GB1576633A - 2-(3-carboxy - s - substituted - isothioureido)-anilines - Google Patents
2-(3-carboxy - s - substituted - isothioureido)-anilines Download PDFInfo
- Publication number
- GB1576633A GB1576633A GB18212/77A GB1821277A GB1576633A GB 1576633 A GB1576633 A GB 1576633A GB 18212/77 A GB18212/77 A GB 18212/77A GB 1821277 A GB1821277 A GB 1821277A GB 1576633 A GB1576633 A GB 1576633A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- carbomethoxy
- mole
- solution
- methylisothioureido
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 5
- 230000000855 fungicidal effect Effects 0.000 claims abstract 3
- -1 phenylsulfinyl Chemical group 0.000 claims description 154
- 239000000203 mixture Substances 0.000 claims description 63
- 239000000725 suspension Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- 241001465754 Metazoa Species 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 11
- 230000000507 anthelmentic effect Effects 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 241000282412 Homo Species 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000005544 phthalimido group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 230000037396 body weight Effects 0.000 claims description 5
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 208000006968 Helminthiasis Diseases 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000009418 agronomic effect Effects 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000003307 slaughter Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000000428 dust Substances 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000004563 wettable powder Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 150
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 135
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
- 239000002244 precipitate Substances 0.000 description 46
- 238000001914 filtration Methods 0.000 description 37
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 25
- SOVIIRRAYRVPQE-UHFFFAOYSA-N methyl n-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C1=C(N)C(NC(=S)NC(=O)OC)=CC(C(=O)C=2C=CC=CC=2)=C1 SOVIIRRAYRVPQE-UHFFFAOYSA-N 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 24
- 238000000921 elemental analysis Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 19
- 239000012065 filter cake Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- LBFAAYMITJMZOC-UHFFFAOYSA-N methyl n-(sulfanylidenemethylidene)carbamate Chemical compound COC(=O)N=C=S LBFAAYMITJMZOC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 150000002540 isothiocyanates Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003828 vacuum filtration Methods 0.000 description 6
- RXCOGDYOZQGGMK-UHFFFAOYSA-N (3,4-diaminophenyl)-phenylmethanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=CC=C1 RXCOGDYOZQGGMK-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 241001494479 Pecora Species 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229940124339 anthelmintic agent Drugs 0.000 description 4
- 239000000921 anthelmintic agent Substances 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- JRYIIOSUGVLIGE-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SC JRYIIOSUGVLIGE-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
- 229940116357 potassium thiocyanate Drugs 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000001119 stannous chloride Substances 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- NDYYWMXJZWHRLZ-UHFFFAOYSA-N 2-methoxyethyl carbonochloridate Chemical compound COCCOC(Cl)=O NDYYWMXJZWHRLZ-UHFFFAOYSA-N 0.000 description 2
- NLCPQMUVBQILMA-UHFFFAOYSA-N 2-nitro-5-propylsulfanylaniline Chemical compound CCCSC1=CC=C([N+]([O-])=O)C(N)=C1 NLCPQMUVBQILMA-UHFFFAOYSA-N 0.000 description 2
- WQEGHHLKDKIWKM-UHFFFAOYSA-N 4-butylbenzene-1,2-diamine Chemical compound CCCCC1=CC=C(N)C(N)=C1 WQEGHHLKDKIWKM-UHFFFAOYSA-N 0.000 description 2
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- YMYINLOPODGORZ-UHFFFAOYSA-N C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCCOC Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCCOC YMYINLOPODGORZ-UHFFFAOYSA-N 0.000 description 2
- 241000242711 Fasciola hepatica Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- AQGIYEAWUUDQCN-UHFFFAOYSA-N [2-(methoxycarbonylcarbamothioylamino)-4-propylphenyl]-oxo-sulfidoazanium Chemical compound C(=O)(OC)NC(NC1=C(C=CC(=C1)CCC)[N+](=S)[O-])=S AQGIYEAWUUDQCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- JMSBOVHHRAVICX-UHFFFAOYSA-N butyl N-[N-(2-amino-5-benzoylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OCCCC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SC JMSBOVHHRAVICX-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- NSKHPCZJWIBPMG-UHFFFAOYSA-N ethyl N-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C(=O)(OCC)NC(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)=S NSKHPCZJWIBPMG-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- ZOPDINBAHICTGW-UHFFFAOYSA-N hexyl N-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C(=O)(OCCCCCC)NC(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)=S ZOPDINBAHICTGW-UHFFFAOYSA-N 0.000 description 2
- NHDHWRNCPHFTDV-UHFFFAOYSA-N hexyl N-[N-(2-amino-5-benzoylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OCCCCCC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SC NHDHWRNCPHFTDV-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- QGXOLBWZIXWVHG-UHFFFAOYSA-N methyl (nz)-n-[(2-amino-4-benzoylanilino)-methylsulfanylmethylidene]carbamate Chemical compound C1=C(N)C(NC(=NC(=O)OC)SC)=CC=C1C(=O)C1=CC=CC=C1 QGXOLBWZIXWVHG-UHFFFAOYSA-N 0.000 description 2
- QHGIOZSQKOCBIW-UHFFFAOYSA-N methyl N-[(2-amino-4-benzoylphenyl)carbamothioyl]carbamate Chemical compound NC1=C(C=CC(=C1)C(C1=CC=CC=C1)=O)NC(=S)NC(OC)=O QHGIOZSQKOCBIW-UHFFFAOYSA-N 0.000 description 2
- RRGMVGAUGAYOAI-UHFFFAOYSA-N methyl N-[N-(2-amino-4-propylsulfanylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SCCC)SC RRGMVGAUGAYOAI-UHFFFAOYSA-N 0.000 description 2
- UBAMNDVNDHWZLP-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-(3-phenoxypropylsulfanyl)carbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCOC1=CC=CC=C1 UBAMNDVNDHWZLP-UHFFFAOYSA-N 0.000 description 2
- HGYWURYIPNBOHP-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-(3-phenylprop-2-enylsulfanyl)carbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCC=CC1=CC=CC=C1 HGYWURYIPNBOHP-UHFFFAOYSA-N 0.000 description 2
- PNLALMXNBCIURH-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-(4-cyanobutylsulfanyl)carbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCCC#N PNLALMXNBCIURH-UHFFFAOYSA-N 0.000 description 2
- HQSROVBAHIINEW-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-[4-(1,3-dioxoisoindol-2-yl)butylsulfanyl]carbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCCN1C(C=2C(C1=O)=CC=CC2)=O HQSROVBAHIINEW-UHFFFAOYSA-N 0.000 description 2
- PGXGYMMLXRCKMJ-UHFFFAOYSA-N methyl N-[N-(2-amino-5-nitrophenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)[N+](=O)[O-])SC PGXGYMMLXRCKMJ-UHFFFAOYSA-N 0.000 description 2
- GAZGTOXHVRBWMB-UHFFFAOYSA-N methyl N-[N-(2-aminophenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC=C1)SC GAZGTOXHVRBWMB-UHFFFAOYSA-N 0.000 description 2
- DNWQLNWKXHENLO-UHFFFAOYSA-N methyl n-[(2-amino-4-butylphenyl)carbamothioyl]carbamate Chemical compound CCCCC1=CC=C(NC(=S)NC(=O)OC)C(N)=C1 DNWQLNWKXHENLO-UHFFFAOYSA-N 0.000 description 2
- OUPBBRVWQIBRIS-UHFFFAOYSA-N methyl n-[(2-amino-5-propylsulfanylphenyl)carbamothioyl]carbamate Chemical compound CCCSC1=CC=C(N)C(NC(=S)NC(=O)OC)=C1 OUPBBRVWQIBRIS-UHFFFAOYSA-N 0.000 description 2
- YTGVAKDRFRGYAM-UHFFFAOYSA-N methyl n-[(2-aminophenyl)carbamothioyl]carbamate Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1N YTGVAKDRFRGYAM-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- RRAHVFGOGBHEHG-UHFFFAOYSA-N phenyl 4-[N'-(2-amino-5-benzoylphenyl)-N-methoxycarbonylcarbamimidoyl]sulfanylbutanoate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCC(=O)OC1=CC=CC=C1 RRAHVFGOGBHEHG-UHFFFAOYSA-N 0.000 description 2
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- 125000002960 margaryl 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])C([H])([H])C([H])([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
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- XPBMIQGYSLKYGQ-UHFFFAOYSA-N methyl (nz)-n-[(2-amino-5-phenylsulfanylanilino)-methylsulfanylmethylidene]carbamate Chemical compound C1=C(N)C(NC(=NC(=O)OC)SC)=CC(SC=2C=CC=CC=2)=C1 XPBMIQGYSLKYGQ-UHFFFAOYSA-N 0.000 description 1
- DFKNQFLAQNQXEA-UHFFFAOYSA-N methyl (nz)-n-[(2-amino-5-propylsulfanylanilino)-methylsulfanylmethylidene]carbamate Chemical compound CCCSC1=CC=C(N)C(NC(SC)=NC(=O)OC)=C1 DFKNQFLAQNQXEA-UHFFFAOYSA-N 0.000 description 1
- XOQJRFZCFRRGJB-UHFFFAOYSA-N methyl 4-[4-amino-3-[[(methoxycarbonylamino)-methylsulfanylmethylidene]amino]phenyl]sulfinylbenzoate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)C1=CC=C(C=C1)C(=O)OC)SC XOQJRFZCFRRGJB-UHFFFAOYSA-N 0.000 description 1
- DZRJUNAGPCRENC-UHFFFAOYSA-N methyl 4-[4-amino-3-[[(methoxycarbonylamino)-methylsulfanylmethylidene]amino]phenyl]sulfonylbenzoate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)(=O)C1=CC=C(C=C1)C(=O)OC)SC DZRJUNAGPCRENC-UHFFFAOYSA-N 0.000 description 1
- AJKIQBMDNWZZER-UHFFFAOYSA-N methyl N-[(2-amino-5-propylsulfonylphenyl)carbamothioyl]carbamate Chemical compound NC1=C(C=C(C=C1)S(=O)(=O)CCC)NC(=S)NC(=O)OC AJKIQBMDNWZZER-UHFFFAOYSA-N 0.000 description 1
- NAJACIUCVBXOIJ-UHFFFAOYSA-N methyl N-[(4-benzoyl-2-nitrophenyl)carbamothioyl]carbamate Chemical compound COC(=O)NC(=S)NC1=C(C=C(C=C1)C(C1=CC=CC=C1)=O)[N+](=O)[O-] NAJACIUCVBXOIJ-UHFFFAOYSA-N 0.000 description 1
- AMYHYEUALBMPRU-UHFFFAOYSA-N methyl N-[N-(2-amino-4-benzylsulfanylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SCC1=CC=CC=C1)SC AMYHYEUALBMPRU-UHFFFAOYSA-N 0.000 description 1
- ZSSFZEQMWWDNKH-UHFFFAOYSA-N methyl N-[N-(2-amino-4-butylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)CCCC)SC ZSSFZEQMWWDNKH-UHFFFAOYSA-N 0.000 description 1
- UVKRPDYTPITBAX-UHFFFAOYSA-N methyl N-[N-(2-amino-4-ethoxyphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)OCC)SC UVKRPDYTPITBAX-UHFFFAOYSA-N 0.000 description 1
- PJVLCUUSYNNERU-UHFFFAOYSA-N methyl N-[N-(2-amino-4-phenoxyphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)OC1=CC=CC=C1)SC PJVLCUUSYNNERU-UHFFFAOYSA-N 0.000 description 1
- FWGGPLFXSNQZOX-UHFFFAOYSA-N methyl N-[N-(2-amino-4-propan-2-yloxyphenyl)-C-butylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)OC(C)C)SCCCC FWGGPLFXSNQZOX-UHFFFAOYSA-N 0.000 description 1
- ZANLZGYHVWQIIN-UHFFFAOYSA-N methyl N-[N-(2-amino-4-propoxyphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)OCCC)SC ZANLZGYHVWQIIN-UHFFFAOYSA-N 0.000 description 1
- JJOHUSYCDNTDEN-UHFFFAOYSA-N methyl N-[N-(2-amino-4-propylsulfinylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)S(=O)CCC)SC JJOHUSYCDNTDEN-UHFFFAOYSA-N 0.000 description 1
- WUZPOJUFGNMNBH-UHFFFAOYSA-N methyl N-[N-(2-amino-4-pyridin-2-yloxyphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)OC1=NC=CC=C1)SC WUZPOJUFGNMNBH-UHFFFAOYSA-N 0.000 description 1
- VEEHACFLNPXLLH-UHFFFAOYSA-N methyl N-[N-(2-amino-4-thiocyanatophenyl)-C-butylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SC#N)SCCCC VEEHACFLNPXLLH-UHFFFAOYSA-N 0.000 description 1
- JJQLLKDLTPHRDQ-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-(2-phenylethylsulfanyl)carbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCC1=CC=CC=C1 JJQLLKDLTPHRDQ-UHFFFAOYSA-N 0.000 description 1
- KOPWWTKXCAMNMP-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-benzylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCC1=CC=CC=C1 KOPWWTKXCAMNMP-UHFFFAOYSA-N 0.000 description 1
- KNDCWHNMGXBHJI-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-butylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCC KNDCWHNMGXBHJI-UHFFFAOYSA-N 0.000 description 1
- CSEDGJPISPESMQ-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-ethylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCC CSEDGJPISPESMQ-UHFFFAOYSA-N 0.000 description 1
- LINGGSBKQZUROT-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-nonadecylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCCCCCCCCCCCCCCCCC LINGGSBKQZUROT-UHFFFAOYSA-N 0.000 description 1
- UHHHRJFVCDXYPH-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-prop-2-ynylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCC#C UHHHRJFVCDXYPH-UHFFFAOYSA-N 0.000 description 1
- FUZAIYFCQSTPSI-UHFFFAOYSA-N methyl N-[N-(2-amino-5-pentanoylphenyl)-C-butylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)C(CCCC)=O)SCCCC FUZAIYFCQSTPSI-UHFFFAOYSA-N 0.000 description 1
- CRAXBRCXRKLYAY-UHFFFAOYSA-N methyl N-[N-(2-amino-5-propanoylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)C(CC)=O)SC CRAXBRCXRKLYAY-UHFFFAOYSA-N 0.000 description 1
- OLZJMTVOFHFBAM-UHFFFAOYSA-N methyl N-[N-(2-amino-5-thiocyanatophenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)SC#N)SC OLZJMTVOFHFBAM-UHFFFAOYSA-N 0.000 description 1
- BNJDDPUYHPYHSD-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(2-phenylsulfanylethylsulfanyl)phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SCCSC1=CC=CC=C1)SC BNJDDPUYHPYHSD-UHFFFAOYSA-N 0.000 description 1
- PRKOGJYKAGXRLM-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(3-chloropropoxy)phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)OCCCCl)SC PRKOGJYKAGXRLM-UHFFFAOYSA-N 0.000 description 1
- YOIBJUAYLWHCHL-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(3-chloropropylsulfanyl)phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SCCCCl)SC YOIBJUAYLWHCHL-UHFFFAOYSA-N 0.000 description 1
- BGIXVDXXALSQQG-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(3-cyanophenyl)sulfanylphenyl]-C-butylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SC1=CC(=CC=C1)C#N)SCCCC BGIXVDXXALSQQG-UHFFFAOYSA-N 0.000 description 1
- MYTUQPQEVLCOKL-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(3-methylsulfanylphenyl)sulfanylphenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SC1=CC(=CC=C1)SC)SC MYTUQPQEVLCOKL-UHFFFAOYSA-N 0.000 description 1
- NDHZVRLVEZUZBI-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(4-methylsulfanylphenyl)sulfanylphenyl]-C-butylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SC1=CC=C(C=C1)SC)SCCCC NDHZVRLVEZUZBI-UHFFFAOYSA-N 0.000 description 1
- HKGFZQRPNNKFKB-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(furan-2-ylsulfanyl)phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SC=1OC=CC1)SC HKGFZQRPNNKFKB-UHFFFAOYSA-N 0.000 description 1
- MROOACBRTKPDHO-UHFFFAOYSA-N methyl N-[N-[2-amino-5-(4-cyanophenyl)sulfinylphenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)C1=CC=C(C=C1)C#N)SC MROOACBRTKPDHO-UHFFFAOYSA-N 0.000 description 1
- FVWXBQIFRNEYHY-UHFFFAOYSA-N methyl N-[N-[2-amino-5-(4-cyanophenyl)sulfonylphenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)(=O)C1=CC=C(C=C1)C#N)SC FVWXBQIFRNEYHY-UHFFFAOYSA-N 0.000 description 1
- MHNUFFPDTGYGNE-UHFFFAOYSA-N methyl N-[N-[2-amino-5-(4-propanoylphenyl)sulfonylphenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)(=O)C1=CC=C(C=C1)C(CC)=O)SC MHNUFFPDTGYGNE-UHFFFAOYSA-N 0.000 description 1
- YEFRSRFBHWEOTN-UHFFFAOYSA-N methyl N-[N-[2-amino-5-(benzenesulfinyl)phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)C1=CC=CC=C1)SC YEFRSRFBHWEOTN-UHFFFAOYSA-N 0.000 description 1
- FFNRGJYEKDXMRZ-UHFFFAOYSA-N methyl N-[N-[2-amino-5-(benzenesulfonyl)phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)(=O)C1=CC=CC=C1)SC FFNRGJYEKDXMRZ-UHFFFAOYSA-N 0.000 description 1
- ISBIDPZKMJJFBE-UHFFFAOYSA-N methyl N-[N-[2-amino-5-[3-(trifluoromethyl)benzoyl]phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)C(C1=CC(=CC=C1)C(F)(F)F)=O)SC ISBIDPZKMJJFBE-UHFFFAOYSA-N 0.000 description 1
- CDQBRDKPMGPXGA-UHFFFAOYSA-N methyl N-[N-[4-(4-acetylphenyl)sulfanyl-2-aminophenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SC1=CC=C(C=C1)C(C)=O)SC CDQBRDKPMGPXGA-UHFFFAOYSA-N 0.000 description 1
- YEJBONWUWODHRP-UHFFFAOYSA-N methyl N-[N-[4-(4-acetylphenyl)sulfinyl-2-aminophenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)S(=O)C1=CC=C(C=C1)C(C)=O)SC YEJBONWUWODHRP-UHFFFAOYSA-N 0.000 description 1
- RFXOSAWVRPXDFD-UHFFFAOYSA-N methyl N-[N-[5-(4-acetylphenyl)sulfinyl-2-aminophenyl]-C-butylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)C1=CC=C(C=C1)C(C)=O)SCCCC RFXOSAWVRPXDFD-UHFFFAOYSA-N 0.000 description 1
- HRSUWLBDLCXAMO-UHFFFAOYSA-N methyl N-[N-[5-(4-acetylphenyl)sulfonyl-2-aminophenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=CC(=C1)S(=O)(=O)C1=CC=C(C=C1)C(C)=O)SC HRSUWLBDLCXAMO-UHFFFAOYSA-N 0.000 description 1
- WLLQBAZOQHUNBF-UHFFFAOYSA-N methyl N-[[2-amino-5-(benzenesulfonyl)phenyl]carbamothioyl]carbamate Chemical compound C(=O)(OC)NC(NC1=C(N)C=CC(=C1)S(=O)(=O)C1=CC=CC=C1)=S WLLQBAZOQHUNBF-UHFFFAOYSA-N 0.000 description 1
- QVXGXKQYZXVOJG-UHFFFAOYSA-N methyl n-[(2-amino-5-nitrophenyl)carbamothioyl]carbamate Chemical compound COC(=O)NC(=S)NC1=CC([N+]([O-])=O)=CC=C1N QVXGXKQYZXVOJG-UHFFFAOYSA-N 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical class N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([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
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl 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])C([H])([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
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000002958 pentadecyl 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])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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ROVPGRDMDASARO-UHFFFAOYSA-N phenyl 3,4-diaminobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)OC1=CC=CC=C1 ROVPGRDMDASARO-UHFFFAOYSA-N 0.000 description 1
- HRXKJBAGXBZJMM-UHFFFAOYSA-N phenyl 3-amino-4-[[(methoxycarbonylamino)-methylsulfanylmethylidene]amino]benzenesulfonate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)S(=O)(=O)OC1=CC=CC=C1)SC HRXKJBAGXBZJMM-UHFFFAOYSA-N 0.000 description 1
- VQMRSSOUOMTFES-UHFFFAOYSA-N phenyl 3-bromobutanoate Chemical compound CC(Br)CC(=O)OC1=CC=CC=C1 VQMRSSOUOMTFES-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- DCYJIQSNTSZXAS-UHFFFAOYSA-N propan-2-yl 2-amino-5-benzoylbenzoate Chemical compound C(=O)(OC(C)C)C=1C=C(C(=O)C2=CC=CC=C2)C=CC1N DCYJIQSNTSZXAS-UHFFFAOYSA-N 0.000 description 1
