GB1495513A - Steroid compounds of the 20(22)-cardenolide series - Google Patents

Steroid compounds of the 20(22)-cardenolide series

Info

Publication number
GB1495513A
GB1495513A GB5026274A GB5026274A GB1495513A GB 1495513 A GB1495513 A GB 1495513A GB 5026274 A GB5026274 A GB 5026274A GB 5026274 A GB5026274 A GB 5026274A GB 1495513 A GB1495513 A GB 1495513A
Authority
GB
United Kingdom
Prior art keywords
carda
dienolide
epoxy
acetoxy
hydroxy
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
GB5026274A
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.)
Steele Chemicals Co Ltd
Original Assignee
Steele Chemicals Co Ltd
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 Steele Chemicals Co Ltd filed Critical Steele Chemicals Co Ltd
Publication of GB1495513A publication Critical patent/GB1495513A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07J71/001—Oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
    • 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
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
    • C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1495513 20(22)-Cardenolides STEELE CHEMICALS CO Ltd 20 Nov 1974 [29 Nov 1973] 50262/74 Heading C2U The invention comprises: (A) a process for preparing compounds of Formula I infra from II by reaction with ZCH 2 CO 2 H or a functional derivative thereof to give III, base-inducec cyclization of which yields I R 1 is H, oxo, OH, OMe, OCOH, OCOMe, OCOCH 2 P(O)(OEt) 2 , OCOCH 2 CO 2 H, OCH 2 Ph, OCH 2 C#CH, or tetrahydropyran - 2 - yloxy; R 2 is CH 3 , CHO, CH 2 Cl, CH 2 OH, CH 2 OMe, CH 2 OCOH, CH 2 OCOMe, CH 2 OCOCH(Me) (OH), CH 2 OCO(CH 2 OH) 2 CO 2 H, CH 2 OCOCH 2 CO 2 H, CH 2 OCH 2 C#CH; tetrahydropyran-2-yloxymethyl, or R 3 is H, CN, CO 2 Me, CO 2 CH 2 Ph, CO 2 CH 2 C # CH, or CO 2 CH 2 CH 2 OH; R 6 (when present) is α-H, #-H, α-Cl, α-Br or α-OH; R 7 is H, or R 2 and R 7 together are -CH 2 -O- (the -O- of which is attached to C 6 ); R 8 is H, or R 2 and R 8 together are -CH 2 -O-, -CO-O-, or -CH(OH)-O- (the -O- of which is attached to C 8 ); X-Y is C(#-OH)-CH 2 , C(α-H)-CH 2 , C(#-H)-CH 2 , C=CH, C(#-OH)-CH(α-Q 1 ) or C(#-OCOQ 2 )-CH 2 -, Q 1 being Br, Cl, OCOMe or OCOBu<SP>t</SP>, and Q 2 being H or Me; Z is a substituent which enhances the acidity of the adjacent CH 2 (Z generally being retained in the product as R 3 except for Z=P(O)(OEt) 2 which results in R 3 = H); and the dotted lines in the ring, represent optional #<SP>4</SP>, #<SP>5</SP> or #<SP>4,6</SP>-ethylenic unsaturation; and (B) the following compounds per se: 3# - acetoxy - 8, 19 - epoxy - 5α - carda - 14,20- (22) - dienolide; 3# - acetoxy - 22 - (benzyloxycarbonyl) - 8,19 - epoxy - 5α - carda - 14,20- (22) - dienolide; 3# - acetoxy - 22 - cyano - 8,19- epoxy - 5α - carda - 14,20(22) - dienolide; 22- cyano - 3# - hydroxy - 8,19 - epoxy - 5α - carda- 14,20(22) - dienolide; 19 - acetoxy - 3 - oxo- 14α - carda - 4,6,20(22 - trienolide; 3 - oxo - 8, 19 - epoxy - 14α - carda - 4,20(22) - dienolide; 3# - [(diethylphosphono)acetoxy] - 14α - carda- 5,20(22) - dienolide; 3# - acetoxy - 22 - cyano- 14α - carda - 5, 20(22) - dienolide; 3# - hydroxy- 22 - cyano - 14α - carda - 5, 20(22) - dienolide; 8,19 - epoxy - 5α - carda - 14,20(22) - dienolide; 19 - formyloxy - 5α - carda - 14,20(22) - dienolide*; 3# - acetoxy - 19 - hydroxy - 5α - carda- 14,20(22) - dienolide*; 3# - acetoxy - 15α- bromo - 19 - formyloxy - 14# - hydroxy - 5α- card - 20(22) - enolide*; coroglaucigenin 3- acetate 19 - formate*; 3# - acetoxy - 19 - formyloxy - 14#,15# - epoxy - 5α - card - 20(22)- enolide*; 3# - acetoxy - 14#, 19 - dihydroxy- 5α - card - 20(22) - enolide*; 14#, 19 - dihydroxy - 5α - card - 20(22) - enolide 19- formate*; 19 - formyloxy - 14,15# - epoxy- 5α,14# - card - 20(22) - enolide*: and 3 - oxo - 6,19 - epoxy - 14α - carda - 4,20(22) - dienolide; all of these being immediate products of process (A) followed in some cases by hydrolysis of 3-ester groups, with the exception of those marked * which are produced in subsequent process steps infra. When the cardenolides produced by the process (A) are 8,19-epoxy-14-enes, subsequent cleavage of the epoxy group with Zn/HCHO (optionally followed by acetylation) yields a 19-hydroxy-14-ene or formate or acetate thereof, reaction of which with N-bromoacetamide yields the corresponding 19-oxygenated-14#- hydroxy-15α-bromo compound, reaction of which with Raney nickel, NH 4 OH or t-butylamine yields the corresponding 19-oxygenated- 14# - hydroxy - 15 - unsubstituted or 19- oxygenated - 14#,15# - epoxy compound, whereafter 3- and 19-ester groups may be hydrolysed and 19-OH oxidized to oxo. These after-processes, which are the subject of Examples 14--28, give both known and novel (supra) compounds.
GB5026274A 1973-11-29 1974-11-20 Steroid compounds of the 20(22)-cardenolide series Expired GB1495513A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA186,960A CA1049498A (en) 1973-11-29 1973-11-29 Steroid compounds and processes therefor

Publications (1)

Publication Number Publication Date
GB1495513A true GB1495513A (en) 1977-12-21

Family

ID=4098526

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5026274A Expired GB1495513A (en) 1973-11-29 1974-11-20 Steroid compounds of the 20(22)-cardenolide series

Country Status (3)

Country Link
CA (1) CA1049498A (en)
DE (1) DE2455272A1 (en)
GB (1) GB1495513A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU77457A1 (en) * 1977-05-31 1979-01-19
US4937237A (en) * 1988-12-23 1990-06-26 Smithkline Beckman Corporation Phosphinic acid substituted aromatic steroids as inhibitors of steroid 5-60 -reductase
US4882319A (en) * 1988-12-23 1989-11-21 Smithkline Beckman Corporation Phosphonic acid substituted aromatic steroids as inhibitors of steroid 5-α-reductase

Also Published As

Publication number Publication date
DE2455272A1 (en) 1975-06-05
CA1049498A (en) 1979-02-27

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Legal Events

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