SU727143A3 - Способ получени производных 2-карбалкоксиаминобензимидазола или их солей - Google Patents
Способ получени производных 2-карбалкоксиаминобензимидазола или их солей Download PDFInfo
- Publication number
- SU727143A3 SU727143A3 SU731980901A SU1980901A SU727143A3 SU 727143 A3 SU727143 A3 SU 727143A3 SU 731980901 A SU731980901 A SU 731980901A SU 1980901 A SU1980901 A SU 1980901A SU 727143 A3 SU727143 A3 SU 727143A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- halogen
- alkyl
- methanol
- nitro
- treated
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 11
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- -1 sulfonyl compound Chemical class 0.000 claims description 64
- 238000009835 boiling Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical group 0.000 claims 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- ZDTDUAYRLVDHEJ-UHFFFAOYSA-N 2-(aziridin-1-yl)-n-[8-[[2-(aziridin-1-yl)acetyl]amino]octyl]acetamide Chemical compound C1CN1CC(=O)NCCCCCCCCNC(=O)CN1CC1 ZDTDUAYRLVDHEJ-UHFFFAOYSA-N 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 124
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- 229960000583 acetic acid Drugs 0.000 description 42
- 235000011054 acetic acid Nutrition 0.000 description 41
- 239000000203 mixture Substances 0.000 description 38
- 238000010992 reflux Methods 0.000 description 35
- 239000000243 solution Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 18
- 239000000284 extract Substances 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000012256 powdered iron Substances 0.000 description 11
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 11
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 10
- KHBXLYPOXVQKJG-UHFFFAOYSA-N methyl n-[(methoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)OC KHBXLYPOXVQKJG-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 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 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000011790 ferrous sulphate Substances 0.000 description 7
- 235000003891 ferrous sulphate Nutrition 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WBAXQRDIKPSTNW-UHFFFAOYSA-N butyl (nz)-n-[(butoxycarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound CCCCOC(=O)NC(SC)=NC(=O)OCCCC WBAXQRDIKPSTNW-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 4
- GOMNLMUKDVTFGZ-UHFFFAOYSA-N 4-(methoxymethylsulfanyl)benzene-1,2-diamine Chemical compound COCSC1=CC=C(N)C(N)=C1 GOMNLMUKDVTFGZ-UHFFFAOYSA-N 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 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 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 4
- OZZKMZSOGAOIFX-UHFFFAOYSA-N n-(4-hydroxy-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(O)C=C1[N+]([O-])=O OZZKMZSOGAOIFX-UHFFFAOYSA-N 0.000 description 4
- QJWXILRSYMNYRS-UHFFFAOYSA-N n-[4-(methoxymethylsulfanyl)-2-nitrophenyl]acetamide Chemical compound COCSC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 QJWXILRSYMNYRS-UHFFFAOYSA-N 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 235000011150 stannous chloride Nutrition 0.000 description 4
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 4
- GIGRWGTZFONRKA-UHFFFAOYSA-N 1-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CBr)C=C1 GIGRWGTZFONRKA-UHFFFAOYSA-N 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 3
- XCKYGWPKCWYBNV-UHFFFAOYSA-N 4-(methylsulfanylmethoxy)-2-nitroaniline Chemical compound CSCOC1=CC=C(N)C([N+]([O-])=O)=C1 XCKYGWPKCWYBNV-UHFFFAOYSA-N 0.000 description 3
- DNJRZKYRBSHVFS-UHFFFAOYSA-N 4-(methylsulfanylmethoxy)benzene-1,2-diamine Chemical compound CSCOC1=CC=C(N)C(N)=C1 DNJRZKYRBSHVFS-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012262 resinous product Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CQOVBHGKTKIWLJ-UHFFFAOYSA-N (3-amino-4-nitrophenyl)sulfanylmethyl thiocyanate Chemical compound NC1=CC(SCSC#N)=CC=C1[N+]([O-])=O CQOVBHGKTKIWLJ-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- BOVGVHPMJHCZOF-UHFFFAOYSA-N 2-(4-amino-3-nitrophenyl)sulfanylacetonitrile Chemical compound NC1=CC=C(SCC#N)C=C1[N+]([O-])=O BOVGVHPMJHCZOF-UHFFFAOYSA-N 0.000 description 2
- JGVXQZRIRQLMHA-UHFFFAOYSA-N 2-nitro-4-phenylmethoxyaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OCC1=CC=CC=C1 JGVXQZRIRQLMHA-UHFFFAOYSA-N 0.000 description 2
- SEUOXNQCSYDBKF-UHFFFAOYSA-N 2-phenylmethoxy-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1OCC1=CC=CC=C1 SEUOXNQCSYDBKF-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
- XTDFRKBAIHNFQA-UHFFFAOYSA-N 4-(2,2,2-trifluoroethylsulfanyl)benzene-1,2-diamine Chemical compound NC1=CC=C(SCC(F)(F)F)C=C1N XTDFRKBAIHNFQA-UHFFFAOYSA-N 0.000 description 2
