IL28656A - 4-hydroxy-3-quinoline-carboxylic acid compounds,their manufacture and animal feedstuffs containing them - Google Patents
4-hydroxy-3-quinoline-carboxylic acid compounds,their manufacture and animal feedstuffs containing themInfo
- Publication number
- IL28656A IL28656A IL28656A IL2865667A IL28656A IL 28656 A IL28656 A IL 28656A IL 28656 A IL28656 A IL 28656A IL 2865667 A IL2865667 A IL 2865667A IL 28656 A IL28656 A IL 28656A
- Authority
- IL
- Israel
- Prior art keywords
- drinking water
- hydroxy
- group
- cyclopropylmethoxy
- animal
- Prior art date
Links
- 241001465754 Metazoa Species 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 108
- 150000001875 compounds Chemical class 0.000 claims description 81
- -1 or la non-toxic Chemical class 0.000 claims description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 239000003651 drinking water Substances 0.000 claims description 43
- 235000020188 drinking water Nutrition 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 37
- 244000144977 poultry Species 0.000 claims description 26
- 239000000654 additive Substances 0.000 claims description 24
- 231100000252 nontoxic Toxicity 0.000 claims description 22
- 230000003000 nontoxic effect Effects 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 238000010010 raising Methods 0.000 claims description 18
- 125000004494 ethyl ester group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000005907 alkyl ester group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 239000003096 antiparasitic agent Substances 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- MOVHABQYRYJYII-UHFFFAOYSA-N ethyl 8-(cyclopropylmethoxy)-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)OC(=O)C=1C=NC2=C(C=CC=C2C1O)OCC1CC1 MOVHABQYRYJYII-UHFFFAOYSA-N 0.000 claims description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- AVYHBVVCZHBAIN-UHFFFAOYSA-N ethyl 6-(cyclopropylmethoxy)-8-methyl-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)OC(=O)C=1C=NC2=C(C=C(C=C2C1O)OCC1CC1)C AVYHBVVCZHBAIN-UHFFFAOYSA-N 0.000 claims 2
- USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000002141 anti-parasite Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- FPZDCULITKYZJX-UHFFFAOYSA-N ethyl 7-(cyclopropylmethoxy)-6-(2-methylpropoxy)-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)OC(=O)C=1C=NC2=CC(=C(C=C2C1O)OCC(C)C)OCC1CC1 FPZDCULITKYZJX-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- XXPDBLUZJRXNNZ-UHFFFAOYSA-N promethazine hydrochloride Chemical compound Cl.C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 XXPDBLUZJRXNNZ-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 239000003204 tranquilizing agent Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- 239000002244 precipitate Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 235000002639 sodium chloride Nutrition 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229960004756 ethanol Drugs 0.000 description 21
- 239000007858 starting material Substances 0.000 description 19
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- 229940083608 sodium hydroxide Drugs 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 8
- 229940076134 benzene Drugs 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 235000013594 poultry meat Nutrition 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 6
- JBCLGHRMQCEPFM-UHFFFAOYSA-N ethyl 6,7-bis(cyclopropylmethoxy)-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1CC1COC=1C=C2C(=O)C(C(=O)OCC)=CNC2=CC=1OCC1CC1 JBCLGHRMQCEPFM-UHFFFAOYSA-N 0.000 description 6
- 235000012054 meals Nutrition 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- XBVXVNUCAUYFKO-UHFFFAOYSA-N 2-(cyclopropylmethoxy)-5-nitrophenol Chemical compound OC=1C=C(C=CC1OCC1CC1)[N+](=O)[O-] XBVXVNUCAUYFKO-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
- 229910003446 platinum oxide Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241000223924 Eimeria Species 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000271566 Aves Species 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 208000021017 Weight Gain Diseases 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 235000013330 chicken meat Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- KVQYRNKTGMYRGM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]-1,3-dioxane-4,6-dione Chemical compound C1(CC(=O)OC(OC(C)(C)C)O1)=O KVQYRNKTGMYRGM-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- XJNPNXSISMKQEX-UHFFFAOYSA-N 4-nitrocatechol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1O XJNPNXSISMKQEX-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 101100059607 Caenorhabditis elegans cec-3 gene Proteins 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000003495 Coccidiosis Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000223931 Eimeria acervulina Species 0.000 description 2
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
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- 240000004658 Medicago sativa Species 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 208000030852 Parasitic disease Diseases 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- BDVRDAZLRCAMCF-UHFFFAOYSA-N [2-(2-methylpropoxy)-5-nitrophenyl] benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C=CC(=C1)[N+](=O)[O-])OCC(C)C BDVRDAZLRCAMCF-UHFFFAOYSA-N 0.000 description 2
- QBWUZJALZFPQMB-UHFFFAOYSA-N [2-(2-methylpropoxy)phenyl] benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C=CC=C1)OCC(C)C QBWUZJALZFPQMB-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000004467 fishmeal Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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- SDHSOSCEIFYVRK-UHFFFAOYSA-N diethyl 2-[[2-(cyclopropylmethoxy)anilino]methylidene]propanedioate Chemical compound C1(CC1)COC1=C(C=CC=C1)NC=C(C(=O)OCC)C(=O)OCC SDHSOSCEIFYVRK-UHFFFAOYSA-N 0.000 description 1
- JTHHWGDOGNSPCA-UHFFFAOYSA-N diethyl 2-[[3-chloro-4-(cyclopropylmethoxy)anilino]methylidene]propanedioate Chemical compound ClC=1C=C(C=CC1OCC1CC1)NC=C(C(=O)OCC)C(=O)OCC JTHHWGDOGNSPCA-UHFFFAOYSA-N 0.000 description 1
- OSVSXHFCRGEDTF-UHFFFAOYSA-N diethyl 2-[[4-(cyclopropylmethoxy)-2-(trifluoromethyl)anilino]methylidene]propanedioate Chemical compound C1(CC1)COC1=CC(=C(C=C1)NC=C(C(=O)OCC)C(=O)OCC)C(F)(F)F OSVSXHFCRGEDTF-UHFFFAOYSA-N 0.000 description 1
- LYEIHMHUIDXIQD-UHFFFAOYSA-N diethyl 2-[[4-(cyclopropylmethoxy)-3-hydroxyanilino]methylidene]propanedioate Chemical compound OC=1C=C(C=CC1OCC1CC1)NC=C(C(=O)OCC)C(=O)OCC LYEIHMHUIDXIQD-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- HBKHRLFQPUEWAJ-UHFFFAOYSA-N dimethyl 2-[[4-butyl-3-(cyclopropylmethoxy)anilino]methylidene]propanedioate Chemical compound C1(CC1)COC=1C=C(C=CC1CCCC)NC=C(C(=O)OC)C(=O)OC HBKHRLFQPUEWAJ-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 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
- GWFQUBRQAMEPNE-UHFFFAOYSA-N ethyl 3-[2-acetamido-5-(cyclopropylmethoxy)phenyl]-3-oxopropanoate Chemical compound C(C)(=O)NC1=C(C(=O)CC(=O)OCC)C=C(C=C1)OCC1CC1 GWFQUBRQAMEPNE-UHFFFAOYSA-N 0.000 description 1
- ITSYOIRBIPRGDQ-UHFFFAOYSA-N ethyl 6,7-diacetyloxy-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)OC(=O)C=1C=NC2=CC(=C(C=C2C1O)OC(C)=O)OC(C)=O ITSYOIRBIPRGDQ-UHFFFAOYSA-N 0.000 description 1
- ZEDQGBZUMQWKLU-UHFFFAOYSA-N ethyl 6-(cyclopropylmethoxy)-7-(2-methylpropoxy)-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)OC(=O)C=1C=NC2=CC(=C(C=C2C1O)OCC1CC1)OCC(C)C ZEDQGBZUMQWKLU-UHFFFAOYSA-N 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940029985 mineral supplement Drugs 0.000 description 1
- 235000020786 mineral supplement Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- WEIMMECSAQVSGO-UHFFFAOYSA-N n-(3-hydroxy-4-propylphenyl)acetamide Chemical compound CCCC1=CC=C(NC(C)=O)C=C1O WEIMMECSAQVSGO-UHFFFAOYSA-N 0.000 description 1
- RSBIKRQPSYDRFZ-UHFFFAOYSA-N n-(4-butanoyl-3-hydroxyphenyl)acetamide Chemical compound CCCC(=O)C1=CC=C(NC(C)=O)C=C1O RSBIKRQPSYDRFZ-UHFFFAOYSA-N 0.000 description 1
- IPWMGFCGVAEIHP-UHFFFAOYSA-N n-(4-butyl-3-hydroxyphenyl)acetamide Chemical compound CCCCC1=CC=C(NC(C)=O)C=C1O IPWMGFCGVAEIHP-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N n-octadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 210000003250 oocyst Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000036281 parasite infection Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 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
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 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
- 229940100486 rice starch Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- ZMGRMOMYXWGAAE-UHFFFAOYSA-N sodium;ethyl 3-oxobutanoate Chemical compound [Na+].CCOC(=O)[CH-]C(C)=O ZMGRMOMYXWGAAE-UHFFFAOYSA-N 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
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940063650 terramycin Drugs 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58310166A | 1966-09-29 | 1966-09-29 | |
| US62908567A | 1967-04-07 | 1967-04-07 | |
| US65065567A | 1967-07-03 | 1967-07-03 | |
| US66154167A | 1967-08-18 | 1967-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28656A true IL28656A (en) | 1971-11-29 |
Family
ID=27504963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL28656A IL28656A (en) | 1966-09-29 | 1967-09-20 | 4-hydroxy-3-quinoline-carboxylic acid compounds,their manufacture and animal feedstuffs containing them |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS4827317B1 (cs) |
| AT (4) | AT281032B (cs) |
| BE (1) | BE704458A (cs) |
| CH (3) | CH538476A (cs) |
| CS (1) | CS158209B2 (cs) |
| DE (1) | DE1670464A1 (cs) |
| DK (1) | DK137492B (cs) |
| FI (1) | FI48733C (cs) |
| FR (1) | FR1578721A (cs) |
| GB (2) | GB1205639A (cs) |
| IL (1) | IL28656A (cs) |
| NL (1) | NL6713219A (cs) |
| SE (2) | SE342042B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS556193U (cs) * | 1978-06-29 | 1980-01-16 | ||
| DE3276432D1 (en) * | 1981-03-24 | 1987-07-02 | Ciba Geigy Ag | Acyl quinolinone derivatives, processes for their preparation, pharmaceutical compositions containing them and their use |
| FR2537140B1 (fr) * | 1982-12-07 | 1986-07-18 | Roussel Uclaf | Nouveaux derives de la 4-hydroxy-3-quinoleine carboxamide, leur sels, procede de preparation, application a titre de medicaments, et compositions les renfermant |
| US7651699B2 (en) | 2001-01-08 | 2010-01-26 | Pathway Intermediates Limited | Autoinducer compounds and their uses |
-
1967
- 1967-09-18 CH CH1300167A patent/CH538476A/de not_active IP Right Cessation
- 1967-09-18 CH CH60570A patent/CH519304A/de not_active IP Right Cessation
- 1967-09-18 CH CH59770A patent/CH529136A/de not_active IP Right Cessation
- 1967-09-20 IL IL28656A patent/IL28656A/en unknown
- 1967-09-21 DE DE19671670464 patent/DE1670464A1/de active Pending
- 1967-09-25 FI FI672548A patent/FI48733C/fi active
- 1967-09-25 GB GB2190/70A patent/GB1205639A/en not_active Expired
- 1967-09-25 GB GB43549/67A patent/GB1205638A/en not_active Expired
- 1967-09-26 FR FR1578721D patent/FR1578721A/fr not_active Expired
- 1967-09-28 DK DK482067AA patent/DK137492B/da unknown
- 1967-09-28 AT AT01616/69A patent/AT281032B/de not_active IP Right Cessation
- 1967-09-28 SE SE13325/67A patent/SE342042B/xx unknown
- 1967-09-28 AT AT162069A patent/AT288841B/de not_active IP Right Cessation
- 1967-09-28 SE SE7001669A patent/SE388759B/xx unknown
- 1967-09-28 AT AT01615/69A patent/AT281031B/de not_active IP Right Cessation
- 1967-09-28 NL NL6713219A patent/NL6713219A/xx unknown
- 1967-09-28 AT AT880867A patent/AT281030B/de not_active IP Right Cessation
- 1967-09-28 BE BE704458D patent/BE704458A/xx unknown
- 1967-09-29 CS CS692767A patent/CS158209B2/cs unknown
- 1967-09-29 JP JP42062612A patent/JPS4827317B1/ja active Pending
-
1971
- 1971-09-23 JP JP46073946A patent/JPS4918205B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK137492C (cs) | 1978-10-02 |
| JPS4827317B1 (cs) | 1973-08-21 |
| CS158209B2 (cs) | 1974-10-15 |
| FI48733C (fi) | 1974-12-10 |
| FI48733B (cs) | 1974-09-02 |
| SE388759B (sv) | 1976-10-18 |
| AT281031B (de) | 1970-05-25 |
| JPS4918205B1 (cs) | 1974-05-08 |
| NL6713219A (cs) | 1968-04-01 |
| CH519304A (de) | 1972-02-29 |
| CH529136A (de) | 1972-10-15 |
| DK137492B (da) | 1978-03-13 |
| AT288841B (de) | 1971-03-25 |
| CH538476A (de) | 1973-06-30 |
| SE342042B (cs) | 1972-01-24 |
| FR1578721A (cs) | 1969-08-22 |
| BE704458A (cs) | 1968-03-28 |
| GB1205639A (en) | 1970-09-16 |
| GB1205638A (en) | 1970-09-16 |
| AT281030B (de) | 1970-05-11 |
| AT281032B (de) | 1970-05-25 |
| DE1670464A1 (de) | 1971-02-11 |
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