DE860217C - Process for the preparation of 1-hexyl-3, 7-dimethylxanthine - Google Patents
Process for the preparation of 1-hexyl-3, 7-dimethylxanthineInfo
- Publication number
- DE860217C DE860217C DEC3334A DEC0003334A DE860217C DE 860217 C DE860217 C DE 860217C DE C3334 A DEC3334 A DE C3334A DE C0003334 A DEC0003334 A DE C0003334A DE 860217 C DE860217 C DE 860217C
- Authority
- DE
- Germany
- Prior art keywords
- hexyl
- dimethylxanthine
- preparation
- theobromine
- effect
- 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 1-Hexyl-3,7-dimethylxanthin Es ist bekannt, in Xanthinderivate durch Umsetzung mit Alkylhalogeniden Alkylreste einzuführen.Process for the preparation of 1-hexyl-3,7-dimethylxanthine It is known to introduce alkyl radicals into xanthine derivatives by reaction with alkyl halides.
Hierbei sind jedoch bisher nur Alkylreste mit i bis 5 Kohlenstoffatomen zur Anwendung gekommen (vgl. z. B. Chem. Zentralblatt 1897,I 28q.; 1928, 11663, 1 1666; 1930, 11 2529; 1940, 11 2024; Liebigs Annalen. der Chemie 414, 69; Berichte der deutschen chemischen Gesellschaft 5o, 292).Up to now, however, only alkyl radicals with 1 to 5 carbon atoms have been used (see e.g. Chem. Zentralblatt 1897, I 28q .; 1928, 11663, 1 1666; 1930, 11 2529; 1940, 11 2024; Liebigs Annalen. der Chemie 414, 69; Reports of the German Chemical Society 50, 292).
Es wurde nun gefunden, daß nach diesen bekannten Verfahren der Alkylierung auch der Hexylrest in Xanthinderivate eingeführt werden kann, wobei eine neue, bisher nicht bekannte Verbindung mit besonderen therapeutischen Wirkungen erhalten wird. Diese Verbindung, die als solche nicht vorbeschrieben ist, besitzt nicht, wie das in dieser Verbindungsklasse als Standardpräparat geltende Coffein, das ein i, 3, 7-Trimethylxanthin ist, eine zentralerregende Wirkung, sondern eine ausgesprochen -sedative Wirkung bei gleichzeitiger Verstärkung der Gefäßspasmolyse.It has now been found that according to these known processes of alkylation the hexyl radical can also be introduced into xanthine derivatives, a new one so far unknown compound with particular therapeutic effects is obtained. This connection, which as such is not described above, does not have, like that Caffeine considered the standard preparation in this class of compounds, which is an i, 3, 7-Trimethylxanthine is a central excitatory effect, but one that is pronounced -sedative effect with simultaneous intensification of vascular spasmolysis.
Es ist bekannt, daß i-Alkyltheobrominderivate, die in der Alkylgruppe 4 oder 5 Kohlenstoffatome enthalten, keine zentralerregende Wirkung mehr aufweisen [Journal of Pharmacology and Experimental Therapeutics, 86 (1946), 113].It is known that i-alkyl theobromine derivatives included in the alkyl group Contain 4 or 5 carbon atoms, no longer have a central stimulating effect [Journal of Pharmacology and Experimental Therapeutics, 86, 113 (1946)].
Es war jedoch bisher nicht bekannt, daß derartige Verbindungen, insbesondere das i-Hexyl-3, 7-dimethylxanthin, zusätzlich noch eine spasmolytische Wirksamkeit an der glatten Muskulatur und eine pheriphere gefäßerweiternde Wirkung aufweisen.However, it was not previously known that such compounds, in particular i-hexyl-3, 7-dimethylxanthine, also has a spasmolytic effect on the smooth muscles and have a peripheral vasodilating effect.
Beispiel i Eine Mischung von 25 g Theobromin, 38 cm3 4 n-Natronlauge, 6o cm3 Isopropylalkohol und 17 g n-Hexylchlorid wird im Autoklaven 24 Stunden auf ioo° erhitzt. Nach dem Verdampfen des Alkohols wird die alkalische Lösung mit Chloroform extrahiert und die, wäßrige Schicht angesäuert. Die Ausbeute an i-Hexyl-3, 7-dimethylxanthin beträgt abzüglich des wiedergewonnenen Theobromins 88 °/o. -- Der Schmelzpunkt liegt bei 82 bis 83°.Example i A mixture of 25 g of theobromine, 38 cm3 of 4 n sodium hydroxide solution, 6o cm3 of isopropyl alcohol and 17 g of n-hexyl chloride are stored in the autoclave for 24 hours ioo ° heated. After the alcohol has evaporated becomes the most alkaline The solution was extracted with chloroform and the aqueous layer was acidified. The yield of i-hexyl-3, 7-dimethylxanthine minus the recovered theobromine 88 ° / o. - The melting point is 82 to 83 °.
Beispiel 2-2o,2 g Theobrominnatriunnwerden mit 2o g n-Hexylbromid und ioo cm3 Toluol io Stunden bei ioo° in der Kugelmühle -gemahlen. Nach dem Aufarbeiten erhält man 22,3 g Hexyltheobromin vom Schmelzpunkt 8q.°, das sind 84,5 °/o der Theorie.Example 2-2o.2 g of theobromine sodium are added with 20 g of n-hexyl bromide and 100 cm3 of toluene -milled for 10 hours at 100 ° in a ball mill. After working up 22.3 g of hexyl theobromine with a melting point of 8 ° are obtained, which is 84.5% of theory.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC3334A DE860217C (en) | 1950-10-28 | 1950-10-28 | Process for the preparation of 1-hexyl-3, 7-dimethylxanthine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC3334A DE860217C (en) | 1950-10-28 | 1950-10-28 | Process for the preparation of 1-hexyl-3, 7-dimethylxanthine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE860217C true DE860217C (en) | 1952-12-18 |
Family
ID=7013035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC3334A Expired DE860217C (en) | 1950-10-28 | 1950-10-28 | Process for the preparation of 1-hexyl-3, 7-dimethylxanthine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE860217C (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004017964A1 (en) | 2002-08-19 | 2004-03-04 | Pfizer Products Inc. | Combination therapy for hyperproliferative diseases |
| WO2007062314A2 (en) | 2005-11-23 | 2007-05-31 | Bristol-Myers Squibb Company | Heterocyclic cetp inhibitors |
| WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| EP2392567A1 (en) | 2005-10-21 | 2011-12-07 | Bristol-Myers Squibb Company | Benzothiazine derivatives and their use as lxr modulators |
| WO2013155465A1 (en) | 2012-04-13 | 2013-10-17 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| WO2014170786A1 (en) | 2013-04-17 | 2014-10-23 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| US10335413B2 (en) | 2009-02-27 | 2019-07-02 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| WO2020150473A2 (en) | 2019-01-18 | 2020-07-23 | Dogma Therapeutics, Inc. | Pcsk9 inhibitors and methods of use thereof |
-
1950
- 1950-10-28 DE DEC3334A patent/DE860217C/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004017964A1 (en) | 2002-08-19 | 2004-03-04 | Pfizer Products Inc. | Combination therapy for hyperproliferative diseases |
| EP2392567A1 (en) | 2005-10-21 | 2011-12-07 | Bristol-Myers Squibb Company | Benzothiazine derivatives and their use as lxr modulators |
| WO2007062314A2 (en) | 2005-11-23 | 2007-05-31 | Bristol-Myers Squibb Company | Heterocyclic cetp inhibitors |
| WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| US10335413B2 (en) | 2009-02-27 | 2019-07-02 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| WO2013155465A1 (en) | 2012-04-13 | 2013-10-17 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| US9328113B2 (en) | 2012-04-13 | 2016-05-03 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| WO2014170786A1 (en) | 2013-04-17 | 2014-10-23 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| WO2020150473A2 (en) | 2019-01-18 | 2020-07-23 | Dogma Therapeutics, Inc. | Pcsk9 inhibitors and methods of use thereof |
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