DE2366069C2 - - Google Patents
Info
- Publication number
- DE2366069C2 DE2366069C2 DE2366069A DE2366069A DE2366069C2 DE 2366069 C2 DE2366069 C2 DE 2366069C2 DE 2366069 A DE2366069 A DE 2366069A DE 2366069 A DE2366069 A DE 2366069A DE 2366069 C2 DE2366069 C2 DE 2366069C2
- Authority
- DE
- Germany
- Prior art keywords
- carbomethoxyaminobenzimidazole
- nitro
- treated
- mixture
- chloroform
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 22
- -1 alkynyl radical Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- KHBXLYPOXVQKJG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)OC KHBXLYPOXVQKJG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- VCKJSKHOGHYRTC-UHFFFAOYSA-N methyl N-(4-sulfanyl-1H-benzimidazol-2-yl)carbamate Chemical compound SC1=CC=CC=2N=C(NC=21)NC(=O)OC VCKJSKHOGHYRTC-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- RLPLNYIDEVVEBK-UHFFFAOYSA-N (4-acetamido-3-nitrophenyl) thiocyanate Chemical compound CC(=O)NC1=CC=C(SC#N)C=C1[N+]([O-])=O RLPLNYIDEVVEBK-UHFFFAOYSA-N 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- QUWHIBBGKKRYFW-UHFFFAOYSA-N (4-amino-3-nitrophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1[N+]([O-])=O QUWHIBBGKKRYFW-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 3
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 3
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- JVSORZTZKODIJB-UHFFFAOYSA-N (3,4-diaminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1N JVSORZTZKODIJB-UHFFFAOYSA-N 0.000 description 2
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 description 2
- VHQCBSZJSOOPBX-UHFFFAOYSA-N 3-amino-4-nitrobenzenethiol Chemical compound NC1=CC(S)=CC=C1[N+]([O-])=O VHQCBSZJSOOPBX-UHFFFAOYSA-N 0.000 description 2
- LSQOETHDRXOYJB-UHFFFAOYSA-N 4-(2-ethoxyethylsulfanyl)benzene-1,2-diamine Chemical compound CCOCCSC1=CC=C(N)C(N)=C1 LSQOETHDRXOYJB-UHFFFAOYSA-N 0.000 description 2
- LZWIKKPNIVNMFH-UHFFFAOYSA-N 4-(methylsulfanylmethylsulfanyl)-2-nitroaniline Chemical compound CSCSC1=CC=C(N)C([N+]([O-])=O)=C1 LZWIKKPNIVNMFH-UHFFFAOYSA-N 0.000 description 2
- 241000760148 Aspiculuris tetraptera Species 0.000 description 2
- JMWOVRYEQBYLJT-UHFFFAOYSA-N C(C)(=O)NC1=C(C(=C(C=C1)COC)S)[N+](=O)[O-] Chemical compound C(C)(=O)NC1=C(C(=C(C=C1)COC)S)[N+](=O)[O-] JMWOVRYEQBYLJT-UHFFFAOYSA-N 0.000 description 2
- 241000244203 Caenorhabditis elegans Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 241001464384 Hymenolepis nana Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 2
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- WWGPFEMUMRARLF-UHFFFAOYSA-N n-(4-benzylsulfanyl-2-nitrophenyl)acetamide Chemical compound C1=C([N+]([O-])=O)C(NC(=O)C)=CC=C1SCC1=CC=CC=C1 WWGPFEMUMRARLF-UHFFFAOYSA-N 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- BZZXQZOBAUXLHZ-UHFFFAOYSA-N (c-methylsulfanylcarbonimidoyl)azanium;sulfate Chemical compound CSC(N)=N.CSC(N)=N.OS(O)(=O)=O BZZXQZOBAUXLHZ-UHFFFAOYSA-N 0.000 description 1
- NEFNOUUWYACOKP-UHFFFAOYSA-N 1-(chloromethoxy)butane Chemical compound CCCCOCCl NEFNOUUWYACOKP-UHFFFAOYSA-N 0.000 description 1
