GB1175212A - Halo-Substituted 5-Phenylbenzoic Acids and their Derivatives - Google Patents

Halo-Substituted 5-Phenylbenzoic Acids and their Derivatives

Info

Publication number
GB1175212A
GB1175212A GB1117867A GB1117867A GB1175212A GB 1175212 A GB1175212 A GB 1175212A GB 1117867 A GB1117867 A GB 1117867A GB 1117867 A GB1117867 A GB 1117867A GB 1175212 A GB1175212 A GB 1175212A
Authority
GB
United Kingdom
Prior art keywords
fluorophenyl
alkoxy
alkyl
acid
fluoro
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
GB1117867A
Inventor
William Vance Ruyle
Lewis Hastings Sarett
Alexander Matzuk
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
Priority to GB1117867A priority Critical patent/GB1175212A/en
Publication of GB1175212A publication Critical patent/GB1175212A/en
Priority to CY67473A priority patent/CY674A/en
Priority to MY7300229A priority patent/MY7300229A/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
    • C07C65/21—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 ether groups, groups, groups, or groups
    • C07C65/28—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 ether groups, groups, groups, or groups having unsaturation outside the aromatic rings
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1,175,212. 5-Phenyl-benzoic acid derivatives. MERCK & CO. Inc. 9 March, 1967, No. 11178/67. Heading C2C. Novel compounds of the formula wherein X is halogen; R is H, halogen, C 1-6 alkyl or C 1-6 alkoxy; R 1 is OH, NH 2 , alkoxy, di-(C 1-6 alkyl)-amino-(C 1-6 alkoxy), hydroxy- C 1-6 alkoxy, C 1-6 alkylamino, di-(C 1-6 alkyl)- amino, C 1-6 polyhydroxyalkoxy, (C 1-6 alkoxy)- (C 1-6 alkoxy), phenyl-(C 1-6 alkoxy), phenoxy, substituted phenoxy, (C 1-6 alkanoylamino)- (C 1-6 alkoxy), di-(C 1-6 alkyl)-amino-(C 1-6 alkyl)- amino, hydrazino, hydroxylamino, N-morpholino, N-[4-(C 1-6 alkyl)-piperidino], N-[4-(C 1-6 hydroxyalkyl)-piperidino], C 1-6 hydroxyalkylamino, a naturally occurring amino acid radical attached at the N, or a radical of the formula in which R, R 2 , R 3 and X are such that the compound is symmetrical; R 2 is H, C 1-6 alkyl, C 1-6 alkanoyl or C 2-6 alkenyl; R 3 is H, C 1-6 alkyl, C 1-6 alkoxy, benzyl, C 2-6 alkenyl, or halogen; the pharmaceutically non-toxic salts; the anhydrides of the acids and the mixed anhydrides of the acids and 2-acetoxybenzoic acid, are prepared by reacting a phenyl-phenolate of the formula where A is alkali metal, with carbon dioxide at elevated temperatures and subsequent acidification to form the compound where R 1 is OH and R 2 is H; and optionally esterifying this compound; amidating the acid or ester; reacting the acid, ester or amide with an alkanoic acid anhydride, a dialkylsulphate or alkyltosylate, or alkenyl halide; neutralizing the acid forms or anhydrides to form salts; or forming the acid halide and reacting with 2-acetoxy-benzoic acid or the acid biphenyl compound to form the desired anhydride. Preparation of the following intermediates is also described: 2 - Fluoro - 5 - nitrophenol, 2 - fluoro - 5- nitroanisole, 4 - fluoro - 3 - methoxyaniline, 4- (4<SP>1</SP> - fluorophenyl) - aniline, 4 - fluoro - 2 - methoxy - 4 - nitrobiphenyl, 2<SP>1</SP>,3<SP>1</SP>,4<SP>1</SP>,5<SP>1</SP>,6<SP>1</SP> - pentafluoro - 4 - nitrobiphenyl, 2<SP>1</SP>- fluoro - 4 - nitrobiphenyl, 4<SP>1 </SP>- fluoro - 3 - methoxy - 4 - nitrobiphenyl, 4 - (4<SP>1</SP> - fluoro - 2<SP>1</SP> or 3<SP>1</SP> - methoxyphenyl) - aniline, 4 - (pentafluorophenyl)- aniline, 4 - (2<SP>1</SP> - fluorophenyl) - aniline, 2- methyl - 4 (4<SP>1</SP> - fluorophenyl) - aniline, 4 - (3<SP>1</SP>- chloro - 4<SP>1</SP>- fluorophenyl) - anisole and similar fluoroanisole compounds and 4 - (4<SP>1</SP> - fluorophenyl)-phenol and similar compounds; 4-(4<SP>1</SP>- fluorophenyl) - 2 - hydroxymethylphenol, 4- (4<SP>1</SP> - fluorophenyl) - 2 - acetoxymethylphenyl acetate, 4 - (4<SP>1</SP>-fluorophenyl)- 2 - methylphenylacetate, and 4 (4<SP>1 </SP>- fluorophenyl) - 2 - methylphenol. Pharmaceutical compositions having antiinflammatory activity comprises an above novel compound of the first general formula with an inert diluent, carrier or coating, preferably in forms suitable for oral administration.
GB1117867A 1967-03-09 1967-03-09 Halo-Substituted 5-Phenylbenzoic Acids and their Derivatives Expired GB1175212A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB1117867A GB1175212A (en) 1967-03-09 1967-03-09 Halo-Substituted 5-Phenylbenzoic Acids and their Derivatives
CY67473A CY674A (en) 1967-03-09 1973-03-08 Halo-substituted 5-phenylbenzoic acids and their derivatives
MY7300229A MY7300229A (en) 1967-03-09 1973-12-31 Halo-substituted 5-phenylbenzoic acids and their derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1117867A GB1175212A (en) 1967-03-09 1967-03-09 Halo-Substituted 5-Phenylbenzoic Acids and their Derivatives

Publications (1)

Publication Number Publication Date
GB1175212A true GB1175212A (en) 1969-12-23

Family

ID=9981435

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1117867A Expired GB1175212A (en) 1967-03-09 1967-03-09 Halo-Substituted 5-Phenylbenzoic Acids and their Derivatives

Country Status (3)

Country Link
CY (1) CY674A (en)
GB (1) GB1175212A (en)
MY (1) MY7300229A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082404A1 (en) * 1981-12-21 1983-06-29 Merck & Co. Inc. Novel forms of diflunisal and related compounds
EP0494419A2 (en) * 1991-01-08 1992-07-15 ZAMBON GROUP S.p.A. Process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid
US5183935A (en) * 1991-08-01 1993-02-02 Zambon Group S.P.A. Process for the preparation of 5-(2',4'difluorophenyl)-salicylic acid in pure form II

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082404A1 (en) * 1981-12-21 1983-06-29 Merck & Co. Inc. Novel forms of diflunisal and related compounds
EP0494419A2 (en) * 1991-01-08 1992-07-15 ZAMBON GROUP S.p.A. Process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid
EP0494419A3 (en) * 1991-01-08 1992-12-09 Zambon Group S.P.A. Process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid
US5183935A (en) * 1991-08-01 1993-02-02 Zambon Group S.P.A. Process for the preparation of 5-(2',4'difluorophenyl)-salicylic acid in pure form II
EP0529279A1 (en) * 1991-08-01 1993-03-03 ZAMBON GROUP S.p.A. Process for the preparation of 5-(2',4'-difluorophenyl)-salicylic acid in pure form II

Also Published As

Publication number Publication date
CY674A (en) 1973-03-08
MY7300229A (en) 1973-12-31

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Legal Events

Date Code Title Description
PS Patent sealed
423P Notice of intention to present a petition (sect. 23/1949)
423P Notice of intention to present a petition (sect. 23/1949)
EPO Patent for which application for extension of term has been made to the comptroller or the court
423G Proceeding under section 23 patents act 1949
EPF Patent extended in pursuance of application for extension of term and in force
PE20 Patent expired after termination of 20 years