ES3009382T3 - Pyrazolo[1,5-a]pyrimidine-based compounds, compositions comprising them and methods of their use - Google Patents
Pyrazolo[1,5-a]pyrimidine-based compounds, compositions comprising them and methods of their use Download PDFInfo
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- ES3009382T3 ES3009382T3 ES14766634T ES14766634T ES3009382T3 ES 3009382 T3 ES3009382 T3 ES 3009382T3 ES 14766634 T ES14766634 T ES 14766634T ES 14766634 T ES14766634 T ES 14766634T ES 3009382 T3 ES3009382 T3 ES 3009382T3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361874395P | 2013-09-06 | 2013-09-06 | |
| PCT/US2014/054209 WO2015035117A1 (en) | 2013-09-06 | 2014-09-05 | PYRAZOLO[1,5-a]PYRIMIDINE-BASED COMPOUNDS, COMPOSITIONS COMPRISING THEM, AND METHODS OF THEIR USE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES3009382T3 true ES3009382T3 (en) | 2025-03-26 |
Family
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| ES14766634T Active ES3009382T3 (en) | 2013-09-06 | 2014-09-05 | Pyrazolo[1,5-a]pyrimidine-based compounds, compositions comprising them and methods of their use |
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| Country | Link |
|---|---|
| US (2) | US20150175610A1 (enExample) |
| EP (1) | EP3041475B1 (enExample) |
| JP (1) | JP6472450B2 (enExample) |
| CN (1) | CN105517553B (enExample) |
| AR (1) | AR097545A1 (enExample) |
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| DK (1) | DK3041475T3 (enExample) |
| ES (1) | ES3009382T3 (enExample) |
| PT (1) | PT3041475T (enExample) |
| TW (1) | TW201542550A (enExample) |
| WO (1) | WO2015035117A1 (enExample) |
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| US9737542B2 (en) | 2013-10-11 | 2017-08-22 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US20170333435A1 (en) | 2014-11-06 | 2017-11-23 | Lysosomal Therapeutics Inc. | Substituted imidazo[1,5-a]pyrimidines and their use in the treatment of medical disorders |
| KR102662215B1 (ko) | 2014-11-06 | 2024-05-02 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 치환된 피라졸로(1,5-a)피리미딘 및 의학적 장애의 치료에서의 그의 용도 |
| EP3215509B1 (en) | 2014-11-06 | 2020-02-26 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders |
| BR112018070586A8 (pt) | 2016-04-06 | 2023-03-14 | Lysosomal Therapeutics Inc | Compostos de pirazol[1,5-a]pirimidinil carboxamida e seu uso no tratamento de distúrbios médicos |
| WO2017176962A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics, Inc. | Pyrrolo[1,2-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| JP7046827B2 (ja) | 2016-04-06 | 2022-04-04 | リソソーマル・セラピューティクス・インコーポレイテッド | イミダゾ［１，５－ａ］ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 |
| CN109311902B (zh) | 2016-05-05 | 2022-07-15 | Bial研发投资股份有限公司 | 取代的咪唑并[1,2-b]哒嗪、咪唑并[1,5-b]哒嗪、相关化合物及其用途 |
| US11345698B2 (en) | 2016-05-05 | 2022-05-31 | Bial—R&D Investments, S.A. | Substituted imidazo[1,2-a]pyridines, substituted imidazo[1,2-a]pyrazines, related compounds, and their use in the treatment of medical disorders |
| CN113271940A (zh) * | 2018-10-15 | 2021-08-17 | 林伯士拉克许米公司 | Tyk2抑制剂和其用途 |
Family Cites Families (22)
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| US5464764A (en) | 1989-08-22 | 1995-11-07 | University Of Utah Research Foundation | Positive-negative selection methods and vectors |
| WO1993004169A1 (en) | 1991-08-20 | 1993-03-04 | Genpharm International, Inc. | Gene targeting in animal cells using isogenic dna constructs |
| US6194410B1 (en) * | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
| KR20040097375A (ko) * | 2002-04-23 | 2004-11-17 | 시오노기 앤드 컴파니, 리미티드 | 피라졸로[1, 5-에이]피리미딘 유도체 및 이를 함유한엔에이디(피)에이취 산화효소 저해제 |
| US7329662B2 (en) | 2003-10-03 | 2008-02-12 | Hoffmann-La Roche Inc. | Pyrazolo-pyridine |
| PT1863818E (pt) | 2005-03-23 | 2010-04-09 | Hoffmann La Roche | Derivados de acetilenil-pirazolo-pirimidina como antagonistas de mglur2 |
| JP5048675B2 (ja) * | 2005-09-27 | 2012-10-17 | エフ．ホフマン−ラ ロシュ アーゲー | ｍＧｌｕＲ２アンタゴニストとしてのオキサジアゾリルピラゾロ−ピリミジン類 |
| JP4847275B2 (ja) * | 2005-10-21 | 2011-12-28 | 田辺三菱製薬株式会社 | ピラゾロ［１，５−ａ］ピリミジン化合物 |
| US20090275586A1 (en) | 2006-10-06 | 2009-11-05 | Kalypsys, Inc. | Heterocyclic inhibitors of pde4 |
| RU2009120389A (ru) * | 2006-10-30 | 2010-12-10 | Новартис АГ (CH) | Гетероциклические соединения в качестве противовоспалительных агентов |
| AR067326A1 (es) | 2007-05-11 | 2009-10-07 | Novartis Ag | Imidazopiridinas y pirrolo -pirimidinas sustituidas como inhibidores de cinasa de lipido |
| KR101324804B1 (ko) * | 2008-05-13 | 2013-11-01 | 아이알엠 엘엘씨 | 키나제 억제제로서의 질소 함유 융합 헤테로사이클 및 그의 조성물 |
| TWI491610B (zh) * | 2008-10-09 | 2015-07-11 | 必治妥美雅史谷比公司 | 作為激酶抑制劑之咪唑并嗒腈 |
| EP2350071B1 (en) * | 2008-10-22 | 2014-01-08 | Array Biopharma, Inc. | SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS TRK KINASE INHIBITORS |
| MX2011012369A (es) * | 2009-05-20 | 2012-03-16 | Cylene Pharmaceuticals Inc | Pirazolopirimidinas y heterociclos relacionados como inhibidores de cinasa. |
| AR077468A1 (es) * | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| WO2011073316A1 (en) * | 2009-12-18 | 2011-06-23 | Novartis Ag | 4-aryl-butane-1,3-diamides |
| US8946237B2 (en) * | 2010-01-14 | 2015-02-03 | Merck Sharp & Dohme Corp. | Pyrazolo[1,5-A]pyrimidines as mark inhibitors |
| RU2598840C2 (ru) * | 2011-05-19 | 2016-09-27 | Фундасион Сентро Насиональ Де Инвестигасионес Онколохикас Карлос Iii | Новые соединения |
| CN104220071A (zh) | 2012-03-09 | 2014-12-17 | 莱西肯医药有限公司 | 抑制转接物关联激酶1以治疗疼痛 |
| WO2013134228A1 (en) * | 2012-03-09 | 2013-09-12 | Lexicon Pharmaceuticals, Inc. | PYRAZOLO[1,5-a]PYRIMIDINE-BASED COMPOUNDS, COMPOSITIONS COMPRISING THEM, AND METHODS OF THEIR USE |
| GB201205669D0 (en) * | 2012-03-30 | 2012-05-16 | Agency Science Tech & Res | Bicyclic heterocyclic derivatives as mnk2 and mnk2 modulators and uses thereof |
-
2014
- 2014-09-02 TW TW103130281A patent/TW201542550A/zh unknown
- 2014-09-03 AR ARP140103297A patent/AR097545A1/es unknown
- 2014-09-05 US US14/478,089 patent/US20150175610A1/en not_active Abandoned
- 2014-09-05 CN CN201480049185.3A patent/CN105517553B/zh active Active
- 2014-09-05 WO PCT/US2014/054209 patent/WO2015035117A1/en not_active Ceased
- 2014-09-05 ES ES14766634T patent/ES3009382T3/es active Active
- 2014-09-05 EP EP14766634.1A patent/EP3041475B1/en active Active
- 2014-09-05 CA CA2923317A patent/CA2923317C/en active Active
- 2014-09-05 JP JP2016540405A patent/JP6472450B2/ja active Active
- 2014-09-05 PT PT147666341T patent/PT3041475T/pt unknown
- 2014-09-05 DK DK14766634.1T patent/DK3041475T3/da active
- 2014-09-05 AU AU2014315113A patent/AU2014315113B2/en active Active
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2016
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Also Published As
| Publication number | Publication date |
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| CN105517553A (zh) | 2016-04-20 |
| US9862724B2 (en) | 2018-01-09 |
| DK3041475T3 (da) | 2024-12-02 |
| PT3041475T (pt) | 2025-01-07 |
| EP3041475A1 (en) | 2016-07-13 |
| CN105517553B (zh) | 2020-03-27 |
| JP6472450B2 (ja) | 2019-02-20 |
| US20150175610A1 (en) | 2015-06-25 |
| CA2923317C (en) | 2023-04-04 |
| HK1217658A1 (zh) | 2017-01-20 |
| WO2015035117A1 (en) | 2015-03-12 |
| EP3041475B1 (en) | 2024-10-09 |
| AU2014315113B2 (en) | 2018-10-04 |
| AR097545A1 (es) | 2016-03-23 |
| US20170081330A1 (en) | 2017-03-23 |
| JP2016529315A (ja) | 2016-09-23 |
| TW201542550A (zh) | 2015-11-16 |
| AU2014315113A1 (en) | 2016-03-10 |
| CA2923317A1 (en) | 2015-03-12 |
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