GB1416277A - 3-keto-7 a or beta-lower alkyl-delta5-steroids and process for preparing same - Google Patents
3-keto-7 a or beta-lower alkyl-delta5-steroids and process for preparing sameInfo
- Publication number
- GB1416277A GB1416277A GB877473A GB877473A GB1416277A GB 1416277 A GB1416277 A GB 1416277A GB 877473 A GB877473 A GB 877473A GB 877473 A GB877473 A GB 877473A GB 1416277 A GB1416277 A GB 1416277A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dien
- acyloxy
- proviso
- prepared
- compounds
- 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
- -1 1-cyclopentenyloxy Chemical group 0.000 abstract 8
- 125000004423 acyloxy group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 abstract 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- NSBNSZAXNUGWDJ-UHFFFAOYSA-O monopyridin-1-ium tribromide Chemical compound Br[Br-]Br.C1=CC=[NH+]C=C1 NSBNSZAXNUGWDJ-UHFFFAOYSA-O 0.000 abstract 2
- ALIWVUVYURWMKL-DEPCRRQNSA-N (8'R,9'S,10'R,13'S,14'S)-10',13'-dimethylspiro[1,3-dioxolane-2,17'-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene]-3'-one Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CCC(=O)C=C3C=C2)C)CC[C@@]11C)CC11OCCO1 ALIWVUVYURWMKL-DEPCRRQNSA-N 0.000 abstract 1
- YEWSFUFGMDJFFG-QAGGRKNESA-N (8r,9s,10r,13s,14s)-10,13-dimethyl-2,8,9,11,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 YEWSFUFGMDJFFG-QAGGRKNESA-N 0.000 abstract 1
- JJKJPXNLLLTMNV-IRIMSJTPSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11,17-trione Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C=CC2=C1 JJKJPXNLLLTMNV-IRIMSJTPSA-N 0.000 abstract 1
- JGMOKGBVKVMRFX-LEKSSAKUSA-N (8s,9s,10r,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 JGMOKGBVKVMRFX-LEKSSAKUSA-N 0.000 abstract 1
- YEWSFUFGMDJFFG-UHFFFAOYSA-N (9beta,10alpha)-Androsta-4,6-diene-3,17-dione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3C=CC2=C1 YEWSFUFGMDJFFG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 230000001195 anabolic effect Effects 0.000 abstract 1
- 230000001548 androgenic effect Effects 0.000 abstract 1
- 230000003509 anti-fertility effect Effects 0.000 abstract 1
- 230000001911 anti-progestational effect Effects 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 230000001072 progestational effect Effects 0.000 abstract 1
- 238000010791 quenching Methods 0.000 abstract 1
- 230000000171 quenching effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00236186A US3833621A (en) | 1972-03-20 | 1972-03-20 | 3-keto-7(alpha,beta)-loweralkyl-delta5 steroids and process for preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1416277A true GB1416277A (en) | 1975-12-03 |
Family
ID=22888483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB877473A Expired GB1416277A (en) | 1972-03-20 | 1973-02-22 | 3-keto-7 a or beta-lower alkyl-delta5-steroids and process for preparing same |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3833621A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS4911870A (cg-RX-API-DMAC7.html) |
| BE (1) | BE796909A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1004667A (cg-RX-API-DMAC7.html) |
| CH (1) | CH586236A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2309328A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2181834B1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1416277A (cg-RX-API-DMAC7.html) |
| IL (1) | IL41454A (cg-RX-API-DMAC7.html) |
| NL (1) | NL7302540A (cg-RX-API-DMAC7.html) |
| SE (1) | SE406591B (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA73718B (cg-RX-API-DMAC7.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3917831A (en) * | 1972-03-20 | 1975-11-04 | Richardson Merrell Inc | 3-Keto-7 {60 ,{62 -loweralkyl-{66 {0 5-steroids |
| DK142289B (da) * | 1973-03-28 | 1980-10-06 | Hoffmann La Roche | Analogifremgangsmåde til fremstilling af D-homopregn-4-en-3,20-dioner. |
| CH601351A5 (cg-RX-API-DMAC7.html) * | 1973-09-26 | 1978-07-14 | Hoffmann La Roche | |
| ES432106A1 (es) * | 1973-11-30 | 1976-11-01 | Schering Ag | Procedimiento para la preparacion de d-homo-20-cetopregna- nos. |
| US4139716A (en) * | 1975-04-09 | 1979-02-13 | Hoffmann-La Roche Inc. | 19-Nor-D-homopregnanes |
| CA2100514C (en) * | 1992-07-29 | 2005-03-29 | Johannes A. M. Hamersma | 17-spiromethylene steroids |
| AU2001267904A1 (en) * | 2000-06-30 | 2002-01-14 | Chugai Seiyaku Kabushiki Kaisha | Novel antiandrogenic agent |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1492868A (fr) * | 1965-04-07 | 1967-08-25 | Upjohn Co | Nouveaux stéroïdes du type androstène et leur procédé de préparation |
-
1972
- 1972-03-20 US US00236186A patent/US3833621A/en not_active Expired - Lifetime
-
1973
- 1973-01-31 ZA ZA730718A patent/ZA73718B/xx unknown
- 1973-02-02 IL IL41454A patent/IL41454A/en unknown
- 1973-02-16 CA CA163,914A patent/CA1004667A/en not_active Expired
- 1973-02-22 GB GB877473A patent/GB1416277A/en not_active Expired
- 1973-02-23 NL NL7302540A patent/NL7302540A/xx not_active Application Discontinuation
- 1973-02-24 DE DE19732309328 patent/DE2309328A1/de active Pending
- 1973-03-01 CH CH304873A patent/CH586236A5/xx not_active IP Right Cessation
- 1973-03-10 JP JP48027642A patent/JPS4911870A/ja active Pending
- 1973-03-16 BE BE128910A patent/BE796909A/xx not_active IP Right Cessation
- 1973-03-19 SE SE7303850A patent/SE406591B/xx unknown
- 1973-03-20 FR FR7309992A patent/FR2181834B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2181834B1 (cg-RX-API-DMAC7.html) | 1977-04-22 |
| CA1004667A (en) | 1977-02-01 |
| IL41454A0 (en) | 1973-04-30 |
| DE2309328A1 (de) | 1973-10-04 |
| US3833621A (en) | 1974-09-03 |
| BE796909A (fr) | 1973-07-16 |
| IL41454A (en) | 1977-08-31 |
| JPS4911870A (cg-RX-API-DMAC7.html) | 1974-02-01 |
| CH586236A5 (cg-RX-API-DMAC7.html) | 1977-03-31 |
| NL7302540A (cg-RX-API-DMAC7.html) | 1973-09-24 |
| AU5197173A (en) | 1974-08-08 |
| SE406591B (sv) | 1979-02-19 |
| FR2181834A1 (cg-RX-API-DMAC7.html) | 1973-12-07 |
| ZA73718B (en) | 1973-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19930221 |