DE936818C - Process for the production of aqueous solutions of drugs that are poorly soluble in water - Google Patents
Process for the production of aqueous solutions of drugs that are poorly soluble in waterInfo
- Publication number
- DE936818C DE936818C DEF10331A DEF0010331A DE936818C DE 936818 C DE936818 C DE 936818C DE F10331 A DEF10331 A DE F10331A DE F0010331 A DEF0010331 A DE F0010331A DE 936818 C DE936818 C DE 936818C
- Authority
- DE
- Germany
- Prior art keywords
- water
- phenyl
- drugs
- pyrazolone
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 10
- 239000007864 aqueous solution Substances 0.000 title claims description 9
- 229940079593 drug Drugs 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 description 7
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 2
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 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 2
- 229960004544 cortisone Drugs 0.000 description 2
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 2
- 229940119740 deoxycorticosterone Drugs 0.000 description 2
- 239000000186 progesterone Substances 0.000 description 2
- 229960003387 progesterone Drugs 0.000 description 2
- LOMDVEFCNVDZMZ-UHFFFAOYSA-N valdetamide Chemical compound CCC(CC)(C(N)=O)CC=C LOMDVEFCNVDZMZ-UHFFFAOYSA-N 0.000 description 2
- 229950008240 valdetamide Drugs 0.000 description 2
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 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 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000003270 steroid hormone Substances 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material 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)
- Medicinal Preparation (AREA)
Description
Verfahren zur Herstellung wäßriger Lösungen von in Wasser schwer löslichen Arzneimitteln Es ist bereits bekannt, wäßrige Lösungen von in Wasser schwer löslichen Arzneimitteln, wie Chinin oder 1-Phenyl-2, 3-dimethyl-4-dimethylaminopyrazolon-(5), dadurch herzustellen, daß man I-Phenyl-2, 3-dimethyl-pyrazolon-(5) als Lösungsvermittler verwendet.Process for the preparation of aqueous solutions of sparingly soluble in water Medicinal products It is already known that aqueous solutions of sparingly soluble in water Drugs, such as quinine or 1-phenyl-2, 3-dimethyl-4-dimethylaminopyrazolone- (5), by using I-phenyl-2, 3-dimethyl-pyrazolone- (5) as a solubilizer used.
Es wurde nun gefunden, daß das I, 2, 4-Trimethyl-3-phenyl-pyrazolon-(5) ein vorzüglicher Lösungsvermittler für in Wasser schwer lösliche Arzneimittel ist und das I-Phenyl-2, 3Zimethyl-pyrazolon-(5) beträchtlich übertrifft. So gelingt es unter Verwendung von I, 2, 4-Trimethyl-3-phenyl-pyrazolon-(5) z. B. konzentriertere Lösungen von I-Phenyl-2, 3-dimethyl-4-dimethylamino-pyrazolon- (5) in Wasser herzustellen, als es bei Verwendung von I-Phenyl-2, 3-dimethylpyrazolon-(5) möglich ist. It has now been found that the I, 2, 4-trimethyl-3-phenyl-pyrazolone- (5) is an excellent solubilizer for drugs that are sparingly soluble in water and the I-phenyl-2,3zimethyl-pyrazolone- (5) considerably exceeds. This is how it works it using I, 2, 4-trimethyl-3-phenyl-pyrazolone- (5) z. B. more focused To produce solutions of I-phenyl-2, 3-dimethyl-4-dimethylamino-pyrazolon- (5) in water, than is possible when using I-phenyl-2, 3-dimethylpyrazolon- (5).
Auch für andere, in Wasser schwer lösliche Arzneimittel, wie z. B. Diäthylallylacetamid und Steroidhormone, hat sich das 1, 2, 4-Tiimethyl-3-phenylpyrazolon-(5) als ein guter Lösungsvermittler erwiesen. Also for other drugs that are sparingly soluble in water, such as B. Diethylallylacetamide and steroid hormones, has the 1, 2, 4-thimethyl-3-phenylpyrazolone- (5) Proven to be a good solubilizer.
Die einzelnen Arzneimittel können für sich allein oder in Kombination miteinander in Lösung gebracht werden. The individual drugs can be used alone or in combination be brought into solution with each other.
Beispiel I 15 Gewichtsteile I, 2, 4-Trimethyl-3 -phenyl-pyrazolon-(5), hergestellt nach dem Verfahren der deutschen Patentschrift 934 948, und I5 Gewichtsteile I-Phenyl-2, 3-dimethyl-4-dimethylamino-pyrazolon- (5) werden mit Wasser zu 100 Volumteilen gelöst. Man erhält eine beständige Lösung, die auch nach längerem Stehen im Eisschrank keine Kristallisation zeigt. Example I 15 parts by weight of I, 2, 4-trimethyl-3-phenyl-pyrazolone- (5), produced according to the process of German patent specification 934 948, and 15 parts by weight I-phenyl-2, 3-dimethyl-4-dimethylamino-pyrazolone- (5) are dissolved in 100 parts by volume with water. The result is a stable solution which, even after standing in the refrigerator for a long time, does not Shows crystallization.
Beispiel 2 20 Gewichtsteile I, 2, 4-Trimethyl-3-phenyl-pyrazolon-(5) und 5 Gewichtsteile Diäthylallylacetamid werden unter schwachem Erwärmen in Wasser zu. Example 2 20 parts by weight of I, 2, 4-trimethyl-3-phenyl-pyrazolone- (5) and 5 parts by weight of diethylallylacetamide are placed in water with gentle heating to.
40 Volumteilen gelöst. Es wird eine stabile Lösung erhalten, welche bei Abkühlung und weiterer Verdünnung mit Wasser keine Kristalle abscheidet.40 parts by volume solved. A stable solution is obtained, which no crystals separate on cooling and further dilution with water.
Beispiel 3 I5 mg Progesteron werden in 3 ccm einer 50°;Oigen wäßrigen Lösung von I, 2, 4-Trimethyl-3-phenyl-pyrazolon-(5) heiß gelöst. Beim Abkühlen kristallisiert das Progesteron nicht aus. Example 3 15 mg of progesterone are dissolved in 3 cc of a 50 ° aqueous Solution of I, 2, 4-trimethyl-3-phenyl-pyrazolone- (5) dissolved hot. Crystallizes on cooling the progesterone doesn't run out.
Beispiel 4 15 mg Desoxycorticosteron werden, wie im Beispiel 3 beschrieben, in 3 ccm einer 50°/Oigen wäßrigen Lösung von 1, 2, 4-Trimethyl-3-phenyl-pyrazolon-(5) gelöst. Man erhält eine stabile Lösung, aus der auch nach längerem Stehen kein Desoxycorticosteron auskristallisiert. Example 4 15 mg of deoxycorticosterone are, as described in Example 3, in 3 cc of a 50% aqueous solution of 1, 2, 4-trimethyl-3-phenyl-pyrazolone- (5) solved. A stable solution is obtained from which no deoxycorticosterone even after prolonged standing crystallized out.
Beispiel 5 20 mg Cortison werden, wie im Beispiel 3 beschrieben, in 5 ccm einer 50°lOigen wäßrigen Lösung von I, 2, 4-Trimethyl-3-phenyl-pyrazolon- (5) gelöst. Selbst beim Aufbewahren im Eisschrank bleibt die Lösung klar, und es scheiden sich keine Kristalle ab. Example 5 20 mg of cortisone are, as described in Example 3, in 5 cc of a 50 ° lOigen aqueous solution of I, 2, 4-trimethyl-3-phenyl-pyrazolone- (5) solved. Even when stored in the freezer, the solution stays clear, and so does it no crystals separate.
Beispiel 6 20 mg Cortison und 600 mg I-Phenyl-2, 3-dimethyl-4-dimethyl-aminopyrazolon-(5) werden unter Erwärmen in etwa 4,5 ccm einer 500'0eigen wäßrigen Lösung von I, 2, 4-Trimethyl-3-phenyl-pyrazolon- (5) gelöst. Example 6 20 mg of cortisone and 600 mg of I-phenyl-2, 3-dimethyl-4-dimethyl-aminopyrazolone- (5) are heated in about 4.5 ccm of a 500% aqueous solution of I, 2, 4-Trimethyl-3-phenyl-pyrazolone- (5) dissolved.
Nach dem Erkalten wird mit 5001,iger wäßriger Lösung des Lösungsvermittlers auf 5 ccm aufgefüllt. Man erhält eine stabile Lösung, die auch beim Aufbewahren im Eisschrank keine Kristalle abscheidet.After cooling, it is mixed with 500 l aqueous solution of the solubilizer filled up to 5 cc. A stable solution is obtained, even when it is stored no crystals separate in the refrigerator.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF10331A DE936818C (en) | 1952-11-08 | 1952-11-08 | Process for the production of aqueous solutions of drugs that are poorly soluble in water |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF10331A DE936818C (en) | 1952-11-08 | 1952-11-08 | Process for the production of aqueous solutions of drugs that are poorly soluble in water |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE936818C true DE936818C (en) | 1955-12-22 |
Family
ID=7086435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF10331A Expired DE936818C (en) | 1952-11-08 | 1952-11-08 | Process for the production of aqueous solutions of drugs that are poorly soluble in water |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE936818C (en) |
-
1952
- 1952-11-08 DE DEF10331A patent/DE936818C/en not_active Expired
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