DE2621583A1 - Pyridinderivate und ihre verwendung als antikokzidiosemittel - Google Patents
Pyridinderivate und ihre verwendung als antikokzidiosemittelInfo
- Publication number
- DE2621583A1 DE2621583A1 DE19762621583 DE2621583A DE2621583A1 DE 2621583 A1 DE2621583 A1 DE 2621583A1 DE 19762621583 DE19762621583 DE 19762621583 DE 2621583 A DE2621583 A DE 2621583A DE 2621583 A1 DE2621583 A1 DE 2621583A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- nitro
- hydrogen atom
- pyridinesulfonamide
- represent
- 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.)
- Withdrawn
Links
- 239000003795 chemical substances by application Substances 0.000 title claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 120
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- -1 2-ethoxyethyl Chemical group 0.000 claims description 78
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 42
- 150000003222 pyridines Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 37
- 125000003277 amino group Chemical group 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 244000144977 poultry Species 0.000 claims description 23
- 208000003495 Coccidiosis Diseases 0.000 claims description 18
- 206010023076 Isosporiasis Diseases 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- DGOADAPOUXCHCC-UHFFFAOYSA-N 5-nitropyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 DGOADAPOUXCHCC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- QFFPFFCAPYLOFR-UHFFFAOYSA-N 2-nitropyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1[N+]([O-])=O QFFPFFCAPYLOFR-UHFFFAOYSA-N 0.000 claims description 5
- LICDCKVYZROEQG-UHFFFAOYSA-N 5-aminopyridine-3-sulfonamide Chemical compound NC1=CN=CC(S(N)(=O)=O)=C1 LICDCKVYZROEQG-UHFFFAOYSA-N 0.000 claims description 5
- NKNHPPSYSOATEJ-UHFFFAOYSA-N 6-amino-n-methyl-5-nitropyridine-3-sulfonamide Chemical compound CNS(=O)(=O)C1=CN=C(N)C([N+]([O-])=O)=C1 NKNHPPSYSOATEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- UQTNLZDZGSZXBQ-UHFFFAOYSA-N n-methyl-6-(methylamino)-5-nitropyridine-3-sulfonamide Chemical compound CNC1=NC=C(S(=O)(=O)NC)C=C1[N+]([O-])=O UQTNLZDZGSZXBQ-UHFFFAOYSA-N 0.000 claims description 4
- URVTYDMISYITNH-UHFFFAOYSA-N n,n-diethyl-5-(ethylamino)pyridine-3-sulfonamide Chemical compound CCNC1=CN=CC(S(=O)(=O)N(CC)CC)=C1 URVTYDMISYITNH-UHFFFAOYSA-N 0.000 claims description 3
- ZDBDJVDUCLKPJD-UHFFFAOYSA-N n-(2-ethoxyethyl)-5-nitropyridine-3-sulfonamide Chemical compound CCOCCNS(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 ZDBDJVDUCLKPJD-UHFFFAOYSA-N 0.000 claims description 3
- HQXCONSTUVKATQ-UHFFFAOYSA-N n-ethyl-5-nitropyridine-3-sulfonamide Chemical compound CCNS(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 HQXCONSTUVKATQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- OOAWCHBAFNRKNW-UHFFFAOYSA-N 5-nitro-n-(3-propan-2-yloxypropyl)pyridine-3-sulfonamide Chemical compound CC(C)OCCCNS(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 OOAWCHBAFNRKNW-UHFFFAOYSA-N 0.000 claims description 2
- HBDIKYDVVNPJSE-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridine-3-sulfonamide Chemical compound CN(C)S(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 HBDIKYDVVNPJSE-UHFFFAOYSA-N 0.000 claims description 2
- SRBFDFAYVYNCCP-UHFFFAOYSA-N n-(5-nitropyridin-3-yl)sulfonyloctanamide Chemical compound CCCCCCCC(=O)NS(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 SRBFDFAYVYNCCP-UHFFFAOYSA-N 0.000 claims description 2
- ADXHKFBFOMDZKK-UHFFFAOYSA-N n-benzyl-5-nitropyridine-3-sulfonamide Chemical compound [O-][N+](=O)C1=CN=CC(S(=O)(=O)NCC=2C=CC=CC=2)=C1 ADXHKFBFOMDZKK-UHFFFAOYSA-N 0.000 claims description 2
- KWPKZSDORSVRPU-UHFFFAOYSA-N n-ethyl-6-(ethylamino)-5-nitropyridine-3-sulfonamide Chemical compound CCNC1=NC=C(S(=O)(=O)NCC)C=C1[N+]([O-])=O KWPKZSDORSVRPU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- KLWICZWDEZHZJL-UHFFFAOYSA-N 5-amino-n,n-diethylpyridine-3-sulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CN=CC(N)=C1 KLWICZWDEZHZJL-UHFFFAOYSA-N 0.000 claims 2
- RLZUTRXQJOHGEA-UHFFFAOYSA-N 6-amino-5-nitropyridine-3-sulfonamide Chemical compound NC1=NC=C(S(N)(=O)=O)C=C1[N+]([O-])=O RLZUTRXQJOHGEA-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- PESYJEJBQYZYSF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-[(4-chlorophenyl)methylamino]-5-nitropyridine-3-sulfonamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NCC=2C=CC(Cl)=CC=2)=CN=C1NCC1=CC=C(Cl)C=C1 PESYJEJBQYZYSF-UHFFFAOYSA-N 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 18
- 241000287828 Gallus gallus Species 0.000 description 15
- 235000013330 chicken meat Nutrition 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- 210000003250 oocyst Anatomy 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 235000013594 poultry meat Nutrition 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- AVILRJQPDYPXFQ-UHFFFAOYSA-N 5-bromopyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CN=CC(Br)=C1 AVILRJQPDYPXFQ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241000252983 Caecum Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000001154 acute effect Effects 0.000 description 6
- 230000001165 anti-coccidial effect Effects 0.000 description 6
- 229940124536 anticoccidial agent Drugs 0.000 description 6
- 210000004534 cecum Anatomy 0.000 description 6
- 239000003224 coccidiostatic agent Substances 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 241000223932 Eimeria tenella Species 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 235000019786 weight gain Nutrition 0.000 description 4
- 230000004584 weight gain Effects 0.000 description 4
- NZELTGPWKVHLRX-UHFFFAOYSA-N 6-amino-n-ethyl-5-nitropyridine-3-sulfonamide Chemical compound CCNS(=O)(=O)C1=CN=C(N)C([N+]([O-])=O)=C1 NZELTGPWKVHLRX-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000019764 Soybean Meal Nutrition 0.000 description 3
- 239000003674 animal food additive Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 210000003608 fece Anatomy 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 3
- 239000004455 soybean meal Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 210000004215 spore Anatomy 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 235000015099 wheat brans Nutrition 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000006227 2-n-butoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- ALOOMEVLNVJJSZ-UHFFFAOYSA-N 5-aminopyridine-3-sulfonic acid Chemical compound NC1=CN=CC(S(O)(=O)=O)=C1 ALOOMEVLNVJJSZ-UHFFFAOYSA-N 0.000 description 2
- CYBIIVMRVXKBJV-UHFFFAOYSA-N 5-nitropyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 CYBIIVMRVXKBJV-UHFFFAOYSA-N 0.000 description 2
- FEWNXUCMZNXXJD-UHFFFAOYSA-N 6-(dimethylamino)-n,n-dimethyl-5-nitropyridine-3-sulfonamide Chemical compound CN(C)C1=NC=C(S(=O)(=O)N(C)C)C=C1[N+]([O-])=O FEWNXUCMZNXXJD-UHFFFAOYSA-N 0.000 description 2
- QUVFMPNHCPUDJB-UHFFFAOYSA-N 6-amino-5-nitropyridin-1-ium-3-sulfonate Chemical compound NC1=NC=C(S(O)(=O)=O)C=C1[N+]([O-])=O QUVFMPNHCPUDJB-UHFFFAOYSA-N 0.000 description 2
- TXVBZEFEKBYHMH-UHFFFAOYSA-N 6-amino-n,n-diethyl-5-nitropyridine-3-sulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CN=C(N)C([N+]([O-])=O)=C1 TXVBZEFEKBYHMH-UHFFFAOYSA-N 0.000 description 2
- UYWDUAQLNWMIMA-UHFFFAOYSA-N 6-chloro-5-nitropyridine-3-sulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CN=C1Cl UYWDUAQLNWMIMA-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 241000271566 Aves Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- ZDPIZLCVJAAHHR-UHFFFAOYSA-N Clopidol Chemical compound CC1=NC(C)=C(Cl)C(O)=C1Cl ZDPIZLCVJAAHHR-UHFFFAOYSA-N 0.000 description 2
- 241000224483 Coccidia Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000223924 Eimeria Species 0.000 description 2
- 241000223931 Eimeria acervulina Species 0.000 description 2
- 241000499563 Eimeria necatrix Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
- 235000021053 average weight gain Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000002192 coccidiostatic effect Effects 0.000 description 2
- BWFPGXWASODCHM-UHFFFAOYSA-N copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- LXAWIPNBMIDTMR-UHFFFAOYSA-N n-methyl-5-nitropyridine-3-sulfonamide Chemical compound CNS(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 LXAWIPNBMIDTMR-UHFFFAOYSA-N 0.000 description 2
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000009374 poultry farming Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 description 2
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 230000000391 smoking effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- LTWIBTYLSRDGHP-HCURTGQUSA-N 1,2-bis[(e)-(4-chlorophenyl)methylideneamino]guanidine;hydrochloride Chemical compound [Cl-].C=1C=C(Cl)C=CC=1\C=N\N=C(/N)N\[NH+]=C\C1=CC=C(Cl)C=C1 LTWIBTYLSRDGHP-HCURTGQUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- RCLSHHDPXFODKH-UHFFFAOYSA-N 2-methyl-N-(5-nitropyridin-3-yl)sulfonylbutanamide Chemical compound [N+](=O)([O-])C=1C=C(C=NC1)S(=O)(=O)NC(C(CC)C)=O RCLSHHDPXFODKH-UHFFFAOYSA-N 0.000 description 1
- KOXMZIAJBIVBMQ-UHFFFAOYSA-N 2-methyl-n-(5-nitropyridin-3-yl)sulfonylpropanamide Chemical compound CC(C)C(=O)NS(=O)(=O)C1=CN=CC([N+]([O-])=O)=C1 KOXMZIAJBIVBMQ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- NHZLNPMOSADWGC-UHFFFAOYSA-N 4-amino-N-(2-quinoxalinyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=C(C=CC=C2)C2=N1 NHZLNPMOSADWGC-UHFFFAOYSA-N 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- 229960000611 pyrimethamine Drugs 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GDANWVKBBCWCIJ-UHFFFAOYSA-N sulfachlorpyrazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=C(Cl)C=N1 GDANWVKBBCWCIJ-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 150000003544 thiamines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50058180A JPS5951524B2 (ja) | 1975-05-15 | 1975-05-15 | 抗コクシジウム剤 |
| JP50146501A JPS5270029A (en) | 1975-12-09 | 1975-12-09 | Coccidiostat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2621583A1 true DE2621583A1 (de) | 1976-12-02 |
Family
ID=26399248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762621583 Withdrawn DE2621583A1 (de) | 1975-05-15 | 1976-05-14 | Pyridinderivate und ihre verwendung als antikokzidiosemittel |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4094982A (enExample) |
| BR (1) | BR7603012A (enExample) |
| CA (1) | CA1083575A (enExample) |
| DE (1) | DE2621583A1 (enExample) |
| FR (1) | FR2310759A1 (enExample) |
| GB (1) | GB1479879A (enExample) |
| IT (1) | IT1070451B (enExample) |
| MX (1) | MX3409E (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3105183C2 (de) * | 1981-02-13 | 1986-09-25 | Günther 2000 Hamburg Spranger | Einrichtung zur Verminderung des Strömungswiderstandes von von Gasen wie Luft oder dergl. umströmten Flügeln |
| DE69400631T2 (de) * | 1993-05-05 | 1997-02-27 | Palo Alto Medical Foundation, Palo Alto, Calif. | Verwendung von rifamycinderivaten zur herstellung eines arzneimittels zur behandlung der toxoplasmose |
| US6022884A (en) | 1997-11-07 | 2000-02-08 | Amgen Inc. | Substituted pyridine compounds and methods of use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2170209A (en) * | 1937-11-24 | 1939-08-22 | Cilag Chemisches Ind Lab A G | Sulphonamides of 2-aminopyridines |
-
1976
- 1976-04-28 US US05/681,154 patent/US4094982A/en not_active Expired - Lifetime
- 1976-05-04 GB GB18130/76A patent/GB1479879A/en not_active Expired
- 1976-05-07 CA CA251,989A patent/CA1083575A/en not_active Expired
- 1976-05-13 BR BR7603012A patent/BR7603012A/pt unknown
- 1976-05-14 FR FR7614608A patent/FR2310759A1/fr active Granted
- 1976-05-14 IT IT68193/76A patent/IT1070451B/it active
- 1976-05-14 MX MX000242U patent/MX3409E/es unknown
- 1976-05-14 DE DE19762621583 patent/DE2621583A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1479879A (en) | 1977-07-13 |
| IT1070451B (it) | 1985-03-29 |
| FR2310759A1 (fr) | 1976-12-10 |
| CA1083575A (en) | 1980-08-12 |
| BR7603012A (pt) | 1977-05-31 |
| AU1392276A (en) | 1977-11-17 |
| MX3409E (es) | 1980-11-03 |
| US4094982A (en) | 1978-06-13 |
| FR2310759B1 (enExample) | 1978-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: STREHL, P., DIPL.-ING. DIPL.-WIRTSCH.-ING. SCHUEBE |
|
| 8141 | Disposal/no request for examination |