GB1293626A - Substituted salicylic acid compounds - Google Patents

Substituted salicylic acid compounds

Info

Publication number
GB1293626A
GB1293626A GB2954370A GB2954370A GB1293626A GB 1293626 A GB1293626 A GB 1293626A GB 2954370 A GB2954370 A GB 2954370A GB 2954370 A GB2954370 A GB 2954370A GB 1293626 A GB1293626 A GB 1293626A
Authority
GB
United Kingdom
Prior art keywords
halogen
alkyl
hydrogen
fluorobenzoyl
prepared
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
GB2954370A
Inventor
Tsung-Ying Shen
Gordon Lyn Walford
Bruce Edward Witzel
Robert Louis Bugianesi
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 GB1293626A publication Critical patent/GB1293626A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • 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
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1293626 Substituted salicylic acids MERCK & CO Inc 18 June 1970 [25 June 1969 20 April 1970] 29543/70 Heading C2C Novel compounds of formula wherein R is hydroxy, amino, alkoxy, alkylamino, dialkylamino, dialkylaminoalkylamino, dialkylaminoalkoxy, hydroxyalkoxy, polyhydroxyalkoxy, alkoxyalkoxy, phenylalkoxy, phenoxy, alkoxyphenoxy, halophenoxy, dialkylaminophenoxy, alkanoylaminophenoxy, carboxyphenoxy, alkoxycarbonylphenoxy, alkanoylaminoalkoxy, anilino, hydrazino, morpholino,N-piperidino, pyrrolidino or hydroxyalkylamino ; R 2 is hydrogen, acyl, alkyl or alkoxycarbonyl ; R 3 is hydrogen, halogen, haloalkyl, alkyl, cycloalkyl or alkoxy; and each X is hydrogen, alkyl, hydroxy, alkoxy, acyloxy, halogen, haloalkyl, nitro, amino, alkylamino, dialkylamino, acylamino, mercapto, alkylthio, alkylsulphinyl, alkylsulphonyl, sulphamoyl, sulphinylamido, aminoalkyl, alkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, alkylthioalkyl, cyano, carboxy, alkoxycarbonyl, carbamoyl, aryl, aralkyl, salicyl, aryloxy or aralkoxy; and Y is methylene, carbonyl, methylenecarbonyl, cyclopropylene, cyclopropylidene or iminocarbonyl; provided that the OR 2 group is always ortho to the group, that when Y is carbonyl, X may not be a halogen other than fluorine, that when Y is methylene, at least one X is other than hydrogen, halogen or amino, and the Xs are such that the compound is not a symmetrical or symmetrically substituted bis-(hydroxycarboxyphenyl)-methane, and that none of the alkyl and alkoxy radicals contain more than 5 carbon atoms and alkanoyl residues contain less than 6 carbon atoms and salts and anhydrides thereof are prepared (a) by carbonation of a compound of Formula II: optionally followed by conversion of the X, hydroxy and/or carboxylic groups into other values given above by standard methods, or (b) by reaction of the appropriate acid chloride with salicylic acid or a derivative thereof in the presence of a Friedel-Crafts catalyst. p-(4-Fluorobenzoyl)-phenol is prepared by demethylation of p-(4-fluorobenzoyl)-anisole obtained by reaction of anisole with p-fluorobenzoic acid and polyphosphoric acid or directly by using phenol for anisole in the last reaction. 4-(p-Fluorobenzoyl)-m-cresol is prepared by reaction of m-cresol and p-fluorobenzoyl chloride in presence of AlCl 3 . ( p-Methoxyphenyl ) - (p-methylphenyl) -methane is prepared by reduction of 4-methoxy-4<SP>1</SP>-methylbenzophenone. Pharmaceutical compositions in conventional forms for oral, rectal, topical or parenteral administration and having anti-inflammatory activity comprise an above novel compound and a carrier or diluent.
GB2954370A 1969-06-25 1970-06-18 Substituted salicylic acid compounds Expired GB1293626A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83660469A 1969-06-25 1969-06-25
US3032070A 1970-04-20 1970-04-20

Publications (1)

Publication Number Publication Date
GB1293626A true GB1293626A (en) 1972-10-18

Family

ID=26705907

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2954370A Expired GB1293626A (en) 1969-06-25 1970-06-18 Substituted salicylic acid compounds

Country Status (7)

Country Link
JP (1) JPS504653B1 (en)
CA (1) CA940146A (en)
CH (1) CH545265A (en)
DE (1) DE2031224A1 (en)
FR (1) FR2053011A1 (en)
GB (1) GB1293626A (en)
NL (1) NL7008627A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0276064A1 (en) * 1987-01-12 1988-07-27 Eli Lilly And Company Anti-inflammatory agents
US4992576A (en) * 1987-01-12 1991-02-12 Eli Lilly And Company Intermediates for leukotriene antagonists
US4996230A (en) * 1990-02-16 1991-02-26 Eli Lilly And Company Leukotriene antagonists
US5171882A (en) * 1987-01-12 1992-12-15 Eli Lilly And Company Leukotriene antagonists
US5235064A (en) * 1987-01-12 1993-08-10 Eli Lilly And Company Leukotriene antagonists
US5683682A (en) * 1989-11-15 1997-11-04 Robertet S.A. Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3635311A1 (en) * 1986-10-17 1988-04-21 Bayer Ag HYDROXYCARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN PRESSURE OR HEAT-SENSITIVE RECORDING MATERIALS
DE3635742A1 (en) * 1986-10-21 1988-05-05 Bayer Ag HYDROXYCARBONIC ACID DERIVATIVES AND THEIR USE IN RECORDING MATERIALS
GB9214120D0 (en) * 1991-07-25 1992-08-12 Ici Plc Therapeutic amides
GB9305295D0 (en) * 1993-03-15 1993-05-05 Zeneca Ltd Therapeutic compounds
GB9310095D0 (en) * 1993-05-17 1993-06-30 Zeneca Ltd Therapeutic compounds
EP0752421B1 (en) * 1995-07-07 2005-10-12 AstraZeneca AB Ortho-substituted aromatic compounds, containing three (het)aryl moieties, their preparation and their use as prostaglandin E2-(PGE2)-antagonists
FR2762839B1 (en) * 1997-04-30 2001-05-11 Oreal NOVEL SALICYLIC ACID DERIVATIVES AND THEIR USE IN A COSMETIC AND / OR DERMATOLOGICAL COMPOSITION
EP1127869A4 (en) * 1998-11-05 2007-05-02 Toyama Chemical Co Ltd Novel compounds and medicinal use thereof

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0276064A1 (en) * 1987-01-12 1988-07-27 Eli Lilly And Company Anti-inflammatory agents
AU601541B2 (en) * 1987-01-12 1990-09-13 Eli Lilly And Company Leukotriene antagonists
US4992576A (en) * 1987-01-12 1991-02-12 Eli Lilly And Company Intermediates for leukotriene antagonists
US5171882A (en) * 1987-01-12 1992-12-15 Eli Lilly And Company Leukotriene antagonists
US5235064A (en) * 1987-01-12 1993-08-10 Eli Lilly And Company Leukotriene antagonists
US5683682A (en) * 1989-11-15 1997-11-04 Robertet S.A. Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms
US4996230A (en) * 1990-02-16 1991-02-26 Eli Lilly And Company Leukotriene antagonists

Also Published As

Publication number Publication date
NL7008627A (en) 1970-12-29
CA940146A (en) 1974-01-15
JPS504653B1 (en) 1975-02-22
FR2053011A1 (en) 1971-04-16
DE2031224A1 (en) 1971-01-07
CH545265A (en) 1973-12-15

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees