GB833582A - New steroid esters and the preparation thereof - Google Patents
New steroid esters and the preparation thereofInfo
- Publication number
- GB833582A GB833582A GB24777/57A GB2477757A GB833582A GB 833582 A GB833582 A GB 833582A GB 24777/57 A GB24777/57 A GB 24777/57A GB 2477757 A GB2477757 A GB 2477757A GB 833582 A GB833582 A GB 833582A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- esters
- group
- esterification
- carbobenzoxy
- 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)
- Steroid Compounds (AREA)
Abstract
The invention comprises 3,17-esters of oestradiol, 17-esters of testosterone and 17-esters of 19-nor-testosterone, and 21-esters of cortisone, hydrocortisone, prednisone and prednisolone (in each case the ester group or groups are derived from glycine, alanine and phenylalanine), and acid addition salts of said esters. The esterification is carried out with the aminocarboxylic acid which may be in one of its optically active forms or as a racenate, the amino group being protected, e.g. by means of the carbobenzoxy group. Thus the esterification may be carried out with an N-carbobenzoxy amino-acid in the presence of a dehydrating agent. e.g. ethoxyacetylene, or by use of the corresponding acid anhydride or acid chloride, preferably in the presence of an organic base, e.g. a tertiary base such as pyridine or quinoline. After the esterification the carbobenzoxy group from the resulting N-carbobenzoxy amino-acid ester of the above steroid compounds can be split off by catalytic reduction or by treatment with a hydrohalogenic acid such as hydrobromic acid, in which case the corresponding hydrohalide salt is formed. The process may be modified in that any oxo groups in the reactants may be protected during esterification such as by ketalization, e.g. to form an ethylenedioxy group. A number of detailed examples are given.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL833582X | 1956-08-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB833582A true GB833582A (en) | 1960-04-27 |
Family
ID=19843052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24777/57A Expired GB833582A (en) | 1956-08-14 | 1957-08-06 | New steroid esters and the preparation thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB833582A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007008474A2 (en) * | 2005-07-12 | 2007-01-18 | Warner Chilcott Company, Inc. | 3 -ester prodrugs of estradiol |
US7795241B2 (en) | 2005-07-12 | 2010-09-14 | Warner Chilcott Company, Llc | Derivative prodrugs of ethinyl estradiol |
-
1957
- 1957-08-06 GB GB24777/57A patent/GB833582A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007008474A2 (en) * | 2005-07-12 | 2007-01-18 | Warner Chilcott Company, Inc. | 3 -ester prodrugs of estradiol |
WO2007008474A3 (en) * | 2005-07-12 | 2007-08-30 | Warner Chilcott Co Inc | 3 -ester prodrugs of estradiol |
US7795241B2 (en) | 2005-07-12 | 2010-09-14 | Warner Chilcott Company, Llc | Derivative prodrugs of ethinyl estradiol |
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