HUE025179T2 - Heterocyclic Compounds - Google Patents
Heterocyclic Compounds Download PDFInfo
- Publication number
- HUE025179T2 HUE025179T2 HUE08874003A HUE08874003A HUE025179T2 HU E025179 T2 HUE025179 T2 HU E025179T2 HU E08874003 A HUE08874003 A HU E08874003A HU E08874003 A HUE08874003 A HU E08874003A HU E025179 T2 HUE025179 T2 HU E025179T2
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- compound
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 179
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000002947 alkylene group Chemical group 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- -1 Mteiotot Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
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- 230000006378 damage Effects 0.000 claims description 8
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- 239000012530 fluid Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
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- 210000003423 ankle Anatomy 0.000 claims 1
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- 125000006413 ring segment Chemical group 0.000 claims 1
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 5
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4649608P | 2008-04-21 | 2008-04-21 |
Publications (1)
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| HUE025179T2 true HUE025179T2 (en) | 2016-02-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE08874003A HUE025179T2 (en) | 2008-04-21 | 2008-11-03 | Heterocyclic Compounds |
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| WO (1) | WO2009131598A1 (enExample) |
| ZA (1) | ZA201008262B (enExample) |
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| WO2010056847A2 (en) * | 2008-11-13 | 2010-05-20 | Taigen Biotechnology Co., Ltd. | Lyophilization formulation |
| CN103204816B (zh) * | 2012-01-16 | 2016-04-27 | 中国人民解放军军事医学科学院毒物药物研究所 | 哌嗪基嘧啶类衍生物及其制备方法和用途 |
| EP2836214B1 (en) * | 2012-04-11 | 2018-06-27 | Acerta Pharma B.V. | Bruton's tyrosine kinase inhibitors for hematopoietic mobilization |
| WO2016048861A2 (en) | 2014-09-22 | 2016-03-31 | National Health Research Institutes | Heterocyclic compounds and use thereof |
| US9375406B2 (en) * | 2014-09-30 | 2016-06-28 | Taigen Biotechnology Co., Ltd. | Substituted pyrimidines for mobilizing cells expressing a type 4 CXC chemokine receptor |
| TWI620748B (zh) | 2016-02-05 | 2018-04-11 | National Health Research Institutes | 氨基噻唑化合物及其用途 |
| WO2018132326A1 (en) * | 2017-01-10 | 2018-07-19 | National Health Research Institutes | Heterocyclic compounds and use thereof |
| CN109553604B (zh) * | 2017-09-25 | 2021-08-27 | 盛世泰科生物医药技术(苏州)有限公司 | 4-氨基嘧啶衍生物作cxcr4抑制剂及其应用 |
| CN108794414B (zh) * | 2018-06-22 | 2021-01-01 | 浙江大学 | 芳酰胺基取代的均三嗪类化合物及制备和应用 |
| CN116120195B (zh) * | 2022-12-29 | 2025-02-25 | 长兴宜生药物科技有限公司 | 一种催化制备培哚普利中间体的方法 |
| PL247377B1 (pl) * | 2023-06-29 | 2025-06-23 | Politechnika Krakowska Im Tadeusza Kosciuszki | Nowa pochodna 1,3,5-triazyny i jej zastosowanie |
Family Cites Families (36)
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| US3007A (en) * | 1843-03-21 | Improvement in salt-boilers | ||
| US6029A (en) * | 1849-01-16 | Method of directing the scoops in dredging machines | ||
| US5034560A (en) | 1990-10-19 | 1991-07-23 | The Standard Oil Company | Synthesis of ethylamines |
| WO1993001498A1 (en) | 1991-07-04 | 1993-01-21 | Immunodex K/S | Water-soluble, polymer-based reagents and conjugates comprising moieties derived from divinyl sulfone |
| US5446090A (en) | 1993-11-12 | 1995-08-29 | Shearwater Polymers, Inc. | Isolatable, water soluble, and hydrolytically stable active sulfones of poly(ethylene glycol) and related polymers for modification of surfaces and molecules |
| ZA951617B (en) | 1994-03-04 | 1997-02-27 | Lilly Co Eli | Antithrombotic agents. |
| AU7692996A (en) | 1995-12-01 | 1997-06-27 | Ciba-Geigy Ag | Receptor antagonists |
| TW440563B (en) | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| EP1007073A4 (en) | 1996-06-04 | 2002-03-27 | Synaptic Pharma Corp | METHODS OF MODIFYING FOOD BEHAVIOR, COMPOUNDS USEFUL IN SAID METHODS, AND DNA ENCODING A HYPOTHALAMIC NEUROPEPTIDE Y / PEPTIDE YY Y5 RECEPTOR |
| NO311614B1 (no) * | 1996-10-01 | 2001-12-17 | Janssen Pharmaceutica Nv | Substituerte diamino-1,3,5-triazinderivater |
| WO1998024782A2 (en) | 1996-12-05 | 1998-06-11 | Amgen Inc. | Substituted pyrimidine compounds and their use |
| WO1999050249A2 (en) | 1998-04-01 | 1999-10-07 | Du Pont Pharmaceuticals Company | Pyrimidines and triazines as integrin antagonists |
| US6420354B1 (en) | 1998-06-08 | 2002-07-16 | Advanced Medicine, Inc. | Sodium channel drugs and uses |
| ES2237966T3 (es) | 1998-08-20 | 2005-08-01 | Agouron Pharmaceuticals, Inc. | Agentes de gnrh no peptidicos, metodos y compuestos intermedios para su preparacion. |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| TW550258B (en) | 1999-05-31 | 2003-09-01 | Hoffmann La Roche | 4-phenyl-pyrimidine derivatives |
| JP2003519143A (ja) * | 1999-12-28 | 2003-06-17 | ファーマコピーア，インコーポレーティッド | ピリミジン及びトリアジン系キナーゼ阻害剤 |
| NZ526468A (en) | 2000-12-21 | 2004-03-26 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| US7595343B2 (en) | 2001-09-14 | 2009-09-29 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US6897220B2 (en) | 2001-09-14 | 2005-05-24 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| WO2003026665A1 (en) | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | 2-phenylamino-4-(5-pyrazolylamino)-pyrimidine derivatives as kinase inhibitors, in particular, src kinase inhibitors |
| US7544690B2 (en) | 2001-10-01 | 2009-06-09 | Taisho Pharmaceutical Co., Ltd. | MCH receptor antagonists |
| MXPA04012855A (es) | 2002-06-28 | 2005-04-19 | Yamanouchi Pharma Co Ltd | Derivado de diaminopirimidincarboxiamida. |
| EP1571146A4 (en) | 2002-12-10 | 2010-09-01 | Ono Pharmaceutical Co | NITROGENIC HETEROCYCLIC COMPOUNDS AND THEIR MEDICAL USE |
| WO2004067516A1 (en) | 2003-01-30 | 2004-08-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | 2,4-diaminopyrimidine derivatives useful as inhibitors of pkc-theta |
| BRPI0414630A (pt) | 2003-09-22 | 2006-11-07 | Hoffmann La Roche | derivados ciclohexìlicos substituìdos com aminoalquilamida |
| MXPA06010900A (es) * | 2004-03-26 | 2007-02-21 | Methylgene Inc | Inhibidores de histona desacetilasa. |
| CA2904275C (en) | 2004-05-23 | 2020-09-01 | Gerard M. Housey | Theramutein modulators |
| JP2006124387A (ja) * | 2004-09-30 | 2006-05-18 | Taisho Pharmaceut Co Ltd | 新規なキノリン、テトラヒドロキナゾリン、及びピリミジン誘導体と、これらを使用することに関連した治療方法 |
| NZ564222A (en) * | 2005-06-14 | 2011-10-28 | Taigen Biotechnology Co Ltd | Pyrimidine compounds |
| KR20080090381A (ko) | 2005-08-29 | 2008-10-08 | 제라드 엠. 하우지 | 테라뮤틴 조절물질 |
| ES2378153T3 (es) | 2005-09-27 | 2012-04-09 | Irm Llc | Conpuestos y composiciones que contienen diarilamina, y su uso como moduladores de receptores c-kit |
| EP1960535B1 (en) | 2005-11-23 | 2024-05-08 | Gerard M. Housey | Compounds and methods of identifying, synthesizing, optimizing and profiling protein modulators |
| BRPI0710181A2 (pt) | 2006-03-16 | 2011-08-09 | Novartis Ag | compostos orgánicos |
| WO2007129195A2 (en) | 2006-05-04 | 2007-11-15 | Pfizer Products Inc. | 4-pyrimidine-5-amino-pyrazole compounds |
| US8222256B2 (en) * | 2006-07-05 | 2012-07-17 | Exelixis, Inc. | Methods of using IGFIR and ABL kinase modulators |
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- 2008-11-03 PL PL08874003T patent/PL2268635T3/pl unknown
- 2008-11-03 PT PT88740030T patent/PT2268635E/pt unknown
- 2008-11-03 WO PCT/US2008/082202 patent/WO2009131598A1/en not_active Ceased
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- 2008-12-01 CN CN2008101796944A patent/CN101565404B/zh active Active
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2010
- 2010-11-18 ZA ZA2010/08262A patent/ZA201008262B/en unknown
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2015
- 2015-09-07 CY CY20151100774T patent/CY1116802T1/el unknown
Also Published As
| Publication number | Publication date |
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| EP2268635B1 (en) | 2015-06-10 |
| EP2268635A4 (en) | 2012-02-22 |
| KR101579999B1 (ko) | 2015-12-23 |
| AU2008355098A1 (en) | 2009-10-29 |
| CY1116802T1 (el) | 2017-03-15 |
| EA019289B1 (ru) | 2014-02-28 |
| DK2268635T3 (en) | 2015-09-14 |
| JP5661607B2 (ja) | 2015-01-28 |
| WO2009131598A1 (en) | 2009-10-29 |
| EA201071221A1 (ru) | 2011-08-30 |
| PL2268635T3 (pl) | 2015-11-30 |
| HRP20150932T2 (hr) | 2017-10-20 |
| AU2008355098B2 (en) | 2012-11-15 |
| JP2011519360A (ja) | 2011-07-07 |
| CA2720229C (en) | 2015-02-17 |
| TWI444188B (zh) | 2014-07-11 |
| US20090264339A1 (en) | 2009-10-22 |
| CN101565404B (zh) | 2012-12-05 |
| KR20110008085A (ko) | 2011-01-25 |
| HRP20150932T1 (xx) | 2015-10-09 |
| NZ588989A (en) | 2012-03-30 |
| US8372849B2 (en) | 2013-02-12 |
| ZA201008262B (en) | 2011-07-27 |
| CN101565404A (zh) | 2009-10-28 |
| SI2268635T1 (sl) | 2015-10-30 |
| HK1138269A1 (en) | 2010-08-20 |
| TW200944206A (en) | 2009-11-01 |
| ES2545731T3 (es) | 2015-09-15 |
| PT2268635E (pt) | 2015-10-06 |
| CA2720229A1 (en) | 2009-10-29 |
| EP2268635A1 (en) | 2011-01-05 |
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