WO2017091041A1 - Nouveau sel de fimasartan - Google Patents

Nouveau sel de fimasartan Download PDF

Info

Publication number
WO2017091041A1
WO2017091041A1 PCT/KR2016/013727 KR2016013727W WO2017091041A1 WO 2017091041 A1 WO2017091041 A1 WO 2017091041A1 KR 2016013727 W KR2016013727 W KR 2016013727W WO 2017091041 A1 WO2017091041 A1 WO 2017091041A1
Authority
WO
WIPO (PCT)
Prior art keywords
salt
fimasartan
organic acid
hydrate
solvate
Prior art date
Application number
PCT/KR2016/013727
Other languages
English (en)
Korean (ko)
Inventor
김지한
김창모
Original Assignee
보령제약 주식회사
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 KR1020150166616A external-priority patent/KR20170061493A/ko
Application filed by 보령제약 주식회사 filed Critical 보령제약 주식회사
Publication of WO2017091041A1 publication Critical patent/WO2017091041A1/fr

Links

Classifications

    • 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
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings

Definitions

  • the present invention relates to novel salts of fimasartan. More specifically, the present invention relates to a novel salt of fimasartan having excellent physicochemical properties such as stability, hygroscopicity, flowability, and anti-adhesion, as well as excellent solubility and bioavailability.
  • the physicochemical properties of the drug also have an important effect on the drug's effect.
  • the drug must meet physicochemical criteria such as good stability, non-hygroscopicity and processability into the formulation, as well as excellent solubility and bioavailability, and research on new salts of pimasartan that can satisfy these properties is ongoing. have.
  • Fimasartan is a hypertensive drug that is an angiotensin II receptor antagonist.
  • Canabra is marketed in three doses of 30, 60, and 120 mg under the trade name, and the main component is fimasartan potassium salt.
  • the fimasartan exhibits excellent pharmacological activity but has low solubility and has been used in the form of fimasartan potassium salt for its improvement.
  • It is an object of the present invention to provide a pharmaceutical composition comprising a novel salt of fimasartan.
  • the present invention provides a novel salt of fimasartan, a method for preparing the same, and a pharmaceutical composition comprising the same.
  • the present invention provides novel salts of fimasartan.
  • the pimasartan novel salt of the present invention may be an organic salt of fimasartan or an amine salt of fimasartan.
  • the present invention provides a hydrate or solvate of the fimasartan organic acid salt or fimasartan amine salt.
  • Fimasartan organic acid salts or fimasartan amine salts, or hydrates or solvates thereof according to the present invention exhibit excellent solubility and bioavailability, have excellent stability and non-hygroscopicity, and have excellent processability and good drug efficacy as formulations.
  • the present invention provides organic salts of fimasaltan or hydrates or solvates thereof.
  • the organic acid salt of fimasartan is methanesulfonate of fimasartan, benzenesulfonate of fimasartan, camphorsulfonate of fimasartan, toluenesulfonate of fimasartan, ethanedisulfonate of fimasartan, and fimasaltan It may be naphthalenedi sulfonate of, preferably may be campa sulfonate or benzene sulfonate of fimasaltan.
  • the fimasaltan organic acid salt may be a compound represented by the following Chemical Formula 1.
  • HX may be methanesulfonic acid, benzenesulfonic acid, campasulfonic acid, toluenesulfonic acid, and preferably may be campasulfonic acid or benzenesulfonic acid.
  • the fimasaltan organic acid salt may be a compound represented by the following Chemical Formula 2.
  • H 2 X may be ethane disulfonic acid or naphthalenedisulfonic acid.
  • the fimasartan organic acid salt may be a crystal. In the present invention, the fimasartan organic acid salt may be anhydrous crystals.
  • the organic acid salt of fimasartan refers to both fimasartan organic acid salts, geometric isomers thereof, optical isomers and racemates.
  • the camphorsulfonate of pimisaltan refers to both the geometric isomers, optical isomers, and racemates together with campasulfonate of pimasaltan.
  • Fimasaltan organic acid salt, or a hydrate or solvate thereof which is a novel salt of fimasartan according to the present invention, has high solubility, excellent oral absorption rate, and can exhibit excellent therapeutic effect even at a small dose, thereby significantly improving the convenience of patient medication. It can be improved.
