CS218187B1 - Method of preparation of the salts /3,4,12-trimetoxy-10,11-methylendioxy-7,8 dihydro-5h-izoindolo/1,2-b//3/benzazepin-5-on-7-yyl-dimethylamonium - Google Patents
Method of preparation of the salts /3,4,12-trimetoxy-10,11-methylendioxy-7,8 dihydro-5h-izoindolo/1,2-b//3/benzazepin-5-on-7-yyl-dimethylamonium Download PDFInfo
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- CS218187B1 CS218187B1 CS467181A CS467181A CS218187B1 CS 218187 B1 CS218187 B1 CS 218187B1 CS 467181 A CS467181 A CS 467181A CS 467181 A CS467181 A CS 467181A CS 218187 B1 CS218187 B1 CS 218187B1
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- Prior art keywords
- dihydro
- carbon number
- acid
- benzazepin
- trimethoxy
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- 150000003839 salts Chemical class 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- -1 organic acid ester Chemical class 0.000 claims description 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- RTFMKOOQVKWDHF-UHFFFAOYSA-N 7-(dimethylamino)-3,4,13-trimethoxy-7,8-dihydro-5h-[1,3]dioxolo[4,5-h]isoindolo[1,2-b][3]benzazepin-5-one Chemical compound C1C(N(C)C)N2C(=O)C3=C(OC)C(OC)=CC=C3C2=CC2=C1C=C(OCO1)C1=C2OC RTFMKOOQVKWDHF-UHFFFAOYSA-N 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 2
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WWVGXWRJWMUFSY-UHFFFAOYSA-N 1-benzazepin-5-one Chemical compound O=C1C=CC=NC2=CC=CC=C12 WWVGXWRJWMUFSY-UHFFFAOYSA-N 0.000 description 1
- HDZZVAMISRMYHH-UHFFFAOYSA-N 9beta-Ribofuranosyl-7-deazaadenin Natural products C1=CC=2C(N)=NC=NC=2N1C1OC(CO)C(O)C1O HDZZVAMISRMYHH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- HDZZVAMISRMYHH-KCGFPETGSA-N tubercidin Chemical compound C1=CC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O HDZZVAMISRMYHH-KCGFPETGSA-N 0.000 description 1
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- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález sa týká sposobu přípravy solí 3,4,12-.trimetoxy-7,8-dihydro-5H-izoindolo (1,2-b) (3)benzazepi'n-5-on-7-yldimetylamónia obecného vzorca IThe present invention relates to a process for the preparation of 3,4,12-trimethoxy-7,8-dihydro-5H-isoindolo (1,2-b) (3) benzazepin-5-one-7-yldimethylammonium salts of the formula I
v ktorom x~ značí anión halogenovodíkovej kyseliny, alifatickej karboxylovej kyseliny s počtom uhlíkov 2 až 3 alebo arénsulfonovej kyseliny s počtom uhlíkov 6 až 8.wherein x - denotes the anion of a hydrohalic acid, an aliphatic carboxylic acid having a carbon number of 2 to 3 or an arenesulfonic acid having a carbon number of 6 to 8.
Sposob přípravy látok vzoroa I podl’a vynálezu je taký, že 3,4,12-trimetoxy-7-dimetylamino-10,1 l-metyléndioxy-7,8-dihydro-5H-izoindolo (1,2,-b) (3) benzazepin-5-ón sa podrobí reakcii s ekvivalentným množstvom kyseliny halogenovodíkovej, alifatickej karboxylovej kyseliny s počtom uhlíkov 2 až 3 alebo arénsulfonovej kyseliny s počtom uhlíkov 6 až 8 rozpustenej v alkohole s počtom uhlíkov 1 až 3 a, roztok sa zahustí ku kryštalizácii, alebo k roztoku sa přidá alifatický keton s počtom uhlíkov 3 až 5, například aceton alebo ester organickej kyseliny s alkanolom s počtom uhlíkov 3 až 5, například octan etylnatý, v pomeře 1:10 až 1:50 a roztok sa nechá kryštalizovať.The process for the preparation of the compounds of formula I according to the invention is such that 3,4,12-trimethoxy-7-dimethylamino-10,11-methylenedioxy-7,8-dihydro-5H-isoindolo (1,2, -b) ( 3) reacting benzazepin-5-one with an equivalent amount of hydrohalic acid, an aliphatic carboxylic acid having a carbon number of 2 to 3 or an arenesulfonic acid having a carbon number of 6 to 8 dissolved in an alcohol having a carbon number of 1-3; or an aliphatic ketone having a carbon number of 3-5, such as acetone or an organic acid ester of an alkanol having a carbon number of 3-5, such as ethyl acetate, is added at a ratio of 1:10 to 1:50 and the solution is allowed to crystallize.
