GB1502513A - Steroid(16,17-b)dioxanes - Google Patents
Steroid(16,17-b)dioxanesInfo
- 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
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)
- 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
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.
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)
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 |
EP0531103B1 (en) * | 1991-09-03 | 1996-08-14 | Shibuya Kogyo Co., Ltd | Apparatus for automatic remodelling of an article processing system |
-
1975
- 1975-05-13 GB GB20206/75A patent/GB1502513A/en not_active Expired
-
1983
- 1983-04-15 JP JP58067670A patent/JPS5942399A/en active Pending
- 1983-04-15 JP JP58067671A patent/JPS5942400A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
JPS5942399A (en) | 1984-03-08 |
JPS5942400A (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 |