  • it is suitable for the preparation of pharmaceutical formulations due to its excellent pharmaceutical physical properties such as stability, non-hygroscopicity and processability as a formulation.
  • the present invention provides fimasartan amine salts or hydrates or solvates thereof.
  • the amine salt of fimasartan may be choline salt, meglumine salt, ammonium salt or arginine salt of fimasartan.
  • Fimasaltan choline salt according to the present invention may be a compound represented by the following formula (3).
  • the meglumine salt of fimasaltan according to the present invention may be a compound represented by the following formula (4).
  • R 1 and R 2 may be H, R 3 is CH 3 and R 4 may be CH 2 (CHOH) 4 CH 2 OH.
  • Ammonium salt of fimasaltan according to the present invention may be a compound represented by Formula 4, and in Formula 4 R 1, R 2 , R 3 and R 4 is H.
  • Arginine salt of fimasaltan according to the present invention may be a compound represented by the following formula (5).
  • Fimasartan choline salts, meglumine salts, fimasartan ammonium salts, fimasartan arginine salts or hydrates or solvates thereof are non-hygroscopic and exhibit good stability in the solid state so that the formulation can maintain a uniform content for a long time.
  • the fimasartan amine salt preferably fimasartan choline salt, meglumine salt, ammonium salt or arginine salt may be a crystal.
  • the fimasartan choline salt, meglumine salt, ammonium salt or arginine salt may be anhydrous crystals or a hydrate, for example, a dihydrate of fimasartan meglumine salt.
  • the choline salt, meglumine salt, ammonium salt or arginine salt of fimasartan includes all of the geometric isomers, optical isomers, and racemates of choline salt, meglumine salt, ammonium salt or arginine salt of fimasartan.
  • Fimasaltan amine salt, or a hydrate or solvate thereof, which is a novel salt of fimasartan according to the present invention shows high bioavailability upon oral administration, and thus can show an excellent therapeutic effect even when a small amount is used. It can be remarkably improved. In addition, it has excellent pharmaceutical physicochemical properties such as stability, non-hygroscopicity and processability as a formulation, making it suitable for the preparation of pharmaceutical formulations compared to fimasartan potassium salt.
  • fimasartan In the case of fimasartan, poor solubility as a poorly soluble drug was not easy to formulate and the bioavailability was not high enough. Therefore, in order to exhibit a sufficient therapeutic effect through oral administration, fimasartan should be included in the formulation in a high content, and as a result, there was a problem in that the patient's convenience of medication was lowered. Has been.
  • the fimasartan organic acid salt and the fimasartan amine salt of the present invention are excellent in physicochemical and pharmacological properties required for drugs such as solubility and bioavailability, and thus are easier to formulate than conventional fimasartan potassium salts, and the convenience of patient medication Can be improved.
  • the fimasartan organic acid salt and the amine salt are non-hygroscopic and exhibit excellent stability in the solid state, so that the formulation can maintain a uniform content for a long time, and the physicochemical properties required for the pharmaceutical are excellent.
  • the excellent physical and chemical properties it is possible to mass-produce the formulation, which is economical, and can produce the fimasartan salt in high yield.
  • the present invention provides a method for preparing the organic acid salt of fimasartan or a hydrate or solvate thereof.
  • the method is a
  • It provides a method for preparing an organic acid salt of fimasartan comprising the step of adding an organic acid to the reactant.
  • the preparing of the reactant may include adding the fimasaltan or a salt thereof to a solvent.
  • the organic acid may be a known acid, for example, the organic acid may be a sulfonic acid, preferably benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, camphorsulfonic acid, ethanedisulfonic acid or naphthalenedi Sulfonic acid.
  • the organic acid may be a sulfonic acid, preferably benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, camphorsulfonic acid, ethanedisulfonic acid or naphthalenedi Sulfonic acid.
