JP2017528519A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017528519A5 JP2017528519A5 JP2017530971A JP2017530971A JP2017528519A5 JP 2017528519 A5 JP2017528519 A5 JP 2017528519A5 JP 2017530971 A JP2017530971 A JP 2017530971A JP 2017530971 A JP2017530971 A JP 2017530971A JP 2017528519 A5 JP2017528519 A5 JP 2017528519A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methoxy
- benzoxazol
- methyl
- methoxypyridin
- Prior art date
- 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.)
- Granted
Links
- 239000012216 imaging agent Substances 0.000 claims description 113
- 125000000217 alkyl group Chemical group 0.000 claims description 107
- -1 phenoxy, benzyloxy Chemical group 0.000 claims description 80
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 66
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000002600 positron emission tomography Methods 0.000 claims description 10
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 208000023105 Huntington disease Diseases 0.000 claims description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 208000037273 Pathologic Processes Diseases 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 4
- 238000002595 magnetic resonance imaging Methods 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 230000009054 pathological process Effects 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- UIMIKAMLPAXJFZ-UHFFFAOYSA-N 3-methoxy-n-[2-(4-methoxyphenyl)-1,3-benzoxazol-5-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(NC(=O)C=3C=C(OC)C=CC=3)=CC=C2O1 UIMIKAMLPAXJFZ-UHFFFAOYSA-N 0.000 claims description 3
- WOADCRRNCZUGKM-UHFFFAOYSA-N 3-phenylmethoxy-n-(2-pyridin-3-yl-1,3-benzoxazol-5-yl)benzamide Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1C(=O)NC(C=C1N=2)=CC=C1OC=2C1=CC=CN=C1 WOADCRRNCZUGKM-UHFFFAOYSA-N 0.000 claims description 3
- SEQHVJYHFBXFJF-UHFFFAOYSA-N 4-methoxy-n-(2-pyridin-3-yl-1,3-benzoxazol-5-yl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(OC(=N2)C=3C=NC=CC=3)C2=C1 SEQHVJYHFBXFJF-UHFFFAOYSA-N 0.000 claims description 3
- XXQQUFJDNPKJKC-UHFFFAOYSA-N 4-methoxy-n-[2-(3-methylphenyl)-1,3-benzoxazol-5-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(OC(=N2)C=3C=C(C)C=CC=3)C2=C1 XXQQUFJDNPKJKC-UHFFFAOYSA-N 0.000 claims description 3
- AZGZJIGRQLPADH-UHFFFAOYSA-N 4-methoxy-n-[2-(4-methoxyphenyl)-1,3-benzoxazol-5-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(OC(=N2)C=3C=CC(OC)=CC=3)C2=C1 AZGZJIGRQLPADH-UHFFFAOYSA-N 0.000 claims description 3
- WAAYKZUJRSODSL-UHFFFAOYSA-N 5-[5-[(5-methoxypyridin-2-yl)methoxy]-1,3-benzoxazol-2-yl]-1H-pyridin-2-one Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(NC=2)=O)C=1 WAAYKZUJRSODSL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 3
- QHHLWCYQCPUDMA-UHFFFAOYSA-N BrC1=C(C#N)C(=CC=C1)C=1OC2=C(C=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound BrC1=C(C#N)C(=CC=C1)C=1OC2=C(C=1)C=C(C=C2)OCC1=NC=C(C=C1)OC QHHLWCYQCPUDMA-UHFFFAOYSA-N 0.000 claims description 3
- CSVYADKQTJYBJA-UHFFFAOYSA-N BrC1=C(N2C(S1)=NCC2)C=1OC2=C(C=1)C=C(C=C2)OCC=1C=NC=CC=1 Chemical compound BrC1=C(N2C(S1)=NCC2)C=1OC2=C(C=1)C=C(C=C2)OCC=1C=NC=CC=1 CSVYADKQTJYBJA-UHFFFAOYSA-N 0.000 claims description 3
- LAHARBSZHZXANE-UHFFFAOYSA-N BrC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound BrC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 LAHARBSZHZXANE-UHFFFAOYSA-N 0.000 claims description 3
- VPNAVESIGYIHTR-UHFFFAOYSA-N BrC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound BrC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 VPNAVESIGYIHTR-UHFFFAOYSA-N 0.000 claims description 3
- TXRNACQIWPORAR-UHFFFAOYSA-N BrC=1C=NC=CC=1C=1SC2=C(N=1)C=CC(=C2)OCCN1CCOCC1 Chemical compound BrC=1C=NC=CC=1C=1SC2=C(N=1)C=CC(=C2)OCCN1CCOCC1 TXRNACQIWPORAR-UHFFFAOYSA-N 0.000 claims description 3
- QDSIMGQQJYDRLR-UHFFFAOYSA-N C(C1=CC=CC=C1)OC=1C=C(C=CC=1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=CC=1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC QDSIMGQQJYDRLR-UHFFFAOYSA-N 0.000 claims description 3
- QJBPZMASKVJLEP-UHFFFAOYSA-N C(C=C)OC=1N=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound C(C=C)OC=1N=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 QJBPZMASKVJLEP-UHFFFAOYSA-N 0.000 claims description 3
- WNWJHGZEERTOGJ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NN=C(O1)C(=O)NC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound C1(=CC=CC=C1)C1=NN=C(O1)C(=O)NC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 WNWJHGZEERTOGJ-UHFFFAOYSA-N 0.000 claims description 3
- VJLLVXLUVWHNAZ-UHFFFAOYSA-N C=1N=CN2C=1CN(CC2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound C=1N=CN2C=1CN(CC2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC VJLLVXLUVWHNAZ-UHFFFAOYSA-N 0.000 claims description 3
- JULWCNLTWUDREK-UHFFFAOYSA-N CN(CCN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1)C Chemical compound CN(CCN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1)C JULWCNLTWUDREK-UHFFFAOYSA-N 0.000 claims description 3
- MEVJLNCDEUUZEN-UHFFFAOYSA-N CN1C(=NC=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound CN1C(=NC=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 MEVJLNCDEUUZEN-UHFFFAOYSA-N 0.000 claims description 3
- YCPMYYOBZAAPBL-UHFFFAOYSA-N CN1C(C=NC(=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O Chemical compound CN1C(C=NC(=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O YCPMYYOBZAAPBL-UHFFFAOYSA-N 0.000 claims description 3
- SRRSKFMMJPXFOO-UHFFFAOYSA-N CN1C=NC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound CN1C=NC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 SRRSKFMMJPXFOO-UHFFFAOYSA-N 0.000 claims description 3
- XBVQBPJQOFGZRA-UHFFFAOYSA-N CN1N=C(C(=C1)C=1OC2=C(C=1)C=C(C=C2)OCC=1C=NC=NC=1)C#N Chemical compound CN1N=C(C(=C1)C=1OC2=C(C=1)C=C(C=C2)OCC=1C=NC=NC=1)C#N XBVQBPJQOFGZRA-UHFFFAOYSA-N 0.000 claims description 3
- CGLNAUGNVVTZEM-UHFFFAOYSA-N CN1N=C(C=CC1=O)C(=O)NC=1C=CC2=C(N=C(O2)C2=NN(C(C=C2)=O)C)C=1 Chemical compound CN1N=C(C=CC1=O)C(=O)NC=1C=CC2=C(N=C(O2)C2=NN(C(C=C2)=O)C)C=1 CGLNAUGNVVTZEM-UHFFFAOYSA-N 0.000 claims description 3
- JZJPSLLERBICRI-UHFFFAOYSA-N CN1N=C(C=CC1=O)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound CN1N=C(C=CC1=O)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 JZJPSLLERBICRI-UHFFFAOYSA-N 0.000 claims description 3
