WO2011087316A2 - 테트라졸 메탄설폰산 염의 제조방법 및 이에 사용되는 신규 화합물 - Google Patents
테트라졸 메탄설폰산 염의 제조방법 및 이에 사용되는 신규 화합물 Download PDFInfo
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- WO2011087316A2 WO2011087316A2 PCT/KR2011/000291 KR2011000291W WO2011087316A2 WO 2011087316 A2 WO2011087316 A2 WO 2011087316A2 KR 2011000291 W KR2011000291 W KR 2011000291W WO 2011087316 A2 WO2011087316 A2 WO 2011087316A2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to methods of preparing tetrazole methanesulfonic acid salts and novel compounds used therein.
- 2005/033097 discloses a method for producing the same.
- the method has a safety problem such as explosion, fire due to the use of hydrogen and metal catalyst in the mass reaction of the compound.
- a silica gel column chromatography method should be used, which is not suitable for large scale production because of the limited size of the column and the amount of material to be loaded.
- expensive silica gel and an excess of a developing solvent have to be used as the column stratifier, there is a disadvantage in that a high cost is required.
- the present invention provides a compound of formula (II), which can be used in the preparation of the tetrazole methanesulfonic acid salt:
- the present invention comprises the step of reacting a compound of formula (V) and a compound of formula (VI) in the presence of triphenylphosphine and a base, the compound of formula (II) It provides a method of manufacturing.
- the preparation method according to the present invention is different from the conventional method of carrying out acylation reaction using a condensing agent in the preparation of tetrazole methanesulfonic acid salt, a novel 4-oxo-4H-chromen-2-carbothioic acid S It is characterized in that tetrazole methanesulfonic acid salt is prepared in high purity and high yield without undergoing a separate purification process such as column chromatography by conducting acylation reaction using -benzothiazol-2-yl ester.
- Me means methyl group.
- the compounds of formula (II) and (III) are acylated in a polar aprotic solvent to prepare a compound of formula (IV).
- ester compound of formula (II) and the compound of formula (III) are selected from the group consisting of dichloromethane, tetrahydrofuran, ethyl ester, acetone, ⁇ , ⁇ - dimethylformamide, acetonitrile, and dimethyl sulfoxide
- a polar aprotic solvent preferably dichloromethane
- the activity of the compound of formula (II) remaining after the reaction is removed by adding methanol.
- acetone can naturally purify the compound to give an efficient and pure compound of formula (IV) having a purity of 98% or more.
- the compound of formula (II) is preferably used in 1 to 5 equivalents based on 1 equivalent of compound of formula (III).
- Acetone may also be used for purification in the reaction, where acetone is preferably used as an aqueous solution dissolved in water. Specifically, 95% acetone aqueous solution can be used. In addition, the acetone is preferably used in 35 to 45 volume ratio (v / w) relative to the total weight of the compound of formula (III).
- the tetrazole methanesulfonic acid salt of formula (I) is then prepared by adding methanesulfonic acid to the compound of formula (IV) prepared in the above step.
- the tetrazole compound of formula (IV) obtained in the above step is dissolved in an organic solvent such as chloroform and methanol, methanesulfonic acid is added thereto, and ethyl acetate and acetone are sequentially added to purify the compound.
- the tetrazole methanesulfonic acid salt of (I) can be obtained in a safe and efficient manner.
- methanesulfonic acid acts as a conjugate acid to the compound of the formula (IV) is preferably used in 1 to 1.5 equivalents based on 1 equivalent of the compound of the formula (IV).
- Ethyl acetate and acetone may also be used for purification in the reaction.
- ethyl acetate is preferably used in a volume ratio (v / w) of 1 to 5 with respect to the total weight of the compound of formula (IV).
- acetone is preferably used as an aqueous solution dissolved in water, preferably in a 95% acetone aqueous solution, and the amount of acetone used is in a volume ratio of 15 to 25 (v / w) based on the total weight of the compound of formula (IV). Is preferably.
- the production method of the present invention is 1_ (3-dimethylaminopropyl) -3-ethylcarbodiimide, ⁇ , ⁇ -dicyclonucleosilimide,
- the target compound can be obtained with high purity only by filtration, Easy mass production method.
- the compound of formula (II) used in the acylation reaction step (Step 1) is, as shown in Scheme 4, the compound of formula (V) and the compound of formula (VI) is triphenylphosphine And by reacting in the presence of a base.
- the compound of formula (VI) is equivalent to 1 equivalent of the compound of formula (V) It is preferably used in 1 to 2 equivalents as a reference.
- triphenylphosphine is preferably used in 1 to 2 equivalents based on 1 equivalent of the compound of formula (V).
- the base is preferably used in 1 to 2 equivalents based on 1 equivalent of chromonic acid of formula (V).
- the compound of formula (III) used as a starting material in the method for preparing tetrazole methanesulfonic acid salt according to the present invention the compound of formula (VII) and formula (VI II) Preparing a compound of formula (IX) by cyclization of a compound of step (Step 1), and reducing the compound of formula (IX) obtained by the step using a metal and an acid (Step 2) It may be prepared by a manufacturing method comprising a.
- Me means methyl group.
- the compound of formula (VII) is cyclized with a compound of formula (VIII) to prepare a nitrophenyl tetrazole compound of formula (IX).
- diazonium salts are prepared by reacting a compound of formula (VII) with a solvent such as 50% ethane in the presence of sodium nitrite and hydrochloric acid, whereupon a compound of formula (VI II) and pyridine are reacted Mix and keep the temperature below 10 ° c. Then the temperature of the resulting mixture is
- the compound of formula (IX) can be obtained by quenching with silver and stirring, washing with 2.5N hydrochloric acid solution, sodium bicarbonate solution and water, extracting with dichloromethane, removing the organic layer and adding methanol to crystallize (Suketaka). Ito et al., Bui lit in of the Chemical Society of Japan, Vol 49 (7), 1920-1923 (1976).
- the compound of Formula (VII) is, as shown in the following reaction formula 6, by reacting a compound of the formula (X) and a compound of the formula (XI) to prepare a compound of the formula (XII), And it can be prepared by reducing the reaction using an acid.
- the compound of formula (X) and the compound of formula (XI) are prepared in a solvent such as ⁇ , ⁇ -dimethylformamide in the presence of anhydrous potassium carbonate (K 2 CO 3 ) and sodium iodide (Nal) at 70 to 100 ° C. Stirring at C affords nitrobenzene isoquinoline of formula (XII).
- the dried compound of formula (XII) obtained above is then subjected to a solvent, for example a metal selected from the group consisting of iron, tin, zinc and nickel in a 50% ethanol solution, preferably iron, hydrochloric acid, nitric acid and sulfuric acid.
- the aminobenzene isoquinoline of formula (VII) can be prepared by reducing the reaction with an acid selected from the group consisting of acetic acid and mixtures thereof.
- the reaction can be carried out at 80 ° C for 3 hours, after reduction reaction Neutralization by addition of 10% aqueous sodium chloride solution, followed by filtration of the saltite, removal of the organic layer and solidification of the residue with ethyl ether afforded the compound of formula (VII).
- the metal may be used in 2 to 10 equivalents based on 1 equivalent of the compound of formula (XII)
- the acid may be used in 0.1 to 0.5 equivalents based on 1 equivalent of compound of formula (XII).
- the compound of formula (VI II) may be prepared by reacting a compound of formula (XIII) and a compound of formula (XIV) as shown in the following reaction formula 7.
- the compound of formula (XIII) and the compound of formula (XIV) can be obtained by reacting the compound of formula (XIV) at ethanol solubility at a reaction temperature of 70 to 80 ° C and then drying the resulting solid by filtration. (See Suuketaka Ito et al., Bullitin of the Chemical Society of Japan, Vol 49 (7), 1920-1923 (1976)). Subsequently, the compound of formula (IX) obtained in step KStep 1) of Scheme 5 is reduced by using a metal and an acid to prepare a compound of formula (III).
- the compound of formula (IX) is an acid selected from the group consisting of hydrochloric acid, nitric acid, sulfuric acid and acetic acid using a metal selected from the group consisting of iron, tin, zinc and nickel, preferably iron, preferably By reducing the reaction in acetic acid (eg 50% acetic acid aqueous solution) Can be converted to the compound of (III).
- acetic acid eg 50% acetic acid aqueous solution
- the reduction reaction is preferably carried out at 80 ° C for 3 hours, after which the organic solvent is removed through celite filtration and neutralization and the methane is stirred in the compound to obtain a compound of formula (III).
- the metal is 5 to 5 based on 1 equivalent of the compound of formula (IX)
- the acid may be used in an amount of 2 to 5 by volume (v / w) based on the total weight of the compound of formula (IX).
- the present invention can reduce the reaction time compared to the method of reducing the reaction using a palladium and hydrogen gas by proceeding a reduction reaction using a metal and an acid when preparing the compounds of Formulas ( ⁇ ) and (VII).
- the safety of the reaction can be improved to reduce the risk of explosion.
- a tetrazole ⁇ regular compound of formula (I) there is provided a tetrazole ⁇ regular compound of formula (I).
- a compound of formula (V) and a compound of formula (VI) are reacted in the presence of a base to
- the resulting organic layer was collected and stirred with 6.6 L of saturated sodium bicarbonate solution slowly added thereto. The resulting organic layer was removed and the aqueous layer was extracted with 1.25 L of chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate, distilled under reduced pressure to remove the solvent, and 10.6 L of methanol was added to the obtained residue and stirred. The resulting solid was filtered and hot-dried in a 40 ° C. dry oven to give the title compound (0.87 kg, 87%).
- the compound thus obtained was first recrystallized using chloroform.
- dichloromethane remained, which was stirred for 16 hours in an aqueous 95% acetone solution, filtered and dried in a 40 ° C dry oven to obtain the title compound (0.84 kg, 70%).
- the compound of formula (IV) prepared by the method of the present invention was superior in yield and purity compared to the compound prepared by the method of the comparative example, and the present invention is also recrystallized without a separate column purification It can be seen that pure compounds can be purified.
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Plural Heterocyclic Compounds (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2786434A CA2786434C (en) | 2010-01-15 | 2011-01-14 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
MX2012007868A MX2012007868A (es) | 2010-01-15 | 2011-01-14 | Metodo para preparar sales de acido tetrazol-mentasulfonico, y un nuevo compuesto utilizado en las mismas. |
RU2012134783/04A RU2509769C1 (ru) | 2010-01-15 | 2011-01-14 | Способ получения солей тетразолметансульфоновой кислоты и новое соединение, используемое в нем |
PL11733103T PL2524916T3 (pl) | 2010-01-15 | 2011-01-14 | Sposób wytwarzania soli kwasu tetrazolometanosulfonowego oraz nowy związek stosowny w tym sposobie |
SG2012050472A SG182430A1 (en) | 2010-01-15 | 2011-01-14 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
CN201180005610.5A CN102812020B (zh) | 2010-01-15 | 2011-01-14 | 用于制备四唑甲磺酸盐的方法及其使用的新化合物 |
DK11733103.3T DK2524916T3 (da) | 2010-01-15 | 2011-01-14 | Fremgangsmåde til fremstilling af tetrazolmethansulfonsyresalte og en ny forbindelse, der anvendes i samme |
NZ601805A NZ601805A (en) | 2010-01-15 | 2011-01-14 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
JP2012548895A JP5575921B2 (ja) | 2010-01-15 | 2011-01-14 | テトラゾールメタンスルホン酸塩の製造方法及びそれに用いられる新規化合物 |
EP11733103.3A EP2524916B1 (en) | 2010-01-15 | 2011-01-14 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
US13/522,272 US8680277B2 (en) | 2010-01-15 | 2011-01-14 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
BR112012017448-7A BR112012017448B1 (pt) | 2010-01-15 | 2011-01-14 | método para a preparação de sais de ácido metanossulfônico de tetrazol, e novo composto empregado no mesmo |
ES11733103.3T ES2514340T3 (es) | 2010-01-15 | 2011-01-14 | Procedimiento para preparar sales de ácido tetrazol metanosulfónico y compuestos novedosos usados en el mismo |
AU2011205891A AU2011205891B2 (en) | 2010-01-15 | 2011-01-14 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
IL220851A IL220851A (en) | 2010-01-15 | 2012-07-10 | Process for the preparation of n - (2 - (2 - (4 - (2 - (7,6-dimethoxy-4,3-dihydro-iso-quinoline-2 - (1 h))) ethyl) phenyl) - h2 - tetrazole - 5-ram (5,4-dimethoxyphenyl) -4-oxo-h4-chromium-2-carboxamide methane-sulfonate, its intermediate and intermediate preparation process |
NO20120841A NO342589B1 (no) | 2010-01-15 | 2012-07-20 | Fremgangsmåte for fremstilling av tetrazol-metansulfonsyresalter og ny forbindelse som anvendes i denne |
ZA2012/06084A ZA201206084B (en) | 2010-01-15 | 2012-08-14 | Method for preparing tetrazole methanesulfonic acid salts,and novel compound used in same |
HK13104698.2A HK1177211A1 (en) | 2010-01-15 | 2013-04-18 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
US14/171,318 US8940908B2 (en) | 2010-01-15 | 2014-02-03 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020100003835A KR101466245B1 (ko) | 2010-01-15 | 2010-01-15 | 테트라졸 메탄설폰산 염의 제조방법 및 이에 사용되는 신규 화합물 |
KR10-2010-0003835 | 2010-01-15 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/522,272 A-371-Of-International US8680277B2 (en) | 2010-01-15 | 2011-01-14 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
US14/171,318 Division US8940908B2 (en) | 2010-01-15 | 2014-02-03 | Method for preparing tetrazole methanesulfonic acid salts, and novel compound used in same |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2011087316A2 true WO2011087316A2 (ko) | 2011-07-21 |
WO2011087316A3 WO2011087316A3 (ko) | 2011-11-10 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2011/000291 WO2011087316A2 (ko) | 2010-01-15 | 2011-01-14 | 테트라졸 메탄설폰산 염의 제조방법 및 이에 사용되는 신규 화합물 |
Country Status (20)
Country | Link |
---|---|
US (2) | US8680277B2 (ko) |
EP (1) | EP2524916B1 (ko) |
JP (1) | JP5575921B2 (ko) |
KR (1) | KR101466245B1 (ko) |
CN (1) | CN102812020B (ko) |
AU (1) | AU2011205891B2 (ko) |
BR (1) | BR112012017448B1 (ko) |
CA (1) | CA2786434C (ko) |
DK (1) | DK2524916T3 (ko) |
ES (1) | ES2514340T3 (ko) |
HK (1) | HK1177211A1 (ko) |
IL (1) | IL220851A (ko) |
MX (1) | MX2012007868A (ko) |
NO (1) | NO342589B1 (ko) |
NZ (1) | NZ601805A (ko) |
PL (1) | PL2524916T3 (ko) |
RU (1) | RU2509769C1 (ko) |
SG (1) | SG182430A1 (ko) |
WO (1) | WO2011087316A2 (ko) |
ZA (1) | ZA201206084B (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020168144A1 (en) | 2019-02-14 | 2020-08-20 | Teva Pharmaceuticals International Gmbh | Solid state forms of n-[2-(2-{4-[2-(6,7-dimethoxy-3,4-dihydro-2(lh)- isoquinolinyl)ethyl] phenyl }-2h-tetrazol-5-yl)-4,5-dimethoxyphenyl] -4- oxo-4h-chromene-2-carboxamide and of its mesylate salt |
WO2022011221A1 (en) | 2020-07-10 | 2022-01-13 | Teva Czech Industries S.R.O | Solid state forms of n-[2-(2-{4-[2-(6,7-dimethoxy-3,4-dihydro-2(1h)-isoquinolinyl)ethyl]phenyl}-2h-tetrazol-5-yl)-4,5-dimethoxyphenyl]-4-oxo-4h-chromene-2-carboxamide mesylate salt |
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KR101986683B1 (ko) * | 2012-12-13 | 2019-06-10 | 한미약품 주식회사 | 테트라졸 유도체를 활성 성분으로 포함하는 용해도가 개선된 고체 분산체 |
CN103804352B (zh) * | 2014-01-23 | 2017-06-13 | 中国药科大学 | 三氮唑苯乙基四氢异喹啉类化合物及其制备方法和应用 |
JO3737B1 (ar) * | 2015-07-21 | 2021-01-31 | Athenex Therapeutics Ltd | تركيبات علاجية من باكليتاكسيل تعطى عن طريق الفم ومثبط P-gp لعلاج السرطان |
US11165722B2 (en) | 2016-06-29 | 2021-11-02 | International Business Machines Corporation | Cognitive messaging with dynamically changing inputs |
WO2020194175A1 (en) * | 2019-03-25 | 2020-10-01 | Dr. Reddy's Laboratories Limited | Solid forms of encequidar mesylate and processes thereof |
WO2020230037A1 (en) * | 2019-05-13 | 2020-11-19 | Dr. Reddy's Laboratories Limited | Alternate process for the preparation of encequidar |
WO2021044350A1 (en) * | 2019-09-04 | 2021-03-11 | Dr. Reddy’S Laboratories Limited | Solid forms of encequidar mesylate and processes thereof |
IL301516A (en) | 2020-10-07 | 2023-05-01 | Athenex Inc | Acetamido-phenyltetrazol derivatives and methods of using them |
Citations (1)
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WO2005033097A1 (en) | 2003-10-07 | 2005-04-14 | Hanmi Pharm. Co., Ltd. | P-glycoprotein inhibitor, method for preparing the same and pharmaceutical composition comprising the same |
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IL129871A (en) * | 1994-05-06 | 2003-11-23 | Pharmacia & Upjohn Inc | Process for preparing 4-phenyl-substituted octanoyl-oxazolidin-2-one intermediates that are useful for preparing pyran-2-ones useful for treating retroviral infections |
KR100508019B1 (ko) * | 2003-07-19 | 2005-08-17 | 한미약품 주식회사 | 고순도 1-안드로스텐 유도체의 제조 방법 |
US7279471B2 (en) * | 2004-04-15 | 2007-10-09 | Boehringer Ingelheim International Gmbh | Selected CGRP-antagonists, process for preparing them and their use as pharmaceutical compositions |
KR100686695B1 (ko) * | 2005-06-11 | 2007-02-26 | 주식회사 에스텍파마 | 프란루카스트 또는 그의 수화물의 제조방법 및 그의 합성중간체 |
US20070161791A1 (en) * | 2006-01-09 | 2007-07-12 | Narsimha Reddy Penthala | Process for the preparation of terazosin hydrocloride dihydrate |
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2010
- 2010-01-15 KR KR1020100003835A patent/KR101466245B1/ko active IP Right Grant
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2011
- 2011-01-14 BR BR112012017448-7A patent/BR112012017448B1/pt active IP Right Grant
- 2011-01-14 PL PL11733103T patent/PL2524916T3/pl unknown
- 2011-01-14 NZ NZ601805A patent/NZ601805A/en unknown
- 2011-01-14 CN CN201180005610.5A patent/CN102812020B/zh active Active
- 2011-01-14 EP EP11733103.3A patent/EP2524916B1/en active Active
- 2011-01-14 JP JP2012548895A patent/JP5575921B2/ja active Active
- 2011-01-14 ES ES11733103.3T patent/ES2514340T3/es active Active
- 2011-01-14 WO PCT/KR2011/000291 patent/WO2011087316A2/ko active Application Filing
- 2011-01-14 MX MX2012007868A patent/MX2012007868A/es active IP Right Grant
- 2011-01-14 CA CA2786434A patent/CA2786434C/en active Active
- 2011-01-14 US US13/522,272 patent/US8680277B2/en active Active
- 2011-01-14 AU AU2011205891A patent/AU2011205891B2/en active Active
- 2011-01-14 RU RU2012134783/04A patent/RU2509769C1/ru active
- 2011-01-14 SG SG2012050472A patent/SG182430A1/en unknown
- 2011-01-14 DK DK11733103.3T patent/DK2524916T3/da active
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2012
- 2012-07-10 IL IL220851A patent/IL220851A/en active IP Right Grant
- 2012-07-20 NO NO20120841A patent/NO342589B1/no unknown
- 2012-08-14 ZA ZA2012/06084A patent/ZA201206084B/en unknown
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2013
- 2013-04-18 HK HK13104698.2A patent/HK1177211A1/xx unknown
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2014
- 2014-02-03 US US14/171,318 patent/US8940908B2/en active Active
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WO2005033097A1 (en) | 2003-10-07 | 2005-04-14 | Hanmi Pharm. Co., Ltd. | P-glycoprotein inhibitor, method for preparing the same and pharmaceutical composition comprising the same |
Non-Patent Citations (3)
Title |
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See also references of EP2524916A4 |
SUKETAKA ITO ET AL., BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 49, no. 7, 1976, pages 1920 - 1923 |
SUKETAKA ITO ET AL.: "Bulletin of the Chemical Society of Japan", vol. 49, 1976, pages: 1920 - 1923 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2020168144A1 (en) | 2019-02-14 | 2020-08-20 | Teva Pharmaceuticals International Gmbh | Solid state forms of n-[2-(2-{4-[2-(6,7-dimethoxy-3,4-dihydro-2(lh)- isoquinolinyl)ethyl] phenyl }-2h-tetrazol-5-yl)-4,5-dimethoxyphenyl] -4- oxo-4h-chromene-2-carboxamide and of its mesylate salt |
WO2022011221A1 (en) | 2020-07-10 | 2022-01-13 | Teva Czech Industries S.R.O | Solid state forms of n-[2-(2-{4-[2-(6,7-dimethoxy-3,4-dihydro-2(1h)-isoquinolinyl)ethyl]phenyl}-2h-tetrazol-5-yl)-4,5-dimethoxyphenyl]-4-oxo-4h-chromene-2-carboxamide mesylate salt |
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