JPH01156975A - （２−チエニルメチル）チオ尿素誘導体及びその製造方法、前記化合物を含む体重増大作用を有する飼料添加物、並びに酪農における前記添加物の使用方法 - Google Patents
（２−チエニルメチル）チオ尿素誘導体及びその製造方法、前記化合物を含む体重増大作用を有する飼料添加物、並びに酪農における前記添加物の使用方法Info
- Publication number
- JPH01156975A JPH01156975A JP63244723A JP24472388A JPH01156975A JP H01156975 A JPH01156975 A JP H01156975A JP 63244723 A JP63244723 A JP 63244723A JP 24472388 A JP24472388 A JP 24472388A JP H01156975 A JPH01156975 A JP H01156975A
- Authority
- JP
- Japan
- Prior art keywords
- group
- thienylmethyl
- general formula
- thiourea
- represented
- 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.)
- Pending
Links
- XARZSESQHPGTIA-UHFFFAOYSA-N thiophen-2-ylmethylthiourea Chemical class NC(=S)NCC1=CC=CS1 XARZSESQHPGTIA-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 title claims description 43
- 239000003674 animal food additive Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 230000001965 increasing effect Effects 0.000 title claims description 5
- 238000003977 dairy farming Methods 0.000 title claims description 4
- 230000037396 body weight Effects 0.000 title claims description 3
- 239000000654 additive Substances 0.000 title description 4
- 230000000996 additive effect Effects 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 230000000694 effects Effects 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- LTAWCHATRSDECJ-UHFFFAOYSA-N n-(thiophen-2-ylmethylcarbamothioyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=S)NCC1=CC=CS1 LTAWCHATRSDECJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 31
- 241001465754 Metazoa Species 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 240000008042 Zea mays Species 0.000 claims description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 9
- 235000005822 corn Nutrition 0.000 claims description 9
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 claims description 9
- OKJOHEAQGOKDDQ-UHFFFAOYSA-N 2-(isothiocyanatomethyl)thiophene Chemical compound S=C=NCC1=CC=CS1 OKJOHEAQGOKDDQ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 244000075850 Avena orientalis Species 0.000 claims description 5
- 235000007319 Avena orientalis Nutrition 0.000 claims description 5
- 244000068988 Glycine max Species 0.000 claims description 5
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- 240000005979 Hordeum vulgare Species 0.000 claims description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 235000012054 meals Nutrition 0.000 claims description 5
- 240000004658 Medicago sativa Species 0.000 claims description 4
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ZAUXSEINZZFHJQ-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(thiophen-2-ylmethyl)thiourea Chemical compound CC1=CC=CC(C)=C1NC(=S)NCC1=CC=CS1 ZAUXSEINZZFHJQ-UHFFFAOYSA-N 0.000 claims description 3
- GGSGFYSXUZNZBK-UHFFFAOYSA-N 4-methoxy-n-(thiophen-2-ylmethylcarbamothioyl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(=S)NCC1=CC=CS1 GGSGFYSXUZNZBK-UHFFFAOYSA-N 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 3
- 235000019733 Fish meal Nutrition 0.000 claims description 3
- 235000007238 Secale cereale Nutrition 0.000 claims description 3
- 239000004467 fishmeal Substances 0.000 claims description 3
- MGJQDYLEYDAZMM-UHFFFAOYSA-N 1-benzyl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C=1C=CC=CC=1CNC(=S)NCC1=CC=CS1 MGJQDYLEYDAZMM-UHFFFAOYSA-N 0.000 claims description 2
- OHIBLLMOWFJKRX-UHFFFAOYSA-N 1-cyclohexyl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C1CCCCC1NC(=S)NCC1=CC=CS1 OHIBLLMOWFJKRX-UHFFFAOYSA-N 0.000 claims description 2
- CHBSEWCHNLDUDL-UHFFFAOYSA-N 3-phenyl-n-(thiophen-2-ylmethylcarbamothioyl)prop-2-enamide Chemical compound C=1C=CC=CC=1C=CC(=O)NC(=S)NCC1=CC=CS1 CHBSEWCHNLDUDL-UHFFFAOYSA-N 0.000 claims description 2
- 241000209056 Secale Species 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 235000013372 meat Nutrition 0.000 claims description 2
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims 4
- JWROELOQCWYKLG-UHFFFAOYSA-N 1,1-dicyclohexyl-3-(thiophen-2-ylmethyl)thiourea Chemical class C1CCCCC1N(C1CCCCC1)C(=S)NCC1=CC=CS1 JWROELOQCWYKLG-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 8
- 241000287828 Gallus gallus Species 0.000 abstract description 6
- 235000019687 Lamb Nutrition 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- -1 phenyl-〇yo- Chemical group 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000283903 Ovis aries Species 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 241000282887 Suidae Species 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000011573 trace mineral Substances 0.000 description 5
- 235000013619 trace mineral Nutrition 0.000 description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229930003270 Vitamin B Natural products 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 239000001506 calcium phosphate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000019156 vitamin B Nutrition 0.000 description 4
- 239000011720 vitamin B Substances 0.000 description 4
- 150000003722 vitamin derivatives Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108010001478 Bacitracin Proteins 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 235000013330 chicken meat Nutrition 0.000 description 3
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 3
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
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- UCRLQOPRDMGYOA-DFTDUNEMSA-L zinc;(4r)-4-[[(2s)-2-[[(4r)-2-[(1s,2s)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2s,3s)-1-[[(3s,6r,9s,12r,15s,18r,21s)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2s)-butan-2-yl]-6-(carbox Chemical compound [Zn+2].C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC([O-])=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2NC=NC=2)C(=O)N[C@H](CC([O-])=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 UCRLQOPRDMGYOA-DFTDUNEMSA-L 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
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- BCZXFFBUYPCTSJ-UHFFFAOYSA-L Calcium propionate Chemical compound [Ca+2].CCC([O-])=O.CCC([O-])=O BCZXFFBUYPCTSJ-UHFFFAOYSA-L 0.000 description 2
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- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- NGFPILQBEUNZPU-UHFFFAOYSA-N 1-(2-phenylethyl)-3-(thiophen-2-ylmethyl)thiourea Chemical compound C=1C=CSC=1CNC(=S)NCCC1=CC=CC=C1 NGFPILQBEUNZPU-UHFFFAOYSA-N 0.000 description 1
- QGXOYUVNSIDKNQ-UHFFFAOYSA-N 1-(4-methylpyridin-2-yl)-1-(thiophen-2-ylmethyl)thiourea Chemical compound CC1=CC(=NC=C1)N(C(=S)N)CC=1SC=CC1 QGXOYUVNSIDKNQ-UHFFFAOYSA-N 0.000 description 1
- GPIGWSZGKHIJPT-UHFFFAOYSA-N 1-naphthalen-1-yl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=S)NCC1=CC=CS1 GPIGWSZGKHIJPT-UHFFFAOYSA-N 0.000 description 1
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- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000002374 bone meal Substances 0.000 description 1
- 229940036811 bone meal Drugs 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229960003563 calcium carbonate Drugs 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- UUVBYOGFRMMMQL-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca].OP(O)(O)=O UUVBYOGFRMMMQL-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MZSJGCPBOVTKHR-UHFFFAOYSA-N isothiocyanatocyclohexane Chemical compound S=C=NC1CCCCC1 MZSJGCPBOVTKHR-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- XWAZIQKMWSJHPK-UHFFFAOYSA-N thiophen-2-ylmethyl thiocyanate Chemical compound C1(=CC=CS1)CSC#N XWAZIQKMWSJHPK-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 230000036346 tooth eruption Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Husbandry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU874437A HU202516B (en) | 1987-10-02 | 1987-10-02 | Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds |
| HU2251-4437/87 | 1987-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01156975A true JPH01156975A (ja) | 1989-06-20 |
Family
ID=10967957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63244723A Pending JPH01156975A (ja) | 1987-10-02 | 1988-09-30 | （２−チエニルメチル）チオ尿素誘導体及びその製造方法、前記化合物を含む体重増大作用を有する飼料添加物、並びに酪農における前記添加物の使用方法 |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPH01156975A (es) |
| KR (1) | KR890006612A (es) |
| AU (1) | AU607811B2 (es) |
| BE (1) | BE1003234A4 (es) |
| CH (1) | CH676849A5 (es) |
| DD (1) | DD282914A5 (es) |
| DE (1) | DE3833603A1 (es) |
| DK (1) | DK549788A (es) |
| ES (1) | ES2012122A6 (es) |
| FR (1) | FR2621315A1 (es) |
| GB (1) | GB2210616B (es) |
| HU (1) | HU202516B (es) |
| IL (1) | IL87874A0 (es) |
| IT (1) | IT1226862B (es) |
| NL (1) | NL8802406A (es) |
| PL (3) | PL151836B1 (es) |
| RU (1) | RU1792415C (es) |
| SU (2) | SU1709909A3 (es) |
| YU (3) | YU182188A (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO20093460A1 (no) * | 2009-12-02 | 2011-06-03 | Ewos Innovation As | Fôrsammensetning til fisk inneholdende en semiokjemisk maskeringsforbindelse samt anvendelse av forbindelsen. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL125059C (es) * | 1963-05-31 | |||
| US4313885A (en) * | 1980-05-21 | 1982-02-02 | American Cyanamid Company | Furfuryl thiourea compounds |
| US4267191A (en) * | 1980-05-21 | 1981-05-12 | American Cyanamid Company | Process for enhancing growth promotion in animals |
| IL82401A0 (en) * | 1986-05-06 | 1987-11-30 | Merrell Dow Pharma | Dopamine beta hydroxy-lase inhibiting imidazole derivatives and pharmaceutical compositions containing them |
| DE3703963A1 (de) * | 1987-02-10 | 1988-08-18 | Hoechst Ag | Pyridin-2,4- und 2,,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben, sowie arzneimittel auf basis dieser verbindungen |
-
1987
- 1987-10-02 HU HU874437A patent/HU202516B/hu not_active IP Right Cessation
-
1988
- 1988-09-29 YU YU01821/88A patent/YU182188A/xx unknown
- 1988-09-29 IL IL87874A patent/IL87874A0/xx unknown
- 1988-09-29 CH CH3625/88A patent/CH676849A5/de not_active IP Right Cessation
- 1988-09-30 FR FR8812802A patent/FR2621315A1/fr not_active Withdrawn
- 1988-09-30 IT IT8822147A patent/IT1226862B/it active
- 1988-09-30 DK DK549788A patent/DK549788A/da not_active Application Discontinuation
- 1988-09-30 RU SU884356919A patent/RU1792415C/ru active
- 1988-09-30 GB GB8823012A patent/GB2210616B/en not_active Expired - Lifetime
- 1988-09-30 PL PL1988277628A patent/PL151836B1/pl unknown
- 1988-09-30 PL PL1988274988A patent/PL151572B1/pl unknown
- 1988-09-30 ES ES8802966A patent/ES2012122A6/es not_active Expired - Lifetime
- 1988-09-30 JP JP63244723A patent/JPH01156975A/ja active Pending
- 1988-09-30 NL NL8802406A patent/NL8802406A/nl unknown
- 1988-09-30 PL PL1988277629A patent/PL151837B1/pl unknown
- 1988-09-30 BE BE8801119A patent/BE1003234A4/fr not_active IP Right Cessation
- 1988-09-30 KR KR1019880012758A patent/KR890006612A/ko not_active Application Discontinuation
- 1988-09-30 DD DD88320334A patent/DD282914A5/de not_active IP Right Cessation
- 1988-09-30 AU AU23329/88A patent/AU607811B2/en not_active Ceased
- 1988-10-03 DE DE3833603A patent/DE3833603A1/de not_active Withdrawn
-
1989
- 1989-04-18 SU SU894613916A patent/SU1709909A3/ru active
- 1989-04-18 SU SU894613899A patent/SU1739847A3/ru active
-
1990
- 1990-02-05 YU YU00205/90A patent/YU20590A/xx unknown
- 1990-02-05 YU YU00204/90A patent/YU20490A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD282914A5 (de) | 1990-09-26 |
| BE1003234A4 (fr) | 1992-02-04 |
| CH676849A5 (es) | 1991-03-15 |
| FR2621315A1 (fr) | 1989-04-07 |
| GB8823012D0 (en) | 1988-11-09 |
| RU1792415C (ru) | 1993-01-30 |
| PL151836B1 (en) | 1990-10-31 |
| DK549788D0 (da) | 1988-09-30 |
| YU20590A (en) | 1990-06-30 |
| DE3833603A1 (de) | 1989-04-13 |
| YU20490A (en) | 1990-06-30 |
| AU607811B2 (en) | 1991-03-14 |
| AU2332988A (en) | 1989-04-06 |
| PL151572B1 (en) | 1990-09-28 |
| PL277629A1 (en) | 1989-08-21 |
| NL8802406A (nl) | 1989-05-01 |
| ES2012122A6 (es) | 1990-03-01 |
| HU202516B (en) | 1991-03-28 |
| IL87874A0 (en) | 1989-03-31 |
| IT1226862B (it) | 1991-02-19 |
| HUT48879A (en) | 1989-07-28 |
| GB2210616B (en) | 1991-03-27 |
| SU1709909A3 (ru) | 1992-01-30 |
| DK549788A (da) | 1989-04-03 |
| PL277628A1 (en) | 1989-08-21 |
| PL274988A1 (en) | 1989-06-12 |
| PL151837B1 (en) | 1990-10-31 |
| GB2210616A (en) | 1989-06-14 |
| IT8822147A0 (it) | 1988-09-30 |
| SU1739847A3 (ru) | 1992-06-07 |
| KR890006612A (ko) | 1989-06-14 |
| YU182188A (en) | 1990-06-30 |
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