RU2516833C2 - Замещенные 2-метилтиоэтилом гетероциклы в качестве добавок к кормам - Google Patents
Замещенные 2-метилтиоэтилом гетероциклы в качестве добавок к кормам Download PDFInfo
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- RU2516833C2 RU2516833C2 RU2010129556/04A RU2010129556A RU2516833C2 RU 2516833 C2 RU2516833 C2 RU 2516833C2 RU 2010129556/04 A RU2010129556/04 A RU 2010129556/04A RU 2010129556 A RU2010129556 A RU 2010129556A RU 2516833 C2 RU2516833 C2 RU 2516833C2
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- Prior art keywords
- compound
- acid
- methylthio
- ethyl
- formula
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- 239000004459 forage Substances 0.000 title abstract 3
- -1 2-methylthioethyl Chemical group 0.000 title description 11
- 239000000654 additive Substances 0.000 title description 3
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 241001465754 Metazoa Species 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 15
- 241000282849 Ruminantia Species 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 241000251468 Actinopterygii Species 0.000 claims abstract description 8
- 241000238424 Crustacea Species 0.000 claims abstract description 8
- 241000282887 Suidae Species 0.000 claims abstract description 6
- 244000144977 poultry Species 0.000 claims abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 14
- 239000007848 Bronsted acid Substances 0.000 claims description 11
- 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 compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000007517 lewis acids Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
- 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 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- 239000000126 substance Substances 0.000 abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
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- 239000000047 product Substances 0.000 description 22
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- 238000002360 preparation method Methods 0.000 description 20
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 18
- 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 17
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- 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 9
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- YALHKEKUMDWQQW-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CSCCC1OCOC1=O YALHKEKUMDWQQW-UHFFFAOYSA-N 0.000 description 6
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- 239000000969 carrier Substances 0.000 description 6
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 6
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 5
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- 235000013594 poultry meat Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PXHFLWCSJYTAFU-UHFFFAOYSA-N 1,3-oxazolidin-4-one Chemical compound O=C1COCN1 PXHFLWCSJYTAFU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 1
- SWMDCXYSYSMCJM-UHFFFAOYSA-N 2-aminopentanethioic s-acid Chemical compound CCCC(N)C(S)=O SWMDCXYSYSMCJM-UHFFFAOYSA-N 0.000 description 1
- DOLNLDKZJKDWLS-UHFFFAOYSA-N 2-hydroxypentanethioamide Chemical compound CCCC(O)C(N)=S DOLNLDKZJKDWLS-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 0 CNCCC(C(*=C)=O)O Chemical compound CNCCC(C(*=C)=O)O 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- 239000005639 Lauric acid Chemical class 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000006038 Mepron® Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229910000503 Na-aluminosilicate Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 210000003165 abomasum Anatomy 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 229940088623 biologically active substance Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 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
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000000383 hazardous chemical 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000006651 lactation Effects 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
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 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 description 1
- 238000005891 transamination reaction Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 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 (2)
| Publication Number | Publication Date |
|---|---|
| RU2010129556A RU2010129556A (ru) | 2012-03-27 |
| RU2516833C2 true RU2516833C2 (ru) | 2014-05-20 |
Family
ID=40378037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010129556/04A RU2516833C2 (ru) | 2007-12-21 | 2008-12-01 | Замещенные 2-метилтиоэтилом гетероциклы в качестве добавок к кормам |
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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU402176A3 (OSRAM) * | 1970-05-27 | 1973-10-12 | ||
| SU1313410A1 (ru) * | 1985-04-02 | 1987-05-30 | Московская ветеринарная академия им.К.И.Скрябина | Способ откорма сельскохоз йственной птицы |
| SU1428193A3 (ru) * | 1983-11-14 | 1988-09-30 | Монсанто Компани (Фирма) | Способ получени 2-окси-4-(метилтио)-масл ной кислоты |
| WO2000028835A1 (en) * | 1998-11-13 | 2000-05-25 | Aventis Animal Nutrition S.A. | A method for supplying bioavailable methionine to a cow |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5249473B2 (OSRAM) * | 1972-08-09 | 1977-12-17 | ||
| DE2324591C2 (de) * | 1973-05-16 | 1985-12-12 | Basf Ag, 6700 Ludwigshafen | Oxazolidin-Derivate |
| 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 |
| 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
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU402176A3 (OSRAM) * | 1970-05-27 | 1973-10-12 | ||
| SU1428193A3 (ru) * | 1983-11-14 | 1988-09-30 | Монсанто Компани (Фирма) | Способ получени 2-окси-4-(метилтио)-масл ной кислоты |
| SU1313410A1 (ru) * | 1985-04-02 | 1987-05-30 | Московская ветеринарная академия им.К.И.Скрябина | Способ откорма сельскохоз йственной птицы |
| WO2000028835A1 (en) * | 1998-11-13 | 2000-05-25 | Aventis Animal Nutrition S.A. | A method for supplying bioavailable methionine to a cow |
Non-Patent Citations (1)
| Title |
|---|
| Hidetoshi Tokuyama et al, Synthesis, 2002,Bd.8,p.1121-1123. * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2222654B1 (de) | 2013-03-20 |
| JP5511679B2 (ja) | 2014-06-04 |
| 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 |
| CA2710170A1 (en) | 2009-07-02 |
| BRPI0821237A2 (pt) | 2015-06-16 |
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