IE42112L - 2-BROMO-6ß-FLUOROPREGNA-1,4-DIENE-3,20-DIONES - Google Patents

2-BROMO-6ß-FLUOROPREGNA-1,4-DIENE-3,20-DIONES

Info

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
Application number
IE750379A
Other versions
IE42112B1 (en
Original Assignee
Pierrel Spa
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Pierrel Spa filed Critical Pierrel Spa
Publication of IE42112L publication Critical patent/IE42112L/en
Publication of IE42112B1 publication Critical patent/IE42112B1/en

Links

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)
  • 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

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]
IE379/75A 1974-02-27 1975-02-24 2-bromo-6-fluoropregna-1,4-diene-3,20-diones IE42112B1 (en)

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)

Also Published As

Publication number Publication date
DE2508136B2 (en) 1978-11-02
NO144527C (en) 1981-09-23
NZ176716A (en) 1978-07-10
SE7502146L (en) 1975-08-28
DE2533377B2 (en) 1978-11-16
CA1064476A (en) 1979-10-16
NO750633L (en) 1975-08-28
JPS50126652A (en) 1975-10-04
FR2261776B1 (en) 1978-07-21
DE2533323B2 (en) 1978-11-16
ES455934A1 (en) 1978-05-01
ES435067A1 (en) 1977-07-01
AR218601A1 (en) 1980-06-30
RO78881A (en) 1982-07-06
FI56188B (en) 1979-08-31
FR2261776A1 (en) 1975-09-19
DE2508136C3 (en) 1979-06-21
DK61575A (en) 1975-10-27
CH608243A5 (en) 1978-12-29
DK144068B (en) 1981-11-30
YU108281A (en) 1982-02-28
DE2508136A1 (en) 1975-10-30
SE410736B (en) 1979-10-29
GB1499822A (en) 1978-02-01
DK144068C (en) 1982-05-03
DE2533323C3 (en) 1979-07-12
LU71908A1 (en) 1975-06-24
FI750537A (en) 1975-08-28
YU108381A (en) 1982-02-28
JPS5614677B2 (en) 1981-04-06
DE2533323A1 (en) 1976-02-12
DE2533377C3 (en) 1979-08-02
ES455933A1 (en) 1978-05-01
BE826030A (en) 1975-06-16
NO144527B (en) 1981-06-09
IE42112B1 (en) 1980-06-04
FI56188C (en) 1979-12-10
YU108481A (en) 1982-02-28
DE2533377A1 (en) 1976-02-05

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