GB907812A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB907812A GB907812A GB3046859A GB3046859A GB907812A GB 907812 A GB907812 A GB 907812A GB 3046859 A GB3046859 A GB 3046859A GB 3046859 A GB3046859 A GB 3046859A GB 907812 A GB907812 A GB 907812A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregnene
- chlorine
- fluorine
- dione
- difluoro
- 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 1
- 150000003431 steroids Chemical class 0.000 title 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 6
- 229910052801 chlorine Inorganic materials 0.000 abstract 6
- 239000000460 chlorine Substances 0.000 abstract 6
- 229910052731 fluorine Inorganic materials 0.000 abstract 6
- 239000011737 fluorine Chemical group 0.000 abstract 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052794 bromium Inorganic materials 0.000 abstract 4
- -1 hydrocarbon carboxylic acids Chemical class 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- 239000011630 iodine Substances 0.000 abstract 2
- 125000000468 ketone group Chemical group 0.000 abstract 2
- 239000002674 ointment Substances 0.000 abstract 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 abstract 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound 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](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 abstract 2
- WHGCGVQCHBFIHZ-PEYRXNPQSA-N (8S,9R,10S,13S,14S,17R)-2,9-difluoro-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione Chemical compound FC1C(C=C2CC[C@H]3[C@@H]4CC[C@](C(CO)=O)([C@]4(CC([C@@]3([C@]2(C1)C)F)=O)C)O)=O WHGCGVQCHBFIHZ-PEYRXNPQSA-N 0.000 abstract 1
- KFVWCRPPBRASEY-WFYXPZBOSA-N (8S,9S,10R,13S,14S,17R)-2-fluoro-17-(2-fluoroacetyl)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione Chemical compound FC1C(C=C2CC[C@H]3[C@@H]4CC[C@](C(CF)=O)([C@]4(CC([C@@H]3[C@]2(C1)C)=O)C)O)=O KFVWCRPPBRASEY-WFYXPZBOSA-N 0.000 abstract 1
- LEFWXNMOYZJRBM-NMKBPFOZSA-N (8s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,6,7,8,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC[C@]2(C)C3=CC[C@]4(C)[C@@H](CC)CC[C@H]4[C@@H]3CCC2=C1 LEFWXNMOYZJRBM-NMKBPFOZSA-N 0.000 abstract 1
- CZWJCQXZZJHHRH-YCRXJPFRSA-N 2-[(1r,2r,3s,4r,5r,6s)-3-(diaminomethylideneamino)-4-[(2r,3r,4r,5s)-3-[(2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine;sulfuric acid 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@](CO)(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@](CO)(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 CZWJCQXZZJHHRH-YCRXJPFRSA-N 0.000 abstract 1
- 108010001478 Bacitracin Proteins 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 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
- 239000004098 Tetracycline Substances 0.000 abstract 1
- 239000002253 acid Substances 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
- UFWLHIVKHDCSHZ-UHFFFAOYSA-N chembl1595789 Chemical group NC1=NC(N)=NC(C=2C(=CC=CC=2)O)=N1 UFWLHIVKHDCSHZ-UHFFFAOYSA-N 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
- YLHJFOAQDDQFIU-UHFFFAOYSA-N circulin Chemical compound CCC(C)C1NC(=O)C(CC(C)C)NC(=O)C(CCN)NC(=O)C(NC(=O)C(CCN)NC(=O)C(NC(=O)C(CCN)NC=O)C(C)O)CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC1=O YLHJFOAQDDQFIU-UHFFFAOYSA-N 0.000 abstract 1
- 108010002696 circulin Proteins 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 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
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 235000015110 jellies Nutrition 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 238000000034 method Methods 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
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Chemical group 0.000 abstract 1
- 235000003270 potassium fluoride Nutrition 0.000 abstract 1
- 239000011698 potassium fluoride Substances 0.000 abstract 1
- RJKFOVLPORLFTN-UHFFFAOYSA-N progesterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 RJKFOVLPORLFTN-UHFFFAOYSA-N 0.000 abstract 1
- 229940096017 silver fluoride Drugs 0.000 abstract 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- 229960005322 streptomycin Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000829 suppository 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
Classifications
-
- 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
- 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)
Abstract
The invention comprises compounds having the formulae <FORM:0907812/IV (b)/1> wherein X is chlorine or fluorine, X11 is bromine, chlorine, fluorine or iodine, R2 is a b -hydroxy or a keto group, X111 is chlorine, fluorine, bromine, iodine or hydrogen, R4 is the sulphonyl radical of a hydrocarbon sulphonic acid containing 1-12 carbon atoms; 21-esters thereof of hydrocarbon carboxylic acids containing 1-12 carbon atoms and processes for the preparation thereof by dehydrating a 2 - halo - 11b ,17a ,21 - trihydroxy-4-pregnene-3,20-dione 21-acylate to obtain a 4,9(11)-pregnadiene II, treating II with hypohalous acid gives a 9a -halo compound III, III is treated with a base to give a 9b ,11b -epoxy compound IV which with HF gives 2,9a -difluoro-17a ,21-dihydroxy-4-pregnene - 3,11,20-trione 21-acylate V; V is treated with an organic sulphonyl halide to produce a 21-sulphonate ester VIII, VIII with sodium iodide gives a 21-iodo compound IX which on treatment with silver fluoride gives 2,21-difluoro17a -hydroxy-4-pregnene - 3,11,20 - trione. The 11b -hydroxy group when present may be oxidised to an 11-keto group. Alternatively the 21-sulphonate is reacted directly with potassium fluoride to obtain the 21-fluoro compound. Illustrative products of the invention are 2,9a - difluoro - 11b ,17a ,21 - trihydroxy - 4 - pregnene-3,20-dione 21-acetate, 2,9a -difluoro-11b ,17a ,21-trihydroxy-4-pregnene - 3,20 - dione and 2,21-difluoro-11b ,17a -dihydroxy - 4 - pregnene-3,20-dione.ALSO:Pharmaceutical compositions comprise compounds having the formula <FORM:0907812/VI/1> wherein X11 is bromine, chlorine, fluorine or iodine, and R2 is a b -hydroxy or a keto group, 21-esters thereof of hydrocarbon carboxylic acids containing 1-12 carbon atoms, inclusive, or compounds having the formula <FORM:0907812/VI/2> wherein X111 is chlorine, fluorine, bromine, iodine or hydrogen, and X is chlorine or fluorine, and a pharmaceutical diluent. They are employed orally as tablets, parenterally, or topically as ointments, lotions, creams, jellies, suppositories, bougies, and aqueous suspensions. An ointment incorporating 2,9-difluoro-11b , 17a , 21 - trihydroxy - 4 - pregnene - 3,20 - dione may contain in addition neomycin sulphate. Alternatively, novobiocin, bacitracin, circulin, polymyxin B sulphate, gramicidin, streptomycin, dihydrostreptomycin sulphate, oxytetracylcine, chlortetracylcine, tetracycline, chloramphenicol, and the sulphonamides may be used.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75940058A | 1958-09-08 | 1958-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB907812A true GB907812A (en) | 1962-10-10 |
Family
ID=25055501
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1896361A Expired GB907813A (en) | 1958-09-08 | 1959-09-07 | Improvements in or relating to steroids and the manufacture thereof |
| GB3046859A Expired GB907812A (en) | 1958-09-08 | 1959-09-07 | Improvements in or relating to steroids and the manufacture thereof |
| GB1896461A Expired GB907814A (en) | 1958-09-08 | 1959-09-07 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1896361A Expired GB907813A (en) | 1958-09-08 | 1959-09-07 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1896461A Expired GB907814A (en) | 1958-09-08 | 1959-09-07 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (2)
| Country | Link |
|---|---|
| CH (2) | CH388954A (en) |
| GB (3) | GB907813A (en) |
-
1959
- 1959-08-28 CH CH458064A patent/CH388954A/en unknown
- 1959-08-28 CH CH7752159A patent/CH388953A/en unknown
- 1959-09-07 GB GB1896361A patent/GB907813A/en not_active Expired
- 1959-09-07 GB GB3046859A patent/GB907812A/en not_active Expired
- 1959-09-07 GB GB1896461A patent/GB907814A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB907813A (en) | 1962-10-10 |
| GB907814A (en) | 1962-10-10 |
| CH388953A (en) | 1965-03-15 |
| CH388954A (en) | 1965-03-15 |
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