GB1180584A - Steroids - Google Patents

Steroids

Info

Publication number
GB1180584A
GB1180584A GB1138367A GB1138367A GB1180584A GB 1180584 A GB1180584 A GB 1180584A GB 1138367 A GB1138367 A GB 1138367A GB 1138367 A GB1138367 A GB 1138367A GB 1180584 A GB1180584 A GB 1180584A
Authority
GB
United Kingdom
Prior art keywords
substituted
nucleus
compound
gona
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
GB1138367A
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.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries 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 Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Priority to GB1138367A priority Critical patent/GB1180584A/en
Priority to FR98416A priority patent/FR1526031A/en
Publication of GB1180584A publication Critical patent/GB1180584A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051—Estrane derivatives
    • C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051—Estrane derivatives
    • C07J1/0062—Estrane derivatives substituted in position 17 alfa not substituted in position 17 beta

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,180,584. Steroids. TAKEDA YAKUHIN KOGYO K.K. 10 March, 1967 [11 March, 1966; 12 March, 1966 (2); 29 April, 1966; 31 May, 1966; 15 Oct., 1966 (5)], No. 11383/67. Heading C2U. The invention comprises a compound having a gonapenta-, tetra- or tri-en-17α-ol nucleus, the nucleus being substituted with a hydrocarbon residue in the 13-position and a process for producing a compound having a 13-substitutedgona-1,3,5(10), 8, 14-pentaen-17α-ol nucleus which comprises: (1) reacting a compound having a 13-substituted 8,14-secogona-1,3,5(10),9- tetraene - 14,17 - dione nucleus with a " metallic complex " to produce a compound having a 13 - substituted - 17α - hydroxy - 8,14 - secogona- 1,3,5(10),9 - tetraene - 14 - one nucleus, the 13- substituent being a hydrocarbon residue; and (2) subjecting the product of step (1) to dehydration in the presence of an acid catalyst. As metallic complex in step (1) there may be used alkali metal boron hydrides, alkali metal aluminium hydrides and aluminium isopropoxide. The 17-hydroxy compounds thus obtained form a racemic mixture which may be resolved to obtain a (+) or (-) 13-substituted-17α- hydroxy - 8,14 - secogona - 1,3,5(10),9 - tetraene- 14-one compound which may be subjected to intramolecular cyclization e.g. in the presence of an acid catalyst to give compounds having a (-) 13-substituted-17α-hydroxy-gona-1,3,5(10), 8,14 pentaen-17-one nucleus which may be catalytically reduced e.g. with Raney nickel to the corresponding 13-substituted gona-1,3,5(10), 8 - tetraen - 17α - ols in which the hydrogen at 14-position is α-orientated. Further reduction of these compounds with an alkali metal in liquid ammonia at position 8 gives the corresponding 13 - substituted gona - 1,3,5(10)- trien-17α-ols which may be reduced in the aromatic ring to produce a 13-substituted-gona- 2,5(10) - dien - 17α - ol. Each of the last two products may be oxidized by e.g. Oppenhauer, to the 17-one compounds. These reactions are applicable to racemic mixtures or optical isomers.
GB1138367A 1966-10-15 1967-03-10 Steroids Expired GB1180584A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB1138367A GB1180584A (en) 1966-10-15 1967-03-10 Steroids
FR98416A FR1526031A (en) 1966-10-15 1967-03-10 Process for the production of novel steroids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP6799666 1966-10-15
GB1138367A GB1180584A (en) 1966-10-15 1967-03-10 Steroids

Publications (1)

Publication Number Publication Date
GB1180584A true GB1180584A (en) 1970-02-04

Family

ID=26248239

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1138367A Expired GB1180584A (en) 1966-10-15 1967-03-10 Steroids

Country Status (1)

Country Link
GB (1) GB1180584A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0069424A1 (en) * 1981-07-07 1983-01-12 Akzo N.V. Process for the selective reduction of a 14, 17-dioxo-8,4-seco-steroid
WO2012110947A1 (en) 2011-02-17 2012-08-23 Lupin Limited An improved process for preparation of levonorgestrel

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0069424A1 (en) * 1981-07-07 1983-01-12 Akzo N.V. Process for the selective reduction of a 14, 17-dioxo-8,4-seco-steroid
WO2012110947A1 (en) 2011-02-17 2012-08-23 Lupin Limited An improved process for preparation of levonorgestrel

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