CA2269674A1 - Method for controlling body fat and/or body weight in animals and pharmaceutical compositions for use therein - Google Patents
Method for controlling body fat and/or body weight in animals and pharmaceutical compositions for use therein Download PDFInfo
- Publication number
- CA2269674A1 CA2269674A1 CA002269674A CA2269674A CA2269674A1 CA 2269674 A1 CA2269674 A1 CA 2269674A1 CA 002269674 A CA002269674 A CA 002269674A CA 2269674 A CA2269674 A CA 2269674A CA 2269674 A1 CA2269674 A1 CA 2269674A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- eicosadienoic
- conjugated
- eicosadienoic acid
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 241001465754 Metazoa Species 0.000 title claims abstract description 18
- 210000000577 adipose tissue Anatomy 0.000 title claims abstract description 14
- 230000037396 body weight Effects 0.000 title claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 18
- 239000000194 fatty acid Substances 0.000 claims abstract description 18
- 229930195729 fatty acid Natural products 0.000 claims abstract description 18
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 18
- 108010013563 Lipoprotein Lipase Proteins 0.000 claims abstract description 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 3
- 102100022119 Lipoprotein lipase Human genes 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 19
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 claims description 17
- 235000021297 Eicosadienoic acid Nutrition 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- UNFHLCKMPAPDAZ-UHFFFAOYSA-N icosa-11,13-dienoic acid Chemical group CCCCCCC=CC=CCCCCCCCCCC(O)=O UNFHLCKMPAPDAZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- JMNOXACVZSHIGZ-UHFFFAOYSA-N icosa-12,14-dienoic acid Chemical compound CCCCCC=CC=CCCCCCCCCCCC(O)=O JMNOXACVZSHIGZ-UHFFFAOYSA-N 0.000 claims description 5
- MTNWQVQXYXBHKL-ZYIZXDEASA-N (5e,8e,12e,14e)-icosa-5,8,12,14-tetraenoic acid Chemical compound CCCCC\C=C\C=C\CC\C=C\C\C=C\CCCC(O)=O MTNWQVQXYXBHKL-ZYIZXDEASA-N 0.000 claims description 4
- 210000001789 adipocyte Anatomy 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- IJAXPCZCTKDWBJ-VAGPFTOWSA-N (5e,8e,11e,13e)-icosa-5,8,11,13-tetraenoic acid Chemical compound CCCCCC\C=C\C=C\C\C=C\C\C=C\CCCC(O)=O IJAXPCZCTKDWBJ-VAGPFTOWSA-N 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- XSXIVVZCUAHUJO-UHFFFAOYSA-N Homo-gamma-linoleic acid Natural products CCCCCC=CCC=CCCCCCCCCCC(O)=O XSXIVVZCUAHUJO-UHFFFAOYSA-N 0.000 claims description 3
- OXTMLVRNMWIZNR-UHFFFAOYSA-N icosa-8,11,13-trienoic acid Chemical compound CCCCCCC=CC=CCC=CCCCCCCC(O)=O OXTMLVRNMWIZNR-UHFFFAOYSA-N 0.000 claims description 3
- ZSWYXLJIFJJAFJ-UHFFFAOYSA-N icosa-8,12,14-trienoic acid Chemical compound CCCCCC=CC=CCCC=CCCCCCCC(O)=O ZSWYXLJIFJJAFJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- GKJZMAHZJGSBKD-UHFFFAOYSA-N (10E,12E)-Octadeca-9,11-dienoic acid Natural products CCCCCC=CC=CCCCCCCCCC(O)=O GKJZMAHZJGSBKD-UHFFFAOYSA-N 0.000 claims 1
- GKJZMAHZJGSBKD-BLHCBFLLSA-N (10e,12e)-octadeca-10,12-dienoic acid Chemical compound CCCCC\C=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-BLHCBFLLSA-N 0.000 claims 1
- GKJZMAHZJGSBKD-ANYPYVPJSA-N 10-trans-12-cis-linoleic acid Natural products CCCCCC=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-ANYPYVPJSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical compound CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006317 isomerization reaction Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000002255 enzymatic effect Effects 0.000 description 6
- 230000003228 microsomal effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 231100000252 nontoxic Toxicity 0.000 description 6
- 230000003000 nontoxic effect Effects 0.000 description 6
- 102000043296 Lipoprotein lipases Human genes 0.000 description 5
- 241000282887 Suidae Species 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 239000002775 capsule Substances 0.000 description 4
- 230000002354 daily effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 235000019626 lipase activity Nutrition 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 235000013372 meat Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 235000020940 control diet Nutrition 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000021003 saturated fats Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- QZGIOJSVUOCUMC-YTXTXJHMSA-N (2e,4e)-octa-2,4-dienoic acid Chemical compound CCC\C=C\C=C\C(O)=O QZGIOJSVUOCUMC-YTXTXJHMSA-N 0.000 description 1
- -1 8,12,13-eicosatrienoic acid Chemical compound 0.000 description 1
- OYHQOLUKZRVURQ-UHFFFAOYSA-N 9,12-Octadecadienoic Acid Chemical compound CCCCCC=CCC=CCCCCCCCC(O)=O OYHQOLUKZRVURQ-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 102000005870 Coenzyme A Ligases Human genes 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 102000004195 Isomerases Human genes 0.000 description 1
- 108090000769 Isomerases Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 108010011449 Long-chain-fatty-acid-CoA ligase Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 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
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 235000001916 dieting Nutrition 0.000 description 1
- 230000037228 dieting effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 235000006486 human diet Nutrition 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 210000000229 preadipocyte Anatomy 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000001993 wax Substances 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/759,496 US5855917A (en) | 1996-12-04 | 1996-12-04 | Method for controlling body fat and/or body weight in animals and pharmaceutical compositions for use therein comprising 20-carbon conjugated unsaturated fatty acids |
| US08/759,496 | 1996-12-04 | ||
| PCT/US1997/022192 WO1998024422A2 (en) | 1996-12-04 | 1997-12-03 | Method for controlling body fat and/or body weight in animals and pharmaceutical compositions for use therein |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2269674A1 true CA2269674A1 (en) | 1998-06-11 |
Family
ID=25055871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002269674A Abandoned CA2269674A1 (en) | 1996-12-04 | 1997-12-03 | Method for controlling body fat and/or body weight in animals and pharmaceutical compositions for use therein |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5855917A (enExample) |
| EP (1) | EP0942717A2 (enExample) |
| JP (1) | JP2001505579A (enExample) |
| AU (1) | AU5592698A (enExample) |
| CA (1) | CA2269674A1 (enExample) |
| WO (1) | WO1998024422A2 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6160141A (en) * | 1997-02-18 | 2000-12-12 | Seidel; Michael C. | Synthesis of conjugated eicosadienoic acid |
| DE69934627T2 (de) | 1998-03-17 | 2007-10-25 | Natural Asa | Konjugierte Linolsäurezusammensetzung |
| US6015833A (en) * | 1998-03-17 | 2000-01-18 | Conlinco., Inc. | Conjugated linoleic acid compositions |
| US7776353B1 (en) | 1998-03-17 | 2010-08-17 | Aker Biomarine Asa | Conjugated linoleic acid compositions |
| US7078051B1 (en) | 1998-08-11 | 2006-07-18 | Natural Asa | Conjugated linoleic acid alkyl esters in feedstuffs and food |
| US6696584B2 (en) | 1998-05-04 | 2004-02-24 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
| MX228618B (es) | 1998-05-04 | 2005-06-21 | Conlinco Inc | Metodos para utilizar composiciones de acido linoleico conjugado enriquecidas por isomeros. |
| US6214372B1 (en) | 1998-05-04 | 2001-04-10 | Con Lin Co., Inc. | Method of using isomer enriched conjugated linoleic acid compositions |
| US7101914B2 (en) * | 1998-05-04 | 2006-09-05 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
| US6060514A (en) * | 1998-05-04 | 2000-05-09 | Conlin Co., Inc. | Isomer enriched conjugated linoleic acid compositions |
| WO2000009118A1 (en) | 1998-08-13 | 2000-02-24 | The Wistar Institute | Methods for reducing atherosclerotic plaques |
| US6071544A (en) * | 1999-04-01 | 2000-06-06 | The Iams Company | Dietary compositions and method for promoting healthy weight loss cats |
| US7947737B1 (en) | 1999-09-30 | 2011-05-24 | Aker Biomarine Asa | Method of treating hypertension and reducing serum lipase activity |