- OKABCAUDCGGHBH-UHFFFAOYSA-N propan-2-yl N-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C(=O)(OC(C)C)NC(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)=S OKABCAUDCGGHBH-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- OQJXCJBEWYTUSU-UHFFFAOYSA-N propyl N-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C(=O)(OCCC)NC(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)=S OQJXCJBEWYTUSU-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OKHILJWKJWMSEP-UHFFFAOYSA-N propylsulfonylbenzene Chemical compound CCCS(=O)(=O)C1=CC=CC=C1 OKHILJWKJWMSEP-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 150000003463 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 239000004753 textile Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68355476A | 1976-05-05 | 1976-05-05 | |
| US78323477A | 1977-03-31 | 1977-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1576633A true GB1576633A (en) | 1980-10-08 |
Family
ID=27103138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18212/77A Expired GB1576633A (en) | 1976-05-05 | 1977-05-02 | 2-(3-carboxy - s - substituted - isothioureido)-anilines |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS537645A (enExample) |
| AR (1) | AR213309A1 (enExample) |
| AU (1) | AU2493077A (enExample) |
| BR (1) | BR7702864A (enExample) |
| CA (1) | CA1105038A (enExample) |
| CH (1) | CH621542A5 (enExample) |
| DE (1) | DE2720290A1 (enExample) |
| DK (1) | DK193177A (enExample) |
| FR (1) | FR2372154A1 (enExample) |
| GB (1) | GB1576633A (enExample) |
| IL (1) | IL52004A (enExample) |
| NL (1) | NL7704975A (enExample) |
| NZ (1) | NZ183993A (enExample) |
| SE (1) | SE7705156L (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4406893A (en) * | 1980-10-20 | 1983-09-27 | Schering Corporation | N-Alkoxycarbonyl-N'-[2-nitro-4 or 5-alkylthiophenyl]-N"-[substituted alkyl]-guanidines useful as anthelmintics |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1177379B (it) * | 1984-12-11 | 1987-08-26 | Anic Spa | Derivati della sostanza p e di suoi frammenti |
| JP5773975B2 (ja) | 2012-12-26 | 2015-09-02 | 本田技研工業株式会社 | 鞍乗り型車両の排気管カバー構造 |
-
1977
- 1977-04-29 AR AR267417A patent/AR213309A1/es active
- 1977-05-02 GB GB18212/77A patent/GB1576633A/en not_active Expired
- 1977-05-03 SE SE7705156A patent/SE7705156L/xx unknown
- 1977-05-03 DK DK193177A patent/DK193177A/da unknown
- 1977-05-03 NZ NZ183993A patent/NZ183993A/xx unknown
- 1977-05-03 CH CH549577A patent/CH621542A5/fr not_active IP Right Cessation
- 1977-05-04 CA CA277,661A patent/CA1105038A/en not_active Expired
- 1977-05-04 BR BR7702864A patent/BR7702864A/pt unknown
- 1977-05-04 IL IL52004A patent/IL52004A/xx unknown
- 1977-05-04 JP JP5166077A patent/JPS537645A/ja active Pending
- 1977-05-05 DE DE19772720290 patent/DE2720290A1/de not_active Withdrawn
- 1977-05-05 AU AU24930/77A patent/AU2493077A/en not_active Expired
- 1977-05-05 FR FR7713728A patent/FR2372154A1/fr active Granted
- 1977-05-05 NL NL7704975A patent/NL7704975A/xx not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4406893A (en) * | 1980-10-20 | 1983-09-27 | Schering Corporation | N-Alkoxycarbonyl-N'-[2-nitro-4 or 5-alkylthiophenyl]-N"-[substituted alkyl]-guanidines useful as anthelmintics |
Also Published As
| Publication number | Publication date |
|---|---|
| AR213309A1 (es) | 1979-01-15 |
| DK193177A (da) | 1977-11-06 |
| NL7704975A (nl) | 1977-11-08 |
| FR2372154A1 (fr) | 1978-06-23 |
| JPS537645A (en) | 1978-01-24 |
| SE7705156L (sv) | 1977-11-06 |
| CH621542A5 (en) | 1981-02-13 |
| FR2372154B1 (enExample) | 1980-03-07 |
| NZ183993A (en) | 1979-11-01 |
| DE2720290A1 (de) | 1977-11-17 |
| BR7702864A (pt) | 1978-03-28 |
| AU2493077A (en) | 1978-11-09 |
| IL52004A (en) | 1981-05-20 |
| IL52004A0 (en) | 1977-07-31 |
| CA1105038A (en) | 1981-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |