EA012334B1 - Производные стильбена и их применение для связывания и визуализации амилоидных бляшек - Google Patents
Производные стильбена и их применение для связывания и визуализации амилоидных бляшек Download PDFInfo
- Publication number
- EA012334B1 EA012334B1 EA200701299A EA200701299A EA012334B1 EA 012334 B1 EA012334 B1 EA 012334B1 EA 200701299 A EA200701299 A EA 200701299A EA 200701299 A EA200701299 A EA 200701299A EA 012334 B1 EA012334 B1 EA 012334B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- ethoxy
- compound
- group
- phenyl
- Prior art date
Links
- 208000037259 Amyloid Plaque Diseases 0.000 title claims abstract description 41
- 238000003384 imaging method Methods 0.000 title abstract description 8
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title description 19
- 230000027455 binding Effects 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 155
- 238000000034 method Methods 0.000 claims abstract description 63
- 230000002776 aggregation Effects 0.000 claims abstract description 8
- 238000004220 aggregation Methods 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
- -1 2- [2- (2- {2- [2- (4- {2- [4- (tert-butoxycarbonylmethylamino) phenyl] vinyl} phenoxy) ethoxy] ethoxy} ethoxy) ethoxy] ethyl methanesulfonic acid ester Chemical class 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 229910052740 iodine Inorganic materials 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052700 potassium Inorganic materials 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 239000012216 imaging agent Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 238000010668 complexation reaction Methods 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- UWPGGJPPQYTXTB-UHFFFAOYSA-N tert-butyl n-[4-[2-[4-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]phenyl]ethenyl]phenyl]-n-methylcarbamate Chemical compound C1=CC(N(C(=O)OC(C)(C)C)C)=CC=C1C=CC1=CC=C(OCCOCCOCCO)C=C1 UWPGGJPPQYTXTB-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 102000009091 Amyloidogenic Proteins Human genes 0.000 abstract description 9
- 108010048112 Amyloidogenic Proteins Proteins 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 3
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
- 210000004556 brain Anatomy 0.000 description 39
- 239000000243 solution Substances 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 238000000921 elemental analysis Methods 0.000 description 19
- 210000001519 tissue Anatomy 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 230000002285 radioactive effect Effects 0.000 description 13
- 235000021286 stilbenes Nutrition 0.000 description 13
- 238000012746 preparative thin layer chromatography Methods 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 238000011272 standard treatment Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 210000000988 bone and bone Anatomy 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 108090000765 processed proteins & peptides Proteins 0.000 description 6
- 238000012800 visualization Methods 0.000 description 6
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 5
- TYYCNSUODPEVQP-UHFFFAOYSA-N 8-[(4-fluorophenyl)sulfonylamino]-4-(3-pyridin-3-ylpropyl)octanoic acid Chemical compound C=1C=CN=CC=1CCCC(CCC(=O)O)CCCCNS(=O)(=O)C1=CC=C(F)C=C1 TYYCNSUODPEVQP-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- HPKJGHVHQWJOOT-ZJOUEHCJSA-N N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide Chemical compound C1C(CCCC1)C[C@H](NC(=O)C=1NC2=CC=CC=C2C=1)C(=O)N[C@@H](C[C@H]1C(=O)NCC1)C=O HPKJGHVHQWJOOT-ZJOUEHCJSA-N 0.000 description 5
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000010253 intravenous injection Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 238000009825 accumulation Methods 0.000 description 4
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
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- 102000004169 proteins and genes Human genes 0.000 description 4
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- 230000002829 reductive effect Effects 0.000 description 4
- DVWOYOSIEJRHKW-UIRZNSHLSA-M sodium (2S)-2-[[(2S)-2-[[(4,4-difluorocyclohexyl)-phenylmethoxy]carbonylamino]-4-methylpentanoyl]amino]-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonate Chemical compound FC1(CCC(CC1)C(OC(=O)N[C@H](C(=O)N[C@H](C(S(=O)(=O)[O-])O)C[C@H]1C(NCC1)=O)CC(C)C)C1=CC=CC=C1)F.[Na+] DVWOYOSIEJRHKW-UIRZNSHLSA-M 0.000 description 4
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- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
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- 230000002739 subcortical effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- GQRCCPYYDNJGRB-UHFFFAOYSA-N tert-butyl n-[4-[2-[4-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]phenyl]ethenyl]phenyl]-n-methylcarbamate Chemical compound C1=CC(N(C(=O)OC(C)(C)C)C)=CC=C1C=CC1=CC=C(OCCOCCOCCOCCOCCO)C=C1 GQRCCPYYDNJGRB-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- BFDBKMOZYNOTPK-UHFFFAOYSA-N vonoprazan Chemical compound C=1C=CN=CC=1S(=O)(=O)N1C=C(CNC)C=C1C1=CC=CC=C1F BFDBKMOZYNOTPK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
-
- 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
- A61K31/11—Aldehydes
- A61K31/115—Formaldehyde
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
-
- 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
- C07B59/001—Acyclic or carbocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Optics & Photonics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hospice & Palliative Care (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63669604P | 2004-12-17 | 2004-12-17 | |
| US68639505P | 2005-06-02 | 2005-06-02 | |
| PCT/US2005/045682 WO2006066104A2 (en) | 2004-12-17 | 2005-12-19 | Stilbene derivatives and their use for binding and imaging amyloid plaques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200701299A1 EA200701299A1 (ru) | 2007-12-28 |
| EA012334B1 true EA012334B1 (ru) | 2009-08-28 |
Family
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| EA200701299A EA012334B1 (ru) | 2004-12-17 | 2005-12-19 | Производные стильбена и их применение для связывания и визуализации амилоидных бляшек |
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|---|---|
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| BE (1) | BE2015C015I2 (enExample) |
| BR (1) | BRPI0516408B8 (enExample) |
| CA (1) | CA2591534C (enExample) |
| DK (1) | DK2213652T3 (enExample) |
| EA (1) | EA012334B1 (enExample) |
| ES (1) | ES2526655T3 (enExample) |
| FR (1) | FR15C0012I2 (enExample) |
| HU (1) | HUS1500014I1 (enExample) |
| IL (2) | IL183946A (enExample) |
| LT (1) | LTC2213652I2 (enExample) |
| LU (1) | LU92647I2 (enExample) |
| MX (1) | MX2007007380A (enExample) |
| NL (1) | NL300719I1 (enExample) |
| NO (1) | NO339195B1 (enExample) |
| NZ (1) | NZ555942A (enExample) |
| PL (1) | PL2213652T3 (enExample) |
| PT (1) | PT2213652E (enExample) |
| SG (1) | SG194363A1 (enExample) |
| SI (1) | SI2213652T1 (enExample) |
| WO (1) | WO2006066104A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2477726C1 (ru) * | 2011-10-18 | 2013-03-20 | Общество С Ограниченной Ответственностью "Ньювак" (Ооо "Ньювак") | Замещенные феноксиуксусные кислоты, их эфиры и амиды, включающие 2,6-диоксо-2,3,6,7-тетрагидро-1н-пурин-8-иловый фрагмент, - антагонисты аденозинового a2a рецептора и их применение |
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|---|---|---|---|---|
| AU2002323417B2 (en) * | 2001-08-27 | 2008-05-15 | The Trustees Of The University Of Pennsylvania | Stilbene derivatives and their use for binding and imaging amyloid plaques |
| WO2006078384A2 (en) * | 2004-12-17 | 2006-07-27 | The Trustees Of The University Of Pennsylvania | Stilbene derivatives and their use |
| CA2591534C (en) * | 2004-12-17 | 2013-08-06 | The Trustees Of The University Of Pennsylvania | Stilbene derivatives and their use for binding and imaging amyloid plaques |
| US20070031328A1 (en) * | 2005-06-24 | 2007-02-08 | Kung Hank F | Radiolabeled-pegylation of ligands for use as imaging agents |
| PL1999109T3 (pl) | 2006-03-30 | 2012-05-31 | Univ Pennsylvania | Pochodne styrylopirydyny i ich zastosowanie do wiązania i obrazowania blaszek amyloidowych |
| US20080253967A1 (en) * | 2007-04-13 | 2008-10-16 | Kung Hank F | Halo-Stilbene Derivatives And Their Use For Binding And Imaging Of Amyloid Plaques |
| WO2009001046A2 (en) * | 2007-06-22 | 2008-12-31 | The University Court Of The University Of Aberdeen | [11c]methoxy-radiolabelled 2,3',4,5'-tetramethylstilbene (tms) and its preparation and use |
| CA2699965A1 (en) * | 2007-07-04 | 2009-01-08 | Tohoku University | Pet probe having an alkoxy group substituted by fluorine and hydroxy group |
| US8779002B2 (en) * | 2007-10-15 | 2014-07-15 | Salk Institute For Biological Studies | Methods for treating a variety of diseases and conditions, and compounds useful therefor |
| EP2599763A1 (en) * | 2008-02-14 | 2013-06-05 | Siemens Molecular Imaging, Inc. | Novel imaging agents for detecting neurological dysfunction |
| US8932557B2 (en) | 2008-02-14 | 2015-01-13 | Eli Lilly And Company | Imaging agents for detecting neurological dysfunction |
| AU2009219406A1 (en) * | 2008-02-27 | 2009-09-03 | Avid Radiopharmaceuticals, Inc. | Gamma probe detection of amyloid plaque using radiolabeled A-beta binding compounds |
| US8557222B2 (en) * | 2008-04-04 | 2013-10-15 | Avid Radiopharmaceuticals, Inc. | Radiopharmaceutical imaging of neurodegenerative diseases |
| WO2010056900A1 (en) * | 2008-11-13 | 2010-05-20 | Avid Radiopharmaceuticals, Inc. | Histogram-based analysis method for the detection and diagnosis of neurodegenerative diseases |
| CN102292461A (zh) * | 2008-12-22 | 2011-12-21 | 拜耳先灵医药股份有限公司 | 使用交换树脂合成放射性核素标记的化合物的方法 |
| AU2009335049B2 (en) * | 2008-12-31 | 2015-07-16 | Avid Radiopharmaceuticals, Inc. | Synthesis of 18F-radiolabeled styrylpyridines from tosylate precursors and stable pharmaceutical compositions thereof |
| CU23844B1 (es) | 2009-04-17 | 2012-10-15 | Ct De Neurociencias De Cuba | Procedimiento de obtención de nuevos derivados de naftaleno para el diagnóstico in vivo de la enfermedad de alzheimer |
| US8968701B2 (en) | 2009-07-10 | 2015-03-03 | Piramal Imaging Sa | Usage of low to medium-pressure liquid chromatography for the purification of radiotracers |
| AU2010334929B2 (en) * | 2009-12-23 | 2015-04-23 | Lantheus Biosciences Ltd. | Formulations suitable for pet imaging with hydrophobic pet agents |
| CA2801530C (en) | 2010-06-04 | 2017-09-12 | Piramal Imaging Sa | Method for production of f-18 labeled amyloid beta ligands |
| BR112012030946A2 (pt) * | 2010-06-04 | 2016-11-01 | Piramal Imaging Sa | método para a produção de ligante para amiloide beta marcado com f-18 |
| TWI504414B (zh) * | 2010-06-04 | 2015-10-21 | Bayer Schering Pharma Ag | 生產Ｆ－１８標記之Ａβ配位體之方法 |
| EA201201647A1 (ru) | 2010-06-04 | 2013-05-30 | Пирамаль Имэджинг Са | Способ получения f-18 меченных лигандов бета-амилоида |
| EP3263136A1 (en) * | 2010-10-12 | 2018-01-03 | Mayo Foundation for Medical Education and Research | Imaging of meningiomas using stilbene, or biphenylalkyne derivatives |
| 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 |
| MY183997A (en) | 2011-06-21 | 2021-03-17 | Life Molecular Imaging Sa | Formulations of fluorinated stilbene suitable for pet imaging |
| KR101291037B1 (ko) * | 2011-10-12 | 2013-08-01 | 사회복지법인 삼성생명공익재단 | 레스베라트롤 유도체와 스티릴-오각형 방향족 화합물 및 이들의 베타-아밀로이드 플라그에 대한 결합제 및 진단영상제의 용도 |
| CA2852840A1 (en) | 2011-10-19 | 2013-04-25 | Piramal Imaging Sa | Improved method for production of f-18 labeled a.beta. ligands |
| CA2869398C (en) | 2012-04-10 | 2019-10-22 | Lantheus Medical Imaging, Inc. | Radiopharmaceutical synthesis methods |
| US9180212B2 (en) * | 2012-05-22 | 2015-11-10 | The Regents Of The University Of California | β-amyloid plaque imaging agents |
| CU20130027A7 (es) | 2013-02-28 | 2014-10-30 | Ct De Neurociencias De Cuba | Chaperoninas químicas como nuevos moduladores moleculares de la beta agregación proteica presente en las enfermedades conformacionales |
| JP6041751B2 (ja) * | 2013-05-07 | 2016-12-14 | 日本メジフィジックス株式会社 | スチリルピリジン誘導体化合物 |
| JP2014218454A (ja) * | 2013-05-07 | 2014-11-20 | 日本メジフィジックス株式会社 | スチリルピリジン誘導体化合物 |
| KR101891404B1 (ko) * | 2015-12-18 | 2018-08-24 | 주식회사 엘지화학 | 변성 단량체, 이를 포함하는 변성 중합체 및 이들의 제조방법 |
| US10675365B2 (en) | 2016-09-29 | 2020-06-09 | Korea Atomic Energy Research Institute | Curcumin derivative, method for producing same, and photo-acoustic imaging agent comprising same for detecting beta-amyloid plaque |
| TWI752098B (zh) | 2016-10-10 | 2022-01-11 | 美商亞雷生物製藥股份有限公司 | 作為ret激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
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| US5521213A (en) * | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
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| US4500507A (en) * | 1981-10-30 | 1985-02-19 | Wong Dennis W | Diagnostic composition for radiologic imaging of neoplasms in the body and method of preparation |
| JPS60247244A (ja) | 1984-05-22 | 1985-12-06 | Mitsubishi Paper Mills Ltd | 電子写真感光体 |
| DD231432A1 (de) | 1984-11-01 | 1985-12-24 | Univ Leipzig | Material zur silberfreien bildaufzeichnung |
| DD234666A1 (de) | 1984-11-01 | 1986-04-09 | Univ Leipzig | Verfahren zur herstellung von einfachen und substituierten 4-dimethylamino-alpha-halogenstilbenen |
| JPH06329566A (ja) | 1993-05-21 | 1994-11-29 | Asahi Glass Co Ltd | ジフルオロスチルベン誘導体化合物およびそれを含有する液晶組成物 |
| TW325458B (en) * | 1993-09-08 | 1998-01-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions comprising the same for anti-cancer |
| US5601801A (en) * | 1994-08-02 | 1997-02-11 | Merck Frosst Canada, Inc. | Radiolabelled angiotensin converting enzyme inhibitors |
| JP4022951B2 (ja) | 1997-08-06 | 2007-12-19 | 大日本インキ化学工業株式会社 | ジフルオロスチルベン誘導体の製造方法 |
| WO2001084937A1 (en) * | 2000-05-08 | 2001-11-15 | Novozymes A/S | Oxidoreductase mediated antimicrobial activity |
| AU2002323417B2 (en) * | 2001-08-27 | 2008-05-15 | The Trustees Of The University Of Pennsylvania | Stilbene derivatives and their use for binding and imaging amyloid plaques |
| KR100789847B1 (ko) * | 2004-12-15 | 2007-12-28 | (주)퓨쳐켐 | 알코올 용매하에서 유기플루오로 화합물의 제조방법 |
| WO2006078384A2 (en) * | 2004-12-17 | 2006-07-27 | The Trustees Of The University Of Pennsylvania | Stilbene derivatives and their use |
| CA2591534C (en) * | 2004-12-17 | 2013-08-06 | The Trustees Of The University Of Pennsylvania | Stilbene derivatives and their use for binding and imaging amyloid plaques |
| US20070031328A1 (en) * | 2005-06-24 | 2007-02-08 | Kung Hank F | Radiolabeled-pegylation of ligands for use as imaging agents |
-
2005
- 2005-12-19 CA CA2591534A patent/CA2591534C/en not_active Expired - Lifetime
- 2005-12-19 PT PT101616043T patent/PT2213652E/pt unknown
- 2005-12-19 ES ES10161604.3T patent/ES2526655T3/es not_active Expired - Lifetime
- 2005-12-19 EA EA200701299A patent/EA012334B1/ru not_active IP Right Cessation
- 2005-12-19 KR KR1020077016290A patent/KR101321619B1/ko not_active Expired - Lifetime
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- 2005-12-19 DK DK10161604.3T patent/DK2213652T3/en active
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- 2005-12-19 MX MX2007007380A patent/MX2007007380A/es active IP Right Grant
- 2005-12-19 WO PCT/US2005/045682 patent/WO2006066104A2/en not_active Ceased
- 2005-12-19 JP JP2007546948A patent/JP5128956B2/ja not_active Expired - Lifetime
- 2005-12-19 SG SG2013070958A patent/SG194363A1/en unknown
- 2005-12-19 BR BRPI0516408A patent/BRPI0516408B8/pt active IP Right Grant
- 2005-12-19 EP EP05854410A patent/EP1841465A4/en not_active Withdrawn
- 2005-12-19 US US11/305,333 patent/US7807135B2/en active Active
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- 2007-06-14 IL IL183946A patent/IL183946A/en active IP Right Grant
- 2007-07-16 NO NO20073650A patent/NO339195B1/no unknown
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- 2010-04-22 US US12/765,397 patent/US8465726B2/en not_active Expired - Lifetime
- 2010-05-31 IL IL206091A patent/IL206091A/en active IP Right Grant
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2015
- 2015-02-02 LT LTPA2015005C patent/LTC2213652I2/lt unknown
- 2015-02-04 LU LU92647C patent/LU92647I2/xx unknown
- 2015-02-11 FR FR15C0012C patent/FR15C0012I2/fr active Active
- 2015-02-12 NL NL300719C patent/NL300719I1/nl unknown
- 2015-03-10 BE BE2015C015C patent/BE2015C015I2/nl unknown
- 2015-03-18 HU HUS1500014C patent/HUS1500014I1/hu unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5521213A (en) * | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2477726C1 (ru) * | 2011-10-18 | 2013-03-20 | Общество С Ограниченной Ответственностью "Ньювак" (Ооо "Ньювак") | Замещенные феноксиуксусные кислоты, их эфиры и амиды, включающие 2,6-диоксо-2,3,6,7-тетрагидро-1н-пурин-8-иловый фрагмент, - антагонисты аденозинового a2a рецептора и их применение |
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