MXPA05001857A - Intermedios esteroideos de 5-androsten-38-ol y procedimientos para su preparacion. - Google Patents
Intermedios esteroideos de 5-androsten-38-ol y procedimientos para su preparacion.Info
- Publication number
- MXPA05001857A MXPA05001857A MXPA05001857A MXPA05001857A MXPA05001857A MX PA05001857 A MXPA05001857 A MX PA05001857A MX PA05001857 A MXPA05001857 A MX PA05001857A MX PA05001857 A MXPA05001857 A MX PA05001857A MX PA05001857 A MXPA05001857 A MX PA05001857A
- Authority
- MX
- Mexico
- Prior art keywords
- further characterized
- preparation
- hydroxysteroid
- formula
- dihydroxysteroid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 108
- 238000002360 preparation method Methods 0.000 title claims abstract description 71
- 239000000543 intermediate Substances 0.000 title abstract description 12
- -1 5 ANDROSTEN-3beta-OL STEROID Chemical class 0.000 title abstract description 11
- LYFPAZBMEUSVNA-UHFFFAOYSA-N (10R)-3c-Hydroxy-10r.13c-dimethyl-(8cH.9tH.14tH)-Delta5-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCCC1(C)CC2 LYFPAZBMEUSVNA-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims description 51
- 238000000855 fermentation Methods 0.000 claims description 45
- 230000004151 fermentation Effects 0.000 claims description 45
- 230000003637 steroidlike Effects 0.000 claims description 42
- 150000002596 lactones Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 241000122824 Aspergillus ochraceus Species 0.000 claims description 17
- 241000190144 Lasiodiplodia theobromae Species 0.000 claims description 17
- 241000228212 Aspergillus Species 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000012141 concentrate Substances 0.000 claims description 12
- 241000293029 Absidia caerulea Species 0.000 claims description 9
- 241000935926 Diplodia Species 0.000 claims description 7
- 241000235389 Absidia Species 0.000 claims description 6
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 4
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 17
- KVUXYQHEESDGIJ-UHFFFAOYSA-N 10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,16-diol Chemical compound C1CC2CC(O)CCC2(C)C2C1C1CC(O)CC1(C)CC2 KVUXYQHEESDGIJ-UHFFFAOYSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 229910001868 water Inorganic materials 0.000 description 29
- 239000000047 product Substances 0.000 description 27
- 239000000203 mixture Substances 0.000 description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 20
- 239000013078 crystal Substances 0.000 description 20
- 238000011081 inoculation Methods 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 238000010899 nucleation Methods 0.000 description 18
- 150000003431 steroids Chemical class 0.000 description 18
- 230000001954 sterilising effect Effects 0.000 description 17
- 238000004659 sterilization and disinfection Methods 0.000 description 17
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- 241000233866 Fungi Species 0.000 description 14
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 150000001721 carbon Chemical group 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 238000005805 hydroxylation reaction Methods 0.000 description 10
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- 238000005119 centrifugation Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 230000033444 hydroxylation Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 5
- AFGDPPHTYUQKOF-QAGGRKNESA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 AFGDPPHTYUQKOF-QAGGRKNESA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 239000004375 Dextrin Substances 0.000 description 3
- 229920001353 Dextrin Polymers 0.000 description 3
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 3
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019764 Soybean Meal Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 235000019425 dextrin Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 description 3
- 229960001208 eplerenone Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
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- SBNLPRGISFUZQE-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 SBNLPRGISFUZQE-VMXHOPILSA-N 0.000 description 2
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- 235000019483 Peanut oil Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 2
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- 239000007791 liquid phase Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Classifications
-
- 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
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40399002P | 2002-08-16 | 2002-08-16 | |
| US41529302P | 2002-10-01 | 2002-10-01 | |
| PCT/US2003/007791 WO2004016640A2 (en) | 2002-08-16 | 2003-03-21 | 5 ANDROSTEN-3β-OL STEROID INTERMEDIATES AND PROCESSES FOR THEIR PREPARATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05001857A true MXPA05001857A (es) | 2005-06-03 |
Family
ID=31891414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05001857A MXPA05001857A (es) | 2002-08-16 | 2003-03-21 | Intermedios esteroideos de 5-androsten-38-ol y procedimientos para su preparacion. |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20040034215A1 (enExample) |
| EP (1) | EP1534732B1 (enExample) |
| JP (1) | JP2006507369A (enExample) |
| AT (1) | ATE339437T1 (enExample) |
| AU (1) | AU2003285485A1 (enExample) |
| BR (1) | BR0313523A (enExample) |
| CA (1) | CA2495412A1 (enExample) |
| DE (1) | DE60308388T2 (enExample) |
| ES (1) | ES2271636T3 (enExample) |
| MX (1) | MXPA05001857A (enExample) |
| TW (1) | TW200406419A (enExample) |
| WO (1) | WO2004016640A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20042338A1 (it) * | 2004-12-06 | 2005-03-06 | Ind Chimica Srl | Processo per la preparazione di drospirenone |
| US8084446B2 (en) * | 2005-04-26 | 2011-12-27 | Eric Marchewitz | Use of DHEA derivatives for enhancing physical performance |
| BRPI0613679A2 (pt) * | 2005-07-21 | 2011-01-25 | Bayer Schering Pharma Ag | processo para a produção de 3-oxo-pregn-4-eno-21,17-carbolactonas pela oxidação livre de metais de 17-(3-hidroxipropil)-3,17-diidroxiandrostanos, bem como referido composto |
| DE502005004948D1 (de) * | 2005-07-21 | 2008-09-18 | Bayer Schering Pharma Ag | Verfahren zur Herstellung von 3-Oxo-pregn-4-en-21,17-carbolactonen durch die metallfreie Oxidation von 17-(3-hydroxypropyl)-3,17-dihydroxyandrostanen |
| US7319154B2 (en) * | 2005-07-21 | 2008-01-15 | Bayer Schering Pharma Ag | Process for the production of 3-oxo-pregn-4-ene-21, 17-carbolactones by the metal free oxidation of 17-(3-hydroxypropyl)-3, 17-dihydroxyandrostanes |
| CN110331182A (zh) * | 2019-08-06 | 2019-10-15 | 江苏远大仙乐药业有限公司 | 一种甾体中间体的生物转化制备方法 |
| CN111057734A (zh) * | 2019-12-24 | 2020-04-24 | 天津科技大学 | 一种甲基睾丸素高效转化生产11α-羟基-甲基睾丸素的方法 |
| CN110885869A (zh) * | 2019-12-24 | 2020-03-17 | 天津科技大学 | 一种利用微生物转化生产7α-羟基-脱氢表雄酮的方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294646A (en) * | 1963-10-23 | 1966-12-27 | American Home Prod | Microbiological hydroxylation of norsteroids using aspergillus ochraceus |
| DE2349022A1 (de) * | 1973-09-26 | 1975-04-10 | Schering Ag | Neue d-homo-steroide |
| DK134348C (da) * | 1973-11-30 | 1977-03-21 | Schering Ag | Analogifremgangsmade til fremstilling af d-homo-20-ketopregnaner |
| US4031074A (en) * | 1974-09-02 | 1977-06-21 | Akzona Incorporated | Process for the preparation of 11β-hydroxy-18-alkyl-estrane compounds |
| IL48628A0 (en) * | 1974-12-23 | 1976-02-29 | Schering Ag | D-homo-20-keto-pregnanes and process for their manufactur |
| US4054563A (en) * | 1975-04-25 | 1977-10-18 | Ciba-Geigy Corporation | Process for the manufacture of spiro compounds of the steroid series |
| IE46010B1 (en) * | 1976-12-10 | 1983-01-26 | Schering Ag | New corticoids |
| US4336332A (en) * | 1979-02-20 | 1982-06-22 | Hoffmann-La Roche, Inc. | Process for the manufacture of hydroxylated steroids |
| DE3042136A1 (de) * | 1980-11-03 | 1982-06-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur herstellung von 3 (beta), 7 (beta) -dihydroxy- (delta) (pfeil hoch)5(pfeil hoch) -steroiden |
| US4559332A (en) * | 1983-04-13 | 1985-12-17 | Ciba Geigy Corporation | 20-Spiroxanes and analogues having an open ring E, processes for their manufacture, and pharmaceutical preparations thereof |
| AU7978794A (en) * | 1993-10-13 | 1995-05-04 | Neurocrine Biosciences, Inc. | 3,17-dihydroxy-3,7,16 and/or 17-methyl-androst-5-ene compounds, derivatives thereof, and their use |
| EP0973791B1 (en) * | 1995-12-11 | 2007-06-20 | G.D. Searle LLC. | Process for the preparation of an epoxy compound |
| CN1138861C (zh) * | 1995-12-12 | 2004-02-18 | 阿克佐诺贝尔公司 | 类固醇的微生物11α-羟基化方法 |
| FR2771105A1 (fr) | 1997-11-20 | 1999-05-21 | Vitasterol | Utilisation du fusarium monoliforme pour la preparation des derives 7alpha-hydroxyles de la dehydroepiandrosterone et de la pregnenolone |
-
2003
- 2003-03-21 CA CA002495412A patent/CA2495412A1/en not_active Abandoned
- 2003-03-21 US US10/392,955 patent/US20040034215A1/en not_active Abandoned
- 2003-03-21 WO PCT/US2003/007791 patent/WO2004016640A2/en not_active Ceased
- 2003-03-21 DE DE60308388T patent/DE60308388T2/de not_active Expired - Fee Related
- 2003-03-21 TW TW092106331A patent/TW200406419A/zh unknown
- 2003-03-21 BR BR0313523-3A patent/BR0313523A/pt not_active IP Right Cessation
- 2003-03-21 JP JP2005502036A patent/JP2006507369A/ja not_active Abandoned
- 2003-03-21 EP EP03756776A patent/EP1534732B1/en not_active Expired - Lifetime
- 2003-03-21 AT AT03756776T patent/ATE339437T1/de not_active IP Right Cessation
- 2003-03-21 MX MXPA05001857A patent/MXPA05001857A/es unknown
- 2003-03-21 AU AU2003285485A patent/AU2003285485A1/en not_active Abandoned
- 2003-03-21 ES ES03756776T patent/ES2271636T3/es not_active Expired - Lifetime
-
2004
- 2004-06-01 US US10/858,177 patent/US7002028B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20040220158A1 (en) | 2004-11-04 |
| DE60308388D1 (de) | 2006-10-26 |
| ES2271636T3 (es) | 2007-04-16 |
| CA2495412A1 (en) | 2004-02-26 |
| TW200406419A (en) | 2004-05-01 |
| WO2004016640A3 (en) | 2004-07-08 |
| ATE339437T1 (de) | 2006-10-15 |
| US20040034215A1 (en) | 2004-02-19 |
| DE60308388T2 (de) | 2007-09-20 |
| EP1534732B1 (en) | 2006-09-13 |
| EP1534732A2 (en) | 2005-06-01 |
| AU2003285485A1 (en) | 2004-03-03 |
| BR0313523A (pt) | 2005-06-28 |
| WO2004016640A2 (en) | 2004-02-26 |
| US7002028B2 (en) | 2006-02-21 |
| JP2006507369A (ja) | 2006-03-02 |
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