DE2718799C2 - - Google Patents
Info
- Publication number
- DE2718799C2 DE2718799C2 DE2718799A DE2718799A DE2718799C2 DE 2718799 C2 DE2718799 C2 DE 2718799C2 DE 2718799 A DE2718799 A DE 2718799A DE 2718799 A DE2718799 A DE 2718799A DE 2718799 C2 DE2718799 C2 DE 2718799C2
- Authority
- DE
- Germany
- Prior art keywords
- atoms
- methyl
- compounds
- formula
- phenyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 6
- IFLUERSJRQLTTD-UHFFFAOYSA-N 1-(4-phenoxyphenyl)-2h-1,3,5-triazine Chemical class C1N=CN=CN1C(C=C1)=CC=C1OC1=CC=CC=C1 IFLUERSJRQLTTD-UHFFFAOYSA-N 0.000 claims description 5
- 208000003495 Coccidiosis Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000370 acceptor Substances 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- YNKDRTCJDFVUTJ-UHFFFAOYSA-N carbonyl diisocyanate Chemical class O=C=NC(=O)N=C=O YNKDRTCJDFVUTJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- ZCLVKRFCNWGTIS-UHFFFAOYSA-N n-carbonochloridoyl-n-methylcarbamoyl chloride Chemical compound ClC(=O)N(C)C(Cl)=O ZCLVKRFCNWGTIS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000001737 promoting effect Effects 0.000 claims 1
- -1 chlorocarbonyl Chemical group 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 241000287828 Gallus gallus Species 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
- 244000144977 poultry Species 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 235000013330 chicken meat Nutrition 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 235000013594 poultry meat Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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
- 206010023076 Isosporiasis Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007952 growth promoter Substances 0.000 description 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 241000224483 Coccidia Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000223932 Eimeria tenella Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003224 coccidiostatic agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 2
- 125000004995 haloalkylthio group Chemical group 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CUUJSCZRXAFXIP-UHFFFAOYSA-N 2-methyl-4,6-dinitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N CUUJSCZRXAFXIP-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- WHEQVHAIRSPYDK-UHFFFAOYSA-N 4,6-dimethyl-1h-pyrimidin-2-one Chemical compound CC1=CC(C)=NC(O)=N1 WHEQVHAIRSPYDK-UHFFFAOYSA-N 0.000 description 1
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical class C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010003011 Appendicitis Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000223931 Eimeria acervulina Species 0.000 description 1
- 241000499566 Eimeria brunetti Species 0.000 description 1
- 241001662550 Eimeria falciformis Species 0.000 description 1
- 241000221513 Eimeria irresidua Species 0.000 description 1
- 241001485852 Eimeria magna Species 0.000 description 1
- 241000223934 Eimeria maxima Species 0.000 description 1
- 241001485868 Eimeria media Species 0.000 description 1
- 241000179199 Eimeria mitis Species 0.000 description 1
- 241000530449 Eimeria mivati Species 0.000 description 1
- 241000499563 Eimeria necatrix Species 0.000 description 1
- 241001485851 Eimeria perforans Species 0.000 description 1
- 241000499544 Eimeria praecox Species 0.000 description 1
- 241001485873 Eimeria stiedai Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 229930182504 Lasalocid Natural products 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 229930191564 Monensin Natural products 0.000 description 1
- 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 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940036811 bone meal Drugs 0.000 description 1
- 239000002374 bone meal Substances 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 230000002192 coccidiostatic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- PJBQYZZKGNOKNJ-UHFFFAOYSA-M hydron;5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;dichloride Chemical compound Cl.[Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C PJBQYZZKGNOKNJ-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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 description 1
- 229960000320 lasalocid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 229960005358 monensin Drugs 0.000 description 1
- 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 description 1
- VBBUFMFZDHLELS-UHFFFAOYSA-N n-(oxomethylidene)carbamoyl chloride Chemical compound ClC(=O)N=C=O VBBUFMFZDHLELS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- DWSGLSZEOZQMSP-UHFFFAOYSA-N potassium;sodium Chemical compound [Na+].[K+] DWSGLSZEOZQMSP-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 235000011844 whole wheat flour Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Obesity (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772718799 DE2718799A1 (de) | 1977-04-27 | 1977-04-27 | 1-(4-phenoxy-phenyl)-1,3,5-triazin- derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel und wachstumsfoerderer |
| IL7854571A IL54571A (en) | 1977-04-27 | 1978-04-24 | Pharmaceutical growth promoting compositions containing certain 1-(4-phenoxy-phenyl)-1,3,5-triazine-2,4-dione derivatives |
| IT22665/78A IT1095611B (it) | 1977-04-27 | 1978-04-24 | Prodotti che favoriscono la crescita |
| JP4838878A JPS53136525A (en) | 1977-04-27 | 1978-04-25 | Growth promoting agent and method |
| LU79519A LU79519A1 (de) | 1977-04-27 | 1978-04-25 | Verfahren zur herstellung eines wachstumsfoerdernden mittels |
| GB16267/78A GB1571368A (en) | 1977-04-27 | 1978-04-25 | Growth promoting agent |
| BE187113A BE866389A (fr) | 1977-04-27 | 1978-04-26 | Composition a base de derives 1-(4-phenoxy-phenyl)-1.3.5. -triaziniques activateurs de croissance des animaux |
| ZA00782382A ZA782382B (en) | 1977-04-26 | 1978-04-26 | Growth promoting agents smoking articles containing thaumatin or monellin |
| FR7812300A FR2388559A1 (fr) | 1977-04-27 | 1978-04-26 | Compositions a base de derives 1-(4-phenoxy-phenyl)-1.3.5.- triaziniques activateurs de croissance des animaux |
| IE827/78A IE47681B1 (en) | 1977-04-27 | 1978-04-26 | Growth promoting agent |
| AU35457/78A AU524141B2 (en) | 1977-04-27 | 1978-04-26 | GROWTH PROMOTING AGENTS CONTAINING l-(4-PHENOXY-PHENYL) 1, 3, 5-TRIAZINE DERIVATIVES |
| US06/019,549 US4219552A (en) | 1977-04-27 | 1979-03-12 | 1-(4-Phenoxy-phenyl)-1,3,5-triazines, their use as growth promoters |
| SG511/83A SG51183G (en) | 1977-04-27 | 1983-08-16 | Growth promoting agent |
| KE3325A KE3325A (en) | 1977-04-27 | 1983-09-01 | Growth promoting agent |
| HK676/83A HK67683A (en) | 1977-04-27 | 1983-12-15 | Growth promoting agent |
| MY1984364A MY8400364A (en) | 1977-04-27 | 1984-12-31 | Growth promoting agent |
| JP62053895A JPS62253346A (ja) | 1977-04-27 | 1987-03-09 | 動物飼料および飲料水 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772718799 DE2718799A1 (de) | 1977-04-27 | 1977-04-27 | 1-(4-phenoxy-phenyl)-1,3,5-triazin- derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel und wachstumsfoerderer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2718799A1 DE2718799A1 (de) | 1978-11-09 |
| DE2718799C2 true DE2718799C2 (en, 2012) | 1989-02-23 |
Family
ID=6007430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772718799 Granted DE2718799A1 (de) | 1977-04-26 | 1977-04-27 | 1-(4-phenoxy-phenyl)-1,3,5-triazin- derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel und wachstumsfoerderer |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4219552A (en, 2012) |
| JP (2) | JPS53136525A (en, 2012) |
| AU (1) | AU524141B2 (en, 2012) |
| BE (1) | BE866389A (en, 2012) |
| DE (1) | DE2718799A1 (en, 2012) |
| FR (1) | FR2388559A1 (en, 2012) |
| GB (1) | GB1571368A (en, 2012) |
| HK (1) | HK67683A (en, 2012) |
| IE (1) | IE47681B1 (en, 2012) |
| IL (1) | IL54571A (en, 2012) |
| IT (1) | IT1095611B (en, 2012) |
| KE (1) | KE3325A (en, 2012) |
| LU (1) | LU79519A1 (en, 2012) |
| MY (1) | MY8400364A (en, 2012) |
| SG (1) | SG51183G (en, 2012) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2718799A1 (de) * | 1977-04-27 | 1978-11-09 | Bayer Ag | 1-(4-phenoxy-phenyl)-1,3,5-triazin- derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel und wachstumsfoerderer |
| EP0042669A3 (en) * | 1980-06-23 | 1982-03-24 | The Upjohn Company | Compounds and compositions for use in animal feeds |
| EP0081142B1 (de) * | 1981-12-03 | 1986-06-25 | BASF Aktiengesellschaft | 1,3,5-Triazinone, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses |
| DE3147879A1 (de) * | 1981-12-03 | 1983-06-16 | Basf Ag, 6700 Ludwigshafen | 1,3,5-triazinone, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| DE3300793A1 (de) * | 1983-01-12 | 1984-07-12 | Bayer Ag, 5090 Leverkusen | Coccidiosemittel |
| US5219853A (en) * | 1983-01-12 | 1993-06-15 | Bayer Aktiengesellschaft | Agent for coccidiosis |
| DE3314739A1 (de) * | 1983-04-23 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | 1-(4-(4-(fluoralkylmethylthio- oder -sulfinyl- oder -sulfonyl-)phenoxy) phenyl)-1,3,5-triazin-2,4,6(1h,3h,5h)-trione, verfahren zu ihrer herstellung und ihre verwendung als coccidiosemittel |
| DE3408768A1 (de) * | 1984-03-09 | 1985-09-12 | Bayer Ag, 5090 Leverkusen | Immunstimulierende mittel |
| JPS6178774A (ja) * | 1984-09-25 | 1986-04-22 | Sumitomo Chem Co Ltd | ６−アルキルチオ−１，３，５−トリアジン−２，４（１ｈ，３ｈ）−ジオン誘導体の製造法 |
| DE3516632A1 (de) * | 1985-05-09 | 1986-11-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1,3,5-triazintrionen |
| DE3516732C1 (de) * | 1985-05-09 | 1986-07-10 | Daimler-Benz Ag, 7000 Stuttgart | Kombinierte Zentralverriegelungs- und Sicherungsanlage für Verschlüsse an einem Kraftfahrzeug |
| DE3703105A1 (de) * | 1987-02-03 | 1988-08-11 | Bayer Ag | Mittel gegen protozoen bei insekten |
| DE3703103A1 (de) * | 1987-02-03 | 1988-08-11 | Bayer Ag | Mittel gegen fischparsiten |
| DE19824483A1 (de) | 1998-06-02 | 1999-12-09 | Bayer Ag | Halbfeste wäßrige Zubereitungen für orale Applikation von Toltrazuril-Sulfon |
| BR9914385A (pt) * | 1998-10-08 | 2001-07-17 | New Ace Res Company | Composição útil para o tratamento e prevenção de infecções protozoárias no homem e em animais, e, método de tratamento de uma infecção protozoária no homem e em animais |
| US6150361A (en) * | 1998-12-22 | 2000-11-21 | Bayer Corporation | Triazineone compounds for treating diseases due to sarcosystis, neospora and toxoplasma |
| DE10040110A1 (de) * | 2000-08-17 | 2002-02-28 | Bayer Ag | Verwendung von Triazintrion-Sulfoxiden zur Bekämpfung von Coccidiosen |
| DE10040174A1 (de) * | 2000-08-17 | 2002-02-28 | Bayer Ag | Verwendung von Triazintrion-Sulfonen zur Bekämpfung von Coccidiosen |
| US7291616B2 (en) | 2001-10-31 | 2007-11-06 | Cell Therapeutics, Inc. | Aryl triazines as LPAAT-β inhibitors and uses thereof |
| US6861523B2 (en) | 2002-02-08 | 2005-03-01 | Torrey Pines Institute For Molecular Studies | 1,3,5- trisubstituted-1,3,5-triazine-2,4,6-trione compounds and libraries |
| US7419984B2 (en) * | 2002-10-17 | 2008-09-02 | Cell Therapeutics, Inc. | Pyrimidines and uses thereof |
| US6875781B2 (en) * | 2003-04-04 | 2005-04-05 | Cell Therapeutics, Inc. | Pyridines and uses thereof |
| KR100592797B1 (ko) | 2005-02-02 | 2006-06-28 | 한국화학연구원 | 3-메틸-4-페녹시페닐아민 유도체의 제조 방법 |
| CN1896068B (zh) * | 2005-07-16 | 2010-12-08 | 凌青云 | 一种制备甲苯三嗪酮的方法 |
| DE102007025908A1 (de) * | 2007-06-01 | 2008-12-04 | Bayer Healthcare Ag | Formulierungen enthaltend Triazinone und Eisen |
| DE102009012423A1 (de) | 2009-03-10 | 2010-09-16 | Bayer Animal Health Gmbh | Zubereitung auf Ölbasis |
| EP2740470A1 (en) | 2012-12-07 | 2014-06-11 | Ceva Sante Animale | Treatment of Coccidiosis with intramuscular triazine composition |
| EP2740492A1 (en) | 2012-12-07 | 2014-06-11 | Ceva Sante Animale | Triazine formulations with a second active ingredient and surfactant(s) |
| EP2740469A1 (en) | 2012-12-07 | 2014-06-11 | Ceva Sante Animale | New treatments with triazines |
| CN103694185B (zh) * | 2013-12-18 | 2016-02-17 | 湖北龙翔药业有限公司 | 托曲珠利碱金属盐的制备方法 |
| CN103690488B (zh) * | 2013-12-18 | 2015-12-30 | 湖北龙翔药业有限公司 | 一种托曲珠利钾盐可溶性粉及其制备方法和用途 |
| JP2020502225A (ja) | 2016-12-21 | 2020-01-23 | アルゼキュア ファーマ アーべー | トリアジントリオン誘導体、ならびにニューロトロフィン受容体および受容体型チロシンキナーゼのモジュレーターとしてのその使用。 |
| CA3090864A1 (en) | 2018-02-26 | 2019-08-29 | AlzeCure Pharma AB | Triazine derivatives for treating diseases relating to neurotrophins |
| EP3578182A1 (en) | 2018-06-05 | 2019-12-11 | Bayer Animal Health GmbH | Formulations containing triazinones and iron with a low amount of free iron ions |
| EP3578181A1 (en) | 2018-06-05 | 2019-12-11 | Bayer Animal Health GmbH | Formulation for use in the simultaneous treatment of coccidial infections and iron deficiencies |
| GB201810668D0 (en) | 2018-06-28 | 2018-08-15 | Stiftelsen Alzecure | New compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2246109A1 (de) * | 1972-09-20 | 1974-03-28 | Bayer Ag | 1-(4-phenoxy-phenyl)-1,3,5-triazinderivate, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2313721A1 (de) * | 1973-03-20 | 1974-10-03 | Bayer Ag | Neue 1-phenylsubstituierte 1,3,5triazine, verfahren zu ihrer herstellung, sowie ihre verwendung als arzneimittel |
| DE2413722C3 (de) * | 1974-03-21 | 1982-04-08 | Bayer Ag, 5090 Leverkusen | Neue 1-(4-Phenoxy-phenyl)-1,3,5-triazin-Derivate, ein Verfahren zu ihrer Herstellung sowie ihre Anwendung als Arzneimittel |
| DE2718799A1 (de) * | 1977-04-27 | 1978-11-09 | Bayer Ag | 1-(4-phenoxy-phenyl)-1,3,5-triazin- derivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel und wachstumsfoerderer |
-
1977
- 1977-04-27 DE DE19772718799 patent/DE2718799A1/de active Granted
-
1978
- 1978-04-24 IL IL7854571A patent/IL54571A/xx unknown
- 1978-04-24 IT IT22665/78A patent/IT1095611B/it active
- 1978-04-25 JP JP4838878A patent/JPS53136525A/ja active Granted
- 1978-04-25 GB GB16267/78A patent/GB1571368A/en not_active Expired
- 1978-04-25 LU LU79519A patent/LU79519A1/de unknown
- 1978-04-26 BE BE187113A patent/BE866389A/xx not_active IP Right Cessation
- 1978-04-26 FR FR7812300A patent/FR2388559A1/fr active Granted
- 1978-04-26 IE IE827/78A patent/IE47681B1/en not_active IP Right Cessation
- 1978-04-26 AU AU35457/78A patent/AU524141B2/en not_active Expired
-
1979
- 1979-03-12 US US06/019,549 patent/US4219552A/en not_active Expired - Lifetime
-
1983
- 1983-08-16 SG SG511/83A patent/SG51183G/en unknown
- 1983-09-01 KE KE3325A patent/KE3325A/xx unknown
- 1983-12-15 HK HK676/83A patent/HK67683A/xx not_active IP Right Cessation
-
1984
- 1984-12-31 MY MY1984364A patent/MY8400364A/xx unknown
-
1987
- 1987-03-09 JP JP62053895A patent/JPS62253346A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT7822665A0 (it) | 1978-04-24 |
| JPS6238324B2 (en, 2012) | 1987-08-17 |
| MY8400364A (en) | 1984-12-31 |
| LU79519A1 (de) | 1978-11-28 |
| JPS53136525A (en) | 1978-11-29 |
| AU524141B2 (en) | 1982-09-02 |
| AU3545778A (en) | 1979-11-01 |
| FR2388559A1 (fr) | 1978-11-24 |
| FR2388559B1 (en, 2012) | 1984-10-19 |
| SG51183G (en) | 1984-04-19 |
| HK67683A (en) | 1983-12-23 |
| JPS62253346A (ja) | 1987-11-05 |
| IT1095611B (it) | 1985-08-10 |
| IL54571A0 (en) | 1978-07-31 |
| BE866389A (fr) | 1978-10-26 |
| KE3325A (en) | 1983-09-16 |
| US4219552A (en) | 1980-08-26 |
| DE2718799A1 (de) | 1978-11-09 |
| JPH038743B2 (en, 2012) | 1991-02-06 |
| IE47681B1 (en) | 1984-05-30 |
| IE780827L (en) | 1978-10-27 |
| GB1571368A (en) | 1980-07-16 |
| IL54571A (en) | 1981-09-13 |
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| 8110 | Request for examination paragraph 44 | ||
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| 8364 | No opposition during term of opposition |