DE2352581A1 - Mittel gegen kokzidiose - Google Patents
Mittel gegen kokzidioseInfo
- Publication number
- DE2352581A1 DE2352581A1 DE19732352581 DE2352581A DE2352581A1 DE 2352581 A1 DE2352581 A1 DE 2352581A1 DE 19732352581 DE19732352581 DE 19732352581 DE 2352581 A DE2352581 A DE 2352581A DE 2352581 A1 DE2352581 A1 DE 2352581A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- methyl
- carbon atoms
- pyridinol
- compound
- 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.)
- Ceased
Links
- 208000003495 Coccidiosis Diseases 0.000 title claims description 17
- 206010023076 Isosporiasis Diseases 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 74
- -1 N-substituted thiocarbamoyl group Chemical group 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 33
- GMUFGAIZRAMTEN-UHFFFAOYSA-N 5-(hydroxymethyl)-2-methylpyridin-3-ol Chemical compound CC1=NC=C(CO)C=C1O GMUFGAIZRAMTEN-UHFFFAOYSA-N 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 244000144977 poultry Species 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 8
- 239000003224 coccidiostatic agent Substances 0.000 claims description 7
- 229940124536 anticoccidial agent Drugs 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- 239000013078 crystal Substances 0.000 description 47
- 238000000034 method Methods 0.000 description 47
- 238000004458 analytical method Methods 0.000 description 46
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
- 239000000047 product Substances 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 26
- 238000002329 infrared spectrum Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 20
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 235000013594 poultry meat Nutrition 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 15
- 210000003250 oocyst Anatomy 0.000 description 15
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 241000287828 Gallus gallus Species 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 235000013330 chicken meat Nutrition 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- 230000004584 weight gain Effects 0.000 description 7
- 235000019786 weight gain Nutrition 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000006052 feed supplement Substances 0.000 description 5
- 210000000936 intestine Anatomy 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- IUKSYUOJRHDWRR-UHFFFAOYSA-N 2-diazonio-4,6-dinitrophenolate Chemical compound [O-]C1=C([N+]#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O IUKSYUOJRHDWRR-UHFFFAOYSA-N 0.000 description 4
- OHBHFJXHFRZANX-UHFFFAOYSA-N 5-(hydroxymethyl)-2-methylpyridin-3-ol;hydrochloride Chemical compound Cl.CC1=NC=C(CO)C=C1O OHBHFJXHFRZANX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 230000001165 anti-coccidial effect Effects 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 210000003608 fece Anatomy 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000000069 prophylactic effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000012384 transportation and delivery Methods 0.000 description 4
- SNCDKYZKTKSKGA-UHFFFAOYSA-N (5-hydroxy-6-methylpyridin-3-yl)methyl pentanoate Chemical compound CCCCC(=O)OCC1=CN=C(C)C(O)=C1 SNCDKYZKTKSKGA-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
- 241000223924 Eimeria Species 0.000 description 3
- 241000223931 Eimeria acervulina Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- REJBBRNPOXARAI-UHFFFAOYSA-N [5-(methoxycarbonyloxymethyl)-2-methylpyridin-3-yl] methyl carbonate Chemical compound COC(=O)OCC1=CN=C(C)C(OC(=O)OC)=C1 REJBBRNPOXARAI-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002192 coccidiostatic effect Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 210000000813 small intestine Anatomy 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 235000015099 wheat brans Nutrition 0.000 description 3
- AUDADIIYSIISJU-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl benzoate Chemical compound N1=C(C)C(OC(=O)C)=CC(COC(=O)C=2C=CC=CC=2)=C1 AUDADIIYSIISJU-UHFFFAOYSA-N 0.000 description 2
- XGLDKNGDYFBFBQ-UHFFFAOYSA-N (5-hydroxy-6-methylpyridin-3-yl)methyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCC1=CN=C(C)C(O)=C1 XGLDKNGDYFBFBQ-UHFFFAOYSA-N 0.000 description 2
- HBULPTOVOXBZGD-UHFFFAOYSA-N (5-hydroxy-6-methylpyridin-3-yl)methyl benzoate Chemical compound C1=C(O)C(C)=NC=C1COC(=O)C1=CC=CC=C1 HBULPTOVOXBZGD-UHFFFAOYSA-N 0.000 description 2
- GHIXHQZYJQLPNP-UHFFFAOYSA-N (5-hydroxy-6-methylpyridin-3-yl)methyl octanoate Chemical compound CCCCCCCC(=O)OCC1=CN=C(C)C(O)=C1 GHIXHQZYJQLPNP-UHFFFAOYSA-N 0.000 description 2
- BWRAEWUYJSPSFN-UHFFFAOYSA-N (5-hydroxy-6-methylpyridin-3-yl)methyl propanoate Chemical compound CCC(=O)OCC1=CN=C(C)C(O)=C1 BWRAEWUYJSPSFN-UHFFFAOYSA-N 0.000 description 2
- CSPRBDVVAYJGMY-UHFFFAOYSA-N (6-methyl-5-phenylmethoxypyridin-3-yl)methanol Chemical compound CC1=NC=C(CO)C=C1OCC1=CC=CC=C1 CSPRBDVVAYJGMY-UHFFFAOYSA-N 0.000 description 2
- ZSUUXLHBPRBHGA-UHFFFAOYSA-N 2-methyl-5-(phenylmethoxymethyl)pyridin-3-ol Chemical compound C1=C(O)C(C)=NC=C1COCC1=CC=CC=C1 ZSUUXLHBPRBHGA-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- ZQKGKAKJYABQAK-UHFFFAOYSA-N 4-(hydroxymethyl)-2-methylpyridin-3-ol Chemical compound CC1=NC=CC(CO)=C1O ZQKGKAKJYABQAK-UHFFFAOYSA-N 0.000 description 2
- BPEQAFGUCPPRIB-UHFFFAOYSA-M 5-[[5-(2-chloroethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]methyl]-2-methylpyrimidin-4-amine;chloride Chemical compound [Cl-].CC1=C(CCCl)SC=[N+]1CC1=CN=C(C)N=C1N BPEQAFGUCPPRIB-UHFFFAOYSA-M 0.000 description 2
- 241000271566 Aves Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000252983 Caecum Species 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- 241000224483 Coccidia Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000019764 Soybean Meal Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 101150052863 THY1 gene Proteins 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- LZOGEQSZPRANDR-UHFFFAOYSA-N [5-(hydroxymethyl)-2-methylpyridin-3-yl] 4-chlorobenzoate Chemical compound CC1=NC=C(CO)C=C1OC(=O)C1=CC=C(Cl)C=C1 LZOGEQSZPRANDR-UHFFFAOYSA-N 0.000 description 2
- MQVZDDNXLKYPHD-UHFFFAOYSA-N [5-(hydroxymethyl)-2-methylpyridin-3-yl] 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OC1=CC(CO)=CN=C1C MQVZDDNXLKYPHD-UHFFFAOYSA-N 0.000 description 2
- HQVJWVPSUIBSSH-UHFFFAOYSA-N [5-(hydroxymethyl)-2-methylpyridin-3-yl] acetate;hydrochloride Chemical compound Cl.CC(=O)OC1=CC(CO)=CN=C1C HQVJWVPSUIBSSH-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 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
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 229950011170 beclotiamine Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 210000004534 cecum Anatomy 0.000 description 2
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 2
- 208000037817 intestinal injury Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 239000004455 soybean meal Substances 0.000 description 2
- 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 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- JEWCRDSKJAOUJK-UHFFFAOYSA-N (3-hydroxy-2-methyl-2H-pyridin-3-yl)methyl hexadecanoate Chemical compound CC1N=CC=CC1(O)COC(CCCCCCCCCCCCCCC)=O JEWCRDSKJAOUJK-UHFFFAOYSA-N 0.000 description 1
- LDDRRLKONGHQBH-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OCC1=CN=C(C)C(OC(C)=O)=C1 LDDRRLKONGHQBH-UHFFFAOYSA-N 0.000 description 1
- FYUYYFMGARVUGT-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl acetate Chemical compound CC(=O)OCC1=CN=C(C)C(OC(C)=O)=C1 FYUYYFMGARVUGT-UHFFFAOYSA-N 0.000 description 1
- RAYKHYPKTWTHNS-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl butanoate Chemical compound CCCC(=O)OCC1=CN=C(C)C(OC(C)=O)=C1 RAYKHYPKTWTHNS-UHFFFAOYSA-N 0.000 description 1
- CFKLLMBNHSQMEJ-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl cyclohexanecarboxylate Chemical compound N1=C(C)C(OC(=O)C)=CC(COC(=O)C2CCCCC2)=C1 CFKLLMBNHSQMEJ-UHFFFAOYSA-N 0.000 description 1
- DMKPTBFWOOAQOM-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl furan-2-carboxylate Chemical compound N1=C(C)C(OC(=O)C)=CC(COC(=O)C=2OC=CC=2)=C1 DMKPTBFWOOAQOM-UHFFFAOYSA-N 0.000 description 1
