CL2020002742A1 - Procedimiento para preparar (4s)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida por separación de racemato mediante éster del ácido tartárico diastereomérico - Google Patents

Procedimiento para preparar (4s)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida por separación de racemato mediante éster del ácido tartárico diastereomérico

Info

Publication number
CL2020002742A1
CL2020002742A1 CL2020002742A CL2020002742A CL2020002742A1 CL 2020002742 A1 CL2020002742 A1 CL 2020002742A1 CL 2020002742 A CL2020002742 A CL 2020002742A CL 2020002742 A CL2020002742 A CL 2020002742A CL 2020002742 A1 CL2020002742 A1 CL 2020002742A1
Authority
CL
Chile
Prior art keywords
naphthyridine
carboxamide
methoxyphenyl
dihydro
ethoxy
Prior art date
Application number
CL2020002742A
Other languages
English (en)
Inventor
Platzek Johannes
Lovis Kai
Joentgen Winfried
Original Assignee
Bayer Ag
Bayer Pharma AG
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 Bayer Ag, Bayer Pharma AG filed Critical Bayer Ag
Publication of CL2020002742A1 publication Critical patent/CL2020002742A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La presente invención se refiere a un procedimiento nuevo y mejorado para la preparación de (4S)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida de la fórmula (I) y la preparación del enantiómero (Ia) por separación de racemato con ésteres del ácido tartárico sustituidos quiralmente de las fórmulas generales (IIIa) y (IIIb), donde Ar es un compuesto aromático o heteroaromático sustituido o no sustituido.
CL2020002742A 2018-04-24 2020-10-22 Procedimiento para preparar (4s)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida por separación de racemato mediante éster del ácido tartárico diastereomérico CL2020002742A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP18169052.0A EP3560922A1 (de) 2018-04-24 2018-04-24 Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid durch racemat-spaltung mittels diastereomerer weinsäureester

Publications (1)

Publication Number Publication Date
CL2020002742A1 true CL2020002742A1 (es) 2021-01-15

Family

ID=62062935

Family Applications (1)

Application Number Title Priority Date Filing Date
CL2020002742A CL2020002742A1 (es) 2018-04-24 2020-10-22 Procedimiento para preparar (4s)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida por separación de racemato mediante éster del ácido tartárico diastereomérico

Country Status (19)

Country Link
US (4) US12054481B2 (es)
EP (2) EP3560922A1 (es)
JP (1) JP7394785B2 (es)
KR (1) KR20210005000A (es)
CN (1) CN112041318A (es)
AR (1) AR114833A1 (es)
AU (1) AU2019258116B2 (es)
CA (1) CA3097924A1 (es)
CL (1) CL2020002742A1 (es)
CO (1) CO2020013150A2 (es)
IL (1) IL278078B2 (es)
JO (1) JOP20200267B1 (es)
MX (1) MX2020011198A (es)
MY (1) MY205489A (es)
PE (1) PE20211903A1 (es)
SG (1) SG11202010504QA (es)
TW (1) TWI865448B (es)
UY (1) UY38197A (es)
WO (1) WO2019206909A1 (es)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3560922A1 (de) * 2018-04-24 2019-10-30 Bayer Aktiengesellschaft Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid durch racemat-spaltung mittels diastereomerer weinsäureester
CN113301963A (zh) * 2019-01-14 2021-08-24 先天肿瘤免疫公司 用于治疗癌症的作为nlrp3调节剂的取代的喹唑啉类
EP4045499A1 (de) * 2019-10-17 2022-08-24 Bayer Aktiengesellschaft Verfahren zur herstellung von 2-cyanoethyl (4s)-4-(4-cyano-2-methoxy-phenyl)-5-hydroxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carboxylat durch racemat-spaltung mittels diastereomerer weinsäureester
US12398144B2 (en) * 2019-10-17 2025-08-26 Bayer Aktiengesellschaft Photochemical process for producing (4R,4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carboxamide
TW202214624A (zh) 2020-06-16 2022-04-16 德商拜耳廠股份有限公司 藉由催化不對稱漢斯（ｈａｎｔｚｓｃｈ）酯還原法進行之製備（４ｓ）－４－（４－氰基－２－甲氧基苯基）－５－乙氧基－２，８－二甲基－１，４－二氫－１，６－㖠啶－３－羧醯胺的方法
CN115340539B (zh) * 2022-01-19 2024-02-27 奥锐特药业股份有限公司 制备非奈利酮及其中间体的方法
CN115340540A (zh) * 2022-01-20 2022-11-15 奥锐特药业股份有限公司 制备非奈利酮及其中间体的方法
CN114605410B (zh) * 2022-04-06 2023-12-29 浙江科聚生物医药有限公司 一种非奈利酮原料药的制备方法
EP4511365A1 (en) 2022-04-18 2025-02-26 Teva Pharmaceuticals International GmbH Processes for the preparation of finerenone
US20250115601A1 (en) * 2022-05-16 2025-04-10 Glenmark Life Sciences Limited Process for the preparation of finerenone and intermediates thereof
WO2024075139A1 (en) * 2022-10-06 2024-04-11 Maithri Drugs Private Limited A process for preparation of finerenone and intermediates thereof
CN117986250A (zh) 2022-11-04 2024-05-07 南京威凯尔生物医药科技有限公司 通过非对映酒石酸酯拆分外消旋体制备非奈利酮的方法
IL321272A (en) 2022-12-16 2025-08-01 Bayer Ag Continuous one-pot synthesis for the preparation of 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-8,2-dimethyl-4,1-dihydro-6,1-naphthyridine-3-carboxamide
WO2024147053A1 (en) * 2023-01-03 2024-07-11 Optimus Drugs Pvt Ltd Improved process for the preparation of finerenone
CN120731206A (zh) * 2023-03-17 2025-09-30 江苏恒瑞医药股份有限公司 一种1,4-二氢-1,6-萘啶酰胺化合物的可药用盐、晶型及其制备方法
WO2025081981A1 (zh) * 2023-10-20 2025-04-24 山东诚创蓝海医药科技有限公司 非奈利酮中间体、其制备方法及非奈利酮的制备方法
CN120081840A (zh) * 2023-12-01 2025-06-03 山东诚创蓝海医药科技有限公司 一种非奈利酮-马来酸共晶及其制备方法
CN117924273A (zh) * 2024-01-05 2024-04-26 江苏德源药业股份有限公司 一种非奈利酮原料药的制备方法
CN117946102A (zh) * 2024-01-08 2024-04-30 江苏德源药业股份有限公司 一种非奈利酮非对映体盐及其制备非奈利酮的方法
WO2025224069A1 (en) * 2024-04-23 2025-10-30 Bayer Aktiengesellschaft Co-crystals of finerenone, pecavaptan, and sglt2 inhibitors
CN118479984B (zh) * 2024-05-11 2026-03-24 山东福长药业有限公司 一种使用酒石酸衍生物拆分剂的非奈利酮拆分方法
WO2026013638A1 (en) * 2024-07-12 2026-01-15 Ami Lifesciences Private Limited A process for the preparation of finerenone and intermediates thereof
CN119143755B (zh) * 2024-09-12 2026-03-13 奥锐特药业股份有限公司 一种由非奈利酮或其中间体的对映体制备外消旋体的方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3906460C1 (es) * 1989-03-01 1990-11-15 Goedecke Ag, 1000 Berlin, De
EP1831166B1 (en) 2004-12-02 2010-10-20 SK Chemicals, Co., Ltd. Optical resolution method of amlodipine
WO2007075790A1 (en) * 2005-12-22 2007-07-05 Schering Corporation Process for the preparation of 6, 6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds and enantiomeric salts thereof
DE102007009494A1 (de) 2007-02-27 2008-08-28 Bayer Healthcare Ag Substituierte 4-Aryl-1, 4-dihydro-1,6-naphthyridinamide und ihre Verwendung
CN101648903A (zh) 2009-09-17 2010-02-17 南京大学 一种制备光学活性的氨氯地平对甲苯磺酸盐的方法
CN101798280B (zh) * 2010-03-22 2012-05-02 河北师范大学 一种手性拆分消旋体氨氯地平制备s-(-)-氨氯地平和r-(+)-氨氯地平的方法
ES2828704T3 (es) 2014-08-01 2021-05-27 Bayer Pharma AG Procedimiento para la preparación de (4S)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida y su purificación para su uso como principio activo farmacéutico
RU2715226C2 (ru) * 2015-08-21 2020-02-26 Байер Фарма Акциенгезельшафт Способ получения (4s)-4-(4-циано-2-метоксифенил)-5-этокси-2,8-диметил-1,4-дигидро-1,6-нафтиридин-3-карбоксамида и выделения (4s)-4-(4-циано-2-метоксифенил)-5-этокси-2,8-диметил-1,4-дигидро-1,6-нафтиридин-3-карбоксамида посредством электрохимических методов
RS59055B1 (sr) 2015-08-21 2019-08-30 Bayer Pharma AG Postupak za proizvodnju (4s)-4-(4-cijano-2-metoksifenil)-5-etoksi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-karboksamida i njegovo prečišćavanje u svrhu upotrebe kao farmaceutski aktivne supstance
EP3560922A1 (de) * 2018-04-24 2019-10-30 Bayer Aktiengesellschaft Verfahren zur herstellung von (4s)- 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridin-3-carbox-amid durch racemat-spaltung mittels diastereomerer weinsäureester

Also Published As

Publication number Publication date
KR20210005000A (ko) 2021-01-13
EP3784668A1 (de) 2021-03-03
MX2020011198A (es) 2020-11-13
US20260015355A1 (en) 2026-01-15
WO2019206909A1 (de) 2019-10-31
IL278078B1 (en) 2023-06-01
SG11202010504QA (en) 2020-11-27
TW202003514A (zh) 2020-01-16
US12448381B1 (en) 2025-10-21
US20240376103A1 (en) 2024-11-14
CA3097924A1 (en) 2019-10-31
AR114833A1 (es) 2020-10-21
IL278078B2 (en) 2023-10-01
MY205489A (en) 2024-10-23
US20210163474A1 (en) 2021-06-03
UY38197A (es) 2019-11-29
JOP20200267B1 (ar) 2020-10-25
CO2020013150A2 (es) 2020-11-10
JP7394785B2 (ja) 2023-12-08
TWI865448B (zh) 2024-12-11
PE20211903A1 (es) 2021-09-27
AU2019258116B2 (en) 2024-07-25
AU2019258116A1 (en) 2020-11-05
JOP20200267A1 (ar) 2020-10-25
US12054481B2 (en) 2024-08-06
IL278078A (en) 2020-11-30
JP2021522236A (ja) 2021-08-30
BR112020018738A2 (pt) 2021-01-05
EP3560922A1 (de) 2019-10-30
US20250340553A1 (en) 2025-11-06
CN112041318A (zh) 2020-12-04

Similar Documents

Publication Publication Date Title
CL2020002742A1 (es) Procedimiento para preparar (4s)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida por separación de racemato mediante éster del ácido tartárico diastereomérico
UY40247A (es) Procedimiento para la preparación de (4S)- 4-(4-Ciano-2-metoxifenilo)-5-etoxi-2,8-dimetilo-1,4-dihid
MX2022004467A (es) Procedimiento para preparar (4s)-4-(4-ciano-2-metoxi-fenil)-5-etox i-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxilato de 2-cianoetilo mediante separacion de racematos utilizando esteres diastereomericos de acido tartarico.
CO2018001759A2 (es) Procedimiento para la preparación de (4s)-4-(4-ciano-2-metoxifenilo)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridina-3-carboxamida y para la recuperación de (4s)-4-(4-ciano-2-metoxifenilo)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridina-3-carboxamida por medio de métodos electroquímicos
PE20200008A1 (es) Isoquinolinas como inhibidores de hpk1
CO2017013229A2 (es) Agonistas de receptor de apelina (apj) de 4-hidroxi-3-(heteroaril)piridin-2-ona como para uso en el tratamiento de trastornos cardiovasculares
PH12013501197B1 (en) Indeno-fused ring compounds
AR105774A1 (es) Procedimiento para la preparación de (4s)-4-(4-ciano-2-metoxifenilo)-5-etoxi-2,8-dimetilo-1,4-dihidro-1,6-naftiridina-3-carboxamida y su purificación para su uso como principio activo farmacéutico
HUE061702T2 (hu) Racém nikotin enantiomer elválasztása egy alacsony optikai tisztaságú O,O'-diszubsztituált borkõsav hozzáadásával
MX2022004480A (es) Procedimiento para preparar esteres aciloximetilicos del acido (4s)-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6- naftiridin-3-carboxilico.
MX2022004468A (es) Procedimiento para la preparacion de (4s)-4-(4-ciano-2-metoxi-feni l)-5-hidroxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxilato de 2-cianoetilo por separacion de racematos por medio de ester de acido tartarico diastereoisomero.
MX2018010199A (es) Proceso para la separacion de enantiomeros de derivados de piperazina.
PE20221420A1 (es) Procedimiento fotoquimico para la preparacion de (4r,4s)-4-(4-ciano-2-metoxifenil)-5-etoxi-2,8-dimetil-1,4-dihidro-1,6-naftiridin-3-carboxamida
EA201590438A1 (ru) 2-оксо-2,3-дигидроиндолы для лечения расстройств центральной нервной системы
LT2012082A (lt) Nauji fotochrominiai junginiai, jų gamybos būdas ir tarpiniai junginiai jiems gauti
MX2022002568A (es) Proceso para preparar (r)-4-aminoindano y amidas correspondientes.
MX2019011001A (es) Proceso para la separacion de isomeros opticos de esteres etilicos de acido 3-alquilpiperidin-carboxilico racemico.
TH2001006145A (th) วิธีสำหรับการเตรียม (4s)-4-(4-ไซยาโน-2-เมธอกซีฟีนิล)-5-เอธอกซี-2,8-ไดเมธิล-1,4-ไดไฮโดร-1,6-แนพธิริดีน-3-คาร์บอกซาไมด์โดยการแยกแรซีเมตด้วยไดอะสเตอริโอเมอริกทาร์ทาริกแอซิดเอสเทอร์
CO6690757A2 (es) Procedimiento para preparar formas enantioméricas de derivados de ácido 2,3-diaminopropiónico
PY1305972A (es) Proceso para la preparación estereoselectiva de una pirazolcarboxamida
NI201300022A (es) Procedimiento para preparar formas enantioméricas de derivados de ácido 2,3 - diaminopropiónico
BR112017007270A2 (pt) processo para a preparação de treprostinila