GB1498132A - Steroidal 1,4-dioxanes - Google Patents

Steroidal 1,4-dioxanes

Info

Publication number
GB1498132A
GB1498132A GB1776/75A GB177675A GB1498132A GB 1498132 A GB1498132 A GB 1498132A GB 1776/75 A GB1776/75 A GB 1776/75A GB 177675 A GB177675 A GB 177675A GB 1498132 A GB1498132 A GB 1498132A
Authority
GB
United Kingdom
Prior art keywords
phenyl
alkyl
aryl
tetrahydropyran
yloxy
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
GB1776/75A
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 GB1498132A publication Critical patent/GB1498132A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
    • 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
    • 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
    • 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
    • C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
    • C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom
    • 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)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1498132 Steroid [16α,17-b]dioxanes E R SQUIBB & SONS Inc 15 Jan 1975 [16 Jan 1974] 1776/75 Headings C2U and C2C The invention comprises 3,20-dioxo pregnenes having an 11#-hydroxy or 11-oxo group and having at position 16,17 a fused-on 1,4-dioxane or dihydro - 1,4 - dioxin ring. Preferred are the #<SP>4</SP>, #<SP>1,4</SP>, #<SP>4,6</SP> and #<SP>1,4,6</SP> compounds of formula wherein A 1 is selected from (the valence on the left being attached to the 17-oxygen atom); R 1 is H, C 1-8 alkyl, or aryl; R 2 is H, C 1-8 alkyl or aryl-(C 1-8 alkyl); R 3 is C 1-8 alkyl, C 3-6 cycloalkyl, or aryl; R 4 and R 5 are each C 1-8 alkyl, or aryl; P is H, Me or Cl; Q is H, Me or F; X is H or halo; Y is H, Y<SP>1</SP> is OH or Y + Y<SP>1</SP> = oxo; Z is H, halo, OH or acyloxy; the term "aryl" signifying phenyl optionally sub stituted with one or more halo, C 1-8 alky or C 1-8 alkoxy groups. The inventive compounds are prepared from analogous 16α,17α-diol cyclic borates by synthesizing the 16,17-dioxane ring as shown in the reaction scheme infra, and subsequently optionally introducing #<SP>6</SP> unsaturation (e.g. with DDQ) acylating at position 21 (this may also be effected on the intermediates marked * and **), hydrolysing a 21-ester group, or converting 21- OH to 21-halo via a 21-sulphonate (this may also be effected on the intermediate marked **) (R 1 , R 3 , R 4 , R 5 and Z are as above; R 6 is alkyl or aryl; R 7 is alkyl or aralkyl; each X is alkyl or the two X's together are ethylene). Reagents: (a) CH 2 :C(R 1 )N 2 ; (b) (XO) 2 C(R 4 )C(R 5 )N 2 ; (d) THP.O.CH 2 CHN 2 ; (e) m-chloroperhenzoic acid; (f) e.g. periodic acid; (g) e.g. f-toluenesulphonic acid; (h) NaBH 4 ; (i) MeSO 2 Y (Y= halo); (j) NaHCO 3 /DMSO; (k) e.g. HCl; (1) (R 3 CO) 2 O; (m) Fetizon's reagent; (n) e.g. acetic acid; (p) tautomerism. A 16,17-cycloborate is prepared from 21-chloro- 9 - fluoro - 11#,16α,17 - trihydroxypregna - 1,4- diene - 3,20 - dione by reaction with boric oxide in methanol. Potassium phthalimide + α - (bromomethyl) styrene # N - (2 - phenyl - 2 - propenyl)phthalimide # ethyl N - (2 - phenyl - 2 - propenyl) carbamate # ethyl N - nitroso - N - (2 - phenyl - 2- propenyl)carbamate # 2 - phenyl - 3 - diazo - 1- propene (Example 4). 2 - (Tetrahydropyran - 2 - yloxy)acetonitrile # 2 - (tetrahydropyran - 2 - yloxy)ethylamine # N - [2 - (tetrahydropyran - 2 - yloxy)ethyl]urea # N - nitroso - N - [2 - (tetrahydropyran - 2 - yloxy) ethyl]urea # 2 - (tetrahydropyran - 2 - yloxy) - 1- diazoethane (Example 18). Potassium phthalimide + α-bromopropiophenone # N - (1 - methyl - 2 - oxo - 2 - phenylethyl) phthalimide # 2 - (1 - phthalimidoethyl) - 2- phenyl - 1,3 - dioxolane # 2 - (1 - aminoethyl) - 2- phenyl - 1,3 - dioxolane # 2 - phenyl - 2 - [1- (ethoxycarbonylamino)ethyl] - 1,3 - dioxolane # 2 - phenyl - 2 - (1 - diazoethyl) - 1,3 - dioxolane (Example 40). Antiinflammatory compositions for oral and topical administration comprise a compound of Formula I and a carrier.
GB1776/75A 1974-01-16 1975-01-15 Steroidal 1,4-dioxanes Expired GB1498132A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US43397474A 1974-01-16 1974-01-16

Publications (1)

Publication Number Publication Date
GB1498132A true GB1498132A (en) 1978-01-18

Family

ID=23722311

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1776/75A Expired GB1498132A (en) 1974-01-16 1975-01-15 Steroidal 1,4-dioxanes

Country Status (20)

Country Link
JP (1) JPS50101358A (en)
AR (1) AR209758A1 (en)
BE (1) BE824405A (en)
CA (1) CA1050966A (en)
CH (1) CH606116A5 (en)
CS (1) CS182829B2 (en)
DD (1) DD117449A5 (en)
DE (1) DE2501041A1 (en)
DK (1) DK9075A (en)
ES (1) ES433814A1 (en)
FI (1) FI750090A (en)
FR (2) FR2257299B1 (en)
GB (1) GB1498132A (en)
IE (1) IE42427B1 (en)
IL (1) IL46436A (en)
NL (1) NL7500458A (en)
NO (1) NO750119L (en)
SE (1) SE7500430L (en)
SU (1) SU581874A3 (en)
ZA (1) ZA75298B (en)

Also Published As

Publication number Publication date
ES433814A1 (en) 1977-02-16
FR2257299A1 (en) 1975-08-08
IL46436A0 (en) 1975-06-25
FR2257299B1 (en) 1978-08-04
DD117449A5 (en) 1976-01-12
CS182829B2 (en) 1978-05-31
SU581874A3 (en) 1977-11-25
NL7500458A (en) 1975-07-18
NO750119L (en) 1975-07-17
CA1050966A (en) 1979-03-20
BE824405A (en) 1975-07-15
FR2279760A1 (en) 1976-02-20
DK9075A (en) 1975-09-15
CH606116A5 (en) 1978-10-13
FR2279760B1 (en) 1978-09-22
JPS50101358A (en) 1975-08-11
IL46436A (en) 1979-05-31
AU7731075A (en) 1976-07-15
AR209758A1 (en) 1977-05-31
ZA75298B (en) 1976-01-28
IE42427L (en) 1975-07-16
FI750090A (en) 1975-07-17
IE42427B1 (en) 1980-08-13
DE2501041A1 (en) 1975-07-17
SE7500430L (en) 1975-07-17

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee