DE156900C - - Google Patents
Info
- Publication number
- DE156900C DE156900C DE1903156900D DE156900DA DE156900C DE 156900 C DE156900 C DE 156900C DE 1903156900 D DE1903156900 D DE 1903156900D DE 156900D A DE156900D A DE 156900DA DE 156900 C DE156900 C DE 156900C
- Authority
- DE
- Germany
- Prior art keywords
- aminotheophylline
- chlorotheophylline
- ammonia
- heated
- colorless
- 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 - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der zusammenfassenden Arbeit von E.Fischer, »Synthesen in der Puringruppe« (Ber. d. d. ehem. Ges. 32, 435) findet sich zwar die Bemerkung: »Ammoniak wirkt bei höherer Temperatur auf die Chlorpurine allgemein unter Bildung von Aminoderivaten«. Es sind aber bis jetzt von den 8-Aminoxanthinen (8-Amino-2,6-dioxypurinen) nur die 8-Aminocaffeine aus dem entsprechenden Chlorderivat, dem 8-Chlorcafrein, durch Umsetzung mit Ammoniak bezw. mit Aminen dargestellt worden. In the summarizing work by E. Fischer, "Syntheses in the Puring Group" (Ber. D. The former Ges. 32, 435) there is the remark: "Ammonia works at higher levels Temperature on the chloropurines in general, with the formation of amino derivatives «. It but so far only the 8-aminocaffeine are of the 8-aminoxanthines (8-amino-2,6-dioxypurines) from the corresponding chlorine derivative, 8-Chlororcafrein, by reaction with Ammonia resp. with amines.
Es wurde nun festgestellt, daß sich
8-ChlortheophyllinIt has now been found that
8-chlorotheophylline
CHN-COCHN-CO
CO C-NHsCO C-NHs
CH3NCH 3 N
C - NC - N
C ClC Cl
das Halogen ebenfalls, wenn auch^ etwas schwieriger als beim Chlorcaffein, durch die Aminogruppe ersetzen läßt.the halogen as well, albeit somewhat more difficult than with chlorocaffeine, can be replaced by the amino group.
Hierbei unterscheidet sich der chemische Vorgang insofern von dem bei der oben erwähnten Gewinnung der Aminocaffeine, als im vorliegenden Falle zunächst Salzbildung eintritt und dann erst der Austausch des Halogens erfolgt.The chemical process here differs from that mentioned above Obtaining the aminocaffeine, as in the present case initially salt formation occurs and only then the replacement of the halogen takes place.
Die nach dem vorliegenden Verfahren erhaltenen, bisher unbekannten 8-Aminotheophylline sind dem chemischen Charakter nach sowohl Säuren wie Basen.The previously unknown 8-aminotheophyllins obtained by the present process are both acids and bases in chemical character.
Durch die Fähigkeit, mit Alkalien Salze zu bilden, unterscheiden sie sich vorteilhaft von dem 8-Aminocaffein, während sie vor dem Stammkörper, dem Theophyllin, den Vorzug der größeren Basizität haben.Their ability to form salts with alkalis is what distinguishes them advantageously of the 8-aminocaffeine, while they are in front of the parent body, theophylline, the Have the advantage of greater basicity.
Infolge dieser Doppelnatur können die neu erhaltenen Xanthinderivate im Organismus leichter zur Wirkung gelangen. Tatsächlich hat auch die physiologische Prüfung der Aminotheophylline deren starke Wirksamkeit ergeben.As a result of this dual nature, the newly obtained xanthine derivatives can be found in the organism reach their effect more easily. Indeed, the physiological examination of the Aminotheophylline give their strong effectiveness.
Es ist also durch das vorliegende Verfahren eine neue Körpergruppe gefunden worden, deren Glieder als Arzneimittel von hervorragender Bedeutung sind.A new body group has thus been found through the present procedure, the limbs of which are of outstanding importance as medicinal products.
In der Ausführung des Verfahrens kann man bei Anwendung von Ammoniak, primären und sekundären Aminen der fetten und aromatischen Reihe zu den 8-Aminotheophyllinen von der allgemeinen Formel C7 H1 O2 Ni - N R1 R2 gelangen, wobei R1 und R2 sowohl Wasserstoff als auch ein Alkyl- oder Arylradikal bedeuten kann.In carrying out the process, when ammonia, primary and secondary amines of the fatty and aromatic series are used, the 8-aminotheophyllins of the general formula C 7 H 1 O 2 N i - NR 1 R 2 can be obtained, where R 1 and R 2 can represent both hydrogen and an alkyl or aryl radical.
Die erhaltenen Produkte zeichnen sich im allgemeinen durch gute Kristallisationsfähigkeit aus.The products obtained are generally characterized by good crystallizability the end.
I. Aminotheophyllin. C1H1N^O2-NH2. I. Aminotheophylline. C 1 H 1 N ^ O 2 -NH 2 .
I Teil Chlortheophyllin wird mit 10 VoL-Teilen alkoholischem Ammoniak in geschlossenem Gefäß mehrere Stunden auf 150 bis 1550 erhitzt. Nach dem Erkalten ist das Aminotheophyllin nahezu rein als feinkristallinischer, farbloser Niederschlag ausgeschieden. ·Chlorotheophylline part I is heated with 10 parts by volume of alcoholic ammonia in a closed vessel for several hours at 150 to 155 0th After cooling, the aminotheophylline is excreted in an almost pure form as a finely crystalline, colorless precipitate. ·
Zur Trennung von noch etwas unverändertem Chlorkörper wird der filtrierte Niederschlag mit heißer Salzsäure ausgelaugt.The filtered chlorine is used to separate the still somewhat unchanged chlorine Precipitate leached with hot hydrochloric acid.
Das Filtrat scheidet beim Erkalten das salzsaure Aminotheophyllin in Nadeln aus. Durch Übergießen mit Wasser wird das Salz sofort in Salzsäure und reines Aminotheophyllin zerlegt.On cooling, the filtrate excretes the hydrochloric aminotheophylline in needles. By Pouring water over the salt immediately turns into hydrochloric acid and pure aminotheophylline disassembled.
Die· Verbindung ist auch in kochendem Wasser sehr schwer löslich. In verdünnten Alkalien löst sie sich leicht; durch Zusatz einer stärkeren Lauge zu dieser Lösung werden die betreffenden Alkalisalze als feine farblose Nädelchen abgeschieden. Beim längeren Erhitzen mit Kali- oder Natronlauge tritt allmählich Zersetzung ein.The compound is very sparingly soluble even in boiling water. In diluted It dissolves easily in alkalis; by adding a stronger lye to this solution the alkali salts in question are deposited as fine, colorless needles. For longer When heated with potassium hydroxide or caustic soda, decomposition occurs gradually.
Beim raschen Erhitzen bräunt sich das Aminotheophyllin über 3100 und schmilzt beim weiteren Erhitzen allmählich zu einer dunklen Flüssigkeit.When rapid heating, the aminotheophylline tans more than 310 0 and melts on further heating gradually to a dark liquid.
II. Phenylaminotheophyjlin.
C7H7O2N4-NHC6H,. II. Phenylaminotheophylline.
C 7 H 7 O 2 N 4 -NHC 6 H ,.
ι Teil Chlortheophyllin wird mit -io Teilen Anilin während 7 bis 8 Stunden auf 175 bis i8o° erhitzt. Beim Erkalten erstarrt das Ganze zu einem festen Kristallbrei, der abgesaugt wird. Durch Waschen mit verdünnter Essigsäure wird das noch anhaftende Anilin entfernt.ι Part of chlorotheophylline is shared with -io Aniline heated to 175 to 180 ° for 7 to 8 hours. When it cools down, it freezes Whole into a solid crystal slurry that is sucked off. By washing with diluted Acetic acid removes the aniline that is still adhering.
