DD144059A5 - Verfahren zur herstellung von d-homosteroiden - Google Patents

Verfahren zur herstellung von d-homosteroiden Download PDF

Info

Publication number: DD144059A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; homo; steroids; esterified; preparation
Prior art date: 1978-05-12

Application number

DD79212784A

Other languages

German (de)

English (en)

Inventor

Leo Alig

Andor Fuerst

Marcel Mueller

Ulrich Kerb

Rudolf Wiechert

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1978-05-12

Filing date

1979-05-10

Publication date

1980-09-24

1979-05-10 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1980-09-24 Publication of DD144059A5 publication Critical patent/DD144059A5/de

Links

150000000795 D-homosteroids Chemical class 0.000 title claims abstract description 17
238000000034 method Methods 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 10
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 8
-1 iodobenzoyl Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
150000003254 radicals Chemical class 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
239000011737 fluorine Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000002906 microbiologic effect Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
230000033444 hydroxylation Effects 0.000 description 2
238000005805 hydroxylation reaction Methods 0.000 description 2
230000036512 infertility Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
244000005700 microbiome Species 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
KVBWBCRPWVKFQT-UHFFFAOYSA-N 3-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC(I)=C1 KVBWBCRPWVKFQT-UHFFFAOYSA-N 0.000 description 1
DTELTOREECFDBC-UHFFFAOYSA-N 3-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(I)=C1 DTELTOREECFDBC-UHFFFAOYSA-N 0.000 description 1
RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
229910017489 Cu I Inorganic materials 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical compound BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000000750 endocrine system Anatomy 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000002419 homosteroids Chemical class 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000013048 microbiological method Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008207 working material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

DD79212784A 1978-05-12 1979-05-10 Verfahren zur herstellung von d-homosteroiden DD144059A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH520778		1978-05-12
CH184179		1979-02-23

Publications (1)

Publication Number	Publication Date
DD144059A5 true DD144059A5 (de)	1980-09-24

Family

ID=25688808

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79212784A DD144059A5 (de)	1978-05-12	1979-05-10	Verfahren zur herstellung von d-homosteroiden

Country Status (7)

Country	Link
US (1)	US4197406A (da)
EP (1)	EP0005523B1 (da)
JP (1)	JPS54148771A (da)
DD (1)	DD144059A5 (da)
DE (1)	DE2960679D1 (da)
DK (1)	DK195979A (da)
HU (1)	HU179028B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1138857A (en) *	1979-01-24	1983-01-04	Leo Alig	D-homosteroids
US5684153A (en)	1984-08-16	1997-11-04	Beecham Group Plc	Process for the preparation of purine derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2442616A1 (de) *	1974-09-04	1976-03-18	Schering Ag	Neue d-homo-steroide
SE427276B (sv) *	1975-04-03	1983-03-21	Hoffmann La Roche	Forfarande for framstellning av d-homosteroider
EP0001737B1 (de) *	1977-10-26	1981-01-07	Schering Aktiengesellschaft	17-Alpha-(3-Jodbenzoyloxy)-9-Alpha-chlor-4-pregnen-3.20-dione, deren D-Homo-analoga und Verfahren zu ihrer Herstellung

1979
- 1979-05-07 US US06/036,476 patent/US4197406A/en not_active Expired - Lifetime
- 1979-05-09 HU HU79HO2150A patent/HU179028B/hu unknown
- 1979-05-10 DD DD79212784A patent/DD144059A5/de unknown
- 1979-05-10 DK DK195979A patent/DK195979A/da not_active Application Discontinuation
- 1979-05-10 JP JP5643679A patent/JPS54148771A/ja active Pending
- 1979-05-11 EP EP79101453A patent/EP0005523B1/de not_active Expired
- 1979-05-11 DE DE7979101453T patent/DE2960679D1/de not_active Expired

