GB1012480A - Anti-inflammatory agents - Google Patents

Anti-inflammatory agents

Info

Publication number
GB1012480A
GB1012480A GB2878062A GB2878062A GB1012480A GB 1012480 A GB1012480 A GB 1012480A GB 2878062 A GB2878062 A GB 2878062A GB 2878062 A GB2878062 A GB 2878062A GB 1012480 A GB1012480 A GB 1012480A
Authority
GB
United Kingdom
Prior art keywords
compounds
acids
ethyl
methyl
butyl
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
GB2878062A
Inventor
John Stuart Nicholson
Stewart Sanders Adams
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.)
Boots Pure Drug Co Ltd
Original Assignee
Boots Pure Drug Co Ltd
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 Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Priority to GB2878062A priority Critical patent/GB1012480A/en
Priority to CH932863A priority patent/CH450382A/en
Publication of GB1012480A publication Critical patent/GB1012480A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • 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
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic 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
    • 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
    • C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings

Landscapes

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

Abstract

The invention comprises compounds of general formula <FORM:1012480/C2/1> wherein R1 represents cycloalkyloxy (C3-C5), cycloalkylthio (C3-C5), alkylthio (C2-C3), when R2 is hydrogen; or R1 represents ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, branched alkyl (C6-C7), cycloalkyl (C3-C5), alkoxy (C3-C4), alkenyloxy (C3-C4), alkylthio (C1-C5), alkenylthio (C3-C5), cycloalkyloxy (C3-C7), cycloalkylthio (C3-C7), phenoxy, phenylthio, alkenyl (C2-C4), when R2 is methyl; X represents CH2OH, COOR3 where R3 is hydrogen or alkyl (C1-C4) or, when R2 is methyl, dialkylamino substituted alkyl (C1-C4), CONH2, CH2NH2; and the non-toxic organic and inorganic salts of the acids, basic esters and amines; provided that X is not CH2OH when R1 is ethyl; and their preparation by methods described, these being analogous to known methods. Processes and intermediate and final compounds in examples are as follows:- 4-Substituted phenyl acetic acids are esterified to form ethyl esters which on treatment with ethyl carbonate yield ethyl 4-substituted phenylmalonates; methyl iodide yields the C-methyl compounds which are hydrolysed to form the malonic acids and these decarboxylated yielding 2-(4-substituted phenyl)-propionic acids. Ethyl esters thereof are obtained and reduced with lithium aluminium hydride to form 2-(4-n-propyl, -n-butyl, and -allyloxy phenyl)-propanols. 2-(4-Propyl and -butyl phenyl)-propionamides are prepared by reacting the acids with thionyl chloride and the acid chlorides with ammonia. 2-(4-Propoxy and -butoxy phenyl)-propionic acids are prepared by hydrogenation of the allyloxy and but-2-enyloxy compounds. 4-Cyclopentyloxyphenyl acetic acid is prepared by hydrolysis of the ethyl ester, obtained from the 4-hydroxy compound by reaction with cyclopentyl iodide. 4-Ethylthioacetophenone, obtained by Friedel-Crafts reaction of thiophenetole and acetyl chloride, yields on reaction with sulphur and morpholine the intermediate thioacetmorpholide which may be hydrolysed to 4-ethylthiophenylacetic acid; 4-n-propyl and -isopropyl thio compounds are similarly obtained. 2-(4-Propylphenyl)-propylamine is obtained by lithium aluminium hydride reduction of the amide.ALSO:Therapeutic compositions comprise compounds of general formula <FORM:1012480/A5-A6/1> wherein R4 represents n-butyl, cycloalkyloxy (C3-C5), cycloalkylthio (C3-C5) or alkylthio (C1-C3) when R2 is hydrogen; or R4 represents n-butyl, n-pentyl, cycloalkyl (C3-C4), alkenyloxy (C4), alkoxy (C4), branched alkyl (C6-C7), alkylthio (C1-C5), alkenylthio (C3-C5), cycloalkyloxy (C3-C7), or cycloalkylthio (C3-C7) when R2 is methyl; and X is CH2OH, COOR3 where R3 is hydrogen or alkyl (C1-C4) or, when R2 is methyl, dialkylamino substituted alkyl (C1-4), CONH2, CH2NH2; and the nontoxic organic and inorganic salts of the acids and amines, in association with a pharmaceutically acceptable diluent or carrier; also solid compositions of 2-41-n-propylphenylpropionic acid its salts and ethyl ester. Forms are described for oral (capsules, tablets, lozenges, granules, mixtures elixirs, syrups, solutions, suspensions), topical (ointments, creams, lotions) and parenteral administration. The compounds have anti-inflammatory, antipyretic and analgesic properties.
GB2878062A 1962-02-02 1962-07-26 Anti-inflammatory agents Expired GB1012480A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2878062A GB1012480A (en) 1962-07-26 1962-07-26 Anti-inflammatory agents
CH932863A CH450382A (en) 1962-02-02 1963-07-26 Process for the preparation of anti-inflammatory agents

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2878062A GB1012480A (en) 1962-07-26 1962-07-26 Anti-inflammatory agents

Publications (1)

Publication Number Publication Date
GB1012480A true GB1012480A (en) 1965-12-08

Family

ID=10281041

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2878062A Expired GB1012480A (en) 1962-02-02 1962-07-26 Anti-inflammatory agents

Country Status (1)

Country Link
GB (1) GB1012480A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001322A (en) 1969-05-28 1977-01-04 Eli Lilly And Company 3-substituted phenylalkyl amines
US4335251A (en) 1976-12-08 1982-06-15 Hisamitsu Pharmaceutical Co. Inc. Phenyl-i-propionic acid esters and pharmaceutical use thereof
EP0057047A1 (en) * 1981-01-24 1982-08-04 Reckitt And Colman Products Limited Process for the preparation of 2-(2,4-dichlorophenoxy) phenylacetic acid
US4362891A (en) 1979-06-18 1982-12-07 Glaxo Group Limited Alkanoic acid derivatives
EP0068222A1 (en) * 1981-06-18 1983-01-05 Technobiotic Ltd. Process for the preparation of 2-(2,4-dichlorophenoxy)phenylacetic acid
EP2129218A1 (en) * 2007-02-16 2009-12-09 Emisphere Technologies, Inc. Compounds having a cyclic moiety and compositions for delivering active agents

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001322A (en) 1969-05-28 1977-01-04 Eli Lilly And Company 3-substituted phenylalkyl amines
US4335251A (en) 1976-12-08 1982-06-15 Hisamitsu Pharmaceutical Co. Inc. Phenyl-i-propionic acid esters and pharmaceutical use thereof
US4362891A (en) 1979-06-18 1982-12-07 Glaxo Group Limited Alkanoic acid derivatives
EP0057047A1 (en) * 1981-01-24 1982-08-04 Reckitt And Colman Products Limited Process for the preparation of 2-(2,4-dichlorophenoxy) phenylacetic acid
EP0068222A1 (en) * 1981-06-18 1983-01-05 Technobiotic Ltd. Process for the preparation of 2-(2,4-dichlorophenoxy)phenylacetic acid
EP2129218A1 (en) * 2007-02-16 2009-12-09 Emisphere Technologies, Inc. Compounds having a cyclic moiety and compositions for delivering active agents
EP2129218A4 (en) * 2007-02-16 2011-11-30 Emisphere Tech Inc Compounds having a cyclic moiety and compositions for delivering active agents

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