CA1058194A - Substituted benzenedisulfonamides as anthelmintics - Google Patents
Substituted benzenedisulfonamides as anthelminticsInfo
- Publication number
- CA1058194A CA1058194A CA241,261A CA241261A CA1058194A CA 1058194 A CA1058194 A CA 1058194A CA 241261 A CA241261 A CA 241261A CA 1058194 A CA1058194 A CA 1058194A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- amino
- formula
- trichlorovinyl
- benzenedisulfonamide
- 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
- VJDZMZAZDFKMSV-UHFFFAOYSA-N benzene-1,2-disulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1S(N)(=O)=O VJDZMZAZDFKMSV-UHFFFAOYSA-N 0.000 title abstract description 17
- 230000000507 anthelmentic effect Effects 0.000 title abstract description 13
- 229940124339 anthelmintic agent Drugs 0.000 title abstract description 7
- 239000000921 anthelmintic agent Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 53
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 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 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
- GAVSRYKULDMFMD-UHFFFAOYSA-N 3-(1,2-dichloroprop-1-enyl)aniline Chemical compound CC(Cl)=C(Cl)C1=CC=CC(N)=C1 GAVSRYKULDMFMD-UHFFFAOYSA-N 0.000 claims description 4
- NDVMLYRTLYSGKS-UHFFFAOYSA-N 4-amino-6-(1,2-dichloroprop-1-enyl)benzene-1,3-disulfonamide Chemical compound CC(Cl)=C(Cl)C1=CC(N)=C(S(N)(=O)=O)C=C1S(N)(=O)=O NDVMLYRTLYSGKS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- QOVTVIYTBRHADL-UHFFFAOYSA-N 4-amino-6-(1,2,2-trichloroethenyl)benzene-1,3-disulfonamide Chemical compound NC1=CC(C(Cl)=C(Cl)Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O QOVTVIYTBRHADL-UHFFFAOYSA-N 0.000 claims description 3
- DKQUUQVSXGNVBL-UHFFFAOYSA-N 4-bromo-6-(1,2,2-trichloroethenyl)benzene-1,3-disulfonamide Chemical compound NS(=O)(=O)C1=CC(S(N)(=O)=O)=C(C(Cl)=C(Cl)Cl)C=C1Br DKQUUQVSXGNVBL-UHFFFAOYSA-N 0.000 claims description 3
- BNBQMMRNNFDVLV-UHFFFAOYSA-N 4-(benzylamino)-6-(1,2,2-trichloroethenyl)benzene-1,3-disulfonamide Chemical compound NS(=O)(=O)C1=CC(S(N)(=O)=O)=C(C(Cl)=C(Cl)Cl)C=C1NCC1=CC=CC=C1 BNBQMMRNNFDVLV-UHFFFAOYSA-N 0.000 claims 2
- BVKPULAJYVKMGW-UHFFFAOYSA-N 4-amino-1-N,3-N-dimethyl-6-(1,2,2-trichloroethenyl)benzene-1,3-disulfonamide Chemical compound CNS(=O)(=O)C1=CC(S(=O)(=O)NC)=C(C(Cl)=C(Cl)Cl)C=C1N BVKPULAJYVKMGW-UHFFFAOYSA-N 0.000 claims 2
- YQBCCKGOIWMSDK-UHFFFAOYSA-N 4-amino-6-(1,2,2-trichloroethenyl)benzene-1,3-disulfonyl chloride Chemical compound NC1=CC(C(Cl)=C(Cl)Cl)=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O YQBCCKGOIWMSDK-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 49
- 241000242711 Fasciola hepatica Species 0.000 abstract description 5
- 208000006275 fascioliasis Diseases 0.000 abstract description 5
- 241001494479 Pecora Species 0.000 abstract description 3
- 241000283690 Bos taurus Species 0.000 abstract description 2
- 241000894007 species Species 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- BOZSDDFQWJUBNG-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonamide Chemical group NC1=CC=C(S(N)(=O)=O)C=C1S(N)(=O)=O BOZSDDFQWJUBNG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- -1 sulfonamide compounds Chemical class 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 241001465754 Metazoa Species 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- 229940093499 ethyl acetate Drugs 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 229940073584 methylene chloride Drugs 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229940124530 sulfonamide Drugs 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000012054 meals Nutrition 0.000 description 6
- 238000006396 nitration reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000003456 sulfonamides Chemical class 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- HUYYFHGIHVULSU-UHFFFAOYSA-N benzene-1-3-disulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(S(N)(=O)=O)=C1 HUYYFHGIHVULSU-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- YBGQXNZTVFEKEN-UHFFFAOYSA-N benzene-1,2-disulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1S(Cl)(=O)=O YBGQXNZTVFEKEN-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229960003280 cupric chloride Drugs 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- YTRHHRCQAWRXBK-UHFFFAOYSA-N 1-(1,2-dichloroethenyl)-3-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC(C(Cl)=CCl)=C1 YTRHHRCQAWRXBK-UHFFFAOYSA-N 0.000 description 2
- GKJYLNNPHBMOBG-UHFFFAOYSA-N 1-nitro-3-(1,2,2-trichloro-1,2-difluoroethyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C(F)(Cl)C(F)(Cl)Cl)=C1 GKJYLNNPHBMOBG-UHFFFAOYSA-N 0.000 description 2
- JYIFJVCSYLUPQI-UHFFFAOYSA-N 2-(1,2,2-trichloroethenyl)benzene-1,3-disulfonamide Chemical compound ClC(=C(Cl)Cl)C1=C(C=CC=C1S(=O)(=O)N)S(=O)(=O)N JYIFJVCSYLUPQI-UHFFFAOYSA-N 0.000 description 2
- WAPDWZMGMVOTAX-UHFFFAOYSA-N 3-(1,2,2-trichloro-1,2-difluoroethyl)aniline Chemical compound NC1=CC=CC(C(F)(Cl)C(F)(Cl)Cl)=C1 WAPDWZMGMVOTAX-UHFFFAOYSA-N 0.000 description 2
- FCLZQAKBHZCBDZ-UHFFFAOYSA-N 3-(1,2,2-trichloroethenyl)aniline Chemical group NC1=CC=CC(C(Cl)=C(Cl)Cl)=C1 FCLZQAKBHZCBDZ-UHFFFAOYSA-N 0.000 description 2
- IQKYEJIVEJPFSB-UHFFFAOYSA-N 3-(1,2-dichloroethenyl)aniline Chemical group NC1=CC=CC(C(Cl)=CCl)=C1 IQKYEJIVEJPFSB-UHFFFAOYSA-N 0.000 description 2
- HPJHTKRAUUDEPC-UHFFFAOYSA-N 3-(2-chloro-1,2-difluoroethenyl)aniline Chemical compound NC1=CC=CC(C(F)=C(F)Cl)=C1 HPJHTKRAUUDEPC-UHFFFAOYSA-N 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 2
- ZQZXLFGCRSXANQ-UHFFFAOYSA-N 4-(1,1-dichloroprop-1-en-2-yl)-2-nitroaniline Chemical compound ClC(Cl)=C(C)C1=CC=C(N)C([N+]([O-])=O)=C1 ZQZXLFGCRSXANQ-UHFFFAOYSA-N 0.000 description 2
- GNSOETXVXKPXCK-UHFFFAOYSA-N 4-amino-6-(2,2-dichloroethenyl)benzene-1,3-disulfonamide Chemical compound NC1=CC(C=C(Cl)Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O GNSOETXVXKPXCK-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000006052 feed supplement Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 244000000013 helminth Species 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- CYFOIVKNURKMPU-UHFFFAOYSA-N n-[4-(1,1-dichloroprop-1-en-2-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C(C)=C(Cl)Cl)C=C1 CYFOIVKNURKMPU-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2637—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions between a compound containing only oxygen and possibly halogen as hetero-atoms and a halogenated hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53335274A | 1974-12-16 | 1974-12-16 | |
| US05/616,331 US4064239A (en) | 1974-12-16 | 1975-09-26 | Halogenated unsaturated alkyl benzenedisulfonamides as anthelmintics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058194A true CA1058194A (en) | 1979-07-10 |
Family
ID=27064157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA241,261A Expired CA1058194A (en) | 1974-12-16 | 1975-12-08 | Substituted benzenedisulfonamides as anthelmintics |
Country Status (16)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107868024A (zh) * | 2017-10-25 | 2018-04-03 | 浙江海正药业股份有限公司 | 克洛索隆的晶型及其制备方法和用途 |
| CN113773235B (zh) * | 2021-08-20 | 2022-06-17 | 北大方正集团有限公司 | 一种氯舒隆的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1483222A (fr) * | 1965-06-24 | 1967-06-02 | Merck & Co Inc | Production de nouveaux dérivés, substitués à l'azote, de la 5-chloro-2, 4-disulfamoylaniline |
| SE410598B (sv) * | 1973-05-11 | 1979-10-22 | Merck & Co Inc | Forfarande for framstellning av bensendisulfonamider med anthelmintisk verkan |
-
1975
- 1975-12-02 SE SE7513569A patent/SE426817B/xx not_active IP Right Cessation
- 1975-12-02 FI FI753392A patent/FI64799C/fi not_active IP Right Cessation
- 1975-12-03 DK DK544775A patent/DK145756C/da not_active IP Right Cessation
- 1975-12-04 NL NLAANVRAGE7514163,A patent/NL187394C/xx active Protection Beyond IP Right Term
- 1975-12-04 NO NO754087A patent/NO142667C/no unknown
- 1975-12-08 IL IL48610A patent/IL48610A/xx unknown
- 1975-12-08 PH PH17844A patent/PH12041A/en unknown
- 1975-12-08 NZ NZ179477A patent/NZ179477A/xx unknown
- 1975-12-08 CA CA241,261A patent/CA1058194A/en not_active Expired
- 1975-12-09 IE IE2666/75A patent/IE42203B1/en unknown
- 1975-12-10 GB GB50628/75A patent/GB1485897A/en not_active Expired
- 1975-12-10 FR FR7537776A patent/FR2294710A1/fr active Granted
- 1975-12-11 AR AR261575A patent/AR218216A1/es active
- 1975-12-12 DE DE2556122A patent/DE2556122C2/de not_active Expired
- 1975-12-12 OA OA55691A patent/OA05183A/xx unknown
- 1975-12-15 LU LU74019A patent/LU74019A1/xx unknown
-
1993
- 1993-06-29 NL NL930115C patent/NL930115I1/nl unknown
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