DE102007062199A1 - 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive - Google Patents
2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive Download PDFInfo
- Publication number
- DE102007062199A1 DE102007062199A1 DE102007062199A DE102007062199A DE102007062199A1 DE 102007062199 A1 DE102007062199 A1 DE 102007062199A1 DE 102007062199 A DE102007062199 A DE 102007062199A DE 102007062199 A DE102007062199 A DE 102007062199A DE 102007062199 A1 DE102007062199 A1 DE 102007062199A1
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- Prior art keywords
- compound
- acid
- methylthio
- formula
- ethyl
- Prior art date
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- 239000003674 animal food additive Substances 0.000 title description 10
- 125000000623 heterocyclic group Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 24
- 230000008569 process Effects 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 244000144972 livestock Species 0.000 claims abstract description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
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- 150000001728 carbonyl compounds Chemical class 0.000 claims description 14
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- 238000006243 chemical reaction Methods 0.000 claims description 13
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
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- 239000004115 Sodium Silicate Substances 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 235000013330 chicken meat Nutrition 0.000 description 1
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- 229940125773 compound 10 Drugs 0.000 description 1
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- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
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- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 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 compound 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 group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 150000002632 lipids Chemical class 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
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- 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
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- 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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007062199A DE102007062199A1 (de) | 2007-12-21 | 2007-12-21 | 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive |
| BRPI0821237A BRPI0821237A8 (pt) | 2007-12-21 | 2008-12-01 | Heterociclos substituídos-2-metil tio etila, seus usos e seus processos de produção, e mistura de alimentação para nutrição de animais de fazenda |
| CA2710170A CA2710170C (en) | 2007-12-21 | 2008-12-01 | 2-methylthioethyl-substituted heterocycles as feed additives |
| RU2010129556/04A RU2516833C2 (ru) | 2007-12-21 | 2008-12-01 | Замещенные 2-метилтиоэтилом гетероциклы в качестве добавок к кормам |
| CN2008801222986A CN101903363A (zh) | 2007-12-21 | 2008-12-01 | 作为饲料添加剂的2-甲硫基乙基-取代的杂环化合物 |
| ES08865833T ES2410357T3 (es) | 2007-12-21 | 2008-12-01 | Heterociclos sustituidos con 2-metiltioetilo en calidad de aditivos para alimentos para animales |
| PCT/EP2008/066525 WO2009080446A1 (de) | 2007-12-21 | 2008-12-01 | 2-methylthioethyl-substituierte heterocyclen als futtermitteladditive |
| JP2010538543A 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 |
| EP08865833A EP2222654B1 (de) | 2007-12-21 | 2008-12-01 | 2-methylthioethyl-substituierte heterocyclen als futtermitteladditive |
| US12/339,284 US8158186B2 (en) | 2007-12-21 | 2008-12-19 | 2-methylthioethyl-substituted heterocycles as feed additives |
| ARP080105567A AR069846A1 (es) | 2007-12-21 | 2008-12-19 | Heterociclos sustituidos con 2-metiltioetilo como aditivos de alimentos para animales |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007062199A DE102007062199A1 (de) | 2007-12-21 | 2007-12-21 | 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102007062199A1 true DE102007062199A1 (de) | 2009-06-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102007062199A Withdrawn DE102007062199A1 (de) | 2007-12-21 | 2007-12-21 | 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8158186B2 (https=) |
