ES2781867T3 - 4-Azaindoles sustituidos y su utilización como moduladores del receptor GluN2B - Google Patents
4-Azaindoles sustituidos y su utilización como moduladores del receptor GluN2B Download PDFInfo
- Publication number
- ES2781867T3 ES2781867T3 ES16741469T ES16741469T ES2781867T3 ES 2781867 T3 ES2781867 T3 ES 2781867T3 ES 16741469 T ES16741469 T ES 16741469T ES 16741469 T ES16741469 T ES 16741469T ES 2781867 T3 ES2781867 T3 ES 2781867T3
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- Prior art keywords
- pyridine
- pyrrolo
- ethanone
- methyl
- fluoro
- Prior art date
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- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical class C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 title description 4
- 108010054200 NR2B NMDA receptor Proteins 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 878
- -1 3-azabicyclo [3.1.0] hexane-3-yl Chemical group 0.000 claims abstract description 529
- 125000005843 halogen group Chemical group 0.000 claims abstract description 85
- 150000003839 salts Chemical class 0.000 claims abstract description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 60
- 239000012453 solvate Substances 0.000 claims abstract description 35
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 31
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 31
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 30
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 25
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 10
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims abstract description 7
- 125000002541 furyl group Chemical group 0.000 claims abstract description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 6
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract description 6
- 125000000466 oxiranyl group Chemical group 0.000 claims abstract description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 6
- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 6
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 6
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims abstract description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 192
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 97
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 81
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 80
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 53
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 29
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 108010038912 Retinoid X Receptors Proteins 0.000 claims description 20
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 18
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 17
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 16
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- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 208000020401 Depressive disease Diseases 0.000 claims description 11
- 230000001404 mediated effect Effects 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 10
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
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- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 238000011161 development Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
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- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 206010003805 Autism Diseases 0.000 claims description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- LPIURYDEKDUCPE-UHFFFAOYSA-N acetaldehyde 2,2,2-trifluoroacetic acid Chemical compound CC=O.OC(=O)C(F)(F)F LPIURYDEKDUCPE-UHFFFAOYSA-N 0.000 claims description 3
- 208000018300 basal ganglia disease Diseases 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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- OFBZRPMIHPTAGU-UHFFFAOYSA-N 2-[2-methyl-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-morpholin-4-ylethanone Chemical compound CC1=CC2=NC=C(C=C2N1CC(=O)N1CCOCC1)C=1C=C(C=CC=1)C OFBZRPMIHPTAGU-UHFFFAOYSA-N 0.000 claims description 2
- CYXJITBNUHYULZ-UHFFFAOYSA-N 2-[6-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=CN2CC(=O)N1CCCC1 CYXJITBNUHYULZ-UHFFFAOYSA-N 0.000 claims description 2
- UEUMZKUBKBVHPT-UHFFFAOYSA-N 2-[6-(3,5-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-morpholin-4-ylethanone Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)C=CN2CC(=O)N1CCOCC1 UEUMZKUBKBVHPT-UHFFFAOYSA-N 0.000 claims description 2
- MGOYXMNOVHUQCC-UHFFFAOYSA-N 2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]acetic acid Chemical compound FC1=C(C=C(C=C1)C=1C=C2C(=NC=1)C=CN2CC(=O)O)C MGOYXMNOVHUQCC-UHFFFAOYSA-N 0.000 claims description 2
- MCUCKFZPDXZFNF-PKLMIRHRSA-N 2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-1-[(3R)-3-fluoropyrrolidin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.FC1=CC=C(C=C1)C=1C=C2C(=NC1)C=CN2CC(=O)N2C[C@@H](CC2)F MCUCKFZPDXZFNF-PKLMIRHRSA-N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
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- MCUCKFZPDXZFNF-NTISSMGPSA-N FC(C(=O)O)(F)F.FC1=CC=C(C=C1)C=1C=C2C(=NC1)C=CN2CC(=O)N2C[C@H](CC2)F Chemical compound FC(C(=O)O)(F)F.FC1=CC=C(C=C1)C=1C=C2C(=NC1)C=CN2CC(=O)N2C[C@H](CC2)F MCUCKFZPDXZFNF-NTISSMGPSA-N 0.000 claims description 2
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
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- DCPBVEYVXTZNEJ-UHFFFAOYSA-N 1-(2,2-dimethylmorpholin-4-yl)-2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.CC1(CN(CCO1)C(CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C)=O)C DCPBVEYVXTZNEJ-UHFFFAOYSA-N 0.000 claims 1
- PKZJNWXWVVQEFU-UHFFFAOYSA-N 1-(2,2-dimethylpyrrolidin-1-yl)-2-[6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.CC1(N(CCC1)C(CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C)=O)C PKZJNWXWVVQEFU-UHFFFAOYSA-N 0.000 claims 1
- ZVVBCUSNXGXCEG-UHFFFAOYSA-N 1-(3,3-difluoropyrrolidin-1-yl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1(CN(CC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O)F ZVVBCUSNXGXCEG-UHFFFAOYSA-N 0.000 claims 1
- BAJLKKDCRRARCS-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound FC1=CC=C(C=C1)C(CN1C=CC2=NC=C(C=C21)C1=CC=C(C=C1)F)=O BAJLKKDCRRARCS-UHFFFAOYSA-N 0.000 claims 1
- ZOQKLKUOEXHOMB-UHFFFAOYSA-N 1-(cyclobutylmethyl)-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridine 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C1(CCC1)CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C ZOQKLKUOEXHOMB-UHFFFAOYSA-N 0.000 claims 1
- LLNDWQBNIZRFOB-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridine 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.C1(CC1)CN1C=CC2=NC=C(C=C21)C2=CC(=C(C=C2)F)C LLNDWQBNIZRFOB-UHFFFAOYSA-N 0.000 claims 1
- NNWNAHVVXRDDEN-UHFFFAOYSA-N 1-(pyridazin-3-ylmethyl)-6-[3-(trifluoromethyl)phenyl]pyrrolo[3,2-b]pyridine Chemical compound N1=NC(=CC=C1)CN1C=CC2=NC=C(C=C21)C1=CC(=CC=C1)C(F)(F)F NNWNAHVVXRDDEN-UHFFFAOYSA-N 0.000 claims 1
- RAIQMPVQGITNBA-UHFFFAOYSA-N 1-[3-fluoro-6-(3-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC(=CC=C1)F)CC(C(C)C)=O RAIQMPVQGITNBA-UHFFFAOYSA-N 0.000 claims 1
- IGTQSEFCWIRZEC-UHFFFAOYSA-N 1-[3-fluoro-6-(3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C=1C=C(C=CC=1)C)CC(C(C)C)=O IGTQSEFCWIRZEC-UHFFFAOYSA-N 0.000 claims 1
- WPJPMOGYAKUTFH-UHFFFAOYSA-N 1-[3-fluoro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC(=C(C=C1)F)C)CC(C(C)C)=O WPJPMOGYAKUTFH-UHFFFAOYSA-N 0.000 claims 1
- IZUICHIJLGXBSD-UHFFFAOYSA-N 1-[3-fluoro-6-(4-fluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC1=CN(C=2C1=NC=C(C=2)C1=CC=C(C=C1)F)CC(C(C)C)=O IZUICHIJLGXBSD-UHFFFAOYSA-N 0.000 claims 1
- MKIYBOZZDZCJMA-UHFFFAOYSA-N 1-[6-(3,4-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-3,3-dimethylbutan-2-one Chemical compound FC=1C=C(C=CC=1F)C=1C=C2C(=NC=1)C=CN2CC(C(C)(C)C)=O MKIYBOZZDZCJMA-UHFFFAOYSA-N 0.000 claims 1
- KPXIRVJUXJPNPQ-UHFFFAOYSA-N 1-[6-(3,5-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-3,3-dimethylbutan-2-one Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)C=CN2CC(C(C)(C)C)=O KPXIRVJUXJPNPQ-UHFFFAOYSA-N 0.000 claims 1
- QFXYCGGWYMINDD-UHFFFAOYSA-N 1-[6-(3,5-difluorophenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound FC=1C=C(C=C(C=1)F)C=1C=C2C(=NC=1)C=CN2CC(C(C)C)=O QFXYCGGWYMINDD-UHFFFAOYSA-N 0.000 claims 1
- DSICMCNZSSQYOX-UHFFFAOYSA-N 1-[6-(3-ethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-3,3-dimethylbutan-2-one Chemical compound C(C)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=CN2CC(C(C)(C)C)=O DSICMCNZSSQYOX-UHFFFAOYSA-N 0.000 claims 1
- CNHWBISBMPBFFD-UHFFFAOYSA-N 1-[6-(3-ethylphenyl)pyrrolo[3,2-b]pyridin-1-yl]-3-methylbutan-2-one Chemical compound C(C)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)C=CN2CC(C(C)C)=O CNHWBISBMPBFFD-UHFFFAOYSA-N 0.000 claims 1
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- HCEUIWXYBYMLDU-UHFFFAOYSA-N 1-cyclopropyl-2-(6-phenylpyrrolo[3,2-b]pyridin-1-yl)ethanone Chemical compound C1(CC1)C(CN1C=CC2=NC=C(C=C21)C1=CC=CC=C1)=O HCEUIWXYBYMLDU-UHFFFAOYSA-N 0.000 claims 1
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- DZLMSOUHOZYOGY-UHFFFAOYSA-N 1-cyclopropyl-2-[3-fluoro-6-(4-fluoro-3-methylphenyl)pyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound C1(CC1)C(CN1C=C(C2=NC=C(C=C21)C1=CC(=C(C=C1)F)C)F)=O DZLMSOUHOZYOGY-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562190416P | 2015-07-09 | 2015-07-09 | |
| PCT/US2016/041339 WO2017007938A1 (en) | 2015-07-09 | 2016-07-07 | Substituted 4-azaindoles and their use as glun2b receptor modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2781867T3 true ES2781867T3 (es) | 2020-09-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16741469T Active ES2781867T3 (es) | 2015-07-09 | 2016-07-07 | 4-Azaindoles sustituidos y su utilización como moduladores del receptor GluN2B |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US9963447B2 (enExample) |
| EP (1) | EP3319963B1 (enExample) |
| JP (2) | JP6964576B2 (enExample) |
| KR (1) | KR20180026760A (enExample) |
| CN (1) | CN108026094B (enExample) |
| AU (1) | AU2016291158B2 (enExample) |
| BR (1) | BR112018000468A2 (enExample) |
| CA (1) | CA2991765C (enExample) |
| CY (1) | CY1123007T1 (enExample) |
| DK (1) | DK3319963T3 (enExample) |
| EA (1) | EA033197B1 (enExample) |
| ES (1) | ES2781867T3 (enExample) |
| HR (1) | HRP20200410T1 (enExample) |
| HU (1) | HUE047460T2 (enExample) |
| IL (1) | IL256758A (enExample) |
| LT (1) | LT3319963T (enExample) |
| MA (1) | MA42397B1 (enExample) |
| MD (1) | MD3319963T2 (enExample) |
| MX (1) | MX2018000352A (enExample) |
| PL (1) | PL3319963T3 (enExample) |
| PT (1) | PT3319963T (enExample) |
| SI (1) | SI3319963T1 (enExample) |
| SM (1) | SMT202000134T1 (enExample) |
| WO (1) | WO2017007938A1 (enExample) |
| ZA (1) | ZA201800827B (enExample) |
Families Citing this family (14)
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| HUE049277T2 (hu) | 2014-08-15 | 2020-09-28 | Janssen Pharmaceuticals Inc | Triazolok mint NR2B receptor inhibitorok |
| WO2016025918A1 (en) | 2014-08-15 | 2016-02-18 | Janssen Pharmaceuticals, Inc. | Pyrazoles |
| BR112018000468A2 (pt) | 2015-07-09 | 2018-09-18 | Janssen Pharmaceutica Nv | 4-azaindóis substituídos e seu uso como moduladores do receptor de glun2b |
| SG11201806750WA (en) | 2016-02-10 | 2018-09-27 | Janssen Pharmaceutica Nv | Substituted 1,2,3-triazoles as nr2b-selective nmda modulators |
| TW201819376A (zh) | 2016-10-06 | 2018-06-01 | 比利時商健生藥品公司 | 經取代之１Ｈ－咪唑並［４，５－ｂ］吡啶－２（３Ｈ）－酮及其作為ＧＬＵＮ２Ｂ受體調節劑之用途 |
| US11447503B2 (en) | 2019-06-14 | 2022-09-20 | Janssen Pharmaceutica Nv | Pyridine carbamates and their use as GLUN2B receptor modulators |
| WO2019193516A2 (en) | 2018-04-04 | 2019-10-10 | Janssen Pharmaceutica Nv | Substituted pyridine and pyrimidines and their use as glun2b receptor modulators |
| CN113950357A (zh) | 2019-06-14 | 2022-01-18 | 詹森药业有限公司 | 吡嗪氨基甲酸酯及其作为GluN2B受体调节剂的用途 |
| KR20220020917A (ko) * | 2019-06-14 | 2022-02-21 | 얀센 파마슈티카 엔.브이. | 치환된 피라졸로[4,3-b]피리딘 및 GLUN2B 수용체 조절제로서의 이들의 용도 |
| TW202115054A (zh) * | 2019-06-14 | 2021-04-16 | 比利時商健生藥品公司 | 經取代的雜芳族吡唑并－吡啶及其作為ｇｌｕｎ２ｂ受體調節劑的用途 |
| BR112021024117A2 (pt) | 2019-06-14 | 2022-03-22 | Janssen Pharmaceutica Nv | Pirazolo-pirazinas substituídas e seu uso como moduladores do receptor de glun2b |
| CN113993868A (zh) | 2019-06-14 | 2022-01-28 | 詹森药业有限公司 | 取代的吡唑并吡啶酰胺以及它们作为glun2b受体调节剂的用途 |
| PH12021552839A1 (en) | 2019-06-14 | 2022-10-03 | Janssen Pharmaceutica Nv | Substituted pyrazolo-pyridine amides and their use as glun2b receptor modulators |
| CN114621125B (zh) * | 2020-12-14 | 2024-07-09 | 中国科学技术大学 | Nlrp3炎症小体抑制剂及其应用 |
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| EP1490364B1 (en) * | 2002-03-28 | 2007-09-26 | Eisai R&D Management Co., Ltd. | 7-azaindoles as inhibitors of c-jun n-terminal kinases for the treatment of neurodegenerative disorders |
| US20070185178A1 (en) | 2004-02-18 | 2007-08-09 | Aatrazeneca Ab | Triazole compounds and their use as metabotropic glutamate receptor antagonists |
| US20060183758A1 (en) * | 2005-02-17 | 2006-08-17 | Cb Research And Development, Inc. | Method for synthesis of AZA-annelated pyrroles, thiophenes, and furans |
| US7807704B2 (en) * | 2006-03-30 | 2010-10-05 | Chemocentryx, Inc. | Bicyclic, nitrogen-containing compounds modulating CXCR4 and/or CCXCKR2 |
| PE20090717A1 (es) * | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| JP5615700B2 (ja) | 2007-05-25 | 2014-10-29 | アボット ゲーエムベーハー ウント カンパニー カーゲー | 代謝型グルタミン酸受容体２（ｍｇｌｕ２受容体）の陽性調節剤としての複素環化合物 |
| WO2009005821A1 (en) | 2007-07-03 | 2009-01-08 | Edward Scott Carlson | Support apparatus for climbing plants |
| US20090270359A1 (en) | 2007-08-30 | 2009-10-29 | Takeda Pharmaceutical Company Limited | Substituted pyrazole derivatives |
| US20100249164A1 (en) | 2007-10-31 | 2010-09-30 | Renger John J | Modulation of sleep with nr2b receptor antagonists |
| KR20100135847A (ko) | 2008-03-27 | 2010-12-27 | 에보텍 뉴로사이언시즈 게엠베하 | Ｎｍｄａ ｎｒ２ｂ―서브타입 선택적 길항제를 사용한 질병 치료 방법 |
| BRPI0917540A2 (pt) | 2008-08-05 | 2015-11-17 | Daiichi Sankyo Co Ltd | composto, sal farmacologicamente aceitavél, composição farmacêutica, e, uso de um composto ou sal farmacologicamente aceitável |
| BRPI0920354A2 (pt) * | 2008-10-16 | 2017-06-27 | Addex Pharmaceuticals Sa | derivados de indol e benzomorfolina como moduladores de receptores de glutamato metabotrópicos |
| EP2379561B1 (en) | 2008-11-25 | 2015-11-04 | University Of Rochester | Mlk inhibitors and methods of use |
| TWI625121B (zh) * | 2009-07-13 | 2018-06-01 | 基利科學股份有限公司 | 調節細胞凋亡信號之激酶的抑制劑 |
| EP2579717A4 (en) | 2010-06-09 | 2013-12-11 | Merck Sharp & Dohme | POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 |
| US9434743B2 (en) | 2012-03-02 | 2016-09-06 | Takeda Pharmaceutical Company Limited | Indazole derivatives |
| WO2014124651A1 (en) * | 2013-02-15 | 2014-08-21 | Københavns Universitet | Pyrrolidine-2-carboxylic acid derivatives as iglur antagonists |
| CN105189481A (zh) * | 2013-03-13 | 2015-12-23 | 艾伯维公司 | 吡啶cdk9激酶抑制剂 |
| RU2680100C9 (ru) * | 2013-03-15 | 2019-04-18 | Плексксикон Инк. | Гетероциклические соединения и их применения |
| CN103626767A (zh) * | 2013-12-04 | 2014-03-12 | 上海药明康德新药开发有限公司 | 区域选择性的氮杂吲哚及其合成方法 |
| WO2016025918A1 (en) | 2014-08-15 | 2016-02-18 | Janssen Pharmaceuticals, Inc. | Pyrazoles |
| HUE049277T2 (hu) | 2014-08-15 | 2020-09-28 | Janssen Pharmaceuticals Inc | Triazolok mint NR2B receptor inhibitorok |
| BR112018000468A2 (pt) | 2015-07-09 | 2018-09-18 | Janssen Pharmaceutica Nv | 4-azaindóis substituídos e seu uso como moduladores do receptor de glun2b |
| SG11201806750WA (en) | 2016-02-10 | 2018-09-27 | Janssen Pharmaceutica Nv | Substituted 1,2,3-triazoles as nr2b-selective nmda modulators |
| TW201819376A (zh) | 2016-10-06 | 2018-06-01 | 比利時商健生藥品公司 | 經取代之１Ｈ－咪唑並［４，５－ｂ］吡啶－２（３Ｈ）－酮及其作為ＧＬＵＮ２Ｂ受體調節劑之用途 |
-
2016
- 2016-07-07 BR BR112018000468-5A patent/BR112018000468A2/pt not_active Application Discontinuation
- 2016-07-07 WO PCT/US2016/041339 patent/WO2017007938A1/en not_active Ceased
- 2016-07-07 DK DK16741469.7T patent/DK3319963T3/da active
- 2016-07-07 SM SM20200134T patent/SMT202000134T1/it unknown
- 2016-07-07 AU AU2016291158A patent/AU2016291158B2/en not_active Ceased
- 2016-07-07 HU HUE16741469A patent/HUE047460T2/hu unknown
- 2016-07-07 SI SI201630594T patent/SI3319963T1/sl unknown
- 2016-07-07 LT LTEP16741469.7T patent/LT3319963T/lt unknown
- 2016-07-07 CA CA2991765A patent/CA2991765C/en active Active
- 2016-07-07 PT PT167414697T patent/PT3319963T/pt unknown
- 2016-07-07 HR HRP20200410TT patent/HRP20200410T1/hr unknown
- 2016-07-07 MA MA42397A patent/MA42397B1/fr unknown
- 2016-07-07 EA EA201890245A patent/EA033197B1/ru not_active IP Right Cessation
- 2016-07-07 EP EP16741469.7A patent/EP3319963B1/en active Active
- 2016-07-07 MD MDE20180505T patent/MD3319963T2/ro not_active IP Right Cessation
- 2016-07-07 CN CN201680052507.9A patent/CN108026094B/zh active Active
- 2016-07-07 PL PL16741469T patent/PL3319963T3/pl unknown
- 2016-07-07 JP JP2018500737A patent/JP6964576B2/ja active Active
- 2016-07-07 MX MX2018000352A patent/MX2018000352A/es unknown
- 2016-07-07 ES ES16741469T patent/ES2781867T3/es active Active
- 2016-07-07 KR KR1020187003560A patent/KR20180026760A/ko not_active Withdrawn
- 2016-07-08 US US15/205,632 patent/US9963447B2/en active Active
-
2018
- 2018-01-07 IL IL256758A patent/IL256758A/en unknown
- 2018-02-08 ZA ZA2018/00827A patent/ZA201800827B/en unknown
- 2018-03-20 US US15/926,440 patent/US10377753B2/en active Active
-
2020
- 2020-03-24 CY CY20201100280T patent/CY1123007T1/el unknown
-
2021
- 2021-08-27 JP JP2021138906A patent/JP7369743B2/ja active Active
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