PL422559A1 - Chiral triazole derivatives of cinchona tree alkaloids and method for producing them - Google Patents
Chiral triazole derivatives of cinchona tree alkaloids and method for producing themInfo
- Publication number
- PL422559A1 PL422559A1 PL422559A PL42255917A PL422559A1 PL 422559 A1 PL422559 A1 PL 422559A1 PL 422559 A PL422559 A PL 422559A PL 42255917 A PL42255917 A PL 42255917A PL 422559 A1 PL422559 A1 PL 422559A1
- Authority
- PL
- Poland
- Prior art keywords
- triazole derivatives
- producing
- alkaloids
- chiral triazole
- chiral
- Prior art date
Links
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title abstract 3
- 235000021513 Cinchona Nutrition 0.000 title 1
- 241000157855 Cinchona Species 0.000 title 1
- 229930013930 alkaloid Natural products 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract 2
- 150000003797 alkaloid derivatives Chemical group 0.000 abstract 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Chemical group 0.000 abstract 1
- 239000001257 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Przedmiotem zgłoszenia są chiralne triazolowe pochodne alkaloidów chinowca, będące 9-deoksy-9-(5-hetarylo-3-merkapto-4H-1,2,4-tetrazol-4-ylo) pochodnymi alkaloidów drzewa chinowego o wzorze ogólnym 1, w którym R1 oznacza grupę metoksylową lub wodór zaś szkielet alkaloidowy stanowi układ cynchonanu, natomiast w pozycji 5 znajduje się grupa 4-pirydylowa. Zgłoszenie dotyczy również sposobu wytwarzania chiralnych pochodnych triazolowych o wzorze ogólnym 1, który polega na tym, że 9-izotiocyjano-(9-deoksy) pochodną alkaloidu o wzorze 2 poddaje się reakcji sprzęgania z równomolową ilością hydrazydu kwasu izonikotynowego w temperaturze 333 K do 353 K, w środowisku rozpuszczalnika organicznego.The subject of the application are chiral triazole derivatives of quinine alkaloids, which are 9-deoxy-9- (5-hetaryl-3-mercapto-4H-1,2,4-tetrazol-4-yl) derivatives of the quinine alkaloids of the general formula 1, in which R1 is methoxy or hydrogen, while the alkaloid backbone is the cinchonane system, while position 5 is the 4-pyridyl group. The application also relates to a process for the preparation of chiral triazole derivatives of general formula 1, which consists in the 9-isothiocyano- (9-deoxy) alkaloid derivative of formula 2 being subjected to a coupling reaction with an equimolar amount of isonicotinic acid hydrazide at 333 K to 353 K in an organic solvent environment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422559A PL237599B1 (en) | 2017-08-16 | 2017-08-16 | Chiral triazole derivatives of cinchona tree alkaloids and method for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422559A PL237599B1 (en) | 2017-08-16 | 2017-08-16 | Chiral triazole derivatives of cinchona tree alkaloids and method for producing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL422559A1 true PL422559A1 (en) | 2018-04-09 |
| PL237599B1 PL237599B1 (en) | 2021-05-04 |
Family
ID=61809981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL422559A PL237599B1 (en) | 2017-08-16 | 2017-08-16 | Chiral triazole derivatives of cinchona tree alkaloids and method for producing them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL237599B1 (en) |
-
2017
- 2017-08-16 PL PL422559A patent/PL237599B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL237599B1 (en) | 2021-05-04 |
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