CH361000A - Process for the preparation of new benzimidazolyl acetic acid amides - Google Patents
Process for the preparation of new benzimidazolyl acetic acid amidesInfo
- Publication number
- CH361000A CH361000A CH361000DA CH361000A CH 361000 A CH361000 A CH 361000A CH 361000D A CH361000D A CH 361000DA CH 361000 A CH361000 A CH 361000A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzimidazolyl
- acetic acid
- formula
- new
- acid amides
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- STRDCKXOEFPOCT-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)acetamide Chemical class C1=CC=C2NC(CC(=O)N)=NC2=C1 STRDCKXOEFPOCT-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 4
- -1 alkylene radical Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229960003424 phenylacetic acid Drugs 0.000 claims description 3
- 239000003279 phenylacetic acid Substances 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- YTLQFZVCLXFFRK-UHFFFAOYSA-N bendazol Chemical class N=1C2=CC=CC=C2NC=1CC1=CC=CC=C1 YTLQFZVCLXFFRK-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung neuer Benzimidazolyl-essigsäureamide Gegenstand der Erfindung ist die Herstellung von Benzimidazolyl-essigsäureamiden der Formel
EMI0001.0003
oder in den Ringen I und 1I substituierten Derivaten davon, wobei A einen niederen Alkylenrest und R eine tertiäre Aminogruppe bedeutet.
A bedeutet insbesondere Äthylen und R eine gegebenenfalls durch ein Heteroatom unterbrochene niedere Alkyleniminogruppe, wie eine Piperidino-, Pyrrolidino- oder Morpholinogruppe, besonders aber eine Di-niederalkylaminogruppe, vor allem die Di- äthylaminogruppe. Der Ring II ist vorzugsweise un- substituiert oder in 3- und/oder 4-Stellung, insbeson dere in 4-Stellung durch Halogen,
Niederalkyl- oder Niederalkoxygruppen substituiert.
Die erfindungsgemäss erhältlichen neuen Verbin dungen besitzen gute analgetische Wirkung und sollen dementsprechend als Arzneimittel Verwen dung finden.
Besonders wertvoll sind die Essigsäureamide der Formel
EMI0001.0026
in denen R1 für Wasserstoff, Halogen, Nied'eralkyl oder Niederalkoxy und R2 für Wasserstoff oder die Nitrogruppe steht, vor allem das a-[1-(ss-Diäthyl= amino - äthyl) - 5 - nitro-benzimidazolyl-(2)]-a-phenyl- essigsäureamid, das a-[1-(ss Diäthylamino-äthyl)
-5- nitro - benzinudazolyl - (2)] - a - (p-chlor-phenyl)-essig- säureamid und das a-[1-(ss Diäthylamino-äthyl)- benzimidazolyl-(2)-a-(p-chlor-phenyl)-essigsäureamid, und deren Salze. Diese Verbindungen sind zudem gute Muskellrelaxantia.
Das erfindungsgemässe Verfahren ist dadurch ge kennzeichnet, dass man 2-Benzyl-benzimid'azole der
EMI0001.0051
Formel
<tb> I <SEP> -N/ <SEP> <B>C <SEP> -CH</B> <SEP> CN <SEP> H
<tb> A
<tb> R oder in den Ringen I und 1I substituierte Derivate davon mit hydrolysierenden Mitteln behandelt. Die Umwandlung wird z. B. in üblicher Weise durch Behandlung mit .sauren oder alkalischen Mitteln vorgenommen.
Die Umsetzungen werden in An- oder Abwesen heit von Verdünnungs- und/oder Kondensationsmit- teln, wenn nötig bei erhöhter Temperatur, im offenen oder im geschlossenen Gefäss, zweckmässig unter Druck, ausgeführt.
Je nach der Arbeitsweise erhält man die neuen Verbindungen in Form der freien Basen oder ihrer Salze. Aus den Salzen können in an sich bekannter Weise die freien Basen gewonnen werden. Von letz teren lassen sich durch Umsetzung mit Säuren, die zur Bildung therapeutisch verwendbarer Salze ge eignet sind, Salze gewinnen, wie z.
B. der Halogen wasserstoffsäuren, Schwefelsäure, Salpetersäure, Phosphorsäure, Rhodanwasserstoffsäure, Essigsäure, Propionsäure, Oxalsäure, Malonsäure, Bernstein säure, Äpfelsäure, Methansulfonsäure, Äthansulfon- säure, Oxyäthansulfonsäure, Benzol- oder Toluol- sulfonsäure oder von therapeutisch wirksamen Säuren.
Die Ausgangsstoffe sind bekannt oder können nach an sich bekannten Methoden gewonnen werden. Die nach dem erfindungsgemässen Verfahren er haltenen neuen Verbindungen können zur Herstel lung pharmazeutischer Präparate Verwendung fin den, welche sie oder ihre Salze in Mischung mit einem für die enterale, parenterale oder topicale Applikation geeigneten pharmazeutischen,
organi schen oder anorganischen festen oder flüssigen Trägermaterial enthalten.
Im folgenden Beispiel sind die Temperaturen in Celsiusgraden angegeben.
<I>Beispiel</I> <I>1 g</I> a-[14ss Diäthylamino-äthyl)-benzimidazolyl- (2)]-a-phenyl essigsäurenitril wird in 5 ml konzen- trierter Schwefelsäure während 44 Stunden bei 25 stehengelassen. Darauf wird mit Eisessig etwas ver dünnt und auf wässerigen Ammoniak gegossen.
Extraktion mit Chloroform, Trocknen mit Magne- siumsulfat, Eindampfen und Kristallisation aus Äther gibt a-[1-(ss Diäthylamino-äthyl)-benzimid- azolyl-(2)]-a-phenyl-essigsäureamid vom F. 136 bis 137 . Das Hydrochlorid schmilzt bei 150-160 .
Das als Ausgangsstoff verwendete a-[1-(ss Di äthylamino2äthyl)-benzirnid'azolyl-(2)];-a-phenyl-essig- säurenitril kann wie folgt erhalten werden: 69,9g Benzimidazolyl-(2) phenyl-acetonitril wer den in 800 ml absolutem Dioxan aufgeschlämmt, portionenweise 8,6 g gepulvertes Natriumamid ein getragen und dann so lange unter Rühren gekocht, bis keine Ammoniak-Entwicklung mehr nachweisbar ist.
Darauf werden 40,0 g Diäthylamino-äthylchlorid bei 60 zugetropft und 16 Stunden bei 60 gerührt. Das Reaktionsgemisch wird mit Eisessig versetzt, im Vakuum eingedampft; der Rückstand in wässeriger Salzsäure ausgezogen und die mit Äther extrahierte saure Lösung mit konzentriertem Ammoniak alka lisch gestellt.
Darauf wird mit Chloroform extrahiert und der mit Soda gewaschene Chloroformextrakt nach Trocknung mit Magnesiumsulfat eingedampft und das verbleibende rohe a-[1-(ss Diäthylamino- äthyl)-benzimidazolyl]-a-phenyl-acetonitril bei 190 bis 210 (0,1 mm Hg) destilliert. Das Destillat kri- stallisiert aus Äther in farblosen Nadeln vom F.<B>106</B> bis 108 .
In analoger Weise kann man folgende Verbin dungen herstellen: a-[1--(,6-Diäthylamino-äthyl)-benzimidazolyl-(2)]- a-(p-chlor-phenyl)-acetamid, F. 189-190 ; F. des Hydrochlorids 174-175 .
a-[1-(ssDiäthylamino-äthyx)-benzimidazolyl-(2)]- a-(m-methoxy-phenyl)-acetamid, F. 153-154 ; F. des Hydrochlorids 162-164 . a-[ 1-(ss-Diäthylamino-äthyl)-5-nitro-benzimidazolyl- (2)] - a - phenyl - acetamid, F. 133-137 ; Doppel schmelzpunkt des Hydrochlorids 105-115 und 140 bis 160 .
a-[1-(ss-Diäthylamino-äthyl)-5-nitro-benzimidazolyl- (2)]-a-[4'-chlor-phenyl]-acetamid, F. 161-163 ; F. des Hydrochlorids 150-155 .
Process for the preparation of new benzimidazolyl-acetic acid amides The invention relates to the preparation of benzimidazolyl-acetic acid amides of the formula
EMI0001.0003
or derivatives thereof substituted in rings I and 1I, where A is a lower alkylene radical and R is a tertiary amino group.
A denotes in particular ethylene and R denotes a lower alkyleneimino group, optionally interrupted by a heteroatom, such as a piperidino, pyrrolidino or morpholino group, but especially a di-lower alkylamino group, especially the diethylamino group. The ring II is preferably unsubstituted or in the 3- and / or 4-position, in particular in the 4-position by halogen,
Lower alkyl or lower alkoxy groups substituted.
The new compounds obtainable according to the invention have a good analgesic effect and should accordingly be used as medicaments.
The acetic acid amides of the formula are particularly valuable
EMI0001.0026
in which R1 is hydrogen, halogen, lower alkyl or lower alkoxy and R2 is hydrogen or the nitro group, especially the a- [1- (ss-diethyl = amino-ethyl) -5-nitro-benzimidazolyl- (2)] -a-phenyl- acetic acid amide, the a- [1- (ss diethylamino-ethyl)
-5- nitro - benzinudazolyl - (2)] - a - (p-chloro-phenyl) -acetic acid amide and the a- [1- (ss diethylamino-ethyl) - benzimidazolyl- (2) -a- (p- chlorophenyl) acetic acid amide, and their salts. These compounds are also good muscle relaxants.
The inventive method is characterized in that 2-benzyl-benzimid'azole the
EMI0001.0051
formula
<tb> I <SEP> -N / <SEP> <B> C <SEP> -CH </B> <SEP> CN <SEP> H
<tb> A
<tb> R or derivatives thereof substituted in rings I and 1I treated with hydrolyzing agents. The conversion is z. B. made in the usual way by treatment with .acid or alkaline agents.
The reactions are carried out in the presence or absence of diluents and / or condensation agents, if necessary at elevated temperature, in an open or in a closed vessel, expediently under pressure.
Depending on the procedure, the new compounds are obtained in the form of the free bases or their salts. The free bases can be obtained from the salts in a manner known per se. Of the latter can be obtained by reacting with acids that are ge for the formation of therapeutically useful salts, salts such.
B. hydrohalic acids, sulfuric acid, nitric acid, phosphoric acid, hydrofluoric acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, malic acid, methanesulphonic acid, ethanesulphonic acid, oxyethanesulphonic acid, benzene or toluenesulphonic acid or therapeutically active acids.
The starting materials are known or can be obtained by methods known per se. The new compounds obtained by the process according to the invention can be used to manufacture pharmaceutical preparations which contain them or their salts in a mixture with a pharmaceutical, parenteral or topical application suitable for enteral,
contain organic or inorganic solid or liquid carrier material.
In the following example the temperatures are given in degrees Celsius.
<I> Example </I> <I> 1 g </I> a- [14ss diethylamino-ethyl) -benzimidazolyl- (2)] - a-phenylacetic acid nitrile is dissolved in 5 ml of concentrated sulfuric acid for 44 hours at 25 ditched. It is then diluted with glacial acetic acid and poured onto aqueous ammonia.
Extraction with chloroform, drying with magnesium sulfate, evaporation and crystallization from ether gives a- [1- (ss diethylamino-ethyl) -benzimid-azolyl- (2)] -a-phenyl-acetic acid amide with a melting point of 136 to 137. The hydrochloride melts at 150-160.
The a- [1- (ss diethylamino2ethyl) -benzirnid'azolyl- (2)]; -a-phenyl-acetic acid nitrile used as starting material can be obtained as follows: 69.9 g of benzimidazolyl- (2) phenyl-acetonitrile slurried in 800 ml of absolute dioxane, carried in portions 8.6 g of powdered sodium amide and then boiled with stirring until no more ammonia evolution can be detected.
40.0 g of diethylaminoethyl chloride are then added dropwise at 60 and the mixture is stirred at 60 for 16 hours. Glacial acetic acid is added to the reaction mixture and the mixture is evaporated in vacuo; the residue is extracted in aqueous hydrochloric acid and the acidic solution extracted with ether is made alkaline with concentrated ammonia.
Then it is extracted with chloroform and the chloroform extract washed with soda is evaporated after drying with magnesium sulfate and the remaining crude α- [1- (ss diethylamino-ethyl) -benzimidazolyl] -a-phenyl-acetonitrile at 190 to 210 (0.1 mm Hg ) distilled. The distillate crystallizes from ether in colorless needles from F. <B> 106 </B> to 108.
The following compounds can be prepared in an analogous manner: a- [1- (, 6-diethylamino-ethyl) -benzimidazolyl- (2)] - a- (p-chlorophenyl) acetamide, F. 189-190; F. the hydrochloride 174-175.
a- [1- (ss-diethylamino-ethyx) -benzimidazolyl- (2)] - a- (m-methoxyphenyl) -acetamide, m.p. 153-154; F. the hydrochloride 162-164. a- [1- (ss-diethylamino-ethyl) -5-nitro-benzimidazolyl- (2)] - a - phenyl - acetamide, mp 133-137; Hydrochloride double melting point 105-115 and 140-160.
a- [1- (ss-diethylamino-ethyl) -5-nitro-benzimidazolyl- (2)] - a- [4'-chlorophenyl] acetamide, mp 161-163; F. the hydrochloride 150-155.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH361000T | 1957-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH361000A true CH361000A (en) | 1962-03-31 |
Family
ID=4512817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH361000D CH361000A (en) | 1957-07-17 | 1957-07-17 | Process for the preparation of new benzimidazolyl acetic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH361000A (en) |
-
1957
- 1957-07-17 CH CH361000D patent/CH361000A/en unknown
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