BR112022019285A2 - Processo para a preparação do ácido (r)-4-(1-(6-(4- (trifluorometil)benzil)-6-azaspiro[2.5]octano-5- carboxamido)-ciclopropil) benzóico ou um sal do mesmo - Google Patents

Processo para a preparação do ácido (r)-4-(1-(6-(4- (trifluorometil)benzil)-6-azaspiro[2.5]octano-5- carboxamido)-ciclopropil) benzóico ou um sal do mesmo

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Publication number
BR112022019285A2
BR112022019285A2 BR112022019285A BR112022019285A BR112022019285A2 BR 112022019285 A2 BR112022019285 A2 BR 112022019285A2 BR 112022019285 A BR112022019285 A BR 112022019285A BR 112022019285 A BR112022019285 A BR 112022019285A BR 112022019285 A2 BR112022019285 A2 BR 112022019285A2
Authority
BR
Brazil
Prior art keywords
azaspiro
octane
salt
carboxamido
cyclopropyl
Prior art date
Application number
BR112022019285A
Other languages
English (en)
Inventor
Claudio Rovati Lucio
Artusi Roberto
Magaraci Filippo
Buzzi Benedetta
Original Assignee
Rottapharm Biotech Srl
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 Rottapharm Biotech Srl filed Critical Rottapharm Biotech Srl
Publication of BR112022019285A2 publication Critical patent/BR112022019285A2/pt

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • 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
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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

Abstract

PROCESSO PARA A PREPARAÇÃO DO ÁCIDO (R)-4-(1-(6-(4- (TRIFLUOROMETIL)BENZIL)-6-AZASPIRO[2.5]OCTANO-5-CARBOXAMIDO)-CICLOPROPIL) BENZÓICO OU UM SAL DO MESMO. A presente invenção fornece um processo para preparar ácido (R)-6-(tert-butoxicarbonil)-6-azaspiro[2,5]octano-5- carboxílico (SM1), o referido processo compreendendo a etapa de: iv) converter um composto de fórmula (VII) num composto de fórmula (VIII) utilizando um reagente de Wittig num solvente adequado; v) reagir através da reação de Makosza o composto de Fórmula (VIII) usando bromofórmio e uma base adequada para obter o composto de ciclopropano de Fórmula (IX); e vi) remoção de átomos de bromo na presença de um agente redutor e uma base em um solvente alcoólico obtendo-se assim (SM1). A invenção se refere também a um processo para a conversão do composto (SM1) para a preparação do ácido (R)-4-(1-(6-(4-(trifluorometil)benzil)-6-azaspiro[2.5] octano-5-carboxamido)ciclopropil) benzóico (IV) ou um sal do mesmo. O sal é, preferencialmente, o sal de sódio, mais preferencialmente, a forma polimórfica A (R)-4-(1-(6-(4- (trifluorometil)benzil)-6-azaspiro[2.5]octano-5- carboxamido)-ciclopropil) benzoato de sódio tendo um espectro de DRX em pó com picos em valores do ângulo 2Theta ±0,2° de 4,3, 5,0, 5,8, 6,4, 7,1, 8,3, 8,7, 12,8, 15,3, 15,9.
BR112022019285A 2020-03-27 2021-03-19 Processo para a preparação do ácido (r)-4-(1-(6-(4- (trifluorometil)benzil)-6-azaspiro[2.5]octano-5- carboxamido)-ciclopropil) benzóico ou um sal do mesmo BR112022019285A2 (pt)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20166480.2A EP3885339A1 (en) 2020-03-27 2020-03-27 Process for the preparation of (r)-4-(1-(6-(4-(trifluoromethyl)benzyl)-6-azaspiro[2.5]octane-5-carboxamido)-cyclopropyl) benzoic acid or a salt thereof
PCT/EP2021/057046 WO2021191062A1 (en) 2020-03-27 2021-03-19 Process for the preparation of (r)-4-(1-(6-(4-(trifluoromethyl)benzyl)-6-azaspiro[2.5]octane-5-carboxamido)-cyclopropyl) benzoic acid or a salt thereof

Publications (1)

Publication Number Publication Date
BR112022019285A2 true BR112022019285A2 (pt) 2022-11-16

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Country Status (11)

Country Link
US (1) US20230127805A1 (pt)
EP (2) EP3885339A1 (pt)
JP (1) JP2023519231A (pt)
KR (1) KR20220160031A (pt)
CN (1) CN115515936A (pt)
AR (1) AR121654A1 (pt)
AU (1) AU2021245014A1 (pt)
BR (1) BR112022019285A2 (pt)
CA (1) CA3172903A1 (pt)
TW (1) TW202140423A (pt)
WO (1) WO2021191062A1 (pt)

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CN114380717A (zh) * 2022-01-28 2022-04-22 郑州猫眼农业科技有限公司 3-(叔丁氧基羰基-甲氧基羰基甲基-氨基)-丙酸甲酯及其中间体的制备方法
CN116143695B (zh) * 2023-02-17 2024-04-05 上海麦克林生化科技股份有限公司 一种1,1-二氟-5-氮杂螺[2.5]辛烷盐酸盐的合成方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101622230B (zh) 2007-02-26 2012-08-22 默克弗罗斯特加拿大有限公司 作为ep4受体拮抗剂的吲哚和二氢吲哚环丙基酰胺衍生物
WO2010026989A1 (ja) * 2008-09-02 2010-03-11 日産化学工業株式会社 オルト置換ハロアルキルスルホンアニリド誘導体及び除草剤
EP2484674A1 (en) * 2011-02-02 2012-08-08 Rottapharm S.P.A. Spiro aminic compounds with NK1 antagonist activity
CN103702980B (zh) * 2011-07-04 2016-10-05 罗达制药生物技术有限责任公司 环胺衍生物作为ep4受体拮抗剂
ITMI20112329A1 (it) * 2011-12-21 2013-06-22 Rottapharm Spa Nuovi derivati spiro amminici
US9056860B2 (en) * 2012-06-05 2015-06-16 Gilead Pharmasset Llc Synthesis of antiviral compound
HUE035698T2 (en) * 2013-12-17 2018-05-28 Lilly Co Eli Phenoxyethyl ring amine derivatives and their activity as EP4 receptor modulator
CN106928127B (zh) * 2015-12-31 2021-07-16 四川海思科制药有限公司 取代哌啶类酰胺衍生物及其制备方法和在药学上的应用
CN107954990A (zh) * 2017-11-14 2018-04-24 安徽诺全药业有限公司 一种雷迪帕维的制备方法

Also Published As

Publication number Publication date
WO2021191062A1 (en) 2021-09-30
AU2021245014A1 (en) 2022-10-27
KR20220160031A (ko) 2022-12-05
CA3172903A1 (en) 2021-09-30
EP4126821A1 (en) 2023-02-08
CN115515936A (zh) 2022-12-23
US20230127805A1 (en) 2023-04-27
JP2023519231A (ja) 2023-05-10
TW202140423A (zh) 2021-11-01
EP4126821B1 (en) 2024-05-15
EP3885339A1 (en) 2021-09-29
AR121654A1 (es) 2022-06-29

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