DE1062390B - Process for increasing the solubility of 2-methyl-2-n-propyl-1,3-propane-diol dicarbamate - Google Patents
Process for increasing the solubility of 2-methyl-2-n-propyl-1,3-propane-diol dicarbamateInfo
- Publication number
- DE1062390B DE1062390B DEU4382A DEU0004382A DE1062390B DE 1062390 B DE1062390 B DE 1062390B DE U4382 A DEU4382 A DE U4382A DE U0004382 A DEU0004382 A DE U0004382A DE 1062390 B DE1062390 B DE 1062390B
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- propyl
- solubility
- increasing
- dicarbamate
- 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.)
- Pending
Links
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 5
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 4
- 229960004025 sodium salicylate Drugs 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- JVZZUPJFERSVRN-UHFFFAOYSA-N 2-methyl-2-propylpropane-1,3-diol Chemical compound CCCC(C)(CO)CO JVZZUPJFERSVRN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Erhöhung der Löslichkeit von 2-Methyl-2-n-propyl-1,3-propandioldicarbamat In neuerer Zeit wurde der Dicarbaminsäureester des 2-Methyl-2-n-propyl-1 ,3-propandiols wegen seiner dämpfenden und beruhigenden Wirkung als wertvolles Arzneimittel in die Therapie eingeführt. Seine Anwendung als Arzneimittel erfolgt allgemein nur auf oralem Wege, vornehmlich in Form von Tabletten. Von dem genannten Wirkstoff müssen, um die erwünschte Heilwirkung zu erzielen, größere Mengen eingesetzt werden, so daß die Handelspräparate, deren wirksamer Bestandteil das 2-Methyl-2-n-propyl-1 ,3-propandioldicarbamat ist, 400 mg dieses Stoffes pro Tablette enthalten. Die Löslichkeit des 2-Methyl-2-n-propyl-1 ,3-propandioldicarbamats in Wasser beträgt nur 30/,, eine Konzentration, die in vielen Fällen bei parenteraler Anwendung oder für pharmakologische Untersuchungen durchaus unzureichend ist.Process for increasing the solubility of 2-methyl-2-n-propyl-1,3-propanediol dicarbamate More recently, the dicarbamic acid ester of 2-methyl-2-n-propyl-1,3-propanediol because of its depressant and calming effect as a valuable medicine in introduced the therapy. Its use as a medicine is only general by the oral route, primarily in the form of tablets. From the named active ingredient larger amounts must be used in order to achieve the desired healing effect, so that the commercial preparations whose active ingredient is 2-methyl-2-n-propyl-1 , 3-propanediol dicarbamate contains 400 mg of this substance per tablet. The solubility of 2-methyl-2-n-propyl-1, 3-propanediol dicarbamate in water is only 30 / ,, one Concentration that in many cases for parenteral use or for pharmacological use Investigation is quite inadequate.
Es wurde nun gefunden, daß man die Löslichkeit des 2-Methyl-2-n-propyl-1 3-propandioldicarbamats in Wasser um 100 und mehr Prozent steigern kann bei Anwendung von Salicylsäure in Form ihrer wasserlöslichen Salze als Lösungsvermittler. Es ist bei Anwendung von Natriumsalicylat möglich, stabile wäßrige Lösungen von 2-Methyl-2-n-propyl-1,3-propandioldicarbamat zu erhalten, welche 6 bis 120!o und mehr dieses Wirkstoffes enthalten, so daß eine Lösungsverbesserung auf 4000/, der normalen Löslichkeit in Wasser leicht durchführbar ist. Die Lösungen sind stabil und sterilisierbar. It has now been found that the solubility of 2-methyl-2-n-propyl-1 3-propanediol dicarbamate in water can increase by 100 and more percent when used of salicylic acid in the form of its water-soluble salts as a solubilizer. It is possible when using sodium salicylate, stable aqueous solutions of 2-methyl-2-n-propyl-1,3-propanediol dicarbamate to obtain, which contain 6 to 120! o and more of this active ingredient, so that one Solution improvement to 4000 /, the normal solubility in water can easily be carried out is. The solutions are stable and sterilizable.
Die Herstellung der Lösungen kann erfolgen, indem man entweder das 2-Methyl-2-n-propyl-1,3-propandioldicarbamat in eine vorbereitete Lösung des Salicylats gegebenenfalls in der Wärme und unter Rühren einträgt. The preparation of the solutions can be done by either the 2-methyl-2-n-propyl-1,3-propanediol dicarbamate in a prepared solution of the salicylate optionally enters in the heat and with stirring.
