LV11183B - Novel process for crystallising of substances of steroidal structure and pharmaceutical compositions containing thereof - Google Patents
Novel process for crystallising of substances of steroidal structure and pharmaceutical compositions containing thereof Download PDFInfo
- Publication number
- LV11183B LV11183B LVP-95-341A LV950341A LV11183B LV 11183 B LV11183 B LV 11183B LV 950341 A LV950341 A LV 950341A LV 11183 B LV11183 B LV 11183B
- Authority
- LV
- Latvia
- Prior art keywords
- esters
- derivative
- hydroxy
- active ingredient
- des
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000008569 process Effects 0.000 title claims abstract description 11
- 230000003637 steroidlike Effects 0.000 title claims abstract 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims 6
- 239000000126 substance Substances 0.000 title description 11
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- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000004094 surface-active agent Substances 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract 4
- 238000009835 boiling Methods 0.000 claims abstract 3
- 230000008025 crystallization Effects 0.000 claims abstract 3
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- 150000002148 esters Chemical class 0.000 claims description 35
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- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 21
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- KZUIYQJTUIACIG-YBZCJVABSA-N nomegestrol Chemical compound C1=C(C)C2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 KZUIYQJTUIACIG-YBZCJVABSA-N 0.000 claims description 13
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- 229960003387 progesterone Drugs 0.000 claims description 11
- -1 testosterone ethers Chemical class 0.000 claims description 11
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- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 7
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 claims description 7
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 108700019146 Transgenes Proteins 0.000 description 1
- 241000609666 Tuber aestivum Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- DPHFJXVKASDMBW-RQRKFSSASA-N [2-[(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;hydrate Chemical compound O.C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)C[C@@H]2O DPHFJXVKASDMBW-RQRKFSSASA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000000227 bioadhesive Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 229960003840 cortivazol Drugs 0.000 description 1
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 1
- 239000001064 degrader Substances 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 229960003657 dexamethasone acetate Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007519 figuring Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VIQCGTZFEYDQMR-UHFFFAOYSA-N fluphenazine decanoate Chemical compound C1CN(CCOC(=O)CCCCCCCCC)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 VIQCGTZFEYDQMR-UHFFFAOYSA-N 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- FRQMUZJSZHZSGN-HBNHAYAOSA-N medroxyprogesterone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FRQMUZJSZHZSGN-HBNHAYAOSA-N 0.000 description 1
- 229960004616 medroxyprogesterone Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003146 progesterones Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 229920000260 silastic Polymers 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 108010012137 spleen derived immunosuppressive peptide Proteins 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0025—Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0074—Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0077—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J11/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9013981A FR2668945B1 (fr) | 1990-11-12 | 1990-11-12 | Nouveau procede de cristallisation des substances organiques et les composes ainsi obtenus. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV11183A LV11183A (lv) | 1996-04-20 |
| LV11183B true LV11183B (en) | 1996-10-20 |
Family
ID=9402062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-95-341A LV11183B (en) | 1990-11-12 | 1995-11-14 | Novel process for crystallising of substances of steroidal structure and pharmaceutical compositions containing thereof |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5266712A (de) |
| EP (1) | EP0510167B1 (de) |
| JP (1) | JP3281954B2 (de) |
| KR (1) | KR100196895B1 (de) |
| AT (1) | ATE126806T1 (de) |
| BR (1) | BR9106012A (de) |
| CA (1) | CA2073760C (de) |
| DE (1) | DE69112379T2 (de) |
| DK (1) | DK0510167T3 (de) |
| ES (1) | ES2079172T3 (de) |
| FI (1) | FI111545B (de) |
| FR (1) | FR2668945B1 (de) |
| GR (1) | GR3018117T3 (de) |
| HU (1) | HU212780B (de) |
| LV (1) | LV11183B (de) |
| RU (1) | RU2126013C1 (de) |
| WO (1) | WO1992008730A1 (de) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2776191B1 (fr) * | 1998-03-23 | 2002-05-31 | Theramex | Composition hormonale topique a effet systemique |
| US6432936B1 (en) | 1999-01-20 | 2002-08-13 | Wisconsin Alumni Research Foundation | Crystalline 1α-hydroxyvitamin D2 and method of purification thereof |
| US8980290B2 (en) | 2000-08-03 | 2015-03-17 | Antares Pharma Ipl Ag | Transdermal compositions for anticholinergic agents |
| WO2002011768A1 (en) | 2000-08-03 | 2002-02-14 | Antares Pharma Ipl Ag | Novel composition for transdermal and/or transmucosal administration of active compounds that ensures adequate therapeutic levels |
| US7198801B2 (en) | 2000-08-03 | 2007-04-03 | Antares Pharma Ipl Ag | Formulations for transdermal or transmucosal application |
| WO2005039531A1 (en) | 2003-10-10 | 2005-05-06 | Antares Pharma Ipl Ag | Transdermal pharmaceutical formulation for minimizing skin residues |
| DK1361881T3 (da) * | 2000-12-14 | 2006-02-20 | Ortho Mcneil Pharm Inc | Steroide hormonprodukter og fremgangsmåder til fremstilling heraf |
| DE10152351B4 (de) * | 2001-10-18 | 2005-09-22 | Schering Ag | Feste Arzneimittelformulierung für ein Piperazinharnstoffderivat |
| DE10218107A1 (de) * | 2002-04-23 | 2003-11-20 | Jenapharm Gmbh | Verfahren zum Herstellen von Kristallen von Steroiden, danach erhältliche Kristalle und deren Verwendung in pharmazeutischen Formulierungen |
| DE10218106A1 (de) * | 2002-04-23 | 2003-11-20 | Jenapharm Gmbh | Verfahren zum Herstellen von Kristallen von Arzneimittelwirkstoffen, danach erhältliche Kristalle und deren Verwendung in pharmazeutischen Formulierungen |
| MY143936A (en) | 2003-03-27 | 2011-07-29 | Nycomed Gmbh | Process for preparing crystalline ciclesonide with defined particle size |
| EP1727520A2 (de) * | 2003-12-09 | 2006-12-06 | Medcrystalforms, Llc | Verfahren zur herstellung von mischphasen-kokristallen mit wirkstoffen |
| WO2005074942A1 (en) * | 2004-02-04 | 2005-08-18 | Retmed Pty Ltd | Slow release steroid composition |
| RU2253453C1 (ru) * | 2004-03-15 | 2005-06-10 | Общество с ограниченной ответственностью "ЮНАЛ" | Противовоспалительная и антиаллергическая композиция |
| US7425340B2 (en) | 2004-05-07 | 2008-09-16 | Antares Pharma Ipl Ag | Permeation enhancing compositions for anticholinergic agents |
| US20060058276A1 (en) * | 2004-07-15 | 2006-03-16 | Oded Friedman | Processes for the preparation and purification of rocuronium bromide |
| WO2006125642A1 (en) | 2005-05-27 | 2006-11-30 | Antares Pharma Ipl Ag | Methods and apparatus for transdermal or transmucosal application of testosterone |
| NZ571460A (en) | 2006-04-21 | 2010-10-29 | Antares Pharma Ipl Ag | Methods of treating hot flashes with formulations for transdermal or transmucosal application |
| EP1931682A2 (de) * | 2006-08-03 | 2008-06-18 | Teva Pharmaceutical Industries Ltd. | Verfahren zur herstellung von clopidogrel-bisulphat |
| CN101961311B (zh) * | 2010-09-21 | 2012-11-21 | 中山大学 | 一种5α-雄甾(烷)-3β,5,6β-三醇注射剂及其制备方法 |
| MX393195B (es) * | 2012-06-18 | 2025-03-24 | Therapeuticsmd Inc | Capsula de estradiol soluble para insercion por via vaginal |
