GB855800A - New cyclopentanophenanthrene derivatives and process for the production thereof - Google Patents
New cyclopentanophenanthrene derivatives and process for the production thereofInfo
- Publication number
- GB855800A GB855800A GB9187/57A GB918757A GB855800A GB 855800 A GB855800 A GB 855800A GB 9187/57 A GB9187/57 A GB 9187/57A GB 918757 A GB918757 A GB 918757A GB 855800 A GB855800 A GB 855800A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- keto
- chloro
- bromo
- hydroxy
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- MRKZAZMYXYSBDG-UHFFFAOYSA-N cyclopentyl propanoate Chemical class CCC(=O)OC1CCCC1 MRKZAZMYXYSBDG-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- 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 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Chemical group 0.000 abstract 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229960004719 nandrolone Drugs 0.000 abstract 2
- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 abstract 1
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- IDWOPWCPFXYGDU-FBPKJDBXSA-N BrC1=C2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@H]43)O)C)[C@]2(CCC1=O)C Chemical compound BrC1=C2CC[C@@H]3[C@H](CC[C@@]4([C@H](CC[C@H]43)O)C)[C@]2(CCC1=O)C IDWOPWCPFXYGDU-FBPKJDBXSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- FGPGANCDNDLUST-CEGNMAFCSA-N Ethyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](CC)(O)[C@@]1(C)CC2 FGPGANCDNDLUST-CEGNMAFCSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229960004544 cortisone Drugs 0.000 abstract 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 abstract 1
- 229960003654 desoxycortone Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- CHNXZKVNWQUJIB-CEGNMAFCSA-N ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229960003387 progesterone Drugs 0.000 abstract 1
- 239000000186 progesterone Substances 0.000 abstract 1
- 229960003604 testosterone Drugs 0.000 abstract 1
Classifications
-
- 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
- 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
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 |
|---|---|---|---|
| MX359130X | 1956-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB855800A true GB855800A (en) | 1960-12-07 |
Family
ID=19742787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9187/57A Expired GB855800A (en) | 1956-03-26 | 1957-03-20 | New cyclopentanophenanthrene derivatives and process for the production thereof |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH359130A (cs) |
| DE (1) | DE1136331B (cs) |
| GB (1) | GB855800A (cs) |
| NL (2) | NL215687A (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042275A1 (de) * | 1999-12-08 | 2001-06-14 | Jenapharm Gmbh & Co. Kg | Ungesättigte 14,15-cyclopropano-androstane, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen |
-
0
- NL NL110102D patent/NL110102C/xx active
- NL NL215687D patent/NL215687A/xx unknown
-
1957
- 1957-03-20 GB GB9187/57A patent/GB855800A/en not_active Expired
- 1957-03-20 DE DES52798A patent/DE1136331B/de active Pending
- 1957-03-26 CH CH359130D patent/CH359130A/de unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001042275A1 (de) * | 1999-12-08 | 2001-06-14 | Jenapharm Gmbh & Co. Kg | Ungesättigte 14,15-cyclopropano-androstane, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen |
| US6710039B1 (en) | 1999-12-08 | 2004-03-23 | Schering Ag | Unsaturated 14,15-cyclopropane-androstanes, a method for their production and pharamceutical compositions containing these compounds |
| USRE39862E1 (en) * | 1999-12-08 | 2007-09-25 | Schering Ag | Unsaturated 14, 15-cyclopropanoandrostanes, a method for their production and pharmaceutical compositions containing these compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1136331B (de) | 1962-09-13 |
| NL215687A (cs) | |
| NL110102C (cs) | |
| CH359130A (de) | 1961-12-31 |
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