CH362411A - Process for the preparation of new derivatives of benzimidazole - Google Patents
Process for the preparation of new derivatives of benzimidazoleInfo
- Publication number
- CH362411A CH362411A CH346261A CH346261A CH362411A CH 362411 A CH362411 A CH 362411A CH 346261 A CH346261 A CH 346261A CH 346261 A CH346261 A CH 346261A CH 362411 A CH362411 A CH 362411A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzimidazole
- formula
- acid
- preparation
- new derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 10
- -1 alkyl radicals Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UFLCBIQQTOCIHZ-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]benzimidazole Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2N=C1 UFLCBIQQTOCIHZ-UHFFFAOYSA-N 0.000 description 2
- LZRQZPHBQJVNIS-UHFFFAOYSA-N 2-n-benzyl-4-chlorobenzene-1,2-diamine Chemical compound NC1=CC=C(Cl)C=C1NCC1=CC=CC=C1 LZRQZPHBQJVNIS-UHFFFAOYSA-N 0.000 description 2
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FARSPAVQUKTXLF-UHFFFAOYSA-N 1h-benzimidazol-1-ium;chloride Chemical compound Cl.C1=CC=C2NC=NC2=C1 FARSPAVQUKTXLF-UHFFFAOYSA-N 0.000 description 1
- UEVXOSBJQSOBOV-UHFFFAOYSA-N 1h-benzimidazole;lead Chemical group [Pb].C1=CC=C2NC=NC2=C1 UEVXOSBJQSOBOV-UHFFFAOYSA-N 0.000 description 1
- MHMTXDMLQZHXRZ-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-2-methyl-1h-benzimidazol-3-ium;chloride Chemical compound [Cl-].CC=1NC2=CC=CC=C2[N+]=1CC1=CC=C(Cl)C=C1 MHMTXDMLQZHXRZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 241001480035 Epidermophyton Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 229960004266 acetylcholine chloride Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WNAQOLSMVPFGTE-UHFFFAOYSA-N chlormidazole Chemical compound CC1=NC2=CC=CC=C2N1CC1=CC=C(Cl)C=C1 WNAQOLSMVPFGTE-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von neuen Derivaten des Benzimidazols
Die therapeutische Wirkung der Substitutionsprodukte des Benzimidazols ist wiederholt untersucht worden,. Man hat festgestellt, dass die Wirkung je nach der Natur der Substituenten stark schwankt.
Bezüglich der Substituenben in der 2-Stellung des Benzimidazols ist festgestellt worden, dass Kohlsn- wasserstoffreste als Substituenten in der 2-Stellung zu Produkten mit sehr geringer spasmolytischer Wirkung führen (J. Am. Chem.
Soc. 71, S. 2035), wäh- rend Substituenten mit basischen N-Atomen in der 2-Stellung des Benzimidazols dann zu praktisch bnauchbaren Produkten führen, wenn die l-Stellung durch einen substituierten oder nichtsubstituierten Aralkyl-, Aryl-oder heterocyclischen, Rest bzw. heterocyclisch substituierten Alkylrest besetzt ist (DBP Nr. 890644).
Es sind auch schon eine Anzahl von Derivaten des Benzimidazols für die Behandlung von Pilzinfek- tionen des menschlichen oder tierischen Körpers vorgeschlagen worden, jedoch haben sich diese Verbin- dungen nicht als völlig zufriedenstellend erwiesen.
Die vorliegende Erfindung bezieht sich nun auf ein Verfahren zur Herstellung von neuen Derivaten des Benzimidazols, welche eine überlegene therapeutische Wirkung ausüben und der Formel I entspre- chen :
EMI1.1
worin X einen gegebenenfalls durch Hydroxylgruppen substituierten Alkylrest mit bis zu 4 Kohlenstoffatomen, Y ein Halogenatom und die Reste Ri bis R4 Wasserstoff, niedere A. t. kylreste, Halogenatome, Nitrogruppen oder gegebenenfalls substituierte Aminogruppen bedeuten.
Das erfindungsgemässe Verfahren, ist dadurch gekennzeichnet, dass man eine Verbindung der Formel II
EMI1.2
mit einer Säure der Formel III X-COOH III oder mit einem funktionellen Derivat einer solchen Säure erhitzt.
Man kann auch das durch Umsetzung einer Verbindung der Formel II mit einer Säure der Formel III o ! daer mit einem funktionellen Derivat einer solchen Säure gebildete Zwischenprodukt der Formel IV
EMI1.3
durch Erhitzen in Gegenwart eines Lösungsmittels in das entsprechende Benzimidazolderivat überführen.
Vorzugsweise wird das Zwischenprodukt nicht isoliert und das erfindungsgemässe Verfahren in einer Stufe durchgeführt.
Die erfindungsgemäss erhältlichen neuen Benz- imidazoiderivate lassen sich in an sich üblicher Weise mit Säuren in, ihre Salze überführen.
Die neuen Derivate des Benzimidazols wirken sehr stark fungistatisch. Daneben haben sie sehr gute spasmolytischle Eigenschaften. Die überlegene Wirkung der neuen Benzimidazolderivate ergibt sich aus Vergleichsversuchen, bei denen die Wirkung der Substanz auf den durch Acetylcholin oder Bariumchlorid hervor, gerufenen Krampf des Meerschweinchendarmes mit dem des Papaverins verglichen wurde.
Die erhaltenen Werte sind aus der folgenden Tabelle ersichtlich :
Substanz Wirkung nach Krampferzeugung durch Acetylcholin BaC12 1. Papaverin (bekannt) 100 100 2.1-p-Chlorbenzyl-2-pyrrolidinomethyl benzimidazol-hydrochlorid (bekannt) 150 100 3.1-p-Chlorbenzyl-2-morpholinomethyl benzimidazol-hydrochlorid (bekannt) 220 60 4. l-p-Chlorbenzyl-2-methyl-benzimidazol- hydrochlorid (Beispiel 1) 450 180 5.1-p-ChlorbLenzyl-2-oxymethyl benzimidazol (Beispiel 2) 300 140
Die überlegene fungistatische Wirksamkeit der neuen Benzimidazolderivate z.
B. im Vergleich zu dem aus dem deutschen Patent Nr. 927993 bekann- ten 1-p-Chlorbenzyl-benzimidazol (Verbindung I) geht aus folgender Tabelle hervor : Produkt : Grenzverdünnungen für die Wirksamkeit gegen Hautpilze
Epidermophyton Sporotrichon Trichophyton Candida Kauffmann-Wolff Beurmann interdigitale albicans 1 1 : 20000 1 : 10000 1 : 20000 1 : 10000 II 1 : 100000 1 : 100000 1 : 100000 1 : 10000 I = 1-p-Chlorbenzylbenzimidazol DBP Nr. 927993.
II = 1-p-Chlorbenzyl-2-methyl-benzimidazol-hydrochlorid.
BeisDiel 1
23,3 g p-Chlorbenzyl-o-phenylendiamin werden mit 75 cm3 Eisessig für 3 Stunden am Rückflusskühler gekocht. Die Hauptmenge der Essigsäure wird dann abdestilliert, der Rückstand mit verdünnter Natron- lauge bis zur schwach alkalischen Reaktion versetzt und die dabei erhaltene Base des 1-p-Chlorbenzyl 2-methylbenzimidazols entweder als solche durch Umkristallisation gereinigt oder in das Hydrochlorid übergeführt, das nach Umkristallisieren aus Wasser bei 227-228 C schmilzt.
Beispiel 2
23,3 g p-Chlorbenzyl-o-phenylendiamin werden mit 50 cm3 18"/ & iger Salzsäure versetzt und dann dazu ein Gemisch aus 35 cm3 36 feiger Glykolsäure- lösung und 22 cm3 36"/ iger Salzsäure zugegeben.
Das Reaktionsgemisch wird 2 Stunden lang am Rückflusskühler gekocht und dann nach Versetzen mit dem gleichen Volumen Wasser mit Kohle ver-setzt, aufgekocht und abgesaugt. Das Filtrat wird mit Ammoniaklösung schwach alkalisch gemacht und die dabei erhaltene Base des 1-p-Chlorbenzyl-2- oxymethylbenzimidazols aus wässrigem Alkohol umkristallisiert (Fp. 165 ).
Process for the preparation of new derivatives of benzimidazole
The therapeutic effect of the substitution products of benzimidazole has been repeatedly investigated. It has been found that the effect varies widely depending on the nature of the substituents.
With regard to the substituents in the 2-position of the benzimidazole, it has been found that hydrocarbon residues as substituents in the 2-position lead to products with a very low spasmolytic effect (J. Am. Chem.
Soc. 71, p. 2035), while substituents with basic N atoms in the 2-position of the benzimidazole lead to practically usable products if the 1-position is replaced by a substituted or unsubstituted aralkyl, aryl or heterocyclic radical or . Heterocyclically substituted alkyl radical is occupied (DBP No. 890644).
A number of derivatives of benzimidazole have also been proposed for the treatment of fungal infections of the human or animal body, but these compounds have not proven to be entirely satisfactory.
The present invention now relates to a process for the preparation of new derivatives of benzimidazole, which have a superior therapeutic effect and correspond to the formula I:
EMI1.1
wherein X is an alkyl radical optionally substituted by hydroxyl groups and having up to 4 carbon atoms, Y is a halogen atom and the radicals Ri to R4 are hydrogen, lower A. t. mean alkyl radicals, halogen atoms, nitro groups or optionally substituted amino groups.
The process according to the invention is characterized in that a compound of the formula II
EMI1.2
heated with an acid of the formula III X-COOH III or with a functional derivative of such an acid.
You can also do that by reacting a compound of the formula II with an acid of the formula III o! the intermediate of formula IV formed with a functional derivative of such an acid
EMI1.3
converted into the corresponding benzimidazole derivative by heating in the presence of a solvent.
The intermediate product is preferably not isolated and the process according to the invention is carried out in one step.
The new benzimidazoid derivatives obtainable according to the invention can be converted into their salts with acids in a conventional manner.
The new derivatives of benzimidazole have a very strong fungistatic effect. They also have very good spasmolytic properties. The superior effect of the new benzimidazole derivatives results from comparative tests in which the effect of the substance on the spasm of the guinea pig intestine caused by acetylcholine or barium chloride was compared with that of papaverine.
The values obtained can be seen in the following table:
Substance Effect after convulsions caused by acetylcholine BaC12 1. Papaverine (known) 100 100 2.1-p-chlorobenzyl-2-pyrrolidinomethyl benzimidazole hydrochloride (known) 150 100 3.1-p-chlorobenzyl-2-morpholinomethyl benzimidazole hydrochloride (known) 220 60 4 lp-chlorobenzyl-2-methyl-benzimidazole hydrochloride (example 1) 450 180 5.1-p-chlorobenzyl-2-oxymethyl benzimidazole (example 2) 300 140
The superior fungistatic effectiveness of the new benzimidazole z.
B. in comparison with the 1-p-chlorobenzylbenzimidazole (compound I) known from German patent no. 927993 is shown in the following table: Product: Limiting dilutions for the effectiveness against skin fungi
Epidermophyton Sporotrichon Trichophyton Candida Kauffmann-Wolff Beurmann interdigitale albicans 1 1: 20000 1: 10000 1: 20000 1: 10000 II 1: 100000 1: 100000 1: 100000 1: 10000 I = 1-p-chlorobenzylbenzimidazole DBP No. 927993.
II = 1-p-chlorobenzyl-2-methyl-benzimidazole hydrochloride.
BeisDiel 1
23.3 g of p-chlorobenzyl-o-phenylenediamine are boiled with 75 cm3 of glacial acetic acid for 3 hours on the reflux condenser. Most of the acetic acid is then distilled off, dilute sodium hydroxide solution is added to the residue until a weakly alkaline reaction occurs, and the 1-p-chlorobenzyl 2-methylbenzimidazole base obtained is either purified as such by recrystallization or converted into the hydrochloride, which is recrystallized melts from water at 227-228 C.
Example 2
23.3 g of p-chlorobenzyl-o-phenylenediamine are mixed with 50 cm3 of 18 "hydrochloric acid and then a mixture of 35 cm3 of 36 fig glycolic acid solution and 22 cm3 of 36" hydrochloric acid are added.
The reaction mixture is boiled for 2 hours on the reflux condenser and then, after addition of the same volume of water, carbon is added, boiled and suction filtered. The filtrate is made weakly alkaline with ammonia solution and the 1-p-chlorobenzyl-2-oxymethylbenzimidazole base obtained is recrystallized from aqueous alcohol (melting point 165).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH346261T | 1956-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH362411A true CH362411A (en) | 1962-06-15 |
Family
ID=4507570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH346261A CH362411A (en) | 1956-10-30 | 1956-10-30 | Process for the preparation of new derivatives of benzimidazole |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH362411A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000574A1 (en) * | 1977-08-01 | 1979-02-07 | Ciba-Geigy Ag | Benzimidazole-2 derivatives, their preparation and their use for the preparation of medicaments |
-
1956
- 1956-10-30 CH CH346261A patent/CH362411A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000574A1 (en) * | 1977-08-01 | 1979-02-07 | Ciba-Geigy Ag | Benzimidazole-2 derivatives, their preparation and their use for the preparation of medicaments |
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