SE444314B - Forfarande for framstellning av bensimidazolderivat - Google Patents

Forfarande for framstellning av bensimidazolderivat

Info

Publication number: SE444314B
Authority: SE; Sweden
Prior art keywords: group; formula; compounds; halogen; methyl group
Prior art date: 1977-04-12

Application number

SE7804058A

Other languages

English (en)

Swedish (sv)

Other versions

SE7804058L (sv

Inventor

E Aufderhaar

J-J Gallay

M Kuhne

A Meyer

O Rechsteiner

M Schellenbaum

J-P Fumeaux

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1977-04-12

Filing date

1978-04-11

Publication date

1986-04-07

1977-04-12 Priority claimed from LU77122A external-priority patent/LU77122A1/xx

1977-04-12 Priority claimed from LU77121A external-priority patent/LU77121A1/xx

1978-03-14 Priority claimed from LU79227A external-priority patent/LU79227A1/de

1978-04-11 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1978-10-13 Publication of SE7804058L publication Critical patent/SE7804058L/xx

1986-04-07 Publication of SE444314B publication Critical patent/SE444314B/sv

Links

238000000034 method Methods 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims description 22
239000000460 chlorine Chemical group 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052717 sulfur Chemical group 0.000 claims description 5
239000011593 sulfur Chemical group 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
239000013543 active substance Substances 0.000 description 17
241001465754 Metazoa Species 0.000 description 11
239000000203 mixture Substances 0.000 description 9
-1 propyl alcohols Chemical class 0.000 description 8
239000000126 substance Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000012876 carrier material Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 4
150000001556 benzimidazoles Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000000507 anthelmentic effect Effects 0.000 description 3
229940124339 anthelmintic agent Drugs 0.000 description 3
239000000921 anthelmintic agent Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
244000000013 helminth Species 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002156 mixing Methods 0.000 description 3
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000242711 Fasciola hepatica Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000005642 Oleic acid Substances 0.000 description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002250 absorbent Substances 0.000 description 2
230000002745 absorbent Effects 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229960003475 cambendazole Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
QZWHWHNCPFEXLL-UHFFFAOYSA-N propan-2-yl n-[2-(1,3-thiazol-4-yl)-3h-benzimidazol-5-yl]carbamate Chemical compound N1C2=CC(NC(=O)OC(C)C)=CC=C2N=C1C1=CSC=N1 QZWHWHNCPFEXLL-UHFFFAOYSA-N 0.000 description 2
238000003307 slaughter Methods 0.000 description 2
235000002639 sodium chloride Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
UDDPPYHULIXFDV-UHFFFAOYSA-N 1-[(6-chloro-2-methoxyacridin-9-yl)amino]-3-(diethylamino)propan-2-ol Chemical compound C1=C(OC)C=C2C(NCC(O)CN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 UDDPPYHULIXFDV-UHFFFAOYSA-N 0.000 description 1
HQXWVXPBRCYGGM-UHFFFAOYSA-N 1-ethyl-2,6-bis[2-(4-pyrrolidin-1-ylphenyl)ethenyl]pyridin-1-ium Chemical compound C1=CC=C(C=CC=2C=CC(=CC=2)N2CCCC2)[N+](CC)=C1C=CC(C=C1)=CC=C1N1CCCC1 HQXWVXPBRCYGGM-UHFFFAOYSA-N 0.000 description 1
QOUSCKKLBRWNSE-UHFFFAOYSA-N 2-octadecyl-1h-benzimidazole Chemical class C1=CC=C2NC(CCCCCCCCCCCCCCCCCC)=NC2=C1 QOUSCKKLBRWNSE-UHFFFAOYSA-N 0.000 description 1
DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 1
ZSIQWWYOUYOECH-UHFFFAOYSA-N 4-bromo-5-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC(Br)=C(C)C=C1O ZSIQWWYOUYOECH-UHFFFAOYSA-N 0.000 description 1
WFJIVOKAWHGMBH-UHFFFAOYSA-N 4-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=CC=C(O)C=C1O WFJIVOKAWHGMBH-UHFFFAOYSA-N 0.000 description 1
ALJHHTHBYJROOG-UHFFFAOYSA-N 7-(dimethylamino)phenothiazin-3-one Chemical compound C1=CC(=O)C=C2SC3=CC(N(C)C)=CC=C3N=C21 ALJHHTHBYJROOG-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
MGYMHQJELJYRQS-UHFFFAOYSA-N Ascaridole Chemical compound C1CC2(C)OOC1(C(C)C)C=C2 MGYMHQJELJYRQS-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
JGLWGLKNDHZFAP-UHFFFAOYSA-N C3-thiacarbocyanine cation Chemical compound S1C2=CC=CC=C2[N+](CC)=C1C=CC=C1N(CC)C2=CC=CC=C2S1 JGLWGLKNDHZFAP-UHFFFAOYSA-N 0.000 description 1
HHLAJTWCKSBJFA-VAWYXSNFSA-N CN1C(=S)SC(\N=N\c2ccc(cc2)[N+]([O-])=O)C1=O Chemical compound CN1C(=S)SC(\N=N\c2ccc(cc2)[N+]([O-])=O)C1=O HHLAJTWCKSBJFA-VAWYXSNFSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
JHJOOSLFWRRSGU-UHFFFAOYSA-N Fenchlorphos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Cl)C=C1Cl JHJOOSLFWRRSGU-UHFFFAOYSA-N 0.000 description 1
