DE2207420A1 - Verfahren zur herstellung von 16,17ungesaettigten steroiden - Google Patents
Verfahren zur herstellung von 16,17ungesaettigten steroidenInfo
- Publication number
- DE2207420A1 DE2207420A1 DE2207420A DE2207420A DE2207420A1 DE 2207420 A1 DE2207420 A1 DE 2207420A1 DE 2207420 A DE2207420 A DE 2207420A DE 2207420 A DE2207420 A DE 2207420A DE 2207420 A1 DE2207420 A1 DE 2207420A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- schering
- acid
- methylene chloride
- preparation
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003431 steroids Chemical class 0.000 title description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 235000011056 potassium acetate Nutrition 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UOQFZGVGGMHGEE-UHFFFAOYSA-N 1,1-dihydroxypropan-2-one Chemical group CC(=O)C(O)O UOQFZGVGGMHGEE-UHFFFAOYSA-N 0.000 description 1
- OFOQKVIQDOHHKF-SSMLKLAUSA-N 2-[(9R,10S,13R)-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12-decahydrocyclopenta[a]phenanthren-17-ylidene]acetaldehyde Chemical compound C(C=C1C=CC2=C3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O OFOQKVIQDOHHKF-SSMLKLAUSA-N 0.000 description 1
- QRFGDGZPNFSNCE-UHFFFAOYSA-N 2-hydroxyprop-2-enal Chemical compound OC(=C)C=O QRFGDGZPNFSNCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000907514 Entebbe bat virus Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- -1 dirnetnylf ormaniid Chemical compound 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE795243D BE795243A (fr) | 1972-02-11 | Procede de preparation de steroides insatures en 16,17 | |
| DE2207420A DE2207420A1 (de) | 1972-02-11 | 1972-02-11 | Verfahren zur herstellung von 16,17ungesaettigten steroiden |
| DD168292A DD100942A5 (US06826419-20041130-M00005.png) | 1972-02-11 | 1973-01-17 | |
| DK48373*#A DK131942C (da) | 1972-02-11 | 1973-01-29 | Fremgangsmadetil fremstilling af delta4,16-11beta-hydroxy-3,20-diketopregnadiener |
| CS722A CS165381B2 (US06826419-20041130-M00005.png) | 1972-02-11 | 1973-01-30 | |
| AU51931/73A AU468856B2 (en) | 1972-02-11 | 1973-02-07 | Process forthe preparation of 16, 17-unsaturated steroids |
| AT112373A AT328102B (de) | 1972-02-11 | 1973-02-08 | Verfahren zur herstellung von delta 4,16-11beta-hydroxy-3,20-diketosteroiden |
| HUSE1665A HU165442B (US06826419-20041130-M00005.png) | 1972-02-11 | 1973-02-09 | |
| FR7304677A FR2171374B1 (US06826419-20041130-M00005.png) | 1972-02-11 | 1973-02-09 | |
| US00331060A US3842105A (en) | 1972-02-11 | 1973-02-09 | Process for the preparation of 16,17-unsaturated steroids |
| CH186473A CH586719A5 (US06826419-20041130-M00005.png) | 1972-02-11 | 1973-02-09 | |
| GB682073A GB1424212A (en) | 1972-02-11 | 1973-02-12 | Process for the manufacture of 16,17-unsaturated steroids |
| JP48017358A JPS4886854A (US06826419-20041130-M00005.png) | 1972-02-11 | 1973-02-12 | |
| NL7301975A NL7301975A (US06826419-20041130-M00005.png) | 1972-02-11 | 1973-02-12 | |
| SE7301934A SE385591B (sv) | 1972-02-11 | 1973-02-12 | Sett att framstella 16,17- omettade steroider tillhorande pregnanserien |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2207420A DE2207420A1 (de) | 1972-02-11 | 1972-02-11 | Verfahren zur herstellung von 16,17ungesaettigten steroiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2207420A1 true DE2207420A1 (de) | 1973-08-16 |
Family
ID=5836210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2207420A Pending DE2207420A1 (de) | 1972-02-11 | 1972-02-11 | Verfahren zur herstellung von 16,17ungesaettigten steroiden |
Country Status (15)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4216159A (en) * | 1978-05-25 | 1980-08-05 | The Upjohn Company | Synthesis of 16-unsaturated pregnanes from 17-keto steroids |
| DE3852252T2 (de) * | 1987-09-11 | 1995-04-06 | Nippon Zeon Co | Verfahren zur Herstellung einer alpha-acyloxy-alpha-beta-ungesättigten Verbindung und eines 20-acyloxy-17(20)-methylen-21-al-steroidderivats. |
| US5169966A (en) * | 1987-09-11 | 1992-12-08 | Nippon Zeon Co., Ltd | Process for producing an α-acyloxy-α, β-unsaturated carbonyl compound and a 20-acyloxy-17(20)-methylen-21-al-steroid compound |
| CN103739647B (zh) * | 2008-05-28 | 2017-06-09 | 雷沃根生物医药有限公司 | 用于治疗疾病的NF‑κB的非激素甾体调节剂 |
| EP2556083A4 (en) | 2010-04-05 | 2013-12-04 | Validus Biopharma Inc | NONHORMONAL STEROID MODULATORS OF NF-KAPPA-B FOR DISEASE TREATMENT |
| CN102603843B (zh) * | 2012-02-20 | 2013-07-31 | 湖南诺凯生物医药有限公司 | 一种地塞米松中间体的制备方法 |
| WO2017004205A1 (en) | 2015-06-29 | 2017-01-05 | Reveragen Biopharma, Inc. | NON-HORMONAL STEROID MODULATORS OF NF-κB FOR TREATMENT OF DISEASE |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
-
0
- BE BE795243D patent/BE795243A/xx unknown
-
1972
- 1972-02-11 DE DE2207420A patent/DE2207420A1/de active Pending
-
1973
- 1973-01-17 DD DD168292A patent/DD100942A5/xx unknown
- 1973-01-29 DK DK48373*#A patent/DK131942C/da active
- 1973-01-30 CS CS722A patent/CS165381B2/cs unknown
- 1973-02-07 AU AU51931/73A patent/AU468856B2/en not_active Expired
- 1973-02-08 AT AT112373A patent/AT328102B/de not_active IP Right Cessation
- 1973-02-09 HU HUSE1665A patent/HU165442B/hu unknown
- 1973-02-09 FR FR7304677A patent/FR2171374B1/fr not_active Expired
- 1973-02-09 CH CH186473A patent/CH586719A5/xx not_active IP Right Cessation
- 1973-02-09 US US00331060A patent/US3842105A/en not_active Expired - Lifetime
- 1973-02-12 GB GB682073A patent/GB1424212A/en not_active Expired
- 1973-02-12 JP JP48017358A patent/JPS4886854A/ja active Pending
- 1973-02-12 NL NL7301975A patent/NL7301975A/xx not_active Application Discontinuation
- 1973-02-12 SE SE7301934A patent/SE385591B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS165381B2 (US06826419-20041130-M00005.png) | 1975-12-22 |
| HU165442B (US06826419-20041130-M00005.png) | 1974-08-28 |
| GB1424212A (en) | 1976-02-11 |
| DD100942A5 (US06826419-20041130-M00005.png) | 1973-10-12 |
| DK131942C (da) | 1976-02-23 |
| AU468856B2 (en) | 1976-01-22 |
| CH586719A5 (US06826419-20041130-M00005.png) | 1977-04-15 |
| ATA112373A (de) | 1975-05-15 |
| NL7301975A (US06826419-20041130-M00005.png) | 1973-08-14 |
| AT328102B (de) | 1976-03-10 |
| JPS4886854A (US06826419-20041130-M00005.png) | 1973-11-15 |
| SE385591B (sv) | 1976-07-12 |
| BE795243A (fr) | 1973-08-09 |
| DK131942B (da) | 1975-09-29 |
| FR2171374A1 (US06826419-20041130-M00005.png) | 1973-09-21 |
| US3842105A (en) | 1974-10-15 |
| AU5193173A (en) | 1974-08-08 |
| FR2171374B1 (US06826419-20041130-M00005.png) | 1976-06-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2526373C2 (de) | Verfahren zur Herstellung von Δ↑9↑↑(↑↑1↑↑1↑↑)↑-5α-20-Ketosteroiden | |
| DE2207420A1 (de) | Verfahren zur herstellung von 16,17ungesaettigten steroiden | |
| DE2301317C2 (de) | Alkylierte 3,20-Diketo-Δ↑4↑-steroide der Pregnanreihe und Verfahren zu deren Herstellung | |
| DE2236115A1 (de) | Verfahren zur herstellung von delta hoch 4.9(11).16 -3.20diketosteroiden | |
| DE2715863A1 (de) | Verfahren zur herstellung von steroidcarbonsaeuren und ihren estern | |
| DE3109459A1 (de) | (delta)(pfeil hoch)9(pfeil hoch)(pfeil hoch)((pfeil hoch)(pfeil hoch)1(pfeil hoch)(pfeil hoch)1(pfeil hoch)(pfeil hoch))(pfeil hoch)- und (delta)(pfeil hoch)1(pfeil hoch)(pfeil hoch)6(pfeil hoch)-21-chlor-20-keto-steroide der pregnan- und d-homo-pregnan-reihe, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte fuer die synthese von hochwirksamen corticoiden | |
| EP0042606B1 (de) | Verfahren zur Herstellung von 17 Alpha-Hydroxy- und 17a Alpha-Hydroxy-D-homo-etiocarbonsäuren | |
| US2793217A (en) | New derivatives of adrenosterone and a process of making same | |
| DE2748442C3 (de) | 17α-(3-Jodbenzoyloxy)-9α -chlor4-pregnen-3.20-dione, Zwischenprodukte und Verfahren zu ihrer Herstellung, 9α -chlor-17α, 21-dihydroxy-1,4-pregnadien-3,20-dion und dieses enthaltende Arzneimittel | |
| DE2625306C2 (de) | Verfahren zur Herstellung von Pregnan-Derivaten | |
| DE2023122C3 (de) | Verfahren zur Herstellung von Pregnen-Derivaten | |
| CH624684A5 (US06826419-20041130-M00005.png) | ||
| EP0001737B1 (de) | 17-Alpha-(3-Jodbenzoyloxy)-9-Alpha-chlor-4-pregnen-3.20-dione, deren D-Homo-analoga und Verfahren zu ihrer Herstellung | |
| US2862011A (en) | Production of 2-bromo-keto-11-oxygenated-4,17-(20)-pregnadiene-21-oic acid esters | |
| US2875201A (en) | Dehydrotigogenone intermediates | |
| CH621130A5 (US06826419-20041130-M00005.png) | ||
| EP0005523B1 (de) | D-Homosteroide, Verfahren zu deren Herstellung | |
| DE2140291C3 (de) | Verfahren zur Herstellung von Pregnan-Derivaten | |
| DE2526372C2 (de) | Verfahren zur Herstellung von Δ↑9↑↑(↑↑1↑↑1↑↑)↑-5α-D-Homo-20-ketosteroiden | |
| AT232657B (de) | Verfahren zur Herstellung von Enolacylaten von 16α-Alkyl-20-ketosteroiden | |
| DE1131213B (de) | Verfahren zur Herstellung neuer Pregnanverbindungen | |
| US3431287A (en) | Process for the preparation of 2-hydroxymethylene-19-nor-steroids | |
| DE1518907C3 (de) | Verfahren zur Herstellung von Delta hoch 14 -3,20-Diketo-21-acyloxysterioden | |
| DE1907804C3 (de) | 4-Chlor-1alpha,2alpha;6alpha,7alphadimethylen-3-keto-4-pregnene, Verfahren zu deren Herstellung sowie diese enthaltendes Mittel | |
| DE2225324C3 (de) | Verfahren zur Herstellung von 6 a, 21-Difluor-20oxopregnansteroiden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHW | Rejection |