ES2841746T3 - Sondas para la imagen de la proteína de Huntington - Google Patents
Sondas para la imagen de la proteína de Huntington Download PDFInfo
- Publication number
- ES2841746T3 ES2841746T3 ES15836970T ES15836970T ES2841746T3 ES 2841746 T3 ES2841746 T3 ES 2841746T3 ES 15836970 T ES15836970 T ES 15836970T ES 15836970 T ES15836970 T ES 15836970T ES 2841746 T3 ES2841746 T3 ES 2841746T3
- Authority
- ES
- Spain
- Prior art keywords
- pyridin
- dihydro
- alkyl
- optionally substituted
- isoindol
- 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.)
- Active
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- 239000000523 sample Substances 0.000 title description 3
- 238000010377 protein imaging Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 64
- 125000003118 aryl group Chemical group 0.000 claims abstract description 58
- 239000012216 imaging agent Substances 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 27
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 18
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 16
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 8
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 8
- -1 cyano, methyl Chemical group 0.000 claims description 90
- 238000000034 method Methods 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 108090000623 proteins and genes Proteins 0.000 claims description 41
- 102000004169 proteins and genes Human genes 0.000 claims description 39
- 238000002600 positron emission tomography Methods 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 208000023105 Huntington disease Diseases 0.000 claims description 18
- 210000004556 brain Anatomy 0.000 claims description 17
- 210000004227 basal ganglia Anatomy 0.000 claims description 13
- 238000003384 imaging method Methods 0.000 claims description 12
- 230000004770 neurodegeneration Effects 0.000 claims description 11
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
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- 125000003277 amino group Chemical group 0.000 claims description 9
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 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
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
- 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
- 102000016252 Huntingtin Human genes 0.000 claims description 5
- 108050004784 Huntingtin Proteins 0.000 claims description 5
- 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 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 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 4
- 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 4
- AMAXXQKKZCHDNG-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C=1C=CC(N(N=1)C)=O Chemical compound COC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C=1C=CC(N(N=1)C)=O AMAXXQKKZCHDNG-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 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 3
- BEDGSVZKCWBILF-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=NC=CC=C1C#N Chemical compound COC=1C=CC(=NC=1)COC=1C=C2CN(CC2=CC=1)C1=NC=CC=C1C#N BEDGSVZKCWBILF-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 3
- 238000002059 diagnostic imaging Methods 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000024777 Prion disease Diseases 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- 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 57
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 125000003367 polycyclic group Chemical group 0.000 description 20
- 125000005843 halogen group Chemical group 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 125000004429 atom Chemical group 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 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
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000003419 tautomerization reaction Methods 0.000 description 12
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 10
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- 239000000284 extract Substances 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- DNWLQCBSEZHTMF-UHFFFAOYSA-N thiadiazolo[5,4-c]pyridine Chemical compound C1=NC=CC2=C1SN=N2 DNWLQCBSEZHTMF-UHFFFAOYSA-N 0.000 description 1
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- SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 1
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 1
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- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
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Classifications
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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
- A61K51/0459—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
-
- 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
- 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
-
- 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
-
- 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
-
- 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
-
- 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)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US201462043644P | 2014-08-29 | 2014-08-29 | |
| PCT/US2015/047396 WO2016033436A1 (en) | 2014-08-29 | 2015-08-28 | Probes for imaging huntingtin protein |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2841746T3 true ES2841746T3 (es) | 2021-07-09 |
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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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| US5726197A (en) * | 1992-11-02 | 1998-03-10 | Syntex (U.S.A.) Inc. | Isoindolinyl derivatives |
| IL146455A0 (en) | 1999-06-10 | 2002-07-25 | Warner Lambert Co | Method of inhibiting amyloid protein aggregation and imaging amyloid deposits using isoindoline derivatives |
| KR101011657B1 (ko) * | 2002-03-01 | 2011-01-28 | 다케다 야쿠힌 고교 가부시키가이샤 | 항우울제 |
| US7968569B2 (en) | 2002-05-17 | 2011-06-28 | Celgene Corporation | Methods for treatment of multiple myeloma using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione |
| US7320992B2 (en) * | 2003-08-25 | 2008-01-22 | Amgen Inc. | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
| US8110681B2 (en) * | 2006-03-17 | 2012-02-07 | The United States Of America As Represented By The Secretary, Department Of Health And Human Services | Compounds for the treatment of spinal muscular atrophy and other uses |
| EP2215074B1 (en) * | 2007-09-27 | 2014-02-19 | The United States of America, as Represented by the Secretary, Department of Health and Human Services | Isoindoline compounds for the treatment of spinal muscular atrophy and other uses |
| WO2009072581A1 (ja) * | 2007-12-05 | 2009-06-11 | Aska Pharmaceutical Co., Ltd. | ラクタム化合物又はその塩及びｐｐａｒ活性化剤 |
| WO2010104324A2 (ko) * | 2009-03-10 | 2010-09-16 | 한국과학기술연구원 | 베타-아밀로이드 집적체 및 피브릴에 우수한 결합 친화도를 가지는 할로겐화 이소인돌론 화합물, 및 이의 제조 방법 및 용도 |
| BR112014026283B1 (pt) * | 2012-04-25 | 2022-08-02 | Raqualia Pharma Inc | Compostos da fórmula (i), (ii), (iii), uso dos mesmos, composição farmacêutica, e processo para a preparação de uma composição farmacêutica |
| WO2015054317A1 (en) * | 2013-10-07 | 2015-04-16 | Kadmon Corporation, Llc | Rho kinase inhibitors |
| 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 |
| US11104691B2 (en) | 2014-08-29 | 2021-08-31 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
| 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 |
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2015
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2017
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- 2017-02-28 MX MX2021005891A patent/MX2021005891A/es unknown
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2020
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2021
- 2021-02-22 JP JP2021026146A patent/JP7042940B2/ja active Active
- 2021-06-21 US US17/353,611 patent/US12036291B2/en active Active
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