PL402467A1 - 1,2,4-triazole derivative: 5-(2,3-dichlorophenyl)-4-pentyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, a method for its preparation and its first medical application - Google Patents
1,2,4-triazole derivative: 5-(2,3-dichlorophenyl)-4-pentyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, a method for its preparation and its first medical applicationInfo
- Publication number
- PL402467A1 PL402467A1 PL402467A PL40246713A PL402467A1 PL 402467 A1 PL402467 A1 PL 402467A1 PL 402467 A PL402467 A PL 402467A PL 40246713 A PL40246713 A PL 40246713A PL 402467 A1 PL402467 A1 PL 402467A1
- Authority
- PL
- Poland
- Prior art keywords
- reaction
- pentyl
- triazole
- pharmaceutically acceptable
- acceptable salts
- Prior art date
Links
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- QAFTZJJVUVPDRY-UHFFFAOYSA-N N1C(=S)N(CCCCC)C(C=2C(=C(Cl)C=CC=2)Cl)=N1 Chemical compound N1C(=S)N(CCCCC)C(C=2C(=C(Cl)C=CC=2)Cl)=N1 QAFTZJJVUVPDRY-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 8
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000002798 polar solvent Substances 0.000 abstract 4
- 235000019441 ethanol Nutrition 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- SGHJUJBYMSVAJY-UHFFFAOYSA-N 1-isothiocyanatopentane Chemical compound CCCCCN=C=S SGHJUJBYMSVAJY-UHFFFAOYSA-N 0.000 abstract 1
- BXJDUQVJADYYCG-UHFFFAOYSA-N 2,3-dichlorobenzohydrazide Chemical compound NNC(=O)C1=CC=CC(Cl)=C1Cl BXJDUQVJADYYCG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000956 alloy Substances 0.000 abstract 1
- 229910045601 alloy Inorganic materials 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 150000003583 thiosemicarbazides Chemical class 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem wynalazku jest pochodna 1,2,4-triazolu o wzorze ogólnym 1, oraz jej farmaceutycznie dopuszczalne sole. Przedmiotem jest także sposób wytwarzania pochodnych 5-(2,3-dichlorofenylo)-4-pentylo- 2,4-dihydro-3H-1,2,4-triazolo-3-tionu o wzorze ogólnym 1 oraz ich farmaceutycznie dopuszczalnych soli, który polega na tym, że hydrazyd kwasu 2,3-dichlorobenzoesowego o poddaje się reakcji z izotiocyjanianem pentylu, przy czym reakcję prowadzi się w stosunku molowym 1:1, w stopie lub w rozpuszczalnikach polarnych. W przypadku prowadzenia reakcji w stopie mieszaninę substratów ogrzewa się w temperaturze 100-140°C przez 1-10 minut, a w przypadku zaś reakcji w środowisku rozpuszczalnika polarnego zwłaszcza alkoholu etylowego proces prowadzi się w temperaturze wrzenia rozpuszczalnika przez okres 5-30 minut wstępnie po schłodzeniu powstały produkt odsącza się i krystalizuje z odpowiedniego rozpuszczalnika polarnego, korzystnie z etanolu i otrzymaną pochodną tiosemikarbazydu poddaje się reakcji cyklizacji w wodnym roztworze wodorotlenku, po czym roztwór zadaje się wodnym roztworem kwasu, korzystnie kwasem solnym do otrzymania odczynu kwasowego, zaś strącony związek o wzorze 1, krystalizuje się z odpowiedniego rozpuszczalnika polarnego, korzystnie z etanolu. Wynalazek obejmuje również pochodna 1,2,4-triazolu o wzorze ogólnym 1, oraz jej farmaceutycznie dopuszczalne sole do zastosowania jako lek.The present invention relates to a 1,2,4-triazole derivative of general formula 1, and pharmaceutically acceptable salts thereof. The subject of the invention is also a process for the preparation of 5- (2,3-dichlorophenyl) -4-pentyl-2,4-dihydro-3H-1,2,4-triazol-3-thione derivatives of general formula 1 and their pharmaceutically acceptable salts, which is that 2,3-dichlorobenzoic acid hydrazide is reacted with pentyl isothiocyanate, the reaction being carried out in a molar ratio of 1: 1, in an alloy or in polar solvents. If the reaction is carried out in the melt, the substrate mixture is heated at 100-140 ° C for 1-10 minutes, and in the case of a reaction in a polar solvent environment, especially ethyl alcohol, the process is carried out at the boiling point of the solvent for a period of 5-30 minutes pre-cooling the resulting product is filtered off and crystallized from a suitable polar solvent, preferably from ethanol, and the thiosemicarbazide derivative obtained is subjected to a cyclization reaction in an aqueous hydroxide solution, then the solution is mixed with an aqueous acid solution, preferably with hydrochloric acid to obtain an acid reaction, and the precipitated compound of formula 1 , crystallized from a suitable polar solvent, preferably from ethanol. The invention also includes the 1,2,4-triazole derivative of general formula 1, and pharmaceutically acceptable salts thereof for use as a medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL402467A PL221233B1 (en) | 2013-01-17 | 2013-01-17 | 1,2,4-triazole derivative: 5-(2,3-dichlorophenyl)-4-pentyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, a method for its preparation and its first medical application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL402467A PL221233B1 (en) | 2013-01-17 | 2013-01-17 | 1,2,4-triazole derivative: 5-(2,3-dichlorophenyl)-4-pentyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, a method for its preparation and its first medical application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL402467A1 true PL402467A1 (en) | 2014-07-21 |
| PL221233B1 PL221233B1 (en) | 2016-03-31 |
Family
ID=51179308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL402467A PL221233B1 (en) | 2013-01-17 | 2013-01-17 | 1,2,4-triazole derivative: 5-(2,3-dichlorophenyl)-4-pentyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, a method for its preparation and its first medical application |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221233B1 (en) |
-
2013
- 2013-01-17 PL PL402467A patent/PL221233B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL221233B1 (en) | 2016-03-31 |
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