GB1014155A - New estrene derivatives and processes for the preparation and use thereof - Google Patents
New estrene derivatives and processes for the preparation and use thereofInfo
- Publication number
- GB1014155A GB1014155A GB756163A GB756163A GB1014155A GB 1014155 A GB1014155 A GB 1014155A GB 756163 A GB756163 A GB 756163A GB 756163 A GB756163 A GB 756163A GB 1014155 A GB1014155 A GB 1014155A
- Authority
- GB
- United Kingdom
- Prior art keywords
- allyl
- estr
- ene
- reacting
- estra
- 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
- 150000002165 estrenes Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 abstract 1
- YSSWSYPWVAXUAU-SMUKYFJDSA-N [(1R,3S,6S,11S,12S,15S,16S)-6-hydroxy-16-methyl-2-oxapentacyclo[9.7.0.01,3.03,8.012,16]octadec-7-en-15-yl] benzoate Chemical compound O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@]34[C@@]2(CC1)O4)OC(C4=CC=CC=C4)=O YSSWSYPWVAXUAU-SMUKYFJDSA-N 0.000 abstract 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- -1 allyl magnesium halide Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000012024 dehydrating agents Substances 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
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises (a) a process for preparing 10b -allyl-17b -hydroxy-estra-4,9 (11)-dien-3-one and its 17-esters by reacting an allyl magnesium halide with 3b ,17b -dihydroxy-9a , 10a epoxy-estr-4-ene, or a 17-ester thereof having in the acid moiety 1 to 7 carbon atoms, to form 10b -allyl-3b ,9a ,17b -trihydroxy-estr-4-ene, reacting this with an oxidizing agent to form 10b - allyl - 9a - hydroxy - estr - 4 - ene - 3,17-dione, reacting this with a dehydrating agent to form 10b -allyl-estra-4,9(11)-diene-3,17-dione, reacting this with an amine of formula HNR1R2, wherein R1 and R2 are alkyl groups having 1 to 6 carbon atoms or in combination with the nitrogen atom a nitrogen- or nitrogen- and oxygen-containing heterocycle, to form a 10b -allyl - 3 - enamino - estra - 3,5,9(11) - trien - 17-one, reducing this to form a 10b -allyl-3- or enamino - estr - 3,5,9(11) trien - 17b - ol, liberating the protected 3-keto group and, if desired, esterifying at the 17-position with an acylating agent derived from an organic carboxylic acid having 1 to 18 carbon atoms; and (b) the intermediates described above and their preparation as indicated. 3b - Hydroxy - 9a ,10a - epoxy - 17b - benzoyloxy-estr-4-ene is prepared by reduction of the corresponding 3-ketone with sodium borohydride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR889098A FR1380411A (en) | 1962-02-24 | 1962-02-24 | New process for the preparation of 10 beta-allyl-steroids and products used in this process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1014155A true GB1014155A (en) | 1965-12-22 |
Family
ID=8773421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB756163A Expired GB1014155A (en) | 1962-02-24 | 1963-02-25 | New estrene derivatives and processes for the preparation and use thereof |
Country Status (7)
| Country | Link |
|---|---|
| BR (1) | BR6347174D0 (en) |
| CH (1) | CH414607A (en) |
| DK (1) | DK102858C (en) |
| ES (1) | ES285390A1 (en) |
| FR (1) | FR1380411A (en) |
| GB (1) | GB1014155A (en) |
| SE (1) | SE301801B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102907A (en) * | 1977-03-07 | 1978-07-25 | The Upjohn Company | Desulfinylation process for preparing androsta-4,9(11)-diene-3,17-dione |
| FR2576025B1 (en) * | 1985-01-14 | 1987-01-23 | Roussel Uclaf | NOVEL SUBSTITUTED STEROIDS IN POSITION 10, THEIR PROCESS AND THE PREPARATION INTERMEDIATES, THEIR APPLICATION AS MEDICAMENTS, THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
-
1962
- 1962-02-24 FR FR889098A patent/FR1380411A/en not_active Expired
-
1963
- 1963-02-15 DK DK70763A patent/DK102858C/en active
- 1963-02-16 SE SE172863A patent/SE301801B/xx unknown
- 1963-02-22 CH CH229363A patent/CH414607A/en unknown
- 1963-02-22 BR BR14717463A patent/BR6347174D0/en unknown
- 1963-02-23 ES ES285390A patent/ES285390A1/en not_active Expired
- 1963-02-25 GB GB756163A patent/GB1014155A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1380411A (en) | 1964-12-04 |
| DK102858C (en) | 1965-10-18 |
| ES285390A1 (en) | 1963-05-01 |
| CH414607A (en) | 1966-06-15 |
| SE301801B (en) | 1968-06-24 |
| BR6347174D0 (en) | 1973-07-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1077392A (en) | New steroids | |
| GB1014155A (en) | New estrene derivatives and processes for the preparation and use thereof | |
| ES290864A1 (en) | Novel steroid esters, their preparation and employment | |
| GB795103A (en) | Improvements in or relating to steroid compounds and the preparation thereof | |
| GB992556A (en) | 2-methyl-í¸-androstene derivatives and process for their production | |
| ES329417A1 (en) | A procedure for preparation of the 3.17 epsilon-dihydroxy (delta2'3 dihydro) (4'5'-16,17) -isoxazolino 13-z gona 1, 3,5 (10) -triene. (Machine-translation by Google Translate, not legally binding) | |
| GB966100A (en) | Novel cyclopentanophenanthrene compounds and a process for the production thereof | |
| ES282861A2 (en) | A procedure for the preparation of derivatives of 6-methyl and 1,6-dimethyl ergoline ii (Machine-translation by Google Translate, not legally binding) | |
| GB1018780A (en) | Steroid (2,3í¬c) furazan compounds and the process for the production thereof | |
| GB996308A (en) | New 19-nor-steroids | |
| GB845442A (en) | Manufacture of steroid compounds | |
| GB908674A (en) | Preparation of 17ª--acyloxy-6ª--methyl-16-methylenepregn-4-ene-3,20-diones | |
| GB1085612A (en) | New 16-alkyl pregnane derivatives and process for the preparation thereof | |
| GB948061A (en) | Improvements in or relating to cyclopentanophenanthrene compounds | |
| GB1099007A (en) | Novel process for preparing unsaturated steroids | |
| GB914738A (en) | Improvements in or relating to processes for the production of compounds useful in steroid synthesis | |
| GB912035A (en) | 11ª--hydroxy-11ª--methyl steroids | |
| GB896027A (en) | New cyclopentanophenanthrene derivatives | |
| GB950615A (en) | Improvements in or relating to 20-(n-alkyl-n-halo-amino) steroids | |
| GB978725A (en) | Novel steroid compounds and processes for their perparation | |
| ES280807A1 (en) | Procedure for preparing 6-alpha-methyl-16-methylene-steroids (Machine-translation by Google Translate, not legally binding) | |
| GB1086461A (en) | 1,1-ethylene-17ª-alkyl-í¸-5ª-androsten-17ª-ols and their 17-esters and a process for their manufacture | |
| ES297535A1 (en) | A procedure for the preparation of 16-methylene-steroids (Machine-translation by Google Translate, not legally binding) | |
| GB1004463A (en) | Process for the production of í¸-androstene and í¸-pregnene compounds | |
| FR2438055A1 (en) | Nor:steroid fertility control agents - of oestrane, androstane and gonane and the corresponding di:homo-steroid(s) |