CH371796A - Verfahren zur Herstellung neuer 21-Hemidicarbonsäureester von im Ring A ungesättigten 3,20-Dioxo-21-hydroxy-steroiden der Pregnanreihe - Google Patents

Verfahren zur Herstellung neuer 21-Hemidicarbonsäureester von im Ring A ungesättigten 3,20-Dioxo-21-hydroxy-steroiden der Pregnanreihe

Info

Publication number: CH371796A
Authority: CH; Switzerland
Prior art keywords: methyl; dehydro; fluoro; hemidiglycolate; hydrocortisone
Prior art date: 1958-06-24

Application number

CH6095358A

Other languages

German (de)

English (en)

Inventor

Albert Dr Wettstein

Ludwig Dr Ehmann

Original Assignee

Ciba Geigy

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.)

1958-06-24

Filing date

1958-06-24

Publication date

1963-09-15

1958-06-24 Application filed by Ciba Geigy filed Critical Ciba Geigy

1958-06-24 Priority to CH6095358A priority Critical patent/CH371796A/de

1959-06-17 Priority to ES0250200A priority patent/ES250200A1/es

1963-09-15 Publication of CH371796A publication Critical patent/CH371796A/de

Links

238000000034 method Methods 0.000 title claims description 15
150000002148 esters Chemical class 0.000 title claims description 9
239000002253 acid Substances 0.000 title claims description 5
150000003128 pregnanes Chemical class 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 79
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 39
PIYNUZCGMLCXKJ-UHFFFAOYSA-N 1,4-dioxane-2,6-dione Chemical compound O=C1COCC(=O)O1 PIYNUZCGMLCXKJ-UHFFFAOYSA-N 0.000 claims description 34
229960000890 hydrocortisone Drugs 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 6
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 5
150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
150000003431 steroids Chemical class 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
JWMFYGXQPXQEEM-WZBAXQLOSA-N pregnane Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 JWMFYGXQPXQEEM-WZBAXQLOSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
239000000243 solution Substances 0.000 description 59
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
159000000000 sodium salts Chemical class 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
229960004584 methylprednisolone Drugs 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
229960004544 cortisone Drugs 0.000 description 24
229910052757 nitrogen Inorganic materials 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
238000009835 boiling Methods 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229960002478 aldosterone Drugs 0.000 description 8
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 8
229960001810 meprednisone Drugs 0.000 description 8
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 7
239000010409 thin film Substances 0.000 description 7
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 6
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 5
PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 5
PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 5
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 5
ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 5
229940119740 deoxycorticosterone Drugs 0.000 description 5
239000000155 melt Substances 0.000 description 5
238000004448 titration Methods 0.000 description 5
DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 4
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 4
RYIDIVDIVPQAGH-UHFFFAOYSA-N 3,6-dihydroxyoxepane-2,7-dione Chemical compound C1CC(C(=O)OC(C1O)=O)O RYIDIVDIVPQAGH-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
235000015096 spirit Nutrition 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
VHRSUDSXCMQTMA-UHFFFAOYSA-N 11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound CC12C=CC(=O)C=C1C(C)CC1C2C(O)CC2(C)C(O)(C(=O)CO)CCC21 VHRSUDSXCMQTMA-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
-1 ethylene bis-glycolic anhydride Chemical compound 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
SHCCNDIEMUQSCR-UHFFFAOYSA-N 2,5-dihydroxyhexanedioic acid Chemical compound OC(=O)C(O)CCC(O)C(O)=O SHCCNDIEMUQSCR-UHFFFAOYSA-N 0.000 description 1
GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000011861 anti-inflammatory therapy Methods 0.000 description 1
UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
RCTFHBWTYQOVGJ-UHFFFAOYSA-N chloroform;dichloromethane Chemical compound ClCCl.ClC(Cl)Cl RCTFHBWTYQOVGJ-UHFFFAOYSA-N 0.000 description 1
NWSBNVVOFKKFNV-UHFFFAOYSA-N chloroform;oxolane Chemical compound ClC(Cl)Cl.C1CCOC1 NWSBNVVOFKKFNV-UHFFFAOYSA-N 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
125000001142 dicarboxylic acid group Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000004070 kidney hormone Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
PIDANAQULIKBQS-RNUIGHNZSA-N meprednisone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)CC2=O PIDANAQULIKBQS-RNUIGHNZSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007858 starting material 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
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH6095358A 1958-06-24 1958-06-24 Verfahren zur Herstellung neuer 21-Hemidicarbonsäureester von im Ring A ungesättigten 3,20-Dioxo-21-hydroxy-steroiden der Pregnanreihe CH371796A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH6095358A CH371796A (de)	1958-06-24	1958-06-24	Verfahren zur Herstellung neuer 21-Hemidicarbonsäureester von im Ring A ungesättigten 3,20-Dioxo-21-hydroxy-steroiden der Pregnanreihe
ES0250200A ES250200A1 (es)	1958-06-24	1959-06-17	Procedimiento para la obtencion de nuevos ésteres

