JP2010513334A5

JP2010513334A5 -

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Publication number: JP2010513334A5
Authority: JP; Japan
Prior art keywords: compound; pyridin; dichloro; dimethoxy; phenyl
Prior art date: 2007-12-21
Legal status : Granted

Application number

JP2009541766A

Other languages

English (en)

Japanese (ja)

Other versions

JP5342451B2 (ja

JP2010513334A (ja

Filing date

2007-12-21

Publication date

2013-08-22

2007-12-21 Application filed filed Critical

2007-12-21 Priority claimed from PCT/DK2007/000564 external-priority patent/WO2008077404A1/en

2010-04-30 Publication of JP2010513334A publication Critical patent/JP2010513334A/ja

2013-08-22 Publication of JP2010513334A5 publication Critical patent/JP2010513334A5/ja

2013-11-13 Application granted granted Critical

2013-11-13 Publication of JP5342451B2 publication Critical patent/JP5342451B2/ja

Status Expired - Fee Related legal-status Critical Current

2027-12-21 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims 207
-1 hydrate Chemical class 0.000 claims 71
239000001257 hydrogen Substances 0.000 claims 37
229910052739 hydrogen Inorganic materials 0.000 claims 37
125000001424 substituent group Chemical group 0.000 claims 28
125000000217 alkyl group Chemical group 0.000 claims 26
150000002431 hydrogen Chemical class 0.000 claims 25
125000001188 haloalkyl group Chemical group 0.000 claims 22
125000002768 hydroxyalkyl group Chemical group 0.000 claims 21
125000003342 alkenyl group Chemical group 0.000 claims 18
125000000304 alkynyl group Chemical group 0.000 claims 18
125000000392 cycloalkenyl group Chemical group 0.000 claims 18
125000003545 alkoxy group Chemical group 0.000 claims 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
125000004043 oxo group Chemical group O=* 0.000 claims 17
125000000753 cycloalkyl group Chemical group 0.000 claims 16
229910052736 halogen Inorganic materials 0.000 claims 15
150000002367 halogens Chemical class 0.000 claims 15
125000003118 aryl group Chemical group 0.000 claims 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
125000004448 alkyl carbonyl group Chemical group 0.000 claims 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
125000004104 aryloxy group Chemical group 0.000 claims 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 11
125000004183 alkoxy alkyl group Chemical group 0.000 claims 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
125000002877 alkyl aryl group Chemical group 0.000 claims 10
125000004414 alkyl thio group Chemical group 0.000 claims 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 10
125000004093 cyano group Chemical group *C#N 0.000 claims 9
201000004624 Dermatitis Diseases 0.000 claims 8
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
125000004366 heterocycloalkenyl group Chemical group 0.000 claims 8
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 7
125000003710 aryl alkyl group Chemical group 0.000 claims 7
239000008194 pharmaceutical composition Substances 0.000 claims 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 6
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 6
125000005129 aryl carbonyl group Chemical group 0.000 claims 6
125000000623 heterocyclic group Chemical group 0.000 claims 6
125000001153 fluoro group Chemical group F* 0.000 claims 5
125000001072 heteroaryl group Chemical group 0.000 claims 5
125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims 5
208000017520 skin disease Diseases 0.000 claims 5
XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims 4
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 4
206010040799 Skin atrophy Diseases 0.000 claims 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 4
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 4
125000001309 chloro group Chemical group Cl* 0.000 claims 4
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
150000001204 N-oxides Chemical class 0.000 claims 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
150000002148 esters Chemical class 0.000 claims 3
125000004076 pyridyl group Chemical group 0.000 claims 3
150000003839 salts Chemical class 0.000 claims 3
239000012453 solvate Substances 0.000 claims 3
208000024891 symptom Diseases 0.000 claims 3
125000003944 tolyl group Chemical group 0.000 claims 3
JMSLXMMWELRQMU-UHFFFAOYSA-N 1-(2-but-2-ynoxy-3,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound CC#CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl JMSLXMMWELRQMU-UHFFFAOYSA-N 0.000 claims 2
GMRZCWUZXHCTOJ-UHFFFAOYSA-N 1-(2-but-3-enoxy-3,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=CCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl GMRZCWUZXHCTOJ-UHFFFAOYSA-N 0.000 claims 2
IAWADUJZYLNTIM-UHFFFAOYSA-N 1-(2-butoxy-3,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C1=CC(OC)=C(OC)C(OCCCC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl IAWADUJZYLNTIM-UHFFFAOYSA-N 0.000 claims 2
NFUFDHIMMGDBHD-UHFFFAOYSA-N 1-(3-but-2-ynoxy-2,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound COC1=C(OCC#CC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl NFUFDHIMMGDBHD-UHFFFAOYSA-N 0.000 claims 2
DOLXLIULMTUVPH-UHFFFAOYSA-N 1-(3-but-3-enoxy-2,4-dimethoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound COC1=C(OCCC=C)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DOLXLIULMTUVPH-UHFFFAOYSA-N 0.000 claims 2
OXLLLXVNJUIDJX-UHFFFAOYSA-N 1-(3-cyclopentyloxy-2-hydroxy-4-methoxyphenyl)-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound OC1=C(OC2CCCC2)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl OXLLLXVNJUIDJX-UHFFFAOYSA-N 0.000 claims 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
VSYDBUNFIWMARN-UHFFFAOYSA-N 1-[2,3-bis(difluoromethoxy)-4-methoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound FC(F)OC1=C(OC(F)F)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VSYDBUNFIWMARN-UHFFFAOYSA-N 0.000 claims 2
DTYNTAQEFRZTOF-UHFFFAOYSA-N 1-[2-(2-cyclohexylethoxy)-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C1CCCCC1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DTYNTAQEFRZTOF-UHFFFAOYSA-N 0.000 claims 2
VWZKDNCXKKHULU-UHFFFAOYSA-N 1-[2-[(2-chlorophenyl)methoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=CC=C(Cl)C=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VWZKDNCXKKHULU-UHFFFAOYSA-N 0.000 claims 2
UUALYBMSYGWDOD-UHFFFAOYSA-N 1-[2-[(3-chlorophenyl)methoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=CC(Cl)=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl UUALYBMSYGWDOD-UHFFFAOYSA-N 0.000 claims 2
FAUONCLSIFGBAE-UHFFFAOYSA-N 1-[2-[(4-chlorophenyl)methoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=C(Cl)C=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl FAUONCLSIFGBAE-UHFFFAOYSA-N 0.000 claims 2
AUDYFIBIJYSVQY-UHFFFAOYSA-N 1-[2-[(5-chlorothiophen-2-yl)methoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=C(Cl)SC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl AUDYFIBIJYSVQY-UHFFFAOYSA-N 0.000 claims 2
DOQIRWPNZIGHBL-UHFFFAOYSA-N 1-[2-[2-(3-bromophenyl)ethoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=CC(Br)=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DOQIRWPNZIGHBL-UHFFFAOYSA-N 0.000 claims 2
MJJGEGJEFXULAU-UHFFFAOYSA-N 1-[2-[2-(4-chlorophenoxy)ethoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=C(Cl)C=CC=1OCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl MJJGEGJEFXULAU-UHFFFAOYSA-N 0.000 claims 2
FIWOJRHNMZWIII-UHFFFAOYSA-N 1-[2-[2-(4-chlorophenyl)ethoxy]-3,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound C=1C=C(Cl)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl FIWOJRHNMZWIII-UHFFFAOYSA-N 0.000 claims 2
XGNROMYEANDWBV-UHFFFAOYSA-N 1-[3-(cyclopropylmethoxy)-2,4-dimethoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound COC1=C(OCC2CC2)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl XGNROMYEANDWBV-UHFFFAOYSA-N 0.000 claims 2
OTRTVVFKCITNML-UHFFFAOYSA-N 1-[3-(cyclopropylmethoxy)-2-hydroxy-4-methoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound OC1=C(OCC2CC2)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl OTRTVVFKCITNML-UHFFFAOYSA-N 0.000 claims 2
SKUOFNDSDASKRV-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2,3-diethoxy-4-methoxyphenyl)ethanone Chemical compound CCOC1=C(OC)C=CC(C(=O)CC=2C(=CN=CC=2Cl)Cl)=C1OCC SKUOFNDSDASKRV-UHFFFAOYSA-N 0.000 claims 2
RLWQQEHPJNNTGF-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2,4-dimethoxy-3-pent-2-enoxyphenyl)ethanone Chemical compound CCC=CCOC1=C(OC)C=CC(C(=O)CC=2C(=CN=CC=2Cl)Cl)=C1OC RLWQQEHPJNNTGF-UHFFFAOYSA-N 0.000 claims 2
ASJWCPHMNSBYKS-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2,4-dimethoxy-3-phenylmethoxyphenyl)ethanone Chemical compound COC1=C(OCC=2C=CC=CC=2)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl ASJWCPHMNSBYKS-UHFFFAOYSA-N 0.000 claims 2
NBXASMDRACSYCU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2,4-dimethoxy-3-prop-2-ynoxyphenyl)ethanone Chemical compound COC1=C(OCC#C)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl NBXASMDRACSYCU-UHFFFAOYSA-N 0.000 claims 2
UUYBYQPDBPQDRD-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2-hexoxy-3,4-dimethoxyphenyl)ethanone Chemical compound C1=CC(OC)=C(OC)C(OCCCCCC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl UUYBYQPDBPQDRD-UHFFFAOYSA-N 0.000 claims 2
CYKNNTIKSOVHEQ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2-hydroxy-4-methoxy-3-prop-2-enoxyphenyl)ethanone Chemical compound OC1=C(OCC=C)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl CYKNNTIKSOVHEQ-UHFFFAOYSA-N 0.000 claims 2
CQNYAUULEGLSKX-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxy-2-pent-2-enoxyphenyl)ethanone Chemical compound CCC=CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl CQNYAUULEGLSKX-UHFFFAOYSA-N 0.000 claims 2
MZVCROAJYCFFBU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxy-2-pent-4-enoxyphenyl)ethanone Chemical compound C=CCCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl MZVCROAJYCFFBU-UHFFFAOYSA-N 0.000 claims 2
ZUZGIAAQIMTXJZ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxy-2-phenylmethoxyphenyl)ethanone Chemical compound C=1C=CC=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl ZUZGIAAQIMTXJZ-UHFFFAOYSA-N 0.000 claims 2
OUECCBYYAPBBGU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3-ethoxy-2,4-dimethoxyphenyl)ethanone Chemical compound CCOC1=C(OC)C=CC(C(=O)CC=2C(=CN=CC=2Cl)Cl)=C1OC OUECCBYYAPBBGU-UHFFFAOYSA-N 0.000 claims 2
SDZOJIYKTNKVMO-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3-ethoxy-2-hydroxy-4-methoxyphenyl)ethanone Chemical compound C1=C(OC)C(OCC)=C(O)C(C(=O)CC=2C(=CN=CC=2Cl)Cl)=C1 SDZOJIYKTNKVMO-UHFFFAOYSA-N 0.000 claims 2
BFSZKUJJMOONNH-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3-hydroxy-2,4-dimethoxyphenyl)ethanone Chemical compound COC1=C(O)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl BFSZKUJJMOONNH-UHFFFAOYSA-N 0.000 claims 2
