GB1116434A - Biphenylyl-substituted aliphatic aldehydes and their acetals - Google Patents

Biphenylyl-substituted aliphatic aldehydes and their acetals

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Publication number
GB1116434A
GB1116434A GB38711/67A GB3871167A GB1116434A GB 1116434 A GB1116434 A GB 1116434A GB 38711/67 A GB38711/67 A GB 38711/67A GB 3871167 A GB3871167 A GB 3871167A GB 1116434 A GB1116434 A GB 1116434A
Authority
GB
United Kingdom
Prior art keywords
alkyl
aldehydes
acetals
groups
halide
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
GB38711/67A
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 GB1116434A publication Critical patent/GB1116434A/en
Expired legal-status Critical Current

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    • 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
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    • 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
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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 aldehydes of the general formula <FORM:1116434/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- represent -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 R11 is H and R1\h is a halogen atom or a C1- 5 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 carboxylic acids (containing -COOH in place of -CHO) by protecting any NH2 or CONH2 group present by benzylation, treating the acid with a thionyl halide or a phosphorus halide or oxyhalide, reducing the resulting acid halide and simultaneously or subsequently debenzylating the protected groups, if any. The aldehydes may be converted to dialkyl acetals by reaction with an alkanol or an alkyl orthoformate in the presence of a strong acid (any groups containing active hydrogen being first protected by benzylation and subsequently regenerated). Pharmaceutical preparations.-Tablets and capsules containing the foregoing aldehydes and acetals have anti-inflammatory, anti-pyretic, analgesic and cholesterol-inhibitory activity.
GB38711/67A 1964-09-10 1965-09-07 Biphenylyl-substituted aliphatic aldehydes and their acetals Expired GB1116434A (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
GB1116434A true GB1116434A (en) 1968-06-06

Family

ID=23563534

Family Applications (4)

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

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB38712/67A Expired GB1116435A (en) 1964-09-10 1965-09-07 Biphenylyl-substituted aliphatic alcohols and their ethers

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB38600/67A Expired GB1116433A (en) 1964-09-10 1965-09-07 Amides of biphenylyl aliphatic acids
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) GB1116435A (en)
IL (1) IL24046A (en)
NL (1) NL6511845A (en)

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US4316850A (en) 1968-03-27 1982-02-23 Ciba-Geigy Corporation Tertiary aminoacids
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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
US4052514A (en) * 1971-03-26 1977-10-04 The Boots Company Limited Trihalosubstituted biphenylyl propionic acids
GB1437783A (en) * 1972-09-22 1976-06-03 Boots Co Ltd 2-substituted biphenylyl acetic acids and derivatives thereof
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
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
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
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FR7048M (en) 1969-06-16
FR7047M (en) 1969-06-16
GB1116433A (en) 1968-06-06
US3624142A (en) 1971-11-30
CH490309A (en) 1970-05-15
BR6572746D0 (en) 1973-08-07
NL6511845A (en) 1966-03-11
ES317635A1 (en) 1966-04-01
GB1116435A (en) 1968-06-06
FR7008M (en) 1969-06-02
BE669347A (en) 1966-03-08
FR7007M (en) 1969-06-02
FR1460659A (en) 1966-01-07
IL24046A (en) 1970-03-22
GB1116432A (en) 1968-06-06

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