CS235199B1 - 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1h-pyrazolo-(3,4-b) quinolines and method of their preparation - Google Patents
4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1h-pyrazolo-(3,4-b) quinolines and method of their preparation Download PDFInfo
- Publication number
- CS235199B1 CS235199B1 CS841310A CS131084A CS235199B1 CS 235199 B1 CS235199 B1 CS 235199B1 CS 841310 A CS841310 A CS 841310A CS 131084 A CS131084 A CS 131084A CS 235199 B1 CS235199 B1 CS 235199B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- pyrazolo
- methyl
- alkyl
- hydroxyethylamino
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 229940111121 antirheumatic drug quinolines Drugs 0.000 title description 2
- 150000003248 quinolines Chemical class 0.000 title description 2
- 150000001414 amino alcohols Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- YGUHVTJIAZNXPY-UHFFFAOYSA-N 4-chloro-3-methyl-2h-pyrazolo[3,4-b]quinoline Chemical compound C1=CC=C2C(Cl)=C3C(C)=NNC3=NC2=C1 YGUHVTJIAZNXPY-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- TXCKXHMVJXTXTK-UHFFFAOYSA-N 1-(2,3-dihydroxypropyl)-3-methyl-9H-pyrazolo[3,4-b]quinolin-4-one Chemical compound Cc1nn(CC(O)CO)c2[nH]c3ccccc3c(=O)c12 TXCKXHMVJXTXTK-UHFFFAOYSA-N 0.000 description 1
- -1 4- (1-ethyl-2-hydroxyethylamino) -3-methyl-1H-pyrazolo [3,4-b] quinoline Chemical compound 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález se týká 4-(l-alkyl-2-hydroxyethylamino)-3-methyl-lH-pyrazolo[ 3,4-b ] chinolinů obecného vzorce IThe invention relates to 4- (1-alkyl-2-hydroxyethylamino) -3-methyl-1H-pyrazolo [3,4-b] quinolines of formula I
kde R značí alkylskupinu o 1 až 5 atomech uhlíku, a způsobu jejich přípravy.wherein R is C 1 -C 5 alkyl, and a process for their preparation.
Tyto nové, dosud nepopsané látky slouží jako meziprodukty pro přípravu 4,9-diihydro-l-(2,3-dihydroxpropyl)-3-meťhy-4-oxo-lHpyrazoloj 3,4-b jchinolinu s proitivirovým účinkem (čs. autorské osvědčení č. 235 188).These novel, hitherto undescribed substances serve as intermediates for the preparation of 4,9-dihydro-1- (2,3-dihydroxypropyl) -3-methyl-4-oxo-1H-pyrazolo [3,4-b] quinoline with a proitiviral effect. No. 235,188).
Sloučeniny obecného vzorce I lze podle vynálezu připravit reakcí o sobě známého 4-chlO'r-3-methyl-lH-pyrazolo[ 3,4-b jchinolinu [Crenshaw R. R., Luke G. M., Simonoff P.: J. Med. Chem. 19, 262 (1976)] 10 až 25 molárním přebytkem amínoalkoholu obecného vzorceThe compounds of the formula I according to the invention can be prepared by the reaction of the known 4-chloro-3-methyl-1H-pyrazolo [3,4-bquinoline] [Crenshaw R. R., Luke G. M., Simonoff P .: J. Med. Chem. 19, 262 (1976)] with a 10 to 25 molar excess of the amino alcohol of formula
RCH(NH2)CH2OH kde R má výše uvedený význam, při teplotě 110 až 150 °C, výhodně při teplotě 130 °C. Výhodně se používá 20 molární přebytek aminoalkoholu, většina přebytečného aminoalkoholu se po skončení reakce regeneruje destilací z reakční směsi.RCH (NH 2) CH 2 OH wherein R is as defined above, at a temperature of 110 to 150 ° C, preferably at 130 ° C. Preferably a 20 molar excess of amino alcohol is used, most of the excess amino alcohol is recovered by distillation from the reaction mixture after the reaction is complete.
Bližší podrobnosti plynou z následujícího příkladu provedení, který uvedený vynález pouze ilustruje, nikoliv omezuje.For further details, reference should be made to the following non-limiting example.
PříkladExample
4- (l-ethyl-2-hydr oxyethylamino j -3-methyl-lH-pyrazolo [ 3,4-b ] chinolin4- (1-ethyl-2-hydroxyethylamino) -3-methyl-1H-pyrazolo [3,4-b] quinoline
Směs 12 g 4-chlor-3-methyl-lH-pyrazolo[ 3,4-b jchinolinu (55 mmol) a 130 ml racemického 2-amino-l-butanOlu byla míchána 12 hodin při teplotě 130 °C. Po oddestilování 100 ml 2-amino-l-butanolu byl zbytek zředěn 100 ml vody a vyloučená látka byla odsáta. Překrystalováním z ethanolu bylo získáno 11,6 g látky (78,0%) o t. t. 223 °C až 225 °C.A mixture of 12 g of 4-chloro-3-methyl-1H-pyrazolo [3,4-bquinoline (55 mmol) and 130 ml of racemic 2-amino-1-butanol was stirred at 130 ° C for 12 hours. After distilling off 100 ml of 2-amino-1-butanol, the residue was diluted with 100 ml of water and the precipitate was filtered off with suction. Recrystallization from ethanol gave 11.6 g (78.0%) of m.p. 223-225 ° C.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS841310A CS235199B1 (en) | 1983-09-09 | 1984-02-24 | 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1h-pyrazolo-(3,4-b) quinolines and method of their preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS658683A CS235167B1 (en) | 1983-09-09 | 1983-09-09 | Substituted 4,9-dihydro-3-methyl-4-oxo-1h-pyrazolo-(3,4-b)quinolines and method of their production |
| CS841310A CS235199B1 (en) | 1983-09-09 | 1984-02-24 | 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1h-pyrazolo-(3,4-b) quinolines and method of their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235199B1 true CS235199B1 (en) | 1985-05-15 |
Family
ID=5413268
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS658683A CS235167B1 (en) | 1983-09-09 | 1983-09-09 | Substituted 4,9-dihydro-3-methyl-4-oxo-1h-pyrazolo-(3,4-b)quinolines and method of their production |
| CS838459A CS235182B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-1,3-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
| CS838460A CS235183B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-3,9-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
| CS839743A CS235188B1 (en) | 1983-09-09 | 1983-12-21 | 4,9-dihydro-1-1(2,3-dihydroxypropyl)-3-methyl-4-oxo-1h-pyrazolo (3,4-b) quinoline and method of its preparation |
| CS841309A CS235198B1 (en) | 1983-09-09 | 1984-02-24 | 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl)-1h-pyrazolo (3,4-b) quinolines and method of their preparation |
| CS841310A CS235199B1 (en) | 1983-09-09 | 1984-02-24 | 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1h-pyrazolo-(3,4-b) quinolines and method of their preparation |
Family Applications Before (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS658683A CS235167B1 (en) | 1983-09-09 | 1983-09-09 | Substituted 4,9-dihydro-3-methyl-4-oxo-1h-pyrazolo-(3,4-b)quinolines and method of their production |
| CS838459A CS235182B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-1,3-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
| CS838460A CS235183B1 (en) | 1983-09-09 | 1983-11-15 | Method of 4,9-dihydro-3,9-dimethyl-4-oxo-1h-pyrazolo-(3,4-b)quinoline preparation |
| CS839743A CS235188B1 (en) | 1983-09-09 | 1983-12-21 | 4,9-dihydro-1-1(2,3-dihydroxypropyl)-3-methyl-4-oxo-1h-pyrazolo (3,4-b) quinoline and method of its preparation |
| CS841309A CS235198B1 (en) | 1983-09-09 | 1984-02-24 | 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl)-1h-pyrazolo (3,4-b) quinolines and method of their preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (6) | CS235167B1 (en) |
-
1983
- 1983-09-09 CS CS658683A patent/CS235167B1/en unknown
- 1983-11-15 CS CS838459A patent/CS235182B1/en unknown
- 1983-11-15 CS CS838460A patent/CS235183B1/en unknown
- 1983-12-21 CS CS839743A patent/CS235188B1/en unknown
-
1984
- 1984-02-24 CS CS841309A patent/CS235198B1/en unknown
- 1984-02-24 CS CS841310A patent/CS235199B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS235167B1 (en) | 1985-05-15 |
| CS235188B1 (en) | 1985-05-15 |
| CS235182B1 (en) | 1985-05-15 |
| CS235198B1 (en) | 1985-05-15 |
| CS235183B1 (en) | 1985-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1731051A3 (en) | Method for synthesis of benzothiazole derivatives or theirs acid-additive salt | |
| SU552025A3 (en) | Method for preparing phenyl-imidazolyl alkane derivatives | |
| US4118417A (en) | Process for resolving cis-1-substituted phenyl-1,2-cyclopropanedicarboxylic acids | |
| PL164955B1 (en) | Method of obtaining novel indolone derivatives | |
| CA1232910A (en) | METHOD OF RESOLVING BICYCLIC IMINO-.alpha.-CARBOXYLIC ACID ESTER RACEMATES | |
| EP0179254A1 (en) | 4,5-Dihydro-4-oxo-2- [(2-trans-phenylcyclopropyl)amino]-3-furancarboxylic acids and derivatives thereof | |
| CA2368815A1 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
| SU722481A3 (en) | Method of preparing aminoketone derivatives or their salts | |
| JPS6324991B2 (en) | ||
| SU428602A3 (en) | METHOD OF OBTAINING BASIC-SUBSTITUTE DERIVATIVES 1 | |
| US4325886A (en) | Optical resolution of acylthiopropionic acid | |
| CS235199B1 (en) | 4-(1-alkyl-2-hydroxyethylamino)-3-methyl-1h-pyrazolo-(3,4-b) quinolines and method of their preparation | |
| ES2167869T3 (en) | PROCEDURE TO PREPARE NICOTINIC ACIDS. | |
| US2540946A (en) | Pyridoxal-histamine and processes for preparing the same | |
| RU2007146394A (en) | METHODS FOR PRODUCING HETEROCYCLIC COMPOUNDS | |
| SU803859A3 (en) | Method of preparing omega-thiopropionamides or their acid-additive salts | |
| SU569287A3 (en) | Method of preparation of benzhydryloxyalkylamine derivatives or salts thereof | |
| JPS6355512B2 (en) | ||
| SU439978A1 (en) | The method of obtaining sulfamoylpyrimidine or its salt | |
| JPS6127977A (en) | 4,5-dihydro-3,3-diphenyl-4-hydrocarbyl aminomethylfuran-2(3h)-one | |
| US4107179A (en) | Method for preparing ticrynafen | |
| CN1035672C (en) | Preparation method of 3-(methyl-imidazolyl) methyl-tetrahydro-carbazolone | |
| US2474822A (en) | Quinoline compounds and process of making same | |
| JPH0174A (en) | Benzimidazole derivatives | |
| JP2767295B2 (en) | Method for producing indole-3-carbonitrile compound |