JJPBTJGCARKTTP-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2,4-dimethoxy-3-(2-methoxyethoxy)phenyl]ethanone Chemical compound COCCOC1=C(OC)C=CC(C(=O)CC=2C(=CN=CC=2Cl)Cl)=C1OC JJPBTJGCARKTTP-UHFFFAOYSA-N 0.000 claims 2
ZXQWTZAJNLCAEQ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2,4-dimethoxy-3-(2-phenylethoxy)phenyl]ethanone Chemical compound COC1=C(OCCC=2C=CC=CC=2)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl ZXQWTZAJNLCAEQ-UHFFFAOYSA-N 0.000 claims 2
QGORXUZXGJYAGV-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2,4-dimethoxy-3-(4-methylpent-3-enoxy)phenyl]ethanone Chemical compound COC1=C(OCCC=C(C)C)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl QGORXUZXGJYAGV-UHFFFAOYSA-N 0.000 claims 2
DVEVGBSUTXMHHE-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-(2-ethylbutoxy)-3,4-dimethoxyphenyl]ethanone Chemical compound C1=CC(OC)=C(OC)C(OCC(CC)CC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl DVEVGBSUTXMHHE-UHFFFAOYSA-N 0.000 claims 2
VPTJUCWNNSOTPJ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-(2-hydroxyethoxy)-3,4-dimethoxyphenyl]ethanone Chemical compound OCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VPTJUCWNNSOTPJ-UHFFFAOYSA-N 0.000 claims 2
WUYLGHHVSYUCOT-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[(2,3-difluoro-4-methylphenyl)methoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(C)C(F)=C(F)C=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl WUYLGHHVSYUCOT-UHFFFAOYSA-N 0.000 claims 2
UUPHXBRXXQYUGE-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[(2-fluorophenyl)methoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=CC=C(F)C=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl UUPHXBRXXQYUGE-UHFFFAOYSA-N 0.000 claims 2
LIADZBYPVJGPAC-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[(4-fluorophenyl)methoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl LIADZBYPVJGPAC-UHFFFAOYSA-N 0.000 claims 2
BOVSNWBYIPDQLD-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[2-(4-fluorophenyl)ethoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl BOVSNWBYIPDQLD-UHFFFAOYSA-N 0.000 claims 2
UDJXJYWFLLZCTC-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[[2-(difluoromethoxy)phenyl]methoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=CC=C(OC(F)F)C=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl UDJXJYWFLLZCTC-UHFFFAOYSA-N 0.000 claims 2
VHLHWBCYWSRXDA-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[[2-fluoro-6-(trifluoromethyl)phenyl]methoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound FC=1C=CC=C(C(F)(F)F)C=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VHLHWBCYWSRXDA-UHFFFAOYSA-N 0.000 claims 2
YMGQRHRYJZAXSJ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[[3-fluoro-5-(trifluoromethyl)phenyl]methoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C(F)=CC(C(F)(F)F)=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl YMGQRHRYJZAXSJ-UHFFFAOYSA-N 0.000 claims 2
DTNGOQXPWQAEBQ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(1-phenylpropan-2-yloxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CC(C)OC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DTNGOQXPWQAEBQ-UHFFFAOYSA-N 0.000 claims 2
YAWQDHGBQCPQID-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(1-phenylpropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1C(CC)OC(C(=C(OC)C=C1)OC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl YAWQDHGBQCPQID-UHFFFAOYSA-N 0.000 claims 2
QGZHZKISGDRSGJ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-methoxyethoxy)phenyl]ethanone Chemical compound C1=CC(OC)=C(OC)C(OCCOC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl QGZHZKISGDRSGJ-UHFFFAOYSA-N 0.000 claims 2
VTZDKIZZAJHJRK-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-methylpropoxy)phenyl]ethanone Chemical compound CC(C)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VTZDKIZZAJHJRK-UHFFFAOYSA-N 0.000 claims 2
XVPBIMZNBYDQEM-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-phenylpropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1C(C)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl XVPBIMZNBYDQEM-UHFFFAOYSA-N 0.000 claims 2
NOKIKIMOIGWLOD-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-pyridin-3-ylethoxy)phenyl]ethanone Chemical compound C=1C=CN=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl NOKIKIMOIGWLOD-UHFFFAOYSA-N 0.000 claims 2
DPXLJUYLWIVAPU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-pyridin-4-ylethoxy)phenyl]ethanone Chemical compound C=1C=NC=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DPXLJUYLWIVAPU-UHFFFAOYSA-N 0.000 claims 2
ZUEQMUBWLSDUJJ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(3-methylbut-2-enoxy)phenyl]ethanone Chemical compound CC(C)=CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl ZUEQMUBWLSDUJJ-UHFFFAOYSA-N 0.000 claims 2
TZJWDASQNDQUNO-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(3-methylbutoxy)phenyl]ethanone Chemical compound CC(C)CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl TZJWDASQNDQUNO-UHFFFAOYSA-N 0.000 claims 2
BUMMGBAYAPXUBP-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(3-phenoxypropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1OCCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl BUMMGBAYAPXUBP-UHFFFAOYSA-N 0.000 claims 2
KOHXGYZDGINMGH-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(3-phenylpropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl KOHXGYZDGINMGH-UHFFFAOYSA-N 0.000 claims 2
VCZXNLUGQYGLGR-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(5-methylhexoxy)phenyl]ethanone Chemical compound CC(C)CCCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VCZXNLUGQYGLGR-UHFFFAOYSA-N 0.000 claims 2
IOBPYOLVXMNYCA-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(naphthalen-2-ylmethoxy)phenyl]ethanone Chemical compound C=1C=C2C=CC=CC2=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl IOBPYOLVXMNYCA-UHFFFAOYSA-N 0.000 claims 2
CJOMHHRTMYLZAU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(2-methylquinolin-6-yl)methoxy]phenyl]ethanone Chemical compound C=1C=C2N=C(C)C=CC2=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl CJOMHHRTMYLZAU-UHFFFAOYSA-N 0.000 claims 2
FKVZZYPDIZUKTJ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(3-methoxyphenyl)methoxy]phenyl]ethanone Chemical compound COC1=CC=CC(COC=2C(=C(OC)C=CC=2C(=O)CC=2C(=CN=CC=2Cl)Cl)OC)=C1 FKVZZYPDIZUKTJ-UHFFFAOYSA-N 0.000 claims 2
VRMIIPPAVGSUCU-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(3-methylphenyl)methoxy]phenyl]ethanone Chemical compound C=1C=CC(C)=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VRMIIPPAVGSUCU-UHFFFAOYSA-N 0.000 claims 2
RQKKDOIXCSBOBP-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(4-methoxyphenyl)methoxy]phenyl]ethanone Chemical compound C1=CC(OC)=CC=C1COC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC RQKKDOIXCSBOBP-UHFFFAOYSA-N 0.000 claims 2
MODAQTRGUVRBRE-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(4-propan-2-ylphenyl)methoxy]phenyl]ethanone Chemical compound C=1C=C(C(C)C)C=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl MODAQTRGUVRBRE-UHFFFAOYSA-N 0.000 claims 2
MDMXGGDDKAESJV-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(5-methyl-1,2-oxazol-3-yl)methoxy]phenyl]ethanone Chemical compound C1=C(C)ON=C1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl MDMXGGDDKAESJV-UHFFFAOYSA-N 0.000 claims 2
CNEKTFIPGQMVJW-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(3-methoxyphenyl)ethoxy]phenyl]ethanone Chemical compound COC1=CC=CC(CCOC=2C(=C(OC)C=CC=2C(=O)CC=2C(=CN=CC=2Cl)Cl)OC)=C1 CNEKTFIPGQMVJW-UHFFFAOYSA-N 0.000 claims 2
DQTZKBDPTUNLNM-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(4-methoxyphenyl)ethoxy]phenyl]ethanone Chemical compound C1=CC(OC)=CC=C1CCOC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC DQTZKBDPTUNLNM-UHFFFAOYSA-N 0.000 claims 2
WRQVXZJNJVCBAV-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(4-methylphenyl)-2-oxoethoxy]phenyl]ethanone Chemical compound C=1C=C(C)C=CC=1C(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl WRQVXZJNJVCBAV-UHFFFAOYSA-N 0.000 claims 2
HZZHHQWQKFBILS-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(4-methylphenyl)ethoxy]phenyl]ethanone Chemical compound C=1C=C(C)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl HZZHHQWQKFBILS-UHFFFAOYSA-N 0.000 claims 2
MVCJYUVOROQFLV-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(4-methylsulfonylphenyl)ethoxy]phenyl]ethanone Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl MVCJYUVOROQFLV-UHFFFAOYSA-N 0.000 claims 2
FZCNCMRCAWZIOE-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[[3-(trifluoromethoxy)phenyl]methoxy]phenyl]ethanone Chemical compound C=1C=CC(OC(F)(F)F)=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl FZCNCMRCAWZIOE-UHFFFAOYSA-N 0.000 claims 2
FZZIYKNFYHUBKK-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]ethanone Chemical compound C=1C=CC(C(F)(F)F)=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl FZZIYKNFYHUBKK-UHFFFAOYSA-N 0.000 claims 2
PSNIDYIRGAGYGG-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3-(2-hydroxyethoxy)-2,4-dimethoxyphenyl]ethanone Chemical compound COC1=C(OCCO)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl PSNIDYIRGAGYGG-UHFFFAOYSA-N 0.000 claims 2
FOMTWKFXAKGMPS-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3-ethoxy-4-methoxy-2-(2-phenylethoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCOC=1C(OCC)=C(OC)C=CC=1C(=O)CC1=C(Cl)C=NC=C1Cl FOMTWKFXAKGMPS-UHFFFAOYSA-N 0.000 claims 2
PDOHITFVBCRDID-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[4-ethoxy-3-methoxy-2-(2-phenylethoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCOC1=C(OC)C(OCC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl PDOHITFVBCRDID-UHFFFAOYSA-N 0.000 claims 2
XMAYLTKCWBYEPQ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[4-methoxy-2,3-bis(prop-2-enoxy)phenyl]ethanone Chemical compound C=CCOC1=C(OCC=C)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl XMAYLTKCWBYEPQ-UHFFFAOYSA-N 0.000 claims 2
GTELPGRUGWWEFG-UHFFFAOYSA-N 2-[2,3-dimethoxy-6-(2-pyrazin-2-ylacetyl)phenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=CN=CC=N1 GTELPGRUGWWEFG-UHFFFAOYSA-N 0.000 claims 2
PPOVHFHWVQELQL-UHFFFAOYSA-N 2-[2,3-dimethoxy-6-(2-pyridazin-3-ylacetyl)phenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=CC=CN=N1 PPOVHFHWVQELQL-UHFFFAOYSA-N 0.000 claims 2
SAHVXWZBQAFGSI-UHFFFAOYSA-N 2-[2,3-dimethoxy-6-(2-pyridin-4-ylacetyl)phenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=CC=NC=C1 SAHVXWZBQAFGSI-UHFFFAOYSA-N 0.000 claims 2
GOVSWHMHBSRKRD-UHFFFAOYSA-N 2-[2,3-dimethoxy-6-(2-quinolin-4-ylacetyl)phenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=CC=NC2=CC=CC=C12 GOVSWHMHBSRKRD-UHFFFAOYSA-N 0.000 claims 2
BVBZISHRASEXBD-UHFFFAOYSA-N 2-[2,3-dimethoxy-6-[2-(2-methoxypyridin-4-yl)acetyl]phenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=CC=NC(OC)=C1 BVBZISHRASEXBD-UHFFFAOYSA-N 0.000 claims 2