  • the acid may be determined according to the kind of fimasaltan organic acid salt to be prepared.
  • the acid when preparing campasulfonic acid salt of fimasaltan, the acid may be campasulfonic acid.
  • the camphorsulfonic acid may be a racemate or a stereoisomer thereof, and may be (S)-(-)-campasulfonic acid, (R)-(-)-campasulfonic acid or racemates thereof, For example, (S)-(-)-campasulfonic acid.
  • the solvent may include an organic solvent.
  • the organic solvent may be ethyl acetate, ethanol, acetonitrile, methanol, isopropanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, butanol, tetrahydrofuran, 1,4-dioxane, methyl acetate or mixtures thereof,
  • it may be ethyl acetate, ethanol, isopropanol, acetonitrile, tetrahydrofuran, or a mixture thereof, more preferably ethanol.
  • the solvent when the organic solvent is a solvent miscible with water, the solvent may further include water in addition to the organic solvent.
  • the starting material in the preparation of the fimasartan organic acid salt, is fimasartan or a fimasartan salt, and preferably may be pimasartan.
  • the starting material is a salt of fimasartan, it may be a fimasartan potassium salt.
  • the method may further include heating after adding an acid.
  • the heating may be performed at 20 ° C to 80 ° C, preferably at 25 ° C to 65 ° C.
  • the method may further include adding an organic solvent after performing the heating step.
  • the type of the organic solvent is as described above.
  • the organic solvent added to the reactant may be the same or different from the previous organic solvent.
  • the present invention provides a process for preparing the amine salt of fimasartan or a hydrate or solvate thereof.
  • the method is a
  • It provides a method for preparing the amine salt of fimasaltan comprising the step of adding an amine to the reactant.
  • the preparing of the reactant may include mixing the fimasaltan or a salt thereof with the solvent.
  • the amine added to the reactant may be choline, choline salt, meglumine, ammonia or arginine.
  • the choline salt may be choline hydroxide (choline hydroxide).
  • a solution containing choline hydroxide may be added to the reactant, and preferably, the solution including choline hydroxide may be a methanol solution including choline hydroxide.
  • the ammonia may be preferably an ammonia solution, and specifically, may be added in a solution state in which ammonia gas is dissolved in methanol.
  • the solvent may include an organic solvent.
  • the organic solvent may be ethyl acetate, ethanol, acetonitrile, methanol, isopropanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, butanol, tetrahydrofuran, 1,4-dioxane, methyl acetate, or mixtures thereof ,
  • the solvent when the organic solvent is a solvent miscible with water, the solvent may further include water in addition to the organic solvent.
  • the solvent may be a mixture of acetonitrile and water, in which case the volume ratio of acetonitrile and water may be about 30 to 10: 1.
  • the starting material in the preparation of the fimasartan amine salt is the fimasartan or the fimasartan salt.
  • the starting material is a salt of fimasartan, it may be a fimasartan potassium salt, preferably fimasartan is used.
  • the method may further include heating after adding the amine.
  • the heating may be performed at 20 ° C to 80 ° C, preferably at 25 ° C to 65 ° C.
  • the method may further include adding an organic solvent after performing the heating step.
  • the type of the organic solvent is as described above.
  • the organic solvent added to the reactant may be the same or different from the previous organic solvent.
  • the present invention provides compositions comprising fimasartan organic acid salts, hydrates or solvates thereof.
  • the present invention relates to methanesulfonate of fimasartan, benzenesulfonate of fimasartan, campasulfonate of fimasartan, toluenesulfonate of fimasartan, ethanedisulfonate of fimasartan or naphthalenedi of fimasartan.
  • compositions comprising sulfonates, hydrates or solvates thereof.
  • the present invention provides compositions comprising fimasartan amine salts, hydrates or solvates thereof.
  • the fimasartan amine salt may be fimasartan choline salt, meglumine salt, ammonium salt or arginine salt.
  • the composition is a pharmaceutical composition as stroke, stroke, cerebral hemorrhage, cerebral infarction, Alzheimer's disease, vascular dementia, Creutzfeldt-Jakob disease, diabetes, obesity, hyperlipidemia, coronary artery disease, angina pectoris, myocardial infarction, hypertension, heart failure, inflammation Or a pharmaceutical composition for treating or preventing renal failure.
  • the pharmaceutical composition may further include a pharmaceutically acceptable additive.
  • the pharmaceutically acceptable is a physiologically acceptable and when administered to a human, usually in the manufacture of self-pharmaceutical compositions having ordinary knowledge in the art without causing gastrointestinal disorders, allergic reactions such as dizziness or the like.
  • the additives may be carriers, excipients, extenders, antioxidants, buffers, fillers, anticoagulants, lubricants, wetting agents, fragrances, emulsifiers, suspending agents, surfactants and preservatives.
  • the additive may include lactose, dextrose, calcium silicate, corn starch, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, Methyl cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, stearic acid, magnesium stearate, calcium stearate, gelatin, mineral oil, saline solution, aqueous glucose solution, pseudosugar solution, alcohol , Glycols, ethers (eg polyethylene glycol 400), oils, fatty acids
  • compositions of the present invention may be formulated according to conventional methods, may be prepared as oral dosage forms or parenteral dosage forms, and may preferably be oral dosage forms.
  • the preparation for oral administration may be a solid preparation such as tablets, pills, powders, granules, capsules, or liquid preparations such as suspensions, solvents, emulsions, and syrups, and preferably solid preparations. Most preferably, more preferably a tablet.
  • the fimasartan organic acid salt or amine salt according to the present invention has excellent stability, excellent solubility in various solvents, and non-hygroscopicity, and thus has excellent physicochemical properties such as processability as a formulation. Therefore, when formulated in the form of tablets or capsules, it is possible to produce a tablet or capsule with excellent dispersibility and uniform pharmacological effect, and does not cause a problem that the pharmacological effect is lowered during the formulation process. Therefore, it is possible to economically produce a formulation having excellent pharmacological effects and having a uniform pharmacological effect.
  • the pharmaceutical composition of the present invention is formulated as an oral solid preparation
  • examples of the additives used are cellulose, calcium silicate, corn starch, lactose, sucrose, dextrose, calcium phosphate, stearic acid, magnesium stearate, calcium stearate , Gelatin, talc and the like.
  • the pharmaceutical composition When the pharmaceutical composition is formulated as a liquid preparation for oral administration, the pharmaceutical composition may be formulated by adding various additives such as water, simple diluents such as liquid paraffin, wetting agents, sweeteners, fragrances, preservatives, preservatives, colorants, and the like. have.
  • additives such as water, simple diluents such as liquid paraffin, wetting agents, sweeteners, fragrances, preservatives, preservatives, colorants, and the like. have.
  • the additives include water, saline solution, aqueous glucose solution, pseudo-aqueous solution, alcohol, glycol, ether (e.g. polyethylene glycol 400), oil, fatty acid, fatty acid ester, glycerol Ride etc. are mentioned.
  • the content of the additive included in the pharmaceutical composition is not particularly limited and may be appropriately adjusted within the content range used in conventional formulation.
  • the pharmaceutical composition may include fimasartan organic acid salt or fimasartan amine salt so that the content of fimasartan is about 1 mg to 240 mg, preferably about 5 to 180 mg. More preferably 10 to 120 mg.
  • the pharmaceutical composition may be administered orally or parenterally (eg, applied intravenously, subcutaneously, intraperitoneally or topically), and the dosage may be weight, age, sex, health of the patient.
  • the range may vary depending on the condition, diet, administration time, administration method, administration period or interval, excretion rate, constitution specificity, nature of the preparation, severity of disease, and the like.
  • the dose of fimasartan may be orally administered so that the dose of fimasartan is about 1 to 240 mg, preferably 5 to 180 mg, more preferably 10 to 120 mg per day, based on a normal adult weighing about 60 kg. It may be applied once or several times.
  • the pharmaceutical composition may further include other pharmacologically active substances in addition to fimasartan organic acid salt or amine salt, hydrate or solvate thereof.
  • the pharmacologically active substance may have the same pharmacological activity as the fimasartan organic acid salt or the amine salt, or may have other pharmacological activity.
  • pharmacologically active substances included in the pharmaceutical composition include anti-hyperlipidemic agents such as amlodipine, lercardidipine, nicardipine, simvastatin, atorvastatin, pravastatin, rosuvastatin, metformin, hydrochlorothiazide, cytagliptin, and billaggle Liptin, linagliptin, saxagliptin, tenelligliptin, anagliptin, melogliptin, dutogliptin, gemigliptin, and the like for diabetes treatment, pharmaceutically acceptable salts or mixtures thereof And more preferably amlodipine, rosuvastatin, atorvastatin, hydrochlorothiazide, citagliptin, bilagliptin, linagliptin and pharmaceutically acceptable salts thereof or mixtures thereof.
  • anti-hyperlipidemic agents such as amlodipine, lercardidipine, ni
  • compositions of the present invention may be used alone or in combination with methods using surgery, hormonal therapy, drug therapy and biological response modifiers to ameliorate, alleviate, treat or prevent disease.
  • novel fimasartan organic acid salts and amine salts according to the present invention have excellent solubility and bioavailability, and thus have excellent therapeutic effects, and are excellent in properties such as stability, adhesiveness, flowability, and non-hygroscopicity, so that they are easy to formulate and the patient's convenience of medication is remarkable. It can be improved.
  • Fimasartan choline salt prepared in Example 7 according to the method described in the Korean Pharmacopoeia, fimasartan meglumine salt prepared in Example 8 and fimasartan arginine salt and fimasaltan potassium salt prepared in Example 10 Solubility for) was measured.
  • the fimasartan novel salts and fimasartan potassium salts prepared in Examples 8, 9 and 11 were added until supersaturated, respectively, and then 25 ° C ⁇ 3 ° C. Stir for 24 h at and stabilize for 1 h. Thereafter, the solution was analyzed by liquid chromatography (HPLC) to determine the amount of dissolution based on fimasartan base (free base), and the results are shown in Table 1 below.
  • the fimasartan novel salts of the present invention are 10 to 100 times at all pHs as compared to conventional fimasartan potassium salts.
  • the fimasartan meglumine salt of Example 8 exhibited about 3 to 50 times higher solubility at all pHs, and the fimasartan arginine salt of Example 10 had a potassium salt at pH 1.2. Similar solubility was shown, and the solubility was about 10 and 50 times higher at pH 4.0 and 6.8, respectively.
  • Ten beagle dogs were divided into five groups of groups 1 to 6 and fasted for one day.
  • the capsule 5 filled in and the capsule 6 filled with gelatin capsules 30 mg of pimasartan potassium salt were prepared.
  • the first group includes a capsule 1 containing 30 mg of pimasartan camphorsulfonic acid salt
  • the second group includes a capsule 2 containing 30 mg of fimasartan benzenesulfonate salt
  • the third group includes a capsule 3 containing 30 mg of pimasartan choline salt
  • the fourth group includes Oral capsule 4 containing 30 mg of fimasartan meglumine salt
  • capsule 5 containing 30 mg of fimasartan arginine salt in group 5
  • capsule 6 containing 30 mg of fimasartan potassium salt in group 6 orally And immediately taken in a negative 30 mL / 1 dose.
  • fimasartan novel salts in particular fimasartan campasulfonate, benzenesulfonate, choline salt, meglumine salt or arginine salt, according to the present invention are higher in blood compared to fimasaltal potassium salt. Concentration. In particular, even when administered in the same content it can be seen that more than three times the Cmax and 1.5 times more than AUC.
  • the novel fimasartan organic acid salt or amine salt according to the present invention is significantly superior in bioavailability as compared to the conventional fimasartan potassium salt, and as a result, can exhibit a significantly high therapeutic effect.

Abstract

La présente invention concerne un nouveau sel de fimasartan ayant d'excellentes propriétés physico-chimiques une excellente solubilité et une excellente biodisponibilité; son procédé de préparation et une composition pharmaceutique le contenant.
PCT/KR2016/013727 2015-11-26 2016-11-25 Nouveau sel de fimasartan WO2017091041A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR1020150166616A KR20170061493A (ko) 2015-11-26 2015-11-26 피마살탄의 신규 염
KR10-2015-0166589 2015-11-26
KR20150166589 2015-11-26
KR10-2015-0166616 2015-11-26
KR10-2015-0166679 2015-11-26
KR20150166679 2015-11-26

Publications (1)

Publication Number Publication Date
WO2017091041A1 true WO2017091041A1 (fr) 2017-06-01

Family

ID=58763347

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2016/013727 WO2017091041A1 (fr) 2015-11-26 2016-11-25 Nouveau sel de fimasartan

Country Status (1)

Country Link
WO (1) WO2017091041A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019212214A1 (fr) * 2018-04-30 2019-11-07 보령제약 주식회사 Préparation pharmaceutique

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012141385A1 (fr) * 2011-04-12 2012-10-18 Boryung Pharmaceutical Co., Ltd. Composition pharmaceutique antihypertensive
KR20140006233A (ko) * 2012-06-28 2014-01-16 보령제약 주식회사 피마살탄 및 히드로클로로티아지드가 함유된 약제학적 조성물
WO2014142607A1 (fr) * 2013-03-14 2014-09-18 보령제약 주식회사 Médicament combiné pharmaceutique
KR20150041223A (ko) * 2013-10-04 2015-04-16 보령제약 주식회사 피마살탄을 포함하는 허혈성 뇌질환 예방 또는 치료용 약학적 조성물
CN104971052A (zh) * 2015-06-15 2015-10-14 北京睿创康泰医药研究院有限公司 含有非马沙坦钾三水合物的药物组合物及其制备方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012141385A1 (fr) * 2011-04-12 2012-10-18 Boryung Pharmaceutical Co., Ltd. Composition pharmaceutique antihypertensive
KR20140006233A (ko) * 2012-06-28 2014-01-16 보령제약 주식회사 피마살탄 및 히드로클로로티아지드가 함유된 약제학적 조성물
WO2014142607A1 (fr) * 2013-03-14 2014-09-18 보령제약 주식회사 Médicament combiné pharmaceutique
KR20150041223A (ko) * 2013-10-04 2015-04-16 보령제약 주식회사 피마살탄을 포함하는 허혈성 뇌질환 예방 또는 치료용 약학적 조성물
CN104971052A (zh) * 2015-06-15 2015-10-14 北京睿创康泰医药研究院有限公司 含有非马沙坦钾三水合物的药物组合物及其制备方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019212214A1 (fr) * 2018-04-30 2019-11-07 보령제약 주식회사 Préparation pharmaceutique

Similar Documents

Publication Publication Date Title
RU2382032C2 (ru) Соли донепезила, подходящие для получения фармацевтических композиций
JP2014510139A (ja) 固体形態のｈｉｖ阻害剤
AU661483B2 (en) Crystalline tiagabine hydrochloride monohydrate, its preparation and use
KR20170061615A (ko) 피마살탄의 신규 염
WO2021137369A1 (fr) Nouveau co-cristal d'empagliflozine
WO2020231146A1 (fr) Nouveau sel de pélubiprofène, son procédé de préparation et composition pharmaceutique le comprenant
CA3206062A1 (fr) Derives d'urolithine et leurs procedes d'utilisation
EP0276752B1 (fr) Dérivé de l'acide thiazolidine-4-carboxylique, sa préparation et compositions pharmaceutiques le contenant
KR20170061616A (ko) 피마살탄의 신규 염
WO2017091041A1 (fr) Nouveau sel de fimasartan
KR100283945B1 (ko) 심장 혈관계에 활성인 2-아미노-1,2,3,4-테트라히드로나프탈렌유도체, 이들의 제조방법 및 이들을 함유하는 약제 조성물
WO2012070701A1 (fr) Composé dérivé de la quinoléine, méthode pour sa préparation, et composition pharmaceutique le contenant
WO2010110622A9 (fr) Nouvelles formes cristallisées de l'adéfovir dipivoxil et leurs procédés de préparation
WO2014003400A1 (fr) Cocristal d'aripiprazole-acide organique, préparation ou composition le contenant et son procédé de préparation
US6538012B2 (en) Amlodipine hemimaleate
RU2294328C2 (ru) Оптически активные производные дигидропиридина, их применение и терапевтическое средство на их основе
CA1162539A (fr) Procede de preparation de nouveaux derives de l'indolobenzoxazine et de leurs sels
WO2017105090A1 (fr) Polymorphe cristallin de l-carnitine orotate, son procédé de production, ou son utilisation
WO2018038297A1 (fr) Nouveau sel de (r)- (1-méthylpyrrolidin-3-yl) méthyl (3'-chloro -4'-fluoro- [1,1'-biphényl]-2-yl) carbamate et forme cristalline de celui-ci
WO2020111524A1 (fr) Sel et forme cristalline d'un composé de puropyrimidine et utilisation pharmaceutique associée
WO2010150984A2 (fr) Dispersion solide d'adefovir dipivoxil amorphe présentant une stabilité améliorée et son procédé de préparation
JPS633866B2 (fr)
WO2023080741A1 (fr) Nouveau sel d'un dérivé d'acide phénylpropionique, son procédé de production et composition pharmaceutique le contenant
WO2023182869A1 (fr) Nouveau sel de composé agoniste du récepteur glp-1, son procédé de préparation et composition pharmaceutique le comprenant
WO2023113458A1 (fr) Nouveau sel de dérivé de 1-sulfonyle pyrrole, son procédé de préparation et composition pharmaceutique le comprenant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16868937

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16868937

Country of ref document: EP

Kind code of ref document: A1