- RIXUVFCKZMKCHG-UHFFFAOYSA-N CN1N=CC(=C1)C(=O)NC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound CN1N=CC(=C1)C(=O)NC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 RIXUVFCKZMKCHG-UHFFFAOYSA-N 0.000 claims description 3
- YWFGNCLDFYQDTH-UHFFFAOYSA-N CN1N=CC(=C1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound CN1N=CC(=C1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 YWFGNCLDFYQDTH-UHFFFAOYSA-N 0.000 claims description 3
- IIFUNXPXGGOYSW-UHFFFAOYSA-N CN1N=CC(=C1)C=1OC2=C(N=1)C=C(C=C2)OCC1=CC=C(C=N1)O Chemical compound CN1N=CC(=C1)C=1OC2=C(N=1)C=C(C=C2)OCC1=CC=C(C=N1)O IIFUNXPXGGOYSW-UHFFFAOYSA-N 0.000 claims description 3
- AXNXAOVUCXAMJB-UHFFFAOYSA-N CN1N=CC(=C1)C=1OC2=NC=C(C=C2N=1)OCC1=CC=C(C=N1)N Chemical compound CN1N=CC(=C1)C=1OC2=NC=C(C=C2N=1)OCC1=CC=C(C=N1)N AXNXAOVUCXAMJB-UHFFFAOYSA-N 0.000 claims description 3
- NVEOVZSQBQDXSU-UHFFFAOYSA-N CN1N=CC(=C1)C=1OC2=NC=C(C=C2N=1)OCC1=NC=CN=C1 Chemical compound CN1N=CC(=C1)C=1OC2=NC=C(C=C2N=1)OCC1=NC=CN=C1 NVEOVZSQBQDXSU-UHFFFAOYSA-N 0.000 claims description 3
- QDTOTZBWPRBYDL-UHFFFAOYSA-N CN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound CN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 QDTOTZBWPRBYDL-UHFFFAOYSA-N 0.000 claims description 3
- RMQPHMFDUOSYIF-UHFFFAOYSA-N CN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C=2C=NC=CC=2C#N)C=1 Chemical compound CN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C=2C=NC=CC=2C#N)C=1 RMQPHMFDUOSYIF-UHFFFAOYSA-N 0.000 claims description 3
- IVCPHTXMOSOONX-UHFFFAOYSA-N CN1N=CC(=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound CN1N=CC(=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 IVCPHTXMOSOONX-UHFFFAOYSA-N 0.000 claims description 3
- TYDXOWRHTWLVHT-UHFFFAOYSA-N CNC=1C=NC(=CC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound CNC=1C=NC(=CC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 TYDXOWRHTWLVHT-UHFFFAOYSA-N 0.000 claims description 3
- TZRPFOKZNIACPP-UHFFFAOYSA-N COC1=CC(=NC=C1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC1=CC(=NC=C1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 TZRPFOKZNIACPP-UHFFFAOYSA-N 0.000 claims description 3
- QSODAKGDHWKBKL-SNAWJCMRSA-N COC1=CC=C(C=C1)/C=C/C=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC1=CC=C(C=C1)/C=C/C=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 QSODAKGDHWKBKL-SNAWJCMRSA-N 0.000 claims description 3
- LWGOPGUUIXLJBX-LFYBBSHMSA-N COC1=CC=C(C=C1)/C=C/C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound COC1=CC=C(C=C1)/C=C/C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC LWGOPGUUIXLJBX-LFYBBSHMSA-N 0.000 claims description 3
- CJUORLZVGHCDKU-UHFFFAOYSA-N COC1=CC=C(C=C1)C#CC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC1=CC=C(C=C1)C#CC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 CJUORLZVGHCDKU-UHFFFAOYSA-N 0.000 claims description 3
- XKELIEPQRRJSKY-UHFFFAOYSA-N COC1=CC=C(C=C1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC1=CC=C(C=C1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 XKELIEPQRRJSKY-UHFFFAOYSA-N 0.000 claims description 3
- SLXLTCAWZAUMEP-UHFFFAOYSA-N COC1=CC=C(C=C1)CNC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC1=CC=C(C=C1)CNC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 SLXLTCAWZAUMEP-UHFFFAOYSA-N 0.000 claims description 3
- MNHRARWXZWKQCG-UHFFFAOYSA-N COC1=CC=C(C=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC1=CC=C(C=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 MNHRARWXZWKQCG-UHFFFAOYSA-N 0.000 claims description 3
- BBYZVKILBPLDIS-UHFFFAOYSA-N COC1=CC=C(C=C1)NC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC1=CC=C(C=C1)NC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 BBYZVKILBPLDIS-UHFFFAOYSA-N 0.000 claims description 3
- SXWBWGPGHVTKTQ-UHFFFAOYSA-N COC1=CC=C(C=N1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC1=CC=C(C=N1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 SXWBWGPGHVTKTQ-UHFFFAOYSA-N 0.000 claims description 3
- GVKNHXWCBKMNDQ-UHFFFAOYSA-N COC1=CC=C(N=N1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC1=CC=C(N=N1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 GVKNHXWCBKMNDQ-UHFFFAOYSA-N 0.000 claims description 3
- OHHUPZCGUNQMHD-UHFFFAOYSA-N COC1=NC=C(C=N1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC1=NC=C(C=N1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 OHHUPZCGUNQMHD-UHFFFAOYSA-N 0.000 claims description 3
- XUGJHMPQOZLKRL-UHFFFAOYSA-N COC1=NC=C(N=C1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NN(C=1)C Chemical compound COC1=NC=C(N=C1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NN(C=1)C XUGJHMPQOZLKRL-UHFFFAOYSA-N 0.000 claims description 3
- FAQVMPZDORAVRK-UHFFFAOYSA-N COC1=NOC(=C1)C(=O)NC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC1=NOC(=C1)C(=O)NC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 FAQVMPZDORAVRK-UHFFFAOYSA-N 0.000 claims description 3
- OHMSNGIDVZPCPY-UHFFFAOYSA-N COC=1C=C(C=CC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=C(C=CC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 OHMSNGIDVZPCPY-UHFFFAOYSA-N 0.000 claims description 3
- VGFWJASAZUUZTD-UHFFFAOYSA-N COC=1C=C(C=NC=1)NC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=C(C=NC=1)NC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 VGFWJASAZUUZTD-UHFFFAOYSA-N 0.000 claims description 3
- PCTPWDLYHLPYDC-UHFFFAOYSA-N COC=1C=C2C(=NC=1)C(N(C2)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O Chemical compound COC=1C=C2C(=NC=1)C(N(C2)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O PCTPWDLYHLPYDC-UHFFFAOYSA-N 0.000 claims description 3
- KRFHCVWQQZZUPP-UHFFFAOYSA-N COC=1C=C2C=CN(C(C2=CC=1)=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=C2C=CN(C(C2=CC=1)=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 KRFHCVWQQZZUPP-UHFFFAOYSA-N 0.000 claims description 3
- GQZDUIWMOXIWFB-UHFFFAOYSA-N COC=1C=C2CCN(C(C2=CC=1)=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=C2CCN(C(C2=CC=1)=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 GQZDUIWMOXIWFB-UHFFFAOYSA-N 0.000 claims description 3
- URLXFTMMNBOBBY-UHFFFAOYSA-N COC=1C=C2CN(C(C2=CC=1)=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=C2CN(C(C2=CC=1)=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 URLXFTMMNBOBBY-UHFFFAOYSA-N 0.000 claims description 3
- PWKSGWLMELETPP-UHFFFAOYSA-N COC=1C=CC(=NC=1)C(C)OC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC=1C=CC(=NC=1)C(C)OC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 PWKSGWLMELETPP-UHFFFAOYSA-N 0.000 claims description 3
- OTMVNNGWJZKRCK-UHFFFAOYSA-N COC=1C=CC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=CC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 OTMVNNGWJZKRCK-UHFFFAOYSA-N 0.000 claims description 3
- KSEPUNGTEKFYDU-UHFFFAOYSA-N COC=1C=CC(=NC=1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound COC=1C=CC(=NC=1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC KSEPUNGTEKFYDU-UHFFFAOYSA-N 0.000 claims description 3
- POUYKCBKWNNVEM-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C1=NC=CN=C1 Chemical compound COC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C1=NC=CN=C1 POUYKCBKWNNVEM-UHFFFAOYSA-N 0.000 claims description 3
- UFYSFMFQHIIZSQ-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=CC(=NC=1)C(=O)NC Chemical compound COC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=CC(=NC=1)C(=O)NC UFYSFMFQHIIZSQ-UHFFFAOYSA-N 0.000 claims description 3
- QAPUEOSNTPNKPV-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=CC(N(N=1)C)=O Chemical compound COC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=CC(N(N=1)C)=O QAPUEOSNTPNKPV-UHFFFAOYSA-N 0.000 claims description 3
- ANOXDTHGNJWGCZ-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 ANOXDTHGNJWGCZ-UHFFFAOYSA-N 0.000 claims description 3
- PSCZMTYXIJXCEM-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(C=C(O2)C2=CC=NC=C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(C=C(O2)C2=CC=NC=C2)C=1 PSCZMTYXIJXCEM-UHFFFAOYSA-N 0.000 claims description 3
- VXQZBTBVGUDZOP-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC(=CC=C2)OC2=CC=CC=C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC(=CC=C2)OC2=CC=CC=C2)C=1 VXQZBTBVGUDZOP-UHFFFAOYSA-N 0.000 claims description 3
- OWMWCRZQISTOBW-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC(=NC=C2)C)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC(=NC=C2)C)C=1 OWMWCRZQISTOBW-UHFFFAOYSA-N 0.000 claims description 3
- SAZVPEXPVOFUTI-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)C2=NC=CC=N2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)C2=NC=CC=N2)C=1 SAZVPEXPVOFUTI-UHFFFAOYSA-N 0.000 claims description 3
- HDWBYFCIQPEJAE-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC=NC=C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC=NC=C2)C=1 HDWBYFCIQPEJAE-UHFFFAOYSA-N 0.000 claims description 3
- DIYUZSHPQXRRME-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CN=CS2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CN=CS2)C=1 DIYUZSHPQXRRME-UHFFFAOYSA-N 0.000 claims description 3
- TXJZRYLJJZMJMV-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CN=NC=C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CN=NC=C2)C=1 TXJZRYLJJZMJMV-UHFFFAOYSA-N 0.000 claims description 3
- IPKVHMLHQKCECQ-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=NC3=CC=CC=C3C=C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=NC3=CC=CC=C3C=C2)C=1 IPKVHMLHQKCECQ-UHFFFAOYSA-N 0.000 claims description 3
- AXOWXAZMEBTPBQ-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=NC=CN=C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=NC=CN=C2)C=1 AXOWXAZMEBTPBQ-UHFFFAOYSA-N 0.000 claims description 3
- VWXUNQFFKVRFOM-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=NC=NC=C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=NC=NC=C2)C=1 VWXUNQFFKVRFOM-UHFFFAOYSA-N 0.000 claims description 3
- SCUDHIQNVIQTLE-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2CCN(CC2)C)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2CCN(CC2)C)C=1 SCUDHIQNVIQTLE-UHFFFAOYSA-N 0.000 claims description 3
- IQLHTMBEQVPTKT-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=C(C#N)C=CC=2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=C(C#N)C=CC=2)C=1 IQLHTMBEQVPTKT-UHFFFAOYSA-N 0.000 claims description 3
- CCDJYWUBYZCZHU-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=C(C=CC=2)CN(C)C)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=C(C=CC=2)CN(C)C)C=1 CCDJYWUBYZCZHU-UHFFFAOYSA-N 0.000 claims description 3
- LPAHWECZXGWGCC-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)C(=O)NC)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)C(=O)NC)C=1 LPAHWECZXGWGCC-UHFFFAOYSA-N 0.000 claims description 3
- QKHQNPVENBDLMY-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)NC(C)=O)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)NC(C)=O)C=1 QKHQNPVENBDLMY-UHFFFAOYSA-N 0.000 claims description 3
- KGDURDDXEKGROH-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)NC)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)NC)C=1 KGDURDDXEKGROH-UHFFFAOYSA-N 0.000 claims description 3
- AZTBVLIRDMHVLL-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(N(C=2)C)=O)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(N(C=2)C)=O)C=1 AZTBVLIRDMHVLL-UHFFFAOYSA-N 0.000 claims description 3
- GKFOHSAOICRNJW-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(N(N=2)C)=O)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(N(N=2)C)=O)C=1 GKFOHSAOICRNJW-UHFFFAOYSA-N 0.000 claims description 3
- TXAHVIRXDPFNLU-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)C(F)(F)F)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)C(F)(F)F)C=1 TXAHVIRXDPFNLU-UHFFFAOYSA-N 0.000 claims description 3
- FYSRZSIHEGDZGH-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=C(C=2)C)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=C(C=2)C)C=1 FYSRZSIHEGDZGH-UHFFFAOYSA-N 0.000 claims description 3
- RXHFQMGFGSOGOW-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 RXHFQMGFGSOGOW-UHFFFAOYSA-N 0.000 claims description 3
- UOWWUZMDRKKORR-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=NC=2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=NC=2)C=1 UOWWUZMDRKKORR-UHFFFAOYSA-N 0.000 claims description 3
- XCZRGULJCGVKTD-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NN(C=2)C)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NN(C=2)C)C=1 XCZRGULJCGVKTD-UHFFFAOYSA-N 0.000 claims description 3
- WUUHEGRVTJAJTN-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2N=CC(N(C=2)C)=O)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2N=CC(N(C=2)C)=O)C=1 WUUHEGRVTJAJTN-UHFFFAOYSA-N 0.000 claims description 3
