CA1052798A - Methyl-5-propylthio-2-benzimidazolecarbamate - Google Patents
Methyl-5-propylthio-2-benzimidazolecarbamateInfo
- Publication number
- CA1052798A CA1052798A CA229,042A CA229042A CA1052798A CA 1052798 A CA1052798 A CA 1052798A CA 229042 A CA229042 A CA 229042A CA 1052798 A CA1052798 A CA 1052798A
- Authority
- CA
- Canada
- Prior art keywords
- propylthio
- methyl
- benzimidazolecarbamate
- phenylenediamine
- reacting
- 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
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 15
- -1 2-amino compound Chemical class 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- YXXYBJDTATZCOJ-UHFFFAOYSA-N 4-propylsulfanylbenzene-1,2-diamine Chemical compound CCCSC1=CC=C(N)C(N)=C1 YXXYBJDTATZCOJ-UHFFFAOYSA-N 0.000 claims 6
- ZSYJMXLJNPEAGP-UHFFFAOYSA-N methyl n-cyanocarbamate Chemical compound COC(=O)NC#N ZSYJMXLJNPEAGP-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- RKMOQLOKJZARIG-UHFFFAOYSA-N 6-propylsulfanyl-1h-benzimidazol-2-amine Chemical compound CCCSC1=CC=C2N=C(N)NC2=C1 RKMOQLOKJZARIG-UHFFFAOYSA-N 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 23
- 239000000203 mixture Substances 0.000 abstract description 17
- 241000243789 Metastrongyloidea Species 0.000 abstract description 8
- 239000004480 active ingredient Substances 0.000 abstract description 6
- 244000000013 helminth Species 0.000 abstract description 4
- 241000242541 Trematoda Species 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 13
- 241001494479 Pecora Species 0.000 description 12
- 230000000694 effects Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000507 anthelmentic effect Effects 0.000 description 7
- 244000045947 parasite Species 0.000 description 7
- 241000283690 Bos taurus Species 0.000 description 6
- 241001147667 Dictyocaulus Species 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 241000243976 Haemonchus Species 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 235000019687 Lamb Nutrition 0.000 description 4
- 241001137882 Nematodirus Species 0.000 description 4
- 239000000039 congener Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000001506 calcium phosphate Substances 0.000 description 3
- 229910000389 calcium phosphate Inorganic materials 0.000 description 3
- 235000011010 calcium phosphates Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 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 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000244188 Ascaris suum Species 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 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 2
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000002550 fecal effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229960001614 levamisole Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- OVVXSJXGGACEQT-UHFFFAOYSA-N (6-propyl-1H-benzimidazol-2-yl)carbamothioic S-acid Chemical compound CCCC1=CC2=C(C=C1)N=C(N2)NC(=O)S OVVXSJXGGACEQT-UHFFFAOYSA-N 0.000 description 1
- KSAPYRIVHFAQGR-UHFFFAOYSA-N 1-sulfanylbenzimidazole Chemical compound C1=CC=C2N(S)C=NC2=C1 KSAPYRIVHFAQGR-UHFFFAOYSA-N 0.000 description 1
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical compound C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 description 1
- 235000006491 Acacia senegal Nutrition 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
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000999616 Avitellina Species 0.000 description 1
- 241000931178 Bunostomum Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000242722 Cestoda Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 241001465696 Dictyocaulidae Species 0.000 description 1
- 241000498255 Enterobius vermicularis Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000986243 Filaroides Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 241000243974 Haemonchus contortus Species 0.000 description 1
- 108010034145 Helminth Proteins Proteins 0.000 description 1
- 206010061201 Helminthic infection Diseases 0.000 description 1
- 206010061217 Infestation Diseases 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
