IE38220B1 - 4(1h)-pyrimidinone compounds,a method for producing them andmedicamentes containing them - Google Patents
4(1h)-pyrimidinone compounds,a method for producing them andmedicamentes containing themInfo
- Publication number
- IE38220B1 IE38220B1 IE158573A IE158573A IE38220B1 IE 38220 B1 IE38220 B1 IE 38220B1 IE 158573 A IE158573 A IE 158573A IE 158573 A IE158573 A IE 158573A IE 38220 B1 IE38220 B1 IE 38220B1
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- hydrogen
- group
- replaced
- acid
- Prior art date
Links
Classifications
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- 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)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pest Control & Pesticides (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Epidemiology (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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.
[GB1427190A]
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU66039 | 1972-09-08 | ||
LU66037 | 1972-09-08 | ||
LU66038 | 1972-09-08 | ||
LU66036 | 1972-09-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
IE38220L IE38220L (en) | 1974-03-08 |
IE38220B1 true IE38220B1 (en) | 1978-01-18 |
Family
ID=27483584
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE158573A IE38220B1 (en) | 1972-09-08 | 1973-09-06 | 4(1h)-pyrimidinone compounds,a method for producing them andmedicamentes 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) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU1520699A (en) | 1997-11-07 | 1999-05-31 | Johns Hopkins University, The | Methods for treatment of disorders of cardiac contractility |
-
1973
- 1973-09-05 CH CH1271973A patent/CH593265A5/xx not_active IP Right Cessation
- 1973-09-05 DE DE19732344757 patent/DE2344757C3/en not_active Expired
- 1973-09-05 GB GB4166873A patent/GB1427190A/en not_active Expired
- 1973-09-06 CA CA180,398A patent/CA1008073A/en not_active Expired
- 1973-09-06 IE IE158573A patent/IE38220B1/en unknown
- 1973-09-07 JP JP48101039A patent/JPS4962488A/ja active Pending
- 1973-09-07 FR FR7332263A patent/FR2198747B1/fr not_active Expired
- 1973-09-07 NL NL7312336A patent/NL7312336A/xx not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
CA1008073A (en) | 1977-04-05 |
FR2198747B1 (en) | 1977-01-28 |
NL7312336A (en) | 1974-03-12 |
CH593265A5 (en) | 1977-11-30 |
JPS4962488A (en) | 1974-06-17 |
GB1427190A (en) | 1976-03-10 |
FR2198747A1 (en) | 1974-04-05 |
IE38220L (en) | 1974-03-08 |
DE2344757B2 (en) | 1978-01-05 |
DE2344757C3 (en) | 1978-09-14 |
DE2344757A1 (en) | 1974-04-11 |
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