JP2012512255A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012512255A5 JP2012512255A5 JP2011542411A JP2011542411A JP2012512255A5 JP 2012512255 A5 JP2012512255 A5 JP 2012512255A5 JP 2011542411 A JP2011542411 A JP 2011542411A JP 2011542411 A JP2011542411 A JP 2011542411A JP 2012512255 A5 JP2012512255 A5 JP 2012512255A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- ylamino
- phenoxy
- phenyl
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- -1 tetrahydropyrani Chemical group 0.000 claims 99
- 150000001875 compounds Chemical class 0.000 claims 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 229920006395 saturated elastomer Polymers 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004429 atom Chemical group 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 4
- 101100055332 Pseudomonas oleovorans alkN gene Proteins 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 2
- MBWWOZAOTCKLFQ-AEFFLSMTSA-N (1s,3r)-3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MBWWOZAOTCKLFQ-AEFFLSMTSA-N 0.000 claims 2
- UMTVKOCJSLGBPV-WBVHZDCISA-N (1s,3r)-3-[3-[4-(pyridin-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=CC=CC=N1 UMTVKOCJSLGBPV-WBVHZDCISA-N 0.000 claims 2
- UMTVKOCJSLGBPV-RDJZCZTQSA-N (1s,3s)-3-[3-[4-(pyridin-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=CC=CC=N1 UMTVKOCJSLGBPV-RDJZCZTQSA-N 0.000 claims 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- PMGLZVXKDHUYHB-UHFFFAOYSA-N 3,5-difluoro-n-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC1=CC(F)=CN=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 PMGLZVXKDHUYHB-UHFFFAOYSA-N 0.000 claims 2
- IETBWTROZWYCIP-UHFFFAOYSA-N 6-methyl-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound CC1=CC=CC(NC=2C=CC(OC=3C(=CC=CN=3)C(F)(F)F)=CC=2)=N1 IETBWTROZWYCIP-UHFFFAOYSA-N 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 210000001159 caudate nucleus Anatomy 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- QBHHPAVYYCLELV-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-[4-(pyridin-2-ylamino)phenoxy]pyridine-3-carboxamide Chemical compound C=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1C(=O)NCC1CC1 QBHHPAVYYCLELV-UHFFFAOYSA-N 0.000 claims 2
- HXFKUNCAQXNCPY-UHFFFAOYSA-N n-[4-(3-pyridin-3-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CN=C1 HXFKUNCAQXNCPY-UHFFFAOYSA-N 0.000 claims 2
- MMPZKSPHWRDPHY-UHFFFAOYSA-N n-[4-[3-(2-methylpyridin-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(C)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 MMPZKSPHWRDPHY-UHFFFAOYSA-N 0.000 claims 2
- KZJDZHRONGUZNO-UHFFFAOYSA-N n-[4-[3-(oxolan-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1OCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 KZJDZHRONGUZNO-UHFFFAOYSA-N 0.000 claims 2
- 230000001898 pallidal effect Effects 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- ODMSXEZLTJFHRC-UZUQRXQVSA-N (1r,3r)-1-methyl-3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclohexan-1-ol Chemical compound C1[C@](C)(O)CCC[C@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 ODMSXEZLTJFHRC-UZUQRXQVSA-N 0.000 claims 1
- YTSQJSLXKWSKBB-NVXWUHKLSA-N (1r,3r)-3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclopentan-1-ol Chemical compound C1[C@H](O)CC[C@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YTSQJSLXKWSKBB-NVXWUHKLSA-N 0.000 claims 1
- UMTVKOCJSLGBPV-NVXWUHKLSA-N (1r,3r)-3-[3-[4-(pyridin-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=CC=CC=N1 UMTVKOCJSLGBPV-NVXWUHKLSA-N 0.000 claims 1
- MBWWOZAOTCKLFQ-FUHWJXTLSA-N (1r,3s)-3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MBWWOZAOTCKLFQ-FUHWJXTLSA-N 0.000 claims 1
- YTSQJSLXKWSKBB-DOTOQJQBSA-N (1r,3s)-3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclopentan-1-ol Chemical compound C1[C@H](O)CC[C@@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YTSQJSLXKWSKBB-DOTOQJQBSA-N 0.000 claims 1
- UMTVKOCJSLGBPV-DOTOQJQBSA-N (1r,3s)-3-[3-[4-(pyridin-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=CC=CC=N1 UMTVKOCJSLGBPV-DOTOQJQBSA-N 0.000 claims 1
- ODMSXEZLTJFHRC-SBUREZEXSA-N (1s,3s)-1-methyl-3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclohexan-1-ol Chemical compound C1[C@@](C)(O)CCC[C@@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 ODMSXEZLTJFHRC-SBUREZEXSA-N 0.000 claims 1
- YTSQJSLXKWSKBB-RDJZCZTQSA-N (1s,3s)-3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclopentan-1-ol Chemical compound C1[C@@H](O)CC[C@@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YTSQJSLXKWSKBB-RDJZCZTQSA-N 0.000 claims 1
- XHDDQRLBRXBUOH-UHFFFAOYSA-N (2-methyl-1,3-thiazolidin-3-yl)-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]methanone Chemical compound CC1SCCN1C(=O)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 XHDDQRLBRXBUOH-UHFFFAOYSA-N 0.000 claims 1
- RNHRUZNNCMCJLV-GOSISDBHSA-N (2r)-2-methoxy-1-[4-[3-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyrazin-2-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](C)OC)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 RNHRUZNNCMCJLV-GOSISDBHSA-N 0.000 claims 1
- RNHRUZNNCMCJLV-SFHVURJKSA-N (2s)-2-methoxy-1-[4-[3-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyrazin-2-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@H](C)OC)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 RNHRUZNNCMCJLV-SFHVURJKSA-N 0.000 claims 1
- PLZWZJSKWCEZIS-HNNXBMFYSA-N (2s)-4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]but-3-yn-2-ol Chemical compound C[C@H](O)C#CC1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 PLZWZJSKWCEZIS-HNNXBMFYSA-N 0.000 claims 1
- VBMBLEBVOTXJTF-UHFFFAOYSA-N (3-methoxypiperidin-1-yl)-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]methanone Chemical compound C1C(OC)CCCN1C(=O)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VBMBLEBVOTXJTF-UHFFFAOYSA-N 0.000 claims 1
- NXVVXBAUUOIKAG-MRXNPFEDSA-N (3r)-1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrrolidin-3-ol Chemical compound C1[C@H](O)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NXVVXBAUUOIKAG-MRXNPFEDSA-N 0.000 claims 1
- SVXFQVQMFCGDOR-OAHLLOKOSA-N (3r)-1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-3-ol Chemical compound C1[C@H](O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 SVXFQVQMFCGDOR-OAHLLOKOSA-N 0.000 claims 1
- NXVVXBAUUOIKAG-INIZCTEOSA-N (3s)-1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NXVVXBAUUOIKAG-INIZCTEOSA-N 0.000 claims 1
- SVXFQVQMFCGDOR-HNNXBMFYSA-N (3s)-1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 SVXFQVQMFCGDOR-HNNXBMFYSA-N 0.000 claims 1
- ADFKONHTCRBTKC-UHFFFAOYSA-N (4-methoxypiperidin-1-yl)-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]methanone Chemical compound C1CC(OC)CCN1C(=O)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 ADFKONHTCRBTKC-UHFFFAOYSA-N 0.000 claims 1
- LHTWKNGXBIRNIY-UHFFFAOYSA-N 1,4-oxazepan-4-yl-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]methanone Chemical compound C=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1C(=O)N1CCCOCC1 LHTWKNGXBIRNIY-UHFFFAOYSA-N 0.000 claims 1
- KTPXENPNDMLGRM-IBGZPJMESA-N 1-[(3r)-3-[2-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC[C@@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 KTPXENPNDMLGRM-IBGZPJMESA-N 0.000 claims 1
- KTPXENPNDMLGRM-LJQANCHMSA-N 1-[(3s)-3-[2-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC[C@H]1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 KTPXENPNDMLGRM-LJQANCHMSA-N 0.000 claims 1
- CSZJRBHFDVKIKS-UHFFFAOYSA-N 1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidin-3-ol Chemical compound C1C(O)CCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 CSZJRBHFDVKIKS-UHFFFAOYSA-N 0.000 claims 1
- JEZLKUAHTOCVLL-UHFFFAOYSA-N 1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 JEZLKUAHTOCVLL-UHFFFAOYSA-N 0.000 claims 1
- CQDQNZHZKWKRRZ-UHFFFAOYSA-N 1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidin-4-one Chemical compound C1CC(=O)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 CQDQNZHZKWKRRZ-UHFFFAOYSA-N 0.000 claims 1
- VFEYWZZOCPDQAO-UHFFFAOYSA-N 1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidine-3-carbonitrile Chemical compound C1C(C#N)CCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VFEYWZZOCPDQAO-UHFFFAOYSA-N 0.000 claims 1
- CDROPJRUCHWGIO-UHFFFAOYSA-N 1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidine-4-carbonitrile Chemical compound C1CC(C#N)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 CDROPJRUCHWGIO-UHFFFAOYSA-N 0.000 claims 1
- QECYJTVEUAEHBF-UHFFFAOYSA-N 1-[3-[2-(pyridine-4-carbonyl)phenoxy]pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound C=1C=CC=C(OC=2C(=NC=CN=2)N2CCC(CC2)C#N)C=1C(=O)C1=CC=NC=C1 QECYJTVEUAEHBF-UHFFFAOYSA-N 0.000 claims 1
- KTPXENPNDMLGRM-UHFFFAOYSA-N 1-[3-[2-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 KTPXENPNDMLGRM-UHFFFAOYSA-N 0.000 claims 1
- HQWUNWMJUYEZRN-UHFFFAOYSA-N 1-[3-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 HQWUNWMJUYEZRN-UHFFFAOYSA-N 0.000 claims 1
- MSLMTQKFEUNANV-UHFFFAOYSA-N 1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MSLMTQKFEUNANV-UHFFFAOYSA-N 0.000 claims 1
- JXMJVRWUTVYLQZ-UHFFFAOYSA-N 1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-3-ol Chemical compound C1C(O)CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 JXMJVRWUTVYLQZ-UHFFFAOYSA-N 0.000 claims 1
- MGOBQJMKELVBHL-UHFFFAOYSA-N 1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MGOBQJMKELVBHL-UHFFFAOYSA-N 0.000 claims 1
- PMNSENSAXPVTRV-UHFFFAOYSA-N 1-[4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 PMNSENSAXPVTRV-UHFFFAOYSA-N 0.000 claims 1
- NYDBTFLHTFVDII-UHFFFAOYSA-N 1-[4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NYDBTFLHTFVDII-UHFFFAOYSA-N 0.000 claims 1
- RCIBWLDLAUIWOQ-UHFFFAOYSA-N 1-[4-[2-[4-[(3-fluoropyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC=CC=C1F RCIBWLDLAUIWOQ-UHFFFAOYSA-N 0.000 claims 1
- VUFZAQWIEMSGMG-UHFFFAOYSA-N 1-[4-[2-[4-[(4-fluoropyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC(F)=CC=N1 VUFZAQWIEMSGMG-UHFFFAOYSA-N 0.000 claims 1
- VIBAYRQTDLTCKX-UHFFFAOYSA-N 1-[4-[2-[4-[(5-chloropyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(Cl)C=N1 VIBAYRQTDLTCKX-UHFFFAOYSA-N 0.000 claims 1
- KTHRVPDOVPWUMY-UHFFFAOYSA-N 1-[4-[2-[4-[(5-fluoropyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(F)C=N1 KTHRVPDOVPWUMY-UHFFFAOYSA-N 0.000 claims 1
- NGPOJTOLJGZDNQ-UHFFFAOYSA-N 1-[4-[2-[4-[(5-methoxypyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound N1=CC(OC)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1CCN(C(C)=O)CC1 NGPOJTOLJGZDNQ-UHFFFAOYSA-N 0.000 claims 1
- JBKGNEWTPLGZFR-UHFFFAOYSA-N 1-[4-[2-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 JBKGNEWTPLGZFR-UHFFFAOYSA-N 0.000 claims 1
- ZKLSZNYDPNAANV-UHFFFAOYSA-N 1-[4-[2-[4-[(6-methylpyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC(C)=N1 ZKLSZNYDPNAANV-UHFFFAOYSA-N 0.000 claims 1
- QTQMKXPIYBIGSW-UHFFFAOYSA-N 1-[4-[3-[2-(pyridine-4-carbonyl)phenoxy]pyrazin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC=CN=C1OC1=CC=CC=C1C(=O)C1=CC=NC=C1 QTQMKXPIYBIGSW-UHFFFAOYSA-N 0.000 claims 1
- KFIQHFSOIUFIPH-UHFFFAOYSA-N 1-[4-[3-[2-fluoro-4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C(=C1)F)=CC=C1NC1=CC=CC=N1 KFIQHFSOIUFIPH-UHFFFAOYSA-N 0.000 claims 1
- SYUPKPLCMNYBDQ-UHFFFAOYSA-N 1-[4-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]-1,4-diazepan-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 SYUPKPLCMNYBDQ-UHFFFAOYSA-N 0.000 claims 1
- JMLMTGQITVTMNI-UHFFFAOYSA-N 1-[4-[3-[4-(pyridin-2-ylamino)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(NC=3N=CC=CC=3)=CC=2)=C1 JMLMTGQITVTMNI-UHFFFAOYSA-N 0.000 claims 1
- JMWAFGOLTQRKJH-UHFFFAOYSA-N 1-[4-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 JMWAFGOLTQRKJH-UHFFFAOYSA-N 0.000 claims 1
- BIIHYKHAFXFPRS-UHFFFAOYSA-N 1-[4-[3-[4-[(5-chloropyridin-2-yl)amino]phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(Cl)C=N1 BIIHYKHAFXFPRS-UHFFFAOYSA-N 0.000 claims 1
- MXJQNCCVEAHQCF-UHFFFAOYSA-N 1-[4-[3-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 MXJQNCCVEAHQCF-UHFFFAOYSA-N 0.000 claims 1
- VQDHXUDBUXSBEX-UHFFFAOYSA-N 1-methyl-3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclopentan-1-ol Chemical compound C1C(C)(O)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VQDHXUDBUXSBEX-UHFFFAOYSA-N 0.000 claims 1
