TW201018678A - Novel heteroaryl substituted benzothiazoles - Google Patents
Novel heteroaryl substituted benzothiazoles Download PDFInfo
- Publication number
- TW201018678A TW201018678A TW098145976A TW98145976A TW201018678A TW 201018678 A TW201018678 A TW 201018678A TW 098145976 A TW098145976 A TW 098145976A TW 98145976 A TW98145976 A TW 98145976A TW 201018678 A TW201018678 A TW 201018678A
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- Taiwan
- Prior art keywords
- alkyl
- fluoroalkyl
- group
- amine
- compound
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 125000001072 heteroaryl group Chemical group 0.000 title abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 325
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 39
- 239000002243 precursor Chemical class 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 208000037259 Amyloid Plaque Diseases 0.000 claims abstract description 27
- 238000001727 in vivo Methods 0.000 claims abstract description 23
- 239000003814 drug Substances 0.000 claims abstract description 19
- 238000003384 imaging method Methods 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 289
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 189
- -1 alkyl hydrazine Chemical compound 0.000 claims description 154
- 238000002360 preparation method Methods 0.000 claims description 59
- 239000002585 base Substances 0.000 claims description 46
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 150000001412 amines Chemical class 0.000 claims description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 41
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 239000007789 gas Substances 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 230000007278 cognition impairment Effects 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- 150000002923 oximes Chemical class 0.000 claims description 9
- 229940067157 phenylhydrazine Drugs 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000006612 decyloxy group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 4
- 108700028369 Alleles Proteins 0.000 claims description 4
- 108010060159 Apolipoprotein E4 Proteins 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
- JVXNCJLLOUQYBF-UHFFFAOYSA-N cyclohex-4-ene-1,3-dione Chemical compound O=C1CC=CC(=O)C1 JVXNCJLLOUQYBF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 208000025688 early-onset autosomal dominant Alzheimer disease Diseases 0.000 claims description 3
- 208000015756 familial Alzheimer disease Diseases 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- MXHZOJAZQKMCLY-UHFFFAOYSA-N 2-(5-fluoro-6-methoxypyridin-3-yl)-6-methoxy-1,3-benzothiazole Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=CN=C(OC)C(F)=C1 MXHZOJAZQKMCLY-UHFFFAOYSA-N 0.000 claims description 2
- JOOYDAXQLRKIDC-UHFFFAOYSA-N 2-(6-ethoxypyridin-3-yl)-6-methoxy-1,3-benzothiazole Chemical compound C1=NC(OCC)=CC=C1C1=NC2=CC=C(OC)C=C2S1 JOOYDAXQLRKIDC-UHFFFAOYSA-N 0.000 claims description 2
- ABFWMVGCOWVGQC-UHFFFAOYSA-N 4-[5-(6-methoxy-1,3-benzothiazol-2-yl)pyridin-2-yl]morpholine Chemical compound S1C2=CC(OC)=CC=C2N=C1C(C=N1)=CC=C1N1CCOCC1 ABFWMVGCOWVGQC-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- RKZUMTJDQXBKFY-UHFFFAOYSA-N n-[2-(6-methoxypyridin-3-yl)-1,3-benzothiazol-6-yl]methanesulfonamide Chemical compound C1=NC(OC)=CC=C1C1=NC2=CC=C(NS(C)(=O)=O)C=C2S1 RKZUMTJDQXBKFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 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 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 1
- XWIYHNUKKMYQKU-UHFFFAOYSA-N 2-[2-(methylamino)pyrimidin-5-yl]-1,3-benzothiazol-6-ol Chemical compound C1=NC(NC)=NC=C1C1=NC2=CC=C(O)C=C2S1 XWIYHNUKKMYQKU-UHFFFAOYSA-N 0.000 claims 1
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims 1
- PEJHEZUYSMYMAF-UHFFFAOYSA-N 5-(5-methoxy-1,3-benzothiazol-2-yl)-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC2=CC(OC)=CC=C2S1 PEJHEZUYSMYMAF-UHFFFAOYSA-N 0.000 claims 1
- WTPFYRRDZLLVQS-UHFFFAOYSA-N 5-(6-methoxy-1,3-benzothiazol-2-yl)-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC2=CC=C(OC)C=C2S1 WTPFYRRDZLLVQS-UHFFFAOYSA-N 0.000 claims 1
- SBGARQOECQWUAY-UHFFFAOYSA-N 5-(6-methoxy-1,3-benzothiazol-2-yl)pyridine-2-carboxamide Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=CC=C(C(N)=O)N=C1 SBGARQOECQWUAY-UHFFFAOYSA-N 0.000 claims 1
- JFSABNXOKOPXSR-UHFFFAOYSA-N 6-methoxy-2-(5-methylsulfanylpyridin-2-yl)-1,3-benzothiazole Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=CC=C(SC)C=N1 JFSABNXOKOPXSR-UHFFFAOYSA-N 0.000 claims 1
- ORTVWKHHSSLPMZ-UHFFFAOYSA-N 6-methoxy-2-(5-methylsulfonylpyridin-2-yl)-1,3-benzothiazole Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=CC=C(S(C)(=O)=O)C=N1 ORTVWKHHSSLPMZ-UHFFFAOYSA-N 0.000 claims 1
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- 229910003322 NiCu Inorganic materials 0.000 claims 1
- UODFNMLKGFTKIQ-UHFFFAOYSA-N [2-(6-methoxypyridin-3-yl)-1,3-benzothiazol-6-yl]-pyrrolidin-1-ylmethanone Chemical compound C1=NC(OC)=CC=C1C1=NC2=CC=C(C(=O)N3CCCC3)C=C2S1 UODFNMLKGFTKIQ-UHFFFAOYSA-N 0.000 claims 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)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76265406P | 2006-01-27 | 2006-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201018678A true TW201018678A (en) | 2010-05-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| TW098145976A TW201018678A (en) | 2006-01-27 | 2007-01-19 | Novel heteroaryl substituted benzothiazoles |
| TW096102118A TW200736252A (en) | 2006-01-27 | 2007-01-19 | Novel heteroaryl substituted benzothiazoles |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096102118A TW200736252A (en) | 2006-01-27 | 2007-01-19 | Novel heteroaryl substituted benzothiazoles |
Country Status (20)
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| US (2) | US8163928B2 (https=) |
| EP (1) | EP1981883A4 (https=) |
| JP (1) | JP5289061B2 (https=) |
| KR (1) | KR101406248B1 (https=) |
| CN (1) | CN101410393B (https=) |
| AR (1) | AR059178A1 (https=) |
| AU (1) | AU2007207904C1 (https=) |
| BR (1) | BRPI0707283A2 (https=) |
| CA (1) | CA2640213A1 (https=) |
| EC (1) | ECSP088645A (https=) |
| IL (1) | IL192876A0 (https=) |
| NO (1) | NO20083394L (https=) |
| NZ (1) | NZ569667A (https=) |
| RU (1) | RU2448106C2 (https=) |
| SA (1) | SA07280009B1 (https=) |
| TW (2) | TW201018678A (https=) |
| UA (1) | UA95267C2 (https=) |
| UY (1) | UY30112A1 (https=) |
| WO (1) | WO2007086800A1 (https=) |
| ZA (1) | ZA200806075B (https=) |
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| EP2699157B1 (en) * | 2011-04-21 | 2018-03-14 | The Regents of The University of California | Functionalized magnetic nanoparticles and use in imaging amyloid deposits and neurofibrillary tangles |
| US20140348748A1 (en) * | 2011-09-16 | 2014-11-27 | Lisheng Cai | Beta-amyloid imaging agents, methods of manufacture, and methods of use thereof |
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| 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 |
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| EP2968296B1 (en) | 2013-03-12 | 2020-09-02 | The Regents of the University of California | Gamma-secretase modulators |
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| 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 |
| EP3170820B1 (en) * | 2014-07-16 | 2019-02-20 | Japan Science and Technology Agency | Benzothiazole compound and medicine containing same |
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| BR112017011661A2 (pt) * | 2014-12-02 | 2018-03-06 | Bayer Cropscience Aktiengesellschaft | compostos bicíclicos como agentes de controle de pragas. |
| EP3227287B1 (de) | 2014-12-02 | 2019-08-07 | Bayer Pharma Aktiengesellschaft | Heteroaryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung |
| BR112017019326B1 (pt) * | 2015-03-12 | 2022-04-26 | Fmc Corporation | Composto, composição e método para controlar uma praga invertebrada |
| MX382156B (es) * | 2015-08-28 | 2025-03-13 | Chdi Foundation Inc | Sondas para formar imagenes de proteina de huntingtina. |
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| US11844846B2 (en) | 2018-05-16 | 2023-12-19 | Emory University | Styrylbenzothiazole derivatives and uses in imaging methods |
| SMT202500291T1 (it) * | 2019-01-31 | 2025-09-12 | Spinogenix Inc | Forme solide di un promotore di spinogenesi |
| GB201914989D0 (en) * | 2019-10-16 | 2019-11-27 | Karin & Sten Mortstedt Cbd Solutions Ab | Selective ligands for TAU Aggregates |
| CN114728071B (zh) | 2019-11-13 | 2024-12-06 | 新旭生技股份有限公司 | 用于降解tau蛋白聚集体的化合物及其用途 |
| 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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-
2007
- 2007-01-19 TW TW098145976A patent/TW201018678A/zh unknown
- 2007-01-19 TW TW096102118A patent/TW200736252A/zh unknown
- 2007-01-24 SA SA7280009A patent/SA07280009B1/ar unknown
- 2007-01-24 AR ARP070100305A patent/AR059178A1/es unknown
- 2007-01-25 NZ NZ569667A patent/NZ569667A/en not_active IP Right Cessation
- 2007-01-25 CN CN2007800112344A patent/CN101410393B/zh not_active Expired - Fee Related
- 2007-01-25 RU RU2008130965/04A patent/RU2448106C2/ru not_active IP Right Cessation
- 2007-01-25 AU AU2007207904A patent/AU2007207904C1/en not_active Ceased
- 2007-01-25 US US12/162,255 patent/US8163928B2/en not_active Expired - Fee Related
- 2007-01-25 BR BRPI0707283-0A patent/BRPI0707283A2/pt not_active IP Right Cessation
- 2007-01-25 EP EP20070709290 patent/EP1981883A4/en not_active Withdrawn
- 2007-01-25 WO PCT/SE2007/000068 patent/WO2007086800A1/en not_active Ceased
- 2007-01-25 UA UAA200809015A patent/UA95267C2/ru unknown
- 2007-01-25 JP JP2008552268A patent/JP5289061B2/ja not_active Expired - Fee Related
- 2007-01-25 CA CA002640213A patent/CA2640213A1/en not_active Abandoned
- 2007-01-25 KR KR1020087020871A patent/KR101406248B1/ko not_active Expired - Fee Related
- 2007-01-26 UY UY30112A patent/UY30112A1/es not_active Application Discontinuation
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2008
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- 2008-07-17 IL IL192876A patent/IL192876A0/en unknown
- 2008-07-22 EC EC2008008645A patent/ECSP088645A/es unknown
- 2008-08-01 NO NO20083394A patent/NO20083394L/no not_active Application Discontinuation
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2012
- 2012-04-23 US US13/453,579 patent/US8957215B2/en not_active Expired - Fee Related
Also Published As
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| US20120207679A1 (en) | 2012-08-16 |
| US8163928B2 (en) | 2012-04-24 |
| NZ569667A (en) | 2011-09-30 |
| NO20083394L (no) | 2008-10-02 |
| AR059178A1 (es) | 2008-03-12 |
| ZA200806075B (en) | 2012-12-27 |
| TW200736252A (en) | 2007-10-01 |
| BRPI0707283A2 (pt) | 2011-04-26 |
| US8957215B2 (en) | 2015-02-17 |
| WO2007086800A1 (en) | 2007-08-02 |
| IL192876A0 (en) | 2009-02-11 |
| UA95267C2 (en) | 2011-07-25 |
| JP5289061B2 (ja) | 2013-09-11 |
| AU2007207904B2 (en) | 2011-03-10 |
| JP2009528271A (ja) | 2009-08-06 |
| CA2640213A1 (en) | 2007-08-02 |
| RU2448106C2 (ru) | 2012-04-20 |
| EP1981883A1 (en) | 2008-10-22 |
| ECSP088645A (es) | 2008-08-29 |
| CN101410393A (zh) | 2009-04-15 |
| KR20080090542A (ko) | 2008-10-08 |
| EP1981883A4 (en) | 2010-10-06 |
| RU2008130965A (ru) | 2010-03-10 |
| AU2007207904A1 (en) | 2007-08-02 |
| AU2007207904C1 (en) | 2011-10-13 |
| CN101410393B (zh) | 2012-01-25 |
| US20090028787A1 (en) | 2009-01-29 |
| UY30112A1 (es) | 2007-08-31 |
| KR101406248B1 (ko) | 2014-06-19 |
| SA07280009B1 (ar) | 2011-07-20 |
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