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WO2017012600A1 - Composition pharmaceutique contenant du valsartan et du sacubitril et procédés de préparation et de stabilisation correspondants - Google Patents

Composition pharmaceutique contenant du valsartan et du sacubitril et procédés de préparation et de stabilisation correspondants Download PDF

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Publication number
WO2017012600A1
WO2017012600A1 PCT/CZ2016/000079 CZ2016000079W WO2017012600A1 WO 2017012600 A1 WO2017012600 A1 WO 2017012600A1 CZ 2016000079 W CZ2016000079 W CZ 2016000079W WO 2017012600 A1 WO2017012600 A1 WO 2017012600A1
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WO
WIPO (PCT)
Prior art keywords
sacubitril
valsartan
pharmaceutically acceptable
salt
pharmaceutical composition
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/CZ2016/000079
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English (en)
Inventor
Jiri Dohnal
Pavel ZVATORA
Pavel KOVACIK
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zentiva KS
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
Priority claimed from CZ2015-508A external-priority patent/CZ2015508A3/cs
Priority claimed from CZ2016-57A external-priority patent/CZ201657A3/cs
Application filed by Zentiva KS filed Critical Zentiva KS
Publication of WO2017012600A1 publication Critical patent/WO2017012600A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing

Definitions

  • the invention relates to pharmaceutical compositions in the form of tablets suitable for oral administration, containing Valsartan of formula (I), systematic name fS)-3-methyl-2-(N- ⁇ [2'- (2H-l,2,3,4-tetrazol-5-yl)biphenyl-4-yl]methyl ⁇ pentanamido)butanoic acid, or its pharmaceutically acceptable salts, in combination with Sacubitril of formula (II), systematic name (2i?,4S)-5-(biphenyl-4-yl)-4-[(3-carboxypropionyl)amino]-2-methylpentanoic acid ethyl ester, or its pharmaceutically acceptable salts, as well as methods for preparation and stabilization thereof.
  • Valsartan of formula (I) systematic name fS)-3-methyl-2-(N- ⁇ [2'- (2H-l,2,3,4-tetrazol-5-yl)biphenyl-4-yl]methyl ⁇ pentanamido
  • Valsartan and Sacubitril are a novel combination of drugs against hypertension and heart failure.
  • a pharmaceutical composition of Valsartan or its pharmaceutically acceptable salts with NEP inhibitors in the presence of pharmaceutically acceptable excipients for the treatment of hypertension is described in the patent application WO03059345.
  • the original product comprises a cocrystal of Valsartan disodium salt with the sodium salt of Sacubitril and two and half molecules of water, referred to as LCZ 696.
  • the summary formula of the cocrystal LCZ 696 is C 48 H5 5 N 6 0 8 Na 3 ⁇ 2.5 H 2 0.
  • Valsartan may form both an amorphous structure and various types of crystalline forms.
  • the patent applications WO2002006253, WO2004083192, WO2007017897, US20080261959, WO2003089417, WO2006076561, WO2003066606 and WO200206253 describe several types of solid forms of Valsartan or its pharmaceutically acceptable salts. These forms differ from each other with their crystal arrangement and their physical properties, especially solubility and bioavailability.
  • Valsartan is classified as BCS II - its solubility is strongly influenced by pH and it is easy to absorb. Valsartan is not a problematic substance from the point of view of stability in the dosage form. Dosage forms containing Valsartan do not exhibit a considerable increase of impurities during storage under various loads.
  • This invention provides a pharmaceutical composition containing Valsartan of formula (I), systematic name (S)-3 -methyl-2-(N- ⁇ [2'-(2H- 1 ,2,3 ,4-tetrazol-5-yl)biphenyl-4-yl]methyl ⁇ - pentanamido)butanoic acid, or its pharmaceutically acceptable salts, and Sacubitril of formula (II), systematic name (2i?,45)-5-(biphenyl-4-yl)-4-[(3-carboxypropionyl)amino]-2- methylpentanoic acid ethyl ester, or its pharmaceutically acceptable salts, with suitable pharmaceutical excipients.
  • Valsartan of formula (I) systematic name (S)-3 -methyl-2-(N- ⁇ [2'-(2H- 1 ,2,3 ,4-tetrazol-5-yl)biphenyl-4-yl]methyl ⁇ - pentanamido)but
  • the invention further provides a pharmaceutical composition containing a mixture of
  • Valsartan free acid and Sacubitril free acid with suitable pharmaceutical excipients are provided.
  • the invention further provides a pharmaceutical composition containing a mixture of Valsartan free acid and the calcium salt of Sacubitril with suitable pharmaceutical excipients.
