DE1545780A1 - Process for the preparation of substituted benzimidazole derivatives - Google Patents
Process for the preparation of substituted benzimidazole derivativesInfo
- Publication number
- DE1545780A1 DE1545780A1 DE19651545780 DE1545780A DE1545780A1 DE 1545780 A1 DE1545780 A1 DE 1545780A1 DE 19651545780 DE19651545780 DE 19651545780 DE 1545780 A DE1545780 A DE 1545780A DE 1545780 A1 DE1545780 A1 DE 1545780A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- group
- preparation
- phenyl
- piperidino
- 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
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 8
- -1 ethylpyridyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 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
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 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
- 150000001408 amides Chemical class 0.000 description 1
- YTLQFZVCLXFFRK-UHFFFAOYSA-N bendazol Chemical class N=1C2=CC=CC=C2NC=1CC1=CC=CC=C1 YTLQFZVCLXFFRK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 208000006379 syphilis Diseases 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
-
- 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
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Beschreibungdescription
zu der
Patentanmeldung Γto the
Patent application Γ
der Firmaof the company
EGYBSÜM GYOGYSZBR- es TAPSZBRGZAR n) Budapest X, Kereszturi ut 30-38 (Ungarn;EGYBSÜM GYOGYSZBR- es TAPSZBRGZAR n) Budapest X, Kereszturi ut 30-38 (Hungary;
betreffendconcerning
Verfahren zur Herstellung von susbstituierten BenzimidazolderivatenProcess for the preparation of substituted Benzimidazole derivatives
Der Gegenstand der Erfindung ist ein Verfahren zur Herstellung von neuen, substituierten Sensimidazol· derivaten der allgemeinen Formel IThe object of the invention is a process for the preparation of new, substituted sensimidazole derivatives of the general formula I
worin R1 für Waeserötoff oder für eine Phenyl·, Methoxyphenyl-, (Primethoxyphenyl-, Puryl-, Pyridiyl- oder Aethylpjrrldylgruppe, Rg tür eine Dia,6thyl*mino-r wherein R 1 is a phenyl or Waeserötoff ·, methoxyphenyl, (Primethoxyphenyl-, Puryl-, Pyridiyl- or Aethylpjrrldylgruppe, R g door, a slide, 6thyl mino- * r
■ " ^ ' 7 BAD ORIGINAL■ "^ '7 BAD ORIGINAL
62/5962/59
009816/185t009816 / 185t
Diäthylaftino-, Morpholine-j Piperidino- ode* Pyrrolidinogruppe stehen, wobei aber in Fällen,- nenn R. eine Phenyl- oder Methoxyphenylgruppe bedeutet, R-keine Dirnethylamino- oder Piperidinogruppe sein kann* η β 2 oder 3.Diethylaftino, morpholine-j piperidino or * pyrrolidino group stand, but in cases - call R. denotes a phenyl or methoxyphenyl group, R-denotes none Can be dirnethylamino or piperidino * η β 2 or 3.
Diese auf das zentrale Nervensystem wirkende neue Benzimidazolderivate werden erfindungegemäsa derart hergestellt, dass man Benzimidazole der allgemeinen Formel II These new benzimidazole derivatives, which act on the central nervous system, are made according to the invention prepared in such a way that benzimidazoles of the general formula II
in an sioh bekannter Weise mit Aminoalkylenhalogenide 4er allgemeinen »owwl IIIin a manner known per se with aminoalkylene halides 4 general »owwl III
X - <CH2)n - R2 IIIX - <CH 2 ) n - R 2 III
kondensiert: in diesen Formeln steht J fü» ein Halo» genatom, während R1, R2 und η die obige Bedeutung haben» Die Kondensation wird in einem organischen Lösungsmittel , ZtB. in Benzolr zweokaässig in Anwesenheit eines Kondensationsmittels durchgeführt\ als Kondensationsmittel können Alkali- oder Erdalkalimetalle, deren Amide, Hydride, Oxyde oder Alkoholate angewendet werden* Die Ausgangsstoffe der Synthese können nach bekannten Methoden hergestellt werden«condensed: in these formulas J stands for a halogen atom, while R 1 , R 2 and η have the above meaning “The condensation takes place in an organic solvent, ZtB. in benzene r zweokaässig in the presence of a condensing agent performed \ as a condensing agent can alkali or alkaline earth metals, their amides, hydrides, oxides or alkoxides are applied * The starting materials of the synthesis can be prepared by known methods "
Die erfindungsgemäss hergeetellten neuen Verindungen bilden mit Säuren waeeer lös Hohe, t he rape-The new compounds produced according to the invention form water-soluble high, temperature-rape-
BADBATH
0098167188t0098167188t
utiseh anwendbare Salze. Als selche salzbildende Säuren können 3.3» Salzsäure, Bromwasseratoffeänre, Schwefelsäure. Salpetersäure, Phosphorsäure, Essigsäure, Apfelsäure, Zimtsäure etc angewendet werden. Die neuen Basen bilden ferner mit Alkylhalogtniden, bei Kochen unter Rttekf lues in polaren Lösungemitteln (z.B. in Aceton oder in einem Alkohol) oder fcei längerem Stehen auch bei Zimmertemperatur, quaternäre Salze.useful salts. As a salt-forming one Acids can 3.3 »hydrochloric acid, hydrobromic acid, Sulfuric acid. Nitric acid, phosphoric acid, acetic acid, Malic acid, cinnamic acid etc. can be used. The new bases also form with alkyl halides, when boiling under Rttekf lues in polar solvents (e.g. in acetone or in an alcohol) or longer Standing even at room temperature, quaternary salts.
Die erfindungsgemäss herstellbaren neuen Verbindungen zeigen verschiedene, bei BenzimidasoMerivaten bisher nicht bekannte Wirkungen auf das zentrale Nervensystem. Sie hemmen u.a. die Sekretion von Magensäure und !-fagensäften. Ein Teil dieser Verbindungen,- vor allem die am Stickstoffatom duroh eine Hydroxy. alkyl~8citenket te substituierten Derivate, haben sedative Wirkung. Diese Verbindungen aeigen keine, für Benzyl-benzimidazole übrigens charakteristische atiaungsdepressante Y/irkung, vielmehr treten bei diesen Verbindungen atmungserregende und zentralerregende Wirkungen· auf.The novel compounds which can be prepared according to the invention show various types of benzimidaseo derivatives previously unknown effects on the central nervous system. Among other things, they inhibit the secretion of Gastric acid and gastric juices. Some of these compounds - especially those on the nitrogen atom duroh one Hydroxy. alkyl-8cite chain substituted derivatives, have a sedative effect. These connections aeigen none, by the way, characteristic of benzylbenzimidazoles Atiaungsdepressante Y / ffekt, rather kicking respiratory and central excitation in these compounds Effects on.
Die erfiniu'i£sgem£s8 herstellbaren Verbindungen können a.i sich oder mit weiteren therapeutisch wirkenden Verbindungen kombiniert, unter Anwendung der üblichen pharmazeutischen Hilfsstoffe und pharmazeutischen Herstellungsverfahren zu gebrauchsfertigen Arzneimittelpräparaten verarbeitet werden.The erfiniu'i £ sgem £ s8 establishable connections can a.i itself or combined with other therapeutically active compounds, using the usual pharmaceutical excipients and pharmaceutical Manufacturing processes are processed into ready-to-use pharmaceutical preparations.
- 3 - BAD ORfQINAL- 3 - BAD ORfQINAL
009816/18B>009816 / 18B>
Das erfindungsgemässe Verfahren wird durch das nachstehende Beispiel näher veranschaulicht.The inventive method is through the the following example is illustrated in more detail.
19,52 g (0,1 Mol) 2-Qi-Pyridyl)--benziraidazol und 11,2 g (0,2 Hol) frisch gepulvertes Kaliumhydroxyd werden in 200 ml trockenem 3enzol suspendiert und mit einer Lösung von 13,6 g (o,l Mol) N-(i'"-Chl6rEthyl)- -diäthylamin-Base in 50 ml Benzol versetzt« Das Gemistih wird unter Rttckflußs bis zur völligen Alkylierung (Auflösung) des 2-( ,K-Pyridyl)-benzimidazole erhitzt. Das benzolisohe Re.: \ tionsgemisch wird durch Filtrieren vom ausgeschiedenen anorganischen Salz (KOI) bzw. vom Überschuss der Base (kOH) befreit. Das Filtrat wird fraktioniert destilliert .19.52 g (0.1 mol) 2-Qi-pyridyl) benziraidazole and 11.2 g (0.2 hol) of freshly powdered potassium hydroxide are suspended in 200 ml of dry 3enzol and treated with a solution of 13.6 g (0.1 mol) N- (i '"- Chl6rEthyl) - diethylamine base in 50 ml of benzene added «Das Gemistih is heated under reflux until complete alkylation (dissolution) of 2- (, K-pyridyl) -benzimidazole. The benzeneohe reaction mixture is filtered by filtration freed from the precipitated inorganic salt (KOI) or from the excess of the base (kOH). The filtrate will fractionally distilled.
Di» l-$-Diäthylaminoäthyl)-2-(V -pyridyl)- -benzimidazol-Base siedet bei 0,8 Torr bei 240-2450O. Das aus der ätheriBch-alkoholisohen Lösung der Base gefällte Hydrochlorid schmilzt bei 225-2270CDi 'l - $ - diethylaminoethyl) -2- (V pyridyl) - benzimidazole base boils The precipitated from the ätheriBch-alkoholisohen solution of the base hydrochloride melts at 225-227 at 0.8 torr at 240-245 0 O. 0 C
In ähnlicher Weise werden, unter Verwendung von äquimolekularen Mengen der entsprechenden Ausgangsstoffe die in der nachstehenden Tabelle aufgezählten weiteren Verbindungen der allgemeinen Formel I hergestellt:Similarly, using equimolecular amounts of the appropriate starting materials the other compounds of general formula I listed in the table below are prepared:
009816/186^009816/186 ^
Kp* °C/ma (Base) Ausbeut· P. 0C (Dihydroohlorid) £Bp * ° C / ma (base) yield · P. 0 C (dihydrochloride) £
•ΟΟΗ,• ΟΟΗ,
H -NH -N
'O2H5 'O 2 H 5
H-NH-N
r-\r- \
-N-N
-H-H
Ν00Η3 Ν 00Η 3
H* -I 240-60/1,0-1,5 196-99 H * -I 240-60 / 1.0-1.5 196-99
220/2,5 230-32220 / 2.5 230-32
230/2,5 225-41/6/230 / 2.5 225-41 / 6 /
230/2,5 120-23230 / 2.5 120-23
232-34/0,2 198-200232-34 / 0.2 198-200
280/0,8 138-41280 / 0.8 138-41
260/0,8 Bi COpt63-64) 203-06260 / 0.8 Bi COpt63-64) 203-06
250-60/1,0 206-00250-60 / 1.0 206-00
0099100991
Ü/2% O2H5 O / 2% O 2 H 5
-N-N
238/0,8 208-10238 / 0.8 208-10
240-45/0,8 225-27240-45 / 0.8 225-27
OoHOoH
2"5 220/Oi9 181-84 2 "5 220 / Oi9 181-84
JOJO
-H
\-H
\
,P2H5 , P 2 H 5
C2H5 24O/l,O-l#5 193-97C 2 H 5 24O / l, Oil # 5 193-97
C2H5 C 2 H 5
V5 232/0,25 182-84 V 5 232 / 0.25 182-84
009816/1851 bad" original009816/1851 bad "original
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEE0030557 | 1965-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1545780A1 true DE1545780A1 (en) | 1970-04-16 |
Family
ID=7074581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651545780 Pending DE1545780A1 (en) | 1965-11-29 | 1965-11-29 | Process for the preparation of substituted benzimidazole derivatives |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1545780A1 (en) |
| GB (1) | GB1060558A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2300018A1 (en) * | 1973-01-02 | 1974-07-04 | Knoll Ag | BASIC SUBSTITUTED BENZIMIDAZOLE COMPONENTS |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102206204B (en) * | 2011-04-08 | 2012-12-12 | 奇方(天津)医药科技有限公司 | Benzimidazole compound and medicinal application thereof |
-
1965
- 1965-11-29 DE DE19651545780 patent/DE1545780A1/en active Pending
-
1966
- 1966-01-19 GB GB253466A patent/GB1060558A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2300018A1 (en) * | 1973-01-02 | 1974-07-04 | Knoll Ag | BASIC SUBSTITUTED BENZIMIDAZOLE COMPONENTS |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1060558A (en) | 1967-03-08 |
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