DE2259220C2 - Isothiocyanatobenzazole, Verfahren zu ihrer Herstellung und anthelmintische Mittel - Google Patents
Isothiocyanatobenzazole, Verfahren zu ihrer Herstellung und anthelmintische MittelInfo
- Publication number
- DE2259220C2 DE2259220C2 DE2259220A DE2259220A DE2259220C2 DE 2259220 C2 DE2259220 C2 DE 2259220C2 DE 2259220 A DE2259220 A DE 2259220A DE 2259220 A DE2259220 A DE 2259220A DE 2259220 C2 DE2259220 C2 DE 2259220C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- isothiocyanatobenzothiazole
- compounds
- formula
- scn
- 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
- KJCGUQFSJWDPTH-UHFFFAOYSA-N 2-isothiocyanato-1h-indole Chemical compound C1=CC=C2NC(N=C=S)=CC2=C1 KJCGUQFSJWDPTH-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title description 14
- 229940124339 anthelmintic agent Drugs 0.000 title description 6
- 239000000921 anthelmintic agent Substances 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 6
- -1 alkyl radical Chemical class 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 25
- 241001465754 Metazoa Species 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 239000002253 acid Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 244000000013 helminth Species 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000000507 anthelmentic effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- UNZKUUJWWXVDCI-UHFFFAOYSA-N 2-isothiocyanato-1,3-benzoxazole Chemical class C1=CC=C2OC(N=C=S)=NC2=C1 UNZKUUJWWXVDCI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 230000003071 parasitic effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- GYAHPKTUKBGNBW-UHFFFAOYSA-N 2-tert-butyl-6-isothiocyanato-1,3-benzothiazole Chemical compound C1=C(N=C=S)C=C2SC(C(C)(C)C)=NC2=C1 GYAHPKTUKBGNBW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000869417 Trematodes Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007366 host health Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000004308 thiabendazole Substances 0.000 description 2
- 235000010296 thiabendazole Nutrition 0.000 description 2
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 2
- 229960004546 thiabendazole Drugs 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 150000003585 thioureas Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000004385 trihaloalkyl group Chemical group 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- XTRNTWFPJIZGBG-UHFFFAOYSA-N 1,3-benzothiazol-2-yl thiocyanate Chemical compound C1=CC=C2SC(SC#N)=NC2=C1 XTRNTWFPJIZGBG-UHFFFAOYSA-N 0.000 description 1
- JPBLHOJFMBOCAF-UHFFFAOYSA-N 1,3-benzoxazol-2-amine Chemical class C1=CC=C2OC(N)=NC2=C1 JPBLHOJFMBOCAF-UHFFFAOYSA-N 0.000 description 1
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- HBZHNVUMFPGVHW-UHFFFAOYSA-N 2-chloro-1h-indole Chemical class C1=CC=C2NC(Cl)=CC2=C1 HBZHNVUMFPGVHW-UHFFFAOYSA-N 0.000 description 1
- CFSSASYPNKWNEJ-UHFFFAOYSA-N 2-cyclopropyl-6-isothiocyanato-1,3-benzothiazole Chemical compound S1C2=CC(N=C=S)=CC=C2N=C1C1CC1 CFSSASYPNKWNEJ-UHFFFAOYSA-N 0.000 description 1
- JBEXHLHFVASCMQ-UHFFFAOYSA-N 2-ethyl-1,3-benzothiazol-6-amine Chemical compound C1=C(N)C=C2SC(CC)=NC2=C1 JBEXHLHFVASCMQ-UHFFFAOYSA-N 0.000 description 1
- YSAXHYQFYVQRPF-UHFFFAOYSA-N 2-ethyl-5-isothiocyanato-1,3-benzothiazole Chemical compound S=C=NC1=CC=C2SC(CC)=NC2=C1 YSAXHYQFYVQRPF-UHFFFAOYSA-N 0.000 description 1
- OGJUAHYUZXOXMH-UHFFFAOYSA-N 2-ethyl-5-isothiocyanato-1,3-benzoxazole Chemical compound S=C=NC1=CC=C2OC(CC)=NC2=C1 OGJUAHYUZXOXMH-UHFFFAOYSA-N 0.000 description 1
- BJUFGMWWTVOPQG-UHFFFAOYSA-N 2-ethyl-6-isothiocyanato-1,3-benzothiazole Chemical compound C1=C(N=C=S)C=C2SC(CC)=NC2=C1 BJUFGMWWTVOPQG-UHFFFAOYSA-N 0.000 description 1
- JVBGZMMWOYACGD-UHFFFAOYSA-N 2-ethyl-6-isothiocyanato-1,3-benzothiazole;hydrochloride Chemical group Cl.C1=C(N=C=S)C=C2SC(CC)=NC2=C1 JVBGZMMWOYACGD-UHFFFAOYSA-N 0.000 description 1
- BOPXGBDKSQDNAT-UHFFFAOYSA-N 2-isothiocyanato-1,3-benzothiazole Chemical class C1=CC=C2SC(N=C=S)=NC2=C1 BOPXGBDKSQDNAT-UHFFFAOYSA-N 0.000 description 1
- NSYKYZBOQLCIHR-UHFFFAOYSA-N 2-nitro-1,3-benzothiazole Chemical class C1=CC=C2SC([N+](=O)[O-])=NC2=C1 NSYKYZBOQLCIHR-UHFFFAOYSA-N 0.000 description 1
- JVDYWBQJOUXQBB-UHFFFAOYSA-N 2-nitro-1,3-benzoxazole Chemical class C1=CC=C2OC([N+](=O)[O-])=NC2=C1 JVDYWBQJOUXQBB-UHFFFAOYSA-N 0.000 description 1
- HCGYMSSYSAKGPK-UHFFFAOYSA-N 2-nitro-1h-indole Chemical class C1=CC=C2NC([N+](=O)[O-])=CC2=C1 HCGYMSSYSAKGPK-UHFFFAOYSA-N 0.000 description 1
- HWXYBXYFYWOVAS-UHFFFAOYSA-N 2-propan-2-yl-1,3-benzothiazol-6-amine Chemical compound C1=C(N)C=C2SC(C(C)C)=NC2=C1 HWXYBXYFYWOVAS-UHFFFAOYSA-N 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
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- CDMGDVBAMGRJLZ-UHFFFAOYSA-N 6-isothiocyanato-2-methoxy-1,3-benzothiazole Chemical compound C1=C(N=C=S)C=C2SC(OC)=NC2=C1 CDMGDVBAMGRJLZ-UHFFFAOYSA-N 0.000 description 1
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- UGVJBJKBJQYTRK-UHFFFAOYSA-N 6-isothiocyanato-2-methyl-1,3-benzoxazole Chemical compound C1=C(N=C=S)C=C2OC(C)=NC2=C1 UGVJBJKBJQYTRK-UHFFFAOYSA-N 0.000 description 1
- JTMFRQQPIHUVPI-UHFFFAOYSA-N 6-isothiocyanato-2-methylsulfanyl-1,3-benzothiazole Chemical compound C1=C(N=C=S)C=C2SC(SC)=NC2=C1 JTMFRQQPIHUVPI-UHFFFAOYSA-N 0.000 description 1
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- JPJDJLGIJZRLTH-UHFFFAOYSA-N 6-isothiocyanato-3h-1,3-benzothiazol-2-one Chemical compound C1=C(N=C=S)C=C2SC(O)=NC2=C1 JPJDJLGIJZRLTH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- 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
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- 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
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- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- 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
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- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
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- 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
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
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- 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
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- 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
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- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
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- 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
- C07D235/26—Oxygen atoms
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- 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
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- 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1787571A CH566321A5 (OSRAM) | 1971-12-07 | 1971-12-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2259220A1 DE2259220A1 (de) | 1973-06-14 |
| DE2259220C2 true DE2259220C2 (de) | 1984-05-17 |
Family
ID=4428743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2259220A Expired DE2259220C2 (de) | 1971-12-07 | 1972-12-04 | Isothiocyanatobenzazole, Verfahren zu ihrer Herstellung und anthelmintische Mittel |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US3849431A (OSRAM) |
| JP (1) | JPS5754511B2 (OSRAM) |
| AR (1) | AR220663A1 (OSRAM) |
| AT (2) | AT322550B (OSRAM) |
| BE (1) | BE792402A (OSRAM) |
| BG (1) | BG21027A3 (OSRAM) |
| BR (1) | BR7208610D0 (OSRAM) |
| CA (1) | CA1014566A (OSRAM) |
| CH (1) | CH566321A5 (OSRAM) |
| CS (2) | CS177148B2 (OSRAM) |
| DD (1) | DD105230A5 (OSRAM) |
| DE (1) | DE2259220C2 (OSRAM) |
| ES (1) | ES409335A1 (OSRAM) |
| FI (1) | FI56531C (OSRAM) |
| GB (1) | GB1413519A (OSRAM) |
| HU (1) | HU167426B (OSRAM) |
| IE (1) | IE37194B1 (OSRAM) |
| IL (1) | IL40935A (OSRAM) |
| IT (1) | IT1048106B (OSRAM) |
| NL (1) | NL7216645A (OSRAM) |
| NO (1) | NO137234C (OSRAM) |
| PL (2) | PL85278B1 (OSRAM) |
| RO (1) | RO60572A (OSRAM) |
| SE (1) | SE402772B (OSRAM) |
| SU (2) | SU589915A3 (OSRAM) |
| YU (1) | YU36711B (OSRAM) |
| ZA (1) | ZA728643B (OSRAM) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3894037A (en) * | 1971-05-24 | 1975-07-08 | Ciba Geigy Corp | Certain isothiocyanobenzimidazoles |
| US3933841A (en) * | 1971-05-24 | 1976-01-20 | Ciba-Geigy Corporation | 2-Phenoxy, -phenylthio-, and -phenyl-amino-benzoxazoles having an isothiocyano substituent |
| US3969351A (en) * | 1974-05-17 | 1976-07-13 | E. R. Squibb & Sons, Inc. | Morpholine containing isothiocyanobenzoxazoles |
| LU75684A1 (OSRAM) * | 1976-08-27 | 1978-04-13 | ||
| US4197307A (en) * | 1977-04-12 | 1980-04-08 | Ciba-Geigy Corporation | 2-Alkylthio-, 2-alkylsulphinyl- and 2-alkylsulfonyl-6-phenylbenzimidazoles as anthelmintic agents |
| EP0007616B1 (de) | 1978-07-27 | 1982-05-12 | Ciba-Geigy Ag | Isothiocyanobenzthiazolderivat, Verfahren zu seiner Herstellung und seine Anwendung in anthelmintischen Mitteln |
| US4287349A (en) * | 1979-04-23 | 1981-09-01 | Standard Oil Company (Indiana) | Beta-alkyl (or aryl) beta-hydroxyethyl heterocyclic sulfoxides |
| FR2459239A1 (fr) * | 1979-06-20 | 1981-01-09 | Logeais Labor Jacques | Nouveaux derives amines du benzothiazole, leur procede de preparation et leur application en therapeutique |
| DE2946524A1 (de) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| US4267348A (en) * | 1979-12-04 | 1981-05-12 | The United States Of America As Represented By The Secretary Of The Air Force | Fluorine-containing benzimidazoles |
| US4375470A (en) * | 1980-02-04 | 1983-03-01 | American Home Products Corporation | 2(1-Piperazinyl)-cycloheptimidazole antihypertensive composition and methods |
| US4258188A (en) * | 1980-02-04 | 1981-03-24 | American Home Products Corporation | 2-(1-Piperazinyl)-cycloheptimidazole derivatives |
| US4321363A (en) * | 1980-02-21 | 1982-03-23 | Nippon Soda Company Limited | Adsorbent for urokinase containing agarose |
| MA19290A1 (fr) * | 1980-05-22 | 1982-04-01 | Ciba Geigy Ag | Derives du benzole,leur preparaton et leur utilisations therapeutiques . |
| DE3027483A1 (de) * | 1980-07-19 | 1982-02-25 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung heterocyclisch substituierter 4-oxiphenoxialkancarbonsaeurederivate |
| DE3039929A1 (de) * | 1980-10-23 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | Isocyanato-oxazolinone, ein verfahren zur herstellung von oxazolin-2-on-ringe aufweisenden kunststoffvorlaeufern und deren verwendung zur herstellung von hochmolekularen kunststoffen |
| FR2521141A1 (fr) * | 1982-02-09 | 1983-08-12 | Rhone Poulenc Agrochimie | Nouveaux derives du cyano-2 benzimidazole, leur preparation et leur utilisation comme fongicides |
| DE3311285A1 (de) * | 1983-03-28 | 1984-10-11 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung heterocyclischer phenylether |
| GB8423697D0 (en) * | 1984-09-19 | 1984-10-24 | Ciba Geigy Ag | Benzazole derivatives |
| US4873346A (en) * | 1985-09-20 | 1989-10-10 | The Upjohn Company | Substituted benzothiazoles, benzimidazoles, and benzoxazoles |
| EP0507464A1 (en) * | 1991-03-28 | 1992-10-07 | Zeneca Limited | Benzoxazole derivatives |
| GB9219634D0 (en) * | 1992-09-16 | 1992-10-28 | Ici Plc | Heterocyclic compounds |
| FR2708608B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés de N-sulfonylbenzimidazolone, leur préparation, les compositions pharmaceutiques en contenant. |
| RU2119334C1 (ru) * | 1996-05-20 | 1998-09-27 | Всероссийский научно-исследовательский институт гельминтологии имени К.И.Скрябина | Антгельминтное средство |
| UA66810C2 (uk) | 1997-10-27 | 2004-06-15 | Агорон Фармацевтикалз Інк. | Похідні 4-амінотіазолу та композиції на їх основі як інгібітори циклінозалежних кіназ |
| CA2553724A1 (en) * | 2004-02-03 | 2005-08-18 | Abbott Laboratories | Aminobenzoxazoles as therapeutic agents |
| US9086416B2 (en) * | 2011-07-12 | 2015-07-21 | Academia Sinica | Removable saccharide-benzimidazole (BIM) tags and conjugates thereof via 1H-position of the benzimidazoles |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH542853A (de) * | 1967-07-26 | 1973-10-15 | Agripat Sa | Verfahren zur Herstellung neuer Isothiocyano-benzazol-Derivate |
| AT286292B (de) * | 1969-01-10 | 1970-12-10 | Agripat Sa | Verfahren zur Herstellung von neuen Isothiocyano-benzimidazol- und -benzoxazolderivaten und ihren Salzen |
-
0
- BE BE792402D patent/BE792402A/xx not_active IP Right Cessation
-
1971
- 1971-12-07 CH CH1787571A patent/CH566321A5/xx not_active IP Right Cessation
-
1972
- 1972-11-09 FI FI3138/72A patent/FI56531C/fi active
- 1972-11-14 SE SE7214765A patent/SE402772B/xx unknown
- 1972-11-27 IL IL40935A patent/IL40935A/en unknown
- 1972-11-27 IE IE1640/72A patent/IE37194B1/xx unknown
- 1972-11-28 CA CA157,628A patent/CA1014566A/en not_active Expired
- 1972-12-01 GB GB5563272A patent/GB1413519A/en not_active Expired
- 1972-12-01 YU YU2980/72A patent/YU36711B/xx unknown
- 1972-12-04 BG BG022033A patent/BG21027A3/xx unknown
- 1972-12-04 US US00311987A patent/US3849431A/en not_active Expired - Lifetime
- 1972-12-04 DE DE2259220A patent/DE2259220C2/de not_active Expired
- 1972-12-05 AR AR245484A patent/AR220663A1/es active
- 1972-12-05 DD DD167302A patent/DD105230A5/xx unknown
- 1972-12-05 PL PL1972159306A patent/PL85278B1/pl unknown
- 1972-12-05 PL PL1972175279A patent/PL86697B1/pl unknown
- 1972-12-06 BR BR8610/72A patent/BR7208610D0/pt unknown
- 1972-12-06 AT AT1037372A patent/AT322550B/de not_active IP Right Cessation
- 1972-12-06 HU HUCI1311A patent/HU167426B/hu unknown
- 1972-12-06 IT IT32618/72A patent/IT1048106B/it active
- 1972-12-06 ES ES409335A patent/ES409335A1/es not_active Expired
- 1972-12-06 ZA ZA728643A patent/ZA728643B/xx unknown
- 1972-12-06 SU SU721855799A patent/SU589915A3/ru active
- 1972-12-06 AT AT449474*1A patent/AT324761B/de not_active IP Right Cessation
- 1972-12-06 NO NO4494/72A patent/NO137234C/no unknown
- 1972-12-07 CS CS227A patent/CS177148B2/cs unknown
- 1972-12-07 JP JP47123021A patent/JPS5754511B2/ja not_active Expired
- 1972-12-07 RO RO73073A patent/RO60572A/ro unknown
- 1972-12-07 NL NL7216645A patent/NL7216645A/xx not_active Application Discontinuation
- 1972-12-07 CS CS8387A patent/CS177109B2/cs unknown
-
1975
- 1975-03-05 SU SU2110985A patent/SU541433A3/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C07D277/62 |
|
| 8126 | Change of the secondary classification |
Free format text: C07D263/54 C07D277/68 C07D277/64 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |