GB1356310A - Indole derivatives - Google Patents

Indole derivatives

Info

Publication number
GB1356310A
GB1356310A GB4481371A GB4481371A GB1356310A GB 1356310 A GB1356310 A GB 1356310A GB 4481371 A GB4481371 A GB 4481371A GB 4481371 A GB4481371 A GB 4481371A GB 1356310 A GB1356310 A GB 1356310A
Authority
GB
United Kingdom
Prior art keywords
alkyl
cycloalkyl
compounds
benzyl
ccme
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
GB4481371A
Inventor
F Troxler
F Seemann
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.)
Sandoz AG
Original Assignee
Sandoz 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
Priority claimed from CH1446770A external-priority patent/CH535763A/en
Priority claimed from CH1489870A external-priority patent/CH535764A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1356310A publication Critical patent/GB1356310A/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
    • 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
    • C07D209/30—Indoles; 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
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

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

Abstract

1356310 Indole derivatives SANDOZ Ltd 27 Sept 1971 [30 Sept 1970 8 Oct 1970] 44813/71 Heading C2C The invention comprises compounds of formula and their acid addition salts, wherein R 1 is C 1-6 alkyl, C 3-6 cycloalkyl, C 8-12 phenylalkyl (in which at least 2 carbon atoms separate Ph and NH), CH #CCMe 2 or allyl; R 2 is H, Me, CONH 2 , CONHR or CON(R) 2 where R is C 1-4 alkyl; R 3 is H or Me; and R 4 is C 1-17 alkyl, C 3-7 cycloalkyl (possibly substituted by one or more C 1-4 alkyl) ; Ph (possibly monosubstituted by Me, MeO, F or Cl) or C 1-7 chloroalkyl, provided that R 4 is not Me 3 C when R 1 is C 1-6 alkyl, C 3-4 cycloalkyl or Ph(CH 2 ) 3 , and R 2 is H or Me. These compounds are prepared by (a) acylating the corresponding alcohols (II), or (b) (except when R 1 is CH # CCMe 2 or allyl) debenzylating I-N-benzyl derivatives (which are themselves prepared from II-N-benzyl derivatives). Intermediates otherwise specified are 2-carbamyl-4-hydroxyindole and its benzyl and glycidyl ethers. Therapeutic compositions having a blocking effect on the adrenergic beta-receptors, and useful for the prophylaxis or treatment of coronary diseases, and for the treatment of heart rhythm disorders, comprise compounds of the above formula in association with a pharmaceutical carrier.
GB4481371A 1970-09-30 1971-09-27 Indole derivatives Expired GB1356310A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1446770A CH535763A (en) 1970-09-30 1970-09-30 4-(2-acyloxy-3-amino-propoxy)-indoles - as beta-adrenergic blocking agents
CH1489870A CH535764A (en) 1970-10-08 1970-10-08 Indolyloxypropanolamine esters - with beta-blocking activity

Publications (1)

Publication Number Publication Date
GB1356310A true GB1356310A (en) 1974-06-12

Family

ID=25714518

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4481371A Expired GB1356310A (en) 1970-09-30 1971-09-27 Indole derivatives

Country Status (9)

Country Link
JP (1) JPS5617345B1 (en)
AU (1) AU469293B2 (en)
BE (1) BE773206A (en)
DE (1) DE2148553A1 (en)
ES (1) ES395496A1 (en)
FR (1) FR2108098B1 (en)
GB (1) GB1356310A (en)
NL (1) NL178592C (en)
SE (1) SE375771B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH578526A5 (en) * 1972-06-23 1976-08-13 Sandoz Ag
DE2635209C2 (en) * 1975-08-15 1983-01-27 Sandoz-Patent-GmbH, 7850 Lörrach 4- (2-Benzoyloxy-3-tert-butylamino-propoxy) -2-methylindole, its (S) -enantiomer, their acid addition salts, processes for their preparation and medicaments containing these compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL131726C (en) * 1965-02-01
BE734126A (en) * 1968-06-07 1969-12-05
FR2019185A1 (en) * 1968-09-30 1970-06-26 Sandoz Sa 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta

Also Published As

Publication number Publication date
ES395496A1 (en) 1974-11-01
NL7112936A (en) 1972-04-05
AU469293B2 (en) 1976-02-12
FR2108098B1 (en) 1975-06-06
BE773206A (en) 1972-03-28
SE375771B (en) 1975-04-28
DE2148553A1 (en) 1972-04-06
FR2108098A1 (en) 1972-05-12
JPS5617345B1 (en) 1981-04-22
NL178592C (en) 1986-04-16
AU3397871A (en) 1973-04-05

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years