DE1249871B - Process for the preparation of 8,8-disubstituted pseudoxanthems - Google Patents
Process for the preparation of 8,8-disubstituted pseudoxanthemsInfo
- Publication number
- DE1249871B DE1249871B DENDAT1249871D DE1249871DA DE1249871B DE 1249871 B DE1249871 B DE 1249871B DE NDAT1249871 D DENDAT1249871 D DE NDAT1249871D DE 1249871D A DE1249871D A DE 1249871DA DE 1249871 B DE1249871 B DE 1249871B
- Authority
- DE
- Germany
- Prior art keywords
- derivatives
- general formula
- disubstituted
- preparation
- alkyl
- 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
- 238000000034 method Methods 0.000 title claims description 7
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 15
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 alkyl radicals Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229940075420 xanthine Drugs 0.000 description 3
- WZBKGWBHAPBSBF-UHFFFAOYSA-N 1,3,8-trimethyl-7h-purine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=C(C)N2 WZBKGWBHAPBSBF-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 229960003116 amyl nitrite Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical class NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 description 1
- RHZHJSCNWUGABX-UHFFFAOYSA-N 7-hydroxy-3h-purine-2,6-dione Chemical class N1C(=O)NC(=O)C2=C1N=CN2O RHZHJSCNWUGABX-UHFFFAOYSA-N 0.000 description 1
- KKOAWTWUOVGSKM-UHFFFAOYSA-N N1C(=O)NC=2N=CNC2C1=O.C(=O)=O Chemical compound N1C(=O)NC=2N=CNC2C1=O.C(=O)=O KKOAWTWUOVGSKM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. CL:
Deutsche Kl.:Int. CL:
German class:
C O 7 DC O 7 D
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
C07dC07d
, 4 73 .-ΜΙ 249871- .'■/
V26852IVd/12p .
25. September 1964
14. September 1967, 4 73.-ΜΙ 249871-. '■ /
V26852IVd / 12p.
September 25, 1964
September 14, 1967
Die Erfindung betrifft ein Verfahren zur Herstellung bisher unbekannter Pseudoxanthinderivate der allgemeinen FormelThe invention relates to a method of manufacture previously unknown pseudoxanthine derivatives of the general formula
Ri-NRi-N
worin Ri und/oder R2 Wasserstoffatome oder Alkylgruppen darstellen, die geradkettig oder verzweigt sein können, während R3 eine gegebenenfalls durch ein Halogenatom, eine Hydroxy- oder tertiäre Aminogruppe substituierte Alkyl-, Cycloalkyl-, Aryl- oder Aralkylgruppe bedeutet, wobei die Alkylreste der tertiären Aminogruppe auch mit dem Stickstoffatom zu einem gegebenenfalls durch ein weiteres Heteroatom unterbrochenen heterocyclischen Ring geschlossen sein können.wherein Ri and / or R2 are hydrogen atoms or alkyl groups represent, which can be straight-chain or branched, while R3 is optionally through a halogen atom, a hydroxy or tertiary amino group substituted alkyl, cycloalkyl, aryl or aralkyl group, where the alkyl radicals of the tertiary amino group also with the nitrogen atom to a heterocyclic ring which is optionally interrupted by a further heteroatom can be closed.
Pseudoxanthinderivate obiger Struktur sind bislang noch nicht beschrieben worden. Als Bezeichnungen für das Ringsystem sind noch Isoxanthin oder 8-H-Xanthin möglich. Es unterscheidet sich vom Xanthin, mit dem es isomer ist, durch die Verschiebung zweiter Doppelbindungen. Diese vom Erfinder erstmals hergestellten Pseudoxanthinderivate enthalten das 2-Isoimidazol- = 2 H-Imidazolgerüst, das zuerst von M. W e i s s in »J. Am. Chem. Soc«, Bd. 74, 1952, S. 5193, aufgeführt wird, im Purinmolekül. Pseudoxanthine derivatives of the above structure have not yet been described. As designations isoxanthine or 8-H-xanthine are also possible for the ring system. It is different from the Xanthine, with which it is isomeric, by shifting two double bonds. This from Pseudoxanthine derivatives produced by the inventor for the first time contain the 2-isoimidazole = 2 H-imidazole structure, that was first mentioned by M. W e i s s in »J. At the. Chem. Soc ", Vol. 74, 1952, p. 5193, in the purine molecule.
Es wurde gefunden, daß man zu den Verbindungen der oben angegebenen allgemeinen Formel auf einem einfachen Weg gelangt, wenn man die entsprechend substituierten Xanthinderivate der allgemeinen Formel It has been found that to the compounds of the general formula given above on a easy way if you get the appropriately substituted xanthine derivatives of the general formula
Verfahren zur Herstellung von
8,8-disubstituierten PseudoxanthinderivatenProcess for the production of
8,8-disubstituted pseudoxanthine derivatives
Anmelder:Applicant:
VEB Arzneimittelwerk Dresden,VEB Arzneimittelwerk Dresden,
Radebeul 1, Wilhelm-Pieck-Str. 35Radebeul 1, Wilhelm-Pieck-Str. 35
Als Erfinder benannt:
Dr. Herbert Goldner, Radebeul;
Dr. Günther Dietz, Dresden;
. Dr. Ernst Carstens, RadebeulNamed as inventor:
Dr. Herbert Goldner, Radebeul;
Dr. Günther Dietz, Dresden;
. Dr. Ernst Carstens, Radebeul
Anwesenheit der Methylgruppe in der 8-Stellung des Xanthinderivates. Die thermische Umlagerung läßt sich sowohl in Abwesenheit als auch in Gegenwart eines indifferenten organischen Lösungsmittels, wie Dimethylformamid, Xylol oder Cyclohexanol, durchführen. Presence of the methyl group in the 8-position des Xanthine derivatives. The thermal rearrangement can be carried out either in the absence or in the presence an inert organic solvent such as dimethylformamide, xylene or cyclohexanol.
Die Herstellung der Ausgangsprodukte erfolgt in nicht beanspruchter Weise durch Einwirkung von Oxydationsmitteln, z. B. i-Amylnitrit oder salpetriger Säure, auf entsprechend substituierte 4-Amino-5-nitrosouracile nach der allgemeinen GleichungThe production of the starting products takes place in a manner not claimed by the action of Oxidizing agents, e.g. B. i-amyl nitrite or nitrous acid, on appropriately substituted 4-amino-5-nitrosouracils according to the general equation
R1-NR 1 -N
NONO
NH — CH2 · CH3 NH - CH 2 • CH 3
OR3 OR 3
Ri-NRi-N
OHOH
HONOHONO
-H2 -H 2
CH3 CH 3
wobei Ri, R2 und R3 obige Bedeutung besitzen, wobei Ri und R2 obige Bedeutung besitzen. Dabei erhitzt.' Das geschieht z. B. durch einfaches Erhitzen 50 kann man vorteilhaft auch so verfahren, daß man daswhere Ri, R 2 and R 3 have the above meaning, where Ri and R 2 have the above meaning. Heated in the process. ' This happens z. B. by simply heating 50 one can advantageously also proceed so that one can
für diefor the
über ihren Schmelzpunkt. Voraussetzung Bildung der Pseudoxanthinderivate ist dabeiabove their melting point. The prerequisite for this is the formation of pseudoxanthine derivatives
entsprechend substituierte 4-Aminouracilderivat nitrosiert, z. B. in Alkohol mit'überschüssigem i-Amyl-appropriately substituted 4-aminouracil derivative nitrosated, z. B. in alcohol with excess i-amyl
709 647/539709 647/539
nitrit und ohne Isolierung der zuerst entstehenden 5-Nitrosoverbindung in der Reaktionsmischung bis zum Verschwinden der Nitrosofarbe unter Rückfluß erhitzt. Die Erhitzungsdauer beträgt im allgemeinen 15 bis 60 Minuten.nitrite and without isolation of the 5-nitroso compound formed first in the reaction mixture up to refluxed to make the nitroso color disappear. The heating time is generally 15 to 60 minutes.
