GB976551A - New barbituric acid derivatives and methods of preparing the same - Google Patents

New barbituric acid derivatives and methods of preparing the same

Info

Publication number
GB976551A
GB976551A GB42969/59A GB4296959A GB976551A GB 976551 A GB976551 A GB 976551A GB 42969/59 A GB42969/59 A GB 42969/59A GB 4296959 A GB4296959 A GB 4296959A GB 976551 A GB976551 A GB 976551A
Authority
GB
United Kingdom
Prior art keywords
compounds
carbon atoms
optionally substituted
group
formula
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
GB42969/59A
Inventor
Leslie Frederick Wiggins
John William James
Maurice Ward Gittos
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.)
Aspro Nicholas Ltd
Original Assignee
Aspro Nicholas 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
Application filed by Aspro Nicholas Ltd filed Critical Aspro Nicholas Ltd
Priority to FR41034A priority Critical patent/FR1466211A/en
Priority to US277431A priority patent/US3312703A/en
Publication of GB976551A publication Critical patent/GB976551A/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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • 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
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C07D239/66—Thiobarbituric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B29/00—Engines characterised by provision for charging or scavenging not provided for in groups F02B25/00, F02B27/00 or F02B33/00 - F02B39/00; Details thereof
    • F02B29/04—Cooling of air intake supply
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F28—HEAT EXCHANGE IN GENERAL
    • F28F—DETAILS OF HEAT-EXCHANGE AND HEAT-TRANSFER APPARATUS, OF GENERAL APPLICATION
    • F28F9/00—Casings; Header boxes; Auxiliary supports for elements; Auxiliary members within casings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
    • Y02T10/00—Road transport of goods or passengers
    • Y02T10/10—Internal combustion engine [ICE] based vehicles
    • Y02T10/12—Improving ICE efficiencies

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises compounds of general formula <FORM:0976551/C1/1> wherein R1 represents a sec. amyl, benzyl or cyclohexyl group, and R2 represents either -A-NR3R4 where A is a straight chain alkylene radical containing 2 or 3 chain carbon atoms, said radical being optionally substituted by one or more methyl groups, and R3 and R4 are hydrogen or lower (1-4 C) alkyl groups or are joined together to form with the nitrogen atom a heterocyclic group which may contain a further hetero atom, or R2 represents -(CH2)n-R5 where n is 1 or 2 and R5 is a saturated or unsaturated heterocyclic group containing a basic nitrogen atom optionally substituted by a lower alkyl group and spaced away from the carbonyl groups in the barbituric acid molecule by from 3 to 5 carbon atoms; and pharmaceutically acceptable acid addition salts thereof; and their preparation (1) by condensing a compound R2Cl with a compound of formula <FORM:0976551/C1/2> where R is lower alkyl, to form a disubstituted malonic ester of formula <FORM:0976551/C1/3> which is then condensed with urea, and (2) as in the examples wherein pyridyl-substituted derivatives are catalytically hydrogenated to piperidyl compounds. Pharmaceutical compositions comprise compounds of the invention with carriers. They are CNS stimulants. In the Provisional Specification R1 is defined as a branched chain alkyl group of 5 carbon atoms or an aralkyl or cycloalkyl group, and R2 as additionally -A-NR3R4 where A is optionally substituted by alkyl groups; compounds wherein X is O, R1 is (CH3)2CHCH2 CH2- and R2 is -(CH2)2-N(CH3)2 or -(CH2)3-N(C2H5)2 are excepted.
GB42969/59A 1959-12-17 1959-12-17 New barbituric acid derivatives and methods of preparing the same Expired GB976551A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FR41034A FR1466211A (en) 1959-12-17 1960-12-17 New derivatives of barbituric acid and process for their preparation
US277431A US3312703A (en) 1959-12-17 1963-05-02 2-pyridyl and 2-piperidinyl phenyl barbituric acids and method of preparing thiobarbituric acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA0043991 1963-09-07

Publications (1)

Publication Number Publication Date
GB976551A true GB976551A (en) 1964-11-25

Family

ID=6933949

Family Applications (2)

Application Number Title Priority Date Filing Date
GB42969/59A Expired GB976551A (en) 1959-12-17 1959-12-17 New barbituric acid derivatives and methods of preparing the same
GB43049/60A Expired GB977321A (en) 1963-09-07 1959-12-17 New barbituric acid derivatives and methods for preparing the same

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB43049/60A Expired GB977321A (en) 1963-09-07 1959-12-17 New barbituric acid derivatives and methods for preparing the same

Country Status (2)

Country Link
DE (1) DE1445426A1 (en)
GB (2) GB976551A (en)

Also Published As

Publication number Publication date
GB977321A (en) 1964-12-09
DE1445426A1 (en) 1968-12-19

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