MX343701B - Procedimiento para alquinilar 17-cetoesteroides 16-sustituidos. - Google Patents

Procedimiento para alquinilar 17-cetoesteroides 16-sustituidos.

Info

Publication number
MX343701B
MX343701B MX2014007761A MX2014007761A MX343701B MX 343701 B MX343701 B MX 343701B MX 2014007761 A MX2014007761 A MX 2014007761A MX 2014007761 A MX2014007761 A MX 2014007761A MX 343701 B MX343701 B MX 343701B
Authority
MX
Mexico
Prior art keywords
alkynylating
substituted
keto steroids
steroids
methylene
Prior art date
Application number
MX2014007761A
Other languages
English (en)
Other versions
MX2014007761A (es
Inventor
Gerardo Gutiérrez Fuentes Luis
Miguel Sandoval Rodríguez Celso
Original Assignee
Crystal Pharma Sau
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 Crystal Pharma Sau filed Critical Crystal Pharma Sau
Publication of MX2014007761A publication Critical patent/MX2014007761A/es
Publication of MX343701B publication Critical patent/MX343701B/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • 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
    • C07J1/0081—Substituted in position 17 alfa and 17 beta
    • C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
    • C07J1/0096—Alkynyl derivatives
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane 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
    • C07J1/0059—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
    • C07J1/0081—Substituted in position 17 alfa and 17 beta
    • 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
    • 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
    • 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
    • C07J7/004—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 substituted in position 17 alfa
    • C07J7/005—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 substituted in position 17 alfa substituted in position 16
    • C07J7/0055—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • 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
    • C07J7/0065—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 an OH group free esterified or etherified
    • C07J7/0075—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 an OH group free esterified or etherified substituted in position 17 alfa
    • 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
    • C07J7/009—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 only one oxygen atom doubly bound

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

La presente invención se refiere a un procedimiento para etinilar 16-metilen-17-cetoesteroides para dar los correspondientes 16-metjlen-17a-etjnjl-17ß-hidroxiesteroides mediante tratamiento con acetiluros de litio protegidos con sililo seguido por desililación adicional. Los productos resultantes son productos intermedios útiles en la preparación de varios principios farmacéuticamente activos, tales como por ejemplo Nestorone(r) o acetato de melengestrol.
MX2014007761A 2011-12-23 2012-12-19 Procedimiento para alquinilar 17-cetoesteroides 16-sustituidos. MX343701B (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161580010P 2011-12-23 2011-12-23
EP11382395 2011-12-23
PCT/EP2012/076095 WO2013092668A1 (en) 2011-12-23 2012-12-19 Process for alkynylating 16-substituted-17-keto steroids

Publications (2)

Publication Number Publication Date
MX2014007761A MX2014007761A (es) 2015-06-05
MX343701B true MX343701B (es) 2016-11-16

Family

ID=48667748

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2014007761A MX343701B (es) 2011-12-23 2012-12-19 Procedimiento para alquinilar 17-cetoesteroides 16-sustituidos.

Country Status (10)

Country Link
US (1) US9296780B2 (es)
EP (1) EP2794632B1 (es)
JP (1) JP6100798B2 (es)
KR (1) KR102028221B1 (es)
CN (2) CN104093732A (es)
CA (1) CA2859852C (es)
ES (1) ES2576231T3 (es)
HU (1) HUE027821T2 (es)
MX (1) MX343701B (es)
WO (1) WO2013092668A1 (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9556206B2 (en) * 2014-09-02 2017-01-31 California Institute Of Technology Base-catalyzed silylation of terminal alkyne C—H bonds
CN106928302B (zh) * 2017-03-30 2019-02-22 浙江医药股份有限公司昌海生物分公司 一种雄烯二酮衍生物及其制备方法和应用
US10632066B1 (en) 2019-02-01 2020-04-28 The Population Council, Inc. Method of providing birth control
US11529308B2 (en) 2019-06-21 2022-12-20 The Population Council, Inc. System for providing birth control
US10918649B2 (en) 2019-06-21 2021-02-16 The Population Council, Inc. System for providing birth control

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2272131A (en) 1937-07-22 1942-02-03 Ciba Pharm Prod Inc Nuclear ketones of the cyclopentanopolyhydrophenanthrene series and process of making same
US2723280A (en) 1953-08-27 1955-11-08 Leo Pharm Prod Ltd 1-methyl-17-ethinyl-estradiol
US2843609A (en) 1955-10-11 1958-07-15 Searle & Co 17-alkenyl and alkynyl derivatives of 4-estrene-3, 17-diol
US2877240A (en) 1958-06-09 1959-03-10 Upjohn Co 6-fluoro-17beta-hydroxy-17alpha-lower aliphatic hydrocarbon-1, 4-androstadienes and 6-fluoro-17alpha-lower aliphatic hydrocarbon estradiols
US3166551A (en) 1962-01-02 1965-01-19 British Drug Houses Ltd Process for the preparation of 3-oxo-delta4-6-methyl steroids
GB1058543A (en) 1963-03-13 1967-02-15 Organon Labor Ltd 16-methylene-steroids
BE652906A (es) 1963-09-11
US3262950A (en) * 1963-12-17 1966-07-26 Syntex Corp 16-methylene-21-halo-19-nor-deta4, 6-pregnadienes
NL6513663A (es) * 1965-10-22 1967-04-24
US3470217A (en) 1966-04-07 1969-09-30 Syntex Corp Process for the preparation of alkynyl carbinols
CH515226A (de) 1968-05-06 1971-11-15 Ciba Geigy Ag Herstellung neuer 6-Fluorsteroide der Androstanreihe
US3516991A (en) 1968-09-19 1970-06-23 Upjohn Co Chemical process
CH547268A (de) * 1968-10-25 1974-03-29 Merck Patent Gmbh Verfahren zur herstellung von n-disubstituierten 3-amino3,5-dien-19-nor-steroiden.
US3704253A (en) * 1970-09-23 1972-11-28 American Home Prod 13 - polycarbonalkyl - 16 - methylgona-1,3,5(10)-trienes and 13-polycarbonalkyl-16-methylgon - 4 - en-3-ones and intermediates for their production
US3755382A (en) * 1972-06-01 1973-08-28 Stanford Research Inst Synthesis of 17alpha-(trimethylsilylethynyl)estradiol
FI54128C (fi) 1972-12-09 1978-10-10 Akzo Nv Foerfarande foer framstaellning av nya 11,11-alkylidensteroider ur oestran- och 19-norpregnanserien med foerbaettrad hormonell verkan
US4055562A (en) 1975-10-06 1977-10-25 Sterling Drug Inc. Process for preparing pregn-20-yne compounds and novel product produced thereby
US4041055A (en) 1975-11-17 1977-08-09 The Upjohn Company Process for the preparation of 17α-hydroxyprogesterones and corticoids from androstenes
CH642936A5 (de) 1979-10-19 1984-05-15 Hoffmann La Roche Aethinylierung alpha,beta-ungesaettigter ketone.
US4416821A (en) 1982-02-17 1983-11-22 The Upjohn Company Process for preparing 16-methylene steroids
EP0179496A1 (en) * 1982-09-20 1986-04-30 The Upjohn Company 16-Sulfinylmethyl-steroids, their preparation and use
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JPS5976100A (ja) * 1982-09-20 1984-04-28 ジ・アツプジヨン・カンパニ− １６−メチレン−１７α−ヒドロキシ−プロゲステロン
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EP0148616B1 (en) * 1984-01-05 1991-04-17 The Upjohn Company Stabilised monolithium acetylide and the ethynylation of steroids
KR960010793B1 (ko) * 1986-10-10 1996-08-08 루쎌 위클라프 소시에떼 아노님 9-알파-히드록시 스테로이드 및 그의 제조방법
AU3582393A (en) 1992-01-28 1993-09-01 Schering Corporation Novel steroid intermediates and processes for their preparation
HU216828B (hu) 1995-12-22 1999-09-28 Richter Gedeon Vegyészeti Gyár Rt. Szteránvázas vegyületek, eljárás ezek előállítására, az ezeket tartalmazó gyógyászati készítmények és intermedierjeik
JP4815083B2 (ja) * 1999-08-31 2011-11-16 メルク・シャープ・エンド・ドーム・コーポレイション 複素環化合物およびそれの使用方法
JP2007512361A (ja) * 2003-11-24 2007-05-17 メルク　エンド　カムパニー　インコーポレーテッド エストロゲン受容体調節剤
US20070015750A1 (en) * 2005-04-14 2007-01-18 Stefan Baeurle Tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents
US20090012321A1 (en) 2007-06-06 2009-01-08 Klaus Annen Process for preparing 17alpha-acetoxy-6-methylenepregn-4-ene-3,20-dione, medroxyprogesterone acetate and megestrol acetate
DK2300489T3 (en) * 2008-06-06 2016-02-15 Neurmedix Inc PROCESSES FOR PREPARING 17-alkynyl-7-HYDROXY STEROIDS AND RELATED COMPOUNDS

Also Published As

Publication number Publication date
MX2014007761A (es) 2015-06-05
EP2794632A1 (en) 2014-10-29
US20150005518A1 (en) 2015-01-01
ES2576231T3 (es) 2016-07-06
CA2859852C (en) 2020-09-15
EP2794632B1 (en) 2016-03-16
CN104093732A (zh) 2014-10-08
HUE027821T2 (en) 2016-11-28
JP6100798B2 (ja) 2017-03-22
KR102028221B1 (ko) 2019-10-02
US9296780B2 (en) 2016-03-29
CA2859852A1 (en) 2013-06-27
KR20140130425A (ko) 2014-11-10
JP2015500857A (ja) 2015-01-08
WO2013092668A1 (en) 2013-06-27
CN107955052A (zh) 2018-04-24

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