DE1286032B - Verfahren zur Herstellung von 9(11)-Dehydro-12-desoxysteroiden der Spirostanreihe - Google Patents

Verfahren zur Herstellung von 9(11)-Dehydro-12-desoxysteroiden der Spirostanreihe

Info

Publication number: DE1286032B
Authority: DE; Germany
Prior art keywords: dehydro; spirost; mixture; room temperature; reduction
Prior art date: 1962-08-17
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

Application number

DEG38144A

Other languages

German (de)

English (en)

Inventor

Thomas David Arthur

Clark Dennis Edward

Phillips Gordon Hanley

Elks Joseph

Stephenson Leslie

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Laboratories Ltd

Original Assignee

Glaxo Laboratories Ltd

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.)

1962-08-17

Filing date

1963-07-10

Publication date

1969-01-02

1963-07-10 Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd

1969-01-02 Publication of DE1286032B publication Critical patent/DE1286032B/de

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 20
230000008569 process Effects 0.000 title claims description 9
INLFWQCRAJUDCR-LYLBMTSKSA-N spirostane Chemical class O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 INLFWQCRAJUDCR-LYLBMTSKSA-N 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
239000000725 suspension Substances 0.000 claims description 11
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 10
230000009467 reduction Effects 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
150000003431 steroids Chemical class 0.000 claims description 7
150000001342 alkaline earth metals Chemical class 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
239000003513 alkali Substances 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
YLZUMNXGXFXZNQ-SMCBIBCGSA-N (1S,2S,4S,5'R,6R,7S,8R,9S,13S,16S,18S)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-11-ene-6,2'-oxane]-10-one Chemical compound O([C@@H]1[C@@H]([C@]2(C(=O)C=C3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 YLZUMNXGXFXZNQ-SMCBIBCGSA-N 0.000 claims description 4
YLZUMNXGXFXZNQ-UHFFFAOYSA-N (25R)-3beta-Hydroxy-5alpha-spirost-9(11)-en-12-on Natural products CC1C(C2(C(=O)C=C3C4(C)CCC(O)CC4CCC3C2C2)C)C2OC11CCC(C)CO1 YLZUMNXGXFXZNQ-UHFFFAOYSA-N 0.000 claims description 4
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
150000004292 cyclic ethers Chemical class 0.000 claims description 4
238000005695 dehalogenation reaction Methods 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
239000007868 Raney catalyst Substances 0.000 claims description 3
229910000564 Raney nickel Inorganic materials 0.000 claims description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
230000026030 halogenation Effects 0.000 claims 1
238000005658 halogenation reaction Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
239000007787 solid Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
238000006722 reduction reaction Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
229910000039 hydrogen halide Inorganic materials 0.000 description 5
239000012433 hydrogen halide Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000012448 Lithium borohydride Substances 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical group O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
QOLRLLFJMZLYQJ-LOBDNJQFSA-N Hecogenin Chemical compound O([C@@H]1[C@@H]([C@]2(C(=O)C[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 QOLRLLFJMZLYQJ-LOBDNJQFSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 2
238000006345 epimerization reaction Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
-1 lithium aluminum hydride Chemical compound 0.000 description 2
239000000391 magnesium silicate Substances 0.000 description 2
229940099273 magnesium trisilicate Drugs 0.000 description 2
229910000386 magnesium trisilicate Inorganic materials 0.000 description 2
235000019793 magnesium trisilicate Nutrition 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
BQNMOLSYHYSCMS-UHFFFAOYSA-N 12-Epirockogenin Natural products CC1C(C2(C(O)CC3C4(C)CCC(O)CC4CCC3C2C2)C)C2OC11CCC(C)CO1 BQNMOLSYHYSCMS-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910020366 ClO 4 Inorganic materials 0.000 description 1
OXLGJTRVVNGJRK-UHFFFAOYSA-N Hecogenin Natural products CC1CCC2(CC3CC4C5CCC6CC(O)CCC6(C)C5CC(=O)C4(C)C3C2C)OC1 OXLGJTRVVNGJRK-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
UVLDESQWQRMYKD-UHFFFAOYSA-N Neobotogenin Natural products CC1C(C2(C(=O)CC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 UVLDESQWQRMYKD-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000009471 action Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000011928 denatured alcohol Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
229930182490 saponin Natural products 0.000 description 1
150000007949 saponins Chemical class 0.000 description 1
235000017709 saponins Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general

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)

DEG38144A 1962-08-17 1963-07-10 Verfahren zur Herstellung von 9(11)-Dehydro-12-desoxysteroiden der Spirostanreihe Pending DE1286032B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB31720/62A GB983125A (en)	1962-08-17	1962-08-17	Preparation of 9(11)-dehydro spirostanes and 3-esters thereof

Publications (1)

Publication Number	Publication Date
DE1286032B true DE1286032B (de)	1969-01-02

Family

ID=10327388

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DEG38144A Pending DE1286032B (de)	1962-08-17	1963-07-10	Verfahren zur Herstellung von 9(11)-Dehydro-12-desoxysteroiden der Spirostanreihe

Country Status (7)

Country	Link
US (1)	US3170921A (2)
JP (1)	JPS49179B1 (2)
CH (1)	CH426792A (2)
DE (1)	DE1286032B (2)
DK (1)	DK115619B (2)
GB (1)	GB983125A (2)
SE (1)	SE316762B (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date
JPS50125480U (2) *	1974-03-28	1975-10-15
JPS52104973U (2) *	1976-02-06	1977-08-10
JPS54151676U (2) *	1978-04-11	1979-10-22

1962
- 1962-08-17 GB GB31720/62A patent/GB983125A/en not_active Expired
1963
- 1963-07-02 CH CH815363A patent/CH426792A/de unknown
- 1963-07-05 US US293172A patent/US3170921A/en not_active Expired - Lifetime
- 1963-07-10 DK DK327863AA patent/DK115619B/da unknown
- 1963-07-10 DE DEG38144A patent/DE1286032B/de active Pending
- 1963-07-10 JP JP38036474A patent/JPS49179B1/ja active Pending
- 1963-07-10 SE SE7676/63A patent/SE316762B/xx unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number	Publication date
JPS49179B1 (2)	1974-01-05
SE316762B (2)	1969-11-03
CH426792A (de)	1966-12-31
US3170921A (en)	1965-02-23
GB983125A (en)	1965-02-10
DK115619B (da)	1969-10-27

Publication	Publication Date	Title
EP0100874A2 (de)	1984-02-22	Neue 6,16-Dimethylkortikoide, ihre Herstellung und Verwendung
DE1668784A1 (de)	1971-09-30	Verfahren zur Oxydation primaerer und sekundaerer Alkohole
DE1152101B (de)	1963-08-01	Verfahren zur Herstellung von mit einem Pyrazolring kondensierten Steroidverbindungen
DE1286032B (de)	1969-01-02	Verfahren zur Herstellung von 9(11)-Dehydro-12-desoxysteroiden der Spirostanreihe
DE4239946C2 (de)	2001-09-13	Estranderivate mit einer 14alpha,15alpha-Methylengruppe und Verfahren zu ihrer Herstellung
CH494216A (de)	1970-07-31	Verfahren zur Herstellung von in 3-Stellung einer verätherte Hydroxygruppe tragenden 6-Aminomethyl- 3,5-steroiden
DE1568308B2 (de)	1976-09-09	Verfahren zur herstellung von delta hoch 4,9,11-trienen der 19-nor- androstanreihe, 17-oxygenierte 3-oxo- 7 alpha-methyl-delta hoch 4,9,11-19 nor- androstatriene und diese enthaltende pharmazeutische praeparate sowie 3-oxo-7 alpha -methyl-delta hoch 5 (10), 9 (11) -19-nor- androstadiene
DE2257132B2 (de)	1981-07-23	Verfahren zur Reduktion von 3-Ketosteroiden
CH500958A (de)	1970-12-31	Verfahren zur Herstellung von Steroidverbindungen
DE1012299B (de)	1957-07-18	Verfahren zur Herstellung eines Pregnan-3-ol-20-on-3-aethers oder -esters
DE1618859C (de)	1973-05-24	Verfahren zur Herstellung von 3 keto lObeta methyl llbeta hydroxy Delta hoch 4 steroiden
DE962791C (de)	1957-04-25	Verfahren zur Herstellung von 21-Bromallopregnanderivaten
DE1593501B2 (de)	1975-01-30	15,16 beta-Methylensteroide der 19-Nor-androstan-Reihe, Verfahren zu deren Herstellung sowie diese enthaltende Mittel
DE2230287C3 (de)	1975-04-17	Verfahren zur Herstellung von 11 beta- Hydroxy-16alpha-methyl-steroiden
DE736848C (de)	1943-06-30	Verfahren zur Darstellung von Verbindungen der Pregnanreihe
DE1179548B (de)	1964-10-15	Verfahren zur Herstellung von 21-Bromsteroiden
DE956955C (de)	1957-01-24	Verfahren zur Herstellung von Pregnan- und Allopregnan-3ª‡-o1-11, 20-dion bzw. von Allopregnan-3ª‰, 11ª‡ diol-20-on
DE1593687C (de)	1972-06-22	Verfahren zur Herstellung von neuen Benzo eckige Klammer auf d,e eckige Klam mer zu steroiden der Androstan und Preg nanreihe
DE2003653B2 (de)	1978-04-13	Verfahren zur Herstellung von Pregnan-20-on-3beta, 5beta, 14beta, 21-tetrol bzw. dessen 3,21-di-tetrahydropyranyläther sowie die entsprechenden Zwischenprodukte
DE1122948B (de)	1962-02-01	Verfahren zur Herstellung von 7,17ª‡-Dimethylsteroidverbindungen der Androstanreihe
DE1668205B2 (de)	1973-04-05	16 alpha-alkylthio-9beta, 10alphasteroide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
CH467763A (de)	1969-01-31	Verfahren zur Ketalisierung der 3-Oxogruppe in 5(10)-3-Oxo-19-nor-steroiden
DE1211637B (de)	1966-03-03	Verfahren zur gegebenenfalls voruebergehenden, selektiven 3-Ketalisierung von weiteren Oxogruppen enthaltenden delta 5(10)-3-Oxo-19-nor-steroiden
DE1145170B (de)	1963-03-14	Verfahren zur Herstellung von 9,11-Oxidosteroiden der Androstan- und Pregnanreihe
DE1008286B (de)	1957-05-16	Verfahren zur Herstellung von in 8(9)-Stellung gesaettigten 11-Oxy- und bzw. oder 11-Ketosteroiden