CA1105038A - 2-amino-substituted isothioureidobenzene - Google Patents
2-amino-substituted isothioureidobenzeneInfo
- Publication number
- CA1105038A CA1105038A CA277,661A CA277661A CA1105038A CA 1105038 A CA1105038 A CA 1105038A CA 277661 A CA277661 A CA 277661A CA 1105038 A CA1105038 A CA 1105038A
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- carbomethoxy
- aminobenzophenone
- mole
- solution
- 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
- -1 2-amino-substituted isothioureidobenzene Chemical class 0.000 title claims abstract description 67
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 23
- 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 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 125000005544 phthalimido group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 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 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 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 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 3
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 claims description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 9
- 238000004519 manufacturing process Methods 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 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 claims 2
- 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 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- XWJFZTFTLJXWQC-UHFFFAOYSA-N methyl N-[(2-amino-4-propylsulfanylphenyl)carbamothioyl]carbamate Chemical compound CCCSC1=CC=C(NC(=S)NC(=O)OC)C(N)=C1 XWJFZTFTLJXWQC-UHFFFAOYSA-N 0.000 claims 1
- NLPFATRXUGIRCS-UHFFFAOYSA-N methyl N-[N-(2-amino-5-benzoylphenyl)-C-(3-hydroxypropylsulfanyl)carbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SCCCO NLPFATRXUGIRCS-UHFFFAOYSA-N 0.000 claims 1
- PEKRQNRYZZPPCL-UHFFFAOYSA-N methyl n-[(2-amino-5-phenylsulfanylphenyl)carbamothioyl]carbamate Chemical compound C1=C(N)C(NC(=S)NC(=O)OC)=CC(SC=2C=CC=CC=2)=C1 PEKRQNRYZZPPCL-UHFFFAOYSA-N 0.000 claims 1
- FWJFBKVUKMVJJN-UHFFFAOYSA-N methyl n-[[2-amino-5-(benzenesulfinyl)phenyl]carbamothioyl]carbamate Chemical compound C1=C(N)C(NC(=S)NC(=O)OC)=CC(S(=O)C=2C=CC=CC=2)=C1 FWJFBKVUKMVJJN-UHFFFAOYSA-N 0.000 claims 1
- 230000000507 anthelmentic effect Effects 0.000 abstract description 8
- 229940124339 anthelmintic agent Drugs 0.000 abstract description 4
- 239000000921 anthelmintic agent Substances 0.000 abstract description 4
- 239000000417 fungicide Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 152
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 102
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 96
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 93
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 92
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
- 239000000203 mixture Substances 0.000 description 50
- 239000002244 precipitate Substances 0.000 description 34
- 238000001914 filtration Methods 0.000 description 30
- 239000000725 suspension Substances 0.000 description 30
- 101150008415 CALCA gene Proteins 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 18
- 239000012065 filter cake Substances 0.000 description 15
- 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
- 241001465754 Metazoa Species 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 150000002540 isothiocyanates Chemical class 0.000 description 7
- LBFAAYMITJMZOC-UHFFFAOYSA-N methyl n-(sulfanylidenemethylidene)carbamate Chemical compound COC(=O)N=C=S LBFAAYMITJMZOC-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229940093499 ethyl acetate Drugs 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241001494479 Pecora Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 3
- 208000006968 Helminthiasis Diseases 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 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
- 239000012965 benzophenone Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 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 2
- GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 2
- 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
- 241000283690 Bos taurus Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000282849 Ruminantia Species 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 101100162169 Xenopus laevis adrm1-a gene Proteins 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic 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
- 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
- 150000002431 hydrogen Chemical group 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 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
- 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
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-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
- 239000008188 pellet Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 229940013123 stannous chloride Drugs 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 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 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HXBMIQJOSHZCFX-UHFFFAOYSA-N 1-(bromomethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CBr HXBMIQJOSHZCFX-UHFFFAOYSA-N 0.000 description 1
- WZRKSPFYXUXINF-UHFFFAOYSA-N 1-(bromomethyl)-4-methylbenzene Chemical compound CC1=CC=C(CBr)C=C1 WZRKSPFYXUXINF-UHFFFAOYSA-N 0.000 description 1
- KWISWUFGPUHDRY-UHFFFAOYSA-N 1-Chloro-2-methylpropene Chemical compound CC(C)=CCl KWISWUFGPUHDRY-UHFFFAOYSA-N 0.000 description 1
- ALOQTNHQNMYBDE-UHFFFAOYSA-N 1-bromo-4-methoxybutane Chemical compound COCCCCBr ALOQTNHQNMYBDE-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- PDFGFQUSSYSWNI-UHFFFAOYSA-N 2-(bromomethyl)-1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1CBr PDFGFQUSSYSWNI-UHFFFAOYSA-N 0.000 description 1
- RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BWSQKOKULIALEW-UHFFFAOYSA-N 2-[2-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[2-(piperidin-3-ylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound FC1=C(C=C(C=C1)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CNCCC1)C(F)(F)F BWSQKOKULIALEW-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- AJGJUXSVUPXOHL-UHFFFAOYSA-N 2-nitro-5-phenylsulfanylaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC(SC=2C=CC=CC=2)=C1 AJGJUXSVUPXOHL-UHFFFAOYSA-N 0.000 description 1
- DKULSTMKCYRQCP-UHFFFAOYSA-N 2-phenylethyl carbonochloridate Chemical compound ClC(=O)OCCC1=CC=CC=C1 DKULSTMKCYRQCP-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical compound BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 description 1
- NIDWUZTTXGJFNN-UHFFFAOYSA-N 3-bromopropoxybenzene Chemical compound BrCCCOC1=CC=CC=C1 NIDWUZTTXGJFNN-UHFFFAOYSA-N 0.000 description 1
- DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 1
- WQEGHHLKDKIWKM-UHFFFAOYSA-N 4-butylbenzene-1,2-diamine Chemical compound CCCCC1=CC=C(N)C(N)=C1 WQEGHHLKDKIWKM-UHFFFAOYSA-N 0.000 description 1
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-IDEBNGHGSA-N 4-nitroaniline Chemical compound N[13C]1=[13CH][13CH]=[13C]([N+]([O-])=O)[13CH]=[13CH]1 TYMLOMAKGOJONV-IDEBNGHGSA-N 0.000 description 1
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 1
- TZQVSGOOKNNDFU-UHFFFAOYSA-N 4-phenylsulfanylaniline Chemical compound C1=CC(N)=CC=C1SC1=CC=CC=C1 TZQVSGOOKNNDFU-UHFFFAOYSA-N 0.000 description 1
- SNNMXLZBXANAFL-UHFFFAOYSA-N 4-propylsulfonylbenzene-1,2-diamine Chemical compound CCCS(=O)(=O)C1=CC=C(N)C(N)=C1 SNNMXLZBXANAFL-UHFFFAOYSA-N 0.000 description 1
- NWWWGAKVHCSAEU-UHFFFAOYSA-N 5-bromopentanenitrile Chemical compound BrCCCCC#N NWWWGAKVHCSAEU-UHFFFAOYSA-N 0.000 description 1
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 101100328884 Caenorhabditis elegans sqt-3 gene Proteins 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241001340534 Eido Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000498255 Enterobius vermicularis Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000243789 Metastrongyloidea Species 0.000 description 1
- QRBVCAWHUSTDOT-UHFFFAOYSA-N Methyridine Chemical compound COCCC1=CC=CC=N1 QRBVCAWHUSTDOT-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101100328463 Mus musculus Cmya5 gene Proteins 0.000 description 1
- 101100128278 Mus musculus Lins1 gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 206010067720 Parasitic gastroenteritis Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000344768 Trichuris ovis Species 0.000 description 1
- TUJNVZMPIUFYFR-UHFFFAOYSA-N [4-(benzenesulfonyl)phenyl]hydrazine Chemical compound C1=CC(NN)=CC=C1S(=O)(=O)C1=CC=CC=C1 TUJNVZMPIUFYFR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000012871 anti-fungal composition Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- ZKXKCDBQTJEDAD-UHFFFAOYSA-N butyl N-[(2-amino-5-benzoylphenyl)carbamothioyl]carbamate Chemical compound C(=O)(OCCCC)NC(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)=S ZKXKCDBQTJEDAD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008395 clarifying agent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 206010014881 enterobiasis Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HVZGPSKQAMWDDV-UHFFFAOYSA-N ethyl 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)OCC HVZGPSKQAMWDDV-UHFFFAOYSA-N 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 1
- KIWBRXCOTCXSSZ-UHFFFAOYSA-N hexyl carbonochloridate Chemical compound CCCCCCOC(Cl)=O KIWBRXCOTCXSSZ-UHFFFAOYSA-N 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 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 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
- 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
- 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
- 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 1
- 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 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
- 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
- VHKYCKNJTSTQME-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(1,3-thiazol-2-ylsulfanyl)phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SC=1SC=CN=1)SC VHKYCKNJTSTQME-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
