SE414402B - Sett att framstella alkyl-bensimidazol-karbamater - Google Patents
Sett att framstella alkyl-bensimidazol-karbamaterInfo
- Publication number
- SE414402B SE414402B SE7317261A SE7317261A SE414402B SE 414402 B SE414402 B SE 414402B SE 7317261 A SE7317261 A SE 7317261A SE 7317261 A SE7317261 A SE 7317261A SE 414402 B SE414402 B SE 414402B
- Authority
- SE
- Sweden
- Prior art keywords
- mixture
- carbomethoxyaminobenzimidazole
- treated
- methanol
- nitro
- Prior art date
Links
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title 1
- -1 sulfinyl compound Chemical class 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 63
- 238000010992 reflux Methods 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000012429 reaction media Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 241000243780 Heligmosomoides polygyrus Species 0.000 claims description 3
- 241001464384 Hymenolepis nana Species 0.000 claims description 3
- 241000975692 Syphacia obvelata Species 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 2
- 241000760148 Aspiculuris tetraptera Species 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- HUKTUOMDJONHJM-UHFFFAOYSA-N methyl N-[4-(2-methoxyethylsulfinyl)-1H-benzimidazol-2-yl]carbamate Chemical compound COCCS(=O)C1=CC=CC2=C1NC(NC(=O)OC)=N2 HUKTUOMDJONHJM-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 198
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 155
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 130
- 239000000203 mixture Substances 0.000 description 122
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 79
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 73
- 235000011054 acetic acid Nutrition 0.000 description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 238000001953 recrystallisation Methods 0.000 description 17
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 235000011167 hydrochloric acid Nutrition 0.000 description 15
- 239000007858 starting material Substances 0.000 description 14
- 239000012279 sodium borohydride Substances 0.000 description 13
- 229910000033 sodium borohydride Inorganic materials 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 235000011181 potassium carbonates Nutrition 0.000 description 11
- 239000011790 ferrous sulphate Substances 0.000 description 10
- 235000003891 ferrous sulphate Nutrition 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- QUWHIBBGKKRYFW-UHFFFAOYSA-N (4-amino-3-nitrophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1[N+]([O-])=O QUWHIBBGKKRYFW-UHFFFAOYSA-N 0.000 description 9
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- RLPLNYIDEVVEBK-UHFFFAOYSA-N (4-acetamido-3-nitrophenyl) thiocyanate Chemical group CC(=O)NC1=CC=C(SC#N)C=C1[N+]([O-])=O RLPLNYIDEVVEBK-UHFFFAOYSA-N 0.000 description 7
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 125000005110 aryl thio group Chemical group 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 235000011150 stannous chloride Nutrition 0.000 description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 7
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 6
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- OZZKMZSOGAOIFX-UHFFFAOYSA-N n-(4-hydroxy-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(O)C=C1[N+]([O-])=O OZZKMZSOGAOIFX-UHFFFAOYSA-N 0.000 description 6
- 150000004965 peroxy acids Chemical class 0.000 description 6
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 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 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 230000000507 anthelmentic effect Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000001119 stannous chloride Substances 0.000 description 5
- 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 4
- VHQCBSZJSOOPBX-UHFFFAOYSA-N 3-amino-4-nitrobenzenethiol Chemical compound NC1=CC(S)=CC=C1[N+]([O-])=O VHQCBSZJSOOPBX-UHFFFAOYSA-N 0.000 description 4
- GOMNLMUKDVTFGZ-UHFFFAOYSA-N 4-(methoxymethylsulfanyl)benzene-1,2-diamine Chemical compound COCSC1=CC=C(N)C(N)=C1 GOMNLMUKDVTFGZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- WWGPFEMUMRARLF-UHFFFAOYSA-N n-(4-benzylsulfanyl-2-nitrophenyl)acetamide Chemical compound C1=C([N+]([O-])=O)C(NC(=O)C)=CC=C1SCC1=CC=CC=C1 WWGPFEMUMRARLF-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 3
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 description 3
- QCMUICPFWNAGBF-UHFFFAOYSA-N 4-(methoxymethylsulfanyl)-2-nitroaniline Chemical compound COCSC1=CC=C(N)C([N+]([O-])=O)=C1 QCMUICPFWNAGBF-UHFFFAOYSA-N 0.000 description 3
- XCKYGWPKCWYBNV-UHFFFAOYSA-N 4-(methylsulfanylmethoxy)-2-nitroaniline Chemical compound CSCOC1=CC=C(N)C([N+]([O-])=O)=C1 XCKYGWPKCWYBNV-UHFFFAOYSA-N 0.000 description 3
- DNJRZKYRBSHVFS-UHFFFAOYSA-N 4-(methylsulfanylmethoxy)benzene-1,2-diamine Chemical compound CSCOC1=CC=C(N)C(N)=C1 DNJRZKYRBSHVFS-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 3
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJWXILRSYMNYRS-UHFFFAOYSA-N n-[4-(methoxymethylsulfanyl)-2-nitrophenyl]acetamide Chemical compound COCSC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 QJWXILRSYMNYRS-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 3
- 241000894007 species Species 0.000 description 3
- JVSORZTZKODIJB-UHFFFAOYSA-N (3,4-diaminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1N JVSORZTZKODIJB-UHFFFAOYSA-N 0.000 description 2
- TYHWOUFVKPTEDK-UHFFFAOYSA-N 1-(bromomethyl)-2-[2-(bromomethyl)phenoxy]benzene Chemical compound BrCC1=CC=CC=C1OC1=CC=CC=C1CBr TYHWOUFVKPTEDK-UHFFFAOYSA-N 0.000 description 2
- MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical compound CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 2
- BQLHMMQUVJCTAN-UHFFFAOYSA-N 1-chloro-3-methoxypropane Chemical compound COCCCCl BQLHMMQUVJCTAN-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- VVMGJYAZRIYYLQ-UHFFFAOYSA-N 2-(3,4-diaminophenyl)sulfanylacetonitrile Chemical compound NC1=CC=C(SCC#N)C=C1N VVMGJYAZRIYYLQ-UHFFFAOYSA-N 0.000 description 2
- BOVGVHPMJHCZOF-UHFFFAOYSA-N 2-(4-amino-3-nitrophenyl)sulfanylacetonitrile Chemical compound NC1=CC=C(SCC#N)C=C1[N+]([O-])=O BOVGVHPMJHCZOF-UHFFFAOYSA-N 0.000 description 2
- MIKWOBKVZYDURQ-UHFFFAOYSA-N 2-nitro-4-(2,2,2-trifluoroethylsulfanyl)aniline Chemical compound NC1=CC=C(SCC(F)(F)F)C=C1[N+]([O-])=O MIKWOBKVZYDURQ-UHFFFAOYSA-N 0.000 description 2
- MEOYQHJOOWJIJS-UHFFFAOYSA-N 2-nitro-4-prop-2-ynylsulfanylaniline Chemical compound NC1=CC=C(SCC#C)C=C1[N+]([O-])=O MEOYQHJOOWJIJS-UHFFFAOYSA-N 0.000 description 2
- CKLDCXPXUFMXCZ-UHFFFAOYSA-N 2-nitro-4-propylsulfinylaniline Chemical compound CCCS(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 CKLDCXPXUFMXCZ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- RJDZBBBICMMMFH-UHFFFAOYSA-N 3-(4-amino-3-nitrophenyl)sulfanylpropanenitrile Chemical compound NC1=CC=C(SCCC#N)C=C1[N+]([O-])=O RJDZBBBICMMMFH-UHFFFAOYSA-N 0.000 description 2
- XTDFRKBAIHNFQA-UHFFFAOYSA-N 4-(2,2,2-trifluoroethylsulfanyl)benzene-1,2-diamine Chemical compound NC1=CC=C(SCC(F)(F)F)C=C1N XTDFRKBAIHNFQA-UHFFFAOYSA-N 0.000 description 2
- ATYQRPFZFUIJDU-UHFFFAOYSA-N 4-(2-ethoxyethoxy)-2-nitroaniline Chemical compound CCOCCOC1=CC=C(N)C([N+]([O-])=O)=C1 ATYQRPFZFUIJDU-UHFFFAOYSA-N 0.000 description 2
- PIWDDCGEUOZMHB-UHFFFAOYSA-N 4-(2-ethoxyethylsulfanyl)-2-nitroaniline Chemical compound CCOCCSC1=CC=C(N)C([N+]([O-])=O)=C1 PIWDDCGEUOZMHB-UHFFFAOYSA-N 0.000 description 2
- LSQOETHDRXOYJB-UHFFFAOYSA-N 4-(2-ethoxyethylsulfanyl)benzene-1,2-diamine Chemical compound CCOCCSC1=CC=C(N)C(N)=C1 LSQOETHDRXOYJB-UHFFFAOYSA-N 0.000 description 2
- QVPUFANJOMCUMA-UHFFFAOYSA-N 4-(2-methoxyethoxy)benzene-1,2-diamine Chemical compound COCCOC1=CC=C(N)C(N)=C1 QVPUFANJOMCUMA-UHFFFAOYSA-N 0.000 description 2
- XZTAIJANGXIZIF-UHFFFAOYSA-N 4-(4-methylphenyl)sulfanylbenzene-1,2-diamine Chemical compound C1=CC(C)=CC=C1SC1=CC=C(N)C(N)=C1 XZTAIJANGXIZIF-UHFFFAOYSA-N 0.000 description 2
- ONRRILQSLJKTMH-UHFFFAOYSA-N 4-(benzenesulfinyl)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)C1=CC=CC=C1 ONRRILQSLJKTMH-UHFFFAOYSA-N 0.000 description 2
- RJQHQUNYKXLSFE-UHFFFAOYSA-N 4-(benzenesulfonyl)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)(=O)C1=CC=CC=C1 RJQHQUNYKXLSFE-UHFFFAOYSA-N 0.000 description 2
- JYMLEEMEKCPXBF-UHFFFAOYSA-N 4-(methoxymethoxy)-2-nitroaniline Chemical compound COCOC1=CC=C(N)C([N+]([O-])=O)=C1 JYMLEEMEKCPXBF-UHFFFAOYSA-N 0.000 description 2
- LNMVKMXZEPKPCR-UHFFFAOYSA-N 4-(methoxymethoxy)benzene-1,2-diamine Chemical compound COCOC1=CC=C(N)C(N)=C1 LNMVKMXZEPKPCR-UHFFFAOYSA-N 0.000 description 2
- GSCJDDJBNFQKBL-UHFFFAOYSA-N 4-(methylsulfanylmethylsulfanyl)benzene-1,2-diamine Chemical compound CSCSC1=CC=C(N)C(N)=C1 GSCJDDJBNFQKBL-UHFFFAOYSA-N 0.000 description 2
- SPZOIXIIJMSYAZ-UHFFFAOYSA-N 4-benzylsulfanyl-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1SCC1=CC=CC=C1 SPZOIXIIJMSYAZ-UHFFFAOYSA-N 0.000 description 2
- UQWBCYRXJLVETQ-UHFFFAOYSA-N 4-benzylsulfinyl-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1S(=O)CC1=CC=CC=C1 UQWBCYRXJLVETQ-UHFFFAOYSA-N 0.000 description 2
- WTQAIQAEAPOCOX-UHFFFAOYSA-N 4-benzylsulfinylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1S(=O)CC1=CC=CC=C1 WTQAIQAEAPOCOX-UHFFFAOYSA-N 0.000 description 2
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 2
- LWFOZCFJVOGQAM-UHFFFAOYSA-N 4-methylsulfanyl-2-nitroaniline Chemical compound CSC1=CC=C(N)C([N+]([O-])=O)=C1 LWFOZCFJVOGQAM-UHFFFAOYSA-N 0.000 description 2
- NDZFWKZHVAUUTN-UHFFFAOYSA-N 4-methylsulfonyl-2-nitroaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 NDZFWKZHVAUUTN-UHFFFAOYSA-N 0.000 description 2
- XWUNCRCMUXPZDR-UHFFFAOYSA-N 4-methylsulfonylbenzene-1,2-diamine Chemical compound CS(=O)(=O)C1=CC=C(N)C(N)=C1 XWUNCRCMUXPZDR-UHFFFAOYSA-N 0.000 description 2
- YLEPPBFOGUYOEI-UHFFFAOYSA-N 4-phenylsulfanylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1SC1=CC=CC=C1 YLEPPBFOGUYOEI-UHFFFAOYSA-N 0.000 description 2
- BJJSNHRXHAHWHT-UHFFFAOYSA-N 4-prop-2-ynylsulfanylbenzene-1,2-diamine Chemical compound NC1=CC=C(SCC#C)C=C1N BJJSNHRXHAHWHT-UHFFFAOYSA-N 0.000 description 2
- VWHBAJDTJAMASB-UHFFFAOYSA-N 5-(2-methoxyethoxy)-2-nitroaniline Chemical compound COCCOC1=CC=C([N+]([O-])=O)C(N)=C1 VWHBAJDTJAMASB-UHFFFAOYSA-N 0.000 description 2
- SRMIYTDFWDHSCC-UHFFFAOYSA-N 5-(4-methylphenyl)sulfanyl-2-nitroaniline Chemical compound C1=CC(C)=CC=C1SC1=CC=C([N+]([O-])=O)C(N)=C1 SRMIYTDFWDHSCC-UHFFFAOYSA-N 0.000 description 2
- AWPYQKOHIPZPFB-UHFFFAOYSA-N 5-(benzenesulfinyl)-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC(S(=O)C=2C=CC=CC=2)=C1 AWPYQKOHIPZPFB-UHFFFAOYSA-N 0.000 description 2
- QXFNQYBWFFJRCI-UHFFFAOYSA-N 5-(benzenesulfonyl)-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 QXFNQYBWFFJRCI-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical group CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SACPOVZYRYEAEN-UHFFFAOYSA-N n-(2-nitro-4-phenylmethoxyphenyl)acetamide Chemical compound C1=C([N+]([O-])=O)C(NC(=O)C)=CC=C1OCC1=CC=CC=C1 SACPOVZYRYEAEN-UHFFFAOYSA-N 0.000 description 2
- JDGNKNLNWLMYQL-UHFFFAOYSA-N n-(2-nitro-4-propylsulfanylphenyl)acetamide Chemical compound CCCSC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 JDGNKNLNWLMYQL-UHFFFAOYSA-N 0.000 description 2
- DENPXLVCFPUIKH-UHFFFAOYSA-N n-(4-benzylsulfinyl-2-nitrophenyl)acetamide Chemical compound C1=C([N+]([O-])=O)C(NC(=O)C)=CC=C1S(=O)CC1=CC=CC=C1 DENPXLVCFPUIKH-UHFFFAOYSA-N 0.000 description 2
- QPAVLELUFRXYRL-UHFFFAOYSA-N n-(4-methylsulfanyl-2-nitrophenyl)acetamide Chemical compound CSC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 QPAVLELUFRXYRL-UHFFFAOYSA-N 0.000 description 2
- SIVNUUNPXWLKGW-UHFFFAOYSA-N n-(4-methylsulfonyl-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(C)(=O)=O)C=C1[N+]([O-])=O SIVNUUNPXWLKGW-UHFFFAOYSA-N 0.000 description 2
- YWANGSCDWBUSBK-UHFFFAOYSA-N n-(5-chloro-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1[N+]([O-])=O YWANGSCDWBUSBK-UHFFFAOYSA-N 0.000 description 2
- OTFHIVXJARJOHC-UHFFFAOYSA-N n-[4-(methylsulfanylmethoxy)-2-nitrophenyl]acetamide Chemical compound CSCOC1=CC=C(NC(C)=O)C([N+]([O-])=O)=C1 OTFHIVXJARJOHC-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012430 organic reaction media Substances 0.000 description 2
- 229950007337 parbendazole Drugs 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- VTSFYUMTCQXCPG-UHFFFAOYSA-N (3,4-diaminophenyl)sulfanylmethyl thiocyanate Chemical compound NC1=CC=C(SCSC#N)C=C1N VTSFYUMTCQXCPG-UHFFFAOYSA-N 0.000 description 1
- CQOVBHGKTKIWLJ-UHFFFAOYSA-N (3-amino-4-nitrophenyl)sulfanylmethyl thiocyanate Chemical compound NC1=CC(SCSC#N)=CC=C1[N+]([O-])=O CQOVBHGKTKIWLJ-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- BZZXQZOBAUXLHZ-UHFFFAOYSA-N (c-methylsulfanylcarbonimidoyl)azanium;sulfate Chemical compound CSC(N)=N.CSC(N)=N.OS(O)(=O)=O BZZXQZOBAUXLHZ-UHFFFAOYSA-N 0.000 description 1
- NEFNOUUWYACOKP-UHFFFAOYSA-N 1-(chloromethoxy)butane Chemical compound CCCCOCCl NEFNOUUWYACOKP-UHFFFAOYSA-N 0.000 description 1
- IFMYFXJJIIGOIS-UHFFFAOYSA-N 1-(pyridin-3-ylmethyl)piperidin-4-amine;trihydrochloride Chemical compound Cl.Cl.Cl.C1CC(N)CCN1CC1=CC=CN=C1 IFMYFXJJIIGOIS-UHFFFAOYSA-N 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- GBNVXYXIRHSYEG-UHFFFAOYSA-N 1-chloro-2-ethylsulfanylethane Chemical compound CCSCCCl GBNVXYXIRHSYEG-UHFFFAOYSA-N 0.000 description 1
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 1
- MYFKLQFBFSHBPA-UHFFFAOYSA-N 1-chloro-2-methylsulfanylethane Chemical compound CSCCCl MYFKLQFBFSHBPA-UHFFFAOYSA-N 0.000 description 1
- XPJUCMIJGVAEGF-UHFFFAOYSA-N 1-chloro-4-(chloromethylsulfanyl)benzene Chemical compound ClCSC1=CC=C(Cl)C=C1 XPJUCMIJGVAEGF-UHFFFAOYSA-N 0.000 description 1
- DFLRARJQZRCCKN-UHFFFAOYSA-N 1-chloro-4-methoxybutane Chemical compound COCCCCCl DFLRARJQZRCCKN-UHFFFAOYSA-N 0.000 description 1
- GEIJLPZQQHHUPS-UHFFFAOYSA-N 1-nitro-3-phenylmethoxybenzene Chemical compound [O-][N+](=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 GEIJLPZQQHHUPS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- JGVXQZRIRQLMHA-UHFFFAOYSA-N 2-nitro-4-phenylmethoxyaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OCC1=CC=CC=C1 JGVXQZRIRQLMHA-UHFFFAOYSA-N 0.000 description 1
- XIYCJELCHVAZQG-UHFFFAOYSA-N 3-(3,4-diaminophenyl)sulfanylpropanenitrile Chemical compound NC1=CC=C(SCCC#N)C=C1N XIYCJELCHVAZQG-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- DQPWALUQKKNAOX-UHFFFAOYSA-N 4-(ethoxymethylsulfanyl)benzene-1,2-diamine Chemical compound CCOCSC1=CC=C(N)C(N)=C1 DQPWALUQKKNAOX-UHFFFAOYSA-N 0.000 description 1
- LAEYZLSHMWWJBZ-UHFFFAOYSA-N 4-(methylsulfanylmethyl)-2-nitroaniline Chemical compound CSCC1=CC=C(N)C([N+]([O-])=O)=C1 LAEYZLSHMWWJBZ-UHFFFAOYSA-N 0.000 description 1
- LZWIKKPNIVNMFH-UHFFFAOYSA-N 4-(methylsulfanylmethylsulfanyl)-2-nitroaniline Chemical compound CSCSC1=CC=C(N)C([N+]([O-])=O)=C1 LZWIKKPNIVNMFH-UHFFFAOYSA-N 0.000 description 1
- IQXUIDYRTHQTET-UHFFFAOYSA-N 4-amino-3-nitrophenol Chemical compound NC1=CC=C(O)C=C1[N+]([O-])=O IQXUIDYRTHQTET-UHFFFAOYSA-N 0.000 description 1
- HLSLIQFXUHQNSS-UHFFFAOYSA-N 4-benzylsulfanylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1SCC1=CC=CC=C1 HLSLIQFXUHQNSS-UHFFFAOYSA-N 0.000 description 1
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- UQVGKXPXBIVFMV-UHFFFAOYSA-N 4-phenylmethoxybenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OCC1=CC=CC=C1 UQVGKXPXBIVFMV-UHFFFAOYSA-N 0.000 description 1
- FSXGIGKQVXNUOY-UHFFFAOYSA-N 5-(ethoxymethylsulfanyl)-2-nitroaniline Chemical compound CCOCSC1=CC=C([N+]([O-])=O)C(N)=C1 FSXGIGKQVXNUOY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 241000244203 Caenorhabditis elegans Species 0.000 description 1
- 241000242722 Cestoda Species 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- UXUCVNXUWOLPRU-UHFFFAOYSA-N Chloromethyl thiocyanate Chemical compound ClCSC#N UXUCVNXUWOLPRU-UHFFFAOYSA-N 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 206010061201 Helminthic infection Diseases 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 241001137882 Nematodirus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920002701 Polyoxyl 40 Stearate Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical class C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 1
- LKXYJYDRLBPHRS-UHFFFAOYSA-N bromocyclopropane Chemical compound BrC1CC1 LKXYJYDRLBPHRS-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical group C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- WRIINKYBVSMNJQ-UHFFFAOYSA-N chloro thiocyanate Chemical compound ClSC#N WRIINKYBVSMNJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- XZCHJYXUPALGHH-UHFFFAOYSA-N chloromethylsulfanylethane Chemical compound CCSCCl XZCHJYXUPALGHH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- JWPATQAGOMXJLZ-UHFFFAOYSA-N ethyl (ne)-n-[amino(methylsulfanyl)methylidene]carbamate Chemical compound CCOC(=O)NC(=N)SC JWPATQAGOMXJLZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WTGSRTORBGXXSX-UHFFFAOYSA-N methyl N-(6-naphthalen-2-ylsulfinyl-1H-benzimidazol-2-yl)carbamate Chemical compound COC(=O)NC1=NC2=CC=C(C=C2N1)S(=O)C1=CC2=CC=CC=C2C=C1 WTGSRTORBGXXSX-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- MMBDAJMDNVQFDV-UHFFFAOYSA-N methyl n-[amino(methylsulfanyl)methylidene]carbamate Chemical compound COC(=O)N=C(N)SC MMBDAJMDNVQFDV-UHFFFAOYSA-N 0.000 description 1
- PAVFCCPMCLCMQC-UHFFFAOYSA-N methyl n-methoxycarbonyl-n-(c-methylsulfanylcarbonimidoyl)carbamate Chemical compound COC(=O)N(C(=O)OC)C(=N)SC PAVFCCPMCLCMQC-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- DELIIGCTPYGZLJ-UHFFFAOYSA-N n-(2-nitro-5-phenylsulfanylphenyl)acetamide Chemical compound C1=C([N+]([O-])=O)C(NC(=O)C)=CC(SC=2C=CC=CC=2)=C1 DELIIGCTPYGZLJ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- UNYQGGGCPWHENG-UHFFFAOYSA-N n-[5-(benzenesulfinyl)-2-nitrophenyl]acetamide Chemical compound C1=C([N+]([O-])=O)C(NC(=O)C)=CC(S(=O)C=2C=CC=CC=2)=C1 UNYQGGGCPWHENG-UHFFFAOYSA-N 0.000 description 1
- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical class [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- BGYRLQHQOKZRLN-UHFFFAOYSA-N propyl n-[amino(methylsulfanyl)methylidene]carbamate Chemical compound CCCOC(=O)NC(=N)SC BGYRLQHQOKZRLN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31929972A | 1972-12-29 | 1972-12-29 | |
| US417963A US3929821A (en) | 1972-12-29 | 1973-11-21 | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE414402B true SE414402B (sv) | 1980-07-28 |
Family
ID=26981949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7317261A SE414402B (sv) | 1972-12-29 | 1973-12-20 | Sett att framstella alkyl-bensimidazol-karbamater |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3929821A (en, 2012) |
| JP (1) | JPS5939428B2 (en, 2012) |
| AR (2) | AR216037A1 (en, 2012) |
| AT (1) | AT332883B (en, 2012) |
| BR (1) | BR7310296D0 (en, 2012) |
| CH (2) | CH613955A5 (en, 2012) |
| CS (1) | CS187390B2 (en, 2012) |
| DE (3) | DE2366069A1 (en, 2012) |
| DK (1) | DK137329B (en, 2012) |
| ES (2) | ES421927A1 (en, 2012) |
| FR (1) | FR2212150B1 (en, 2012) |
| GB (2) | GB1456497A (en, 2012) |
| HK (1) | HK8280A (en, 2012) |
| HU (1) | HU169272B (en, 2012) |
| IE (1) | IE40046B1 (en, 2012) |
| IL (1) | IL43860A (en, 2012) |
| IN (1) | IN138644B (en, 2012) |
| IT (1) | IT1046097B (en, 2012) |
| MY (1) | MY8000273A (en, 2012) |
| NL (1) | NL169738C (en, 2012) |
| PL (1) | PL95987B1 (en, 2012) |
| RO (1) | RO67150A (en, 2012) |
| SE (1) | SE414402B (en, 2012) |
| SU (1) | SU727143A3 (en, 2012) |
| YU (2) | YU36706B (en, 2012) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002640A (en) * | 1972-12-29 | 1977-01-11 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US4258198A (en) * | 1973-05-29 | 1981-03-24 | Smithkline Corporation | 5-Cycloalkyl thio- and oxy-2-carbalkoxyaminobenzimidazoles |
| DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
| DE2441202C2 (de) * | 1974-08-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | 2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel |
| US4086235A (en) * | 1976-04-12 | 1978-04-25 | Syntex (U.S.A.) Inc. | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| USRE30990E (en) * | 1976-07-16 | 1982-07-06 | E. R. Squibb & Sons, Inc. | Benzimidazole derivatives, compositions thereof and method of use as anthelmintics |
| US4046908A (en) * | 1976-07-16 | 1977-09-06 | E. R. Squibb & Sons, Inc. | Benzimidazole derivatives, compositions thereof and method of use as anthelmintics |
| DE2736507A1 (de) * | 1976-08-13 | 1978-02-16 | Wellcome Found | Antihelminthische zubereitungen |
| IE45741B1 (en) * | 1976-08-13 | 1982-11-17 | Wellcome Found | An anthelmintic ether combination |
| FR2362116A1 (fr) * | 1976-08-20 | 1978-03-17 | Oreal | Metaphenylenediamines et compositions tinctoriales les contenant |
| US4093732A (en) * | 1977-02-17 | 1978-06-06 | E. R. Squibb & Sons, Inc. | Sulfoxide derivatives of benzimidazoles |
| IT1076022B (it) * | 1977-04-20 | 1985-04-22 | Montedison Spa | Benzimidazolcarbammati antielmintici |
| IT1107749B (it) * | 1977-10-06 | 1985-11-25 | Montedison Spa | Benzimidazolcarbammato particolarmente attivo contro i parassiti gastroenterici e polmonari |
| US4152522A (en) * | 1978-01-03 | 1979-05-01 | Ethyl Corporation | Process for the preparation of 2-benzimidazole carbamates |
| US4156006A (en) * | 1978-01-09 | 1979-05-22 | E. R. Squibb & Sons, Inc. | Vinyl sulfide derivatives of benzimidazoles |
| US4136174A (en) * | 1978-01-18 | 1979-01-23 | E. R. Squibb & Sons, Inc. | Benzimidazolecarbamates and method |
| JPS54104837A (en) * | 1978-02-03 | 1979-08-17 | Nippon Denso Co Ltd | Controller of copying machines |
| US4145431A (en) * | 1978-02-16 | 1979-03-20 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral administration of sulfide- and sulfoxide-derivatives of benzimidazoles |
| US4154846A (en) * | 1978-06-16 | 1979-05-15 | E. R. Squibb & Sons, Inc. | Substituted thio-, sulfinyl-, and sulfonyl-alkyl benzimidazole carbamates |
| US4174400A (en) * | 1978-09-13 | 1979-11-13 | Merck & Co., Inc. | Anthelmintic benzimidazoles |
| DE2845537A1 (de) * | 1978-10-19 | 1980-04-30 | Bayer Ag | Benzimidazolylcarbamidsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DD147539A5 (de) * | 1978-12-06 | 1981-04-08 | Montedison Spa | Herstellung von in 5(6)-stellung substituierten benzimidazol-carbamaten |
| IT1100788B (it) * | 1978-12-06 | 1985-09-28 | Montedison Spa | Benzimidazol-carbammati |
| US4198422A (en) * | 1979-05-17 | 1980-04-15 | E. R. Squibb & Sons, Inc. | Substituted 2,3-naphthimidazole carbamates and method |
