MX2022012998A - Procedimiento para la preparacion de (3s)-3-(4-cloro-3-{[(2s,3r)-2 -(4-clorofenil)-4,4,4-trifluor-3-metilbutanoil]amino}fenil)-3-aci do ciclo-propilpropanoico y su forma cristalina para uso como principio activo farmaceutico. - Google Patents

Procedimiento para la preparacion de (3s)-3-(4-cloro-3-{[(2s,3r)-2 -(4-clorofenil)-4,4,4-trifluor-3-metilbutanoil]amino}fenil)-3-aci do ciclo-propilpropanoico y su forma cristalina para uso como principio activo farmaceutico.

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Publication number
MX2022012998A
MX2022012998A MX2022012998A MX2022012998A MX2022012998A MX 2022012998 A MX2022012998 A MX 2022012998A MX 2022012998 A MX2022012998 A MX 2022012998A MX 2022012998 A MX2022012998 A MX 2022012998A MX 2022012998 A MX2022012998 A MX 2022012998A
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Mexico
Prior art keywords
trifluor
methylbutanoyl
chlorphenyl
chlor
cyclo
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Application number
MX2022012998A
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English (en)
Inventor
Peter Fey
Britta Olenik
Kai Lovis
Philipp Rubenbauer
Julia Küsel
Felix Spindler
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Bayer Pharma AG
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Application filed by Bayer Pharma AG filed Critical Bayer Pharma AG
Publication of MX2022012998A publication Critical patent/MX2022012998A/es

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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    • C07C233/54—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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    • C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
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    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
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    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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Abstract

La presente invención se refiere a un procedimiento nuevo y mejorado para la preparación de (3S)-3-(4-cloro-3-{[(2S,3R)-2-(4-c lorofenil)-4,4,4-trifluor-3-metilbutanoil]amino}fenil)-3-ácido ciclopropilpropanoico de la fórmula (I), el compuesto de la fórmula (I) en la forma cristalina y su uso para el tratamiento y / o la prevención de enfermedades, en particular para el tratamiento y / o la prevención de enfermedades cardiovasculares, cardiopulmonares y cardiorrenales. Lo descrito en el estado de la técnica, respecto al procedimiento de síntesis, tiene como desventaja el hecho de que este no es adecuado para un proceso a gran escala, ya que, entre otras cosas, son necesarias muchas etapas de purificación cromatográfica. Estas suelen ser técnicamente muy complicadas, caras y requieren un alto consumo de disolventes. Por lo tanto, había una necesidad de una síntesis practicable a gran escala que proporcionara el compuesto en la modificación cristalina 1 (I-1) reproducible en un alto rendimiento global, con bajos costos de producción y una pureza elevada, y que cumpliera con todos los requisitos reglamentarios. El procedimiento descrito en la presente invención proporciona una solución a este problema técnico.
MX2022012998A 2017-12-01 2020-07-13 Procedimiento para la preparacion de (3s)-3-(4-cloro-3-{[(2s,3r)-2 -(4-clorofenil)-4,4,4-trifluor-3-metilbutanoil]amino}fenil)-3-aci do ciclo-propilpropanoico y su forma cristalina para uso como principio activo farmaceutico. MX2022012998A (es)

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MX2020005646A MX2020005646A (es) 2017-12-01 2018-11-26 Procedimiento para la preparacion de (3s)-3-(4-cloro-3-{[(2s,3r)-2 -(4-clorofenil)-4,4,4-trifluor-3-metilbutanoil]amino}fenil)-3-aci do ciclo-propilpropanoico y su forma cristalina para uso como principio activo farmaceutico.
MX2022012998A MX2022012998A (es) 2017-12-01 2020-07-13 Procedimiento para la preparacion de (3s)-3-(4-cloro-3-{[(2s,3r)-2 -(4-clorofenil)-4,4,4-trifluor-3-metilbutanoil]amino}fenil)-3-aci do ciclo-propilpropanoico y su forma cristalina para uso como principio activo farmaceutico.

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US (2) US11332435B2 (es)
EP (1) EP3717480A1 (es)
JP (1) JP2021504396A (es)
KR (1) KR20200094762A (es)
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AU (1) AU2018374452A1 (es)
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MX (2) MX2020005646A (es)
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RU (1) RU2020121714A (es)
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Families Citing this family (4)

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DE102011007272A1 (de) 2011-04-13 2012-10-18 Bayer Pharma Aktiengesellschaft Verzweigte 3-Phenylpropionsäure-Derivate und ihre Verwendung
EP3826627B1 (de) 2018-07-24 2023-10-18 Bayer Aktiengesellschaft Oral applizierbare pharmazeutische darreichungsform mit modifizierter freisetzung
CN112998965B (zh) * 2021-02-22 2022-02-08 杭州可靠护理用品股份有限公司 具有粪便提示功能的婴儿纸尿裤
CN120152950A (zh) * 2022-11-08 2025-06-13 康臣药业(内蒙古)有限责任公司 一种烷基羧酸类化合物的晶型及其应用

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2174491A (en) 1985-04-24 1986-11-05 Univ Strathclyde A displacement measuring system
GB8521943D0 (en) 1985-09-04 1985-10-09 Elliott M Pesticides
DE19834047A1 (de) 1998-07-29 2000-02-03 Bayer Ag Substituierte Pyrazolderivate
DE19834044A1 (de) 1998-07-29 2000-02-03 Bayer Ag Neue substituierte Pyrazolderivate
AR031176A1 (es) 2000-11-22 2003-09-10 Bayer Ag Nuevos derivados de pirazolpiridina sustituidos con piridina
DE10220570A1 (de) 2002-05-08 2003-11-20 Bayer Ag Carbamat-substituierte Pyrazolopyridine
TW200804269A (en) 2005-11-16 2008-01-16 Astrazeneca Ab Chemical process
CN101235024A (zh) * 2008-02-01 2008-08-06 中国科学院上海有机化学研究所 一类苯并二氢吡喃类化合物、合成方法和用途
DE102009046115A1 (de) * 2009-10-28 2011-09-08 Bayer Schering Pharma Aktiengesellschaft Substituierte 3-Phenylpropansäuren und ihre Verwendung
DE102010021637A1 (de) 2010-05-26 2011-12-01 Bayer Schering Pharma Aktiengesellschaft Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung
PH12013500055A1 (en) 2010-07-09 2017-08-23 Bayer Ip Gmbh Ring-fused pyrimidines and triazines and use thereof for the treatment and/or prophylaxis of cardiovascular diseases
DE102010040233A1 (de) 2010-09-03 2012-03-08 Bayer Schering Pharma Aktiengesellschaft Bicyclische Aza-Heterocyclen und ihre Verwendung
DE102010043379A1 (de) 2010-11-04 2012-05-10 Bayer Schering Pharma Aktiengesellschaft Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung
KR20130136504A (ko) * 2010-12-07 2013-12-12 바이엘 인텔렉쳐 프로퍼티 게엠베하 치환된 1-벤질사이클로알킬카르복실산 및 그의 용도
DE102011007272A1 (de) * 2011-04-13 2012-10-18 Bayer Pharma Aktiengesellschaft Verzweigte 3-Phenylpropionsäure-Derivate und ihre Verwendung

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JOP20200133A1 (ar) 2020-05-31
WO2019105881A1 (de) 2019-06-06
AU2018374452A1 (en) 2020-06-04
IL274715A (en) 2020-07-30
US20220234996A1 (en) 2022-07-28
US20210179541A1 (en) 2021-06-17
BR112020010837A2 (pt) 2020-11-10
JP2021504396A (ja) 2021-02-15
RU2020121714A (ru) 2022-01-04
US11332435B2 (en) 2022-05-17
CL2020001420A1 (es) 2020-10-23
PE20211391A1 (es) 2021-07-27
UY37987A (es) 2019-06-28
SG11202004577VA (en) 2020-06-29
KR20200094762A (ko) 2020-08-07
CN111433204A (zh) 2020-07-17
AR113852A1 (es) 2020-06-17
MX2020005646A (es) 2020-08-20
EP3717480A1 (de) 2020-10-07
CO2020006789A2 (es) 2020-08-31
CA3083986A1 (en) 2019-06-06
TW201936568A (zh) 2019-09-16

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