EA039923B1 - Зонды для визуализации белка хантингтина - Google Patents
Зонды для визуализации белка хантингтина Download PDFInfo
- Publication number
- EA039923B1 EA039923B1 EA201790400A EA201790400A EA039923B1 EA 039923 B1 EA039923 B1 EA 039923B1 EA 201790400 A EA201790400 A EA 201790400A EA 201790400 A EA201790400 A EA 201790400A EA 039923 B1 EA039923 B1 EA 039923B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- imidazo
- pyridine
- methoxy
- methylamino
- carbonitrile
- Prior art date
Links
- 102000016252 Huntingtin Human genes 0.000 title claims abstract description 6
- 108050004784 Huntingtin Proteins 0.000 title claims abstract description 6
- 238000003384 imaging method Methods 0.000 title claims description 14
- 239000000523 sample Substances 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 160
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 29
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 210000004556 brain Anatomy 0.000 claims abstract description 17
- 239000012216 imaging agent Substances 0.000 claims abstract description 9
- 208000037273 Pathologic Processes Diseases 0.000 claims abstract description 6
- 230000009054 pathological process Effects 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims abstract description 5
- -1 methoxy, hydroxyl Chemical group 0.000 claims description 138
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 229910052717 sulfur Inorganic materials 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000005842 heteroatom Chemical group 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 30
- KIYOXVPZRXLLDR-UHFFFAOYSA-N imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound C1=C(C#N)C=CN2C=CN=C21 KIYOXVPZRXLLDR-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 238000002600 positron emission tomography Methods 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 208000023105 Huntington disease Diseases 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 15
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
- 210000004227 basal ganglia Anatomy 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- ZHXPGZQNJIWLDI-UHFFFAOYSA-N COC1=CC=C2OC(=CC2=C1)C1=C(N(C)C)N2C=CC(=CC2=N1)C#N Chemical compound COC1=CC=C2OC(=CC2=C1)C1=C(N(C)C)N2C=CC(=CC2=N1)C#N ZHXPGZQNJIWLDI-UHFFFAOYSA-N 0.000 claims description 5
- RCFTZJKADPJHHQ-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC1=CC=C(C=N1)C=1N=C2N(C=CC(=C2)C#N)C=1NC Chemical compound COC=1N=CC(=NC=1)COC1=CC=C(C=N1)C=1N=C2N(C=CC(=C2)C#N)C=1NC RCFTZJKADPJHHQ-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- YKJICSLWCNWWFD-UHFFFAOYSA-N FC=1C=CC=2N(C=1)C(=C(N=2)C=1OC2=C(C=1)C=C(C=C2)O)NC Chemical compound FC=1C=CC=2N(C=1)C(=C(N=2)C=1OC2=C(C=1)C=C(C=C2)O)NC YKJICSLWCNWWFD-UHFFFAOYSA-N 0.000 claims description 5
- KZMRYMBBISTXTB-UHFFFAOYSA-N NC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC(OCCF)=CC=C2O1 Chemical compound NC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC(OCCF)=CC=C2O1 KZMRYMBBISTXTB-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000001514 detection method Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- RVYYSUMYBRASNN-UHFFFAOYSA-N CN(CCOC=1C=CC2=C(C=C(O2)C=2N=C3N(C=CC(=C3)C#N)C=2NC)C=1)C Chemical compound CN(CCOC=1C=CC2=C(C=C(O2)C=2N=C3N(C=CC(=C3)C#N)C=2NC)C=1)C RVYYSUMYBRASNN-UHFFFAOYSA-N 0.000 claims description 4
- XOAVMCHKAMGNEK-UHFFFAOYSA-N CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC(OC)=CC=C2O1 Chemical compound CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC(OC)=CC=C2O1 XOAVMCHKAMGNEK-UHFFFAOYSA-N 0.000 claims description 4
- ZWJAOVYQCAOPFB-UHFFFAOYSA-N CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC(OCCF)=CC=C2O1 Chemical compound CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC(OCCF)=CC=C2O1 ZWJAOVYQCAOPFB-UHFFFAOYSA-N 0.000 claims description 4
- ZWENFEJTOGNBJA-UHFFFAOYSA-N CNC1=C(N=C2C=CC=CN12)C1=CC2=CC(F)=CC=C2O1 Chemical compound CNC1=C(N=C2C=CC=CN12)C1=CC2=CC(F)=CC=C2O1 ZWENFEJTOGNBJA-UHFFFAOYSA-N 0.000 claims description 4
- POEHWOYCAHVSBZ-UHFFFAOYSA-N CNC1=C(N=C2N1C=CC(=C2)C#N)C1=CC(=CC=C1)C1=NC=CN=C1 Chemical compound CNC1=C(N=C2N1C=CC(=C2)C#N)C1=CC(=CC=C1)C1=NC=CN=C1 POEHWOYCAHVSBZ-UHFFFAOYSA-N 0.000 claims description 4
- MEZXIRVFTDTRHP-UHFFFAOYSA-N COC1=CC=C2OC(=CC2=C1)C1=C(NCCN(C)C)N2C=CC(=CC2=N1)C#N Chemical compound COC1=CC=C2OC(=CC2=C1)C1=C(NCCN(C)C)N2C=CC(=CC2=N1)C#N MEZXIRVFTDTRHP-UHFFFAOYSA-N 0.000 claims description 4
- KSZOWDYOWNPZHE-UHFFFAOYSA-N OCCNC1=C(N=C2N1C=CC=C2)C=1OC2=C(C=1)C=C(C=C2)O Chemical compound OCCNC1=C(N=C2N1C=CC=C2)C=1OC2=C(C=1)C=C(C=C2)O KSZOWDYOWNPZHE-UHFFFAOYSA-N 0.000 claims description 4
- 238000012879 PET imaging Methods 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 238000002591 computed tomography Methods 0.000 claims description 4
- 238000002595 magnetic resonance imaging Methods 0.000 claims description 4
- ZPMWXDOTBGBOJU-UHFFFAOYSA-N 2-(5-bromo-1-benzofuran-2-yl)-3-(methylamino)imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound BrC=1C=CC2=C(C=C(O2)C=2N=C3N(C=CC(=C3)C#N)C=2NC)C=1 ZPMWXDOTBGBOJU-UHFFFAOYSA-N 0.000 claims description 3
- PYKSYJJOIRRNGO-VMPITWQZSA-N 2-[(E)-2-(4-methoxyphenyl)ethenyl]-3-(methylamino)imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound COC1=CC=C(C=C1)/C=C/C=1N=C2N(C=CC(=C2)C#N)C=1NC PYKSYJJOIRRNGO-VMPITWQZSA-N 0.000 claims description 3
- VJFJMCSJLDRDRR-UHFFFAOYSA-N 2-[5-[(5-methoxypyrazin-2-yl)methoxy]pyridin-2-yl]-3-(methylamino)imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound COC=1N=CC(=NC=1)COC=1C=CC(=NC=1)C=1N=C2N(C=CC(=C2)C#N)C=1NC VJFJMCSJLDRDRR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- GSDQMGHKNLDKGS-UHFFFAOYSA-N C(#C)C1=CC=2N(C=C1)C(=C(N=2)C=1OC2=C(C=1)C=C(C=C2)OC)NC Chemical compound C(#C)C1=CC=2N(C=C1)C(=C(N=2)C=1OC2=C(C=1)C=C(C=C2)OC)NC GSDQMGHKNLDKGS-UHFFFAOYSA-N 0.000 claims description 3
- VTOJVPBRAFYQFG-UHFFFAOYSA-N C(#N)C1=CC=2N(C=C1)C(=C(N=2)C1=CC=2CN(CCC=2O1)C(=O)OC(C)(C)C)NC Chemical compound C(#N)C1=CC=2N(C=C1)C(=C(N=2)C1=CC=2CN(CCC=2O1)C(=O)OC(C)(C)C)NC VTOJVPBRAFYQFG-UHFFFAOYSA-N 0.000 claims description 3
- SJLUGUZBAJMBQF-UHFFFAOYSA-N CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC(OCC2=CC=CN=C2)=CC=C1 Chemical compound CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC(OCC2=CC=CN=C2)=CC=C1 SJLUGUZBAJMBQF-UHFFFAOYSA-N 0.000 claims description 3
- RBKJEYGQBCKLGM-UHFFFAOYSA-N CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC(F)=CC=C2O1 Chemical compound CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC(F)=CC=C2O1 RBKJEYGQBCKLGM-UHFFFAOYSA-N 0.000 claims description 3
- NPCDZMJJDWIPMB-UHFFFAOYSA-N CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC=C(OC)C=C2O1 Chemical compound CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC2=CC=C(OC)C=C2O1 NPCDZMJJDWIPMB-UHFFFAOYSA-N 0.000 claims description 3
- AJYCMRRMPQDPSD-UHFFFAOYSA-N CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC=C(Br)O1 Chemical compound CNC1=C(N=C2C=C(C=CN12)C#N)C1=CC=C(Br)O1 AJYCMRRMPQDPSD-UHFFFAOYSA-N 0.000 claims description 3
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- LYLXYCVZZZHIKK-UHFFFAOYSA-N CNC1=C(N=C2N1C=CC(=C2)C#N)C1=CC=C(C=C1)OCC#C Chemical compound CNC1=C(N=C2N1C=CC(=C2)C#N)C1=CC=C(C=C1)OCC#C LYLXYCVZZZHIKK-UHFFFAOYSA-N 0.000 claims description 3
- KYYQKHITWXMMTA-UHFFFAOYSA-N COC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C#N)C=1NC Chemical compound COC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C#N)C=1NC KYYQKHITWXMMTA-UHFFFAOYSA-N 0.000 claims description 3
- GECCHUDLYZTUMC-UHFFFAOYSA-N FC1=CC=2N(C=C1)C(=C(N=2)C=1OC2=C(C=1)C=C(C=C2)O)NC Chemical compound FC1=CC=2N(C=C1)C(=C(N=2)C=1OC2=C(C=1)C=C(C=C2)O)NC GECCHUDLYZTUMC-UHFFFAOYSA-N 0.000 claims description 3
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- OIKDVDYRHLAKRU-UHFFFAOYSA-N OC=1C=CC2=C(C=C(O2)C=2N=C3N(C=CC(=C3)C#N)C=2NC)C=1 Chemical compound OC=1C=CC2=C(C=C(O2)C=2N=C3N(C=CC(=C3)C#N)C=2NC)C=1 OIKDVDYRHLAKRU-UHFFFAOYSA-N 0.000 claims description 3
- SYARCGGAUZTGOC-UHFFFAOYSA-N S1C=2N(C(=C1)COC1=CC=C(C=C1)C=1N=C3N(C=CC(=C3)C#N)C=1NC)CCN=2 Chemical compound S1C=2N(C(=C1)COC1=CC=C(C=C1)C=1N=C3N(C=CC(=C3)C#N)C=1NC)CCN=2 SYARCGGAUZTGOC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 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
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- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 2
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 238000002059 diagnostic imaging Methods 0.000 claims description 2
- MPRMRYWPRROMHA-UHFFFAOYSA-N 2-(5-methoxy-1-methylbenzimidazol-2-yl)-3-(methylamino)imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound COC1=CC2=C(N(C(=N2)C=2N=C3N(C=CC(=C3)C#N)C=2NC)C)C=C1 MPRMRYWPRROMHA-UHFFFAOYSA-N 0.000 claims 2
- XAWNDICSNACTDK-UHFFFAOYSA-N 3-(methylamino)-2-[3-(pyridin-3-ylmethoxymethyl)phenyl]imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound CNC1=C(N=C2N1C=CC(=C2)C#N)C1=CC(=CC=C1)COCC=1C=NC=CC=1 XAWNDICSNACTDK-UHFFFAOYSA-N 0.000 claims 2
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- A61K51/04—Organic compounds
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- 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
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- A61K51/0453—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- 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
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- 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
- A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
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- Peptides Or Proteins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| SG11201701578YA (en) | 2014-08-29 | 2017-03-30 | Chdi Foundation Inc | Probes for imaging huntingtin protein |
| SG11201701580XA (en) | 2014-08-29 | 2017-03-30 | Chdi Foundation Inc | Probes for imaging huntingtin protein |
| PL3197277T3 (pl) | 2014-08-29 | 2022-04-04 | Chdi Foundation, Inc. | Sondy do obrazowania molekularnego białka huntingtyny |
| CA2995847C (en) | 2015-08-28 | 2024-05-28 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
| AU2018346962A1 (en) * | 2017-10-12 | 2020-05-28 | BCN Biosciences L.L.C. | Methods of treating radiation induced gastrointestinal syndrome |
| WO2020176424A1 (en) | 2019-02-25 | 2020-09-03 | Chdi Foundation, Inc. | Compounds for targeting mutant huntingtin protein and uses thereof |
| CA3138873C (en) | 2019-05-09 | 2024-01-09 | Kyle Bradley Pascual CLAGG | Synthesis of labeled imidazo[1,2-a]pyrimidines |
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| US20110171739A1 (en) * | 2008-09-23 | 2011-07-14 | Wista Laboratories Ltd. | Ligands for aggregated tau molecules |
| WO2015044095A1 (en) * | 2013-09-26 | 2015-04-02 | F. Hoffmann-La Roche Ag | Imidazo[1,2-a]pyridin-7-amines as imaging tools |
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| WO2008059714A1 (en) * | 2006-11-17 | 2008-05-22 | Nihon Medi-Physics Co., Ltd. | Novel compounds with affinity for amyloid |
| CN101595108A (zh) * | 2006-11-30 | 2009-12-02 | 日本医事物理股份有限公司 | 对淀粉状蛋白具有亲和性的新化合物 |
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| KR20140040722A (ko) * | 2011-05-20 | 2014-04-03 | 니혼 메디피직스 가부시키가이샤 | 신규 아밀로이드 친화성 화합물 |
| IN2014DN00185A (enExample) * | 2011-06-24 | 2015-07-10 | Nihon Mediphysics Co Ltd | |
| JP2013237655A (ja) * | 2012-05-17 | 2013-11-28 | Kyoto Univ | コンフォメーション病診断用分子プローブ |
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| WO2014139882A1 (en) | 2013-03-14 | 2014-09-18 | Galapagos Nv | Compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders |
| SG11201701580XA (en) | 2014-08-29 | 2017-03-30 | Chdi Foundation Inc | Probes for imaging huntingtin protein |
| PL3197277T3 (pl) | 2014-08-29 | 2022-04-04 | Chdi Foundation, Inc. | Sondy do obrazowania molekularnego białka huntingtyny |
| HRP20211778T1 (hr) | 2014-08-29 | 2022-03-18 | Chdi Foundation, Inc. | Kontrastna sredstva za slikovnu dijagnostiku huntingtin proteina |
| SG11201701578YA (en) | 2014-08-29 | 2017-03-30 | Chdi Foundation Inc | Probes for imaging huntingtin protein |
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