GB888165A - Improvements in or relating to 4-methyl-3-oxo-í~-steroids - Google Patents
Improvements in or relating to 4-methyl-3-oxo-í~-steroidsInfo
- Publication number
- GB888165A GB888165A GB37287/58A GB3728758A GB888165A GB 888165 A GB888165 A GB 888165A GB 37287/58 A GB37287/58 A GB 37287/58A GB 3728758 A GB3728758 A GB 3728758A GB 888165 A GB888165 A GB 888165A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxy
- acetoxy
- dione
- methylpregn
- 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
- 150000003431 steroids Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 3
- 239000003638 chemical reducing agent Substances 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- VFWYHGLPLLLMDD-SZGKAOMTSA-N (2R,8'R,9'S,10'R,13'S,14'S)-3,4',10',13'-tetramethylspiro[1,4-dioxane-2,17'-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-3'-one Chemical compound C1OC(C)[C@]2(CC[C@H]3[C@@H]4CCC5=C(C(CC[C@]5(C)[C@H]4CC[C@]23C)=O)C)OC1 VFWYHGLPLLLMDD-SZGKAOMTSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- ZALBIEJCFBSSHX-OFLOQBSOSA-N (1R,2S,10R,11S,14S,15R)-10-hydroxy-9,11,15,19-tetramethyl-5,8-dioxapentacyclo[12.8.0.02,11.04,10.015,20]docos-19-en-18-one Chemical compound C1OC(C)[C@]2(C(C[C@H]3[C@@H]4CCC5=C(C(CC[C@]5(C)[C@H]4CC[C@]23C)=O)C)OC1)O ZALBIEJCFBSSHX-OFLOQBSOSA-N 0.000 abstract 1
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 abstract 1
- MEMGUVRVJGYLPA-KBBKRBAUSA-N (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-4-(phenylsulfanylmethyl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1(=CC=CC=C1)SCC1=C2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@H]43)O)C)[C@]2(CCC1=O)C MEMGUVRVJGYLPA-KBBKRBAUSA-N 0.000 abstract 1
- ISTFVSGVYPSGKE-QGQWSAILSA-N (8S,9S,10R,13S,14S,17S)-17-acetyl-4,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound CC1=C2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(CCC1=O)C)C)C(C)=O ISTFVSGVYPSGKE-QGQWSAILSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 abstract 1
- VWIGOBCYZDKRDK-UHFFFAOYSA-N 4,10,13-trimethyl-17-(6-methylheptan-2-yl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=C(C)C(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 VWIGOBCYZDKRDK-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- FTWFWIYWVOBQQG-LQUXNCDFSA-N [(8r,9s,10r,13s,14s,17s)-4,10,13-trimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1CC2=C(C)C(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 FTWFWIYWVOBQQG-LQUXNCDFSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000005907 ketalization reaction Methods 0.000 abstract 1
- GSOQEUYHQOEZLX-UHARQNSMSA-N methyl (4R)-4-[(8S,9S,10R,13R,14S,17R)-4,10,13-trimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound COC(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=C(C(CC[C@]4(C)[C@H]3CC[C@]12C)=O)C)=O GSOQEUYHQOEZLX-UHARQNSMSA-N 0.000 abstract 1
- 229960004719 nandrolone Drugs 0.000 abstract 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 abstract 1
- 229960003387 progesterone Drugs 0.000 abstract 1
- 239000000186 progesterone Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB37287/58A GB888165A (en) | 1958-11-19 | 1958-11-19 | Improvements in or relating to 4-methyl-3-oxo-í~-steroids |
| BE584788A BE584788A (fr) | 1958-11-19 | 1959-11-18 | Composés stéroïdes et leur préparation |
| CH8079159A CH380112A (fr) | 1958-11-19 | 1959-11-19 | Verfahren zur Herstellung von Steroidverbindungen |
| FR837321A FR534M (enrdf_load_stackoverflow) | 1958-11-19 | 1960-08-31 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB37287/58A GB888165A (en) | 1958-11-19 | 1958-11-19 | Improvements in or relating to 4-methyl-3-oxo-í~-steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB888165A true GB888165A (en) | 1962-01-24 |
Family
ID=10395256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37287/58A Expired GB888165A (en) | 1958-11-19 | 1958-11-19 | Improvements in or relating to 4-methyl-3-oxo-í~-steroids |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE584788A (enrdf_load_stackoverflow) |
| CH (1) | CH380112A (enrdf_load_stackoverflow) |
| FR (1) | FR534M (enrdf_load_stackoverflow) |
| GB (1) | GB888165A (enrdf_load_stackoverflow) |
-
1958
- 1958-11-19 GB GB37287/58A patent/GB888165A/en not_active Expired
-
1959
- 1959-11-18 BE BE584788A patent/BE584788A/fr unknown
- 1959-11-19 CH CH8079159A patent/CH380112A/fr unknown
-
1960
- 1960-08-31 FR FR837321A patent/FR534M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| FR534M (enrdf_load_stackoverflow) | 1961-05-23 |
| CH380112A (fr) | 1964-07-31 |
| BE584788A (fr) | 1960-05-18 |
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