- WGBYUKYQWKMKGB-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC1=CN=C(C)C(OC(C)=O)=C1 WGBYUKYQWKMKGB-UHFFFAOYSA-N 0.000 description 1
- KYFJFGZOWUSVJH-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC1=CN=C(C)C(OC(C)=O)=C1 KYFJFGZOWUSVJH-UHFFFAOYSA-N 0.000 description 1
- WDSAISONZNRSFI-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl octanoate Chemical compound CCCCCCCC(=O)OCC1=CN=C(C)C(OC(C)=O)=C1 WDSAISONZNRSFI-UHFFFAOYSA-N 0.000 description 1
- XYHABHDCZUGZCU-UHFFFAOYSA-N (5-acetyloxy-6-methylpyridin-3-yl)methyl propanoate Chemical compound CCC(=O)OCC1=CN=C(C)C(OC(C)=O)=C1 XYHABHDCZUGZCU-UHFFFAOYSA-N 0.000 description 1
- ROQOMKDKPRYOHD-UHFFFAOYSA-N (5-benzoyloxy-6-methylpyridin-3-yl)methyl benzoate Chemical compound C1=C(OC(=O)C=2C=CC=CC=2)C(C)=NC=C1COC(=O)C1=CC=CC=C1 ROQOMKDKPRYOHD-UHFFFAOYSA-N 0.000 description 1
- SHTJQVWNODTDAW-UHFFFAOYSA-N (5-benzoyloxy-6-methylpyridin-3-yl)methyl furan-2-carboxylate Chemical compound C1=C(OC(=O)C=2C=CC=CC=2)C(C)=NC=C1COC(=O)C1=CC=CO1 SHTJQVWNODTDAW-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960000731 clopidol Drugs 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- LDBTVAXGKYIFHO-UHFFFAOYSA-N diaveridine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N LDBTVAXGKYIFHO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000004052 folic acid antagonist Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000005005 gametogony Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 229940093920 gynecological arsenic compound Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 230000000266 injurious effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 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
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 229940073485 nicarbazin Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- RQXCLMGKHJWMOA-UHFFFAOYSA-N pridinol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 RQXCLMGKHJWMOA-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 208000037974 severe injury Diseases 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 210000004215 spore Anatomy 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
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003544 thiamines Chemical class 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- 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
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10509072A JPS5537529B2 (cg-RX-API-DMAC10.html) | 1972-10-20 | 1972-10-20 | |
| JP48041111A JPS49125510A (cg-RX-API-DMAC10.html) | 1973-04-11 | 1973-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2352581A1 true DE2352581A1 (de) | 1974-05-02 |
Family
ID=26380658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732352581 Ceased DE2352581A1 (de) | 1972-10-20 | 1973-10-19 | Mittel gegen kokzidiose |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3897556A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2352581A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2203636B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1394038A (cg-RX-API-DMAC10.html) |
| IT (1) | IT1009053B (cg-RX-API-DMAC10.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6436972B1 (en) | 2000-04-10 | 2002-08-20 | Dalhousie University | Pyridones and their use as modulators of serine hydrolase enzymes |
-
1973
- 1973-10-09 US US404641A patent/US3897556A/en not_active Expired - Lifetime
- 1973-10-12 GB GB4783673A patent/GB1394038A/en not_active Expired
- 1973-10-19 DE DE19732352581 patent/DE2352581A1/de not_active Ceased
- 1973-10-22 FR FR7337527A patent/FR2203636B1/fr not_active Expired
- 1973-10-22 IT IT70111/73A patent/IT1009053B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2203636B1 (cg-RX-API-DMAC10.html) | 1977-09-09 |
| FR2203636A1 (cg-RX-API-DMAC10.html) | 1974-05-17 |
| GB1394038A (en) | 1975-05-14 |
| US3897556A (en) | 1975-07-29 |
| IT1009053B (it) | 1976-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |