GB975291A - Derivatives of 1-phenyl-2-aminoethanol - Google Patents

Derivatives of 1-phenyl-2-aminoethanol

Info

Publication number
GB975291A
GB975291A GB34894/62A GB3489462A GB975291A GB 975291 A GB975291 A GB 975291A GB 34894/62 A GB34894/62 A GB 34894/62A GB 3489462 A GB3489462 A GB 3489462A GB 975291 A GB975291 A GB 975291A
Authority
GB
United Kingdom
Prior art keywords
eto
compounds
meo
ethoxy
prepared
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
GB34894/62A
Inventor
Bernard Joseph Mcloughlin
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 DK441664AA priority Critical patent/DK104466C/en
Priority to DK441464AA priority patent/DK106041C/en
Priority to DK441564AA priority patent/DK105277C/en
Priority to DK427163AA priority patent/DK104465C/en
Priority to FR956840A priority patent/FR3077M/en
Publication of GB975291A publication Critical patent/GB975291A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of formula <FORM:0975291/C1/1> wherein X is halogen, alkoxy, alkoxycarbonyl or nitro, Y is alkoxy, R1 and R2 are H or alkyl, R3 is optionally substituted branched-chain alkyl (but specifically excluding those compounds in which X=Y=CH3O-, R1=R2=H and R3=i-Pr, t-Bu, alphamethylbenzyl or 1-methyl -3-phenylpropyl) and salts thereof. A number of general methods of preparing the compounds are described. In examples (1)-(5), the following are prepared by reacting NaBH4 with the appropriate phenylglyoxal in presence of isopropylamine: R1=R2=H, R3=i-Pr and (1) X=Y=EtO, (2) X=MeO, Y=n-BuO, (3) X=MeO2C, Y=MeO, (4) X=MeO,Y=EtO, (5) X=Cl, Y=EtO; the required phenylglyoxals are prepared by oxidation of the corresponding acetophenones with SeO2. In examples (6), (7) and (9) the reaction product of isopropylamine, butylamine or 2-amino -2- methylpropanol-1 with 4-ethoxy -3- nitrophenacyl bromide is reduced with NaBH4 giving compounds R1=R2=H, R3=i-Pr, t-Bu or hydroxy-t-Bu, X=NO2 and Y=EtO; the required phenacyl bromide is made directly from the acetophenone by bromination. In Example 8, the compound R1=H, R2=R3= i-Pr, X=NO2 and Y=EtO is made by reaction of a mixture of 1-(4-ethoxy -3- nitrophenyl) -2- bromoethanol and 4-ethoxy -3- nitrophenyl ethylene oxide with diisopropylamine. In Example 10, 3,4-diethoxyphenyl 1-hydroxyiminoethyl ketone is reduced (H2/Pt) in presence of acetone giving the compound R1=Me, R2=H, R3= i-Pr, X=Y=MeO. In Examples 11 and 12, the compounds R1=Me, R2=H, R3=i-Pr or 1-methyloctyl, X=Y=EtO were prepared by reduction (H2/Pd-C) of a mixture of 1-(3, 4-diethoxyphenyl) -2- aminopropanol and acetone or 2-nonanone. The mixture required for Example 8 is prepared by reacting NaBH4 with 4-ethoxy-3-nitrophenacy bromide. It is stated that the compounds of the invention possess b -adrenergic blocking activity but not sympathominetic activity and are therefore useful for the treatment or prophylaxis of coronary artery disease. They may be used, together with a diluent or carrier, in the form of tablets, capsules, aqueous or oily solutions or suspensions (which may be injectable) or dispersible powders. Suitable diluents are specified and examples are provided.
GB34894/62A 1962-09-12 1962-09-12 Derivatives of 1-phenyl-2-aminoethanol Expired GB975291A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DK441664AA DK104466C (en) 1962-09-12 1963-09-10 Process for the preparation of 1-phenyl-2-alkylaminoethanol derivatives or acid addition salts thereof.
DK441464AA DK106041C (en) 1962-09-12 1963-09-10 Process for the preparation of 1-phenyl-2-alkylaminoalkanol derivatives or acid addition salts thereof.
DK441564AA DK105277C (en) 1962-09-12 1963-09-10 Process for the preparation of 1-phenyl-2-alkylaminoalkanol derivatives or acid addition salts thereof.
DK427163AA DK104465C (en) 1962-09-12 1963-09-10 Process for the preparation of 1-phenyl-2-alkylaminoalkanol derivatives or acid addition salts thereof.
FR956840A FR3077M (en) 1962-09-12 1963-12-11 New drugs based on benzene derivatives for the treatment of coronary artery disease.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR988029A FR3877M (en) 1964-09-14 1964-09-14 New basic amino salts for the treatment of protein deficiency states.

Publications (1)

Publication Number Publication Date
GB975291A true GB975291A (en) 1964-11-11

Family

ID=8838299

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34894/62A Expired GB975291A (en) 1962-09-12 1962-09-12 Derivatives of 1-phenyl-2-aminoethanol

Country Status (4)

Country Link
BE (1) BE637333A (en)
FR (1) FR3877M (en)
GB (1) GB975291A (en)
NL (1) NL297595A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115465853A (en) * 2022-09-07 2022-12-13 西华大学 Orange light carbon dot based on citric acid and chiral 2-amino-1, 2-diphenylethanol and preparation method and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115465853A (en) * 2022-09-07 2022-12-13 西华大学 Orange light carbon dot based on citric acid and chiral 2-amino-1, 2-diphenylethanol and preparation method and application thereof

Also Published As

Publication number Publication date
NL297595A (en)
FR3877M (en) 1966-01-31
BE637333A (en)

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