FR2338245A1 - CNS-depressant, antiadrenergic 4-fluoro-butyro-phenone derivs - Google Patents

CNS-depressant, antiadrenergic 4-fluoro-butyro-phenone derivs

Info

Publication number
FR2338245A1
FR2338245A1 FR7704817A FR7704817A FR2338245A1 FR 2338245 A1 FR2338245 A1 FR 2338245A1 FR 7704817 A FR7704817 A FR 7704817A FR 7704817 A FR7704817 A FR 7704817A FR 2338245 A1 FR2338245 A1 FR 2338245A1
Authority
FR
France
Prior art keywords
lower alkyl
opt
alkoxy
halogen
substd
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.)
Granted
Application number
FR7704817A
Other languages
French (fr)
Other versions
FR2338245B1 (en
Inventor
Kikuo Sasajima
Keiichi Ono
Hisao Yamamoto
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.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co 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
Priority claimed from JP50027489A external-priority patent/JPS51125239A/en
Priority claimed from JP50138836A external-priority patent/JPS596304B2/en
Priority claimed from FR7606032A external-priority patent/FR2302728A1/en
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of FR2338245A1 publication Critical patent/FR2338245A1/en
Application granted granted Critical
Publication of FR2338245B1 publication Critical patent/FR2338245B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C07C45/46—Friedel-Crafts reactions
    • 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
    • C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
    • 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
    • C07D211/36—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 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • 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
    • C07D211/36—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 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4

Landscapes

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

Abstract

Cpds. of formula (I) and their pharmaceutically acceptable acid addn. salts are new (where Z is morpholino, or pyrrolidino or one of the following gps. R1 is benzyl (opt. 4-chloro, or 2,4- or 3,4-dichlorosubstd) or phenyl substd. by 3-CF3-, 3-CF3-4-Cl or 3,4-dichloro; R2 and R3 are each H, halogen, Cf3, lower alkyl or lower alkoxy, the dashed line is an opt. double bond; R4 and R5 are H or lower alkyl; R6 is H or halogen; R7 is H or lower alkoxy; R8 and r9 are each H, lower alkyl or Ph opt. substd. by halogen, lower alkyl or lower alkoxy; R10 is H, lower alkyl, lower alkoxy or CF3; n in integer 1-4; R" is H, lower alkyl or Ph opt. substd. by 1 or 2 haalogen, lower alkyl, lower alkoxy or CF3; Y is O, S, CO, -NR12 or -C(R12)(OH)- R12 is H, lower alkyl or Ph opt. substd. by 1 or 2 halogen lower alkyl, lower alkoxy or CF3; m is 1-4; lower alkyl and alkoxy gps. are 1-4C).(I) are CNS depressants, and anti-adrenergics, and are useful as antipsychotics and antihypertensives. They have antiapomorphine activity greater than that of e.g. chlorpromazine in the rate. (I; Z = phenoxyalkylamino) have alpha adrengergic blocking props. Doses are usually 1-200 mg/day p.o. Pref. uses are as psychotropes and for treating hypertention and metal illness
FR7704817A 1975-03-05 1977-02-18 CNS-depressant, antiadrenergic 4-fluoro-butyro-phenone derivs Granted FR2338245A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP50027489A JPS51125239A (en) 1975-03-05 1975-03-05 Process for preparing new bytyrophenone derivatives
JP50138836A JPS596304B2 (en) 1975-11-18 1975-11-18 Synkinabutyrophenol
FR7606032A FR2302728A1 (en) 1975-03-05 1976-03-03 PROCESS FOR THE PRODUCTION OF BUTYROPHENONE COMPOUNDS, NEW PRODUCTS THUS OBTAINED AND THEIR USE AS AGENTS WITH A DEPRESSION OF THE CENTRAL NERVOUS SYSTEM

Publications (2)

Publication Number Publication Date
FR2338245A1 true FR2338245A1 (en) 1977-08-12
FR2338245B1 FR2338245B1 (en) 1979-03-09

Family

ID=27250592

Family Applications (2)

Application Number Title Priority Date Filing Date
FR7704817A Granted FR2338245A1 (en) 1975-03-05 1977-02-18 CNS-depressant, antiadrenergic 4-fluoro-butyro-phenone derivs
FR7704815A Granted FR2338260A1 (en) 1975-03-05 1977-02-18 PROCESS FOR PREPARATION OF BUTYROPHENONE COMPOUNDS WITH A PIPERIDINO, MORPHOLINO, PYRROLIDINO OR PIPERAZINO GROUP AND NEW PRODUCTS THUS OBTAINED, WITH PSYCHOTROPIC ACTIVITY

Family Applications After (1)

Application Number Title Priority Date Filing Date
FR7704815A Granted FR2338260A1 (en) 1975-03-05 1977-02-18 PROCESS FOR PREPARATION OF BUTYROPHENONE COMPOUNDS WITH A PIPERIDINO, MORPHOLINO, PYRROLIDINO OR PIPERAZINO GROUP AND NEW PRODUCTS THUS OBTAINED, WITH PSYCHOTROPIC ACTIVITY

Country Status (1)

Country Link
FR (2) FR2338245A1 (en)

Also Published As

Publication number Publication date
FR2338260A1 (en) 1977-08-12
FR2338260B1 (en) 1980-08-14
FR2338245B1 (en) 1979-03-09

Similar Documents

Publication Publication Date Title
ES459348A1 (en) Tetracyclic compounds
MY108261A (en) Water soluble camptothecin derivatives
LU88579I2 (en) ATOVAQUONE and its pharmaceutically acceptable salts (WELLVONE R)
SE8900039L (en) ISOQINOLINE DERIVATIVES, THEIR PREPARATION AND THEIR USE
SE8301412D0 (en) SUBSTITUTED 1H-PYRAZOLO (1,5) PYRIMIDINES AND PROCEDURE FOR THEIR PREPARATION
YU182581A (en) Process for preparing new 5,10-dihydro-11h-dibenzo-(b,e)(1,4)diazepine-11-ones substituted in position 5
FR2338245A1 (en) CNS-depressant, antiadrenergic 4-fluoro-butyro-phenone derivs
FR2338274A1 (en) CNS-depressant, antiadrenergic 4-fluoro-butyro-phenone derivs
GB1187259A (en) New Aminoalkyl Esters of 2-Anilino-Nicotinic Acids and process for their manufacture
DK394189A (en) ARYLAL CYLAMINES AND AMIDES WITH ANTI-CONVULSIVE AND NEUROBATIVE PROPERTIES
HRP940721B1 (en) New 3,4-dihydroisoquinoline derivatives, processes for the preparation thereof and pharmaceutical ingredients containing new compounds
ES8602698A1 (en) Novel quinazolinone derivative, a process for preparing the same and a pharmaceutical composition.
ES376688A1 (en) Benzdiazepine derivatives
ES416614A1 (en) Novel 1-(2{40 -benzoyl eth-1{40 -yl)-2-(4{41 -cinnamyl piperazin-1{41 -yl methyl) benzimidazoles, their process of preparation and their therapeutic application
ES8602785A1 (en) Pyrazolopyridine derivatives, therapeutic compositions comprising same, and process thereof.
FR2258840A1 (en) (4-Phenylpiperazino) alkyl esters - with analgesic activity for human and veterinary use
GB1309485A (en) 6-substituted-indolo 1,2-c-quinazolines
BG97231A (en) 1,2,3,3A,8,8A-HEXAXHYDRO-1,3A,8-TRIMETHYLPYRROLO(2,3-B)INDOLE TETRAHYDROISOQUINOLINYLCARBAMATES
ES369304A1 (en) IMIDAZO-3H-(4,5-b)-PYRIDINE DERIVATIVES
ES8502115A1 (en) 4-Hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides, process for their preparation, their use and therapeutic agents containing them.
ES375495A1 (en) Ketones derived from -1-(2-hydroxyethyl)-piperazine
ES394461A1 (en) Benzhydril-pyridodiazepines - as antihistaminics and anticholinergics from dihaloalkylpiperidines and arylalkylamines with condensing agent
NL7209299A (en) Delta-4-3-oxo-11-beta-halo steroids - with hormonal activity
ES2094551T3 (en) PROCEDURE FOR PREPARING DERIVATIVES OF 1,3-DIOXOLANE.
GB1311419A (en) Derivatives of 1-cinnamyl benzimidazole their process of preparation and their therapeutic application

Legal Events

Date Code Title Description
ST Notification of lapse