CA2610873A1 - Tetrahydroquinolinones et leur utilisation comme modulateurs de recepteurs metabotropique de glutamate - Google Patents
Tetrahydroquinolinones et leur utilisation comme modulateurs de recepteurs metabotropique de glutamate Download PDFInfo
- Publication number
- CA2610873A1 CA2610873A1 CA002610873A CA2610873A CA2610873A1 CA 2610873 A1 CA2610873 A1 CA 2610873A1 CA 002610873 A CA002610873 A CA 002610873A CA 2610873 A CA2610873 A CA 2610873A CA 2610873 A1 CA2610873 A1 CA 2610873A1
- Authority
- CA
- Canada
- Prior art keywords
- quinolin
- dihydro
- dimethyl
- ylethynyl
- phenylethynyl
- 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.)
- Granted
Links
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title abstract 2
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title abstract 2
- 150000003530 tetrahydroquinolines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- -1 ethynyl-substituted tetrahydroquinolinone Chemical class 0.000 claims abstract 14
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 230000002265 prevention Effects 0.000 claims abstract 4
- 230000001154 acute effect Effects 0.000 claims abstract 2
- 230000001684 chronic effect Effects 0.000 claims abstract 2
- 239000000460 chlorine Chemical group 0.000 claims 26
- 229910052801 chlorine Inorganic materials 0.000 claims 26
- 229910052731 fluorine Inorganic materials 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 16
- 125000001246 bromo group Chemical group Br* 0.000 claims 16
- 239000011737 fluorine Substances 0.000 claims 16
- 125000001153 fluoro group Chemical group F* 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 15
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 229910052794 bromium Inorganic materials 0.000 claims 10
- 125000002541 furyl group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000002883 imidazolyl group Chemical group 0.000 claims 10
- 125000000842 isoxazolyl group Chemical group 0.000 claims 10
- 125000002757 morpholinyl group Chemical group 0.000 claims 10
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 10
- 125000002971 oxazolyl group Chemical group 0.000 claims 10
- 125000003386 piperidinyl group Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims 10
- 125000000335 thiazolyl group Chemical group 0.000 claims 10
- 125000001544 thienyl group Chemical group 0.000 claims 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000002393 azetidinyl group Chemical group 0.000 claims 8
- 229910052740 iodine Inorganic materials 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 150000004677 hydrates Chemical class 0.000 claims 6
- 230000003287 optical effect Effects 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 4
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 4
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- XNVDHQYDSCNZML-UHFFFAOYSA-N 2-[2-(2-phenyl-1,3-thiazol-5-yl)ethynyl]-7,8-dihydro-6h-quinolin-5-one Chemical compound C=1C=C2C(=O)CCCC2=NC=1C#CC(S1)=CN=C1C1=CC=CC=C1 XNVDHQYDSCNZML-UHFFFAOYSA-N 0.000 claims 3
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- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 3
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- 208000010877 cognitive disease Diseases 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- QLVQNCUDTHFEPO-UHFFFAOYSA-N 2-[2-(3-fluorophenyl)ethynyl]-7,7-dimethyl-6,8-dihydroquinolin-5-one;2-[2-(3-methoxyphenyl)ethynyl]-7,7-dimethyl-6,8-dihydroquinolin-5-one Chemical compound N1=C2CC(C)(C)CC(=O)C2=CC=C1C#CC1=CC=CC(F)=C1.COC1=CC=CC(C#CC=2N=C3CC(C)(C)CC(=O)C3=CC=2)=C1 QLVQNCUDTHFEPO-UHFFFAOYSA-N 0.000 claims 2
- PQIPQTFRKQAFKG-UHFFFAOYSA-N 7,7-dimethyl-2-[2-(1,3-oxazol-5-yl)ethynyl]-6,8-dihydroquinolin-5-one;2-[2-(2-phenyl-1,3-oxazol-5-yl)ethynyl]-7,8-dihydro-6h-quinolin-5-one Chemical compound N1=C2CC(C)(C)CC(=O)C2=CC=C1C#CC1=CN=CO1.C=1C=C2C(=O)CCCC2=NC=1C#CC(O1)=CN=C1C1=CC=CC=C1 PQIPQTFRKQAFKG-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- POXKAIBLBPVHSW-UHFFFAOYSA-N BrC=1C=C(C=CC1)C#CC1=NC=2CC(CC(C2C=C1)=O)(C)C.ClC=1C=C(C=CC1)C#CC1=NC=2CC(CC(C2C=C1)=O)(C)C Chemical compound BrC=1C=C(C=CC1)C#CC1=NC=2CC(CC(C2C=C1)=O)(C)C.ClC=1C=C(C=CC1)C#CC1=NC=2CC(CC(C2C=C1)=O)(C)C POXKAIBLBPVHSW-UHFFFAOYSA-N 0.000 claims 2
- NETJLSVFWHJZNP-UHFFFAOYSA-N C1(=CC(=CC=C1)C#CC1=NC=2CCCC(C2C=C1)=O)C.N1=CC(=CC=C1)C#CC1=NC=2CCCC(C2C=C1)=O.C1(=CC=CC=C1)C#CC1=NC=2CCCC(C2C=C1)=O Chemical compound C1(=CC(=CC=C1)C#CC1=NC=2CCCC(C2C=C1)=O)C.N1=CC(=CC=C1)C#CC1=NC=2CCCC(C2C=C1)=O.C1(=CC=CC=C1)C#CC1=NC=2CCCC(C2C=C1)=O NETJLSVFWHJZNP-UHFFFAOYSA-N 0.000 claims 2
- AHXXHJCLJTYXSP-UHFFFAOYSA-N CC1(CC(C=2C=CC(=NC2C1)C#CC=1C=NC=CC1)=O)C.O1C=NC=C1C#CC1=NC=2CCCC(C2C=C1)=O.S1C=NC=C1C#CC1=NC=2CCCC(C2C=C1)=O Chemical compound CC1(CC(C=2C=CC(=NC2C1)C#CC=1C=NC=CC1)=O)C.O1C=NC=C1C#CC1=NC=2CCCC(C2C=C1)=O.S1C=NC=C1C#CC1=NC=2CCCC(C2C=C1)=O AHXXHJCLJTYXSP-UHFFFAOYSA-N 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- YCUZIWUOCSLOOY-UHFFFAOYSA-N FC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O.COC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O.OC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O Chemical compound FC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O.COC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O.OC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O YCUZIWUOCSLOOY-UHFFFAOYSA-N 0.000 claims 2
- 208000001914 Fragile X syndrome Diseases 0.000 claims 2
- 208000004454 Hyperalgesia Diseases 0.000 claims 2
- DWSMCWUEZIVSGM-UHFFFAOYSA-N O=C1C=2C=CC(=NC2CCC1)C#CC=1C=C(C#N)C=CC1.BrC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O.ClC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O Chemical compound O=C1C=2C=CC(=NC2CCC1)C#CC=1C=C(C#N)C=CC1.BrC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O.ClC=1C=C(C=CC1)C#CC1=NC=2CCCC(C2C=C1)=O DWSMCWUEZIVSGM-UHFFFAOYSA-N 0.000 claims 2
- UWBIMCLHNNQQQB-UHFFFAOYSA-N OC=1C=C(C=CC1)C#CC1=NC=2CC(CC(C2C=C1)=O)(C)C.CC1(CC(C=2C=CC(=NC2C1)C#CC=1C=C(C=CC1)C)=O)C Chemical compound OC=1C=C(C=CC1)C#CC1=NC=2CC(CC(C2C=C1)=O)(C)C.CC1(CC(C=2C=CC(=NC2C1)C#CC=1C=C(C=CC1)C)=O)C UWBIMCLHNNQQQB-UHFFFAOYSA-N 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000018756 Variant Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000005881 bovine spongiform encephalopathy Diseases 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 230000037410 cognitive enhancement Effects 0.000 claims 2
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- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 230000004112 neuroprotection Effects 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
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- 208000024891 symptom Diseases 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- PEMXOKOYRLFDDT-UHFFFAOYSA-N 2-(2-pyridin-2-ylethynyl)-7,8-dihydro-6h-quinolin-5-one Chemical compound C=1C=C2C(=O)CCCC2=NC=1C#CC1=CC=CC=N1 PEMXOKOYRLFDDT-UHFFFAOYSA-N 0.000 claims 1
- QMEDLAZYJXJINI-UHFFFAOYSA-N 2-[2-(1,3,4-oxadiazol-2-yl)ethynyl]-7,8-dihydro-6h-quinolin-5-one Chemical compound C=1C=C2C(=O)CCCC2=NC=1C#CC1=NN=CO1 QMEDLAZYJXJINI-UHFFFAOYSA-N 0.000 claims 1
- IICLTQRYRFSOHN-UHFFFAOYSA-N 2-[2-(1,3,4-thiadiazol-2-yl)ethynyl]-7,8-dihydro-6h-quinolin-5-one Chemical compound C=1C=C2C(=O)CCCC2=NC=1C#CC1=NN=CS1 IICLTQRYRFSOHN-UHFFFAOYSA-N 0.000 claims 1
- GTVYIZYSMKVYAN-UHFFFAOYSA-N 2-[2-(1,3-oxazol-2-yl)ethynyl]-7,8-dihydro-6h-quinolin-5-one Chemical compound C=1C=C2C(=O)CCCC2=NC=1C#CC1=NC=CO1 GTVYIZYSMKVYAN-UHFFFAOYSA-N 0.000 claims 1
- SDATUZQSEBHCAT-UHFFFAOYSA-N 2-[2-(1,3-thiazol-2-yl)ethynyl]-7,8-dihydro-6h-quinolin-5-one Chemical compound C=1C=C2C(=O)CCCC2=NC=1C#CC1=NC=CS1 SDATUZQSEBHCAT-UHFFFAOYSA-N 0.000 claims 1
- OWGWDIPIBGISDF-UHFFFAOYSA-N 2-[2-(2h-tetrazol-5-yl)ethynyl]-7,8-dihydro-6h-quinolin-5-one Chemical compound C=1C=C2C(=O)CCCC2=NC=1C#CC1=NN=NN1 OWGWDIPIBGISDF-UHFFFAOYSA-N 0.000 claims 1
- ZJFXBSKAHWJPQZ-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)ethynyl]-6,6-dimethyl-7,8-dihydroquinolin-5-one Chemical compound C=1C=C2C(=O)C(C)(C)CCC2=NC=1C#CC1=CC=CC(Cl)=C1 ZJFXBSKAHWJPQZ-UHFFFAOYSA-N 0.000 claims 1
- YROKDIOYNZGTMR-UHFFFAOYSA-N 2-[2-(3-fluorophenyl)ethynyl]-6,6-dimethyl-7,8-dihydroquinolin-5-one Chemical compound C=1C=C2C(=O)C(C)(C)CCC2=NC=1C#CC1=CC=CC(F)=C1 YROKDIOYNZGTMR-UHFFFAOYSA-N 0.000 claims 1
- CBNSFYLAWVPDRL-UHFFFAOYSA-N 2-[2-(3-hydroxyphenyl)ethynyl]-6,6-dimethyl-7,8-dihydroquinolin-5-one Chemical compound C=1C=C2C(=O)C(C)(C)CCC2=NC=1C#CC1=CC=CC(O)=C1 CBNSFYLAWVPDRL-UHFFFAOYSA-N 0.000 claims 1
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- AZKTVIVFHLROFO-UHFFFAOYSA-N 2-[2-(3-morpholin-4-ylphenyl)ethynyl]-7,8-dihydro-6h-quinolin-5-one Chemical compound C=1C=C2C(=O)CCCC2=NC=1C#CC(C=1)=CC=CC=1N1CCOCC1 AZKTVIVFHLROFO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/20—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/GB2005/003285 WO2007023242A1 (fr) | 2005-08-24 | 2005-08-24 | Tétrahydroquinolinones et leur usage en tant que modulateurs des récepteurs de glutamate métabotropiques |
GBPCT/GB2005/003285 | 2005-08-24 | ||
PCT/GB2006/003170 WO2007023290A1 (fr) | 2005-08-24 | 2006-08-24 | Tétrahydroquinolinones et leur utilisation comme modulateurs de récepteurs métabotropique de glutamate |
Publications (2)
Publication Number | Publication Date |
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CA2610873A1 true CA2610873A1 (fr) | 2007-03-01 |
CA2610873C CA2610873C (fr) | 2010-08-03 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA2610873A Expired - Fee Related CA2610873C (fr) | 2005-08-24 | 2006-08-24 | Tetrahydroquinolinones et leur utilisation comme modulateurs de recepteurs metabotropique de glutamate |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP1931635A1 (fr) |
JP (1) | JP2009506018A (fr) |
KR (1) | KR20080031972A (fr) |
CN (1) | CN101223142A (fr) |
AR (1) | AR056044A1 (fr) |
AU (1) | AU2006283359B2 (fr) |
BR (1) | BRPI0615059A2 (fr) |
CA (1) | CA2610873C (fr) |
EA (1) | EA200800660A1 (fr) |
IL (1) | IL189617A (fr) |
MX (1) | MX2008001871A (fr) |
NO (1) | NO20081428L (fr) |
TW (1) | TWI329635B (fr) |
WO (2) | WO2007023242A1 (fr) |
ZA (1) | ZA200710668B (fr) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
WO2011075699A2 (fr) | 2009-12-18 | 2011-06-23 | Sunovion Pharmaceuticals Inc. | Composés pour le traitement des troubles médiés par le récepteur métabotropique 5 du glutamate, et leurs méthodes d'utilisation |
ES2437166T3 (es) * | 2009-12-18 | 2014-01-09 | Janssen Pharmaceutica, N.V. | Tiazoles bicíclicos como moduladores alostéricos de receptores mGluR5 |
SG181716A1 (en) * | 2009-12-18 | 2012-07-30 | Janssen Pharmaceutica Nv | Bicyclic thiazoles as allosteric modulators of mglur5 receptors |
JP2013518085A (ja) | 2010-02-01 | 2013-05-20 | ノバルティス アーゲー | CRF−1受容体アンタゴニストとしてのピラゾロ[5,1b]オキサゾール誘導体 |
WO2011092293A2 (fr) | 2010-02-01 | 2011-08-04 | Novartis Ag | Dérivés de cyclohexylamide utilisés en tant qu'antagonistes du récepteur du crf |
WO2011095450A1 (fr) | 2010-02-02 | 2011-08-11 | Novartis Ag | Dérivés de cyclohexylamide à titre d'antagonistes du récepteur crf |
WO2012052451A1 (fr) | 2010-10-18 | 2012-04-26 | Merz Pharma Gmbh & Co. Kgaa | Modulateurs des récepteurs métabotropes au glutamate |
WO2012139876A1 (fr) | 2011-04-14 | 2012-10-18 | Merz Pharma Gmbh & Co. Kgaa | Formulations entériques de modulateurs de récepteur de glutamate métabotropique |
WO2012172093A1 (fr) * | 2011-06-17 | 2012-12-20 | Merz Pharma Gmbh & Co. Kgaa | Dérivé de dihydroindolizine à titre de modulateurs des récepteurs métabotropes de glutamate |
WO2013050527A1 (fr) | 2011-10-05 | 2013-04-11 | H. Lundbeck A/S | Dérivés de quinazoline en tant qu'inhibiteurs de l'enzyme pde10a |
EP2650284A1 (fr) * | 2012-04-10 | 2013-10-16 | Merz Pharma GmbH & Co. KGaA | Dérivés hétérocycliques comme modulateurs de récepteurs du glutamate métabotropique |
KR101418078B1 (ko) * | 2013-01-23 | 2014-07-10 | 한국과학기술연구원 | mGluR5 길항제로서의 2-(치환된에티닐)퀴놀린 유도체 |
US9856214B2 (en) * | 2013-11-15 | 2018-01-02 | The Wistar Institute Of Anatomy And Biology | EBNA1 inhibitors and their method of use |
KR101579496B1 (ko) * | 2014-07-03 | 2015-12-23 | 한국과학기술연구원 | mGluR5의 표식용 방사성 조성물 |
WO2016154527A1 (fr) * | 2015-03-26 | 2016-09-29 | Merck Sharp & Dohme Corp. | Dérivés de quinolizine substitués par un phosphate utiles en tant qu'inhibiteurs de l'intégrase du vih |
WO2016183534A1 (fr) | 2015-05-14 | 2016-11-17 | The Wistar Institute Of Anatomy And Biology | Inhibiteurs d'ebna1 et méthodes les utilisant |
RS59220B1 (sr) | 2015-06-03 | 2019-10-31 | Bristol Myers Squibb Co | 4-hidroksi-3-(heteroaril)piridin-2-on apj agonisti za primenu u lečenju kardiovaskularnih poremećaja |
EP3459939A1 (fr) * | 2017-09-26 | 2019-03-27 | Pragma Therapeutics | Nouveaux composés hétérocycliques comme modulateurs de mglur7 |
TW201946919A (zh) | 2018-05-17 | 2019-12-16 | 威斯塔研究所 | Ebna1抑制劑晶形、其製備方法及其使用方法 |
CA3155209A1 (fr) | 2019-10-21 | 2021-04-29 | Chan Mi Joung | Utilisation de composes d'imidazopyrimidine ou d'imidazotriazine pour la prevention, le soulagement ou le traitement de troubles cognitifs, ou pour ameliorer la fonction cognitive |
KR20220086607A (ko) * | 2019-10-21 | 2022-06-23 | 에스케이바이오팜 주식회사 | 발달 장애의 예방, 경감 또는 치료를 위한 이미다조피리미딘 또는 이미다조트리아진 화합물의 용도 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL155163A0 (en) * | 2000-10-02 | 2003-10-31 | Janssen Pharmaceutica Nv | Metabotropic glutamate receptor antagonists |
TWI301760B (en) * | 2004-02-27 | 2008-10-11 | Merz Pharma Gmbh & Co Kgaa | Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors |
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2005
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2006
- 2006-08-21 TW TW095130667A patent/TWI329635B/zh not_active IP Right Cessation
- 2006-08-24 EP EP06779201A patent/EP1931635A1/fr not_active Withdrawn
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- 2006-08-24 KR KR1020087004382A patent/KR20080031972A/ko not_active Application Discontinuation
- 2006-08-24 CN CNA2006800260106A patent/CN101223142A/zh active Pending
- 2006-08-24 BR BRPI0615059-4A patent/BRPI0615059A2/pt not_active IP Right Cessation
- 2006-08-24 CA CA2610873A patent/CA2610873C/fr not_active Expired - Fee Related
- 2006-08-24 AU AU2006283359A patent/AU2006283359B2/en not_active Ceased
- 2006-08-24 WO PCT/GB2006/003170 patent/WO2007023290A1/fr active Application Filing
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2008
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Also Published As
Publication number | Publication date |
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AR056044A1 (es) | 2007-09-12 |
NO20081428L (no) | 2008-03-18 |
WO2007023242A1 (fr) | 2007-03-01 |
AU2006283359B2 (en) | 2010-05-27 |
MX2008001871A (es) | 2008-04-09 |
TW200728283A (en) | 2007-08-01 |
EA200800660A1 (ru) | 2008-06-30 |
ZA200710668B (en) | 2009-08-26 |
AU2006283359A1 (en) | 2007-03-01 |
JP2009506018A (ja) | 2009-02-12 |
WO2007023290A1 (fr) | 2007-03-01 |
EP1931635A1 (fr) | 2008-06-18 |
CA2610873C (fr) | 2010-08-03 |
IL189617A0 (en) | 2008-06-05 |
IL189617A (en) | 2012-08-30 |
BRPI0615059A2 (pt) | 2011-04-26 |
TWI329635B (en) | 2010-09-01 |
KR20080031972A (ko) | 2008-04-11 |
CN101223142A (zh) | 2008-07-16 |
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