CA2285242C - Mixture of primary fatty acids obtained from sugar cane wax - Google Patents
Mixture of primary fatty acids obtained from sugar cane wax Download PDFInfo
- Publication number
- CA2285242C CA2285242C CA002285242A CA2285242A CA2285242C CA 2285242 C CA2285242 C CA 2285242C CA 002285242 A CA002285242 A CA 002285242A CA 2285242 A CA2285242 A CA 2285242A CA 2285242 C CA2285242 C CA 2285242C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- group
- fatty acids
- mixture
- mixtures
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 47
- 239000000194 fatty acid Substances 0.000 title claims abstract description 47
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 47
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 46
- 240000000111 Saccharum officinarum Species 0.000 title claims abstract description 21
- 235000007201 Saccharum officinarum Nutrition 0.000 title claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 208000007107 Stomach Ulcer Diseases 0.000 claims abstract description 13
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- 238000007127 saponification reaction Methods 0.000 claims description 10
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 208000007536 Thrombosis Diseases 0.000 claims description 8
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 238000000956 solid--liquid extraction Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 5
- 229960001701 chloroform Drugs 0.000 claims description 5
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 5
- 239000003826 tablet Substances 0.000 claims description 5
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 claims description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 108010010803 Gelatin Proteins 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000008273 gelatin Substances 0.000 claims description 2
- 229920000159 gelatin Polymers 0.000 claims description 2
- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 239000011707 mineral Chemical class 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 230000009286 beneficial effect Effects 0.000 claims 14
- 238000001953 recrystallisation Methods 0.000 claims 10
- IHEJEKZAKSNRLY-UHFFFAOYSA-N Acido n-nonacosanoico Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O IHEJEKZAKSNRLY-UHFFFAOYSA-N 0.000 claims 8
- ONLMUMPTRGEPCH-UHFFFAOYSA-N Hentriacontanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O ONLMUMPTRGEPCH-UHFFFAOYSA-N 0.000 claims 8
- UTGPYHWDXYRYGT-UHFFFAOYSA-N Tetratriacontanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTGPYHWDXYRYGT-UHFFFAOYSA-N 0.000 claims 8
- 238000000605 extraction Methods 0.000 claims 8
- LRKATBAZQAWAGV-UHFFFAOYSA-N hexatriacontanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O LRKATBAZQAWAGV-UHFFFAOYSA-N 0.000 claims 8
- ICAIHSUWWZJGHD-UHFFFAOYSA-N n-dotriacontanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O ICAIHSUWWZJGHD-UHFFFAOYSA-N 0.000 claims 8
- XMHIUKTWLZUKEX-UHFFFAOYSA-N n-hexacosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 claims 8
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 claims 8
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 claims 8
- 239000006186 oral dosage form Substances 0.000 claims 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 6
- HVUCKZJUWZBJDP-UHFFFAOYSA-N Ceroplastic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O HVUCKZJUWZBJDP-UHFFFAOYSA-N 0.000 claims 4
- HQRWEDFDJHDPJC-UHFFFAOYSA-N Psyllic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O HQRWEDFDJHDPJC-UHFFFAOYSA-N 0.000 claims 4
- 230000008929 regeneration Effects 0.000 claims 4
- 238000011069 regeneration method Methods 0.000 claims 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 2
- GQDSSPVCELQEFY-UHFFFAOYSA-N phenol;1,4-xylene Chemical compound OC1=CC=CC=C1.CC1=CC=C(C)C=C1 GQDSSPVCELQEFY-UHFFFAOYSA-N 0.000 claims 2
- 229920002261 Corn starch Polymers 0.000 claims 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000008120 corn starch Substances 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 229940057948 magnesium stearate Drugs 0.000 claims 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims 1
- 239000008108 microcrystalline cellulose Substances 0.000 claims 1
- 229940016286 microcrystalline cellulose Drugs 0.000 claims 1
- 239000006201 parenteral dosage form Substances 0.000 claims 1
- 230000001172 regenerating effect Effects 0.000 claims 1
- 235000015424 sodium Nutrition 0.000 claims 1
- 229940033134 talc Drugs 0.000 claims 1
- 235000012222 talc Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 13
- 239000003146 anticoagulant agent Substances 0.000 abstract description 7
- 230000002785 anti-thrombosis Effects 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 230000002253 anti-ischaemic effect Effects 0.000 abstract description 5
- 230000000871 hypocholesterolemic effect Effects 0.000 abstract description 3
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 230000000702 anti-platelet effect Effects 0.000 abstract description 2
- 238000011282 treatment Methods 0.000 description 29
- 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 18
- 239000001993 wax Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 230000008569 process Effects 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 13
- 239000007787 solid Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000002496 gastric effect Effects 0.000 description 9
- 235000012000 cholesterol Nutrition 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 230000037396 body weight Effects 0.000 description 7
- 108010028554 LDL Cholesterol Proteins 0.000 description 6
- -1 aliphatic alcohols Chemical class 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 108010023302 HDL Cholesterol Proteins 0.000 description 4
- 238000000585 Mann–Whitney U test Methods 0.000 description 4
- 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 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000003304 gavage Methods 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 229940127218 antiplatelet drug Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229940032007 methylethyl ketone Drugs 0.000 description 3
- 238000007474 nonparametric Mann- Whitney U test Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229960001412 pentobarbital Drugs 0.000 description 3
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 210000001015 abdomen Anatomy 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- 235000019994 cava Nutrition 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 201000005917 gastric ulcer Diseases 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000220479 Acacia Species 0.000 description 1
- 241001502050 Acis Species 0.000 description 1
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 1
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 1
- 108010010234 HDL Lipoproteins Proteins 0.000 description 1
- 102000015779 HDL Lipoproteins Human genes 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 235000005318 Serenoa repens Nutrition 0.000 description 1
- 240000006661 Serenoa repens Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 239000012164 animal wax Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 229940127217 antithrombotic drug Drugs 0.000 description 1
- 239000003699 antiulcer agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 239000003114 blood coagulation factor Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000020931 dietary conditions Nutrition 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- DVSZKTAMJJTWFG-UHFFFAOYSA-N docosa-2,4,6,8,10,12-hexaenoic acid Chemical class CCCCCCCCCC=CC=CC=CC=CC=CC=CC(O)=O DVSZKTAMJJTWFG-UHFFFAOYSA-N 0.000 description 1
- FPRKGXIOSIUDSE-UHFFFAOYSA-N docosa-2,4,6,8-tetraenoic acid Chemical class CCCCCCCCCCCCCC=CC=CC=CC=CC(O)=O FPRKGXIOSIUDSE-UHFFFAOYSA-N 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid ester group Chemical group C(CCCCCCCCCCC)(=O)O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 150000002192 fatty aldehydes Chemical class 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940012843 omega-3 fatty acid Drugs 0.000 description 1
- 239000006014 omega-3 oil Substances 0.000 description 1
- 239000008184 oral solid dosage form Substances 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 235000013311 vegetables 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
- A61K31/185—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
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CU1997035A CU22723A1 (es) | 1997-04-02 | 1997-04-02 | Mezcla de ácidos grasos primarios de alto peso molecular obtenidos de la cera de cana de azúcar y sus usos farmacéuticos |
| CU35/97 | 1997-04-02 | ||
| PCT/IB1998/000870 WO1998043631A1 (en) | 1997-04-02 | 1998-04-01 | Mixture of primary fatty acids obtained from sugar cane wax |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2285242A1 CA2285242A1 (en) | 1998-10-08 |
| CA2285242C true CA2285242C (en) | 2008-12-16 |
Family
ID=5459247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002285242A Expired - Lifetime CA2285242C (en) | 1997-04-02 | 1998-04-01 | Mixture of primary fatty acids obtained from sugar cane wax |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6486205B2 (enExample) |
| EP (1) | EP0969827B1 (enExample) |
| JP (2) | JP4907750B2 (enExample) |
| CN (1) | CN1230158C (enExample) |
| AR (1) | AR016054A1 (enExample) |
| AT (1) | ATE233087T1 (enExample) |
| AU (1) | AU732045B2 (enExample) |
| BR (1) | BR9808470A (enExample) |
| CA (1) | CA2285242C (enExample) |
| CO (1) | CO4940484A1 (enExample) |
| CU (1) | CU22723A1 (enExample) |
| DE (1) | DE69811643T2 (enExample) |
| DK (1) | DK0969827T3 (enExample) |
| ES (1) | ES2192769T3 (enExample) |
| MY (1) | MY120318A (enExample) |
| PT (1) | PT969827E (enExample) |
| RU (1) | RU2217130C2 (enExample) |
| WO (1) | WO1998043631A1 (enExample) |
| ZA (1) | ZA982744B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4666705B2 (ja) * | 1999-12-07 | 2011-04-06 | 三井製糖株式会社 | 消化管潰瘍予防剤または改善剤 |
| US20030203854A1 (en) * | 2002-04-23 | 2003-10-30 | Ivo Pischel | Composition for effecting serum cholesterol levels |
| PT1515714E (pt) * | 2002-06-17 | 2009-10-06 | Medestea Res & Production S P | Compostos oxigenados insaturados de cadeia longa e sua utilização no campo terapêutico, cosmético e nutracêutico |
| US20050074443A1 (en) * | 2003-10-03 | 2005-04-07 | Treadwell Benjamin V. | Methods of attenuating autoimmune disease and compositions useful therefor |
| US20060013842A1 (en) * | 2004-07-15 | 2006-01-19 | Matkin John R | Natural mixture of long-chain fatty alcohols and long-chain fatty acids, its obtension from animal and vegetable waxes and its nutraceutical uses |
| US7542034B2 (en) * | 2004-09-23 | 2009-06-02 | Conversion Works, Inc. | System and method for processing video images |
| KR100723950B1 (ko) * | 2005-01-04 | 2007-05-31 | 주식회사 하이폭시 | 벼과 식물 추출물을 포함하는 허혈성 질환 및 퇴행성뇌질환의 예방 및 치료를 위한 조성물 |
| KR100685681B1 (ko) * | 2005-07-26 | 2007-02-26 | 전북대학교산학협력단 | 수수에서 폴리코사놀 또는 옥타코사놀 함량이 높은긴사슬지방을 제조하는 방법 |
| TW200730518A (en) * | 2005-10-12 | 2007-08-16 | Sicor Inc | Crystalline forms of docetaxel and processes for their preparation |
| US20070295326A1 (en) * | 2006-06-07 | 2007-12-27 | Rafael Almagro | Method for obtaining long chain aliphatic alcohols and fatty acids from sugar cane mud and related wax esters |
| US20080207748A1 (en) * | 2007-02-22 | 2008-08-28 | Innovation Labs, Inc. | Vitamin c preparation |
| DE102010052789A1 (de) * | 2010-11-27 | 2012-05-31 | Wachs-Chemie Elsteraue E.K. | Herstellung und Reinigung von PC-Wachs und deren technische Anwendungen |