Látky uvedeného vzorca I, ktoré doteraz neboli popísané, sú cennými farmakodynamicky účinnými látkami. Například látka vzorca I, kde X značí chloridový anión zvyšuje účinok tubercidínu na proliferáciu buniek lymfoleukémie P-388 o 20 %.The compounds of the formula I which have not been described so far are valuable pharmacodynamically active substances. For example, a compound of formula I wherein X is a chloride anion increases the effect of tubercidine on the proliferation of P-388 lympholeukemia cells by 20%.
Podrobnosti postupu vyplývajú z príkladov prevedenia.The details of the procedure follow from the exemplary embodiments.
Příklad 1Example 1
3,4,12-trimetoxy-7-dimetylamino-10,ll-metyléndoxy-7,8-idihydro-5H-izoindolo (1,2-b) (3) benzazepin-5-ón (7,90 g) sa zmieša s 25 cm3 metylalkoholu a 1,8 cm3 kyseliny chlorovodíkové j (o koncentrácii 11,3 mol. I1), k roztoku sa přidá aceton (300 cm3) a roztok sa nechá krystalizovat pri teplote -j- 4 °C. Vylúčené kryštály sa odfiltrujú a vysušia. Týmto spósobom sa získalo 5,2 g 3,4,12-trimetoxy-l 0,11 -metyléndioxy-7,8-dihydro-5H-izoindolo (1,2-b) (3)benzazepin-5-on-7-yldimetylamóniumchloridu s teplotou topenia 200 °C za rozkladu. Pre C23H25N2OcC1 o molekulovej hmotnosti 460,9 je vypočítané: C 59',94 % H 5,47 %, N 6,08 % a nájdené: C 59,82 %, H 5,53 %, N 6,02 %.3,4,12-trimethoxy-7-dimethylamino-10,11-methylenedoxy-7,8-idihydro-5H-isoindolo (1,2-b) (3) benzazepin-5-one (7.90 g) was mixed with 25 cm @ 3 of methanol and 1.8 cm @ 3 of hydrochloric acid (11.3 mol. m @ 1 ), acetone (300 cm @ 3 ) is added to the solution, and the solution is allowed to crystallize at -4 DEG. The precipitated crystals are filtered off and dried. In this way 5.2 g of 3,4,12-trimethoxy-11,11-methylenedioxy-7,8-dihydro-5H-isoindolo (1,2-b) (3) benzazepin-5-one-7- Yldimethylammonium chloride, m.p. 200 DEG C. with decomposition. For C 2 H 25 N 2 O c Cl having a molecular weight of 460.9 it is calculated: C 59 ', 94% H 5.47%, N 6.08% and found: C 59.82%, H 5.53%, N 6.02%.
