IL27590A - אלקיל 7-דיאלקילאמינו-4-הידרוקסי- כינולין -3-קרבאוקסילטים הכנתם ותכשירים נגד מחלת כנימת המגן המכילים אותם - Google Patents

אלקיל 7-דיאלקילאמינו-4-הידרוקסי- כינולין -3-קרבאוקסילטים הכנתם ותכשירים נגד מחלת כנימת המגן המכילים אותם

Info

Publication number: IL27590A
Authority: IL; Israel
Prior art keywords: hydroxy; loweralkyl; formula; compound; quinoline
Prior art date: 1965-12-22

Application number

IL27590A

Other languages

English (en)

Original Assignee

Merck & Co Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1965-12-22

Filing date

1967-03-13

Publication date

1971-02-25

1967-03-01 Priority claimed from US619546A external-priority patent/US3377352A/en

1967-03-13 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1971-02-25 Publication of IL27590A publication Critical patent/IL27590A/he

Links

239000000203 mixture Substances 0.000 title claims description 38
230000001165 anti-coccidial effect Effects 0.000 title claims description 9
125000000217 alkyl group Chemical group 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
244000144977 poultry Species 0.000 claims description 14
208000003495 Coccidiosis Diseases 0.000 claims description 12
206010023076 Isosporiasis Diseases 0.000 claims description 12
150000007942 carboxylates Chemical class 0.000 claims description 11
150000003839 salts Chemical group 0.000 claims description 10
239000007787 solid Substances 0.000 claims description 10
238000010438 heat treatment Methods 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000003674 animal food additive Substances 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
-1 alkyl radical Chemical class 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
238000001914 filtration Methods 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000003224 coccidiostatic agent Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
230000000875 corresponding effect Effects 0.000 description 6
239000006052 feed supplement Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XJDDLMJULQGRLU-UHFFFAOYSA-N 1,3-dioxane-4,6-dione Chemical compound O=C1CC(=O)OCO1 XJDDLMJULQGRLU-UHFFFAOYSA-N 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
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241000271566 Aves Species 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
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239000000047 product Substances 0.000 description 4
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
241000894007 species Species 0.000 description 4
241000223934 Eimeria maxima Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
229940107816 ammonium iodide Drugs 0.000 description 3
229960003683 amprolium Drugs 0.000 description 3
150000001448 anilines Chemical class 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
RHFZTBSULNJWEI-UHFFFAOYSA-N dimethyl 2-(methoxymethylidene)propanedioate Chemical compound COC=C(C(=O)OC)C(=O)OC RHFZTBSULNJWEI-UHFFFAOYSA-N 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
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 3
239000004615 ingredient Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241000224483 Coccidia Species 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
241000499566 Eimeria brunetti Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
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238000003556 assay Methods 0.000 description 2
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OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
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238000002474 experimental method Methods 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
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235000010755 mineral Nutrition 0.000 description 2
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150000002828 nitro derivatives Chemical class 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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238000007363 ring formation reaction Methods 0.000 description 2
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HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
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TYPCPVCAXMMOQN-UHFFFAOYSA-N 2-butyl-n,n-diethylaniline Chemical compound CCCCC1=CC=CC=C1N(CC)CC TYPCPVCAXMMOQN-UHFFFAOYSA-N 0.000 description 1
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101100111799 Caenorhabditis elegans best-22 gene Proteins 0.000 description 1
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241001452550 Eimeria meleagridis Species 0.000 description 1
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LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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IXCKOXLJNNFOCM-UHFFFAOYSA-N n,n,2-triethylaniline Chemical compound CCN(CC)C1=CC=CC=C1CC IXCKOXLJNNFOCM-UHFFFAOYSA-N 0.000 description 1
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230000000069 prophylactic effect Effects 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
244000000040 protozoan parasite Species 0.000 description 1
DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000003303 reheating Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000036642 wellbeing Effects 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Fodder In General (AREA)

IL27590A 1965-12-22 1967-03-13 אלקיל 7-דיאלקילאמינו-4-הידרוקסי- כינולין -3-קרבאוקסילטים הכנתם ותכשירים נגד מחלת כנימת המגן המכילים אותם IL27590A (he)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US51575765A	1965-12-22	1965-12-22
US54049566A	1966-04-06	1966-04-06
US57222566A	1966-08-15	1966-08-15
US57346966A	1966-08-19	1966-08-19
US61955567A	1967-03-01	1967-03-01
US619546A US3377352A (en)	1965-12-22	1967-03-01	Alkylamino-4-hydroxy quinoline-3-carboxylic esters

Publications (1)

Publication Number	Publication Date
IL27590A true IL27590A (he)	1971-02-25

Family

ID=27560088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL27590A IL27590A (he)	1965-12-22	1967-03-13	אלקיל 7-דיאלקילאמינו-4-הידרוקסי- כינולין -3-קרבאוקסילטים הכנתם ותכשירים נגד מחלת כנימת המגן המכילים אותם

Country Status (9)

Country	Link
BE (1)	BE696688A (he)
CH (1)	CH486460A (he)
DE (1)	DE1695406A1 (he)
DK (1)	DK118605B (he)
ES (1)	ES339427A1 (he)
GB (1)	GB1153649A (he)
IL (1)	IL27590A (he)
NL (1)	NL6704778A (he)
SE (1)	SE323680B (he)

1967
- 1967-03-13 IL IL27590A patent/IL27590A/he unknown
- 1967-03-31 DK DK182167AA patent/DK118605B/da unknown
- 1967-04-04 SE SE4663/67A patent/SE323680B/xx unknown
- 1967-04-04 NL NL6704778A patent/NL6704778A/xx unknown
- 1967-04-04 GB GB05317/67A patent/GB1153649A/en not_active Expired
- 1967-04-05 DE DE19671695406 patent/DE1695406A1/de active Pending
- 1967-04-05 ES ES339427A patent/ES339427A1/es not_active Expired
- 1967-04-06 BE BE696688D patent/BE696688A/xx unknown
- 1967-04-06 CH CH487167A patent/CH486460A/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE696688A (he)	1967-10-06
SE323680B (he)	1970-05-11
CH486460A (de)	1970-02-28
DK118605B (da)	1970-09-14
NL6704778A (he)	1967-10-09
ES339427A1 (es)	1968-05-01
DE1695406A1 (de)	1971-04-08
GB1153649A (en)	1969-05-29

Publication	Publication Date	Title
US3316147A (en)	1967-04-25	Coccidial compositions containing lower alkyl esters of 6, 7-di(lower) alkoxy-4-hydroxy-3-quinolinecarboxylic acid
EP0035393A1 (en)	1981-09-09	Poultry feeds containing and methods of using anovulatory compounds, and novel anovulatory imidazolines
US3377352A (en)	1968-04-09	Alkylamino-4-hydroxy quinoline-3-carboxylic esters
US3211610A (en)	1965-10-12	Benzoic acid ester derivatives for treating coccidiosis and method of using same
US3020277A (en)	1962-02-06	1-(2-n-propyl-4-amino-5-pyrimidyl-methyl)-2(or 4)-methyl pyridinium salts
EP0098589B1 (en)	1987-12-09	Quinazoline derivatives which are active against coccidiosis
US3560496A (en)	1971-02-02	2-benzyl-as-triazine-3,5(2h,4h) diones
US3399203A (en)	1968-08-27	6-loweralkoxy-7-loweralkyl quinolates
IL27590A (he)	1971-02-25	אלקיל 7-דיאלקילאמינו-4-הידרוקסי- כינולין -3-קרבאוקסילטים הכנתם ותכשירים נגד מחלת כנימת המגן המכילים אותם
US3542851A (en)	1970-11-24	Novel acrylate,amines and ethers
US3830928A (en)	1974-08-20	Substituted phenyltetrazoles as coccidiostats
US3795692A (en)	1974-03-05	Compounds and processes
US4311710A (en)	1982-01-19	Anticoccidial formulation and method
US3816530A (en)	1974-06-11	Novel chemical compounds and processes for preparing same
US3399202A (en)	1968-08-27	6, 7-disubstituted quinolates
US3474169A (en)	1969-10-21	Anticoccidial compositions containing substituted quinoline-3-carboxylates
US3449403A (en)	1969-06-10	Novel acrylates
US3542781A (en)	1970-11-24	7-alkylamino 7-hydroxy quinoline 3-carboxylates
US4130661A (en)	1978-12-19	Substituted benzoylacrylanilides
US3155572A (en)	1964-11-03	Compositions and methods for treating coccidiosis
US3357884A (en)	1967-12-12	Anthelmintic compositions containing benzimidazole derivatives
US3549642A (en)	1970-12-22	6,7-disubstituted-4-hydroxy-quinoline-3-carboxylates
US3715395A (en)	1973-02-06	Substituted thiobenzanilides
US3439019A (en)	1969-04-15	N-benzoyloxymethyl benzamides and their preparation
US3448193A (en)	1969-06-03	Anticoccidial composition containing 6,7 - disubstituted-quinoline - 3-carboxylates