AP874A - Iodinated fatty acid esters, iodinated fatty acids and derivatives thereof, produced by iodohydrination using alkysilylated derivatives and alkaline iodides, and pharmacological activities thereof. - Google Patents
Iodinated fatty acid esters, iodinated fatty acids and derivatives thereof, produced by iodohydrination using alkysilylated derivatives and alkaline iodides, and pharmacological activities thereof. Download PDFInfo
- Publication number
- AP874A AP874A APAP/P/1998/001180A AP9801180A AP874A AP 874 A AP874 A AP 874A AP 9801180 A AP9801180 A AP 9801180A AP 874 A AP874 A AP 874A
- Authority
- AP
- ARIPO
- Prior art keywords
- oil
- fatty acid
- iodinated
- derivatives
- process according
- Prior art date
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 75
- 239000000194 fatty acid Substances 0.000 title claims abstract description 75
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 75
- -1 fatty acid esters Chemical class 0.000 title claims abstract description 46
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 29
- 150000004694 iodide salts Chemical class 0.000 title description 2
- 230000000144 pharmacologic effect Effects 0.000 title 1
- 235000019484 Rapeseed oil Nutrition 0.000 claims abstract description 18
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 15
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims abstract description 14
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims abstract description 8
- 229940071870 hydroiodic acid Drugs 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 206010018498 Goitre Diseases 0.000 claims abstract description 6
- 235000009518 sodium iodide Nutrition 0.000 claims abstract description 5
- 239000000446 fuel Substances 0.000 claims abstract description 4
- 239000005051 trimethylchlorosilane Substances 0.000 claims abstract description 4
- 201000003872 goiter Diseases 0.000 claims abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 239000011630 iodine Substances 0.000 claims description 9
- 235000019482 Palm oil Nutrition 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 239000002540 palm oil Substances 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 6
- 235000019198 oils Nutrition 0.000 claims description 6
- 239000004006 olive oil Substances 0.000 claims description 6
- 235000008390 olive oil Nutrition 0.000 claims description 6
- 239000010491 poppyseed oil Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 235000019483 Peanut oil Nutrition 0.000 claims description 5
- 235000019485 Safflower oil Nutrition 0.000 claims description 5
- 235000019486 Sunflower oil Nutrition 0.000 claims description 5
- 239000003240 coconut oil Substances 0.000 claims description 5
- 235000019864 coconut oil Nutrition 0.000 claims description 5
- 239000008169 grapeseed oil Substances 0.000 claims description 5
- 239000000944 linseed oil Substances 0.000 claims description 5
- 235000021388 linseed oil Nutrition 0.000 claims description 5
- 239000000312 peanut oil Substances 0.000 claims description 5
- 235000005713 safflower oil Nutrition 0.000 claims description 5
- 239000003813 safflower oil Substances 0.000 claims description 5
- 239000008159 sesame oil Substances 0.000 claims description 5
- 235000011803 sesame oil Nutrition 0.000 claims description 5
- 235000012424 soybean oil Nutrition 0.000 claims description 5
- 239000002600 sunflower oil Substances 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 5
- 239000008158 vegetable oil Substances 0.000 claims description 5
- 239000010497 wheat germ oil Substances 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 4
- 235000005687 corn oil Nutrition 0.000 claims description 4
- 239000002285 corn oil Substances 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- 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 claims description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims description 2
- 229940114079 arachidonic acid Drugs 0.000 claims description 2
- 235000021342 arachidonic acid Nutrition 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000003449 preventive effect Effects 0.000 claims description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 2
- 229960003656 ricinoleic acid Drugs 0.000 claims description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001173 tumoral effect Effects 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 150000002194 fatty esters Chemical class 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- 230000009471 action Effects 0.000 abstract description 4
- 239000012530 fluid Substances 0.000 abstract description 2
- 238000010952 in-situ formation Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 15
- 238000001228 spectrum Methods 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 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 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 230000009469 supplementation Effects 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 206010067997 Iodine deficiency Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- YMEKEHSRPZAOGO-UHFFFAOYSA-N boron triiodide Chemical compound IB(I)I YMEKEHSRPZAOGO-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 230000000378 dietary effect Effects 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 235000006479 iodine deficiency Nutrition 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- UEILPVLZADSHBO-UHFFFAOYSA-N 2-bromohexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCC(Br)C(Cl)=O UEILPVLZADSHBO-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- 235000005637 Brassica campestris Nutrition 0.000 description 1
- 241001301148 Brassica rapa subsp. oleifera Species 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 206010010510 Congenital hypothyroidism Diseases 0.000 description 1
- 208000027219 Deficiency disease Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 206010020880 Hypertrophy 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
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 206010039840 Secondary hypothyroidism Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- XVJFCWCVLJOKRP-UHFFFAOYSA-N boron;n-ethylethanamine Chemical compound [B].CCNCC XVJFCWCVLJOKRP-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 208000029305 central congenital hypothyroidism Diseases 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- 208000003532 hypothyroidism Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 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
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000006016 thyroid dysfunction Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9508582A FR2736549B1 (fr) | 1995-07-11 | 1995-07-11 | Esters d'acides gras iodes, acides gras iodes et leurs derives, obtenus par iodohydrination faisant intervenir des derives alkylsilyles avec des iodures alcalins et leurs activites pharmacologiques |
| PCT/FR1996/001075 WO1997003038A1 (fr) | 1995-07-11 | 1996-07-10 | Esters d'acides gras iodes, acides gras iodes et leurs derives, obtenus par iodohydrination, faisant intervenir des derives alkylsilyles avec des iodures alcalins et leurs activites pharmacologiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AP874A true AP874A (en) | 2000-09-13 |
Family
ID=9481022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1998/001180A AP874A (en) | 1995-07-11 | 1996-07-10 | Iodinated fatty acid esters, iodinated fatty acids and derivatives thereof, produced by iodohydrination using alkysilylated derivatives and alkaline iodides, and pharmacological activities thereof. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6124357A (en, 2012) |
| EP (1) | EP0840720B1 (en, 2012) |
| CN (1) | CN1077880C (en, 2012) |
| AP (1) | AP874A (en, 2012) |
| AT (1) | ATE249414T1 (en, 2012) |
| AU (1) | AU6523496A (en, 2012) |
| BG (1) | BG63802B1 (en, 2012) |
| BR (1) | BR9609610A (en, 2012) |
| DE (1) | DE69629928T2 (en, 2012) |
| EA (1) | EA001719B1 (en, 2012) |
| FR (1) | FR2736549B1 (en, 2012) |
| GE (1) | GEP20002238B (en, 2012) |
| HU (1) | HUP9901340A3 (en, 2012) |
| IN (1) | IN185195B (en, 2012) |
| MA (1) | MA23935A1 (en, 2012) |
| OA (1) | OA10650A (en, 2012) |
| PL (1) | PL185807B1 (en, 2012) |
| RO (1) | RO120337B1 (en, 2012) |
| TR (1) | TR199800031T1 (en, 2012) |
| UA (1) | UA56142C2 (en, 2012) |
| WO (1) | WO1997003038A1 (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6426367B1 (en) * | 1999-09-09 | 2002-07-30 | Efa Sciences Llc | Methods for selectively occluding blood supplies to neoplasias |
| FR2891461B1 (fr) * | 2005-09-30 | 2010-09-03 | Jacques Theron | Preparation medicamenteuse visqueuse injectable comprenant de l'ethanol et un compose liposoluble opaque aux rayons x. |
| CN101245007B (zh) * | 2008-03-13 | 2011-03-23 | 武汉工程大学 | 一种稳定的碘化植物油脂肪酸乙酯的制备方法 |
| FR2976491B1 (fr) * | 2011-06-14 | 2015-07-10 | R I P H | Esters d'acides gras iodes contenant au minimum 50 pour cent d'esters d'acide monoiodo stearique ou derives sous forme de capsule molle ou de gelule, utile lors d'un accident nucleaire. |
| CN107287029B (zh) * | 2016-05-30 | 2021-04-06 | 江苏恒瑞医药股份有限公司 | 一种碘化植物油脂肪酸乙酯的制备方法 |
| CN109251144B (zh) * | 2017-07-12 | 2021-06-18 | 财团法人食品工业发展研究所 | 碘化脂肪酸乙酯的制备方法 |
| CN109251142A (zh) * | 2017-07-12 | 2019-01-22 | 财团法人食品工业发展研究所 | 碘化脂肪酸乙酯的制备方法 |
| JP7210542B2 (ja) * | 2017-08-07 | 2023-01-23 | ユニベルシテ ドゥ ジュネーブ | Ｃｔイメージング用のヨウ素化脂肪酸のナノエマルジョン |
| CN110387286A (zh) * | 2018-04-18 | 2019-10-29 | 江苏恒瑞医药股份有限公司 | 一种碘化植物油脂肪酸乙酯的制备方法 |
| CN109438240B (zh) * | 2018-09-10 | 2022-05-03 | 季珉 | 一种稳定的碘化亚油酸酯的制备方法 |
| CN114606055B (zh) * | 2020-12-08 | 2024-02-13 | 成都西岭源药业有限公司 | 一种去除碘化植物油脂肪酸乙酯中结合不稳定的碘的方法 |
| US20240336552A1 (en) * | 2021-08-02 | 2024-10-10 | Microvention, Inc. | Compounds |
| PL245039B1 (pl) * | 2022-02-15 | 2024-04-22 | Centrum Badan I Rozwoju Tech Dla Przemyslu Spolka Akcyjna | Świeca bioaktywna oraz sposób wytwarzania świecy bioaktywnej. |
| WO2025145066A1 (en) * | 2023-12-28 | 2025-07-03 | Navinta, Llc | An improved process for preparation of ethiodized oil |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3513323A1 (de) * | 1985-04-13 | 1986-10-23 | Merck Patent Gmbh, 6100 Darmstadt | Stabilisierte iodfette und verfahren zu deren herstellung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53119817A (en) * | 1977-03-26 | 1978-10-19 | Sinloihi Co Ltd | Glycerilltri*22iodoohexadecanoate* and process for preparing same |
-
1995
- 1995-07-11 FR FR9508582A patent/FR2736549B1/fr not_active Expired - Fee Related
-
1996
- 1996-07-10 PL PL96324383A patent/PL185807B1/pl not_active IP Right Cessation
- 1996-07-10 DE DE69629928T patent/DE69629928T2/de not_active Expired - Lifetime
- 1996-07-10 EP EP96924964A patent/EP0840720B1/fr not_active Expired - Lifetime
- 1996-07-10 AU AU65234/96A patent/AU6523496A/en not_active Abandoned
- 1996-07-10 BR BR9609610-1A patent/BR9609610A/pt active Search and Examination
- 1996-07-10 GE GEAP19964133A patent/GEP20002238B/en unknown
- 1996-07-10 TR TR1998/00031T patent/TR199800031T1/xx unknown
- 1996-07-10 WO PCT/FR1996/001075 patent/WO1997003038A1/fr active IP Right Grant
- 1996-07-10 RO RO98-00028A patent/RO120337B1/ro unknown
- 1996-07-10 HU HU9901340A patent/HUP9901340A3/hu unknown
- 1996-07-10 EA EA199800120A patent/EA001719B1/ru not_active IP Right Cessation
- 1996-07-10 AP APAP/P/1998/001180A patent/AP874A/en active
- 1996-07-10 US US08/981,931 patent/US6124357A/en not_active Expired - Lifetime
- 1996-07-10 AT AT96924964T patent/ATE249414T1/de not_active IP Right Cessation
- 1996-07-11 IN IN1552DE1996 patent/IN185195B/en unknown
- 1996-07-11 MA MA24310A patent/MA23935A1/fr unknown
- 1996-07-11 CN CN96107188A patent/CN1077880C/zh not_active Expired - Fee Related
- 1996-10-07 UA UA98020668A patent/UA56142C2/uk unknown
-
1998
- 1998-01-09 OA OA9800001A patent/OA10650A/fr unknown
- 1998-02-05 BG BG102234A patent/BG63802B1/bg unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3513323A1 (de) * | 1985-04-13 | 1986-10-23 | Merck Patent Gmbh, 6100 Darmstadt | Stabilisierte iodfette und verfahren zu deren herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6523496A (en) | 1997-02-10 |
| CN1077880C (zh) | 2002-01-16 |
| IN185195B (en, 2012) | 2000-12-02 |
| EP0840720A1 (fr) | 1998-05-13 |
| MX9800322A (es) | 1998-09-30 |
| PL324383A1 (en) | 1998-05-25 |
| HUP9901340A2 (hu) | 1999-09-28 |
| MA23935A1 (fr) | 1997-04-01 |
| FR2736549A1 (fr) | 1997-01-17 |
| ATE249414T1 (de) | 2003-09-15 |
| GEP20002238B (en) | 2000-09-25 |
| FR2736549B1 (fr) | 1997-10-10 |
| CN1143067A (zh) | 1997-02-19 |
| DE69629928T2 (de) | 2004-07-22 |
| EA001719B1 (ru) | 2001-08-27 |
| TR199800031T1 (xx) | 1998-05-21 |
| BG63802B1 (bg) | 2003-01-31 |
| DE69629928D1 (de) | 2003-10-16 |
| OA10650A (fr) | 2002-09-18 |
| WO1997003038A1 (fr) | 1997-01-30 |
| PL185807B1 (pl) | 2003-08-29 |
| EP0840720B1 (fr) | 2003-09-10 |
| EA199800120A1 (ru) | 1998-10-29 |
| UA56142C2 (uk) | 2003-05-15 |
| RO120337B1 (ro) | 2005-12-30 |
| BG102234A (en) | 1998-09-30 |
| HUP9901340A3 (en) | 1999-11-29 |
| BR9609610A (pt) | 2002-05-07 |
| US6124357A (en) | 2000-09-26 |
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