GB1391443A - Ester of betamethasone and its 9alpha-chloro analogue - Google Patents
Ester of betamethasone and its 9alpha-chloro analogueInfo
- Publication number
- GB1391443A GB1391443A GB3134971A GB3134971A GB1391443A GB 1391443 A GB1391443 A GB 1391443A GB 3134971 A GB3134971 A GB 3134971A GB 3134971 A GB3134971 A GB 3134971A GB 1391443 A GB1391443 A GB 1391443A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyl
- comparison
- 9alpha
- betamethasone
- ester
- 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
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 title 1
- 229960002537 betamethasone Drugs 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000003431 steroids Chemical class 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 abstract 1
- 230000002411 adverse Effects 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 229910052801 chlorine Chemical group 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000009885 systemic effect Effects 0.000 abstract 1
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
-
- 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
- C07J5/0053—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 not substituted in position 16
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
21-Adamantoyloxysteroids of the formula I <IMAGE> in which A is hydroxyl and B is fluorine or chlorine, or A and B together represent a carbon-carbon bond, are distinguished by a systemic antiinflammatory activity with a duration of action which is considerably prolonged by comparison with known antiinflammatory steroids and, furthermore, adversely affect the function of the adrenals considerably less by comparison with known steroids. The said compounds are prepared by reacting the corresponding compounds which are substituted in position 21 by hydroxyl, iodine or a hydrocarbon-sulphonyloxy group with a compound supplying the adamantoyl group, namely a halide, anhydride or salt of adamantane-1-carboxylic acid.
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE785812D BE785812A (en) | 1971-07-05 | NEW STEROID COMPOUNDS | |
GB3134971A GB1391443A (en) | 1971-07-05 | 1971-07-05 | Ester of betamethasone and its 9alpha-chloro analogue |
FR7224132A FR2144761B1 (en) | 1971-07-05 | 1972-07-04 | |
CH1003472A CH609065A5 (en) | 1971-07-05 | 1972-07-04 | Process for the preparation of 21-adamantoyloxysteroids |
NO2406/72A NO137754C (en) | 1971-07-05 | 1972-07-04 | ANALOGICAL PROCEDURE FOR PREPARING THERAPEUTICALLY ACTIVE STEROID COMPOUNDS |
AU44205/72A AU464251B2 (en) | 1971-07-05 | 1972-07-04 | Steroid compounds |
IL39821A IL39821A (en) | 1971-07-05 | 1972-07-04 | Betamethasone-and 9alpha-chlorobetamethasone 21-adamantoate |
NLAANVRAGE7209345,A NL169882C (en) | 1971-07-05 | 1972-07-04 | PROCESS FOR PREPARING A PHARMACEUTICAL PREPARATION, FORMED PHARMACEUTICAL PREPARATION AND PROCESS FOR PREPARING 21-STEROID ALCOHOL (1-ADAMANANIC CARBONIC ACID) ESTERS. |
JP6640472A JPS5644079B1 (en) | 1971-07-05 | 1972-07-04 | |
SE7208817A SE385904B (en) | 1971-07-05 | 1972-07-04 | PROCEDURE FOR THE PREPARATION OF THE 21-ADAMANTOATS OF BERAMETASON AND ITS 9ALFA-CHLORINE ANALOG |
AR242889A AR194120A1 (en) | 1971-07-05 | 1972-07-04 | A PROCEDURE FOR PREPARING A STEROID COMPUTER |
DK331372AA DK131474B (en) | 1971-07-05 | 1972-07-04 | Analogous process for the preparation of 9alpha-halogen-11beta, 17alpha, 21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione-21-adamantane-1'-carboxylates. |
ZA724598A ZA724598B (en) | 1971-07-05 | 1972-07-04 | Steroid compounds |
CA146,248A CA983919A (en) | 1971-07-05 | 1972-07-04 | Steroid compounds |
IE939/72A IE36529B1 (en) | 1971-07-05 | 1972-07-04 | Esters of betamethasone and its 9alpha-chloro analogue |
DE2232827A DE2232827A1 (en) | 1971-07-05 | 1972-07-04 | NEW STEROIDS AND THE METHOD OF MANUFACTURING THEM |
PH13687A PH13195A (en) | 1971-07-05 | 1972-07-05 | Beta methasone-21-adamantane-1'-carboxylate,its chloro analogue,composition and method of use |
AR248131A AR194553A1 (en) | 1971-07-05 | 1973-05-21 | A PROCEDURE FOR PREPARING A STEROID COMPOUND |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3134971A GB1391443A (en) | 1971-07-05 | 1971-07-05 | Ester of betamethasone and its 9alpha-chloro analogue |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1391443A true GB1391443A (en) | 1975-04-23 |
Family
ID=10321802
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3134971A Expired GB1391443A (en) | 1971-07-05 | 1971-07-05 | Ester of betamethasone and its 9alpha-chloro analogue |
Country Status (17)
Country | Link |
---|---|
JP (1) | JPS5644079B1 (en) |
AR (2) | AR194120A1 (en) |
AU (1) | AU464251B2 (en) |
BE (1) | BE785812A (en) |
CA (1) | CA983919A (en) |
CH (1) | CH609065A5 (en) |
DE (1) | DE2232827A1 (en) |
DK (1) | DK131474B (en) |
FR (1) | FR2144761B1 (en) |
GB (1) | GB1391443A (en) |
IE (1) | IE36529B1 (en) |
IL (1) | IL39821A (en) |
NL (1) | NL169882C (en) |
NO (1) | NO137754C (en) |
PH (1) | PH13195A (en) |
SE (1) | SE385904B (en) |
ZA (1) | ZA724598B (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS49116217A (en) * | 1973-01-03 | 1974-11-06 | ||
DE2512915A1 (en) * | 1974-03-27 | 1975-10-09 | Plurichemie Anstalt | 16-METHYL-9 ALPHA-HALOGEN-STEROID ESTERS, ETHERS AND METHOD FOR THEIR PRODUCTION |
JPS6163976U (en) * | 1984-10-01 | 1986-05-01 | ||
KR101749032B1 (en) | 2008-05-28 | 2017-06-20 | 레베라겐 바이오파마 인코포레이티드 | NON-HORMONAL STEROID MODULATORS OF NF-κB FOR TREATMENT OF DISEASE |
WO2011127048A2 (en) | 2010-04-05 | 2011-10-13 | Validus Biopharma | NON-HORMONAL STEROID MODULATORS OF NF-ĸB FOR TREATMENT OF DISEASE |
WO2017004205A1 (en) | 2015-06-29 | 2017-01-05 | Reveragen Biopharma, Inc. | NON-HORMONAL STEROID MODULATORS OF NF-κB FOR TREATMENT OF DISEASE |
US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
-
0
- BE BE785812D patent/BE785812A/en not_active IP Right Cessation
-
1971
- 1971-07-05 GB GB3134971A patent/GB1391443A/en not_active Expired
-
1972
- 1972-07-04 CH CH1003472A patent/CH609065A5/en not_active IP Right Cessation
- 1972-07-04 NL NLAANVRAGE7209345,A patent/NL169882C/en not_active IP Right Cessation
- 1972-07-04 CA CA146,248A patent/CA983919A/en not_active Expired
- 1972-07-04 ZA ZA724598A patent/ZA724598B/en unknown
- 1972-07-04 FR FR7224132A patent/FR2144761B1/fr not_active Expired
- 1972-07-04 SE SE7208817A patent/SE385904B/en unknown
- 1972-07-04 DE DE2232827A patent/DE2232827A1/en not_active Ceased
- 1972-07-04 AR AR242889A patent/AR194120A1/en active
- 1972-07-04 AU AU44205/72A patent/AU464251B2/en not_active Expired
- 1972-07-04 DK DK331372AA patent/DK131474B/en unknown
- 1972-07-04 NO NO2406/72A patent/NO137754C/en unknown
- 1972-07-04 JP JP6640472A patent/JPS5644079B1/ja active Pending
- 1972-07-04 IL IL39821A patent/IL39821A/en unknown
- 1972-07-04 IE IE939/72A patent/IE36529B1/en unknown
- 1972-07-05 PH PH13687A patent/PH13195A/en unknown
-
1973
- 1973-05-21 AR AR248131A patent/AR194553A1/en active
Also Published As
Publication number | Publication date |
---|---|
JPS5644079B1 (en) | 1981-10-16 |
DK131474C (en) | 1975-12-08 |
AU464251B2 (en) | 1975-08-21 |
AR194553A1 (en) | 1973-07-23 |
AU4420572A (en) | 1974-01-10 |
DK131474B (en) | 1975-07-21 |
IL39821A0 (en) | 1972-09-28 |
BE785812A (en) | 1973-01-04 |
PH13195A (en) | 1980-01-18 |
NO137754B (en) | 1978-01-09 |
NO137754C (en) | 1978-04-19 |
CA983919A (en) | 1976-02-17 |
NL169882C (en) | 1982-09-01 |
FR2144761B1 (en) | 1976-03-05 |
IL39821A (en) | 1976-02-29 |
IE36529L (en) | 1973-01-05 |
NL169882B (en) | 1982-04-01 |
NL7209345A (en) | 1973-01-09 |
SE385904B (en) | 1976-07-26 |
FR2144761A1 (en) | 1973-02-16 |
CH609065A5 (en) | 1979-02-15 |
AR194120A1 (en) | 1973-06-22 |
DE2232827A1 (en) | 1973-01-18 |
ZA724598B (en) | 1973-03-28 |
IE36529B1 (en) | 1976-11-24 |
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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 |