AR071312A1 - Proceso para la preparacion de analogos de prostaglandina y sus intermediarios - Google Patents

Proceso para la preparacion de analogos de prostaglandina y sus intermediarios

Info

Publication number
AR071312A1
AR071312A1 ARP090101272A ARP090101272A AR071312A1 AR 071312 A1 AR071312 A1 AR 071312A1 AR P090101272 A ARP090101272 A AR P090101272A AR P090101272 A ARP090101272 A AR P090101272A AR 071312 A1 AR071312 A1 AR 071312A1
Authority
AR
Argentina
Prior art keywords
formula
compound
converting
alkyl
protecting group
Prior art date
Application number
ARP090101272A
Other languages
English (en)
Inventor
Yung Fa Chen
Dechao Meng
Julian Paul Henschke
Yuanlian Liu
Ting Sun
Original Assignee
Scinopharm Taiwan 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 Scinopharm Taiwan Ltd filed Critical Scinopharm Taiwan Ltd
Publication of AR071312A1 publication Critical patent/AR071312A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

Intermediarios para preparar análogos de prostaglandina y procesos para preparar análogos de prostaglandina y sus intermediarios. Un compuesto de formula (1) donde R1 representa H, alquilo C1-5 o bencilo, en particular isopropilo. Reivindicacion 1: Un proceso para preparar un análogo de prostaglandina de formula (2) donde R1 representa H, alquilo C1-5, o bencilo; X representa CH2, O o S; Z representa O o NH; y R' representa alquilo C2-4; fenilo opcionalmente sustituido con halogeno, alquilo C1-5, alcoxi C1-4, CF3, polihaloalquilo C2-4, o acilamino C1-3 alifático; heterociclo de 5 o 6 miembros que contiene uno o más heteroátomos seleccionados entre el grupo que consiste en nitrogeno, oxígeno y azufre; cicloalquilo C3-7; o cicloalquenilo C3-7; el proceso comprende los pasos de: (a) convertir un compuesto de formula (3) a un compuesto de formula (4) donde R2 representa un grupo protector de hidroxi; (b) esterificar y desproteger el compuesto de formula (4) para dar un compuesto de formula (1); (c) convertir el compuesto de formula (1) a un compuesto de formula (5) donde R3 representa un grupo protector de hidroxi; (d) hacer reaccionar el compuesto de formula (5) con un compuesto de formula (6) para dar un compuesto de formula (7) donde y representa un complejo metálico, R'' representa un grupo protector de hidroxi, y (e) convertir el compuesto de formula (7) para dar el compuesto de formula (2). Reivindicacion 7: Un proceso para preparar una ciclopentenona de la formula (5) donde R1 representa H, alquilo C1-5, o bencilo; y R3 representa un grupo protector de hidroxi; el proceso comprende los pasos de: (a) convertir un compuesto de formula (3) a un compuesto de formula (4) donde R2 representa un grupo protector de hidroxi; (b) esterificar y desproteger el compuesto de formula (4) para dar un compuesto de formula (1); (c) convertir el compuesto de formula (1) para obtener el compuesto de formula (5).
ARP090101272A 2008-04-09 2009-04-08 Proceso para la preparacion de analogos de prostaglandina y sus intermediarios AR071312A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12352708P 2008-04-09 2008-04-09

Publications (1)

Publication Number Publication Date
AR071312A1 true AR071312A1 (es) 2010-06-09

Family

ID=41164537

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP090101272A AR071312A1 (es) 2008-04-09 2009-04-08 Proceso para la preparacion de analogos de prostaglandina y sus intermediarios

Country Status (11)

Country Link
US (3) US7897795B2 (es)
EP (1) EP2274266B1 (es)
JP (1) JP5485980B2 (es)
KR (1) KR101634818B1 (es)
CN (1) CN102056887B (es)
AR (1) AR071312A1 (es)
AU (1) AU2009250938B2 (es)
CA (1) CA2721102C (es)
ES (1) ES2524884T3 (es)
TW (1) TWI367206B (es)
WO (1) WO2009141718A2 (es)

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AR071312A1 (es) * 2008-04-09 2010-06-09 Scinopharm Taiwan Ltd Proceso para la preparacion de analogos de prostaglandina y sus intermediarios
KR101045935B1 (ko) 2009-03-11 2011-07-01 연성정밀화학(주) 프로스타글란딘 유도체의 제조방법
EP2454227B1 (en) 2009-07-13 2020-08-19 Patheon API Services Inc. Synthesis of prostanoids
IN2013MN00733A (es) * 2010-10-15 2015-06-12 Scinopharm Kunshan Biochemical Technology Co Ltd
JP2012111720A (ja) * 2010-11-25 2012-06-14 Fuji Flavor Kk ５−ウンデセン酸の製造方法
CN106349138A (zh) * 2011-06-02 2017-01-25 奇诺因私人有限公司 用于制备前列腺素酰胺的新的方法
US9115109B2 (en) 2013-08-15 2015-08-25 Chirogate International Inc. Processes and intermediates for the preparations of isomer free prostaglandins
CA2925927C (en) 2013-09-30 2022-09-06 George Petros Yiannikouros Novel synthesis routes for prostaglandins and prostaglandin intermediates using metathesis
CN105254657B (zh) * 2014-07-10 2018-06-15 台湾神隆股份有限公司 金属催化不对称1,4-共轭加成反应产生前列腺素和前列腺素类似物
JP2015120693A (ja) * 2014-12-19 2015-07-02 サイノファーム （クンシャン） バイオケミカル テクノロジ カンパニー リミテッド ルビプロストンの調製方法
CN105801533B (zh) * 2014-12-30 2019-01-08 常州博海威医药科技股份有限公司 一种制备利马前列腺素的关键中间体及其应用
CN105801534B (zh) * 2014-12-30 2019-01-08 常州博海威医药科技股份有限公司 一种制备利马前列腺素的关键中间体及其应用
WO2017062770A1 (en) 2015-10-08 2017-04-13 Silverberg Noah Punctal plug and bioadhesives
WO2020255164A1 (en) * 2019-06-21 2020-12-24 Council Of Scientific And Industrial Research A chemo-enzymatic process for the preparation of homopropargylic alcohol
IL295357A (en) 2020-02-06 2022-10-01 Ocular Therapeutix Inc Preparations and methods for the treatment of eye diseases
CN113105329B (zh) * 2021-04-22 2023-10-03 成都道合尔医药技术有限公司 一种(e)-甲酯3-(3,5-二氟-4-甲酰基苯基)丙烯酸的合成方法

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Also Published As

Publication number Publication date
TWI367206B (en) 2012-07-01
EP2274266B1 (en) 2014-10-15
WO2009141718A3 (en) 2010-01-21
US8742143B2 (en) 2014-06-03
CN102056887B (zh) 2014-03-19
US7897795B2 (en) 2011-03-01
JP2011518134A (ja) 2011-06-23
TW201002658A (en) 2010-01-16
WO2009141718A2 (en) 2009-11-26
US20130211128A1 (en) 2013-08-15
EP2274266A4 (en) 2012-10-10
JP5485980B2 (ja) 2014-05-07
AU2009250938B2 (en) 2013-03-07
CA2721102C (en) 2015-12-29
KR20110004432A (ko) 2011-01-13
AU2009250938A1 (en) 2009-11-26
EP2274266A2 (en) 2011-01-19
US8436194B2 (en) 2013-05-07
ES2524884T3 (es) 2014-12-15
KR101634818B1 (ko) 2016-06-29
US20090259058A1 (en) 2009-10-15
US20110130577A1 (en) 2011-06-02
CA2721102A1 (en) 2009-11-26
CN102056887A (zh) 2011-05-11

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