GB1299282A - Indole derivatives - Google Patents

Indole derivatives

Info

Publication number
GB1299282A
GB1299282A GB1215570A GB1215570A GB1299282A GB 1299282 A GB1299282 A GB 1299282A GB 1215570 A GB1215570 A GB 1215570A GB 1215570 A GB1215570 A GB 1215570A GB 1299282 A GB1299282 A GB 1299282A
Authority
GB
United Kingdom
Prior art keywords
alkyl
hydrogen
chr
oxo
formula
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
GB1215570A
Inventor
David Richard Herbst
Herchel Smith
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.)
Wyeth LLC
Original Assignee
American Home Products Corp
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 American Home Products Corp filed Critical American Home Products Corp
Priority to GB1215570A priority Critical patent/GB1299282A/en
Publication of GB1299282A publication Critical patent/GB1299282A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems

Landscapes

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

Abstract

1299282 Indole derivatives AMERICAN HOME PRODUCTS CORP 13 March 1970 12155/70 Heading C2C Novel indole derivatives of the general formula where A is in which Y is Z is -CHR<SP>9</SP>- or -CHR 10 -CHR 11 -; R is hydrogen, C 1-12 alkyl optionally substituted by a hydroxy or oxo or ketalized oxo group; R<SP>1</SP> is hydrogen, or oxo; R<SP>2</SP>, R<SP>7</SP>, R<SP>8</SP>, B<SP>9</SP>, R<SP>1</SP> 0 and R<SP>11</SP> are hydrogen or C 1-12 alkyl; R<SP>4</SP> is C 1-12 alkyl or phenyl R<SP>5</SP> is C 1-12 alkyl, C 2-12 alkenyl, di-C 1-12 -alkyl amino-C 1-1 -alkyl, phen-C 1-12 -alkyl, C 1-12 alkoxycarbonyl or pyrrolidino-C 1-12 -alkyl with the proviso that when A is D 2 R<SP>5</SP> is C 1-12 alkyl and when A is E or F R<SP>5</SP> is not di(C 1-12 alkyl)amino-C 1-12 -alkyl or pyrrolidino-(C 1-12 )- alkyl; R 6 is hydrogen C 1-12 alkyl, C 1-12 alkoxy, phlu-C 1-12 -alkoxy, halo, C 1-12 alkanoyloxy, phen- C 1-12 -alkanoyloxy, or hydroxy except when A is D2 R<SP>6</SP> is hydrogen-C 1-12 -alkyl, or C 1-12 alkoxy; R<SP>14</SP> is C 1-12 alkyl optionally substituted by a hydroxy, oxo or ketalized oxo group; and X is an amino for example of a strong inorganic acid or organic sulphonic acid or pharmaceutically acceptable non-toxic addition salt thereof may be prepared by a suitable combination (a) reduction of where W is oxygen or sulphur; (b) Fischer indole synthesis using IB and IC (c) alkylation of the indole nitrogen; (d) condensation cyclisation of the amine with and acid R<SP>4</SP>CO CHR<SP>2</SP>-Z-COOH or a functional derivative thereof; (e) reduction of a quaternary ammonium salt of formula E; (f) alkylation of the nitrogen atom to produce the quaternary of formula E; or (g) reductive clearage of the C-N bond in E by alkali metal in liquid ammonia to give D2. Pharmaceutical compositions of compounds of Formula III with a diluent are diuretics and some show antiinflammatory activity when administered orally, compounds IV and XV show analgesic activity when administered orally or parenterally and III, IV and XV show anti-inflammatory activity when administered orally.
GB1215570A 1970-03-13 1970-03-13 Indole derivatives Expired GB1299282A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1215570A GB1299282A (en) 1970-03-13 1970-03-13 Indole derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1215570A GB1299282A (en) 1970-03-13 1970-03-13 Indole derivatives

Publications (1)

Publication Number Publication Date
GB1299282A true GB1299282A (en) 1972-12-13

Family

ID=9999351

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1215570A Expired GB1299282A (en) 1970-03-13 1970-03-13 Indole derivatives

Country Status (1)

Country Link
GB (1) GB1299282A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4572911A (en) * 1984-08-02 1986-02-25 Mcneilab, Inc. Hexahydroindolinzine compounds, pharmaceutical compositions and methods and intermediates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4572911A (en) * 1984-08-02 1986-02-25 Mcneilab, Inc. Hexahydroindolinzine compounds, pharmaceutical compositions and methods and intermediates

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees