IE39593L - Novel alkylated pregnanes. - Google Patents
Novel alkylated pregnanes.Info
- Publication number
- IE39593L IE39593L IE741428A IE142874A IE39593L IE 39593 L IE39593 L IE 39593L IE 741428 A IE741428 A IE 741428A IE 142874 A IE142874 A IE 142874A IE 39593 L IE39593 L IE 39593L
- Authority
- IE
- Ireland
- Prior art keywords
- methyl
- dione
- hydroxy
- pregnen
- pregnadiene
- Prior art date
Links
- 150000003128 pregnanes Chemical class 0.000 title 1
- 239000004593 Epoxy Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 150000003431 steroids Chemical class 0.000 abstract 3
- 229940126062 Compound A Drugs 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000001118 alkylidene group Chemical group 0.000 abstract 2
- 150000002009 diols Chemical class 0.000 abstract 2
- GUHFLRTWNHWJBS-VLTGGNAYSA-N (8r,9s,10s,13s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1C1=CC=C(C(=O)C)[C@@]1(C)CC2 GUHFLRTWNHWJBS-VLTGGNAYSA-N 0.000 abstract 1
- NBLHTECOWAHOPA-LVUPHWHUSA-N (9r,10s,13s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,9,11,12-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@@H](CC[C@@]3(C(C(=O)C)=CC=C33)C)C3=CCC21 NBLHTECOWAHOPA-LVUPHWHUSA-N 0.000 abstract 1
- OUNLEGKRZUPPOS-ONTSXIIYSA-N 1-[(8r,9s,10s,13s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12-decahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1C1=CC=C(C(=O)C)[C@@]1(C)CC2 OUNLEGKRZUPPOS-ONTSXIIYSA-N 0.000 abstract 1
- PQGMAKFMGGZKBA-SRJGTTDWSA-N 1-[(8r,9s,10s,13s,14s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 PQGMAKFMGGZKBA-SRJGTTDWSA-N 0.000 abstract 1
- KBXXJWDSHUJCMA-UHFFFAOYSA-N 3-(oxan-3-yloxy)oxane Chemical compound C1CCOCC1OC1COCCC1 KBXXJWDSHUJCMA-UHFFFAOYSA-N 0.000 abstract 1
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- YLIAINUFORNGRF-PPFHTQHNSA-N C(C)(=O)O.CC(C1=CC=C2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O Chemical compound C(C)(=O)O.CC(C1=CC=C2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C)=O YLIAINUFORNGRF-PPFHTQHNSA-N 0.000 abstract 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000950 dibromo group Chemical group Br* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000004970 halomethyl group Chemical group 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 101150086745 pre gene Proteins 0.000 abstract 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1478968 21-Alkylated-pregnanes AKZO NV 10 July 1974 [11 July 1973] 33149/73 Heading C2U Novel steroids have the formula wherein X is H, F or Cl; Y is H 2 , H(OH), H(O acyl), =0, H(F) except when X is F, or H(C1); R 1 is C 1-4 alkyl; R 2 is H or C 1-4 alkyl; R 3 is H, CH 3 or halogen; Z is OH, O alkyl or O acyl or forms together with R 4 a group as indicated hereinafter; Q is, when #<SP>15</SP> is absent, C 1-4 alkylidene or (#-H) (α-R 4 ) in which R 4 is, together with Z, C 3-5 alkylidenedioxy, C 1-4 alkylidene, C 7-8 aralkylidene, alkylone of the formula in which A is H or halogen and B is H, halogen, C 1-4 alkyl, haloalkyl, alkoxy or phenyl, or a [17α,16α-d]- or [16α,17α-d]-oxazolino group wherein the 2<SP>1</SP>-position may be C 1-4 alkyl- or phenyl-substituted, or Q (when A<SP>15</SP> is present) is CH 3 or halomethyl; and #<SP>1</SP>- and #<SP>6</SP>-double bonds are optionally present. They are prepared from corresponding #<SP>16</SP>-steroids by introducing the required substituents into the D ring or from corresponding steroids containing -COCH 2 R 5 (wherein R 5 is H or halogen) in place of -COCHR 1 R 2 by mono- or di-alkylation. In representative examples (i) 3#-hydroxy- #<SP>9(11),16</SP> - 5α - pregnadien - 20 - one 3 - tetrahydropyranyl ether (from the free 3-ol) is 21- methylated with 3-hydrolysis, the 3#-hydroxy- 21 - methyl - #<SP>9(11),16</SP> - 5α- pregnadien - 20 - one is epoxidized, the 3#-hydroxy-16α,17α-epoxy-21- methyl - #<SP>9(11)</SP> -5α pregnen - 20 - one is converted to 3#,16α,17α - trihydroxy - 21 - methyl- #<SP>9(11)</SP>- 5α-pregnen - 20 - one 16 - acetate 20 - carbethoxyhydrazone, this is converted to 3#,16α,17α - trihydroxy - 21 - methyl - #<SP>9(11)</SP> 5α - pregnen - 20 - one 16 - acetate, this to 3# - hydroxy - 16α,17α - isopropylidenedioxy- 21 - methyl - #<SP>9(11)</SP>5α - pregnen - 20 - one, this to the corresponding 3,20-dione, this to the corresponding #<SP>1</SP>'<SP>4,9(11)</SP> -pregnatriene, this to 9α - bromo - 11# - hydroxy - 16α,17α - isoprpylidenedioxy - 21 - methyl - #<SP>1,4</SP>-pregnadiene- 3,20-dione and this to 11#-hydroxy-16α,17α- isopropylidenedioxy -21 - methyl - #<SP>1</SP>'<SP>4</SP>- pregnadiene - 3,20 - dione; (ii) 3# - hydroxy- 16α,17α - epoxy - 21 - methyl - #<SP>9(11)</SP>5α- pregnen - 20 - one is converted via 3#,17α-dihydroxy - 16# - azido - 21 - methyl - #<SP>9(11)</SP>- 5α - pregnen - 20 - one, 3,17 - diacetate, the corresponding 16#-amino, 16#-chloramino and 16 - imino compounds, 3#,17α - dihydroxy- 16 - acetamido - 21 - methyl - #<SP>9(11),15</SP> - pregnadien - 20 - one diacetate, the corresponding free diol, the 3-monoacetate, 3#,17α-dihydroxy- 16α - acetamido - 21 - methyl - #<SP>9(11)</SP>5α- prenen - 20 - one 3 - acetate, the corresponding free diol, the corresponding 3,20-dione, [16α, 17α-d] - 2<SP>1</SP>- methyl - oxazoline - 21 - methyl- #<SP>9(11)</SP>5α- pregnene - 3,30 - dione, a crude 2,4 - di bromo derivative, [16α,17α-d] - 2<SP>1</SP>- methyl - oxazoline - 21 - methyl - #<SP>1,4,9(11)</SP> pregnatriene - 3,20 - dione, and the corresponding 9α - bromo - 11#-hydroxy - #<SP>1,4</SP>- pregnadiene to 11#- hydroxy - [16α,17α,-d]- 21 - methyloxazoline - 21 - methyl - #<SP>1,4</SP>- pregnadiene - 3,20 - dione; (iii) 3#,11#- diacetoxy - 21 - methyl - #<SP>16</SP> - 5α - pregnen - 20- one is converted via 3#,11# - diacetoxy- 16,21 - dimethyl - #<SP>16</SP> - 5α- pregnen - 20 - one, 3#,11# - dihydroxy - 16#,21 - dimethyl - 16α,17α- epoxy - 5α - pregnan - 20 - one 11# - acetate (compound A), 3#,11#,17α - trihydroxy - 16- methylene - 21 - methyl - 5α - pregnan - 20- one 11#- acetate and the corresponding #<SP>1,4</SP>-3,20 - dione into 11#-17α, - dihydroxy- 16 - methylene - 21 - methyl - #<SP>1,4</SP>-pregnadiene- 3,20 - dione; (iv) 3#,11#- dihydroxy - #<SP>16</SP>- 5α - pregnen - 20 - one is converted via its 3,11 - ditetrahydropyranyl ether, 3#,11#- dihydroxy - 21 - methyl - #<SP>16</SP> - 5α - pregnen- 20 - one, its diacetate, 3#,11#,16# - trihydroxy- 17α - bromo - 21 - methyl - 5α - pregnan - 20- one 3,11 - diacetate 16 - formate, 3#,11#- dihydroxy - 16#,17# - epoxy - 21 - methyl- 5α - isopregnan - 20 - one 11 - acetate, 3#,11#,- 16α - trihydroxy - 17α - azido - 21 - methyl - 5α- pregnan - 20 - one 11 - acetate, the corresponding triacetate, the corresponding 17α-amino compound, 3#,11# - dihydroxy - [17α,16α-d]- 2<SP>1</SP> - methyloxazoline - 21 - methyl - 5α - pregnan- 20 - one 3,11 - diacetate, the corresponding 11 - monoacetate, the corresponding 3,20- dione and the corresponding #<SP>1,4</SP>-compound to 11# - hydroxy[17α,16α-d] - 2<SP>1</SP> - methyloxazoline 21 - methyl - #<SP>1,4</SP> - pregnadiene - 3,20 - dione; (v) 3# - hydroxy - [17α,16α-d] - 2<SP>1</SP> - methyloxazoline - #<SP>9(11)</SP> - 5α - pregnen - 20 - one is converted via the corresponding 3-thp-ether, 3#- hydroxy - [17α,16α,-d] - 2<SP>1</SP> - methyloxazoline- 21 - methyl - #<SP>9(11)</SP> - 5α - pregnen - 20 - one and the corresponding 3,20-dione to [17α, 16α,-d]-2<SP>1</SP>- methyloxazoline - 21 - methyl - #<SP>1</SP>'<SP>4,9(11)</SP>- pregnatriene - 3,20-dione; (vi) compound A (see (iii)) is converted via 3#,11#,17α,-trihydroxy- 16,21 - dimethyl - #<SP>15</SP> - 5α - pregnen - 20 - one 11# - acetate, the corresponding 3-ones, and 11#,17α, - dihydroxy - 16,21 - dimethyl - #<SP>1,4,15</SP>- pregnatriene - 3,20 - dione 11# - acetate into 11#,17α - dihydroxy - 16,21 - dimethyl - #<SP>1,4,15</SP> - pregnatriene - 3,20 - dione; (viii) 3# - hydroxy- #<SP>9(11)</SP>,<SP>16</SP> - 5α , pregnadien - 20 - one acetate is converted via a crude pyrazoline, 3#-hydroxy- 16α,17α - methylene - #<SP>9(11) </SP>- 5α - pregnen - 20- one acetate, the corresponding free 3 - ol, its 3,3-dimethyl ketal and 16α,17α-methylene-21- methyl - #<SP>9(11)</SP> - 5α - pregene - 3,20 - dione to 11# - hydroxy - 16α,17α - methylene - 21- methyl - #<SP>1,4</SP> - pregnadiene - 3,20 - dione; (viii) 16α,17α - isopropylidenedioxy - 21 - methyl - #<SP>9(11)</SP> - 5α - pregnene - 3,20 - dione is converted via a crude 2α-bromo derivative, the corresponding #<SP>1,9(11)</SP> - pregnadiene, and 16α,- 17α, - isopropylidenedioxy - 21 - methyl- #<SP>1,4,9(11)</SP> - pregnatriene - 3,20 - dione (which may also be prepared via a dibromo derivative of the starting material) to 9α-fluoro-11#- hydroxy - 16α,17α - isopropylidenedioxy - 21- methyl - #<SP>1,4</SP> - pregnadiene - 3,20 - dione; (ix) 3#,11# - diacetoxy - 21 - methyl - #<SP>16</SP> - 5α- pregnen - 20 - one is converted via 3#,11#- diacetoxy-16α,17α - ethylene - 21 - methyl- 5α - pregnan - 20 - one, the corresponding 11- monoacetate, the corresponding 3,20-dione and the corresponding #<SP>1</SP>'<SP>4</SP>- compound to 11#- hydroxy - 16α,17α - ethylene - 21 - methyl- #<SP>1,4</SP> - pregnadiene - 3,20 - dione; (x) and (xi) various 11#-ols of the invention are converted via the corresponding #<SP>9(11)</SP>-compounds, 9α- bromo - 11#-ols and 9#,11# - epoxides into 9α-fluoro-11#-ols, and there are oxidized to the corresponding 11-ones; (xii), (Xiii) and (xiv) 9α,11# - dichloro-16α,17α - isopropylidenedioxy- 21 - methyl - #<SP>1,4</SP> - pregnadiene - 3,20 - dione is prepared from the corresponding #<SP>1,4,9(11)</SP> - compound and other inventive compounds are prepared similarly, as are 9α - chloro- 11#- hydroxy - 16α,17α - methylene - 21- methyl - #<SP>1,4</SP> - pregnadiene - 3,20 - dione and 9α - chloro - 11# - fluoro - [16α,17α-d] - 2<SP>1</SP> - methyloxazoline - 21 - methyl - #<SP>1,4</SP> - pregnadiene - 3,20 - dione; (xv) 11# - hydroxy- 16α,17α - isopropylidenedioxy - 21 - methyl- #<SP>1,4,</SP>6 - pregnatriene - 3,20 - dione 11 - acetate is prepared from the corresponding #<SP>1,4</SP>- pregnadiene; and (xvi) 3# - hydroxy - 21- methyl - #<SP>5,16</SP>pregnadien - 20 - one is converted via 3# - hydroxy - 16α,17α - isopropylidenedioxy - 21 - methyl - #<SP>5</SP>- pregnen - 20 - one, 3#- acetoxy - 5α,6α - epoxy - 16α,17α - ipdo- 21 - methyl - 5α - pregnan - 20 - one, the corresponding 5α - hydroxy - 6# - fluoro compound, the corresponding 3#-ol and 3-one and 6α - fluoro - 16α,17α-ipdo - 21 - methyl - #<SP>4</SP>- pregnene - 3,20 - dione to 6α - fluoro - 16α,17α- isopropylidenedioxy - 21 - methyl - #<SP>1,4</SP> pregnadiene-3,20-dione. Corresponding reactions are also effected on the coresponding 21,21-dimethyl compounds, prepared by remethylation of the 21-methyl compounds generally immediately after the first 21-methylation. The novel steroids are anti-inflammatory agents and they may be made up into standard pharmaceutical compositions.
[GB1478968A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33149/73A GB1478968A (en) | 1973-07-11 | 1973-07-11 | Alkylated pregnanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39593L true IE39593L (en) | 1975-01-11 |
| IE39593B1 IE39593B1 (en) | 1978-11-22 |
Family
ID=10349189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1428/74A IE39593B1 (en) | 1973-07-11 | 1974-07-05 | Novel alkylated pregnanes |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5047968A (en) |
| BE (1) | BE817543A (en) |
| CA (1) | CA1050529A (en) |
| DE (1) | DE2433178A1 (en) |
| DK (1) | DK134700B (en) |
| ES (1) | ES428132A1 (en) |
| FI (1) | FI52100C (en) |
| FR (1) | FR2236508B1 (en) |
| GB (1) | GB1478968A (en) |
| HU (1) | HU171711B (en) |
| IE (1) | IE39593B1 (en) |
| NL (1) | NL7409298A (en) |
| SE (1) | SE402920B (en) |
| ZA (1) | ZA744381B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3064460D1 (en) * | 1979-01-24 | 1983-09-08 | Akzo Nv | Novel alkylated pregnanes, processes for their preparation and pharmaceutical compositions containing same |
| IT1134455B (en) * | 1980-11-26 | 1986-08-13 | Lepetit Spa | PROCEDURE FOR THE PREPARATION OF 16ALPHA-HYDROXY-17ALPHA-AMINOPREGNANIC DERIVATIVES |
| EP0523132A1 (en) * | 1990-03-27 | 1993-01-20 | Schering Corporation | PROCESS FOR 9$g(a)-HYDROXY STEROID DEHYDRATION |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3064017A (en) * | 1962-11-13 | Preparation viii | ||
| GB1416427A (en) * | 1972-01-12 | 1975-12-03 | Akzo Nv | Alkylated pregnanes and process for obtaining same |
-
1973
- 1973-07-11 GB GB33149/73A patent/GB1478968A/en not_active Expired
-
1974
- 1974-07-05 IE IE1428/74A patent/IE39593B1/en unknown
- 1974-07-08 ZA ZA00744381A patent/ZA744381B/en unknown
- 1974-07-09 FI FI742103A patent/FI52100C/en active
- 1974-07-10 DK DK371174AA patent/DK134700B/en unknown
- 1974-07-10 CA CA204,503A patent/CA1050529A/en not_active Expired
- 1974-07-10 NL NL7409298A patent/NL7409298A/en not_active Application Discontinuation
- 1974-07-10 DE DE2433178A patent/DE2433178A1/en active Pending
- 1974-07-10 ES ES428132A patent/ES428132A1/en not_active Expired
- 1974-07-10 SE SE7409046A patent/SE402920B/en unknown
- 1974-07-10 JP JP49079023A patent/JPS5047968A/ja active Pending
- 1974-07-11 BE BE146467A patent/BE817543A/en unknown
- 1974-07-11 HU HU74AO00000386A patent/HU171711B/en unknown
- 1974-07-11 FR FR7424189A patent/FR2236508B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI52100C (en) | 1977-06-10 |
| IE39593B1 (en) | 1978-11-22 |
| AU7104074A (en) | 1976-01-15 |
| BE817543A (en) | 1975-01-13 |
| SE402920B (en) | 1978-07-24 |
| FR2236508B1 (en) | 1978-07-28 |
| JPS5047968A (en) | 1975-04-28 |
| ZA744381B (en) | 1975-07-30 |
| DK134700C (en) | 1977-07-11 |
| HU171711B (en) | 1978-03-28 |
| FI210374A7 (en) | 1975-01-12 |
| FI52100B (en) | 1977-02-28 |
| DE2433178A1 (en) | 1975-01-30 |
| FR2236508A1 (en) | 1975-02-07 |
| ES428132A1 (en) | 1976-07-16 |
| SE7409046L (en) | 1975-01-13 |
| GB1478968A (en) | 1977-07-06 |
| CA1050529A (en) | 1979-03-13 |
| DK134700B (en) | 1976-12-27 |
| DK371174A (en) | 1975-03-17 |
| NL7409298A (en) | 1975-01-14 |
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