CS204999B2 - Způsob výroby nových benzimidazolovýcb derivátů - Google Patents
Způsob výroby nových benzimidazolovýcb derivátů Download PDFInfo
- Publication number
- CS204999B2 CS204999B2 CS752989A CS640677A CS204999B2 CS 204999 B2 CS204999 B2 CS 204999B2 CS 752989 A CS752989 A CS 752989A CS 640677 A CS640677 A CS 640677A CS 204999 B2 CS204999 B2 CS 204999B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- salts
- chloroform
- stirred
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates 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 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000013078 crystal Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 7
- -1 3,4-Dichlorophenylcarbamoyl Chemical group 0.000 description 7
- 150000001556 benzimidazoles Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 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
- 239000003960 organic solvent Substances 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 |
|---|---|
| CS204999B2 true CS204999B2 (cs) | 1981-04-30 |
Family
ID=10994517
Family Applications (3)
| 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 |
| CS752989A CS204998B2 (cs) | 1974-05-02 | 1975-04-29 | Způsob výroby nových benzimidazolových derivátů |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS752989A CS205000B2 (cs) | 1974-05-02 | 1975-04-29 | Fungicídní prostředek |
| CS752989A CS204998B2 (cs) | 1974-05-02 | 1975-04-29 | Způsob výroby nových benzimidazolových derivátů |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2012295805B2 (en) * | 2011-08-18 | 2017-05-04 | Nippon Shinyaku Co., Ltd. | Heterocyclic derivative and pharmaceutical drug |
-
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/CS204999B2/cs unknown
- 1975-04-29 FI FI751289A patent/FI751289A7/fi not_active Application Discontinuation
- 1975-04-29 CS CS752989A patent/CS205000B2/cs unknown
- 1975-04-29 SE SE7505025A patent/SE7505025L/xx unknown
- 1975-04-29 DD DD185755A patent/DD120194A1/xx unknown
- 1975-04-29 YU YU01091/75A patent/YU109175A/xx unknown
- 1975-04-29 CS CS752989A patent/CS204998B2/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 |
|---|---|
| PL193636A1 (pl) | 1978-02-13 |
| SE7505025L (sv) | 1975-11-03 |
| HU171244B (hu) | 1977-12-28 |
| PL102170B1 (pl) | 1979-03-31 |
| PL193637A1 (pl) | 1978-02-27 |
| CS205000B2 (cs) | 1981-04-30 |
| YU109175A (en) | 1982-02-28 |
| FI751289A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-03 |
| CS204998B2 (cs) | 1981-04-30 |
| PL106064B1 (pl) | 1979-11-30 |
| DD120194A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-06-05 |
| SU626694A3 (ru) | 1978-09-30 |
| PL99545B1 (pl) | 1978-07-31 |
| YU108181A (en) | 1982-02-28 |
| DK190675A (da) | 1975-11-03 |
| IN141703B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-09 |
| IL47185A0 (en) | 1975-06-25 |
| SU584769A3 (ru) | 1977-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wright | The chemistry of the benzimidazoles. | |
| US4584383A (en) | Substituted 2-mercapto-imidazoles and their preparation | |
| CA1120471A (en) | Adamantylmethyl hydrazines, their preparation and pharmaceutical composition containing them | |
| US3812145A (en) | Process for the preparation of pyrazolone derivatives | |
| US4018790A (en) | Substituted 1-sulfonylbenzimidazoles | |
| US4436913A (en) | 1H- and 2H- indazole derivatives | |
| CH647237A5 (de) | 5-thiobenzimidazol-derivate, verfahren zur herstellung derselben und deren verwendung in anthelmintischen praeparaten. | |
| CS204999B2 (cs) | Způsob výroby nových benzimidazolovýcb derivátů | |
| EP0179408B1 (de) | Neue Amidoalkylmelamine und Aminoalkylmelamine und Verfahren zu ihrer Herstellung | |
| US3234217A (en) | Pyrazole carboxylic acid hydrazides | |
| Heymann et al. | Derivatives of p, p'-Diaminodiphenyl Sulfone1a | |
| DE2124907A1 (de) | 3 Amino 1,2,4 oxadiazole, Verfahren zu ihrer Herstellung und Arzneipraparate | |
| US3900476A (en) | 2(2'-pyrimidylamino)quinazolines and their preparation | |
| US3455948A (en) | 2-aminobenzimidazole and a process for preparing 2-aminobenzimidazoles | |
| US3501492A (en) | Preparation of benzimidazoles | |
| HU188074B (en) | Process for the preparation of cimetidin | |
| US4316021A (en) | Substituted 1-sulfonylbenzimidazoles | |
| DK164052B (da) | Substituerede azabicycloheptaner og syreadditionssalte deraf, farmaceutiske praeparater indeholdende disse forbindelser, fremgangsmaade til fremstilling deraf samt anvendelse af disse forbindelser til fremstilling af laegemidler | |
| CA1050552A (en) | Benzimidazole derivatives | |
| SU740780A1 (ru) | Способ получени производных 2- /2-/5"-нитрофурил-2" /винил или бутадиенил/ хинолин - 4- карбоновых кислот | |
| CA1087195A (en) | Benzimidazole derivatives | |
| CA1248960A (en) | Substituted 2-mercapto-imidazoles | |
| US2728765A (en) | Penicillin salts of bis-aralkylalkenylenediamines | |
| Ebetino et al. | Chemotherapeutic Nitrofurans. IX. 1 2-[1-Acyl-2-(5-nitrofurfurylidene) hydrazino] acetamides | |
| US3914242A (en) | 3-Imino-1,2-benzisothiazolines |