GB1315830A - Halophenyl-2-hydroxyphenylacetic acids and their derivatives - Google Patents

Halophenyl-2-hydroxyphenylacetic acids and their derivatives

Info

Publication number
GB1315830A
GB1315830A GB5932370A GB5932370A GB1315830A GB 1315830 A GB1315830 A GB 1315830A GB 5932370 A GB5932370 A GB 5932370A GB 5932370 A GB5932370 A GB 5932370A GB 1315830 A GB1315830 A GB 1315830A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
alkyl
amino
fluorophenyl
acid
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
GB5932370A
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 GB1315830A publication Critical patent/GB1315830A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
    • C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • 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
    • 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

Landscapes

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

Abstract

1315830 Substituted phenyl-benzoic acids MERCK & CO Inc 14 Dec 1970 [22 Dec 1969] 14 Dec 1970 [22 Dec 1969] 59323/70 Heading C2C Novel compounds of the formula wherein X is halogen, R is H, halo, C 1-6 alkyl or C 1-6 alkoxy, R 1 is OH, NH 2 , C 1-6 alkoxy, di- (C 1-6 alkyl)amino-C 1-5 alkoxy, hydroxy C 1-6 alkoxy, C 1-6 alkylamino, di-(C 1-6 alkyl)amino, polyhydroxy C 1-6 alkoxy, (C 1-6 alkoxy)-(C 1-6 alkoxy), phenyl C 1-5 alkoxy, phenoxy, (C 1-6 alkoxy)phenoxy di-(C 1-5 alkyl)aminophenoxy, (C 1-6 alkanoylamino)phenoxy, 2-carboxy-4-(4<SP>1</SP>- fluorophenyl) - benzyloxy, (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 or di-(C 1-5 alkyl)amino (C 1-5 alkyl)amino radical, or a naturally occurring amino acid radical with attachment at the nitrogen, and R 2 is H, C 1-6 alkanoyl or C 2-6 alkenyl radical, R 3 is H, halogen, or a C 1-6 alkyl, C 1-6 alkoxy, benzyl or C 2-6 alkenyl radical; and the left hand ring is para to the OR 2 or CH 2 COR 1 residue, may be obtained by reacting a phenylbenzoic acid of formula with thionyl chloride, phosphorus oxychloride, or an alkanoyl, aroyl or heteroaroyl chloride to form an acid chloride, reacting the latter with diazomethane to form a diazoketone and rearranging the latter with loss of nitrogen in the presence of water and a metal catalyst (e.g. Ag, Pt or Cu) to form the phenylacetic acid compound. The alkali metal, alkaline earth metal, amine, aluminium, iron, choline, glucosamine, S-methyl methionine, piperazine, dimethylaminoethanol, chloroquine and hydroxychloroquine salts may be formed, and the anhydrides of the acids and the mixed anhydrides of the acids and 2-acetoxyphenylacetic acid, esters and amides may be obtained by conventional methods. Preparation of the following intermediates is also described: 4-(3- or 4<SP>1</SP>-fluorophenyl)aniline, 4-(pentafluorophenyl)aniline and similar alkyl, halo or alkoxy substituted fluorophenyl anilines; pentafluoro-nitrobiphenyls, chloro-fluorophenyl-anisole and alkyl, benzyl or halosubstituted derivatives, similar chlorofluorophenylphenols, 2-hydroxy-5-(4<SP>1</SP>-fluorophenyl)- benzoic acid and derivatives thereof. Pharmaceutical compositions, useful in reducing inflammation and relieving pain in rheumatoid arthritis, osteoarthritis, gout, infectious arthritis and rheumatic fever, comprise compounds of Formula I above, together with a pharmaceutically acceptable carrier in forms suitable for administration orally, parenterally, topically or rectally.
GB5932370A 1969-12-22 1970-12-14 Halophenyl-2-hydroxyphenylacetic acids and their derivatives Expired GB1315830A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US88741669A 1969-12-22 1969-12-22

Publications (1)

Publication Number Publication Date
GB1315830A true GB1315830A (en) 1973-05-02

Family

ID=25391088

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5932370A Expired GB1315830A (en) 1969-12-22 1970-12-14 Halophenyl-2-hydroxyphenylacetic acids and their derivatives

Country Status (6)

Country Link
US (1) US3671580A (en)
AU (1) AU2326070A (en)
DE (1) DE2062956A1 (en)
FR (1) FR2081392B1 (en)
GB (1) GB1315830A (en)
NL (1) NL7017781A (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4192890A (en) * 1970-04-15 1980-03-11 Roussel Uclaf Novel benzoylphenylacetic acid esters
US3860640A (en) * 1972-04-12 1975-01-14 Nippon Shinyaku Co Ltd 3-alkoxy-5-substituted phenylacetic acids
GB1396726A (en) * 1972-06-15 1975-06-04 Boots Co Ltd Phenylalkanoic acids
US4048332A (en) * 1972-06-15 1977-09-13 The Boots Company Limited Phenylalkanoic acids
US3860636A (en) * 1972-12-06 1975-01-14 Merck & Co Inc Substituted indenyl phosphonic acids having anti-inflammatory activity
US5028629A (en) * 1990-03-28 1991-07-02 Eli Lilly And Company 5-Lipoxygenase inhibitors
PH30449A (en) * 1991-11-25 1997-05-28 Lilly Co Eli Substituted phenyl phenol leukotriene antagonists
DK0745063T3 (en) * 1994-02-17 1999-10-11 American Home Prod Substituted biphenyl derivatives with phosphodiesterase inhibitory effect
US5691376A (en) * 1994-02-17 1997-11-25 American Home Products Corporation Substituted biphenyl derivatives

Family Cites Families (3)

* 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
US3457300A (en) * 1965-06-11 1969-07-22 Merck & Co Inc Acetic acid type compounds
FR1583830A (en) * 1968-04-25 1969-12-05

Also Published As

Publication number Publication date
DE2062956A1 (en) 1971-06-24
FR2081392A1 (en) 1971-12-03
NL7017781A (en) 1971-06-24
FR2081392B1 (en) 1974-08-30
AU2326070A (en) 1972-06-15
US3671580A (en) 1972-06-20

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Legal Events

Date Code Title Description
CSNS Application of which complete specification have been accepted and published, but patent is not sealed