- BKVOUJAANVLAER-UHFFFAOYSA-N 1-methyl-4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidin-2-one Chemical compound C1C(=O)N(C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 BKVOUJAANVLAER-UHFFFAOYSA-N 0.000 claims 1
- SUZRZWHGIGFGAM-UHFFFAOYSA-N 1-methyl-4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrrolidin-2-one Chemical compound C1C(=O)N(C)CC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 SUZRZWHGIGFGAM-UHFFFAOYSA-N 0.000 claims 1
- QBJYYCXHDUQBNM-UHFFFAOYSA-N 2,2,2-trifluoro-1-[4-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C(F)(F)F)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 QBJYYCXHDUQBNM-UHFFFAOYSA-N 0.000 claims 1
- RSVXVQYOXHXHSY-UHFFFAOYSA-N 2,5-dihydropyrrol-1-yl-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]methanone Chemical compound C=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1C(=O)N1CC=CC1 RSVXVQYOXHXHSY-UHFFFAOYSA-N 0.000 claims 1
- NLVNEPISTCEXEZ-UHFFFAOYSA-N 2-[1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidin-4-yl]propan-2-ol Chemical compound C1CC(C(C)(O)C)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NLVNEPISTCEXEZ-UHFFFAOYSA-N 0.000 claims 1
- BFMWYIYQFQLISR-UHFFFAOYSA-N 2-[1-[3-[4-(pyridin-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=CC=CC=N1 BFMWYIYQFQLISR-UHFFFAOYSA-N 0.000 claims 1
- ULMXCNUWTRIXHA-UHFFFAOYSA-N 2-[1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-3-yl]propan-2-ol Chemical compound C1C(C(C)(O)C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 ULMXCNUWTRIXHA-UHFFFAOYSA-N 0.000 claims 1
- GNZSCWCNWZHORF-UHFFFAOYSA-N 2-[4-(3-phenylpyridin-2-yl)oxyanilino]pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3C=CC=CC=3)=CC=2)=C1 GNZSCWCNWZHORF-UHFFFAOYSA-N 0.000 claims 1
- FODQRRJCTHATNT-UHFFFAOYSA-N 2-[4-(3-pyridin-4-ylpyridin-2-yl)oxyanilino]pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3C=CN=CC=3)=CC=2)=C1 FODQRRJCTHATNT-UHFFFAOYSA-N 0.000 claims 1
- UMINZWVDTVMQTI-UHFFFAOYSA-N 2-[4-(3-pyrimidin-4-ylpyridin-2-yl)oxyanilino]pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3N=CN=CC=3)=CC=2)=C1 UMINZWVDTVMQTI-UHFFFAOYSA-N 0.000 claims 1
- SPIALCGTKGNSOV-UHFFFAOYSA-N 2-[4-(pyridin-2-ylamino)phenoxy]pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 SPIALCGTKGNSOV-UHFFFAOYSA-N 0.000 claims 1
- LGGVIUMRKXGROF-UHFFFAOYSA-N 2-[4-(pyridin-2-ylamino)phenoxy]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 LGGVIUMRKXGROF-UHFFFAOYSA-N 0.000 claims 1
- IXXZWVVVDONLGV-UHFFFAOYSA-N 2-[4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 IXXZWVVVDONLGV-UHFFFAOYSA-N 0.000 claims 1
- DCCRFVUNVQAQGI-UHFFFAOYSA-N 2-[[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]amino]ethanol Chemical compound OCCNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 DCCRFVUNVQAQGI-UHFFFAOYSA-N 0.000 claims 1
- NNNWNIVDLPJMML-UHFFFAOYSA-N 2-fluoro-3-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]benzonitrile Chemical compound FC1=C(C#N)C=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NNNWNIVDLPJMML-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- SOOQDEQDWKSDPO-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 SOOQDEQDWKSDPO-UHFFFAOYSA-N 0.000 claims 1
- OBIWVFIYXKPNBD-UHFFFAOYSA-N 2-methoxy-1-[4-[3-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 OBIWVFIYXKPNBD-UHFFFAOYSA-N 0.000 claims 1
- QZBCULJJCAXKLK-UHFFFAOYSA-N 2-methyl-1-[4-[2-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyridin-3-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)C(C)C)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 QZBCULJJCAXKLK-UHFFFAOYSA-N 0.000 claims 1
- VRNXSNGKGWFHNQ-UHFFFAOYSA-N 2-methyl-1-[4-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)C(C)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VRNXSNGKGWFHNQ-UHFFFAOYSA-N 0.000 claims 1
- FARYSMHUCWCRNE-UHFFFAOYSA-N 2-methyl-1-[4-[3-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyrazin-2-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)C(C)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 FARYSMHUCWCRNE-UHFFFAOYSA-N 0.000 claims 1
- FMWOSHRUYNNLOT-UHFFFAOYSA-N 2-methyl-4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]but-3-yn-2-ol Chemical compound CC(C)(O)C#CC1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 FMWOSHRUYNNLOT-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- MJACPPVDWOZLFD-UHFFFAOYSA-N 3-(trifluoromethyl)-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CN=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C(F)(F)F MJACPPVDWOZLFD-UHFFFAOYSA-N 0.000 claims 1
- HVFCGKSCFUZRNX-UHFFFAOYSA-N 3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 HVFCGKSCFUZRNX-UHFFFAOYSA-N 0.000 claims 1
- GOTUFSIPQGIMRB-UHFFFAOYSA-N 3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclopent-2-en-1-one Chemical compound O=C1CCC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 GOTUFSIPQGIMRB-UHFFFAOYSA-N 0.000 claims 1
- YTSQJSLXKWSKBB-UHFFFAOYSA-N 3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclopentan-1-ol Chemical compound C1C(O)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YTSQJSLXKWSKBB-UHFFFAOYSA-N 0.000 claims 1
- FNRLXEOXNCVTIG-UHFFFAOYSA-N 3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]phenol Chemical compound OC1=CC=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 FNRLXEOXNCVTIG-UHFFFAOYSA-N 0.000 claims 1
- OOGYQLSCIDNKTJ-UHFFFAOYSA-N 3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 OOGYQLSCIDNKTJ-UHFFFAOYSA-N 0.000 claims 1
- IZYSNSZMIWDMFQ-UHFFFAOYSA-N 3-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 IZYSNSZMIWDMFQ-UHFFFAOYSA-N 0.000 claims 1
- XNBOEAQXKHKWRV-UHFFFAOYSA-N 3-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]phenol Chemical compound OC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 XNBOEAQXKHKWRV-UHFFFAOYSA-N 0.000 claims 1
- JJQQUTCMLCIDGF-UHFFFAOYSA-N 3-[4-(pyridin-2-ylamino)phenoxy]-n-(2-pyridin-2-ylethyl)pyrazin-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1NCCC1=CC=CC=N1 JJQQUTCMLCIDGF-UHFFFAOYSA-N 0.000 claims 1
