JP5511679B2 - 飼料添加物としての２−メチルチオエチル置換複素環 - Google Patents
飼料添加物としての２−メチルチオエチル置換複素環 Download PDFInfo
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- JP5511679B2 JP5511679B2 JP2010538543A JP2010538543A JP5511679B2 JP 5511679 B2 JP5511679 B2 JP 5511679B2 JP 2010538543 A JP2010538543 A JP 2010538543A JP 2010538543 A JP2010538543 A JP 2010538543A JP 5511679 B2 JP5511679 B2 JP 5511679B2
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- methylthio
- methionine
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- -1 2-Methylthioethyl Chemical group 0.000 title claims description 10
- 239000003674 animal food additive Substances 0.000 title description 8
- 125000000623 heterocyclic group Chemical group 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 14
- 241000282849 Ruminantia Species 0.000 claims description 13
- 239000007848 Bronsted acid Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 235000016709 nutrition Nutrition 0.000 claims description 9
- 230000035764 nutrition Effects 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 244000144972 livestock Species 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 241000251468 Actinopterygii Species 0.000 claims description 7
- 241000238424 Crustacea Species 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 241000282887 Suidae Species 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
- 244000144977 poultry Species 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 241000023320 Luma <angiosperm> Species 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 229960004452 methionine Drugs 0.000 description 35
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 33
- 229930182817 methionine Natural products 0.000 description 33
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 22
- INTUDBWOILOBCE-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanamide Chemical compound CSCCC(O)C(N)=O INTUDBWOILOBCE-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 18
- 210000004767 rumen Anatomy 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- CTTWBUQGUOUQIT-UHFFFAOYSA-N 2,2-dimethyl-5-(2-methylsulfanylethyl)-1,3-oxazolidin-4-one Chemical compound CSCCC1OC(C)(C)NC1=O CTTWBUQGUOUQIT-UHFFFAOYSA-N 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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- 230000007062 hydrolysis Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
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- HLUFSGZOJZQPRX-UHFFFAOYSA-N 2,2-dimethyl-5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CSCCC1OC(C)(C)OC1=O HLUFSGZOJZQPRX-UHFFFAOYSA-N 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- 230000008901 benefit Effects 0.000 description 11
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- ABRVDWASZFDIEH-UHFFFAOYSA-L calcium;2-hydroxy-4-methylsulfanylbutanoate Chemical compound [Ca+2].CSCCC(O)C([O-])=O.CSCCC(O)C([O-])=O ABRVDWASZFDIEH-UHFFFAOYSA-L 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 description 7
- YALHKEKUMDWQQW-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CSCCC1OCOC1=O YALHKEKUMDWQQW-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- ZDQALIYDUIRZCA-UHFFFAOYSA-N 2-tert-butyl-5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CSCCC1OC(C(C)(C)C)OC1=O ZDQALIYDUIRZCA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 6
- LJBFBDLCZLTVJF-UHFFFAOYSA-N 2-(2-methylsulfanylethyl)-1,4-dioxaspiro[4.5]decan-3-one Chemical compound O1C(=O)C(CCSC)OC11CCCCC1 LJBFBDLCZLTVJF-UHFFFAOYSA-N 0.000 description 5
- YOSPHIZGZLRVMR-UHFFFAOYSA-N 2-ethyl-2-methyl-5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CCC1(C)OC(CCSC)C(=O)O1 YOSPHIZGZLRVMR-UHFFFAOYSA-N 0.000 description 5
- IGGRDSLFGFXYJP-UHFFFAOYSA-N 2-ethyl-2-methyl-5-(2-methylsulfanylethyl)-1,3-oxazolidin-4-one Chemical compound CCC1(C)NC(=O)C(CCSC)O1 IGGRDSLFGFXYJP-UHFFFAOYSA-N 0.000 description 5
- YAFPYSRADZDBFU-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)-1,3-oxazolidine-2,4-dione Chemical compound CSCCC1OC(=O)NC1=O YAFPYSRADZDBFU-UHFFFAOYSA-N 0.000 description 5
- AODCCOKATSAQOI-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)-2-phenyl-1,3-oxazolidin-4-one Chemical compound N1C(=O)C(CCSC)OC1C1=CC=CC=C1 AODCCOKATSAQOI-UHFFFAOYSA-N 0.000 description 5
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- WWIXLTJRDZJIOK-UHFFFAOYSA-N 2-(2-methylsulfanylethyl)-1-oxa-4-azaspiro[4.5]decan-3-one Chemical compound N1C(=O)C(CCSC)OC11CCCCC1 WWIXLTJRDZJIOK-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
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- 235000010210 aluminium Nutrition 0.000 description 1
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- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- 235000010410 calcium alginate Nutrition 0.000 description 1
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
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- 238000006482 condensation reaction Methods 0.000 description 1
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- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 235000021245 dietary protein Nutrition 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical group C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002741 methionine derivatives Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005891 transamination reaction Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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
- C07D317/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007062199A DE102007062199A1 (de) | 2007-12-21 | 2007-12-21 | 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive |
| DE102007062199.1 | 2007-12-21 | ||
| PCT/EP2008/066525 WO2009080446A1 (de) | 2007-12-21 | 2008-12-01 | 2-methylthioethyl-substituierte heterocyclen als futtermitteladditive |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011509240A JP2011509240A (ja) | 2011-03-24 |
| JP2011509240A5 JP2011509240A5 (OSRAM) | 2012-01-26 |
| JP5511679B2 true JP5511679B2 (ja) | 2014-06-04 |
Family
ID=40378037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538543A Active JP5511679B2 (ja) | 2007-12-21 | 2008-12-01 | 飼料添加物としての２−メチルチオエチル置換複素環 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8158186B2 (OSRAM) |
| EP (1) | EP2222654B1 (OSRAM) |
| JP (1) | JP5511679B2 (OSRAM) |
| CN (1) | CN101903363A (OSRAM) |
| AR (1) | AR069846A1 (OSRAM) |
| BR (1) | BRPI0821237A8 (OSRAM) |
| CA (1) | CA2710170C (OSRAM) |
| DE (1) | DE102007062199A1 (OSRAM) |
| ES (1) | ES2410357T3 (OSRAM) |
| RU (1) | RU2516833C2 (OSRAM) |
| WO (1) | WO2009080446A1 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007031917A1 (de) * | 2007-07-09 | 2009-01-15 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Ketosäuren und deren Derivaten |
| DE102008042932A1 (de) | 2008-10-17 | 2010-04-22 | Evonik Degussa Gmbh | Herstellung und Verwendung von Methionylmethionin als Futtermitteladditiv für Fische und Krustentiere |
| DE102009002044A1 (de) * | 2009-03-31 | 2010-10-07 | Evonik Degussa Gmbh | Dipeptide als Futtermitteladditive |
| JP5355373B2 (ja) * | 2009-08-28 | 2013-11-27 | 株式会社日本触媒 | 熱可塑性樹脂組成物および光学フィルム |
| JP5914240B2 (ja) * | 2012-08-07 | 2016-05-11 | 株式会社トクヤマ | 多結晶シリコンの製造方法 |
| EP4615941A2 (en) * | 2022-11-11 | 2025-09-17 | Basf Se | Substituted 1,3-dioxolan-4-ones and 1,3-dioxan-4-ones as fragrance ingredients |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU162377B (OSRAM) * | 1970-05-27 | 1973-02-28 | ||
| JPS5249473B2 (OSRAM) * | 1972-08-09 | 1977-12-17 | ||
| DE2324591C2 (de) * | 1973-05-16 | 1985-12-12 | Basf Ag, 6700 Ludwigshafen | Oxazolidin-Derivate |
| US4524077A (en) * | 1983-11-14 | 1985-06-18 | Monsanto Company | Liquid 2-hydroxy-4-methylthiobutyric acid and process for the preparation thereof |
| SU1313410A1 (ru) * | 1985-04-02 | 1987-05-30 | Московская ветеринарная академия им.К.И.Скрябина | Способ откорма сельскохоз йственной птицы |
| GB9215665D0 (en) * | 1992-07-23 | 1992-09-09 | British Bio Technology | Compounds |
| US6017563A (en) | 1997-07-25 | 2000-01-25 | Novus International, Inc. | Process for optimizing milk production |
| FR2785773B1 (fr) * | 1998-11-13 | 2001-04-20 | Rhone Poulenc Nutrition Animal | Utilisation d'esters de methionine en nutrition animale |
| FR2791673B1 (fr) | 1999-04-02 | 2001-06-08 | Rhone Poulenc Animal Nutrition | Procede de preparation des esters de l'acide hydroxymethylthiobutyrique |
| WO2001058864A1 (en) | 2000-02-07 | 2001-08-16 | Rhone-Poulenc Animal Nutrition | Process for the preparation of 2-hydroxy-4-methylthio butyric acid esters |
| EP1358805A1 (en) | 2002-04-30 | 2003-11-05 | Aventis Animal Nutrition S.A. | Animal feed supplement |
| WO2004008874A1 (en) | 2002-07-19 | 2004-01-29 | Novus International, Inc. | Feed rations and methods of feeding growing ruminants |
| DE102006055470A1 (de) * | 2006-11-24 | 2008-05-29 | Evonik Degussa Gmbh | Ketomethioninketale und deren Derivate |
-
2007
- 2007-12-21 DE DE102007062199A patent/DE102007062199A1/de not_active Withdrawn
-
2008
- 2008-12-01 EP EP08865833A patent/EP2222654B1/de not_active Not-in-force
- 2008-12-01 JP JP2010538543A patent/JP5511679B2/ja active Active
- 2008-12-01 CN CN2008801222986A patent/CN101903363A/zh active Pending
- 2008-12-01 RU RU2010129556/04A patent/RU2516833C2/ru not_active IP Right Cessation
- 2008-12-01 CA CA2710170A patent/CA2710170C/en not_active Expired - Fee Related
- 2008-12-01 ES ES08865833T patent/ES2410357T3/es active Active
- 2008-12-01 WO PCT/EP2008/066525 patent/WO2009080446A1/de not_active Ceased
- 2008-12-01 BR BRPI0821237A patent/BRPI0821237A8/pt not_active IP Right Cessation
- 2008-12-19 AR ARP080105567A patent/AR069846A1/es unknown
- 2008-12-19 US US12/339,284 patent/US8158186B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2222654B1 (de) | 2013-03-20 |
| ES2410357T3 (es) | 2013-07-01 |
| US20090162474A1 (en) | 2009-06-25 |
| EP2222654A1 (de) | 2010-09-01 |
| WO2009080446A1 (de) | 2009-07-02 |
| CA2710170C (en) | 2016-03-22 |
| DE102007062199A1 (de) | 2009-06-25 |
| BRPI0821237A8 (pt) | 2016-11-08 |
| RU2010129556A (ru) | 2012-03-27 |
| JP2011509240A (ja) | 2011-03-24 |
| CN101903363A (zh) | 2010-12-01 |
| AR069846A1 (es) | 2010-02-24 |
| US8158186B2 (en) | 2012-04-17 |
| RU2516833C2 (ru) | 2014-05-20 |
| CA2710170A1 (en) | 2009-07-02 |
| BRPI0821237A2 (pt) | 2015-06-16 |
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