CN103319416B - 新型兽药三氯苯达唑亚砜及其制备方法 - Google Patents
新型兽药三氯苯达唑亚砜及其制备方法 Download PDFInfo
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- CN103319416B CN103319416B CN201310252812.0A CN201310252812A CN103319416B CN 103319416 B CN103319416 B CN 103319416B CN 201310252812 A CN201310252812 A CN 201310252812A CN 103319416 B CN103319416 B CN 103319416B
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- triclabendazole
- veterinary drug
- sulfoxide
- triclabendazole sulfoxide
- novel
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- IMPKVMRTXBRHRB-UHFFFAOYSA-N cyclohexane-1,2,3,4,5-pentol Chemical compound OC1CC(O)C(O)C(O)C1O IMPKVMRTXBRHRB-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 239000000273 veterinary drug Substances 0.000 title abstract description 14
- 241000282994 Cervidae Species 0.000 claims abstract description 9
- 241000283707 Capra Species 0.000 claims abstract description 7
- 241001494479 Pecora Species 0.000 claims abstract description 7
- 241000242711 Fasciola hepatica Species 0.000 claims abstract description 5
- 241000283073 Equus caballus Species 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
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- 241000935974 Paralichthys dentatus Species 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 28
- NQPDXQQQCQDHHW-UHFFFAOYSA-N 6-chloro-5-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole Chemical compound ClC=1C=C2NC(SC)=NC2=CC=1OC1=CC=CC(Cl)=C1Cl NQPDXQQQCQDHHW-UHFFFAOYSA-N 0.000 abstract description 20
- 229960000323 triclabendazole Drugs 0.000 abstract description 20
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
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- FSGTULQLEVAYRS-UHFFFAOYSA-N 4,5-dichloro-2-nitroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O FSGTULQLEVAYRS-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
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- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
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- 238000010792 warming Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical group O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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CN103319417B (zh) * | 2013-06-24 | 2014-07-09 | 常州佳灵药业有限公司 | 三氯苯达唑亚砜的制备方法 |
CN103864695A (zh) * | 2014-03-19 | 2014-06-18 | 连云港市亚晖医药化工有限公司 | 三氯苯达唑亚砜的制备方法 |
RU2602679C1 (ru) * | 2015-09-24 | 2016-11-20 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский ветеринарный институт Нечернозёмной зоны Российской Федерации (ФГБНУ "НИВИ НЗ России") | Способ пастбищной профилактики фасциолёза жвачных животных |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4197307A (en) * | 1977-04-12 | 1980-04-08 | Ciba-Geigy Corporation | 2-Alkylthio-, 2-alkylsulphinyl- and 2-alkylsulfonyl-6-phenylbenzimidazoles as anthelmintic agents |
CN101555231A (zh) * | 2009-05-04 | 2009-10-14 | 扬州天和药业有限公司 | 一种制备三氯苯达唑的方法 |
CN102070498A (zh) * | 2011-01-12 | 2011-05-25 | 华东师范大学 | 一种亚砜的制备方法 |
WO2012070068A2 (en) * | 2010-11-24 | 2012-05-31 | Sequent Scientific Limited | Process for preparation of triclabendazole |
CN103319417A (zh) * | 2013-06-24 | 2013-09-25 | 常州佳灵药业有限公司 | 三氯苯达唑亚砜的制备方法 |
-
2013
- 2013-06-24 CN CN201310252812.0A patent/CN103319416B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4197307A (en) * | 1977-04-12 | 1980-04-08 | Ciba-Geigy Corporation | 2-Alkylthio-, 2-alkylsulphinyl- and 2-alkylsulfonyl-6-phenylbenzimidazoles as anthelmintic agents |
CN101555231A (zh) * | 2009-05-04 | 2009-10-14 | 扬州天和药业有限公司 | 一种制备三氯苯达唑的方法 |
WO2012070068A2 (en) * | 2010-11-24 | 2012-05-31 | Sequent Scientific Limited | Process for preparation of triclabendazole |
CN102070498A (zh) * | 2011-01-12 | 2011-05-25 | 华东师范大学 | 一种亚砜的制备方法 |
CN103319417A (zh) * | 2013-06-24 | 2013-09-25 | 常州佳灵药业有限公司 | 三氯苯达唑亚砜的制备方法 |
Non-Patent Citations (3)
Title |
---|
2H-Benzimidazoles (Isobenzimidazoles). Part 7. A New Route to Triclabendazole [5-Chloro-6- (2,3-dichlorophenoxy)-2-methylthio-lH-benzimidazole] and Congeneric Benzimidazoles;Brian Iddon et al;《J. CHEM. SOC. PERKIN TRANS. 1》;19921231;第3132页 * |
2H-Benzimidazoles (Isobenzimidazoles). Part 7. A New Route to Triclabendazole [5-Chloro-6-(2,3-dichlorophenoxy)-2-methylthio-lH-benzimidazole] and Congeneric Benzimidazoles;Brian Iddon et al;《J. CHEM. SOC. PERKIN TRANS. 1》;19921231;第3132页 * |
崔志芹,王志祥.5-(2,3-二氯苯氧基)-4-氯-2-硝基苯胺合成工艺的研究.《化工时刊》.2006,第20卷(第8期),第24-26页. * |
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Application publication date: 20130925 Assignee: Changzhou best Biotechnology Co., Ltd. Assignor: Changzhou Jialing Medicine Industry Co., Ltd. Contract record no.: 2015320000285 Denomination of invention: Novel veterinary drug triclabendazole sulfoxide and preparation method thereof Granted publication date: 20150225 License type: Exclusive License Record date: 20150424 |
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Denomination of invention: Novel veterinary drug triclabendazole sulfoxide and preparation method thereof Effective date of registration: 20150805 Granted publication date: 20150225 Pledgee: Jiangsu Jiangnan Rural Commercial Bank Limited by Share Ltd Pledgor: Changzhou Jialing Medicine Industry Co., Ltd. Registration number: 2015990000642 |
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Date of cancellation: 20161220 Granted publication date: 20150225 Pledgee: Jiangsu Jiangnan Rural Commercial Bank Limited by Share Ltd Pledgor: Changzhou Jialing Medicine Industry Co., Ltd. Registration number: 2015990000642 |
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Denomination of invention: Novel veterinary drug triclabendazole sulfoxide and preparation method thereof Effective date of registration: 20161220 Granted publication date: 20150225 Pledgee: Jiangsu Jiangnan Rural Commercial Bank Limited by Share Ltd Pledgor: Changzhou Jialing Medicine Industry Co., Ltd. Registration number: 2016990001139 |
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