NO322460B1 - Heteropolysykliske forbindelser og deres anvendelse som metabotropiske glutamatreseptorantagonister - Google Patents

Info

Publication number

NO322460B1

NO322460B1 NO20020823A NO20020823A NO322460B1 NO 322460 B1 NO322460 B1 NO 322460B1 NO 20020823 A NO20020823 A NO 20020823A NO 20020823 A NO20020823 A NO 20020823A NO 322460 B1 NO322460 B1 NO 322460B1

Authority

NO

Norway

Prior art keywords

pyridyl

oxazole

oxadiazole

cyanophenyl

chloro

Prior art date

1999-08-19

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• 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims abstract description 56
• 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims abstract description 56
• 239000003825 glutamate receptor antagonist Substances 0.000 title 1
• 125000004585 polycyclic heterocycle group Chemical group 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 70
• 125000003118 aryl group Chemical group 0.000 claims abstract description 15
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• 208000025966 Neurological disease Diseases 0.000 claims abstract description 9
• 239000000203 mixture Substances 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
• CQXOVXIKDZNZMV-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound ClC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 CQXOVXIKDZNZMV-UHFFFAOYSA-N 0.000 claims description 12
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
• 150000003839 salts Chemical class 0.000 claims description 11
• FPYLVHWPDOYNOI-UHFFFAOYSA-N 4-pyridin-2-yl-2-(2,3,6-trifluorophenyl)-1,3-oxazole Chemical compound FC1=CC=C(F)C(C=2OC=C(N=2)C=2N=CC=CC=2)=C1F FPYLVHWPDOYNOI-UHFFFAOYSA-N 0.000 claims description 9
• NGKWCJCCZGCLID-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound ClC1=CC=CC=C1C1=NC(C=2N=CC=CC=2)=NO1 NGKWCJCCZGCLID-UHFFFAOYSA-N 0.000 claims description 9
• 208000035475 disorder Diseases 0.000 claims description 9
• XZDUVAVPEQYRJT-UHFFFAOYSA-N 3-(4-pyridin-2-yl-1,3-oxazol-2-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 XZDUVAVPEQYRJT-UHFFFAOYSA-N 0.000 claims description 8
• OTAZWJWYCGCZPY-UHFFFAOYSA-N 3-pyridin-2-yl-5-(2,3,6-trifluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=CC=C(F)C(C=2ON=C(N=2)C=2N=CC=CC=2)=C1F OTAZWJWYCGCZPY-UHFFFAOYSA-N 0.000 claims description 8
• FZTXNLFUEFOVRO-UHFFFAOYSA-N 3-pyridin-2-yl-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 FZTXNLFUEFOVRO-UHFFFAOYSA-N 0.000 claims description 8
• PBVARAUVAZZUHN-UHFFFAOYSA-N 5-(3,5-dimethoxyphenyl)-3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazole Chemical compound COC1=CC(OC)=CC(C=2ON=C(N=2)C=2N=CC(F)=CC=2)=C1 PBVARAUVAZZUHN-UHFFFAOYSA-N 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• HFGWLRAJYOVQAY-UHFFFAOYSA-N 2-(3-bromophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound BrC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 HFGWLRAJYOVQAY-UHFFFAOYSA-N 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• XKZXZXODZDSMKN-UHFFFAOYSA-N 3-[3-(5-methoxypyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N1=CC(OC)=CC=C1C1=NOC(C=2C=C(C=CC=2)C#N)=N1 XKZXZXODZDSMKN-UHFFFAOYSA-N 0.000 claims description 7
• DKASLOPISBVXCX-UHFFFAOYSA-N 3-pyridin-2-yl-5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)OC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 DKASLOPISBVXCX-UHFFFAOYSA-N 0.000 claims description 7
• GIHMKZCHBTWVSO-UHFFFAOYSA-N 5-(2,3-difluorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound FC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1F GIHMKZCHBTWVSO-UHFFFAOYSA-N 0.000 claims description 7
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• NEBUBOGLNXERLF-UHFFFAOYSA-N 3-chloro-5-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound ClC1=CC(C#N)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 NEBUBOGLNXERLF-UHFFFAOYSA-N 0.000 claims description 6
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• JWGWZTPLPSOQLP-UHFFFAOYSA-N 5-(2,5-difluorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound FC1=CC=C(F)C(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 JWGWZTPLPSOQLP-UHFFFAOYSA-N 0.000 claims description 6
• NFNZGNPPPSUBSN-UHFFFAOYSA-N 5-(3,5-dimethoxyphenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound COC1=CC(OC)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 NFNZGNPPPSUBSN-UHFFFAOYSA-N 0.000 claims description 6
• QAWYDHMYEBUWOI-UHFFFAOYSA-N 5-(3-chloro-5-fluorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound FC1=CC(Cl)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 QAWYDHMYEBUWOI-UHFFFAOYSA-N 0.000 claims description 6
• NPHDXXRKYHPQLD-UHFFFAOYSA-N 5-(3-methylphenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 NPHDXXRKYHPQLD-UHFFFAOYSA-N 0.000 claims description 6
• PREUPKHXEHMSKI-UHFFFAOYSA-N 5-(5-chloro-2-methoxyphenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound COC1=CC=C(Cl)C=C1C1=NC(C=2N=CC=CC=2)=NO1 PREUPKHXEHMSKI-UHFFFAOYSA-N 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• AAWCNLJAPJLNKK-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound ClC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1Cl AAWCNLJAPJLNKK-UHFFFAOYSA-N 0.000 claims description 5
• RJOREFFZIBPFKY-UHFFFAOYSA-N 2-(2,3-difluorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound FC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1F RJOREFFZIBPFKY-UHFFFAOYSA-N 0.000 claims description 5
• LRFMDDYKWJYVBK-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound FC1=CC=C(F)C(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 LRFMDDYKWJYVBK-UHFFFAOYSA-N 0.000 claims description 5
• ZLPWRJCQPWCDGU-UHFFFAOYSA-N 2-(2-bromo-5-methoxyphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound COC1=CC=C(Br)C(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 ZLPWRJCQPWCDGU-UHFFFAOYSA-N 0.000 claims description 5
• DEMSILUPLXBKQE-UHFFFAOYSA-N 2-(2-chloro-5-methylsulfanylphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound CSC1=CC=C(Cl)C(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 DEMSILUPLXBKQE-UHFFFAOYSA-N 0.000 claims description 5
• YXDVCVJVOFDWQF-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound ClC1=CC=CC=C1C1=NC(C=2N=CC=CC=2)=CO1 YXDVCVJVOFDWQF-UHFFFAOYSA-N 0.000 claims description 5
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• SOXYQDMUEKECIH-UHFFFAOYSA-N 3-[4-(3-fluoropyridin-2-yl)-1,3-oxazol-2-yl]benzonitrile Chemical compound FC1=CC=CN=C1C1=COC(C=2C=C(C=CC=2)C#N)=N1 SOXYQDMUEKECIH-UHFFFAOYSA-N 0.000 claims description 5
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• IOQSPWXNEANOEM-UHFFFAOYSA-N 4-pyridin-2-yl-2-[3-(trifluoromethoxy)phenyl]-1,3-oxazole Chemical compound FC(F)(F)OC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 IOQSPWXNEANOEM-UHFFFAOYSA-N 0.000 claims description 5
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