IE35778B1 - 4-(4-(alpha-hydroxybenzyl)piperidino)-4'-fluorobutyrophenone derivatives - Google Patents

4-(4-(alpha-hydroxybenzyl)piperidino)-4'-fluorobutyrophenone derivatives

Info

Publication number
IE35778B1
IE35778B1 IE1361/71A IE136171A IE35778B1 IE 35778 B1 IE35778 B1 IE 35778B1 IE 1361/71 A IE1361/71 A IE 1361/71A IE 136171 A IE136171 A IE 136171A IE 35778 B1 IE35778 B1 IE 35778B1
Authority
IE
Ireland
Prior art keywords
phenyl
fluorobutyrophenone
followed
substituted
reduction
Prior art date
Application number
IE1361/71A
Other versions
IE35778L (en
Original Assignee
Richardson Merrell 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 Richardson Merrell Inc filed Critical Richardson Merrell Inc
Publication of IE35778L publication Critical patent/IE35778L/en
Publication of IE35778B1 publication Critical patent/IE35778B1/en

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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

Landscapes

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

Abstract

1314955 Fluorobutyrophenone derivatives RICHARDSON-MERRELL Inc 27 Oct 1971 [27 Nov 1970] 49942/71 Heading C2C Novel compounds of the Formula I wherein R is hydrogen, chlorine, bromine, fluorine, C 1-4 alkyl or alkoxy, C 1-3 alkylthio, trifluoro methyl, phenyl, or phenoxy and salts thereof may be prepared by (a) condensing an appropriately substituted α-phenyl 4-piperidinemethanol with a 4-halo-4<SP>1</SP>-fluorobutyrophenone or (b) condensing an appropriately substituted 4-piperidylphenone with a 2-(3- halopropyl)-2-(p-fluorophenyl)-dioxolane to give an α-phenyl-1-{3-[2-(p-fluorophenyl) dioxolan- 2-yl]} propyl piperidyl ketone, followed by reduction of the keto group to give an α-phenyl- 1 - { 3 - [2 - (pfluorophenyl) dioxolan - 2 - yl]}- propyl-4-piperidinemethanol followed by hydrolysis of the dioxolane ring to form a keto group. The intermediate substituted α-phenyl-4- piperidine methanols may be prepared by (a) reduction of the corresponding ketone, (b) reacting a substituted phenyl Grignard reagent with 4-pyridine carboxaldehyde or 4-cyanopyridine followed by catalytic reduction of the intermediate. Pharmaceutical compositions of the compounds I show tranquillizing activity when administered orally or parenterally with the usual excipients. [GB1314955A]
IE1361/71A 1970-11-27 1971-10-27 4-(4-(alpha-hydroxybenzyl)piperidino)-4'-fluorobutyrophenone derivatives IE35778B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US9349570A 1970-11-27 1970-11-27

Publications (2)

Publication Number Publication Date
IE35778L IE35778L (en) 1972-05-27
IE35778B1 true IE35778B1 (en) 1976-05-26

Family

ID=22239276

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1361/71A IE35778B1 (en) 1970-11-27 1971-10-27 4-(4-(alpha-hydroxybenzyl)piperidino)-4'-fluorobutyrophenone derivatives

Country Status (16)

Country Link
JP (1) JPS5623985B2 (en)
BE (1) BE775593A (en)
CA (1) CA957376A (en)
CH (1) CH562215A5 (en)
DE (1) DE2158136C2 (en)
DK (1) DK135895B (en)
ES (1) ES397370A1 (en)
FR (1) FR2115451B1 (en)
GB (1) GB1314955A (en)
IE (1) IE35778B1 (en)
IL (1) IL38079A (en)
NL (1) NL175411C (en)
NO (1) NO135248C (en)
PH (1) PH9306A (en)
SE (1) SE369900B (en)
ZA (1) ZA717147B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE7409245L (en) * 1973-07-19 1975-01-20 Robins Co Inc A H
US4246268A (en) * 1979-02-09 1981-01-20 Richardson-Merrell Inc. Neuroleptic-4-(naphthylmethyl)piperidine derivatives
IE49998B1 (en) * 1979-08-06 1986-01-22 Merrell Dow Pharma 4-(naphthalenyloxy)piperidine derivatives
US4284636A (en) * 1979-09-04 1981-08-18 Richardson-Merrell Inc. Cinnamoylpiperidinobutyrophenone antipsychotic agents
US4283404A (en) * 1979-09-04 1981-08-11 Richardson-Merrell Inc. Aroylethenylpiperidinobutyrophenone antipsychotic agents
ZA806501B (en) * 1979-10-27 1981-10-28 Richardson Merrell Inc 4-(4-alkyl-aroyl-1-piperidino)butyrophenone antipsychotic agents
US4783471A (en) * 1985-07-02 1988-11-08 Merrell Dow Pharmaceuticals Inc. N-aralkyl piperidine methanol derivatives and the uses thereof
ZA864772B (en) * 1985-07-02 1987-02-25 Merrell Dow Pharma Novel chemical compounds
IL117149A0 (en) * 1995-02-23 1996-06-18 Schering Corp Muscarinic antagonists
EP1794144A2 (en) * 2004-09-13 2007-06-13 Bayer CropScience AG Processes for prepating n-(substituted arylmethyl)-4-(disubstituted methyl)piperidines and intermediates

Also Published As

Publication number Publication date
ES397370A1 (en) 1974-05-16
NO135248B (en) 1976-11-29
NL175411C (en) 1984-11-01
SE369900B (en) 1974-09-23
JPS5623985B2 (en) 1981-06-03
CH562215A5 (en) 1975-05-30
NO135248C (en) 1977-03-09
ZA717147B (en) 1972-07-26
NL7116194A (en) 1972-05-30
GB1314955A (en) 1973-04-26
BE775593A (en) 1972-03-16
IL38079A (en) 1974-10-22
DK135895C (en) 1977-12-12
NL175411B (en) 1984-06-01
FR2115451A1 (en) 1972-07-07
IL38079A0 (en) 1972-01-27
CA957376A (en) 1974-11-05
DE2158136A1 (en) 1972-05-31
IE35778L (en) 1972-05-27
DE2158136C2 (en) 1982-11-18
DK135895B (en) 1977-07-11
FR2115451B1 (en) 1975-02-07
PH9306A (en) 1975-08-18

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