GB1604161A - Compositions containing prostaglandin analogues - Google Patents
Compositions containing prostaglandin analogues Download PDFInfo
- Publication number
- GB1604161A GB1604161A GB18064/78A GB1806478A GB1604161A GB 1604161 A GB1604161 A GB 1604161A GB 18064/78 A GB18064/78 A GB 18064/78A GB 1806478 A GB1806478 A GB 1806478A GB 1604161 A GB1604161 A GB 1604161A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pgi
- analogue
- ester
- methyl
- cyclodextrin clathrate
- 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 title description 10
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 title description 3
- 101710129448 Glucose-6-phosphate isomerase 2 Proteins 0.000 claims description 85
- 229920000858 Cyclodextrin Polymers 0.000 claims description 41
- -1 ( 2 ethyl)cyclopentyl Chemical group 0.000 claims description 37
- 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 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- HEPKWABQTOCTFQ-CXTOUWENSA-N methyl (5e)-5-[(3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoate Chemical compound O1\C(=C\CCCC(=O)OC)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 HEPKWABQTOCTFQ-CXTOUWENSA-N 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 16
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-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)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 HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 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 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000001367 artery Anatomy 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000001772 blood platelet Anatomy 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 210000001589 microsome Anatomy 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010048620 Intracardiac thrombus Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700159 Rattus Species 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
- 239000013543 active substance Substances 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000003500 enol ether group Chemical group 0.000 description 1
- 229960001123 epoprostenol Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- 230000003228 microsomal effect Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- SGUKUZOVHSFKPH-YNNPMVKQSA-N prostaglandin G2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](OO)CCCCC)[C@H]2C\C=C/CCCC(O)=O SGUKUZOVHSFKPH-YNNPMVKQSA-N 0.000 description 1
- KAQKFAOMNZTLHT-OZUDYXHBSA-M prostaglandin I2(1-) 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-M 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- 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
-
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nanotechnology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Biophysics (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5127877A JPS53136513A (en) | 1977-05-06 | 1977-05-06 | Stabilization of prostaglandin-x-related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1604161A true GB1604161A (en) | 1981-12-02 |
Family
ID=12882465
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18064/78A Expired GB1604161A (en) | 1977-05-06 | 1978-05-05 | Compositions containing prostaglandin analogues |
| GB34230/80A Expired GB1604162A (en) | 1977-05-06 | 1978-05-05 | Compositions containing prostaglandin analogues |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34230/80A Expired GB1604162A (en) | 1977-05-06 | 1978-05-05 | Compositions containing prostaglandin analogues |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4479944A (enExample) |
| JP (1) | JPS53136513A (enExample) |
| DE (1) | DE2819447A1 (enExample) |
| FR (2) | FR2389375B1 (enExample) |
| GB (2) | GB1604161A (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU179141B (enExample) * | 1977-09-23 | 1982-08-28 | ||
| DE2811950A1 (de) * | 1978-03-18 | 1979-12-13 | Hoechst Ag | Neue analoga von prostacyclin |
| US4430340A (en) * | 1978-07-17 | 1984-02-07 | The Upjohn Company | Stabilization of PGI2 compounds with surfactants |
| DE2902809A1 (de) | 1979-01-25 | 1980-08-07 | Hoechst Ag | Neue analoga von prostacyclin |
| US4211793A (en) * | 1979-03-19 | 1980-07-08 | American Cyanamid Company | Triethyl citrate solutions of PGE-type compounds |
| US4303671A (en) | 1980-07-10 | 1981-12-01 | The Upjohn Company | Albumin stabilized prostacyclin |
| JPS6013779A (ja) * | 1983-07-05 | 1985-01-24 | Green Cross Corp:The | プロスタグランジンｉ↓２誘導体 |
| KR880012221A (ko) * | 1987-04-13 | 1988-11-26 | 사노 가즈오 | 에스테르 또는 아미드를 활성성분으로 함유하는 약제 조성물 |
| US5002935A (en) * | 1987-12-30 | 1991-03-26 | University Of Florida | Improvements in redox systems for brain-targeted drug delivery |
| US5017566A (en) * | 1987-12-30 | 1991-05-21 | University Of Florida | Redox systems for brain-targeted drug delivery |
| US5997856A (en) * | 1988-10-05 | 1999-12-07 | Chiron Corporation | Method and compositions for solubilization and stabilization of polypeptides, especially proteins |
| US20040014695A1 (en) * | 1992-06-19 | 2004-01-22 | Supergen, Inc. | Pharmaceutical formulation |
| US5602112A (en) * | 1992-06-19 | 1997-02-11 | Supergen, Inc. | Pharmaceutical formulation |
| US5824668A (en) * | 1996-11-07 | 1998-10-20 | Supergen, Inc. | Formulation for administration of steroid compounds |
| US20070010478A1 (en) * | 2005-07-06 | 2007-01-11 | Branimir Sikic | Zosuquidar, daunorubicin, and cytarabine for the treatment of cancer |
| US20070010487A1 (en) * | 2005-07-06 | 2007-01-11 | Jeff Schwegman | Chemotherapeutic formulations of zosuquidar trihydrochloride and modified cyclodextrins |
| US20070010485A1 (en) * | 2005-07-06 | 2007-01-11 | Jeff Schwegman | Chemotherapeutic formulations of zosuquidar trihydrochloride and modified cyclodextrins |
| US20070009532A1 (en) * | 2005-07-06 | 2007-01-11 | Branimir Sikic | Treatment of patients with cancer using a calicheamicin-antibody conjugate in combination with zosuquidar |
| US20070010486A1 (en) * | 2005-07-06 | 2007-01-11 | Jeff Schwegman | Chemotherapeutic formulations of zosuquidar trihydrochloride and modified cyclodextrins |
| JP5925158B2 (ja) * | 2013-06-04 | 2016-05-25 | テックフィールズ バイオケム カンパニー リミテッド | 非常に高い皮膚浸透率を有するプロスタグランジン及び関連化合物の正荷電水溶性プロドラッグ |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS503362B1 (enExample) * | 1970-06-10 | 1975-02-04 | ||
| US3829579A (en) * | 1971-11-01 | 1974-08-13 | Upjohn Co | Stable solutions of pge-type compounds |
| DE2357953A1 (de) * | 1973-11-21 | 1975-05-28 | Hoechst Ag | Neue, natuerlich nicht vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung |
| JPS51128948A (en) * | 1975-10-20 | 1976-11-10 | Ono Pharmaceut Co Ltd | Prostaglandin analogues, process for preparing thereof and pharmaceuti cal compositions containing said analofues |
| IL51189A (en) * | 1976-02-04 | 1985-08-30 | Upjohn Co | Prostaglandin analogs |
| GB1595056A (en) * | 1976-10-12 | 1981-08-05 | Wellcome Found | Pharmaceutical combination |
| 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 |
| HU179141B (enExample) * | 1977-09-23 | 1982-08-28 | ||
| JPS54115368A (en) * | 1978-03-01 | 1979-09-07 | Ono Pharmaceut Co Ltd | Prostaglandin i2 analog, its preparation, and drug composition containing it as active constituent |
-
1977
- 1977-05-06 JP JP5127877A patent/JPS53136513A/ja active Pending
-
1978
- 1978-05-02 US US05/902,118 patent/US4479944A/en not_active Expired - Lifetime
- 1978-05-03 FR FR7813047A patent/FR2389375B1/fr not_active Expired
- 1978-05-03 DE DE19782819447 patent/DE2819447A1/de not_active Withdrawn
- 1978-05-05 GB GB18064/78A patent/GB1604161A/en not_active Expired
- 1978-05-05 GB GB34230/80A patent/GB1604162A/en not_active Expired
- 1978-11-02 FR FR7831038A patent/FR2398498A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4479944A (en) | 1984-10-30 |
| FR2398498B1 (enExample) | 1982-12-17 |
| JPS53136513A (en) | 1978-11-29 |
| DE2819447A1 (de) | 1978-11-09 |
| GB1604162A (en) | 1981-12-02 |
| FR2389375A1 (enExample) | 1978-12-01 |
| FR2389375B1 (enExample) | 1982-08-06 |
| FR2398498A1 (fr) | 1979-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |