GB1458517A - 21-sulphinyl steroids - Google Patents
21-sulphinyl steroidsInfo
- Publication number
- GB1458517A GB1458517A GB5739173A GB5739173A GB1458517A GB 1458517 A GB1458517 A GB 1458517A GB 5739173 A GB5739173 A GB 5739173A GB 5739173 A GB5739173 A GB 5739173A GB 1458517 A GB1458517 A GB 1458517A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- halo
- steroids
- dec
- 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
- 150000003431 steroids Chemical class 0.000 title abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 2
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003862 glucocorticoid Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229960002317 succinimide Drugs 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
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)
- Steroid Compounds (AREA)
Abstract
1458517 21-Sulphinyl steroids E R SQUIBB & SONS Inc 11 Dec 1973 [15 Dec 1972] 57391/73 Heading C2U The invention comprises compounds of formula wherein R 1 is C 1-6 alkyl, C 3-7 cycloalkyl or a monocyclic carbocyclic aryl or aryl-C 1-6 -alkyl group optionally bearing halogen, C 1-6 alkyl or C 1-6 alkoxy substituents on the ring; R 2 is H, OH or C 1-6 alkyl; R 3 is H, OH, C 1-6 alkyl or methylene; or R 2 and R 3 together form a group of formula wherein R 4 and R 5 are each H, C 1-6 alkyl or a monocyclic carbocyclic aryl group optionally bearing halogen, C 1-6 alkyl or C 1-6 alkoxy substituents on the ring; or R 4 , R 5 and the intervening carbon atom together form a C 3-7 cycloalkyl group; R 6 is C 1-6 alkyl; X1 is OH or halo; X 2 is H or halo; X 3 is H, C 1-6 alkyl or halo; and the intracyclic broken lines indicate optical unsaturation in the 1,6 and 15 positions. Compounds I are prepared by oxidation of the corresponding 21-S-R 1 steroids, e.g. with iodosobenzene diacetate, iodobenzene dichloride, sodium metaperiodate or N-(chloro or bromo)- succinimide. The preparation of the products and intermediates is shown in the following scheme wherein K is the remainder of the steroid connected through the 17-position, and R 7 has the same definition as R 1 : (In Example 18, 9-fluoro-11#,16α,17,21-tetrahydroxypregna - 1,4 - diene - 3,20 - dione 21-p-toluenesulphonate is prepared in the form of its 16-acetate). Antiinflammatory and glucocorticoid compositions for oral and topical administration comprise a compound I and a carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00315701A US3803133A (en) | 1972-12-15 | 1972-12-15 | 21-sulfinyl steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1458517A true GB1458517A (en) | 1976-12-15 |
Family
ID=23225665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5739173A Expired GB1458517A (en) | 1972-12-15 | 1973-12-11 | 21-sulphinyl steroids |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3803133A (en) |
| CA (1) | CA1020546A (en) |
| DE (1) | DE2362280A1 (en) |
| FR (1) | FR2210410B1 (en) |
| GB (1) | GB1458517A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2231374B1 (en) * | 1973-05-30 | 1976-10-22 | Jouveinal Sa | |
| US4098803A (en) * | 1973-05-30 | 1978-07-04 | Jouveinal S.A. | Esters of 21-thiol-steroids hydrocortisone and cortisone |
| US4177268A (en) * | 1973-05-30 | 1979-12-04 | Jouveinal S.A. | Method of alleviating inflammation by administration of dexamethasone derivatives |
| US4221917A (en) * | 1978-03-03 | 1980-09-09 | Phillips Petroleum Company | Production of esters from monoolefins and diolefins |
| FR2442856A1 (en) * | 1978-12-01 | 1980-06-27 | Sipsy | PROCESS FOR THE PREPARATION OF STEROIDS |
| US5420120A (en) * | 1993-12-17 | 1995-05-30 | Alcon Laboratories, Inc. | Anti-inflammatory glucocorticoid compounds for topical ophthalmic use |
-
1972
- 1972-12-15 US US00315701A patent/US3803133A/en not_active Expired - Lifetime
-
1973
- 1973-12-07 CA CA187,699A patent/CA1020546A/en not_active Expired
- 1973-12-11 GB GB5739173A patent/GB1458517A/en not_active Expired
- 1973-12-14 DE DE2362280A patent/DE2362280A1/en not_active Ceased
- 1973-12-17 FR FR7345076A patent/FR2210410B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2362280A1 (en) | 1974-06-20 |
| FR2210410A1 (en) | 1974-07-12 |
| FR2210410B1 (en) | 1977-01-28 |
| CA1020546A (en) | 1977-11-08 |
| US3803133A (en) | 1974-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |