CS252342B1 - O,n-substituted 4,9-didydro-6-hydroxy-2,3-dimethyl-4-oxo-2h-pyrazolo(3,4-)quinolones - Google Patents
O,n-substituted 4,9-didydro-6-hydroxy-2,3-dimethyl-4-oxo-2h-pyrazolo(3,4-)quinolones Download PDFInfo
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- CS252342B1 CS252342B1 CS863353A CS335386A CS252342B1 CS 252342 B1 CS252342 B1 CS 252342B1 CS 863353 A CS863353 A CS 863353A CS 335386 A CS335386 A CS 335386A CS 252342 B1 CS252342 B1 CS 252342B1
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- Czechoslovakia
- Prior art keywords
- pyrazolo
- oxo
- dimethyl
- hydroxy
- substituted
- Prior art date
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- 150000007660 quinolones Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- -1 N-substituted 4,9-dihydro-6-hydroxy-2,3-dimethyl-4-oxo-2H-pyrazolo [3,4-b] quinolines Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 235000012745 brilliant blue FCF Nutrition 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 238000010186 staining Methods 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- KKIITVHSDBKAMI-UHFFFAOYSA-N 6-methoxy-2,3,9-trimethylpyrazolo[3,4-b]quinolin-4-one Chemical compound CN1C2=NN(C)C(C)=C2C(=O)C2=CC(OC)=CC=C21 KKIITVHSDBKAMI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- HVMWGSINXRRRCT-UHFFFAOYSA-N 6-hydroxy-2,3,9-trimethylpyrazolo[3,4-b]quinolin-4-one Chemical compound C1=C(O)C=C2C(=O)C3=C(C)N(C)N=C3N(C)C2=C1 HVMWGSINXRRRCT-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ZNMSDGGOBMBEPZ-UHFFFAOYSA-N [ClH]1C=CCC1 Chemical compound [ClH]1C=CCC1 ZNMSDGGOBMBEPZ-UHFFFAOYSA-N 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Modré 1:2 chromkomplexní barvivo pro barvení vlny a PADu ze slabě kyselé neutrální lázně je tvořeno směsí barviva obecného vzorce I konstituce A, kde M znamená Na, K, NH^ a X NO2 a Y H a konstituce B, kde M znamená Na, K, NH^ a X H a Y Cl v poměru konstituce A:B * 0,05 až 99,5:99,5 až 0,5.Blue 1: 2 chrome complex dye for wool staining and PAD of weakly acid neutral the bath consists of a mixture of dye of formula I wherein A is M, K, NH 2 and X NO 2 and Y H and Constitution B, where M represents Na, K, NH 4 and X H and Y Cl in the ratio constitution A: B * 0.05 to 99.5: 99.5 to 0.5.
Description
Vynález se týká O,N-substituovaných /3,4-b/ chinolinů obecného vzorce IThe invention relates to O, N-substituted (3,4-b) quinolines of the formula I
4,9-dihydro-6-hydroxy-2,3-dimetyl-4-oxo-2H-pyrazolo4,9-Dihydro-6-hydroxy-2,3-dimethyl-4-oxo-2H-pyrazolo
R1OR 1 O
ΧΧΛΧΧΧΛΧ
CH, /1/,CH, / 1 /,
2 kde R a R je atom vodíku nebo metylskupina.Wherein R and R are hydrogen or methyl.
Tyto nové, dosud nepopsané látky, jsou použitelné jako meziprodukty pro přípravu látek vykazujících významné biologické účinky, zvláště protivirový a protinádorový účinek.These novel substances, which have not been described yet, are useful as intermediates for the preparation of substances having significant biological effects, in particular antiviral and antitumor activity.
22
Sloučeninu obecného vzorce I, kde R je metylskupina a R je atom vodíku, lze podle vynálezu připravit cyklizací o sobě známé 3-/4-methoxyanilino/-l,5-dimetyl-lH-pyrazol-4-karboxylové kyseliny polyfosforečnou kyselinou za zvýšené teploty. Sloučeninu obecného vzorce I, kde R1 i R2 je metylskupina, lze podle vynálezu připravit metylaci sodné soliThe compound of formula I wherein R is methyl and R is hydrogen may be prepared by cyclization of the well-known 3- (4-methoxyanilino) -1,5-dimethyl-1H-pyrazole-4-carboxylic acid by polyphosphoric acid at elevated temperature . A compound of formula (I) wherein both R 1 and R 2 is methyl may be prepared by methylation of the sodium salt according to the invention
4.9- dihydro-6-methoxy-2,3-dimetyl-4-oxo-2H-pyrazolo/3,4-b/ chimolinu metyljodidem, výhodně za teploty místnosti v dimetylformamidu. Sloučeninu obecného vzorce X, kde R1 je atom vodíku 9 a R je metylskupina, lze podle vynálezu připravit z 4,9-dihydro-6-methoxy-2,3,9-trlmetyl-4-oxo-2H-pyrazolo/3,4-b/chinolinu demetylací azeotropiokou bromovodíkovou kyselinou.4.9-Dihydro-6-methoxy-2,3-dimethyl-4-oxo-2H-pyrazolo [3,4-b] chimoline with methyl iodide, preferably at room temperature in dimethylformamide. The compound of formula X wherein R 1 is hydrogen 9 and R is methyl may be prepared according to the invention from 4,9-dihydro-6-methoxy-2,3,9-trimethyl-4-oxo-2H-pyrazolo / 3, 4-b) quinoline by demethylation with azeotropic hydrobromic acid.
Způsob přípravy látek je jednoduchý a poskytuje látky v uspokojivých výtěžcích. Získané produkty jsou přímo použitelné k dalšímu zpracování.. Bližší podrobnosti vyplývají z následujících příkladů provedení. Uvedené příklady vynález pouze ilustrují, nikoliv omezují.The process for preparing the substances is simple and provides the substances in satisfactory yields. The products obtained are directly usable for further processing. The examples given are merely illustrative and not limiting.
PřikladlHe did
4.9- Dlhydro-6-methoxy-2,3-dimetyl-4-oxo-2H-pyrazolo/3,4-b/chlnolln4.9-Dihydro-6-methoxy-2,3-dimethyl-4-oxo-2H-pyrazolo [3,4-b] chloroline
Směs 3-/4-methoxvanllino/-l,5-dlmetyl-lH-pyrazols4-karboxylové kyseliny /13,1 g, 50 mmol/ a polyfosforečné kyseliny /75 g, 85 % Ρ2°5^ byla míchána 4 hodiny při teplotě 90 °C. Po přidání /500 ml/ byla směs ochlazena, nerozpustný podíl byl odsát a překrystalován z 50% vodného dimetylformamidu. Bylo získáno 9,6 g látky /79 %/ netající do 360 °C.A mixture of 3- (4-methoxvanylino) -1,5-dimethyl-1H-pyrazole-4-carboxylic acid (13.1 g, 50 mmol) and polyphosphoric acid (75 g, 85% Ρ 2 ° 5) was stirred at room temperature for 4 hours. 90 ° C. After addition (500 ml), the mixture was cooled, the insoluble material was aspirated and recrystallized from 50% aqueous dimethylformamide. 9.6 g (79%) of a melting point of 360 ° C were obtained.
Příklad 2Example 2
4,9-Dihydro-6-methoxy-2,3,9-trimetyl-4-oxo-2H-pyrazolo/3,4-b/chinolin4,9-Dihydro-6-methoxy-2,3,9-trimethyl-4-oxo-2H-pyrazolo [3,4-b] quinoline
K míchané suspenzi 4,9-dihydro-6-methoxy-2,3-dimetyl-4-oxo-2H-pyrazolo/3,4-b/chinolinu /12,2 g, 50 mmol/ v dlmetylformamidu /200 ml/ byl přidán 80%. hydrid-sodný /1,8 g, 60 mmol/ a směs byla míchána 1 hodinu za teploty místnosti. Po přidá-lí metyljódidu /8,5 g 60 mmol/ byla směs míchána 8 hodin za teploty místnosti. Po přidání vody /250 ml/ byla směs ochlazena, nerozpustný podíl byl odsát a krystalován z etanolu. Bylo získáno 12,1 g látky /94 %/ o t.t. 191 až 193 °C.To a stirred suspension of 4,9-dihydro-6-methoxy-2,3-dimethyl-4-oxo-2H-pyrazolo [3,4-b] quinoline (12.2 g, 50 mmol) in dimethylformamide (200 mL) was added added 80%. sodium hydride (1.8 g, 60 mmol) and the mixture was stirred at room temperature for 1 hour. After addition of methyl iodide (8.5 g of 60 mmol), the mixture was stirred at room temperature for 8 hours. After addition of water (250 ml), the mixture was cooled, the insoluble material was aspirated and crystallized from ethanol. 12.1 g (94%) of m.p. Mp 191-193 ° C.
Příklad 3Example 3
4,9-Dihydro-6-hydroxy-2,3,9-trimetyl-4-oxo-2H-pyrazolo/3,4-b/chlnolin4,9-Dihydro-6-hydroxy-2,3,9-trimethyl-4-oxo-2H-pyrazolo [3,4-b] quinoline
Směs 4,9-dihydro-6-methoxy-2,3,9-trimetyl-4-oxo-2H-pyrazolo/3,4-b/chinollnu /5,1 g, mmol/ a azetropické bromovodíkové kyseliny /70 ml/ byla vařena 5 hodin pod zpětným chladičem. Nerozpustný podíl vyloučený po ochlazení byl odsát a krystalizován z etanolu. Bylo získáno 3,9 g látky /79 %/ netající do 360 °C.A mixture of 4,9-dihydro-6-methoxy-2,3,9-trimethyl-4-oxo-2H-pyrazolo [3,4-b] quinoline (5.1 g, mmol) and azetropic hydrobromic acid (70 ml) was refluxed for 5 hours. The insoluble matter precipitated upon cooling was aspirated and crystallized from ethanol. 3.9 g (79%) of a melting point of 360 ° C were obtained.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863353A CS252342B1 (en) | 1986-05-08 | 1986-05-08 | O,n-substituted 4,9-didydro-6-hydroxy-2,3-dimethyl-4-oxo-2h-pyrazolo(3,4-)quinolones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS863353A CS252342B1 (en) | 1986-05-08 | 1986-05-08 | O,n-substituted 4,9-didydro-6-hydroxy-2,3-dimethyl-4-oxo-2h-pyrazolo(3,4-)quinolones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS335386A1 CS335386A1 (en) | 1987-01-15 |
| CS252342B1 true CS252342B1 (en) | 1987-08-13 |
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ID=5373319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS863353A CS252342B1 (en) | 1986-05-08 | 1986-05-08 | O,n-substituted 4,9-didydro-6-hydroxy-2,3-dimethyl-4-oxo-2h-pyrazolo(3,4-)quinolones |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS252342B1 (en) |
-
1986
- 1986-05-08 CS CS863353A patent/CS252342B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS335386A1 (en) | 1987-01-15 |
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