- IFMYFXJJIIGOIS-UHFFFAOYSA-N 1-(pyridin-3-ylmethyl)piperidin-4-amine;trihydrochloride Chemical compound Cl.Cl.Cl.C1CC(N)CCN1CC1=CC=CN=C1 IFMYFXJJIIGOIS-UHFFFAOYSA-N 0.000 description 1
- MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical compound CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- AVMHMVJVHYGDOO-UHFFFAOYSA-N 1-bromobut-2-ene Chemical compound CC=CCBr AVMHMVJVHYGDOO-UHFFFAOYSA-N 0.000 description 1
- LNNXOEHOXSYWLD-UHFFFAOYSA-N 1-bromobut-2-yne Chemical compound CC#CCBr LNNXOEHOXSYWLD-UHFFFAOYSA-N 0.000 description 1
- SGEUYXUPUOLFHQ-UHFFFAOYSA-N 1-bromohex-2-ene Chemical compound CCCC=CCBr SGEUYXUPUOLFHQ-UHFFFAOYSA-N 0.000 description 1
- VIXOOIRHFJMNBT-UHFFFAOYSA-N 1-bromohex-2-yne Chemical compound CCCC#CCBr VIXOOIRHFJMNBT-UHFFFAOYSA-N 0.000 description 1
- FTBPZRNURKMEFD-UHFFFAOYSA-N 1-bromopent-2-ene Chemical compound CCC=CCBr FTBPZRNURKMEFD-UHFFFAOYSA-N 0.000 description 1
- VDHGRVFJBGRHMD-UHFFFAOYSA-N 1-bromopent-2-yne Chemical compound CCC#CCBr VDHGRVFJBGRHMD-UHFFFAOYSA-N 0.000 description 1
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 1
- BQLHMMQUVJCTAN-UHFFFAOYSA-N 1-chloro-3-methoxypropane Chemical compound COCCCCl BQLHMMQUVJCTAN-UHFFFAOYSA-N 0.000 description 1
- XPJUCMIJGVAEGF-UHFFFAOYSA-N 1-chloro-4-(chloromethylsulfanyl)benzene Chemical compound ClCSC1=CC=C(Cl)C=C1 XPJUCMIJGVAEGF-UHFFFAOYSA-N 0.000 description 1
- DFLRARJQZRCCKN-UHFFFAOYSA-N 1-chloro-4-methoxybutane Chemical compound COCCCCCl DFLRARJQZRCCKN-UHFFFAOYSA-N 0.000 description 1
- OCZWFZLAGGQRDL-UHFFFAOYSA-N 1-chlorobutane-1-thiol Chemical compound CCCC(S)Cl OCZWFZLAGGQRDL-UHFFFAOYSA-N 0.000 description 1
- QXRYSTFZBZQNDU-UHFFFAOYSA-N 1-chlorobutane-2-thiol Chemical compound CCC(S)CCl QXRYSTFZBZQNDU-UHFFFAOYSA-N 0.000 description 1
- AVNKBORAZHJHQE-UHFFFAOYSA-N 1-chloroethanethiol Chemical compound CC(S)Cl AVNKBORAZHJHQE-UHFFFAOYSA-N 0.000 description 1
- LKYGHVSDLFQQBM-UHFFFAOYSA-N 1-chloropentane-1-thiol Chemical compound CCCCC(S)Cl LKYGHVSDLFQQBM-UHFFFAOYSA-N 0.000 description 1
- AABRDTBRQHKNGS-UHFFFAOYSA-N 1-chloropropane-1-thiol Chemical compound CCC(S)Cl AABRDTBRQHKNGS-UHFFFAOYSA-N 0.000 description 1
- MFBBDMRTISGAGR-UHFFFAOYSA-N 1-chloropropane-2-thiol Chemical compound CC(S)CCl MFBBDMRTISGAGR-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QTKHXEAIGWJFPO-UHFFFAOYSA-N 2-benzylbenzenethiol Chemical compound SC1=CC=CC=C1CC1=CC=CC=C1 QTKHXEAIGWJFPO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- PIWDDCGEUOZMHB-UHFFFAOYSA-N 4-(2-ethoxyethylsulfanyl)-2-nitroaniline Chemical compound CCOCCSC1=CC=C(N)C([N+]([O-])=O)=C1 PIWDDCGEUOZMHB-UHFFFAOYSA-N 0.000 description 1
- QCMUICPFWNAGBF-UHFFFAOYSA-N 4-(methoxymethylsulfanyl)-2-nitroaniline Chemical compound COCSC1=CC=C(N)C([N+]([O-])=O)=C1 QCMUICPFWNAGBF-UHFFFAOYSA-N 0.000 description 1
- SPZOIXIIJMSYAZ-UHFFFAOYSA-N 4-benzylsulfanyl-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1SCC1=CC=CC=C1 SPZOIXIIJMSYAZ-UHFFFAOYSA-N 0.000 description 1
- HLSLIQFXUHQNSS-UHFFFAOYSA-N 4-benzylsulfanylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1SCC1=CC=CC=C1 HLSLIQFXUHQNSS-UHFFFAOYSA-N 0.000 description 1
- DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 1
- XLYOGWXIKVUXCL-UHFFFAOYSA-N 4-bromobut-1-yne Chemical compound BrCCC#C XLYOGWXIKVUXCL-UHFFFAOYSA-N 0.000 description 1
- BOJDKUAGPMFMLS-UHFFFAOYSA-N 4-chlorobutane-2-thiol Chemical compound CC(S)CCCl BOJDKUAGPMFMLS-UHFFFAOYSA-N 0.000 description 1
- FSXGIGKQVXNUOY-UHFFFAOYSA-N 5-(ethoxymethylsulfanyl)-2-nitroaniline Chemical compound CCOCSC1=CC=C([N+]([O-])=O)C(N)=C1 FSXGIGKQVXNUOY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- LWKVZXOPKJSQOX-UHFFFAOYSA-N C(C)C(CCCl)S Chemical compound C(C)C(CCCl)S LWKVZXOPKJSQOX-UHFFFAOYSA-N 0.000 description 1
- JJTAFKVXCJEEMS-UHFFFAOYSA-N CC(CCCCl)S Chemical compound CC(CCCCl)S JJTAFKVXCJEEMS-UHFFFAOYSA-N 0.000 description 1
- 241000242722 Cestoda Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- BTKLCGFHSUJYNL-UHFFFAOYSA-N NC1=C(C(=C(C=C1)COC)S)N Chemical compound NC1=C(C(=C(C=C1)COC)S)N BTKLCGFHSUJYNL-UHFFFAOYSA-N 0.000 description 1
- MOFVVZIZAGGEIN-UHFFFAOYSA-N NC1=C(C(=C(C=C1)COC)S)[N+](=O)[O-] Chemical compound NC1=C(C(=C(C=C1)COC)S)[N+](=O)[O-] MOFVVZIZAGGEIN-UHFFFAOYSA-N 0.000 description 1
- BLSDUQQHDONRHO-UHFFFAOYSA-N NC1=C(C(=C(C=C1)COCC)S)N Chemical compound NC1=C(C(=C(C=C1)COCC)S)N BLSDUQQHDONRHO-UHFFFAOYSA-N 0.000 description 1
- BVXVNTYGWKRBDQ-UHFFFAOYSA-N NC1=C(C(=CC=C1)SCCOCC)[N+](=O)[O-] Chemical compound NC1=C(C(=CC=C1)SCCOCC)[N+](=O)[O-] BVXVNTYGWKRBDQ-UHFFFAOYSA-N 0.000 description 1
- 241001137882 Nematodirus Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 244000046127 Sorghum vulgare var. technicum Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000975692 Syphacia obvelata Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- ARVKQNGPHHAWOW-UHFFFAOYSA-N sulfanyl cyanate Chemical group SOC#N ARVKQNGPHHAWOW-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- 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
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31929972A | 1972-12-29 | 1972-12-29 | |
| US417963A US3929821A (en) | 1972-12-29 | 1973-11-21 | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2366069A1 DE2366069A1 (de) | 1977-11-10 |
| DE2366069C2 true DE2366069C2 (en, 2012) | 1987-06-11 |
Family
ID=26981949
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732366069 Granted DE2366069A1 (de) | 1972-12-29 | 1973-12-20 | Substituierte 5(6)-mercaptobenzimidazol-2- carbaminsaeuremethylester, ihre herstellung und diese enthaltende mittel |
| DE2363351A Expired DE2363351C2 (de) | 1972-12-29 | 1973-12-20 | Substituierte 5(6)-Hydroxy-benzimidazol-2-carbaminsäuremethylester und diese enthaltende Heilmittel |
| DE2366070A Expired DE2366070C2 (en, 2012) | 1972-12-29 | 1973-12-20 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2363351A Expired DE2363351C2 (de) | 1972-12-29 | 1973-12-20 | Substituierte 5(6)-Hydroxy-benzimidazol-2-carbaminsäuremethylester und diese enthaltende Heilmittel |
| DE2366070A Expired DE2366070C2 (en, 2012) | 1972-12-29 | 1973-12-20 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3929821A (en, 2012) |
| JP (1) | JPS5939428B2 (en, 2012) |