| EP (1) | EP2222654B1 (https=) |
| JP (1) | JP5511679B2 (https=) |
| CN (1) | CN101903363A (https=) |
| AR (1) | AR069846A1 (https=) |
| BR (1) | BRPI0821237A8 (https=) |
| CA (1) | CA2710170C (https=) |
| DE (1) | DE102007062199A1 (https=) |
| ES (1) | ES2410357T3 (https=) |
| RU (1) | RU2516833C2 (https=) |
| WO (1) | WO2009080446A1 (https=) |
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 |
| CN120202281A (zh) * | 2022-11-11 | 2025-06-24 | 巴斯夫欧洲公司 | 作为香料成分的取代的1,3-二氧戊环-4-酮和1,3-二噁烷-4-酮 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999004647A1 (en) | 1997-07-25 | 1999-02-04 | Novus International, Inc. | Process for optimizing milk production |
| WO2000028835A1 (en) | 1998-11-13 | 2000-05-25 | Aventis Animal Nutrition S.A. | A method for supplying bioavailable methionine to a cow |
| WO2000059877A1 (en) | 1999-04-02 | 2000-10-12 | Aventis Animal Nutrition S.A. | Process for the preparation of hydroxy methylthiobutyric acid esters |
| WO2001056980A1 (en) | 2000-02-07 | 2001-08-09 | Aventis Animal Nutrition S.A. | Process for the preparation of 2-hydroxy-4-methylthiobutyric 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU162377B (https=) * | 1970-05-27 | 1973-02-28 | ||
| JPS5249473B2 (https=) * | 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 |
| 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 BR BRPI0821237A patent/BRPI0821237A8/pt not_active IP Right Cessation
- 2008-12-01 WO PCT/EP2008/066525 patent/WO2009080446A1/de not_active Ceased
- 2008-12-01 CA CA2710170A patent/CA2710170C/en not_active Expired - Fee Related
- 2008-12-01 RU RU2010129556/04A patent/RU2516833C2/ru not_active IP Right Cessation
- 2008-12-01 CN CN2008801222986A patent/CN101903363A/zh active Pending
- 2008-12-01 ES ES08865833T patent/ES2410357T3/es active Active
- 2008-12-19 US US12/339,284 patent/US8158186B2/en not_active Expired - Fee Related
- 2008-12-19 AR ARP080105567A patent/AR069846A1/es unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999004647A1 (en) | 1997-07-25 | 1999-02-04 | Novus International, Inc. | Process for optimizing milk production |
| WO2000028835A1 (en) | 1998-11-13 | 2000-05-25 | Aventis Animal Nutrition S.A. | A method for supplying bioavailable methionine to a cow |
| WO2000059877A1 (en) | 1999-04-02 | 2000-10-12 | Aventis Animal Nutrition S.A. | Process for the preparation of hydroxy methylthiobutyric acid esters |
| WO2001056980A1 (en) | 2000-02-07 | 2001-08-09 | Aventis Animal Nutrition S.A. | Process for the preparation of 2-hydroxy-4-methylthiobutyric acid esters |
| 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 |
Non-Patent Citations (6)
| Title |
|---|
| European Commission: Report of the Scientific Committee an Animal Nutrition an the Use of HMBi; 25 April 2003 |
| Fond and Agriculture Organization of the United Nation (FAO) Fisheries Department "State of World Aquaculture 2006", 2006, Rome. |
| Graulet et al. ver�ffentlichte 2004 im Journal of Animal and Feed Science (269) |
| Graulet et al., J. Animal and Feed Sciences (2004), 269 |
| International Food Policy Research Institute (IFPRI) "Fish 2020: Supply and Demand in Changing Markets", 2003, Washington, D. C. |
| Loerch und Oke; "Rumen Protected Amino Acids in Ruminant Nutrition" in "Absorption and Utilization of Amino Acids" Vol. 3, 1989, 187-200, CRC Press Boca Raton, Florida |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011509240A (ja) | 2011-03-24 |
| CA2710170C (en) | 2016-03-22 |
| RU2010129556A (ru) | 2012-03-27 |
| CN101903363A (zh) | 2010-12-01 |
| BRPI0821237A2 (pt) | 2015-06-16 |
| US20090162474A1 (en) | 2009-06-25 |
| RU2516833C2 (ru) | 2014-05-20 |
| EP2222654B1 (de) | 2013-03-20 |
| ES2410357T3 (es) | 2013-07-01 |
| JP5511679B2 (ja) | 2014-06-04 |
| US8158186B2 (en) | 2012-04-17 |
| AR069846A1 (es) | 2010-02-24 |
| BRPI0821237A8 (pt) | 2016-11-08 |
| WO2009080446A1 (de) | 2009-07-02 |
| CA2710170A1 (en) | 2009-07-02 |
| EP2222654A1 (de) | 2010-09-01 |
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