Das Anilinotheophyllin zeigt gegen Alkalien und Säuren ein ähnliches Verhalten wie dieThe anilinotheophylline shows a similar behavior to alkalis and acids as the
Aminoverbindung. In heißem Wasser ist 30 es sehr schwer löslich, leichter in kochendem Alkohol, woraus es in farblosen Nadeln kristallisiert.Amino compound. It is very sparingly soluble in hot water, more easily in boiling water Alcohol, from which it crystallizes in colorless needles.
Es schmilzt gegen 3200 zu einer farblosen Flüssigkeit.It melts at around 320 ° to a colorless liquid.
III. Dimethylaminotheophyllin.
C7H7O2N4-N(CHJ2. III. Dimethylaminotheophylline.
C 7 H 7 O 2 N 4 -N (CHI 2 .
ι Teil Chlortheophyllin wird mit 1,2 Teilen einer 33 prozentigen Dimethylaminlösung und 5 Teilen Alkohol in geschlossenem Gefäß während 5 Stunden auf 1500 erhitzt. Nach dem Erkalten ist der ganze Inhalt zu einem dicken Brei von langen Kristallnadeln erstarrt.ι part chlorotheophylline is heated with 1.2 parts of a 33 percent dimethyl amine and 5 parts of alcohol in a closed vessel for 5 hours at 150 0th After cooling, the entire contents have solidified into a thick paste of long crystal needles.
Das Dimethylaminotheophyllin gleicht in seinen Eigenschaften den beiden zuvor beschriebenen Verbindungen. In heißem Wasser und heißem Alkohol ist es ziemlich schwer löslich; es schmilzt beim raschen Erhitzen gegen 3300 zu einer farblosen Flüssigkeit.Dimethylaminotheophyllin has the same properties as the two compounds described above. It is rather sparingly soluble in hot water and hot alcohol; it melts upon rapid heating to 330 0 to a colorless liquid.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT21550D AT21550B (en) | 1903-09-01 | 1904-12-09 | Process for the preparation of 8-aminotheophylline and its alkyl or aryl derivatives. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE164425T |
Publications (1)
Publication Number | Publication Date |
---|---|
DE156900C true DE156900C (en) |
Family
ID=33035644
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT164425D Active DE164425C (en) | |||
DE1903156900D Expired - Lifetime DE156900C (en) | 1903-09-01 | 1903-09-01 | |
DE1903156901D Expired - Lifetime DE156901C (en) | 1903-09-01 | 1903-09-01 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT164425D Active DE164425C (en) |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1903156901D Expired - Lifetime DE156901C (en) | 1903-09-01 | 1903-09-01 |
Country Status (1)
Country | Link |
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DE (3) | DE156900C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1024968B (en) * | 1956-03-31 | 1958-02-27 | Asal Fabrik Biolog Und Pharmaz | Process for the preparation of 7-ketonyl-8-amino-theophyllines |
DE1085530B (en) * | 1958-08-15 | 1960-07-21 | Josef Klosa Dipl Chem Dr | Process for the preparation of caffeine derivatives with basic substitution in the 8-position |
US3443501A (en) * | 1966-03-09 | 1969-05-13 | Hans Wolfgang F Domnick | Photographic camera and film magazine therefor |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1005517B (en) * | 1955-12-30 | 1957-04-04 | Cassella Farbwerke Mainkur Ag | Process for the production of new xanthine compounds containing mercury |
-
0
- DE DENDAT164425D patent/DE164425C/de active Active
-
1903
- 1903-09-01 DE DE1903156900D patent/DE156900C/de not_active Expired - Lifetime
- 1903-09-01 DE DE1903156901D patent/DE156901C/de not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1024968B (en) * | 1956-03-31 | 1958-02-27 | Asal Fabrik Biolog Und Pharmaz | Process for the preparation of 7-ketonyl-8-amino-theophyllines |
DE1085530B (en) * | 1958-08-15 | 1960-07-21 | Josef Klosa Dipl Chem Dr | Process for the preparation of caffeine derivatives with basic substitution in the 8-position |
US3443501A (en) * | 1966-03-09 | 1969-05-13 | Hans Wolfgang F Domnick | Photographic camera and film magazine therefor |
Also Published As
Publication number | Publication date |
---|---|
DE156901C (en) | |
DE164425C (en) |
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