- AVVJRFLLNMZKGB-UHFFFAOYSA-N 3-[4-(pyridin-2-ylamino)phenoxy]-n-(2-pyridin-3-ylethyl)pyrazin-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1NCCC1=CC=CN=C1 AVVJRFLLNMZKGB-UHFFFAOYSA-N 0.000 claims 1
- RTFGXNQXGCQXQL-UHFFFAOYSA-N 3-[4-(pyridin-2-ylamino)phenoxy]-n-(2-pyridin-4-ylethyl)pyrazin-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1NCCC1=CC=NC=C1 RTFGXNQXGCQXQL-UHFFFAOYSA-N 0.000 claims 1
- BLKVDSLXXIDWRS-UHFFFAOYSA-N 3-[4-(pyridin-2-ylamino)phenoxy]-n-(pyridin-2-ylmethyl)pyrazin-2-amine Chemical compound C=1C=CC=NC=1CNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 BLKVDSLXXIDWRS-UHFFFAOYSA-N 0.000 claims 1
- MRDJHMRIXGLWCX-UHFFFAOYSA-N 3-[4-(pyridin-2-ylamino)phenoxy]-n-(pyridin-3-ylmethyl)pyrazin-2-amine Chemical compound C=1C=CN=CC=1CNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MRDJHMRIXGLWCX-UHFFFAOYSA-N 0.000 claims 1
- UKDXZVUJBKOQRZ-UHFFFAOYSA-N 3-[4-(pyridin-2-ylamino)phenoxy]-n-(pyridin-4-ylmethyl)pyrazin-2-amine Chemical compound C=1C=NC=CC=1CNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 UKDXZVUJBKOQRZ-UHFFFAOYSA-N 0.000 claims 1
- GNYSQAGPXFMKMJ-UHFFFAOYSA-N 3-[4-(pyridin-2-ylamino)phenoxy]pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 GNYSQAGPXFMKMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims 1
- ATGKNHPWMWNWRQ-UHFFFAOYSA-N 3-fluoro-5-methyl-n-[4-(3-pyridin-4-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound FC1=CC(C)=CN=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=NC=C1 ATGKNHPWMWNWRQ-UHFFFAOYSA-N 0.000 claims 1
- CLUZVKYVJYIIJD-UHFFFAOYSA-N 3-fluoro-n-[4-(3-phenylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound FC1=CC=CN=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=CC=C1 CLUZVKYVJYIIJD-UHFFFAOYSA-N 0.000 claims 1
- AARQJTSTJLXWBA-UHFFFAOYSA-N 3-fluoro-n-[4-[3-(2-fluoropyridin-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(F)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3C(=CC=CN=3)F)=CC=2)=C1 AARQJTSTJLXWBA-UHFFFAOYSA-N 0.000 claims 1
- ODJBXQUBCORCAC-UHFFFAOYSA-N 3-fluoro-n-[4-[3-(2-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=NC=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC=CC=C1F ODJBXQUBCORCAC-UHFFFAOYSA-N 0.000 claims 1
- KZDALXNTKOJCBC-UHFFFAOYSA-N 3-fluoro-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC1=CC=CN=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 KZDALXNTKOJCBC-UHFFFAOYSA-N 0.000 claims 1
- ZTJMEDZSQNWSAN-UHFFFAOYSA-N 3-methyl-n-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound CC1=CC=CN=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 ZTJMEDZSQNWSAN-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- YYRUJULDGQSICL-UHFFFAOYSA-N 4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YYRUJULDGQSICL-UHFFFAOYSA-N 0.000 claims 1
- PRUBAUPIANPDBG-UHFFFAOYSA-N 4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 PRUBAUPIANPDBG-UHFFFAOYSA-N 0.000 claims 1
- HOSGJQOAQJHUCH-UHFFFAOYSA-N 4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]cyclohexan-1-one Chemical compound C1CC(=O)CCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 HOSGJQOAQJHUCH-UHFFFAOYSA-N 0.000 claims 1
- OCVMVBVXCCXQTE-UHFFFAOYSA-N 4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]oxan-4-ol Chemical compound C=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1C1(O)CCOCC1 OCVMVBVXCCXQTE-UHFFFAOYSA-N 0.000 claims 1
- KZIQTJUTZXQUJZ-UHFFFAOYSA-N 4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 KZIQTJUTZXQUJZ-UHFFFAOYSA-N 0.000 claims 1
- DPENAVGIUMMHFM-UHFFFAOYSA-N 4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]quinoline-7-carbonitrile Chemical compound C=1C=NC2=CC(C#N)=CC=C2C=1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 DPENAVGIUMMHFM-UHFFFAOYSA-N 0.000 claims 1
- LJLUWTGUWSOJSE-UHFFFAOYSA-N 4-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 LJLUWTGUWSOJSE-UHFFFAOYSA-N 0.000 claims 1
- CHOQKALQDARTHC-UHFFFAOYSA-N 4-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 CHOQKALQDARTHC-UHFFFAOYSA-N 0.000 claims 1
- ZYZUKUZTNRPCLM-UHFFFAOYSA-N 4-chloro-n-[4-(3-pyridin-4-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound ClC1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3C=CN=CC=3)=CC=2)=C1 ZYZUKUZTNRPCLM-UHFFFAOYSA-N 0.000 claims 1
- QEEOSIWNWGPPNQ-UHFFFAOYSA-N 4-chloro-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC(Cl)=CC=N1 QEEOSIWNWGPPNQ-UHFFFAOYSA-N 0.000 claims 1
- MREVXKNVUFFIIC-UHFFFAOYSA-N 4-fluoro-3-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]benzonitrile Chemical compound FC1=CC=C(C#N)C=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MREVXKNVUFFIIC-UHFFFAOYSA-N 0.000 claims 1
- NODDSMDTQVVEGK-UHFFFAOYSA-N 4-fluoro-n-[4-(3-pyrimidin-4-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound FC1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3N=CN=CC=3)=CC=2)=C1 NODDSMDTQVVEGK-UHFFFAOYSA-N 0.000 claims 1
- CGIAIDAOVGEVPI-UHFFFAOYSA-N 4-methyl-n-[4-(3-phenylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound CC1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3C=CC=CC=3)=CC=2)=C1 CGIAIDAOVGEVPI-UHFFFAOYSA-N 0.000 claims 1
- MLUJXNAYJXRYSP-UHFFFAOYSA-N 4-methyl-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound CC1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C(F)(F)F)=CC=2)=C1 MLUJXNAYJXRYSP-UHFFFAOYSA-N 0.000 claims 1
- JAACSJZZEXDPMW-UHFFFAOYSA-N 5-(morpholin-4-ylmethyl)-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CN=C1OC(C=C1)=CC=C1NC(N=C1)=CC=C1CN1CCOCC1 JAACSJZZEXDPMW-UHFFFAOYSA-N 0.000 claims 1
- AIWDORFNMVGMJD-UHFFFAOYSA-N 5-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 AIWDORFNMVGMJD-UHFFFAOYSA-N 0.000 claims 1
- MLPHXTOWKZZEIT-UHFFFAOYSA-N 5-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MLPHXTOWKZZEIT-UHFFFAOYSA-N 0.000 claims 1
- PLJLTHQUVASHMK-UHFFFAOYSA-N 5-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 PLJLTHQUVASHMK-UHFFFAOYSA-N 0.000 claims 1
- YGIYWCDJRHQTRG-UHFFFAOYSA-N 5-chloro-3-fluoro-n-[4-[3-(2-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=NC=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC=C(Cl)C=C1F YGIYWCDJRHQTRG-UHFFFAOYSA-N 0.000 claims 1
- KGKSRWCGHALRRF-UHFFFAOYSA-N 5-chloro-n-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound N1=CC(Cl)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 KGKSRWCGHALRRF-UHFFFAOYSA-N 0.000 claims 1
- OMTROKRCCUUCNC-UHFFFAOYSA-N 5-chloro-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(Cl)C=N1 OMTROKRCCUUCNC-UHFFFAOYSA-N 0.000 claims 1
- BQEITPRBALFOBQ-UHFFFAOYSA-N 5-ethyl-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound N1=CC(CC)=CC=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 BQEITPRBALFOBQ-UHFFFAOYSA-N 0.000 claims 1
- QJQUYSADPAQACR-UHFFFAOYSA-N 5-fluoro-3-methyl-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound CC1=CC(F)=CN=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C(F)(F)F QJQUYSADPAQACR-UHFFFAOYSA-N 0.000 claims 1
- RXYNCXQLCZANTO-UHFFFAOYSA-N 5-fluoro-n-[4-(3-pyridin-4-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound N1=CC(F)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=NC=C1 RXYNCXQLCZANTO-UHFFFAOYSA-N 0.000 claims 1
- JAVRQEODRDFCRN-UHFFFAOYSA-N 5-fluoro-n-[4-[3-(2-methylpyridin-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(C)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC(F)=CC=3)=CC=2)=C1 JAVRQEODRDFCRN-UHFFFAOYSA-N 0.000 claims 1
- NMXXKCZHCDXTAG-UHFFFAOYSA-N 5-methoxy-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound N1=CC(OC)=CC=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 NMXXKCZHCDXTAG-UHFFFAOYSA-N 0.000 claims 1
- MOALDTSEYGSILQ-UHFFFAOYSA-N 5-methyl-n-[4-[3-(1-methylsulfonylpiperidin-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound N1=CC(C)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1CCN(S(C)(=O)=O)CC1 MOALDTSEYGSILQ-UHFFFAOYSA-N 0.000 claims 1
- CUGDWPFDKZPNAJ-UHFFFAOYSA-N 5-methyl-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound N1=CC(C)=CC=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 CUGDWPFDKZPNAJ-UHFFFAOYSA-N 0.000 claims 1
- RDPSJUJEPIUILE-UHFFFAOYSA-N 5-methyl-n-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound N1=CC(C)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 RDPSJUJEPIUILE-UHFFFAOYSA-N 0.000 claims 1
- HLOIWKOQAQRBCC-UHFFFAOYSA-N 6-(trifluoromethyl)-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CC(NC=2C=CC(OC=3C(=CC=CN=3)C(F)(F)F)=CC=2)=N1 HLOIWKOQAQRBCC-UHFFFAOYSA-N 0.000 claims 1
- DFPYWSCIAGBUAT-UHFFFAOYSA-N 6-[(2-methylpropan-2-yl)oxy]-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound CC(C)(C)OC1=CC=CC(NC=2C=CC(OC=3C(=CC=CN=3)C(F)(F)F)=CC=2)=N1 DFPYWSCIAGBUAT-UHFFFAOYSA-N 0.000 claims 1
- MODNBKRMYUCIRR-UHFFFAOYSA-N 6-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyanilino]pyridine-3-carbonitrile Chemical compound N1=CC(C#N)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 MODNBKRMYUCIRR-UHFFFAOYSA-N 0.000 claims 1
- JEOMZJURSXBXMW-UHFFFAOYSA-N 6-methoxy-n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=CC=CC(NC=2C=CC(OC=3C(=CC=CN=3)C(F)(F)F)=CC=2)=N1 JEOMZJURSXBXMW-UHFFFAOYSA-N 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010008748 Chorea Diseases 0.000 claims 1
- 206010010219 Compulsions Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 206010034719 Personality change Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- CGLMOGQLNPWIFU-QGZVFWFLSA-N [(2r)-1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrrolidin-2-yl]methanol Chemical compound OC[C@H]1CCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 CGLMOGQLNPWIFU-QGZVFWFLSA-N 0.000 claims 1
- FIFPJHZEOCRFPJ-MRXNPFEDSA-N [(2r)-1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-2-yl]methanol Chemical compound OC[C@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 FIFPJHZEOCRFPJ-MRXNPFEDSA-N 0.000 claims 1
- CGLMOGQLNPWIFU-KRWDZBQOSA-N [(2s)-1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 CGLMOGQLNPWIFU-KRWDZBQOSA-N 0.000 claims 1
- FIFPJHZEOCRFPJ-INIZCTEOSA-N [(2s)-1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 FIFPJHZEOCRFPJ-INIZCTEOSA-N 0.000 claims 1
- SYIJBYVZCWPAAM-MRXNPFEDSA-N [(3r)-1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrrolidin-3-yl]methanol Chemical compound C1[C@H](CO)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 SYIJBYVZCWPAAM-MRXNPFEDSA-N 0.000 claims 1
- LPHDUFGYMDTZPU-OAHLLOKOSA-N [(3r)-1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-3-yl]methanol Chemical compound C1[C@H](CO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 LPHDUFGYMDTZPU-OAHLLOKOSA-N 0.000 claims 1
- SYIJBYVZCWPAAM-INIZCTEOSA-N [(3s)-1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrrolidin-3-yl]methanol Chemical compound C1[C@@H](CO)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 SYIJBYVZCWPAAM-INIZCTEOSA-N 0.000 claims 1
- LPHDUFGYMDTZPU-HNNXBMFYSA-N [(3s)-1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-3-yl]methanol Chemical compound C1[C@@H](CO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 LPHDUFGYMDTZPU-HNNXBMFYSA-N 0.000 claims 1
- FWEDJUOFXVKFDV-UHFFFAOYSA-N [1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 FWEDJUOFXVKFDV-UHFFFAOYSA-N 0.000 claims 1
- CEOWZGDETRETFE-UHFFFAOYSA-N [1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 CEOWZGDETRETFE-UHFFFAOYSA-N 0.000 claims 1
- GSUDKNFSKMKOHJ-UHFFFAOYSA-N [1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-2-yl]methanol Chemical compound OCC1CCCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 GSUDKNFSKMKOHJ-UHFFFAOYSA-N 0.000 claims 1
- WREKRZIPQYUDOD-UHFFFAOYSA-N [1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 WREKRZIPQYUDOD-UHFFFAOYSA-N 0.000 claims 1
- MXBCYVAFJBFGKW-UHFFFAOYSA-N [2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]-(1,3-thiazolidin-3-yl)methanone Chemical compound C=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1C(=O)N1CCSC1 MXBCYVAFJBFGKW-UHFFFAOYSA-N 0.000 claims 1
- LTPOACJAKSJFPB-UHFFFAOYSA-N [2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]-[3-[3-(trifluoromethyl)phenoxy]azetidin-1-yl]methanone Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 LTPOACJAKSJFPB-UHFFFAOYSA-N 0.000 claims 1
- WXIPXKBERUARNQ-UHFFFAOYSA-N [2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1C(=O)N1CCCC1 WXIPXKBERUARNQ-UHFFFAOYSA-N 0.000 claims 1
- VWZHTHKFPWBMSB-UHFFFAOYSA-N [3-(4-chlorophenoxy)azetidin-1-yl]-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]methanone Chemical compound C1=CC(Cl)=CC=C1OC1CN(C(=O)C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C1 VWZHTHKFPWBMSB-UHFFFAOYSA-N 0.000 claims 1
- WDQIABDPPBTPTL-UHFFFAOYSA-N [3-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]phenyl]methanol Chemical compound OCC1=CC=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 WDQIABDPPBTPTL-UHFFFAOYSA-N 0.000 claims 1
- OAFYTJIKNKPOSC-UHFFFAOYSA-N [3-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]phenyl]methanol Chemical compound OCC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 OAFYTJIKNKPOSC-UHFFFAOYSA-N 0.000 claims 1
- COMCORKQVOAQLV-UHFFFAOYSA-N [4-(3-chloropyrazin-2-yl)oxyphenyl]-pyridin-2-ylmethanone Chemical compound ClC1=NC=CN=C1OC1=CC=C(C(=O)C=2N=CC=CC=2)C=C1 COMCORKQVOAQLV-UHFFFAOYSA-N 0.000 claims 1
- FBQOKHKWNUUTHG-UHFFFAOYSA-N [4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-pyridin-2-ylmethanone Chemical compound C=1C=CC=NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 FBQOKHKWNUUTHG-UHFFFAOYSA-N 0.000 claims 1
- DMIXVMKHTQBPGM-UHFFFAOYSA-N [4-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]oxyphenyl]-pyridin-2-ylmethanone Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2N=CC=CC=2)=C1 DMIXVMKHTQBPGM-UHFFFAOYSA-N 0.000 claims 1
- ULWPBJCVQMSIRT-UHFFFAOYSA-N [4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]-pyridin-2-ylmethanone Chemical compound C=1C=CC=NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1CCOCC1 ULWPBJCVQMSIRT-UHFFFAOYSA-N 0.000 claims 1
- OQWHVLHQKZBAIA-KRWDZBQOSA-N [4-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]-pyridin-2-ylmethanone Chemical compound COC[C@@H]1CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N=CC=CC=2)C=C1 OQWHVLHQKZBAIA-KRWDZBQOSA-N 0.000 claims 1
- VXRLSNNZLSOQSI-UHFFFAOYSA-N [4-[3-[4-(2-hydroxyethyl)piperazin-1-yl]pyrazin-2-yl]oxyphenyl]-pyridin-2-ylmethanone Chemical compound C1CN(CCO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N=CC=CC=2)C=C1 VXRLSNNZLSOQSI-UHFFFAOYSA-N 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- PJWFTRKZYKEGCB-UHFFFAOYSA-N azetidin-1-yl-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]methanone Chemical compound C=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1C(=O)N1CCC1 PJWFTRKZYKEGCB-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 208000012601 choreatic disease Diseases 0.000 claims 1
- 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 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 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 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- PPPYSZLHBZXEOE-UHFFFAOYSA-N cyclopropyl-[4-[3-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyrazin-2-yl]piperidin-1-yl]methanone Chemical compound N1=CC(C)=CC=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCN(C(=O)C2CC2)CC1 PPPYSZLHBZXEOE-UHFFFAOYSA-N 0.000 claims 1
- 125000005959 diazepanyl group Chemical group 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 1
- LRTRDJKXHRFEJI-UHFFFAOYSA-N ethyl 1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 LRTRDJKXHRFEJI-UHFFFAOYSA-N 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005394 methallyl group Chemical group 0.000 claims 1
- DYYQZFYPGAOIDP-UHFFFAOYSA-N methyl 1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 DYYQZFYPGAOIDP-UHFFFAOYSA-N 0.000 claims 1
- NGTCMRXABCXPKB-UHFFFAOYSA-N methyl 1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OC)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NGTCMRXABCXPKB-UHFFFAOYSA-N 0.000 claims 1
- ZSEKMSKLSQNRSU-UHFFFAOYSA-N methyl 1-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidine-3-carboxylate Chemical compound C1C(C(=O)OC)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 ZSEKMSKLSQNRSU-UHFFFAOYSA-N 0.000 claims 1
- QCQONIKODKIMCO-UHFFFAOYSA-N methyl 4-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 QCQONIKODKIMCO-UHFFFAOYSA-N 0.000 claims 1
- IPPBPLNONHESMQ-UHFFFAOYSA-N methyl 4-[3-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyrazin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 IPPBPLNONHESMQ-UHFFFAOYSA-N 0.000 claims 1
- 230000002969 morbid Effects 0.000 claims 1
- VFMWMJGKMIXIDP-UHFFFAOYSA-N n',n'-dimethyl-2-[4-(pyridin-2-ylamino)phenoxy]pyridine-3-carbohydrazide Chemical compound CN(C)NC(=O)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VFMWMJGKMIXIDP-UHFFFAOYSA-N 0.000 claims 1
- SKONCKVWSYBQFX-UHFFFAOYSA-N n-(1-benzylcyclopropyl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazine-2-carboxamide Chemical compound N=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1C(=O)NC1(CC=2C=CC=CC=2)CC1 SKONCKVWSYBQFX-UHFFFAOYSA-N 0.000 claims 1
- QATOLQPRBYHATE-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazine-2-carboxamide Chemical compound OCCNC(=O)C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 QATOLQPRBYHATE-UHFFFAOYSA-N 0.000 claims 1
- UGOYLDLWHYTYLC-UHFFFAOYSA-N n-(2-methoxyethyl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound COCCNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 UGOYLDLWHYTYLC-UHFFFAOYSA-N 0.000 claims 1
- KXRMXTHGJCSVAW-UHFFFAOYSA-N n-(2-methylpropyl)-2-[4-(pyridin-2-ylamino)phenoxy]pyridine-3-carboxamide Chemical compound CC(C)CNC(=O)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 KXRMXTHGJCSVAW-UHFFFAOYSA-N 0.000 claims 1
- BTEQBLZHCLSRGE-UHFFFAOYSA-N n-(2-methylpropyl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound CC(C)CNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 BTEQBLZHCLSRGE-UHFFFAOYSA-N 0.000 claims 1
- GPEIANYLEYGJDE-UHFFFAOYSA-N n-(2-phenylethyl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1NCCC1=CC=CC=C1 GPEIANYLEYGJDE-UHFFFAOYSA-N 0.000 claims 1
- QHNXQDBGQQVWGT-UHFFFAOYSA-N n-(2-piperidin-1-ylethyl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1NCCN1CCCCC1 QHNXQDBGQQVWGT-UHFFFAOYSA-N 0.000 claims 1
- AIVRICGHIVKXLZ-UHFFFAOYSA-N n-(4-pyrazin-2-yloxyphenyl)pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=CN=CC=N1 AIVRICGHIVKXLZ-UHFFFAOYSA-N 0.000 claims 1
- GLTISMKGQAZAKU-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound C1CC1CNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 GLTISMKGQAZAKU-UHFFFAOYSA-N 0.000 claims 1
