GB869775A - 3-indolyl ketones - Google Patents

3-indolyl ketones

Info

Publication number
GB869775A
GB869775A GB31457/59A GB3145759A GB869775A GB 869775 A GB869775 A GB 869775A GB 31457/59 A GB31457/59 A GB 31457/59A GB 3145759 A GB3145759 A GB 3145759A GB 869775 A GB869775 A GB 869775A
Authority
GB
United Kingdom
Prior art keywords
alkyl
aralkyl
ketones
groups
aralkoxy
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
GB31457/59A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB869775A publication Critical patent/GB869775A/en
Expired legal-status Critical Current

Links

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
    • C07D209/12Radicals substituted by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0869775/IV (b)/1> wherein A and B represent hydrogen or C1-8 branched-chain alkyl group, and the preparation of 3-indoyl ketones by reacting an indole unsubstituted in the 3-position with phosphorus oxychloride and a carboxylic acid amide of a hydrocarbon carboxylic acid optionally substituted by one or more inert substituents such as halo, cyano, nitro, tertiary amino, alkoxy, aryloxy, aralkoxy, alkylmercapto, aralkylmercapto or arylmercapto and a C1-8 alkylamine. The indoles may be substituted in the 1-position by C1-8 alkyl or C7-13 aralkyl groups, in the 2 position by C1-8 alkyl, C7-13 aralkyl, C6-12 aryl or haloaryl groups and in the 4,5,6 and -7 positions by C1-8 alkyl or alkoxy, C7-13 aralkyl or aralkoxy, C6-12 aryl or aryloxy, hydroxy groups, or halogen atoms. Indolyl ketones containing free hydroxy groups in the 4,5,6 or 7 positions are prepared from the corresponding benzyloxy compound, e.g. by catalytic hydrogenation. Specification 744,774 and German Specification 614,326 are referred to.ALSO:Pharmaceutical compositions comprise compounds of the general formula <FORM:0869775/VI/1> wherein A and B are hydrogen atoms or C1-5 alkyl radicals and R5 is a branched-chain C4-8 alkyl group and a solid or liquid pharmaceutical carrier. The compositions may be in the form of tablets, powder packets or capsules or dissolved or suspended in a solvent, for oral or parenteral administration.
GB31457/59A 1958-09-24 1959-09-15 3-indolyl ketones Expired GB869775A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US869775XA 1958-09-24 1958-09-24

Publications (1)

Publication Number Publication Date
GB869775A true GB869775A (en) 1961-06-07

Family

ID=22202086

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31457/59A Expired GB869775A (en) 1958-09-24 1959-09-15 3-indolyl ketones

Country Status (1)

Country Link
GB (1) GB869775A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3226399A (en) * 1964-08-07 1965-12-28 American Cyanamid Co Substituted 3-formylindoles
US3259622A (en) * 1962-09-07 1966-07-05 Merck & Co Inc 1-benzyl-3-indolyl-alpha-haloalkyl and alkylidenyl acetic acids
US3352856A (en) * 1965-12-20 1967-11-14 Upjohn Co 2-(p-alkoxyphenyl)-3-substituted indoles
EP0022634A1 (en) * 1979-06-28 1981-01-21 Teijin Limited Acylated indole derivatives, processes for their preparation and pharmaceutical compositions and drugs comprising them
AU574383B2 (en) * 1983-09-28 1988-07-07 Nippon Zoki Pharmaceutical Co., Ltd. Acylindole derivatives
WO2001032621A1 (en) * 1999-10-29 2001-05-10 Wakunaga Pharmaceutical Co., Ltd. Novel indole derivatives and drugs containing the same as the active ingredient
US7125906B2 (en) 2002-04-03 2006-10-24 Astrazeneca Ab Indole derivatives having anti-angiogenetic activity

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3259622A (en) * 1962-09-07 1966-07-05 Merck & Co Inc 1-benzyl-3-indolyl-alpha-haloalkyl and alkylidenyl acetic acids
US3226399A (en) * 1964-08-07 1965-12-28 American Cyanamid Co Substituted 3-formylindoles
US3352856A (en) * 1965-12-20 1967-11-14 Upjohn Co 2-(p-alkoxyphenyl)-3-substituted indoles
EP0022634A1 (en) * 1979-06-28 1981-01-21 Teijin Limited Acylated indole derivatives, processes for their preparation and pharmaceutical compositions and drugs comprising them
AU574383B2 (en) * 1983-09-28 1988-07-07 Nippon Zoki Pharmaceutical Co., Ltd. Acylindole derivatives
WO2001032621A1 (en) * 1999-10-29 2001-05-10 Wakunaga Pharmaceutical Co., Ltd. Novel indole derivatives and drugs containing the same as the active ingredient
US7125906B2 (en) 2002-04-03 2006-10-24 Astrazeneca Ab Indole derivatives having anti-angiogenetic activity

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