GB1473000A - Processes for preparing a triazolinone derivative - Google Patents

Processes for preparing a triazolinone derivative

Info

Publication number
GB1473000A
GB1473000A GB4441674A GB4441674A GB1473000A GB 1473000 A GB1473000 A GB 1473000A GB 4441674 A GB4441674 A GB 4441674A GB 4441674 A GB4441674 A GB 4441674A GB 1473000 A GB1473000 A GB 1473000A
Authority
GB
United Kingdom
Prior art keywords
piperazinyl
chlorophenyl
propyl
image
iii
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
GB4441674A
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.)
Sigma Tau Industrie Farmaceutiche Riunite SpA
Original Assignee
Sigma Tau Industrie Farmaceutiche Riunite SpA
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 Sigma Tau Industrie Farmaceutiche Riunite SpA filed Critical Sigma Tau Industrie Farmaceutiche Riunite SpA
Publication of GB1473000A publication Critical patent/GB1473000A/en
Expired 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
    • C07D295/12—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 singly or doubly bound nitrogen atoms
    • C07D295/125—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1-[3-(4-m-Chlorophenyl-1-piperazinyl)-propyl]-3,4-diethyl- DELTA 2-1,2,4- triazolin-5-one of the formula (I) <IMAGE> shows tranquillising properties in human therapy. (I) is prepared by cyclisation of 2-[3-(4-m-chlorophenyl-1-piperazinyl)-propyl]-4-ethyl-1-propionyl-semi carbazide (III) <IMAGE> or, which is chemically equivalent, by reacting N-[3-(4-m-chlorophenyl-1-piperazinyl)-propyl]-N'-propionylhydrazine with ethyl isocyanate <IMAGE> In fact, in the reaction between (II) and ethyl isocyanate, (III) is formed as an intermediate which can easily be isolated. The most convenient way of synthesising (III), which is not described in the literature, is precisely the method just described. (I) is also prepared by reacting 3-(4-m-chlorophenyl-1-piperazinyl)-propyl-hydrazine (IV) with an alkylpropionylcarbamate (V) such as, for example, propionylurethane. <IMAGE> In the formula (V), R is lower alkyl. Equimolar mixtures of the two reagents are heated for several hours in an inert solvent in the presence of a dehydrating agent.
GB4441674A 1973-10-15 1974-10-14 Processes for preparing a triazolinone derivative Expired GB1473000A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT53134/73A IT1052130B (en) 1973-10-15 1973-10-15 TRIAZOLINONE DERIVATIVES AND PROCEDURE FOR THEIR PREPARATION

Publications (1)

Publication Number Publication Date
GB1473000A true GB1473000A (en) 1977-05-11

Family

ID=11280220

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4441674A Expired GB1473000A (en) 1973-10-15 1974-10-14 Processes for preparing a triazolinone derivative

Country Status (14)

Country Link
AR (1) AR210845A1 (en)
AT (1) AT340431B (en)
BE (1) BE821084R (en)
CH (1) CH618167A5 (en)
DK (1) DK537574A (en)
FI (1) FI299474A (en)
FR (1) FR2247244B2 (en)
GB (1) GB1473000A (en)
IN (1) IN140467B (en)
IT (1) IT1052130B (en)
NL (1) NL183239C (en)
NO (1) NO743683L (en)
SE (1) SE418183B (en)
YU (1) YU41552B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0185909A1 (en) * 1984-11-24 1986-07-02 Kali-Chemie Pharma GmbH 5-Alkyl-1-phenyl-2-piperazino alkylpyrazolin-3-one compounds as well as processes and intermediates for their preparation and medicaments containing these compounds
GB2184446A (en) * 1983-06-29 1987-06-24 Bristol Myers Co Piperazinylalkyltriazolones and their preparation
US5900485A (en) * 1996-07-29 1999-05-04 Apotex, Inc. Methods for the manufacture of neofazodone

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1047702B (en) * 1975-07-24 1980-10-20 Acraf NEW SYNTHESIS OF THE PSYCHOPARMACIES NAMED TRAZODONE AND HETEROPERIDONE
RU2670622C1 (en) * 2018-07-19 2018-10-24 Федеральное государственное бюджетное образовательное учреждение высшего образования "МИРЭА - Российский технологический университет" Method for obtaining 2-alkyl-substituted semicarbazides

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2184446A (en) * 1983-06-29 1987-06-24 Bristol Myers Co Piperazinylalkyltriazolones and their preparation
EP0185909A1 (en) * 1984-11-24 1986-07-02 Kali-Chemie Pharma GmbH 5-Alkyl-1-phenyl-2-piperazino alkylpyrazolin-3-one compounds as well as processes and intermediates for their preparation and medicaments containing these compounds
US4672063A (en) * 1984-11-24 1987-06-09 Kali-Chemie Pharma Gmbh Antiallergic 5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-one compounds
US5900485A (en) * 1996-07-29 1999-05-04 Apotex, Inc. Methods for the manufacture of neofazodone

Also Published As

Publication number Publication date
IT1052130B (en) 1981-06-20
SE7412891L (en) 1975-04-16
FR2247244A2 (en) 1975-05-09
FR2247244B2 (en) 1978-07-07
SE418183B (en) 1981-05-11
NL183239C (en) 1988-09-01
AU7431874A (en) 1976-04-15
YU41552B (en) 1987-10-31
NL183239B (en) 1988-04-05
CH618167A5 (en) 1980-07-15
BE821084R (en) 1975-02-03
AT340431B (en) 1977-12-12
DK537574A (en) 1975-07-07
YU340874A (en) 1983-02-28
NO743683L (en) 1975-05-12
IN140467B (en) 1976-11-13
AR210845A1 (en) 1977-09-30
ATA826174A (en) 1977-04-15
NL7413565A (en) 1975-04-17
FI299474A (en) 1975-04-16

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]