CA1057300A - Substituted phenylisothioureas and processes for their preparation and use - Google Patents
Substituted phenylisothioureas and processes for their preparation and useInfo
- Publication number
- CA1057300A CA1057300A CA231,347A CA231347A CA1057300A CA 1057300 A CA1057300 A CA 1057300A CA 231347 A CA231347 A CA 231347A CA 1057300 A CA1057300 A CA 1057300A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- carbomethoxy
- methylisothiourea
- compound
- amino
- 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
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- -1 phenoxy, phenylthio, phenylsulfinyl Chemical group 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 105
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- CLVFHUDVUDZVCZ-UHFFFAOYSA-N methyl n-[chloro(methylsulfanyl)methylidene]carbamate Chemical compound COC(=O)N=C(Cl)SC CLVFHUDVUDZVCZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
- KACDYCFFQBLRHD-UHFFFAOYSA-N methyl n-[(2-acetamido-4-phenoxyanilino)-methylsulfanylmethylidene]carbamate Chemical compound C1=C(NC(C)=O)C(NC(=NC(=O)OC)SC)=CC=C1OC1=CC=CC=C1 KACDYCFFQBLRHD-UHFFFAOYSA-N 0.000 claims description 5
- SGCYOEIBEYTYDH-UHFFFAOYSA-N methyl n-[(2-acetamido-4-phenoxyphenyl)carbamothioyl]carbamate Chemical compound C1=C(NC(C)=O)C(NC(=S)NC(=O)OC)=CC=C1OC1=CC=CC=C1 SGCYOEIBEYTYDH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- NFMRTELNNJQYAC-UHFFFAOYSA-N methyl n-[(2-benzamido-4-phenoxyanilino)-methylsulfanylmethylidene]carbamate Chemical compound C1=C(NC(=O)C=2C=CC=CC=2)C(NC(=NC(=O)OC)SC)=CC=C1OC1=CC=CC=C1 NFMRTELNNJQYAC-UHFFFAOYSA-N 0.000 claims description 3
- WSLCEDNAFSUAIX-UHFFFAOYSA-N n-(2-amino-5-phenylsulfanylphenyl)propanamide Chemical compound C1=C(N)C(NC(=O)CC)=CC(SC=2C=CC=CC=2)=C1 WSLCEDNAFSUAIX-UHFFFAOYSA-N 0.000 claims description 3
- IETMGVRZQRZHTE-UHFFFAOYSA-N 2-methoxy-n'-(4-phenylsulfanylphenyl)acetohydrazide Chemical compound C1=CC(NNC(=O)COC)=CC=C1SC1=CC=CC=C1 IETMGVRZQRZHTE-UHFFFAOYSA-N 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
- ZIOORLDAHBGLPB-UHFFFAOYSA-N ethyl n-[[2-(butanoylamino)-4-phenoxyanilino]-methylsulfanylmethylidene]carbamate Chemical compound C1=C(NC(SC)=NC(=O)OCC)C(NC(=O)CCC)=CC(OC=2C=CC=CC=2)=C1 ZIOORLDAHBGLPB-UHFFFAOYSA-N 0.000 claims description 2
- XKNUPGTUKJAHEA-UHFFFAOYSA-N ethyl n-[chloro(methylsulfanyl)methylidene]carbamate Chemical compound CCOC(=O)N=C(Cl)SC XKNUPGTUKJAHEA-UHFFFAOYSA-N 0.000 claims description 2
- DKDJNQPVELOXMR-UHFFFAOYSA-N methyl n-[(e)-n-[3-[(2-methoxyacetyl)amino]-4-phenylthiophen-2-yl]-c-methylsulfanylcarbonimidoyl]carbamate Chemical compound S1C(N=C(NC(=O)OC)SC)=C(NC(=O)COC)C(C=2C=CC=CC=2)=C1 DKDJNQPVELOXMR-UHFFFAOYSA-N 0.000 claims description 2
- AMRUAUCJPDMKEH-UHFFFAOYSA-N methyl n-[[2-(butanoylamino)-4-phenylsulfanylanilino]-methylsulfanylmethylidene]carbamate Chemical compound C1=C(NC(SC)=NC(=O)OC)C(NC(=O)CCC)=CC(SC=2C=CC=CC=2)=C1 AMRUAUCJPDMKEH-UHFFFAOYSA-N 0.000 claims description 2
- BKOGKVVQBGUYAR-UHFFFAOYSA-N methyl n-[methylsulfanyl-[4-phenoxy-2-(propanoylamino)anilino]methylidene]carbamate Chemical compound C1=C(NC(SC)=NC(=O)OC)C(NC(=O)CC)=CC(OC=2C=CC=CC=2)=C1 BKOGKVVQBGUYAR-UHFFFAOYSA-N 0.000 claims description 2
- VDOHADSHBBTLPW-UHFFFAOYSA-N methyl n-[methylsulfanyl-[5-phenoxy-2-(propanoylamino)anilino]methylidene]carbamate Chemical compound C1=C(NC(SC)=NC(=O)OC)C(NC(=O)CC)=CC=C1OC1=CC=CC=C1 VDOHADSHBBTLPW-UHFFFAOYSA-N 0.000 claims description 2
- DQHJVIJMMAJPGG-UHFFFAOYSA-N n-(2-amino-4-phenoxyphenyl)propanamide Chemical compound C1=C(N)C(NC(=O)CC)=CC=C1OC1=CC=CC=C1 DQHJVIJMMAJPGG-UHFFFAOYSA-N 0.000 claims description 2
- WWSRSEBEVNMGJI-UHFFFAOYSA-N n-(2-amino-5-phenylsulfanylphenyl)butanamide Chemical compound C1=C(N)C(NC(=O)CCC)=CC(SC=2C=CC=CC=2)=C1 WWSRSEBEVNMGJI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 12
- YDQBFLOXGJGCFU-UHFFFAOYSA-N methyl n-[methylsulfanyl-[4-phenylsulfanyl-2-(propanoylamino)anilino]methylidene]carbamate Chemical compound C1=C(NC(SC)=NC(=O)OC)C(NC(=O)CC)=CC(SC=2C=CC=CC=2)=C1 YDQBFLOXGJGCFU-UHFFFAOYSA-N 0.000 claims 1
- NMQPRVWGJVXBNU-UHFFFAOYSA-N n-(2-amino-5-phenoxyphenyl)benzamide Chemical compound C1=C(NC(=O)C=2C=CC=CC=2)C(N)=CC=C1OC1=CC=CC=C1 NMQPRVWGJVXBNU-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 229940124339 anthelmintic agent Drugs 0.000 abstract description 3
- 239000000921 anthelmintic agent Substances 0.000 abstract description 3
- 150000003585 thioureas Chemical class 0.000 abstract description 3
- 150000002541 isothioureas Chemical group 0.000 abstract description 2
- 125000003368 amide group Chemical group 0.000 abstract 2
- AOUJZLXCDRVPBJ-UHFFFAOYSA-O CC(NC1=CC(OC2=CC=CC=C2)=CC=C1NC(NC(OC)=O)=[S+]C)=O Chemical compound CC(NC1=CC(OC2=CC=CC=C2)=CC=C1NC(NC(OC)=O)=[S+]C)=O AOUJZLXCDRVPBJ-UHFFFAOYSA-O 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 244000045947 parasite Species 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005133 alkynyloxy group Chemical group 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000002224 dissection Methods 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 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 description 2
- 241001465677 Ancylostomatoidea Species 0.000 description 2
- 241000244188 Ascaris suum Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 2
- 241001480236 Strongyloides ratti Species 0.000 description 2
- 241001221734 Trichuris muris Species 0.000 description 2
- 241000571980 Uncinaria stenocephala Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000005236 alkanoylamino group Chemical group 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 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
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000009491 slugging Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 239000004308 thiabendazole Substances 0.000 description 2