| EP0028455A1 (en) * | 1979-10-12 | 1981-05-13 | Imperial Chemical Industries Plc | 5-Phenylselenobenzimidazole derivatives, their preparation and anthelmintic or fasciolicidal compositions containing them |
| IL61232A (en) * | 1979-10-19 | 1985-09-29 | Chinoin Gyogyszer Es Vegyeszet | Process for the preparation of 2-amino(or alkoxycarbonylamino)-5(6)-thiocyanato(or thiol)benzimidazole derivatives |
| US4599428A (en) * | 1979-10-19 | 1986-07-08 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt | Process for the preparation of 5(6)-thio substituted benzimidazoles |
| HU182763B (hu) * | 1979-10-19 | 1984-03-28 | Chinoin Gyogyszer Es Vegyeszet | Eljárás 5(6)-alkiltio-benzimidazolil-alkil-karbamátok előállítására |
| US4299837A (en) | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
| DE3719783A1 (de) * | 1987-06-13 | 1988-12-22 | Hoechst Ag | Verfahren zur herstellung von 5-phenylsulfinyl-1h-2-(methoxycarbonylamino)- benzimidazol |
| GB9205368D0 (en) * | 1992-03-12 | 1992-04-22 | Pfizer Ltd | Benzimidozole anthelmintic agents |
| US6593466B1 (en) * | 1999-07-07 | 2003-07-15 | Isis Pharmaceuticals, Inc. | Guanidinium functionalized nucleotides and precursors thereof |
| DK1913009T3 (da) * | 2005-07-28 | 2010-08-16 | Intervet Int Bv | Nye benzimidazol(thio)carbamater med antiparasitisk virkning samt syntese heraf |
| CN102283698B (zh) * | 2006-06-12 | 2016-02-24 | 史密夫和内修有限公司 | 用于进行胫骨切除的引导装置 |
| AR061351A1 (es) | 2006-06-14 | 2008-08-20 | Intervet Int Bv | Composicion de carbamato de bencimidazol |
| CN102241635A (zh) * | 2011-04-28 | 2011-11-16 | 江苏宝众宝达药业有限公司 | 一种苯并咪唑类驱虫药苯硫咪唑的制备方法 |
| CN102863392A (zh) * | 2012-10-18 | 2013-01-09 | 江苏宝众宝达药业有限公司 | 一种奥芬达唑生产过程中大幅减少溶剂使用量的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2933502A (en) * | 1958-02-12 | 1960-04-19 | Du Pont | Benzimidazolone derivatives |
| US2933504A (en) * | 1959-08-10 | 1960-04-19 | Du Pont | Derivatives of polyalkoxycarbonyl imine |
| US3010968A (en) * | 1959-11-25 | 1961-11-28 | Du Pont | Process for manufacture of certain alkyl esters of benzimidazole carbamic acids |
| BE666795A (en, 2012) * | 1964-08-04 | 1966-01-13 | ||
| US3506767A (en) * | 1965-08-06 | 1970-04-14 | Geigy Chem Corp | Benzimidazole compositions and methods of use |
| US3401171A (en) * | 1966-03-11 | 1968-09-10 | Smithkline Corp | 2-amidobenzimidazoles |
| CH456236A (de) * | 1966-05-06 | 1968-07-15 | Agripat Sa | Verfahren zum Schützen textiler Keratinfasermaterialien vor Insektenfrass und Mittel zur Durchführung dieses Verfahrens |
| US3480642A (en) * | 1967-03-22 | 1969-11-25 | Smithkline Corp | Process for producing 2-carbalkoxyaminobenzimidazoles |
| CH490010A (de) * | 1967-10-26 | 1970-05-15 | Ciba Geigy | Schädlingsbekämpfungsmittel |
| US3562290A (en) * | 1967-11-07 | 1971-02-09 | Du Pont | Process for making 2-benzimidazolecarbamic acid alkyl esters |
| FR2059938A1 (en) * | 1969-03-14 | 1971-06-11 | Aries Robert | 1-haloalk(en)yl sulphenyl-2-aryloxycarbon-yl - |
| US3657267A (en) * | 1969-06-20 | 1972-04-18 | Janssen Pharmaceutica Nv | Benzimidazole carbamates |
| US3714180A (en) * | 1970-08-12 | 1973-01-30 | Squibb & Sons Inc | Sulfonyl benzimidazoles |
| US3694455A (en) * | 1970-11-19 | 1972-09-26 | Smith Kline French Lab | Acyloxyalkyl amidobenzimidazoles |
| US3720686A (en) * | 1971-04-01 | 1973-03-13 | Squibb & Sons Inc | Mercaptobenzimidazole derivatives |
-
1973
- 1973-11-21 US US417963A patent/US3929821A/en not_active Expired - Lifetime
- 1973-12-10 IN IN2692/CAL/73A patent/IN138644B/en unknown
- 1973-12-13 GB GB3023476A patent/GB1456497A/en not_active Expired
- 1973-12-13 GB GB5792573A patent/GB1455728A/en not_active Expired
- 1973-12-14 CH CH1760073A patent/CH613955A5/xx not_active IP Right Cessation
- 1973-12-14 CH CH68577A patent/CH608006A5/xx not_active IP Right Cessation
- 1973-12-17 DK DK685273AA patent/DK137329B/da not_active IP Right Cessation
- 1973-12-19 IL IL43860A patent/IL43860A/en unknown
- 1973-12-20 DE DE19732366069 patent/DE2366069A1/de active Granted
- 1973-12-20 SE SE7317261A patent/SE414402B/sv unknown
- 1973-12-20 DE DE2363351A patent/DE2363351C2/de not_active Expired
- 1973-12-20 DE DE2366070A patent/DE2366070C2/de not_active Expired
- 1973-12-20 HU HUSI1367A patent/HU169272B/hu unknown
- 1973-12-21 RO RO7377156A patent/RO67150A/ro unknown
- 1973-12-21 IE IE2322/73A patent/IE40046B1/xx unknown
- 1973-12-21 AT AT1075173A patent/AT332883B/de active
- 1973-12-21 CS CS738891A patent/CS187390B2/cs unknown
- 1973-12-26 JP JP744829A patent/JPS5939428B2/ja not_active Expired
- 1973-12-27 YU YU3371/73A patent/YU36706B/xx unknown
- 1973-12-28 BR BR10296/73A patent/BR7310296D0/pt unknown
- 1973-12-28 IT IT7901/73A patent/IT1046097B/it active Protection Beyond IP Right Term
- 1973-12-28 FR FR7346946A patent/FR2212150B1/fr not_active Expired
- 1973-12-28 AR AR251776A patent/AR216037A1/es active
- 1973-12-28 SU SU731980901A patent/SU727143A3/ru active
- 1973-12-28 NL NLAANVRAGE7317797,A patent/NL169738C/xx not_active IP Right Cessation
- 1973-12-29 ES ES421927A patent/ES421927A1/es not_active Expired
- 1973-12-29 PL PL1973167768A patent/PL95987B1/pl unknown
-
1976
- 1976-02-17 ES ES445257A patent/ES445257A1/es not_active Expired
- 1976-05-06 AR AR263212A patent/AR221816A1/es active
-
1980
- 1980-03-06 HK HK82/80A patent/HK8280A/xx unknown
- 1980-03-07 YU YU641/80A patent/YU40868B/xx unknown
- 1980-12-30 MY MY273/80A patent/MY8000273A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE414402B (sv) | Sett att framstella alkyl-bensimidazol-karbamater | |
| Godefroi et al. | DL-1-(1-arylalkyl) imidazole-5-carboxylate esters. A novel type of hypnotic agents | |
| CA2050908A1 (en) | Benzimidazole derivatives | |
| US3929823A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| KR910000045B1 (ko) | 치환된 페닐설포닐옥시벤즈이미다졸 카바메이트의 제조방법 | |
| US4002640A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| US3935209A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| US3965113A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| CN116655557B (zh) | 苯并噻唑类化合物、其制备方法及应用 | |
| US4026936A (en) | Anthelmintic pyridine and thiazole substituted benzimidazole carbamates | |
| US9018393B2 (en) | Method for preparing 2-(N-substituted)-amino-benzimidazole derivatives | |
| JPS6254786B2 (en, 2012) | ||
| US4005202A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| US4021571A (en) | Substituted phenylisothioureas and processes for their preparation and use | |
| FI85473C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-(isoxazolyl)-tiazol-2-oxaminsyraderivat och mellanprodukter. | |
| US3929822A (en) | 1,5(6)-Disubstituted benzizimidazole-2-carbamate derivatives having anthelmintic activity | |
| US4072696A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| US4504490A (en) | Substituted benzenesulfonic esters and their use as medicaments for combatting helminths | |
| CN106008653B (zh) | 甘草次酸酰腙类衍生物及其制备方法和用途 | |
| IE41655B1 (en) | Anthelmintically active-2-carbalkoxyamino benzimidazolyl-5(6) sulfonic acid phenyl esters and process for their manufacture | |
| US4254143A (en) | Monocarboxylates of phenylguanidinesulfonic acid esters, a process for their manufacture, compositions containing them and their use for combating helminths | |
| US3901901A (en) | 5(6)-benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| US4031234A (en) | 1,5(6)-Disubstituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| US4080461A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| US4136174A (en) | Benzimidazolecarbamates and method |