DE1225659B - Process for the production of flavone-magnesium double salts - Google Patents
Process for the production of flavone-magnesium double saltsInfo
- Publication number
- DE1225659B DE1225659B DEV23264A DEV0023264A DE1225659B DE 1225659 B DE1225659 B DE 1225659B DE V23264 A DEV23264 A DE V23264A DE V0023264 A DEV0023264 A DE V0023264A DE 1225659 B DE1225659 B DE 1225659B
- Authority
- DE
- Germany
- Prior art keywords
- flavone
- magnesium
- double salts
- acid
- production
- 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
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- ZKHJUTPWJUBZIT-UHFFFAOYSA-N [Mg].O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 Chemical compound [Mg].O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 ZKHJUTPWJUBZIT-UHFFFAOYSA-N 0.000 title description 6
- YEHGDIWRWAAVCV-UHFFFAOYSA-N 2-(4-oxo-2-phenylchromen-7-yl)oxyacetic acid Chemical compound C=1C(OCC(=O)O)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 YEHGDIWRWAAVCV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 159000000003 magnesium salts Chemical class 0.000 claims description 3
- 229940091250 magnesium supplement Drugs 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
- OFJWFSNDPCAWDK-UHFFFAOYSA-N 2-phenylbutyric acid Chemical group CCC(C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- -1 α-Phenylbutyric acid magnesium Chemical compound 0.000 description 5
- MQGPSCMMNJKMHQ-UHFFFAOYSA-N 7-hydroxyflavone Chemical compound C=1C(O)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 MQGPSCMMNJKMHQ-UHFFFAOYSA-N 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000011147 magnesium chloride Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229960003512 nicotinic acid Drugs 0.000 description 3
- 235000001968 nicotinic acid Nutrition 0.000 description 3
- 239000011664 nicotinic acid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002212 flavone derivatives Chemical class 0.000 description 2
- 229960002337 magnesium chloride Drugs 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SUNCCQBNDWHMPR-UHFFFAOYSA-N 7-hydroxy-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=CC(O)=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 SUNCCQBNDWHMPR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000002484 anti-cholesterolemic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000000627 niacin group Chemical group 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Flavon-Magnesium-Doppelsalzen Die Erfindung betrifft ein Verfahren zur Herstellung von Flavon-Magnesium-Doppelsalzen der allgemeinen Formel: R-COO-Mg-O-R1 in der R einen Alkylaryl-, Pyridyl- oder Pyridylalkylrest und R1 einen Flavonyl-7-rest bedeuten.Process for the preparation of flavone-magnesium double salts The invention relates to a process for the preparation of flavone-magnesium double salts of the general Formula: R-COO-Mg-O-R1 in which R is an alkylaryl, pyridyl or pyridylalkyl radical and R1 is a flavonyl-7 radical.
Es wurde gefunden, daß die Flavon-Magnesium-Doppelsalze der oben angegebenen allgemeinen Formel gegen die experimentell hervorgerufene Arteriosklerose wirksam sind und ferner eine außerordentlich geringe Toxizität aufweisen. So werden 3 bis 4 g dieser Salze pro Kilogramm Maus oder Ratte anstandslos vertragen. It has been found that the flavone-magnesium double salts of the above given general formula against the experimentally caused arteriosclerosis are effective and also have extremely low toxicity. Be like that 3 to 4 g of these salts per kilogram of mouse or rat can be tolerated without hesitation.
Es sind zwar schon Magnesiumsalze der o;-Phenylbuttersäure beschrieben worden, die bei Arterie sklerose wirksam sind (vgl. die deutsche Patentschrift - 1 082 897), und auch die o;-Phenylbuttersäure ist wirksam, jedoch besitzen diese Verbindungen bei der therapeutischen Anwendung erhebliche Nachteile insofern, als sie einerseits in hohen Dosen verabreicht werden müssen, und andererseits treten unliebsame Nebenwirkungen ein. Magnesium salts of o; -phenylbutyric acid have already been described which are effective in artery sclerosis (cf. the German patent specification - 1 082 897), and o; -phenylbutyric acid is also effective, but have this Compounds in the therapeutic application significant disadvantages insofar as they have to be administered in high doses on the one hand, and occur on the other unpleasant side effects.
Demgegenüber besitzen die Verfahrensprodukte, die den Phenylbuttersäurerest
oder auch einen anderen Alkyl-phenyl-essigsäurerest oder den Nikotinsäurerest enthalten,
erhebliche Vorteile dadurch, daß sie das Blutcholesterin im Tierversuch rasch senken
und wenig toxisch sind. In Vergleichsversuchen wurden zwei Verfahrensprodukte gegenüber
bekannten Ver-
Die Flavon-Magnesium-Doppelsalze der oben angegebenen allgemeinen Formel werden erfindungsgemäß dadurch hergestellt, daß man eine Carbonsäure der allgemeinen Formel R - CO OH, in der R die obenbindungen geprüft. Die Versuche wurden in der Weise durchgeführt, daß bei Kaninchen durch Verfütterung von Eidottercholesterin eine Cholesterinämie erzeugt wurde. Der Blutcholesteringehalt der Versuchstiere wurde nach der von A. Z 1 a t t e i 5 und Mitarbeiter im Journal of Laboratory and Clinical Medicine, 41, S. 486 bis 498 (1964), beschriebenen Methode bestimmt und betrug 2,4 bis 2,5 mg %. Die zu prüfenden Substanzen wurden in einheitlichen Dosen von 100 mglkg täglich durch eine Schlundsonde verabreicht. Für jeden Ansatz und jede Substanz wurden je 20 Kaninchen herangezogen, wobei die Versuchsdauer 2 Monate betrug. In dieser Zeit wurde regelmäßig alle 8 Tage der Blutcholesteringehalt bestimmt. The flavone-magnesium double salts of the general ones given above Formula are prepared according to the invention by a carboxylic acid of the general formula R - CO OH, in which R the top bonds are checked. The trials were carried out in such a way that in rabbits by feeding them egg yolk cholesterol cholesterolemia was produced. The blood cholesterol content of the test animals was after the by A. Z 1 a t t e i 5 and coworkers in the Journal of Laboratory and Clinical Medicine, 41, pp. 486 to 498 (1964), and described was 2.4 to 2.5 mg%. The substances to be tested were given in uniform doses of 100 mglkg administered daily through a stomach tube. For every approach and 20 rabbits were used for each substance, the duration of the experiment being 2 months fraud. During this time, the blood cholesterol content was determined regularly every 8 days.
Die Tiere wurden dann nicht mehr als cholesterinanämisch angesehen, sobald der Blutcholesteringehalt unter 1,9 mg 0/o gesunken war.The animals were then no longer considered to be cholesterol anemic, as soon as the blood cholesterol level had fallen below 1.9 mg 0 / o.
Die erhaltenen Ergebnisse sind in der nachstehenden Tabelle zusammengestellt, aus~der ersichtlich ist, bei wievielen Tieren nach dem Versuche die Cholesterinämie beseitigt war. genannte Bedeutung besitzt und ein 7-Oxy-flavon oder Flavon-7-oxyessigsäure in an sich bekannter Weise mit einem Magniumsalz in äquimolekularen Mengen umsetzt. The results obtained are summarized in the table below, from which it can be seen in how many animals the cholesterolemia after the experiment was eliminated. has mentioned meaning and a 7-oxy-flavone or flavone-7-oxyacetic acid Reacts in a manner known per se with a magnesium salt in equimolecular amounts.
Als Carbonsäuren eignen sich z. B. oc-Phenylz-äthylessigsäure, a-Phenyl-ol-butylessigsäure, Phenylessigsäure und Pyridyl-3-essigsäure. Als Flavon- komponente kommen in Frage z. B. 7-Hydroxyflavon, 3-Methyl-7-hydroxyflavon, 2-(p-Methoxyphenyl)-7-hydroxyflavon, Flavon-7-oxyessigsäure. Suitable carboxylic acids are, for. B. oc-phenylz-ethyl acetic acid, a-phenyl-ol-butyl acetic acid, Phenylacetic acid and pyridyl-3-acetic acid. As a flavone component come into question z. B. 7-hydroxyflavone, 3-methyl-7-hydroxyflavone, 2- (p-methoxyphenyl) -7-hydroxyflavone, Flavone-7-oxyacetic acid.
Als Magnesiumsalze eignen sich vorzüglich Magnesiumhalogenide, wie Magnesiumdichlorid oder aber Magnesiumoxyd oder Maglresiumhydroxyd. Vorteilhafterweise werden die Alkalisalze der-entsprechenden Carbonsäuren und Flavonderivate in wäßriger Lösung mit der berechneten Menge an Magnesiumhalogeniden versetzt, wobei die entsprechenden Magn6sium-Doppelsalze entweder sofort ausfallen oder durch Eindampfen erhalten werden. Magnesium halides, such as Magnesium dichloride or else magnesium oxide or magnesium hydroxide. Advantageously the alkali salts of the corresponding carboxylic acids and flavone derivatives are in aqueous Solution mixed with the calculated amount of magnesium halides, the corresponding Magn6sium double salts either precipitate immediately or can be obtained by evaporation.
Beispiel 1 16,4 g α-Phenylbuttersäure werden in 60 ccm Wasser suspendiert, und die Suspension wird mit der äquimolekularen Menge an 2n-Natriumlauge versetzt, so daß alles in Lösung geht. Diese Lösung wird nun mit einer Lösung von 25,3 g 7-Hydroxyflavon und 4,5 g Natriumhydroxyd in 100 ccm Wasser unter Rühren vereinigt. Dann wird das Ganze auf dem Wasserbad unter Rührend auf 50 bis 60°C erwärmt und eine Lösung von 21 g Magnesiumchloridhexahydrat in 60 ccm Wasser hinzugegeben. Nachdem die Hälfte der Magnesiumchloridlösung zugeführt ist, beginnt sich ein kanariengelber körniger Niede-rschlag abzuscheiden. Example 1 16.4 g of α-phenylbutyric acid are dissolved in 60 cc of water suspended, and the suspension is with the equimolecular amount of 2N sodium hydroxide so that everything goes into solution. This solution is now combined with a solution of 25.3 g of 7-hydroxyflavone and 4.5 g of sodium hydroxide in 100 cc of water with stirring united. Then the whole thing is heated to 50 to 60 ° C on the water bath while stirring and a solution of 21 g of magnesium chloride hexahydrate in 60 cc of water was added. After half of the magnesium chloride solution has been supplied, a canary-yellow color begins granular precipitate to be deposited.
Nach vollständiger Zugabe- - der M:agnesiumchloridlösung wird das Gemisch noch 20 bis 30 Minuten auf dem Wasserbad gerührt, dann läßt man erkalten, saugt den Niederschlag ab und wäscht ihn mit eiskaltem Wasser aus. Die Kristalle werden anschließend im Trockenschrank bei 50 bis 60°C getrocknet. Man erhält das α-phenylbuttersaure Magnesium-7-hydroxyfiavon in einer Ausbeute von 95% der Theorie. Die Verbindung schmilzt ab 220°C unter Dunkelbraunfärbung und wird über 300°C zersetzt.After all of the magnesium chloride solution has been added, the Mixture stirred on the water bath for 20 to 30 minutes, then allowed to cool, sucks off the precipitate and washes it with ice-cold water. The crystals are then dried in a drying cabinet at 50 to 60 ° C. You get that α-phenylbutyric acid magnesium-7-hydroxyfiavon in a yield of 95% of the Theory. The compound melts from 220 ° C with a dark brown color and is over 300 ° C decomposed.
In analoger Weise wird bei Verwendung von Nikotinsäure an Stelle von a-Phenylbuttersäure das nikotinsaure Magnesium-7-hydroxyflavon in einer Ausbeute von 90 % der Theorie erhalten. Die - Verbindung 'schrnilzt über 300°C unter Zersetzung. In an analogous manner when using nicotinic acid in place of a-phenylbutyric acid, the nicotinic acid magnesium-7-hydroxyflavone in one yield obtained from 90% of theory. The compound melts above 300 ° C. with decomposition.
Beispiel 2 16,4 g α-Phenylbuttersäure, 4,03 g Magnesiumoxyd und 29,6 g Flavon-7-oxy-essigsäure werden innig miteinander verrieben und mit wenig Wasser angefeuchtet und das Ganze 24 Stunden sich selbst überlassen. Example 2 16.4 g of α-phenylbutyric acid, 4.03 g of magnesium oxide and 29.6 g of flavone-7-oxy-acetic acid are thoroughly rubbed together and with a little Moistened the water and leave the whole thing to itself for 24 hours.
Anschließend wird das Gemisch in einem Mörser gepulvert, mit 250 ccm 95%igem Äthanol 10 Minuten gerührt, abgesaugt und getrocknet. Man erhält das ol-Phenylduttersäure- Magnesium-Flavon-7- QxX-acetat in einer Ausbeute von 95% der Theorie. Die Verbindung schmilzt ab 250°C unter Dunkelfärbung und zersetzt sich bei 360°C.Then the mixture is powdered in a mortar, with 250 ccm 95% ethanol stirred for 10 minutes, filtered off with suction and dried. The ol-phenyldutyric acid is obtained Magnesium flavone 7-QxX acetate in a yield of 95% of theory. The connection melts from 250 ° C with a dark color and decomposes at 360 ° C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV23264A DE1225659B (en) | 1962-11-12 | 1962-11-12 | Process for the production of flavone-magnesium double salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV23264A DE1225659B (en) | 1962-11-12 | 1962-11-12 | Process for the production of flavone-magnesium double salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1225659B true DE1225659B (en) | 1966-09-29 |
Family
ID=7580418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEV23264A Pending DE1225659B (en) | 1962-11-12 | 1962-11-12 | Process for the production of flavone-magnesium double salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1225659B (en) |
-
1962
- 1962-11-12 DE DEV23264A patent/DE1225659B/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3878790T2 (en) | ORGANO-INORGANIC VANADYL COMPOUND, METHOD FOR PRODUCING SUCH A COMPOUND, PHARMACEUTICAL COMPOSITION CONTAINING THIS ORGANO-INORGANIC COMPOUND. | |
| DE1179556B (en) | PROCESS FOR THE PREPARATION OF FREE OR ACYLATED N- (4-DIETYLAMINOBUTYL) -SALICYCLIC ACID | |
| DE3000743A1 (en) | MEDICINAL PRODUCT ON THE BASIS OF A SALT OF ACETYLSALICYL ACID AND A BASIC AMINO ACID AND METHOD FOR THE PRODUCTION THEREOF | |
| EP0100516A2 (en) | 3-Beta-(3'-(carboxypropionyloxy))-ursa-9(11),12-dience-28-carboxylic acid and its salts, process for its preparation and medicines containing these compounds | |
| DE1445446A1 (en) | Benzylpenicillin derivative and method of production | |
| DE1225659B (en) | Process for the production of flavone-magnesium double salts | |
| DE2655130C3 (en) | A practically solvent-free crystal form of the cefacetrile sodium salt | |
| DE3840744C2 (en) | Activator for osteoblasts | |
| DE2327193C3 (en) | N- (Diethylaminoethyl) -2-methoxy-5methylsulfonylbenzamide, its salts, processes for the preparation of these compounds and medicaments containing these compounds | |
| DE951567C (en) | Process for the preparation of antibiotic apparatus antothenates | |
| DE955060C (en) | Process for the preparation of penicillin salts | |
| DE2241076B2 (en) | Tetracycline complex and its salts, process for its preparation and pharmaceutical compositions containing this complex | |
| DE3044736A1 (en) | ANTITUMOR AGENTS, METHOD FOR THE PRODUCTION THEREOF AND DOSAGE FORMS | |
| DE1793309C3 (en) | Chloramphenicol succinate salts of basic amino acids | |
| AT247519B (en) | Process for the preparation of new addition compounds of antibiotics | |
| AT207999B (en) | Process for the production of less toxic compounds of the basic Streptomyces antibiotics | |
| DE2932968C2 (en) | ||
| DE3431273A1 (en) | CRYSTALLINE SODIUM SALT OF THE D-6 - ((ALPHA) - (2-OXO-3-FURFURYL-IDEN-AMINO-IMIDAZOLIDIN-1-YL) -CARBONYLAMINO) -THIENYL-2-ACETAMIDO) -PENICILLANIC ACID, METHODS OF PROCESSING IN MEDICINAL PRODUCTS | |
| DE1695998C3 (en) | N to the power of 2, N to the power of 3-di-spiro-tripiperazinium salts and process for their preparation | |
| DE454701C (en) | Process for the preparation of derivatives of arsenostibiobenzene which are symmetrically disubstituted in the 3,4-position | |
| DE1089771B (en) | Process for the preparation of coccidiostatically active 5-nitrofurfurol-N-acyl-alkylhydrazones | |
| DEB0018759MA (en) | ||
| CH260991A (en) | Process for the manufacture of a solid pharmaceutical preparation with antihemorrhagic properties. | |
| DE1930005A1 (en) | Alpha naphthoxy isobutyric acid deriv prepn | |
| DE2406849A1 (en) | NICOTIC ACID TRANS-3,3,5-TRIMETHYLCYCLOHEX-1-YL-ESTER, THE METHOD FOR THEIR MANUFACTURING AND THE MEDICINAL PRODUCT CONTAINING THIS ESTER |