RU2018137882A - Способ получения 1-(4-(4-(3,4-дихлор-2-фторфениламино)-7-метоксихиназолин-6-илокси)пиперидин-1-ил)проп-2-ен-1-она - Google Patents
Способ получения 1-(4-(4-(3,4-дихлор-2-фторфениламино)-7-метоксихиназолин-6-илокси)пиперидин-1-ил)проп-2-ен-1-она Download PDFInfo
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- RU2018137882A RU2018137882A RU2018137882A RU2018137882A RU2018137882A RU 2018137882 A RU2018137882 A RU 2018137882A RU 2018137882 A RU2018137882 A RU 2018137882A RU 2018137882 A RU2018137882 A RU 2018137882A RU 2018137882 A RU2018137882 A RU 2018137882A
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- RU
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- Prior art keywords
- formula
- compound
- temperature
- salt
- base
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- LPFWVDIFUFFKJU-UHFFFAOYSA-N 1-[4-[4-(3,4-dichloro-2-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]prop-2-en-1-one Chemical compound C=12C=C(OC3CCN(CC3)C(=O)C=C)C(OC)=CC2=NC=NC=1NC1=CC=C(Cl)C(Cl)=C1F LPFWVDIFUFFKJU-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 20
- 238000000034 method Methods 0.000 claims 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 239000002585 base Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 claims 2
- 125000004969 haloethyl group Chemical group 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000005905 mesyloxy group Chemical group 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 2
- 239000003586 protic polar solvent Substances 0.000 claims 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020130009282A KR20140096571A (ko) | 2013-01-28 | 2013-01-28 | 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온의 제조방법 |
| KR10-2013-0009282 | 2013-01-28 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015129994A Division RU2671843C2 (ru) | 2013-01-28 | 2014-01-27 | Способ получения 1-(4-(4-(3,4-дихлор-2-фторфениламино)-7-метоксихиназолин-6-илокси)пиперидин-1-ил)проп-2-ен-1-она |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2018137882A true RU2018137882A (ru) | 2019-03-21 |
Family
ID=51227806
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018137882A RU2018137882A (ru) | 2013-01-28 | 2014-01-27 | Способ получения 1-(4-(4-(3,4-дихлор-2-фторфениламино)-7-метоксихиназолин-6-илокси)пиперидин-1-ил)проп-2-ен-1-она |
| RU2015129994A RU2671843C2 (ru) | 2013-01-28 | 2014-01-27 | Способ получения 1-(4-(4-(3,4-дихлор-2-фторфениламино)-7-метоксихиназолин-6-илокси)пиперидин-1-ил)проп-2-ен-1-она |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015129994A RU2671843C2 (ru) | 2013-01-28 | 2014-01-27 | Способ получения 1-(4-(4-(3,4-дихлор-2-фторфениламино)-7-метоксихиназолин-6-илокси)пиперидин-1-ил)проп-2-ен-1-она |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9518043B2 (enExample) |
| EP (1) | EP2948441B1 (enExample) |
| JP (4) | JP6461011B2 (enExample) |
| KR (1) | KR20140096571A (enExample) |
| CN (1) | CN104981467B (enExample) |
| AU (1) | AU2014210494B2 (enExample) |
| BR (1) | BR112015017597B1 (enExample) |
| CA (2) | CA2898433C (enExample) |
| DK (1) | DK2948441T3 (enExample) |
| ES (1) | ES2662863T3 (enExample) |
| IL (2) | IL240197B (enExample) |
| MX (2) | MX362763B (enExample) |
| NO (1) | NO2948441T3 (enExample) |
| PH (2) | PH12015501636B1 (enExample) |
| RU (2) | RU2018137882A (enExample) |
| WO (1) | WO2014116070A1 (enExample) |
| ZA (1) | ZA201506241B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140096571A (ko) * | 2013-01-28 | 2014-08-06 | 한미약품 주식회사 | 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온의 제조방법 |
| EP3334735B1 (en) * | 2015-08-11 | 2025-08-13 | Principia Biopharma Inc. | Processes for preparing an fgfr inhibitor |
| EP3903828A4 (en) | 2018-12-21 | 2022-10-05 | Daiichi Sankyo Company, Limited | ANTIBODY-DRUG CONJUGATE AND KINAS INHIBITOR COMBINATION |
| US20210221792A1 (en) * | 2020-01-16 | 2021-07-22 | Hanmi Pharm Co., Ltd. | Convergent synthesis of poziotinib derivative |
| WO2022043923A1 (en) * | 2020-08-28 | 2022-03-03 | Hanmi Science Co., Ltd. | Synthesis of poziotinib derivative |
| CN117567466B (zh) * | 2024-01-16 | 2024-04-16 | 成都金瑞基业生物科技有限公司 | 一种喹唑啉衍生物的制备方法 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02275891A (ja) | 1988-12-29 | 1990-11-09 | Tsumura & Co | 新規な複核白金錯体および該錯体を有効成分とする抗腫瘍剤 |
| JP3874793B2 (ja) | 1994-08-23 | 2007-01-31 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | イブプロフェンおよびコデイン含有の改良された医薬処方 |
| KR980008219A (ko) | 1996-07-16 | 1998-04-30 | 김상응 | 안정화된 주사제용 약제학적 조성물 |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| JP3687025B2 (ja) | 1998-06-04 | 2005-08-24 | 東和薬品株式会社 | 安定なマレイン酸エナラプリル錠剤 |
| PL354323A1 (en) | 1999-09-21 | 2004-01-12 | Astrazeneca Ab | Quinazoline derivatives and their use as pharmaceuticals |
| DE10042058A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE10042061A1 (de) | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen,diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| TW200813014A (en) * | 2002-03-28 | 2008-03-16 | Astrazeneca Ab | Quinazoline derivatives |
| MXPA04009536A (es) | 2002-03-30 | 2005-01-25 | Boehringer Ingelheim Pharma | Compuestos heterociclos biciclicos, composiciones farmaceuticas que contienen estos compuestos, su utilizacion y procesos para su preparacion. |
| DE602004004553T2 (de) * | 2003-09-19 | 2007-10-25 | Astrazeneca Ab | Chinazolinderivate |
| US20070037837A1 (en) | 2003-09-19 | 2007-02-15 | Hennequin Laurent Francois A | Quinazoline derivatives |
| BRPI0414735A (pt) | 2003-09-25 | 2006-11-21 | Astrazeneca Ab | derivado de quinazolina, composto, composição farmacêutica, uso de derivado de quinazolina, método para produzir um efeito anti-proliferativo em um animal de sangue quente, e, processo para a preparação de um derivado de quinazolina |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| DE10345875A1 (de) * | 2003-09-30 | 2005-04-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Vewendung und Verfahren zu ihrer Herstellung |
| WO2005090332A1 (ja) | 2004-03-23 | 2005-09-29 | Banyu Pharmaceutical Co., Ltd | 置換キナゾリン又はピリドピリミジン誘導体 |
| KR20050104152A (ko) | 2004-04-28 | 2005-11-02 | 최승호 | 경구용 약물의 흡수를 증진하는 약제학적 조성물 |
| JP5054544B2 (ja) * | 2005-02-26 | 2012-10-24 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害剤としてのキナゾリン誘導体 |
| CA2619037A1 (en) | 2005-08-22 | 2007-03-01 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles medicaments comprising said compounds use and method for production thereof |
| AU2006326157A1 (en) | 2005-12-12 | 2007-06-21 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, medicaments containing said compounds, use thereof, and method for the production thereof |
| WO2007118854A1 (en) * | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and the use thereof |
| EP1847258B2 (de) | 2006-04-13 | 2013-01-16 | Acino Pharma AG | Partialglyceride als Schmiermittel für pharmazeutische Zusammensetzungen enthaltend Thieno[3,2-c]pyridin-Derivate |
| US7998949B2 (en) * | 2007-02-06 | 2011-08-16 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, drugs containing said compounds, use thereof, and method for production thereof |
| TWI377944B (en) | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| JP2010530890A (ja) | 2007-06-22 | 2010-09-16 | ブリストル−マイヤーズ スクイブ カンパニー | アタザナビルを含む錠剤組成物 |
| WO2010059239A2 (en) * | 2008-11-21 | 2010-05-27 | Millennium Pharmaceuticals, Inc | Lactate salt of 4-(6-methoxy-7-(3-piperidin-1-yl-propoxy)quinazolin-4-yl]piperazine-1-carboxylic acid(4-isopropoxyphenyl)-amide and pharmaceutical compositions thereof for the treatment of cancer and other diseases or disorders |
| MY144136A (en) | 2009-04-20 | 2011-08-10 | Univ Sains Malaysia | Throttle and brake lock |
| CN102822676B (zh) | 2010-01-12 | 2015-02-18 | 雀巢产品技术援助有限公司 | 用于预测三阴性乳腺癌对疗法的应答的方法 |
| KR101217526B1 (ko) * | 2010-06-11 | 2013-01-02 | 한미사이언스 주식회사 | 아마이드 유도체 또는 이의 약학적으로 허용 가능한 염을 포함하는 약제학적 조성물 |
| KR101317809B1 (ko) * | 2011-06-07 | 2013-10-16 | 한미약품 주식회사 | 암세포의 성장을 억제하는 아마이드 유도체 및 비금속염 활택제를 포함하는 약학 조성물 |
| KR101272613B1 (ko) * | 2011-10-05 | 2013-06-10 | 한미사이언스 주식회사 | 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온 염산염의 제조 방법 및 이에 사용되는 중간체 |
| KR20140096571A (ko) * | 2013-01-28 | 2014-08-06 | 한미약품 주식회사 | 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온의 제조방법 |
-
2013
- 2013-01-28 KR KR1020130009282A patent/KR20140096571A/ko not_active Withdrawn
-
2014
- 2014-01-27 MX MX2015009232A patent/MX362763B/es active IP Right Grant
- 2014-01-27 DK DK14743689.3T patent/DK2948441T3/en active
- 2014-01-27 RU RU2018137882A patent/RU2018137882A/ru unknown
- 2014-01-27 AU AU2014210494A patent/AU2014210494B2/en active Active
- 2014-01-27 MX MX2019000647A patent/MX388687B/es unknown
- 2014-01-27 EP EP14743689.3A patent/EP2948441B1/en active Active
- 2014-01-27 JP JP2015555109A patent/JP6461011B2/ja active Active
- 2014-01-27 CA CA2898433A patent/CA2898433C/en active Active
- 2014-01-27 RU RU2015129994A patent/RU2671843C2/ru active
- 2014-01-27 CA CA3129936A patent/CA3129936A1/en not_active Abandoned
- 2014-01-27 BR BR112015017597-0A patent/BR112015017597B1/pt not_active IP Right Cessation
- 2014-01-27 NO NO14743689A patent/NO2948441T3/no unknown
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