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CO2018005941A2 - Solid forms of (2r, 4s) -5- (biphenyl-4-yl) -4 - [(3-carboxypropionyl) amino] -2-methyl-pentanoic acid ethyl ester, its salts and a preparation method - Google Patents

Solid forms of (2r, 4s) -5- (biphenyl-4-yl) -4 - [(3-carboxypropionyl) amino] -2-methyl-pentanoic acid ethyl ester, its salts and a preparation method

Info

Publication number
CO2018005941A2
CO2018005941A2 CONC2018/0005941A CO2018005941A CO2018005941A2 CO 2018005941 A2 CO2018005941 A2 CO 2018005941A2 CO 2018005941 A CO2018005941 A CO 2018005941A CO 2018005941 A2 CO2018005941 A2 CO 2018005941A2
Authority
CO
Colombia
Prior art keywords
sacubitrile
formula
salts
salt
preparation
Prior art date
Application number
CONC2018/0005941A
Other languages
Spanish (es)
Inventor
Ales Halama
Pavel Zvatora
Michal Voslar
Jan Stach
Michal Zapadlo
Ondrej Dammer
Lukas Krejcik
Lenka Dvorakova
Marketa Rezankova
Rostislav Vyslouzil
Original Assignee
Zentiva Ks
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=57614098&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CO2018005941(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from CZ2015-891A external-priority patent/CZ2015891A3/en
Priority claimed from CZ2015-896A external-priority patent/CZ2015896A3/en
Application filed by Zentiva Ks filed Critical Zentiva Ks
Publication of CO2018005941A2 publication Critical patent/CO2018005941A2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—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
    • C07C233/46—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 an acyclic carbon atom
    • C07C233/47—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 an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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

Landscapes

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

Abstract

La invención se refiere a formas sólidas del ácido libre de sacubitrilo de fórmula 1, especialmente una forma cristalina, incl. un método para eliminar impurezas químicas del ácido libre en bruto de sacubitrilo que se caracteriza por el uso de sales de sacubitrilo que cristalizan bien con las aminas de fórmula 9, donde R1, R2, R3 representan independientemente hidrógeno o un alquilo C1-C7, preferiblemente la sal con ciclohexilamina, terc-butilamina o iso-propilamina. La invención también se refiere a un sólido novedoso, forma cristalina de sacubitrilo (8) - hemisolvato de la sal de potasio de sacubitrilo, incl. métodos de preparación directos, altamente eficaces e industrialmente útiles de una forma sólida de ácido libre de sacubitrilo y sus sales farmacéuticamente aplicables, especialmente la sal de sodio cristalina de fórmula 5, sal de calcio de sacubitrilo de fórmula 6 y el hemisolvato de la sal de potasio de sacubitrilo de fórmula 8.The invention relates to solid forms of the sacubitrile free acid of formula 1, especially a crystalline form, incl. a method for removing chemical impurities from the crude free acid of sacubitrile which is characterized by the use of sacubitrile salts that crystallize well with the amines of formula 9, where R1, R2, R3 independently represent hydrogen or a C1-C7 alkyl, preferably the salt with cyclohexylamine, tert-butylamine or iso-propylamine. The invention also relates to a novel solid, crystalline form of sacubitrile (8) - hemisolvate of the potassium salt of sacubitrile, incl. Direct, highly effective and industrially useful methods of preparation of a solid form of sacubitrile free acid and its pharmaceutically applicable salts, especially the crystalline sodium salt of formula 5, sacubitrile calcium salt of formula 6 and the hemisolvate of the salt of Sacubitrile potassium of formula 8.

CONC2018/0005941A 2015-12-11 2018-06-12 Solid forms of (2r, 4s) -5- (biphenyl-4-yl) -4 - [(3-carboxypropionyl) amino] -2-methyl-pentanoic acid ethyl ester, its salts and a preparation method CO2018005941A2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CZ2015-891A CZ2015891A3 (en) 2015-12-11 2015-12-11 The crystalline form of potassium salt of ethyl ester (2R,4S)-5-(biphenyl-4-yl)-4-[(3-carboxypropionyl)amino]-2-methylpentanoic acid and the industrially applicable method of its preparation
CZ2015-896A CZ2015896A3 (en) 2015-12-14 2015-12-14 The solid forms of the ethyl ester of (2R,4S)-5-(biphenyl-4-yl)-4-[3-carboxy-propionyl)amino]-2—methylpentanoic acid, its salts and the method of its preparation
PCT/CZ2016/000130 WO2017097275A1 (en) 2015-12-11 2016-12-12 Solid forms of (2r,4s)-5-(biphenyl-4-yl)-4-[(3-carboxypropionyl)amino]-2- -methylpentanoic acid ethyl ester, its salts and a preparation method

Publications (1)

Publication Number Publication Date
CO2018005941A2 true CO2018005941A2 (en) 2018-07-10

Family

ID=57614098

Family Applications (1)

Application Number Title Priority Date Filing Date
CONC2018/0005941A CO2018005941A2 (en) 2015-12-11 2018-06-12 Solid forms of (2r, 4s) -5- (biphenyl-4-yl) -4 - [(3-carboxypropionyl) amino] -2-methyl-pentanoic acid ethyl ester, its salts and a preparation method

Country Status (6)

Country Link
EP (1) EP3386945A1 (en)
BR (1) BR112018011788A2 (en)
CO (1) CO2018005941A2 (en)
MX (1) MX2018007129A (en)
WO (1) WO2017097275A1 (en)
ZA (1) ZA201803749B (en)

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WO2018045505A1 (en) * 2016-09-07 2018-03-15 诺瑞特国际药业股份有限公司 New crystalline form of sacubitril sodium salt
US10857132B2 (en) 2016-10-10 2020-12-08 Laurus Labs Limited Stable amorphous form of sacubitril valsartan trisodium complex and processes for preparation thereof
JP7022747B2 (en) 2016-10-28 2022-02-18 バイオコン・リミテッド Amorphous sacubitril valsartan trisodium and the process for its preparation
CN107311909A (en) * 2017-06-22 2017-11-03 东南大学 A kind of preparation method of LCZ696 impurity reference substance
ES2881317T3 (en) 2017-07-28 2021-11-29 Synthon Bv Pharmaceutical composition comprising sacubitril and valsartan
CN109400493B (en) * 2017-08-15 2021-07-09 成都博腾药业有限公司 Preparation method of Sacubitril and intermediate thereof
CN107602410A (en) * 2017-09-13 2018-01-19 浙江三门恒康制药有限公司 Sha Ku is than crystal formation II of bent sodium salt and preparation method thereof
WO2019127994A1 (en) * 2017-12-27 2019-07-04 浙江天宇药业股份有限公司 Sacubitril sodium salt, eutectic of sacubitril free acid and acetic acid, crystal form thereof, method for preparing crystal form, and use thereof
CN108558693A (en) * 2018-04-24 2018-09-21 南京双科医药开发有限公司 The method that one planting sand library Ba Qu free acids and its metal salt are applied in medicine preparation
GB201810326D0 (en) * 2018-06-22 2018-08-08 Johnson Matthey Plc Crystalline form of sacubitril, its preparation and use
CN109912486B (en) * 2019-04-25 2022-09-27 东北制药集团股份有限公司 Preparation method of biphenyl methyl lactam compound
CN110878039A (en) * 2019-12-18 2020-03-13 株洲千金药业股份有限公司 Preparation method of Sacubitril valsartan sodium impurity
CN115677521B (en) * 2022-11-16 2024-02-02 迪嘉药业集团股份有限公司 Preparation method of high-purity Sha Kuba koji calcium

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US5217996A (en) 1992-01-22 1993-06-08 Ciba-Geigy Corporation Biaryl substituted 4-amino-butyric acid amides
ES2290429T3 (en) 2002-01-17 2008-02-16 Novartis Ag PHARMACEUTICAL COMPOSITIONS THAT INCLUDE VALSARTAN AND NEP INHIBITORS.
WO2007045663A2 (en) 2005-10-19 2007-04-26 Novartis Ag Combination of an ati receptor antagonist and a np inhibitor fro treating ia hypertension and heartfailure
AR057882A1 (en) 2005-11-09 2007-12-26 Novartis Ag DOUBLE ACTION COMPOUNDS OF ANGIOTENSIN RECEPTOR BLOCKERS AND NEUTRAL ENDOPEPTIDASE INHIBITORS
EP1903027A1 (en) 2006-09-13 2008-03-26 Novartis AG Process for preparing biaryl substituted 4-amino-butyric acid or derivatives thereof and their use in the production of NEP inhibitors
SG185318A1 (en) 2007-01-12 2012-11-29 Novartis Ag Process for preparing 5-biphenyl-4-amino-2-methyl pentanoic acid
AR070176A1 (en) 2008-01-17 2010-03-17 Novartis Ag SYNTHESIS PROCESSES OF NEP INHIBITORS, INTERMEDIATE COMPOUNDS AND USE OF THE SAME IN SYNTHESIS
CN104262228B (en) 2010-01-22 2017-01-18 诺华股份有限公司 Neutral endopeptidase inhibitor intermediate and preparation method thereof
ES2608780T3 (en) 2010-08-23 2017-04-17 Novartis Ag New process for the preparation of intermediaries useful for the preparation of NEP inhibitors
ES2576179T3 (en) 2010-08-23 2016-07-06 Novartis Ag Process for the preparation of intermediaries for the preparation of NEP inhibitors
AR092278A1 (en) 2012-08-31 2015-04-08 Novartis Ag PROCESS FOR OBTAINING N-ACILIC DERIVATIVES OF BIFENYL-ALANINE AND RELATED INTERMEDIARIES
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CN105461587A (en) * 2014-08-27 2016-04-06 上海翰森生物医药科技有限公司 AHU-377 hemicalcium salt crystal form, preparation method and application thereof
CN105622452A (en) * 2014-08-27 2016-06-01 上海翰森生物医药科技有限公司 AHU-377 crystal-type free acid, preparation method and applications thereof
WO2016029828A1 (en) * 2014-08-27 2016-03-03 上海翰森生物医药科技有限公司 Crystalline free acid, hemicalcium salt and α-phenylethylamine salt of ahu-377 as well as preparation method therefor and application thereof
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Also Published As

Publication number Publication date
MX2018007129A (en) 2018-11-09
WO2017097275A1 (en) 2017-06-15
EP3386945A1 (en) 2018-10-17
BR112018011788A2 (en) 2018-12-04
ZA201803749B (en) 2019-04-24

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