JPH0326165B2 - - Google Patents
Info
- Publication number
- JPH0326165B2 JPH0326165B2 JP58181628A JP18162883A JPH0326165B2 JP H0326165 B2 JPH0326165 B2 JP H0326165B2 JP 58181628 A JP58181628 A JP 58181628A JP 18162883 A JP18162883 A JP 18162883A JP H0326165 B2 JPH0326165 B2 JP H0326165B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbon group
- carbon atoms
- vesicles
- ammonium
- group
- 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
- 239000000203 mixture Substances 0.000 claims description 25
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 18
- -1 Phosphate ester salt Chemical class 0.000 claims description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- WZEMSIKSCALWJZ-UHFFFAOYSA-N azane;ethanol Chemical group N.CCO.CCO WZEMSIKSCALWJZ-UHFFFAOYSA-N 0.000 claims 1
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical group N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 claims 1
- KQQCTWHSWXCZHB-UHFFFAOYSA-N azane;propan-2-ol Chemical group N.CC(C)O KQQCTWHSWXCZHB-UHFFFAOYSA-N 0.000 claims 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical group CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 claims 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims 1
- GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 claims 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical group OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims 1
- 238000000034 method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 239000002502 liposome Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000003937 drug carrier Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- SJZZDLZBGLQGCG-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;dioctadecyl hydrogen phosphate Chemical compound OCCN(CCO)CCO.CCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCC SJZZDLZBGLQGCG-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 210000002472 endoplasmic reticulum Anatomy 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- GBMTXDSKXXXLHM-ZSCHJXSPSA-N (2s)-2,6-diaminohexanoic acid;dioctadecyl hydrogen phosphate Chemical compound NCCCC[C@H](N)C(O)=O.CCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCC GBMTXDSKXXXLHM-ZSCHJXSPSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- UJUWNSRXIGHHKM-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;didodecyl hydrogen phosphate Chemical compound OCC[NH+](CCO)CCO.CCCCCCCCCCCCOP([O-])(=O)OCCCCCCCCCCCC UJUWNSRXIGHHKM-UHFFFAOYSA-N 0.000 description 1
- ZJUUTZOYDQREOQ-UHFFFAOYSA-N C(O)CN.P(=O)(OCCCCCCCCCCCCCCCCCC)(OCCCCCCCCCCCCCCCCCC)O Chemical compound C(O)CN.P(=O)(OCCCCCCCCCCCCCCCCCC)(OCCCCCCCCCCCCCCCCCC)O ZJUUTZOYDQREOQ-UHFFFAOYSA-N 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- SRSLTXZRJNCQFO-UHFFFAOYSA-N N(CCO)CCO.P(=O)(OCCCCCCCCCCCCCCCCCC)(OCCCCCCCCCCCCCCCCCC)O Chemical compound N(CCO)CCO.P(=O)(OCCCCCCCCCCCCCCCCCC)(OCCCCCCCCCCCCCCCCCC)O SRSLTXZRJNCQFO-UHFFFAOYSA-N 0.000 description 1
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- WFFZELZOEWLYNK-CLFAGFIQSA-N bis[(z)-octadec-9-enyl] hydrogen phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCCOP(O)(=O)OCCCCCCCC\C=C/CCCCCCCC WFFZELZOEWLYNK-CLFAGFIQSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- OTOYAWQBIJQTRP-UHFFFAOYSA-N dihexadecyl phosphate;tris(2-hydroxyethyl)azanium Chemical compound OCC[NH+](CCO)CCO.CCCCCCCCCCCCCCCCOP([O-])(=O)OCCCCCCCCCCCCCCCC OTOYAWQBIJQTRP-UHFFFAOYSA-N 0.000 description 1
- FRXGWNKDEMTFPL-UHFFFAOYSA-N dioctadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCC FRXGWNKDEMTFPL-UHFFFAOYSA-N 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JSMHQMIPUOPQLR-UHFFFAOYSA-M sodium;dioctadecyl phosphate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOP([O-])(=O)OCCCCCCCCCCCCCCCCCC JSMHQMIPUOPQLR-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 230000007332 vesicle formation Effects 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biophysics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58181628A JPS6072830A (ja) | 1983-09-29 | 1983-09-29 | ベシクル用組成物 |
