HRP20030669A2 - N-substituted nonaryl-heterocyclic nmda/nr2b antagonists - Google Patents
N-substituted nonaryl-heterocyclic nmda/nr2b antagonistsInfo
- Publication number
- HRP20030669A2 HRP20030669A2 HR20030669A HRP20030669A HRP20030669A2 HR P20030669 A2 HRP20030669 A2 HR P20030669A2 HR 20030669 A HR20030669 A HR 20030669A HR P20030669 A HRP20030669 A HR P20030669A HR P20030669 A2 HRP20030669 A2 HR P20030669A2
- Authority
- HR
- Croatia
- Prior art keywords
- 4alkyl
- 2alkyl
- chloro
- fluoro
- pharmaceutically acceptable
- Prior art date
Links
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 title description 14
- 239000005557 antagonist Substances 0.000 title description 13
- -1 or isosazolyl Chemical group 0.000 claims description 469
- 125000001424 substituent group Chemical group 0.000 claims description 260
- 150000001875 compounds Chemical class 0.000 claims description 257
- 125000003118 aryl group Chemical group 0.000 claims description 155
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 140
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 130
- 125000001153 fluoro group Chemical group F* 0.000 claims description 129
- 150000003839 salts Chemical class 0.000 claims description 111
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 106
- 229910052757 nitrogen Inorganic materials 0.000 claims description 85
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 83
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 54
- 125000001246 bromo group Chemical group Br* 0.000 claims description 54
- 229910052799 carbon Inorganic materials 0.000 claims description 51
- 229910052731 fluorine Inorganic materials 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 29
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 20
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 17
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 16
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 15
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 15
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 14
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
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- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
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- ABJVEAFRFGTATH-UHFFFAOYSA-N benzyl 4-(aminomethyl)piperidine-1-carboxylate Chemical compound C1CC(CN)CCN1C(=O)OCC1=CC=CC=C1 ABJVEAFRFGTATH-UHFFFAOYSA-N 0.000 description 30
- 229910052739 hydrogen Inorganic materials 0.000 description 27
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
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Classifications
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
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2002
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