- ATYQRPFZFUIJDU-UHFFFAOYSA-N 4-(2-ethoxyethoxy)-2-nitroaniline Chemical compound CCOCCOC1=CC=C(N)C([N+]([O-])=O)=C1 ATYQRPFZFUIJDU-UHFFFAOYSA-N 0.000 description 2
- XWTAVSTZHGDWTP-UHFFFAOYSA-N 4-(2-ethoxyethoxy)benzene-1,2-diamine Chemical compound CCOCCOC1=CC=C(N)C(N)=C1 XWTAVSTZHGDWTP-UHFFFAOYSA-N 0.000 description 2
- QVPUFANJOMCUMA-UHFFFAOYSA-N 4-(2-methoxyethoxy)benzene-1,2-diamine Chemical compound COCCOC1=CC=C(N)C(N)=C1 QVPUFANJOMCUMA-UHFFFAOYSA-N 0.000 description 2
- JYMLEEMEKCPXBF-UHFFFAOYSA-N 4-(methoxymethoxy)-2-nitroaniline Chemical compound COCOC1=CC=C(N)C([N+]([O-])=O)=C1 JYMLEEMEKCPXBF-UHFFFAOYSA-N 0.000 description 2
- LNMVKMXZEPKPCR-UHFFFAOYSA-N 4-(methoxymethoxy)benzene-1,2-diamine Chemical compound COCOC1=CC=C(N)C(N)=C1 LNMVKMXZEPKPCR-UHFFFAOYSA-N 0.000 description 2
- GSCJDDJBNFQKBL-UHFFFAOYSA-N 4-(methylsulfanylmethylsulfanyl)benzene-1,2-diamine Chemical compound CSCSC1=CC=C(N)C(N)=C1 GSCJDDJBNFQKBL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UQWBCYRXJLVETQ-UHFFFAOYSA-N 4-benzylsulfinyl-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)CC1=CC=CC=C1 UQWBCYRXJLVETQ-UHFFFAOYSA-N 0.000 description 2
- WTQAIQAEAPOCOX-UHFFFAOYSA-N 4-benzylsulfinylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)CC1=CC=CC=C1 WTQAIQAEAPOCOX-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 2
- NDZFWKZHVAUUTN-UHFFFAOYSA-N 4-methylsulfonyl-2-nitroaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 NDZFWKZHVAUUTN-UHFFFAOYSA-N 0.000 description 2
- UQVGKXPXBIVFMV-UHFFFAOYSA-N 4-phenylmethoxybenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OCC1=CC=CC=C1 UQVGKXPXBIVFMV-UHFFFAOYSA-N 0.000 description 2
- VWHBAJDTJAMASB-UHFFFAOYSA-N 5-(2-methoxyethoxy)-2-nitroaniline Chemical compound COCCOC1=CC=C([N+]([O-])=O)C(N)=C1 VWHBAJDTJAMASB-UHFFFAOYSA-N 0.000 description 2
- QXFNQYBWFFJRCI-UHFFFAOYSA-N 5-(benzenesulfonyl)-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 QXFNQYBWFFJRCI-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000005569 Iron sulphate Substances 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
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UXUCVNXUWOLPRU-UHFFFAOYSA-N Chloromethyl thiocyanate Chemical compound ClCSC#N UXUCVNXUWOLPRU-UHFFFAOYSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
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- 240000007182 Ochroma pyramidale Species 0.000 description 1
- 241000238413 Octopus Species 0.000 description 1
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- 241000169121 Toxicum Species 0.000 description 1
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- UTPUUJFGVVUXFR-UHFFFAOYSA-N [H]C([H])C([H])[Cl]C([H])([H])Cl Chemical compound [H]C([H])C([H])[Cl]C([H])([H])Cl UTPUUJFGVVUXFR-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
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- HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 1
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical class C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- KRIFIIWBVJKVST-UHFFFAOYSA-N chloro(chloromethylsulfanyl)methane Chemical compound ClCSCCl KRIFIIWBVJKVST-UHFFFAOYSA-N 0.000 description 1
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 235000008957 cocaer Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004148 curcumin Substances 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
- 208000031513 cyst Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AEHWKBXBXYNPCX-UHFFFAOYSA-N ethylsulfanylbenzene Chemical compound CCSC1=CC=CC=C1 AEHWKBXBXYNPCX-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- HMPZNFNMVMTRSL-UHFFFAOYSA-N methyl n-[[n-(methoxycarbonylamino)-c-methylsulfanylcarbonimidoyl]amino]carbamate Chemical compound COC(=O)NNC(SC)=NNC(=O)OC HMPZNFNMVMTRSL-UHFFFAOYSA-N 0.000 description 1
- JDGNKNLNWLMYQL-UHFFFAOYSA-N n-(2-nitro-4-propylsulfanylphenyl)acetamide Chemical compound CCCSC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 JDGNKNLNWLMYQL-UHFFFAOYSA-N 0.000 description 1
- YWANGSCDWBUSBK-UHFFFAOYSA-N n-(5-chloro-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1[N+]([O-])=O YWANGSCDWBUSBK-UHFFFAOYSA-N 0.000 description 1
- UNYQGGGCPWHENG-UHFFFAOYSA-N n-[5-(benzenesulfinyl)-2-nitrophenyl]acetamide Chemical compound C1=C([N+]([O-])=O)C(NC(=O)C)=CC(S(=O)C=2C=CC=CC=2)=C1 UNYQGGGCPWHENG-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 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 (1)
| Publication Number | Publication Date |
|---|---|
| SU727143A3 true SU727143A3 (ru) | 1980-04-05 |
Family
ID=26981949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU731980901A SU727143A3 (ru) | 1972-12-29 | 1973-12-28 | Способ получени производных 2-карбалкоксиаминобензимидазола или их солей |
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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