CA2873963C - Carboline and carbazole based imaging agents for detecting neurological dysfunction - Google Patents
Carboline and carbazole based imaging agents for detecting neurological dysfunction Download PDFInfo
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- CA2873963C CA2873963C CA2873963A CA2873963A CA2873963C CA 2873963 C CA2873963 C CA 2873963C CA 2873963 A CA2873963 A CA 2873963A CA 2873963 A CA2873963 A CA 2873963A CA 2873963 C CA2873963 C CA 2873963C
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title description 78
- 239000012216 imaging agent Substances 0.000 title description 10
- 230000009251 neurologic dysfunction Effects 0.000 title description 2
- 208000015015 neurological dysfunction Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 154
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 46
- 238000003384 imaging method Methods 0.000 claims abstract description 23
- 210000005013 brain tissue Anatomy 0.000 claims abstract description 22
- 241000124008 Mammalia Species 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LTQKXJQXVGFYEJ-UHFFFAOYSA-N 7-(3-fluoropropyl)-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(CCCF)C=C3NC2=C1 LTQKXJQXVGFYEJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- KOZHNZIZUPCYIY-UHFFFAOYSA-N 7-(2-fluoroethyl)-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(CCF)C=C3NC2=C1 KOZHNZIZUPCYIY-UHFFFAOYSA-N 0.000 claims 1
- WYTGDRQOERRVOD-UHFFFAOYSA-N 7-(2-nitroethyl)-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(CC[N+](=O)[O-])C=C3NC2=C1 WYTGDRQOERRVOD-UHFFFAOYSA-N 0.000 claims 1
- GUBGZQXFESJSEM-UHFFFAOYSA-N 7-(3-fluoropropoxy)-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(OCCCF)C=C3NC2=C1 GUBGZQXFESJSEM-UHFFFAOYSA-N 0.000 claims 1
- SLACXXPWBNDWSW-UHFFFAOYSA-N 7-(3-nitropropyl)-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(CCC[N+](=O)[O-])C=C3NC2=C1 SLACXXPWBNDWSW-UHFFFAOYSA-N 0.000 claims 1
- HCOLWFHEOAJVJC-UHFFFAOYSA-N 7-[2-(2-fluoroethoxy)ethoxy]-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(OCCOCCF)C=C3NC2=C1 HCOLWFHEOAJVJC-UHFFFAOYSA-N 0.000 claims 1
- PGQPLORRJVHERS-UHFFFAOYSA-N 7-[2-(2-fluoroethoxy)ethoxymethyl]-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(COCCOCCF)C=C3NC2=C1 PGQPLORRJVHERS-UHFFFAOYSA-N 0.000 claims 1
- NEKSMXSTDNEBFB-UHFFFAOYSA-N 7-[2-[2-(2-fluoroethoxy)ethoxy]ethoxy]-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(OCCOCCOCCF)C=C3NC2=C1 NEKSMXSTDNEBFB-UHFFFAOYSA-N 0.000 claims 1
- BTZWEODKMIMOLZ-UHFFFAOYSA-N 7-[2-[2-(2-fluoroethoxy)ethoxy]ethyl]-5h-pyrido[4,3-b]indole Chemical compound C1=NC=C2C3=CC=C(CCOCCOCCF)C=C3NC2=C1 BTZWEODKMIMOLZ-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 63
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- 125000001475 halogen functional group Chemical group 0.000 abstract 2
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- 125000005843 halogen group Chemical group 0.000 description 92
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- 238000002360 preparation method Methods 0.000 description 58
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 30
- 101150041968 CDC13 gene Proteins 0.000 description 29
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 24
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- 208000037259 Amyloid Plaque Diseases 0.000 description 22
- 239000012043 crude product Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 19
- 238000010828 elution Methods 0.000 description 19
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
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- 241000699670 Mus sp. Species 0.000 description 18
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 18
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 18
- 239000012267 brine Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
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- 229910052739 hydrogen Inorganic materials 0.000 description 15
- IAVCEBMLYVGBLA-UHFFFAOYSA-N 2-[1-[6-[2-fluoroethyl(methyl)amino]naphthalen-2-yl]ethylidene]propanedinitrile Chemical compound C1=C(C(C)=C(C#N)C#N)C=CC2=CC(N(CCF)C)=CC=C21 IAVCEBMLYVGBLA-UHFFFAOYSA-N 0.000 description 14
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- LSODCCFQUIMPIG-UHFFFAOYSA-N tert-butyl 2-[formyl(methyl)amino]-7-hydroxycarbazole-9-carboxylate Chemical compound OC1=CC=C2C3=CC=C(N(C=O)C)C=C3N(C(=O)OC(C)(C)C)C2=C1 LSODCCFQUIMPIG-UHFFFAOYSA-N 0.000 description 1
- WJGWOUVJOHLKSO-UHFFFAOYSA-N tert-butyl 2-[formyl(methyl)amino]-7-phenylmethoxycarbazole-9-carboxylate Chemical compound C=1C(N(C=O)C)=CC=C(C2=CC=3)C=1N(C(=O)OC(C)(C)C)C2=CC=3OCC1=CC=CC=C1 WJGWOUVJOHLKSO-UHFFFAOYSA-N 0.000 description 1
- SLQBJTZWOXLOAE-UHFFFAOYSA-N tert-butyl 7-(2-hydroxyethyl)-1,5-dihydropyrrolo[3,2-i]isoquinoline-5-carboxylate Chemical compound OCCC1=CN=CC23C1=CC(C=C3C=CN2)C(=O)OC(C)(C)C SLQBJTZWOXLOAE-UHFFFAOYSA-N 0.000 description 1
- OSCNJFAGWRCOCE-UHFFFAOYSA-N tert-butyl n-(2-phenylmethoxy-9h-pyrido[2,3-b]indol-7-yl)carbamate Chemical compound C=1C(NC(=O)OC(C)(C)C)=CC=C(C2=CC=3)C=1NC2=NC=3OCC1=CC=CC=C1 OSCNJFAGWRCOCE-UHFFFAOYSA-N 0.000 description 1
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- HRVLUGFFZLDSGT-UHFFFAOYSA-N tert-butyl n-[7-[2-[2-(2-fluoroethoxy)ethoxy]ethoxy]-9h-carbazol-2-yl]carbamate Chemical compound FCCOCCOCCOC1=CC=C2C3=CC=C(NC(=O)OC(C)(C)C)C=C3NC2=C1 HRVLUGFFZLDSGT-UHFFFAOYSA-N 0.000 description 1
- UXWVQHXKKOGTSY-UHFFFAOYSA-N tert-butyl phenyl carbonate Chemical compound CC(C)(C)OC(=O)OC1=CC=CC=C1 UXWVQHXKKOGTSY-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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- 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
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0446—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0455—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
-
- 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
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
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| US13/477,095 US8932557B2 (en) | 2008-02-14 | 2012-05-22 | Imaging agents for detecting neurological dysfunction |
| US13/477,095 | 2012-05-22 | ||
| PCT/US2012/061912 WO2013176698A1 (en) | 2012-05-22 | 2012-10-25 | Carboline and carbazole based imaging agents for detecting neurological dysfunction |
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| CA2873963A1 CA2873963A1 (en) | 2013-11-28 |
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| CO (1) | CO7131359A2 (enExample) |
| ES (1) | ES2792830T3 (enExample) |
| WO (1) | WO2013176698A1 (enExample) |
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| US10662193B2 (en) * | 2014-01-21 | 2020-05-26 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyloid-like proteins |
| CN106414445B (zh) * | 2014-04-22 | 2020-07-03 | 蒙特利尔大学 | 化合物及其在扩增造血干细胞和/或造血祖细胞中的应用 |
| LT3143011T (lt) | 2014-05-13 | 2021-05-10 | F. Hoffmann-La Roche Ag | Deuterinti heterocikliniai junginiai ir jų naudojimas kaip vaizdinimo agentų |
| EA036518B1 (ru) * | 2015-02-02 | 2020-11-18 | Юсб Байофарма Спрл | Производные 9h-пирролодипиридина |
| KR20170123306A (ko) * | 2015-03-04 | 2017-11-07 | 고쿠리츠 다이가쿠 호진 교토 다이가쿠 | 방사성 요오드 표지 피리도[1,2-a]벤조이미다졸 유도체 화합물 |
| TW201707726A (zh) | 2015-08-19 | 2017-03-01 | 國立大學法人京都大學 | 放射性鹵素標誌吡啶并［１，２－ａ］苯并咪唑衍生物化合物 |
| AU2016351609B2 (en) | 2015-11-13 | 2019-08-08 | Eli Lilly And Company | Azetidine derivatives for tau imaging |
| EP3487545A1 (en) | 2016-07-22 | 2019-05-29 | AC Immune S.A. | Compounds for imaging tau protein aggregates |
| US10835624B2 (en) | 2016-07-22 | 2020-11-17 | Ac Immune S.A. | Compounds for imaging Tau protein aggregates |
| WO2018024643A1 (en) | 2016-08-02 | 2018-02-08 | Ucb Biopharma Sprl | 9h-pyrrolo-dipyridine derivatives |
| WO2018024642A1 (en) | 2016-08-02 | 2018-02-08 | Ucb Biopharma Sprl | 9h-pyrrolo-dipyridine derivatives |
| IL290809B2 (en) * | 2016-11-01 | 2024-01-01 | Arvinas Operations Inc | Tau-protein targeting protacs and associated methods of use |
| CN109884194A (zh) * | 2017-12-06 | 2019-06-14 | 新疆维吾尔药业有限责任公司 | 一种药用植物的分离方法及其产品和应用 |
| US11306089B2 (en) | 2018-01-24 | 2022-04-19 | Life Molecular Imaging Limited | Gamma-carboline compounds for the detection of Tau aggregates |
| EP3743426A1 (en) | 2018-01-24 | 2020-12-02 | AC Immune SA | Azacarboline compounds for the detection of tau aggregates |
| CN108409634B (zh) * | 2018-05-10 | 2021-04-27 | 曲阜师范大学 | 咔唑类荧光胺类化合物标记试剂、合成和应用 |
| EP3841100A1 (en) | 2018-08-20 | 2021-06-30 | Arvinas Operations, Inc. | Proteolysis targeting chimeric (protac) compound with e3 ubiquitin ligase binding activity and targeting alpha-synuclein protein for treating neurodegenerative diseases |
| KR102215255B1 (ko) * | 2019-06-12 | 2021-02-15 | 한국과학기술연구원 | 타우 응집체에 선택적으로 결합하는 형광 탐침자로서 유효한 신규 화합물 및 이의 제조 방법 |
| JP7548992B2 (ja) | 2019-07-17 | 2024-09-10 | アルビナス・オペレーションズ・インコーポレイテッド | タウタンパク質標的化化合物および関連する使用方法 |
| US11618751B1 (en) | 2022-03-25 | 2023-04-04 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives |
| US11319319B1 (en) | 2021-04-07 | 2022-05-03 | Ventus Therapeutics U.S., Inc. | Compounds for inhibiting NLRP3 and uses thereof |
| CN116003402B (zh) * | 2021-11-02 | 2025-08-29 | 上海如絮生物科技有限公司 | 一种三环类化合物、其中间体、制备方法和应用 |
| CN114539250B (zh) * | 2022-03-04 | 2023-08-29 | 上海裕兰生物科技有限公司 | 一种阿尔兹海默症PET-tau示踪剂的制备方法 |
| US12331048B2 (en) | 2022-10-31 | 2025-06-17 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors |
| EP4658651A1 (en) | 2023-02-02 | 2025-12-10 | Eli Lilly and Company | Novel compounds for tau imaging |
| CN117050070B (zh) * | 2023-07-05 | 2025-10-14 | 湘潭大学 | 一种荧光探针及其制备方法和在Aβ检测中的应用 |
| WO2025155625A1 (en) | 2024-01-16 | 2025-07-24 | Eli Lilly And Company | Novel compounds for tau imaging |
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| WO2006005063A2 (en) * | 2004-06-30 | 2006-01-12 | Smithkline Beecham Corporation | Methods and compositions |
| FR2885905A1 (fr) * | 2005-05-23 | 2006-11-24 | Trophos Sa | Nouveaux composes chimiques et leurs utilisations comme medicament |
| DE102006062203A1 (de) * | 2006-12-22 | 2008-06-26 | Curacyte Discovery Gmbh | Substituierte 5H-Pyrimido[5,4-b]indole als Induktoren der Apoptose bei B-CLL Zellen |
| WO2008132454A1 (en) * | 2007-04-26 | 2008-11-06 | Ge Healthcare Limited | Carbolines and their use as imaging agents |
| PT2247558T (pt) * | 2008-02-14 | 2022-03-21 | Lilly Co Eli | Novos agentes de imagiologia para deteção de disfunção neurológica |
| KR20110046503A (ko) * | 2008-07-24 | 2011-05-04 | 지멘스 메디컬 솔루션즈 유에스에이, 인크. | Ａｄ 병인을 확인하기에 유용한 영상화제 |
| JP2012051804A (ja) * | 2008-12-26 | 2012-03-15 | Kyoto Univ | Ｅｇ５阻害剤 |
| US8691187B2 (en) * | 2009-03-23 | 2014-04-08 | Eli Lilly And Company | Imaging agents for detecting neurological disorders |
| CN102438660A (zh) * | 2009-03-23 | 2012-05-02 | 美国西门子医疗解决公司 | 用于检测神经障碍的显像剂 |
| US10639608B2 (en) * | 2010-04-08 | 2020-05-05 | Siemens Medical Solutions Usa, Inc. | System, device and method for preparing tracers and transferring materials during radiosynthesis |
| JP5585382B2 (ja) * | 2010-10-22 | 2014-09-10 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20150002854A (ko) | 2015-01-07 |
| WO2013176698A1 (en) | 2013-11-28 |
| CN107011342A (zh) | 2017-08-04 |
| EP2852572A1 (en) | 2015-04-01 |
| KR101609504B1 (ko) | 2016-04-05 |
| ES2792830T3 (es) | 2020-11-12 |
| CO7131359A2 (es) | 2014-12-01 |
| AU2012381042A1 (en) | 2014-11-20 |
| JP2015517572A (ja) | 2015-06-22 |
| CA2873963A1 (en) | 2013-11-28 |
| JP5976206B2 (ja) | 2016-08-23 |
| AU2012381042B2 (en) | 2015-10-01 |
| EP2852572B1 (en) | 2020-04-01 |
| CN104781234A (zh) | 2015-07-15 |
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