GB1510617A - 16-methyl-9alpha-halo steroid esters and ethers and preparation thereof - Google Patents
16-methyl-9alpha-halo steroid esters and ethers and preparation thereofInfo
- Publication number
- GB1510617A GB1510617A GB12608/75A GB1260875A GB1510617A GB 1510617 A GB1510617 A GB 1510617A GB 12608/75 A GB12608/75 A GB 12608/75A GB 1260875 A GB1260875 A GB 1260875A GB 1510617 A GB1510617 A GB 1510617A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethers
- methyl
- tetrahydropyran
- acyloxy
- preparation
- 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 -halo steroid esters Chemical class 0.000 title abstract 2
- 150000002170 ethers Chemical class 0.000 title abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 229940051868 antimigraine drug corticosteroid derivative Drugs 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical class OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 238000003797 solvolysis reaction Methods 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- 230000000699 topical effect Effects 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
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07J5/0046—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 substituted in position 17 alfa
- C07J5/0061—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 substituted in position 17 alfa substituted in position 16
- C07J5/0069—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
-
- 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
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16
- C07J7/0055—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1510617 21 - Deoxy - 16 - methyl corticosteroid derivatives PLURICHEMIE ANSTALT 26 March 1975 [27 March 1974 (2) 10 May 1975] 12608/75 Heading C2U The invention comprises compounds of formula wherein X is Cl or F, and either (i) R 1 is OH or C 1-16 acyloxy and R 2 is tetrahydropyran-2-yloxy, or (ii) R 1 is C 6-16 acyloxy and R 2 is OH, or (iii) R 1 and R 2 are each C 1-16 acyloxy. Preparation of I is from the corresponding 11, 17-diols by conversion to their 11-(tetrahydropyran-2-yl) ethers or 11-(di- or tri-chloro- or fluoro-acetates), followed as appropriate by 17-esterification, selective 11-hydrolysis (or solvolysis in the presence of silica gel) and 11- esterification. 21 - Deoxybeclomethasone and its 16α- epimer are prepared from their 9,11-epoxy analogues by reaction with HCl. 21 - Deoxybeclomethasone 11 - propionate is prepared from its 11-(tetrahydropyran-2-yloxy) analogue by reaction with EtCO 2 H. Anti-inflammatory compositions for oral, topical and parenteral administration comprise a compound I and a carrier.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT6163674 | 1974-03-27 | ||
| PT6163774 | 1974-03-27 | ||
| PT6163675 | 1975-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1510617A true GB1510617A (en) | 1978-05-10 |
Family
ID=27354092
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47940/77A Expired GB1511820A (en) | 1974-03-27 | 1975-03-26 | 16-methyl-9alpha-halo steroid ethers and esters and their preparation |
| GB12608/75A Expired GB1510617A (en) | 1974-03-27 | 1975-03-26 | 16-methyl-9alpha-halo steroid esters and ethers and preparation thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47940/77A Expired GB1511820A (en) | 1974-03-27 | 1975-03-26 | 16-methyl-9alpha-halo steroid ethers and esters and their preparation |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE827275A (en) |
| CH (2) | CH622811A5 (en) |
| DK (1) | DK153556C (en) |
| FR (1) | FR2274309A1 (en) |
| GB (2) | GB1511820A (en) |
| IE (2) | IE41137B1 (en) |
| NZ (1) | NZ177056A (en) |
| SE (1) | SE440656B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR890000664B1 (en) * | 1981-10-19 | 1989-03-22 | 바리 안소니 뉴우샘 | Preparation method for micronised be clomethasone dispropionate mono-hydrate |
| IT1285770B1 (en) | 1996-10-04 | 1998-06-18 | Nicox Sa | CORTICOID COMPOUNDS |
| CN102516348B (en) * | 2011-11-10 | 2013-11-13 | 中国科学院上海有机化学研究所 | 16S-Methyl-20S-droxypregna compound, and synthesis method and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1070751A (en) * | 1964-01-28 | 1967-06-01 | Glaxo Lab Ltd | 17-esters of 17-hydroxy-21-desoxy-steroids |
| GB1139505A (en) * | 1965-06-23 | 1969-01-08 | Glaxo Lab Ltd | A process for the production of 17-‡-monoesters of 17-‡-hydroxy-20-keto-steroids |
| US3383394A (en) * | 1965-08-30 | 1968-05-14 | Schering Corp | Novel 17-acylating process and products thereof |
| CH481085A (en) * | 1965-08-30 | 1969-11-15 | Scherico Ltd | Process for the preparation of 11B-hydroxy-17 -alkanoyloxysteroids of the pregnane series |
| BE788355A (en) * | 1971-09-07 | 1973-03-05 | Merck Patent Gmbh | 9 ALPHA-FLUORO-16-METHYLENE-PREDNISOLONE ESTERS |
-
1975
- 1975-03-26 NZ NZ177056A patent/NZ177056A/en unknown
- 1975-03-26 DK DK129575A patent/DK153556C/en not_active IP Right Cessation
- 1975-03-26 CH CH392475A patent/CH622811A5/de not_active IP Right Cessation
- 1975-03-26 GB GB47940/77A patent/GB1511820A/en not_active Expired
- 1975-03-26 GB GB12608/75A patent/GB1510617A/en not_active Expired
- 1975-03-27 IE IE693/75A patent/IE41137B1/en unknown
- 1975-03-27 FR FR7509621A patent/FR2274309A1/en active Granted
- 1975-03-27 BE BE154849A patent/BE827275A/en not_active IP Right Cessation
- 1975-03-27 IE IE2062/75A patent/IE41138B1/en unknown
-
1978
- 1978-03-16 SE SE7803041A patent/SE440656B/en not_active IP Right Cessation
-
1979
- 1979-10-22 CH CH946879A patent/CH625254A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2274309B1 (en) | 1978-11-24 |
| IE41137L (en) | 1975-09-27 |
| NZ177056A (en) | 1978-09-20 |
| CH625254A5 (en) | 1981-09-15 |
| GB1511820A (en) | 1978-05-24 |
| DK129575A (en) | 1975-09-28 |
| BE827275A (en) | 1975-07-16 |
| SE440656B (en) | 1985-08-12 |
| SE7803041L (en) | 1978-03-16 |
| IE41138B1 (en) | 1979-10-24 |
| DK153556B (en) | 1988-07-25 |
| IE41137B1 (en) | 1979-10-24 |
| FR2274309A1 (en) | 1976-01-09 |
| DK153556C (en) | 1988-12-05 |
| CH622811A5 (en) | 1981-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19950325 |