GB1384994A - Pregnane-21-aldehydes and their derivatives and a process for the production thereof - Google Patents
Pregnane-21-aldehydes and their derivatives and a process for the production thereofInfo
- Publication number
- GB1384994A GB1384994A GB1029073A GB1029073A GB1384994A GB 1384994 A GB1384994 A GB 1384994A GB 1029073 A GB1029073 A GB 1029073A GB 1029073 A GB1029073 A GB 1029073A GB 1384994 A GB1384994 A GB 1384994A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- ols
- steroids
- esterified
- aldehydes
- 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
- UJWPMRYSXHLYMB-XFNFOBRPSA-N pregnan-21-al Chemical class C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)CC=O)[C@@H]4[C@@H]3CCC21 UJWPMRYSXHLYMB-XFNFOBRPSA-N 0.000 title 1
- 150000003431 steroids Chemical class 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003128 pregnanes Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1384994 Aldehydes of the pregnane series CIBA-GEIGY AG 2 March 1973 [3 March 1972] 10290/73 Heading C2U Novel steroids of the formula wherein R 1 and R 2 together are 0 or each is a free, esterified or etherified OH group; R 3 is a free or esterified OH group; B 4 is O or H (#-OH); and one of R 5 and R 6 is F and the other is H or F, are prepared (a) by oxidation of the corresponding 21-ols(which may contain an 11-acyloxy group, in which case this is subsequently hydrolysed to an 11-OH group); (b) by addition of HF to the corresponding 9#,11#- epoxides, to give the 9α-fluoro-11#-ols; or (c) by addition of Cl 2 to the corresponding 2-unsubstituted steroids, if necessary with temporary protection of the 11-OH and/or 20-oxo group, e.g. by formation of an 11-trifluoroacetate, followed by elimination of HCl from the resulting 1,2-dichloro-steroids. Resulting 21-ols and als may be treated with esterifying or etherifying agents; 21-esterified or etherified diols may be hydrolysed; and 11-ols may. be oxidized to 11-ones. 2 - Chloro - 3,20,21 - trioxo - 6α -fluoro 9#,11#- oxido - 16α - methyl - 17α - hydroxy. - #<SP>1,4</SP> - pregnadiene is prepared by oxidation of the corresponding 21-ol. The novel steroids are anti-inflammatory agents and they may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH313472A CH592113A5 (en) | 1972-03-03 | 1972-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1384994A true GB1384994A (en) | 1975-02-26 |
Family
ID=4249348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1029073A Expired GB1384994A (en) | 1972-03-03 | 1973-03-02 | Pregnane-21-aldehydes and their derivatives and a process for the production thereof |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS4899156A (en) |
| AR (2) | AR205525A1 (en) |
| AT (1) | AT335081B (en) |
| AU (1) | AU470390B2 (en) |
| BE (1) | BE796181A (en) |
| CA (1) | CA994754A (en) |
| CH (1) | CH592113A5 (en) |
| DD (1) | DD102692A5 (en) |
| DE (1) | DE2309030A1 (en) |
| DK (1) | DK132440C (en) |
| ES (2) | ES412196A1 (en) |
| FI (1) | FI52097C (en) |
| FR (1) | FR2181783B1 (en) |
| GB (1) | GB1384994A (en) |
| IE (1) | IE37311B1 (en) |
| IL (1) | IL41579A (en) |
| NL (1) | NL7302832A (en) |
| SE (1) | SE398505B (en) |
| ZA (1) | ZA731218B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5420120A (en) * | 1993-12-17 | 1995-05-30 | Alcon Laboratories, Inc. | Anti-inflammatory glucocorticoid compounds for topical ophthalmic use |
| US5446177A (en) * | 1984-12-28 | 1995-08-29 | Alcon Laboratories, Inc. | Anti-inflammatory compounds for ophthalmic use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2010551A1 (en) * | 1968-06-10 | 1970-02-20 | Ciba Geigy Ag | |
| DE1961867A1 (en) * | 1968-12-12 | 1970-07-02 | Ciba Geigy | Process for the preparation of aldehydes of the pregnane series and their derivatives |
-
1972
- 1972-03-03 CH CH313472A patent/CH592113A5/xx not_active IP Right Cessation
-
1973
- 1973-01-01 AR AR250325A patent/AR205525A1/en active
- 1973-02-12 FI FI730397A patent/FI52097C/en active
- 1973-02-15 SE SE7302147A patent/SE398505B/en unknown
- 1973-02-19 IL IL41579A patent/IL41579A/en unknown
- 1973-02-21 ZA ZA731218A patent/ZA731218B/en unknown
- 1973-02-21 IE IE273/73A patent/IE37311B1/en unknown
- 1973-02-23 CA CA164,420A patent/CA994754A/en not_active Expired
- 1973-02-23 DE DE19732309030 patent/DE2309030A1/en active Pending
- 1973-02-28 NL NL7302832A patent/NL7302832A/xx not_active Application Discontinuation
- 1973-03-01 ES ES412196A patent/ES412196A1/en not_active Expired
- 1973-03-01 DD DD169150A patent/DD102692A5/xx unknown
- 1973-03-01 AU AU52746/73A patent/AU470390B2/en not_active Expired
- 1973-03-02 DK DK115873A patent/DK132440C/en active
- 1973-03-02 FR FR7307477A patent/FR2181783B1/fr not_active Expired
- 1973-03-02 BE BE128286A patent/BE796181A/en unknown
- 1973-03-02 AT AT188773A patent/AT335081B/en not_active IP Right Cessation
- 1973-03-02 GB GB1029073A patent/GB1384994A/en not_active Expired
- 1973-03-03 JP JP48024818A patent/JPS4899156A/ja active Pending
- 1973-03-07 AR AR246927A patent/AR197125A1/en active
-
1975
- 1975-07-16 ES ES439489A patent/ES439489A1/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446177A (en) * | 1984-12-28 | 1995-08-29 | Alcon Laboratories, Inc. | Anti-inflammatory compounds for ophthalmic use |
| US5420120A (en) * | 1993-12-17 | 1995-05-30 | Alcon Laboratories, Inc. | Anti-inflammatory glucocorticoid compounds for topical ophthalmic use |
Also Published As
| Publication number | Publication date |
|---|---|
| ES412196A1 (en) | 1976-05-16 |
| IE37311L (en) | 1973-09-03 |
| BE796181A (en) | 1973-09-03 |
| IE37311B1 (en) | 1977-06-22 |
| ZA731218B (en) | 1973-11-28 |
| FI52097B (en) | 1977-02-28 |
| SE398505B (en) | 1977-12-27 |
| DD102692A5 (en) | 1973-12-20 |
| AU470390B2 (en) | 1976-03-11 |
| JPS4899156A (en) | 1973-12-15 |
| FR2181783B1 (en) | 1975-10-31 |
| IL41579A (en) | 1976-09-30 |
| AR197125A1 (en) | 1974-03-15 |
| CA994754A (en) | 1976-08-10 |
| DK132440B (en) | 1975-12-08 |
| FR2181783A1 (en) | 1973-12-07 |
| FI52097C (en) | 1977-06-10 |
| AU5274673A (en) | 1974-09-05 |
| AT335081B (en) | 1977-02-25 |
| ES439489A1 (en) | 1977-02-16 |
| AR205525A1 (en) | 1976-05-14 |
| DK132440C (en) | 1976-05-10 |
| ATA188773A (en) | 1976-06-15 |
| CH592113A5 (en) | 1977-10-14 |
| DE2309030A1 (en) | 1973-09-13 |
| NL7302832A (en) | 1973-09-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |