CA2381975A1 - Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists - Google Patents

Info

Publication number

CA2381975A1

CA2381975A1 CA002381975A CA2381975A CA2381975A1 CA 2381975 A1 CA2381975 A1 CA 2381975A1 CA 002381975 A CA002381975 A CA 002381975A CA 2381975 A CA2381975 A CA 2381975A CA 2381975 A1 CA2381975 A1 CA 2381975A1

Authority

CA

Canada

Prior art keywords

pyridyl

oxadiazole

oxazole

group

cyanophenyl

Prior art date

1999-08-19

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims abstract description 59
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims abstract description 59
• 239000003825 glutamate receptor antagonist Substances 0.000 title description 2
• 125000004585 polycyclic heterocycle group Chemical group 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 63
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
• 125000003118 aryl group Chemical group 0.000 claims abstract description 13
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 12
• 208000025966 Neurological disease Diseases 0.000 claims abstract description 11
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
• 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 6
• 238000000034 method Methods 0.000 claims description 81
• -1 anthrenyl Chemical group 0.000 claims description 50
• 239000000203 mixture Substances 0.000 claims description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 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
• 150000003839 salts Chemical class 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 9
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
• 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 8
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 7
• 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
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 7
• KZOBYFBUONCLFZ-UHFFFAOYSA-N 3-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 KZOBYFBUONCLFZ-UHFFFAOYSA-N 0.000 claims description 6
• FKZJTFVDFGPXSB-UHFFFAOYSA-N 3-(3-quinolin-2-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2ON=C(N=2)C=2N=C3C=CC=CC3=CC=2)=C1 FKZJTFVDFGPXSB-UHFFFAOYSA-N 0.000 claims description 6
• ACEMLHPTBCVQEO-UHFFFAOYSA-N 3-[3-(3-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound FC1=CC=CN=C1C1=NOC(C=2C=C(C=CC=2)C#N)=N1 ACEMLHPTBCVQEO-UHFFFAOYSA-N 0.000 claims description 6
• SQUAEZRORGDMPG-UHFFFAOYSA-N 3-[3-(5-chloropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N1=CC(Cl)=CC=C1C1=NOC(C=2C=C(C=CC=2)C#N)=N1 SQUAEZRORGDMPG-UHFFFAOYSA-N 0.000 claims description 6
• JTCHHBMKZRITLW-UHFFFAOYSA-N 3-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NOC(C=2C=C(C=CC=2)C#N)=N1 JTCHHBMKZRITLW-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• GELAFISMURFRCA-UHFFFAOYSA-N 3-fluoro-5-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound FC1=CC(C#N)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 GELAFISMURFRCA-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 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 6
• 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 6
• IBIPNEKWIOPNFP-UHFFFAOYSA-N 5-(2,3-dichlorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1Cl IBIPNEKWIOPNFP-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• XUZXZGGCOASVTJ-UHFFFAOYSA-N 5-(2-bromo-5-methoxyphenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound COC1=CC=C(Br)C(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 XUZXZGGCOASVTJ-UHFFFAOYSA-N 0.000 claims description 6
• BAHKRFBCZDXBRK-UHFFFAOYSA-N 5-(2-chloro-5-methylsulfanylphenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound CSC1=CC=C(Cl)C(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 BAHKRFBCZDXBRK-UHFFFAOYSA-N 0.000 claims description 6
• MWFUWMAFXIIDOK-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound FC1=CC(F)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 MWFUWMAFXIIDOK-UHFFFAOYSA-N 0.000 claims description 6
• 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 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
• UTVLFQJTGRGDDM-UHFFFAOYSA-N 5-(3-methoxyphenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound COC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 UTVLFQJTGRGDDM-UHFFFAOYSA-N 0.000 claims description 6
• YGUDIHOQAIXIFH-UHFFFAOYSA-N 5-naphthalen-1-yl-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound N1=CC=CC=C1C1=NOC(C=2C3=CC=CC=C3C=CC=2)=N1 YGUDIHOQAIXIFH-UHFFFAOYSA-N 0.000 claims description 6
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
• BRSJLLPXGUAIGO-UHFFFAOYSA-N 3-[3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound ClC1=CC(C(F)(F)F)=CN=C1C1=NOC(C=2C=C(C=CC=2)C#N)=N1 BRSJLLPXGUAIGO-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• HSLAPYCDJGEODS-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound ClC1=CC(Cl)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 HSLAPYCDJGEODS-UHFFFAOYSA-N 0.000 claims description 5
• IMLLSKDXLVDFRH-UHFFFAOYSA-N 5-(3-chlorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound ClC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 IMLLSKDXLVDFRH-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 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 5
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 5
• 208000020016 psychiatric disease Diseases 0.000 claims description 5
• 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 4
• 206010019196 Head injury Diseases 0.000 claims description 4
• 208000037906 ischaemic injury Diseases 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• ASQZRZJOTGTSSV-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound ClC1=CC(Cl)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 ASQZRZJOTGTSSV-UHFFFAOYSA-N 0.000 claims description 3
• YHRDDEHPQTZUOC-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound FC1=CC(F)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 YHRDDEHPQTZUOC-UHFFFAOYSA-N 0.000 claims description 3
• IUSLSOMMUPIHNA-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-4-(5-fluoropyridin-2-yl)-1,3-oxazole Chemical compound COC1=CC(OC)=CC(C=2OC=C(N=2)C=2N=CC(F)=CC=2)=C1 IUSLSOMMUPIHNA-UHFFFAOYSA-N 0.000 claims description 3
• LPMYOKHUPLYHGH-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound COC1=CC(OC)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 LPMYOKHUPLYHGH-UHFFFAOYSA-N 0.000 claims description 3
• DVWPIPCIVDZTFL-UHFFFAOYSA-N 2-(3-chloro-5-fluorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound FC1=CC(Cl)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 DVWPIPCIVDZTFL-UHFFFAOYSA-N 0.000 claims description 3
• SIWHIGOKGZLPDD-UHFFFAOYSA-N 2-(3-methoxyphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound COC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 SIWHIGOKGZLPDD-UHFFFAOYSA-N 0.000 claims description 3
• MMOZNJWTGXWZAK-UHFFFAOYSA-N 2-(3-methylphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound CC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 MMOZNJWTGXWZAK-UHFFFAOYSA-N 0.000 claims description 3
• DTCUYJPWUOVEAD-UHFFFAOYSA-N 2-naphthalen-1-yl-4-pyridin-2-yl-1,3-oxazole Chemical compound C=1OC(C=2C3=CC=CC=C3C=CC=2)=NC=1C1=CC=CC=N1 DTCUYJPWUOVEAD-UHFFFAOYSA-N 0.000 claims description 3
• WILMXYZSNMNDTC-UHFFFAOYSA-N 3-(4-quinolin-2-yl-1,3-oxazol-2-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2OC=C(N=2)C=2N=C3C=CC=CC3=CC=2)=C1 WILMXYZSNMNDTC-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• LTWCNRAEKVTUGX-UHFFFAOYSA-N 3-[4-(5-chloropyridin-2-yl)-1,3-oxazol-2-yl]benzonitrile Chemical compound N1=CC(Cl)=CC=C1C1=COC(C=2C=C(C=CC=2)C#N)=N1 LTWCNRAEKVTUGX-UHFFFAOYSA-N 0.000 claims description 3
• FQISOUJORHQCKI-UHFFFAOYSA-N 3-[4-(5-fluoropyridin-2-yl)-1,3-oxazol-2-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1C1=COC(C=2C=C(C=CC=2)C#N)=N1 FQISOUJORHQCKI-UHFFFAOYSA-N 0.000 claims description 3
• WOTTVHZQQOFUGF-UHFFFAOYSA-N 3-[4-(5-methoxypyridin-2-yl)-1,3-oxazol-2-yl]benzonitrile Chemical compound N1=CC(OC)=CC=C1C1=COC(C=2C=C(C=CC=2)C#N)=N1 WOTTVHZQQOFUGF-UHFFFAOYSA-N 0.000 claims description 3
• ROQYQCOWQVBTHR-UHFFFAOYSA-N 3-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1,3-oxazol-2-yl]benzonitrile Chemical compound ClC1=CC(C(F)(F)F)=CN=C1C1=COC(C=2C=C(C=CC=2)C#N)=N1 ROQYQCOWQVBTHR-UHFFFAOYSA-N 0.000 claims description 3
• BCWHYTSDRPOETF-UHFFFAOYSA-N 3-chloro-5-(4-pyridin-2-yl-1,3-oxazol-2-yl)benzonitrile Chemical compound ClC1=CC(C#N)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 BCWHYTSDRPOETF-UHFFFAOYSA-N 0.000 claims description 3
• PURMTHHDJDASBS-UHFFFAOYSA-N 3-fluoro-5-(4-pyridin-2-yl-1,3-oxazol-2-yl)benzonitrile Chemical compound FC1=CC(C#N)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 PURMTHHDJDASBS-UHFFFAOYSA-N 0.000 claims description 3
• RBSPCALDSNXWEP-UHFFFAOYSA-N 3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NOC(C=2C=C(C=C(F)C=2)C#N)=N1 RBSPCALDSNXWEP-UHFFFAOYSA-N 0.000 claims description 3
• LARWPXDSCLBOFH-UHFFFAOYSA-N 3-fluoro-5-[4-(5-fluoropyridin-2-yl)-1,3-oxazol-2-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1C1=COC(C=2C=C(C=C(F)C=2)C#N)=N1 LARWPXDSCLBOFH-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• YWSNJWSAQDJCBJ-UHFFFAOYSA-N 5-(3-bromophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound BrC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 YWSNJWSAQDJCBJ-UHFFFAOYSA-N 0.000 claims description 3
• YYKRPCBJFTUNFZ-UHFFFAOYSA-N 5-(3-nitrophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 YYKRPCBJFTUNFZ-UHFFFAOYSA-N 0.000 claims description 3
• 208000023105 Huntington disease Diseases 0.000 claims description 3
• 208000019695 Migraine disease Diseases 0.000 claims description 3
• 206010027603 Migraine headaches Diseases 0.000 claims description 3
• 208000002193 Pain Diseases 0.000 claims description 3
• 208000018737 Parkinson disease Diseases 0.000 claims description 3
• 206010039966 Senile dementia Diseases 0.000 claims description 3
• 230000036407 pain Effects 0.000 claims description 3
• 201000000980 schizophrenia Diseases 0.000 claims description 3
• BWGHUEIUTYJJMM-UHFFFAOYSA-N 2-(5-chloro-2-methoxyphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound COC1=CC=C(Cl)C=C1C1=NC(C=2N=CC=CC=2)=CO1 BWGHUEIUTYJJMM-UHFFFAOYSA-N 0.000 claims description 2
• 208000013016 Hypoglycemia Diseases 0.000 claims description 2
• 230000002218 hypoglycaemic effect Effects 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 12
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
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