CA1171782A - Combinaison d'un polyether antibiotique et d'un carbanilide utilisee contre les coccidioses - Google Patents

Combinaison d'un polyether antibiotique et d'un carbanilide utilisee contre les coccidioses

Info

Publication number: CA1171782A
Authority: CA; Canada
Prior art keywords: carbanilide; trifluoromethyl; bis; nitro; chloro
Prior art date: 1979-12-26
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

Application number

CA000367322A

Other languages

English (en)

Inventor

George O.P. O'doherty

Albert J. Clinton, (Deceased)

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

Priority date (The priority date 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 date listed.)

1979-12-26

Filing date

1980-12-22

Publication date

1984-07-31

1980-12-22 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1984-07-31 Application granted granted Critical

1984-07-31 Publication of CA1171782A publication Critical patent/CA1171782A/fr

Status Expired legal-status Critical Current

Links

230000001165 anti-coccidial effect Effects 0.000 title claims abstract description 22
229920000570 polyether Polymers 0.000 title description 14
239000004721 Polyphenylene oxide Substances 0.000 title description 12
239000003242 anti bacterial agent Substances 0.000 title description 11
229940088710 antibiotic agent Drugs 0.000 title description 11
GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims abstract description 383
239000000203 mixture Substances 0.000 claims abstract description 25
239000002460 polyether antibiotic agent Substances 0.000 claims abstract description 15
244000144977 poultry Species 0.000 claims abstract description 13
208000003495 Coccidiosis Diseases 0.000 claims abstract description 5
206010023076 Isosporiasis Diseases 0.000 claims abstract description 5
GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 claims description 30
229930191564 Monensin Natural products 0.000 claims description 29
229960005358 monensin Drugs 0.000 claims description 29
GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 claims description 24
239000007983 Tris buffer Substances 0.000 claims description 23
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
-1 2-chloro-1,1,2-trifluoroethoxy Chemical group 0.000 claims description 11
229960001325 triclocarban Drugs 0.000 claims description 10
241000223924 Eimeria Species 0.000 claims description 7
FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 claims description 6
229930182504 Lasalocid Natural products 0.000 claims description 5
VHKXXVVRRDYCIK-UHFFFAOYSA-N Narasin Natural products CC1CC(C)C(C(CC)C(O)=O)OC1C(C)C(O)C(C)C(=O)C(CC)C1C(C)CC(C)C2(C=CC(O)C3(OC(C)(CC3)C3OC(C)C(O)(CC)CC3)O2)O1 VHKXXVVRRDYCIK-UHFFFAOYSA-N 0.000 claims description 5
VHKXXVVRRDYCIK-CWCPJSEDSA-N Narasin Chemical compound C[C@H]1C[C@H](C)[C@H]([C@@H](CC)C(O)=O)O[C@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 VHKXXVVRRDYCIK-CWCPJSEDSA-N 0.000 claims description 5
BBMULGJBVDDDNI-OWKLGTHSSA-N lasalocid Chemical compound C([C@@H]1[C@@]2(CC)O[C@@H]([C@H](C2)C)[C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)CCC=2C(=C(O)C(C)=CC=2)C(O)=O)C[C@](O)(CC)[C@H](C)O1 BBMULGJBVDDDNI-OWKLGTHSSA-N 0.000 claims description 5
229960000320 lasalocid Drugs 0.000 claims description 5
229960001851 narasin Drugs 0.000 claims description 5
BKZOUCVNTCLNFF-IGXZVFLKSA-N (2s)-2-[(2r,3r,4s,5r,6s)-2-hydroxy-6-[(1s)-1-[(2s,5r,7s,8r,9s)-2-[(2r,5s)-5-[(2r,3s,4r,5r)-5-[(2s,3s,4s,5r,6s)-6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl]-4-methoxy-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,8-dimethyl-1,10-dioxaspiro[4.5]dec Chemical compound O([C@@H]1[C@@H]2O[C@H]([C@@H](C)[C@H]2OC)[C@@]2(C)O[C@H](CC2)[C@@]2(C)O[C@]3(O[C@@H]([C@H](C)[C@@H](OC)C3)[C@@H](C)[C@@H]3[C@@H]([C@H](OC)[C@@H](C)[C@](O)([C@H](C)C(O)=O)O3)C)CC2)[C@](C)(O)[C@H](C)[C@@H](OC)[C@@H]1C BKZOUCVNTCLNFF-IGXZVFLKSA-N 0.000 claims description 4
RHDSQRNKIIRGBB-UHFFFAOYSA-N 2-[2-hydroxy-6-[[2-[5-[5-(6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl)oxolan-2-yl]oxolan-2-yl]-3,7-dimethoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-5-methoxy-4-(5-methoxy-6-methyloxan-2-yl)oxy-3,5-dimethyloxan-2-yl]propanoic acid Chemical compound COC1C(C)C2(C(C(OC)CC(CC3C(C(OC4OC(C)C(OC)CC4)C(C)C(O)(C(C)C(O)=O)O3)(C)OC)O2)C)OC1(C)C(O1)CCC1C(O1)CCC1C1OC(C)(O)C(C)C(OC)C1C RHDSQRNKIIRGBB-UHFFFAOYSA-N 0.000 claims description 4
BKZOUCVNTCLNFF-UHFFFAOYSA-N Lonomycin Natural products COC1C(C)C(C2(C)OC(CC2)C2(C)OC3(OC(C(C)C(OC)C3)C(C)C3C(C(OC)C(C)C(O)(C(C)C(O)=O)O3)C)CC2)OC1C1OC(C)(O)C(C)C(OC)C1C BKZOUCVNTCLNFF-UHFFFAOYSA-N 0.000 claims description 4
239000004189 Salinomycin Substances 0.000 claims description 4
KQXDHUJYNAXLNZ-XQSDOZFQSA-N Salinomycin Chemical compound O1[C@@H]([C@@H](CC)C(O)=O)CC[C@H](C)[C@@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 KQXDHUJYNAXLNZ-XQSDOZFQSA-N 0.000 claims description 4
DANUORFCFTYTSZ-UHFFFAOYSA-N epinigericin Natural products O1C2(C(CC(C)(O2)C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)C)C(C)C(OC)CC1CC1CCC(C)C(C(C)C(O)=O)O1 DANUORFCFTYTSZ-UHFFFAOYSA-N 0.000 claims description 4
DANUORFCFTYTSZ-BIBFWWMMSA-N nigericin Chemical compound C([C@@H]1C[C@H]([C@H]([C@]2([C@@H](C[C@](C)(O2)C2O[C@@](C)(CC2)C2[C@H](CC(O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C)O1)C)OC)[C@H]1CC[C@H](C)C([C@@H](C)C(O)=O)O1 DANUORFCFTYTSZ-BIBFWWMMSA-N 0.000 claims description 4
229960001548 salinomycin Drugs 0.000 claims description 4
235000019378 salinomycin Nutrition 0.000 claims description 4
FELYAZAWTURXNF-KWJIWYEDSA-N (E,2S,4R,8S)-8-[(2S,5R,7S,8R,9R)-7-hydroxy-2-[(2R,4S,5S,7R,9S,10R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-[(2S,5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoic acid Chemical compound O1[C@H](C)[C@@H](OC)CC[C@H]1O[C@@H]1[C@@H](C)[C@]2([C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)O[C@@H]([C@@]2(C)O[C@]3(O[C@@H]([C@H](C)[C@@H](O)C3)[C@@H](C)\C=C(/C)C(=O)[C@H](C)C[C@H](C)C(O)=O)CC2)C1 FELYAZAWTURXNF-KWJIWYEDSA-N 0.000 claims description 3
FDJGIYFXRLDEJB-UHFFFAOYSA-N 1,3-dimethyl-1,3-bis(4-nitrophenyl)urea Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(C)C(=O)N(C)C1=CC=C([N+]([O-])=O)C=C1 FDJGIYFXRLDEJB-UHFFFAOYSA-N 0.000 claims description 3
XSBSGLXIQBCTKN-SARHNJKISA-N X-206 Chemical compound C1C[C@](O)(C)[C@H](CC)O[C@H]1[C@@]1(C)O[C@@](O)([C@@]2(C)O[C@@H](CC2)[C@@H](O)[C@@]2(O)[C@@H](C[C@H](C)[C@@H](C[C@]3(O)[C@H](CC[C@@H](O3)[C@@H](C)[C@H](O)C[C@@H]3O[C@@H]([C@@H](C)CC3)[C@@H](C)C(O)=O)C)O2)C)[C@H](C)C1 XSBSGLXIQBCTKN-SARHNJKISA-N 0.000 claims description 3
XSBSGLXIQBCTKN-UHFFFAOYSA-N X-206 Natural products C1CC(O)(C)C(CC)OC1C1(C)OC(O)(C2(C)OC(CC2)C(O)C2(O)C(CC(C)C(CC3(O)C(CCC(O3)C(C)C(O)CC3OC(C(C)CC3)C(C)C(O)=O)C)O2)C)C(C)C1 XSBSGLXIQBCTKN-UHFFFAOYSA-N 0.000 claims description 3
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims description 2
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
238000000034 method Methods 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 description 21
230000003902 lesion Effects 0.000 description 13
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
235000013594 poultry meat Nutrition 0.000 description 11
239000000047 product Substances 0.000 description 11
238000000921 elemental analysis Methods 0.000 description 10
241000223932 Eimeria tenella Species 0.000 description 9
150000003839 salts Chemical class 0.000 description 8
239000011573 trace mineral Substances 0.000 description 8
235000013619 trace mineral Nutrition 0.000 description 8
WQRYZWVAWJMKPB-UHFFFAOYSA-N 3-nitro-5-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1N WQRYZWVAWJMKPB-UHFFFAOYSA-N 0.000 description 7
235000019739 Dicalciumphosphate Nutrition 0.000 description 7
239000001506 calcium phosphate Substances 0.000 description 7
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 7
229940038472 dicalcium phosphate Drugs 0.000 description 7
229910000390 dicalcium phosphate Inorganic materials 0.000 description 7
239000004615 ingredient Substances 0.000 description 7
235000012054 meals Nutrition 0.000 description 7
239000002904 solvent Substances 0.000 description 7
235000019764 Soybean Meal Nutrition 0.000 description 6
230000000694 effects Effects 0.000 description 6
229930182817 methionine Natural products 0.000 description 6
210000003250 oocyst Anatomy 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
239000004455 soybean meal Substances 0.000 description 6
230000002195 synergetic effect Effects 0.000 description 6
241000287828 Gallus gallus Species 0.000 description 5
240000008042 Zea mays Species 0.000 description 5
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
235000002017 Zea mays subsp mays Nutrition 0.000 description 5
229910000019 calcium carbonate Inorganic materials 0.000 description 5
235000005822 corn Nutrition 0.000 description 5
229930003231 vitamin Natural products 0.000 description 5
235000013343 vitamin Nutrition 0.000 description 5
239000011782 vitamin Substances 0.000 description 5
229940088594 vitamin Drugs 0.000 description 5
150000003722 vitamin derivatives Chemical class 0.000 description 5
241000223931 Eimeria acervulina Species 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
241000271566 Aves Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
240000004658 Medicago sativa Species 0.000 description 3
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 3
241000286209 Phasianidae Species 0.000 description 3
235000019742 Vitamins premix Nutrition 0.000 description 3
229940124536 anticoccidial agent Drugs 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
DIKYHBWGIUNGIW-UHFFFAOYSA-N 2-[2,4-dihydroxy-6-[1-[2-[5-[5-(6-hydroxy-4-methoxy-3,5,6-trimethyloxan-2-yl)oxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-5-(5-methoxy-6-methyloxan-2-yl)oxy-3,5-dimethyloxan-2-yl]propanoic acid Chemical compound O1C(C)C(OC)CCC1OC1(C)C(C(C)C2OC3(OC(C)(CC3)C3OC(C)(CC3)C3OC(CC3)C3C(C(OC)C(C)C(C)(O)O3)C)C(C)C(OC)C2)OC(O)(C(C)C(O)=O)C(C)C1O DIKYHBWGIUNGIW-UHFFFAOYSA-N 0.000 description 2
235000019737 Animal fat Nutrition 0.000 description 2
241000272517 Anseriformes Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
241000223934 Eimeria maxima Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
235000019752 Wheat Middilings Nutrition 0.000 description 2
JETSKDPKURDVNI-UHFFFAOYSA-N [C].[Ca] Chemical compound [C].[Ca] JETSKDPKURDVNI-UHFFFAOYSA-N 0.000 description 2
235000015278 beef Nutrition 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
235000013330 chicken meat Nutrition 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
235000013305 food Nutrition 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
239000003760 tallow Substances 0.000 description 2
ZITSQIZMRMDQLE-SJSJOXFOSA-N (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid Chemical compound CO[C@@H]1C[C@@H](C[C@H]2CC[C@H](C)[C@@H](O2)[C@@H](C)C(O)=O)O[C@]2(O[C@@](C)(C[C@H]2C)[C@H]2CC[C@](C)(O2)[C@@H]2O[C@H](C[C@@H]2C)[C@H]2O[C@](C)(O)[C@H](C)C[C@@H]2C)[C@@H]1C ZITSQIZMRMDQLE-SJSJOXFOSA-N 0.000 description 1
QZVSDERYSHAHPU-LFEMCTADSA-N (2r)-2-[(2s,3r,4s,5s,6s)-2-hydroxy-6-[[(2r,3r,4r,5s,6r,7r,9s)-2-[(5s)-5-[(2r,5r)-5-[(3s,5r,6s)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]oxolan-2-yl]-3,7-dimethoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-4-methoxy-5-[(2s,5s,6r)-5-metho Chemical compound C1([C@H]2CC[C@@H](O2)[C@@H]2CCC(O2)[C@@]2(C)O[C@]3([C@H](C)[C@H]2OC)[C@@H]([C@H](OC)C[C@@H](C[C@H]2[C@]([C@@H](OC)[C@@H](C)[C@@](O)([C@@H](C)C(O)=O)O2)(C)O[C@@H]2O[C@H](C)[C@@H](OC)CC2)O3)C)O[C@](C)(O)[C@H](C)C[C@@H]1C QZVSDERYSHAHPU-LFEMCTADSA-N 0.000 description 1
PYUBINRDIXNWEP-BSSZEUCBSA-N (2r)-2-[(2s,3s,6r)-6-[(2r,3s)-3-[(2r,5s,6r)-6-[[(2r,3s,6r)-6-[(1r)-1-[(2s,5s)-5-[(2r,5s)-5-[(2r,5r,6s)-6-ethyl-5-hydroxy-5-methyloxan-2-yl]-2-hydroxyoxolan-2-yl]-5-methyloxolan-2-yl]ethyl]-6-hydroxy-3-methyloxan-2-yl]methyl]-6-hydroxy-5-methyloxan-2-yl]-2 Chemical compound C1C[C@](O)(C)[C@H](CC)O[C@H]1[C@H]1O[C@@](O)([C@@]2(C)O[C@@H](CC2)[C@@H](C)[C@]2(O)O[C@H](C[C@]3(O)[C@H](CC[C@@H](O3)[C@@H](C)[C@H](O)C[C@@H]3O[C@@H]([C@@H](C)CC3)[C@@H](C)C(O)=O)C)[C@@H](C)CC2)CC1 PYUBINRDIXNWEP-BSSZEUCBSA-N 0.000 description 1
ZNBNBTIDJSKEAM-NISBWGIBSA-N (2s,3r,4r)-4-[(2s,5r,7s,8r,9s)-7-hydroxy-2-[(2r,5s)-5-[(2r,3s,5r)-5-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic a Chemical compound C1[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC(=O)CC)[C@H](C)C(O)=O)O[C@]11O[C@](C)([C@@H]2O[C@@](C)(CC2)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-NISBWGIBSA-N 0.000 description 1
LQFPDTISEHAMNQ-JRSQRZRGSA-N (e,2s,4r,8s)-8-[(2s,5r,6r,7r,9s)-2-[(2r,4s,5r,6r,9r)-2-[(2s,3s,5r,6r)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-4,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-7-[(2r,5s,6r)-5-methoxy-6-methyloxan-2-yl]oxy-2,6-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl Chemical compound O1[C@H](C)[C@@H](OC)CC[C@@H]1O[C@H]1[C@@H](C)[C@@]2(O[C@@](C)(CC2)[C@@H]2O[C@@]3([C@H](C[C@@H](O3)[C@@H]3[C@H](C[C@@H](C)[C@](O)(CO)O3)C)C)[C@H](C)CC2)O[C@H]([C@@H](C)\C=C(/C)C(=O)[C@H](C)C[C@H](C)C(O)=O)C1 LQFPDTISEHAMNQ-JRSQRZRGSA-N 0.000 description 1
RDUIJJYNVCVETK-UHFFFAOYSA-N 1,2,4-trichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=C(N=C=O)C=C1Cl RDUIJJYNVCVETK-UHFFFAOYSA-N 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
NYPBOWHIPOBXBA-UHFFFAOYSA-N 1,3-dibromo-5-fluoro-2-isocyanatobenzene Chemical compound FC1=CC(Br)=C(N=C=O)C(Br)=C1 NYPBOWHIPOBXBA-UHFFFAOYSA-N 0.000 description 1
NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 description 1
ZCPHLSPLEGBTCZ-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(N=C=O)=CC=C1Cl ZCPHLSPLEGBTCZ-UHFFFAOYSA-N 0.000 description 1
XCDYDLFUPMSLGZ-UHFFFAOYSA-N 1-fluoro-2-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(N=C=O)=C1 XCDYDLFUPMSLGZ-UHFFFAOYSA-N 0.000 description 1
QUOBVYPFBJUOAJ-UHFFFAOYSA-N 1-isocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1 QUOBVYPFBJUOAJ-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
POLDSAUWRJCSOK-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C(Cl)=C1 POLDSAUWRJCSOK-UHFFFAOYSA-N 0.000 description 1
ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 1
RQWJHUJJBYMJMN-UHFFFAOYSA-N 4-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC=C(C(F)(F)F)C=C1N RQWJHUJJBYMJMN-UHFFFAOYSA-N 0.000 description 1
XZJLJFYPIJKWCY-ANXQGEBNSA-N 6-[(3r,4s,5s,7r)-7-[(2s,3s,5s)-5-ethyl-5-[(2r,5s)-5-ethyl-5-[(1r)-1-hydroxyethyl]oxolan-2-yl]-3-methyloxolan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid Chemical compound C([C@@H]1[C@@]2(CC)O[C@@H]([C@H](C2)C)[C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)CCC=2C(=C(O)C(C)=CC=2)C(O)=O)C[C@@](CC)([C@@H](C)O)O1 XZJLJFYPIJKWCY-ANXQGEBNSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000208140 Acer Species 0.000 description 1
WWDHGOLBPBWCNJ-UHFFFAOYSA-N Alborixin Natural products C1CC(O)(C)C(CC)OC1C1(C)OC(O)(C2(C)OC(CC2)C(O)C2(O)C(CC(C)C(CC3(O)C(CCC(O3)C(C)C(O)CC3C(CC(C)C(C(C)C(O)=O)O3)C)C)O2)C)C(C)C1 WWDHGOLBPBWCNJ-UHFFFAOYSA-N 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
HIYAVKIYRIFSCZ-CVXKHCKVSA-N Calcimycin Chemical compound CC([C@H]1OC2([C@@H](C[C@H]1C)C)O[C@H]([C@H](CC2)C)CC=1OC2=CC=C(C(=C2N=1)C(O)=O)NC)C(=O)C1=CC=CN1 HIYAVKIYRIFSCZ-CVXKHCKVSA-N 0.000 description 1
GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
241000207199 Citrus Species 0.000 description 1
AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
239000004258 Ethoxyquin Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
ZITSQIZMRMDQLE-UHFFFAOYSA-N Grisorixin Natural products O1C2(C(CC(C)(O2)C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(C)(O)O2)C)C)C)C(C)C(OC)CC1CC1CCC(C)C(C(C)C(O)=O)O1 ZITSQIZMRMDQLE-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
241000597310 Imeria <wasp> Species 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
RWWSBGHRGAQGJE-UHFFFAOYSA-N Laidlomycin Natural products CC(C(CCC(=O)O)C(C)C(=O)O)C1OC2(CCC(C)(O2)C3CCC(C)(O3)C4OC(CC4C)C5OC(O)(CO)C(C)CC5C)CC(O)C1C RWWSBGHRGAQGJE-UHFFFAOYSA-N 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
KTQFYFLZDLTLAH-UHFFFAOYSA-N Lysocellin Natural products CCC(O)C1(CC)CC(C)C(O)(O1)C2(C)CC(C)C(O2)C(CC)C(=O)C(C)C(O)C(C)C3OC(O)(CC(=O)O)C(C)CC3C KTQFYFLZDLTLAH-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000004183 Monensin A Substances 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
QZVSDERYSHAHPU-UHFFFAOYSA-N Septamycin Natural products COC1C(C)C2(C(C(OC)CC(CC3C(C(OC)C(C)C(O)(C(C)C(O)=O)O3)(C)OC3OC(C)C(OC)CC3)O2)C)OC1(C)C(O1)CCC1C(O1)CCC1C1OC(C)(O)C(C)CC1C QZVSDERYSHAHPU-UHFFFAOYSA-N 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
229930003779 Vitamin B12 Natural products 0.000 description 1
229930003316 Vitamin D Natural products 0.000 description 1
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
229930003427 Vitamin E Natural products 0.000 description 1
229930003448 Vitamin K Natural products 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
WWDHGOLBPBWCNJ-GXXSWWTOSA-N alborixin Chemical compound C1C[C@](O)(C)[C@H](CC)O[C@H]1[C@@]1(C)O[C@@](O)([C@@]2(C)O[C@@H](CC2)[C@@H](O)[C@@]2(O)[C@@H](C[C@H](C)[C@@H](C[C@]3(O)[C@H](CC[C@@H](O3)[C@@H](C)[C@H](O)C[C@H]3[C@@H](C[C@H](C)[C@@H]([C@@H](C)C(O)=O)O3)C)C)O2)C)[C@H](C)C1 WWDHGOLBPBWCNJ-GXXSWWTOSA-N 0.000 description 1
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229960002685 biotin Drugs 0.000 description 1
235000020958 biotin Nutrition 0.000 description 1
239000011616 biotin Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
229940093500 ethoxyquin Drugs 0.000 description 1
235000019285 ethoxyquin Nutrition 0.000 description 1
HXVGHXDQGUPUKY-UHFFFAOYSA-N ethyl 2-isocyanatobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N=C=O HXVGHXDQGUPUKY-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
238000003304 gavage Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000003455 independent Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
229960004561 laidlomycin Drugs 0.000 description 1
239000006028 limestone Substances 0.000 description 1
KTQFYFLZDLTLAH-DESDHLEASA-N lysocellin Chemical compound O1[C@]([C@@H](O)CC)(CC)C[C@@H](C)[C@]1(O)[C@@]1(C)O[C@H]([C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CC(O)=O)O2)C)[C@@H](C)C1 KTQFYFLZDLTLAH-DESDHLEASA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229940073584 methylene chloride Drugs 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000019376 monensin A Nutrition 0.000 description 1
STICFDGTCMULDT-UHFFFAOYSA-N n-[3,5-bis(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC(F)(F)C1=CC(NC(Cl)=O)=CC(C(F)(F)F)=C1 STICFDGTCMULDT-UHFFFAOYSA-N 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229940055726 pantothenic acid Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229960002477 riboflavin Drugs 0.000 description 1
235000019192 riboflavin Nutrition 0.000 description 1
239000002151 riboflavin Substances 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
235000019155 vitamin A Nutrition 0.000 description 1
239000011719 vitamin A Substances 0.000 description 1
235000019163 vitamin B12 Nutrition 0.000 description 1
239000011715 vitamin B12 Substances 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
150000003710 vitamin D derivatives Chemical class 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
235000019168 vitamin K Nutrition 0.000 description 1
239000011712 vitamin K Substances 0.000 description 1
150000003721 vitamin K derivatives Chemical class 0.000 description 1
229940045997 vitamin a Drugs 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
229940046010 vitamin k Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000367322A 1979-12-26 1980-12-22 Combinaison d'un polyether antibiotique et d'un carbanilide utilisee contre les coccidioses Expired CA1171782A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US10730479A	1979-12-26	1979-12-26
US107,304		1979-12-26