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 2
- 229960004546 thiabendazole Drugs 0.000 description 2
- 235000010296 thiabendazole Nutrition 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- UGOQMSPZBURERW-UHFFFAOYSA-N 2-(2-amino-4-phenoxyphenoxy)-n-phenylacetamide Chemical compound C=1C=C(OCC(=O)NC=2C=CC=CC=2)C(N)=CC=1OC1=CC=CC=C1 UGOQMSPZBURERW-UHFFFAOYSA-N 0.000 description 1
- NKYWLDWELCRXGG-UHFFFAOYSA-N 2-(2-amino-4-phenoxyphenyl)-n-phenylacetamide Chemical compound C=1C=C(CC(=O)NC=2C=CC=CC=2)C(N)=CC=1OC1=CC=CC=C1 NKYWLDWELCRXGG-UHFFFAOYSA-N 0.000 description 1
- WIEXXPGGHLXNAW-UHFFFAOYSA-N 2-(2-amino-4-phenylphenyl)sulfanyl-n-phenylacetamide Chemical compound NC1=CC(C=2C=CC=CC=2)=CC=C1SCC(=O)NC1=CC=CC=C1 WIEXXPGGHLXNAW-UHFFFAOYSA-N 0.000 description 1
- JZEJKGGWEBZVEN-UHFFFAOYSA-N 2-(2-amino-4-phenylsulfanylphenyl)-n-phenylacetamide Chemical compound C=1C=C(CC(=O)NC=2C=CC=CC=2)C(N)=CC=1SC1=CC=CC=C1 JZEJKGGWEBZVEN-UHFFFAOYSA-N 0.000 description 1
- MMRYTCQPNBQEPO-UHFFFAOYSA-N 2-(2-amino-5-phenylphenyl)sulfanyl-n-phenylacetamide Chemical compound NC1=CC=C(C=2C=CC=CC=2)C=C1SCC(=O)NC1=CC=CC=C1 MMRYTCQPNBQEPO-UHFFFAOYSA-N 0.000 description 1
- YNFWVYWMTJZHHM-UHFFFAOYSA-N 2-amino-4-(2-chlorophenoxy)-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(N)CCOC1=CC=CC=C1Cl YNFWVYWMTJZHHM-UHFFFAOYSA-N 0.000 description 1
- DUIXZIGKRXSBTD-UHFFFAOYSA-N 2-amino-4-(3-chlorophenoxy)-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(N)CCOC1=CC=CC(Cl)=C1 DUIXZIGKRXSBTD-UHFFFAOYSA-N 0.000 description 1
- RQKYICOSJUHBKE-UHFFFAOYSA-N 2-amino-4-(3-chlorophenyl)sulfanyl-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(N)CCSC1=CC=CC(Cl)=C1 RQKYICOSJUHBKE-UHFFFAOYSA-N 0.000 description 1
- NWMZCMLMJONCBO-UHFFFAOYSA-N 2-amino-4-(3-methoxyphenoxy)-n-phenylbutanamide Chemical compound COC1=CC=CC(OCCC(N)C(=O)NC=2C=CC=CC=2)=C1 NWMZCMLMJONCBO-UHFFFAOYSA-N 0.000 description 1
- PYQAXJWUTSFXSC-UHFFFAOYSA-N 2-amino-4-(4-chlorophenoxy)-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(N)CCOC1=CC=C(Cl)C=C1 PYQAXJWUTSFXSC-UHFFFAOYSA-N 0.000 description 1
- BWKOXCJZZLCDPG-UHFFFAOYSA-N 2-amino-4-(4-chlorophenyl)sulfanyl-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(N)CCSC1=CC=C(Cl)C=C1 BWKOXCJZZLCDPG-UHFFFAOYSA-N 0.000 description 1
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- HWUNPRDUCHAGAF-UHFFFAOYSA-N n-(2-amino-5-phenoxyphenyl)cyclohexanecarboxamide Chemical compound C1=C(NC(=O)C2CCCCC2)C(N)=CC=C1OC1=CC=CC=C1 HWUNPRDUCHAGAF-UHFFFAOYSA-N 0.000 description 1
- DTRBTWJVVIJCSB-UHFFFAOYSA-N n-[2-amino-5-(3-methoxyphenoxy)phenyl]propanamide Chemical compound C1=C(N)C(NC(=O)CC)=CC(OC=2C=C(OC)C=CC=2)=C1 DTRBTWJVVIJCSB-UHFFFAOYSA-N 0.000 description 1
- FPSSXQKRDRQTLU-UHFFFAOYSA-N n-[2-amino-5-(3-methoxyphenyl)sulfanylphenyl]propanamide Chemical compound C1=C(N)C(NC(=O)CC)=CC(SC=2C=C(OC)C=CC=2)=C1 FPSSXQKRDRQTLU-UHFFFAOYSA-N 0.000 description 1
