GB1502513A - Steroid(16,17-b)dioxanes - Google Patents

Steroid(16,17-b)dioxanes

Info

Publication number
GB1502513A
GB1502513A GB20206/75A GB2020675A GB1502513A GB 1502513 A GB1502513 A GB 1502513A GB 20206/75 A GB20206/75 A GB 20206/75A GB 2020675 A GB2020675 A GB 2020675A GB 1502513 A GB1502513 A GB 1502513A
Authority
GB
United Kingdom
Prior art keywords
alkyl
halo
chn
dione
diene
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
Application number
GB20206/75A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ER Squibb and Sons LLC
Original Assignee
ER Squibb and Sons LLC
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 ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC
Publication of GB1502513A publication Critical patent/GB1502513A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • 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
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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

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

1502513 Steroid[16α,17-b] dioxanes E R SQUIBB & SONS Inc 13 May 1975 [8 Nov 1974] 20206/75 Heading C2U The invention comprises #<SP>4</SP> steroids of Formula I and their #<SP>1,4</SP>, #<SP>4,6</SP> and #<SP>1,4,6</SP> analogues wherein A 1 is selected from (the valency on the left being attached to the 17- oxygen atom); P and Q are each H, Me or halo; X is Cl or F; Z is H, halo, OH or OCOR<SP>5</SP>; R<SP>1</SP> is H, C 1-8 alkyl, Ph, or Ph substituted with C 1-8 alkyl, C 1-8 alkoxy or halo; R<SP>2</SP> is H or C 1-8 alkyl; and R<SP>3</SP> and R<SP>5</SP> are each C 1-8 alkyl, C 3-6 cycloalkyl, Ph, or Ph substituted with C 1-8 alkyl, C 1-8 alkoxy or halo. The inventive compounds are prepared from compounds of formula by synthesizing the 16α,17α-dioxane ring as shown in the reaction scheme infra and, at any of the stages marked *, producing a 9,11-dihalo grouping by dehydrating to #<SP>9(11)</SP>-compounds (e.g. with POCL 3 /py or MsCl/py) followed by reaction with N-chlorosuccinimide and HX. Also at any appropriate stage #<SP>6</SP> unsaturation may be introduced (e.g. with DDQ), a 21-ester group hydrolysed, or a 21-hydroxy group replaced by H or halo via the 21-methanesulphonate. (R<SP>1</SP> and R<SP>3</SP> are as above; R is alkyl; R<SP>4</SP> is as R<SP>1</SP> except H). Reagents.- (a) THP . O-CH 2 CHN 2 ; (b) AcOH/H 2 O; (c) MsCl/py; (d) NaHCO 3 /DMS; (e) (RO) 2 CH-CHN 2 ; (f) TsOH/PhH; (g) HCl/THF; (h) CH 2 =C(R<SP>1</SP>)-CHN 2 ; (i) mchloroperbenzoic acid; (j) H 5 IO 6 ; (k) NaBH 4 ; (l) (R<SP>3</SP>CO) 2 O or R<SP>3</SP>COCl; (m) K 2 CO 3 /MeOH; (n) Fetizon's reagent; (p) H 5 IO 6 ; (q) and (r) TsOH/PhH. 16,17-Cycloborates are prepared from 6α- fluoro-11#,16α,17,21 - tetrahydroxypregna - 1,4- diene-3,20-dione, 21-chloro-11#,16α,17-trihydroxypregna - 1,4 - diene - 3,20 - dione and 11#,16α,17,21 - tetrahydroxy - 6α - methylpregna-1,4-diene-3,20-dione by reaction with boric anhydride in methanol (Examples 5, 8, 18). 2 - (Tetrahydropyran - 2 - yloxy) - 1 - diazoethane (Example 1) and 2-phenyl-3-diazo-1- propane (Example 7) and their precursors are prepared as described in Specification 1,498,132. Anti-inflammatory compositions for oral and topical administration comprise a compound of the invention and a carrier.
GB20206/75A 1974-11-08 1975-05-13 Steroid(16,17-b)dioxanes Expired GB1502513A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US52219574A 1974-11-08 1974-11-08

Publications (1)

Publication Number Publication Date
GB1502513A true GB1502513A (en) 1978-03-01

Family

ID=24079846

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20206/75A Expired GB1502513A (en) 1974-11-08 1975-05-13 Steroid(16,17-b)dioxanes

Country Status (2)

Country Link
JP (2) JPS5942399A (en)
GB (1) GB1502513A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2691280B2 (en) * 1988-05-12 1997-12-17 三菱電機株式会社 Semiconductor memory device
DE69212746T2 (en) * 1991-09-03 1997-01-30 Shibuya Kogyo Co Ltd Device for automatically changing a system for treating objects

Also Published As

Publication number Publication date
JPS5942400A (en) 1984-03-08
JPS5942399A (en) 1984-03-08

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee