GB849098A - 4-substituted steroid compounds and the preparation thereof - Google Patents
4-substituted steroid compounds and the preparation thereofInfo
- Publication number
- GB849098A GB849098A GB10340/57A GB1034057A GB849098A GB 849098 A GB849098 A GB 849098A GB 10340/57 A GB10340/57 A GB 10340/57A GB 1034057 A GB1034057 A GB 1034057A GB 849098 A GB849098 A GB 849098A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- ococh3
- chloro
- general formula
- acyloxy group
- 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 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- JWMFYGXQPXQEEM-GCOKGBOCSA-N 5α-pregnane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-GCOKGBOCSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 230000001225 therapeutic effect Effects 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 4b , 5a -substituted steroid compounds of the general formula: <FORM:0849098/IV(b)/1> wherein R represents (H)OH, (H)OCOCH3, O, (H)COCH3, (H)COCH2OH or (H)COCH2 OCOCH3, R1 represents (H)H, (H)OH or O, and R111 represents a hydroxyl or acyloxy group or a bromine, fluorine or chlorine atom, and the preparation thereof by reacting a 4a ,5-epoxy-3-keto-steroid of the general formula: <FORM:0849098/IV(b)/2> wherein R and R1 have the above significance, with a non-halogen containing mineral acid such as sulphuric acid in the presence of acetone to obtain compounds in which R1 is OH or with a hydrohalic acid in the presence of acetic acid to obtain compounds wherein R111 represents the halogen atom, compounds in which R111 represents an acyloxy group being obtained by acylating the compounds in which R111 represents a hydroxy group. In the examples allopregnane -4b , 5a -diol-3, 20-dione, androstane-4b , 5a , 17b -triol-3-one-17-acetate, 4b -bromo (and chloro) -allopregnan-5a -ol-3, 20-dione 4b -bromo (and chloro)-allopregnan-5a -ol-3, 11, 20-trione, and 4b -chloro-androstane-5a , 17b -diol-3-one-17-acetate are prepared. Specifications 838,771,838,772, and 838,773 are referred to.ALSO:A therapeutic composition comprises at least one compound of the general formula:- <FORM:0849098/VI/1> wherein R represents (H)OH, (H)(OCOCH3, O, (H)COCH3, (H)COCH2OH or (H)COCH2 OCOCH3, R1 represents (H)H, (H)OH or O, and R111 represents a hydroxy or acyloxy group or a bromine, fluorine or chlorine atom, and a therapeutically acceptable carrier compatible therewith.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT849098X | 1956-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB849098A true GB849098A (en) | 1960-09-21 |
Family
ID=11325570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10340/57A Expired GB849098A (en) | 1956-04-11 | 1957-03-29 | 4-substituted steroid compounds and the preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB849098A (en) |
-
1957
- 1957-03-29 GB GB10340/57A patent/GB849098A/en not_active Expired
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