MXWZBLXSYIHAKD-UHFFFAOYSA-N 2-[2-(tert-butylamino)-3,5-dichloropyridin-4-yl]-1-[2-[2-(4-fluorophenyl)ethoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC(NC(C)(C)C)=C1Cl MXWZBLXSYIHAKD-UHFFFAOYSA-N 0.000 claims 2
ZJLHGVYDTFGFSU-UHFFFAOYSA-N 2-[2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl ZJLHGVYDTFGFSU-UHFFFAOYSA-N 0.000 claims 2
TWMITTAXSZKQCQ-UHFFFAOYSA-N 2-[3-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]propyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl TWMITTAXSZKQCQ-UHFFFAOYSA-N 0.000 claims 2
ZHYPFUMETNJBAS-UHFFFAOYSA-N 2-[6-[2-(2,6-dichlorophenyl)acetyl]-2,3-dimethoxyphenoxy]-n-propylacetamide Chemical compound CCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=CC=C1Cl ZHYPFUMETNJBAS-UHFFFAOYSA-N 0.000 claims 2
SRDGRNRVWSQIPY-UHFFFAOYSA-N 2-[6-[2-(2-chloropyridin-3-yl)acetyl]-2,3-dimethoxyphenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=CC=CN=C1Cl SRDGRNRVWSQIPY-UHFFFAOYSA-N 0.000 claims 2
IUYGCCZNVGAMTQ-UHFFFAOYSA-N 2-[6-[2-(2-cyanopyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-propylacetamide Chemical compound CCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=CC=NC(C#N)=C1 IUYGCCZNVGAMTQ-UHFFFAOYSA-N 0.000 claims 2
FZPSRUQKZQAUHY-UHFFFAOYSA-N 2-[6-[2-(3,5-dibromopyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-propylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCCC)=C1C(=O)CC1=C(Br)C=NC=C1Br FZPSRUQKZQAUHY-UHFFFAOYSA-N 0.000 claims 2
QLROCGFGPAAMFW-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-hydroxyethyl)acetamide Chemical compound OCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl QLROCGFGPAAMFW-UHFFFAOYSA-N 0.000 claims 2
DKXYEGNIOKXIKZ-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-phenoxyethyl)acetamide Chemical compound C=1C=CC=CC=1OCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DKXYEGNIOKXIKZ-UHFFFAOYSA-N 0.000 claims 2
OHEMRPAPVBTGHV-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-phenylethyl)acetamide Chemical compound C=1C=CC=CC=1CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl OHEMRPAPVBTGHV-UHFFFAOYSA-N 0.000 claims 2
GKXQOALDXIWVFF-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(3-hydroxypropyl)acetamide Chemical compound OCCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl GKXQOALDXIWVFF-UHFFFAOYSA-N 0.000 claims 2
XKKGUHTYRDBTBF-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(3-methylbutyl)acetamide Chemical compound CC(C)CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl XKKGUHTYRDBTBF-UHFFFAOYSA-N 0.000 claims 2
LMURGDBDJMITHN-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(3-phenylpropyl)acetamide Chemical compound C=1C=CC=CC=1CCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl LMURGDBDJMITHN-UHFFFAOYSA-N 0.000 claims 2
OZJYFBGKTLVAOL-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(3-propan-2-yloxypropyl)acetamide Chemical compound CC(C)OCCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl OZJYFBGKTLVAOL-UHFFFAOYSA-N 0.000 claims 2
HKNSROOPYNMQTL-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(furan-2-ylmethyl)acetamide Chemical compound C=1C=COC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl HKNSROOPYNMQTL-UHFFFAOYSA-N 0.000 claims 2
QHPZKVVWEIDCES-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(pyridin-3-ylmethyl)acetamide Chemical compound C=1C=CN=CC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl QHPZKVVWEIDCES-UHFFFAOYSA-N 0.000 claims 2
GESICGOMVYWZOU-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(pyridin-4-ylmethyl)acetamide Chemical compound C=1C=NC=CC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl GESICGOMVYWZOU-UHFFFAOYSA-N 0.000 claims 2
DFMCGOTUZIRANW-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(2-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC=C1CNC(=O)COC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC DFMCGOTUZIRANW-UHFFFAOYSA-N 0.000 claims 2
JMQFQPXNSUABPG-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(2-methylphenyl)methyl]acetamide Chemical compound C=1C=CC=C(C)C=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl JMQFQPXNSUABPG-UHFFFAOYSA-N 0.000 claims 2
LFUPPELHGPIHFO-CILPGNKCSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]acetamide Chemical compound C([C@H]1O)C2=CC=CC=C2C1NC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl LFUPPELHGPIHFO-CILPGNKCSA-N 0.000 claims 2
MUMWJPRJSGPLNT-NRFANRHFSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(2r)-2-hydroxy-2-phenylethyl]acetamide Chemical compound C([C@H](O)C=1C=CC=CC=1)NC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl MUMWJPRJSGPLNT-NRFANRHFSA-N 0.000 claims 2
MUMWJPRJSGPLNT-OAQYLSRUSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(2s)-2-hydroxy-2-phenylethyl]acetamide Chemical compound C([C@@H](O)C=1C=CC=CC=1)NC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl MUMWJPRJSGPLNT-OAQYLSRUSA-N 0.000 claims 2
JVPFOYGOQMGFDN-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(3-fluorophenyl)methyl]acetamide Chemical compound C=1C=CC(F)=CC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl JVPFOYGOQMGFDN-UHFFFAOYSA-N 0.000 claims 2
NTKPBNIVYQNNMP-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(3-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC(CNC(=O)COC=2C(=C(OC)C=CC=2C(=O)CC=2C(=CN=CC=2Cl)Cl)OC)=C1 NTKPBNIVYQNNMP-UHFFFAOYSA-N 0.000 claims 2
WYCSOVCXNRWLKJ-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(3-methylphenyl)methyl]acetamide Chemical compound C=1C=CC(C)=CC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl WYCSOVCXNRWLKJ-UHFFFAOYSA-N 0.000 claims 2
