DD250319A5 - Verfahren zur herstellung von 1-methyl-15alpha-alkyl-androst-1,4-dien-3,17-dienen - Google Patents

Verfahren zur herstellung von 1-methyl-15alpha-alkyl-androst-1,4-dien-3,17-dienen Download PDF

Info

Publication number: DD250319A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; diene; dione; androsta; hydroxy
Prior art date: 1985-11-01

Application number

DD86295752A

Other languages

German (de)

English (en)

Inventor

Ulrich Kerb

Original Assignee

��@��k��

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.)

1985-11-01

Filing date

1986-10-30

Publication date

1987-10-08

1986-10-30 Application filed by ��@��k�� filed Critical ��@��k��

1987-10-08 Publication of DD250319A5 publication Critical patent/DD250319A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 26
229940011871 estrogen Drugs 0.000 claims abstract description 19
239000000262 estrogen Substances 0.000 claims abstract description 19
238000011282 treatment Methods 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
230000015572 biosynthetic process Effects 0.000 claims abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
201000010099 disease Diseases 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
238000000034 method Methods 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 8
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 claims description 7
102000014654 Aromatase Human genes 0.000 claims description 3
108010078554 Aromatase Proteins 0.000 claims description 3
IAINSPSNQUZMBD-HNRVFZENSA-N (8r,9s,10s,13s,14r,15s)-15-(1,2-dihydroxypropyl)-1,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C(C)[C@]2(C)[C@H]3CC[C@]4(C)C(=O)C[C@H](C(O)C(O)C)[C@H]4[C@@H]3CCC2=C1 IAINSPSNQUZMBD-HNRVFZENSA-N 0.000 claims description 2
JSPJLYZMQGIXRE-GTYZJQRUSA-N 1-[(8R,9S,10S,13R,14S)-1,10-dimethyl-3,17-dioxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-13-yl]pentan-2-yl acetate Chemical compound C(C)(=O)OC(CCC)C[C@@]12C(CC[C@H]1[C@@H]1CCC3=CC(C=C([C@]3(C)[C@H]1CC2)C)=O)=O JSPJLYZMQGIXRE-GTYZJQRUSA-N 0.000 claims description 2
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
230000000144 pharmacologic effect Effects 0.000 claims description 2
YSXJHBCXROSVHR-OKBDFUAMSA-N [(8r,9s,10s,13s,14r,15s)-1,10,13-trimethyl-3,17-dioxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-15-yl]methyl pentanoate Chemical compound O=C1C=C(C)[C@]2(C)[C@H]3CC[C@]4(C)C(=O)C[C@H](COC(=O)CCCC)[C@H]4[C@@H]3CCC2=C1 YSXJHBCXROSVHR-OKBDFUAMSA-N 0.000 claims 1
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238000002844 melting Methods 0.000 description 47
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
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238000007254 oxidation reaction Methods 0.000 description 5
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238000004458 analytical method Methods 0.000 description 1
LUJVUUWNAPIQQI-QAGGRKNESA-N androsta-1,4-diene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 LUJVUUWNAPIQQI-QAGGRKNESA-N 0.000 description 1
PEPMWUSGRKINHX-TXTPUJOMSA-N atamestane Chemical compound C1C[C@@H]2[C@@]3(C)C(C)=CC(=O)C=C3CC[C@H]2[C@@H]2CCC(=O)[C@]21C PEPMWUSGRKINHX-TXTPUJOMSA-N 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
239000004621 biodegradable polymer Substances 0.000 description 1
229920002988 biodegradable polymer Polymers 0.000 description 1
201000008275 breast carcinoma Diseases 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003433 contraceptive agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000005661 deetherification reaction Methods 0.000 description 1
238000007269 dehydrobromination reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
NKRNGKIEDAVMHL-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1 NKRNGKIEDAVMHL-UHFFFAOYSA-L 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000012173 estrus Effects 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000003958 fumigation Methods 0.000 description 1
238000002309 gasification Methods 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
239000002622 gonadotropin Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
238000005907 ketalization reaction Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000005644 metestrus Effects 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000002547 new drug Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000016087 ovulation Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000011505 plaster Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000011421 subcutaneous treatment Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000003786 synthesis reaction Methods 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
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003981 vehicle Substances 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD86295752A 1985-11-01 1986-10-30 Verfahren zur herstellung von 1-methyl-15alpha-alkyl-androst-1,4-dien-3,17-dienen DD250319A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853539244 DE3539244A1 (de)	1985-11-01	1985-11-01	1-methyl-15(alpha)-alkyl-androsta- 1,4-dien-3,17-dione, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate

Publications (1)

Publication Number	Publication Date
DD250319A5 true DD250319A5 (de)	1987-10-08

Family

ID=6285220

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86295752A DD250319A5 (de)	1985-11-01	1986-10-30	Verfahren zur herstellung von 1-methyl-15alpha-alkyl-androst-1,4-dien-3,17-dienen

Country Status (16)

Country	Link
EP (1)	EP0225272B1 (da)
JP (1)	JPS62155294A (da)
CN (1)	CN86107158A (da)
AT (1)	ATE41936T1 (da)
AU (1)	AU6432986A (da)
DD (1)	DD250319A5 (da)
DE (2)	DE3539244A1 (da)
DK (1)	DK515486A (da)
FI (1)	FI864329A7 (da)
GR (1)	GR880300115T1 (da)
HU (1)	HU196079B (da)
IL (1)	IL80176A0 (da)
NO (1)	NO864365L (da)
NZ (1)	NZ218071A (da)
PT (1)	PT83659B (da)
ZA (1)	ZA868333B (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3703722A1 (de) *	1987-02-04	1988-08-18	Schering Ag	1-methyl-15(alpha)-(1,2-dialkanoyloxyalkyl)-androsta-1,4-dien-3,17-dione, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate
DE3705990A1 (de) *	1987-02-20	1988-09-01	Schering Ag	1-methyl-15(alpha)-(1-oxyalkyl)-androsta-1,4-dien- 3,17-dione, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate
DE3715869A1 (de) *	1987-05-07	1988-11-17	Schering Ag	Verfahren zur herstellung von 1-methyl-androsta-1,4-dien-3,17-dion und die neuen zwischenprodukte fuer dieses verfahren
CH683151A5 (de) *	1991-04-24	1994-01-31	Ciba Geigy Ag	Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus.
DE4435368A1 (de) *	1994-09-22	1996-03-28	Schering Ag	Verwendung von Aromatasehemmern zur Herstellung eines Arzneimittels zur Behandlung eines relativen Androgenmangels beim Mann

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3766224A (en) *	1971-06-03	1973-10-16	Sandoz Ag	15-methyl-substituted steroids
DE3322285A1 (de) *	1983-06-18	1984-12-20	Schering AG, 1000 Berlin und 4709 Bergkamen	1-alkyl-androsta-1,4-dien-3,17-dione, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate

1985
- 1985-11-01 DE DE19853539244 patent/DE3539244A1/de not_active Withdrawn
1986
- 1986-09-29 IL IL80176A patent/IL80176A0/xx unknown
- 1986-10-23 AU AU64329/86A patent/AU6432986A/en not_active Abandoned
- 1986-10-24 FI FI864329A patent/FI864329A7/fi not_active Application Discontinuation
- 1986-10-28 DK DK515486A patent/DK515486A/da not_active Application Discontinuation
- 1986-10-28 NZ NZ218071A patent/NZ218071A/xx unknown
- 1986-10-29 DE DE8686730177T patent/DE3662693D1/de not_active Expired
- 1986-10-29 AT AT86730177T patent/ATE41936T1/de not_active IP Right Cessation
- 1986-10-29 EP EP86730177A patent/EP0225272B1/de not_active Expired
- 1986-10-30 DD DD86295752A patent/DD250319A5/de unknown
- 1986-10-31 JP JP61258659A patent/JPS62155294A/ja active Pending
- 1986-10-31 NO NO864365A patent/NO864365L/no unknown
- 1986-10-31 PT PT83659A patent/PT83659B/pt unknown
- 1986-10-31 ZA ZA868333A patent/ZA868333B/xx unknown
- 1986-10-31 HU HU864575A patent/HU196079B/hu not_active IP Right Cessation
- 1986-11-01 CN CN198686107158A patent/CN86107158A/zh active Pending
1989
- 1989-06-22 GR GR88300115T patent/GR880300115T1/el unknown

Also Published As

Publication number	Publication date
JPS62155294A (ja)	1987-07-10
NO864365L (no)	1987-05-04
DE3539244A1 (de)	1987-05-07
NO864365D0 (no)	1986-10-31
FI864329A7 (fi)	1987-05-02
HU196079B (en)	1988-09-28
PT83659B (en)	1988-08-30
DK515486D0 (da)	1986-10-28
ATE41936T1 (de)	1989-04-15
CN86107158A (zh)	1987-08-05
IL80176A0 (en)	1986-12-31
EP0225272A1 (de)	1987-06-10
GR880300115T1 (en)	1989-06-22
ZA868333B (en)	1987-06-24
HUT43618A (en)	1987-11-30
FI864329A0 (fi)	1986-10-24
DE3662693D1 (en)	1989-05-11
EP0225272B1 (de)	1989-04-05
NZ218071A (en)	1989-01-06
AU6432986A (en)	1987-05-07
PT83659A (en)	1986-11-01
DK515486A (da)	1987-05-02

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DE1618830C3 (de)	1975-02-20	In 3-und 17-Stellung sauerstoffhaltige 11 beta-OB-13beta-C-gona-1,3,5(10)-triene und Verfahren zu ihrer Herstellung
DE3124780C2 (da)	1992-04-23
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DD250319A5 (de)	1987-10-08	Verfahren zur herstellung von 1-methyl-15alpha-alkyl-androst-1,4-dien-3,17-dienen
DE4021433A1 (de)	1992-01-09	Antiandrogene mit steroid(3,2-c)pyrazol-struktur
EP0289451B1 (de)	1993-10-27	3-Methylen-4-androsten-17-one, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
WO1993013122A1 (de)	1993-07-08	3-methylsulfonylhydrazono- und 3-oxyimino-steroide, ein verfahren zu deren herstellung, diese steroide enthaltende pharmazeutische präparate sowie ihre verwendung zur herstellung von arzneimitteln
EP0286578A1 (de)	1988-10-12	4,15-Disubstituierte 4-Androsten-3,17-dione und Verfahren zu deren Herstellung
DE2413559A1 (de)	1974-10-17	Neue steroide, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate
EP0164699A2 (de)	1985-12-18	1,2Beta-Methylen-4-androsten-und 4,6-androstadien-3,17-dione
DE2636405C2 (de)	1982-07-08	&Delta;&uarr;1&uarr;&uarr;5&uarr;-17&alpha;-Chloräthinyl- und -Propinylsteroide der Östranreihe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Präparate
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EP0280119A1 (de)	1988-08-31	1-Methyl-15alpha-(1-Oxyalkyl)-androsta-1,4-dien-3,17-dione, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
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