NO134373B - - Google Patents
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- Publication number
- NO134373B NO134373B NO2171/71A NO217171A NO134373B NO 134373 B NO134373 B NO 134373B NO 2171/71 A NO2171/71 A NO 2171/71A NO 217171 A NO217171 A NO 217171A NO 134373 B NO134373 B NO 134373B
- Authority
- NO
- Norway
- Prior art keywords
- cyclodextrin
- dissolving
- prostaglandins
- pge2
- solution prepared
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 150000003180 prostaglandins Chemical class 0.000 claims abstract description 40
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 39
- 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 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- -1 substituted Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 239000000047 product Substances 0.000 description 37
- 239000000203 mixture Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 229960002986 dinoprostone Drugs 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 21
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 21
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 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 description 11
- 239000002775 capsule Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000003 vaginal tablet Substances 0.000 description 6
- IMPVDANDCDGWFM-SLESNMHTSA-N (z)-7-[(1r,2r,3r)-3-hydroxy-2-[(e,3s)-3-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid Chemical compound CCCCC(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O IMPVDANDCDGWFM-SLESNMHTSA-N 0.000 description 5
- 101100310593 Candida albicans (strain SC5314 / ATCC MYA-2876) SOD4 gene Proteins 0.000 description 5
- 101100190148 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PGA2 gene Proteins 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000002220 antihypertensive agent Substances 0.000 description 5
- 239000003433 contraceptive agent Substances 0.000 description 5
- MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229940124558 contraceptive agent Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 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 description 2
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 2
- 239000000924 antiasthmatic agent Substances 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 229960004676 antithrombotic agent Drugs 0.000 description 2
- 239000003699 antiulcer agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000001595 contractor effect Effects 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 210000001215 vagina Anatomy 0.000 description 2
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 description 1
- 102100036465 Autoimmune regulator Human genes 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 101000928549 Homo sapiens Autoimmune regulator Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical group 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000002254 contraceptive effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- BGKHCLZFGPIKKU-LDDQNKHRSA-N prostaglandin A1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(O)=O BGKHCLZFGPIKKU-LDDQNKHRSA-N 0.000 description 1
- 125000003259 prostaglandin group Chemical group 0.000 description 1
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229940044977 vaginal tablet Drugs 0.000 description 1
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nanotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Medical Informatics (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45050119A JPS503362B1 (zh) | 1970-06-10 | 1970-06-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134373B true NO134373B (zh) | 1976-06-21 |
| NO134373C NO134373C (zh) | 1976-09-29 |
Family
ID=12850213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2171/71A NO134373C (zh) | 1970-06-10 | 1971-06-08 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3816393A (zh) |
| JP (1) | JPS503362B1 (zh) |
| AT (1) | AT332570B (zh) |
| BE (1) | BE768288A (zh) |
| CA (1) | CA958007A (zh) |
| CH (1) | CH568259A5 (zh) |
| CS (1) | CS170169B2 (zh) |
| CY (1) | CY895A (zh) |
| DE (1) | DE2128674C2 (zh) |
| DK (1) | DK140837B (zh) |
| ES (1) | ES392074A1 (zh) |
| FR (1) | FR2100745B1 (zh) |
| GB (1) | GB1351238A (zh) |
| HK (1) | HK17577A (zh) |
| HU (1) | HU163135B (zh) |
| IE (1) | IE35326B1 (zh) |
| NL (1) | NL162901C (zh) |
| NO (1) | NO134373C (zh) |
| RO (1) | RO62182A (zh) |
| SE (1) | SE390818B (zh) |
| SU (1) | SU404225A3 (zh) |
| ZA (1) | ZA713398B (zh) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163108A (en) * | 1967-02-16 | 1979-07-31 | Lever Brothers Company | Prostaglandins |
| US4054736A (en) * | 1970-06-10 | 1977-10-18 | Ono Pharmaceutical Co., Ltd. | Clathrate compounds of prostaglandins or their analogues with cyclodextrin |
| US3954833A (en) * | 1971-04-12 | 1976-05-04 | The Upjohn Company | 16,16-Methyl and ethyl substituted PGF2.sub.α compounds |
| CA984387A (en) * | 1971-04-12 | 1976-02-24 | Barney J. Magerlein | Analogs of prostaglandins |
| US3903131A (en) * | 1971-04-12 | 1975-09-02 | Upjohn Co | 16 and 16,16-dimethyl PGE{HD 2{B |
| FR2134673A1 (en) * | 1971-04-30 | 1972-12-08 | Ono Pharmaceutical Co | Novel optically active isomers of prostaglandin analoguesof natural configuration useful as hypotensive agents, diuretics,contraceptives, for treating gastric ulcer and asthma, and forinhibiting platelet aggregation |
| US4045467A (en) * | 1972-02-18 | 1977-08-30 | May & Baker Limited | Cyclopentane derivatives |
| US4082789A (en) * | 1972-03-28 | 1978-04-04 | The University Court Of The University Of Edinburgh | Prostaglandins C2 |
| JPS4926258A (zh) * | 1972-07-06 | 1974-03-08 | ||
| US4130721A (en) * | 1972-07-24 | 1978-12-19 | The Upjohn Company | 11-Deoxy PGE2 compounds |
| US4110368A (en) * | 1972-07-24 | 1978-08-29 | American Cyanamid Company | Hydro substituted prostanoic acids and esters |
| US4141914A (en) * | 1972-07-24 | 1979-02-27 | American Cyanamid Company | Novel 11-deoxy-11-substituted prostaglandins of the E and F series |
| JPS4942648A (zh) * | 1972-08-24 | 1974-04-22 | ||
| US3962312A (en) * | 1972-09-21 | 1976-06-08 | Ono Pharmaceutical Company | 9,11,15-Trihydroxy prost-5-enoic acid analogues |
| JPS5443570B2 (zh) * | 1972-10-27 | 1979-12-20 | ||
| US3972917A (en) * | 1972-10-27 | 1976-08-03 | American Home Products Corporation | 11-Deoxy 15-methyl prostaglandin E1 |
| US4092427A (en) * | 1973-04-16 | 1978-05-30 | American Home Products Corporation | Method of inducing abortion using alkyl derivatives of prostanoic acids |
| JPS5623984B2 (zh) * | 1973-04-19 | 1981-06-03 | ||
| US4052446A (en) * | 1973-08-06 | 1977-10-04 | Hoffmann-La Roche Inc. | 11,16-substituted prostaglandins |
| US4059576A (en) * | 1973-08-06 | 1977-11-22 | Hoffmann-La Roche, Inc. | 11-Substituted prostaglandins |
| US4246426A (en) * | 1973-08-06 | 1981-01-20 | Hoffmann-La Roche Inc. | 11-Substituted prostaglandins |
| US4026927A (en) * | 1973-09-25 | 1977-05-31 | Yamanouchi Pharmaceutical Co., Ltd. | Novel prostaglandin derivatives |
| US4036954A (en) * | 1973-11-02 | 1977-07-19 | Yamanouchi Pharmaceutical Co., Ltd. | Stable prostaglandin E group-containing formulation |
| GB1448268A (en) * | 1973-11-13 | 1976-09-02 | May & Baker Ltd | Cyclopentane derivatives |
| GB1441564A (en) * | 1974-02-07 | 1976-07-07 | Upjohn Co | Prostaglandins |
| US4041066A (en) * | 1974-02-07 | 1977-08-09 | The Upjohn Company | 4,5-Cis-didehydro-PGE1 compounds |
| DE2416193C2 (de) * | 1974-04-03 | 1985-08-14 | Hoechst Ag, 6230 Frankfurt | Prostaglandin-Analoge, Verfahren zu ihrer Herstellung sowie ihre Verwendung als cytoprotektives Mittel |
| US4256651A (en) * | 1974-10-02 | 1981-03-17 | The Upjohn Company | 2a,2b-Dihomo-15-alkyl-PGF1β compounds |