| GB08422629A GB2151203B (en) | 1983-09-29 | 1984-09-07 | Compositions for making vesicles |
| FR8414761A FR2552666B1 (fr) | 1983-09-29 | 1984-09-26 | Compositions vesiculaires a base de sel de phosphate et d'agent tensio-actif |
| DE19843435517 DE3435517A1 (de) | 1983-09-29 | 1984-09-27 | Vesikel bildende massen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58181628A JPS6072830A (ja) | 1983-09-29 | 1983-09-29 | ベシクル用組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6072830A JPS6072830A (ja) | 1985-04-24 |
| JPH0326165B2 true JPH0326165B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-04-10 |
Family
ID=16104098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58181628A Granted JPS6072830A (ja) | 1983-09-29 | 1983-09-29 | ベシクル用組成物 |
Country Status (4)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK86988A (da) * | 1987-02-25 | 1988-08-26 | Takeda Chemical Industries Ltd | Liposompraeparat og anvendelse deraf |
| US4911928A (en) * | 1987-03-13 | 1990-03-27 | Micro-Pak, Inc. | Paucilamellar lipid vesicles |
| JPH0720857B2 (ja) * | 1988-08-11 | 1995-03-08 | テルモ株式会社 | リポソームおよびその製法 |
| US6132763A (en) * | 1988-10-20 | 2000-10-17 | Polymasc Pharmaceuticals Plc | Liposomes |
| CA2073680C (en) * | 1990-04-18 | 2001-07-03 | Katsumi Iga | Liposome composition |
| DE4107152C2 (de) * | 1991-03-06 | 1994-03-24 | Gregor Cevc | Präparate zur nichtinvasiven Verabreichung von Antidiabetica |
| DE4107153A1 (de) * | 1991-03-06 | 1992-09-10 | Gregor Cevc | Praeparat zur wirkstoffapplikation in kleinsttroepfchenform |
| ATE139691T1 (de) * | 1990-09-06 | 1996-07-15 | Johnson & Son Inc S C | Verfahren zur stabilisierung von liposomen sowie diese enthaltende mittel |
| FR2694893A1 (fr) * | 1992-08-03 | 1994-02-25 | Oreal | Composition formée d'une dispersion aqueuse de vésicules de lipides amphiphiles non-ioniques stabilisées. |
| US5741518A (en) * | 1992-08-03 | 1998-04-21 | L'oreal | Composition composed of an aqueous dispersion of stabilized vesicles of nonionic amphiphilic lipids |
| FR2694884B1 (fr) * | 1992-08-03 | 1996-10-18 | Oreal | Composition formee d'une dispersion aqueuse de vesicules de lipides amphiphiles non-ioniques stabilisees. |
| US5464696A (en) * | 1992-08-13 | 1995-11-07 | Bracco International B.V. | Particles for NMR imaging |
| BR9816014A (pt) * | 1998-09-01 | 2001-05-08 | Idea Ag | Transporte eletricamente controlado de penetrantes carregados através de barreiras |
| US6080211A (en) * | 1999-02-19 | 2000-06-27 | Igen, Inc. | Lipid vesicle-based fuel additives and liquid energy sources containing same |
| EP1264632A1 (de) * | 2001-06-08 | 2002-12-11 | Cognis Iberia, S.L. | Verwendung von Alkyl(ether)phosphaten(III) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2193871B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-07-25 | 1977-07-22 | Colgate Palmolive Co | |
| SE408714B (sv) * | 1974-11-25 | 1979-07-02 | Berol Kemi Ab | Flytande vattenhaltigt tvett- och rengoringsmedel innehallande en ytaktiv del och komplexbildare |
| FR2315991A1 (fr) * | 1975-06-30 | 1977-01-28 | Oreal | Procede de fabrication de dispersions aqueuses de spherules lipidiques et nouvelles compositions correspondantes |
| FR2416008A1 (fr) * | 1978-02-02 | 1979-08-31 | Oreal | Lyophilisats de liposomes |
| EP0102324A3 (de) * | 1982-07-29 | 1984-11-07 | Ciba-Geigy Ag | Lipide und Tenside in wässriger Phase |
-
1983
- 1983-09-29 JP JP58181628A patent/JPS6072830A/ja active Granted
-
1984
- 1984-09-07 GB GB08422629A patent/GB2151203B/en not_active Expired
- 1984-09-26 FR FR8414761A patent/FR2552666B1/fr not_active Expired
- 1984-09-27 DE DE19843435517 patent/DE3435517A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2151203A (en) | 1985-07-17 |
| DE3435517A1 (de) | 1985-04-18 |
| JPS6072830A (ja) | 1985-04-24 |
| GB2151203B (en) | 1987-01-07 |
| FR2552666A1 (fr) | 1985-04-05 |
| GB8422629D0 (en) | 1984-10-10 |
| FR2552666B1 (fr) | 1988-05-27 |
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