GB1131545A - Indole derivatives - Google Patents

Indole derivatives

Info

Publication number
GB1131545A
GB1131545A GB1780966A GB1780966A GB1131545A GB 1131545 A GB1131545 A GB 1131545A GB 1780966 A GB1780966 A GB 1780966A GB 1780966 A GB1780966 A GB 1780966A GB 1131545 A GB1131545 A GB 1131545A
Authority
GB
United Kingdom
Prior art keywords
carboxylic acid
acid
alkyl
hydrogen
methoxy
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
GB1780966A
Inventor
Svend Age Christensen
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.)
Xellia Pharmaceuticals ApS
Original Assignee
Dumex AS
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 Dumex AS filed Critical Dumex AS
Priority to GB1780966A priority Critical patent/GB1131545A/en
Priority to DE19671645966 priority patent/DE1645966A1/en
Priority to NL6705634A priority patent/NL6705634A/xx
Priority to SE561067A priority patent/SE316772B/xx
Publication of GB1131545A publication Critical patent/GB1131545A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26—Radicals 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
    • C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Abstract

1,131,545. Preparing indole 3-carboxylic acid derivatives. DUMEX (DUMEX Ltd) A.S. 21 July, 1967 [22 April, 1966], No. 17809/66. Heading C2C. Indole derivatives of the general formula wherein R<SP>1</SP> is hydrogen, halogen, or a hydroxyl, amino, nitro, C 1 -C 4 alkyl or C 1 -C 4 alkoxy group, R 2 is hydroxyl, C 1 -C 4 alkoxy, NH 2 , or benzyloxy, R<SP>3</SP> is hydrogen, C 1 -C 4 alkyl, phenyl, or benzyl, and R<SP>4</SP> is hydrogen, halogen or C 1 -C 4 alkyl, are prepared by the Arndt- Eistert synthesis from the required 3-indole carboxylic acid, via the 3-acid chloride and 3-diazoketone. As a starting material, 1-(pchlorobenzoyl) - 5 - methoxy - 2 - methylindole- 3-carboxylic acid is prepared by reacting #-aminocrotonic acid ethyl ester with quinone to give 2-methyl-3-carbethoxy-5-hydroxyindole, which is methylated to the corresponding 5-methoxy compound, this being transesterified at the 3-position to the benzyl ester. The ester is acylated by a Schotten-Baumann reaction to 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-carboxylic acid benzyl ester, which is hydrogenated to give the required acid. This is treated according to the invention to yield the corresponding 3-acetic acid, which is optionally esterified, amidized or benzylated.
GB1780966A 1966-04-22 1966-04-22 Indole derivatives Expired GB1131545A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB1780966A GB1131545A (en) 1966-04-22 1966-04-22 Indole derivatives
DE19671645966 DE1645966A1 (en) 1966-04-22 1967-04-21 Process for the production of indole derivatives
NL6705634A NL6705634A (en) 1966-04-22 1967-04-21
SE561067A SE316772B (en) 1966-04-22 1967-04-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1780966A GB1131545A (en) 1966-04-22 1966-04-22 Indole derivatives

Publications (1)

Publication Number Publication Date
GB1131545A true GB1131545A (en) 1968-10-23

Family

ID=10101614

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1780966A Expired GB1131545A (en) 1966-04-22 1966-04-22 Indole derivatives

Country Status (4)

Country Link
DE (1) DE1645966A1 (en)
GB (1) GB1131545A (en)
NL (1) NL6705634A (en)
SE (1) SE316772B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585880A (en) * 1982-02-26 1986-04-29 Troponwerke Gmbh & Co. Kg Process for the preparation of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4585880A (en) * 1982-02-26 1986-04-29 Troponwerke Gmbh & Co. Kg Process for the preparation of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetic acid

Also Published As

Publication number Publication date
DE1645966A1 (en) 1970-12-23
SE316772B (en) 1969-11-03
NL6705634A (en) 1967-10-23

Similar Documents

Publication Publication Date Title
GB1260868A (en) 0,2,3,6-tetrasubstituted indoles
GB1063385A (en) Substituted -a-halogenated methylenyl 3-indolyl acetic acids
US3489767A (en) 1-(phenylsulfonyl)-3-indolyl aliphatic acid derivatives
GB1131545A (en) Indole derivatives
Somei et al. 1-Aminoindoles
TW429259B (en) Palladium catalyzed indolization
USRE35631E (en) Method of production of essentially pure melatonin and the method of solubilizing melatonin in water
GB1455100A (en) Derivatives of 3,3-bis-4-hydroxyphenyl-2-indolinone and process for the preparation thereof
Bognar et al. Flavonoids—VI: The preparation and reactions of the epoxides of 2′-hydroxy-chalcone derivatives
CA1331602C (en) Preparation process of acemetacin
GB1304599A (en)
US3483220A (en) Process for preparing 1-aroylindole-3-acetic acid compounds
Manske The Synthesis of Some Indol Derivatives
HU194180B (en) Process for production of derivatives of 1 /4-nitrophenil/-3-azabyciclo /3,1/ heptane-2,4-dion
GB1390304A (en) 1,2,3,4-tetrahydro-9h-pyrido-3,4b indole derivatives and their use as intermediates in the synthesis of eburnamonine
ES271789A1 (en) 5, 5-diloweralkyl-4-omicron-lower alkyl-2, 3-cyclocarbonato-l-pyranosyl halides
GB2098205A (en) Indoles
US3564011A (en) Method for preparing 1-acyl-3-indolyl aliphatic acid derivatives
GB1304622A (en)
JPS6122081A (en) Preparation of hydantoin compound
US2944064A (en) Process for preparing 5-hydroxy-tryptamine through new intermediates
GB1198752A (en) Substituted p-Chlorobenzoylanilines
GB1195174A (en) Amino-Substituted Esters and their Reactions
US4506077A (en) Tin complexes of indoline-2-carboxylic acids and esters prepared from o-nitrophenylpyruvic acids and esters
US3471514A (en) Process for alpha-(5-nitroindolyl-3)-alkanoic acids