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- RAOCRURYZCVHMG-UHFFFAOYSA-N N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)NC2=C1 RAOCRURYZCVHMG-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 241000283903 Ovis aries 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
- 206010035664 Pneumonia Diseases 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 241000244031 Toxocara Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 241001638368 Trichuris vulpis Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- QXAITBQSYVNQDR-UHFFFAOYSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1N=CN(C)C=NC1=CC=C(C)C=C1C QXAITBQSYVNQDR-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 206010014881 enterobiasis Diseases 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- DQHTZKGBEYDBCS-UHFFFAOYSA-N ethyl n-(6-methylsulfanyl-1h-benzimidazol-2-yl)carbamate Chemical group C1=C(SC)C=C2NC(NC(=O)OCC)=NC2=C1 DQHTZKGBEYDBCS-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 244000000050 gastrointestinal parasite Species 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000003304 gavage Methods 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
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- WEXOIPBOPIVXDZ-UHFFFAOYSA-N hydron;4-propylsulfanylbenzene-1,2-diamine;chloride Chemical compound Cl.CCCSC1=CC=C(N)C(N)=C1 WEXOIPBOPIVXDZ-UHFFFAOYSA-N 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- UQFPFHWFXRTWRP-UHFFFAOYSA-N methoxycyanamide Chemical compound CONC#N UQFPFHWFXRTWRP-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229960002762 oxibendazole Drugs 0.000 description 1
- 239000012057 packaged powder Substances 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
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US480646A US3915986A (en) | 1974-06-19 | 1974-06-19 | Methyl 5-propylthio-2-benzimidazolecarbamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052798A true CA1052798A (en) | 1979-04-17 |
Family
ID=23908789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA229,042A Expired CA1052798A (en) | 1974-06-19 | 1975-06-11 | Methyl-5-propylthio-2-benzimidazolecarbamate |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US3915986A (en, 2012) |
| JP (2) | JPS609488B2 (en, 2012) |
| AR (1) | AR207248A1 (en, 2012) |
| BE (1) | BE830203A (en, 2012) |
| CA (1) | CA1052798A (en, 2012) |
| CH (1) | CH616157A5 (en, 2012) |
| CY (1) | CY1039A (en, 2012) |
| DD (1) | DD118089A5 (en, 2012) |
| DE (1) | DE2527065C3 (en, 2012) |
| DK (1) | DK135716B (en, 2012) |
| ES (1) | ES438452A1 (en, 2012) |
| FI (1) | FI59247C (en, 2012) |
| FR (1) | FR2275203A1 (en, 2012) |
| GB (1) | GB1464326A (en, 2012) |
| GT (1) | GT198062984A (en, 2012) |
| HK (1) | HK6880A (en, 2012) |
| HU (1) | HU172538B (en, 2012) |
| IE (1) | IE41379B1 (en, 2012) |
| IL (1) | IL47465A (en, 2012) |
| IT (1) | IT1038925B (en, 2012) |
| KE (1) | KE3014A (en, 2012) |
| LU (1) | LU72740A1 (en, 2012) |
| MX (1) | MX3978E (en, 2012) |
| MY (1) | MY8000260A (en, 2012) |
| NL (1) | NL170144C (en, 2012) |
| NO (1) | NO142813C (en, 2012) |
| OA (1) | OA05107A (en, 2012) |
| PH (1) | PH14561A (en, 2012) |
| PL (1) | PL99359B1 (en, 2012) |
| SE (1) | SE420313B (en, 2012) |
| SU (1) | SU572201A3 (en, 2012) |
| YU (1) | YU39322B (en, 2012) |
| ZA (1) | ZA753236B (en, 2012) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1076022B (it) * | 1977-04-20 | 1985-04-22 | Montedison Spa | Benzimidazolcarbammati antielmintici |
| SE443977B (sv) * | 1977-05-10 | 1986-03-17 | Chinoin Gyogyszer Es Vegyeszet | Forfarande for framstellning av 5(6)-tio-bensimidazolderivat |
| 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 |
| DE2840927A1 (de) * | 1978-09-20 | 1980-04-10 | Bayer Ag | 3,4-dihydroisochinoline, 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 |
| JPS5836122B2 (ja) * | 1979-11-19 | 1983-08-06 | 名古屋高速道路公社 | 回転支保工による橋脚の張出し梁施工法 |
| US4299837A (en) * | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
| EP0167491A3 (de) * | 1984-07-06 | 1986-12-30 | Ciba-Geigy Ag | Thiobarbitursäurederivate |