  • the invention further provides a pharmaceutical composition containing a mixture of Valsartan free acid and the sodium salt of Sacubitril with suitable pharmaceutical excipients.
  • the invention further provides a pharmaceutical composition containing a mixture of Valsartan free acid and the cyclohexylammonium salt of Sacubitril with suitable pharmaceutical excipients.
  • the invention further provides a pharmaceutical composition containing a mixture of the sodium salt of Valsartan and the calcium salt of Sacubitril with suitable pharmaceutical excipients.
  • the invention further provides a pharmaceutical composition containing a mixture of the sodium salt of Valsartan and the sodium salt of Sacubitril with suitable pharmaceutical excipients.
  • the invention further provides a pharmaceutical composition containing a mixture of the sodium salt of Valsartan and the cyclohexylammonium salt of Sacubitril with suitable pharmaceutical excipients.
  • the invention further provides a pharmaceutical composition containing Valsartan or its pharmaceutically acceptable salts and Sacubitril or its pharmaceutically acceptable salts, at least one excipient being selected from the group of fillers, binders, disintegrants, lubricants, surfactants and/or glidants.
  • a preferred embodiment of the above mentioned pharmaceutical composition is such that at least one excipient from the group of fillers is selected from the group comprising: microcrystalline cellulose, meglumine, lactose, mannitol, sorbitol, xylitol, trehalose, carbonate salts, colloidal silica, fructose and other common pharmaceutical fillers.
  • Another preferred embodiment of the above mentioned pharmaceutical composition is such that at least one excipient from the group of disintegrants is selected from the group comprising: sodium salt of croscarmellose, crospovidone, starch and its derivatives and other common pharmaceutical disintegrants.
  • the invention further provides a pharmaceutical composition, which is in a form suitable for oral administration.
  • the pharmaceutical composition contains Valsartan or its pharmaceutically acceptable salts and Sacubitril or its pharmaceutically acceptable salts in a composition where individual active ingredients are physically separated from each other.
  • it is a pharmaceutical composition that is in the form of a tablet. Further, it is a pharmaceutical composition where individual active ingredients are contained in a single-layered tablet. In a preferred embodiment it is a pharmaceutical composition where the active ingredients are separated from each other in a double-layered tablet.
  • Another object of this invention is a pharmaceutical composition characterized in that the content of the active ingredient is 10 wt.% to 70 wt.%, preferably 15 wt.% to 50 wt.%.
  • this invention provides a method for preparation of the pharmaceutical composition containing Valsartan or its pharmaceutically acceptable salts and Sacubitril or its pharmaceutically acceptable salts, characterized in that the method comprises at least one processing method selected from the group: wet granulation, dry granulation, admixing the mixture to the tabletting matter, fluid drying, fluid granulation, compaction, briquetting, direct tabletting or a combination of these methods.
  • the invention further provides a method for preparation, where Valsartan or its pharmaceutically acceptable salt and Sacubitril or its pharmaceutically acceptable salt are sieved together with at least one pharmaceutically acceptable excipient and tabletted by means of direct tabletting.
  • the invention further provides a method for preparation comprising steps where a) Valsartan or its pharmaceutically acceptable salt is granulated together with at least one pharmaceutically acceptable excipient with the use of a solvent, preferably water, b) Sacubitril or its pharmaceutically acceptable salt is directly admixed to the granulate of Valsartan from step a) together with at least one pharmaceutically acceptable excipient, and c) the tabletting matter prepared this way is tabletted.
  • the invention further provides a method for preparation, characterized in that it comprises the following steps: a) Valsartan or its pharmaceutically acceptable salt is processed by fluid granulation together with at least one pharmaceutically acceptable excipient with the use of a solvent, preferably water, b) Sacubitril or its pharmaceutically acceptable salt is compacted together with at least one pharmaceutically acceptable excipient, and c) the granulate of Valsartan and compactate of Sacubitril are mixed and tabletted into a single- layered tablet.
  • the invention further provides a method for preparation, characterized in that it comprises the following steps: a) Valsartan or its pharmaceutically acceptable salt is granulated together with at least one pharmaceutically acceptable excipient with the use of a solvent, preferably water, b) Sacubitril or its pharmaceutically acceptable salt is compacted together with at least one pharmaceutically acceptable excipient, and c) the tabletting matter containing Valsartan and Sacubitril is tabletted into a double-layered tablet with separated active ingredients.
  • the preparation method is characterized in that Sacubitril is in the form of the free acid, sodium salt, calcium salt, potassium salt, magnesium salt or cyclohexylammonium salt.
  • the preparation method is characterized in that Valsartan is in the form of the free acid, sodium salt, calcium salt, potassium salt or magnesium salt.
  • the preparation method is characterized in that at least one pharmaceutically acceptable excipient is selected from the group comprising a filler, binder, disintegrant, lubricant, surfactant and/or glidant and or any combinations thereof.
  • the method is characterized in that at least one excipient from the group of fillers is selected from the group comprising: macrocrystalline cellulose, meglumine, lactose, mannitol, sorbitol, xylitol, trehalose, carbonate salts, colloidal silica, fructose and other common pharmaceutical fillers.
  • the preparation method is characterized in that at least one excipient from the group of disintegrants is selected from the group comprising: sodium salt of croscarmellose, crospovidone, starch and its derivatives and other common pharmaceutical disintegrants.
  • the preparation method is characterized in that it further contains at least one excipient from the group of lubricants, selected from the group comprising: magnesium stearate, stearic acid, calcium stearate, sodium stearyl fumarate, glycerol dibehenate, talc and other common pharmaceutical lubricants.
  • the preparation method is characterized in that it further contains at least one excipient for local pH adjustment, such as meglumine, Na 2 HP0 4 , Mg(OH) 2 , sodium hydroxide, carbonates, potassium citrate, sodium citrate and other pharmaceutically acceptable alkalizing salts.
  • excipient for local pH adjustment such as meglumine, Na 2 HP0 4 , Mg(OH) 2 , sodium hydroxide, carbonates, potassium citrate, sodium citrate and other pharmaceutically acceptable alkalizing salts.
  • this invention provides a method for stabilization of a pharmaceutical composition containing Valsartan of formula I, systematic name (25j-3-methyl-2-(N- ⁇ [2'-(2H- l,2,3,4-tetrazol-5-yl)biphenyl-4-yl]methyl ⁇ pentanamido)butanoic acid, or its pharmaceutically acceptable salts, and Sacubitril of formula II, systematic name (2i?,4S)-5-(biphenyl-4-yl)-4- [(3-carboxypropionyl)amino]-2-methylpentanoic acid ethyl ester, or its pharmaceutically acceptable salts with suitable pharmaceutical excipients, wherein the composition is stored in a pharmaceutical package where an inert atmosphere is maintained by means of nitrogen.
  • Sacubitril In the free acid form, Sacubitril is difficult to isolate in the solid state. This substance is unstable at higher temperatures or when exposed to higher relative humidity.
  • the formulations described in this patent are stable dosage forms that contain Valsartan and Sacubitril or their pharmaceutically acceptable salts as separate components, namely in a single-layered or double-layered tablet.
  • the dose of the preparation varies from 20 to 400 mg of Valsartan and from 20 to 400 mg of Sacubitril.
  • the content of each dosage form in the tablet varies in the range from 10 to 70 wt.%. Not only direct tabletting, but also wet granulation and dry granulation are used for the preparation of these dosage forms.
  • the pharmaceutical package of the composition is a blister pack whose material is selected from the group of the type: OPA/ALU/PVC, PVC/ACLAR/PVC, PVC, PVC/PE PVDC, PVC/PVDC, PVC/PVDC, where OPA stands for oriented polyamide film, ALU stands for aluminium, PVC stands for polyvinyl chloride, ACLAR stands for poly-chloro-tri-fluoro- ethylene, PVDC stands for polyvinylidene chloride a PE stands for polyethylene.
  • OPA stands for oriented polyamide film
  • ALU stands for aluminium
  • PVC stands for polyvinyl chloride
  • ACLAR stands for poly-chloro-tri-fluoro- ethylene
  • PVDC stands for polyvinylidene chloride
  • PE stands for polyethylene.
  • Valsartan and Sacubitril or its pharmaceutically acceptable salts thereof in one tablet as separate substances is that the preparation of the dosage form is shorter and simpler and the demanding production of the cocrystal is avoided. But at the same time, the described product retains the properties of the original product - i.e. releasing of the active ingredients and their stability.
  • the formulation of both the single- layered and double-layered tablet with the active ingredients Valsartan and Sacubitril separated prevents excessive degradation of Sacubitril at higher temperatures, increasing the stability of the product. Thanks to this, the storage conditions of the drug do not need to be modified.
  • Sacubitril free acid and Valsartan free acid were mixed together with microcrystalline cellulose, sodium salt of croscarmellose, colloidal silica and magnesium stearate. The mixture was sieved through a sieve and tabletted.
  • Sacubitril sodium salt and Valsartan sodium salt were mixed together with microcrystalline cellulose, sodium salt of croscarmellose, colloidal silica and magnesium stearate. The mixture was sieved through a sieve and tabletted.
  • Magnesium stearate Lubricant Sacubitril cyclohexylammonium salt and Valsartan sodium salt were mixed together with microcrystalline cellulose, sodium salt of croscarmellose, colloidal silica and magnesium stearate. The mixture was sieved through a sieve and tabletted.
  • Valsartan free acid was granulated together with Prosolv, lauryl sulphate, sorbitol, povidone and crospovidone. Purified water was used as the granulating solvent. The dried granulate was sieved. Sacubitril sodium salt was admixed to the granulate of Valsartan free acid together with sodium hydrogen carbonate, crospovidone, pre-gelatinized starch, sodium stearyl fumarate and colloidal silica. The tabletting matter prepared this way was tabletted into single- layered tablets.
  • Valsartan free acid was processed by means of fluid granulation together with Prosolv, sodium lauryl sulphate, sorbitol, povidone and crospovidone. Purified water was used as the granulating solvent. The dried granulate was sieved. Sacubitril calcium salt was compacted and sieved together with microcrystalline cellulose, colloidal silica, crospovidone, sodium stearyl fumarate and pre-gelatinized starch. The granulate of Valsartan and compactate of Sacubitril is mixed together with sodium hydrogen carbonate, crospovidone, colloidal silica and sodium stearyl fumarate. The mixture prepared this way was tabletted.
  • Crospovidone Disintegrant Colloidal silica Glidant
  • Valsartan free acid was granulated together with Prosolv, sodium lauryl sulphate, sorbitol, povidone and crospovidone. Purified water was used as the granulating solvent. The dried granulate was sieved and microcrystalline cellulose, colloidal silica, crospovidone and sodium stearyl fumarate were admixed to it. Sacubitril cyclohexylammonium salt was compacted together with microcrystalline cellulose, colloidal silica, crospovidone, sodium stearyl fumarate and pre-gelatinized starch and mixed with sieved microcrystalline cellulose, colloidal silica, crospovidone, sodium stearyl fumarate. The tabletting matters containing Valsartan free acid and Sacubitril cyclohexylammonium salt were tabletted into double-layered tablets with separated active ingredients.
  • Sacubitril calcium salt and Valsartan sodium salt were mixed together with microcrystalline cellulose, sodium salt of croscarmellose, colloidal silica and magnesium stearate. The mixture was sieved through a sieve and tabletted.
  • OPA is oriented polyamide film (Nylon)
  • ALU is aluminium
  • PVC is polyvinyl chloride
  • ACLAR is poly-chloro-tri-fluoro-ethylene
  • PVDC is polyvinylidene chloride
  • PE is polyethylene.
  • Table 1 Total amount of impurities in the formulation - packing under an air atmosphere - 3 months
  • Table 2 Total amount of impurities in the formulation - packing under a nitrogen atmosphere
  • Example 1 O.05 % ⁇ 0.05 % n/a ⁇ 0.05 % n a 0.08 %
  • Example 2 ⁇ 0.05 % ⁇ 0.05 % n/a ⁇ 0.05 % n/a ⁇ 0.05 %
  • Example 3 ⁇ 0.05 % O.05 % n/a 0.07 % n/a 0.09 %
  • Example 8 ⁇ 0.05 % ⁇ 0.05 % n/a 0.15 % n/a 0.15 %
  • Example 10 ⁇ 0.05 % ⁇ 0.05 % n/a ⁇ 0.05 % n/a ⁇ 0.05 %

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

Abstract

L'invention concerne des compositions administrées par voie orale contenant du Valsartan de formule (I), de nom systématique suivant : acide (S)-3-méthyl-2-(N--{[2'-(2H-1,2,3,4-tétrazol-5-yl)biphényl-4-yl]méthyl}-pentanamido)butanoïque, ou ses sels pharmaceutiquement acceptables, et le Sacubitril de formule (II), de nom systématique suivant : ester éthylique d'acide (2R,4S)-5-(biphényl-4-yl)-4-[(3-carboxypropionyl)amino]-2-méthyl-pentanoïque, ou ses sels pharmaceutiquement acceptables comportant des excipients pharmaceutiques appropriés, et également leur préparation et leur stabilisation, la composition étant conservée dans un conditionnement pharmaceutique où une atmosphère inerte est maintenue au moyen d'azote.
PCT/CZ2016/000079 2015-07-20 2016-07-20 Composition pharmaceutique contenant du valsartan et du sacubitril et procédés de préparation et de stabilisation correspondants Ceased WO2017012600A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CZ2015-508A CZ2015508A3 (cs) 2015-07-20 2015-07-20 Farmaceutická kompozice obsahující Valsartan a Sacubitril a způsob její přípravy
CZPV2015-508 2015-07-20
CZ2016-57A CZ201657A3 (cs) 2016-02-04 2016-02-04 Způsob stabilizace farmaceutické kompozice obsahující Sacubitril a Valsartan
CZPV2016-57 2016-02-04

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WO2017012600A1 true WO2017012600A1 (fr) 2017-01-26

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107188817A (zh) * 2017-05-22 2017-09-22 杭州瑞法康科技有限公司 一种高纯度沙库比曲半钙盐一水合物的新晶型及其制备方法
CN107602410A (zh) * 2017-09-13 2018-01-19 浙江三门恒康制药有限公司 沙库比曲钠盐的晶型ii及其制备方法
WO2018069937A1 (fr) 2016-10-13 2018-04-19 Mylan Laboratories Limited Dispersions solides de sacubitril/valsartan trisodique et procédé de leur préparation
WO2018178295A1 (fr) 2017-03-31 2018-10-04 Alfred E. Tiefenbacher (Gmbh & Co. Kg) Extrudat thermofusible stable contenant du valsartan et du sacubitril
WO2018211479A1 (fr) * 2017-05-19 2018-11-22 Lupin Limited Compositions stabilisées d'inhibiteurs de l'angiotensine ii et d'inhibiteurs de l'endopeptidase neutre, et leur procédé de préparation
WO2019020706A1 (fr) 2017-07-28 2019-01-31 Synthon B.V. Composition pharmaceutique comprenant du sacubitril et du valsartan
WO2019073062A1 (fr) 2017-10-13 2019-04-18 Alfred E. Tiefenbacher (Gmbh & Co. Kg) Comprimé contenant du valsartan et du sacubitril
CN111358783A (zh) * 2018-12-25 2020-07-03 北京福元医药股份有限公司 一种沙库巴曲缬沙坦钠药物制剂
EP3766484A1 (fr) 2019-07-19 2021-01-20 Zentiva, K.S. Forme posologique pharmaceutique solide comprenant du valsartan et du sacubitril
KR20210108913A (ko) 2020-02-26 2021-09-03 에리슨제약(주) 사쿠비트릴 및 발사르탄을 포함하는 심부전 치료용 서방성 제제, 및 이를 포함하는 다중방출 복합제제와 이의 제조방법
KR20210138510A (ko) 2020-05-12 2021-11-19 에리슨제약(주) 사쿠비트릴, 발사르탄 및 네비보롤을 포함하는 심부전 및 허혈성 심질환의 예방 또는 치료용 약제학적 조성물 및 이를 포함하는 약제학적 복합제제
US11382866B2 (en) 2017-07-06 2022-07-12 Mankind Pharma Ltd. Fixed dose pharmaceutical composition of valsartan and sacubitril
EP4088715A1 (fr) 2021-05-14 2022-11-16 KRKA, d.d., Novo mesto Formulation pharmaceutique de valsartan et sacubitril
EP4268806A1 (fr) 2022-04-26 2023-11-01 Sanovel Ilac Sanayi Ve Ticaret A.S. Comprimé comprenant du sacubitril et du valsartan traité par granulation sèche

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EP0555175A1 (fr) 1992-01-22 1993-08-11 Ciba-Geigy Ag Amides de l'acide amino-4 butyrique comprenant un groupment biaryle
WO2002006253A1 (fr) 2000-07-19 2002-01-24 Novartis Ag Sels de valsartan
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WO2018069937A1 (fr) 2016-10-13 2018-04-19 Mylan Laboratories Limited Dispersions solides de sacubitril/valsartan trisodique et procédé de leur préparation
WO2018178295A1 (fr) 2017-03-31 2018-10-04 Alfred E. Tiefenbacher (Gmbh & Co. Kg) Extrudat thermofusible stable contenant du valsartan et du sacubitril
WO2018211479A1 (fr) * 2017-05-19 2018-11-22 Lupin Limited Compositions stabilisées d'inhibiteurs de l'angiotensine ii et d'inhibiteurs de l'endopeptidase neutre, et leur procédé de préparation
CN107188817A (zh) * 2017-05-22 2017-09-22 杭州瑞法康科技有限公司 一种高纯度沙库比曲半钙盐一水合物的新晶型及其制备方法
US11382866B2 (en) 2017-07-06 2022-07-12 Mankind Pharma Ltd. Fixed dose pharmaceutical composition of valsartan and sacubitril
US11819577B2 (en) 2017-07-06 2023-11-21 Mankind Pharma Ltd. Fixed dose pharmaceutical composition of valsartan and sacubitril
WO2019020706A1 (fr) 2017-07-28 2019-01-31 Synthon B.V. Composition pharmaceutique comprenant du sacubitril et du valsartan
US10588892B2 (en) 2017-07-28 2020-03-17 Synthon B.V. Pharmaceutical composition comprising sacubitril and valsartan
CN107602410A (zh) * 2017-09-13 2018-01-19 浙江三门恒康制药有限公司 沙库比曲钠盐的晶型ii及其制备方法
WO2019073062A1 (fr) 2017-10-13 2019-04-18 Alfred E. Tiefenbacher (Gmbh & Co. Kg) Comprimé contenant du valsartan et du sacubitril
CN111358783A (zh) * 2018-12-25 2020-07-03 北京福元医药股份有限公司 一种沙库巴曲缬沙坦钠药物制剂
EP3766484A1 (fr) 2019-07-19 2021-01-20 Zentiva, K.S. Forme posologique pharmaceutique solide comprenant du valsartan et du sacubitril
KR20210108913A (ko) 2020-02-26 2021-09-03 에리슨제약(주) 사쿠비트릴 및 발사르탄을 포함하는 심부전 치료용 서방성 제제, 및 이를 포함하는 다중방출 복합제제와 이의 제조방법
KR20210138510A (ko) 2020-05-12 2021-11-19 에리슨제약(주) 사쿠비트릴, 발사르탄 및 네비보롤을 포함하는 심부전 및 허혈성 심질환의 예방 또는 치료용 약제학적 조성물 및 이를 포함하는 약제학적 복합제제
EP4088715A1 (fr) 2021-05-14 2022-11-16 KRKA, d.d., Novo mesto Formulation pharmaceutique de valsartan et sacubitril
WO2022238563A1 (fr) 2021-05-14 2022-11-17 Krka, D.D., Novo Mesto Formulation pharmaceutique de valsartan et de sacubitril
EP4268806A1 (fr) 2022-04-26 2023-11-01 Sanovel Ilac Sanayi Ve Ticaret A.S. Comprimé comprenant du sacubitril et du valsartan traité par granulation sèche

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