GB1050737A - - Google Patents

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Publication number
GB1050737A
GB1050737A GB1050737DA GB1050737A GB 1050737 A GB1050737 A GB 1050737A GB 1050737D A GB1050737D A GB 1050737DA GB 1050737 A GB1050737 A GB 1050737A
Authority
GB
United Kingdom
Prior art keywords
aryl
alkyl
hydrogen
indole
acetic 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.)
Active
Application number
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.)
Publication of GB1050737A publication Critical patent/GB1050737A/en
Active legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
    • C07D209/281-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/30Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32Oxygen atoms
    • C07D209/36Oxygen atoms in position 3, e.g. adrenochrome

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1,050,737. Indole derivatives. MERCK & CO. Inc. Jan. 29, 1964 [Feb. 1, 1963], No. 2068/66. Divided out of 1,050,728. Heading C2C. Indole-3-acetic acid derivatives of the formula wherein R 1 is an aryl, heterocyclic aryl or substituted aryl or heterocyclic aryl group, e.g. pchlorophenyls, R 2 is a hydrogen atom or a C 1-5 alkyl, C 2-5 alkenyl, aryl, aralkyl, alkaryl or substituted alkyl or aryl radical, R 3 is hydrogen or a C 1-5 alkyl or C 2-5 alkenyl radical and R 5 is a hydrogen or halogen atom or a C 1-5 alkyl, C 1-5 alkoxy, e.g. CH 3 O, haloalkyl, nitro, amino, substituted amino, cyano, aminomethyl, alkylsubstituted amino methyl, mercapto, dialkysulphamoyl or benzyl mercapto radical, are made by reacting the corresponding 1-unsub stituted compound with at least two equivalents of sodium hydride in an inert solvent, cooling the mixture below room temperature, adding the acyl halide of a carboxylic acid of the formula R 1 COOH to form the mixed anhydride of the acid R 2 COOH and the 1-R.CO-indole-3- acetic acid and agitating this in a dilute aqueous hydrogen halide at a temperature below ambient. The exemplified product is 1-p-chlorobenzoyl - 2 - methyl - 5 - methoxyindole - 3 - acetic acid.
GB1050737D 1963-02-01 Active GB1050737A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US25564263A 1963-02-01 1963-02-01

Publications (1)

Publication Number Publication Date
GB1050737A true GB1050737A (en)

Family

ID=22969254

Family Applications (13)

Application Number Title Priority Date Filing Date
GB1050738D Active GB1050738A (en) 1963-02-01
GB1050733D Active GB1050733A (en) 1963-02-01
GB1050739D Active GB1050739A (en) 1963-02-01
GB1050737D Active GB1050737A (en) 1963-02-01
GB1050735D Active GB1050735A (en) 1963-02-01
GB1050730D Active GB1050730A (en) 1963-02-01
GB1050729D Active GB1050729A (en) 1963-02-01
GB1050734D Active GB1050734A (en) 1963-02-01
GB1050736D Active GB1050736A (en) 1963-02-01
GB1050728D Active GB1050728A (en) 1963-02-01
GB1050731D Active GB1050731A (en) 1963-02-01
GB1050732D Active GB1050732A (en) 1963-02-01
GB1050740D Active GB1050740A (en) 1963-02-01

Family Applications Before (3)

Application Number Title Priority Date Filing Date
GB1050738D Active GB1050738A (en) 1963-02-01
GB1050733D Active GB1050733A (en) 1963-02-01
GB1050739D Active GB1050739A (en) 1963-02-01

Family Applications After (9)

Application Number Title Priority Date Filing Date
GB1050735D Active GB1050735A (en) 1963-02-01
GB1050730D Active GB1050730A (en) 1963-02-01
GB1050729D Active GB1050729A (en) 1963-02-01
GB1050734D Active GB1050734A (en) 1963-02-01
GB1050736D Active GB1050736A (en) 1963-02-01
GB1050728D Active GB1050728A (en) 1963-02-01
GB1050731D Active GB1050731A (en) 1963-02-01
GB1050732D Active GB1050732A (en) 1963-02-01
GB1050740D Active GB1050740A (en) 1963-02-01

Country Status (11)

Country Link
AT (1) AT277992B (en)
BE (1) BE643268A (en)
BR (1) BR6456479D0 (en)
CH (16) CH466290A (en)
DE (16) DE1695492A1 (en)
DK (11) DK109334C (en)
FI (9) FI46955C (en)
FR (1) FR1559559A (en)
GB (13) GB1050740A (en)
NL (1) NL6400813A (en)
SE (12) SE317975B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU163233B (en) * 1970-07-31 1973-07-28
WO1989012436A1 (en) * 1988-06-21 1989-12-28 Vita Zahnfabrik H. Rauter Gmbh & Co. Kg Disperse ceramic mass
GB9518994D0 (en) * 1995-09-16 1995-11-15 Agrevo Uk Ltd Fungicides

Also Published As

Publication number Publication date
FI47098C (en) 1973-09-10
BR6456479D0 (en) 1973-09-20
SE307133B (en) 1968-12-23
DE1695486A1 (en) 1971-04-15
FI47100B (en) 1973-05-31
DK112314B (en) 1968-12-02
FI47101B (en) 1973-05-31
GB1050738A (en)
SE320069B (en) 1970-02-02
CH464203A (en) 1968-10-31
GB1050740A (en)
CH466288A (en) 1968-12-15
SE302133B (en) 1968-07-08
FI46955C (en) 1973-08-10
SE320666B (en) 1970-02-16
CH466287A (en) 1968-12-15
CH466283A (en) 1968-12-15
DE1695488A1 (en) 1970-09-17
CH457437A (en) 1968-06-15
GB1050729A (en)
BE643268A (en) 1964-07-31
FI47096C (en) 1973-09-10
DE1695489A1 (en) 1970-08-13
CH457434A (en) 1968-06-15
DE1695491A1 (en) 1971-04-15
GB1050739A (en)
FI47101C (en) 1973-09-10
DE1695490A1 (en) 1971-04-15
CH457436A (en) 1968-06-15
NL6400813A (en) 1964-08-03
SE317975B (en) 1969-12-01
FI47100C (en) 1973-09-10
DE1770116A1 (en) 1971-10-14
FI47099B (en) 1973-05-31
SE307948B (en) 1969-01-27
FI47097C (en) 1973-09-10
SE320367B (en) 1970-02-09
AT277992B (en) 1970-01-12
DK109514C (en) 1968-05-06
FI47097B (en) 1973-05-31
FI46955B (en) 1973-05-02
DK112238B (en) 1968-11-25
GB1050735A (en)
FI47098B (en) 1973-05-31
GB1050731A (en)
FI47185C (en) 1973-10-10
DE1695485A1 (en) 1971-04-15
DE1770134A1 (en) 1971-09-30
SE304995B (en) 1968-10-14
GB1050732A (en)
CH466286A (en) 1968-12-15
DE1695484A1 (en) 1971-04-15
DE1470059B1 (en) 1970-01-29
DK113501B (en) 1969-03-31
GB1050728A (en)
FI47096B (en) 1973-05-31
FR1559559A (en) 1969-03-14
GB1050736A (en)
SE302132B (en) 1968-07-08
CH457435A (en) 1968-06-15
CH464202A (en) 1968-10-31
DK112447B (en) 1968-12-16
FI47099C (en) 1973-09-10
DK112239B (en) 1968-11-25
DK109562C (en) 1968-05-13
DE1770802A1 (en) 1972-02-17
CH466285A (en) 1968-12-15
SE302131B (en) 1968-07-08
DK111751B (en) 1968-10-07
CH466284A (en) 1968-12-15
CH466289A (en) 1968-12-15
DK109334C (en) 1968-04-16
FI47185B (en) 1973-07-02
GB1050734A (en)
DE1695487A1 (en) 1970-10-01
DE1793561A1 (en) 1972-01-20
GB1050730A (en)
SE302130B (en) 1968-07-08
DK112313B (en) 1968-12-02
DE1695493A1 (en) 1971-04-01
CH466290A (en) 1968-12-15
SE302463B (en) 1968-07-22
CH489495A (en) 1970-04-30
DK112446B (en) 1968-12-16
GB1050733A (en)
DE1770132A1 (en) 1971-09-30
DE1695492A1 (en) 1971-04-01
CH557815A (en) 1975-01-15

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