IE781077L - Phenylalanines and phenylethylamines - Google Patents

Phenylalanines and phenylethylamines

Info

Publication number
IE781077L
IE781077L IE781077A IE107778A IE781077L IE 781077 L IE781077 L IE 781077L IE 781077 A IE781077 A IE 781077A IE 107778 A IE107778 A IE 107778A IE 781077 L IE781077 L IE 781077L
Authority
IE
Ireland
Prior art keywords
difluoromethyl
veratryl
alpha
ketone
phenylalanines
Prior art date
Application number
IE781077A
Other versions
IE47542B1 (en
Original Assignee
Merck & Co Inc
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 Merck & Co Inc filed Critical Merck & Co Inc
Publication of IE781077L publication Critical patent/IE781077L/en
Publication of IE47542B1 publication Critical patent/IE47542B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C07D233/78—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

alpha -Difluoromethyl-3,4-di- OR-phenylalanines and its esters, and (1-difluoromethyl)- and 1-(trifluoromethyl)-2-(3,4-di-OR- phenyl) ethylamines, wherein R is hydrogen or a C2-C6 alkanoyl, have been prepared. Homoveratric acid is transformed into veratryl-difluoromethyl- ketone or veratryl- trifluoro- methyl- ketone, this reacts with methoxyamine, and the obtained O-methyl-oxime is reduced to the amine. The 3- and 4-methoxygroups are hydrolysed into hydroxy-groups. Reaction of veratryl- difluoromethylketone with ammonium-carbonate and sodium cyanide yields alpha -difluoromethyl-5-(3 min , 4 min -dimethoxybenzyl)-2,4-imidazolidine-dione, hydrolysis results in alpha -difluoromethyl-3- hydroxytyrosine. The compounds have Dopa-decarboxylase inhibiting activity and some of them are antihypertensive agents. [EP0000034A1]
IE1077/78A 1977-06-01 1978-05-30 Di-and tri-fluoromethyl amino acids and amines,compositions and processes for preparing said compounds IE47542B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US80238877A 1977-06-01 1977-06-01

Publications (2)

Publication Number Publication Date
IE781077L true IE781077L (en) 1978-12-01
IE47542B1 IE47542B1 (en) 1984-04-18

Family

ID=25183563

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1077/78A IE47542B1 (en) 1977-06-01 1978-05-30 Di-and tri-fluoromethyl amino acids and amines,compositions and processes for preparing said compounds

Country Status (6)

Country Link
EP (1) EP0000034B1 (en)
JP (1) JPS5416437A (en)
DE (1) DE2862407D1 (en)
DK (1) DK240678A (en)
IE (1) IE47542B1 (en)
IT (1) IT7849635A0 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA783273B (en) * 1977-07-11 1979-06-27 Merrell Toraude & Co A-halomethyl amino acids
IL59481A0 (en) * 1977-07-11 1980-05-30 Merrell Toraude & Co -halomethyl amino acids
AU3872678A (en) * 1977-09-01 1980-02-14 Merrell Toraude & Co Alpha-halomethyl amines
IE49522B1 (en) * 1979-04-26 1985-10-16 Merrell Toraude & Co Alpha-halomethylaminoacids
NZ194348A (en) * 1979-07-26 1982-09-14 Merrell Toraude & Co Fluorinated methyl-beta-alanine derivatives and pharmaceutical compositions
US4421767A (en) * 1981-06-01 1983-12-20 Merrell Toraude Et Compagnie Compounds and methods for treating depression
JP5902575B2 (en) * 2012-07-20 2016-04-13 国立大学法人お茶の水女子大学 Process for producing optically active fluorinated amine compound and optically active fluorinated amine compound

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3046300A (en) * 1960-10-21 1962-07-24 Merck & Co Inc alpha-trifluoromethyloxyphenylalanines
GB1218135A (en) * 1967-07-28 1971-01-06 Abbott Lab Substituted phenethylamine derivatives

Also Published As

Publication number Publication date
JPS5416437A (en) 1979-02-07
IT7849635A0 (en) 1978-05-31
EP0000034A1 (en) 1978-12-20
IE47542B1 (en) 1984-04-18
DK240678A (en) 1978-12-02
DE2862407D1 (en) 1984-06-28
EP0000034B1 (en) 1984-05-23

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