CS235189B1 - 4-Alkoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) quinolines and a process for their preparation - Google Patents
4-Alkoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) quinolines and a process for their preparation Download PDFInfo
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- CS235189B1 CS235189B1 CS839744A CS974483A CS235189B1 CS 235189 B1 CS235189 B1 CS 235189B1 CS 839744 A CS839744 A CS 839744A CS 974483 A CS974483 A CS 974483A CS 235189 B1 CS235189 B1 CS 235189B1
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- pyrazolo
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Abstract
Vynález se týká 4-alkoxykarbonylmethylamino-l,3-dimethyl-lH-pyrazolo(3,4-b)-chlnolinů obecného vzorce I kde R je alkylskupina s 1 až 3 atomy uhlíku a způsobu jejich přípravy. Tyto nové, dosud nepopsané látky slouží jako meziprodukty pro přípravu 4-karboxymethylamino-l,3-dimethyl-lH-pyrazolo- (3,4-b)-chinolinu, který je protivirově účinný.The invention relates to 4-alkoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo(3,4-b)-quinolines of the general formula I where R is an alkyl group with 1 to 3 carbon atoms and a process for their preparation. These new, previously undescribed substances serve as intermediates for the preparation of 4-carboxymethylamino-1,3-dimethyl-1H-pyrazolo-(3,4-b)-quinoline, which is antivirally active.
Description
Vynález se týká 4-alkoxykarbonylmethylamino-l,3-dimethyl-lH-pyrazolo( 3,4-b )-chlnolinů obecného vzorce IThe present invention relates to 4-alkoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) -quinoline of formula I
kde R značí alkylskupinu s 1 až 3 atomy uhlíku.wherein R is C 1 -C 3 alkyl.
Uvedené sloučeniny jsou nové a jsou použitelné jako meziprodukty pro přípravu biologicky účinných 4-karboxyalkylamino-1,3-dimethyl-lH-pyrazolo.(3,4-b) chinolinů s protivirovým účinkem podle čs. autorského osvědčení č. 235 177.Said compounds are novel and useful as intermediates for the preparation of biologically active 4-carboxyalkylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) quinolines having antiviral activity according to U.S. Pat. Certificate No. 235 177.
Sloučeniny obecného vzorce I lze podle vynálezu připravit reakcí 4-(4-methoxyfenoxyj- nebo 4-fenoxy-l,3-dimethyl-lH-pyrazolo( 3,4-b) chinolinů podle čs. autorského osvědčení č. 235 176, s hydrochloridy alkylesterů glycinu, kde alkyl značí alkylskupinu s 1 až 3 atomy uhlíku, výhodně s 0,1 molárním přebytkem hydrochloridu, ve fenolu, při teplotě 80 až 120 °C, výhodně při teplotě 100 °C.The compounds of the formula I according to the invention can be prepared by reacting 4- (4-methoxyphenoxy) - or 4-phenoxy-1,3-dimethyl-1H-pyrazolo (3,4-b) quinolines according to the author's certificate No. 235 176 with hydrochlorides alkyl esters of glycine, wherein alkyl is C 1 -C 3 alkyl, preferably with a 0.1 molar excess of hydrochloride, in phenol, at 80 to 120 ° C, preferably at 100 ° C.
Následující příklady provedení vynález dokládají, ale nikterak neomezují.The following examples illustrate the invention but do not limit it in any way.
Příklad 1Example 1
Hydrochlorid 4-ethoxykarbonylmethylamino-1,3-dimethyl-lH-pyrazolo (3,4-b) chinolinů4-Ethoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) quinoline hydrochloride
Směs 5,76 g 4-fenoxy-l,3-dlmethyl-lH-pyrazolof 3,4-b) chinolinů (20 mmol), 3,07 g hydrochloridu ethylesteru glycinu (22 mmol) a 20 g fenolu byla míchána 4 hodiny při teplotě 100 °C. Reakční směs byla zředěna 50 ml ethanolu a chladný roztok byl sražen etherem. Překrystalováním z ethanolu bylo získáno 6,45 g látky (96,3 %) o t. t. 196,2 až 198,7 °C.A mixture of 5.76 g of 4-phenoxy-1,3-dlmethyl-1H-pyrazolof 3,4-b) quinolines (20 mmol), 3.07 g of glycine ethyl ester hydrochloride (22 mmol) and 20 g of phenol was stirred for 4 hours at temperature 100 ° C. The reaction mixture was diluted with 50 mL of ethanol and the cold solution was precipitated with ether. Recrystallization from ethanol gave 6.45 g (96.3%) of m.p. 196.2-198.7 ° C.
Příklad 2Example 2
Hydrochlorid 4-ethoxykarbonylmethylamino-1,3-dimethyl-lH-pyrazolo (3,4-b) chinolinů4-Ethoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) quinoline hydrochloride
Směs 3,19 g 4-(4-methoxyf enoxy )-l,3-dimethyl-lH-pyrazolo(3,4-b)chinolinů (10 mmol), 1,53 g hydrochloridu ethylesteru glycinu (11 mmol) a 10 g fenolu byla míchána 3 hodiny při teplotě 100 °C. Reakční směs byla zředěna 25 ml ethanolu a chladný roztok byl srážen etherem. Překrystolaváním z ethanolu bylo získáno 3,1 g látky (92,6 %) a 1.1. 196 až 199 °C.A mixture of 3.19 g of 4- (4-methoxyphenoxy) -1,3-dimethyl-1H-pyrazolo (3,4-b) quinolines (10 mmol), 1.53 g of glycine ethyl ester hydrochloride (11 mmol) and 10 g The phenol was stirred at 100 ° C for 3 hours. The reaction mixture was diluted with 25 mL of ethanol and the cold solution was precipitated with ether. Recrystallization from ethanol gave 3.1 g (92.6%) and 1.1. Mp 196-199 ° C.
PREDMETSUBJECT
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS839744A CS235189B1 (en) | 1983-10-26 | 1983-12-21 | 4-Alkoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) quinolines and a process for their preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS787183A CS235177B1 (en) | 1983-10-26 | 1983-10-26 | 4-Carboxyalkylamino-1,3-dimethyl-1H-pyrazolo (3,4-bquinoline and method for its preparation) |
| CS839744A CS235189B1 (en) | 1983-10-26 | 1983-12-21 | 4-Alkoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) quinolines and a process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235189B1 true CS235189B1 (en) | 1985-05-15 |
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ID=5428601
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS787183A CS235177B1 (en) | 1983-10-26 | 1983-10-26 | 4-Carboxyalkylamino-1,3-dimethyl-1H-pyrazolo (3,4-bquinoline and method for its preparation) |
| CS839744A CS235189B1 (en) | 1983-10-26 | 1983-12-21 | 4-Alkoxycarbonylmethylamino-1,3-dimethyl-1H-pyrazolo (3,4-b) quinolines and a process for their preparation |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS787183A CS235177B1 (en) | 1983-10-26 | 1983-10-26 | 4-Carboxyalkylamino-1,3-dimethyl-1H-pyrazolo (3,4-bquinoline and method for its preparation) |
Country Status (1)
| Country | Link |
|---|---|
| CS (2) | CS235177B1 (en) |
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1983
- 1983-10-26 CS CS787183A patent/CS235177B1/en unknown
- 1983-12-21 CS CS839744A patent/CS235189B1/en unknown
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| Publication number | Publication date |
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| CS235177B1 (en) | 1985-05-15 |
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