FI65912C - Foerfarande foer framstaellning av farmaceutiskt anvaendbara inklusionskomplexer av prostacyklin och prostacyklin-c1-4-estrar med beta-cyklodextrin - Google Patents
Foerfarande foer framstaellning av farmaceutiskt anvaendbara inklusionskomplexer av prostacyklin och prostacyklin-c1-4-estrar med beta-cyklodextrin Download PDFInfo
- Publication number
- FI65912C FI65912C FI782878A FI782878A FI65912C FI 65912 C FI65912 C FI 65912C FI 782878 A FI782878 A FI 782878A FI 782878 A FI782878 A FI 782878A FI 65912 C FI65912 C FI 65912C
- Authority
- FI
- Finland
- Prior art keywords
- prostacyclin
- cyclodextrin
- solution
- prostacyklin
- complex
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 39
- 229960001123 epoprostenol Drugs 0.000 claims description 34
- 239000000243 solution Substances 0.000 claims description 23
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000001116 FEMA 4028 Substances 0.000 claims description 14
- 229960004853 betadex Drugs 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 12
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 12
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- -1 prostacyclin methyl ester Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000872 buffer Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 239000003708 ampul Substances 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 125000001033 ether group Chemical group 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 239000008176 lyophilized powder Substances 0.000 claims 1
- 239000008363 phosphate buffer Substances 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 31
- 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 11
- 208000007536 Thrombosis Diseases 0.000 description 9
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- 229940097362 cyclodextrins Drugs 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 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 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000035508 accumulation Effects 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006190 sub-lingual tablet Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000945 Amylopectin Polymers 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 229940114079 arachidonic acid Drugs 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010050902 Postoperative thrombosis Diseases 0.000 description 1
- 108010081391 Ristocetin Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- BGTFCAQCKWKTRL-YDEUACAXSA-N chembl1095986 Chemical compound C1[C@@H](N)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]([C@H]1C(N[C@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(C(=C(O)C=4)C)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@@H](C(=O)N3)[C@H](O)C=3C=CC(O4)=CC=3)C(=O)N1)C(O)=O)=O)C(C=C1)=CC=C1OC1=C(O[C@@H]3[C@H]([C@H](O)[C@@H](O)[C@H](CO[C@@H]5[C@H]([C@@H](O)[C@H](O)[C@@H](C)O5)O)O3)O[C@@H]3[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@@H]3[C@H]([C@H](O)[C@@H](CO)O3)O)C4=CC2=C1 BGTFCAQCKWKTRL-YDEUACAXSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- JZULKTSSLJNBQJ-UHFFFAOYSA-N chromium;sulfuric acid Chemical compound [Cr].OS(O)(=O)=O JZULKTSSLJNBQJ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003815 prostacyclins Chemical class 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229950004257 ristocetin Drugs 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229940098466 sublingual tablet Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nanotechnology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77CI1770A HU179141B (en, 2012) | 1977-09-23 | 1977-09-23 | |
| HUCI001770 | 1977-09-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI782878A7 FI782878A7 (fi) | 1979-03-24 |
| FI65912B FI65912B (fi) | 1984-04-30 |
| FI65912C true FI65912C (fi) | 1984-08-10 |
Family
ID=10994670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI782878A FI65912C (fi) | 1977-09-23 | 1978-09-21 | Foerfarande foer framstaellning av farmaceutiskt anvaendbara inklusionskomplexer av prostacyklin och prostacyklin-c1-4-estrar med beta-cyklodextrin |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5456685A (en, 2012) |
| AT (1) | AT369362B (en, 2012) |
| BE (1) | BE870646A (en, 2012) |
| CH (1) | CH637388A5 (en, 2012) |
| CS (1) | CS200242B2 (en, 2012) |
| DD (1) | DD138600A5 (en, 2012) |
| DE (1) | DE2840142A1 (en, 2012) |
| DK (1) | DK420778A (en, 2012) |
| FI (1) | FI65912C (en, 2012) |
| FR (1) | FR2404006A1 (en, 2012) |
| GB (1) | GB2006193B (en, 2012) |
| GR (1) | GR65001B (en, 2012) |
| HU (1) | HU179141B (en, 2012) |
| IL (1) | IL55569A (en, 2012) |
| IT (1) | IT1160661B (en, 2012) |
| NL (1) | NL7809643A (en, 2012) |
| PL (1) | PL121664B1 (en, 2012) |
| SE (1) | SE447574B (en, 2012) |
| SU (1) | SU847914A3 (en, 2012) |
| YU (1) | YU220678A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53136513A (en) * | 1977-05-06 | 1978-11-29 | Ono Pharmaceut Co Ltd | Stabilization of prostaglandin-x-related compounds |
| US4352793A (en) * | 1979-04-26 | 1982-10-05 | Sumitomo Chemical Company, Limited | Pharmaceutical composition comprising bencyclane fumarate and cyclodextrin |
| JPS5920230A (ja) * | 1982-07-19 | 1984-02-01 | チバ−ガイギ−・アクチエンゲゼルシヤフト | ピルプロフエン含有薬剤 |
| JPS61289034A (ja) * | 1985-06-17 | 1986-12-19 | Teijin Ltd | イソカルバサイクリン類脂肪乳剤 |
| DE3608088C2 (de) * | 1986-03-07 | 1995-11-16 | Schering Ag | Pharmazeutische Präparate, enthaltend Cyclodextrinclathrate von Carbacyclinderivaten |
| DE3740838A1 (de) * | 1987-11-27 | 1989-06-08 | Schering Ag | Cyclodextrinclathrate von 5-cyano-prostacyclinderivaten und ihre verwendung als arzneimittel |
| KR20060127946A (ko) | 2004-01-29 | 2006-12-13 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 매크롤라이드계 화합물의 안정화 방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS503362B1 (en, 2012) * | 1970-06-10 | 1975-02-04 | ||
| US3953435A (en) * | 1974-01-10 | 1976-04-27 | Ono Pharmaceutical Company | Aldehyde derivatives of prostaglandins |
| JPS5395958A (en) * | 1977-01-31 | 1978-08-22 | Ono Pharmaceut Co Ltd | Prostaglandin analogues and process for their preparation |
| US4178367A (en) * | 1977-02-21 | 1979-12-11 | Ono Pharmaceutical Co. Ltd. | Prostaglandin I2 analogues |
| JPS53136513A (en) * | 1977-05-06 | 1978-11-29 | Ono Pharmaceut Co Ltd | Stabilization of prostaglandin-x-related compounds |
-
1977
- 1977-09-23 HU HU77CI1770A patent/HU179141B/hu not_active IP Right Cessation
-
1978
- 1978-09-13 IL IL55569A patent/IL55569A/xx unknown
- 1978-09-13 GR GR57216A patent/GR65001B/el unknown
- 1978-09-15 DE DE19782840142 patent/DE2840142A1/de not_active Ceased
- 1978-09-18 CS CS786036A patent/CS200242B2/cs unknown
- 1978-09-19 YU YU02206/78A patent/YU220678A/xx unknown
- 1978-09-19 IT IT69160/78A patent/IT1160661B/it active
- 1978-09-20 AT AT0677478A patent/AT369362B/de not_active IP Right Cessation
- 1978-09-21 FR FR7827079A patent/FR2404006A1/fr active Granted
- 1978-09-21 BE BE190613A patent/BE870646A/xx not_active IP Right Cessation
- 1978-09-21 SE SE7809946A patent/SE447574B/sv not_active IP Right Cessation
- 1978-09-21 FI FI782878A patent/FI65912C/fi not_active IP Right Cessation
- 1978-09-21 DD DD78208003A patent/DD138600A5/xx unknown
- 1978-09-22 GB GB7837834A patent/GB2006193B/en not_active Expired
- 1978-09-22 CH CH995078A patent/CH637388A5/de not_active IP Right Cessation
- 1978-09-22 NL NL7809643A patent/NL7809643A/xx not_active Application Discontinuation
- 1978-09-22 JP JP11738378A patent/JPS5456685A/ja active Pending
- 1978-09-22 DK DK420778A patent/DK420778A/da not_active Application Discontinuation
- 1978-09-22 SU SU782668853A patent/SU847914A3/ru active
- 1978-09-22 PL PL1978209773A patent/PL121664B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK420778A (da) | 1979-03-24 |
| IT7869160A0 (it) | 1978-09-19 |
| JPS5456685A (en) | 1979-05-07 |
| DE2840142A1 (de) | 1979-04-05 |
| IL55569A (en) | 1981-12-31 |
| IT1160661B (it) | 1987-03-11 |
| SE447574B (sv) | 1986-11-24 |
| YU220678A (en) | 1983-10-31 |
| PL209773A1 (pl) | 1979-06-04 |
| FR2404006A1 (fr) | 1979-04-20 |
| GR65001B (en) | 1980-06-12 |
| AT369362B (de) | 1982-12-27 |
| IL55569A0 (en) | 1978-12-17 |
| SU847914A3 (ru) | 1981-07-15 |
| FI65912B (fi) | 1984-04-30 |
| GB2006193A (en) | 1979-05-02 |
| NL7809643A (nl) | 1979-03-27 |
| BE870646A (fr) | 1979-01-15 |
| GB2006193B (en) | 1982-05-26 |
| FR2404006B1 (en, 2012) | 1981-07-31 |
| CH637388A5 (de) | 1983-07-29 |
| HU179141B (en, 2012) | 1982-08-28 |
| DD138600A5 (de) | 1979-11-14 |
| FI782878A7 (fi) | 1979-03-24 |
| CS200242B2 (en) | 1980-08-29 |
| PL121664B1 (en) | 1982-05-31 |
| ATA677478A (de) | 1982-05-15 |
| SE7809946L (sv) | 1979-03-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: CHINOIN GYOGUSZER ES VEGYESZETI TERMEKEK |