DE924085C - Process for the preparation of nitric acid esters of oxyalkylxanthines - Google Patents
Process for the preparation of nitric acid esters of oxyalkylxanthinesInfo
- Publication number
- DE924085C DE924085C DES34639A DES0034639A DE924085C DE 924085 C DE924085 C DE 924085C DE S34639 A DES34639 A DE S34639A DE S0034639 A DES0034639 A DE S0034639A DE 924085 C DE924085 C DE 924085C
- Authority
- DE
- Germany
- Prior art keywords
- nitric acid
- acid esters
- oxyalkylxanthines
- preparation
- theophylline
- 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 229910017604 nitric acid Inorganic materials 0.000 description 10
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 8
- -1 nitric acid ester Chemical class 0.000 description 7
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 5
- 229960000278 theophylline Drugs 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229960004559 theobromine Drugs 0.000 description 3
- 229940075420 xanthine Drugs 0.000 description 3
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- QVGLHVDBDYLFON-UHFFFAOYSA-M sodium;1,3-dimethylpurin-7-ide-2,6-dione Chemical compound [Na+].O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 QVGLHVDBDYLFON-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KKWIVMCCCHOXGV-UHFFFAOYSA-N 1-ethyl-3,7-dihydropurine-2,6-dione Chemical compound O=C1N(CC)C(=O)NC2=C1NC=N2 KKWIVMCCCHOXGV-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- NHAXKHSVJBVINX-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione;sodium Chemical compound [Na].CN1C(=O)NC(=O)C2=C1N=CN2C NHAXKHSVJBVINX-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 239000000006 Nitroglycerin Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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
- 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)
Description
Verfahren zur Herstellung von Salpetersäureestern von Oxalkylxanthinen In der Therapie werden an Stelle von Xanthinbasen, z. B. von Theophyllin und Theobromin oder deren salzartigen Verbindungen, mit Vorliebe die entsprechenden Oxalkylderivate verwendet. Sie zeichnen sich bei gleichem Wirkungscharakter durch bessere Verträglichkeit aus.Process for the preparation of nitric acid esters of oxalkylxanthines In therapy, instead of xanthine bases, e.g. B. of theophylline and theobromine or their salt-like compounds, preferably the corresponding oxyalkyl derivatives used. They are characterized by better tolerability with the same effect the end.
Es wurde gefunden, daß sich derartige Oxalkylxanthine, die im Oxalkylrest mindestens 2 Kohlenstoffatome enthalten, durch Behandlung mit Nitrierungsmitteln, z. B. wasserfreier Salpetersäure, auf einfache Weise und mit guter Ausbeute in Salpetersäureester überführen lassen. Bei Anwendung eines entsprechenden Überschusses an Salpetersäure werden bei vorzugsweise niedriger Temperatur und bei relativ kurzer Einwirkungszeit sämtliche OH-Gruppen verestert, ohne daß eine nennenswerte oxydative Aufspaltung des Xanthinmoleküls erfolgt. An Stelle von wasserfreier Salpetersäure läßt sich auch das bekannte Gemisch von hochprozentiger Salpetersäure und konzentrierter Schwefelsäure verwenden.It has been found that such oxalkylxanthines in the oxalkyl radical contain at least 2 carbon atoms by treatment with nitrating agents, z. B. anhydrous nitric acid, in a simple manner and with good yield in nitric acid ester get convicted. When using an appropriate excess of nitric acid are preferably at a low temperature and with a relatively short exposure time all OH groups are esterified without any significant oxidative splitting of the xanthine molecule takes place. Instead of anhydrous nitric acid can also the well-known mixture of high percentage nitric acid and concentrated sulfuric acid use.
Die neuen Verbindungen besitzen gleichzeitig die pharmakologische Wirkung der Xanthinbasen und der Nitrokörper, wie Nitroglycerin. Sie zeichnen sich insbesondere bei einem höheren Gehalt an Nitrogruppen durch ihre therapeutische, namentlich blutdrucksenkende Wirkung aus.The new compounds also have the pharmacological one Effect of the xanthine bases and the nitro bodies, such as nitroglycerin. You stand out especially with a higher content of nitro groups due to their therapeutic, especially antihypertensive effects.
Es wurde bereits ein Verfahren zur Herstellung der Salpetersäureester der I, 3-Dialkyl-7-oxymethylxanthine beschrieben (vgl. die USA.-Patentschrift 2 351 843). Danach werden I, 3-Dialkyl-xanthine durch Formaldehyd in die 7-Oxymethylverbindungen und anschließend mittels Thionylchlorid in die 7-Chlormethyl-xanthine übergeführt. Durch Umsetzung dieser Chlorverbindungen mit Silbernitrat entstehen die Salpetersäureester der 1, 3-Dialkyl-oxymethylxanthine. Eine direkte Veresterung der i, 3-Dialkyl-7-oxym.ethyl-xanthine mit Salpetersäure ist nach diesen Literaturangaben nicht durchführbar. Auf analoge Weise wurde auch der Salpetersäureester des 71-Oxy-8-chlorcoffeins dargestellt (vgl. die USA.-Patentschrift 2 35z 844).There has already been a process for making the nitric acid esters the I, 3-dialkyl-7-oxymethylxanthine described (see. The USA. Patent 2 351 843). Then 1,3-dialkyl-xanthines are converted into 7-oxymethyl compounds by means of formaldehyde and then converted into the 7-chloromethyl-xanthine by means of thionyl chloride. The reaction of these chlorine compounds with silver nitrate results in them the Nitric acid esters of 1,3-dialkyl-oxymethylxanthines. A direct esterification the i, 3-dialkyl-7-oxym.ethyl-xanthine with nitric acid is according to this literature not feasible. The nitric acid ester of 71-oxy-8-chlorocaffeine was also made in an analogous manner (see U.S. Patent 2 35z 844).
Nach diesem sehr umständlichen und spezifischen Verfahren werden nur Mono-Salpetersäureester erhalten.Following this very cumbersome and specific procedure will only be Obtained mono-nitric acid ester.
Ein anderes Verfahren beschreibt die Nitrierufig von Theophyllin, wobei jedoch Nitroverbindungen, die keine Salpetersäureester sind, entstehen.Another method describes the nitration of theophylline, however, nitro compounds that are not nitric acid esters are formed.
Diesen bekannten und spezifischen Verfahren gegenüber ist das vorstehende Verfahren allgemein auf oxallkylierte Xanthine anwendbar. Es gestattet die Herstellung ein- und mehrwertiger Salpetersäureester oxalkylierter Xanthine auf einfache und wirtschaftliche Weise bei guter Ausbeute, sofern die Oxalkylgruppen mindestens 2 Kohlenstoffatome enthalten. Beispiel i 2o g wasserfreies 7-Oxäthyl-theophylhn, beispielsweise durch Einwirkung von Äthylenchlorhydrin auf Theophyllinnatrium hergestellt, werden bei -io° in ioo g wasserfreier Salpetersäure unter Rühren aufgelöst. Man hält die klare Lösung 3o Minuten auf o° und gießt dann in 21 Eiswasser. Nach einigen Stunden ist der Salpetersäureester völlig ausgefallen. Er ist schwer löslich in Wasser und Alkoholen, leichter in Aceton, Chlorkohlenwasserstoffen, Dioxan, Formamid, Eisessig. Durch Umkristallisieren, beispielsweise aus viel Wasser, erhält man aus obiger Menge 15 g des reinen Salpetersäureesters des 7-Oxäthyl-theophyllins in farblosen Nadeln. Die neue Verbindung schmilzt bei 187° unter Zersetzung.Opposite these known and specific methods is the above Process generally applicable to oxalkylated xanthines. It allows manufacture mono- and polyvalent nitric acid esters of oxalkylated xanthines on simple and economical way with good yield, provided that the oxalkyl groups are at least 2 Contain carbon atoms. Example i 2o g of anhydrous 7-Oxäthyl-theophylhn, for example produced by the action of ethylene chlorohydrin on theophylline sodium Dissolved at -io ° in 100 g of anhydrous nitric acid with stirring. You keep that clear solution to 0 ° for 30 minutes and then pour into 21 ice water. After a few hours the nitric acid ester has failed completely. It is sparingly soluble in water and Alcohols, lighter in acetone, chlorinated hydrocarbons, dioxane, formamide, glacial acetic acid. Recrystallization, for example from a lot of water, gives the above amount 15 g of the pure nitric acid ester of 7-oxethyl-theophylline in colorless needles. The new compound melts at 187 ° with decomposition.
Beispiel 2 409 wasserfreies 7-Dioxypropyl-theophyllin, aus Theophyllinnatrium und Glycerin-a-monochlorhydrin hergestellt, werden bei -io bis -5° in Zoo g wasserfreier Salpetersäure aufgelöst. Man läßt die klare, wenig gefärbte Lösung 2o bis 30 Minuten stehen, wobei man die Temperatur auf 5° ansteigen läßt. Man gießt unter Rühren in 2 bis 31 Eiswasser, läßt einen Tag stehen, trennt den Salpetersäureester ab, wäscht mit ammoniakhaltigem Wasser säurefrei und trocknet bei gelinder Wärme. Man erhält 39 g des Disalpetersäureesters des Dioxypropyl-theophyllins, der beim Umkristallisieren aus Butanol oder aus 3o°/piger Essigsäure in farblosen, bei 175 bis z76° unter Zersetzung schmelzenden Nadeln erhalten wird.Example 2 409 anhydrous 7-dioxypropyl-theophylline, produced from sodium theophylline and glycerol-a-monochlorohydrin, are dissolved at -io to -5 ° in zoo g of anhydrous nitric acid. The clear, slightly colored solution is left to stand for 20 to 30 minutes, the temperature being allowed to rise to 5 °. It is poured into 2 to 31 ice water with stirring, left to stand for a day, the nitric acid ester is separated off, washed acid-free with ammonia-containing water and dried under mild heat. 39 g of the disnitric acid ester of dioxypropyl-theophylline are obtained, which is obtained on recrystallization from butanol or from 30% acetic acid in colorless needles which melt at 175 to z76 ° with decomposition.
. Beispiel 3 Man löst io g trockenes.i-Dioxypropyl-theobromin, aus Theobrominnatrium und Glycerin-a-monochlorhydrin dargestellt, in 5o g wasserfreier Salpetersäure bei -io bis -5° unter Rühren auf. Zur Vervollständigung der Nitrierung läßt man die Temperatur des Nitrierungsgemisches im Laufe von 15 bis 2o Minuten auf io° ansteigen. Wenn sich die Mischung durch nitrose Gase braun färbt, ist die Temperatur zu erniedrigen. Man gießt in 21 kaltes Wasser oder etwa 3o°/oige Essigsäure, regt die Ausscheidung des Salpetersäureesters durch Reiben der Gefäßwand an und läßt zur Vervollständigung der Kristallisation mehrere Stunden stehen. Ausbeute 9 g. Durch Umkristallisieren aus 3o°/oiger Essigsäure erhält man den Disalpetersäureester des Dioxypropyltheobromins in farblosen Nadeln, die bei 153 bis 154° unter Zersetzung schmelzen.. EXAMPLE 3 10 g of dry i-dioxypropyl-theobromine, prepared from theobromine sodium and glycerol-a-monochlorohydrin, are dissolved in 50 g of anhydrous nitric acid at -io to -5 ° with stirring. To complete the nitration, the temperature of the nitration mixture is allowed to rise to 10 ° in the course of 15 to 20 minutes. If the mixture turns brown from nitrous gases, lower the temperature. It is poured into 21% cold water or about 30% acetic acid, the excretion of the nitric acid ester is stimulated by rubbing the wall of the vessel and left to stand for several hours to complete the crystallization. Yield 9 g. Recrystallization from 30% acetic acid gives the disnitric acid ester of dioxypropyl theobromine in colorless needles which melt at 153 to 154 ° with decomposition.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES34639A DE924085C (en) | 1953-08-01 | 1953-08-01 | Process for the preparation of nitric acid esters of oxyalkylxanthines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES34639A DE924085C (en) | 1953-08-01 | 1953-08-01 | Process for the preparation of nitric acid esters of oxyalkylxanthines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE924085C true DE924085C (en) | 1955-02-24 |
Family
ID=7481594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES34639A Expired DE924085C (en) | 1953-08-01 | 1953-08-01 | Process for the preparation of nitric acid esters of oxyalkylxanthines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE924085C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1090219B (en) * | 1957-01-28 | 1960-10-06 | Arzneimittelfabrik Krewel Leuf | Process for the preparation of nitric acid esters of dimethylxanthine derivatives |
| DE1100028B (en) * | 1956-03-28 | 1961-02-23 | Arzneimittelfabrik Krewel Leuf | Process for the preparation of nitric acid esters of dialkyl-xanthine-carboxylic acidoxyalkylamides |
| DE1118205B (en) * | 1959-05-30 | 1961-11-30 | Dresden Arzneimittel | Process for the preparation of nitric acid esters of Oxyalkyltheophyllinen |
| DE1225649B (en) * | 1961-10-05 | 1966-09-29 | Robert Pfleger Chem Fab Dr | Process for the preparation of salts of the nitric acid esters of 7-hydroxyalkylaminoalkyltheophyllines |
| EP1829523A1 (en) * | 2006-03-01 | 2007-09-05 | L'oreal | Cosmetic use of an N-oxide derivative of theophylline |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19106C (en) * | AD. LEXOW in Berlin S., Dresdenerstr. 43 | Special machine for the mass production of the individual parts for piano mechanics | ||
| DE193799C (en) * | ||||
| FR377382A (en) * | 1906-08-08 | 1907-09-05 | Societe Farbenfabriken Vorm. Friedr. Bayer & C° | Process for the production of oxyalkylated derivatives of xanthine or its homologues |
| US2517410A (en) * | 1947-08-15 | 1950-08-01 | Searle & Co | Hydroxy alkyl xanthines and the production thereof |
| US2575344A (en) * | 1946-03-01 | 1951-11-20 | State Of Iowa | Dihydroxypropyl theophylline |
| DE859470C (en) * | 1943-07-11 | 1952-12-15 | Byk Gulden Lomberg Chem Fab | Process for the production of therapeutically active substances from theophylline |
-
1953
- 1953-08-01 DE DES34639A patent/DE924085C/en not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19106C (en) * | AD. LEXOW in Berlin S., Dresdenerstr. 43 | Special machine for the mass production of the individual parts for piano mechanics | ||
| DE193799C (en) * | ||||
| FR377382A (en) * | 1906-08-08 | 1907-09-05 | Societe Farbenfabriken Vorm. Friedr. Bayer & C° | Process for the production of oxyalkylated derivatives of xanthine or its homologues |
| DE859470C (en) * | 1943-07-11 | 1952-12-15 | Byk Gulden Lomberg Chem Fab | Process for the production of therapeutically active substances from theophylline |
| US2575344A (en) * | 1946-03-01 | 1951-11-20 | State Of Iowa | Dihydroxypropyl theophylline |
| US2517410A (en) * | 1947-08-15 | 1950-08-01 | Searle & Co | Hydroxy alkyl xanthines and the production thereof |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1100028B (en) * | 1956-03-28 | 1961-02-23 | Arzneimittelfabrik Krewel Leuf | Process for the preparation of nitric acid esters of dialkyl-xanthine-carboxylic acidoxyalkylamides |
| DE1090219B (en) * | 1957-01-28 | 1960-10-06 | Arzneimittelfabrik Krewel Leuf | Process for the preparation of nitric acid esters of dimethylxanthine derivatives |
| DE1118205B (en) * | 1959-05-30 | 1961-11-30 | Dresden Arzneimittel | Process for the preparation of nitric acid esters of Oxyalkyltheophyllinen |
| DE1225649B (en) * | 1961-10-05 | 1966-09-29 | Robert Pfleger Chem Fab Dr | Process for the preparation of salts of the nitric acid esters of 7-hydroxyalkylaminoalkyltheophyllines |
| EP1829523A1 (en) * | 2006-03-01 | 2007-09-05 | L'oreal | Cosmetic use of an N-oxide derivative of theophylline |
| FR2898048A1 (en) * | 2006-03-01 | 2007-09-07 | Oreal | COSMETIC USE OF THEOPHYLLINE N-OXIDE DERIVATIVE |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE617508C (en) | Process for the production of pure lecithin | |
| DE924085C (en) | Process for the preparation of nitric acid esters of oxyalkylxanthines | |
| DE629662C (en) | Process for the production of a concentrated, durable, aqueous theophylline solution | |
| DE907293C (en) | Process for the preparation of polysulfuric acid esters and salts thereof | |
| DE876441C (en) | Process for the production of a knitted body from hawthorn | |
| US3071511A (en) | Prednisolone-21-oenanthate octyldodecanol eye lotion | |
| DE137207C (en) | ||
| DE706341C (en) | Process for the production of water-swollen shrink capsules | |
| AT69784B (en) | Process for the preparation of acetone-soluble acidyl celluloses. | |
| AT253677B (en) | Process for the isolation of a centrally sedative isovaleric acid ester from non-aqueous valerian extracts | |
| DE859470C (en) | Process for the production of therapeutically active substances from theophylline | |
| AT223326B (en) | Process for the preparation of complex compounds of chloramphenicol | |
| DE977653C (en) | Process for the direct production of mixed nitric acid esters from polyalcohols | |
| DE65110C (en) | Process for the preparation of o-methoxy-ana-acetylamidoquinoline. (2 | |
| DE508167C (en) | Production of shelf-stable chlorinated lime | |
| DE1568062C3 (en) | Process for the preparation of 17alpha-acetoxy-Sbeta-hydroxy-o-chlorpregnan-4,6-dien-20-one. Eliminated from: 1241825 | |
| DE1058520B (en) | Process for obtaining reserpine-free deserpidine | |
| AT223330B (en) | Process for the preparation of new morphine-bis-pyridinecarboxylic acid esters | |
| DE653934C (en) | Process for the preparation of carbonic acid esters of sex hormones | |
| AT219591B (en) | Process for the production of sodium acetyl salicylate or of double salts of sodium acetyl salicylate with sodium bicarbonate | |
| DE528268C (en) | Process for the preparation of porphyrins | |
| AT217159B (en) | Process for the preparation of aqueous solutions of corticosteroids | |
| DE957030C (en) | Process for the preparation of the phenylpropionic acid esters of steroid hormones | |
| DE1147222B (en) | Process for the production of chemically pure dihydrostrophanthin | |
| DE936208C (en) | Process for the production of crystallized glycosides from Folia Digitalis lanata |