Also Published As

Publication number	Publication date
EP0005523A1 (de)	1979-11-28
EP0005523B1 (de)	1981-08-26
JPS54148771A (en)	1979-11-21
DE2960679D1 (en)	1981-11-19
DK195979A (da)	1979-11-13
US4197406A (en)	1980-04-08
HU179028B (en)	1982-08-28

Publication	Publication Date	Title
AT363201B (de)	1981-07-27	Verfahren zur herstellung von neuen 9alpha,21-dihalogen-11beta,17alpha-dihydroxy-6alpha-
DE2445817C2 (de)	1985-09-05	D-Homosteroide und diese enthaltende Präparate
AT363203B (de)	1981-07-27	Verfahren zur herstellung von neuen 9alpha,21-
CH493449A (de)	1970-07-15	Verfahren zur Oxydation primärer und sekundärer Alkohole
DD144059A5 (de)	1980-09-24	Verfahren zur herstellung von d-homosteroiden
DE2748442C3 (de)	1981-08-27	17&alpha;-(3-Jodbenzoyloxy)-9&alpha; -chlor4-pregnen-3.20-dione, Zwischenprodukte und Verfahren zu ihrer Herstellung, 9&alpha; -chlor-17&alpha;, 21-dihydroxy-1,4-pregnadien-3,20-dion und dieses enthaltende Arzneimittel
DE1568308A1 (de)	1970-02-05	Verfahren zur Herstellung von delta4,9,11-Trienen der 19-Nor-androstanreihe
DE2061183C3 (de)	1980-01-17	15,16 ß -Verbindungen der Pregnanreihe, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2148631C3 (de)	1973-10-18	Verfahren zur Herstellung von in der 9(11)- und/oder 16-Stellung ungesättigten Steroiden
DD143780A5 (de)	1980-09-10	Verfahren zu ihrer herstellung neuer steroide
DE1468900A1 (de)	1969-01-09	Verfahren zur Dehalogenierung
DE960009C (de)	1957-03-14	Verfahren zur Herstellung von 17 ª‡-Oxy-20-ketopregnanen
AT363200B (de)	1981-07-10	Verfahren zur herstellung von neuen 9alpha, 21-dihalogen-11beta, 17alpha-dihydroxy-6alpha-
DE1593407C3 (de)	1976-08-26	17beta-Hydroxy-2-oxaöstra-4,9(10)dien-3-on sowie Verfahren zur Herstellung dieser Verbindung
AT361645B (de)	1981-03-25	Verfahren zur herstellung von neuen d-homosteroiden
DE1241825C2 (de)	1975-10-16	Verfahren zur herstellung von 6-chlor-4,6-dienverbindungen der pregnan-, androstan- oder cholestanreihe
DE957661C (de)	1957-01-17	Verfahren zur Herstellung von 17-Oxy-20-keto-21acyl-oxypregnanen
CH508611A (de)	1971-06-15	Verfahren zur 17a-Alkylierung von 20-Ketosteroiden der Pregnanreihe
DE2646994A1 (de)	1977-04-28	Neue steroide
AT363199B (de)	1981-07-10	Verfahren zur herstellung von neuen 9alpha,21-dihalogen-11beta,17alpha-dihydroxy-6alpha-flour-16alpha-methyl-pregna-1,4-dien-3,20-dion-verbindungen
AT361644B (de)	1981-03-25	Verfahren zur herstellung von neuen d-homosteroiden
DE2409971A1 (de)	1974-09-05	5-cholestenderivate und verfahren zu ihrer herstellung
AT275054B (de)	1969-10-10	Verfahren zur Herstellung von neuen 9β,10α-Steroiden
DE2403985A1 (de)	1974-08-08	Verfahren zur herstellung von racemischem 13beta-aethyl-3-methoxy-8,14-secogona1,3,5(10),8-tetraen-17beta-ol-14-on
DE1173466B (de)	1964-07-09	Verfahren zur Herstellung von Fluorsteroiden der Pregnan- oder Androstanreihe