CS204998B2 - Způsob výroby nových benzimidazolových derivátů - Google Patents
Způsob výroby nových benzimidazolových derivátů Download PDFInfo
- Publication number
- CS204998B2 CS204998B2 CS752989A CS298975A CS204998B2 CS 204998 B2 CS204998 B2 CS 204998B2 CS 752989 A CS752989 A CS 752989A CS 298975 A CS298975 A CS 298975A CS 204998 B2 CS204998 B2 CS 204998B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- salts
- benzimidazole derivatives
- group
- producing new
- Prior art date
Links
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- BMVMKBKGIWYRGM-UHFFFAOYSA-N 2-(5-nitrofuran-2-yl)-2-oxoacetyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(=O)C(Cl)=O)O1 BMVMKBKGIWYRGM-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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 group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OLEFNFXYGGTROA-UHFFFAOYSA-N 5-nitrofuran-2-carbonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)O1 OLEFNFXYGGTROA-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- -1 alkyl radical Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU74CI00001473A HU171244B (hu) | 1974-05-02 | 1974-05-02 | Sposob poluchenija novykh proizvodnykh benzimidazola i gerbicidy soderzhahhie takie soedinenija |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS204998B2 true CS204998B2 (cs) | 1981-04-30 |
Family
ID=10994517
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS752989A CS204998B2 (cs) | 1974-05-02 | 1975-04-29 | Způsob výroby nových benzimidazolových derivátů |
| CS752989A CS204999B2 (cs) | 1974-05-02 | 1975-04-29 | Způsob výroby nových benzimidazolovýcb derivátů |
| CS752989A CS205000B2 (cs) | 1974-05-02 | 1975-04-29 | Fungicídní prostředek |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS752989A CS204999B2 (cs) | 1974-05-02 | 1975-04-29 | Způsob výroby nových benzimidazolovýcb derivátů |
| CS752989A CS205000B2 (cs) | 1974-05-02 | 1975-04-29 | Fungicídní prostředek |
Country Status (11)
| Country | Link |
|---|---|
| CS (3) | CS204998B2 (pl) |
| DD (1) | DD120194A1 (pl) |
| DK (1) | DK190675A (pl) |
| FI (1) | FI751289A (pl) |
| HU (1) | HU171244B (pl) |
| IL (1) | IL47185A0 (pl) |
| IN (1) | IN141703B (pl) |
| PL (3) | PL102170B1 (pl) |
| SE (1) | SE7505025L (pl) |
| SU (2) | SU584769A3 (pl) |
| YU (2) | YU109175A (pl) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2844794C (en) * | 2011-08-18 | 2018-02-20 | Nippon Shinyaku Co., Ltd. | Heterocyclic derivatives with mpges-1 inhibitory activity |
-
1974
- 1974-05-02 HU HU74CI00001473A patent/HU171244B/hu unknown
-
1975
- 1975-04-26 IN IN847/CAL/75A patent/IN141703B/en unknown
- 1975-04-28 IL IL47185A patent/IL47185A0/xx unknown
- 1975-04-29 CS CS752989A patent/CS204998B2/cs unknown
- 1975-04-29 SE SE7505025A patent/SE7505025L/xx unknown
- 1975-04-29 YU YU01091/75A patent/YU109175A/xx unknown
- 1975-04-29 CS CS752989A patent/CS204999B2/cs unknown
- 1975-04-29 FI FI751289A patent/FI751289A/fi not_active Application Discontinuation
- 1975-04-29 DD DD185755A patent/DD120194A1/xx unknown
- 1975-04-29 CS CS752989A patent/CS205000B2/cs unknown
- 1975-04-30 SU SU7502131951A patent/SU584769A3/ru active
- 1975-05-01 DK DK190675A patent/DK190675A/da not_active Application Discontinuation
- 1975-05-02 PL PL1975193636A patent/PL102170B1/pl unknown
- 1975-05-02 PL PL1975180100A patent/PL99545B1/pl unknown
- 1975-05-02 PL PL1975193637A patent/PL106064B1/pl unknown
-
1976
- 1976-04-15 SU SU762348905A patent/SU626694A3/ru active
-
1981
- 1981-04-27 YU YU01081/81A patent/YU108181A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK190675A (da) | 1975-11-03 |
| CS205000B2 (cs) | 1981-04-30 |
| PL99545B1 (pl) | 1978-07-31 |
| SE7505025L (sv) | 1975-11-03 |
| SU626694A3 (ru) | 1978-09-30 |
| YU108181A (en) | 1982-02-28 |
| SU584769A3 (ru) | 1977-12-15 |
| PL193636A1 (pl) | 1978-02-13 |
| PL193637A1 (pl) | 1978-02-27 |
| IN141703B (pl) | 1977-04-09 |
| PL106064B1 (pl) | 1979-11-30 |
| PL102170B1 (pl) | 1979-03-31 |
| YU109175A (en) | 1982-02-28 |
| CS204999B2 (cs) | 1981-04-30 |
| DD120194A1 (pl) | 1976-06-05 |
| FI751289A (pl) | 1975-11-03 |
| HU171244B (hu) | 1977-12-28 |
| IL47185A0 (en) | 1975-06-25 |
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