GB1318050A - Indole derivatives - Google Patents

Indole derivatives

Info

Publication number
GB1318050A
GB1318050A GB3509970A GB3509970A GB1318050A GB 1318050 A GB1318050 A GB 1318050A GB 3509970 A GB3509970 A GB 3509970A GB 3509970 A GB3509970 A GB 3509970A GB 1318050 A GB1318050 A GB 1318050A
Authority
GB
United Kingdom
Prior art keywords
benzyloxy
indole
chohch
hydroxy
alkyl
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
GB3509970A
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 CH1191869A external-priority patent/CH514586A/en
Priority claimed from CH438370A external-priority patent/CH525884A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB1318050A publication Critical patent/GB1318050A/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
    • C07D209/30—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
    • 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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms

Landscapes

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

Abstract

1318050 Indole-derived hydroxyamines SANDOZ Ltd 20 July 1970 [5 Aug 1969 24 Oct 1969 (2) 24 March 1970 24 June 1970] 35099/70 Heading C2C The invention comprises compounds of formula and their acid addition salts, wherein R 1 is C 1-6 alkyl, C 3-4 cycloalkyl or 3-phenylpropyl, and R 2 is Me, HOCH 2 , MeOCH 2 , or CO 2 H or its C 1-4 alkyl ester. The carboxylic acids are obtained by hydrolysing the esters, but otherwise the above compounds are prepared by (1) reacting the corresponding 4-glycidyloxy- or/and 4-(3- halo-2-hydroxy)propoxy-indoles with R 1 NH 2 ; (2) reducing the corresponding N-benzyl- and/or 3-dialkylaminomethyl-indole; (3) reducing the corresponding 4-RR<SP>1</SP>C : NCH 2 CHOHCH 2 O-indole, where R, R<SP>1</SP> are each C 1-3 alkyl, or R-R<SP>1</SP> is (CH 2 ) 3 . Intermediates also prepared are 4- hydroxy and 4-benzyloxy analogues of the above compounds; ethyl 4-hydroxy, 4-benzyloxy, or 4-(3-substituted amino-2-hydroxypropoxy)-indole - 2 - carboxylates; 4 - hydroxy and 4 benzyloxy-2-methyl (or hydroxymethyl) indoles; 4 - benzyloxy - 2 - dimethylaminomethylindole; 4 - benzyloxy - 3 - dimethylaminomethyl- 2 - methyl (or hydroxymethyl) indole; 4- ([PhCH 2 ] 2 N- or H 2 N-CH 2 CHOHCH 2 O)-2,3- dimethylindole; 4 - (isoPrNHCH 2 CHOHCH 2 O) - 2 - hydroxymethylindole; PhCH 2 N(isoPr)CH 2 - CHOHCH 2 Cl; and ethyl 4-benzyloxy-3-dimethylaminomethylindole-2-carboxylate. Therapeutic compositions for oral administration comprise compounds of the above formula, which have a blocking effect on vascular adrenergic beta-receptors, and an antiarrhythmic effect. Reference has been directed by the Comptroller to Specification 1,129,072.
GB3509970A 1969-08-05 1970-07-20 Indole derivatives Expired GB1318050A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH1191869A CH514586A (en) 1969-08-05 1969-08-05 4-indolyl basic ethers prepn
CH1586669 1969-10-24
CH1586569 1969-10-24
CH438370A CH525884A (en) 1970-03-24 1970-03-24 4-indolyl basic ethers prepn
CH953670 1970-06-24

Publications (1)

Publication Number Publication Date
GB1318050A true GB1318050A (en) 1973-05-23

Family

ID=27509196

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3509970A Expired GB1318050A (en) 1969-08-05 1970-07-20 Indole derivatives

Country Status (8)

Country Link
US (1) US3696120A (en)
JP (1) JPS5022555B1 (en)
BE (1) BE754360A (en)
DE (1) DE2038482A1 (en)
FR (1) FR2068461B1 (en)
GB (1) GB1318050A (en)
PL (1) PL81365B1 (en)
SE (1) SE369522B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU586691B2 (en) * 1985-07-01 1989-07-20 Richter Gedeon Vegyeszeti Gyar Rt. Diamino-androstane derivatives, process for their preparation and pharmaceutical compositions containing them

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2508251C2 (en) * 1975-02-26 1983-12-29 Boehringer Mannheim Gmbh, 6800 Mannheim Derivatives of indole, processes for their preparation and medicaments containing them
US4076829A (en) * 1974-11-16 1978-02-28 Boehringer Mannheim Gmbh Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases
US4152446A (en) * 1974-11-16 1979-05-01 Boehringer Mannheim Gmbh Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases
US4340541A (en) * 1975-08-15 1982-07-20 Sandoz Ltd. 4-(2-Benzoyloxy-3-tert.-butylaminopropoxy-2-methyl indole
US4235919A (en) * 1977-07-21 1980-11-25 Sandoz Ltd. 1-(Indol-4-yloxy)-3-(2-substituted amino)-2-propanols and pharmaceutical use thereof
JPS54156272U (en) * 1978-04-24 1979-10-30
JPS5746200Y2 (en) * 1978-06-26 1982-10-12
EP0025111B1 (en) * 1979-08-10 1984-07-25 Sandoz Ag 3-aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them
DE3115993A1 (en) * 1981-04-13 1982-11-11 Schering Ag, 1000 Berlin Und 4619 Bergkamen NEW INDOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS THAT CONTAIN THESE COMPOUNDS
US5013761A (en) * 1988-06-03 1991-05-07 Eli Lilly And Company Serotonin antagonists

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1129072A (en) * 1966-02-01 1968-10-02 Ici Ltd Benzofuran and indole derivatives
US3471515A (en) * 1965-02-01 1969-10-07 Sandoz Ag (2-hydroxy-3-substituted aminopropoxy)indoles
FR353F (en) * 1968-06-07 1972-01-07
DE1948507C2 (en) * 1969-09-25 1982-10-21 Sandoz-Patent-GmbH, 7850 Lörrach 4- (2-Hydroxy-3-aminopropoxy) indole derivatives, their salts, processes for their preparation and medicines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU586691B2 (en) * 1985-07-01 1989-07-20 Richter Gedeon Vegyeszeti Gyar Rt. Diamino-androstane derivatives, process for their preparation and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
US3696120A (en) 1972-10-03
BE754360A (en) 1971-02-03
FR2068461A1 (en) 1971-08-27
PL81365B1 (en) 1975-08-30
SE369522B (en) 1974-09-02
JPS5022555B1 (en) 1975-07-31
DE2038482A1 (en) 1971-02-18
FR2068461B1 (en) 1974-01-11

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
426 Order made revoking patent and granting patent of addition in lieu thereof (sect. 26(2)/1949)
SP Amendment (slips) printed
PCNP Patent ceased through non-payment of renewal fee