AR090618A1 - Proceso para la preparacion de inhibidores de sglt2 de derivados de bencilbenceno - Google Patents

Proceso para la preparacion de inhibidores de sglt2 de derivados de bencilbenceno

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Publication number
AR090618A1
AR090618A1 ARP130101120A ARP130101120A AR090618A1 AR 090618 A1 AR090618 A1 AR 090618A1 AR P130101120 A ARP130101120 A AR P130101120A AR P130101120 A ARP130101120 A AR P130101120A AR 090618 A1 AR090618 A1 AR 090618A1
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AR
Argentina
Prior art keywords
alkoxy
alkyl
cycloalkyl
group
alkynyloxy
Prior art date
Application number
ARP130101120A
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English (en)
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Theracos Inc
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Publication of AR090618A1 publication Critical patent/AR090618A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • C07H7/04—Carbocyclic radicals
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Endocrinology (AREA)
  • Medicinal Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Emergency Medicine (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrane Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Compuestos útiles para tratar la hiperglucemia. Reivindicación 1: Un método para preparar un compuesto de la fórmula (1), caracterizado porque comprende: (a) formar una primera mezcla de reacción que comprende un compuesto de la fórmula (2), un complejo de alquilmagnesio seleccionado entre el grupo que consiste en cloruro de alquil C₁₋₄magnesio, bromuro de alquil C₁₋₄magnesio, di(alquil C₁₋₄)magnesio, cloruro de cicloalquil C₃₋₇magnesio, bromuro de cicloalquil C₃₋₇magnesio, y di(cicloalquil C₃₋₇)magnesio, y un primer solvente orgánico, donde la proporción del complejo de alquilmagnesio al compuesto de la fórmula (2) es menor o igual a 1,0 (mol/mol), y donde la primera mezcla de reacción se encuentra a una temperatura menor a aproximadamente -50ºC, para dar un compuesto intermediario; y (b) formar una segunda mezcla de reacción que comprende el intermediario, un segundo solvente orgánico, y un compuesto de la fórmula (3) preparando así el compuesto de la fórmula (1), donde X es bromo o iodo; Y se selecciona entre el grupo que consiste en CHRᶜ, C(=O), O y S; Z se selecciona entre el grupo que consiste en CH₂ORᵃ, ORᵃ, SRᵃ, S(O)ₘ-Rᵃ; R¹ es cloro; cada R² y R³ se selecciona en forma independiente entre el grupo que consiste en hidrógeno, halo, hidroxi, alquilo C₁₋₃, -CH₂ORᵃ, alquenilo C₂₋₄, alcoxi C₁₋₃, cicloalquilo C₃₋₆, (alcoxi C₁₋₃)alquilo C₁₋₃, (haloalcoxi C₁₋₃)alquilo C₁₋₃, (alqueniloxi C₂₋₄)alquilo C₁₋₃, (alquiniloxi C₂₋₄)alquilo C₁₋₃, (cicloalcoxi C₃₋₆)alquilo C₁₋₃, hidroxialcoxi C₁₋₃, cicloalcoxi C₃₋₆, heterocicloalcoxi C₃₋₆, (alcoxi C₁₋₃)alcoxi C₁₋₃, (haloalcoxi C₁₋₃)alcoxi C₁₋₃, (alqueniloxi C₂₋₄)alcoxi C₁₋₃, (alquiniloxi C₂₋₄)alcoxi C₁₋₃, (cicloalcoxi C₃₋₆)alcoxi C₁₋₃, (heterocicloalcoxi C₃₋₆)alcoxi C₁₋₃, (cicloalquil C₃₋₆)alcoxi C₁₋₃, (cicloalquil C₃₋₆)alqueniloxi C₂₋₄ y (cicloalquil C₃₋₆)alquiniloxi C₂₋₄, donde al menos uno de R² y R³ se selecciona entre el grupo que consiste en hidrógeno, halo, hidroxi, alquilo C₁₋₃, alcoxi C₁₋₃, y cicloalquilo C₃₋₆, donde al menos uno de R² y R³ se selecciona entre el grupo que consiste en alquilo C₁₋₃, alcoxi C₁₋₃, cicloalquilo C₃₋₆, (alcoxi C₁₋₃)alquilo C₁₋₃, (haloalcoxi C₁₋₃)alquilo C₁₋₃, (alqueniloxi C₂₋₄)alquilo C₁₋₃, (alquiniloxi C₂₋₄)alquilo C₁₋₃, (cicloalcoxi C₃₋₆)alquilo C₁₋₃, hidroxialcoxi C₁₋₃, cicloalcoxi C₃₋₆, heterocicloalcoxi C₃₋₆, (alcoxi C₁₋₃)alcoxi C₁₋₃, (haloalcoxi C₁₋₃)alcoxi C₁₋₃, (alqueniloxi C₂₋₄)alcoxi C₁₋₃, (alquiniloxi C₂₋₄)alcoxi C₁₋₃, (cicloalcoxi C₃₋₆)alcoxi C₁₋₃, (heterocicloalcoxi C₃₋₆)alcoxi C₁₋₃, (cicloalquil C₃₋₆)alcoxi C₁₋₃, (cicloalquil C₃₋₆) alqueniloxi C₂₋₄ y (cicloalquil C₃₋₆) alquiniloxi C₂₋₄; R⁴ se selecciona entre el grupo que consiste en H y OR⁴ᵃ, donde R⁴ᵃ se selecciona entre el grupo que consiste en H y alquilo C₁₋₃, de manera alternativa, R² y R⁴ se combinan con los átomos a los cuales se une cada uno para formar un cicloalquilo o heterocicloalquilo de 5 ó 6 miembros; R⁵ se selecciona entre el grupo que consiste en H y -CH₂ORᵃ, de manera alternativa, R⁴ y R⁵ se combinan con los átomos a los cuales se une cada uno para formar un heterocicloalquilo de 5 ó 6 miembros; cada Rᵃ se selecciona en forma independiente entre el grupo que consiste en H, alquilo C₁₋₃ y Rᵇ; Rᵇ es un grupo protector; Rᶜ se selecciona entre el grupo que consiste en H, OH y alcoxi C₁₋₃, de manera alternativa, Rᶜ se combina con R⁴ o R⁵ para formar una unión; el anillo C es un arilo o heteroarilo; el anillo D se encuentra ausente o es un heteroarilo; el subíndice m es un entero entre 1 y 2; el subíndice n es un entero entre 1 y 4; donde los grupos o unidades alquilo, alcoxi, cicloalquilo, alqueniloxi, alquiniloxi, cicloalcoxi, hidroxialcoxi, y heterocicloalcoxi del mismo opcionalmente pueden estar parcial o completamente fluorados, y uno o más átomos de hidrógeno opcionalmente puede reemplazarse por deuterio.
ARP130101120A 2012-04-10 2013-04-05 Proceso para la preparacion de inhibidores de sglt2 de derivados de bencilbenceno AR090618A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2012/073697 WO2013152476A1 (en) 2012-04-10 2012-04-10 Process for the preparation of benzylbenzene sglt2 inhibitors

