DE863118C - Process for the preparation of oil solutions of strychnine oxide - Google Patents
Process for the preparation of oil solutions of strychnine oxideInfo
- Publication number
- DE863118C DE863118C DEK3177D DEK0003177D DE863118C DE 863118 C DE863118 C DE 863118C DE K3177 D DEK3177 D DE K3177D DE K0003177 D DEK0003177 D DE K0003177D DE 863118 C DE863118 C DE 863118C
- Authority
- DE
- Germany
- Prior art keywords
- strychnine
- oxide
- preparation
- oil solutions
- oil
- 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
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 title claims description 28
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 title claims description 14
- 241001279009 Strychnos toxifera Species 0.000 title claims description 14
- 229960005453 strychnine Drugs 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000010685 fatty oil Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000010497 wheat germ oil Substances 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 fatty acid salt Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Preparation (AREA)
- Fats And Perfumes (AREA)
Description
Verfahren zur Herstellung von Ollösungen von Strydininoxyd Strychninoxyd entfaltet eine sehr günstige Kreislaufwirkung, wobei ein wesentlicher Vorteil darin liegt, daß das Strychninoxyd etwa zehnmal weniger toxisch ist als Strychnin. Da nun bekanntlich bei solchen analeptisch wirkenden Präparaten eine möglichst lange Wirkungsdauer erwünscht ist, schien es von Vorteil, ölige Lösungen von Strychninoxyd herzustellen. Dies scheiterte zunächst daran, daß Strychninoxyd in Olen sehr schwer löslich ist.Process for the preparation of oil solutions of strydinine oxide Strychnine oxide unfolds a very favorable circulatory effect, with a major advantage in it is that strychnine oxide is about ten times less toxic than strychnine. There now, as is well known, for such analeptically acting preparations as long as possible If the duration of action is desired, it seemed advantageous to use oily solutions of strychnine oxide to manufacture. This initially failed because strychnine oxide was very difficult in oils is soluble.
Es wurde nun gefunden, daß man haltbare, ölige Lösungen von Strychninoxyd dadurch erhalten kann, daß man Salze des Strychninoxyds mit höheren Fettsäuren anwendet, wobei es sich als zweckmäßig erwies, die Fettsäure im Überschuß anzuwenden. Es ist anzunehmen, daß dadurch das Dissoziationsgleichgewicht zugunsten des undissoziierten, fettsauren Salzes zurückgedrängt wird, das in fetten Olen leichter löslich ist als die freie Base. Dies war um so überraschender, als im allgemeinen die Salze von Basen in Ölen noch schwerer löslich sind als die freien Basen selbst. It has now been found that durable, oily solutions of strychnine oxide can be obtained can be obtained by using salts of strychnine oxide with higher fatty acids, it was found to be expedient to use the fatty acid in excess. It is to assume that thereby the dissociation equilibrium in favor of the undissociated, fatty acid salt is pushed back, which is more soluble in fatty oils than the free base. This was all the more surprising as in general the salts of Bases are even more difficult to dissolve in oils than the free bases themselves.
Beispiele I. 2 g Strychninoxyd werden mit 6 g Ölsäure und 2 ccm reinem Alkohol versetzt und das Ge- menge unter Erwärmen verschmolzen. Die klare Schmelze wird in 200 ccm Sesamöl aufgelöst und der Alkohol im Vakuum unter Erwärmen entfernt. Examples I. 2 g of strychnine oxide are mixed with 6 g of oleic acid and 2 cc of pure Alcohol and the amount melted under heating. The clear melt is dissolved in 200 cc of sesame oil and the alcohol under vacuum Heating away.
2. o,sg Strychninoxyd werden mit g Stearinsäure und 1 ccm reinem Alkohol versetzt und das Gemenge unter Erwärmen verschmolzen. Die klare Schmelze wird in IOO ccm Olivenöl aufgelöst und der Alkohol im Vakuum unter Erwärmen entfernt. 2. O, so-called strychnine oxide are mixed with g stearic acid and 1 cc of pure Alcohol was added and the mixture melted while heating. The clear melt is dissolved in 100 cc of olive oil and the alcohol is removed in vacuo with heating.
3. 2 g Strychninoxyd werden mit 6 g Linolsäure und 2 ccm reinem Alkohol versetzt und das Gemenge unter Erwärmen verschmolzen. Die klare Schmelze wird in 100 ccm Weizenkeimöl aufgelöst und der Alkohol im Vakuum unter Erwärmen entfernt. 3. 2 g of strychnine oxide are mixed with 6 g of linoleic acid and 2 cc of pure alcohol added and the mixture melted while heating. The clear melt is in Dissolve 100 cc of wheat germ oil and remove the alcohol in vacuo while heating.
4. 4 g Strychninoxyd werden unter Erwärmen in 20 g Ölsäure gelöst und mit IOO ccm Weizenkeimöl verdünnt. 4. 4 g of strychnine oxide are dissolved in 20 g of oleic acid while warming and diluted with 100 cc wheat germ oil.
Claims (2)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK3177D DE863118C (en) | 1942-09-19 | 1942-09-19 | Process for the preparation of oil solutions of strychnine oxide |
| DK212743A DK63620C (en) | 1942-09-19 | 1943-08-06 | Procedure for Preparing Oil Solutions of Strychnine Oxide. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK3177D DE863118C (en) | 1942-09-19 | 1942-09-19 | Process for the preparation of oil solutions of strychnine oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE863118C true DE863118C (en) | 1953-01-15 |
Family
ID=7209757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK3177D Expired DE863118C (en) | 1942-09-19 | 1942-09-19 | Process for the preparation of oil solutions of strychnine oxide |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE863118C (en) |
| DK (1) | DK63620C (en) |
-
1942
- 1942-09-19 DE DEK3177D patent/DE863118C/en not_active Expired
-
1943
- 1943-08-06 DK DK212743A patent/DK63620C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DK63620C (en) | 1945-06-18 |
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