AU2007207904C1 - Novel heteroaryl substituted benzothiazoles - Google Patents
Novel heteroaryl substituted benzothiazoles Download PDFInfo
- Publication number
- AU2007207904C1 AU2007207904C1 AU2007207904A AU2007207904A AU2007207904C1 AU 2007207904 C1 AU2007207904 C1 AU 2007207904C1 AU 2007207904 A AU2007207904 A AU 2007207904A AU 2007207904 A AU2007207904 A AU 2007207904A AU 2007207904 C1 AU2007207904 C1 AU 2007207904C1
- Authority
- AU
- Australia
- Prior art keywords
- benzothiazol
- compound
- mmol
- pyridin
- benzothiazole
- 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.)
- Ceased
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title abstract description 41
- 125000001072 heteroaryl group Chemical group 0.000 title abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 345
- 238000000034 method Methods 0.000 claims abstract description 110
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- 239000002243 precursor Chemical class 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 32
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- 238000003384 imaging method Methods 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 78
- 230000027455 binding Effects 0.000 claims description 46
- 238000011282 treatment Methods 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 238000001514 detection method Methods 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 12
- 230000002265 prevention Effects 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 238000011503 in vivo imaging Methods 0.000 claims description 11
- FYTAUNFPOYWHBC-UHFFFAOYSA-N 2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol Chemical compound C1=NC(NC)=CC=C1C1=NC2=CC=C(O)C=C2S1 FYTAUNFPOYWHBC-UHFFFAOYSA-N 0.000 claims description 10
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
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Classifications
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- 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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| PCT/SE2007/000068 WO2007086800A1 (en) | 2006-01-27 | 2007-01-25 | Novel heteroaryl substituted benzothiazoles |
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| TW201018678A (en) | 2006-01-27 | 2010-05-16 | Astrazeneca Ab | Novel heteroaryl substituted benzothiazoles |
| TW200813035A (en) | 2006-06-19 | 2008-03-16 | Astrazeneca Ab | Novel heteroaryl substituted benzoxazoles |
| TW200901998A (en) | 2007-03-06 | 2009-01-16 | Astrazeneca Ab | Novel 2-heteroaryl substituted benzothiophenes and benzofuranes |
| US8557222B2 (en) | 2008-04-04 | 2013-10-15 | Avid Radiopharmaceuticals, Inc. | Radiopharmaceutical imaging of neurodegenerative diseases |
| ES2554772T3 (es) | 2008-05-30 | 2015-12-23 | Merck Sharp & Dohme Corp. | Azabenzoxazoles sustituidos novedosos |
| US8193363B2 (en) * | 2008-08-29 | 2012-06-05 | Astrazeneca Ab | Compounds suitable as precursors to compounds that are useful for imaging amyloid deposits |
| CA2741668A1 (en) * | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel substituted azabenzoxazoles |
| EP2501696B1 (en) * | 2009-10-15 | 2016-12-28 | Guerbet | Imaging agents and their use for the diagnostic in vivo of neurodegenerative diseases, notably alzheimer's disease and derivative diseases |
| WO2011163636A2 (en) * | 2010-06-24 | 2011-12-29 | The Regents Of The University Of California | Compounds and uses thereof in modulating levels of various amyloid beta peptide alloforms |
| WO2012145169A2 (en) * | 2011-04-21 | 2012-10-26 | The Regents Of The University Of California | Functionalized magnetic nanoparticles and use in imaging amyloid deposits and neurofibrillary tangles |
| WO2013040183A1 (en) * | 2011-09-16 | 2013-03-21 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Beta-amyloid imaging agents, methods of manufacture, and methods of use thereof |
