GB1094809A - Unsaturated 4,5-seco-steroid compounds, and processes for their preparation - Google Patents

Unsaturated 4,5-seco-steroid compounds, and processes for their preparation

Info

Publication number
GB1094809A
GB1094809A GB17464/67A GB1746467A GB1094809A GB 1094809 A GB1094809 A GB 1094809A GB 17464/67 A GB17464/67 A GB 17464/67A GB 1746467 A GB1746467 A GB 1746467A GB 1094809 A GB1094809 A GB 1094809A
Authority
GB
United Kingdom
Prior art keywords
seco
dinor
pregna
dialkyl
chloro
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
GB17464/67A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB1094809A publication Critical patent/GB1094809A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

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

Novel 4,5-deco-steroids having the formulae <FORM:1094809/C2/1> <FORM:1094809/C2/2> <FORM:1094809/C2/3> <FORM:1094809/C2/4> <FORM:1094809/C2/5> <FORM:1094809/C2/6> wherein R and R1 each represent alkyl radicals containing from 1-4 carbon atoms, and Acyl represents an acyl group, are obtained by reacting a 5-enamino-13b ,17a -dialkyl-20-acyl-oxy - des - A - 18, 19 - dinor - pregna - 5(10),9(11)-diene with 1,3-dichloro-2-butene to form the corresponding 3 - chloro - 13b ,17a - dialkyl - 20 - acyloxy - 4,5 - seco - 18,19 - dinor - pregna-2,9-dien-5-one, reacting the latter with an acetylating agent to form a 3-chloro-5-acetoxy-13b ,17a -dialkyl - 20 - acyloxy - 4,5 - seco - 18,19 - dinor-pregna - 2,5(10),9(11) - triene, reacting the latter with a brominating agent to form a 3-chloro - 11 - bromo - 13b ,17a - dialkyl - 20 - acyloxy - 4,5 - seco - 18,19 - dinor - pregna - 2,9-dien-5-one, dehydrobrominating the latter with a basic material to form a 3-chloro-13b ,17a -dialkyl - 20 - acyloxy - 4,5 - seco - 18,19 - dinor-pregna-2,9,11-trien-5-one, reacting the latter with a saponifying agent to form a 3-chloro-13b , 17a - dialkyl - 20 - hydroxy - 4,5 - seco - 18,19-dinor - pregna - 2,9,11 - trien - 5 - one and reacting the latter with an oxidizing agent to obtain the desired 3-chloro-13b ,17a -dialkyl-4,5-seco - 18,19 - dinor - pregna - 2,9,11 - triene-5,20-dione.
GB17464/67A 1964-11-04 1965-11-04 Unsaturated 4,5-seco-steroid compounds, and processes for their preparation Expired GB1094809A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR993811A FR1492772A (en) 1964-11-04 1964-11-04 New triene steroid derivatives and method of preparation
FR15549A FR6534M (en) 1964-11-04 1965-05-03

Publications (1)

Publication Number Publication Date
GB1094809A true GB1094809A (en) 1967-12-13

Family

ID=26163557

Family Applications (5)

Application Number Title Priority Date Filing Date
GB17465/67A Expired GB1094810A (en) 1964-11-04 1965-11-04 Unsaturated 4,5-seco-steroid compounds, and processes for their preparation
GB17464/67A Expired GB1094809A (en) 1964-11-04 1965-11-04 Unsaturated 4,5-seco-steroid compounds, and processes for their preparation
GB17462/67A Expired GB1094807A (en) 1964-11-04 1965-11-04 Unsaturated des-a steroid compounds, and processes for their preparation
GB46744/65A Expired GB1094806A (en) 1964-11-04 1965-11-04 Unsaturated steroid compounds and processes for their preparation
GB17463/67A Expired GB1094808A (en) 1964-11-04 1965-11-04 Unsaturated des-a steroid compounds, and processes for their preparation

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB17465/67A Expired GB1094810A (en) 1964-11-04 1965-11-04 Unsaturated 4,5-seco-steroid compounds, and processes for their preparation

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB17462/67A Expired GB1094807A (en) 1964-11-04 1965-11-04 Unsaturated des-a steroid compounds, and processes for their preparation
GB46744/65A Expired GB1094806A (en) 1964-11-04 1965-11-04 Unsaturated steroid compounds and processes for their preparation
GB17463/67A Expired GB1094808A (en) 1964-11-04 1965-11-04 Unsaturated des-a steroid compounds, and processes for their preparation

Country Status (10)

Country Link
BE (1) BE671482A (en)
BR (2) BR6574582D0 (en)
CH (2) CH448079A (en)
DE (1) DE1468940A1 (en)
DK (2) DK111891B (en)
FR (2) FR1492772A (en)
GB (5) GB1094810A (en)
IL (4) IL24528A (en)
NL (3) NL6514226A (en)
SE (2) SE323367B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7329654B2 (en) 2001-12-19 2008-02-12 Janssen Pharmaceutica N.V. Heteroatom containing tetracyclic derivatives as selective estrogen receptor modulators
JP2005513133A (en) * 2001-12-19 2005-05-12 オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド Tetracyclic complex compounds as estrogen receptor modulators
US7105679B2 (en) 2001-12-19 2006-09-12 Kanojia Ramesh M Heteroatom containing tetracyclic derivatives as selective estrogen receptor modulators

Also Published As

Publication number Publication date
CH448079A (en) 1967-12-15
GB1094808A (en) 1967-12-13
NL6514226A (en) 1966-05-05
DK112031B (en) 1968-11-04
DK111891B (en) 1968-10-21
NL124481C (en)
IL34614A (en) 1970-11-30
IL33432A (en) 1970-11-30
DE1468940A1 (en) 1969-02-06
FR6534M (en) 1968-12-16
SE309234B (en) 1969-03-17
IL33395A (en) 1970-10-30
BE671482A (en) 1966-04-27
IL24528A (en) 1970-09-17
FR1492772A (en) 1967-08-25
BR6574582D0 (en) 1973-09-06
CH448078A (en) 1967-12-15
GB1094807A (en) 1967-12-13
SE323367B (en) 1970-05-04
DE1468941A1 (en) 1969-03-13
GB1094810A (en) 1967-12-13
BR6574583D0 (en) 1973-09-06
NL6514225A (en) 1966-05-05
GB1094806A (en) 1967-12-13

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