GB898292A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB898292A GB898292A GB892460A GB892460A GB898292A GB 898292 A GB898292 A GB 898292A GB 892460 A GB892460 A GB 892460A GB 892460 A GB892460 A GB 892460A GB 898292 A GB898292 A GB 898292A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnadiene
- dione
- dihydroxy
- fluorine
- hydrogen
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000003431 steroids Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 229910052731 fluorine Chemical group 0.000 abstract 4
- 239000011737 fluorine Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- SUPOKHOQAKXOHJ-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 SUPOKHOQAKXOHJ-BYZMTCBYSA-N 0.000 abstract 1
- -1 17-disubstituted aminoacetate ester Chemical class 0.000 abstract 1
- BGWSMDYVVVJGBB-UHFFFAOYSA-N 2-(diethylamino)acetic acid;hydrochloride Chemical compound Cl.CCN(CC)CC(O)=O BGWSMDYVVVJGBB-UHFFFAOYSA-N 0.000 abstract 1
- 108010001478 Bacitracin Proteins 0.000 abstract 1
- ASXBYYWOLISCLQ-UHFFFAOYSA-N Dihydrostreptomycin Natural products O1C(CO)C(O)C(O)C(NC)C1OC1C(CO)(O)C(C)OC1OC1C(N=C(N)N)C(O)C(N=C(N)N)C(O)C1O ASXBYYWOLISCLQ-UHFFFAOYSA-N 0.000 abstract 1
- 108010026389 Gramicidin Proteins 0.000 abstract 1
- SBKRTALNRRAOJP-BWSIXKJUSA-N N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(3S,6S,9S,12S,15R,18R,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-6-methylheptanamide (6S)-N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(3S,6S,9S,12S,15R,18R,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-6-methyloctanamide sulfuric acid Polymers OS(O)(=O)=O.CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@@H](CCN)NC1=O)[C@@H](C)O.CC[C@H](C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@@H](CCN)NC1=O)[C@@H](C)O SBKRTALNRRAOJP-BWSIXKJUSA-N 0.000 abstract 1
- YJQPYGGHQPGBLI-UHFFFAOYSA-N Novobiocin Natural products O1C(C)(C)C(OC)C(OC(N)=O)C(O)C1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 239000004098 Tetracycline Substances 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 229960003071 bacitracin Drugs 0.000 abstract 1
- 229930184125 bacitracin Natural products 0.000 abstract 1
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229960005091 chloramphenicol Drugs 0.000 abstract 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- ASXBYYWOLISCLQ-HZYVHMACSA-N dihydrostreptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O ASXBYYWOLISCLQ-HZYVHMACSA-N 0.000 abstract 1
- 229960002222 dihydrostreptomycin Drugs 0.000 abstract 1
- 239000003221 ear drop Substances 0.000 abstract 1
- 229960003276 erythromycin Drugs 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 229960004905 gramicidin Drugs 0.000 abstract 1
- ZWCXYZRRTRDGQE-SORVKSEFSA-N gramicidina Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)CC(C)C)C(=O)NCCO)=CNC2=C1 ZWCXYZRRTRDGQE-SORVKSEFSA-N 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 abstract 1
- 229960002950 novobiocin Drugs 0.000 abstract 1
- YJQPYGGHQPGBLI-KGSXXDOSSA-N novobiocin Chemical compound O1C(C)(C)[C@H](OC)[C@@H](OC(N)=O)[C@@H](O)[C@@H]1OC1=CC=C(C(O)=C(NC(=O)C=2C=C(CC=C(C)C)C(O)=CC=2)C(=O)O2)C2=C1C YJQPYGGHQPGBLI-KGSXXDOSSA-N 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 229960002180 tetracycline Drugs 0.000 abstract 1
- 229930101283 tetracycline Natural products 0.000 abstract 1
- 235000019364 tetracycline Nutrition 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0898292/IV (b)/1> <FORM:0898292/IV (b)/2> <FORM:0898292/IV (b)/3> <FORM:0898292/IV (b)/4> wherein R is H or a hydrocarbyl radical containing 1-12 carbon atoms, o -carboxy-lower-hydrocarbyl containing 1-12 carbon atoms, including metal salts thereof, disubstituted-amino-methylene radicals including salts thereof, R1 is hydrogen or fluorine, Y is b -hydroxymethylene or carbonyl, and Z is hydrogen, fluorine, chlorine or bromine and processes for the production thereof (a) by esterifying the corresponding 17a -hydroxy compound with an acid anhydride in the presence of an acidic esterification catalyst and then, if desired, thereafter hydrolysing any 3-enol ester formed under mild conditions with a base, (b) dehydrating the corresponding 17-hydroxy compound to produce the corresponding D 9(11)-compound, esterifying, reacting the resulting 17-acyloxy ester with N-bromoacetamide to form the 9-bromo derivative and removing the bromine atom with zinc and acetic acid, (c) converting the corresponding 17-hydroxy compound to a 17-bromoacetate ester, reacting the latter with a secondary amine to produce the 17-disubstituted aminoacetate ester, treating with an acid to form an acid salt or with an alkyl halide to form a quaternary ammonium salt. Illustrative products of the invention are 6a ,16-dimethyl - 9a - fluoro - 11b , 17a - dihydroxy - 1, 4 - pregnadiene-3,20-dione 17-acetate, the corresponding diethylaminoacetate hydrochloride, 6a , 9a - difluoro - 11b , 17a - dihydroxy - 16a - methyl - 1,4-pregnadiene-3,20-dione 17-acetate and the corresponding 4-pregnene compounds. Specifications 898,291, 898,293 and 898,294 are referred to.ALSO:Pharmaceutical compositions comprise compounds of the formula <FORM:0898292/VI/1> <FORM:0898292/VI/2> <FORM:0898292/VI/3> <FORM:0898292/VI/4> wherein R is H or a hydocarbyl radical containing 1-12 carbon atoms, o -carboxy-lower hydrocarbyl containing 1-12 carbon atoms, including metal salts thereof, disubstituted-amino methylene radicals including salts thereof, R1 is hydrogen or fluorine, Y is b -hydroxymethylene or carbonyl and Z is hydrogen, fluorine, chlorine or bromine together with a pharmaceutical diluent. They are employed orally as tablets, powders, pills or capsules, parenterally as solutions and aqueous suspensions, and topically as creams, lotions with or without coacting antibiotics e.g. penicillins, tetracycline, bacitracin, novobiocin, erythromycin polymyxin B sulphate, gramicidin, streptomycin sulphate, dihydrostreptomycin, and chloramphenicol. Examples describe an eye-ear drop composition containing 6a ,16a -dimethyl-9a -fluoro-11b ,17a -dihydroxy - 1,4 - pregnadiene - 3,20 - dione and an ointment containing 6a ,16a -dimethyl-9a -fluoro - 11b ,17a - dihydroxy - 1,4 - pregnadiene-3,20-dione 17-acetate. Specifications 898,291, 898,293 and 898,294 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80008259A | 1959-03-18 | 1959-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB898292A true GB898292A (en) | 1962-06-06 |
Family
ID=25177449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB892460A Expired GB898292A (en) | 1959-03-18 | 1960-03-14 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH390242A (en) |
| GB (1) | GB898292A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2655570A1 (en) * | 1975-12-12 | 1977-06-16 | Ciba Geigy Ag | NEW POLYHALOGSTEROIDS AND METHODS FOR THEIR PRODUCTION |
| DE2743069A1 (en) * | 1976-09-29 | 1978-03-30 | Ciba Geigy Ag | METHOD FOR PRODUCING MULTIPLE HALOGENED STEROIDS |
| EP0039311A1 (en) * | 1980-04-29 | 1981-11-04 | Ciba-Geigy Ag | Halogenated steroids |
| EP0078235A3 (en) * | 1981-10-23 | 1983-06-29 | Ciba-Geigy Ag | Dihalogenated steroids |
| DE3227312A1 (en) * | 1982-07-19 | 1984-01-19 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE |
| EP0149222A3 (en) * | 1984-01-02 | 1986-05-14 | Schering Aktiengesellschaft Berlin Und Bergkamen | 6-alpha, 16 alpha-dimethyl corticoids |
| EP0149464A3 (en) * | 1984-01-16 | 1986-05-28 | Schering Aktiengesellschaft Berlin Und Bergkamen | 6-alpha, 16-beta-dimethyl steroids |
-
1960
- 1960-03-14 GB GB892460A patent/GB898292A/en not_active Expired
- 1960-03-15 CH CH291160A patent/CH390242A/en unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2655570A1 (en) * | 1975-12-12 | 1977-06-16 | Ciba Geigy Ag | NEW POLYHALOGSTEROIDS AND METHODS FOR THEIR PRODUCTION |
| DE2743069A1 (en) * | 1976-09-29 | 1978-03-30 | Ciba Geigy Ag | METHOD FOR PRODUCING MULTIPLE HALOGENED STEROIDS |
| EP0039311A1 (en) * | 1980-04-29 | 1981-11-04 | Ciba-Geigy Ag | Halogenated steroids |
| EP0078235A3 (en) * | 1981-10-23 | 1983-06-29 | Ciba-Geigy Ag | Dihalogenated steroids |
| DE3227312A1 (en) * | 1982-07-19 | 1984-01-19 | Schering AG, 1000 Berlin und 4709 Bergkamen | NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE |
| EP0100874A3 (en) * | 1982-07-19 | 1985-04-17 | Schering Aktiengesellschaft Berlin Und Bergkamen | 6,16-dimethyl corticoids, their preparation and their use |
| US4555507A (en) * | 1982-07-19 | 1985-11-26 | Schering Aktiengesellschaft | Novel 6, 16-dimethylcorticoids, their preparation and use |
| EP0149222A3 (en) * | 1984-01-02 | 1986-05-14 | Schering Aktiengesellschaft Berlin Und Bergkamen | 6-alpha, 16 alpha-dimethyl corticoids |
| EP0149464A3 (en) * | 1984-01-16 | 1986-05-28 | Schering Aktiengesellschaft Berlin Und Bergkamen | 6-alpha, 16-beta-dimethyl steroids |
| US4777165A (en) * | 1984-01-16 | 1988-10-11 | Schering Aktiengesellschaft | 6α, 16β-dimethyl corticoids and their anti-inflammatory use |
Also Published As
| Publication number | Publication date |
|---|---|
| CH390242A (en) | 1965-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2816902A (en) | Hydroxylated steroids | |
| GB898292A (en) | Improvements in or relating to steroids and the manufacture thereof | |
| GB901293A (en) | Improvements in or relating to steroids | |
| GB1118976A (en) | New bisnorcholane derivatives and process for their manufacture | |
| GB1031905A (en) | Novel steroid compounds, their preparation and pharmaceutical compositions containing them | |
| US2818408A (en) | Steroid compounds and process | |
| US3038912A (en) | 20(bets)-[(monoalkylamino)methyl]pregn-5-en-3beta-ols, esters corresponding and intermediates thereto | |
| GB876192A (en) | Improvements in or relating to steroids and the manufacture thereof | |
| GB857114A (en) | Improvements in or relating to 16-substituted steroid compounds | |
| US3507857A (en) | Amidinohydrazones of ketosteroids | |
| US3458541A (en) | 13 - alkyl - 17 - (bis(2-hydroxyethyl)amino)-gon-4-en-3-ones,dinitrates | |
| US2950281A (en) | delta5-3-ethylenedioxy-11, 20-diketo-21-iodopregnene | |
| GB894605A (en) | Improvements in or relating to steroids and the manufacture thereof | |
| US3192249A (en) | Methyl 3beta, 5beta-dihydroxy-b-norpregnan-20-one-6beta-carboxylate | |
| US2870141A (en) | 6-fluoro-20-hydroxy-4-pregnen-3-ones and the 20-acylates thereof | |
| GB1030754A (en) | Novel d-nor steroids and processes for their manufacture | |
| US3372174A (en) | Process for converting 17alpha-hydroperoxy-20-keto-pregnanes into the corresponding 17-keto-androstanes | |
| US3043835A (en) | 11-oxygenated 17alpha-carboxyethyl-17beta-hydroxyandrosta-1, 4-dien-3-one lactones | |
| GB878069A (en) | Improvements in or relating to steroids and the manufacture thereof | |
| GB933151A (en) | New steroid derivatives and methods for their production | |
| GB894642A (en) | Improvements in or relating to steroids and the manufacture thereof | |
| GB826629A (en) | Improvements in or relating to steroids and the manufacture thereof | |
| US3408372A (en) | Preparation of 3-keto-10beta-methyl-11beta-hydroxy-delta4 steroids | |
| GB959793A (en) | Improvements in or relating to steroids | |
| GB980245A (en) | New-6-alkyl-steroids |