IE39102B1 - Method for the preparation of piperazine derivatives - Google Patents

Method for the preparation of piperazine derivatives

Info

Publication number
IE39102B1
IE39102B1 IE00650/74A IE65074A IE39102B1 IE 39102 B1 IE39102 B1 IE 39102B1 IE 00650/74 A IE00650/74 A IE 00650/74A IE 65074 A IE65074 A IE 65074A IE 39102 B1 IE39102 B1 IE 39102B1
Authority
IE
Ireland
Prior art keywords
ethyl
piperazinyl
oxo
dihydro
pyrimidine
Prior art date
Application number
IE00650/74A
Other versions
IE39102L (en
Original Assignee
Dainippon Pharmaceutical Co
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 JP3845373A external-priority patent/JPS5546400B2/ja
Priority claimed from JP5654473A external-priority patent/JPS565753B2/ja
Priority claimed from JP6446473A external-priority patent/JPS565755B2/ja
Application filed by Dainippon Pharmaceutical Co filed Critical Dainippon Pharmaceutical Co
Publication of IE39102L publication Critical patent/IE39102L/en
Publication of IE39102B1 publication Critical patent/IE39102B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

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

Abstract

A process for preparing 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-c arboxylic acids(I) and its pharmaceutically acceptable salts, which comprises hydrolyzing 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-c arbonitrils(II') oxidizing 6-lower alkanoyl-8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrim idines (II"), and if desired, hydrolyzing the product; or subjecting alkyl 4-(N-substituted ethyl-N-ethyl)amino 2-(1-piperazinyl)-pyrimidine-5-carboxylates(IV) to a Dieckmann reaction, dehydrogenating the resulting 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6,7,8-tetrahydropyrido(2,3-d) pyrimidines (III), then oxidizing or hydrolyzing the resulting 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxo-pyrido(2,3-d)pyrimidines(II) and if desired, converting the resulting 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido2,3-d) pyrimidine-6-carboxylic acids(II) to a pharmaceutically acceptable salt, and a process for proparing 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido(2,3-d)pyrimidines(II), which comprises dehydrogenating 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6.7.8-tetrahydropyrido(2,3-d)pyrimid ines (III), or subjecting alkyl 4-(N-substituted ethyl-N-ethyl)amino-2-(1-piperazinyl)-pyrimidine-5-carboxylates(IV) to a Dieckmann reaction, and dehydrogenating the resulting 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6,7,8-tetrahydropyrido(2,3-d)pyrimid ines(III). The 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl) pyrido(2,3-d)pyrimidine-6-carboxylic acids (I) and their pharmaceutically acceptable salts are useful as antibacterial agents, and 5 8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido(2,3-c)pyrimidines (II) are used as intermediates for producing the 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl) pyrido(2,3-d)pyrimidine-6-carboxylic acids (I). A process for preparing 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acids(I) and its pharmaceutically acceptable salts, which comprises hydrolyzing 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carbonitrils(II') oxidizing 6-lower alkanoyl-8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidines (II"), and if desired, hydrolyzing the product; or subjecting alkyl 4-(N-substituted ethyl-N-ethyl)amino 2-(1-piperazinyl)-pyrimidine-5-carboxylates(IV) to a Dieckmann reaction, dehydrogenating the resulting 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6,7,8-tetrahydropyrido(2,3-d) pyrimidines (III), then oxidizing or hydrolyzing the resulting 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxo-pyrido(2,3-d)pyrimidines(II) and if desired, converting the resulting 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido¢2,3-d) pyrimidine-6-carboxylic acids(II) to a pharmaceutically acceptable salt, and a process for proparing 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido(2,3-d)pyrimidines(II), which comprises dehydrogenating 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6.7.8-tetrahydropyrido(2,3-d)pyrimidines (III), or subjecting alkyl 4-(N-substituted ethyl-N-ethyl)amino-2-(1-piperazinyl)-pyrimidine-5-carboxylates(IV) to a Dieckmann reaction, and dehydrogenating the resulting 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6,7,8-tetrahydropyrido(2,3-d)pyrimidines(III). The 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl) pyrido(2,3-d)pyrimidine-6-carboxylic acids (I) and their pharmaceutically acceptable salts are useful as antibacterial agents, and 5 8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido(2,3-c)pyrimidines (II) are used as intermediates for producing the 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl) pyrido(2,3-d)pyrimidine-6-carboxylic acids (I). [CA1066701A]
IE00650/74A 1973-04-03 1974-03-25 Method for the preparation of piperazine derivatives IE39102B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP3845373A JPS5546400B2 (en) 1973-04-03 1973-04-03
JP5654473A JPS565753B2 (en) 1973-05-21 1973-05-21
JP6446473A JPS565755B2 (en) 1973-06-07 1973-06-07

Publications (2)

Publication Number Publication Date
IE39102L IE39102L (en) 1974-10-03
IE39102B1 true IE39102B1 (en) 1978-08-02

Family

ID=27289838

Family Applications (1)

Application Number Title Priority Date Filing Date
IE00650/74A IE39102B1 (en) 1973-04-03 1974-03-25 Method for the preparation of piperazine derivatives

Country Status (11)

Country Link
AR (2) AR204003A1 (en)
AT (1) AT340931B (en)
CA (1) CA1066701A (en)
CH (1) CH593281A5 (en)
ES (1) ES424851A1 (en)
FI (1) FI56011C (en)
IE (1) IE39102B1 (en)
NL (1) NL186087C (en)
NO (1) NO142221C (en)
PH (2) PH10529A (en)
SE (1) SE416051B (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1209163B (en) * 1979-12-21 1989-07-10 Unibios S P A Trecate Novara PROCEDURE FOR THE MANUFACTURE OF: 6-ALCOSSICARBONIL-8-ETHYL-5-OXO-5,8 DIIDRO-APERTA PAR. SQUARE 2,3-DCHIUSA PAR. SQUARE-PRIMIDINE 2-REPLACED AND ACID CORRESPONDING BOOKS.
NZ597050A (en) 2009-06-29 2014-02-28 Incyte Corp Pyrimidinones as pi3k inhibitors
US8759359B2 (en) 2009-12-18 2014-06-24 Incyte Corporation Substituted heteroaryl fused derivatives as PI3K inhibitors
US8680108B2 (en) 2009-12-18 2014-03-25 Incyte Corporation Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors
AR084366A1 (en) 2010-12-20 2013-05-08 Incyte Corp N- (1- (REPLACED PHENYL) ETIL) -9H-PURIN-6-AMINAS AS PI3K INHIBITORS
BR122019020716B1 (en) 2011-09-02 2021-02-17 Incyte Holdings Corporation heterocyclylamines as pi3k inhibitors and pharmaceutical composition comprising them
AR090548A1 (en) 2012-04-02 2014-11-19 Incyte Corp BICYCLIC AZAHETEROCICLOBENCILAMINS AS PI3K INHIBITORS
US10077277B2 (en) 2014-06-11 2018-09-18 Incyte Corporation Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
MD3262046T2 (en) 2015-02-27 2021-03-31 Incyte Corp Salts of pi3k inhibitor and processes for their preparation
US9732097B2 (en) 2015-05-11 2017-08-15 Incyte Corporation Process for the synthesis of a phosphoinositide 3-kinase inhibitor
WO2016183063A1 (en) 2015-05-11 2016-11-17 Incyte Corporation Crystalline forms of a pi3k inhibitor

Also Published As

Publication number Publication date
AR204660A1 (en) 1976-02-20
NL7401509A (en) 1974-10-07
CH593281A5 (en) 1977-11-30
NO740349L (en) 1974-10-04
NO142221C (en) 1980-07-16
FI56011B (en) 1979-07-31
ATA277774A (en) 1977-05-15
IE39102L (en) 1974-10-03
AR204003A1 (en) 1975-11-12
PH10529A (en) 1977-05-30
NL186087C (en) 1990-09-17
NO142221B (en) 1980-04-08
SE416051B (en) 1980-11-24
FI56011C (en) 1979-11-12
CA1066701A (en) 1979-11-20
PH10984A (en) 1977-10-18
AT340931B (en) 1978-01-10
ES424851A1 (en) 1976-06-01
NL186087B (en) 1990-04-17

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