| AR (2) | AR216037A1 (en, 2012) |
| AT (1) | AT332883B (en, 2012) |
| BR (1) | BR7310296D0 (en, 2012) |
| CH (2) | CH613955A5 (en, 2012) |
| CS (1) | CS187390B2 (en, 2012) |
| DE (3) | DE2366069A1 (en, 2012) |
| DK (1) | DK137329B (en, 2012) |
| ES (2) | ES421927A1 (en, 2012) |
| FR (1) | FR2212150B1 (en, 2012) |
| GB (2) | GB1456497A (en, 2012) |
| HK (1) | HK8280A (en, 2012) |
| HU (1) | HU169272B (en, 2012) |
| IE (1) | IE40046B1 (en, 2012) |
| IL (1) | IL43860A (en, 2012) |
| IN (1) | IN138644B (en, 2012) |
| IT (1) | IT1046097B (en, 2012) |
| MY (1) | MY8000273A (en, 2012) |
| NL (1) | NL169738C (en, 2012) |
| PL (1) | PL95987B1 (en, 2012) |
| RO (1) | RO67150A (en, 2012) |
| SE (1) | SE414402B (en, 2012) |
| SU (1) | SU727143A3 (en, 2012) |
| YU (2) | YU36706B (en, 2012) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002640A (en) * | 1972-12-29 | 1977-01-11 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US4258198A (en) * | 1973-05-29 | 1981-03-24 | Smithkline Corporation | 5-Cycloalkyl thio- and oxy-2-carbalkoxyaminobenzimidazoles |
| DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
| DE2441202C2 (de) * | 1974-08-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | 2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel |
| US4086235A (en) * | 1976-04-12 | 1978-04-25 | Syntex (U.S.A.) Inc. | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| USRE30990E (en) * | 1976-07-16 | 1982-07-06 | E. R. Squibb & Sons, Inc. | Benzimidazole derivatives, compositions thereof and method of use as anthelmintics |
| US4046908A (en) * | 1976-07-16 | 1977-09-06 | E. R. Squibb & Sons, Inc. | Benzimidazole derivatives, compositions thereof and method of use as anthelmintics |
| DE2736507A1 (de) * | 1976-08-13 | 1978-02-16 | Wellcome Found | Antihelminthische zubereitungen |
| IE45741B1 (en) * | 1976-08-13 | 1982-11-17 | Wellcome Found | An anthelmintic ether combination |
| FR2362116A1 (fr) * | 1976-08-20 | 1978-03-17 | Oreal | Metaphenylenediamines et compositions tinctoriales les contenant |
| US4093732A (en) * | 1977-02-17 | 1978-06-06 | E. R. Squibb & Sons, Inc. | Sulfoxide derivatives of benzimidazoles |
| IT1076022B (it) * | 1977-04-20 | 1985-04-22 | Montedison Spa | Benzimidazolcarbammati antielmintici |
| IT1107749B (it) * | 1977-10-06 | 1985-11-25 | Montedison Spa | Benzimidazolcarbammato particolarmente attivo contro i parassiti gastroenterici e polmonari |
| US4152522A (en) * | 1978-01-03 | 1979-05-01 | Ethyl Corporation | Process for the preparation of 2-benzimidazole carbamates |
| US4156006A (en) * | 1978-01-09 | 1979-05-22 | E. R. Squibb & Sons, Inc. | Vinyl sulfide derivatives of benzimidazoles |
| US4136174A (en) * | 1978-01-18 | 1979-01-23 | E. R. Squibb & Sons, Inc. | Benzimidazolecarbamates and method |
| JPS54104837A (en) * | 1978-02-03 | 1979-08-17 | Nippon Denso Co Ltd | Controller of copying machines |
| US4145431A (en) * | 1978-02-16 | 1979-03-20 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral administration of sulfide- and sulfoxide-derivatives of benzimidazoles |
| US4154846A (en) * | 1978-06-16 | 1979-05-15 | E. R. Squibb & Sons, Inc. | Substituted thio-, sulfinyl-, and sulfonyl-alkyl benzimidazole carbamates |
| US4174400A (en) * | 1978-09-13 | 1979-11-13 | Merck & Co., Inc. | Anthelmintic benzimidazoles |
| DE2845537A1 (de) * | 1978-10-19 | 1980-04-30 | Bayer Ag | Benzimidazolylcarbamidsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DD147539A5 (de) * | 1978-12-06 | 1981-04-08 | Montedison Spa | Herstellung von in 5(6)-stellung substituierten benzimidazol-carbamaten |
| IT1100788B (it) * | 1978-12-06 | 1985-09-28 | Montedison Spa | Benzimidazol-carbammati |
| US4198422A (en) * | 1979-05-17 | 1980-04-15 | E. R. Squibb & Sons, Inc. | Substituted 2,3-naphthimidazole carbamates and method |
| EP0028455A1 (en) * | 1979-10-12 | 1981-05-13 | Imperial Chemical Industries Plc | 5-Phenylselenobenzimidazole derivatives, their preparation and anthelmintic or fasciolicidal compositions containing them |
| IL61232A (en) * | 1979-10-19 | 1985-09-29 | Chinoin Gyogyszer Es Vegyeszet | Process for the preparation of 2-amino(or alkoxycarbonylamino)-5(6)-thiocyanato(or thiol)benzimidazole derivatives |
| US4599428A (en) * | 1979-10-19 | 1986-07-08 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt | Process for the preparation of 5(6)-thio substituted benzimidazoles |
| HU182763B (hu) * | 1979-10-19 | 1984-03-28 | Chinoin Gyogyszer Es Vegyeszet | Eljárás 5(6)-alkiltio-benzimidazolil-alkil-karbamátok előállítására |
| US4299837A (en) | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
| DE3719783A1 (de) * | 1987-06-13 | 1988-12-22 | Hoechst Ag | Verfahren zur herstellung von 5-phenylsulfinyl-1h-2-(methoxycarbonylamino)- benzimidazol |
| GB9205368D0 (en) * | 1992-03-12 | 1992-04-22 | Pfizer Ltd | Benzimidozole anthelmintic agents |
| US6593466B1 (en) * | 1999-07-07 | 2003-07-15 | Isis Pharmaceuticals, Inc. | Guanidinium functionalized nucleotides and precursors thereof |
| DK1913009T3 (da) * | 2005-07-28 | 2010-08-16 | Intervet Int Bv | Nye benzimidazol(thio)carbamater med antiparasitisk virkning samt syntese heraf |
| CN102283698B (zh) * | 2006-06-12 | 2016-02-24 | 史密夫和内修有限公司 | 用于进行胫骨切除的引导装置 |
| AR061351A1 (es) | 2006-06-14 | 2008-08-20 | Intervet Int Bv | Composicion de carbamato de bencimidazol |
| CN102241635A (zh) * | 2011-04-28 | 2011-11-16 | 江苏宝众宝达药业有限公司 | 一种苯并咪唑类驱虫药苯硫咪唑的制备方法 |
| CN102863392A (zh) * | 2012-10-18 | 2013-01-09 | 江苏宝众宝达药业有限公司 | 一种奥芬达唑生产过程中大幅减少溶剂使用量的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2933502A (en) * | 1958-02-12 | 1960-04-19 | Du Pont | Benzimidazolone derivatives |
| US2933504A (en) * | 1959-08-10 | 1960-04-19 | Du Pont | Derivatives of polyalkoxycarbonyl imine |
| US3010968A (en) * | 1959-11-25 | 1961-11-28 | Du Pont | Process for manufacture of certain alkyl esters of benzimidazole carbamic acids |
| BE666795A (en, 2012) * | 1964-08-04 | 1966-01-13 | ||
| US3506767A (en) * | 1965-08-06 | 1970-04-14 | Geigy Chem Corp | Benzimidazole compositions and methods of use |
| US3401171A (en) * | 1966-03-11 | 1968-09-10 | Smithkline Corp | 2-amidobenzimidazoles |
| CH456236A (de) * | 1966-05-06 | 1968-07-15 | Agripat Sa | Verfahren zum Schützen textiler Keratinfasermaterialien vor Insektenfrass und Mittel zur Durchführung dieses Verfahrens |
| US3480642A (en) * | 1967-03-22 | 1969-11-25 | Smithkline Corp | Process for producing 2-carbalkoxyaminobenzimidazoles |
| CH490010A (de) * | 1967-10-26 | 1970-05-15 | Ciba Geigy | Schädlingsbekämpfungsmittel |
| US3562290A (en) * | 1967-11-07 | 1971-02-09 | Du Pont | Process for making 2-benzimidazolecarbamic acid alkyl esters |
| FR2059938A1 (en) * | 1969-03-14 | 1971-06-11 | Aries Robert | 1-haloalk(en)yl sulphenyl-2-aryloxycarbon-yl - |
| US3657267A (en) * | 1969-06-20 | 1972-04-18 | Janssen Pharmaceutica Nv | Benzimidazole carbamates |
| US3714180A (en) * | 1970-08-12 | 1973-01-30 | Squibb & Sons Inc | Sulfonyl benzimidazoles |
| US3694455A (en) * | 1970-11-19 | 1972-09-26 | Smith Kline French Lab | Acyloxyalkyl amidobenzimidazoles |
| US3720686A (en) * | 1971-04-01 | 1973-03-13 | Squibb & Sons Inc | Mercaptobenzimidazole derivatives |
-
1973
- 1973-11-21 US US417963A patent/US3929821A/en not_active Expired - Lifetime
- 1973-12-10 IN IN2692/CAL/73A patent/IN138644B/en unknown
- 1973-12-13 GB GB3023476A patent/GB1456497A/en not_active Expired
- 1973-12-13 GB GB5792573A patent/GB1455728A/en not_active Expired
- 1973-12-14 CH CH1760073A patent/CH613955A5/xx not_active IP Right Cessation
- 1973-12-14 CH CH68577A patent/CH608006A5/xx not_active IP Right Cessation
- 1973-12-17 DK DK685273AA patent/DK137329B/da not_active IP Right Cessation
- 1973-12-19 IL IL43860A patent/IL43860A/en unknown
- 1973-12-20 DE DE19732366069 patent/DE2366069A1/de active Granted
- 1973-12-20 SE SE7317261A patent/SE414402B/sv unknown
- 1973-12-20 DE DE2363351A patent/DE2363351C2/de not_active Expired
- 1973-12-20 DE DE2366070A patent/DE2366070C2/de not_active Expired
- 1973-12-20 HU HUSI1367A patent/HU169272B/hu unknown
- 1973-12-21 RO RO7377156A patent/RO67150A/ro unknown
- 1973-12-21 IE IE2322/73A patent/IE40046B1/xx unknown
- 1973-12-21 AT AT1075173A patent/AT332883B/de active
- 1973-12-21 CS CS738891A patent/CS187390B2/cs unknown
- 1973-12-26 JP JP744829A patent/JPS5939428B2/ja not_active Expired
- 1973-12-27 YU YU3371/73A patent/YU36706B/xx unknown
- 1973-12-28 BR BR10296/73A patent/BR7310296D0/pt unknown
- 1973-12-28 IT IT7901/73A patent/IT1046097B/it active Protection Beyond IP Right Term
- 1973-12-28 FR FR7346946A patent/FR2212150B1/fr not_active Expired
- 1973-12-28 AR AR251776A patent/AR216037A1/es active
- 1973-12-28 SU SU731980901A patent/SU727143A3/ru active
- 1973-12-28 NL NLAANVRAGE7317797,A patent/NL169738C/xx not_active IP Right Cessation
- 1973-12-29 ES ES421927A patent/ES421927A1/es not_active Expired
- 1973-12-29 PL PL1973167768A patent/PL95987B1/pl unknown
-
1976
- 1976-02-17 ES ES445257A patent/ES445257A1/es not_active Expired
- 1976-05-06 AR AR263212A patent/AR221816A1/es active
-
1980
- 1980-03-06 HK HK82/80A patent/HK8280A/xx unknown
- 1980-03-07 YU YU641/80A patent/YU40868B/xx unknown
- 1980-12-30 MY MY273/80A patent/MY8000273A/xx unknown
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