PL429162A1 - 3-(trifluoromethyl)-7,8-dihydroimidazo[2,1-c][1,2,4]triazine-4(6H)-ones substituted with monochlorophenyl or dichlorophenyl, method of their preparation and medical use - Google Patents
3-(trifluoromethyl)-7,8-dihydroimidazo[2,1-c][1,2,4]triazine-4(6H)-ones substituted with monochlorophenyl or dichlorophenyl, method of their preparation and medical useInfo
- Publication number
- PL429162A1 PL429162A1 PL429162A PL42916219A PL429162A1 PL 429162 A1 PL429162 A1 PL 429162A1 PL 429162 A PL429162 A PL 429162A PL 42916219 A PL42916219 A PL 42916219A PL 429162 A1 PL429162 A1 PL 429162A1
- Authority
- PL
- Poland
- Prior art keywords
- dichlorophenyl
- monochlorophenyl
- chlorophenyl
- compounds
- general formula
- Prior art date
Links
- -1 monochlorophenyl Chemical group 0.000 title abstract 4
- 125000004188 dichlorophenyl group Chemical group 0.000 title abstract 3
- SYQKWUZEGJKCLM-UHFFFAOYSA-N 3-(trifluoromethyl)-7,8-dihydro-6H-imidazo[2,1-c][1,2,4]triazin-4-one Chemical group FC(C=1C(N2C(=NN=1)NCC2)=O)(F)F SYQKWUZEGJKCLM-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 241000252212 Danio rerio Species 0.000 abstract 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 abstract 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 1
- 206010006187 Breast cancer Diseases 0.000 abstract 1
- 208000026310 Breast neoplasm Diseases 0.000 abstract 1
- 206010008342 Cervix carcinoma Diseases 0.000 abstract 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 201000010881 cervical cancer Diseases 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 210000002257 embryonic structure Anatomy 0.000 abstract 1
- 210000003743 erythrocyte Anatomy 0.000 abstract 1
- KJHQVUNUOIEYSV-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-oxopropanoate Chemical compound CCOC(=O)C(=O)C(F)(F)F KJHQVUNUOIEYSV-UHFFFAOYSA-N 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 201000005202 lung cancer Diseases 0.000 abstract 1
- 208000020816 lung neoplasm Diseases 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 238000001050 pharmacotherapy Methods 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 239000003642 reactive oxygen metabolite Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem zgłoszenia są 3-(trifluorometylo)-7,8-dihydroimidazo[2,1-c][1,2,4]triazyn-4(6H)-ony podstawione monochlorofenylem lub dichlorofenylem o wzorze ogólnym 1, w którym R oznacza monochlorofenyl - zwłaszcza 2-chlorofenyl, 3-chlorofenyl, 4-chlorofenyl, lub dichlorofenyl - zwłaszcza 3,4-dichlorofenyl, wykazujące działanie przeciwnowotworowe i antyhemolityczne, a jednocześnie będące nietoksycznymi dla zarodków/larw danio pręgowanego (Danio rerio). Przedmiotem zgłoszenia jest również zastosowanie związków o wzorze ogólnym 1 w farmakoterapii nowotworów, takich jak rak piersi, rak szyjki macicy oraz rak płuc. Ponadto przedmiotem wynalazku jest zastosowanie związków o wzorze ogólnym 1 jako preparaty o działaniu ochronnym na erytrocyty narażone na reaktywne formy tlenu. Związki będące przedmiotem zgłoszenia otrzymuje się w wyniku kondensacji odpowiednio podstawionych halogenowodorków hydrazonów imidazolidyno-2-onów z estrem etylowym kwasu 3,3,3-trifluoropirogronowego, stosując stosunek molowy substratów 1:1, w środowisku rozpuszczalników organicznych w obecności substancji zasadowych wiążących wydzielający się halogenowodór. Produkt oczyszcza się przez krystalizację z mieszaniny alkoholu metylowego i dimetyloformamidu.The subject of the application is 3- (trifluoromethyl) -7,8-dihydroimidazo [2,1-c] [1,2,4] triazin-4 (6H) -one substituted with monochlorophenyl or dichlorophenyl of general formula I, in which R is monochlorophenyl - especially 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, or dichlorophenyl - especially 3,4-dichlorophenyl, having antitumor and antihaemolytic activity and at the same time being non-toxic to zebrafish embryos / larvae (Danio rerio). The application also relates to the use of compounds of general formula I in the pharmacotherapy of cancers such as breast cancer, cervical cancer and lung cancer. The invention furthermore relates to the use of compounds of the general formula I as preparations with a protective effect on erythrocytes exposed to reactive oxygen species. The compounds that are the subject of the application are obtained by condensation of appropriately substituted imidazolidin-2-one hydrazone hydrazone halides with 3,3,3-trifluoropyruvic acid ethyl ester using a molar ratio of substrates of 1: 1, in an organic solvent medium in the presence of basic substances binding the evolved hydrogen halide . The product is purified by crystallization from a mixture of methyl alcohol and dimethylformamide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL429162A PL236363B1 (en) | 2019-03-06 | 2019-03-06 | 3-(trifluoromethyl)-7,8-dihydroimidazo[2,1-c][1,2,4]triazine-4(6H)-ones substituted with monochlorophenyl or dichlorophenyl, method of their preparation and medical use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL429162A PL236363B1 (en) | 2019-03-06 | 2019-03-06 | 3-(trifluoromethyl)-7,8-dihydroimidazo[2,1-c][1,2,4]triazine-4(6H)-ones substituted with monochlorophenyl or dichlorophenyl, method of their preparation and medical use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL429162A1 true PL429162A1 (en) | 2020-01-02 |
| PL236363B1 PL236363B1 (en) | 2021-01-11 |
Family
ID=69160889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL429162A PL236363B1 (en) | 2019-03-06 | 2019-03-06 | 3-(trifluoromethyl)-7,8-dihydroimidazo[2,1-c][1,2,4]triazine-4(6H)-ones substituted with monochlorophenyl or dichlorophenyl, method of their preparation and medical use |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL236363B1 (en) |
-
2019
- 2019-03-06 PL PL429162A patent/PL236363B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL236363B1 (en) | 2021-01-11 |
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