GB984291A - Aminoethanol derivatives - Google Patents

Aminoethanol derivatives

Info

Publication number
GB984291A
GB984291A GB46032/61A GB4603261A GB984291A GB 984291 A GB984291 A GB 984291A GB 46032/61 A GB46032/61 A GB 46032/61A GB 4603261 A GB4603261 A GB 4603261A GB 984291 A GB984291 A GB 984291A
Authority
GB
United Kingdom
Prior art keywords
stands
bromoacetylphenanthrene
phenanthryl
bromo
ethanol
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
GB46032/61A
Inventor
Ralph Howe
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 GB46032/61A priority Critical patent/GB984291A/en
Publication of GB984291A publication Critical patent/GB984291A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises compounds of the general formula RCHOHCH2NR1R2 (wherein R stands for a phenanthryl, fluorenyl or anthryl radical, R1 stands for a hydrogen atom or an alkyl radical containing not more than four carbon atoms, and R2 stands for a branched-chain alkyl radical, optionally substituted by one or more hydroxyl or aryl radicals) and pharmaceutically-acceptable acid addition salts thereof, pharmaceutical preparations containing them, and their preparation by (a) reducing RCOCH2X (wherein X stands for a halogen atom) followed by reaction of the reduction product with NHR1R2; (b) reacting RA (wherein A stands for the group <FORM:0984291/C2/1> or -CHOHCH2X) with NHR1R2; (c) reducing RCOCH2NR1R2 or an acid addition salt thereof, (d) reducing RCOR5 (wherein R5 stands for the group -CHO or -CH(OH)2) in the presence of NHR1R2, or (e)-in the case of compounds wherein R1 stands for a hydrogen atom and R2 stands for the radical -CHR3R4 (wherein R3 and R4 may be the same or different and stand for straight- or branched-chain alkyl radicals, optionally substituted by one or more hydroxyl or aryl radicals, or R3 stands for a hydrogen atom and R4 stands for a branched-chain alkyl radical, optionally substituted by one or more hydroxyl or aryl radicals)-reacting RCOCH2 NH2 with R3R4CO under reducing conditions, optionally followed in each case by acid addition salt formation. The following intermediates are prepared from the starting materials indicated in parentheses: 2-bromo-1-(2-phenanthryl) ethanol (2-bromoacetylphenanthrene)- 2 - bromo - 1 - (3-phenanthryl) ethanol (3 - bromoacetylphenanthrene); 2 - bromo - 1 - (9 - phenanthryl) ethanol (9 - bromoacetylphenanthrene); 2-bromo - 1 - (2 - anthryl) ethanol (2 - bromoacetylanthracene); 3 - phenanthrylglyoxal hydrate (3-bromoacetylphenanthrene); 9 - phenanthrylglyoxal (9 - bromoacetylphenanthrene); 3 - aminoacetylphenanthrene hydrobromide (3 - bromoacetylphenanthrene); 9 - isopropylmethylaminoacetylphenanthrenehydrochloride (9-bromoacetylphenanthrene). The compounds of the invention are of value in the treatment, or prophylaxis of cronary artery disease, and may be administered orally or parenterally in the form of pharmaceutical preparations (e.g. tablets, capsules, aqueous or oily solutions, aqueous or oily suspensions, emulsions, injectable aqueous or oily solutions or suspensions, and dispersible powders) containing them together with a diluent or carrier. The Provisional Specification defines the invention in wider terms.
GB46032/61A 1961-12-22 1961-12-22 Aminoethanol derivatives Expired GB984291A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB46032/61A GB984291A (en) 1961-12-22 1961-12-22 Aminoethanol derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB46032/61A GB984291A (en) 1961-12-22 1961-12-22 Aminoethanol derivatives

Publications (1)

Publication Number Publication Date
GB984291A true GB984291A (en) 1965-02-24

Family

ID=10439564

Family Applications (1)

Application Number Title Priority Date Filing Date
GB46032/61A Expired GB984291A (en) 1961-12-22 1961-12-22 Aminoethanol derivatives

Country Status (1)

Country Link
GB (1) GB984291A (en)

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