Publications (1)

Publication Number	Publication Date
CA1171782A true CA1171782A (fr)	1984-07-31

Family

ID=22315944

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000367322A Expired CA1171782A (fr)	1979-12-26	1980-12-22	Combinaison d'un polyether antibiotique et d'un carbanilide utilisee contre les coccidioses

Country Status (2)

Country	Link
CA (1)	CA1171782A (fr)
PH (1)	PH21525A (fr)

1980
- 1980-12-22 CA CA000367322A patent/CA1171782A/fr not_active Expired
- 1980-12-23 PH PH25027A patent/PH21525A/en unknown

Also Published As

Publication number	Publication date
PH21525A (en)	1987-11-16

Legal Events

Date	Code	Title	Description
2001-07-31	MKEX	Expiry

Publication	Publication Date	Title
US4468380A (en)	1984-08-28	Anticoccidial combinations comprising polyether antibiotics and carbanilides
US4526997A (en)	1985-07-02	Anticoccidial combinations comprising polyether antibiotics and carbanilides
EP0015110B1 (fr)	1985-08-21	Composition contre la coccidiose, carbanilides et procédé pour leur préparation
US3933814A (en)	1976-01-20	1-(4-Phenoxyphenyl)-1,3,5-triazines
JPS6018658B2 (ja)	1985-05-11	１−（４−フエノキシ−フエニル）−１，３，５−トリアジン誘導体の製造方法
US4366168A (en)	1982-12-28	Anticoccidial combinations
CA1171782A (fr)	1984-07-31	Combinaison d'un polyether antibiotique et d'un carbanilide utilisee contre les coccidioses
JPS6339569B2 (fr)	1988-08-05
US3970752A (en)	1976-07-20	Coccidiocidal compositions utilizing 1-phenyl-substituted 1,3,5-triazine
US4088770A (en)	1978-05-09	Substituted 2-anilinobenzoxazoles used as immunosuppressive agents
US3903275A (en)	1975-09-02	Medicated fish feeds and the treatment of fish diseases caused by bacteria
Morrison et al.	1979	Efficacy of salinomycin and stenorol against various species of Eimeria and effect on chick performance
JPS63196515A (ja)	1988-08-15	殺コクシジウム組成物
EP0750499A1 (fr)	1997-01-02	Coccidiostats a base de carbanilide
US3958008A (en)	1976-05-18	Anthelmintic methods of use
US4061755A (en)	1977-12-06	Coccidiocidal combination of monensin and metichlorpindol
US4764534A (en)	1988-08-16	Anticoccidial naphthalenamines and combinations thereof
US4659713A (en)	1987-04-21	Quinoxalinedione compounds useful for controlling coccidiosis
US2823160A (en)	1958-02-11	Substituted pyrimidines compositions for chemotherapy of coccidiosis
US3928437A (en)	1975-12-23	Phenoxy-phenyl, phenylthiophenyl, phenylsulfonylphenyl and phenylaminophenyl diaminothioureas
US3555085A (en)	1971-01-12	Nitro-trifluoromethylthiobenzamides
EP1210950B1 (fr)	2005-10-19	Composition contre la coccidiose
US4275210A (en)	1981-06-23	Substituted 2-anilinobenzoxazoles
Meingassner et al.	1977	Laboratory studies on the anticoccidial activity of septamycin
US4042703A (en)	1977-08-16	Method of treating and preventing coccidiosis