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GB1116433A - Amides of biphenylyl aliphatic acids - Google Patents

Amides of biphenylyl aliphatic acids

Info

Publication number
GB1116433A
GB1116433A GB38600/67A GB3860067A GB1116433A GB 1116433 A GB1116433 A GB 1116433A GB 38600/67 A GB38600/67 A GB 38600/67A GB 3860067 A GB3860067 A GB 3860067A GB 1116433 A GB1116433 A GB 1116433A
Authority
GB
United Kingdom
Prior art keywords
alkyl
amides
acid
conh2
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
GB38600/67A
Inventor
Tsung-Ying Shen
Conrad Peter Dorn
Bruce Edward Witzel
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 GB1116433A publication Critical patent/GB1116433A/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
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    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/16—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by oxidation of thiols, sulfides, hydropolysulfides, or polysulfides with formation of sulfo or halosulfonyl groups
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    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
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    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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    • 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
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    • 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
    • C07C45/63—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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
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    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
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    • C07—ORGANIC CHEMISTRY
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    • 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
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    • C07C59/40—Unsaturated compounds
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    • C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
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    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
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    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
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    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
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    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
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    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Novel amides of the general formula <FORM:1116433/C2/1> (wherein R3 and R4 each represent a halogen atom or a C1- 5 alkyl, alkylthio or alkylsulphonyl, di-(C1- 5 alkyl)-sulphamoyl, trihalomethyl, benzylthio, SH, NH2, di-(C1- 5 alkyl)-amino, CN, NO2, CONH2, di-(C1- 5 alkyl) -carbamoyl, C1- 6 alkanoylamino or phenyl radical, -X- represents -CH2-, -CH(CF3)-, -CR1R2-, where R1 is H and R2 is C1- 5 alkyl or haloalkyl or C2- 5 alkenyl or alkynyl or R1 and R2 together form a methylene, C2- 5 alkylidene or ethylene group, or -CR1R11-, where R1 is H and R11 is a halogen atom or a C1- 5 alkyl alkoxy group or R1 and R11 are both C1- 5 alkyl groups, and each of n and m is 0, 1 or 2 provided n + m is 1, 2 or 3, or may be zero when -X- is -CH(CF3)-) are prepared from the corresponding acids by the following processes: (a) (except when R3 or R4 is NH2, dialkylamino or CONH2) treating the acid with a thionyl or phosphorus halide in an inert solvent and reacting the resulting acid halide with a compound HN(Y)2, any substituent containing an active hydrogen atom being first protected by benzylation and subsequently regenerated by hydrogenation; or (b) reacting the acid with the compound HN(Y)2 in the presence of cyclohexylcarbodiimide or after reaction with isobutyl chloroformate. The amides of the invention are stated to have anti-inflammatory, antipyretic, analgesic, cholesterol inhibiting and fatty acid synthesis inhibiting activity, and they may be administered orally as tablets or capsules.
GB38600/67A 1964-09-10 1965-09-07 Amides of biphenylyl aliphatic acids Expired GB1116433A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US39555364A 1964-09-10 1964-09-10

Publications (1)

Publication Number Publication Date
GB1116433A true GB1116433A (en) 1968-06-06

Family

ID=23563534

Family Applications (4)

Application Number Title Priority Date Filing Date
GB38711/67A Expired GB1116434A (en) 1964-09-10 1965-09-07 Biphenylyl-substituted aliphatic aldehydes and their acetals
GB38712/67A Expired GB1116435A (en) 1964-09-10 1965-09-07 Biphenylyl-substituted aliphatic alcohols and their ethers
GB38168/65A Expired GB1116432A (en) 1964-09-10 1965-09-07 Biphenylyl aliphatic acids and their salts and esters
GB38600/67A Expired GB1116433A (en) 1964-09-10 1965-09-07 Amides of biphenylyl aliphatic acids

Family Applications Before (3)

Application Number Title Priority Date Filing Date
GB38711/67A Expired GB1116434A (en) 1964-09-10 1965-09-07 Biphenylyl-substituted aliphatic aldehydes and their acetals
GB38712/67A Expired GB1116435A (en) 1964-09-10 1965-09-07 Biphenylyl-substituted aliphatic alcohols and their ethers
GB38168/65A Expired GB1116432A (en) 1964-09-10 1965-09-07 Biphenylyl aliphatic acids and their salts and esters

Country Status (9)

Country Link
US (1) US3624142A (en)
BE (1) BE669347A (en)
BR (1) BR6572746D0 (en)
CH (1) CH490309A (en)
ES (1) ES317635A1 (en)
FR (5) FR1460659A (en)
GB (4) GB1116434A (en)
IL (1) IL24046A (en)
NL (1) NL6511845A (en)

Families Citing this family (46)

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US4053639A (en) * 1964-01-24 1977-10-11 The Boots Company Limited Therapeutically active phenylalkane derivatives
US4316850A (en) 1968-03-27 1982-02-23 Ciba-Geigy Corporation Tertiary aminoacids
US4163788A (en) 1968-03-27 1979-08-07 Ciba-Geigy Corporation Tertiary aminoacids
US3674832A (en) * 1968-08-22 1972-07-04 Schering Corp Cyclopropane carboxylic acid derivatives
SE365788B (en) * 1968-10-25 1974-04-01 Ciba Geigy Ag
GB1268008A (en) * 1969-07-09 1972-03-22 Bdh Pharmaceuticals Ltd ESTERS OF p-BYPHENYLYLACETIC ACID
GB1275927A (en) * 1969-07-16 1972-06-01 Bdh Pharmaceuticals Ltd ESTERS OF p-BIPHENYLYLACETIC ACID
US3981905A (en) * 1970-03-16 1976-09-21 Boots Pure Drug Company Limited 2-(Substituted phenyl) propionic acids
US4192890A (en) * 1970-04-15 1980-03-11 Roussel Uclaf Novel benzoylphenylacetic acid esters
US3864384A (en) * 1970-05-05 1975-02-04 Rorer Inc William H Substituted phenylacetic acid compounds
US3941821A (en) * 1970-05-05 1976-03-02 William H. Rorer, Inc. 2-Thiosulfo biphenylylacetic acids
GB1312642A (en) * 1970-07-13 1973-04-04 Science Union & Cie Pyrazole compounds and process for their manufacture
GB1359987A (en) * 1970-10-12 1974-07-17 Boots Co Ltd 2-substituted biphenylyl propionic acids
GB1437783A (en) * 1972-09-22 1976-06-03 Boots Co Ltd 2-substituted biphenylyl acetic acids and derivatives thereof
US4052514A (en) * 1971-03-26 1977-10-04 The Boots Company Limited Trihalosubstituted biphenylyl propionic acids
US3857880A (en) * 1971-07-20 1974-12-31 Schering Corp Cyclopropane carboxylic acid derivatives
BE787782A (en) * 1971-08-20 1973-02-19 Thomae Gmbh Dr K NEW 4- (4-BIPHENYLYL) -BUTYRAMIDES
DE2205732A1 (en) * 1972-02-08 1973-08-16 Thomae Gmbh Dr K NEW 4- (4-BIPHENYLYL) -BUTIC ACID DERIVATIVES
US4048332A (en) * 1972-06-15 1977-09-13 The Boots Company Limited Phenylalkanoic acids
GB1396726A (en) * 1972-06-15 1975-06-04 Boots Co Ltd Phenylalkanoic acids
US3987197A (en) * 1972-08-17 1976-10-19 Boehringer Ingelheim Gmbh 3-(2'-fluoro-4-biphenylyl)-butyric acid and salts thereof
DE2341506A1 (en) * 1973-08-16 1975-02-27 Thomae Gmbh Dr K NEW BIPHENYL DERIVATIVES AND THE PROCESS FOR THEIR PRODUCTION
US3957861A (en) * 1973-11-07 1976-05-18 The Upjohn Company Biphenylylpropionic acids and esters
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GB1116432A (en) 1968-06-06
FR1460659A (en) 1966-01-07
FR7047M (en) 1969-06-16
ES317635A1 (en) 1966-04-01
GB1116434A (en) 1968-06-06
FR7008M (en) 1969-06-02
BR6572746D0 (en) 1973-08-07
CH490309A (en) 1970-05-15
GB1116435A (en) 1968-06-06
NL6511845A (en) 1966-03-11
BE669347A (en) 1966-03-08
IL24046A (en) 1970-03-22
FR7007M (en) 1969-06-02
US3624142A (en) 1971-11-30
FR7048M (en) 1969-06-16

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