CN102617556A - 新的2-杂芳基取代的苯并噻吩和苯并呋喃709 - Google Patents
新的2-杂芳基取代的苯并噻吩和苯并呋喃709 Download PDFInfo
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- CN102617556A CN102617556A CN2012100933476A CN201210093347A CN102617556A CN 102617556 A CN102617556 A CN 102617556A CN 2012100933476 A CN2012100933476 A CN 2012100933476A CN 201210093347 A CN201210093347 A CN 201210093347A CN 102617556 A CN102617556 A CN 102617556A
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- alkyl
- fluoroalkyl
- compound
- radical
- alkylene
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title abstract description 26
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical class C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 235
- 238000000034 method Methods 0.000 claims abstract description 54
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- 208000037259 Amyloid Plaque Diseases 0.000 claims abstract description 32
- 239000002243 precursor Chemical class 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 6
- -1 hydroxy, methoxy Chemical group 0.000 claims description 93
- 150000003254 radicals Chemical class 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000004429 atom Chemical group 0.000 claims description 31
- 239000000470 constituent Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 9
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 125000002346 iodo group Chemical group I* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 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 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 29
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- 238000003384 imaging method Methods 0.000 abstract description 20
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- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
- 239000000243 solution Substances 0.000 description 38
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
- 229910001868 water Inorganic materials 0.000 description 25
- 239000000460 chlorine Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 125000003118 aryl group Chemical group 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000543 intermediate Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 230000027455 binding Effects 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 125000006239 protecting group Chemical group 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 238000001514 detection method Methods 0.000 description 13
- 238000002372 labelling Methods 0.000 description 13
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 12
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 206010002022 amyloidosis Diseases 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 210000001519 tissue Anatomy 0.000 description 10
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
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- 229910052760 oxygen Inorganic materials 0.000 description 9
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- 238000002600 positron emission tomography Methods 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- XLIQZZGLIJLKTF-UHFFFAOYSA-N (5-methoxy-1-benzofuran-2-yl)boronic acid Chemical compound COC1=CC=C2OC(B(O)O)=CC2=C1 XLIQZZGLIJLKTF-UHFFFAOYSA-N 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 8
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 8
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- 125000000623 heterocyclic group Chemical group 0.000 description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
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- 230000029936 alkylation Effects 0.000 description 7
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical group CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- UKHQRARQNZOXRL-UHFFFAOYSA-N trimethyltin Chemical group C[SnH](C)C UKHQRARQNZOXRL-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen 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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (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 Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89314907P | 2007-03-06 | 2007-03-06 | |
| US60/893,149 | 2007-03-06 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2008800149945A Division CN101675042B (zh) | 2007-03-06 | 2008-03-05 | 新的2-杂芳基取代的苯并噻吩和苯并呋喃709 |
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| Publication Number | Publication Date |
|---|---|
| CN102617556A true CN102617556A (zh) | 2012-08-01 |
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| CN2012100933476A Pending CN102617556A (zh) | 2007-03-06 | 2008-03-05 | 新的2-杂芳基取代的苯并噻吩和苯并呋喃709 |
| CN2008800149945A Active CN101675042B (zh) | 2007-03-06 | 2008-03-05 | 新的2-杂芳基取代的苯并噻吩和苯并呋喃709 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2008800149945A Active CN101675042B (zh) | 2007-03-06 | 2008-03-05 | 新的2-杂芳基取代的苯并噻吩和苯并呋喃709 |
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| EP (1) | EP2132201B1 (enExample) |
| JP (1) | JP5631009B2 (enExample) |
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| AU (1) | AU2008221668B2 (enExample) |
| BR (1) | BRPI0808503B8 (enExample) |
| CA (1) | CA2680157C (enExample) |
| CL (1) | CL2008000645A1 (enExample) |
| CO (1) | CO6220965A2 (enExample) |
| EC (1) | ECSP099641A (enExample) |
| ES (1) | ES2615381T3 (enExample) |
| IL (1) | IL200524A0 (enExample) |
| MX (1) | MX2009009469A (enExample) |
| MY (1) | MY147347A (enExample) |
| NZ (1) | NZ579157A (enExample) |
| PE (1) | PE20090164A1 (enExample) |
| SA (1) | SA08290097B1 (enExample) |
| TW (1) | TW200901998A (enExample) |
| UA (1) | UA98481C2 (enExample) |
| UY (1) | UY30951A1 (enExample) |
| WO (1) | WO2008108730A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200901998A (en) * | 2007-03-06 | 2009-01-16 | Astrazeneca Ab | Novel 2-heteroaryl substituted benzothiophenes and benzofuranes |
| EP2300481B1 (en) | 2008-05-30 | 2015-09-30 | Merck Sharp & Dohme Corp. | Novel substituted azabenzoxazoles |
| BRPI0917540A2 (pt) | 2008-08-05 | 2015-11-17 | Daiichi Sankyo Co Ltd | composto, sal farmacologicamente aceitavél, composição farmacêutica, e, uso de um composto ou sal farmacologicamente aceitável |
| US8193363B2 (en) * | 2008-08-29 | 2012-06-05 | Astrazeneca Ab | Compounds suitable as precursors to compounds that are useful for imaging amyloid deposits |
| KR101123178B1 (ko) * | 2009-04-09 | 2012-06-13 | (주)에스메디 | 2-아릴벤조싸이오펜 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 퇴행성 뇌질환의 진단 또는 치료용 약학적 조성물 |
| WO2011059080A1 (ja) * | 2009-11-16 | 2011-05-19 | 第一三共株式会社 | 同位体置換されたジアミン誘導体 |
| EP2388255A1 (en) * | 2010-05-11 | 2011-11-23 | Ikerchem, S.L. | Polysubstituted benzofurans and medicinal applications thereof |
| JP5825608B2 (ja) * | 2010-08-06 | 2015-12-02 | 国立大学法人京都大学 | ピリジルベンゾフラン誘導体 |
| MX2020008082A (es) * | 2018-02-05 | 2020-09-24 | Univ Strasbourg | Compuestos y composiciones para el tratamiento del dolor. |
| BR112021026837A2 (pt) * | 2019-08-06 | 2022-02-22 | Domain Therapeutics | Compostos de 5-heteroaril-piridin-2-amina como anta-gonistas do receptor de neuropeptídeo ff |
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| WO1995017095A1 (en) * | 1993-12-21 | 1995-06-29 | Eli Lilly And Company | Methods for the treatment or prevention of conditions associated with amyloidogenic reptides |
| WO2003051859A1 (en) * | 2001-12-19 | 2003-06-26 | Amersham Plc | Compounds for imaging alzheimer's disease |
| CN101675042B (zh) * | 2007-03-06 | 2012-06-13 | 阿斯利康(瑞典)有限公司 | 新的2-杂芳基取代的苯并噻吩和苯并呋喃709 |
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| AU523040B2 (en) | 1978-05-15 | 1982-07-08 | Kanebo Limited | Calcium -antagonistic composition |
| GB8305245D0 (en) | 1983-02-25 | 1983-03-30 | Fujisawa Pharmaceutical Co | Imidazo-heterocyclic compounds |
| CA2034309C (en) | 1990-01-22 | 1997-04-01 | Takashi Iwaki | Mesomorphic compound, liquid crystal composition containing same, liquid crystal device using same and display apparatus |
| US5518713A (en) | 1995-02-13 | 1996-05-21 | 3V Inc. | Benzoxazole derivatives, the use thereof as sunscreens and cosmetic compositions containing them |
| JPH11116476A (ja) | 1997-10-16 | 1999-04-27 | Sankyo Co Ltd | 縮合複素環化合物 |
| SI1334091T1 (sl) | 2000-08-24 | 2013-01-31 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Derivati tioflavina in njihova uporaba pri diagnozi in terapiji pri Alzheimerjevi bolezni |
| JP2004524289A (ja) | 2000-12-22 | 2004-08-12 | アストラゼネカ・アクチエボラーグ | 治療化合物 |
| US20040077654A1 (en) * | 2001-01-15 | 2004-04-22 | Bouillot Anne Marie Jeanne | Aryl piperidine and piperazine derivatives as inducers of ldl-receptor expression |
| JP4307001B2 (ja) * | 2001-03-14 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
| US6596731B2 (en) | 2001-03-27 | 2003-07-22 | Hoffmann-La Roche Inc. | Substituted imidazo[1,2-A] pyridine derivatives |
| KR20040058111A (ko) | 2001-04-23 | 2004-07-03 | 더 트러스티스 오브 더 유니버시티 오브 펜실바니아 | 아밀로이드 플라크 응집 억제제 및 진단 영상화제 |
| EP1460067A4 (en) | 2001-11-26 | 2005-12-07 | Takeda Pharmaceutical | BICYCLIC DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE |
| AU2003242233A1 (en) | 2002-06-12 | 2003-12-31 | Bf Research Institute, Inc. | Probe compound for image diagnosis of disease with amyloid accumulation, compound for staining age spots/diffuse age spots, and remedy for disease with amyloid accumulation |
| TW200401194A (en) | 2002-07-11 | 2004-01-16 | Advanced Micro Devices Inc | Method and apparatus for determining a processor state without interrupting processor operation |
| ATE425753T1 (de) | 2002-08-02 | 2009-04-15 | Genesoft Pharmaceuticals Inc | Biaryl-verbindungen mit antiinfektiver wirkung |
| JP2004250411A (ja) | 2003-02-21 | 2004-09-09 | Bf Kenkyusho:Kk | アミロイドβ蓄積性疾患の診断プローブおよび治療用化合物 |
| CA2438032C (en) | 2003-03-14 | 2013-05-07 | University Of Pittsburgh | Benzothiazole derivative compounds, compositions and uses |
| JPWO2004087641A1 (ja) | 2003-03-31 | 2006-06-29 | 第一製薬株式会社 | ヒドラゾン誘導体 |
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| EP1644365A2 (en) * | 2003-07-02 | 2006-04-12 | Biofocus Discovery Ltd | Pyrazine and pyridine derivatives as rho kinase inhibitors |
| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
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| TW200813035A (en) | 2006-06-19 | 2008-03-16 | Astrazeneca Ab | Novel heteroaryl substituted benzoxazoles |
| EP2125800A1 (en) | 2007-01-22 | 2009-12-02 | AstraZeneca AB | Novel heteroaryl substituted imidazo ý1,2 -a¨pyridine derivatives |
-
2008
- 2008-03-03 TW TW097107378A patent/TW200901998A/zh unknown
- 2008-03-04 SA SA8290097A patent/SA08290097B1/ar unknown
- 2008-03-04 CL CL200800645A patent/CL2008000645A1/es unknown
- 2008-03-05 MX MX2009009469A patent/MX2009009469A/es active IP Right Grant
- 2008-03-05 AR ARP080100905A patent/AR065599A1/es active IP Right Grant
- 2008-03-05 CA CA2680157A patent/CA2680157C/en active Active
- 2008-03-05 MY MYPI20093695A patent/MY147347A/en unknown
- 2008-03-05 AU AU2008221668A patent/AU2008221668B2/en active Active
- 2008-03-05 BR BRPI0808503A patent/BRPI0808503B8/pt active IP Right Grant
- 2008-03-05 WO PCT/SE2008/050243 patent/WO2008108730A1/en not_active Ceased
- 2008-03-05 ES ES08724190.7T patent/ES2615381T3/es active Active
- 2008-03-05 KR KR1020097018603A patent/KR101530392B1/ko active Active
- 2008-03-05 PE PE2008000429A patent/PE20090164A1/es not_active Application Discontinuation
- 2008-03-05 CN CN2012100933476A patent/CN102617556A/zh active Pending
- 2008-03-05 JP JP2009552641A patent/JP5631009B2/ja active Active
- 2008-03-05 CN CN2008800149945A patent/CN101675042B/zh active Active
- 2008-03-05 EP EP08724190.7A patent/EP2132201B1/en active Active
- 2008-03-05 US US12/042,795 patent/US7772256B2/en active Active
- 2008-03-05 NZ NZ579157A patent/NZ579157A/en not_active IP Right Cessation
- 2008-03-05 UY UY30951A patent/UY30951A1/es not_active Application Discontinuation
- 2008-05-03 UA UAA200908596A patent/UA98481C2/ru unknown
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2009
- 2009-08-20 IL IL200524A patent/IL200524A0/en unknown
- 2009-09-07 CO CO09095235A patent/CO6220965A2/es not_active Application Discontinuation
- 2009-09-21 EC EC2009009641A patent/ECSP099641A/es unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995017095A1 (en) * | 1993-12-21 | 1995-06-29 | Eli Lilly And Company | Methods for the treatment or prevention of conditions associated with amyloidogenic reptides |
| WO2003051859A1 (en) * | 2001-12-19 | 2003-06-26 | Amersham Plc | Compounds for imaging alzheimer's disease |
| CN101675042B (zh) * | 2007-03-06 | 2012-06-13 | 阿斯利康(瑞典)有限公司 | 新的2-杂芳基取代的苯并噻吩和苯并呋喃709 |
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