| US3974195A (en) * | 1974-10-02 | 1976-08-10 | The Upjohn Company | 2A,2B-Dihomo-15-alkyl-PGF2.sub.α analogs |
| GB1482010A (en) * | 1974-10-28 | 1977-08-03 | Ono Pharmaceutical Co | Prostaglandin analogues |
| DK142235B (da) * | 1974-12-20 | 1980-09-29 | Yamanouchi Pharma Co Ltd | Analogifremgangsmåde til fremstilling af 20-alkoxy-16-methyl-prostadiensyre-derivater. |
| US4209637A (en) * | 1975-02-24 | 1980-06-24 | The Upjohn Company | 2,2-Difluoro-PGF2 analogs |
| US4207420A (en) * | 1975-02-24 | 1980-06-10 | The Upjohn Company | 2,2-Difluoro-PGF1 analogs |
| US4059701A (en) * | 1975-04-17 | 1977-11-22 | American Home Products Corporation | 15-Substituted prostanoic acids for treating bronchial spasm |
| FR2313019A2 (fr) * | 1975-06-04 | 1976-12-31 | Ono Pharmaceutical Co | Nouveaux analogues de prostaglandines et leur procede de preparation |
| US4086269A (en) * | 1975-07-07 | 1978-04-25 | American Home Products Corporation | 11-Deoxy-15-substituted prostaglandins |
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| US5376645A (en) * | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
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| JP6052175B2 (ja) | 2011-08-02 | 2016-12-27 | 小野薬品工業株式会社 | 左室拡張機能改善剤 |
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| JPWO2023037934A1 (zh) * | 2021-09-13 | 2023-03-16 |
-
1970
- 1970-06-10 JP JP45050119A patent/JPS503362B1/ja active Pending
-
1971
- 1971-05-26 ZA ZA713398A patent/ZA713398B/xx unknown
- 1971-05-26 US US00147255A patent/US3816393A/en not_active Expired - Lifetime
- 1971-06-03 AT AT480371A patent/AT332570B/de not_active IP Right Cessation
- 1971-06-04 CH CH813871A patent/CH568259A5/xx not_active IP Right Cessation
- 1971-06-07 RO RO67198A patent/RO62182A/ro unknown
- 1971-06-08 NO NO2171/71A patent/NO134373C/no unknown
- 1971-06-09 ES ES392074A patent/ES392074A1/es not_active Expired
- 1971-06-09 DK DK279771AA patent/DK140837B/da not_active IP Right Cessation
- 1971-06-09 NL NL7107894.A patent/NL162901C/xx not_active IP Right Cessation
- 1971-06-09 BE BE768288A patent/BE768288A/xx not_active IP Right Cessation
- 1971-06-09 CY CY895A patent/CY895A/xx unknown
- 1971-06-09 DE DE2128674A patent/DE2128674C2/de not_active Expired
- 1971-06-09 IE IE710/71A patent/IE35326B1/xx unknown
- 1971-06-09 GB GB1978571*[A patent/GB1351238A/en not_active Expired
- 1971-06-09 SE SE7107486A patent/SE390818B/xx unknown
- 1971-06-09 SU SU1668708A patent/SU404225A3/ru active
- 1971-06-10 CA CA115,284A patent/CA958007A/en not_active Expired
- 1971-06-10 HU HUOO173A patent/HU163135B/hu not_active IP Right Cessation
- 1971-06-10 FR FR7121129A patent/FR2100745B1/fr not_active Expired
- 1971-06-10 CS CS4254A patent/CS170169B2/cs unknown
-
1977
- 1977-04-14 HK HK175/77A patent/HK17577A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL162901C (nl) | 1980-07-15 |
| IE35326B1 (en) | 1976-01-07 |
| US3816393A (en) | 1974-06-11 |
| ATA480371A (de) | 1976-01-15 |
| CS170169B2 (zh) | 1976-08-27 |
| GB1351238A (en) | 1974-04-24 |
| ZA713398B (en) | 1972-01-26 |
| CH568259A5 (zh) | 1975-10-31 |
| NO134373C (zh) | 1976-09-29 |
| DE2128674C2 (de) | 1982-06-24 |
| ES392074A1 (es) | 1974-08-01 |
| JPS503362B1 (zh) | 1975-02-04 |
| RO62182A (zh) | 1977-07-15 |
| CY895A (en) | 1977-10-07 |
| BE768288A (fr) | 1971-11-03 |
| CA958007A (en) | 1974-11-19 |
| IE35326L (en) | 1971-12-10 |
| AT332570B (de) | 1976-10-11 |
| NL162901B (nl) | 1980-02-15 |
| SE390818B (sv) | 1977-01-24 |
| FR2100745B1 (zh) | 1974-08-30 |
| DE2128674A1 (de) | 1971-12-16 |
| HU163135B (zh) | 1973-06-28 |
| HK17577A (en) | 1977-04-22 |
| DK140837C (zh) | 1981-09-07 |
| DK140837B (da) | 1979-11-26 |
| SU404225A3 (zh) | 1973-10-26 |
| NL7107894A (zh) | 1971-12-14 |
| FR2100745A1 (zh) | 1972-03-24 |
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