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GB1332824A - Alpha-phenoxyacetic acids and derivatives thereof - Google Patents

Alpha-phenoxyacetic acids and derivatives thereof

Info

Publication number
GB1332824A
GB1332824A GB5997570A GB5997570A GB1332824A GB 1332824 A GB1332824 A GB 1332824A GB 5997570 A GB5997570 A GB 5997570A GB 5997570 A GB5997570 A GB 5997570A GB 1332824 A GB1332824 A GB 1332824A
Authority
GB
United Kingdom
Prior art keywords
cycloalkenyl
residue
substituted
reacting
polycyclic
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
GB5997570A
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1332824A publication Critical patent/GB1332824A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/708—Ethers
    • C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1332824 α-Phenoxyacetic acids and derivatives thereof CIBA-GEIGY AG 17 Dec 1970 [18 Dec 1969 30 Oct 1970] 59975/70 Heading C2C Novel α-phenoxyacetic acids in which the α position is substituted by one or two C 1-4 alkyl or -alkenyl residues and the phenyl residue is substituted by a lower alkylated 5- or 6- membered monocyclic or polycyclic 1-cycloalkenyl residue, an unsubstituted 5- or 6- membered polycyclic 1-cycloalkenyl residue or an unsubstituted or lower alkylated 7- to 12- membered monocyclic or polycyclic 1-cycloalkenyl residue, wherein 1-cycloalkenyl means a singly unsaturated cycloalkenyl residue, the double bond of which extends from the carbon atom which is adjacent to the phenyl residue to an adjacent carbon atom, and ester and amides thereof may be prepared by (a) condensing a phenol which is substituted by an appropriate 1-cycloalkenyl residue with an α-halogenoacetic acid ester which is further substituted in the α- position by one or two C 1-4 alkyl or -alkenyl residues; (b) reacting a phenol as in (a) with an aldehyde or ketone derived from a C 1-4 alkane or -alkene in the presence of a tri- or tetrahalogenated methane derivative and a strong base or (c) forming a carboxylic acid or ester or amide thereof by reacting a corresponding compound having a modified carboxylic acid group with water, an alcohol, ammonia or an amine and thereafter optionally inter-converting the compounds of the invention by known methods. The intermediate p-(1-cycloalkenyl)phenols may be prepared by forming the Grignard reagent of a bromoanisole and reacting it with a cycloalkanone and dehydrating the hydrolysis product if dehydration does not occur on distillation followed by demethylating the obtained anisole. Pharmaceutical compositions of the compounds of the invention show a serum triglyceride lowering action, serum cholesterol lowering action and bring about a lowering of liver lipids when administered orally or parenterally with the usual excipients.
GB5997570A 1969-12-18 1970-12-17 Alpha-phenoxyacetic acids and derivatives thereof Expired GB1332824A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1899069 1969-12-18
CH1607770 1970-10-30

Publications (1)

Publication Number Publication Date
GB1332824A true GB1332824A (en) 1973-10-03

Family

ID=25717373

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5997570A Expired GB1332824A (en) 1969-12-18 1970-12-17 Alpha-phenoxyacetic acids and derivatives thereof

Country Status (8)

Country Link
AR (2) AR192704A1 (en)
BE (1) BE760449A (en)
CA (1) CA987337A (en)
DE (1) DE2060573A1 (en)
FR (1) FR2081376B1 (en)
GB (1) GB1332824A (en)
IE (1) IE34820B1 (en)
NL (1) NL7018444A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2598146B1 (en) * 1986-04-30 1989-01-20 Rech Ind NEW PROCESS FOR THE PREPARATION OF FIBRATES.

Also Published As

Publication number Publication date
AR192704A1 (en) 1973-03-14
CA987337A (en) 1976-04-13
NL7018444A (en) 1971-06-22
DE2060573A1 (en) 1971-06-24
AR192896A1 (en) 1973-03-21
IE34820B1 (en) 1975-08-20
BE760449A (en) 1971-06-17
FR2081376A1 (en) 1971-12-03
FR2081376B1 (en) 1975-12-26
IE34820L (en) 1971-06-18

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Legal Events

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