IE42112L - 2-BROMO-6ß-FLUOROPREGNA-1,4-DIENE-3,20-DIONES - Google Patents
2-BROMO-6ß-FLUOROPREGNA-1,4-DIENE-3,20-DIONESInfo
- Publication number
- IE42112L IE42112L IE750379A IE37975A IE42112L IE 42112 L IE42112 L IE 42112L IE 750379 A IE750379 A IE 750379A IE 37975 A IE37975 A IE 37975A IE 42112 L IE42112 L IE 42112L
- Authority
- IE
- Ireland
- Prior art keywords
- acyloxy
- hydrocarbyl
- prepared
- fluoropregna
- diones
- Prior art date
Links
- 125000004423 acyloxy group Chemical group 0.000 abstract 4
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 4
- 150000003431 steroids Chemical class 0.000 abstract 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- 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
- 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
- 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
- C07J5/0092—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 an OH group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (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
1499822 2 - Bromo - 6# - fluoropregna- 1,4-diene-3,20-diones PIERREL SpA 6 Feb 1975 [27 Feb 1974 5 July 1974 25 July 1974 19 Nov 1974] 8928/74 29984/74 32945/74 and 49982/74 Heading C2U Novel steroids have the formula wherein either X is OH and Y is F, Cl or Br, or X and Y are each Cl, and (i) R 1 is OH, R 2 is OH and R 3 is H, α-CH 3 or #-CH 3 ; or (ii) R 1 is acyloxy, R 2 is OH and R 3 is H, α-acyloxy, α-CH 3 or #-CH 3 ; or (iii) R 1 is OH or acyloxy, R 2 is acyloxy and R 3 is H, α-ChH 3 or #-CH 3 ; or (iv) R 1 is OH or acyloxy and either R 2 is OH and R 3 is α-OH or R 2 , and R 3 together are wherein R 4 is H or hydrocarbyl and R 5 is hydrocarbyl; or (v) R 1 and R 2 together are wherein R 6 is H, hydrocarbyl or alkoxy and R 7 is hydrocarbyl, and R 3 is H, α-CH 3 or #-CH 3 . They may be prepared as illustrated in the following reaction scheme which is largely self-explanatory. (XI)#(XIV) is the reaction of a 17α-acetoxy-16-unsubstituted compound with KOAc in hot DMF. 17α- Esters are prepared from 17α,21-diols via 17,21- o - esters. 17,21 - Acetonides are prepared from the 17α,21-diols and 2,2-dimethoxypropane. The novel steroids have anti-inflammatory activity and they may be made up into pharmaceutical compositions with suitable carriers.
[GB1499822A]
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8928/74A GB1499822A (en) | 1974-02-27 | 1974-02-27 | 2-bromo-6beta-fluoropregna-1,4-diene-3,20-diones |
| GB2998474 | 1974-07-05 | ||
| GB3294574 | 1974-07-25 | ||
| GB4998274 | 1974-11-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42112L true IE42112L (en) | 1975-08-27 |
| IE42112B1 IE42112B1 (en) | 1980-06-04 |
Family
ID=27447687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE379/75A IE42112B1 (en) | 1974-02-27 | 1975-02-24 | 2-bromo-6-fluoropregna-1,4-diene-3,20-diones |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5614677B2 (en) |
| AR (1) | AR218601A1 (en) |
| BE (1) | BE826030A (en) |
| CA (1) | CA1064476A (en) |
| CH (1) | CH608243A5 (en) |
| DE (3) | DE2508136C3 (en) |
| DK (1) | DK144068C (en) |
| ES (3) | ES435067A1 (en) |
| FI (1) | FI56188C (en) |
| FR (1) | FR2261776B1 (en) |
| GB (1) | GB1499822A (en) |
| IE (1) | IE42112B1 (en) |
| LU (1) | LU71908A1 (en) |
| NO (1) | NO144527C (en) |
| NZ (1) | NZ176716A (en) |
| RO (1) | RO78881A (en) |
| SE (1) | SE410736B (en) |
| YU (3) | YU108381A (en) |
-
1974
- 1974-02-27 GB GB8928/74A patent/GB1499822A/en not_active Expired
-
1975
- 1975-02-10 CA CA219,681A patent/CA1064476A/en not_active Expired
- 1975-02-14 FR FR7504616A patent/FR2261776B1/fr not_active Expired
- 1975-02-19 DK DK61575A patent/DK144068C/en not_active IP Right Cessation
- 1975-02-20 NZ NZ176716A patent/NZ176716A/en unknown
- 1975-02-24 AR AR257732A patent/AR218601A1/en active
- 1975-02-24 IE IE379/75A patent/IE42112B1/en unknown
- 1975-02-25 ES ES435067A patent/ES435067A1/en not_active Expired
- 1975-02-25 NO NO750633A patent/NO144527C/en unknown
- 1975-02-25 LU LU71908A patent/LU71908A1/xx unknown
- 1975-02-25 FI FI750537A patent/FI56188C/en not_active IP Right Cessation
- 1975-02-25 DE DE2508136A patent/DE2508136C3/en not_active Expired
- 1975-02-25 CH CH232575A patent/CH608243A5/en not_active IP Right Cessation
- 1975-02-26 SE SE7502146A patent/SE410736B/en unknown
- 1975-02-26 RO RO7581496A patent/RO78881A/en unknown
- 1975-02-26 BE BE153787A patent/BE826030A/en not_active IP Right Cessation
- 1975-02-26 JP JP2298075A patent/JPS5614677B2/ja not_active Expired
- 1975-07-25 DE DE2533323A patent/DE2533323C3/en not_active Expired
- 1975-07-25 DE DE2533377A patent/DE2533377C3/en not_active Expired
-
1977
- 1977-02-15 ES ES455933A patent/ES455933A1/en not_active Expired
- 1977-02-15 ES ES455934A patent/ES455934A1/en not_active Expired
-
1981
- 1981-04-27 YU YU01083/81A patent/YU108381A/en unknown
- 1981-04-27 YU YU01082/81A patent/YU108281A/en unknown
- 1981-04-27 YU YU01084/81A patent/YU108481A/en unknown
Also Published As
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