JPH0372079B2 - - Google Patents
Info
- Publication number
- JPH0372079B2 JPH0372079B2 JP17435383A JP17435383A JPH0372079B2 JP H0372079 B2 JPH0372079 B2 JP H0372079B2 JP 17435383 A JP17435383 A JP 17435383A JP 17435383 A JP17435383 A JP 17435383A JP H0372079 B2 JPH0372079 B2 JP H0372079B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- diene
- lecithin
- reaction
- gpc
- 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
Links
- 239000002253 acid Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- SUHOQUVVVLNYQR-MRVPVSSYSA-N choline alfoscerate Chemical compound C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 235000010445 lecithin Nutrition 0.000 description 27
- 239000000787 lecithin Substances 0.000 description 27
- 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 26
- 229940067606 lecithin Drugs 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 23
- 150000001993 dienes Chemical class 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000005227 gel permeation chromatography Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- -1 diene carboxylic acids Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229960004979 fampridine Drugs 0.000 description 4
- 239000002502 liposome Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000000560 biocompatible material Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 1
- YKHVVNDSWHSBPA-BLHCBFLLSA-N (2E,4E)-deca-2,4-dienoic acid Chemical compound CCCCC\C=C\C=C\C(O)=O YKHVVNDSWHSBPA-BLHCBFLLSA-N 0.000 description 1
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- YKHVVNDSWHSBPA-UHFFFAOYSA-N 2,4-Decadienoic acid Natural products CCCCCC=CC=CC(O)=O YKHVVNDSWHSBPA-UHFFFAOYSA-N 0.000 description 1
- ADHNUPOJJCKWRT-UHFFFAOYSA-N 2,4-octadecadienoic acid Natural products CCCCCCCCCCCCCC=CC=CC(O)=O ADHNUPOJJCKWRT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WXUGSDBMQDMRMU-XBLVEGMJSA-N 2E,4E-undecadienoic acid Chemical compound CCCCCC\C=C\C=C\C(O)=O WXUGSDBMQDMRMU-XBLVEGMJSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000008777 Glycerylphosphorylcholine Substances 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960004788 choline alfoscerate Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960004956 glycerylphosphorylcholine Drugs 0.000 description 1
- PJNOTBMYNJXRIV-UHFFFAOYSA-N henicosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCC=CC=CC(O)=O PJNOTBMYNJXRIV-UHFFFAOYSA-N 0.000 description 1
- OOJGMLFHAQOYIL-UHFFFAOYSA-N hexadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCC=CC=CC(O)=O OOJGMLFHAQOYIL-UHFFFAOYSA-N 0.000 description 1
- LNAVIIOBBICBIS-UHFFFAOYSA-N icosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCC=CC=CC(O)=O LNAVIIOBBICBIS-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- ABCNOPCASVAZFN-UHFFFAOYSA-N nonadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCC=CC=CC(O)=O ABCNOPCASVAZFN-UHFFFAOYSA-N 0.000 description 1
- XXQINHWMBIXTGY-UHFFFAOYSA-N pentadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCC=CC=CC(O)=O XXQINHWMBIXTGY-UHFFFAOYSA-N 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 229950004354 phosphorylcholine Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000013269 sustained drug release Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- WNLVXSRACLAFOL-UHFFFAOYSA-N tetradeca-2,4-dienoic acid Chemical compound CCCCCCCCCC=CC=CC(O)=O WNLVXSRACLAFOL-UHFFFAOYSA-N 0.000 description 1
- SUEKUALWVJZYCO-UHFFFAOYSA-N trideca-2,4-dienoic acid Chemical compound CCCCCCCCC=CC=CC(O)=O SUEKUALWVJZYCO-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Eyeglasses (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17435383A JPS6067489A (ja) | 1983-09-22 | 1983-09-22 | 重合性リン脂質の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17435383A JPS6067489A (ja) | 1983-09-22 | 1983-09-22 | 重合性リン脂質の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6067489A JPS6067489A (ja) | 1985-04-17 |
| JPH0372079B2 true JPH0372079B2 (el) | 1991-11-15 |
Family
ID=15977144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17435383A Granted JPS6067489A (ja) | 1983-09-22 | 1983-09-22 | 重合性リン脂質の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6067489A (el) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6281394A (ja) * | 1985-10-04 | 1987-04-14 | Toyo Soda Mfg Co Ltd | 混合酸型重合性リン脂質誘導体およびその製造方法 |
| GB9023498D0 (en) | 1990-10-29 | 1990-12-12 | Biocompatibles Ltd | Soft contact lens material |
| US6743878B2 (en) | 1991-07-05 | 2004-06-01 | Biocompatibles Uk Limited | Polymeric surface coatings |
| RU2167886C2 (ru) * | 1991-07-05 | 2001-05-27 | Биокомпэтиблз Лимитед. | Полимер, способ получения полимера, поверхность с покрытием, способ покрытия поверхности |
| US6090901A (en) * | 1991-07-05 | 2000-07-18 | Biocompatibles Limited | Polymeric surface coatings |
| KR101539804B1 (ko) | 2008-03-31 | 2015-07-27 | 가부시키가이샤 시세이도 | 폴리실록산, 아크릴계 화합물 및 비닐계 화합물 |
-
1983
- 1983-09-22 JP JP17435383A patent/JPS6067489A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6067489A (ja) | 1985-04-17 |
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