CA1098445A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1098445A
Authority: CA; Canada
Prior art keywords: heparin; process according; liposomes; lipid; liposome
Prior art date: 1977-08-16
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

Application number

CA289,445A

Other languages

English (en)

Inventor

Edgar Sache

Henri Bertrand

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Choay SA

Original Assignee

Choay SA

Priority date (The priority date 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 date listed.)

1977-08-16

Filing date

1977-10-25

Publication date

1981-03-31

1977-10-25 Application filed by Choay SA filed Critical Choay SA

1981-03-31 Application granted granted Critical

1981-03-31 Publication of CA1098445A publication Critical patent/CA1098445A/fr

Status Expired legal-status Critical Current

Links

229960002897 heparin Drugs 0.000 title claims abstract description 92
229920000669 heparin Polymers 0.000 title claims abstract description 92
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 title claims abstract description 90
239000002502 liposome Substances 0.000 title claims abstract description 85
238000000034 method Methods 0.000 title claims description 27
230000008569 process Effects 0.000 title claims description 21
150000002632 lipids Chemical class 0.000 claims abstract description 37
150000003904 phospholipids Chemical class 0.000 claims abstract description 22
230000000717 retained effect Effects 0.000 claims abstract description 8
125000002252 acyl group Chemical group 0.000 claims abstract 2
239000000243 solution Substances 0.000 claims description 23
239000006185 dispersion Substances 0.000 claims description 11
239000007864 aqueous solution Substances 0.000 claims description 10
239000003599 detergent Substances 0.000 claims description 6
238000003756 stirring Methods 0.000 claims description 6
235000004626 essential fatty acids Nutrition 0.000 claims description 5
150000004665 fatty acids Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
235000014113 dietary fatty acids Nutrition 0.000 claims description 4
239000000194 fatty acid Substances 0.000 claims description 4
229930195729 fatty acid Natural products 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
230000005855 radiation Effects 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
125000000129 anionic group Chemical group 0.000 claims description 2
125000002091 cationic group Chemical group 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
125000001924 fatty-acyl group Chemical group 0.000 claims description 2
150000002270 gangliosides Chemical class 0.000 claims description 2
150000002327 glycerophospholipids Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
150000003408 sphingolipids Chemical class 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims 2
239000011541 reaction mixture Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 21
230000009471 action Effects 0.000 abstract description 8
238000001727 in vivo Methods 0.000 abstract description 5
239000002253 acid Substances 0.000 abstract description 4
150000007513 acids Chemical class 0.000 abstract description 4
150000004671 saturated fatty acids Chemical class 0.000 abstract description 4
230000001371 heparinic effect Effects 0.000 abstract 1
235000003441 saturated fatty acids Nutrition 0.000 abstract 1
239000000725 suspension Substances 0.000 description 26
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 15
241000283973 Oryctolagus cuniculus Species 0.000 description 14
230000015271 coagulation Effects 0.000 description 14
238000005345 coagulation Methods 0.000 description 14
238000000527 sonication Methods 0.000 description 14
239000000203 mixture Substances 0.000 description 13
230000000694 effects Effects 0.000 description 12
238000012360 testing method Methods 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000008280 blood Substances 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
235000012000 cholesterol Nutrition 0.000 description 8
108090000190 Thrombin Proteins 0.000 description 7
229960004072 thrombin Drugs 0.000 description 7
239000012736 aqueous medium Substances 0.000 description 6
239000011521 glass Substances 0.000 description 6
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 5
241000700159 Rattus Species 0.000 description 5
229940067606 lecithin Drugs 0.000 description 5
239000000787 lecithin Substances 0.000 description 5
235000010445 lecithin Nutrition 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
239000000872 buffer Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000002609 medium Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
-1 phosphoryl group Chemical group 0.000 description 4
239000000523 sample Substances 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
230000002429 anti-coagulating effect Effects 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000000740 bleeding effect Effects 0.000 description 3
RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 description 3
229940093541 dicetylphosphate Drugs 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
150000008105 phosphatidylcholines Chemical class 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000010409 thin film Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
239000011324 bead Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229910001424 calcium ion Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000003111 delayed effect Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000010355 oscillation Effects 0.000 description 2
230000010412 perfusion Effects 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
241000894007 species Species 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
239000002691 unilamellar liposome Substances 0.000 description 2
230000002792 vascular Effects 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
PVPBBTJXIKFICP-UHFFFAOYSA-N (7-aminophenothiazin-3-ylidene)azanium;chloride Chemical compound [Cl-].C1=CC(=[NH2+])C=C2SC3=CC(N)=CC=C3N=C21 PVPBBTJXIKFICP-UHFFFAOYSA-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
TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 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
102100037651 AP-2 complex subunit sigma Human genes 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
102000002322 Egg Proteins Human genes 0.000 description 1
108010000912 Egg Proteins Proteins 0.000 description 1
108010049003 Fibrinogen Proteins 0.000 description 1
102000008946 Fibrinogen Human genes 0.000 description 1
ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
206010019708 Hepatic steatosis Diseases 0.000 description 1
SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
101710195119 Inner capsid protein sigma-2 Proteins 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 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
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
238000001994 activation Methods 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000013019 agitation Methods 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
239000003146 anticoagulant agent Substances 0.000 description 1
229940127219 anticoagulant drug Drugs 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
230000004856 capillary permeability Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229940107161 cholesterol Drugs 0.000 description 1
229960001231 choline Drugs 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
230000001112 coagulating effect Effects 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
235000013345 egg yolk Nutrition 0.000 description 1
210000002969 egg yolk Anatomy 0.000 description 1
229940068998 egg yolk phospholipid Drugs 0.000 description 1
239000008344 egg yolk phospholipid Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
229940031098 ethanolamine Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229940012952 fibrinogen Drugs 0.000 description 1
239000010408 film Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
229960000367 inositol Drugs 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000000644 isotonic solution Substances 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
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
238000011866 long-term treatment Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
210000004779 membrane envelope Anatomy 0.000 description 1
150000001457 metallic cations Chemical class 0.000 description 1
230000014508 negative regulation of coagulation Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000002674 ointment 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
230000003534 oscillatory effect Effects 0.000 description 1
238000011176 pooling Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002633 protecting effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000021003 saturated fats Nutrition 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
201000005665 thrombophilia Diseases 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
238000011282 treatment Methods 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
238000005199 ultracentrifugation Methods 0.000 description 1
238000002525 ultrasonication Methods 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
238000005406 washing Methods 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Dispersion Chemistry (AREA)
Molecular Biology (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA289,445A 1977-08-16 1977-10-25 Traduction non-disponible Expired CA1098445A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB34.410/77		1977-08-16
GB3441077		1977-08-16

Publications (1)

Publication Number	Publication Date
CA1098445A true CA1098445A (fr)	1981-03-31

Family

ID=10365289

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA289,445A Expired CA1098445A (fr)	1977-08-16	1977-10-25	Traduction non-disponible

Country Status (2)

Country	Link
CA (1)	CA1098445A (fr)
CH (1)	CH637294A5 (fr)

1977
- 1977-10-25 CA CA289,445A patent/CA1098445A/fr not_active Expired
1978
- 1978-01-01 CH CH1286577A patent/CH637294A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH637294A5 (en)	1983-07-29

Legal Events

Date	Code	Title	Description
1998-03-31	MKEX	Expiry

Publication	Publication Date	Title
US4239754A (en)	1980-12-16	Liposomes containing heparin and a process for obtaining them
EP0094692B1 (fr)	1986-08-27	Liposomes enrobées contenant de l'ubidecarénone
US4241046A (en)	1980-12-23	Method of encapsulating biologically active materials in lipid vesicles
JP3577312B2 (ja)	2004-10-13	定義された脂質系を含有する薬剤組成物
EP0278465B1 (fr)	1992-04-01	Liposomes encapsulant d'agents antinéoplastiques
FI92463C (fi)	1994-11-25	Menetelmä sterolirakkuloiden valmistamiseksi ja yhdisteen sulkemiseksi niiden sisään
US4756910A (en)	1988-07-12	Adriamycin-entrapping liposome preparation
EP0161445A1 (fr)	1985-11-21	Complexe hydrosoluble d'un médicament et procédé pour sa préparation
AU2022338905B2 (en)	2025-06-26	Atherosclerosis-targeted liposome nanocarrier delivery system and preparation method therefor
EP0069399B1 (fr)	1986-10-29	Composition pharamceutique contenant des liposomes qui contiennent l'ubidecarenone
JPH11507628A (ja)	1999-07-06	改良されたリポソーム製剤
Davis et al.	1985	The influence of emulsifying agents on the phagocytosis of lipid emulsions by macrophages
JPH08134026A (ja)	1996-05-28	アミノアルコール類の塩およびこれを含有する医薬処方物
US4942036A (en)	1990-07-17	Therapy by vesicle delivery to the hydroxyapatite of bone
PL103082B1 (pl)	1979-05-31	Sposob wytwarzania nowego preparatu antygenowego
JPH06178930A (ja)	1994-06-28	被膜安定化リポソーム及びその製造方法
CA1098445A (fr)	1981-03-31	Traduction non-disponible
Kuipers et al.	1987	Biliary lipid secretion in the rat. The uncoupling of biliary cholesterol and phospholipid secretion from bile acid secretion by sulfated glycolithocholic acid
WO1980001456A1 (fr)	1980-07-24	Composition pharmaceutique et procede pour sa preparation
GB1591306A (en)	1981-06-17	Liposomes containing heparin and a process for obtaining them
PT1427394E (pt)	2007-04-30	Processo para acelerar a recuperação de um traumatismo utilizando entidades sintéticas ou naturais que simulam a apoptose
Feldman et al.	1977	Calcium binding to rat heart plasma membranes: Isolation and purification of a lipoprotein component with a high calcium binding capacity
JPH0455433B2 (fr)	1992-09-03
Lupu et al.	1988	Alterations of phospholipid asymmetry in the membrane of spontaneously aggregated platelets in diabetes
JPS6362490B2 (fr)	1988-12-02