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6095358A CH371796A (de)	1958-06-24	1958-06-24	Verfahren zur Herstellung neuer 21-Hemidicarbonsäureester von im Ring A ungesättigten 3,20-Dioxo-21-hydroxy-steroiden der Pregnanreihe

Publications (1)

Publication Number	Publication Date
CH371796A true CH371796A (de)	1963-09-15

Family

ID=4523303

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6095358A CH371796A (de)	1958-06-24	1958-06-24	Verfahren zur Herstellung neuer 21-Hemidicarbonsäureester von im Ring A ungesättigten 3,20-Dioxo-21-hydroxy-steroiden der Pregnanreihe

Country Status (2)

Country	Link
CH (1)	CH371796A (es)
ES (1)	ES250200A1 (es)

1958
- 1958-06-24 CH CH6095358A patent/CH371796A/de unknown
1959
- 1959-06-17 ES ES0250200A patent/ES250200A1/es not_active Expired

Also Published As

Publication number	Publication date
ES250200A1 (es)	1959-10-01

Publication	Publication Date	Title
CH540244A (de)	1973-08-15	Verfahren zur Herstellung neuer Halogenpregnadiene
DE1153745B (de)	1963-09-05	Verfahren zur Herstellung von 4-Halogen-3-sulfamoylbenzoesaeureestern
CH371796A (de)	1963-09-15	Verfahren zur Herstellung neuer 21-Hemidicarbonsäureester von im Ring A ungesättigten 3,20-Dioxo-21-hydroxy-steroiden der Pregnanreihe
DE1468890B1 (de)	1971-07-29	Verfahren zur Herstellung von Tetrahydroindan-Zwischenprodukten fuer Steroidderivate
EP0011121B1 (de)	1982-05-05	Hydrocortisonester, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung
US3128291A (en)	1964-04-07	New hemiacetals and hemicaetal esters of the androstane series and a method for their production
AT205678B (de)	1959-10-10	Verfahren zur Herstellung neuer progestativ wirksamer Ester des 17 α-Oxyprogesterons mit protrahierter Wirkungsdauer
DE1111627B (de)	1961-07-27	Verfahren zur Herstellung von neuen Estern
DE871152C (de)	1953-03-19	Verfahren zur Herstellung neuer Ester von 20, 21-Ketolen der Pregnanreihe
DE931947C (de)	1955-08-22	Verfahren zur Herstellung von 20, 21-Pregnanketolestern
AT233176B (de)	1964-04-25	Verfahren zur Herstellung neuer 21-Halbester von im Ring A ungesättigten 3, 20-Dioxo-21-hydroxypregnanverbindungen
DE1593310C (de)	1972-02-24	Verfahren zur Herstellung von Derivaten des l,5-Dioxo-5,6,7,7alpha-tetrahydroindans
DE901415C (de)	1954-01-11	Verfahren zur Herstellung von í¸-Androstadienol-(17)-on-(3) bzw. seiner funktionellen Derivate der Hydroxylgruppe
DE1468531C2 (de)	1977-11-17	Rechtsdrehende Hexahydroindanpropionsäurederivate und Verfahren zu ihrer Herstellung
AT224821B (de)	1962-12-10	Verfahren zur Herstellung von Δ1, 4-Pregnadien-17α, 21-diol-3, 20-dion
DE2022695A1 (de)	1970-11-19	Verfahren zur Herstellung von 21-Phosphaten von Steroiden der Pregnanreihe
AT221723B (de)	1962-06-12	Verfahren zur Herstellung therapeutisch wertvoller Carbonsäureester von 17-Alkyl-19-nor-testosteronen
DE1770674A1 (de)	1970-02-19	Pyrimidinbasen
DE1143514B (de)	1963-02-14	Verfahren zur Herstellung von OEstriol-16, 17-dihemisuccinat bzw. von dessen wasserloeslichen Salzen
Ünseren et al.	1907	ÇEKMECE NUCLEAR RESEARCH CENTER
CH370776A (de)	1963-07-31	Verfahren zur Herstellung von neuen Estern einer Pregnenverbindung
CH571023A5 (en)	1975-12-31	D-homo-corticosteroids - anti-inflammatories
DE2410232A1 (de)	1975-07-03	Verfahren zur herstellung von oestriol16,17-di-m-sulfobenzoat bzw. dessen wasserloeslichen salzen
DE1090207B (de)	1960-10-06	Verfahren zur Herstellung wasserloeslicher Corticosteroidderivate
CH346539A (de)	1960-05-31	Verfahren zur Herstellung von 21-Monoestern von Retrocortin