CA2343116C - Methods and compositions for increasing intestinal absorption of fats - Google Patents
Methods and compositions for increasing intestinal absorption of fats Download PDFInfo
- Publication number
- CA2343116C CA2343116C CA002343116A CA2343116A CA2343116C CA 2343116 C CA2343116 C CA 2343116C CA 002343116 A CA002343116 A CA 002343116A CA 2343116 A CA2343116 A CA 2343116A CA 2343116 C CA2343116 C CA 2343116C
- Authority
- CA
- Canada
- Prior art keywords
- fatty acid
- lysophosphatidylcholine
- acid esters
- agent
- fat
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 61
- 238000000034 method Methods 0.000 title abstract description 23
- 239000003925 fat Substances 0.000 title description 27
- 230000031891 intestinal absorption Effects 0.000 title description 4
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 claims abstract description 72
- 210000000936 intestine Anatomy 0.000 claims abstract description 14
- 239000000194 fatty acid Substances 0.000 claims description 104
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 103
- 229930195729 fatty acid Natural products 0.000 claims description 103
- -1 fatty acid esters Chemical class 0.000 claims description 63
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 60
- 150000004665 fatty acids Chemical class 0.000 claims description 49
- 150000002632 lipids Chemical class 0.000 claims description 36
- 239000003795 chemical substances by application Substances 0.000 claims description 34
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 27
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 23
- 206010025476 Malabsorption Diseases 0.000 claims description 21
- 208000004155 Malabsorption Syndromes Diseases 0.000 claims description 21
- 108010058864 Phospholipases A2 Proteins 0.000 claims description 20
- 229930006000 Sucrose Natural products 0.000 claims description 20
- 239000005720 sucrose Substances 0.000 claims description 20
- 229920000223 polyglycerol Polymers 0.000 claims description 19
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 16
- 150000001840 cholesterol esters Chemical class 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000003626 triacylglycerols Chemical class 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 4
- 210000002966 serum Anatomy 0.000 claims description 4
- 102100037611 Lysophospholipase Human genes 0.000 claims 7
- 238000010521 absorption reaction Methods 0.000 abstract description 10
- 230000000968 intestinal effect Effects 0.000 abstract description 7
- 102100026918 Phospholipase A2 Human genes 0.000 description 14
- 102000015439 Phospholipases Human genes 0.000 description 9
- 108010064785 Phospholipases Proteins 0.000 description 9
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 201000003883 Cystic fibrosis Diseases 0.000 description 5
- 229910001424 calcium ion Inorganic materials 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 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 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010041969 Steatorrhoea Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001841 cholesterols Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000013367 dietary fats Nutrition 0.000 description 3
- 125000005313 fatty acid group Chemical group 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 208000001162 steatorrhea Diseases 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 101710096328 Phospholipase A2 Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
- 239000006172 buffering agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000032258 transport Effects 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 208000003807 Graves Disease Diseases 0.000 description 1
- 208000015023 Graves' disease Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 239000003833 bile salt Substances 0.000 description 1
- 229940093761 bile salts Drugs 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000001842 enterocyte Anatomy 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000036449 good health Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 235000018343 nutrient deficiency Nutrition 0.000 description 1
- 235000021231 nutrient uptake Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000006180 nutrition needs Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 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
- A61K31/66—Phosphorus compounds
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/43—Enzymes; Proenzymes; Derivatives thereof
- A61K38/46—Hydrolases (3)
- A61K38/465—Hydrolases (3) acting on ester bonds (3.1), e.g. lipases, ribonucleases
-
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
- C12Y301/01004—Phospholipase A2 (3.1.1.4)
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Gastroenterology & Hepatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9943098P | 1998-09-08 | 1998-09-08 | |
| US60/099,430 | 1998-09-08 | ||
| PCT/US1999/020427 WO2000013689A1 (en) | 1998-09-08 | 1999-09-07 | Methods and compositions for increasing intestinal absorption of fats |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2343116A1 CA2343116A1 (en) | 2000-03-16 |
| CA2343116C true CA2343116C (en) | 2008-11-18 |
Family
ID=22274976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002343116A Expired - Fee Related CA2343116C (en) | 1998-09-08 | 1999-09-07 | Methods and compositions for increasing intestinal absorption of fats |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6426069B1 (https=) |
| EP (1) | EP1119360B1 (https=) |
| JP (1) | JP4700193B2 (https=) |
| CN (1) | CN1321089A (https=) |
| AT (1) | ATE347371T1 (https=) |
| AU (1) | AU771901B2 (https=) |
| CA (1) | CA2343116C (https=) |
| DE (1) | DE69934325T2 (https=) |
| IL (2) | IL141801A0 (https=) |
| NO (1) | NO20011173L (https=) |
| NZ (1) | NZ510536A (https=) |
| WO (1) | WO2000013689A1 (https=) |
| ZA (1) | ZA200102268B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL161178A0 (en) * | 2001-10-11 | 2004-08-31 | Biomolecular Products Inc | MODIFICATIONS OF SOLID 3-sn-PHOSPHOGLYCERIDES |
| DE60238663D1 (de) | 2002-04-05 | 2011-02-03 | Nestle Sa | Zusammensetzungen und Verfahren zur Verbesserung von Lipidassimilation in Haustieren |
| DE10217555A1 (de) * | 2002-04-19 | 2004-02-19 | Degussa Bioactives Deutschland Gmbh | Physiologisch verträgliche, Phospholipid-haltige, stabile und harte Matrix |
| JP2006518384A (ja) * | 2003-01-31 | 2006-08-10 | チルドレンズ・ホスピタル・ロス・アンジエルス | 改善されたバイオアベイラビリティを有するフェンレチニドの経口組成物、およびその使用方法 |
| US7758884B2 (en) * | 2005-01-28 | 2010-07-20 | Kemin Industries, Inc. | Formulation for increasing the deposition of dietary carotenoids in eggs |
| EP1688049A1 (de) * | 2005-02-03 | 2006-08-09 | findusFit Sportdiätetika GmbH | Diätetisches Lebensmittel |
| FR2918846B1 (fr) * | 2007-07-20 | 2013-07-26 | Isl Innovation Sante Lipides | Composition alimentaire pour ameliorer la digestibilite des lipides alimentaires |
| US10463229B2 (en) * | 2010-10-22 | 2019-11-05 | Fukuoka University | Endoscopic observation method and composition for improving diagnostic performance involving applying useful white opaque substance to diagnosis of gastric epithelial tumors (adenoma or gastric cancer) |
| CA2817957C (en) * | 2010-11-15 | 2016-05-10 | Texas Tech University | Substance for increasing the production of a specific acyl-chain dihydroceramide(s) for improving the effectiveness of cancer treatments |
| AU2019342421B2 (en) * | 2018-09-21 | 2024-09-05 | Société des Produits Nestlé S.A. | Compositions and methods for treatment of exocrine pancreatic insufficiency (EPI) |
| WO2025148196A1 (zh) * | 2024-01-12 | 2025-07-17 | 小藻科技(安吉)有限公司 | 一种促进脂肪酸吸收及跨越血脑屏障的微藻提取物及其组合物的应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4874795A (en) * | 1985-04-02 | 1989-10-17 | Yesair David W | Composition for delivery of orally administered drugs and other substances |
| US4849132A (en) | 1986-05-16 | 1989-07-18 | Asahi Denka Kogyo Kabushiki Kaisha | Surfactant composition having improved functions |
| US5571517A (en) | 1990-08-13 | 1996-11-05 | Yesair; David W. | Mixed lipid-bicarbonate colloidal particles for delivering drugs or calories |
| ES2071332T3 (es) | 1990-08-13 | 1995-06-16 | David W Yesair | Particulas coloidales de lipidos mixtos-bicarbonato para administrar farmacos o calorias. |
| US5302400A (en) * | 1992-06-22 | 1994-04-12 | Digestive Care Inc. | Preparation of gastric acid-resistant microspheres containing digestive enzymes and buffered-bile acids |
| JPH08143469A (ja) * | 1994-11-14 | 1996-06-04 | Amano Pharmaceut Co Ltd | 膵外分泌機能不全症治療剤 |
| JPH11506780A (ja) * | 1995-06-06 | 1999-06-15 | バイオモレキュラー プロダクツ，インク． | 薬またはカロリー送達用の混合脂質−重炭酸塩コロイド粒子 |
| US5716814A (en) | 1996-02-02 | 1998-02-10 | Biomolecular Products, Inc. | Methods for making lysophosphatidylcholine |
| WO1998010776A1 (en) * | 1996-09-11 | 1998-03-19 | Shanahan Prendergast Elizabeth | Therapeutic formulations containing venom or venom anti-serum either alone or in combination for the therapeutic prophylaxis and therapy of neoplasms |
-
1999
- 1999-09-07 DE DE69934325T patent/DE69934325T2/de not_active Expired - Lifetime
- 1999-09-07 AU AU57052/99A patent/AU771901B2/en not_active Ceased
- 1999-09-07 NZ NZ510536A patent/NZ510536A/en not_active IP Right Cessation
- 1999-09-07 AT AT99944090T patent/ATE347371T1/de not_active IP Right Cessation
- 1999-09-07 CA CA002343116A patent/CA2343116C/en not_active Expired - Fee Related
- 1999-09-07 IL IL14180199A patent/IL141801A0/xx active IP Right Grant
- 1999-09-07 JP JP2000568497A patent/JP4700193B2/ja not_active Expired - Fee Related
- 1999-09-07 US US09/786,695 patent/US6426069B1/en not_active Expired - Lifetime
- 1999-09-07 WO PCT/US1999/020427 patent/WO2000013689A1/en not_active Ceased
- 1999-09-07 ZA ZA200102268A patent/ZA200102268B/en unknown
- 1999-09-07 CN CN99811075A patent/CN1321089A/zh active Pending
- 1999-09-07 EP EP99944090A patent/EP1119360B1/en not_active Expired - Lifetime
-
2001
- 2001-03-04 IL IL141801A patent/IL141801A/en not_active IP Right Cessation
- 2001-03-07 NO NO20011173A patent/NO20011173L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69934325D1 (de) | 2007-01-18 |
| US6426069B1 (en) | 2002-07-30 |
| WO2000013689A1 (en) | 2000-03-16 |
| ZA200102268B (en) | 2001-09-19 |
| EP1119360A4 (en) | 2003-06-04 |
| CN1321089A (zh) | 2001-11-07 |
| IL141801A (en) | 2009-02-11 |
| NO20011173D0 (no) | 2001-03-07 |
| JP4700193B2 (ja) | 2011-06-15 |
| ATE347371T1 (de) | 2006-12-15 |
| JP2002524417A (ja) | 2002-08-06 |
| NZ510536A (en) | 2003-07-25 |
| NO20011173L (no) | 2001-05-08 |
| EP1119360B1 (en) | 2006-12-06 |
| CA2343116A1 (en) | 2000-03-16 |
| EP1119360A1 (en) | 2001-08-01 |
| AU771901B2 (en) | 2004-04-08 |
| AU5705299A (en) | 2000-03-27 |
| IL141801A0 (en) | 2002-03-10 |
| DE69934325T2 (de) | 2007-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100418519C (zh) | 用于增强认知能力的含有花生四烯酸或其与二十二碳六烯酸的组合的组合物 | |
| Jensen et al. | The lipolytic triad human lingual, breast milk, and pancreatic lipases: physiological implications of their characteristics in digestion of dietary fats | |
| CA2343116C (en) | Methods and compositions for increasing intestinal absorption of fats | |
| CN101336913A (zh) | 具有预防或改善脑功能降低引起的症状或疾病的作用的组合物 | |
| KR20040004652A (ko) | 조효소 ｑ 및 에이코사펜타에노산（ｅｐａ） | |
| SK112399A3 (en) | Methods and compositions for reducing the incidence of necrotizing enterocolitis | |
| JPH08193028A (ja) | ヘリコバクターの阻害 | |
| WO2008149177A2 (en) | Marine lipid compositions and uses thereof | |
| JPH08500332A (ja) | 炎症性疾患の治療のための非経口的に投与される医薬を調製するためのエマルジョンの使用 | |
| JP3467794B2 (ja) | 学習能向上剤 | |
| Hayes et al. | Review of triacylglycerol digestion, absorption, and metabolism with respect to SALATRIM triacylglycerols | |
| Nishimukai et al. | Enteral administration of soyabean lecithin enhanced lymphatic absorption of triacylglycerol in rats | |
| EP1106181A1 (en) | Nutritional compositions for preventing or treating hyperlipoproteinemia | |
| CN1345188A (zh) | 含七碳脂肪酸甘油三酯的营养补充剂或药物制剂 | |
| US7842679B2 (en) | Phospholipid derivatives of DHA and methods for treating respiratory failure using the same | |
| US4626527A (en) | Process for utilizing choline to sustain muscular performance | |
| Tamargo et al. | Pharmacokinetics and safety profile of omega-3 polyunsaturated fatty acids | |
| CN118416114A (zh) | 一种促进脂肪酸吸收及跨越血脑屏障的微藻提取物及其组合物的应用 | |
| Chen et al. | Docosahexaenoic acid-containing phospholipids and triglycerides based nutritional supplements | |
| US20200085774A1 (en) | Omega-3 Fatty Acid Composition for Preventing and/or Treating Cachexia | |
| JP5158715B2 (ja) | 平滑筋収縮抑制剤 | |
| US20030032672A1 (en) | Method for preparing a conjugated linoleic acid-containing structured lipid and use of the same | |
| JPS62111926A (ja) | コリン作働性神経系活性化剤 | |
| Staggers | Lipid digestion and absorption in the suckling rat. | |
| British Nutrition Foundation | Digestion of Lipids to Unsaturated Fatty Acids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150908 |