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
QRBVCAWHUSTDOT-UHFFFAOYSA-N Methyridine Chemical compound COCCC1=CC=CC=N1 QRBVCAWHUSTDOT-UHFFFAOYSA-N 0.000 description 1
YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-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
241000244206 Nematoda Species 0.000 description 1
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241000269908 Platichthys flesus Species 0.000 description 1
OOPDAHSJBRZRPH-UHFFFAOYSA-L Pyrvinium pamoate Chemical compound C1=CC2=CC(N(C)C)=CC=C2[N+](C)=C1C=CC(=C1C)C=C(C)N1C1=CC=CC=C1.C1=CC2=CC(N(C)C)=CC=C2[N+](C)=C1C=CC(=C1C)C=C(C)N1C1=CC=CC=C1.C12=CC=CC=C2C=C(C([O-])=O)C(O)=C1CC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 OOPDAHSJBRZRPH-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000869417 Trematodes Species 0.000 description 1
YYQRGCZGSFRBAM-UHFFFAOYSA-N Triclofos Chemical compound OP(O)(=O)OCC(Cl)(Cl)Cl YYQRGCZGSFRBAM-UHFFFAOYSA-N 0.000 description 1
XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
229960002669 albendazole Drugs 0.000 description 1
HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
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230000001195 anabolic effect Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 1
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PMPQCPQAHTXCDK-UHFFFAOYSA-M benzyl-dimethyl-(2-phenoxyethyl)azanium;3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1.C=1C=CC=CC=1C[N+](C)(C)CCOC1=CC=CC=C1 PMPQCPQAHTXCDK-UHFFFAOYSA-M 0.000 description 1
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OMWQUXGVXQELIX-UHFFFAOYSA-N bitoscanate Chemical compound S=C=NC1=CC=C(N=C=S)C=C1 OMWQUXGVXQELIX-UHFFFAOYSA-N 0.000 description 1
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BXNANOICGRISHX-UHFFFAOYSA-N coumaphos Chemical compound CC1=C(Cl)C(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 BXNANOICGRISHX-UHFFFAOYSA-N 0.000 description 1
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239000003085 diluting agent Substances 0.000 description 1
SBOSGIJGEHWBKV-UHFFFAOYSA-L dioctyltin(2+);dichloride Chemical compound CCCCCCCC[Sn](Cl)(Cl)CCCCCCCC SBOSGIJGEHWBKV-UHFFFAOYSA-L 0.000 description 1
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OPXLLQIJSORQAM-UHFFFAOYSA-N mebendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(=O)C1=CC=CC=C1 OPXLLQIJSORQAM-UHFFFAOYSA-N 0.000 description 1
YQCIWBXEVYWRCW-UHFFFAOYSA-N methane;sulfane Chemical compound C.S YQCIWBXEVYWRCW-UHFFFAOYSA-N 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
FGGFIMIICGZCCJ-UHFFFAOYSA-N n,n-dibutyl-4-hexoxynaphthalene-1-carboximidamide Chemical compound C1=CC=C2C(OCCCCCC)=CC=C(C(=N)N(CCCC)CCCC)C2=C1 FGGFIMIICGZCCJ-UHFFFAOYSA-N 0.000 description 1
IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 1
QNSIFYWAPWSAIJ-UHFFFAOYSA-N naftalofos Chemical compound C1=CC(C(N(OP(=O)(OCC)OCC)C2=O)=O)=C3C2=CC=CC3=C1 QNSIFYWAPWSAIJ-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
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150000007530 organic bases Chemical class 0.000 description 1
229960004454 oxfendazole Drugs 0.000 description 1
BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 description 1
229960002762 oxibendazole Drugs 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
229950007337 parbendazole Drugs 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
229960005134 pyrantel Drugs 0.000 description 1
YSAUAVHXTIETRK-AATRIKPKSA-N pyrantel Chemical compound CN1CCCN=C1\C=C\C1=CC=CS1 YSAUAVHXTIETRK-AATRIKPKSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229960002778 pyrvinium Drugs 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229960004546 thiabendazole Drugs 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
235000010296 thiabendazole Nutrition 0.000 description 1
239000004308 thiabendazole Substances 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000723 toxicological property Toxicity 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
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004563 wettable powder Substances 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
- C07D235/28—Sulfur atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
- 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)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Dentistry (AREA)
Agronomy & Crop Science (AREA)
Environmental Sciences (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
Veterinary Medicine (AREA)
Pest Control & Pesticides (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SE7804058A 1977-04-12 1978-04-11 Forfarande for framstellning av bensimidazolderivat SE444314B (sv)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
LU77122A LU77122A1 (de)	1977-04-12	1977-04-12
LU77121A LU77121A1 (de)	1977-04-12	1977-04-12
LU79227A LU79227A1 (de)	1978-03-14	1978-03-14	Verfahren zur herstellung von anthelmintika

Publications (2)

Publication Number	Publication Date
SE7804058L SE7804058L (sv)	1978-10-13
SE444314B true SE444314B (sv)	1986-04-07

Family

ID=27350729

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7804058A SE444314B (sv)	1977-04-12	1978-04-11	Forfarande for framstellning av bensimidazolderivat

Country Status (23)

Country	Link
US (1)	US4205077A (de)
JP (1)	JPS53127477A (de)
AR (2)	AR225611A1 (de)
AT (1)	AT363077B (de)
AU (1)	AU525025B2 (de)
BE (1)	BE865871A (de)
CA (1)	CA1100978A (de)
CH (1)	CH634307A5 (de)
DE (1)	DE2815675A1 (de)
DK (1)	DK159378A (de)
EG (1)	EG13403A (de)
FR (1)	FR2387221A1 (de)
GB (1)	GB1599915A (de)
HU (1)	HU181860B (de)
IE (1)	IE46605B1 (de)
IL (1)	IL54480A (de)
IT (1)	IT1109968B (de)
MX (1)	MX5935E (de)
NL (1)	NL7803884A (de)
NZ (1)	NZ186933A (de)
PH (1)	PH14823A (de)
SE (1)	SE444314B (de)
YU (1)	YU41310B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4790868A (en) *	1986-03-17	1988-12-13	Ppg Industries, Inc.	Herbicidally active substituted phenoxy or phenylthio benzoxazolone (or benzthiazolone) compounds
JPS62246587A (ja) *	1986-03-17	1987-10-27	ピ−ピ−ジ−　インダストリイズ，インコ−ポレイテツド	除草活性を有する置換ベンゾオキサゾロン（またはベンゾチアゾロン）化合物
ES2083526T3 (es) *	1990-06-21	1996-04-16	Zeneca Ltd	Derivados piranicos biciclicos y su uso como inhibidores de 5-lipoxigenasa.
EP0474109A1 (de) *	1990-09-03	1992-03-11	Richter Gedeon Vegyeszeti Gyar R.T.	Neue 5-Benzyl-substituierte Benzimidazolin-2-Thion-Derivate und Verfahren zu ihrer Herstellung
US5371102A (en) *	1992-03-11	1994-12-06	University Of Hawaii	Compositions and methods of inhibiting thyroid activity
FR2708608B1 (fr) *	1993-07-30	1995-10-27	Sanofi Sa	Dérivés de N-sulfonylbenzimidazolone, leur préparation, les compositions pharmaceutiques en contenant.
ATE402924T1 (de) *	2003-03-03	2008-08-15	Mycosol Inc	Pyridiniumsalze und deren verwendung
BR122015032741B1 (pt)	2012-04-20	2019-11-26	Merial Ltd	composições parasiticídicas compreendendo derivados de benzimidazol, métodos e seus usos
AU2016255424B2 (en) *	2015-04-29	2020-10-08	Janssen Pharmaceutica Nv	Benzimidazolone and benzothiazolone compounds and their use as AMPA receptor modulators
AU2020231319A1 (en)	2019-03-01	2021-10-21	Boehringer Ingelheim Animal Health USA Inc.	Injectable clorsulon compositions, methods and uses thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1452948A (fr) *	1964-09-15	1966-04-15	Upjohn Co	1-phénylsulfonyl-2-benzimidazolinones et benzimidazolinethiones et leur procédé de fabrication
US3506767A (en) *	1965-08-06	1970-04-14	Geigy Chem Corp	Benzimidazole compositions and methods of use
FR1476588A (fr) *	1965-10-19	1967-04-14		Appareillage destiné à la fabrication mécanique des tapis
DE1542886A1 (de) *	1966-10-04	1970-05-14	Bayer Ag	Fungizide Mittel
DE2041324A1 (de) *	1970-08-20	1972-02-24	Agfa Gevaert Ag	Neue Benzimidazolderivate,sowie ein Verfahren zu ihrer Herstellung
US3894037A (en) *	1971-05-24	1975-07-08	Ciba Geigy Corp	Certain isothiocyanobenzimidazoles
DK645374A (de) *	1974-01-22	1975-09-29	Ciba Geigy Ag

1978
- 1978-04-10 CH CH382778A patent/CH634307A5/de not_active IP Right Cessation
- 1978-04-10 US US05/894,974 patent/US4205077A/en not_active Expired - Lifetime
- 1978-04-11 IT IT22188/78A patent/IT1109968B/it active
- 1978-04-11 IL IL54480A patent/IL54480A/xx unknown
- 1978-04-11 DE DE19782815675 patent/DE2815675A1/de not_active Ceased
- 1978-04-11 GB GB14184/78A patent/GB1599915A/en not_active Expired
- 1978-04-11 AT AT0253378A patent/AT363077B/de active
- 1978-04-11 EG EG251/78A patent/EG13403A/xx active
- 1978-04-11 HU HU78CI1823A patent/HU181860B/hu unknown
- 1978-04-11 YU YU858/78A patent/YU41310B/xx unknown
- 1978-04-11 IE IE705/78A patent/IE46605B1/en unknown
- 1978-04-11 DK DK159378A patent/DK159378A/da not_active IP Right Cessation
- 1978-04-11 BE BE186706A patent/BE865871A/xx not_active IP Right Cessation
- 1978-04-11 SE SE7804058A patent/SE444314B/sv not_active IP Right Cessation
- 1978-04-11 MX MX787012U patent/MX5935E/es unknown
- 1978-04-11 NZ NZ186933A patent/NZ186933A/xx unknown
- 1978-04-12 JP JP4305978A patent/JPS53127477A/ja active Granted
- 1978-04-12 CA CA300,990A patent/CA1100978A/en not_active Expired
- 1978-04-12 PH PH21000A patent/PH14823A/en unknown
- 1978-04-12 FR FR7810732A patent/FR2387221A1/fr active Granted
- 1978-04-12 AU AU35018/78A patent/AU525025B2/en not_active Expired
- 1978-04-12 NL NL7803884A patent/NL7803884A/xx not_active Application Discontinuation
1979
- 1979-05-15 AR AR276520A patent/AR225611A1/es active
- 1979-05-15 AR AR276521A patent/AR224734A1/es active

Also Published As

Publication number	Publication date
SE7804058L (sv)	1978-10-13
HU181860B (en)	1983-11-28
JPS6339592B2 (de)	1988-08-05
AU525025B2 (en)	1982-10-14
NL7803884A (nl)	1978-10-16
FR2387221A1 (fr)	1978-11-10
DE2815675A1 (de)	1978-10-19
YU41310B (en)	1987-02-28
AT363077B (de)	1981-07-10
BE865871A (fr)	1978-10-11
AR224734A1 (es)	1982-01-15
ATA253378A (de)	1980-12-15
CH634307A5 (de)	1983-01-31
CA1100978A (en)	1981-05-12
IT1109968B (it)	1985-12-23
AR225611A1 (es)	1982-04-15
EG13403A (en)	1981-06-30
AU3501878A (en)	1979-10-18
IE780705L (en)	1978-10-12
IL54480A0 (en)	1978-07-31
PH14823A (en)	1981-12-16
IE46605B1 (en)	1983-07-27
JPS53127477A (en)	1978-11-07
GB1599915A (en)	1981-10-07
FR2387221B1 (de)	1982-06-25
US4205077A (en)	1980-05-27
IL54480A (en)	1982-04-30
YU85878A (en)	1984-02-29
IT7822188A0 (it)	1978-04-11
MX5935E (es)	1984-08-30
NZ186933A (en)	1980-10-24
DK159378A (da)	1978-10-13

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1995-01-31

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Publication	Publication Date	Title
SE444315B (sv)	1986-04-07	Forfarande for framstellning av bensimidazolderivat
US3743738A (en)	1973-07-03	Substituted benzimidazoles as anthelmintic agents
US3586670A (en)	1971-06-22	Isothiocyanobenzazoles and use thereof as anthelmintics
JPH0153276B2 (de)	1989-11-13
PL85278B1 (de)	1976-04-30
SE444314B (sv)	1986-04-07	Forfarande for framstellning av bensimidazolderivat
DE69712608T2 (de)	2002-08-29	Protonenpumpinhibitoren
US3759938A (en)	1973-09-18	Thiazolidine derivatives
US3686110A (en)	1972-08-22	1-oxybenzimidazoles
WO2023160634A1 (zh)	2023-08-31	苯并噻唑类化合物、其制备方法及应用
US3840550A (en)	1974-10-08	Certain 6-isothiocyanobenzothiazoles
US3705174A (en)	1972-12-05	Polyhaloalkyl benzimidazoles
PL101396B1 (pl)	1978-12-30	Sposob wytwarzania estrow fenylowych kwasu 2-karboalkoksyaminobenzimidazolilo-5 /6/-sulfonowego
US3929822A (en)	1975-12-30	1,5(6)-Disubstituted benzizimidazole-2-carbamate derivatives having anthelmintic activity
CS197255B2 (en)	1980-04-30	Method of producing basicly substituted 2-alkoxycarbonyl-amino-benzimidazol-5/6/-ylphenyl esters and ketones
US3894037A (en)	1975-07-08	Certain isothiocyanobenzimidazoles
JPH0114235B2 (de)	1989-03-10
CS209519B2 (cs)	1981-12-31	Způsob výroby nových derivátů benzimidazolu
US3901901A (en)	1975-08-26	5(6)-benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity
US3933841A (en)	1976-01-20	2-Phenoxy, -phenylthio-, and -phenyl-amino-benzoxazoles having an isothiocyano substituent
US3772322A (en)	1973-11-13	1-carbamoyl-2-carboalkoxyamino benzimidazoles
CS209518B2 (cs)	1981-12-31	Způsob výroby nových derivátů benzimidazolu
MAHMOUD et al.	2019	Synthesis, Characterization, and Antibacterial Screening of Some New Benzimidazole Derivatives Having1, 3, 4 Thiadiazole Ring
IE48383B1 (en)	1984-12-26	Benzothiazole derivatives anthelmintics
US3962437A (en)	1976-06-08	5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity