CA2742993C - Pyrazine compounds as phosphodiesterase 10 inhibitors - Google Patents

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Publication number

CA2742993C

CA2742993C CA2742993A CA2742993A CA2742993C CA 2742993 C CA2742993 C CA 2742993C CA 2742993 A CA2742993 A CA 2742993A CA 2742993 A CA2742993 A CA 2742993A CA 2742993 C CA2742993 C CA 2742993C

Authority

CA

Canada

Prior art keywords

benzo

pyrazin

phenyl

yloxy

methanone

Prior art date

2008-11-14

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.)

Expired - Fee Related

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• 239000003112 inhibitor Substances 0.000 title claims description 32
• 150000003216 pyrazines Chemical class 0.000 title abstract description 4
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title description 10
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title description 8
• 239000000203 mixture Substances 0.000 claims abstract description 185
• 150000001875 compounds Chemical class 0.000 claims abstract description 174
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 54
• 201000010099 disease Diseases 0.000 claims abstract description 42
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 26
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 22
• 208000020925 Bipolar disease Diseases 0.000 claims abstract description 16
• -1 oxaspiro[3.5]nonyl Chemical group 0.000 claims description 218
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 196
• 229920006395 saturated elastomer Polymers 0.000 claims description 119
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 85
• 229910052757 nitrogen Inorganic materials 0.000 claims description 83
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 67
• 229910052731 fluorine Inorganic materials 0.000 claims description 65
• 229910052801 chlorine Inorganic materials 0.000 claims description 60
• 229910052794 bromium Inorganic materials 0.000 claims description 59
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 53
• 229910052799 carbon Inorganic materials 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
• 125000002950 monocyclic group Chemical group 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 206010012289 Dementia Diseases 0.000 claims description 19
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 125000002619 bicyclic group Chemical group 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 13
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 208000018737 Parkinson disease Diseases 0.000 claims description 12
• 208000028017 Psychotic disease Diseases 0.000 claims description 12
• 230000001898 pallidal effect Effects 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 125000004434 sulfur atom Chemical group 0.000 claims description 11
• 206010008748 Chorea Diseases 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 7
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 7
• 208000011117 substance-related disease Diseases 0.000 claims description 7
• IAHTUGZTRUZUTH-UHFFFAOYSA-N 1-o-tert-butyl 4-o-methyl 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidine-1,4-dicarboxylate Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 IAHTUGZTRUZUTH-UHFFFAOYSA-N 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 206010010219 Compulsions Diseases 0.000 claims description 6
• 206010026749 Mania Diseases 0.000 claims description 6
• 208000019022 Mood disease Diseases 0.000 claims description 6
• 206010034719 Personality change Diseases 0.000 claims description 6
• 125000003725 azepanyl group Chemical group 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 6
• 206010013663 drug dependence Diseases 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• CSQHJQJUFABKBU-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 CSQHJQJUFABKBU-UHFFFAOYSA-N 0.000 claims description 6
• 125000003551 oxepanyl group Chemical group 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 210000002637 putamen Anatomy 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 5
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 5
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• LKOQPLBSNVGZAI-UHFFFAOYSA-N methyl 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 LKOQPLBSNVGZAI-UHFFFAOYSA-N 0.000 claims description 5
• KRRMOUBLHUGKFX-KRWDZBQOSA-N n-[4-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KRRMOUBLHUGKFX-KRWDZBQOSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• GRZACTBGKFAAHZ-UHFFFAOYSA-N 1-[3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]azetidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 GRZACTBGKFAAHZ-UHFFFAOYSA-N 0.000 claims description 4
• ZNPDAYJZIRPRFQ-FIBGUPNXSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2,2,2-trideuterioethanone Chemical compound C1CN(C(=O)C([2H])([2H])[2H])CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ZNPDAYJZIRPRFQ-FIBGUPNXSA-N 0.000 claims description 4
• CKKWDWPXKBMQAE-UHFFFAOYSA-N 1-[4-[3-[6-(1,3-benzothiazol-2-ylamino)pyridin-3-yl]oxypyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C=N1)=CC=C1NC1=NC2=CC=CC=C2S1 CKKWDWPXKBMQAE-UHFFFAOYSA-N 0.000 claims description 4
• YWFDAAMTUBHJGI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 YWFDAAMTUBHJGI-UHFFFAOYSA-N 0.000 claims description 4
• RETLSFLATJJXAP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-piperidin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCNCC1 RETLSFLATJJXAP-UHFFFAOYSA-N 0.000 claims description 4
• MRMLYEPTQBRISE-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 MRMLYEPTQBRISE-UHFFFAOYSA-N 0.000 claims description 4
• PYCDSETUWLDZCK-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenoxy]pyrazin-2-yl]cyclohex-2-en-1-ol Chemical compound OC1CCCC(C=2C(=NC=CN=2)OC=2C=C(F)C(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 PYCDSETUWLDZCK-UHFFFAOYSA-N 0.000 claims description 4
• KLDFOQPHBRUMBD-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenoxy]pyrazin-2-yl]cyclohex-2-en-1-one Chemical compound C=1C=C(NC=2SC3=CC=CC=C3N=2)C(F)=CC=1OC1=NC=CN=C1C1=CC(=O)CCC1 KLDFOQPHBRUMBD-UHFFFAOYSA-N 0.000 claims description 4
• XKONAADIEGAKLP-UHFFFAOYSA-N 3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-1h-pyridin-2-one Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CNC1=O XKONAADIEGAKLP-UHFFFAOYSA-N 0.000 claims description 4
• ANYKNJNYLGGMOX-UHFFFAOYSA-N n-[4-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 ANYKNJNYLGGMOX-UHFFFAOYSA-N 0.000 claims description 4
• SOOCRXWTSFOYSK-UHFFFAOYSA-N n-[4-[3-(4-fluorooxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(F)CCOCC1 SOOCRXWTSFOYSK-UHFFFAOYSA-N 0.000 claims description 4
• QNHDLOODKNRIRQ-UHFFFAOYSA-N n-[4-[3-(oxan-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCOCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 QNHDLOODKNRIRQ-UHFFFAOYSA-N 0.000 claims description 4
• ROZAUDGDBWPBMH-UHFFFAOYSA-N n-methyl-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 ROZAUDGDBWPBMH-UHFFFAOYSA-N 0.000 claims description 4
• LIUKTCWPZUWMKH-WBVHZDCISA-N (1s,3r)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-WBVHZDCISA-N 0.000 claims description 3
• LIUKTCWPZUWMKH-RDJZCZTQSA-N (1s,3s)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-RDJZCZTQSA-N 0.000 claims description 3
• DVBCTQVDMKFPPK-UHFFFAOYSA-N 1,3-benzothiazol-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2SC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 DVBCTQVDMKFPPK-UHFFFAOYSA-N 0.000 claims description 3
• XDJJEQSKDPNXSQ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-cyclopentylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCC1 XDJJEQSKDPNXSQ-UHFFFAOYSA-N 0.000 claims description 3
• FQSMBMOXHXXZFB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanol Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(O)C=2NC3=CC=CC=C3N=2)C=C1 FQSMBMOXHXXZFB-UHFFFAOYSA-N 0.000 claims description 3
• QHDKAYNNBNHBEI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4,4-difluorocyclohexen-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(F)(F)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 QHDKAYNNBNHBEI-UHFFFAOYSA-N 0.000 claims description 3
• VQQUKLCJIHBWMK-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-fluorooxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C=CN=C(OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)C=1C1(F)CCOCC1 VQQUKLCJIHBWMK-UHFFFAOYSA-N 0.000 claims description 3
• OXOUFDALYKGXIH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-hydroxycyclohexyl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(O)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OXOUFDALYKGXIH-UHFFFAOYSA-N 0.000 claims description 3
• LXMLTIANVJGYBZ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methoxycyclohexen-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(OC)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 LXMLTIANVJGYBZ-UHFFFAOYSA-N 0.000 claims description 3
• VOFJMVKNCQVTIF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(thian-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCSCC1 VOFJMVKNCQVTIF-UHFFFAOYSA-N 0.000 claims description 3
• VIZVTXGNPQLHRZ-IRXDYDNUSA-N 1h-benzimidazol-2-yl-[4-[3-[(1s,3s)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@@H](O)CCC[C@@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-IRXDYDNUSA-N 0.000 claims description 3
• CBTCHLZKZTYQSJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[1-(2-fluoroethyl)piperidin-4-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CN(CCF)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 CBTCHLZKZTYQSJ-UHFFFAOYSA-N 0.000 claims description 3
• BLLKHCJAOCXHCW-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-UHFFFAOYSA-N 0.000 claims description 3
• WCMGHWBMVDXNQE-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]oxane-4-carbonitrile Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(C#N)CCOCC1 WCMGHWBMVDXNQE-UHFFFAOYSA-N 0.000 claims description 3
• PSLBMKSKQBUSDG-UHFFFAOYSA-N 4-methoxy-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1h-benzimidazol-2-amine Chemical compound N1C=2C(OC)=CC=CC=2N=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 PSLBMKSKQBUSDG-UHFFFAOYSA-N 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• AYQCPWIILRLNBK-UHFFFAOYSA-N n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-1h-benzimidazol-2-amine Chemical compound C1COCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2N1 AYQCPWIILRLNBK-UHFFFAOYSA-N 0.000 claims description 3
• YWNIKPNVTJLBHN-UHFFFAOYSA-N n-[4-[3-(oxan-3-ylamino)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCOCC1NC1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YWNIKPNVTJLBHN-UHFFFAOYSA-N 0.000 claims description 3
• QNKGFWCQMGOKAR-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1h-benzimidazol-2-amine Chemical compound C1COCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2N1 QNKGFWCQMGOKAR-UHFFFAOYSA-N 0.000 claims description 3
• UJVGWVCHGJXURF-UHFFFAOYSA-N n-[4-[3-(oxolan-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1OCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UJVGWVCHGJXURF-UHFFFAOYSA-N 0.000 claims description 3
