GB1070243A - S-triazolopyrimidones, their preparation and compositions containing them - Google Patents
S-triazolopyrimidones, their preparation and compositions containing themInfo
- Publication number
- GB1070243A GB1070243A GB2915164A GB2915164A GB1070243A GB 1070243 A GB1070243 A GB 1070243A GB 2915164 A GB2915164 A GB 2915164A GB 2915164 A GB2915164 A GB 2915164A GB 1070243 A GB1070243 A GB 1070243A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- halogen
- formula
- hydrogen
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Novel 8-triazolo(1,5-a)pyrimid-5-ones of general formula <FORM:1070243/C2/1> <FORM:1070243/C2/2> wherein, in Formula I, R3 represents an alkyl group or an aralkyl group which may be substituted by halogen, R5 represents hydrogen, or an alkyl group and R6 represents a carbalkoxy group, or R3 represents an alkyl group or an aralkyl group which may be substituted by halogen, and R5 and R6 are halogen, or R3 represents an aralkyl group which may be substituted by halogen, R5 represents hydrogen or alkyl or aryl and R6 represents hydrogen provided that when R3 is an unsubstituted benzyl group, R5 is not hydrogen or methyl, in Formula II R2 represents an aryl group, R4 represents an optionally substituted aralkyl group (where the substituent is halogen), R5 represents hydrogen or an alkyl group and R6 is hydrogen or a carbalkoxy group, or R2 represents hydrogen, R4 represents alkyl or aralkyl which may be substituted by halogen and R5 and R6 represent hydrogen, and novel s-triazolo(1,5-a)-pyrimid-7-ones of formulae <FORM:1070243/C2/3> AND <FORM:1070243/C2/4> wherein in Formula III R3 represents an aralkyl group which may be substituted by halogen, R6 represents a carbalkoxy group and R7 represents hydrogen or an alkyl group, and in Formula IV R2 represents an aryl group, R4 represents an aralkyl group, which may be substituted by halogen, R6 represents a carbalkoxy group and R7 represents hydrogen or an alkyl group, are prepared by condensing in a suitable solvent, e.g. acetic acid, a 3-amino (or aralkylamino)-1,2,4-triazole-5-R2 substituted as defined above, with either a b -keto ester of formula R5-CO-CH-COOR1 wherein R5 and R6 are as defined above and R1 is an alkyl group, or with an alkylalkoxymethylene malonate of formula <FORM:1070243/C2/5> or <FORM:1070243/C2/6> The compounds may also be prepared by N-alkylation or N-aralkylation of a hydroxy-triazolo pyrimidine of formula <FORM:1070243/C2/7> AND <FORM:1070243/C2/8> wherein R2, R5, R6 and R7 are as defined above and 4 - Benzyl - 6 - carbethoxy - 2 - phenyl - s - triazolo(1,5-a)-pyrimid-5-one is prepared by adding a solution of lead tetra-acetate in methylene dichloride to 1-benzyl-2-benzylidenehydrazine-5 -carbethoxypyrimid-6-one in the same solvent. 5 - R2 - substituted 3 - amino (or aralkylamino)-thiazoles, wherein R2 is defined above, and the aralkyl radical may be chloro-substituted, are prepared by cyclization with formic acid of the corresponding substituted aminoguanidines. N - Benzyl - N1 - (benzylideneamino) - guanidine is prepared by refluxing N-amino-N1-benzylguanidine hydriodide and benzaldehyde in ethanol. Pharmaceutical compositions having analgesic and anti-inflammatory activity and which may be administered orally or parenterally and contain a compound of any of the first four general formula above, as the active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2915164A GB1070243A (en) | 1964-07-15 | 1964-07-15 | S-triazolopyrimidones, their preparation and compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2915164A GB1070243A (en) | 1964-07-15 | 1964-07-15 | S-triazolopyrimidones, their preparation and compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1070243A true GB1070243A (en) | 1967-06-01 |
Family
ID=10286952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2915164A Expired GB1070243A (en) | 1964-07-15 | 1964-07-15 | S-triazolopyrimidones, their preparation and compositions containing them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1070243A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2018077A1 (en) * | 1968-09-13 | 1970-05-29 | Ici Ltd | |
| FR2424924A1 (en) * | 1978-05-05 | 1979-11-30 | Bristol Myers Co | NEW AZOLOPYRIMIDINONES, THEIR PRODUCTION PROCESS AND THE MEDICINAL PRODUCT CONTAINING THEM |
| WO1985002846A1 (en) * | 1983-12-27 | 1985-07-04 | Schering Corporation | 4,7-DIMETHYL-2-(4-PYRIDINYL)-1,2,4-TRIAZOLO AD1,5-a BDPYRIMIDIN-5(4H)-ONE |
| GR900100149A (en) * | 1989-03-03 | 1990-07-31 | Egyt Gyogyszervegyeszeti Gyar | Preparation method of new triazolo-pyrimidine derivatives |
| EP4161494A4 (en) * | 2020-06-02 | 2024-07-17 | KSQ Therapeutics, Inc. | NITROGEN-CONTAINING CONDENSED BICYCLIC COMPOUNDS AND THEIR USE AS UBIQUITIN-SPECIFIC PROCESSING PROTEASE 1 (USP1) INHIBITORS |
-
1964
- 1964-07-15 GB GB2915164A patent/GB1070243A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2018077A1 (en) * | 1968-09-13 | 1970-05-29 | Ici Ltd | |
| FR2424924A1 (en) * | 1978-05-05 | 1979-11-30 | Bristol Myers Co | NEW AZOLOPYRIMIDINONES, THEIR PRODUCTION PROCESS AND THE MEDICINAL PRODUCT CONTAINING THEM |
| WO1985002846A1 (en) * | 1983-12-27 | 1985-07-04 | Schering Corporation | 4,7-DIMETHYL-2-(4-PYRIDINYL)-1,2,4-TRIAZOLO AD1,5-a BDPYRIMIDIN-5(4H)-ONE |
| EP0147774A3 (en) * | 1983-12-27 | 1985-08-07 | Schering Corporation | 4,7-dimethyl-2-(4-pyridinyl)-1,2,4-triazolo(1,5-a)pyrimidine-5(4h)-one |
| US4614743A (en) * | 1983-12-27 | 1986-09-30 | Schering Corporation | Methods of treating pain and inflammation with 4,7-dimethyl-2-(4-pyridinyl)-1,2,4,-triazolo[1,5-a]pyrimidin-5(4H)-one or the pharmaceutically acceptable salts or solvates thereof |
| GR900100149A (en) * | 1989-03-03 | 1990-07-31 | Egyt Gyogyszervegyeszeti Gyar | Preparation method of new triazolo-pyrimidine derivatives |
| FR2643904A1 (en) * | 1989-03-03 | 1990-09-07 | Egyt Gyogyszervegyeszeti Gyar | NOVEL TRIAZOLO-PYRIMIDINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
| EP4161494A4 (en) * | 2020-06-02 | 2024-07-17 | KSQ Therapeutics, Inc. | NITROGEN-CONTAINING CONDENSED BICYCLIC COMPOUNDS AND THEIR USE AS UBIQUITIN-SPECIFIC PROCESSING PROTEASE 1 (USP1) INHIBITORS |
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