DE890644C - Verfahren zur Darstellung von Derivaten des Imidazole - Google Patents
Verfahren zur Darstellung von Derivaten des ImidazoleInfo
- Publication number
- DE890644C DE890644C DE1950SC001391 DESC001391D DE890644C DE 890644 C DE890644 C DE 890644C DE 1950SC001391 DE1950SC001391 DE 1950SC001391 DE SC001391 D DESC001391 D DE SC001391D DE 890644 C DE890644 C DE 890644C
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- compounds
- heterocyclic
- imidazole
- heterocyclic radical
- 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.)
- Expired
Links
- 150000002460 imidazoles Chemical class 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 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
- 150000001412 amines Chemical class 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- -1 alkylaminoalkyl radical Chemical class 0.000 description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 2
- MMJRINZEHFQMLN-UHFFFAOYSA-N 2-n-(4-methoxyphenyl)benzene-1,2-diamine Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1N MMJRINZEHFQMLN-UHFFFAOYSA-N 0.000 description 2
- ZOBQXWFQMOJTJF-UHFFFAOYSA-N 2-n-benzylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NCC1=CC=CC=C1 ZOBQXWFQMOJTJF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000005001 aminoaryl group Chemical group 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- JLIRPISIPQMEDU-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-nitroaniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1[N+]([O-])=O JLIRPISIPQMEDU-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AIEZSIAPQGBFRC-UHFFFAOYSA-N 1-benzyl-2-(chloromethyl)benzimidazole Chemical compound ClCC1=NC2=CC=CC=C2N1CC1=CC=CC=C1 AIEZSIAPQGBFRC-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- FMSSTWGVVMAWCY-UHFFFAOYSA-N ClO.CNC Chemical compound ClO.CNC FMSSTWGVVMAWCY-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000320 amidine group Chemical group 0.000 description 1
- REYFJDPCWQRWAA-UHFFFAOYSA-N antazoline Chemical compound N=1CCNC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 REYFJDPCWQRWAA-UHFFFAOYSA-N 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LAOUKNRSKBRAMQ-UHFFFAOYSA-N n-benzyl-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NCC1=CC=CC=C1 LAOUKNRSKBRAMQ-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000010792 warming 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
- C07D235/14—Radicals substituted by nitrogen 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
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL73080D NL73080C (enrdf_load_stackoverflow) | 1950-03-03 | ||
| DE1950SC001391 DE890644C (de) | 1950-03-03 | 1950-03-03 | Verfahren zur Darstellung von Derivaten des Imidazole |
| DESCH9058D DE911261C (de) | 1950-03-03 | 1951-01-15 | Verfahren zur Herstellung von Derivaten des Imidazols |
| CH295243D CH295243A (de) | 1950-03-03 | 1951-02-28 | Verfahren zur Darstellung eines Imidazolderivates. |
| FR1056760D FR1056760A (enrdf_load_stackoverflow) | 1950-03-03 | 1951-03-02 | |
| GB516151A GB703272A (en) | 1950-03-03 | 1951-03-02 | Manufacture of new derivatives of benzimidazole |
| GB516251A GB703273A (en) | 1950-03-03 | 1951-03-02 | Manufacture of new derivatives of imidazole |
| DESCH7116D DE901649C (de) | 1950-03-03 | 1951-07-16 | Verfahren zur Herstellung von Derivaten des Imidazols |
| DESCH7115D DE895904C (de) | 1950-03-03 | 1951-07-16 | Verfahren zur Darstellung von Derivaten des Imidazols |
| FR64911D FR64911E (fr) | 1950-03-03 | 1952-07-11 | Dérivés d'imidazol et leur préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1950SC001391 DE890644C (de) | 1950-03-03 | 1950-03-03 | Verfahren zur Darstellung von Derivaten des Imidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE890644C true DE890644C (de) | 1954-07-05 |
Family
ID=31983835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1950SC001391 Expired DE890644C (de) | 1950-03-03 | 1950-03-03 | Verfahren zur Darstellung von Derivaten des Imidazole |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH295243A (enrdf_load_stackoverflow) |
| DE (1) | DE890644C (enrdf_load_stackoverflow) |
| FR (1) | FR1056760A (enrdf_load_stackoverflow) |
| GB (2) | GB703272A (enrdf_load_stackoverflow) |
| NL (1) | NL73080C (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2876233A (en) * | 1956-10-29 | 1959-03-03 | Gruenenthal Chemie | 1-(p-halobenzyl)-2-methyl benzimidazoles and salts |
| CH650768A5 (de) * | 1982-08-27 | 1985-08-15 | Pharmaton Sa | Basische acetanilide, verfahren zu deren herstellung und arzneimittel, die diese acetanilide enthalten. |
| FR2998697A1 (fr) | 2012-11-23 | 2014-05-30 | Univ Bretagne Sud | Architecture de reseau de neurone, procede d'obtention et programmes correspondants |
| GB201702160D0 (en) | 2017-02-09 | 2017-03-29 | Univ Leeds Innovations Ltd | Inhibitors for use in therapy |
-
0
- NL NL73080D patent/NL73080C/xx active
-
1950
- 1950-03-03 DE DE1950SC001391 patent/DE890644C/de not_active Expired
-
1951
- 1951-02-28 CH CH295243D patent/CH295243A/de unknown
- 1951-03-02 FR FR1056760D patent/FR1056760A/fr not_active Expired
- 1951-03-02 GB GB516151A patent/GB703272A/en not_active Expired
- 1951-03-02 GB GB516251A patent/GB703273A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB703273A (en) | 1954-02-03 |
| CH295243A (de) | 1953-12-15 |
| FR1056760A (enrdf_load_stackoverflow) | 1954-03-02 |
| GB703272A (en) | 1954-02-03 |
| NL73080C (enrdf_load_stackoverflow) |
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