| CN102558091B (zh) * | 2011-12-22 | 2014-10-08 | 合肥工业大学 | 一种苯并噻唑类衍生物及其用途 |
| CN102659772B (zh) * | 2012-05-03 | 2015-02-11 | 北京师范大学 | 一种与Aβ斑块有亲和力的2-芳基苯并杂环化合物及其制备方法和应用 |
| KR102053484B1 (ko) * | 2012-12-21 | 2019-12-06 | 국립연구개발법인 양자과학기술연구개발기구 | 뇌 안에 축적된 타우 단백질을 이미징하기 위한 신규한 화합물 |
| EP2968296B1 (en) | 2013-03-12 | 2020-09-02 | The Regents of the University of California | Gamma-secretase modulators |
| TWI652014B (zh) * | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | 雜環取代之雙環唑殺蟲劑 |
| WO2015051188A1 (en) | 2013-10-02 | 2015-04-09 | Washington University | Heterocyclic molecules for biomedical imaging and therapeutic applications |
| WO2016004513A1 (en) * | 2014-07-11 | 2016-01-14 | Simon Fraser University | Anti-bacterial pyruvate kinase modulator compounds, compositions, uses and methods |
| JP6562361B2 (ja) * | 2014-07-16 | 2019-08-21 | 国立研究開発法人科学技術振興機構 | ベンゾチアゾール化合物及びこれを含有する医薬 |
| WO2016070107A1 (en) | 2014-10-31 | 2016-05-06 | The General Hospital Corporation | Potent gamma-secretase modulators |
| EP3227287B1 (de) | 2014-12-02 | 2019-08-07 | Bayer Pharma Aktiengesellschaft | Heteroaryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung |
| JP2017537916A (ja) * | 2014-12-02 | 2017-12-21 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 有害生物防除剤としての二環式化合物 |
| EP3268359B1 (en) * | 2015-03-12 | 2019-12-18 | FMC Corporation | Heterocycle-substituted bicyclic azole pesticides |
| MX382156B (es) | 2015-08-28 | 2025-03-13 | Chdi Foundation Inc | Sondas para formar imagenes de proteina de huntingtina. |
| GB201617339D0 (en) * | 2016-10-12 | 2016-11-23 | Lytix Biopharma As | Therapeutic compounds |
| AU2018312558B2 (en) | 2017-08-02 | 2022-09-29 | Spinogenix, Inc. | Benzothiazole and related compounds |
| CA3099318C (en) | 2018-05-09 | 2024-02-13 | Aprinoia Therapeutics Inc. | Heteroaryl compounds and uses thereof |
| CA3100235A1 (en) | 2018-05-16 | 2019-11-21 | Emory University | Styrylbenzothiazole derivatives and uses in imaging |
| HUE072464T2 (hu) | 2019-01-31 | 2025-11-28 | Spinogenix Inc | Spinogenézis egy promoterének szilárd formái |
| GB201914989D0 (en) * | 2019-10-16 | 2019-11-27 | Karin & Sten Mortstedt Cbd Solutions Ab | Selective ligands for TAU Aggregates |
| CA3161455A1 (en) | 2019-11-13 | 2021-05-20 | Aprinoia Therapeutics Limited | Compounds for degrading tau protein aggregates and uses thereof |
| KR102682408B1 (ko) * | 2021-05-12 | 2024-07-05 | 에이치케이이노엔 주식회사 | 신규한 벤조티아졸 유도체, 이의 제조방법 및 이의 간질환 예방 또는 치료 용도 |
| CN114478431B (zh) * | 2022-03-09 | 2024-07-02 | 台州学院 | 一种双取代苯并噻吩类钾离子通道激动剂的制备方法 |
| CN114380731B (zh) * | 2022-03-09 | 2024-07-02 | 台州学院 | 一种kcnq钾离子通道激动剂、药物组合物及其应用 |
| JP2025540931A (ja) | 2022-11-03 | 2025-12-17 | セントニックス インコーポレイテッド | タウ凝集体に対する選択的リガンド |
| WO2025202955A1 (en) | 2024-03-28 | 2025-10-02 | Pi Industries Ltd. | Fused bicyclic compounds and their use as pest control agents |
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| JP5289061B2 (ja) | 2013-09-11 |
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| US8163928B2 (en) | 2012-04-24 |
| NO20083394L (no) | 2008-10-02 |
| AR059178A1 (es) | 2008-03-12 |
| IL192876A0 (en) | 2009-02-11 |
| ZA200806075B (en) | 2012-12-27 |
| UY30112A1 (es) | 2007-08-31 |
| RU2008130965A (ru) | 2010-03-10 |
| US20090028787A1 (en) | 2009-01-29 |
| US20120207679A1 (en) | 2012-08-16 |
| UA95267C2 (en) | 2011-07-25 |
| US8957215B2 (en) | 2015-02-17 |
| AU2007207904B2 (en) | 2011-03-10 |
| SA07280009B1 (ar) | 2011-07-20 |
| CA2640213A1 (en) | 2007-08-02 |
| CN101410393A (zh) | 2009-04-15 |
| BRPI0707283A2 (pt) | 2011-04-26 |
| KR101406248B1 (ko) | 2014-06-19 |
| CN101410393B (zh) | 2012-01-25 |
| JP2009528271A (ja) | 2009-08-06 |
| AU2007207904A1 (en) | 2007-08-02 |
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