NO328761B1 - Fremgangsmate for a tilfore biotilgjengelig metionin for ikke-terapeutisk behandling til en ku - Google Patents
Fremgangsmate for a tilfore biotilgjengelig metionin for ikke-terapeutisk behandling til en ku Download PDFInfo
- Publication number
- NO328761B1 NO328761B1 NO20012355A NO20012355A NO328761B1 NO 328761 B1 NO328761 B1 NO 328761B1 NO 20012355 A NO20012355 A NO 20012355A NO 20012355 A NO20012355 A NO 20012355A NO 328761 B1 NO328761 B1 NO 328761B1
- Authority
- NO
- Norway
- Prior art keywords
- methionine
- ester
- cow
- stated
- ration
- Prior art date
Links
- 229930182817 methionine Natural products 0.000 title claims description 123
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 title claims description 91
- 238000000034 method Methods 0.000 title claims description 37
- 230000001225 therapeutic effect Effects 0.000 title claims description 7
- 150000002148 esters Chemical class 0.000 claims description 70
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- -1 isopropyl ester Chemical class 0.000 claims description 48
- 125000005907 alkyl ester group Chemical group 0.000 claims description 27
- 235000013336 milk Nutrition 0.000 claims description 26
- 239000008267 milk Substances 0.000 claims description 26
- 210000004080 milk Anatomy 0.000 claims description 26
- 239000013589 supplement Substances 0.000 claims description 18
- 235000013365 dairy product Nutrition 0.000 claims description 14
- 230000006872 improvement Effects 0.000 claims description 13
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 13
- 230000008901 benefit Effects 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000012141 concentrate Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000035558 fertility Effects 0.000 claims description 4
- 230000003908 liver function Effects 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 235000006109 methionine Nutrition 0.000 description 99
- 229960004452 methionine Drugs 0.000 description 97
- 241000283690 Bos taurus Species 0.000 description 64
- 210000004767 rumen Anatomy 0.000 description 31
- 210000004369 blood Anatomy 0.000 description 19
- 239000008280 blood Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 235000018102 proteins Nutrition 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- 102000004169 proteins and genes Human genes 0.000 description 9
- 235000010469 Glycine max Nutrition 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 235000005911 diet Nutrition 0.000 description 8
- 230000037213 diet Effects 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 244000068988 Glycine max Species 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- FVKIZZKHMXMSOE-QMMMGPOBSA-N (2s)-2-(butylamino)-4-methylsulfanylbutanoic acid Chemical compound CCCCN[C@H](C(O)=O)CCSC FVKIZZKHMXMSOE-QMMMGPOBSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004460 silage Substances 0.000 description 4
- AQGPJOBMCFDRBW-JTQLQIEISA-N (2S)-2-(hexylamino)-4-methylsulfanylbutanoic acid Chemical compound C(CCCCC)N[C@@H](CCSC)C(=O)O AQGPJOBMCFDRBW-JTQLQIEISA-N 0.000 description 3
- BUTMIMGUVFPEFI-INIZCTEOSA-N (2s)-2-(dodecylamino)-4-methylsulfanylbutanoic acid Chemical group CCCCCCCCCCCCN[C@H](C(O)=O)CCSC BUTMIMGUVFPEFI-INIZCTEOSA-N 0.000 description 3
- MFDKQSVENSFSEN-QFIPXVFZSA-N (2s)-4-methylsulfanyl-2-(octadecylamino)butanoic acid Chemical compound CCCCCCCCCCCCCCCCCCN[C@H](C(O)=O)CCSC MFDKQSVENSFSEN-QFIPXVFZSA-N 0.000 description 3
- SRMCAKWGHOOMDV-ZETCQYMHSA-N (2s)-4-methylsulfanyl-2-(propan-2-ylamino)butanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(C)C SRMCAKWGHOOMDV-ZETCQYMHSA-N 0.000 description 3
- XUBATEVJJZIKPI-ZETCQYMHSA-N (2s)-4-methylsulfanyl-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCSC XUBATEVJJZIKPI-ZETCQYMHSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- YDBYJHTYSHBBAU-YFKPBYRVSA-N S-methyl-L-methioninate Chemical compound C[S+](C)CC[C@H](N)C([O-])=O YDBYJHTYSHBBAU-YFKPBYRVSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- KPWCQEUBJAIORR-RGMNGODLSA-N ethyl (2s)-2-amino-4-methylsulfanylbutanoate;hydrochloride Chemical compound Cl.CCOC(=O)[C@@H](N)CCSC KPWCQEUBJAIORR-RGMNGODLSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 210000000936 intestine Anatomy 0.000 description 3
- 235000009973 maize Nutrition 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- MEVUPUNLVKELNV-JEDNCBNOSA-N methyl (2s)-2-amino-4-methylsulfanylbutanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CCSC MEVUPUNLVKELNV-JEDNCBNOSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004470 DL Methionine Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000031891 intestinal absorption Effects 0.000 description 2
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000001502 supplementing effect Effects 0.000 description 2
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 1
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000019737 Animal fat Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 239000005996 Blood meal Substances 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000012677 beetroot red Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 239000004461 grass silage Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000009027 insemination Effects 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000004140 ketosis Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000002741 methionine derivatives Chemical class 0.000 description 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
-
- 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
-
- 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
- A23K20/105—Aliphatic or alicyclic compounds
-
- 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
- A23K20/142—Amino acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Animal Husbandry (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Birds (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Fodder In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Feed For Specific Animals (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9814249A FR2785772B1 (fr) | 1998-11-13 | 1998-11-13 | Utilisation d'esters de methionine en nutrition animale |
| FR9910050A FR2785773B1 (fr) | 1998-11-13 | 1999-07-29 | Utilisation d'esters de methionine en nutrition animale |
| PCT/EP1999/009021 WO2000028835A1 (en) | 1998-11-13 | 1999-11-10 | A method for supplying bioavailable methionine to a cow |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20012355D0 NO20012355D0 (no) | 2001-05-11 |
| NO20012355L NO20012355L (no) | 2001-07-13 |
| NO328761B1 true NO328761B1 (no) | 2010-05-03 |
Family
ID=26234645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20012355A NO328761B1 (no) | 1998-11-13 | 2001-05-11 | Fremgangsmate for a tilfore biotilgjengelig metionin for ikke-terapeutisk behandling til en ku |
Country Status (25)
| Country | Link |
|---|---|
| US (6) | US6221909B1 (da) |
| EP (2) | EP1442664B1 (da) |
| JP (1) | JP4703853B2 (da) |
| KR (2) | KR100748051B1 (da) |
| CN (1) | CN1301660C (da) |
| AP (1) | AP1812A (da) |
| AR (1) | AR021264A1 (da) |
| AT (2) | ATE266323T1 (da) |
| AU (2) | AU775693B2 (da) |
| BR (2) | BR9917851B1 (da) |
| CA (1) | CA2348440C (da) |
| DE (2) | DE69917314T2 (da) |
| DK (2) | DK1442664T3 (da) |
| EA (1) | EA002558B1 (da) |
| ES (1) | ES2221486T3 (da) |
| FR (1) | FR2785773B1 (da) |
| ID (1) | ID30016A (da) |
| IL (2) | IL142955A0 (da) |
| MA (1) | MA25270A1 (da) |
| MX (1) | MXPA01004747A (da) |
| NO (1) | NO328761B1 (da) |
| NZ (1) | NZ511427A (da) |
| PT (2) | PT1442664E (da) |
| TR (1) | TR200101323T2 (da) |
| WO (1) | WO2000028835A1 (da) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP1358805A1 (en) * | 2002-04-30 | 2003-11-05 | Aventis Animal Nutrition S.A. | Animal feed supplement |
| US20040170669A1 (en) * | 2002-07-19 | 2004-09-02 | Kunkle William E. | Feed rations and methods of feeding growing ruminants |
| ES2279719B1 (es) * | 2006-01-26 | 2008-07-16 | Timac Agro España, S.A. | Nuevo activador metabolico y nutricional para las plantas. |
| EP2001460A4 (en) * | 2006-03-28 | 2011-01-12 | Novus Int Inc | COMPOSITIONS FOR PROMOTING HAIR GROWTH |
| US20070292485A1 (en) * | 2006-06-16 | 2007-12-20 | Novus International Inc. | Polyol ester compounds |
| DE102006055470A1 (de) * | 2006-11-24 | 2008-05-29 | Evonik Degussa Gmbh | Ketomethioninketale und deren Derivate |
| US7704521B2 (en) * | 2007-04-11 | 2010-04-27 | Zinpro Corporation | Rumen protected essential amino acids |
| DE102007062199A1 (de) * | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive |
| DE102009002044A1 (de) | 2009-03-31 | 2010-10-07 | Evonik Degussa Gmbh | Dipeptide als Futtermitteladditive |
| CN102549138B (zh) | 2009-06-29 | 2015-04-01 | 伊诺莱克斯投资公司 | 不含石化衍生中性氨基酸酯的阳离子型乳化剂及其组合物和方法 |
| DE102010029399A1 (de) | 2010-05-27 | 2011-12-01 | Evonik Degussa Gmbh | Cyclische Dipeptide als Futtermitteladditive |
| WO2013103598A2 (en) | 2012-01-06 | 2013-07-11 | Novus International Inc. | Sulfoxide-based surfactants |
| CA2878617A1 (en) * | 2012-07-12 | 2014-01-16 | Houston Stephen Smith | Matrix and layer compositions for protection of bioactives |
| SG11201803979PA (en) | 2015-11-12 | 2018-06-28 | Novus Int Inc | Sulfur-containing compounds as solvents |
| US11185524B2 (en) * | 2019-05-15 | 2021-11-30 | Novus International, Inc. | Means for protecting methionine hydroxy analog from rumen degradation |
| BR112022003547A2 (pt) * | 2019-09-06 | 2022-05-17 | Kemin Ind Inc | Processos para a preparação de ésteres alfa-hidróxi por esterificação de ácidos alfa-hidróxi |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU478542B2 (en) * | 1973-03-20 | 1975-09-18 | Commonwealth Scientific And Industrial Research Organisation | Supplements for grazing ruminants |
| US3952115A (en) * | 1975-04-02 | 1976-04-20 | The Procter & Gamble Company | Fortification of foodstuffs with N-acyl derivatives of sulfur-containing L-amino acid esters |
| US4388327A (en) * | 1981-10-30 | 1983-06-14 | E. I. Du Pont De Nemours & Co. | Method of increasing milk production of dairy cattle |
| US5084482A (en) * | 1990-04-10 | 1992-01-28 | The Lithox Corporation | Methods for inhibiting inflammatory ischemic, thrombotic and cholesterolemic disease response with methionine compounds |
| US5871773A (en) * | 1994-02-23 | 1999-02-16 | Ajinomoto Co., Inc. | Method for supplementing amino acid levels in ruminant animals |
| US5885610A (en) * | 1997-03-04 | 1999-03-23 | Zinpro Corporation | By-pass rumen product |
| US6017563A (en) * | 1997-07-25 | 2000-01-25 | Novus International, Inc. | Process for optimizing milk production |
| FR2785609B1 (fr) * | 1998-11-06 | 2000-12-15 | Rhone Poulenc Nutrition Animal | Procede de preparation de la methionine |
| FR2785773B1 (fr) * | 1998-11-13 | 2001-04-20 | Rhone Poulenc Nutrition Animal | Utilisation d'esters de methionine en nutrition animale |
| US6545179B2 (en) * | 2000-02-15 | 2003-04-08 | Aventis Animal Nutrition, Sa | Process for the production of methionine |
-
1999
- 1999-07-29 FR FR9910050A patent/FR2785773B1/fr not_active Expired - Lifetime
- 1999-11-10 EP EP04010767A patent/EP1442664B1/en not_active Expired - Lifetime
- 1999-11-10 KR KR1020017005853A patent/KR100748051B1/ko active IP Right Grant
- 1999-11-10 EA EA200100531A patent/EA002558B1/ru not_active IP Right Cessation
- 1999-11-10 KR KR1020067018219A patent/KR100756572B1/ko active IP Right Grant
- 1999-11-10 AT AT99972074T patent/ATE266323T1/de active
- 1999-11-10 AP APAP/P/2001/002162A patent/AP1812A/en active
- 1999-11-10 AT AT04010767T patent/ATE482627T1/de active
- 1999-11-10 IL IL14295599A patent/IL142955A0/xx not_active IP Right Cessation
- 1999-11-10 BR BRPI9917851-6B1A patent/BR9917851B1/pt active IP Right Grant
- 1999-11-10 NZ NZ511427A patent/NZ511427A/en not_active IP Right Cessation
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2001
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2002
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2003
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