GB1427190A - 4-1h-pyrimidinone compounds a method for producing them and medicamentss containing them - Google Patents

4-1h-pyrimidinone compounds a method for producing them and medicamentss containing them

Info

Publication number
GB1427190A
GB1427190A GB4166873A GB4166873A GB1427190A GB 1427190 A GB1427190 A GB 1427190A GB 4166873 A GB4166873 A GB 4166873A GB 4166873 A GB4166873 A GB 4166873A GB 1427190 A GB1427190 A GB 1427190A
Authority
GB
United Kingdom
Prior art keywords
alkyl
hydrogen
group
replaced
acid
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
GB4166873A
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.)
Takeda GmbH
Original Assignee
Byk Gulden Lomberg Chemische Fabrik GmbH
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 Byk Gulden Lomberg Chemische Fabrik GmbH filed Critical Byk Gulden Lomberg Chemische Fabrik GmbH
Publication of GB1427190A publication Critical patent/GB1427190A/en
Expired legal-status Critical Current

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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/275—Nitriles; Isonitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1427190 5-Cyano-4-pyrimidinone derivatives BYK GULDEN LOMBERG CHEMISCHE FABRIK GmbH 5 Sept 1973 [8 Sept 1972 (4)] 41668/73 Heading C2C Novel compounds I in which R<SP>3</SP> is in which R<SP>4</SP> is hydrogen, a C 1-14 alkyl C 2-7 alkenyl or C 2-7 alkynyl group in which a methylene group may be replaced by oxygen and the alkyl group may be substituted by an NR<SP>5</SP>R<SP>6</SP> group C 3-6 cycloalkyl optionally substituted by an NR<SP>5</SP>R<SP>6</SP> group, a phenyl or phenyl-C 1-6 alkyl group (optionally substituted in the ring by C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkylthio, C 2-5 alkoxycarbonyl halogen, trifluoromethyl, nitro and/or cyano) R<SP>5</SP> and R<SP>6</SP> are hydrogen, a C 1-7 alkyl, C 2-7 alkenyl or C 2-7 alkynyl group in which a methylene group may be replaced by oxygen, or C 3-6 cycloalkyl or R 5 and R 6 together represent C 2-5 alkylene (in which one or more methylene groups may be replaced by O, S or NR<SP>7</SP>), X is O, S or NR<SP>7</SP>, Y is O, S or NH and R<SP>7</SP> is hydrogen, C 1-7 alkyl, C 2-7 alkenyl or C 2-7 alkynyl and their salts are prepared by (1) treating a compound II in which R<SP>1</SP> and R<SP>2</SP> are C 1-7 alkyl or R<SP>1</SP> and R<SP>2</SP> together represent C 2-5 alkylene in which one or more methylene groups may be replaced by O, S or NR<SP>7</SP> (in which R<SP>7</SP> is hydrogen or C 1-7 alkyl) with an acid (2) heating or reacting with an acid or compound III in which A and B are hydrogen, hydroxy, C 1-7 alkoxy NR<SP>8</SP>R<SP>9</SP> or NR<SP>8</SP>-COR<SP>9</SP> (in which R<SP>8</SP> and R<SP>9</SP> are hydrogen, C 1-7 alkyl in which a methylene group may be replaced by oxygen, C 3-6 cycloalkyl or R<SP>8</SP> and R<SP>9</SP> together represent C 2-5 alkylene in which one or more methylene groups may be replaced by O, S or NR<SP>7</SP> and R<SP>7</SP> is hydrogen or C 1-7 alkyl) (3) heating or treating with an acid a compound IV in which R<SP>1</SP> and R<SP>2</SP> is addition to the above definitions, may be a phenyl group or one of R<SP>1</SP> and R<SP>2</SP> may additionally be hydrogen or (4) cyanacetamide is reacted with a trialkyl orthoformate HC(OR) 3 or a dialkoxymethyl ester of an organic carboxylic acid R*COOCH(OR) 2 (in which R is C 1-7 alkyl, and R* is hydrogen, C 1-7 alkyl, aryl, aralkyl or cycloalkyl) in the presence of an acid anhydride and the resulting product reacted with a hydrazine R 3 -NHNH 2 . In the compounds prepared R<SP>3</SP> is C 1-12 alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl cyclohexyloxycarbonyl, #-methoxyethoxycarbonyl, benzamido, #-iso-propoxyethoxycarbonyl, allyloxycarbonyl, acetyl or pmethoxybenzoyl. 2 - Morpholinomethylidene - 3 - oxo - 4 - aza- 5 - (N<SP>1</SP> - acetylhydrazino) - 4 - pentenenitrile is prepared by heating together 3-morpholino-2- cyano-acrylamide, triethylorthoformate, acetic anhydride and formic acid. Compounds I are used to prepare compounds IV or its tautomers by reaction with an amine R 1 R 2 NH; compound IV (R 1 R 2 N=N-methylpiperazine, R<SP>3</SP>=COOMe) is prepared. Compounds I may be used to treat gout, coronary insufficiency and arrhythmia. They form with a suitable vehicle a pharmaceutical composition which may be administered orally or parenterally.
GB4166873A 1972-09-08 1973-09-05 4-1h-pyrimidinone compounds a method for producing them and medicamentss containing them Expired GB1427190A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
LU66037 1972-09-08
LU66038 1972-09-08
LU66036 1972-09-08
LU66039 1972-09-08

Publications (1)

Publication Number Publication Date
GB1427190A true GB1427190A (en) 1976-03-10

Family

ID=27483584

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4166873A Expired GB1427190A (en) 1972-09-08 1973-09-05 4-1h-pyrimidinone compounds a method for producing them and medicamentss containing them

Country Status (8)

Country Link
JP (1) JPS4962488A (en)
CA (1) CA1008073A (en)
CH (1) CH593265A5 (en)
DE (1) DE2344757C3 (en)
FR (1) FR2198747B1 (en)
GB (1) GB1427190A (en)
IE (1) IE38220B1 (en)
NL (1) NL7312336A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6191136B1 (en) 1997-11-07 2001-02-20 Johns Hopkins University Methods for treatment of disorders of cardiac contractility

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6191136B1 (en) 1997-11-07 2001-02-20 Johns Hopkins University Methods for treatment of disorders of cardiac contractility
US6569862B1 (en) 1997-11-07 2003-05-27 Johns Hopkins University Methods for treatment of disorders of cardiac contractility

Also Published As

Publication number Publication date
JPS4962488A (en) 1974-06-17
DE2344757B2 (en) 1978-01-05
CH593265A5 (en) 1977-11-30
DE2344757C3 (en) 1978-09-14
IE38220B1 (en) 1978-01-18
IE38220L (en) 1974-03-08
FR2198747B1 (en) 1977-01-28
CA1008073A (en) 1977-04-05
NL7312336A (en) 1974-03-12
FR2198747A1 (en) 1974-04-05
DE2344757A1 (en) 1974-04-11

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee