GB1050733A - - Google Patents

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Publication number
GB1050733A
GB1050733A GB1050733DA GB1050733A GB 1050733 A GB1050733 A GB 1050733A GB 1050733D A GB1050733D A GB 1050733DA GB 1050733 A GB1050733 A GB 1050733A
Authority
GB
United Kingdom
Prior art keywords
methyl
chlorobenzoyl
methoxy
butyl
aryl
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 GB1050733A publication Critical patent/GB1050733A/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)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (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)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1,050,733. Indole derivatives. MERCK & CO. Inc. Jan. 29, 1964 [Feb. 1, 1963], No. 2064/66. Divided out of 1,050,728. Heading C2C. Indolyl aliphatic acids of the formula wherein R 1 is an aryl, substituted aryl, heterocyclic aryl or substituted heterocyclic aryl radical; 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 hydrogen or halogen or a C 1-5 alkyl, C 1-5 alkoxy, haloalkyl, nitro, amino, substituted amino, cyano, aminomethyl, mercapto, dialkylsulphamoyl or benzylmercapto radical, e.g. 1-p-chlorobenzoyl- 2-methyl-5-methoxy-indole-3-acetic acid, are made by heating the t.-butyl ester with a strong acid in an inert solvent, e.g. by heating at a temperature above 50‹ C. in the presence of p-toluenesulphonic acid in benzene. A number of methods for preparing the t.-butyl ester used as a starting material are described. Other intermediates include ethyl α-(1-p-chlorobenzoyl- 2-methyl-5-methoxy-3-indolyl)-acetate, ethyl- and t.-butyl - (2 - methyl - 5 - methoxy - 3 - indolyl) - acetate, ethyl # - acetyl - # - (2 - nitro - 5 - methoxy - phenyl) - propionate, methyl 2 - nitro - 5 - methoxybenzyl ketone, t.-butyl 1 - p - chlorobenzoyl - 2 - methyl - 5 - methoxyindole - 3 - glycollate, 1 - butyl 1 - p - chlorobenzoyl - 2 - methyl - 5 - methoxy - 3 - indole glyoxylic acid, t.-butyl 1 - p - chlorobenzoyl - 2 - methyl - 5 - methoxyindole - (3) - glyoxalate, 1 - p - chlorobenzoyl - 2 - methyl - 5 - methoxyindole - 3 - glyoxylyl chloride and the corresponding 1-unsubstituted indole- (3)-glyoxalate and glyoxylyl chloride.
GB1050733D 1963-02-01 Active GB1050733A (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
GB1050733A true GB1050733A (en)

Family

ID=22969254

Family Applications (13)

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

Family Applications After (12)

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

Country Status (11)

Country Link
AT (1) AT277992B (en)
BE (1) BE643268A (en)
BR (1) BR6456479D0 (en)
CH (16) CH457434A (en)
DE (16) DE1695492A1 (en)
DK (11) DK109514C (en)
FI (9) FI46955C (en)
FR (1) FR1559559A (en)
GB (13) GB1050735A (en)
NL (1) NL6400813A (en)
SE (12) SE302463B (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
DK112238B (en) 1968-11-25
DE1770802A1 (en) 1972-02-17
GB1050738A (en)
FI47100C (en) 1973-09-10
DK112239B (en) 1968-11-25
BE643268A (en) 1964-07-31
DE1695492A1 (en) 1971-04-01
DE1695486A1 (en) 1971-04-15
FI47098B (en) 1973-05-31
CH464203A (en) 1968-10-31
GB1050737A (en)
FI47096B (en) 1973-05-31
FR1559559A (en) 1969-03-14
FI46955B (en) 1973-05-02
DE1770116A1 (en) 1971-10-14
FI47101B (en) 1973-05-31
DK112313B (en) 1968-12-02
CH457434A (en) 1968-06-15
FI47101C (en) 1973-09-10
DK113501B (en) 1969-03-31
CH464202A (en) 1968-10-31
SE320666B (en) 1970-02-16
DE1695484A1 (en) 1971-04-15
DE1695487A1 (en) 1970-10-01
SE302463B (en) 1968-07-22
DE1695488A1 (en) 1970-09-17
CH489495A (en) 1970-04-30
SE302133B (en) 1968-07-08
FI47097B (en) 1973-05-31
FI46955C (en) 1973-08-10
FI47185C (en) 1973-10-10
FI47100B (en) 1973-05-31
DE1695485A1 (en) 1971-04-15
CH466284A (en) 1968-12-15
CH466289A (en) 1968-12-15
DK112314B (en) 1968-12-02
CH457437A (en) 1968-06-15
DE1695489A1 (en) 1970-08-13
CH466286A (en) 1968-12-15
SE302130B (en) 1968-07-08
CH457435A (en) 1968-06-15
SE302131B (en) 1968-07-08
DK112446B (en) 1968-12-16
SE317975B (en) 1969-12-01
GB1050729A (en)
DK109334C (en) 1968-04-16
CH466288A (en) 1968-12-15
GB1050736A (en)
GB1050728A (en)
DE1770134A1 (en) 1971-09-30
GB1050739A (en)
FI47098C (en) 1973-09-10
FI47185B (en) 1973-07-02
DE1793561A1 (en) 1972-01-20
GB1050730A (en)
BR6456479D0 (en) 1973-09-20
DE1770132A1 (en) 1971-09-30
DK112447B (en) 1968-12-16
DE1470059B1 (en) 1970-01-29
DE1695491A1 (en) 1971-04-15
CH466285A (en) 1968-12-15
AT277992B (en) 1970-01-12
CH457436A (en) 1968-06-15
DE1695493A1 (en) 1971-04-01
SE320367B (en) 1970-02-09
FI47099B (en) 1973-05-31
CH466283A (en) 1968-12-15
SE304995B (en) 1968-10-14
GB1050732A (en)
FI47097C (en) 1973-09-10
FI47096C (en) 1973-09-10
DK111751B (en) 1968-10-07
DK109562C (en) 1968-05-13
SE307133B (en) 1968-12-23
SE307948B (en) 1969-01-27
SE302132B (en) 1968-07-08
DE1695490A1 (en) 1971-04-15
CH557815A (en) 1975-01-15
GB1050731A (en)
DK109514C (en) 1968-05-06
FI47099C (en) 1973-09-10
CH466290A (en) 1968-12-15
CH466287A (en) 1968-12-15
GB1050740A (en)
GB1050734A (en)
NL6400813A (en) 1964-08-03
GB1050735A (en)
SE320069B (en) 1970-02-02

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