KR102410760B1 - 헌팅틴 단백질을 영상화하기 위한 프로브 - Google Patents
헌팅틴 단백질을 영상화하기 위한 프로브 Download PDFInfo
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- KR102410760B1 KR102410760B1 KR1020177008418A KR20177008418A KR102410760B1 KR 102410760 B1 KR102410760 B1 KR 102410760B1 KR 1020177008418 A KR1020177008418 A KR 1020177008418A KR 20177008418 A KR20177008418 A KR 20177008418A KR 102410760 B1 KR102410760 B1 KR 102410760B1
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- amino
- dihydro
- isoindol
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000003384 imaging method Methods 0.000 title claims description 13
- 102000016252 Huntingtin Human genes 0.000 title claims description 5
- 108050004784 Huntingtin Proteins 0.000 title claims description 5
- 239000000523 sample Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 65
- 239000012216 imaging agent Substances 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- -1 cyano, amino Chemical group 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 108090000623 proteins and genes Proteins 0.000 claims description 34
- 102000004169 proteins and genes Human genes 0.000 claims description 32
- 238000002600 positron emission tomography Methods 0.000 claims description 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 208000023105 Huntington disease Diseases 0.000 claims description 17
- 210000004556 brain Anatomy 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
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- 208000037273 Pathologic Processes Diseases 0.000 claims description 11
- 238000002595 magnetic resonance imaging Methods 0.000 claims description 11
- 230000009054 pathological process Effects 0.000 claims description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- REHYONXLVUWYNH-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=C(C=NC=C1)C#N Chemical compound COC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=C(C=NC=C1)C#N REHYONXLVUWYNH-UHFFFAOYSA-N 0.000 claims description 6
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- VNSRTBKAWDJHOP-UHFFFAOYSA-N N1=CN=CC(=C1)COC=1C=C2CN(CC2=CC=1)C1=C(C=NC=C1)C#N Chemical compound N1=CN=CC(=C1)COC=1C=C2CN(CC2=CC=1)C1=C(C=NC=C1)C#N VNSRTBKAWDJHOP-UHFFFAOYSA-N 0.000 claims description 6
- NVXYCFAAMKMACA-UHFFFAOYSA-N N1=CN=CC(=C1)COC=1C=C2CN(CC2=CC=1)C1=NC=CC=C1C#N Chemical compound N1=CN=CC(=C1)COC=1C=C2CN(CC2=CC=1)C1=NC=CC=C1C#N NVXYCFAAMKMACA-UHFFFAOYSA-N 0.000 claims description 6
- DCRUQOOGKROGBZ-UHFFFAOYSA-N OC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=C(C=NC=C1)C#N Chemical compound OC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=C(C=NC=C1)C#N DCRUQOOGKROGBZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- RWEYYSNPCVRJSQ-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=C2CN(CC2=CC=1)C1=NC=NC=C1C#N Chemical compound C(C1=CC=CC=C1)OC=1C=C2CN(CC2=CC=1)C1=NC=NC=C1C#N RWEYYSNPCVRJSQ-UHFFFAOYSA-N 0.000 claims description 5
- HUGKALXNRWBIQE-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2CN(C(C2=CC=1)=O)C1=CC=NC=C1 Chemical compound COC=1C=CC(=NC=1)COC=1C=C2CN(C(C2=CC=1)=O)C1=CC=NC=C1 HUGKALXNRWBIQE-UHFFFAOYSA-N 0.000 claims description 5
- KQORCPPKKYMCPM-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=NC=NC=C1C#N Chemical compound COC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=NC=NC=C1C#N KQORCPPKKYMCPM-UHFFFAOYSA-N 0.000 claims description 5
- QRTPOXXFPDZCES-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=CC=NC=C1 Chemical compound COC=1N=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=CC=NC=C1 QRTPOXXFPDZCES-UHFFFAOYSA-N 0.000 claims description 5
- JWFNVWRPBFZRLQ-UHFFFAOYSA-N OC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=NC=NC=C1C#N Chemical compound OC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=NC=NC=C1C#N JWFNVWRPBFZRLQ-UHFFFAOYSA-N 0.000 claims description 5
- 238000013170 computed tomography imaging Methods 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 102000014461 Ataxins Human genes 0.000 claims description 2
- 108010078286 Ataxins Proteins 0.000 claims description 2
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 2
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 2
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 6
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- 125000003277 amino group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 229910052799 carbon Inorganic materials 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- 125000003367 polycyclic group Chemical group 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