Man kann auch das 2-Methyl-2-n-propyl-1 3-propandiol dicarbamat und die berechnete Menge Salicylat gemeinsam in die erforderliche Menge Wasser gegebenenfalls unter Rühren und Erwärmen eintragen.You can also dicarbamate and 2-methyl-2-n-propyl-1 3-propanediol the calculated amount of salicylate together in the required amount of water if necessary Enter while stirring and warming.
Beispiel 1 12 g Natriumsalicylat werden in 100 ccm Wasser gelöst. In die klare Lösung werden unter Rühren und Erwärmen 6 g 2-Methyl-2-n-propyi4 ,3-propandioldicarbamat eingetragen. Es entsteht eine klare Lösung, welche nach dem Abkühlen erforderlichenfalls auf genau 100 ccm eingestellt wird. Die Lösung ist stabil, läßt sich in Ampullen abfüllen und sterilisieren. Die Erhöhung der Löslichkeit gegenüber normal beträgt 100 O!o. Example 1 12 g of sodium salicylate are dissolved in 100 cc of water. 6 g of 2-methyl-2-n-propyi4, 3-propanediol dicarbamate are added to the clear solution with stirring and heating registered. A clear solution results, which, if necessary, after cooling is set to exactly 100 cc. The solution is stable and can be put into ampoules Fill and sterilize. The increase in solubility compared to normal is 100 O! O.
Beispiel 2 12 g Natriumsalicylat und 6 g 2-Methyl-2-n-propyl-1,3-propandioldicarbamat werden gemeinsam in etwa 80 bis 90 ccm destilliertem Wasser unter Rühren und Erwärmen gelöst. Die klare Lösung wird nach dem Abkühlen auf 100 ccm eingestellt. Sie ist stabil und läßt sich ampullieren und sterilisieren. Example 2 12 g of sodium salicylate and 6 g of 2-methyl-2-n-propyl-1,3-propanediol dicarbamate are mixed together in about 80 to 90 ccm of distilled water while stirring and heating solved. The clear solution is adjusted to 100 ccm after cooling. she is stable and can be ampouled and sterilized.
Beispiel 3 15 g Natriumsalicylat und 12 g 2-Methyl-2-n-propyl-1, 3-pi opandioldicarbamat werden gemeinsam in etwa 90 ccm destilliertem Wasser unter Rühren und Erwärmen in Lösung gebracht und die klare Lösung nach dem Abkühlen auf 100 ccm eingestellt. Die Lösung wird erforderlichenfalls filtriert und kann in Ampullen abgezogen und sterilisiert werden. Die Konzentration an 2-Methyl-2-n-propyl-1,3-propandioldicarbamat beträgt 400°/0 der normalen Löslichkeit ohne Lösungsvermittler. Example 3 15 g of sodium salicylate and 12 g of 2-methyl-2-n-propyl-1, 3-pi opandioldicarbamate are taken together in about 90 ccm of distilled water Stirring and heating brought into solution and the clear solution after cooling on 100 cc set. The solution is filtered if necessary and can be put into ampoules peeled off and sterilized. The concentration of 2-methyl-2-n-propyl-1,3-propanediol dicarbamate is 400 ° / 0 of the normal solubility without a solubilizer.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU4382A DE1062390B (en) | 1957-02-20 | 1957-02-20 | Process for increasing the solubility of 2-methyl-2-n-propyl-1,3-propane-diol dicarbamate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU4382A DE1062390B (en) | 1957-02-20 | 1957-02-20 | Process for increasing the solubility of 2-methyl-2-n-propyl-1,3-propane-diol dicarbamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1062390B true DE1062390B (en) | 1959-07-30 |
Family
ID=7565524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU4382A Pending DE1062390B (en) | 1957-02-20 | 1957-02-20 | Process for increasing the solubility of 2-methyl-2-n-propyl-1,3-propane-diol dicarbamate |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1062390B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0208519A3 (en) * | 1985-07-09 | 1987-08-12 | Takeda Chemical Industries, Ltd. | Solubilized composition of hardly-soluble pharmaceutical product |
-
1957
- 1957-02-20 DE DEU4382A patent/DE1062390B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0208519A3 (en) * | 1985-07-09 | 1987-08-12 | Takeda Chemical Industries, Ltd. | Solubilized composition of hardly-soluble pharmaceutical product |
| US4866044A (en) * | 1985-07-09 | 1989-09-12 | Takeda Chemical Industries, Ltd. | Solubilized composition of poorly-soluble pharmaceutical product |
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