GB427436A - The manufacture of acyl derivatives of the dihydrofollicle hormone - Google Patents
The manufacture of acyl derivatives of the dihydrofollicle hormoneInfo
- Publication number
- GB427436A GB427436A GB36135/33A GB3613533A GB427436A GB 427436 A GB427436 A GB 427436A GB 36135/33 A GB36135/33 A GB 36135/33A GB 3613533 A GB3613533 A GB 3613533A GB 427436 A GB427436 A GB 427436A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hormone
- yield
- dihydrofollicle
- dissolved
- follicle
- 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
- 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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
Acyl derivatives of dihydrofollicle hormone (described in Specification 428,132) are obtained (1) by treatment thereof with acylating agents, or (2) by subjecting acyl derivatives of the follicle hormone to the action of reducing agents or to catalytic hydrogenation, or (3) by subjecting the follicle hormone to said reduction process in an acylating medium. The first process may be carried out in a solvent in which the mono-acyl derivative is insoluble so as to yield the mono-acyl derivative, or the solvent may be chosen so that di-acyl derivatives are obtained. The second process yields monoacyl derivatives which may be further acylated. The hormones treated may be follicle hormone C18H22O2, equilin C18H20O2, or hippolin C18H18O2, and the dihydrofollicle hormone may be such reduction products of any of these as contain a secondary hydroxyl group in the molecule, but in which the benzene nucleus remains unchanged. According to examples: (1) the dihydrofollicle hormone in caustic soda solution is treated with benzoyl chloride to yield a precipitate of the monobenzoyl compound, which is then recrystallized from dilute alcohol; (2) the same starting material is dissolved in pyridine and treated with benzoyl chloride to yield the di-benzoyl derivative which is precipitated on dilution with hydrochloric acid; (3) the same starting material dissolved in acetic anhydride together with sodium acetate is boiled under reflux and then poured into water to yield a precipitate which is recrystallized from dilute acetic acid, or the product of example 1 may be similarly treated to yield a benzoyl acetyl dihydrofollicle hormone; (4) benzoyl follicle hormone dissolved in alcohol is hydrogenated at 130 DEG C. using a nickel-chromium catalyst, to yield the monobenzoyl dihydrofollicle hormone; (5) follicle hormone is dissolved in acetic anhydride together with sodium acetate and the reaction mixture to which zinc dust has been added is maintained at boiling point and then poured into water to yield a resinous precipitate of diacetyl dihydrofollicle hormone which is recrystallized from dilute alcohol.ALSO:Acyl derivatives of dihydrofollicle hormone (described in Specification 428,132) are obtained (1) by treatment thereof with acylating agents, or (2) by subjecting the acyl derivatives of the follicle hormone to the action of reducing agents or to catalytic hydrogenation, or (3) by subjecting the follicle hormone to said reduction process in an acylating medium. The first process may be carried out in a solvent in which the mono-acyl derivative is insoluble so as to yield the mono-acyl derivative, or the solvent may be chosen so that di-acyl derivatives are obtained. The second process yields mono-acyl derivatives which may be further acylated. The hormones treated may be follicle hormone C18H22O2, equilin C18H20O2, hippolin C18H18O2, and the dihydrofollicle hormone may be such reduction products of any of these as contain a secondary hydroxyl group in the molecule, but in which the benzene nucleus remains unchanged. According to examples: (1) the dihydrofollicle hormone in caustic soda solution is treated with benzoyl chloride to yield a precipitate of the monobenzoyl compound, which is then recrystallized from dilute alcohol; (2) the same starting material is dissolved in pyridine and treated with benzoyl chloride to yield the di-benzoyl derivative which is precipitated on dilution with hydrochloric acid; (3) the same starting material dissolved in acetic anhydride together with sodium acetate is boiled under reflux and then poured into water to yield a precipitate which is recrystallized from dilute acetic acid, or the product of example 1 may be similarly treated to yield a benzoyl acetyl dihydrofollicle hormone; (4) benzoyl follicle hormone dissolved in alcohol is hydrogenated at 130 DEG C. using a nickel-chromium catalyst, to yield the monobenzoyl dihydrofollicle hormone; (5) follicle hormone is dissolved in acetic anhydride together with sodium acetate and the reaction mixture to which zinc dust has been added is maintained at boiling point and then poured into water to yield a resinous precipitate of diacetyl dihydrofollicle hormone which is recrystallized from dilute alcohol.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE427436X | 1932-12-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB427436A true GB427436A (en) | 1935-04-24 |
Family
ID=6477312
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB36135/33A Expired GB427436A (en) | 1932-12-23 | 1933-12-22 | The manufacture of acyl derivatives of the dihydrofollicle hormone |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB427436A (en) |
-
1933
- 1933-12-22 GB GB36135/33A patent/GB427436A/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB427436A (en) | The manufacture of acyl derivatives of the dihydrofollicle hormone | |
US2560939A (en) | - methylenebis | |
US2548922A (en) | Process for preparation of steroidal hydroxy ketones | |
US2212363A (en) | Process of preparing compounds having the character of the male sexual hormones | |
US2033487A (en) | Acyl derivatives of the dihydrofollicle hormone and method of making the same | |
US2422904A (en) | Method of preparing delta1,4-androstadienol-17-one-3 and its derivatives | |
GB497394A (en) | Manufacture of í¸-unsaturated 3-ketones of the cyclopentanopolyhydrophenanthrene series | |
US2088792A (en) | Sexual hormone compounds and process of producing same | |
US2140480A (en) | 3-keto-d-pentonic acid lactone and process for the manufacture of same | |
SU148046A1 (en) | Method for producing cortisone acetate | |
US2231017A (en) | Allo-pregnane compounds and method of obtaining the same | |
US2283913A (en) | Compounds of the cyclopentanopolyhydrophenanthrene series and a method for producing them | |
US2280858A (en) | Acyl derivatives of germinal gland hormone preparations of high activity, and a method of producing the same | |
US2395232A (en) | Process for producing sterol derivatives | |
US3535314A (en) | Process for the preparation of 14beta-hydroxy-3-keto-5beta-card-20(22)-enolides | |
DE508096C (en) | Process for the preparation of acyl bonds of k-strophanthidine | |
US2312484A (en) | Method of preparing cyclopentanopolyhydrophenanthrene ketols and esters thereof | |
US2041856A (en) | Method of acetylating diphenol | |
DE484358C (en) | Process for the preparation of 1,8-naphthoxypenthiophenes | |
SU31430A1 (en) | Linatiole acetylation method | |
US2071804A (en) | Acyl octahydrofollicle hormones and their production | |
US2168379A (en) | Process for preparing derivatives of halogenated sterols and the products thus obtained | |
US1527951A (en) | Derivatives of aminoargentomercaptobenzene carboxylic acid | |
US2670359A (en) | Treatment of steroid quaternary ammonium salts | |
NO146986B (en) | PROCEDURE FOR PENICILLIN OR CEPHALOSPORINES. |