| IT201700089258A1 (it) | 2017-08-02 | 2019-02-02 | Pharmanutra S P A | Composizione per uso nella prevenzione e nel trattamento di carenza di ferro |
| KR102429853B1 (ko) * | 2017-11-30 | 2022-08-05 | (주)아모레퍼시픽 | 천연 왁스를 이용한 지방산 조성물 제조방법 및 그에 따라 제조된 지방산 조성물 |
| IT201900007326A1 (it) | 2019-05-27 | 2020-11-27 | Alesco Srl | Composizioni comprendenti acidi grassi cetilati e loro uso nel trattamento di artriti e stati infiammatori articolari |
| IT201900007311A1 (it) | 2019-05-27 | 2020-11-27 | Alesco Srl | Procedimento per la preparazione di una composizione comprendente acidi grassi cetilati |
| IT201900007329A1 (it) * | 2019-05-27 | 2020-11-27 | Alesco Srl | Composizioni comprendenti acidi grassi cetilati per uso nel trattamento della mucosa gastrica, diabete e alti livelli di glicemia |
| CU24638B1 (es) * | 2020-02-03 | 2023-01-16 | Centro Nac De Investigaciones Cientificas | Suspensión oral con efecto antiulceroso y quimioprotector sobre el cáncer de colon |
| CU24732B1 (es) * | 2021-07-13 | 2025-02-07 | Centro Nac De Investigaciones Cientificas | Mezcla de compuestos con altos pesos moleculares, obtenida a partir de la cera de caña de azúcar (saccharum officinarum l.) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5160207A (en) * | 1974-11-22 | 1976-05-26 | Dai Ichi Kogyo Seiyaku Co Ltd | Shibosanto kokyuarukooruno bunriho |
| JPH0610146B2 (ja) * | 1985-10-12 | 1994-02-09 | 住友精化株式会社 | 直鎖第１級脂肪族高級アルコ−ルの抽出法 |
| CA2044162A1 (fr) * | 1989-10-13 | 1991-04-14 | Jacques Borg | Derives des alcools gras a longue chaine, leurs applications, notamment en tant que molecules cytotrophes et cytoprotectrices, et compositions pharmaceutiques les contenant |
| CU22225A1 (es) * | 1990-11-30 | 1995-01-31 | Cent Nac Investig Scient | Composicion farmacautica que contiene mezcla de alcoholes alifaticos primarios superiores para el tratamiento de hipercolesterolemia y la hiperlipoproteinemia tipo ii asi como estimulante de la conducta sexual en animales y humanos |
| CU22229A1 (es) * | 1992-09-29 | 1996-01-31 | Dalmer Lab Sa | Policosanol, una mezcla de alcoholes alifaticos primarios superiores para hipergregabilidad plaquetaria, los accidentes isquemicos, trombosis e incluso efectividad contra ulceras gastricas quimicamente inducidas y su proceso de obtencion de la caña de azucar. el tratamiento de complicaciones ateroscleroticas tales como la |
| JPH06122892A (ja) * | 1992-10-09 | 1994-05-06 | Nippon Petrochem Co Ltd | 粗ワックスの製造方法 |
| CU22412A1 (es) * | 1993-11-09 | 1996-01-31 | Dalmer Lab Sa | Una mezcla natural compuesta por alcoholes alifaticos primarios superiores obtenidos de la cera de abejas para el tratamiento de las ulceras gastricas y duodenales que presenta tambien actividad antiinflamatoria |
| US5554379A (en) * | 1994-06-20 | 1996-09-10 | Kv Pharmaceutical Company | Long acting GI and esophageal protectant |
| JP2804445B2 (ja) * | 1994-11-30 | 1998-09-24 | ラボラトリオス ダルマー ソシエダッド アノニマ | 胃潰瘍および十二指腸潰瘍の処置剤および抗炎症剤 |
| US6039950A (en) * | 1995-04-14 | 2000-03-21 | University Of Southern California | Pharmaceutical grade saw palmetto |
| US6080787A (en) * | 1997-02-21 | 2000-06-27 | Abbott Laboratories | Methods for reducing the incidence of necrotizing enterocolitis |
| AUPO605097A0 (en) * | 1997-04-07 | 1997-05-01 | James Cook University Of North Queensland | Food grade wax and process for preparing same |
-
1997
- 1997-04-02 CU CU1997035A patent/CU22723A1/es unknown
-
1998
- 1998-04-01 BR BR9808470-4A patent/BR9808470A/pt not_active Application Discontinuation
- 1998-04-01 US US09/402,292 patent/US6486205B2/en not_active Expired - Fee Related
- 1998-04-01 DK DK98920719T patent/DK0969827T3/da active
- 1998-04-01 JP JP54135598A patent/JP4907750B2/ja not_active Expired - Lifetime
- 1998-04-01 AU AU73494/98A patent/AU732045B2/en not_active Expired
- 1998-04-01 WO PCT/IB1998/000870 patent/WO1998043631A1/en not_active Ceased
- 1998-04-01 CN CNB988055880A patent/CN1230158C/zh not_active Expired - Lifetime
- 1998-04-01 RU RU99123062/14A patent/RU2217130C2/ru active
- 1998-04-01 EP EP98920719A patent/EP0969827B1/en not_active Expired - Lifetime
- 1998-04-01 DE DE69811643T patent/DE69811643T2/de not_active Expired - Lifetime
- 1998-04-01 AT AT98920719T patent/ATE233087T1/de not_active IP Right Cessation
- 1998-04-01 PT PT98920719T patent/PT969827E/pt unknown
- 1998-04-01 ES ES98920719T patent/ES2192769T3/es not_active Expired - Lifetime
- 1998-04-01 CO CO98018329A patent/CO4940484A1/es unknown
- 1998-04-01 MY MYPI98001431A patent/MY120318A/en unknown
- 1998-04-01 CA CA002285242A patent/CA2285242C/en not_active Expired - Lifetime
- 1998-04-01 ZA ZA982744A patent/ZA982744B/xx unknown
- 1998-04-02 AR ARP980101504A patent/AR016054A1/es active IP Right Grant
-
2011
- 2011-11-16 JP JP2011250436A patent/JP2012067119A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU732045B2 (en) | 2001-04-12 |
| RU2217130C2 (ru) | 2003-11-27 |
| JP2012067119A (ja) | 2012-04-05 |
| EP0969827A1 (en) | 2000-01-12 |
| WO1998043631A1 (en) | 1998-10-08 |
| CN1258218A (zh) | 2000-06-28 |
| MY120318A (en) | 2005-10-31 |
| PT969827E (pt) | 2003-07-31 |
| BR9808470A (pt) | 2000-05-23 |
| ES2192769T3 (es) | 2003-10-16 |
| CU22723A1 (es) | 2002-02-28 |
| US20020058705A1 (en) | 2002-05-16 |
| CO4940484A1 (es) | 2000-07-24 |
| HK1029054A1 (en) | 2001-03-23 |
| ATE233087T1 (de) | 2003-03-15 |
| ZA982744B (en) | 1998-10-08 |
| JP2001518092A (ja) | 2001-10-09 |
| CA2285242A1 (en) | 1998-10-08 |
| DE69811643D1 (de) | 2003-04-03 |
| CN1230158C (zh) | 2005-12-07 |
| DE69811643T2 (de) | 2003-12-24 |
| AU7349498A (en) | 1998-10-22 |
| JP4907750B2 (ja) | 2012-04-04 |
| EP0969827B1 (en) | 2003-02-26 |
| US6486205B2 (en) | 2002-11-26 |
| DK0969827T3 (da) | 2003-06-16 |
| AR016054A1 (es) | 2001-06-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2285242C (en) | Mixture of primary fatty acids obtained from sugar cane wax | |
| US5200198A (en) | Medicament and its production and use in the treatment of pain, inflammation and fever in man and animals | |
| JP3602531B2 (ja) | 高級脂肪族第一級アルコール混合物，これをサトウキビワックスから得る方法，およびこれを含有する医薬品 | |
| KR0126286B1 (ko) | 지방산 조성물 | |
| JPH0733655A (ja) | 医薬組成物 | |
| US6235795B1 (en) | Natural mixture composed of higher primary aliphatic alcohols obtained from bee wax for the treatment of gastric and duodenal ulcers that also present antiinflamatory activity | |
| RU99123062A (ru) | Смесь первичных жирных кислот, получаемых из сахарно-тросникового воска | |
| JPH0761923A (ja) | アルツハイマー病治療剤 | |
| EP0201159B1 (en) | Pharmaceutical and dietary compositions containing linolenic acids for the treatment of benign prostatic hypertrophy | |
| CN113398109A (zh) | 一种预防或治疗炎性肠病的酮体混合物及其应用 | |
| US6465526B1 (en) | Natural mixture composed of higher primary aliphatic alcohols obtained from bee wax for the treatment of gastric and duodenal ulcers that also present antiinflamatory activity | |
| EP0107188B1 (en) | A pharmaceutical composition and the use thereof for the treatment of inflammation | |
| JPH01503713A (ja) | チオスルフイン酸誘導体、炎症疾患の治療のためのその使用、ならびに当該化合物を含有する薬剤 | |
| CA2709119C (en) | Preventive or therapeutic agent for inflammatory bowel diseases | |
| HK1029054B (en) | Mixture of primary fatty acids obtained from sugar cane wax | |
| JPS58164507A (ja) | ジベンゾシクロヘプテニリデン類による免疫変化剤 | |
| JPH05246857A (ja) | 痴呆症治療剤 | |
| JPH08119864A (ja) | 鎮吐薬 | |
| JP2821575B2 (ja) | 肝障害改善剤 | |
| JP2804445B2 (ja) | 胃潰瘍および十二指腸潰瘍の処置剤および抗炎症剤 | |
| JPH0825883B2 (ja) | 腎炎治療剤 | |
| Reynolds et al. | Pharmacotherapy of inflammatory bowel disease | |
| US3798322A (en) | 6 or 7-substituted 4 or 8-(amino-1-methyl-butylamino)quinolines as hypolipidemic agents | |
| JPH05937A (ja) | 抗潰瘍剤 | |
| JP2000044470A (ja) | 高脂血症薬 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20180403 |