GB1015015A - New steroid compounds and processes - Google Patents
New steroid compounds and processesInfo
- Publication number
- GB1015015A GB1015015A GB3172262A GB3172262A GB1015015A GB 1015015 A GB1015015 A GB 1015015A GB 3172262 A GB3172262 A GB 3172262A GB 3172262 A GB3172262 A GB 3172262A GB 1015015 A GB1015015 A GB 1015015A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pregn
- epoxy
- acyloxy
- ethylenedioxy
- methyl
- 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
- -1 steroid compounds Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 abstract 1
- 229960002537 betamethasone Drugs 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000007269 dehydrobromination reaction Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03F—AMPLIFIERS
- H03F3/00—Amplifiers with only discharge tubes or only semiconductor devices as amplifying elements
- H03F3/60—Amplifiers in which coupling networks have distributed constants, e.g. with waveguide resonators
-
- 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
- C07J75/00—Processes for the preparation of steroids in general
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03F—AMPLIFIERS
- H03F1/00—Details of amplifiers with only discharge tubes, only semiconductor devices or only unspecified devices as amplifying elements
- H03F1/52—Circuit arrangements for protecting such amplifiers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 17a -hydroxy-16b -methyl - pregn - 9(11) - en - 3,20 - dione and a process for the preparation of a 17a -hydroxy-16b - methyl - pregn - 9(11) - en - 20 - one derivative of the general formula <FORM:1015015/C2/1> in which X is a 3a -hydroxyl group and Y represents in each case two hydrogen atoms, or X is a 3-oxo group (=O) and Y represents either two hydrogen atoms or a double bond, in which case a 3a -acyloxy-16a ,17a -epoxy-20-ethylenedioxy - 5b - pregn - 9(11) - ene is treated with methyl lithium or methyl magnesium halide so as to form 3a ,17a -dihydroxy-16b -methyl-5b -pregn - 9(11) - en - 20 - one. The starting 3a -acyloxy - 16a ,17a - epoxy - 20 - ethylenedioxy - 5b -pregn-9(11)-ene may be obtained by protecting a 3a -acyloxy-16a ,17a -epoxy-5b -pregna-11,20-dione by ketalation to form a 20-ketal, reducing the latter with simultaneous saponification to form 16a ,17a -epoxy-20-ethylenedioxy - 3a ,11b - dihydroxy - 5b - pregnane by means of an alkali metal borohydride, esterifying the latter to form the corresponding 3a -acyloxy - 16a ,17a - epoxy - 20 - ethylenedioxy - 11b -hydroxy-5b -pregnane followed by dehydration to obtain the desired 3a -acyloxy-16a ,17a -epoxy - 20 - ethylenedioxy - 5b - pregn - 9(11) - ene. The 3-hydroxy compound may be oxidized to obtain a 3-keto compound while unsaturation in 1 and 4 positions may be introduced by dibromination and dehydrobromination. A 21-acyloxy group may be introduced by treatment with iodine follow by an alkali metal acylate. The products are useful in the preparation of betamethasone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR871086A FR1346960A (en) | 1961-08-18 | 1961-08-18 | New process for the preparation of a 16-methyl steroid and intermediates used in this process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1015015A true GB1015015A (en) | 1965-12-31 |
Family
ID=8761437
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4440164A Expired GB1015016A (en) | 1961-08-18 | 1962-08-17 | New steroid compounds and processes |
| GB4440264A Expired GB1015017A (en) | 1961-08-18 | 1962-08-17 | New steroid compounds and processes |
| GB3172262A Expired GB1015015A (en) | 1961-08-18 | 1962-08-17 | New steroid compounds and processes |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4440164A Expired GB1015016A (en) | 1961-08-18 | 1962-08-17 | New steroid compounds and processes |
| GB4440264A Expired GB1015017A (en) | 1961-08-18 | 1962-08-17 | New steroid compounds and processes |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH414615A (en) |
| DK (1) | DK105270C (en) |
| FR (1) | FR1346960A (en) |
| GB (3) | GB1015016A (en) |
-
1961
- 1961-08-18 FR FR871086A patent/FR1346960A/en not_active Expired
-
1962
- 1962-08-14 CH CH971462A patent/CH414615A/en unknown
- 1962-08-17 GB GB4440164A patent/GB1015016A/en not_active Expired
- 1962-08-17 DK DK361562A patent/DK105270C/en active
- 1962-08-17 GB GB4440264A patent/GB1015017A/en not_active Expired
- 1962-08-17 GB GB3172262A patent/GB1015015A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1015016A (en) | 1965-12-31 |
| DK105270C (en) | 1966-09-12 |
| CH414615A (en) | 1966-06-15 |
| GB1015017A (en) | 1965-12-31 |
| FR1346960A (en) | 1963-12-27 |
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