ES2587304T3 - Derivados de diaminopirimidina y procedimientos para la preparación de los mismos - Google Patents
Derivados de diaminopirimidina y procedimientos para la preparación de los mismos Download PDFInfo
- Publication number
- ES2587304T3 ES2587304T3 ES12750114.6T ES12750114T ES2587304T3 ES 2587304 T3 ES2587304 T3 ES 2587304T3 ES 12750114 T ES12750114 T ES 12750114T ES 2587304 T3 ES2587304 T3 ES 2587304T3
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- Spain
- Prior art keywords
- group
- optionally substituted
- halogen
- alkoxy
- alkyl
- 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.)
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- 238000000034 method Methods 0.000 title 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 title 1
- -1 hydroxy, amino Chemical group 0.000 abstract 8
- 229910052736 halogen Inorganic materials 0.000 abstract 7
- 150000002367 halogens Chemical group 0.000 abstract 7
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003282 alkyl amino group Chemical group 0.000 abstract 5
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000006560 (C1-C5)alkylcarbonylamino group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000004064 dysfunction Effects 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 230000005176 gastrointestinal motility Effects 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000001425 triazolyl group Chemical group 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/12—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 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/14—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 three or more hetero 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
- C07D405/14—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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20110016981 | 2011-02-25 | ||
| KR20110016981 | 2011-02-25 | ||
| PCT/KR2012/001427 WO2012115480A2 (en) | 2011-02-25 | 2012-02-24 | Diaminopyrimidine derivatives and processes for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2587304T3 true ES2587304T3 (es) | 2016-10-21 |
Family
ID=46721361
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12750114.6T Active ES2587304T3 (es) | 2011-02-25 | 2012-02-24 | Derivados de diaminopirimidina y procedimientos para la preparación de los mismos |
| ES12749916.8T Active ES2579830T3 (es) | 2011-02-25 | 2012-02-24 | Derivados de diaminopirimidina y procedimientos para la preparación de los mismos |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12749916.8T Active ES2579830T3 (es) | 2011-02-25 | 2012-02-24 | Derivados de diaminopirimidina y procedimientos para la preparación de los mismos |
Country Status (17)
| Country | Link |
|---|---|
| US (4) | US9890138B2 (enExample) |
| EP (2) | EP2678331B1 (enExample) |
| JP (2) | JP5890436B2 (enExample) |
| KR (2) | KR101671348B1 (enExample) |
| CN (2) | CN103402997B (enExample) |
| AU (2) | AU2012221925B2 (enExample) |
| BR (2) | BR112013020641B1 (enExample) |
| CA (2) | CA2827030C (enExample) |
| DK (1) | DK2678332T3 (enExample) |
| ES (2) | ES2587304T3 (enExample) |
| HU (1) | HUE029988T2 (enExample) |
| IN (1) | IN2013MN01519A (enExample) |
| MX (2) | MX336155B (enExample) |
| PL (2) | PL2678331T3 (enExample) |
| PT (1) | PT2678332T (enExample) |
| RU (1) | RU2587493C2 (enExample) |
| WO (2) | WO2012115478A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9890138B2 (en) * | 2011-02-25 | 2018-02-13 | Yuhan Corporation | Diaminopyrimidine derivatives and processes for the preparation thereof |
| KR20220143164A (ko) | 2012-11-21 | 2022-10-24 | 피티씨 테라퓨틱스, 인크. | 치환된 리버스 피리미딘 ｂｍｉ-1 저해제 |
| KR101657616B1 (ko) * | 2013-05-24 | 2016-09-19 | 주식회사유한양행 | 피리미딘 고리를 포함하는 바이사이클릭 유도체 및 그의 제조방법 |
| CA2922657C (en) * | 2013-08-30 | 2022-04-12 | Ptc Therapeutics, Inc. | Substituted pyrimidine bmi-1 inhibitors |
| US10584115B2 (en) | 2013-11-21 | 2020-03-10 | Ptc Therapeutics, Inc. | Substituted pyridine and pyrazine BMI-1 inhibitors |
| CN104003944B (zh) * | 2014-05-29 | 2016-08-24 | 西北师范大学 | 一种嘧菌胺的制备方法 |
| TWI730331B (zh) | 2014-10-13 | 2021-06-11 | 南韓商柳韓洋行股份有限公司 | 用於調節ｅｇｆｒ突變型激酶活性的化合物及組成物 |
| US10300155B2 (en) | 2015-12-31 | 2019-05-28 | Washington University | Alpha-synuclein ligands |
| CN105646321A (zh) * | 2016-01-07 | 2016-06-08 | 中国药科大学 | (s)-3-羟基吡咯烷盐酸盐的制备方法 |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| KR102441327B1 (ko) * | 2018-05-18 | 2022-09-07 | 주식회사유한양행 | 다이아미노피리미딘 유도체 또는 이의 산부가염의 신규의 제조방법 |
| BR112021002630A2 (pt) | 2018-08-17 | 2021-05-11 | Ptc Therapeutics, Inc. | método para tratar câncer pancreático |
| BR112021011330A2 (pt) | 2018-12-18 | 2021-08-31 | Astrazeneca Ab | Processo farmacêutico e intermediários |
| CN110317176A (zh) * | 2019-07-04 | 2019-10-11 | 沈阳药科大学 | 2-氨基嘧啶类化合物及其用途 |
| KR20220006776A (ko) * | 2020-07-09 | 2022-01-18 | 주식회사유한양행 | 다이아미노피리미딘 유도체 또는 이의 약학적으로 허용가능한 염을 포함하는 약학 조성물 및 이의 제조방법 |
| WO2025104079A1 (en) * | 2023-11-17 | 2025-05-22 | Helmholtz-Zentrum für Infektionsforschung GmbH | Salicylic acid and picolinic acid derivatives as inhibitors of energy coupling factor (ecf) transporters for the treatment of bacterial infections |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4962115A (en) | 1981-10-01 | 1990-10-09 | Janssen Pharmaceutica N.V. | Novel N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
| US4870074A (en) | 1986-04-30 | 1989-09-26 | Dainippon Pharmaceutical Co., Ltd. | Substituted benzamide derivatives, for enhancing gastrointestinal motility |
| GB9005014D0 (en) | 1990-03-06 | 1990-05-02 | Janssen Pharmaceutica Nv | N.(4.piperidinyl)(dihydrobenzofuran or dihydro.2h.benzopyran)carboxamide derivatives |
| HUT64023A (en) | 1991-03-22 | 1993-11-29 | Sandoz Ag | Process for producing aminoguanidine derivatives and pharmaceutical compositions comprising such compounds |
| HUT74464A (en) | 1993-10-12 | 1996-12-30 | Du Pont Merck Pharma | 1n-alkyl-n-arylpyrimidinamines and derivatives thereof, and pharmaceutical compositions containing them |
| CN1142817A (zh) * | 1993-10-12 | 1997-02-12 | 杜邦麦克制药有限公司 | 1n-烷基-n-芳基嘧啶胺及其衍生物 |
| IL112024A (en) * | 1993-12-21 | 1999-07-14 | Novo Nordisk As | Pharmaceutical compositions comprising tetrahydropyridine derivatives substituted with oxadiazole or thiadiazole for treating gastrointestinal motility disorders |
| JP2896532B2 (ja) * | 1994-08-13 | 1999-05-31 | ユーハン コーポレーション | 新規なピリミジン誘導体およびその製造方法 |
| US5739151A (en) * | 1996-07-19 | 1998-04-14 | Sepracor Inc. | Method for treating emesis and central nervous system disorders using optically pure (+) norcisapride |
| IN188411B (enExample) | 1997-03-27 | 2002-09-21 | Yuhan Corp | |
| US6825198B2 (en) * | 2001-06-21 | 2004-11-30 | Pfizer Inc | 5-HT receptor ligands and uses thereof |
| EP1648524B1 (en) * | 2003-07-25 | 2009-01-14 | Ciba Holding Inc. | Use of substituted 2,4-bis (alkylamino) pyrimidines or -quinazolines as antimicrobials |
| JP2007507425A (ja) * | 2003-08-29 | 2007-03-29 | ダイノゲン ファーマシューティカルズ，インコーポレイテッド | 胃腸管運動障害を処置するために有用な組成物 |
| US20060057972A1 (en) | 2004-09-14 | 2006-03-16 | Wikel Harold L | Adapter for a modular wireless communication device |
| US20060128726A1 (en) * | 2004-11-24 | 2006-06-15 | Xuebao Wang | Process for preparing novel crystalline forms of (2S)-1-[[(7R)-7-(3,4-dichlorophenyl)-4,7-dihydro-5-methylpyrazolo[1,5]pyrimidine-6-yl]carbonyl]-2-(4-fluorophenyl)pyrrolidine, novel stable forms produced therein and formulations |
| JP4970290B2 (ja) * | 2005-02-25 | 2012-07-04 | ファイザー株式会社 | ベンズイソキサゾール誘導体 |
| US20070032514A1 (en) * | 2005-07-01 | 2007-02-08 | Zahn Stephan K | 2,4-diamino-pyrimidines as aurora inhibitors |
| US20080293942A1 (en) * | 2005-11-28 | 2008-11-27 | Cousins Russell D | Methods of Preparing 2-Imidazol-1-Yl-4-Methyl-6-Pyrrolidin-2-Yl-Pyrimidine and 4-(1-Alkylpyrrolidin-2-Yl)-2-(1H-Imidazol-1-Yl)-6-Methylpyrimidine Derivatives |
| US8044068B2 (en) * | 2006-04-04 | 2011-10-25 | Taisho Pharmaceutical Co., Ltd | Aminopyrrolidine compound |
| EP2007754A1 (en) * | 2006-04-10 | 2008-12-31 | Boehringer Ingelheim International GmbH | 2, 4-diaminopyrimidine derivatives and their use for the treatment of cancer |
| RU2010137300A (ru) * | 2008-02-22 | 2012-03-27 | Ф. Хоффманн-Ля Рош Аг (Ch) | Модуляторы бета-амилоида |
| JP5918693B2 (ja) * | 2009-05-05 | 2016-05-18 | ダナ ファーバー キャンサー インスティテュート インコーポレイテッド | Ｅｇｆｒ阻害剤及び疾患の治療方法 |
| US9890138B2 (en) * | 2011-02-25 | 2018-02-13 | Yuhan Corporation | Diaminopyrimidine derivatives and processes for the preparation thereof |
-
2012
- 2012-02-24 US US14/001,489 patent/US9890138B2/en active Active
- 2012-02-24 CN CN201280010406.7A patent/CN103402997B/zh active Active
- 2012-02-24 PL PL12749916.8T patent/PL2678331T3/pl unknown
- 2012-02-24 CN CN201280010354.3A patent/CN103391935B/zh active Active
- 2012-02-24 EP EP12749916.8A patent/EP2678331B1/en active Active
- 2012-02-24 ES ES12750114.6T patent/ES2587304T3/es active Active
- 2012-02-24 CA CA2827030A patent/CA2827030C/en active Active
- 2012-02-24 RU RU2013142187/04A patent/RU2587493C2/ru active
- 2012-02-24 US US14/001,475 patent/US9850227B2/en active Active
- 2012-02-24 KR KR1020120018933A patent/KR101671348B1/ko active Active
- 2012-02-24 JP JP2013555369A patent/JP5890436B2/ja active Active
- 2012-02-24 JP JP2013555368A patent/JP5980236B2/ja active Active
- 2012-02-24 PL PL12750114.6T patent/PL2678332T3/pl unknown
- 2012-02-24 IN IN1519MUN2013 patent/IN2013MN01519A/en unknown
- 2012-02-24 BR BR112013020641-1A patent/BR112013020641B1/pt active IP Right Grant
- 2012-02-24 CA CA2827072A patent/CA2827072C/en active Active
- 2012-02-24 MX MX2013009627A patent/MX336155B/es unknown
- 2012-02-24 WO PCT/KR2012/001423 patent/WO2012115478A2/en not_active Ceased
- 2012-02-24 EP EP12750114.6A patent/EP2678332B1/en active Active
- 2012-02-24 ES ES12749916.8T patent/ES2579830T3/es active Active
- 2012-02-24 WO PCT/KR2012/001427 patent/WO2012115480A2/en not_active Ceased
- 2012-02-24 DK DK12750114.6T patent/DK2678332T3/en active
- 2012-02-24 HU HUE12750114A patent/HUE029988T2/en unknown
- 2012-02-24 AU AU2012221925A patent/AU2012221925B2/en active Active
- 2012-02-24 AU AU2012221927A patent/AU2012221927B2/en active Active
- 2012-02-24 BR BR112013019942-3A patent/BR112013019942B1/pt active IP Right Grant
- 2012-02-24 MX MX2013009549A patent/MX337477B/es active IP Right Grant
- 2012-02-24 PT PT127501146T patent/PT2678332T/pt unknown
- 2012-02-24 KR KR1020120018926A patent/KR101671341B1/ko active Active
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2017
- 2017-11-15 US US15/813,741 patent/US10640490B2/en active Active
- 2017-12-20 US US15/848,760 patent/US10227330B2/en active Active
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