- YOIBJUAYLWHCHL-UHFFFAOYSA-N methyl N-[N-[2-amino-4-(3-chloropropylsulfanyl)phenyl]-C-methylsulfanylcarbonimidoyl]carbamate Chemical class C(=O)(OC)N=C(NC1=C(N)C=C(C=C1)SCCCCl)SC YOIBJUAYLWHCHL-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
- 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
- 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
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- YOVQDZPAVARTTR-UHFFFAOYSA-N methyl n-(oxomethylidene)carbamate Chemical compound COC(=O)N=C=O YOVQDZPAVARTTR-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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical class N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 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
- 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
- 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
- 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
- VQMRSSOUOMTFES-UHFFFAOYSA-N phenyl 3-bromobutanoate Chemical compound CC(Br)CC(=O)OC1=CC=CC=C1 VQMRSSOUOMTFES-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- NSYAKUNTVKLTAU-UHFFFAOYSA-N propan-2-yl N-[N-(2-amino-5-benzoylphenyl)-C-methylsulfanylcarbonimidoyl]carbamate Chemical compound C(=O)(OC(C)C)N=C(NC=1C=C(C(=O)C2=CC=CC=C2)C=CC1N)SC NSYAKUNTVKLTAU-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
- 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 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
- 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
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 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
- 231100000057 systemic toxicity Toxicity 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
- 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
- 239000002023 wood Substances 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68355476A | 1976-05-05 | 1976-05-05 | |
| US683,554 | 1976-05-05 | ||
| US78323477A | 1977-03-31 | 1977-03-31 | |
| US783,234 | 1977-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105038A true CA1105038A (en) | 1981-07-14 |
Family
ID=27103138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA277,661A Expired CA1105038A (en) | 1976-05-05 | 1977-05-04 | 2-amino-substituted isothioureidobenzene |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS537645A (OSRAM) |
| AR (1) | AR213309A1 (OSRAM) |
| AU (1) | AU2493077A (OSRAM) |
| BR (1) | BR7702864A (OSRAM) |
| CA (1) | CA1105038A (OSRAM) |
| CH (1) | CH621542A5 (OSRAM) |
| DE (1) | DE2720290A1 (OSRAM) |
| DK (1) | DK193177A (OSRAM) |
| FR (1) | FR2372154A1 (OSRAM) |
| GB (1) | GB1576633A (OSRAM) |
| IL (1) | IL52004A (OSRAM) |
| NL (1) | NL7704975A (OSRAM) |
| NZ (1) | NZ183993A (OSRAM) |
| SE (1) | SE7705156L (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348406A (en) * | 1980-10-20 | 1982-09-07 | Schering Corporation | Novel guanidine derivatives |
| 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
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 |
| GB1576633A (en) | 1980-10-08 |
| CH621542A5 (en) | 1981-02-13 |
| FR2372154B1 (OSRAM) | 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0091596B1 (de) | Neue Hydantoine, ihre Herstellung und Verwendung | |
| EP0115039B1 (de) | Substituierte Phenylsulfonyloxybenzimidazolcarbaminate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| US3839575A (en) | 2-(pyrazolyl-(1))-benzimidazole fungicidal,and bactericidal agents | |
| EP0189473A1 (de) | Neue dopamin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. | |
| US3965113A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| CA1105038A (en) | 2-amino-substituted isothioureidobenzene | |
| US4053598A (en) | Preparation of 2,4-dioxo-1,2,3,4-tetrahydro-s-triazino-[1,2-a]-benzimidazoles | |
| US3850954A (en) | 1-acyl-3-aminosulfonyl-2-imino-benzimidazolines | |
| US3780089A (en) | Substituted ureidophenyl thioureas | |
| US3843715A (en) | Amidophenylisothioureas | |
| EP0008367A1 (de) | N-Arylsulfonylpyrrole, ihre Herstellung und diese enthaltende therapeutische Mittel | |
| US4176192A (en) | Substituted phenylguanidines and process for their manufacture | |
| US3956307A (en) | Benzimidazole-1-carboximidic acid esters | |
| US3629458A (en) | Fungicidal methods and compositions comprising trichloroacetaldehyde aminals | |
| US4136189A (en) | 2-(5-nitro-furfurylidene)-amino-benzimidoles and fungicidal compositions containing the same | |
| EP0000030B1 (de) | Schwefelhaltige Diurethane, Verfahren zu deren Herstellung und deren Verwendung als Herbizide | |
| PL103009B1 (pl) | Sposob wytwarzania nowych pochodnych benzenu | |
| EP0094562B1 (de) | Diaminderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| US3835164A (en) | N-alkoxycarbonyl-n{40 -acyl-n{41 12-acylamidophenyl-guanidines | |
| CA1050552A (en) | Benzimidazole derivatives | |
| EP0003974B1 (de) | Trifluormethylimino-thiazolidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| US3513237A (en) | Pesticidal 2-trihalomethylbenzothiazoles | |
| EP0132734B1 (de) | Neopentylisocyanate und ihre Herstellung | |
| US4031234A (en) | 1,5(6)-Disubstituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| US3915983A (en) | Substituted benzimidazoles |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |