GB996079A - 17ª‡,21-substituted methylenedioxy steroids and methods therefor - Google Patents
17ª‡,21-substituted methylenedioxy steroids and methods thereforInfo
- Publication number
- GB996079A GB996079A GB2274262A GB2274262A GB996079A GB 996079 A GB996079 A GB 996079A GB 2274262 A GB2274262 A GB 2274262A GB 2274262 A GB2274262 A GB 2274262A GB 996079 A GB996079 A GB 996079A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- keto
- carbon atoms
- hydroxy
- hydroxy group
- 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
- -1 methylenedioxy steroids Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 150000003431 steroids Chemical class 0.000 abstract 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 3
- 229930194542 Keto Natural products 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 239000011737 fluorine Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000000468 ketone group Chemical group 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 abstract 1
- 229940071536 silver acetate Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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 steroids having at the 17, 20 and 21 positions the general formula <FORM:0996079/C2/1> wherein R1 represents an alkyl radical containing 1 to 3 carbon atoms and R represents an aliphatic hydrocarbon radical containing 1 to 9 carbon atoms, a cycloaliphatic hydrocarbon radical containing 4 to 6 carbon atoms, an arylaliphatic hydrocarbon radical containing 7 or 8 carbon atoms, a phenyl, a b -carboxyethyl, a b -carbomethoxyethyl or b -carbethoxyethyl radical, and the preparation thereof by reacting a 17a ,21-dihydroxy-20-keto-steroid having no free hydroxy group at the 16-position with an orthoester of the formula R-C(OR1)3 wherein R and R1 have the above significance in the presence of an acid catalyst and in solution in an organic solvent. The steroids of the above formula may contain at the 3-position a keto or hydroxy group, an alkoxy group of 1 to 3 carbon atoms, an alkoxyloxy group of 1 to 3 carbon atoms or a benzoyloxy group. Other substituents such as hydroxy, keto, halogen, ether and methyl groups, may be present, for example at positions 1,2,4,6,7,9,11 or 16. The steroid nucleus may be saturated or have one or more double bonds, for example in the 1 :2, 3 : 4, 4 : 5, 5 : 6 or 9 : 11 positions-particularly at positions 4 : 5, or 1 : 2 and 4 : 5 in which case the preferred steroids having a 3-keto group, an 11-keto or b -hydroxy group, and coupled with the 11b -hydroxy group an a -halogen atom-particularly fluorine, at the 9-position. Other substituents may occur at the 6- or 16-position, for example a 16a -acetoxy group. The particularly preferred steroids containing the structure detailed above have the general formula <FORM:0996079/C2/2> wherein R and R1 have the above significance, X represents a keto or b -hydroxy group, Y represents hydrogen or fluorine, W represents hydrogen or fluorine or the methyl group, and R2 represents hydrogen, an a or b -methyl group or an a -hydroxy group, and the corresponding 1 : 2-unsaturated derivatives thereof. If the product of the above process contains a 16b -bromine atom, this may be reacted with silver acetate to form a 16b -acetoxy substituent which may then be hydrolysed, for example with potassium carbonate, to form a 16a -hydroxy substituent. Specifications 963,829 and 996,080 are referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1078961 | 1961-06-13 | ||
| IT1165961 | 1961-06-24 | ||
| DEV21321A DE1173897B (en) | 1961-06-24 | 1961-09-18 | Process for the preparation of cyclic 17ª ‡, 21-orthoformic acid esters of? -3-keto steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB996079A true GB996079A (en) | 1965-06-23 |
Family
ID=27213296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2274262A Expired GB996079A (en) | 1961-06-13 | 1962-06-13 | 17ª‡,21-substituted methylenedioxy steroids and methods therefor |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH432513A (en) |
| GB (1) | GB996079A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069322A (en) * | 1976-10-12 | 1978-01-17 | Interx Research Corporation | Pro-drugs for the improved delivery of certain selected anti-inflammatory steroids |
| IT202100008429A1 (en) * | 2021-04-06 | 2022-10-06 | Farmabios Spa | Process for the preparation of cortexolone 17α-propionate and its new hydrated crystalline form |
| CN116023425A (en) * | 2023-03-28 | 2023-04-28 | 南京师范大学 | Triamcinolone derivatives and their medicinal uses |
-
1962
- 1962-06-01 CH CH666762A patent/CH432513A/en unknown
- 1962-06-13 GB GB2274262A patent/GB996079A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069322A (en) * | 1976-10-12 | 1978-01-17 | Interx Research Corporation | Pro-drugs for the improved delivery of certain selected anti-inflammatory steroids |
| IT202100008429A1 (en) * | 2021-04-06 | 2022-10-06 | Farmabios Spa | Process for the preparation of cortexolone 17α-propionate and its new hydrated crystalline form |
| EP4071160A1 (en) * | 2021-04-06 | 2022-10-12 | Farmabios S.p.A. | Process for the preparation of cortexolone 17 a-propionate and new hydrated crystalline form thereof |
| US12247048B2 (en) | 2021-04-06 | 2025-03-11 | Farmabios S.P.A. | Process for the preparation of cortexolone 17α-propionate and new hydrated crystalline form thereof |
| CN116023425A (en) * | 2023-03-28 | 2023-04-28 | 南京师范大学 | Triamcinolone derivatives and their medicinal uses |
Also Published As
| Publication number | Publication date |
|---|---|
| CH432513A (en) | 1967-03-31 |
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