en

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)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pain & Pain Management (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Rheumatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (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. [GB1315542A]
IE599/70A 1969-05-12 1970-05-08 4-phenyl-butric acid derivatives IE34139B1 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number Publication Date
IE34139L IE34139L (en) 1970-11-12
IE34139B1 true IE34139B1 (en) 1975-02-19

Family

ID=9033892

Family Applications (1)

Application Number Title Priority Date Filing Date
IE599/70A IE34139B1 (en) 1969-05-12 1970-05-08 4-phenyl-butric 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)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1382267A (en) * 1970-05-05 1975-01-29 Rorer Inc William H Phenylalkanoic acid derivatives
DE3881770T2 (en) * 1987-07-20 1993-10-07 Cometec Srl Compositions for promoting animal growth.
JPH0262858A (en) * 1988-05-09 1990-03-02 Zeria Pharmaceut Co Ltd New phenylalkanoylamine derivatives, production methods and uses
EP0619290B1 (en) * 1993-04-07 1996-10-09 Ciba-Geigy Ag Salts of alkaline earth metals and transition metals as well as complexes of transition metals of ketocarboxylic acids and their use as corrosion inhibitors

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

Also Published As

Publication number Publication date
NL7006851A (en) 1970-11-16
JPS4945859B1 (en) 1974-12-06
GB1315542A (en) 1973-05-02
PL73072B1 (en) 1974-08-30
AT297691B (en) 1972-04-10
CS159770B2 (en) 1975-01-31
FR2043467A1 (en) 1971-02-19
SE379039B (en) 1975-09-22
BE750233A (en) 1970-10-16
IE34139L (en) 1970-11-12

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