| EP0430885A3 (en) * | 1989-12-01 | 1991-11-06 | Ciba-Geigy Ag | Anthelmintical compounds |
| GB9106278D0 (en) * | 1991-03-25 | 1991-05-08 | Smithkline Beecham Plc | Method of treatment |
| GB9115272D0 (en) * | 1991-07-15 | 1991-08-28 | Pfizer Ltd | Benzimidazole anthelmintics |
| GB9124002D0 (en) * | 1991-11-12 | 1992-01-02 | Pfizer Ltd | Benzimidazole anthelmintic agents |
| GB9205368D0 (en) * | 1992-03-12 | 1992-04-22 | Pfizer Ltd | Benzimidozole anthelmintic agents |
| US5645819A (en) * | 1995-03-13 | 1997-07-08 | Klapow; Lawrence A. | Methods of diagnosing and treating an intestinal and lung roundworm infection |
| US5861142A (en) * | 1996-03-25 | 1999-01-19 | Schick; Mary Pichler | Method for promoting hair, nail, and skin keratinization |
| AU2962397A (en) * | 1996-06-07 | 1998-01-07 | Novartis Ag | Benzazole derivatives |
| 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 |
| WO2016157064A1 (en) | 2015-03-30 | 2016-10-06 | Deva Holding Anonim Sirketi | Stable ricobendazole formulations |
| MA41623A (fr) | 2015-11-26 | 2018-01-09 | Verano Ilac Sanayi Ve Ticaret A S | Composition lyophilisée de composé de benzimidazole |
| EP3178479A1 (en) | 2015-12-08 | 2017-06-14 | Verano Ilac Sanayi Ve Ticaret A.S. | An injectable composition of ricobendazole |
| CN107935939A (zh) * | 2017-11-09 | 2018-04-20 | 华中药业股份有限公司 | 一种阿苯达唑的精制方法 |
| BR102020021181A2 (pt) | 2020-10-16 | 2022-04-26 | Ipanema Industria De Produtos Veterinarios Ltda | Microssuspensão contra parasitas e método para sua obtenção |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE666795A (en, 2012) * | 1964-08-04 | 1966-01-13 | ||
| US3847932A (en) * | 1967-10-26 | 1974-11-12 | Ciba Geigy Ag | Benzimidazole compounds and pesticidal preparations containing them |
| US3840550A (en) * | 1971-05-24 | 1974-10-08 | Ciba Geigy Corp | Certain 6-isothiocyanobenzothiazoles |
-
1974
- 1974-06-19 US US480646A patent/US3915986A/en not_active Expired - Lifetime
-
1975
- 1975-01-01 AR AR259133A patent/AR207248A1/es active
- 1975-05-20 ZA ZA00753236A patent/ZA753236B/xx unknown
- 1975-06-11 ES ES438452A patent/ES438452A1/es not_active Expired
- 1975-06-11 IE IE1317/75A patent/IE41379B1/xx not_active IP Right Cessation
- 1975-06-11 IL IL47465A patent/IL47465A/xx unknown
- 1975-06-11 CY CY1039A patent/CY1039A/xx unknown
- 1975-06-11 CA CA229,042A patent/CA1052798A/en not_active Expired
- 1975-06-11 GB GB2495575A patent/GB1464326A/en not_active Expired
- 1975-06-12 DK DK266175AA patent/DK135716B/da not_active IP Right Cessation
- 1975-06-13 BE BE157297A patent/BE830203A/xx not_active IP Right Cessation
- 1975-06-13 IT IT24364/75A patent/IT1038925B/it active
- 1975-06-14 JP JP50072616A patent/JPS609488B2/ja not_active Expired
- 1975-06-16 LU LU72740A patent/LU72740A1/xx unknown
- 1975-06-17 YU YU1559/75A patent/YU39322B/xx unknown
- 1975-06-17 NL NLAANVRAGE7507190,A patent/NL170144C/xx not_active IP Right Cessation
- 1975-06-17 DD DD186697A patent/DD118089A5/xx unknown
- 1975-06-17 FI FI751804A patent/FI59247C/fi not_active IP Right Cessation
- 1975-06-17 NO NO752152A patent/NO142813C/no unknown
- 1975-06-18 FR FR7519035A patent/FR2275203A1/fr active Granted
- 1975-06-18 SE SE7506996A patent/SE420313B/xx not_active IP Right Cessation
- 1975-06-18 PL PL1975181318A patent/PL99359B1/pl unknown
- 1975-06-18 CH CH794275A patent/CH616157A5/de not_active IP Right Cessation
- 1975-06-18 DE DE2527065A patent/DE2527065C3/de not_active Expired
- 1975-06-18 SU SU7502145903A patent/SU572201A3/ru active
- 1975-06-18 HU HU75SI00001473A patent/HU172538B/hu unknown
- 1975-06-19 MX MX755193U patent/MX3978E/es unknown
- 1975-08-07 US US05/602,704 patent/US3956499A/en not_active Expired - Lifetime
- 1975-09-09 OA OA55607A patent/OA05107A/xx unknown
-
1976
- 1976-10-08 PH PH18989A patent/PH14561A/en unknown
-
1980
- 1980-01-23 KE KE3014A patent/KE3014A/xx unknown
- 1980-02-28 HK HK68/80A patent/HK6880A/xx unknown
- 1980-04-18 GT GT198062984A patent/GT198062984A/es unknown
- 1980-12-30 MY MY260/80A patent/MY8000260A/xx unknown
-
1984
- 1984-10-03 JP JP59209002A patent/JPS60120871A/ja active Granted
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