JPH0327555B2 - - Google Patents
Info
- Publication number
- JPH0327555B2 JPH0327555B2 JP61036988A JP3698886A JPH0327555B2 JP H0327555 B2 JPH0327555 B2 JP H0327555B2 JP 61036988 A JP61036988 A JP 61036988A JP 3698886 A JP3698886 A JP 3698886A JP H0327555 B2 JPH0327555 B2 JP H0327555B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- reaction
- membranes
- fluorine
- compound
- 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
- -1 phosphate ester Chemical class 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- 239000010452 phosphate Substances 0.000 claims description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000003839 salts Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 17
- 239000012528 membrane Substances 0.000 description 12
- 235000011007 phosphoric acid Nutrition 0.000 description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 9
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 9
- 238000001338 self-assembly Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 210000000170 cell membrane Anatomy 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002502 liposome Substances 0.000 description 5
- 150000003904 phospholipids Chemical class 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 239000003012 bilayer membrane Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920005597 polymer membrane Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 230000000865 phosphorylative effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940042880 natural phospholipid Drugs 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- UPSJKWVICNHZIJ-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl] phosphate Chemical compound [Na+].CC(=C)C(=O)OCC(O)COP([O-])(=O)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F UPSJKWVICNHZIJ-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KOWOGKUTCSIJFZ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl dihydrogen phosphate Chemical compound OP(O)(=O)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F KOWOGKUTCSIJFZ-UHFFFAOYSA-N 0.000 description 1
- LZHCVNIARUXHAL-UHFFFAOYSA-N 2-tert-butyl-4-ethylphenol Chemical compound CCC1=CC=C(O)C(C(C)(C)C)=C1 LZHCVNIARUXHAL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- DHCGNXDXGPMUER-UHFFFAOYSA-N [1,1,2,3,3,4,4,5,5,6,10,10,10-tridecafluoro-2-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)decyl] dihydrogen phosphate Chemical compound C(CC(C(C(C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(OP(=O)(O)O)(F)F)F)(F)F)(F)F)(F)F)F)CC(F)(F)F DHCGNXDXGPMUER-UHFFFAOYSA-N 0.000 description 1
- WKUISSZJLAODLR-UHFFFAOYSA-N [3-[1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecoxy(hydroxy)phosphoryl]oxy-2-hydroxypropyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COP(O)(=O)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F WKUISSZJLAODLR-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000009087 cell motility Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61036988A JPS62195390A (ja) | 1986-02-21 | 1986-02-21 | 含フツ素リン酸エステル |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61036988A JPS62195390A (ja) | 1986-02-21 | 1986-02-21 | 含フツ素リン酸エステル |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62195390A JPS62195390A (ja) | 1987-08-28 |
| JPH0327555B2 true JPH0327555B2 (enExample) | 1991-04-16 |
Family
ID=12485129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61036988A Granted JPS62195390A (ja) | 1986-02-21 | 1986-02-21 | 含フツ素リン酸エステル |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62195390A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5846516A (en) * | 1992-06-03 | 1998-12-08 | Alliance Pharmaceutial Corp. | Perfluoroalkylated amphiphilic phosphorus compounds: preparation and biomedical applications |
-
1986
- 1986-02-21 JP JP61036988A patent/JPS62195390A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62195390A (ja) | 1987-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2877958B2 (ja) | エチレン系不飽和化合物 | |
| US4736051A (en) | Process for the preparation of an alkali metal salt of a diester phosphoric acid | |
| JP3052923B2 (ja) | （メタ）アクリレート誘導体の製造方法 | |
| GB2172889A (en) | Phosphoric esters | |
| JPH0327555B2 (enExample) | ||
| US4740609A (en) | Phosphoric esters and process for preparing same | |
| EP0242781B1 (en) | Phosphoric esters and process for preparing the same | |
| US7202228B2 (en) | Hydrogelation agents | |
| JPH0327557B2 (enExample) | ||
| CN101928301B (zh) | 从右旋磷霉素左旋苯乙胺盐合成左旋磷霉素右旋苯乙胺盐的方法 | |
| JP3419030B2 (ja) | ホスホリルコリン誘導体の製造方法 | |
| JP7723413B2 (ja) | 双性イオン化合物の製造方法 | |
| JPS61229888A (ja) | リン酸エステルの製造法 | |
| JPS6215210A (ja) | リン酸基を含有する新規な重合体の製造法 | |
| JP3171279B2 (ja) | 炭素原子数１４〜１８を有するアルキルホスホコリンの製法及びアルキルホスホコリンの精製法 | |
| CN111057100A (zh) | 含两种不同侧链的磷脂酰甘油单钠盐的制备方法 | |
| JPH0148914B2 (enExample) | ||
| JP2649343B2 (ja) | リン酸エステルの製造法 | |
| JP3526369B2 (ja) | フルオロアルキル基含有リン酸トリエステルおよびその製造方法 | |
| JPH0660185B2 (ja) | リン酸エステルの製造法 | |
| JPS63178842A (ja) | リポソ−ム形成剤 | |
| JPH10226696A (ja) | Ａｍｐアルキルエステル誘導体の製造方法 | |
| JPS6215211A (ja) | 増粘剤 | |
| JPS63287545A (ja) | リポソ−ム形成剤 | |
| JPS6251690A (ja) | リン酸エステル |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |