TW200821305A - MGluR5 modulators - Google Patents

Info

Publication number

TW200821305A

TW200821305A TW096135382A TW96135382A TW200821305A TW 200821305 A TW200821305 A TW 200821305A TW 096135382 A TW096135382 A TW 096135382A TW 96135382 A TW96135382 A TW 96135382A TW 200821305 A TW200821305 A TW 200821305A

Authority

TW

Taiwan

Prior art keywords

methyl

triazol

ethoxy

group

compound

Prior art date

2006-10-05

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims abstract description 183
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 108
• 239000002253 acid Substances 0.000 claims description 49
• -1 acridine-4-carboxylic acid hydrazine Chemical compound 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 41
• 238000011282 treatment Methods 0.000 claims description 37
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• 239000003814 drug Substances 0.000 claims description 17
• 239000000126 substance Substances 0.000 claims description 17
• 210000000111 lower esophageal sphincter Anatomy 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
• 229940079593 drug Drugs 0.000 claims description 12
• 239000007789 gas Substances 0.000 claims description 11
• 208000002193 Pain Diseases 0.000 claims description 10
• 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 10
• 150000002431 hydrogen Chemical group 0.000 claims description 9
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 8
• 150000003536 tetrazoles Chemical class 0.000 claims description 8
• 239000004480 active ingredient Substances 0.000 claims description 7
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 230000003287 optical effect Effects 0.000 claims description 6
• 230000036407 pain Effects 0.000 claims description 6
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 150000002576 ketones Chemical class 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000011737 fluorine Chemical group 0.000 claims description 4
• 229910052731 fluorine Chemical group 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 230000001052 transient effect Effects 0.000 claims description 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
• 208000019901 Anxiety disease Diseases 0.000 claims description 3
• 230000036506 anxiety Effects 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 2
• OPADHMIOKMGTAZ-UHFFFAOYSA-N 5-(3-methylphenyl)-1,2-oxazole-3-carbaldehyde Chemical compound CC1=CC=CC(C=2ON=C(C=O)C=2)=C1 OPADHMIOKMGTAZ-UHFFFAOYSA-N 0.000 claims description 2
• HFAKLRWDIHVCSP-SECBINFHSA-N [(1r)-1-[2-(3-methylphenyl)tetrazol-5-yl]ethyl] acetate Chemical compound N1=C([C@H](OC(C)=O)C)N=NN1C1=CC=CC(C)=C1 HFAKLRWDIHVCSP-SECBINFHSA-N 0.000 claims description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 3
• 125000003944 tolyl group Chemical group 0.000 claims 2
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims 1
• CFYQBZOVTJXQDQ-UHFFFAOYSA-N 5-(3-chlorophenyl)-1,2-oxazole Chemical compound ClC1=CC=CC(C=2ON=CC=2)=C1 CFYQBZOVTJXQDQ-UHFFFAOYSA-N 0.000 claims 1
• FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 1
• MCRPKBUFXAKDKI-UHFFFAOYSA-N ethyl pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1 MCRPKBUFXAKDKI-UHFFFAOYSA-N 0.000 claims 1
• 230000000968 intestinal effect Effects 0.000 claims 1
• 230000007794 irritation Effects 0.000 claims 1
• MQUPWTBHHPUUMC-UHFFFAOYSA-N isoindole Chemical compound C1=CC=C[C]2C=NC=C21 MQUPWTBHHPUUMC-UHFFFAOYSA-N 0.000 claims 1
• TVPRCLHSULCNLV-UHFFFAOYSA-N pyridazin-3-one Chemical compound O=C1C=CC=N[N]1 TVPRCLHSULCNLV-UHFFFAOYSA-N 0.000 claims 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 39
• 239000000543 intermediate Substances 0.000 abstract description 15
• 238000002360 preparation method Methods 0.000 abstract description 11
• 230000008569 process Effects 0.000 abstract description 5
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• 238000005481 NMR spectroscopy Methods 0.000 description 76
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• 101150041968 CDC13 gene Proteins 0.000 description 72
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 72
• 235000019439 ethyl acetate Nutrition 0.000 description 67
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 65
• 239000000203 mixture Substances 0.000 description 50
• 239000000243 solution Substances 0.000 description 49
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
• 239000011541 reaction mixture Substances 0.000 description 41
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 206010057190 Respiratory tract infections Diseases 0.000 description 37
• 239000002904 solvent Substances 0.000 description 31
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 29
• 239000007787 solid Substances 0.000 description 28
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• 201000010099 disease Diseases 0.000 description 26
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 25
• 239000000047 product Substances 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
• 239000002585 base Substances 0.000 description 22
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
• 238000007792 addition Methods 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 230000004913 activation Effects 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 17
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• 102000005962 receptors Human genes 0.000 description 16
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
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• 235000011152 sodium sulphate Nutrition 0.000 description 15
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
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