YTPBNBBKIGKMLN-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(4-ethylphenyl)methyl]acetamide Chemical compound C1=CC(CC)=CC=C1CNC(=O)COC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC YTPBNBBKIGKMLN-UHFFFAOYSA-N 0.000 claims 2
OLDIYUJTPRQJRO-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(4-methoxyphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)COC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC OLDIYUJTPRQJRO-UHFFFAOYSA-N 0.000 claims 2
VAIHIXFLZNDIAJ-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(4-methylphenyl)methyl]acetamide Chemical compound C=1C=C(C)C=CC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl VAIHIXFLZNDIAJ-UHFFFAOYSA-N 0.000 claims 2
KUFLBGLZLOSZOB-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[2-(2-hydroxyethoxy)ethyl]acetamide Chemical compound OCCOCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl KUFLBGLZLOSZOB-UHFFFAOYSA-N 0.000 claims 2
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206010061218 Inflammation Diseases 0.000 claims 2
241000023320 Luma <angiosperm> Species 0.000 claims 2
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MODKMHXGCGKTLE-UHFFFAOYSA-N N-acetylphenylethylamine Chemical compound CC(=O)NCCC1=CC=CC=C1 MODKMHXGCGKTLE-UHFFFAOYSA-N 0.000 claims 2
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206010028980 Neoplasm Diseases 0.000 claims 2
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206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 2
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208000024780 Urticaria Diseases 0.000 claims 2
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230000001154 acute effect Effects 0.000 claims 2
238000007083 alkoxycarbonylation reaction Methods 0.000 claims 2
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FSRQJAINYVJYDS-UHFFFAOYSA-N 1-[2-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methoxy]-3-ethoxy-4-methoxyphenyl]-2-(3,5-dichloropyridin-4-yl)ethanone Chemical compound N=1N=C(C2CC2)SC=1COC=1C(OCC)=C(OC)C=CC=1C(=O)CC1=C(Cl)C=NC=C1Cl FSRQJAINYVJYDS-UHFFFAOYSA-N 0.000 claims 1
ZRFJYAZQMFCUIX-UHFFFAOYSA-N 1-bromo-3-ethylbenzene Chemical compound CCC1=CC=CC(Br)=C1 ZRFJYAZQMFCUIX-UHFFFAOYSA-N 0.000 claims 1
LOXUEGMPESDGBQ-UHFFFAOYSA-N 1-chloro-3-ethylbenzene Chemical compound CCC1=CC=CC(Cl)=C1 LOXUEGMPESDGBQ-UHFFFAOYSA-N 0.000 claims 1
IXLSVQMYQRAMEW-UHFFFAOYSA-N 1-chloro-4-ethoxybenzene Chemical compound CCOC1=CC=C(Cl)C=C1 IXLSVQMYQRAMEW-UHFFFAOYSA-N 0.000 claims 1
GPOFSFLJOIAMSA-UHFFFAOYSA-N 1-chloro-4-ethylbenzene Chemical compound CCC1=CC=C(Cl)C=C1 GPOFSFLJOIAMSA-UHFFFAOYSA-N 0.000 claims 1
NIEHEMAZEULEKB-UHFFFAOYSA-N 1-ethyl-2-methoxybenzene Chemical compound CCC1=CC=CC=C1OC NIEHEMAZEULEKB-UHFFFAOYSA-N 0.000 claims 1
DWLZULQNIPIABE-UHFFFAOYSA-N 1-ethyl-3-methoxybenzene Chemical compound CCC1=CC=CC(OC)=C1 DWLZULQNIPIABE-UHFFFAOYSA-N 0.000 claims 1
BLDNWXVISIXWKZ-UHFFFAOYSA-N 1-ethyl-4-fluorobenzene Chemical compound CCC1=CC=C(F)C=C1 BLDNWXVISIXWKZ-UHFFFAOYSA-N 0.000 claims 1
HDNRAPAFJLXKBV-UHFFFAOYSA-N 1-ethyl-4-methoxybenzene Chemical compound CCC1=CC=C(OC)C=C1 HDNRAPAFJLXKBV-UHFFFAOYSA-N 0.000 claims 1
JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 claims 1
CVMCYLJMZRSPEV-UHFFFAOYSA-N 1-ethyl-4-methylsulfinylbenzene Chemical compound CCC1=CC=C(S(C)=O)C=C1 CVMCYLJMZRSPEV-UHFFFAOYSA-N 0.000 claims 1
KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 claims 1
LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 claims 1
125000005938 2,3-dihydro-1H-isoindolyl group Chemical group 0.000 claims 1
OBSLLHNATPQFMJ-UHFFFAOYSA-N 2,4-Dimethylthiazole Chemical compound CC1=CSC(C)=N1 OBSLLHNATPQFMJ-UHFFFAOYSA-N 0.000 claims 1
JJPSZKIOGBRMHK-UHFFFAOYSA-N 2,6-dimethylquinoline Chemical compound N1=C(C)C=CC2=CC(C)=CC=C21 JJPSZKIOGBRMHK-UHFFFAOYSA-N 0.000 claims 1
QCFYWMAMQISZND-UHFFFAOYSA-N 2-(2-amino-3,5-dichloropyridin-4-yl)-1-[2-[2-(4-fluorophenyl)ethoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C=1C=C(F)C=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC(N)=C1Cl QCFYWMAMQISZND-UHFFFAOYSA-N 0.000 claims 1
IRKBYACLGSSVDO-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(2-hydroxy-3,4-dimethoxyphenyl)ethanone Chemical compound OC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl IRKBYACLGSSVDO-UHFFFAOYSA-N 0.000 claims 1
KHMSWQIKMLFUAB-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxy-2-pentoxyphenyl)ethanone Chemical compound C1=CC(OC)=C(OC)C(OCCCCC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl KHMSWQIKMLFUAB-UHFFFAOYSA-N 0.000 claims 1
AQEWEHADDCHYCX-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxy-2-propoxyphenyl)ethanone Chemical compound C1=CC(OC)=C(OC)C(OCCC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl AQEWEHADDCHYCX-UHFFFAOYSA-N 0.000 claims 1
FCXXXTKTEFHAEV-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[2-[2-(3,4-dimethoxyphenyl)ethoxy]-3,4-dimethoxyphenyl]ethanone Chemical compound C1=C(OC)C(OC)=CC=C1CCOC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC FCXXXTKTEFHAEV-UHFFFAOYSA-N 0.000 claims 1
HJSFPBSTAKNRHW-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(1,2,4-oxadiazol-3-ylmethoxy)phenyl]ethanone Chemical compound N1=CON=C1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl HJSFPBSTAKNRHW-UHFFFAOYSA-N 0.000 claims 1
ZTHWKDBQIAHIMC-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-morpholin-4-yl-2-oxoethoxy)phenyl]ethanone Chemical compound C1COCCN1C(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl ZTHWKDBQIAHIMC-UHFFFAOYSA-N 0.000 claims 1
DNEYMHMAIBKOOM-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-naphthalen-2-yl-2-oxoethoxy)phenyl]ethanone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DNEYMHMAIBKOOM-UHFFFAOYSA-N 0.000 claims 1
UHTFRAHGZQQMHW-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-oxo-2-pyrrolidin-1-ylethoxy)phenyl]ethanone Chemical compound C1CCCN1C(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl UHTFRAHGZQQMHW-UHFFFAOYSA-N 0.000 claims 1
IRRTWELLHXGREF-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-phenoxyethoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1OCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl IRRTWELLHXGREF-UHFFFAOYSA-N 0.000 claims 1
DYUBQXVOBFCBPQ-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-phenylethoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DYUBQXVOBFCBPQ-UHFFFAOYSA-N 0.000 claims 1
BFWWMLDZLPHSOH-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(2-pyridin-2-ylethoxy)phenyl]ethanone Chemical compound C=1C=CC=NC=1CCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl BFWWMLDZLPHSOH-UHFFFAOYSA-N 0.000 claims 1
FIEYQQJHJGAQID-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-(3-phenylmethoxypropoxy)phenyl]ethanone Chemical compound C=1C=CC=CC=1COCCCOC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl FIEYQQJHJGAQID-UHFFFAOYSA-N 0.000 claims 1
DZXIZOTVHDKLGC-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl]ethanone Chemical compound C=1SC(C)=NC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl DZXIZOTVHDKLGC-UHFFFAOYSA-N 0.000 claims 1
SKCAOGYWGHQINO-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(2-methylphenyl)methoxy]phenyl]ethanone Chemical compound C=1C=CC=C(C)C=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl SKCAOGYWGHQINO-UHFFFAOYSA-N 0.000 claims 1
BPVKRCODOFEANK-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[(4-methylphenyl)methoxy]phenyl]ethanone Chemical compound C=1C=C(C)C=CC=1COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl BPVKRCODOFEANK-UHFFFAOYSA-N 0.000 claims 1
RVNQFIXYWCIIQE-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(2-methoxyphenyl)-2-oxoethoxy]phenyl]ethanone Chemical compound COC1=CC=CC=C1C(=O)COC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC RVNQFIXYWCIIQE-UHFFFAOYSA-N 0.000 claims 1
JCHWKYHHLNFXBH-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(2-methoxyphenyl)ethoxy]phenyl]ethanone Chemical compound COC1=CC=CC=C1CCOC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC JCHWKYHHLNFXBH-UHFFFAOYSA-N 0.000 claims 1
XLCLLFRIVQWTLX-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-[3,4-dimethoxy-2-[2-(4-methoxyphenyl)-2-oxoethoxy]phenyl]ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)COC1=C(C(=O)CC=2C(=CN=CC=2Cl)Cl)C=CC(OC)=C1OC XLCLLFRIVQWTLX-UHFFFAOYSA-N 0.000 claims 1
QTMAZYGAVHCKKX-UHFFFAOYSA-N 2-[(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]propane-1,3-diol Chemical compound NC1=NC=NC2=C1C(Br)=CN2COC(CO)CO QTMAZYGAVHCKKX-UHFFFAOYSA-N 0.000 claims 1
LHIWCSFZBFQJCF-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2,2-dimethylpropyl)acetamide Chemical compound CC(C)(C)CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl LHIWCSFZBFQJCF-UHFFFAOYSA-N 0.000 claims 1
OXELKHLBXLWGSE-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-morpholin-4-ylethyl)acetamide Chemical compound C1COCCN1CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl OXELKHLBXLWGSE-UHFFFAOYSA-N 0.000 claims 1
CQHSTOSZSOZOFN-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-piperidin-1-ylethyl)acetamide Chemical compound C1CCCCN1CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl CQHSTOSZSOZOFN-UHFFFAOYSA-N 0.000 claims 1
GCXWZSXFEFDTNP-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-pyridin-2-ylethyl)acetamide Chemical compound C=1C=CC=NC=1CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl GCXWZSXFEFDTNP-UHFFFAOYSA-N 0.000 claims 1
OSWLDBCTQUNZTF-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-pyridin-3-ylethyl)acetamide Chemical compound C=1C=CN=CC=1CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl OSWLDBCTQUNZTF-UHFFFAOYSA-N 0.000 claims 1
LXWXOTBRKRMBKT-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-pyridin-4-ylethyl)acetamide Chemical compound C=1C=NC=CC=1CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl LXWXOTBRKRMBKT-UHFFFAOYSA-N 0.000 claims 1
JMIFKLFYZSZDOT-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(2-pyrrolidin-1-ylethyl)acetamide Chemical compound C1CCCN1CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl JMIFKLFYZSZDOT-UHFFFAOYSA-N 0.000 claims 1
KFSVMHDPZSHQAM-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(3-hydroxy-3-methylbutyl)acetamide Chemical compound CC(O)(C)CCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl KFSVMHDPZSHQAM-UHFFFAOYSA-N 0.000 claims 1
IZZVTUZQEJWHIH-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C=1C=CC=NC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl IZZVTUZQEJWHIH-UHFFFAOYSA-N 0.000 claims 1
KMQMVRHYIQQCJZ-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-(thiophen-2-ylmethyl)acetamide Chemical compound C=1C=CSC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl KMQMVRHYIQQCJZ-UHFFFAOYSA-N 0.000 claims 1
RZTSOPUGHSQOHC-OAHLLOKOSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(1r)-1-phenylethyl]acetamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl RZTSOPUGHSQOHC-OAHLLOKOSA-N 0.000 claims 1
RZTSOPUGHSQOHC-HNNXBMFYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(1s)-1-phenylethyl]acetamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl RZTSOPUGHSQOHC-HNNXBMFYSA-N 0.000 claims 1
PPABKJXQFJBVGP-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(2,3-difluorophenyl)methyl]acetamide Chemical compound C=1C=CC(F)=C(F)C=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl PPABKJXQFJBVGP-UHFFFAOYSA-N 0.000 claims 1
XRXLKFSTDZQTOX-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[(3,5-difluorophenyl)methyl]acetamide Chemical compound C=1C(F)=CC(F)=CC=1CNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl XRXLKFSTDZQTOX-UHFFFAOYSA-N 0.000 claims 1
HSWHSVIVZVHNKR-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-[3-(dimethylamino)propyl]acetamide Chemical compound CN(C)CCCNC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl HSWHSVIVZVHNKR-UHFFFAOYSA-N 0.000 claims 1
ULRSLYOKYFRMBD-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-ethylacetamide Chemical compound C1=CC(OC)=C(OC)C(OCC(=O)NCC)=C1C(=O)CC1=C(Cl)C=NC=C1Cl ULRSLYOKYFRMBD-UHFFFAOYSA-N 0.000 claims 1
WKSFCOZRBMJURF-UHFFFAOYSA-N 2-[6-[2-(3,5-dichloropyridin-4-yl)acetyl]-2,3-dimethoxyphenoxy]-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)COC1=C(OC)C(OC)=CC=C1C(=O)CC1=C(Cl)C=NC=C1Cl WKSFCOZRBMJURF-UHFFFAOYSA-N 0.000 claims 1
PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims 1
XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 claims 1
JSMMZMYGEVUURX-UHFFFAOYSA-N 2-chloro-5-methylthiophene Chemical compound CC1=CC=C(Cl)S1 JSMMZMYGEVUURX-UHFFFAOYSA-N 0.000 claims 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
VLWIWIVUSSYIIB-UHFFFAOYSA-N 2-cyclopropyl-5-methyl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1C1CC1 VLWIWIVUSSYIIB-UHFFFAOYSA-N 0.000 claims 1
JZDSOQSUCWVBMV-UHFFFAOYSA-N 2-ethylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CC)C(=O)C2=C1 JZDSOQSUCWVBMV-UHFFFAOYSA-N 0.000 claims 1
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
DQSHFKPKFISSNM-UHFFFAOYSA-N 2-methylbenzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1 DQSHFKPKFISSNM-UHFFFAOYSA-N 0.000 claims 1
GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 claims 1
RLARUBPTQYKZKA-UHFFFAOYSA-N 2-propylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCC)C(=O)C2=C1 RLARUBPTQYKZKA-UHFFFAOYSA-N 0.000 claims 1
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
DBRZAWITJCPDAD-UHFFFAOYSA-N 2h-naphthalen-1-ylidenemethanone Chemical compound C1=CC=C2C(=C=O)CC=CC2=C1 DBRZAWITJCPDAD-UHFFFAOYSA-N 0.000 claims 1
FICAQKBMCKEFDI-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole Chemical compound CC=1C=C(C)ON=1 FICAQKBMCKEFDI-UHFFFAOYSA-N 0.000 claims 1
SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 claims 1
MFEIKQPHQINPRI-UHFFFAOYSA-N 3-Ethylpyridine Chemical compound CCC1=CC=CN=C1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 claims 1
WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims 1
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
FZAXBPZVVJOFKX-UHFFFAOYSA-N 3-methyl-1,2,4-oxadiazole Chemical compound CC=1N=CON=1 FZAXBPZVVJOFKX-UHFFFAOYSA-N 0.000 claims 1
BOHCMQZJWOGWTA-UHFFFAOYSA-N 3-methylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1 BOHCMQZJWOGWTA-UHFFFAOYSA-N 0.000 claims 1
PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 claims 1
GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 claims 1
GVCLNACSYKYUHP-UHFFFAOYSA-N 4-amino-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine-5-carbothioamide Chemical compound C1=NC(N)=C2C(C(=S)N)=CN(COCCO)C2=N1 GVCLNACSYKYUHP-UHFFFAOYSA-N 0.000 claims 1
GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
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ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 claims 1
XWDCLPNMPBQWCW-UHFFFAOYSA-N N-(3-Methylbutyl)acetamide Chemical compound CC(C)CCNC(C)=O XWDCLPNMPBQWCW-UHFFFAOYSA-N 0.000 claims 1
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YGPZYYDTPXVBRA-RTDBHSBRSA-N [(2r,3s,4r,5r,6s)-2-[[(2r,3r,4r,5s,6r)-3-[[(3r)-3-dodecanoyloxytetradecanoyl]amino]-6-(hydroxymethyl)-5-phosphonooxy-4-[(3r)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]oxymethyl]-3,6-dihydroxy-5-[[(3r)-3-hydroxytetradecanoyl]amino]oxan-4-yl] (3r)-3-hydr Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](O)O1 YGPZYYDTPXVBRA-RTDBHSBRSA-N 0.000 claims 1
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QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims 1
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims 1
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical compound CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims 1
RPTKMZRQBREOMV-UHFFFAOYSA-N propoxymethylbenzene Chemical compound CCCOCC1=CC=CC=C1 RPTKMZRQBREOMV-UHFFFAOYSA-N 0.000 claims 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
125000002098 pyridazinyl group Chemical group 0.000 claims 1
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
125000005493 quinolyl group Chemical group 0.000 claims 1
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
125000001544 thienyl group Chemical group 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
0 *C1(*)*=C(CC(c(ccc(O*)c2O*)c2OC=[U])=O)[C@](C2)C2=*1 Chemical compound *C1(*)*=C(CC(c(ccc(O*)c2O*)c2OC=[U])=O)[C@](C2)C2=*1 0.000 description 2

JP2009541766A 2006-12-22 2007-12-21 Ｐｄｅ４阻害剤として有用な置換アセトフェノン Expired - Fee Related JP5342451B2 (ja)