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GB1129072A - Benzofuran and indole derivatives - Google Patents

Benzofuran and indole derivatives

Info

Publication number
GB1129072A
GB1129072A GB4421/66A GB442166A GB1129072A GB 1129072 A GB1129072 A GB 1129072A GB 4421/66 A GB4421/66 A GB 4421/66A GB 442166 A GB442166 A GB 442166A GB 1129072 A GB1129072 A GB 1129072A
Authority
GB
United Kingdom
Prior art keywords
stands
formula
radical
compound
case
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
GB4421/66A
Inventor
Ralph William Turner
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB4421/66A priority Critical patent/GB1129072A/en
Priority to DE1967J0032795 priority patent/DE1593901B2/en
Priority to SE01103/67A priority patent/SE360653B/xx
Priority to CH1629569A priority patent/CH489490A/en
Priority to CH140167A priority patent/CH486441A/en
Priority to CH1629269A priority patent/CH492696A/en
Priority to CH1629469A priority patent/CH489489A/en
Priority to CH1629369A priority patent/CH489488A/en
Priority to NL6701573A priority patent/NL6701573A/xx
Priority to BE693518D priority patent/BE693518A/xx
Priority to FR93353A priority patent/FR96649E/fr
Publication of GB1129072A publication Critical patent/GB1129072A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1,129,072. Benzofuran and indole derivatives. IMPERIAL CHEMICAL INDUSTRIES Ltd. 2 Jan., 1967 [1 Feb., 1966], No. 4421/66. Addition to 1,058,822. Heading C2C. Racemic compounds of the general Formula (I) (wherein R<SP>1</SP> stands for hydrogen or an alkyl radical, R<SP>2</SP> stands for an alkyl, hydroxyalkyl, cycloalkyl, alkenyl or aralkyl radical, and wherein the ring A is a furan or pyrrole ring which together with the benzene ring forms the benzofuran or indole nucleus, said ring A optionally bearing one or more alkyl substituents) and the esters thereof and the acid addition salts of the alcohols and esters are prepared by (a)-in the case of the alcoholsreacting a compound of the Formula (II) (wherein Y stands for the group -CHOH.CH 2 X or wherein X stands for a halogen atom), or a mixture of the halohydrin and epoxide, with NHR<SP>1</SP>R<SP>2</SP>, (b)-in the case of the alcoholsreacting a compound of the Formula (III) with a compound of the Formula (IV) (which may be generated in situ) or (V) (c)-in the case of the alcohols wherein R<SP>1</SP> stands for hydrogen and R<SP>2</SP> stands for an alkyl, hydroxyalkyl, cycloalkyl or aralkyl radical, apart from a benzyl or substituted benzyl radical-hydrogenolysing a compound of the Formula (VI) (wherein R<SP>4</SP> stands for a hydrogenolysable radical) or an acid addition salt thereof, (d)-in the case of the alcohols wherein R<SP>1</SP> stands for hydrogen and R<SP>2</SP> stands for a radical of the formula -CHR<SP>5</SP>R<SP>6</SP>, wherein R<SP>5</SP> stands for hydrogen or an alkyl radical and R<SP>6</SP> stands for an alkyl, hydroxyalkyl, alkenyl, aryl or aralkyl radical, or R<SP>5</SP> and R<SP>6</SP> are joined together with the adjacent carbon atom to form a cycloalkyl radical-reacting a compound of the Formula (VIII) with R<SP>5</SP>COR<SP>6</SP> under reducing conditions, (e)-in the case of the alcohols wherein R<SP>1</SP> stands for hydrogen-reacting a compound of the Formula (VII) with R<SP>2</SP>X or (f)-in the case of the estersreacting an acid addition salt of a compound of the Formula (I) with an acylating agent, optionally followed in each case by salt formation or conversion to the free base as appropriate. The preparation of starting materials of Formulµ (II), (III) and (VII) is described. The compounds of the invention are #- adrenergic blocking agents, and may be administered in the form of pharmaceutical preparations containing them together with a diluent or carrier.
GB4421/66A 1963-07-30 1966-02-01 Benzofuran and indole derivatives Expired GB1129072A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
GB4421/66A GB1129072A (en) 1966-02-01 1966-02-01 Benzofuran and indole derivatives
DE1967J0032795 DE1593901B2 (en) 1966-02-01 1967-01-17 BASIC SUBSTITUTED BENZOFURANS OR INDOLES AND PROCESS FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
SE01103/67A SE360653B (en) 1966-02-01 1967-01-25
CH1629569A CH489490A (en) 1963-07-30 1967-01-31 Process for the preparation of propanolamine derivatives
CH140167A CH486441A (en) 1963-07-30 1967-01-31 Process for the preparation of propanolamine derivatives
CH1629269A CH492696A (en) 1963-07-30 1967-01-31 Process for the preparation of propanolamine derivatives
CH1629469A CH489489A (en) 1963-07-30 1967-01-31 Process for the preparation of propanolamine derivatives
CH1629369A CH489488A (en) 1963-07-30 1967-01-31 Process for the preparation of propanolamine derivatives
NL6701573A NL6701573A (en) 1966-02-01 1967-02-01
BE693518D BE693518A (en) 1966-02-01 1967-02-01
FR93353A FR96649E (en) 1966-02-01 1967-02-01

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4421/66A GB1129072A (en) 1966-02-01 1966-02-01 Benzofuran and indole derivatives

Publications (1)

Publication Number Publication Date
GB1129072A true GB1129072A (en) 1968-10-02

Family

ID=9776870

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4421/66A Expired GB1129072A (en) 1963-07-30 1966-02-01 Benzofuran and indole derivatives

Country Status (6)

Country Link
BE (1) BE693518A (en)
DE (1) DE1593901B2 (en)
FR (1) FR96649E (en)
GB (1) GB1129072A (en)
NL (1) NL6701573A (en)
SE (1) SE360653B (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2059558A1 (en) * 1969-07-25 1971-06-04 Sandoz Sa
FR2068461A1 (en) * 1969-08-05 1971-08-27 Sandoz Sa
FR2121607A1 (en) * 1971-01-07 1972-08-25 Sandoz Sa
JPS4943960A (en) * 1972-08-30 1974-04-25
US4235919A (en) 1977-07-21 1980-11-25 Sandoz Ltd. 1-(Indol-4-yloxy)-3-(2-substituted amino)-2-propanols and pharmaceutical use thereof
WO1982002550A1 (en) * 1981-01-16 1982-08-05 Ag Sandoz Derivatives of 3-aminopropoxy-aryl compounds,preparation thereof and drugs containing them
US6022894A (en) * 1996-04-09 2000-02-08 Nps Pharmaceuticals, Inc. Method of using calcilytic compounds
WO2000037464A3 (en) * 1998-12-18 2000-11-02 Hoffmann La Roche 4-(aminoalkoxy)benzofurans as n-myristoyltransferase inhibitors
US6432656B1 (en) 1996-12-03 2002-08-13 Nps Pharmaceuticals, Inc. Calcilytic compounds
US6818660B2 (en) 1996-04-09 2004-11-16 Nps Pharmaceuticals, Inc. Calcilytic compounds
US7202261B2 (en) 1996-12-03 2007-04-10 Nps Pharmaceuticals, Inc. Calcilytic compounds
CN117024880A (en) * 2023-09-14 2023-11-10 美新科技股份有限公司 High-temperature-resistant plastic-wood material composition and plastic-wood product

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH495983A (en) * 1968-02-09 1970-09-15 Sandoz Ag Process for the preparation of levorotatory 4- (2-hydroxy-3-isopropylaminopropoxy) indole
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
US3699123A (en) * 1970-03-24 1972-10-17 Sandoz Ltd 4-(3-amino-2-hydroxy-propoxy) indole derivatives
WO1980000152A1 (en) * 1978-07-03 1980-02-07 Sandoz Ag 3-aminopropoxy-aryl derivates,preparation and use thereof
EP0013878A1 (en) * 1979-01-18 1980-08-06 Sandoz Ag 3-Aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them
DE3310891A1 (en) * 1983-03-25 1984-09-27 Boehringer Mannheim Gmbh, 6800 Mannheim NEW INDOLINON (2) DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS AND INTERMEDIATE PRODUCTS

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2059558A1 (en) * 1969-07-25 1971-06-04 Sandoz Sa
FR2068461A1 (en) * 1969-08-05 1971-08-27 Sandoz Sa
FR2121607A1 (en) * 1971-01-07 1972-08-25 Sandoz Sa
JPS4943960A (en) * 1972-08-30 1974-04-25
US4235919A (en) 1977-07-21 1980-11-25 Sandoz Ltd. 1-(Indol-4-yloxy)-3-(2-substituted amino)-2-propanols and pharmaceutical use thereof
WO1982002550A1 (en) * 1981-01-16 1982-08-05 Ag Sandoz Derivatives of 3-aminopropoxy-aryl compounds,preparation thereof and drugs containing them
US6022894A (en) * 1996-04-09 2000-02-08 Nps Pharmaceuticals, Inc. Method of using calcilytic compounds
US6521667B1 (en) 1996-04-09 2003-02-18 Nps Pharmaceuticals, Inc. Calcilytic compounds
US6818660B2 (en) 1996-04-09 2004-11-16 Nps Pharmaceuticals, Inc. Calcilytic compounds
US6432656B1 (en) 1996-12-03 2002-08-13 Nps Pharmaceuticals, Inc. Calcilytic compounds
US7202261B2 (en) 1996-12-03 2007-04-10 Nps Pharmaceuticals, Inc. Calcilytic compounds
WO2000037464A3 (en) * 1998-12-18 2000-11-02 Hoffmann La Roche 4-(aminoalkoxy)benzofurans as n-myristoyltransferase inhibitors
US6376491B1 (en) 1998-12-18 2002-04-23 Basilea Pharmaceutica Ag Bicyclic compounds
CN117024880A (en) * 2023-09-14 2023-11-10 美新科技股份有限公司 High-temperature-resistant plastic-wood material composition and plastic-wood product
CN117024880B (en) * 2023-09-14 2024-05-24 美新科技股份有限公司 High-temperature-resistant plastic-wood material composition and plastic-wood product

Also Published As

Publication number Publication date
DE1593901B2 (en) 1976-12-23
DE1593901A1 (en) 1970-10-29
NL6701573A (en) 1967-08-02
SE360653B (en) 1973-10-01
BE693518A (en) 1967-08-01
FR96649E (en) 1976-02-27

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