| CA2404799C (en) * | 2000-04-06 | 2007-08-07 | Conlinco, Inc. | Conjugated linoleic acid compositions |
| US20030149288A1 (en) * | 2000-04-18 | 2003-08-07 | Natural Asa | Conjugated linoleic acid powder |
| US6756405B2 (en) | 2000-04-18 | 2004-06-29 | Natural Asa | Conjugated linoleic acid powder |
| US6380409B1 (en) * | 2000-04-24 | 2002-04-30 | Conlin Co., Inc. | Methods for preparing CLA isomers |
| DE10044846A1 (de) * | 2000-09-11 | 2002-04-04 | Guenther Beisel | Mittel mit verlängerter Magenverweilzeit zur Erzeugung eines langanhaltenden Sättigungseffektes sowie dessen Verwendung |
| CN1665566A (zh) * | 2000-09-21 | 2005-09-07 | 营养21公司 | 用铬络合物、共轭脂肪酸和 /或共轭脂肪醇治疗糖尿病、减少身体脂肪、改善胰岛素敏感性、缓解高血糖症和高胆固醇血症的方法和组合物 |
| US6869766B2 (en) * | 2000-12-22 | 2005-03-22 | The Regents Of The University Of California | Gene associated with regulation of adiposity and insulin response |
| US6395782B1 (en) | 2001-03-02 | 2002-05-28 | Wisconsin Alumni Research Foundation | Method of increasing longevity and preventing body weight wasting in autoimmune disease by using conjugated linoleic acid |
| US6479683B1 (en) | 2001-03-06 | 2002-11-12 | Ag Processing Inc | Process for conjugating fatty acid esters |
| JP2002265360A (ja) * | 2001-03-06 | 2002-09-18 | Asahi Denka Kogyo Kk | 中性脂肪低減剤 |
| DE10131188B4 (de) * | 2001-05-03 | 2005-06-16 | Coletica, S.A. | Verfahren zum Testen einer Substanz, die potentiell auf dem Gebiet der Lipolyse wirksam ist, und die hauptsächliche kosmetische Verwendung hiervon |
| FR2824334B1 (fr) * | 2001-05-03 | 2003-10-10 | Coletica | Procede pour tester une substance eventuellement active dans le domaine de la lipolyse et son utilisation principalement cosmetique |
| CA2448241A1 (en) * | 2001-05-31 | 2002-12-05 | Wisconsin Alumni Research Foundation | Conjugated nonadecadienoic acid compositions |
| US6677470B2 (en) | 2001-11-20 | 2004-01-13 | Natural Asa | Functional acylglycerides |
| JP4600969B2 (ja) * | 2002-01-22 | 2010-12-22 | マース インコーポレーテッド | 肥満動物のための体重管理システム |
| US20030138547A1 (en) * | 2002-01-22 | 2003-07-24 | Mars, Incorporated | Weight management system for animals |
| US6743931B2 (en) | 2002-09-24 | 2004-06-01 | Natural Asa | Conjugated linoleic acid compositions |
| JP2006519229A (ja) * | 2003-02-13 | 2006-08-24 | アルバート・アインシュタイン・カレッジ・オヴ・メディシン・オヴ・イェシヴァ・ユニヴァーシティ | 視床下部内の長鎖脂肪アシルＣｏＡレベルの変調による摂食量およびグルコース産生量の調節 |
| US7091369B2 (en) * | 2003-07-15 | 2006-08-15 | Board Of Trustees Operating Michigan State University | Synthesis of polyconjugated fatty acids |
| WO2006041922A2 (en) * | 2004-10-08 | 2006-04-20 | Dara Biosciences, Inc. | Agents and methods for administration to the central nervous system |
| US20070026079A1 (en) * | 2005-02-14 | 2007-02-01 | Louis Herlands | Intranasal administration of modulators of hypothalamic ATP-sensitive potassium channels |
| WO2009058799A1 (en) * | 2007-11-01 | 2009-05-07 | Wake Forest University School Of Medicine | Compositions and methods for prevention and treatment of mammalian diseases |
| US8343753B2 (en) * | 2007-11-01 | 2013-01-01 | Wake Forest University School Of Medicine | Compositions, methods, and kits for polyunsaturated fatty acids from microalgae |
| GB201522296D0 (en) | 2015-12-17 | 2016-02-03 | Mars Inc | Food product to reduce body fat |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3291816A (en) * | 1963-10-02 | 1966-12-13 | Leo A Goldblatt | Dehydration of lesquerolates |
| US3645822A (en) * | 1969-01-31 | 1972-02-29 | Dow Chemical Co | Method for providing multilayer films having improved slip properties |
| US4273763A (en) * | 1978-01-23 | 1981-06-16 | Efamol Limited | Pharmaceutical and dietary compositions |
| US4761425A (en) * | 1983-12-27 | 1988-08-02 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
| US4560514A (en) * | 1984-05-04 | 1985-12-24 | Bengt Samuelsson | Inflammatory lipoxin A and anti-anflammatory lipoxin B compounds |
| US5079261A (en) * | 1989-04-28 | 1992-01-07 | Brigham And Women's Hospital | Use of lipoxin a4 and its derivatives as antagonists for slow-reacting substances of anaphylaxis |
| JPH0324018A (ja) * | 1989-06-22 | 1991-02-01 | Tosoh Corp | 脂質代謝改善剤 |
| JPH0394655A (ja) * | 1989-09-06 | 1991-04-19 | Otsuka Pharmaceut Co Ltd | 栄養補給用組成物 |
| JPH0591886A (ja) * | 1991-09-30 | 1993-04-16 | Suntory Ltd | ８，１１−エイコサジエン酸及びこれを含有する脂質の製造方法 |
| JP3354582B2 (ja) * | 1991-09-30 | 2002-12-09 | サントリー株式会社 | オメガ９系高度不飽和脂肪酸およびこれを含有する脂質の製造方法 |
| US5504114A (en) * | 1992-04-29 | 1996-04-02 | Wisconsin Alumni Research Foundation | Method for controlling bird populations |
| US5554646A (en) * | 1992-04-29 | 1996-09-10 | Wisconsin Alumni Research Foundation | Method for reducing body fat in animals |
| US5569677A (en) * | 1995-06-05 | 1996-10-29 | Smithkline Beecham Corporation | Diphenyl-2-propenoates for treating diseases associated with leukotriene B4 |
| US5789441A (en) | 1996-02-15 | 1998-08-04 | Virocell Inc. | Leukotriene B4 as an antiviral and anti-neoplastic agent |
-
1996
- 1996-12-04 US US08/759,496 patent/US5855917A/en not_active Expired - Lifetime
-
1997
- 1997-12-03 WO PCT/US1997/022192 patent/WO1998024422A2/en not_active Ceased
- 1997-12-03 EP EP97952278A patent/EP0942717A2/en not_active Withdrawn
- 1997-12-03 CA CA002269674A patent/CA2269674A1/en not_active Abandoned
- 1997-12-03 JP JP52577898A patent/JP2001505579A/ja not_active Ceased
- 1997-12-03 AU AU55926/98A patent/AU5592698A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001505579A (ja) | 2001-04-24 |
| EP0942717A2 (en) | 1999-09-22 |
| WO1998024422A2 (en) | 1998-06-11 |
| AU5592698A (en) | 1998-06-29 |
| US5855917A (en) | 1999-01-05 |
| WO1998024422A3 (en) | 1998-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5855917A (en) | Method for controlling body fat and/or body weight in animals and pharmaceutical compositions for use therein comprising 20-carbon conjugated unsaturated fatty acids | |
| James et al. | Dietary polyunsaturated fatty acids and inflammatory mediator production | |
| Tahin et al. | The fatty acid composition of subcellular membranes of rat liver, heart, and brain: diet‐induced modifications | |
| CA2289648C (en) | Conjugated linoleic acid compositions | |
| Chamruspollert et al. | Transfer of dietary conjugated linoleic acid to egg yolks of chickens | |
| Raes et al. | Effect of double-muscling in Belgian Blue young bulls on the intramuscular fatty acid composition with emphasis on conjugated linoleic acid and polyunsaturated fatty acids | |
| US5804210A (en) | Methods of treating animals to maintain or enhance bone mineral content and compositions for use therein | |
| Shantha et al. | A RESEARCH NOTE CONJUGATED LINOLEIC ACID CONCENTRATION IN SEMIMEMBRANOSUS MUSCLE OF GRASS‐AND GRAIN‐FED AND ZERANOL‐IMPLANTED BEEF CATTLE 1 | |
| JP2015044810A (ja) | 異性体濃縮共役リノール酸組成物の使用方法 | |
| JPH08501777A (ja) | 総コレステロールおよび低密度リポタンパク質コレステロールの血中レベルを減少させる方法 | |
| EP1166652A1 (en) | Utilization of material containing docosapentaenoic acid | |
| KR20040030787A (ko) | 다중 불포화 지방산 함유 트라이글리세라이드를 포함하는 지방의 제조 방법 | |
| US20070015795A1 (en) | Composition comprising protein material and compounds comprising non-oxidizable fatty acid entities | |
| EP1037624B1 (en) | Use of conjugated linoleic acid for treating type ii diabetes | |
| US6077525A (en) | Use of conjugated linoleic acids | |
| AU2001257627B2 (en) | Methods for preparing cla isomers | |
| Terroine | Physiology and biochemistry of biotin | |
| JP2002188096A (ja) | 新規なグリセリドおよびその製造法並びにその用途 | |
| US7078051B1 (en) | Conjugated linoleic acid alkyl esters in feedstuffs and food | |
| Cleland et al. | Inhibition of human neutrophil leukotriene B4 synthesis in essential fatty acid deficiency: role of leukotriene A hydrolase | |
| Reber et al. | Absorption and metabolism of 1‐14C‐hydroxy octadecadienoate in the rat | |
| KR19990073078A (ko) | 공역화리놀레인산(ｃｌａ)을함유한사료조성물 | |
| Loï et al. | Effects of three trans isomers of eicosapentaenoic acid on rat platelet aggregation and arachidonic acid metabolism | |
| JP2005179264A (ja) | 体重増加抑制剤 | |
| US20030032672A1 (en) | Method for preparing a conjugated linoleic acid-containing structured lipid and use of the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |