JP2010529135A5 - - Google Patents
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- JP2010529135A5 JP2010529135A5 JP2010511277A JP2010511277A JP2010529135A5 JP 2010529135 A5 JP2010529135 A5 JP 2010529135A5 JP 2010511277 A JP2010511277 A JP 2010511277A JP 2010511277 A JP2010511277 A JP 2010511277A JP 2010529135 A5 JP2010529135 A5 JP 2010529135A5
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- Prior art keywords
- optionally substituted
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- hydrogen
- amino
- radical containing
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 201
- 239000001257 hydrogen Substances 0.000 claims description 201
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 177
- 150000002431 hydrogen Chemical group 0.000 claims description 149
- 229910052736 halogen Inorganic materials 0.000 claims description 125
- 150000002367 halogens Chemical group 0.000 claims description 125
- 150000001875 compounds Chemical class 0.000 claims description 121
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 104
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 104
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 104
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 104
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 94
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 94
- 125000001072 heteroaryl group Chemical group 0.000 claims description 93
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 91
- 125000003107 substituted aryl group Chemical group 0.000 claims description 90
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 71
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 62
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 62
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 62
- 125000004001 thioalkyl group Chemical group 0.000 claims description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims description 61
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 56
- 125000000304 alkynyl group Chemical group 0.000 claims description 54
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 54
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 54
- VDNGBJSXAZNOFK-UHFFFAOYSA-N aminosulfanylazanide Chemical class NS[NH-] VDNGBJSXAZNOFK-UHFFFAOYSA-N 0.000 claims description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 48
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 150000003973 alkyl amines Chemical class 0.000 claims description 37
- 229940049906 Glutamate Drugs 0.000 claims description 30
- 230000004044 response Effects 0.000 claims description 30
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 26
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 25
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims description 24
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
- 241000124008 Mammalia Species 0.000 claims description 21
- 238000010276 construction Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000011780 sodium chloride Substances 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 20
- 150000001204 N-oxides Chemical class 0.000 claims description 19
- -1 bicyclic compound Chemical class 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 241000700159 Rattus Species 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 150000003857 carboxamides Chemical class 0.000 claims description 13
- 125000005518 carboxamido group Chemical group 0.000 claims description 13
- 210000003292 kidney cell Anatomy 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 11
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 11
- 229960002989 Glutamic Acid Drugs 0.000 claims description 11
- 125000002837 carbocyclic group Chemical group 0.000 claims description 11
- 235000013922 glutamic acid Nutrition 0.000 claims description 11
- 239000004220 glutamic acid Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 206010014551 Emotional disease Diseases 0.000 claims description 8
- 206010061920 Psychotic disease Diseases 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 8
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- PXXJHWLDUBFPOL-UHFFFAOYSA-N Benzamidine Chemical group NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- XKJCHHZQLQNZHY-UHFFFAOYSA-N Phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 5
- 206010037175 Psychiatric disease Diseases 0.000 claims description 5
- 125000004429 atoms Chemical group 0.000 claims description 5
- 230000004064 dysfunction Effects 0.000 claims description 5
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 5
- YWPMKTWUFVOFPL-UHFFFAOYSA-N 3,4-dihydro-2H-isoquinolin-1-one Chemical class C1=CC=C2C(=O)NCCC2=C1 YWPMKTWUFVOFPL-UHFFFAOYSA-N 0.000 claims description 4
- QGNQEODJYRGEJX-UHFFFAOYSA-N 4H-isoquinoline-1,3-dione Chemical class C1=CC=C2C(=O)NC(=O)CC2=C1 QGNQEODJYRGEJX-UHFFFAOYSA-N 0.000 claims description 4
- 206010001497 Agitation Diseases 0.000 claims description 4
- 208000000044 Amnesia Diseases 0.000 claims description 4
- 206010001954 Amnestic disease Diseases 0.000 claims description 4
- 206010002855 Anxiety Diseases 0.000 claims description 4
- 206010057666 Anxiety disease Diseases 0.000 claims description 4
- 206010004938 Bipolar disease Diseases 0.000 claims description 4
- 208000006752 Brain Edema Diseases 0.000 claims description 4
- 206010048962 Brain oedema Diseases 0.000 claims description 4
- 206010008748 Chorea Diseases 0.000 claims description 4
- 206010057668 Cognitive disease Diseases 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 206010012601 Diabetes mellitus Diseases 0.000 claims description 4
- 208000010118 Dystonia Diseases 0.000 claims description 4
- 206010015037 Epilepsy Diseases 0.000 claims description 4
- 206010057840 Major depression Diseases 0.000 claims description 4
- 206010027599 Migraine Diseases 0.000 claims description 4
- 208000008085 Migraine Disorders Diseases 0.000 claims description 4
- 208000009025 Nervous System Disease Diseases 0.000 claims description 4
- 206010029305 Neurological disorder Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
- 206010033664 Panic attack Diseases 0.000 claims description 4
- 208000000639 Paranoid Disorders Diseases 0.000 claims description 4
- 206010040984 Sleep disease Diseases 0.000 claims description 4
- 230000032683 aging Effects 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 201000001973 choreatic disease Diseases 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 201000006180 eating disease Diseases 0.000 claims description 4
- 201000009457 movement disease Diseases 0.000 claims description 4
- 201000003631 narcolepsy Diseases 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 230000000698 schizophrenic Effects 0.000 claims description 4
- 201000009031 substance-related disease Diseases 0.000 claims description 4
- 125000006617 triphenylamine group Chemical group 0.000 claims description 3
- AQLZTHZLYFFVIJ-UHFFFAOYSA-N 2-(2-aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound O=C1N(C)C(C(C)(C)N)=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O AQLZTHZLYFFVIJ-UHFFFAOYSA-N 0.000 claims 12
- 241000282941 Rangifer tarandus Species 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical compound C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 24
- MOIPGXQKZSZOQX-UHFFFAOYSA-N Carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 0 CCCC*(*)*(C(C(C(C)=N)=C(*)**=C(C)C)=O)N Chemical compound CCCC*(*)*(C(C(C(C)=N)=C(*)**=C(C)C)=O)N 0.000 description 6
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 5
- 102000016193 Metabotropic Glutamate Receptors Human genes 0.000 description 4
- 108010010914 Metabotropic Glutamate Receptors Proteins 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002708 enhancing Effects 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N Triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatoms Chemical group 0.000 description 3
- MCFDHXXQFUDVES-UHFFFAOYSA-N Cc1n[o]c([IH]C)n1 Chemical compound Cc1n[o]c([IH]C)n1 MCFDHXXQFUDVES-UHFFFAOYSA-N 0.000 description 2
- 230000019771 cognition Effects 0.000 description 2
- 230000037410 cognitive enhancement Effects 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000003213 activating Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000000926 neurological Effects 0.000 description 1
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US94168607P | 2007-06-03 | 2007-06-03 | |
US60/941,686 | 2007-06-03 | ||
US98504107P | 2007-11-02 | 2007-11-02 | |
US60/985,041 | 2007-11-02 | ||
PCT/US2008/065647 WO2008151184A1 (en) | 2007-06-03 | 2008-06-03 | Benzamide mglur5 positive allosteric modulators and methods of making and using same |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010529135A JP2010529135A (ja) | 2010-08-26 |
JP2010529135A5 true JP2010529135A5 (ru) | 2012-07-12 |
JP5622568B2 JP5622568B2 (ja) | 2014-11-12 |
Family
ID=41480433
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010511277A Expired - Fee Related JP5622568B2 (ja) | 2007-06-03 | 2008-06-03 | ベンズアミドmGluR5の正のアロステリック調節因子ならびにその作製および使用方法 |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP2162136A4 (ru) |
JP (1) | JP5622568B2 (ru) |
KR (1) | KR20100033981A (ru) |
CN (1) | CN101795689B (ru) |
AU (1) | AU2008259776A1 (ru) |
BR (1) | BRPI0812363A2 (ru) |
CA (1) | CA2689282A1 (ru) |
EA (1) | EA200971143A1 (ru) |
HK (1) | HK1147068A1 (ru) |
IL (1) | IL202508A0 (ru) |
MX (1) | MX2009013169A (ru) |
NZ (1) | NZ581817A (ru) |
SG (1) | SG185285A1 (ru) |
WO (1) | WO2008151184A1 (ru) |
Families Citing this family (72)
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NZ577111A (en) | 2006-12-15 | 2012-05-25 | Abbott Lab | Novel oxadiazole compounds |
US8853392B2 (en) | 2007-06-03 | 2014-10-07 | Vanderbilt University | Benzamide mGluR5 positive allosteric modulators and methods of making and using same |
US8034806B2 (en) | 2007-11-02 | 2011-10-11 | Vanderbilt University | Bicyclic mGluR5 positive allosteric modulators and methods of making and using same |
GB0811643D0 (en) | 2008-06-25 | 2008-07-30 | Cancer Rec Tech Ltd | New therapeutic agents |
TW201028421A (en) * | 2009-01-15 | 2010-08-01 | Abbott Lab | Novel benzenesulfonamides as calcium channel blockers |
US8389536B2 (en) * | 2009-10-27 | 2013-03-05 | Hoffmann-La Roche Inc. | Positive allosteric modulators (PAM) |
US8586581B2 (en) | 2009-12-17 | 2013-11-19 | Hoffmann-La Roche Inc | Ethynyl compounds useful for treatment of CNS disorders |
CA2784830C (en) | 2009-12-18 | 2018-03-27 | Sunovion Pharmaceuticals Inc. | Compounds for treating disorders mediated by metabotropic glutamate receptor 5, and methods of use thereof |
EP2513118B1 (en) | 2009-12-18 | 2013-09-18 | Janssen Pharmaceutica, N.V. | Bicyclic thiazoles as allosteric modulators of mglur5 receptors |
WO2011073339A1 (en) | 2009-12-18 | 2011-06-23 | Janssen Pharmaceutica Nv | Bicyclic thiazoles as allosteric modulators of mglur5 receptors |
PL2516434T3 (pl) | 2009-12-23 | 2015-11-30 | Takeda Pharmaceuticals Co | Skondensowane heteroaromatyczne pirolidynony jako inhibitory SYK |
US8420661B2 (en) | 2010-04-13 | 2013-04-16 | Hoffmann-La Roche Inc. | Arylethynyl derivatives |
EA201291327A1 (ru) | 2010-05-24 | 2013-05-30 | Вандербилт Юниверсити | Замещенные 6-метилникотинамиды как позитивные аллостерические модуляторы mglur5 |
WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
US8772300B2 (en) | 2011-04-19 | 2014-07-08 | Hoffmann-La Roche Inc. | Phenyl or pyridinyl-ethynyl derivatives |
CA2829171C (en) | 2011-04-26 | 2019-02-26 | F. Hoffmann-La Roche Ag | Pyrazolidin-3-one derivatives |
SI2702051T1 (sl) * | 2011-04-26 | 2015-06-30 | F. Hoffmann-La Roche Ag | Etinilni derivati kot pozitivni alosteriäśni modulatorji mglur5 |
US9056873B2 (en) | 2011-06-22 | 2015-06-16 | Takeda Pharmaceutical Company Limited | Substituted 6-aza-isoindolin-1-one derivatives |
US20130123254A1 (en) | 2011-09-30 | 2013-05-16 | Barbara Biemans | Pharmaceutically acceptable mglur5 positive allosteric modulators and their methods of identification |
UA110862C2 (uk) * | 2011-10-07 | 2016-02-25 | Ф. Хоффманн-Ля Рош Аг | Похідні етинілу як алостеричні модулятори метаботропного рецептора глутамату mglur 5 |
UA110995C2 (uk) | 2011-10-07 | 2016-03-10 | Ф. Хоффманн-Ля Рош Аг | Етинільні похідні як модулятори метаботропного глутаматного рецептора |
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PE20150184A1 (es) | 2012-07-17 | 2015-02-13 | Hoffmann La Roche | Derivados de ariletinilo |
WO2014026125A1 (en) | 2012-08-10 | 2014-02-13 | Incyte Corporation | Pyrazine derivatives as fgfr inhibitors |
UA113223C2 (xx) * | 2012-08-13 | 2016-12-26 | Арилетинілпіримідини | |
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EA025667B1 (ru) * | 2012-10-18 | 2017-01-30 | Ф. Хоффманн-Ля Рош Аг | ПРОИЗВОДНЫЕ ЭТИНИЛА В КАЧЕСТВЕ МОДУЛЯТОРОВ АКТИВНОСТИ РЕЦЕПТОРА mGluR5 |
UA114934C2 (uk) * | 2012-10-18 | 2017-08-28 | Ф. Хоффманн-Ля Рош Аг | Похідне етинілу як модулятор активності метаботропного глутаматного рецептора підтипу 5 |
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AU2014327504B2 (en) * | 2013-09-25 | 2018-01-04 | F. Hoffmann-La Roche Ag | Ethynyl derivatives |
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TW544448B (en) * | 1997-07-11 | 2003-08-01 | Novartis Ag | Pyridine derivatives |
GB9823871D0 (en) * | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
WO2003009807A2 (en) * | 2001-07-23 | 2003-02-06 | Galileo Laboratories, Inc. | Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods |
AU2003249983A1 (en) * | 2002-07-18 | 2004-02-09 | Actelion Pharmaceuticals Ltd | Piperidines useful for the treatment of central nervous system disorders |
AU2004226450A1 (en) * | 2003-03-26 | 2004-10-14 | Merck & Co. Inc. | Benzamide modulators of metabotropic glutamate receptors |
EP1680109A4 (en) * | 2003-10-07 | 2009-05-06 | Renovis Inc | AMIDE DERIVATIVES AS ION CHANNEL LIGANDS AND PHARMACEUTICAL COMPOSITIONS AND METHODS OF USING THE DERIVATIVES |
GB0324159D0 (en) * | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
GB0325956D0 (en) * | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
US7566781B2 (en) * | 2004-05-10 | 2009-07-28 | Banyu Pharmaceutical Co., Ltd. | Imidazopyridine compound |
GB0503646D0 (en) * | 2005-02-22 | 2005-03-30 | Novartis Ag | Organic compounds |
AP2007004119A0 (en) * | 2005-02-28 | 2007-08-31 | Renovis Inc | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
-
2008
- 2008-06-03 MX MX2009013169A patent/MX2009013169A/es not_active Application Discontinuation
- 2008-06-03 WO PCT/US2008/065647 patent/WO2008151184A1/en active Application Filing
- 2008-06-03 EP EP08770045A patent/EP2162136A4/en not_active Withdrawn
- 2008-06-03 AU AU2008259776A patent/AU2008259776A1/en not_active Abandoned
- 2008-06-03 EA EA200971143A patent/EA200971143A1/ru unknown
- 2008-06-03 JP JP2010511277A patent/JP5622568B2/ja not_active Expired - Fee Related
- 2008-06-03 BR BRPI0812363-2A2A patent/BRPI0812363A2/pt not_active IP Right Cessation
- 2008-06-03 SG SG2012074621A patent/SG185285A1/en unknown
- 2008-06-03 KR KR1020097027281A patent/KR20100033981A/ko not_active Application Discontinuation
- 2008-06-03 CN CN200880100770.6A patent/CN101795689B/zh not_active Expired - Fee Related
- 2008-06-03 CA CA002689282A patent/CA2689282A1/en not_active Abandoned
- 2008-06-03 NZ NZ581817A patent/NZ581817A/en not_active IP Right Cessation
-
2009
- 2009-12-03 IL IL202508A patent/IL202508A0/en unknown
-
2011
- 2011-02-07 HK HK11101174.3A patent/HK1147068A1/xx not_active IP Right Cessation
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