GB1111361A - 4-phenoxyalkanoic acids and derivatives thereof - Google Patents

4-phenoxyalkanoic acids and derivatives thereof

Info

Publication number
GB1111361A
GB1111361A GB2338666A GB2338666A GB1111361A GB 1111361 A GB1111361 A GB 1111361A GB 2338666 A GB2338666 A GB 2338666A GB 2338666 A GB2338666 A GB 2338666A GB 1111361 A GB1111361 A GB 1111361A
Authority
GB
United Kingdom
Prior art keywords
acid
alkyl
radical
carbon atoms
reacting
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
GB2338666A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1111361A publication Critical patent/GB1111361A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)

Abstract

Novel compounds of formula <FORM:1111361/C2/1> where R is a hydrogen atom or a C1- 5 alkyl radical; each of R1 and R2 is a C1- 5 alky radical; X is a halogen atom or a C1- 5 alkyl, C1- 5 haloalkyl, cycloalkyl, C1- 5 alkoxy, C1- 5 alkylthio, aryl, aralkyl, aryloxy or aralkoxy radical, or, taken together, two X radicals on adjacent carbon atoms of the benzene ring may be combined to form a hydrocarbylene chain containing 3 or 4 carbon atoms between its points of attachment; and n is 0, 1, 2 or 3, and the non-toxic pharmacologically acceptable salts, esters or amides thereof, are prepared by treating a compound of Formula II <FORM:1111361/C2/2> wherein R3 is an alkyl radical, with a reducing agent, and, if desired, hydrolysing the 4-phenoxy-alkanoic acid ester obtained. The salts are produced by reacting the acid with a base having a non-toxic pharmacologically acceptable cation. Esters may be obtained from the corresponding acid, e.g. by reacting the acid with an alcohol, or by converting the acid to its halide, and reacting the halide with an alcohol. Amides may aso be prepared from the acid or acid halide or from the ester. The 4 - phenoxy - 2 - alkenoic acid ester starting materials may be prepared by treating a 2-phenoxyalkanal with an alkoxycarbonyl-alkylidene - triarylphosphorane or an alkyl dialkoxyphosphinylalkanoate.ALSO:Therapeutic compositions having hypocholesterolemic activity and which can be administered orally or parenterally, contain as active ingredient a compound of formula <FORM:1111361/A5-A6/1> where R is a hydrogen atom or C1-5 alkyl group, each of R1 and R2 is a C1-5 alkyl radical; X is a halogen atom, or a C1-5 alkyl, C1-5 haloalkyl, cycloalkyl, C1-5 alkoxy, C1-5 alkylthio, aryl, aralkyl, aryloxy or aralkoxy radical, or taken together, two X radicals on adjacent carbon atoms may be combined to form a hydrocarbylene chain containing 3 or 4 carbon atoms between its points of attachment, and n is 0, 1, 2 or 3, or non-toxic pharmaceutically acceptable salt, ester or amide thereof, if desired, in association with a further pharmaceutically active compound, e.g. a known hypocholesterolemic or nutritive agent.
GB2338666A 1965-05-27 1966-05-25 4-phenoxyalkanoic acids and derivatives thereof Expired GB1111361A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US45943665A 1965-05-27 1965-05-27

Publications (1)

Publication Number Publication Date
GB1111361A true GB1111361A (en) 1968-04-24

Family

ID=23824762

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2338666A Expired GB1111361A (en) 1965-05-27 1966-05-25 4-phenoxyalkanoic acids and derivatives thereof

Country Status (6)

Country Link
BR (1) BR6679625D0 (en)
CH (1) CH471063A (en)
DE (1) DE1543764A1 (en)
FR (1) FR5865M (en)
GB (1) GB1111361A (en)
NL (1) NL6607056A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0132367A2 (en) * 1983-07-18 1985-01-30 Eli Lilly And Company Leukotriene antagonists
US4764521A (en) * 1983-07-18 1988-08-16 Eli Lilly And Company Leukotriene antagonists and a method of use there as
US5462954A (en) * 1991-11-25 1995-10-31 Eli Lilly And Company Substituted phenyl phenol leukotriene antagonists

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3674836A (en) * 1968-05-21 1972-07-04 Parke Davis & Co 2,2-dimethyl-{11 -aryloxy-alkanoic acids and salts and esters thereof
US4172146A (en) * 1973-05-08 1979-10-23 Ciba-Geigy Corporation Substituted phenyl derivatives
US4416687A (en) * 1982-02-01 1983-11-22 Monsanto Company 3,5-Bis (trifluoromethyl)phenoxy carboxylic acids and derivatives thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0132367A2 (en) * 1983-07-18 1985-01-30 Eli Lilly And Company Leukotriene antagonists
EP0132367A3 (en) * 1983-07-18 1985-05-15 Eli Lilly And Company Leukotriene antagonists
US4764521A (en) * 1983-07-18 1988-08-16 Eli Lilly And Company Leukotriene antagonists and a method of use there as
US5462954A (en) * 1991-11-25 1995-10-31 Eli Lilly And Company Substituted phenyl phenol leukotriene antagonists

Also Published As

Publication number Publication date
NL6607056A (en) 1966-11-28
CH471063A (en) 1969-04-15
DE1543764A1 (en) 1970-01-02
BR6679625D0 (en) 1973-10-23
FR5865M (en) 1968-03-11

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