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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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012301 transgenic model Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000006478 transmetalation reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 description 1
- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000007492 two-way ANOVA Methods 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Classifications
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- 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
-
- 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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| US60/762,654 | 2006-01-27 | ||
| PCT/SE2007/000068 WO2007086800A1 (en) | 2006-01-27 | 2007-01-25 | Novel heteroaryl substituted benzothiazoles |
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| AU2007207904B2 AU2007207904B2 (en) | 2011-03-10 |
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| TW200736252A (en) | 2006-01-27 | 2007-10-01 | 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 |
| JP5603855B2 (ja) | 2008-04-04 | 2014-10-08 | アビッド レディオファーマシューティカルズ、インク． | 神経変成疾患の放射性薬剤による画像化 |
| WO2009155017A2 (en) | 2008-05-30 | 2009-12-23 | Merck & Co., Inc. | Novel substituted azabenzoxazoles |
| US8193363B2 (en) * | 2008-08-29 | 2012-06-05 | Astrazeneca Ab | Compounds suitable as precursors to compounds that are useful for imaging amyloid deposits |
| WO2010051196A1 (en) * | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel substituted azabenzoxazoles |
| ES2620177T3 (es) | 2009-10-15 | 2017-06-27 | Guerbet | Agentes de formación de imágenes y su uso para el diagnóstico in vivo de enfermedades neurodegenerativas, particularmente la enfermedad de Alzheimer y enfermedades derivadas |
| EP2585455B1 (en) * | 2010-06-24 | 2019-08-07 | The Regents of the University of California | Compounds and uses thereof in modulating levels of various amyloid beta peptide alloforms |
| KR20140012732A (ko) * | 2011-04-21 | 2014-02-03 | 더 리젠츠 오브 더 유니버시티 오브 캘리포니아 | 작용화된 자성 나노입자, 그리고 아밀로이드 침착물 및 신경섬유매듭의 영상화에서의 용도 |
| US20140348748A1 (en) * | 2011-09-16 | 2014-11-27 | Lisheng Cai | 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 |
| DK2767532T3 (en) * | 2012-12-21 | 2016-09-12 | Nat Inst For Quantum And Radiological Science And Tech | New connection for reproduction of tau protein heavy in the brain. |
| US9938263B2 (en) | 2013-03-12 | 2018-04-10 | The General Hospital Corporation | 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 |
| US9932333B2 (en) | 2014-07-16 | 2018-04-03 | Japan Science And Technology Agency | Benzothiazole compound and medicine containing same |
| EP3212633B1 (en) | 2014-10-31 | 2019-12-04 | The General Hospital Corporation | Potent gamma-secretase modulators |
| EP3227283A1 (de) * | 2014-12-02 | 2017-10-11 | Bayer CropScience AG | Bicyclische verbindungen als schädlingsbekämpfungsmittel |
| CN107001361A (zh) | 2014-12-02 | 2017-08-01 | 拜耳医药股份有限公司 | 杂芳基取代的咪唑并[1，2‑a]吡啶及其用途 |
| MX2017011579A (es) * | 2015-03-12 | 2018-03-15 | Du Pont | Pesticidas de tipo azol bicíclicos sustituidos con un heterociclo. |
| RU2721419C2 (ru) * | 2015-08-28 | 2020-05-19 | СиЭйчДиАй ФАУНДЕЙШН, ИНК. | Зонды визуализации белка гентингтина |
| 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 |
| JP7293343B2 (ja) | 2018-05-09 | 2023-06-19 | アプリノイア セラピューティクス リミテッド | ヘテロアリール化合物及びその使用 |
| CA3100235A1 (en) | 2018-05-16 | 2019-11-21 | Emory University | Styrylbenzothiazole derivatives and uses in imaging |
| WO2020160332A1 (en) | 2019-01-31 | 2020-08-06 | Spinogenix, Inc. | Solid forms of a promoter of spinogenesis |
| GB201914989D0 (en) * | 2019-10-16 | 2019-11-27 | Karin & Sten Mortstedt Cbd Solutions Ab | Selective ligands for TAU Aggregates |
| AU2020383593A1 (en) | 2019-11-13 | 2022-06-09 | 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 |
| 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 |
| 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 |
| EP4612139A1 (en) | 2022-11-03 | 2025-09-10 | Sentonix, Inc. | Selective ligands for tau aggregates |
| 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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| JP2010516672A (ja) | 2007-01-22 | 2010-05-20 | アストラゼネカ・アクチエボラーグ | 新規なヘテロアリール置換されたイミダゾ［１，２−ａ］ピリジン誘導体 |
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2007
- 2007-01-19 TW TW096102118A patent/TW200736252A/zh unknown
- 2007-01-19 TW TW098145976A patent/TW201018678A/zh unknown
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| WO2002051821A1 (en) * | 2000-12-22 | 2002-07-04 | Astrazeneca Ab | Therapeutic compounds |
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| RU2448106C2 (ru) | 2012-04-20 |
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| UY30112A1 (es) | 2007-08-31 |
| TW200736252A (en) | 2007-10-01 |
| EP1981883A4 (en) | 2010-10-06 |
| US20090028787A1 (en) | 2009-01-29 |
| CA2640213A1 (en) | 2007-08-02 |
| ECSP088645A (es) | 2008-08-29 |
| CN101410393A (zh) | 2009-04-15 |
| KR20080090542A (ko) | 2008-10-08 |
| JP2009528271A (ja) | 2009-08-06 |
| UA95267C2 (en) | 2011-07-25 |
| US8957215B2 (en) | 2015-02-17 |
| CN101410393B (zh) | 2012-01-25 |
| WO2007086800A1 (en) | 2007-08-02 |
| RU2008130965A (ru) | 2010-03-10 |
| AR059178A1 (es) | 2008-03-12 |
| IL192876A0 (en) | 2009-02-11 |
| SA07280009B1 (ar) | 2011-07-20 |
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