| CN112871079B (zh) * | 2021-01-27 | 2023-05-16 | 丽江映华生物药业有限公司 | 醋酸诺美孕酮微粒的制备方法及制备装置 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2096744A (en) * | 1932-10-27 | 1937-10-26 | Schering Corp | Hydrogenation products of follicle hormones and method of producing same |
| US2361847A (en) * | 1937-09-04 | 1944-10-31 | Schering Corp | Aromatization of steroid compounds and more especially to the production of estrone-and estradiollike compounds and of their derivatives from delta 1, 2, 4, 5-androstadienol-17-one-3 |
| US2897216A (en) * | 1954-11-01 | 1959-07-28 | Schering Corp | Process for the preparation of steroidal dienes and intermediates obtained thereby |
| US3053865A (en) * | 1958-03-19 | 1962-09-11 | Merck & Co Inc | Novel 16-alkyl and 16-alkylene steroids and processes |
| US3007923A (en) * | 1959-01-22 | 1961-11-07 | Lab Francais Chimiotherapie | Process for the fluorination of 9beta, 11beta-epoxy and 5alpha, 6alpha-epoxy steroids |
| US3836628A (en) | 1972-05-22 | 1974-09-17 | Int Research & Dev Co Ltd | Crystal growth modifier |
| DE2323812A1 (de) * | 1973-05-11 | 1974-11-28 | Jenapharm Veb | Verfahren zur herstellung von kohlensaeurederivaten der oestranreihe |
| GB1515284A (en) * | 1974-05-21 | 1978-06-21 | Gastaud J | Pharmaceutical compositions containing progestogens derived from the 17-alpha-hydroxy-19-nor-progesterone series |
| US4634694A (en) * | 1984-01-14 | 1987-01-06 | Akzo N.V. | Novel Δ4 - and Δ5 -androstene derivatives and pharmaceutical compositions containing these derivatives |
| US4795747A (en) * | 1985-12-23 | 1989-01-03 | Latman Neal S | 16-epiestriol to prevent, inhibit or reduce inflammation |
| US4956600A (en) * | 1988-07-01 | 1990-09-11 | Viteq Corporation | High frequency current detector for a low frequency line |
-
1990
- 1990-11-12 FR FR9013981A patent/FR2668945B1/fr not_active Expired - Fee Related
-
1991
- 1991-11-12 JP JP50041592A patent/JP3281954B2/ja not_active Expired - Lifetime
- 1991-11-12 RU SU5052919A patent/RU2126013C1/ru active
- 1991-11-12 CA CA002073760A patent/CA2073760C/fr not_active Expired - Lifetime
- 1991-11-12 AT AT92900237T patent/ATE126806T1/de not_active IP Right Cessation
- 1991-11-12 WO PCT/FR1991/000888 patent/WO1992008730A1/fr not_active Ceased
- 1991-11-12 BR BR919106012A patent/BR9106012A/pt not_active Application Discontinuation
- 1991-11-12 ES ES92900237T patent/ES2079172T3/es not_active Expired - Lifetime
- 1991-11-12 EP EP92900237A patent/EP0510167B1/de not_active Expired - Lifetime
- 1991-11-12 US US07/910,284 patent/US5266712A/en not_active Expired - Lifetime
- 1991-11-12 DE DE69112379T patent/DE69112379T2/de not_active Expired - Lifetime
- 1991-11-12 KR KR1019920701658A patent/KR100196895B1/ko not_active Expired - Lifetime
- 1991-11-12 HU HU9202608A patent/HU212780B/hu unknown
- 1991-11-12 DK DK92900237.6T patent/DK0510167T3/da active
-
1992
- 1992-07-10 FI FI923188A patent/FI111545B/fi not_active IP Right Cessation
-
1995
- 1995-11-14 LV LVP-95-341A patent/LV11183B/lv unknown
- 1995-11-20 GR GR950403233T patent/GR3018117T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP3281954B2 (ja) | 2002-05-13 |
| HU212780B (en) | 1996-11-28 |
| DE69112379D1 (de) | 1995-09-28 |
| GR3018117T3 (en) | 1996-02-29 |
| RU2126013C1 (ru) | 1999-02-10 |
| EP0510167A1 (de) | 1992-10-28 |
| FR2668945A1 (fr) | 1992-05-15 |
| US5266712A (en) | 1993-11-30 |
| KR927003617A (ko) | 1992-12-18 |
| DK0510167T3 (da) | 1996-01-02 |
| CA2073760C (fr) | 2003-09-23 |
| JPH05503305A (ja) | 1993-06-03 |
| ES2079172T3 (es) | 1996-01-01 |
| KR100196895B1 (ko) | 1999-06-15 |
| HUT61319A (en) | 1992-12-28 |
| BR9106012A (pt) | 1993-01-05 |
| FR2668945B1 (fr) | 1993-02-19 |
| DE69112379T2 (de) | 1996-03-28 |
| ATE126806T1 (de) | 1995-09-15 |
| LV11183A (lv) | 1996-04-20 |
| HU9202608D0 (en) | 1992-10-28 |
| FI923188L (fi) | 1992-07-10 |
| CA2073760A1 (fr) | 1992-05-13 |
| FI111545B (fi) | 2003-08-15 |
| EP0510167B1 (de) | 1995-08-23 |
| WO1992008730A1 (fr) | 1992-05-29 |
| FI923188A0 (fi) | 1992-07-10 |
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