DE640859C - Process for the production of aqueous solutions of phenol ethers of morphine or its derivatives with salts of halogen-free barbituric acids - Google Patents
Process for the production of aqueous solutions of phenol ethers of morphine or its derivatives with salts of halogen-free barbituric acidsInfo
- Publication number
- DE640859C DE640859C DES112766D DES0112766D DE640859C DE 640859 C DE640859 C DE 640859C DE S112766 D DES112766 D DE S112766D DE S0112766 D DES0112766 D DE S0112766D DE 640859 C DE640859 C DE 640859C
- Authority
- DE
- Germany
- Prior art keywords
- salts
- morphine
- derivatives
- halogen
- aqueous solutions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
- A61K31/515—Barbituric acids; Derivatives thereof, e.g. sodium pentobarbital
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Es ist bekannt, schwer lösliche barbitursaure Salze durch doppelte Umsetzung der Natriumsalze von Barbitursäuren mit Hydrochloriden von Basen herzustellen. Weiter ist schön vorgeschlagen worden, Verbindungen aus Pyrazolonen und solchen G, C-substituierten Barbitursäuren, welche Halogen an doppelt gebundenem C-Atom enthalten, herzustellen. Durch die Einführung des starkIt is known that barbituric acid salts are poorly soluble by double implementation of the To prepare sodium salts of barbituric acids with hydrochlorides of bases. Next is Nicely proposed compounds made from pyrazolones and those G, C-substituted ones To produce barbituric acids, which contain halogen on a double bonded carbon atom. By introducing the stark
ίο negativen Chloratoms (überdies noch an doppelt gebundenem Kohlenstoff) erhöht sich bekanntlich die Stärke der Säure ganz wesentlich. Daß die Monoalkalisalze solcher stark sauren zweibasischen Halogenbarbitursäuren noch weiter mit basischen Pyrazolonen Salze zu bilden vermögen, ist daher durch den besonderen Bau der verwendeten Barbitursäuren bedingt.ίο negative chlorine atom (moreover still on doubly bonded carbon) increased As is well known, the strength of the acid is very important. That the monoalkali salts such strongly acidic dibasic halobarbituric acids even further with basic pyrazolones Ability to form salts is therefore due to the special structure of the barbituric acids used conditional.
Es ist also möglich, nach diesem Verfahren gegebenenfalls wäßrige Lösungen von halogenhaltigen ungesättigten Barbitursäuren und Pyrazolonen herzustellen. Bekannt sind ferner Verbindungen der Phenoläther des Morphins und seiner Derivate mit substituierten Barbitursäuren. " Diese" Verbindungen sind jedoch in Wasser schwer löslich. Ein Verfahren, nach dem genügend konzentrierte Lösungen von Phenoläthern des Morphins oder seiner Derivate und substituierten Barbitursäuren erhalten werden können, war bisher nicht bekanntgeworden.It is therefore possible, if appropriate, aqueous solutions of to produce halogen-containing unsaturated barbituric acids and pyrazolones. Are known also compounds of the phenol ethers of morphine and its derivatives with substituted Barbituric acids. However, "these" compounds are sparingly soluble in water. A process after which enough concentrated Solutions of phenolic ethers of morphine or its derivatives and substituted ones Barbituric acids can be obtained, had not previously become known.
Es -war daher eine überraschende Feststellung, daß die wäßrigen Lösungen der Alkalisalze halogenfreier Barbitursäuren, die an sich in Wasser schwer löslichen Phenoläther des Morphins bzw. seiner'Derivate zu lösen vermögen, wenn dabei die Alkalisalze der Barbitursäure im Überschuß verwendet werden. So können erstmalig barbitursaur,e Salze zusammen mit Morphinäthern gemeinsam in wäßriger Lösung Verwendung finden.It was, therefore, a surprising finding that the aqueous solutions of the alkali salts of halogen-free barbituric acids, the phenol ethers, which are poorly soluble in water of the morphine or its derivatives are able to dissolve when doing the alkali metal salts the barbituric acid can be used in excess. For the first time, barbitursaurs, e Find salts together with morphine ethers together in aqueous solution use.
2 Teile Natriumsalz der 5-Cyclohexenyl-5-methyl-N-methylbarbitursäure und 2,473 Teile Dihydrocodeinbase werden in wenig absolutem Alkohol gelöst und einige Zeit auf dem Wasserbade erwärmt. Nach Zusatz von absolutem Äther wird die Substanz von dem Lösungsmittel durch Abdampfen im Vakuum befreit und bildet so eine trockene, schaumigspröde, farblose Masse, o, 11 g dieser Substanz lösen sich bereits in 1,5 ecm io°/0iger wäßriger Lösung der Natriumsalze von Barbitursäuren.2 parts of the sodium salt of 5-cyclohexenyl-5-methyl-N-methylbarbituric acid and 2.473 parts of dihydrocodeine base are dissolved in a little absolute alcohol and heated on the water bath for some time. After addition of absolute ether, the substance is freed of the solvent by evaporation under vacuum, thus forming a dry, schaumigspröde, colorless mass, o, 11 g of this substance dissolve already in 1.5 cc io ° / 0 aqueous solution of the sodium salts of barbituric acids.
2,56 Teile Natriumsalz der 5-Cyclohexenyl-5-methyl-N-methylbarbitursäure und 3,17 Teile Codeinbase werden in wenig Alkohol gelöst und kurze Zeit erwärmt. Nach Zusatz von absolutem Äther im Vakuum wird2.56 parts of the sodium salt of 5-cyclohexenyl-5-methyl-N-methylbarbituric acid and 3.17 parts of codeine base are dissolved in a little alcohol and heated for a short time. To Addition of absolute ether in a vacuum is made
das Lösungsmittel abgedampft. Die Masse wird auf diese Weise ebenfalls als feste trockene Substanz erhalten. 0,1 g dieser Substanz lösen sich in 1,5 ecm io°/0iger wäßriger Lösung eines barbitursäuren Salzes.the solvent evaporated. The mass is also obtained in this way as a solid dry substance. 0.1 g of this substance will dissolve in 1.5 cc io ° / 0 aqueous solution of a barbituric salt.
2,07 Teile Natriumsalz der Diäthylbarbitursäureund 3,i9TeileDihydrocodein wercten in wäßrigem Alkohol gelöst, auf dem Wasserbade erwärmt. Die Substanz wird ebenfalls nach Zufügung von Äther durch Abdunsten des Lösungsmittels im Vakuum erhalten. ο, ι g dieser Substanz lösen sich in 1,1 ecm der wäßrigen Lösung eines barbitursäuren Salzes.2.07 parts of the sodium salt of diethylbarbituric acid and 3, 19 parts dihydrocodeine works dissolved in aqueous alcohol, warmed on the water bath. The substance will too obtained after the addition of ether by evaporation of the solvent in vacuo. ο, ι g of this substance dissolve in 1.1 ecm of the aqueous solution of a barbituric acid salt.
2,55 Teile Natriumsalz der 5-Phenyl-5-äthylbarbitursäure und 3,17 Teile Dihydrocodeinbase werden in verdünntem Alkohol gelöst und längere Zeit auf dem Wasserbade erwärmt. 0,11 g der auf die beschriebene Weise erhaltenen Substanz sind bereits in 1,8 ecm io°/0iger wäßriger Lösung des Natriumsalzes der 5-Phenyl-5-äthylbarbitursäure löslich.2.55 parts of the sodium salt of 5-phenyl-5-ethylbarbituric acid and 3.17 parts of dihydrocodeine base are dissolved in dilute alcohol and heated for a long time on the water bath. 0.11 g of the substance obtained in the manner described already in 1.8 cc io ° / 0 aqueous solution of the sodium salt of 5-phenyl-5-äthylbarbitursäure soluble.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES112766D DE640859C (en) | 1934-02-06 | 1934-02-06 | Process for the production of aqueous solutions of phenol ethers of morphine or its derivatives with salts of halogen-free barbituric acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES112766D DE640859C (en) | 1934-02-06 | 1934-02-06 | Process for the production of aqueous solutions of phenol ethers of morphine or its derivatives with salts of halogen-free barbituric acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE640859C true DE640859C (en) | 1937-01-14 |
Family
ID=7532012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES112766D Expired DE640859C (en) | 1934-02-06 | 1934-02-06 | Process for the production of aqueous solutions of phenol ethers of morphine or its derivatives with salts of halogen-free barbituric acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE640859C (en) |
-
1934
- 1934-02-06 DE DES112766D patent/DE640859C/en not_active Expired
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