CH608243A5 - Process for the preparation of steroids - Google Patents

Process for the preparation of steroids

Info

Publication number
CH608243A5
CH608243A5 CH232575A CH232575A CH608243A5 CH 608243 A5 CH608243 A5 CH 608243A5 CH 232575 A CH232575 A CH 232575A CH 232575 A CH232575 A CH 232575A CH 608243 A5 CH608243 A5 CH 608243A5
Authority
CH
Switzerland
Prior art keywords
steroids
alpha
prepared
preparation
ketals
Prior art date
Application number
CH232575A
Inventor
Mario Riva
Luciano Toscano
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
Priority to CH1401177A priority Critical patent/CH608244A5/en
Publication of CH608243A5 publication Critical patent/CH608243A5/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

The steroids of the formula below, in which Y represents Cl or F, R1 and R2 are acyloxy groups and R3 a hydrogen atom or an ( alpha or ss) CH3 group, are prepared from a corresponding DELTA <9,11>-steroid by transformation to 9,11-epoxide and reaction of the intermediate product with HF or HCl. The 17 alpha ,21-dihydroxy derivatives of these steroids as well as their 17 alpha - or 21-monoesters and their cyclic 17,21-ketals and acetals are also prepared. All these compounds are pharmacologically useful as anti-inflammatory agents, especially against rheumatoid arthritis and dermatological conditions. <IMAGE>
CH232575A 1974-02-27 1975-02-25 Process for the preparation of steroids CH608243A5 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1401177A CH608244A5 (en) 1974-02-27 1975-02-25 Process for the preparation of steroids

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 (1)

Publication Number Publication Date
CH608243A5 true CH608243A5 (en) 1978-12-29

Family

ID=27447687

Family Applications (1)

Application Number Title Priority Date Filing Date
CH232575A CH608243A5 (en) 1974-02-27 1975-02-25 Process for the preparation of steroids

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) YU108281A (en)

Also Published As

Publication number Publication date
LU71908A1 (en) 1975-06-24
DE2508136C3 (en) 1979-06-21
FR2261776A1 (en) 1975-09-19
IE42112L (en) 1975-08-27
DE2508136B2 (en) 1978-11-02
NO144527C (en) 1981-09-23
ES455934A1 (en) 1978-05-01
DK144068C (en) 1982-05-03
DE2508136A1 (en) 1975-10-30
BE826030A (en) 1975-06-16
FI750537A (en) 1975-08-28
YU108481A (en) 1982-02-28
JPS5614677B2 (en) 1981-04-06
NO144527B (en) 1981-06-09
YU108281A (en) 1982-02-28
DK144068B (en) 1981-11-30
FI56188C (en) 1979-12-10
DE2533377B2 (en) 1978-11-16
CA1064476A (en) 1979-10-16
DE2533377A1 (en) 1976-02-05
YU108381A (en) 1982-02-28
JPS50126652A (en) 1975-10-04
DK61575A (en) 1975-10-27
ES435067A1 (en) 1977-07-01
IE42112B1 (en) 1980-06-04
RO78881A (en) 1982-07-06
AR218601A1 (en) 1980-06-30
GB1499822A (en) 1978-02-01
FI56188B (en) 1979-08-31
ES455933A1 (en) 1978-05-01
SE7502146L (en) 1975-08-28
DE2533323B2 (en) 1978-11-16
DE2533323A1 (en) 1976-02-12
NO750633L (en) 1975-08-28
FR2261776B1 (en) 1978-07-21
NZ176716A (en) 1978-07-10
SE410736B (en) 1979-10-29
DE2533323C3 (en) 1979-07-12
DE2533377C3 (en) 1979-08-02

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Legal Events

Date Code Title Description
PL Patent ceased