- UZVYNGHVTFHRIS-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2N=CN(C=2)C)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2N=CN(C=2)C)C=1 UZVYNGHVTFHRIS-UHFFFAOYSA-N 0.000 claims description 3
- OEJPYWMPDNGVTF-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2N=NC=CC=2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2N=NC=CC=2)C=1 OEJPYWMPDNGVTF-UHFFFAOYSA-N 0.000 claims description 3
- UKTFEFCFYKOPAL-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CC3=NC=CC=C3C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CC3=NC=CC=C3C2)C=1 UKTFEFCFYKOPAL-UHFFFAOYSA-N 0.000 claims description 3
- MSIXFGIKUFERRG-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CC=3C(CC2)=NNC=3)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CC=3C(CC2)=NNC=3)C=1 MSIXFGIKUFERRG-UHFFFAOYSA-N 0.000 claims description 3
- VLFKDTKNQFDAND-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CCC=3C=CC=NC=3C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CCC=3C=CC=NC=3C2)C=1 VLFKDTKNQFDAND-UHFFFAOYSA-N 0.000 claims description 3
- SGLKHXPUUXJCTL-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CCNCC2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)N2CCNCC2)C=1 SGLKHXPUUXJCTL-UHFFFAOYSA-N 0.000 claims description 3
- ULJGSBGCSAUSIG-UHFFFAOYSA-N COC=1C=CC(=NC=1)NCC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=CC(=NC=1)NCC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 ULJGSBGCSAUSIG-UHFFFAOYSA-N 0.000 claims description 3
- GJXUMIICPRVTBV-UHFFFAOYSA-N COC=1C=CC(=NC=1)OCC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=CC(=NC=1)OCC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 GJXUMIICPRVTBV-UHFFFAOYSA-N 0.000 claims description 3
- MBIBEFJCLZGBPQ-UHFFFAOYSA-N COC=1C=NC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=NC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 MBIBEFJCLZGBPQ-UHFFFAOYSA-N 0.000 claims description 3
- SGAQGVHZPUVJMZ-UHFFFAOYSA-N COC=1C=NC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC=1C=NC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 SGAQGVHZPUVJMZ-UHFFFAOYSA-N 0.000 claims description 3
- HZDAYHHTAGHJSO-UHFFFAOYSA-N COC=1C=NC(=NC=1)N1CCN(CC1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1C=NC(=NC=1)N1CCN(CC1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 HZDAYHHTAGHJSO-UHFFFAOYSA-N 0.000 claims description 3
- FUJGIKLMUXHASX-UHFFFAOYSA-N COC=1C=NC=C(C=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC=1C=NC=C(C=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 FUJGIKLMUXHASX-UHFFFAOYSA-N 0.000 claims description 3
- DJWWLNGSTPBMGB-UHFFFAOYSA-N COC=1N=CC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1N=CC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 DJWWLNGSTPBMGB-UHFFFAOYSA-N 0.000 claims description 3
- MELZCQRHPUPBMY-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC1=CC2=C(N(C(=N2)C=2C=NC=CC=2)C)C=C1 Chemical compound COC=1N=CC(=NC=1)COC1=CC2=C(N(C(=N2)C=2C=NC=CC=2)C)C=C1 MELZCQRHPUPBMY-UHFFFAOYSA-N 0.000 claims description 3
- LJWXQQPKOXRVRF-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC1=CC2=C(NC(=N2)C=2C=NC=CC=2)C=C1 Chemical compound COC=1N=CC(=NC=1)COC1=CC2=C(NC(=N2)C=2C=NC=CC=2)C=C1 LJWXQQPKOXRVRF-UHFFFAOYSA-N 0.000 claims description 3
- GNKQXQWCLYCQRF-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound COC=1N=CC(=NC=1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 GNKQXQWCLYCQRF-UHFFFAOYSA-N 0.000 claims description 3
- GREFHIPTOJHKRQ-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC=1C=CC2=C(N(C(=N2)C=2C=NC=CC=2)C)C=1 Chemical compound COC=1N=CC(=NC=1)COC=1C=CC2=C(N(C(=N2)C=2C=NC=CC=2)C)C=1 GREFHIPTOJHKRQ-UHFFFAOYSA-N 0.000 claims description 3
- IOKDQUAIBOQSON-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COC=1N=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 IOKDQUAIBOQSON-UHFFFAOYSA-N 0.000 claims description 3
- OBQFPBPGGHFEJQ-UHFFFAOYSA-N COC=1N=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NN(C=2)C)C=1 Chemical compound COC=1N=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NN(C=2)C)C=1 OBQFPBPGGHFEJQ-UHFFFAOYSA-N 0.000 claims description 3
- BJFSNDWYSUQREZ-UHFFFAOYSA-N COC=1N=NC(=CC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC=1N=NC(=CC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 BJFSNDWYSUQREZ-UHFFFAOYSA-N 0.000 claims description 3
- MNLVRNFYHSILBG-UHFFFAOYSA-N COCCN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound COCCN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 MNLVRNFYHSILBG-UHFFFAOYSA-N 0.000 claims description 3
- FVZDDMNRMQYVNN-UHFFFAOYSA-N COCCOC=1C=C(C=NC=1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound COCCOC=1C=C(C=NC=1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC FVZDDMNRMQYVNN-UHFFFAOYSA-N 0.000 claims description 3
- ZCJNSWVHUFRULS-UHFFFAOYSA-N COCCOC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COCCOC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 ZCJNSWVHUFRULS-UHFFFAOYSA-N 0.000 claims description 3
- HACIYTVPVWNGJR-UHFFFAOYSA-N COCCOC=1C=NC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound COCCOC=1C=NC(=NC=1)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 HACIYTVPVWNGJR-UHFFFAOYSA-N 0.000 claims description 3
- WCSNDBWUARSQMB-UHFFFAOYSA-N FC1CN(C1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound FC1CN(C1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC WCSNDBWUARSQMB-UHFFFAOYSA-N 0.000 claims description 3
- IWIJWMQVUSPAMS-UHFFFAOYSA-N FCCOC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=CC(N(N=1)C)=O Chemical compound FCCOC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=CC(N(N=1)C)=O IWIJWMQVUSPAMS-UHFFFAOYSA-N 0.000 claims description 3
- FRVJIENULWNPPG-UHFFFAOYSA-N N1(C=NC=C1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound N1(C=NC=C1)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC FRVJIENULWNPPG-UHFFFAOYSA-N 0.000 claims description 3
- SEMYLGFZSADBCF-UHFFFAOYSA-N N1(CCOCC1)CCOC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound N1(CCOCC1)CCOC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 SEMYLGFZSADBCF-UHFFFAOYSA-N 0.000 claims description 3
- MPNMFPMIKIBHKP-UHFFFAOYSA-N N1=C(C=CC=C1)C(CC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O Chemical compound N1=C(C=CC=C1)C(CC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)=O MPNMFPMIKIBHKP-UHFFFAOYSA-N 0.000 claims description 3
- FHFAETRLOAKTQV-UHFFFAOYSA-N N1=C(C=CC=C1)C(CC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)O Chemical compound N1=C(C=CC=C1)C(CC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1)O FHFAETRLOAKTQV-UHFFFAOYSA-N 0.000 claims description 3
- RWDYRDKUKVAWLA-UHFFFAOYSA-N N1=C(C=CC=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound N1=C(C=CC=C1)COC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 RWDYRDKUKVAWLA-UHFFFAOYSA-N 0.000 claims description 3
- DNKNTYLNTKWYCP-UHFFFAOYSA-N N1=C(C=CC=C1)OCCOC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 Chemical compound N1=C(C=CC=C1)OCCOC=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 DNKNTYLNTKWYCP-UHFFFAOYSA-N 0.000 claims description 3
- IXYWKXBNGSTQKU-UHFFFAOYSA-N N1=CC(=CC=C1)C#CC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound N1=CC(=CC=C1)C#CC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 IXYWKXBNGSTQKU-UHFFFAOYSA-N 0.000 claims description 3
- OUIWIAVJIMCJHF-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)C=1N=CC(=NC=1)O Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)C=1N=CC(=NC=1)O OUIWIAVJIMCJHF-UHFFFAOYSA-N 0.000 claims description 3
- NRRMVHJONIRQSU-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C1=NC2=CC=CC=C2C=C1 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C1=NC2=CC=CC=C2C=C1 NRRMVHJONIRQSU-UHFFFAOYSA-N 0.000 claims description 3
- URVLMCOWBBZDHC-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C1=NC2=CC=CC=C2N=C1 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C1=NC2=CC=CC=C2N=C1 URVLMCOWBBZDHC-UHFFFAOYSA-N 0.000 claims description 3
- XFEHCUFBFQMQDK-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C1OC2=C(C1)C=CC=C2 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C1OC2=C(C1)C=CC=C2 XFEHCUFBFQMQDK-UHFFFAOYSA-N 0.000 claims description 3
- DKAZJNQHGPTRPQ-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C=1C=C2N=CC=NC2=CC=1 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C=1C=C2N=CC=NC2=CC=1 DKAZJNQHGPTRPQ-UHFFFAOYSA-N 0.000 claims description 3
- JNYWYUVARGLJLP-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C=1C=CC2=C(C=CO2)C=1 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC(=O)C=1C=CC2=C(C=CO2)C=1 JNYWYUVARGLJLP-UHFFFAOYSA-N 0.000 claims description 3
- MRFZQTLYRDYMDB-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC1=NC=CC=N1 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC1=NC=CC=N1 MRFZQTLYRDYMDB-UHFFFAOYSA-N 0.000 claims description 3
- HXYDOFJSHCUDBK-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC1=NC=NC=C1 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC1=NC=NC=C1 HXYDOFJSHCUDBK-UHFFFAOYSA-N 0.000 claims description 3
- ZTUPXUKSBBOGRY-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC1=NN=C2N1C=CC=C2 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)NC1=NN=C2N1C=CC=C2 ZTUPXUKSBBOGRY-UHFFFAOYSA-N 0.000 claims description 3
- PRSXGIUVLGTJER-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)OCC1=CC=C(C=N1)O Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)OCC1=CC=C(C=N1)O PRSXGIUVLGTJER-UHFFFAOYSA-N 0.000 claims description 3
- HMZURCYJUDDSHQ-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)OCC=1C=NC=CC=1 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)OCC=1C=NC=CC=1 HMZURCYJUDDSHQ-UHFFFAOYSA-N 0.000 claims description 3
- ORNRUECCHKMIQH-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)OCC=1N=CC(NC=1)=O Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=C(C=C2)OCC=1N=CC(NC=1)=O ORNRUECCHKMIQH-UHFFFAOYSA-N 0.000 claims description 3
- XCDHOZLYTSOTDT-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=C(N=1)C=CC(=C2)OCC=1C=NC=CC=1 Chemical compound N1=CC(=CC=C1)C=1OC2=C(N=1)C=CC(=C2)OCC=1C=NC=CC=1 XCDHOZLYTSOTDT-UHFFFAOYSA-N 0.000 claims description 3
- PLIYCIJRPAXBCY-UHFFFAOYSA-N N1=CC(=CC=C1)C=1OC2=NC=C(C=C2N=1)NC(C(F)(F)F)C1=CC=C(C=C1)OC Chemical compound N1=CC(=CC=C1)C=1OC2=NC=C(C=C2N=1)NC(C(F)(F)F)C1=CC=C(C=C1)OC PLIYCIJRPAXBCY-UHFFFAOYSA-N 0.000 claims description 3
- HTFWERWOXVMYGN-UHFFFAOYSA-N N1=CC(=CC=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound N1=CC(=CC=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 HTFWERWOXVMYGN-UHFFFAOYSA-N 0.000 claims description 3
- KMPANRNBVZXXSB-UHFFFAOYSA-N N1=CC(=CC=C1)COC=1C=CC2=C(C=C(O2)C=2C=NC=CC=2C#N)C=1 Chemical compound N1=CC(=CC=C1)COC=1C=CC2=C(C=C(O2)C=2C=NC=CC=2C#N)C=1 KMPANRNBVZXXSB-UHFFFAOYSA-N 0.000 claims description 3
- ILFBBAFQGPLQHX-UHFFFAOYSA-N N1=CC(=CC=C1)COC=1C=CC2=C(C=C(O2)C=2N3C(SC=2C#N)=NCC3)C=1 Chemical compound N1=CC(=CC=C1)COC=1C=CC2=C(C=C(O2)C=2N3C(SC=2C#N)=NCC3)C=1 ILFBBAFQGPLQHX-UHFFFAOYSA-N 0.000 claims description 3
- RMHINQXNUDKXOG-UHFFFAOYSA-N N1=CC(=CC=C1)OC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound N1=CC(=CC=C1)OC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 RMHINQXNUDKXOG-UHFFFAOYSA-N 0.000 claims description 3
- VUYUGHFNKILAOW-UHFFFAOYSA-N N1=CN=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound N1=CN=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 VUYUGHFNKILAOW-UHFFFAOYSA-N 0.000 claims description 3
- JQKRPMGAFXSMOK-UHFFFAOYSA-N N1=CNC=2CN(CCC=21)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound N1=CNC=2CN(CCC=21)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC JQKRPMGAFXSMOK-UHFFFAOYSA-N 0.000 claims description 3
- GGKVSYOZVMVKSM-UHFFFAOYSA-N N1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound N1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 GGKVSYOZVMVKSM-UHFFFAOYSA-N 0.000 claims description 3
- VJWGAIMNOREJGC-UHFFFAOYSA-N N=1C=CN2C=1CN(CC2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound N=1C=CN2C=1CN(CC2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC VJWGAIMNOREJGC-UHFFFAOYSA-N 0.000 claims description 3
- DIFQBWLTWFKERI-UHFFFAOYSA-N O1C(=CC2=C1C=CC=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound O1C(=CC2=C1C=CC=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC DIFQBWLTWFKERI-UHFFFAOYSA-N 0.000 claims description 3
- CLMUFZCKOUFRKL-UHFFFAOYSA-N O1C(CC2=C1C=CC=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound O1C(CC2=C1C=CC=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC CLMUFZCKOUFRKL-UHFFFAOYSA-N 0.000 claims description 3
- RYEPUIVPXNEULS-UHFFFAOYSA-N O1C=CC2=C1C=CC(=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound O1C=CC2=C1C=CC(=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC RYEPUIVPXNEULS-UHFFFAOYSA-N 0.000 claims description 3
- CLMUFZCKOUFRKL-NRFANRHFSA-N O1[C@@H](CC2=C1C=CC=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound O1[C@@H](CC2=C1C=CC=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC CLMUFZCKOUFRKL-NRFANRHFSA-N 0.000 claims description 3
- CLMUFZCKOUFRKL-OAQYLSRUSA-N O1[C@H](CC2=C1C=CC=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC Chemical compound O1[C@H](CC2=C1C=CC=C2)C=1OC2=C(N=1)C=C(C=C2)OCC1=NC=C(C=C1)OC CLMUFZCKOUFRKL-OAQYLSRUSA-N 0.000 claims description 3
- ZGPCQTYUOLAZNV-UHFFFAOYSA-N OC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(N(N=2)C)=O)C=1 Chemical compound OC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(N(N=2)C)=O)C=1 ZGPCQTYUOLAZNV-UHFFFAOYSA-N 0.000 claims description 3
- SWPCNVACXUXUQW-UHFFFAOYSA-N OCCN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 Chemical compound OCCN1N=CC(=C1)COC=1C=CC2=C(C=C(O2)C2=C(C=NC=C2)C#N)C=1 SWPCNVACXUXUQW-UHFFFAOYSA-N 0.000 claims description 3
- MCSZYSJFHJCDCJ-UHFFFAOYSA-N S1C=2N(C(=C1)C=1OC3=C(C=1)C=C(C=C3)OCC=1C=NC=CC=1)CCN=2 Chemical compound S1C=2N(C(=C1)C=1OC3=C(C=1)C=C(C=C3)OCC=1C=NC=CC=1)CCN=2 MCSZYSJFHJCDCJ-UHFFFAOYSA-N 0.000 claims description 3
- GVOALBUQWHDBAP-UHFFFAOYSA-N S1C=2N(C(=C1)COC=1C=CC3=C(C=C(O3)C3=C(C=NC=C3)C#N)C=1)CCN=2 Chemical compound S1C=2N(C(=C1)COC=1C=CC3=C(C=C(O3)C3=C(C=NC=C3)C#N)C=1)CCN=2 GVOALBUQWHDBAP-UHFFFAOYSA-N 0.000 claims description 3
- NFGMXAUDEUEPCA-UHFFFAOYSA-N S1C=2N(C(=C1)COC=1C=CC3=C(N=C(O3)C=3C=NC=CC=3)C=1)CCN=2 Chemical compound S1C=2N(C(=C1)COC=1C=CC3=C(N=C(O3)C=3C=NC=CC=3)C=1)CCN=2 NFGMXAUDEUEPCA-UHFFFAOYSA-N 0.000 claims description 3
- KXGNMGWKTVFLDX-UHFFFAOYSA-N [4-[[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]carbamoyl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C(=O)NC1=CC=C(OC(=N2)C=3C=CC(Cl)=CC=3)C2=C1 KXGNMGWKTVFLDX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- FDVPIOYDRRNLPY-UHFFFAOYSA-N n-(2-phenyl-1,3-benzoxazol-5-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=C1N=2)=CC=C1OC=2C1=CC=CC=C1 FDVPIOYDRRNLPY-UHFFFAOYSA-N 0.000 claims description 3
- KJGHWYJJBAHACU-UHFFFAOYSA-N n-(2-pyridin-3-yl-1,3-benzoxazol-5-yl)-1,3-benzodioxole-5-carboxamide Chemical compound C=1C=C2OCOC2=CC=1C(=O)NC(C=C1N=2)=CC=C1OC=2C1=CC=CN=C1 KJGHWYJJBAHACU-UHFFFAOYSA-N 0.000 claims description 3
- YETMHINSGRFIIU-UHFFFAOYSA-N n-(2-pyridin-3-yl-1,3-benzoxazol-5-yl)-1-benzofuran-2-carboxamide Chemical compound C=1C2=CC=CC=C2OC=1C(=O)NC(C=C1N=2)=CC=C1OC=2C1=CC=CN=C1 YETMHINSGRFIIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 102000014461 Ataxins Human genes 0.000 claims description 2
- 108010078286 Ataxins Proteins 0.000 claims description 2
- QSODAKGDHWKBKL-PLNGDYQASA-N COC1=CC=C(C=C1)\C=C/C=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC1=CC=C(C=C1)\C=C/C=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 QSODAKGDHWKBKL-PLNGDYQASA-N 0.000 claims description 2
- OKQJTVBUUMCXPU-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 OKQJTVBUUMCXPU-UHFFFAOYSA-N 0.000 claims description 2
- GNHDNZJUEBUFAD-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC=C(C#N)C=C2)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C2=CC=C(C#N)C=C2)C=1 GNHDNZJUEBUFAD-UHFFFAOYSA-N 0.000 claims description 2
- 206010008025 Cerebellar ataxia Diseases 0.000 claims description 2
- 102000016252 Huntingtin Human genes 0.000 claims description 2
- 108050004784 Huntingtin Proteins 0.000 claims description 2
- NYKUJMPQVPJIJC-UHFFFAOYSA-N OC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)C(=O)NC)C=1 Chemical compound OC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)C(=O)NC)C=1 NYKUJMPQVPJIJC-UHFFFAOYSA-N 0.000 claims description 2
- 238000012879 PET imaging Methods 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 208000024777 Prion disease Diseases 0.000 claims description 2
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims description 2
- 210000004227 basal ganglia Anatomy 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 238000013170 computed tomography imaging Methods 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 claims description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- UDOLCLUEPHEEIA-UHFFFAOYSA-N CN1N=CC(=C1)C=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 Chemical compound CN1N=CC(=C1)C=1C=CC(=NC=1)COC=1C=C2C(=NC=1)OC(=N2)C=1C=NC=CC=1 UDOLCLUEPHEEIA-UHFFFAOYSA-N 0.000 claims 2
- ZFJFJZXRNGRKKC-UHFFFAOYSA-N COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)N)C=1 Chemical compound COC=1C=CC(=NC=1)COC=1C=CC2=C(N=C(O2)C=2C=CC(=NC=2)N)C=1 ZFJFJZXRNGRKKC-UHFFFAOYSA-N 0.000 claims 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- DQPBINMBSNANNP-UHFFFAOYSA-N COC1=CN=C(COC(C=C2)=CC3=C2OC(C2=CC=CN=C2N)=N3)C=C1 Chemical compound COC1=CN=C(COC(C=C2)=CC3=C2OC(C2=CC=CN=C2N)=N3)C=C1 DQPBINMBSNANNP-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462043603P | 2014-08-29 | 2014-08-29 | |
| US62/043,603 | 2014-08-29 | ||
| PCT/US2015/047407 WO2016033445A1 (en) | 2014-08-29 | 2015-08-28 | Probes for imaging huntingtin protein |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020214504A Division JP7126541B2 (ja) | 2014-08-29 | 2020-12-24 | ハンチントンタンパク質のイメージング用プローブ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017528519A JP2017528519A (ja) | 2017-09-28 |
| JP2017528519A5 true JP2017528519A5 (OSRAM) | 2018-10-04 |
| JP6817207B2 JP6817207B2 (ja) | 2021-01-20 |
Family
ID=55400648
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017530971A Active JP6817207B2 (ja) | 2014-08-29 | 2015-08-28 | ハンチントンタンパク質のイメージング用プローブ |
| JP2020214504A Active JP7126541B2 (ja) | 2014-08-29 | 2020-12-24 | ハンチントンタンパク質のイメージング用プローブ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020214504A Active JP7126541B2 (ja) | 2014-08-29 | 2020-12-24 | ハンチントンタンパク質のイメージング用プローブ |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US10479802B2 (OSRAM) |
| EP (2) | EP3186233B8 (OSRAM) |
| JP (2) | JP6817207B2 (OSRAM) |
| KR (2) | KR102456946B1 (OSRAM) |
| CN (2) | CN116655618B (OSRAM) |
| AU (1) | AU2015308774B2 (OSRAM) |
| BR (1) | BR112017004141B8 (OSRAM) |
| CA (1) | CA2959501C (OSRAM) |
| DK (1) | DK3186233T3 (OSRAM) |
| EA (1) | EA035646B1 (OSRAM) |
| ES (1) | ES2898965T3 (OSRAM) |
| HR (1) | HRP20211778T1 (OSRAM) |
| HU (1) | HUE056957T2 (OSRAM) |
| IL (1) | IL250803B (OSRAM) |
| MX (2) | MX380810B (OSRAM) |
| PL (1) | PL3186233T3 (OSRAM) |
| PT (1) | PT3186233T (OSRAM) |
| SG (1) | SG11201701600QA (OSRAM) |
| SI (1) | SI3186233T1 (OSRAM) |
| WO (1) | WO2016033445A1 (OSRAM) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107074817B (zh) | 2014-08-29 | 2023-12-15 | Chdi基金会股份有限公司 | 用于成像亨廷顿蛋白的探针 |
| DK3197277T3 (da) | 2014-08-29 | 2022-01-31 | Chdi Foundation Inc | Prober til billeddannelse af huntingtin-protein |
| KR102456946B1 (ko) | 2014-08-29 | 2022-10-21 | 씨에이치디아이 파운데이션, 인코포레이티드 | 헌팅틴을 단백질 영상화하기 위한 프로브 |
| SG11201701580XA (en) | 2014-08-29 | 2017-03-30 | Chdi Foundation Inc | Probes for imaging huntingtin protein |
| MX382156B (es) | 2015-08-28 | 2025-03-13 | Chdi Foundation Inc | Sondas para formar imagenes de proteina de huntingtina. |
| BR112018068066B1 (pt) | 2016-03-11 | 2023-11-28 | Ac Immune Sa | Compostos bicíclicos e seu uso, composição diagnóstica e farmacêutica, misturas, métodos de coleção de dados para diagnóstico, para determinar uma predisposição a, para monitorar transtorno residual e para prever a capacidade de resposta de um paciente sofrendo de transtorno ou anormalidade associado com agregados de alfa-sinucleína, métodos para determinar a quantidade de agregados de alfa-sinucleína e para preparar um composto, kit teste e kit para preparar uma preparação radio farmacêutica |
| CN107056723A (zh) * | 2017-04-21 | 2017-08-18 | 云南大学 | 一种具有抑制血管内皮生长因子受体信号传导的化合物 |
| NZ763299A (en) | 2017-09-14 | 2025-09-26 | Daiichi Sankyo Co Ltd | Compound having cyclic structure |
| US20210169080A1 (en) | 2018-04-20 | 2021-06-10 | Bayer Aktiengesellschaft | Heterocycle derivatives as pesticides |
| JP7397492B2 (ja) | 2018-06-08 | 2023-12-13 | エーシー・イミューン・エス・アー | 診断のための二環式化合物 |
| EP3897630B1 (en) | 2018-12-21 | 2024-01-10 | Celgene Corporation | Thienopyridine inhibitors of ripk2 |
| US11389438B2 (en) | 2019-02-25 | 2022-07-19 | Chdi Foundation, Inc. | Compounds for targeting mutant huntingtin protein and uses thereof |
| CN111635400A (zh) | 2019-03-02 | 2020-09-08 | 察略盛医药科技(上海)有限公司 | 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途 |
| ES3029867T3 (en) * | 2019-12-18 | 2025-06-25 | Chdi Foundation Inc | Compounds and probes for imaging huntingtin protein |
| MX2022008627A (es) | 2020-01-13 | 2022-11-08 | Verge Analytics Inc | Pirazolo-pirimidinas sustituidas y usos de las mismas. |
| EP4146653A1 (en) | 2020-05-07 | 2023-03-15 | AC Immune SA | Novel compounds for diagnosis |
| WO2022031946A1 (en) * | 2020-08-06 | 2022-02-10 | Chdi Foundation, Inc. | Heterobiaryl compounds and imaging agents for imaging huntingtin protein |
| CA3214756A1 (en) * | 2021-04-08 | 2022-10-13 | Longbin Liu | Isoindolinone compounds and imaging agents for imaging huntingtin protein |
| MX2023012652A (es) * | 2021-04-27 | 2024-01-08 | Chdi Foundation Inc | Compuestos deuterados y agentes de imagen para representar la proteína huntingtina. |
| WO2023283425A1 (en) | 2021-07-09 | 2023-01-12 | Plexium, Inc. | Aryl compounds and pharmaceutical compositions that modulate ikzf2 |
| WO2023083961A1 (en) | 2021-11-10 | 2023-05-19 | Ac Immune Sa | Dihydropyrrolo[3,4-c]pyrazole derivatives and their use in diagnosis |
| CA3235230A1 (en) | 2021-11-10 | 2023-05-19 | Jerome Molette | 4h-imidazo[1,5-b]pyrazole derivatives for diagnosis |
| JP2024544521A (ja) | 2021-11-10 | 2024-12-03 | エーシー・イミューン・エス・アー | ジヒドロピロロ［３，４ｃ］－ピラゾール誘導体及び診断におけるその使用 |
| TW202425965A (zh) | 2022-09-30 | 2024-07-01 | 日商科研製藥股份有限公司 | 縮環化合物及含有其之醫藥 |
| WO2024126842A1 (en) | 2022-12-16 | 2024-06-20 | Ac Immune Sa | Novel compounds for diagnosis |
| CN120344536A (zh) | 2022-12-16 | 2025-07-18 | Ac免疫有限公司 | 用于诊断的新化合物 |
| AU2024271346A1 (en) * | 2023-05-18 | 2025-11-27 | Enveda Therapeutics, Inc. | G-protein coupled receptor antagonist |
| WO2025037013A1 (en) | 2023-08-16 | 2025-02-20 | Ac Immune Sa | Diagnostic compounds that bind to alpha-synuclein |
| WO2025106920A1 (en) * | 2023-11-15 | 2025-05-22 | Yale University | Parp pet imaging agents and methods of using the same |
| CN119264072B (zh) * | 2024-12-06 | 2025-05-02 | 国科大杭州高等研究院 | 对细胞成像的荧光探针及其合成方法和应用 |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985755A (en) | 1972-06-02 | 1976-10-12 | E. R. Squibb & Sons, Inc. | Pyridine containing isothiocyanobenzoxazoles |
| US4198416A (en) | 1976-09-30 | 1980-04-15 | Meiji Seika Kaisha, Ltd. | 5-Alkoxy-picolinic esters and anti-hypertensive composition containing 5-alkoxy-picolinic esters |
| DE2909754A1 (de) * | 1979-03-13 | 1980-09-18 | Thomae Gmbh Dr K | Neue benzofuran- und benzothiophenderivate, deren herstellung und deren verwendung als arzneimittel |
| FR2524468B1 (fr) | 1982-04-06 | 1985-10-18 | Sandoz Sa | Nouveaux derives condenses du thiophene, leur preparation et leur utilisation comme azurants optiques |
| JP2869561B2 (ja) * | 1989-05-22 | 1999-03-10 | 大塚製薬株式会社 | 血小板粘着抑制剤 |
| US5041453A (en) | 1990-05-30 | 1991-08-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Quinolinyl-benzoheterobicyclic derivatives as antagonists of leukotriene D4 |
| JP2600644B2 (ja) | 1991-08-16 | 1997-04-16 | 藤沢薬品工業株式会社 | チアゾリルベンゾフラン誘導体 |
| GB9203798D0 (en) | 1992-02-21 | 1992-04-08 | Fujisawa Pharmaceutical Co | Quinolylbenzofuran derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
| WO1994022846A1 (en) * | 1993-03-30 | 1994-10-13 | Pfizer Inc. | Compounds enhancing antitumor activity of other cytotoxic agents |
| GB9317949D0 (en) * | 1993-08-28 | 1993-10-13 | Stevens Malcolm F G | Benzothiazole compounds |
| ES2163587T3 (es) | 1995-02-28 | 2002-02-01 | Lilly Co Eli | Compuestos de benzotiofeno, productos intermedios, composiciones y procedimientos. |
| JPH08325265A (ja) * | 1995-05-29 | 1996-12-10 | Fujisawa Pharmaceut Co Ltd | チアゾリルベンゾフラン誘導体の製造方法、および該製造方法に用いられる化合物 |
| WO1997027190A1 (en) | 1996-01-22 | 1997-07-31 | Fujisawa Pharmaceutical Co., Ltd. | Thiazolylbenzofuran derivatives and pharmaceutical compositions containing them |
| JPH11171886A (ja) | 1997-12-08 | 1999-06-29 | Mitsui Chem Inc | アミジンまたはグアニジンを側鎖にもつピロリルベンズイミダゾール誘導体 |
| US6573264B1 (en) | 2000-10-23 | 2003-06-03 | Cv Therapeutics, Inc. | Heteroaryl alkyl piperazine derivatives |
| US7163952B2 (en) * | 2001-12-03 | 2007-01-16 | Japan Tobacco Inc. | Azole compound and medicinal use thereof |
| PL210413B1 (pl) | 2001-12-20 | 2012-01-31 | Wyeth Corp | Pochodne indoliloalkiloaminy |
| CA2438032C (en) | 2003-03-14 | 2013-05-07 | University Of Pittsburgh | Benzothiazole derivative compounds, compositions and uses |
| WO2005040337A2 (en) | 2003-05-20 | 2005-05-06 | The Regents Of The University Of California | METHODS FOR BINDING AGENTS TO β-AMYLOID PLAQUES |
| WO2005016384A1 (ja) | 2003-08-13 | 2005-02-24 | Bf Research Institute, Inc. | アミロイド蓄積性疾患のプローブ、アミロイド染色剤、アミロイド蓄積性疾患の治療および予防薬、ならびに神経原線維変化の診断プローブおよび染色剤 |
| TW200616974A (en) | 2004-07-01 | 2006-06-01 | Astrazeneca Ab | Chemical compounds |
| KR20080094699A (ko) | 2006-02-15 | 2008-10-23 | 사노피-아벤티스 | 신규 아미노알콜-치환된 아릴디하이드로이소퀴놀리논, 이의제조 방법 및 이의 약물로서의 용도 |
| EP2054060B1 (en) | 2006-08-24 | 2014-04-02 | Australian Nuclear Science & Technology Organisation | Fluorinated ligands for targeting peripheral benzodiazepine receptors |
| JP5190893B2 (ja) * | 2006-12-25 | 2013-04-24 | 国立大学法人東北大学 | ベンゾキサゾール誘導体 |
| US7858803B2 (en) | 2007-04-27 | 2010-12-28 | The General Hospital Corporation | Imaging tracers for early detection and treatment of amyloid plaques caused by Alzheimer's disease and related disorders |
| KR101469275B1 (ko) | 2007-06-01 | 2014-12-08 | 재단법인서울대학교산학협력재단 | 베타아밀로이드 침착의 영상화를 위한 헤테로사이클릭 인덴계열의 유도체 및 그의 방사성 동위원소 표지화합물 |
| CA2700841A1 (en) | 2007-09-27 | 2009-04-02 | The United States Of America, As Represented By The Secretary, Departmen T Of Health And Human Services | Isoindoline compounds for the treatment of spinal muscular atrophy and other uses |
| US20090123373A1 (en) * | 2007-11-05 | 2009-05-14 | Yanming Wang | Amyloid-imaging agents |
| US8153813B2 (en) | 2007-12-20 | 2012-04-10 | Abbott Laboratories | Benzothiazole and benzooxazole derivatives and methods of use |
| WO2009146388A1 (en) | 2008-05-28 | 2009-12-03 | The Trustees Of Columbia University In The City Of New York | Voxel-based methods for assessing subjects using positron emission tomography |
| ES2554772T3 (es) * | 2008-05-30 | 2015-12-23 | Merck Sharp & Dohme Corp. | Azabenzoxazoles sustituidos novedosos |
| WO2009155024A1 (en) * | 2008-05-30 | 2009-12-23 | Merck & Co., Inc. | Novel substituted indoles |
| US20110212031A1 (en) * | 2008-10-31 | 2011-09-01 | Cyrille Sur | Novel substituted azabenzoxazoles |
| US8691187B2 (en) | 2009-03-23 | 2014-04-08 | Eli Lilly And Company | Imaging agents for detecting neurological disorders |
| GB0905664D0 (en) * | 2009-04-02 | 2009-05-13 | Summit Corp Plc | Compounds for treatment of duchenne muscular dystrophy |
| PL2414369T3 (pl) | 2009-04-02 | 2016-04-29 | Fundacion Centro Nac De Investigaciones Oncologicas Carlos Iii | Pochodne imidazo[2,1-b][1,3,4]tiadiazolu |
| ES2620177T3 (es) | 2009-10-15 | 2017-06-27 | Guerbet | Agentes de formación de imágenes y su uso para el diagnóstico in vivo de enfermedades neurodegenerativas, particularmente la enfermedad de Alzheimer y enfermedades derivadas |
| JP2011168515A (ja) | 2010-02-17 | 2011-09-01 | Kowa Co | エリスロポエチン産生促進作用を有する２−アリールベンゾオキサゾール化合物 |
| WO2012007510A1 (en) * | 2010-07-14 | 2012-01-19 | Bayer Pharma Aktiengesellschaft | Compounds for binding and imaging amyloid plaques and their use |
| PH12013501099A1 (en) | 2010-11-30 | 2013-07-08 | Takeda Pharmaceuticals Co | Bicyclic compound |
| CN102391260B (zh) | 2011-09-29 | 2014-12-10 | 上海交通大学 | 3-甲酮-6-取代-苯并呋喃类化合物及其制备方法和用途 |
| CN104540835B (zh) | 2012-04-26 | 2017-08-08 | 百时美施贵宝公司 | 用于治疗血小板聚集的作为蛋白酶激活受体4(par4)抑制剂的咪唑并噻二唑衍生物 |
| US9370588B2 (en) | 2013-01-04 | 2016-06-21 | University Of Massachusetts | Luciferin amides |
| GB201306248D0 (en) * | 2013-04-05 | 2013-05-22 | Ucl Business Plc | Compounds and their uses |
| JP6503336B2 (ja) | 2013-07-17 | 2019-04-17 | 大塚製薬株式会社 | シアノトリアゾール化合物 |
| DK3197277T3 (da) | 2014-08-29 | 2022-01-31 | Chdi Foundation Inc | Prober til billeddannelse af huntingtin-protein |
| SG11201701580XA (en) | 2014-08-29 | 2017-03-30 | Chdi Foundation Inc | Probes for imaging huntingtin protein |
| CN107074817B (zh) | 2014-08-29 | 2023-12-15 | Chdi基金会股份有限公司 | 用于成像亨廷顿蛋白的探针 |
| KR102456946B1 (ko) | 2014-08-29 | 2022-10-21 | 씨에이치디아이 파운데이션, 인코포레이티드 | 헌팅틴을 단백질 영상화하기 위한 프로브 |
| MX382156B (es) | 2015-08-28 | 2025-03-13 | Chdi Foundation Inc | Sondas para formar imagenes de proteina de huntingtina. |
-
2015
- 2015-08-28 KR KR1020177008383A patent/KR102456946B1/ko active Active
- 2015-08-28 JP JP2017530971A patent/JP6817207B2/ja active Active
- 2015-08-28 AU AU2015308774A patent/AU2015308774B2/en active Active
- 2015-08-28 ES ES15836321T patent/ES2898965T3/es active Active
- 2015-08-28 EP EP15836321.8A patent/EP3186233B8/en active Active
- 2015-08-28 CN CN202310475134.8A patent/CN116655618B/zh active Active
- 2015-08-28 CN CN201580058282.3A patent/CN107108534B/zh active Active
- 2015-08-28 PL PL15836321T patent/PL3186233T3/pl unknown
- 2015-08-28 US US15/507,208 patent/US10479802B2/en active Active
- 2015-08-28 CA CA2959501A patent/CA2959501C/en active Active
- 2015-08-28 KR KR1020227035965A patent/KR102586736B1/ko active Active
- 2015-08-28 EP EP21192872.6A patent/EP4006016A3/en not_active Withdrawn
- 2015-08-28 HR HRP20211778TT patent/HRP20211778T1/hr unknown
- 2015-08-28 DK DK15836321.8T patent/DK3186233T3/da active
- 2015-08-28 PT PT158363218T patent/PT3186233T/pt unknown
- 2015-08-28 BR BR112017004141A patent/BR112017004141B8/pt active IP Right Grant
- 2015-08-28 WO PCT/US2015/047407 patent/WO2016033445A1/en not_active Ceased
- 2015-08-28 SG SG11201701600QA patent/SG11201701600QA/en unknown
- 2015-08-28 HU HUE15836321A patent/HUE056957T2/hu unknown
- 2015-08-28 EA EA201790407A patent/EA035646B1/ru unknown
- 2015-08-28 SI SI201531751T patent/SI3186233T1/sl unknown
- 2015-08-28 MX MX2017002703A patent/MX380810B/es unknown
-
2017
- 2017-02-27 IL IL250803A patent/IL250803B/en active IP Right Grant
- 2017-02-28 MX MX2021003311A patent/MX2021003311A/es unknown
-
2019
- 2019-08-02 US US16/530,594 patent/US11059836B2/en active Active
-
2020
- 2020-12-24 JP JP2020214504A patent/JP7126541B2/ja active Active
-
2022
- 2022-08-05 US US17/881,895 patent/US12258355B2/en active Active