- ZKSIOWBWIMGLHC-UHFFFAOYSA-N n-[2-amino-5-(4-chlorophenoxy)phenyl]acetamide Chemical compound C1=C(N)C(NC(=O)C)=CC(OC=2C=CC(Cl)=CC=2)=C1 ZKSIOWBWIMGLHC-UHFFFAOYSA-N 0.000 description 1
- JAOGKMGQXYMPNL-UHFFFAOYSA-N n-[2-amino-5-(4-chlorophenyl)sulfanylphenyl]acetamide Chemical compound C1=C(N)C(NC(=O)C)=CC(SC=2C=CC(Cl)=CC=2)=C1 JAOGKMGQXYMPNL-UHFFFAOYSA-N 0.000 description 1
- LTKQAFKTPDBCAV-UHFFFAOYSA-N n-[2-amino-5-(benzenesulfinyl)phenyl]propanamide Chemical compound C1=C(N)C(NC(=O)CC)=CC(S(=O)C=2C=CC=CC=2)=C1 LTKQAFKTPDBCAV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- GPOAQDUODWWFHQ-UHFFFAOYSA-N propan-2-yl n-[(2-acetamido-4-phenoxyphenyl)carbamothioyl]carbamate Chemical compound C1=C(NC(C)=O)C(NC(=S)NC(=O)OC(C)C)=CC=C1OC1=CC=CC=C1 GPOAQDUODWWFHQ-UHFFFAOYSA-N 0.000 description 1
- MHDZZTOQSGHLMO-UHFFFAOYSA-N propan-2-yl n-[(2-acetamido-4-phenylsulfanylphenyl)carbamothioyl]carbamate Chemical compound C1=C(NC(C)=O)C(NC(=S)NC(=O)OC(C)C)=CC=C1SC1=CC=CC=C1 MHDZZTOQSGHLMO-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2434183A DE2434183C2 (de) | 1974-07-16 | 1974-07-16 | Substituierte Phenylisothioharnstoffe, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057300A true CA1057300A (en) | 1979-06-26 |
Family
ID=5920708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,347A Expired CA1057300A (en) | 1974-07-16 | 1975-07-14 | Substituted phenylisothioureas and processes for their preparation and use |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US4005123A (enExample) |
| JP (1) | JPS5136434A (enExample) |
| AT (2) | AT338820B (enExample) |
| BE (1) | BE831421A (enExample) |
| CA (1) | CA1057300A (enExample) |
| DE (1) | DE2434183C2 (enExample) |
| DK (1) | DK143556C (enExample) |
| FR (1) | FR2278330A1 (enExample) |
| GB (1) | GB1465025A (enExample) |
| IE (1) | IE41424B1 (enExample) |
| LU (1) | LU72975A1 (enExample) |
| NL (1) | NL7508397A (enExample) |
| PH (1) | PH12712A (enExample) |
| ZA (1) | ZA754558B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2608238A1 (de) * | 1976-02-28 | 1977-09-08 | Hoechst Ag | Substituierte phenylguanidine und verfahren zu ihrer herstellung |
| DE2653766A1 (de) * | 1976-11-26 | 1978-06-01 | Bayer Ag | Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4290971A (en) * | 1979-01-19 | 1981-09-22 | Dso "Pharmachim" | Method of preparing 2-(phenylamino)-imidazolines-(2) |
| EP0025010B1 (de) * | 1979-07-03 | 1983-07-20 | Ciba-Geigy Ag | Thioharnstoffderivate und Isothioharnstoffderivate, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel und ihre Verwendung zur Bekämpfung von Schädlingen |
| US4613356A (en) * | 1984-08-06 | 1986-09-23 | Stauffer Chemical Company | Aryloxyphenoxy propionylthioureas which are useful as herbicides |
| FR2636064B1 (fr) * | 1988-09-08 | 1990-12-07 | Fabre Sa Pierre | Thioformamidines, leur preparation et leur application en tant que medicaments |
| TW344649B (en) * | 1995-04-05 | 1998-11-11 | Novartis Ag | Pesticidal composition |
| KR100352942B1 (ko) * | 1999-09-08 | 2002-09-16 | 한국화학연구원 | 술파이드 또는 술폰기가 치환된 불소화 비닐옥시아세트아미드 유도체, 이의 제조 방법 및 이를 포함하는 제초제 조성물 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD90361A (enExample) * | ||||
| US3775463A (en) * | 1966-07-19 | 1973-11-27 | Basf Ag | N-phenyl-n'-alkoxy ester ureas |
| US3649679A (en) * | 1968-08-15 | 1972-03-14 | Lilly Co Eli | Substituted phenylalkanoic acid derivatives ii |
| DE2025412A1 (de) * | 1970-05-25 | 1971-12-02 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
| DE2025413A1 (de) * | 1970-05-25 | 1971-12-02 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Ureidophenylisothioharnstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
| DE2252691A1 (de) * | 1972-10-27 | 1974-05-02 | Bayer Ag | Amidophenylisothioharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US3843215A (en) * | 1973-04-02 | 1974-10-22 | Rockwell International Corp | Linear bearing |
-
1974
- 1974-07-16 DE DE2434183A patent/DE2434183C2/de not_active Expired
-
1975
- 1975-05-23 GB GB2268075A patent/GB1465025A/en not_active Expired
- 1975-07-11 US US05/595,040 patent/US4005123A/en not_active Expired - Lifetime
- 1975-07-14 CA CA231,347A patent/CA1057300A/en not_active Expired
- 1975-07-14 NL NL7508397A patent/NL7508397A/xx not_active Application Discontinuation
- 1975-07-14 PH PH17382A patent/PH12712A/en unknown
- 1975-07-14 LU LU72975A patent/LU72975A1/xx unknown
- 1975-07-15 ZA ZA00754558A patent/ZA754558B/xx unknown
- 1975-07-15 IE IE1567/75A patent/IE41424B1/en not_active IP Right Cessation
- 1975-07-15 DK DK321775A patent/DK143556C/da not_active IP Right Cessation
- 1975-07-16 BE BE158343A patent/BE831421A/xx unknown
- 1975-07-16 FR FR7522200A patent/FR2278330A1/fr active Granted
- 1975-07-16 AT AT549775A patent/AT338820B/de not_active IP Right Cessation
- 1975-07-16 JP JP50086261A patent/JPS5136434A/ja active Pending
-
1976
- 1976-06-04 US US05/693,097 patent/US4021571A/en not_active Expired - Lifetime
- 1976-09-27 AT AT714076A patent/AT339329B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE41424L (en) | 1976-01-16 |
| GB1465025A (en) | 1977-02-16 |
| FR2278330B1 (enExample) | 1979-08-10 |
| JPS5136434A (enExample) | 1976-03-27 |
| AU8305675A (en) | 1977-01-20 |
| ZA754558B (en) | 1976-06-30 |
| US4005123A (en) | 1977-01-25 |
| AT339329B (de) | 1977-10-10 |
| BE831421A (fr) | 1976-01-16 |
| ATA714076A (de) | 1977-02-15 |
| ATA549775A (de) | 1977-01-15 |
| US4021571A (en) | 1977-05-03 |
| PH12712A (en) | 1979-07-20 |
| DK143556B (da) | 1981-09-07 |
| AT338820B (de) | 1977-09-12 |
| DK321775A (da) | 1976-01-17 |
| LU72975A1 (enExample) | 1976-05-31 |
| DK143556C (da) | 1982-02-15 |
| IE41424B1 (en) | 1980-01-02 |
| DE2434183C2 (de) | 1982-07-01 |
| NL7508397A (nl) | 1976-01-20 |
| FR2278330A1 (fr) | 1976-02-13 |
| DE2434183A1 (de) | 1976-02-05 |
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