GB753793A - Aryloxy esters of testosterone, and therapeutic compositions thereof - Google Patents
Aryloxy esters of testosterone, and therapeutic compositions thereofInfo
- Publication number
- GB753793A GB753793A GB20814/54A GB2081454A GB753793A GB 753793 A GB753793 A GB 753793A GB 20814/54 A GB20814/54 A GB 20814/54A GB 2081454 A GB2081454 A GB 2081454A GB 753793 A GB753793 A GB 753793A
- Authority
- GB
- United Kingdom
- Prior art keywords
- testosterone
- acid
- esters
- lower alkyl
- appropriate
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention comprises testosterone esters of the general formula <FORM:0753793/IV(a)/1> where R is an aryl radical or a lower alkyl, alkoxy or halogen substitution product thereof, X is H or lower alkyl (1-6 carbon atoms) and n is 0, 1 or 2; and a process for their preparation by esterifying testosterone by a method normally used for esterifying hydroxylated steroids. Specified methods are (1) treatment of testosterone with (a) the appropriate acid halide or anhydride, preferably in an inert solvent, e.g. benzene, tetrahydrofuran, and using an acid-binding agent, e.g. pyridine; (b) the appropriate free acid in an inert solvent, e.g. toluene, and using an acid catalyst, e.g. p-toluene sulphonic acid; (2) reaction of a 17-halogenated derivative of testosterone with the silver salt of the appropriate phenoxy acid. In examples: (1) testosterone is refluxed with phenoxyacetic anhydride in benzene to yield testosterone phenoxyacetate; (2) testosterone in tetrahydrofuran is refluxed with p-chlorophenoxyacetyl chloride to yield testosterone p-chlorophenoxyacetate. Similarly, using the appropriate acid chlorides, testosterone 2 : 4-dichlorophenoxyacetate, a - phenoxybutyrate and b -phenoxypropionate are prepared. Other esters listed are the p-methyl-, p-bromo-, p-methoxy-, o-chloro- and p-tert-butyl-phenoxyacetates, and the (-) and (+)-a -phenoxypropionates.ALSO:Pharmaceutical compositions for androgenic therapy comprises an androgenic agent consisting essentially of a testosterone ester of the general formula: <FORM:0753793/VI/1> (wherein R is an aryl radical or a lower alkyl, alkoxy or halogen substitution product thereof, X is H or lower alkyl, and n is O, 1 or 2) together with a non-toxic vehicle. The esters may be formulated as an injectable suspension a) in aqueous media, incorporating a wetting agent; (b) in an anhydrous hydrophilic base e.g. polyethylene glycol; or (c) in an oleaginous vehicle, e.g. sesame oil containing aluminium monostearate and propyl paraben. A typical aqueous injectable suspension incorporates dibasic sodium phosphate, monobasic potassium phosphate, polysorbate 80, sorbitan monolaurate, and thimerosal in addition to testosterone phenoxyacetates. The esters may also be administered as ointments, tablets or suppositories, specified diluents being cetyl alcohol, glyceryl laurate, glyceryl monostearate, magnesium stearate, glycerine, propyl paraben, begamot, starch, gelatin, lactose, ol. theobroma, and alcohol.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US753793XA | 1953-07-17 | 1953-07-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB753793A true GB753793A (en) | 1956-08-01 |
Family
ID=22125327
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20814/54A Expired GB753793A (en) | 1953-07-17 | 1954-07-16 | Aryloxy esters of testosterone, and therapeutic compositions thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB753793A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2904562A (en) * | 1958-01-20 | 1959-09-15 | Leo Ab | Esters of testosterone and 19-nortestosterone and method for the production thereof |
FR2100770A1 (en) * | 1970-06-17 | 1972-03-24 | Gastaud Jean | |
US6598371B1 (en) | 1998-10-06 | 2003-07-29 | Stanelco Fibre Optics Ltd. | Capsules |
US10624903B2 (en) * | 2017-10-19 | 2020-04-21 | Evestra, Inc. | Longer-acting progestin prodrug contraceptives |
-
1954
- 1954-07-16 GB GB20814/54A patent/GB753793A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2904562A (en) * | 1958-01-20 | 1959-09-15 | Leo Ab | Esters of testosterone and 19-nortestosterone and method for the production thereof |
FR2100770A1 (en) * | 1970-06-17 | 1972-03-24 | Gastaud Jean | |
US6598371B1 (en) | 1998-10-06 | 2003-07-29 | Stanelco Fibre Optics Ltd. | Capsules |
US10624903B2 (en) * | 2017-10-19 | 2020-04-21 | Evestra, Inc. | Longer-acting progestin prodrug contraceptives |
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