- 125000005843 halogen group Chemical group 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
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- 125000004429 atom Chemical group 0.000 description 15
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 238000003419 tautomerization reaction Methods 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 8
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 8
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 150000002431 hydrogen Chemical group 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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- 235000019253 formic acid Nutrition 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 210000004940 nucleus Anatomy 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
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- 125000002619 bicyclic group Chemical group 0.000 description 6
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- 238000000746 purification Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
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- QQLPPRIZUPEKMV-UHFFFAOYSA-N 2-(2-phenylethenyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1C=CC1=CC=CC=C1 QQLPPRIZUPEKMV-UHFFFAOYSA-N 0.000 description 4
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- 230000000875 corresponding effect Effects 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- CNUNPQXDDJYAEE-UHFFFAOYSA-N (5-methoxypyrazin-2-yl)methanol Chemical compound COC1=CN=C(CO)C=N1 CNUNPQXDDJYAEE-UHFFFAOYSA-N 0.000 description 2
- YSGIZFIQWAPBLG-UHFFFAOYSA-N (5-methoxypyridin-2-yl)methanol Chemical compound COC1=CC=C(CO)N=C1 YSGIZFIQWAPBLG-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 description 2
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- XTBAPWCYTNCZTO-UHFFFAOYSA-N 1H-isoindolone Natural products C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 description 2
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 2
- KSBXDCBRSKRVDC-UHFFFAOYSA-N 2-(chloromethyl)-5-methoxypyridine Chemical compound COC1=CC=C(CCl)N=C1 KSBXDCBRSKRVDC-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- A61K51/0459—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
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- 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
- C07D513/12—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 three hetero rings
- C07D513/14—Ortho-condensed systems
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- 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)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
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- Medicinal Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
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| US11104691B2 (en) | 2014-08-29 | 2021-08-31 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
| EP3186233B8 (en) | 2014-08-29 | 2021-09-29 | CHDI Foundation, Inc. | Probes for imaging huntingtin protein |
| EA037275B1 (ru) | 2014-08-29 | 2021-03-03 | Сиэйчдиай Фаундэйшн, Инк. | Зонды для визуализации белка хантингтина |
| SG11201701580XA (en) | 2014-08-29 | 2017-03-30 | Chdi Foundation Inc | Probes for imaging huntingtin protein |
| DK3340796T3 (da) | 2015-08-28 | 2021-07-26 | Chdi Foundation Inc | Sonder til afbildning af huntingtin-protein |
| US10865201B2 (en) | 2016-09-12 | 2020-12-15 | Valo Health, Inc. | Bicyclic compounds useful as GPR120 modulators |
| EP3509587B1 (en) | 2016-09-12 | 2023-12-06 | Valo Health, Inc. | Monocyclic compounds useful as gpr120 modulators |
| WO2020176424A1 (en) | 2019-02-25 | 2020-09-03 | Chdi Foundation, Inc. | Compounds for targeting mutant huntingtin protein and uses thereof |
| US11992535B2 (en) | 2019-12-18 | 2024-05-28 | Chdi Foundation, Inc. | Compounds and probes for imaging huntingtin protein |
| BR112022025238A2 (pt) * | 2020-06-11 | 2023-02-14 | Chdi Foundation Inc | Compostos heterocíclicos e agentes de imageamento para formar imagem da proteína huntingtina |
| WO2022216947A1 (en) * | 2021-04-08 | 2022-10-13 | Chdi Foundation, Inc. | Isoindolinone compounds and imaging agents for imaging huntingtin protein |
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| WO2000076969A1 (en) | 1999-06-10 | 2000-12-21 | Warner-Lambert Company | Method of inhibiting amyloid protein aggregation and imaging amyloid deposits using isoindoline derivatives |
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