DE1109698B - Process for the preparation of 4-amino 1,5,7-triaza-indanes - Google Patents
Process for the preparation of 4-amino 1,5,7-triaza-indanesInfo
- Publication number
- DE1109698B DE1109698B DEK37738A DEK0037738A DE1109698B DE 1109698 B DE1109698 B DE 1109698B DE K37738 A DEK37738 A DE K37738A DE K0037738 A DEK0037738 A DE K0037738A DE 1109698 B DE1109698 B DE 1109698B
- Authority
- DE
- Germany
- Prior art keywords
- triaza
- amino
- hydrogen atom
- indanes
- halides
- 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
- JTAXQEXXMJBSMX-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class NC1=NC=NC2=C1CCN2 JTAXQEXXMJBSMX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000004715 keto acids Chemical class 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 108091036732 NRON Proteins 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012188 paraffin wax Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung von 4-Amino 1,5,7-triaza-indanen Es wurde gefunden, daß man zu 4-Amino-1,5,7 triaza-indanen der allgemeinen Formel in welcher R ein Wasserstoffatom oder einen Alkyl-, Cycloalkyl-, Aralkyl- oder Arylrest und R1 ein Wasserstoffatom oder einen niedermolekularen Alkylrest bedeutet, und ihren quartären Ammoniumsalzen gelangt, wenn man substituierte Pyrimidine der allgemeinen Formel worin R und Rt die oben angegebene Bedeutung besitzen, R2 ein Wasserstoffatom oder einen niedermolekularen Alkylrest, R3 eine freie oder acylierte, primäre Aminogruppe und Y eine Hydroxylgruppe oder ein Halogenatom darstellt, durch Behandlung mit Halogeniden der Sauerstoffsäuren des Phosphors, Schwefels oder Kohlenstoffs oder einem Oxalsäurehalogenid bei Temperaturen von 100 bis 2000 C in Gegenwart eines organischen Lösungsmittels oder eines Überschusses der genannten Halogenide cyclisiert und gegebenenfalls anschließend erhaltene 4-Acylamino-1,5,7-triaza-indane in an sich bekannter Weise verseift und/oder erhaltene l-Alkyl-1 , 5,7-triaza-indanderivate in ihre quartären Ammoniumsalze überführt.Process for the preparation of 4-amino-1,5,7-triaza-indanes It has been found that 4-amino-1,5,7-triaza-indanes of the general formula can be obtained in which R is a hydrogen atom or an alkyl, cycloalkyl, aralkyl or aryl radical and R1 is a hydrogen atom or a low molecular weight alkyl radical, and its quaternary ammonium salts are obtained when substituted pyrimidines of the general formula where R and Rt have the meaning given above, R2 is a hydrogen atom or a low molecular weight alkyl radical, R3 is a free or acylated, primary amino group and Y is a hydroxyl group or a halogen atom, by treatment with halides of the oxo acids of phosphorus, sulfur or carbon or an oxalic acid halide cyclized at temperatures of 100 to 2000 C in the presence of an organic solvent or an excess of the halides mentioned and optionally then obtained 4-acylamino-1,5,7-triaza-indanes saponified in a known manner and / or obtained l-alkyl 1, 5,7-triaza-indane derivatives converted into their quaternary ammonium salts.
Die als Ausgangsverbindungen benötigten, substituierten 6-Hydroxypyrimidine lassen sich durch Umsetzung von Derivaten des Amidins mit in c;-Stellung basisch substituierten Cyanessigsäureestern darstellen. The substituted 6-hydroxypyrimidines required as starting compounds can be made basic by reacting derivatives of amidine with in the c; -position represent substituted cyanoacetic acid esters.
Aus diesen werden durch Behandlung mit Phosphoroxyhalogeniden bei Temperaturen unter 1000 C die ebenfalls als Ausgangsstoffe benötigten 6-Halogenpyrimidine erhalten.These are treated with phosphorus oxyhalides Temperatures below 1000 C, the 6-halopyrimidines also required as starting materials obtain.
Als Cyclisierungsmittel geeignete Säurechloride von Sauerstoffsäuren des Phosphors, Schwefels oder Kohlenstoffs oder der Oxalsäure sind z. B. Phosphortrichlorid, Phosphoroxychlorid, Phosphorpentachlorid, Thionylchlorid, Phosgen und Oxalylchlorid. Acid chlorides of oxo acids suitable as cyclizing agents of phosphorus, sulfur or Carbon or oxalic acid are z. B. phosphorus trichloride, Phosphorus oxychloride, phosphorus pentachloride, thionyl chloride, phosgene and oxalyl chloride.
Als Lösungsmittel für die Reaktion kommen aromatische Kohlenwasserstoffe, halogenierte aromatische Kohlenwasserstoffe, höhere Paraffinkohlenwasserstoffe und gemischte aliphatisch-aromatische Äther in Frage, welche mit den als Cyclisierungsmfttel benutzten Säurehalogeniden bei den erforderlichen Temperaturen nicht in Reaktion treten. Als. Lösungsmittel ist ferner ein Überschuß eines der genannten Cyclisierungsmittel besonders geeignet. Aromatic hydrocarbons are used as solvents for the reaction, halogenated aromatic hydrocarbons, paraffin higher hydrocarbons and mixed aliphatic-aromatic ethers in question, which with the as Cyclisierungsmfttel used acid halides not in reaction at the required temperatures step. As. The solvent is also an excess of one of the cyclizing agents mentioned particularly suitable.
Als Quaternisierungsmittel zur Umwandlung der l-Alkyl-1,5,7-triaza-indanderivate in die entsprechenden quartären Verbindungen sind z. B. Dialkylsulfate, Alkylhalogenide oder Aralkylhalogenide geeignet. As a quaternizing agent for converting the 1-alkyl-1,5,7-triaza-indane derivatives in the corresponding quaternary compounds are z. B. dialkyl sulfates, alkyl halides or aralkyl halides are suitable.
Die Cyclisierung erfolgt unter normalem Druck oder auch bei erhöhtem oder vermindertem Druck in geschlossenen Gefäßen. The cyclization takes place under normal pressure or at increased pressure or reduced pressure in closed vessels.
Die neuen Verbindungen können als Arzneimittel oder als Zwischenprodukte zur Herstellung von Arzneimitteln Verwendung finden. The new compounds can be used as drugs or as intermediates for the production of pharmaceuticals use.
Beispiel 1 1,6-Dimethyl-4-amino-1,5,7-triaza-indan In 150 ccm Phosphoroxychlorid werden nacheinander 30 g 2-Methyl-4-acetylamino-5-( -dimethylaminoäthyl)-6-hydroxypyrimidin und 20 g Phoshporpentachlorid allmählich eingetragen und durch mäßiges Erwärmen gelöst. Nach mehrstündigem Stehenlassen wird der Ansatz etwa 3 Stunden auf 110"C erwärmt. Anschließend entfernt man das Phosphoroxychlorid durch Vakuumdestillation, worauf der Rückstand durch Zusatz einer Eis-Wasser-Mischung gelöst und unter Kühlung vermittels konzentrierter Natronlauge stark alkalisch gemacht wird. Die organische Base wird ausgeäthert, die wäßrige Schicht mit Natriumchlorid gesättigt und bei etwa 40° C mit Butanol ausgeschüttelt. Aus den vereinigten, getrockneten Äther- und Butanolauszügen erhält man durch Einengen das rohe 1,6-Dimethyl-4-amino-1,5,7-triazaindan. Die Substanz läßt sich aus Aceton oder Isopropylalkohol umkristallisieren; F. 213 bis 215"C (Zersetzung); Ausbeute 3,9 g (18,85 0/o der Theorie). Example 1 1,6-Dimethyl-4-amino-1,5,7-triaza-indane In 150 cc of phosphorus oxychloride are successively 30 g of 2-methyl-4-acetylamino-5- (-dimethylaminoethyl) -6-hydroxypyrimidine and 20 g of phosphorus pentachloride gradually added and by moderate heating solved. After standing for several hours, the batch is heated to 110.degree. C. for about 3 hours warmed up. The phosphorus oxychloride is then removed by Vacuum distillation, followed by the addition of an ice-water mixture dissolved and made strongly alkaline with cooling by means of concentrated sodium hydroxide solution will. The organic base is extracted with ether, the aqueous layer with sodium chloride saturated and extracted with butanol at about 40 ° C. From the combined, dried Ether and butanol extracts are obtained by concentrating the crude 1,6-dimethyl-4-amino-1,5,7-triazaindane. The substance can be recrystallized from acetone or isopropyl alcohol; F. 213 up to 215 "C (decomposition); yield 3.9 g (18.85% of theory).
4,0 g 6-Dimethyl-4-amino- 1 ,5,7-triaza-indan werden in 40 ccm Methanol gelöst und mit 12,0 ccm Methyljodid 10 Minuten zum Sieden erhitzt, wobei rasch Fällung eintritt. Nach lstündigem Stehenlassen in der Wärme wird gekühlt. Durch Absaugen und Trocknen erhält man 3,0 g l,6-Dimethyl-4-aminol,5,7-triaza-indan-1-methojodid; F. 285° C. An Stelle des Methanols kann man als Lösungsmittel auch Acetonitril oder eine Methanol-Acetonitril-Mischung verwenden. 4.0 g of 6-dimethyl-4-amino-1, 5,7-triaza-indane are dissolved in 40 cc of methanol dissolved and heated to boiling with 12.0 ccm of methyl iodide for 10 minutes, with rapid precipitation entry. After standing in the heat for one hour, it is cooled. By suction and drying gives 3.0 g of 1,6-dimethyl-4-aminol, 5,7-triaza-indan-1-methoiodide; F. 285 ° C. Instead of methanol, acetonitrile or acetonitrile can be used as a solvent use a methanol-acetonitrile mixture.
In entsprechender Weise erhält man aus 40 g 2-Methyl-4-amino-5-(,B-diäthylaminoäthyl)-6-hydroxypyrimidin durch Ringschluß 9,7 g 1-Äthyl-4-amino-6-methyl-1,5,7-triaza-indan (30,6°/o der Theorie); F. 185 bis 186° C. In a corresponding manner, 40 g of 2-methyl-4-amino-5 - (, B-diethylaminoethyl) -6-hydroxypyrimidine are obtained by ring closure 9.7 g of 1-ethyl-4-amino-6-methyl-1,5,7-triaza-indane (30.6% Theory); F. 185 to 186 ° C.
Beispiel 2 1 -Äthyl-4-amino-6-methyl- 1,5,7-triaza-indan 20 g 2- Methyl-4- amino - 5- (ß- diäthylaminoäthyl)-6-chlorpyrimidin (F. 127 bis 1280 C, erhalten durch Einwirkung von Phosphoroxychlorid auf 2-Methyl-4-amino-5-[-diäthylaminoäthyl]-6-oxypyn.midin bei 30 bis 600 C) werden in 100 ccm Phosphoroxychlorid unter Zusatz von 13 g Phosphorpentachlorid durch Erwärmen auf 110"C verflüssigt und die Mischung etwa 3 Stunden auf dieser Temperatur gehalten. Anschließend wird der Ansatz noch 1/2 Stunde auf 1400 C erhitzt. Nach dem Erkalten wird das Reaktionsprodukt, wie im Beispiel 1 angegeben, aufgearbeitet. Man erhält l-Äthyl-4-amino-6-methyl-1,5,7-triaza-indan; F. 185 bis 1860 C (nach dem Umkristallisieren aus Athylenchlorid oder Aceton); Ausbeute 10,29 g (70 (70°/0 der Theorie). Example 2 1 -ethyl-4-amino-6-methyl-1,5,7-triaza-indane 20 g 2- Methyl-4- amino - 5- (ß-diethylaminoethyl) -6-chloropyrimidine (mp 127 to 1280 C, obtained by the action of phosphorus oxychloride on 2-methyl-4-amino-5 - [- diethylaminoethyl] -6-oxypyn.midine at 30 to 600 C) in 100 cc of phosphorus oxychloride with the addition of 13 g of phosphorus pentachloride liquefied by heating to 110 "C and the mixture on this for about 3 hours Temperature held. The batch is then heated to 1400 ° C. for a further 1/2 hour. After cooling, the reaction product is worked up as indicated in Example 1. 1-ethyl-4-amino-6-methyl-1,5,7-triaza-indane is obtained; F. 185 to 1860 C (after recrystallization from ethylene chloride or acetone); Yield 10.29 g (70 (70 ° / 0 the theory).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK37738A DE1109698B (en) | 1959-05-14 | 1959-05-14 | Process for the preparation of 4-amino 1,5,7-triaza-indanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK37738A DE1109698B (en) | 1959-05-14 | 1959-05-14 | Process for the preparation of 4-amino 1,5,7-triaza-indanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1109698B true DE1109698B (en) | 1961-06-29 |
Family
ID=7221126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK37738A Pending DE1109698B (en) | 1959-05-14 | 1959-05-14 | Process for the preparation of 4-amino 1,5,7-triaza-indanes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1109698B (en) |
-
1959
- 1959-05-14 DE DEK37738A patent/DE1109698B/en active Pending
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