GB1004283A - Steroid compounds - Google Patents
Steroid compoundsInfo
- Publication number
- GB1004283A GB1004283A GB38788/61A GB3878861A GB1004283A GB 1004283 A GB1004283 A GB 1004283A GB 38788/61 A GB38788/61 A GB 38788/61A GB 3878861 A GB3878861 A GB 3878861A GB 1004283 A GB1004283 A GB 1004283A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroids
- general formula
- compounds
- reacting
- prepared
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- 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
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- 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)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises 17a ,20; 20,21-bis-(methylenedioxy) - 11b - formyloxy - 16a -methyl - 11 - phenyl - [3,2 - c] pyrazolo - 4,6-pregnadiene and steroids of the general formulae <PICT:1004283/C2/1> wherein R1 represents b -halogen, b -hydroxy or keto, but R1 is b -halogen only when X is halogen, R11 represents hydrogen, fluorine or methyl, R* represents hydrogen or a - or b -methyl or methylene, R0 is hydrogen, iodine, fluorine, acyloxy or hydroxy, R is hydrogen, alkyl, aralkyl, aryl or acyl and X is hydrogen or halogen, and in which the pyrazole ring structure has the formula shown above or has the following isomeric formula <PICT:1004283/C2/2> wherein R has the above significance and the hydrochloride, sulphate, chlorate, perchlorate, picrate and trichloroacetate salts and the 21-dihydrogen phosphate esters and their mono-and di-alkali metal salts of the steroids of the first general formula; the preparation of the steroids of the second general formula above in which R represents hydrogen or an alkyl, aralkyl or aryl group by reacting on the corresponding 17a ,20; 20,21-bis(methylenedioxy)-2-hydroxy - methylene - 4,6 - pregnadienes with hydrazine hydrate or an alkylhydrazine, aralkylhydrazine, or arylhydrazine or a salt thereof in an inert atmosphere in which process the starting compounds may be prepared by reacting the corresponding 2-unsubstituted steroids with an alkyl formate and sodium hydride in an inert atmosphere to form steroids of the general formula <PICT:1004283/C2/3> wherein R00 is b -halogen, b -hydroxy, b -formyloxy or keto, but R00 is b -halogen only when X is halogen, and R11, R* and X have the above significance (the subsequent reaction with hydrazine or substituted hydrazine may also result in the formation of the corresponding 11b - formyloxy - [3,2-c] pyrazolo-4,6-pregnadiene); the steroids of the second general formula above in which R represents an alkyl, aralkyl or acyl group are prepared by reacting the corresponding compounds in which R represents hydrogen (which may be prepared by the method previously referred to) with an alkyl halide, an aralkyl halide or acylating agent respectively; the preparation of the steroids of the second general formula above in which R1 is b -hydroxy are prepared by reducing the corresponding 11-keto compounds with an alkali metal borohydride; the preparation of steroids of the first general formula above in which R0 represents an acyloxy or hydroxy group and R is other than hydrogen by reacting steroids of the second general formula above or the corresponding 11b -formyloxy steroids with an organic acid (any 11- and/or 21-acyl groups may be removed by treating with alkali metal methoxide, a 11-acyl-21-acylate may be prepared by acylating a 11-acyl-21-hydroxy compound, the 21-acylates having a hydrogen atom at the 11-position are prepared by reacting a 11-acyl-21 acylate with aqueous acetic acid other 11-acyl-groups may be removed by reacting with methanolic sodium methoxide); the preparation of the 21-methanesulphonates of the first general formula above by reacting the corresponding 21-hydroxy compounds with methane sulphonyl chloride and optionally treating the 21-methanesulphonates with an alkali metal iodide, excess benzenesulphonyl chloride and benzene sulphonyl bromide to form the corresponding 21-iodo-, 21-chloro- and 21-bromo-compounds respectively; the 21-desoxy compounds of the first general formula above are prepared by treating the corresponding 21-iodo compounds with an alkali metal bisulphate (the 21-desoxy compounds may be converted to the corresponding 21-bromo compounds by reacting the desoxy compounds with bromine in chloroform); the 21-dihydrogen phosphates of the first general formula above may be prepared by reacting the corresponding 21-iodo-, 21-chloro-and 21-bromo-compounds with a mixture of silver phosphate and phosphoric acid and may subsequently be converted into the mono- and di-alkali metal salts by neutralising the 2x-di-hydrogen phosphates with an alkali metal methoxide-further treatment converts the 11-acyl group into 11-hydrogen; the preparation of a mixture of steroids having the general formulae <PICT:1004283/C2/4> wherein the pyrazole ring structure, R, R1, R11, R* and X have the significance indicated for the first general formula above, by reacting the above corresponding 21-methanesulphonates with an alkali metal fluoride; and the preparation of salts of any of the steroids of the first three general formulae above by treating the steroids with an acid to form salts such as the hydrochloride, sulphate, chlorate, perchlorate, picrate and trichloroacetate. Pharmaceutical compositions having anti-inflammatory activity-particularly for the treatment of arthritis contain as the active ingredients steroids of the first three general formula above and 17a ,20; 20,21-bis(methylenedioxy) - 11b - formyloxy - 16a - methyl - 11-phenyl - [3,2 - c] pyrazolo - 4,6 - pregnadiene. Steroids of the general formula <PICT:1004283/C2/5> wherein R111 represents b -hydroxy or b -halogen and R11, R* and X have the significance indicated for the first three general formulae above, are prepared by treating the corresponding free 17a ,21 - dihydroxy - 20 - keto - compounds with aqueous formaldehyde in the presence of a strong acid. The 11-keto compound may also be prepared by oxidizing the corresponding 11b -hydroxy compound. Specification 877,085 is referred to.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6717260A | 1960-11-04 | 1960-11-04 | |
US10653961A | 1961-05-01 | 1961-05-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1004283A true GB1004283A (en) | 1965-09-15 |
Family
ID=26747553
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38788/61A Expired GB1004283A (en) | 1960-11-04 | 1961-10-30 | Steroid compounds |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH437274A (en) |
FR (2) | FR1482808A (en) |
GB (1) | GB1004283A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE795574A (en) * | 1972-02-18 | 1973-08-16 | Roussel Uclaf | 21-M-SULFOBENZOATE DERIVATIVES OF 6, 16 ALPHA-DIMETHYL 2,4,6-OLO / 3,2 C / PYRAZOLE 20-ONE AND PROCESS FOR PREPARATION |
-
1961
- 1961-10-30 GB GB38788/61A patent/GB1004283A/en not_active Expired
- 1961-11-03 FR FR877942A patent/FR1482808A/en not_active Expired
- 1961-11-04 CH CH1279161A patent/CH437274A/en unknown
-
1962
- 1962-02-01 FR FR886637A patent/FR1925M/en active Active
Also Published As
Publication number | Publication date |
---|---|
FR1482808A (en) | 1967-06-02 |
FR1925M (en) | 1963-07-22 |
CH437274A (en) | 1967-06-15 |
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