Die zum Teil bei dem Erhitzen durch Wasserabspaltung aus den 5-Nitrosoverbindungen mit entstandenen entsprechenden Xanthinderivate können beispielsweise durch Umkristallisieren abgetrennt werden. Auch können die7-Hydroxyxanthin-Xanthin-Gemische z. B. durch Lösen in 1 η-Natronlauge und fraktionierte Ausfällung mit Kohlendioxid (Xanthin) und anschließende Fällung mit Salzsäure .(7-Hydroxyderivat) gereinigt werden.The corresponding xanthine derivatives, some of which are formed during the heating by splitting off water from the 5-nitroso compounds, can be separated off, for example, by recrystallization. Also die7-Hydroxyxanthin xanthine mixtures z. B. by dissolving in 1 η sodium hydroxide solution and fractional precipitation with carbon dioxide (xanthine) and subsequent precipitation with hydrochloric acid. (7-hydroxy derivative).
Durch Umsetzungen der 7-Hydroxyxanthine mit einer entsprechenden Halogenverbindung der allgemeinen Formel R3 — Hai, worin R3 die obengenannte Bedeutung besitzt und Hai ein Halogenatom bedeutet, werden schließlich nach an sich bekannten Methoden die als Ausgangsstoffe verwendeten sub- 20 gefunden stituierten 7-Hydroxy-8-methylxanthinderivate erhalten. By reacting the 7-hydroxyxanthines with a corresponding halogen compound of the general Formula R3 - Hai, where R3 is the above Has meaning and Hai is a halogen atom means, the sub-20 used as starting materials are finally found by methods known per se obtained substituted 7-hydroxy-8-methylxanthine derivatives.
Die neuen Pseudoxanthinderivate können als Arzneimittel, z. B. Herz- und Kreislaufmittel, Verwendung finden. Die folgenden Beispiele sollen die Erfindung näher erläutern.The new pseudoxanthine derivatives can be used as drugs, e.g. B. Cardiovascular drugs, use Find. The following examples are intended to explain the invention in more detail.
2,25 g (0,01 Mol) 7-Methoxy-8-methyltheophyllin, Fp. 187 bis 187,50C, werden in einem offenen Kolben im ölbad geschmolzen und 10 Minuten auf dieser Temperatur gehalten. Die Substanz zeigt nach dem Abkühlen und einer Umkristallisation aus Alkohol einen Schmelzpunkt von 232 bis 232,50C, Ausbeute: 92°/o S-Methoxy-S-methylpseudotheophyllin. Molekulargewicht: C9H12N4O3: 224.2.25 g (0.01 mol) of 7-methoxy-8-methyltheophyllin, mp. 187 to 187.5 0 C, are kept in an open flask in an oil bath melted and 10 minutes at this temperature. The substance is, after cooling and recrystallization from alcohol a melting point 232 to 232.5 0 C, yield: 92 ° / o S-methoxy-S-methylpseudotheophyllin. Molecular weight: C9H12N4O3: 224.
Berechnet... C 48,2%, H 5,4%; gefunden ... C 48,4%, H 5,5%.Calculated ... C 48.2%, H 5.4%; found ... C 48.4%, H 5.5%.
Das als Ausgangsmaterial benötigte 7-Methoxy-8-methyltheophyllin ist auf folgendem Wege zugänglich: 18,3 g (0,01 Mol) l,3-Dimethyl-4-äthylaminouracil werden in 100 ml Alkohol gelöst und durch Zugabe von 35 ml i-Amylnitrit und wenigen Tropfen äthanolischer Salzsäure nitrosiert. Danach wird 20 Minuten unter Rückfluß zum Sieden erhitzt. Nach dem Abkühlen wird das mitgebildete 8-Methyltheophyllin abgesaugt und die Mutterlauge eingeengt, wobei in der Hauptsache die 7-Hydroxyverbindung isoliert wird (12 g). Fp. (nach Umkristallisation aus Wasser) 183 bis 184°C. Die Reinigung durch Lösen in 1 η-Natronlauge und fraktionierte Ausfällung mit Kohlendioxyd ergibt kein 8-Methyltheophyllin mehr. Durch Ansäuern mit Salzsäure fällt das 7-Hydroxy-8-methyltheophyllin aus, Fp. 184 bis 184,5° C, Ausbeute: 10 g, welches 1 Mol Kristallwasser enthält. Ein weiterer Teil kann aus den Umkristallisationsmutterlaugen des ersten und zweiten Teiles gewonnen und anschließend gereinigt werden.The 7-methoxy-8-methyltheophylline required as starting material is accessible in the following way: 18.3 g (0.01 mol) of 1,3-dimethyl-4-ethylaminouracil are dissolved in 100 ml of alcohol and by adding 35 ml of i-amyl nitrite and a few Drops of ethanolic hydrochloric acid nitrosated. It is then refluxed for 20 minutes. After cooling, the co-formed 8-methyltheophylline becomes suctioned off and the mother liquor concentrated, the main thing being the 7-hydroxy compound is isolated (12 g). Mp. (After recrystallization from water) 183 to 184 ° C. The cleaning dissolving in 1 η sodium hydroxide solution and fractional precipitation with carbon dioxide does not give 8-methyltheophylline more. Acidification with hydrochloric acid precipitates 7-hydroxy-8-methyltheophylline, melting point 184 up to 184.5 ° C, yield: 10 g, which contains 1 mol of water of crystallization contains. Another part can be obtained from the recrystallization mother liquors of the first and second Part won and then cleaned.
Molekulargewicht: C8Hi0N4O3: 210+ IH2O: 228.Molecular weight: C 8 Hi 0 N 4 O 3 : 210+ IH 2 O: 228.
Berechnet ... C 42,1%, H 5,3%; gefunden ... C 41,9%, H 5,4%.Calculated ... C 42.1%, H 5.3%; found ... C 41.9%, H 5.4%.
2,3 g (0,01 Mol) 7-Hydroxy-8-methyltheophyllin werden mit 5 ml Methyljodid in 150 ml Aceton und in Gegenwart von 2,5 g Kaliumcarbonat 2 Stunden unter Rückfluß erhitzt. Es wird heiß abgesaugt und das Aceton abdestilliert. Das erhaltene Rohprodukt wird aus Wasser umkristallisiert. Ausbeute: 81% 7-Methoxy-8-methyItheophyllin, Fp. 187 bis 187,50C.2.3 g (0.01 mol) of 7-hydroxy-8-methyltheophylline are refluxed for 2 hours with 5 ml of methyl iodide in 150 ml of acetone and in the presence of 2.5 g of potassium carbonate. It is filtered off with suction while hot and the acetone is distilled off. The crude product obtained is recrystallized from water. Yield: 81% of 7-methoxy-8-methyItheophyllin, mp 187 to 187.5 0C.
Molekulargewicht: CgHi2N4O3: 224.Molecular weight: CgHi 2 N 4 O 3 : 224.
Berechnet ... C 48,2%, H 5,4%; gefunden ... C 48,15%, H 5,3%.Calculated ... C 48.2%, H 5.4%; found ... C 48.15%, H 5.3%.
2,4 g (0,01 Mol) 7-Äthoxy-8-methyltheophyllin, Fp. 144,5 bis 146°C, erhalten aus 7-Hydroxy-8-methyltheophyllin und Äthyljodid, werden in einem offenen Kolben 10 Minuten auf 180°C erhitzt. Die Substanz zeigt nach dem Umkristallisieren aus Alkohol einen Schmelzpunkt von 172 bis 174° C, Ausbeute: 83% S-Äthoxy-S-methylpseudotheophyllin.2.4 g (0.01 mol) 7-ethoxy-8-methyltheophylline, Mp. 144.5 to 146 ° C, obtained from 7-hydroxy-8-methyltheophylline and ethyl iodide, are heated to 180 ° C for 10 minutes in an open flask. the After recrystallization from alcohol, the substance has a melting point of 172 to 174 ° C, yield: 83% S-ethoxy-S-methylpseudotheophylline.
Molekulargewicht: C10H14N4O3: 238. Berechnet ... C 50,4%, H 5,9%;Molecular weight: C10H14N4O3: 238. Calculated ... C 50.4%, H 5.9%;
C 50,7%, H 6,1%. Beispiel 3C 50.7%, H 6.1%. Example 3
2,4 g (0,01 Mol) 7-Äthoxy-8-methyltheophyllin werden in 20 ml Dimethylformamid 10 Minuten unter Rückfluß erhitzt. Nach dem Einengen werden g 8-Äthoxy-8-methylpseudotheophyllin, Fp. 171 bis 1730C, erhalten.2.4 g (0.01 mol) of 7-ethoxy-8-methyltheophylline are refluxed for 10 minutes in 20 ml of dimethylformamide. After concentration, 8-ethoxy-8-methylpseudotheophyllin be g, Fp. 171 to 173 0 C, was obtained.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV0026852 | 1964-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1249871B true DE1249871B (en) | 1967-09-14 |
Family
ID=7582956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1249871D Pending DE1249871B (en) | 1964-09-25 | Process for the preparation of 8,8-disubstituted pseudoxanthems |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1249871B (en) |
-
0
- DE DENDAT1249871D patent/DE1249871B/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH396927A (en) | Process for the preparation of new pyrazolopyrimidines | |
| DE2220256C3 (en) | N- (O- OR P-NITROBENZOYL) SULFOXIMINE, PROCESS FOR THEIR PREPARATION AND USE OF THE SAME | |
| DE1249871B (en) | Process for the preparation of 8,8-disubstituted pseudoxanthems | |
| DE870418C (en) | Process for the preparation of pyrazoline compounds | |
| DE2138528A1 (en) | Pyrazolo (3,4 b) pyndin 5 carboxamides and their salts, processes for producing such substances and medicaments containing them | |
| DE1229526B (en) | Process for the preparation of delta 4,1-3-oxo-11beta-hydroxy-19-nor-steroids by introducing oxygen in the 11-position by chemical means | |
| DE1238479B (en) | Process for the preparation of 5, 6-dihydro-5-oxo-11H-pyrido- [2, 3-b] [1, 5] -benzodiazepines | |
| DE1912941B2 (en) | 1 -PhenyM-amino-e-methoxypridazinium salts | |
| AT252262B (en) | Process for the production of new xanthine-7-N-oxides (7-hydroxy-xanthines) | |
| DE1254631B (en) | Process for the preparation of xanthine derivatives substituted in the 8-position | |
| DE1770538C3 (en) | Process for the preparation of 6,7-benzomorphane derivatives | |
| DE1695893C (en) | Process for the preparation of 4 amino 5 acylamidomethyl pynmidines | |
| DE2331044A1 (en) | DIPHENYLMETHANE DERIVATIVES AND PROCESS FOR THEIR PRODUCTION | |
| DE1199275B (en) | Process for the preparation of 5,6,7,8-tetra-hydro-3H-pyrimido [5,4-c] [1,2,5] -oxadiazines | |
| DE834105C (en) | Process for the production of xanthine or alkyl and aryl xanthines | |
| DE1000820C2 (en) | Process for the preparation of iminodibenzylene | |
| DE915938C (en) | Process for the preparation of oxoacylamines of the cyclopentanopolyhydrophenanthrene series | |
| AT235299B (en) | Process for the preparation of new pyrimidone derivatives | |
| DE1190464B (en) | Process for the preparation of pyridine derivatives | |
| DE2222186C3 (en) | Process for the preparation of vincamine and analogous compounds | |
| DE1246742B (en) | Process for the production of new phenothiazines | |
| AT249681B (en) | Process for the preparation of new 3H-pyrimido- [5,4-c] 1,2,5-oxadiazines | |
| DE1024968B (en) | Process for the preparation of 7-ketonyl-8-amino-theophyllines | |
| DE1695893B1 (en) | Process for the preparation of 4-amino-5-acylamidomethylpyrimidines | |
| DE1141995B (en) | Process for the preparation of derivatives of 4-oxycoumarin |