• LKOZXUZYHCPBES-UHFFFAOYSA-N tert-butyl 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(CO)C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LKOZXUZYHCPBES-UHFFFAOYSA-N 0.000 claims description 3
• YNCIDBYSTGADKV-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 YNCIDBYSTGADKV-UHFFFAOYSA-N 0.000 claims description 2
• LIUKTCWPZUWMKH-DOTOQJQBSA-N (1r,3s)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-DOTOQJQBSA-N 0.000 claims description 2
• UHRZMABESCXDJW-HNNXBMFYSA-N (3r)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CC[C@@H](C#N)C1 UHRZMABESCXDJW-HNNXBMFYSA-N 0.000 claims description 2
• BLLKHCJAOCXHCW-OAHLLOKOSA-N (3r)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCC[C@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-OAHLLOKOSA-N 0.000 claims description 2
• UHRZMABESCXDJW-OAHLLOKOSA-N (3s)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CC[C@H](C#N)C1 UHRZMABESCXDJW-OAHLLOKOSA-N 0.000 claims description 2
• BLLKHCJAOCXHCW-HNNXBMFYSA-N (3s)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCC[C@@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-HNNXBMFYSA-N 0.000 claims description 2
• GNWKATFENPQMIQ-UHFFFAOYSA-N 1-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]ethanol Chemical compound C1CC(C(O)C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 GNWKATFENPQMIQ-UHFFFAOYSA-N 0.000 claims description 2
• XCPAHAVUYOTWLH-UHFFFAOYSA-N 1-[3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 XCPAHAVUYOTWLH-UHFFFAOYSA-N 0.000 claims description 2
• JCZBUCAABGISNU-UHFFFAOYSA-N 1-[3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 JCZBUCAABGISNU-UHFFFAOYSA-N 0.000 claims description 2
• UPHRCPFKIVBQFD-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-3-ol Chemical compound C1C(O)CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UPHRCPFKIVBQFD-UHFFFAOYSA-N 0.000 claims description 2
• UHSVYLFWFQNXRY-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UHSVYLFWFQNXRY-UHFFFAOYSA-N 0.000 claims description 2
• YVTPALHJEBAVFC-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound C1CC(C#N)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YVTPALHJEBAVFC-UHFFFAOYSA-N 0.000 claims description 2
• UQQAALQDDBGGJU-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidine-3-carbonitrile Chemical compound C1C(C#N)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UQQAALQDDBGGJU-UHFFFAOYSA-N 0.000 claims description 2
• ZTGZWFZNVOVCSI-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-4-one Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCC(=O)CC1 ZTGZWFZNVOVCSI-UHFFFAOYSA-N 0.000 claims description 2
• OLXGCABQYDQRKC-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OLXGCABQYDQRKC-UHFFFAOYSA-N 0.000 claims description 2
• LYBQDBKBWCXHLB-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LYBQDBKBWCXHLB-UHFFFAOYSA-N 0.000 claims description 2
• ZNPDAYJZIRPRFQ-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ZNPDAYJZIRPRFQ-UHFFFAOYSA-N 0.000 claims description 2
• NVZBDCOGNZHANV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxepan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCOCC1 NVZBDCOGNZHANV-UHFFFAOYSA-N 0.000 claims description 2
• BKUZKFYKHUKHQD-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(trifluoromethyl)pyridin-4-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(C(F)(F)F)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 BKUZKFYKHUKHQD-UHFFFAOYSA-N 0.000 claims description 2
• MEAZAXUDNCFOIG-FQEVSTJZSA-N 2-[(2s)-1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-2-yl]propan-2-ol Chemical compound CC(C)(O)[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 MEAZAXUDNCFOIG-FQEVSTJZSA-N 0.000 claims description 2
• LSXLNZAVKKFYLI-UHFFFAOYSA-N 2-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LSXLNZAVKKFYLI-UHFFFAOYSA-N 0.000 claims description 2
• ARBDZNDJQUKKDD-UHFFFAOYSA-N 2-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]propan-2-ol Chemical compound C1CC(C(C)(O)C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 ARBDZNDJQUKKDD-UHFFFAOYSA-N 0.000 claims description 2
• VQBSHRMJYCLXMB-UHFFFAOYSA-N 2-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 VQBSHRMJYCLXMB-UHFFFAOYSA-N 0.000 claims description 2
• UWXGULKLJNSGCD-UHFFFAOYSA-N 3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]benzonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CC(C#N)=C1 UWXGULKLJNSGCD-UHFFFAOYSA-N 0.000 claims description 2
• RUSRKRHQDCIFAK-UHFFFAOYSA-N 3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCC(=O)C1 RUSRKRHQDCIFAK-UHFFFAOYSA-N 0.000 claims description 2
• PHKDBPOGMAQERV-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperazin-2-one Chemical compound C1CNC(=O)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 PHKDBPOGMAQERV-UHFFFAOYSA-N 0.000 claims description 2
• ZXQSIZFCBGTLEV-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ZXQSIZFCBGTLEV-UHFFFAOYSA-N 0.000 claims description 2
• UHCCFVNTZKQAGF-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]benzonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=C(C#N)C=C1 UHCCFVNTZKQAGF-UHFFFAOYSA-N 0.000 claims description 2
• BIFVLRHOLAYNMO-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCC(=O)CC1 BIFVLRHOLAYNMO-UHFFFAOYSA-N 0.000 claims description 2
• FQOWBVCZKJZQOG-UHFFFAOYSA-N 5-fluoro-n-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC(F)=CC=C2S1 FQOWBVCZKJZQOG-UHFFFAOYSA-N 0.000 claims description 2
• SMYDNCOXQKJCTH-UHFFFAOYSA-N 5-fluoro-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC(F)=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 SMYDNCOXQKJCTH-UHFFFAOYSA-N 0.000 claims description 2
• KERONYYLEGQYEG-UHFFFAOYSA-N 6-fluoro-n-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=C(F)C=C2S1 KERONYYLEGQYEG-UHFFFAOYSA-N 0.000 claims description 2
• BSGFESLJQKRQEU-UHFFFAOYSA-N 6-fluoro-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound S1C2=CC(F)=CC=C2N=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 BSGFESLJQKRQEU-UHFFFAOYSA-N 0.000 claims description 2
• MVFREHJVIKPVSY-UHFFFAOYSA-N 7-fluoro-n-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC(F)=C2S1 MVFREHJVIKPVSY-UHFFFAOYSA-N 0.000 claims description 2
• JIPQSVBYFDEBMH-INIZCTEOSA-N [(2s)-1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 JIPQSVBYFDEBMH-INIZCTEOSA-N 0.000 claims description 2
• KSDGDEIZWGGUDZ-UHFFFAOYSA-N [1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-2-yl]methanol Chemical compound OCC1CCCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KSDGDEIZWGGUDZ-UHFFFAOYSA-N 0.000 claims description 2
• WLRYRZNBAXGEKR-UHFFFAOYSA-N [1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 WLRYRZNBAXGEKR-UHFFFAOYSA-N 0.000 claims description 2
• UNKROODATZENFE-UHFFFAOYSA-N [4-[3-(3,6-dihydro-2h-pyran-4-yl)pyrazin-2-yl]oxyphenyl]-(1h-imidazo[4,5-b]pyridin-2-yl)methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CCOCC1 UNKROODATZENFE-UHFFFAOYSA-N 0.000 claims description 2
• QSVXRNXNORDCIH-SFHVURJKSA-N ethyl (3s)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-3-carboxylate Chemical compound C1[C@@H](C(=O)OCC)CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QSVXRNXNORDCIH-SFHVURJKSA-N 0.000 claims description 2
• CKXZBMOIYNDXRY-UHFFFAOYSA-N ethyl 2-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 CKXZBMOIYNDXRY-UHFFFAOYSA-N 0.000 claims description 2
• ZQFKEWBKDYUSFD-MRXNPFEDSA-N methyl (3r)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidine-3-carboxylate Chemical compound C1[C@H](C(=O)OC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ZQFKEWBKDYUSFD-MRXNPFEDSA-N 0.000 claims description 2
• ZQFKEWBKDYUSFD-INIZCTEOSA-N methyl (3s)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidine-3-carboxylate Chemical compound C1[C@@H](C(=O)OC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ZQFKEWBKDYUSFD-INIZCTEOSA-N 0.000 claims description 2
• SQZRXWUIHAQLRV-UHFFFAOYSA-N methyl 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]azetidine-3-carboxylate Chemical compound C1C(C(=O)OC)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 SQZRXWUIHAQLRV-UHFFFAOYSA-N 0.000 claims description 2
• DRHYJGCSAVJECO-UHFFFAOYSA-N methyl 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OC)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 DRHYJGCSAVJECO-UHFFFAOYSA-N 0.000 claims description 2
• OYEMMCMQHPPZRE-UHFFFAOYSA-N methyl 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]oxane-4-carboxylate Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(C(=O)OC)CCOCC1 OYEMMCMQHPPZRE-UHFFFAOYSA-N 0.000 claims description 2
• OCQDDOPNHKDUIT-UHFFFAOYSA-N n-[2-fluoro-4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1F)=CC=C1NC1=NC2=CC=CC=C2S1 OCQDDOPNHKDUIT-UHFFFAOYSA-N 0.000 claims description 2
• QHQXBNYKAMDUDS-UHFFFAOYSA-N n-[4-(3-cyclopentylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 QHQXBNYKAMDUDS-UHFFFAOYSA-N 0.000 claims description 2
• MCPHJRVZGYLLFS-UHFFFAOYSA-N n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 MCPHJRVZGYLLFS-UHFFFAOYSA-N 0.000 claims description 2
• KZQUGAMNOZLLRA-UHFFFAOYSA-N n-[4-(3-pyridin-3-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CN=C1 KZQUGAMNOZLLRA-UHFFFAOYSA-N 0.000 claims description 2
• LHQWYDHZOBIFCY-UHFFFAOYSA-N n-[4-(3-quinolin-5-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2C(C3=NC=CN=C3OC3=CC=C(C=C3)NC=3SC4=CC=CC=C4N=3)=CC=CC2=N1 LHQWYDHZOBIFCY-UHFFFAOYSA-N 0.000 claims description 2
• OAIAEZMDZTUQTO-UHFFFAOYSA-N n-[4-[3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound O1CCOC11CCN(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)CC1 OAIAEZMDZTUQTO-UHFFFAOYSA-N 0.000 claims description 2
• DLBUCAJUNWPCLY-UHFFFAOYSA-N n-[4-[3-(1-methylpiperidin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 DLBUCAJUNWPCLY-UHFFFAOYSA-N 0.000 claims description 2
• YLSRTMOLPMOJMY-UHFFFAOYSA-N n-[4-[3-(2,6-dimethylmorpholin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1C(C)OC(C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YLSRTMOLPMOJMY-UHFFFAOYSA-N 0.000 claims description 2
• VGLPMMNLRBDBMX-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(OC)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 VGLPMMNLRBDBMX-UHFFFAOYSA-N 0.000 claims description 2
• CRKFRXWSFJBSLF-UHFFFAOYSA-N n-[4-[3-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(NC3=CC=C(C=C3)OC3=NC=CN=C3N3CC=4N=CNC=4CC3)=NC2=C1 CRKFRXWSFJBSLF-UHFFFAOYSA-N 0.000 claims description 2
• OJPKDYDFGPBSEW-UHFFFAOYSA-N n-[4-[3-(3-methoxyphenyl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 OJPKDYDFGPBSEW-UHFFFAOYSA-N 0.000 claims description 2
• BJDKNNDIYCAXMV-UHFFFAOYSA-N n-[4-[3-(3-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=CN=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BJDKNNDIYCAXMV-UHFFFAOYSA-N 0.000 claims description 2
• QHUHGALOARSWFD-UHFFFAOYSA-N n-[4-[3-(4-methylpiperazin-1-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 QHUHGALOARSWFD-UHFFFAOYSA-N 0.000 claims description 2
• KMGSAXQZYDPDMN-UHFFFAOYSA-N n-[4-[3-(6-methylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KMGSAXQZYDPDMN-UHFFFAOYSA-N 0.000 claims description 2
• AOBDSAPMYHFWOL-UHFFFAOYSA-N n-[4-[3-(6-morpholin-4-ylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCN1C1=CC=C(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=N1 AOBDSAPMYHFWOL-UHFFFAOYSA-N 0.000 claims description 2
• PAUMHWVEIXSVLQ-UHFFFAOYSA-N n-[4-[3-(azetidin-1-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 PAUMHWVEIXSVLQ-UHFFFAOYSA-N 0.000 claims description 2
• JQCVMLPLLIQFMP-UHFFFAOYSA-N n-[4-[3-[3-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1C(COC)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 JQCVMLPLLIQFMP-UHFFFAOYSA-N 0.000 claims description 2
• UQNGKGCQRCJBTD-UHFFFAOYSA-N n-[4-[3-[4-(methoxymethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CC(COC)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UQNGKGCQRCJBTD-UHFFFAOYSA-N 0.000 claims description 2
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 14
• BHGBMGVTLFZRCP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methoxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(OC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 BHGBMGVTLFZRCP-UHFFFAOYSA-N 0.000 claims 2
• VIZVTXGNPQLHRZ-DLBZAZTESA-N 1h-benzimidazol-2-yl-[4-[3-[(1s,3r)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@H](O)CCC[C@@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-DLBZAZTESA-N 0.000 claims 2
• GCQAVHNIIDWDIK-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)-[4-[3-(2-methylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound CC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)C)C=C1 GCQAVHNIIDWDIK-UHFFFAOYSA-N 0.000 claims 1
• JZSMZKJZDCZCGJ-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 JZSMZKJZDCZCGJ-UHFFFAOYSA-N 0.000 claims 1
• LIUKTCWPZUWMKH-NVXWUHKLSA-N (1r,3r)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-NVXWUHKLSA-N 0.000 claims 1
• NFJWUVZWQQNUEZ-MRXNPFEDSA-N (2r)-1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@H](F)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NFJWUVZWQQNUEZ-MRXNPFEDSA-N 0.000 claims 1
• NWONINZVPVTBGN-MRXNPFEDSA-N (2r)-1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@H](F)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NWONINZVPVTBGN-MRXNPFEDSA-N 0.000 claims 1
• NFJWUVZWQQNUEZ-INIZCTEOSA-N (2s)-1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@@H](F)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NFJWUVZWQQNUEZ-INIZCTEOSA-N 0.000 claims 1
• NWONINZVPVTBGN-INIZCTEOSA-N (2s)-1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@@H](F)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NWONINZVPVTBGN-INIZCTEOSA-N 0.000 claims 1
• AFWSQFMTRFITGY-UHFFFAOYSA-N (5-fluoro-1-methylbenzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC(F)=CC=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 AFWSQFMTRFITGY-UHFFFAOYSA-N 0.000 claims 1
• CYYBRDFIVOTWLR-UHFFFAOYSA-N (6-fluoro-1-methylbenzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=C(F)C=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 CYYBRDFIVOTWLR-UHFFFAOYSA-N 0.000 claims 1
• WOMJZGSOHCMFTN-UHFFFAOYSA-N (6-fluoro-1h-benzimidazol-2-yl)-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=C(F)C=C3N=2)C=C1 WOMJZGSOHCMFTN-UHFFFAOYSA-N 0.000 claims 1
• JRIRUWHLHRZROS-UHFFFAOYSA-N (6-fluoro-1h-benzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N1C2=CC(F)=CC=C2N=C1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 JRIRUWHLHRZROS-UHFFFAOYSA-N 0.000 claims 1
• AFVMYKZMYQFDLR-CQSZACIVSA-N (6r)-4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)N[C@H](C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AFVMYKZMYQFDLR-CQSZACIVSA-N 0.000 claims 1
• AFVMYKZMYQFDLR-AWEZNQCLSA-N (6s)-4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)N[C@@H](C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AFVMYKZMYQFDLR-AWEZNQCLSA-N 0.000 claims 1
• GZSNDCOIZXWXRF-UHFFFAOYSA-N 1-[3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 GZSNDCOIZXWXRF-UHFFFAOYSA-N 0.000 claims 1
• PODKIINFHOBJKF-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 PODKIINFHOBJKF-UHFFFAOYSA-N 0.000 claims 1
• KFCTWWLEMAKQQT-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]azetidine-3-carbonitrile Chemical compound C1C(C#N)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KFCTWWLEMAKQQT-UHFFFAOYSA-N 0.000 claims 1
• OMJGZDVNBSTDBW-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 OMJGZDVNBSTDBW-UHFFFAOYSA-N 0.000 claims 1
• ZHPLRZTVNKJRBB-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 ZHPLRZTVNKJRBB-UHFFFAOYSA-N 0.000 claims 1
• YSQISUXUOMBANZ-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCC(C#N)CC1 YSQISUXUOMBANZ-UHFFFAOYSA-N 0.000 claims 1
• BFSXGZFTNAZQQI-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)-2-fluorophenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C(=C1)F)=CC=C1NC1=NC2=CC=CC=C2S1 BFSXGZFTNAZQQI-UHFFFAOYSA-N 0.000 claims 1
• CHAZKGHHVDIGDH-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 CHAZKGHHVDIGDH-UHFFFAOYSA-N 0.000 claims 1
• JVXPQSSXFIEQET-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 JVXPQSSXFIEQET-UHFFFAOYSA-N 0.000 claims 1
• NFJWUVZWQQNUEZ-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)C(F)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NFJWUVZWQQNUEZ-UHFFFAOYSA-N 0.000 claims 1
• YYQXJEOOPHCARO-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)C(O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YYQXJEOOPHCARO-UHFFFAOYSA-N 0.000 claims 1
• AJWGKNQBAKXMGL-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AJWGKNQBAKXMGL-UHFFFAOYSA-N 0.000 claims 1
• FGCGQRSGPBXQSO-UHFFFAOYSA-N 1-[4-[3-[4-(1-methylbenzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)C)C=C1 FGCGQRSGPBXQSO-UHFFFAOYSA-N 0.000 claims 1
• CDKHCVAKJVNZMB-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 CDKHCVAKJVNZMB-UHFFFAOYSA-N 0.000 claims 1
• MRTTVYSHGAWTBQ-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 MRTTVYSHGAWTBQ-UHFFFAOYSA-N 0.000 claims 1
• LIPDYWGPFVKQEM-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 LIPDYWGPFVKQEM-UHFFFAOYSA-N 0.000 claims 1
• NWONINZVPVTBGN-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)C(F)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NWONINZVPVTBGN-UHFFFAOYSA-N 0.000 claims 1
• LXMWZAOZSLGOQC-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 LXMWZAOZSLGOQC-UHFFFAOYSA-N 0.000 claims 1
• GGDCZBXCIWBJKS-UHFFFAOYSA-N 1-[4-[3-[4-[1h-benzimidazol-2-yl(hydroxy)methyl]phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(O)C=2NC3=CC=CC=C3N=2)C=C1 GGDCZBXCIWBJKS-UHFFFAOYSA-N 0.000 claims 1
• IRKXWIGDPRTXGR-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-phenoxypyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OC1=CC=CC=C1 IRKXWIGDPRTXGR-UHFFFAOYSA-N 0.000 claims 1
• YZVPBDASJFHUAL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-piperidin-1-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCCCC1 YZVPBDASJFHUAL-UHFFFAOYSA-N 0.000 claims 1
• ZCFIQKOLFBWTNU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-3-yloxypyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OC1=CC=CN=C1 ZCFIQKOLFBWTNU-UHFFFAOYSA-N 0.000 claims 1
• SKXVGFCQSAGRMV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-3-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CN=C1 SKXVGFCQSAGRMV-UHFFFAOYSA-N 0.000 claims 1
• BXZUDQZZCUTONO-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=NC=C1 BXZUDQZZCUTONO-UHFFFAOYSA-N 0.000 claims 1
• ARDZLOLLOQEMHJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyrrolidin-1-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCCC1 ARDZLOLLOQEMHJ-UHFFFAOYSA-N 0.000 claims 1
• ARGSJRSVVCPPON-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-quinolin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound C1=CC=C2C(C3=NC=CN=C3OC3=CC=C(C=C3)C(C=3NC4=CC=CC=C4N=3)=O)=CC=NC2=C1 ARGSJRSVVCPPON-UHFFFAOYSA-N 0.000 claims 1
• HTWNAFJOAGRRBM-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-quinolin-5-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound C1=CC=C2C(C3=NC=CN=C3OC3=CC=C(C=C3)C(C=3NC4=CC=CC=C4N=3)=O)=CC=CC2=N1 HTWNAFJOAGRRBM-UHFFFAOYSA-N 0.000 claims 1
• FSOBJGLZSZGYOL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(1,4-oxazepan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCCOCC1 FSOBJGLZSZGYOL-UHFFFAOYSA-N 0.000 claims 1
• RPOWDMWZGNQSBU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2,6-dimethoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC(OC)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 RPOWDMWZGNQSBU-UHFFFAOYSA-N 0.000 claims 1
• WZICCIUGDUKRRN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2,6-dimethylmorpholin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(C)OC(C)CN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WZICCIUGDUKRRN-UHFFFAOYSA-N 0.000 claims 1
• VLYJRGUWIXOODC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxyphenyl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VLYJRGUWIXOODC-UHFFFAOYSA-N 0.000 claims 1
• VLBHJGKQIHPSBA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VLBHJGKQIHPSBA-UHFFFAOYSA-N 0.000 claims 1
• YLASKEPHIYXYHN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(OC)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 YLASKEPHIYXYHN-UHFFFAOYSA-N 0.000 claims 1
• NASLEEKYYZHLMU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxyquinolin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=CC=C2NC(C(=O)C3=CC=C(C=C3)OC3=NC=CN=C3C3=CC4=CC=CC=C4N=C3OC)=NC2=C1 NASLEEKYYZHLMU-UHFFFAOYSA-N 0.000 claims 1
• WINCBLQQJITJLB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound CC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WINCBLQQJITJLB-UHFFFAOYSA-N 0.000 claims 1
• MOMKNNQNCSGNRV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 MOMKNNQNCSGNRV-UHFFFAOYSA-N 0.000 claims 1
• OYMQPGWLPLRUOX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-morpholin-4-ylethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCN1CCOCC1 OYMQPGWLPLRUOX-UHFFFAOYSA-N 0.000 claims 1
• OBRWVGKIAUHLFT-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-pyridin-2-ylethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCC1=CC=CC=N1 OBRWVGKIAUHLFT-UHFFFAOYSA-N 0.000 claims 1
• OGHGNHXUOKXZCX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-pyrrolidin-1-ylethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCN1CCCC1 OGHGNHXUOKXZCX-UHFFFAOYSA-N 0.000 claims 1
• JGLJRVWZCSNEDY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N(C1)CCC2=C1N=CN2 JGLJRVWZCSNEDY-UHFFFAOYSA-N 0.000 claims 1
• TZBWLCHZJRCGOQ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-hydroxyazetidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(O)CN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 TZBWLCHZJRCGOQ-UHFFFAOYSA-N 0.000 claims 1
• NOXUPUUDBQZEQB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-hydroxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(O)CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NOXUPUUDBQZEQB-UHFFFAOYSA-N 0.000 claims 1
• GYAHJLWOOSIHGS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methoxyphenyl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 GYAHJLWOOSIHGS-UHFFFAOYSA-N 0.000 claims 1
• AXMKWTHOPXEJGI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CN=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 AXMKWTHOPXEJGI-UHFFFAOYSA-N 0.000 claims 1
• PIBYUXDUMHDTHI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-pyridin-3-ylpropoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCCC1=CC=CN=C1 PIBYUXDUMHDTHI-UHFFFAOYSA-N 0.000 claims 1
• MSLMVJKRPSMSRP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-hydroxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(O)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 MSLMVJKRPSMSRP-UHFFFAOYSA-N 0.000 claims 1
• DLHLXYVYQGDEPM-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=NC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 DLHLXYVYQGDEPM-UHFFFAOYSA-N 0.000 claims 1
• DEPGKFSRVIIJKU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methylpiperazin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CN(C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 DEPGKFSRVIIJKU-UHFFFAOYSA-N 0.000 claims 1
• RSFBEXTXIDVAHU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-morpholin-4-ylpiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N(CC1)CCC1N1CCOCC1 RSFBEXTXIDVAHU-UHFFFAOYSA-N 0.000 claims 1
• BXRWUPRQTKCGON-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(5-fluoro-2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=C(F)C=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 BXRWUPRQTKCGON-UHFFFAOYSA-N 0.000 claims 1
• QBFPMCPDBZLNIY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(5-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CN=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 QBFPMCPDBZLNIY-UHFFFAOYSA-N 0.000 claims 1
• UYKPWRCLQFWBMS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(6-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(OC)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 UYKPWRCLQFWBMS-UHFFFAOYSA-N 0.000 claims 1
• MEDCWBFNYPAKKN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(cyclopropylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1CC1 MEDCWBFNYPAKKN-UHFFFAOYSA-N 0.000 claims 1
• BKTPDUKLTUVKDY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCOC1 BKTPDUKLTUVKDY-UHFFFAOYSA-N 0.000 claims 1
• VJEDECJAJOUHQS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-3-ylamino)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1NC1CCCOC1 VJEDECJAJOUHQS-UHFFFAOYSA-N 0.000 claims 1
• YAQXVILTNUOAIK-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-4-ylamino)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1NC1CCOCC1 YAQXVILTNUOAIK-UHFFFAOYSA-N 0.000 claims 1
• FLFJGUVHSXRKII-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxolan-3-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1CCOC1 FLFJGUVHSXRKII-UHFFFAOYSA-N 0.000 claims 1
• KUWDSKWHERONCX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(pyridin-2-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1=CC=CC=N1 KUWDSKWHERONCX-UHFFFAOYSA-N 0.000 claims 1
• JEUOFPDZFFENPA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(pyridin-3-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1=CC=CN=C1 JEUOFPDZFFENPA-UHFFFAOYSA-N 0.000 claims 1
• UZKSBOFNIMRSDU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(pyridin-4-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1=CC=NC=C1 UZKSBOFNIMRSDU-UHFFFAOYSA-N 0.000 claims 1
• VIZVTXGNPQLHRZ-IAGOWNOFSA-N 1h-benzimidazol-2-yl-[4-[3-[(1r,3r)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@H](O)CCC[C@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-IAGOWNOFSA-N 0.000 claims 1
• VIZVTXGNPQLHRZ-SJORKVTESA-N 1h-benzimidazol-2-yl-[4-[3-[(1r,3s)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@@H](O)CCC[C@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-SJORKVTESA-N 0.000 claims 1
• PIZNUGDDGNOQHG-QGZVFWFLSA-N 1h-benzimidazol-2-yl-[4-[3-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC[C@H]1CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PIZNUGDDGNOQHG-QGZVFWFLSA-N 0.000 claims 1
• PCUFMTNTOOPRHU-INIZCTEOSA-N 1h-benzimidazol-2-yl-[4-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound OC[C@@H]1CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PCUFMTNTOOPRHU-INIZCTEOSA-N 0.000 claims 1
• WIJUCVHWNZQALU-OAHLLOKOSA-N 1h-benzimidazol-2-yl-[4-[3-[(3r)-3-(hydroxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@H](CO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WIJUCVHWNZQALU-OAHLLOKOSA-N 0.000 claims 1
• PLJXWUBEQUVCBH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(1-methylpyrrolidin-2-yl)ethoxy]pyrazin-2-yl]oxyphenyl]methanone Chemical compound CN1CCCC1CCOC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PLJXWUBEQUVCBH-UHFFFAOYSA-N 0.000 claims 1
• XQFKWIKPJOIRMC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]pyrazin-2-yl]oxyphenyl]methanone Chemical compound N1=CSC(CCOC=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1C XQFKWIKPJOIRMC-UHFFFAOYSA-N 0.000 claims 1
• QJEPBHICDVQIMD-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(2-hydroxyethyl)piperazin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CN(CCO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QJEPBHICDVQIMD-UHFFFAOYSA-N 0.000 claims 1
• KANNKAQVIUSRKP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(2-hydroxyethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(CCO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 KANNKAQVIUSRKP-UHFFFAOYSA-N 0.000 claims 1
• OVOUUAFYHZWGSH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(hydroxymethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(CO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OVOUUAFYHZWGSH-UHFFFAOYSA-N 0.000 claims 1
• OZUQEIMBSCUUPC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(methoxymethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(COC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OZUQEIMBSCUUPC-UHFFFAOYSA-N 0.000 claims 1
• ILOXGTYENJEMOX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(trifluoromethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(C(F)(F)F)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ILOXGTYENJEMOX-UHFFFAOYSA-N 0.000 claims 1
• ADMPHCQUPDYFKW-VWLOTQADSA-N 1h-benzimidazol-2-yl-[4-[3-[4-[(2s)-1,1,1-trifluoro-2-hydroxypropan-2-yl]piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC([C@@](O)(C)C(F)(F)F)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ADMPHCQUPDYFKW-VWLOTQADSA-N 0.000 claims 1
• SGVADHZEXLKTJV-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridin-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 SGVADHZEXLKTJV-UHFFFAOYSA-N 0.000 claims 1
• QAKJQHVIJCQZKR-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridin-2-yl-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 QAKJQHVIJCQZKR-UHFFFAOYSA-N 0.000 claims 1
• DXWVYUAWMGHOEQ-UHFFFAOYSA-N 2-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]-1,1,1-trifluoropropan-2-ol Chemical compound C1CC(C(O)(C)C(F)(F)F)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 DXWVYUAWMGHOEQ-UHFFFAOYSA-N 0.000 claims 1
• HTFXSBUOJAQECG-UHFFFAOYSA-N 2-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 HTFXSBUOJAQECG-UHFFFAOYSA-N 0.000 claims 1
• GXNWIQSFJQCNPM-UHFFFAOYSA-N 2-methoxy-1-[4-[3-[4-(1-methylbenzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)C)C=C1 GXNWIQSFJQCNPM-UHFFFAOYSA-N 0.000 claims 1
• VLXIWTVVCJCPGQ-UHFFFAOYSA-N 3-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-3-oxopropanenitrile Chemical compound C1CN(C(CC#N)=O)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VLXIWTVVCJCPGQ-UHFFFAOYSA-N 0.000 claims 1
• RPCSCZBLOGROPY-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-1-propan-2-ylpiperazin-2-one Chemical compound C1C(=O)N(C(C)C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 RPCSCZBLOGROPY-UHFFFAOYSA-N 0.000 claims 1
• AFVMYKZMYQFDLR-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)NC(C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AFVMYKZMYQFDLR-UHFFFAOYSA-N 0.000 claims 1
• GFIJTCIBSLRCRB-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]oxan-4-ol Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(O)CCOCC1 GFIJTCIBSLRCRB-UHFFFAOYSA-N 0.000 claims 1
• MNBKHXOOKZPRRO-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-1-methyl-2,3-dihydropyridin-6-one Chemical compound O=C1N(C)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 MNBKHXOOKZPRRO-UHFFFAOYSA-N 0.000 claims 1
• OUGAZDLWIKVYON-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OUGAZDLWIKVYON-UHFFFAOYSA-N 0.000 claims 1
• AYGYYFLHDJHALN-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-1-methylpiperidin-2-one Chemical compound C1C(=O)N(C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 AYGYYFLHDJHALN-UHFFFAOYSA-N 0.000 claims 1
• QDGUFUYNPQKEQO-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]oxane-4-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1(C#N)CCOCC1 QDGUFUYNPQKEQO-UHFFFAOYSA-N 0.000 claims 1
• DDGZIRXCBJYJFR-UHFFFAOYSA-N 4-[3-[4-[1h-benzimidazol-2-yl(difluoro)methyl]phenoxy]pyrazin-2-yl]morpholine;1h-benzimidazol-2-yl-[4-[3-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(F)(F)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1.C1CC(C(C)(O)C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 DDGZIRXCBJYJFR-UHFFFAOYSA-N 0.000 claims 1
• IWEVCNNWMFEVKS-UHFFFAOYSA-N 5-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyridine-2-carbonitrile;n-[4-(3-pyrimidin-5-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CN=CN=C1.C1=NC(C#N)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 IWEVCNNWMFEVKS-UHFFFAOYSA-N 0.000 claims 1
• HRQSHDCWHGQGAC-UHFFFAOYSA-N 6-fluoro-n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-1h-benzimidazol-2-amine Chemical compound N=1C2=CC(F)=CC=C2NC=1NC(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 HRQSHDCWHGQGAC-UHFFFAOYSA-N 0.000 claims 1
• FPXFNDLAKFLGMO-UHFFFAOYSA-N 8-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-2-methyl-2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1N(C)CCC11CCN(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)CC1 FPXFNDLAKFLGMO-UHFFFAOYSA-N 0.000 claims 1
• 241000687983 Cerobasis alpha Species 0.000 claims 1
• XQQVEIPSNNREQS-OAHLLOKOSA-N [(3r)-1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-3-yl]methanol Chemical compound C1[C@H](CO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 XQQVEIPSNNREQS-OAHLLOKOSA-N 0.000 claims 1
• CBPDLAAUWWVMKL-UHFFFAOYSA-N [1-(2-fluoroethyl)benzimidazol-2-yl]-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)CCF)C=C1 CBPDLAAUWWVMKL-UHFFFAOYSA-N 0.000 claims 1
• NBNXTDSTFXNNPW-UHFFFAOYSA-N [1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-1-oxopropan-2-yl] acetate Chemical compound C1CN(C(=O)C(OC(C)=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NBNXTDSTFXNNPW-UHFFFAOYSA-N 0.000 claims 1
• PGPFEPMKFZYZLU-UHFFFAOYSA-N [2-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-oxoethyl] acetate Chemical compound C1CN(C(=O)COC(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PGPFEPMKFZYZLU-UHFFFAOYSA-N 0.000 claims 1
• RPIVFFXGWTXQJQ-UHFFFAOYSA-N [4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-(1-methylbenzimidazol-2-yl)methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)C)C=C1 RPIVFFXGWTXQJQ-UHFFFAOYSA-N 0.000 claims 1
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