AT87692B - Process for the preparation of therapeutically valuable compounds of the alkaloids of the quinine group. - Google Patents
Process for the preparation of therapeutically valuable compounds of the alkaloids of the quinine group.Info
- Publication number
- AT87692B AT87692B AT87692DA AT87692B AT 87692 B AT87692 B AT 87692B AT 87692D A AT87692D A AT 87692DA AT 87692 B AT87692 B AT 87692B
- Authority
- AT
- Austria
- Prior art keywords
- alkaloids
- preparation
- quinine
- therapeutically valuable
- valuable compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 229930013930 alkaloid Natural products 0.000 title claims description 7
- 125000003410 quininyl group Chemical group 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- FDQGNLOWMMVRQL-UHFFFAOYSA-N Allobarbital Chemical compound C=CCC1(CC=C)C(=O)NC(=O)NC1=O FDQGNLOWMMVRQL-UHFFFAOYSA-N 0.000 claims description 6
- 229960000880 allobarbital Drugs 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 6
- 235000001258 Cinchona calisaya Nutrition 0.000 description 5
- 229960000948 quinine Drugs 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- NSBRKSWSLRQPJW-ZEBIKNNBSA-N Quinine ethylcarbonate (TN) Chemical compound C1=C(OC)C=C2C([C@H]([C@H]3N4CCC([C@H](C4)C=C)C3)OC(=O)OCC)=CC=NC2=C1 NSBRKSWSLRQPJW-ZEBIKNNBSA-N 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- LJOQGZACKSYWCH-WZBLMQSHSA-N hydroquinine Chemical compound C1=C(OC)C=C2C([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 LJOQGZACKSYWCH-WZBLMQSHSA-N 0.000 description 1
- 229960004251 hydroquinine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von therapeutisch wertvollen Verbindungen der Alkaloide der
Chiningruppe.
Es wurde gefunden, dass man zu therapeutisch wertvollen Verbindungen der Alkaloide der Chiningruppe gelangen kann, wenn man die Alkaloide der Chiningruppe oder deren Derivate, wie z. B. Chinin, Cinchonin, Euchinin, Apochinin, Äthylcuprein, Hydrochinin, Äthylhydrocuprein usw. einerseits und Diallylbarbitursäure oder Allylalkylbarbitursäuren andrerseits entweder in Form der freien Verbindungen oder in Form ihrer Salze in molekularen Mengen gegebenenfalls in Gegenwart geeigneter Lösungs- bzw. Verdünnungsmittel aufeinander einwirken lässt. Die neuen Verbindungen sind ausgezeichnete Wehenmittel von ausserordentlich zuverlässiger und starker Wirkung, die gleichzeitig eine erwünschte, sedative und beruhigende Wirksamkeit ausüben.
Beispiel I : 65 g wasserfreie Chininbase und 4I36 g Diallylbarbitursäure werden mit 200 g wasserfreiem Methylalkohol eine halbe Stunde am Rückflusskühler gekocht. Nach längerem Stehen scheidet sich die entstandene Chinindiallylbarbitursäure in nadelförmigen Kristallen ab, die bei 1280 schmelzen und in Wasser ziemlich schwer, in Alkohol, Methylalkohol und Essigäther leicht, und in Petroläther unlöslich sind. Die neue Verbindung enthält 60'9I% Chinin und 39. 09% Diallylbarbitursäure ; dieselbe gibt mit den üblichen Alkaloidreagentien charakteristische Reaktionen.
Beispiel 2 : 65 g wasserfreie Chininbase und 4I#6 g Diallylbarbitursäure werden während einiger Zeit zusammengeschmolzen. Die zähe Masse wird aus Essigäther umkristallisiert, wobei dieselbe Verbindung erhalten wird wie nach Beispiel I.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of therapeutically valuable compounds of the alkaloids of
Chin group.
It has been found that therapeutically valuable compounds of the alkaloids of the quinine group can be obtained if the alkaloids of the quinine group or their derivatives, such as. B. quinine, cinchonine, euchinine, apochinine, ethylcuprein, hydroquinine, ethylhydrocuprein, etc. on the one hand and diallylbarbituric acid or allylalkylbarbituric acids on the other hand, either in the form of the free compounds or in the form of their salts in molecular amounts, if necessary in the presence of suitable solvents or diluents. The new compounds are excellent contraceptive pills with an extremely reliable and strong effect, which at the same time exert a desired sedative and calming effect.
Example I: 65 g of anhydrous quinine base and 4136 g of diallyl barbituric acid are refluxed with 200 g of anhydrous methyl alcohol for half an hour. After standing for a long time, the quinine diallyl barbituric acid formed separates out in needle-shaped crystals, which melt at 1280 and are rather heavy in water, easy in alcohol, methyl alcohol and acetic ether, and insoluble in petroleum ether. The new compound contains 60.91% quinine and 39.09% diallylbarbituric acid; it gives characteristic reactions with the usual alkaloid reagents.
Example 2: 65 g of anhydrous quinine base and 4I # 6 g of diallyl barbituric acid are melted together over a period of time. The viscous mass is recrystallized from vinegar ether, the same compound being obtained as in Example I.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT87692T | 1917-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT87692B true AT87692B (en) | 1922-03-27 |
Family
ID=3608377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT87692D AT87692B (en) | 1917-01-17 | 1917-01-17 | Process for the preparation of therapeutically valuable compounds of the alkaloids of the quinine group. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT87692B (en) |
-
1917
- 1917-01-17 AT AT87692D patent/AT87692B/en active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH174811A (en) | Process for the preparation of tropic acid-2,2-dimethyl-3-diethylaminopropanol ester. | |
| DE2000030C3 (en) | 3-alkoxy- and 3-phenoxy-2- (diphenylhydroxy) methyl-propylamines and medicaments containing them | |
| DE2144077C3 (en) | New Hydroxyäthylaminoalkylpiperazines and processes for their preparation | |
| DE578213C (en) | Process for the production of water-soluble antimony salts | |
| AT158301B (en) | Process for the production of vitamin B1. | |
| DE329772C (en) | Process for the preparation of compounds of the alkaloids of the quinine group | |
| DE539178C (en) | Process for the preparation of hydrogenated amides of nicotinic acid | |
| AT227707B (en) | Process for the production of new quinazolinone derivatives | |
| AT78703B (en) | Process for the preparation of therapeutically valuable compounds of the alkaloids of the morphine group. | |
| AT113002B (en) | Process for the preparation of monoboric acid choline. | |
| DE647056C (en) | Process for the preparation of compounds from hexamethylenetetramine rhodanide | |
| AT125233B (en) | Process for the preparation of salt-like compounds from higher homologues of polyoxybenzenes. | |
| AT146635B (en) | Process for the preparation of compounds of dihydrocodeine, which are readily soluble in water, with alkylated barbituric acids. | |
| DE2816627A1 (en) | Antihypertensive isoindolinyl-amino-imidazoline - prepd. by reacting 2-amino-isoindoline with 2-alkylthio-2-imidazoline | |
| AT123399B (en) | Process for the preparation of compounds from C.C-disubstituted barbituric acids and 1-phenyl-2,3-dimethyl-4-dimethylamino-5-pyrazolone. | |
| CH235953A (en) | Process for the preparation of a new therapeutically effective amidine. | |
| DE587428C (en) | Process for the preparation of 1, 5, 5- and 1, 3, 5, 5-substituted barbituric acids | |
| DE835927C (en) | Process for the production of stable aqueous solutions of theophylline | |
| DE432420C (en) | Process for the preparation of N-methylsulphurous acid salts of secondary amines | |
| AT144906B (en) | Process for the preparation of compounds from C.C-disubstituted barbituric acids and pyrazolone derivatives. | |
| DE531009C (en) | Process for the preparation of compounds of the higher homologues of polyoxybenzenes | |
| AT144033B (en) | Process for the preparation of a compound of theophylline with diethylolamine. | |
| DE633981C (en) | Process for the preparation of well-defined crystalline nitrates of phenylmercuric hydroxide | |
| DE710225C (en) | Process for the preparation of compounds of dioxydialkylstilbenes | |
| DE1813275C3 (en) | Molecular compounds from 1-phenyl-2,3-dimethyl-4- (aminoethanesulfonylamino) -pyrazolon-5 and barbituric acids |