DE1068271B - Process for the preparation of therapeutically active salts of 5-halo-4,6-dioxyisophthalic acids - Google Patents
Process for the preparation of therapeutically active salts of 5-halo-4,6-dioxyisophthalic acidsInfo
- Publication number
- DE1068271B DE1068271B DENDAT1068271D DE1068271DA DE1068271B DE 1068271 B DE1068271 B DE 1068271B DE NDAT1068271 D DENDAT1068271 D DE NDAT1068271D DE 1068271D A DE1068271D A DE 1068271DA DE 1068271 B DE1068271 B DE 1068271B
- Authority
- DE
- Germany
- Prior art keywords
- dioxyisophthalic
- acids
- halo
- salts
- preparation
- 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
- 239000002253 acid Substances 0.000 title description 17
- 150000003839 salts Chemical class 0.000 title description 13
- 150000007513 acids Chemical class 0.000 title description 9
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000004129 fatty acid metabolism Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von therapeutisch wirksamen Salzen der 5-Halogen-4,6-dioxyisophthalsäuren Die 5-Chlor- und die 5-Brom-4,6-dioxyisophthalsäure sind bekannt. Zu ihrer Herstellung dient z.B. das Verfahren von F. Hemmelmayr und Th. Meyer (Monatshefte für Chemie, 46 [1925], S. 143). Eine pharmakologische oder andere medizinische bzw. biochemische Untersuchung dieser Verbindungen ist noch nicht bekanntgeworden. Process for the preparation of therapeutically effective salts of the 5-halo-4,6-dioxyisophthalic acids 5-chloro and 5-bromo-4,6-dioxyisophthalic acids are known. The process of F. Hemmelmayr and Th. Meyer (monthly magazine for chemistry, 46 [1925], p. 143). A pharmacological or other medical or biochemical investigation of these compounds is still ongoing not known.
Es wurde nun überraschenderweise gefunden, daß man therapeutisch wirksame Salze der Halogen-4,6-dioxyisophthalsäuren, welche den Fettsäurestoffwechsel stark hemmen, dadurch erhält, daß man eine 5-Halogen-4,6-dioxyisophthalsäure, deren Halogen ein Atomgewicht größer als 19 aufweist, oder deren Salze, gegebenenfalls in Gegenwart eines Lösungsmittels, mit Calcium- oder Magnesiumhydroxyd oder einem anorganischen Calcium-oder Magnesiumsalz umsetzt. Die erhaltenen Salze weisen auch eine gute analgetische Wirkung auf und sind sehr gut verträglich. Am wirksamsten erweisen sich hierbei die 5-Jod-4,6-dioxyisophthalsäuren und deren Salze, die nach dem Verfahren der deutschen Patentschrift 1 047 790 hergestellt werden. It has now surprisingly been found that you can therapeutically effective salts of the halogen-4,6-dioxyisophthalic acids, which the fatty acid metabolism strongly inhibit, obtained by a 5-halo-4,6-dioxyisophthalic acid, whose Halogen has an atomic weight greater than 19, or its salts, optionally in the presence of a solvent, with calcium or magnesium hydroxide or a converts inorganic calcium or magnesium salt. The salts obtained also have have a good analgesic effect and are very well tolerated. Most effective prove to be the 5-iodo-4,6-dioxyisophthalic acids and their salts, which after the process of German patent specification 1,047,790.
Die 5-Halogen-4,6-dioxyisophthalsäuren selbst besitzen zwar auch schon eine günstige pharmakologische Wirkung bei geringer Toxizität, jedoch sind sie als relativ starke organische Säuren schlecht magenverträglich. Die Alkalisalze dieser Säure besitzen zwar diese unangenehme Wirkung nicht, haben jedoch den Nachteil, daß bei ihrer längeren Anwendung dem Körper beträchtliche Mengen Natrium oder Kalium zugeführt würden, was bei den zu behandelnden chronischen Stoffwechselerkrankungen unvorteilhaft wäre. The 5-halo-4,6-dioxyisophthalic acids themselves also have already have a beneficial pharmacological effect with low toxicity, however as relatively strong organic acids, they are poorly tolerated by the stomach. The alkali salts this acid do not have this unpleasant effect, but have the disadvantage that with their prolonged use the body receives considerable amounts of sodium or potassium would be fed, what in the chronic metabolic diseases to be treated would be disadvantageous.
Alle diese Nachteile können vermieden werden, wenn man die Calcium- oder Magnesiumsalze der 5-Halogen-4,6-dioxyisophthalsäuren verwendet. Diese zeigen bei sehr guter Wirkung eine ausgezeichnete Verträglichkeit. All of these disadvantages can be avoided by taking the calcium or magnesium salts of 5-halo-4,6-dioxyisophthalic acids are used. These show excellent tolerability with very good effect.
Einige dieser Salze haben darüber hinaus den Vorteil einer verzögerten Ausscheidung. Dies bedeutet, daß ein therapeutisch wirksamer Blutspiegel über eine längere Zeit eingehalten wird.Some of these salts also have the benefit of being delayed Excretion. This means that a therapeutically effective blood level is above one is adhered to for a long time.
Die Herstellung der Salze erfolgt entweder durch inniges Vermischen der Säuren mit Calcium- oder Magnesiumhydroxyd, gegebenenfalls in Gegenwart eines Lösungs- oder Verdünnungsmittels oder durch doppelte Umsetzung eines Salzes der 5-Halogen-4,6-dioxyisophthalsäuren mit Calcium- oder Magnesiumsalzen. Als Lösungsmittel wählt man vorteilhaft ein solches, aus dem das Salz auch umkristallisiert werden kann. The salts are produced either by intimate mixing the acids with calcium or magnesium hydroxide, optionally in the presence of one Solvent or diluent or by double reaction of a salt of 5-halo-4,6-dioxyisophthalic acids with calcium or magnesium salts. As a solvent it is advantageous to choose one from which the salt can also be recrystallized can.
Man verwendet bevorzugt 2 Mol einer monobasischen oder 1 Mol einer dibasischen Verbindung auf 1 Mol der 5-Halogen-4,6-dioxyisophthalsäure. Man kann aber auch Salze aus 1 Mol Base und 1 Mol 5-Halogen-4,6-dioxyisophthalsäure herstellen; diese haben jedoch den Nachteil, in wäßriger Lösung zu disproportionieren. It is preferred to use 2 moles of a monobasic or 1 mole of a monobasic dibasic compound to 1 mole of 5-halo-4,6-dioxyisophthalic acid. One can but also produce salts from 1 mole of base and 1 mole of 5-halo-4,6-dioxyisophthalic acid; however, these have the disadvantage that they are disproportionate in aqueous solution.
Beispiel 32 g 5-Jod-4,6-dioxyisophthalsäure werden in 80 ccm 10°/Õiger Natronlauge gelöst und mit einer Lösung von 25 g Calciumchlorid in 50 ccm Wasser versetzt. Nach dem Abkühlen wird das ausgefallene Calciumsalz der 5-Jod4,6-dioxyisophthalsäure abgesaugt und mit kaltem Wasser nachgewaschen. Example 32 g of 5-iodo-4,6-dioxyisophthalic acid are dissolved in 80 ccm at 10 ° / Õiger Sodium hydroxide solution and a solution of 25 g calcium chloride in 50 ccm water offset. After cooling, the precipitated calcium salt is 5-iodo-4,6-dioxyisophthalic acid Aspirated and washed with cold water.
PATENTANSPRUCH Verfahren zur Herstellung von therapeutisch wirksamen Salzen der 5-Halogen-4,6-dioxyisophthalsäuren, dadurch gekennzeichnet, daß man eine 5-Halogen-4,6-dioxyisophthalsäure, deren Halogen ein Atomgewicht größer als 19 aufweist, oder deren Salze, gegebenenfalls in Gegenwart eines Lösungsmittels, mit Calcium- oder Magnesiumhydroxyd oder einem anorganischen Calcium- oder Magnesiumsalz umsetzt. PATENT CLAIM Process for the production of therapeutically effective Salts of 5-halo-4,6-dioxyisophthalic acids, characterized in that one 5-halo-4,6-dioxyisophthalic acid, the halogen of which has an atomic weight greater than 19, or their salts, optionally in the presence of a solvent, with calcium or magnesium hydroxide or an inorganic calcium or magnesium salt.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1068271B true DE1068271B (en) | 1959-11-05 |
Family
ID=593634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1068271D Pending DE1068271B (en) | Process for the preparation of therapeutically active salts of 5-halo-4,6-dioxyisophthalic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1068271B (en) |
-
0
- DE DENDAT1068271D patent/DE1068271B/en active Pending
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