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AR090618A1 true AR090618A1 (es) 2014-11-26

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EP (1) EP2836500A4 (es)
JP (1) JP6208745B2 (es)
KR (1) KR102106310B1 (es)
AR (1) AR090618A1 (es)
AU (1) AU2013247304B2 (es)
BR (1) BR112014025105B1 (es)
CA (1) CA2867057C (es)
HK (1) HK1207084A1 (es)
IL (1) IL234800B (es)
MX (1) MX353307B (es)
NZ (1) NZ630408A (es)
RU (1) RU2625795C2 (es)
SG (1) SG11201406434PA (es)
TW (1) TWI597289B (es)
WO (2) WO2013152476A1 (es)
ZA (1) ZA201406899B (es)

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CN104478675B (zh) * 2015-01-15 2016-01-06 佛山市赛维斯医药科技有限公司 一类含烷氧苯基和三氟甲苯基丙二醇结构的衍生物和用途
CN104478674B (zh) * 2015-01-15 2016-03-09 佛山市赛维斯医药科技有限公司 一类烷氧苯基丙二醇衍生物和用途
CN104478671B (zh) * 2015-01-15 2016-03-09 佛山市赛维斯医药科技有限公司 一类双烷氧苯基丙二醇衍生物和用途
WO2016128995A1 (en) 2015-02-09 2016-08-18 Indoco Remedies Limited Process for the preparation of sglt inhibitor compounds
CZ2015729A3 (cs) * 2015-10-13 2017-04-26 Zentiva, K.S. Příprava intermediátů pro syntézu Canagliflozinu a Dapagliflozinu
CN107641139A (zh) 2016-07-22 2018-01-30 江苏豪森药业集团有限公司 达格列净中间体的晶型及其制备方法
WO2018207111A1 (en) * 2017-05-09 2018-11-15 Piramal Enterprises Limited A process for the preparation of sglt2 inhibitors and intermediates thereof
US20190343853A1 (en) * 2018-04-25 2019-11-14 Theracos Sub, Llc Methods of treating hypertension
CN114570303A (zh) * 2022-03-02 2022-06-03 南京市计量监督检测院 微通道反应器及基于反应器制备达格列净中间体的方法

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AR051446A1 (es) * 2004-09-23 2007-01-17 Bristol Myers Squibb Co Glucosidos de c-arilo como inhibidores selectivos de transportadores de glucosa (sglt2)
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HK1207084A1 (en) 2016-01-22
RU2014144944A (ru) 2016-06-10
IL234800B (en) 2018-06-28
CA2867057A1 (en) 2013-10-17
EP2836500A4 (en) 2016-03-23
EP2836500A1 (en) 2015-02-18
JP2015514118A (ja) 2015-05-18
AU2013247304A1 (en) 2014-09-25
TWI597289B (zh) 2017-09-01
BR112014025105B1 (pt) 2022-03-29
SG11201406434PA (en) 2014-11-27
MX2014012268A (es) 2015-03-09
JP6208745B2 (ja) 2017-10-04
KR102106310B1 (ko) 2020-05-04
CA2867057C (en) 2020-03-31
NZ630408A (en) 2016-09-30
TW201402593A (zh) 2014-01-16
ZA201406899B (en) 2023-07-26
MX353307B (es) 2018-01-08
BR112014025105A2 (es) 2017-06-20
AU2013247304B2 (en) 2017-03-30
KR20150001811A (ko) 2015-01-06
WO2013152654A1 (en) 2013-10-17
WO2013152476A1 (en) 2013-10-17
RU2625795C2 (ru) 2017-07-19

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