IE39102L - Piperazine derivatives - Google Patents

Piperazine derivatives

Info

Publication number
IE39102L
IE39102L IE740650A IE65074A IE39102L IE 39102 L IE39102 L IE 39102L IE 740650 A IE740650 A IE 740650A IE 65074 A IE65074 A IE 65074A IE 39102 L IE39102 L IE 39102L
Authority
IE
Ireland
Prior art keywords
ethyl
piperazinyl
oxo
dihydro
pyrimidine
Prior art date
Application number
IE740650A
Other versions
IE39102B1 (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 true IE39102L (en) 1974-10-03
IE39102B1 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.
PL2448938T3 (en) 2009-06-29 2014-11-28 Incyte Holdings Corp Pyrimidinones as pi3k inhibitors
AR079529A1 (en) 2009-12-18 2012-02-01 Incyte Corp ARILO AND HETEROARILO DERIVATIVES REPLACED AND FOUNDED AS INHIBITORS OF THE PI3K
WO2011075643A1 (en) 2009-12-18 2011-06-23 Incyte Corporation Substituted heteroaryl fused derivatives as pi3k inhibitors
TW201249844A (en) 2010-12-20 2012-12-16 Incyte Corp N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors
KR102131612B1 (en) 2011-09-02 2020-07-08 인사이트 홀딩스 코포레이션 Heterocyclylamines as pi3k inhibitors
AR090548A1 (en) 2012-04-02 2014-11-19 Incyte Corp BICYCLIC AZAHETEROCICLOBENCILAMINS AS PI3K INHIBITORS
WO2015191677A1 (en) 2014-06-11 2015-12-17 Incyte Corporation Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors
MA41607B1 (en) 2015-02-27 2021-01-29 Incyte Corp Salts of a pi3k inhibitor and methods of preparing these salts
WO2016183060A1 (en) 2015-05-11 2016-11-17 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
SE416051B (en) 1980-11-24
NO142221B (en) 1980-04-08
AR204003A1 (en) 1975-11-12
NO740349L (en) 1974-10-04
IE39102B1 (en) 1978-08-02
NO142221C (en) 1980-07-16
FI56011B (en) 1979-07-31
ES424851A1 (en) 1976-06-01
ATA277774A (en) 1977-05-15
PH10984A (en) 1977-10-18
CH593281A5 (en) 1977-11-30
FI56011C (en) 1979-11-12
CA1066701A (en) 1979-11-20
NL186087C (en) 1990-09-17
PH10529A (en) 1977-05-30
NL186087B (en) 1990-04-17
NL7401509A (en) 1974-10-07
AR204660A1 (en) 1976-02-20
AT340931B (en) 1978-01-10

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