GB991937A - Indoline derivatives and process for preparing them - Google Patents

Indoline derivatives and process for preparing them

Info

Publication number
GB991937A
GB991937A GB3015161A GB3015161A GB991937A GB 991937 A GB991937 A GB 991937A GB 3015161 A GB3015161 A GB 3015161A GB 3015161 A GB3015161 A GB 3015161A GB 991937 A GB991937 A GB 991937A
Authority
GB
United Kingdom
Prior art keywords
indoline
chloride
methylcrotonyl
bromoindoline
bromobutyryl
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
GB3015161A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB991937A publication Critical patent/GB991937A/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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

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:0991937/C2/1> (wherein R represents a hydrogen or halogen atom, R1 represents a hydrogen atom or a methyl group, and R2 and R3 represent hydrogen atoms or C1-4 alkyl groups or, together with the nitrogen atom, form an indoline ring which may be halogenated in the 5-position, or a saturated 5- or 6-membered heterocyclic ring) and physiologically tolerable acid addition salts thereof, pharmaceutical preparations containing them, and their preparation by known methods, e.g. from indoline or a 5-haloindoline. The following intermediates are prepared from the starting materials indicated in parentheses: 1 - crotonylindoline (indoline and crotonyl chloride); 1-(b -ethylaminocrotonyl)-indoline (indoline and diketene, via 1-acetoacetylindoline); 1 - crotonyl - 5 - fluoroindoline - (5-fluoroindole, via 5-fluoroindoline); 1-(b -methylcrotonyl)-indoline (indoline and b -methylcrotonyl chloride); b -bromoisovaleryl chloride (b -bromoisovaleric acid); 1-(b -methylcrotonyl)-5-bromoindoline (1 - acetyl - 5 - bromoindoline, via 5 - bromoindoline); b - bromobutyryl chloride (b -bromobutyric acid); 1-(b -bromobutyryl) - indoline (1 - acetoacetylindoline or 1 - acetoacetylindole, via 1 - (b - hydroxybutyryl)-indoline, or indoline and b -bromobutyryl chloride). The compounds of the invention have sympathicolytic activity and lower the blood pressure; they may be administered orally or parenterally in the form of pharmaceutical preparations (e.g. tablets, dragees and sterile aqueous solutions) containing them in admixture or conjunction with a carrier.
GB3015161A 1960-08-19 1961-08-21 Indoline derivatives and process for preparing them Expired GB991937A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF31914A DE1169450B (en) 1960-08-19 1960-08-19 Process for the production of indoline derivatives and their salts

Publications (1)

Publication Number Publication Date
GB991937A true GB991937A (en) 1965-05-12

Family

ID=7094412

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3015161A Expired GB991937A (en) 1960-08-19 1961-08-21 Indoline derivatives and process for preparing them

Country Status (3)

Country Link
CH (3) CH430714A (en)
DE (1) DE1169450B (en)
GB (1) GB991937A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1136474A1 (en) * 1994-09-20 2001-09-26 Sankyo Company Limited 1-Acetyl-5-bromo-4,6-dimethyl-indoline

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1136474A1 (en) * 1994-09-20 2001-09-26 Sankyo Company Limited 1-Acetyl-5-bromo-4,6-dimethyl-indoline
US6414012B1 (en) 1994-09-20 2002-07-02 Sankyo Company, Limited Heterocyclic derivatives, method of production thereof and pharmaceutical use thereof
US6489475B2 (en) 1994-09-20 2002-12-03 Sankyo Company, Limited Method of producing heterocyclic derivatives

Also Published As

Publication number Publication date
DE1169450B (en) 1964-05-06
CH420154A (en) 1966-09-15
CH420153A (en) 1966-09-15
CH430714A (en) 1967-02-28

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