GB887815A - Steroids - Google Patents
SteroidsInfo
- Publication number
- GB887815A GB887815A GB1384/60A GB138460A GB887815A GB 887815 A GB887815 A GB 887815A GB 1384/60 A GB1384/60 A GB 1384/60A GB 138460 A GB138460 A GB 138460A GB 887815 A GB887815 A GB 887815A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acylamino
- group
- amino
- compound
- pregnane
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 11a - and 11b -acylamino - D 4 - pregnene - 17a , 21 - diol - 3, 20 - diones and the corresponding D 1,4-pregnadienes and 11a -amino-steroids of the pregnane and allopregnane series of the general formula <FORM:0887815/IV (b)/1> wherein X represents hydrogen or an a -hydroxy group, Y represents hydrogen or a hydroxyl or alkanoyloxy group, Z represents a hydroxy, keto or ketal group and R represents hydrogen or an alkanoyl group (the alkanoyloxy and alkanoyl groups are saturated aliphatic groups having not more than 4 carbon atoms) and the corresponding N-acylated compounds, and a process for the preparation of 11a and 11b -amino-steroids of the pregnane and allopregnane series of the above general formula wherein X, Y, Z and R have the above significance, by reducing the corresponding 11-oximino compounds by any method known for the direct reduction of an oxime to the corresponding amine, and, if necessary, removing the 20-ketal group to form a 20-keto group. The above process may be extended in that the 11-amino group may be acylated to form the corresponding 11-acylamino compounds. When the above reduction process is carried out with sodium in alcohol or sodium amalgam in an aqueous medium on 11a -amino-steroids is formed and when the reduction is carried out with lithium aluminium hydride or by catalytic hydrogenation in an acid medium an 11b -amino-steroid is formed. The 11a -amino-pregnane-3a ,17a ,20b -triol may be acylated to form an N-aryl-3,20-diacyloxy compound the ester groups of which may be hydrolysed by treatment with refluxing aqueous methanolic sodium hydroxide for a short period to form an 11a -acylaminopregnane-3a ,17a ,20b -triol. The latter compound or the corresponding 11b -acylamino compound may be converted to 11a -acylaminopregnane-17a -ol-3,20-dione or the corresponding 11b -acylamino-compound by oxidising with chromium trioxide in pyridine with N-bromo-acetamide or with N-bromo-succinimide. Further treatment by selectively reducing the 3-keto group to form an 11a (or b )-acylamino-pregnane-3a ,17a -diol-20-one, e.g. with sodium borohydride or hydrogen in the presence of Raney nickel, brominating to form the corresponding 21-bromo compound, reacting with potassium acetate to form 11a (or b )-acylamino - 21 - acetoxy - pregnane - 3a , 17a - 3,20-dione, brominating at C4 to form the corresponding 4-bromo-compound, dehydrobrominating to form 11a (or b )-acylamino-21-acetoxy-D 4-pregnene-17a -ol-3,20-dione, and hydrolysing with acid or alkali forms 11a -acylamino-D 4-pregnene-17a ,21-diol-3,20-dione, and optionally dehydrogenating with selenium dioxide or dehydrogenating by means of a biochemical method forms 11a (or b )-acylamino-D 1,4-pregnadiene-17a ,21-diol-3,20-dione. Detailed examples are given.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US887815XA | 1957-05-06 | 1957-05-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB887815A true GB887815A (en) | 1962-01-24 |
Family
ID=22213414
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1384/60A Expired GB887815A (en) | 1957-05-06 | 1958-05-02 | Steroids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB887815A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4352798A (en) * | 1980-07-16 | 1982-10-05 | Glaxo Group Limited | 11 α-Amino-androstanes |
US4353898A (en) * | 1980-07-16 | 1982-10-12 | Glaxo Group Limited | 11α-Amino-androstanes |
-
1958
- 1958-05-02 GB GB1384/60A patent/GB887815A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4352798A (en) * | 1980-07-16 | 1982-10-05 | Glaxo Group Limited | 11 α-Amino-androstanes |
US4353898A (en) * | 1980-07-16 | 1982-10-12 | Glaxo Group Limited | 11α-Amino-androstanes |
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