Příklad 2Example 2
3,0 g 3,4,12-trimetoxy-7-dimetylamino-10, 11 -metyléňdioxy-7,8-dihydro-5H-izoi'ndolo (1, 2-b) (3) benzazepin-5-ónu sa rozpustilo v zmesi 15 cm3 etanolu a 1,0 cm3 kyseliny octovéj. Roztok sa vákuovo zahustil a zvyšok sa kryštalizoval z octanu etylnatého. Získalo sa 2,8 g 3,4,12-trimetoxy-l 0,11 -metyléndioxy-7,8-dihydro-5H-izoindolo (1,2-ťb) (3) benzazepin5-ón-7-yldimetylamónium acetátu s teplotou topenia 180 °C za rozkladu pre C25H28N2O8 o molekulovej hmotnosti 484,5 a vypočítané: C 61,97%, H 5,83%, N 5,78% a nájdené: C 61,82 %, H 5,71 %, N 5,74 %.3.0 g of 3,4,12-trimethoxy-7-dimethylamino-10,11-methylenedioxy-7,8-dihydro-5H-isoindolo (1,2-b) (3) benzazepin-5-one was dissolved in a mixture of 15 cm 3 of ethanol and 1.0 cm 3 of acetic acid. The solution was concentrated in vacuo and the residue was crystallized from ethyl acetate. 2.8 g of 3,4,12-trimethoxy-11,11-methylenedioxy-7,8-dihydro-5H-isoindolo (1,2-b) (3) benzazepin-5-one-7-yldimethylammonium acetate were obtained at a temperature. mp 180 ° C dec. for C 25 H 28 N 2 O 8 484.5 and calculated: C 61.97%, H 5.83%, N 5.78% and found: C 61.82%, H 5.71%, N 5.74%.
Příklad 3Example 3
3,2 g 3,4,12-trimetoxy-7-dimetylamino-l 0, 11 -metyléndioxy-7,8-dihydro~5H-izoindolo (1, 2-b) (3) benzazepin-5-ónu sa zmiešalo s 1,44 g kyselitny p-toluénsulfoinovej v 30 cm3 metanolu, roztok sa zahustil na objem 10 cm3, k zvyšku sa přidalo 100 cm3 acetonu a roztok sa nechal krystalizovat. Získalo sa 2,6 g 3,4, 12-trimetoxy-l 0, 11 -metyléndioxy-7,8-dihy dro-5H-izoindolo (1,2-b) (3) benziazepin-5-on-7-yldimetylamónium -p-toluénsulfonátu s teplotou topenia 215 °C za rozkladu, pre C30H32 N2O9S s molekulovou hmotnosťou 596,66 bolo vypočítané: C 60,39 %, H 5,41 %, N 4,69 % a nájdené: C 60,27 %, H 5,52 %, N 4,71 %.3,2 g 3,4,12-trimethoxy-7-dimethylamino-10,11-methylenedioxy-7,8-dihydro-5H-isoindolo (1,2-b) (3) benzazepin-5-one was mixed with 1.44 g of p-toluenesulfoic acid in 30 cm 3 of methanol, the solution was concentrated to a volume of 10 cm 3 , 100 cm 3 of acetone were added to the residue and the solution was allowed to crystallize. 2.6 g of 3,4,12-trimethoxy-10,11-methylenedioxy-7,8-dihydro-5H-isoindolo (1,2-b) (3) benziazepin-5-on-7-yldimethylammonium were obtained. p-toluenesulphonate, m.p. 215 ° dec. for C30 H32 N2 O 9 with a molecular weight of 596.66 was calculated: C 60.39%, H 5.41%, N 4.69% found, and %: C 60.27%, H 5.52%, N 4.71%.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS467181A CS218187B1 (en) | 1981-06-22 | 1981-06-22 | Method of preparation of the salts /3,4,12-trimetoxy-10,11-methylendioxy-7,8 dihydro-5h-izoindolo/1,2-b//3/benzazepin-5-on-7-yyl-dimethylamonium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS467181A CS218187B1 (en) | 1981-06-22 | 1981-06-22 | Method of preparation of the salts /3,4,12-trimetoxy-10,11-methylendioxy-7,8 dihydro-5h-izoindolo/1,2-b//3/benzazepin-5-on-7-yyl-dimethylamonium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS218187B1 true CS218187B1 (en) | 1983-02-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS467181A CS218187B1 (en) | 1981-06-22 | 1981-06-22 | Method of preparation of the salts /3,4,12-trimetoxy-10,11-methylendioxy-7,8 dihydro-5h-izoindolo/1,2-b//3/benzazepin-5-on-7-yyl-dimethylamonium |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS218187B1 (en) |
-
1981
- 1981-06-22 CS CS467181A patent/CS218187B1/en unknown
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