- XJXVLWGMXTXAKQ-UHFFFAOYSA-N n-(oxan-4-yl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound C1COCCC1NC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 XJXVLWGMXTXAKQ-UHFFFAOYSA-N 0.000 claims 1
- VVSYHEGYISRUIN-UHFFFAOYSA-N n-(oxolan-3-yl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound C1OCCC1NC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VVSYHEGYISRUIN-UHFFFAOYSA-N 0.000 claims 1
- KACUOAXJJTUXOH-UHFFFAOYSA-N n-(piperidin-4-ylmethyl)-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound C1CNCCC1CNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 KACUOAXJJTUXOH-UHFFFAOYSA-N 0.000 claims 1
- FXFIHRXDRFMUDB-UHFFFAOYSA-N n-[2-fluoro-4-[3-(2-fluoropyridin-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(F)=CC(C=2C(=NC=CN=2)OC=2C=C(F)C(NC=3N=CC=CC=3)=CC=2)=C1 FXFIHRXDRFMUDB-UHFFFAOYSA-N 0.000 claims 1
- FLGSYQDCLVWROB-UHFFFAOYSA-N n-[2-fluoro-4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1F)=CC=C1NC1=CC=CC=N1 FLGSYQDCLVWROB-UHFFFAOYSA-N 0.000 claims 1
- BVZWZSBZWRSAIS-UHFFFAOYSA-N n-[2-fluoro-4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(NC=2N=CC=CC=2)C(F)=CC=1OC1=NC=CN=C1C1CCOCC1 BVZWZSBZWRSAIS-UHFFFAOYSA-N 0.000 claims 1
- KXQZFJHYULQDOX-UHFFFAOYSA-N n-[4-(3-benzylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C=1CC1=CC=CC=C1 KXQZFJHYULQDOX-UHFFFAOYSA-N 0.000 claims 1
- QSMBDCSSADAFTO-UHFFFAOYSA-N n-[4-(3-cyclohexylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CCCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 QSMBDCSSADAFTO-UHFFFAOYSA-N 0.000 claims 1
- VMHICSKJDAGROO-UHFFFAOYSA-N n-[4-(3-cyclopentylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VMHICSKJDAGROO-UHFFFAOYSA-N 0.000 claims 1
- NSUFIEDRLXRAPK-UHFFFAOYSA-N n-[4-(3-cyclopentylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NSUFIEDRLXRAPK-UHFFFAOYSA-N 0.000 claims 1
- FSNPNYLOTUHRKH-UHFFFAOYSA-N n-[4-(3-cyclopropylpyridin-2-yl)oxyphenyl]-3-fluoro-5-methylpyridin-2-amine Chemical compound FC1=CC(C)=CN=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1CC1 FSNPNYLOTUHRKH-UHFFFAOYSA-N 0.000 claims 1
- WPADOIWBNDOXLF-UHFFFAOYSA-N n-[4-(3-isoquinolin-5-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(OC=2C(=NC=CN=2)C=2C3=CC=NC=C3C=CC=2)C=CC=1NC1=CC=CC=N1 WPADOIWBNDOXLF-UHFFFAOYSA-N 0.000 claims 1
- GHVPHZMCQNSHFW-UHFFFAOYSA-N n-[4-(3-isoquinolin-5-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(OC=2C(=CC=CN=2)C=2C3=CC=NC=C3C=CC=2)C=CC=1NC1=CC=CC=N1 GHVPHZMCQNSHFW-UHFFFAOYSA-N 0.000 claims 1
- VGCLMLVSRISONU-UHFFFAOYSA-N n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1COCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VGCLMLVSRISONU-UHFFFAOYSA-N 0.000 claims 1
- BIQNAKZOAJGBDF-UHFFFAOYSA-N n-[4-(3-naphthalen-1-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(OC=2C(=NC=CN=2)C=2C3=CC=CC=C3C=CC=2)C=CC=1NC1=CC=CC=N1 BIQNAKZOAJGBDF-UHFFFAOYSA-N 0.000 claims 1
- BDLNOBIWFLKESC-UHFFFAOYSA-N n-[4-(3-phenylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CC=C1 BDLNOBIWFLKESC-UHFFFAOYSA-N 0.000 claims 1
- XWZNMOLWONEQNQ-UHFFFAOYSA-N n-[4-(3-phenylpyridin-2-yl)oxyphenyl]-4-(trifluoromethyl)pyridin-2-amine Chemical compound FC(F)(F)C1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3C=CC=CC=3)=CC=2)=C1 XWZNMOLWONEQNQ-UHFFFAOYSA-N 0.000 claims 1
- JBLITTKKJNUABI-UHFFFAOYSA-N n-[4-(3-phenylpyridin-2-yl)oxyphenyl]-5-(trifluoromethyl)pyridin-2-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=CC=C1 JBLITTKKJNUABI-UHFFFAOYSA-N 0.000 claims 1
- WXIBVYHNQSLJMN-UHFFFAOYSA-N n-[4-(3-phenylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=CC=C1 WXIBVYHNQSLJMN-UHFFFAOYSA-N 0.000 claims 1
- QJLBJXFDKCOIED-UHFFFAOYSA-N n-[4-(3-piperazin-1-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CNCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 QJLBJXFDKCOIED-UHFFFAOYSA-N 0.000 claims 1
- NYRFJXOBUPFYBG-UHFFFAOYSA-N n-[4-(3-piperidin-1-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CCCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NYRFJXOBUPFYBG-UHFFFAOYSA-N 0.000 claims 1
- MEMRLRMKYOCWSK-UHFFFAOYSA-N n-[4-(3-piperidin-1-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CCCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MEMRLRMKYOCWSK-UHFFFAOYSA-N 0.000 claims 1
- AWZGBLGLZBIAGX-UHFFFAOYSA-N n-[4-(3-piperidin-4-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CNCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 AWZGBLGLZBIAGX-UHFFFAOYSA-N 0.000 claims 1
- YFJZZLDKHIQQQH-UHFFFAOYSA-N n-[4-(3-pyridin-3-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=CN=C1 YFJZZLDKHIQQQH-UHFFFAOYSA-N 0.000 claims 1
- RFGOJFDMXXDVHC-UHFFFAOYSA-N n-[4-(3-pyridin-4-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=NC=C1 RFGOJFDMXXDVHC-UHFFFAOYSA-N 0.000 claims 1
- RCPSOGCIFCTQKG-UHFFFAOYSA-N n-[4-(3-pyridin-4-ylpyridin-2-yl)oxyphenyl]-4-(trifluoromethyl)pyridin-2-amine Chemical compound FC(F)(F)C1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3C=CN=CC=3)=CC=2)=C1 RCPSOGCIFCTQKG-UHFFFAOYSA-N 0.000 claims 1
- JEKVYTJPEIHSFF-UHFFFAOYSA-N n-[4-(3-pyridin-4-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=NC=C1 JEKVYTJPEIHSFF-UHFFFAOYSA-N 0.000 claims 1
- ZMEVCFJFTBJUNK-UHFFFAOYSA-N n-[4-(3-pyridin-4-ylpyridin-2-yl)oxyphenyl]quinolin-2-amine Chemical compound C=1C=C2C=CC=CC2=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=NC=C1 ZMEVCFJFTBJUNK-UHFFFAOYSA-N 0.000 claims 1
- FAPSQNXQJXQPMT-UHFFFAOYSA-N n-[4-(3-pyrimidin-4-ylpyridin-2-yl)oxyphenyl]-4-(trifluoromethyl)pyridin-2-amine Chemical compound FC(F)(F)C1=CC=NC(NC=2C=CC(OC=3C(=CC=CN=3)C=3N=CN=CC=3)=CC=2)=C1 FAPSQNXQJXQPMT-UHFFFAOYSA-N 0.000 claims 1
- RGQUCNBSUPMXAX-UHFFFAOYSA-N n-[4-(3-pyrimidin-4-ylpyridin-2-yl)oxyphenyl]-5-(trifluoromethyl)pyridin-2-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=NC=N1 RGQUCNBSUPMXAX-UHFFFAOYSA-N 0.000 claims 1
- QRCOJBWGNFFJTP-UHFFFAOYSA-N n-[4-(3-pyrimidin-4-ylpyridin-2-yl)oxyphenyl]-6-(trifluoromethyl)pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CC(NC=2C=CC(OC=3C(=CC=CN=3)C=3N=CN=CC=3)=CC=2)=N1 QRCOJBWGNFFJTP-UHFFFAOYSA-N 0.000 claims 1
- VXFGFZRXADIAEG-UHFFFAOYSA-N n-[4-(3-pyrimidin-4-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=NC=N1 VXFGFZRXADIAEG-UHFFFAOYSA-N 0.000 claims 1
- MHUCRBALVIICPI-UHFFFAOYSA-N n-[4-(3-pyrimidin-5-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CN=CN=C1 MHUCRBALVIICPI-UHFFFAOYSA-N 0.000 claims 1
- HCFFDQNXNAEGCV-UHFFFAOYSA-N n-[4-(3-pyrimidin-5-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CN=CN=C1 HCFFDQNXNAEGCV-UHFFFAOYSA-N 0.000 claims 1
- CMQJIEOYOVEUAB-UHFFFAOYSA-N n-[4-(3-pyrrolidin-1-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 CMQJIEOYOVEUAB-UHFFFAOYSA-N 0.000 claims 1
- PXEVDDDOJWZTFR-UHFFFAOYSA-N n-[4-(3-pyrrolidin-1-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C1CCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 PXEVDDDOJWZTFR-UHFFFAOYSA-N 0.000 claims 1
- XNVDKMFUWXXKPB-UHFFFAOYSA-N n-[4-(3-quinolin-4-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(OC=2C(=NC=CN=2)C=2C3=CC=CC=C3N=CC=2)C=CC=1NC1=CC=CC=N1 XNVDKMFUWXXKPB-UHFFFAOYSA-N 0.000 claims 1
- JWBYTLIHXIXHFZ-UHFFFAOYSA-N n-[4-(3-quinolin-4-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(OC=2C(=CC=CN=2)C=2C3=CC=CC=C3N=CC=2)C=CC=1NC1=CC=CC=N1 JWBYTLIHXIXHFZ-UHFFFAOYSA-N 0.000 claims 1
- HGEDTONSABSXLZ-UHFFFAOYSA-N n-[4-(3-quinolin-5-ylpyrazin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(OC=2C(=NC=CN=2)C=2C3=CC=CN=C3C=CC=2)C=CC=1NC1=CC=CC=N1 HGEDTONSABSXLZ-UHFFFAOYSA-N 0.000 claims 1
- PZMOAQJHMKVTCJ-UHFFFAOYSA-N n-[4-(3-quinolin-5-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(OC=2C(=CC=CN=2)C=2C3=CC=CN=C3C=CC=2)C=CC=1NC1=CC=CC=N1 PZMOAQJHMKVTCJ-UHFFFAOYSA-N 0.000 claims 1
- LTLDTSWFPOCDLW-UHFFFAOYSA-N n-[4-(3-thiophen-3-ylpyridin-2-yl)oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C=1C=CSC=1 LTLDTSWFPOCDLW-UHFFFAOYSA-N 0.000 claims 1
- ZXODMHLTAJWMHW-UHFFFAOYSA-N n-[4-[3-(1,3-benzodioxol-5-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=C2OCOC2=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 ZXODMHLTAJWMHW-UHFFFAOYSA-N 0.000 claims 1
- HAYCEKVXLJCWSW-UHFFFAOYSA-N n-[4-[3-(1,4-oxazepan-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCOCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 HAYCEKVXLJCWSW-UHFFFAOYSA-N 0.000 claims 1
- VQARPLYWKHOQFM-UHFFFAOYSA-N n-[4-[3-(1-benzothiophen-7-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C=1C=C(OC=2C(=NC=CN=2)C=2C=3SC=CC=3C=CC=2)C=CC=1NC1=CC=CC=N1 VQARPLYWKHOQFM-UHFFFAOYSA-N 0.000 claims 1
- VKAAYQKQIWOSFC-UHFFFAOYSA-N n-[4-[3-(1-methylpyrazol-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NN(C)C=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 VKAAYQKQIWOSFC-UHFFFAOYSA-N 0.000 claims 1
- IWZHGAPOISFNPW-UHFFFAOYSA-N n-[4-[3-(1-methylsulfonylpiperidin-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 IWZHGAPOISFNPW-UHFFFAOYSA-N 0.000 claims 1
- CSCVNSBTZJACSI-UHFFFAOYSA-N n-[4-[3-(1-piperidin-4-ylpyrazol-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CNCCC1N1N=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 CSCVNSBTZJACSI-UHFFFAOYSA-N 0.000 claims 1
- GKHQJLQGFWMHKW-UHFFFAOYSA-N n-[4-[3-(1h-pyrazol-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1C=1C=NNC=1 GKHQJLQGFWMHKW-UHFFFAOYSA-N 0.000 claims 1
- WZVFZAYRVSYWTJ-UHFFFAOYSA-N n-[4-[3-(2,3-dihydrofuran-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1OC=CC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 WZVFZAYRVSYWTJ-UHFFFAOYSA-N 0.000 claims 1
- QMRRPCBYJHVKFM-UHFFFAOYSA-N n-[4-[3-(2,6-dimethylmorpholin-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1C(C)OC(C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 QMRRPCBYJHVKFM-UHFFFAOYSA-N 0.000 claims 1
- SPCPWLJUPQKRSH-UHFFFAOYSA-N n-[4-[3-(2-chloropyridin-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(Cl)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 SPCPWLJUPQKRSH-UHFFFAOYSA-N 0.000 claims 1
- SWOBIOUUDOXMFM-UHFFFAOYSA-N n-[4-[3-(2-fluoropyridin-4-yl)-6-methoxypyridin-2-yl]oxyphenyl]-5-methylpyridin-2-amine Chemical compound N=1C(OC)=CC=C(C=2C=C(F)N=CC=2)C=1OC(C=C1)=CC=C1NC1=CC=C(C)C=N1 SWOBIOUUDOXMFM-UHFFFAOYSA-N 0.000 claims 1
- NMOSIKNIMSJPAY-UHFFFAOYSA-N n-[4-[3-(2-fluoropyridin-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(F)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 NMOSIKNIMSJPAY-UHFFFAOYSA-N 0.000 claims 1
- RNCFJBHEJLHXRO-UHFFFAOYSA-N n-[4-[3-(2-fluoropyridin-4-yl)pyridin-2-yl]oxyphenyl]-5-methylpyridin-2-amine Chemical compound N1=CC(C)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CC=NC(F)=C1 RNCFJBHEJLHXRO-UHFFFAOYSA-N 0.000 claims 1
- YPJCWOMXMMRMFT-UHFFFAOYSA-N n-[4-[3-(2-fluoropyridin-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(F)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 YPJCWOMXMMRMFT-UHFFFAOYSA-N 0.000 claims 1
- YUGLENOKOORRBI-UHFFFAOYSA-N n-[4-[3-(2-methoxyphenyl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=CC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YUGLENOKOORRBI-UHFFFAOYSA-N 0.000 claims 1
- KTLHWJMWJVXLSJ-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 KTLHWJMWJVXLSJ-UHFFFAOYSA-N 0.000 claims 1
- LEORVLZLCOYRDC-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=NC=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 LEORVLZLCOYRDC-UHFFFAOYSA-N 0.000 claims 1
- ANBTWORMKYOQHP-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(OC)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 ANBTWORMKYOQHP-UHFFFAOYSA-N 0.000 claims 1
- BUSTUSMUWONVMV-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-4-yl)pyridin-2-yl]oxyphenyl]-5-methylpyridin-2-amine Chemical compound C1=NC(OC)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC(C)=CC=3)=CC=2)=C1 BUSTUSMUWONVMV-UHFFFAOYSA-N 0.000 claims 1
- NNGQJZZBQQNMCU-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(OC)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 NNGQJZZBQQNMCU-UHFFFAOYSA-N 0.000 claims 1
- PDCMTRVXJKBSPY-UHFFFAOYSA-N n-[4-[3-(2-methoxypyrimidin-5-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(OC)=NC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 PDCMTRVXJKBSPY-UHFFFAOYSA-N 0.000 claims 1
- UBHCRVBISXFJLC-UHFFFAOYSA-N n-[4-[3-(2-methoxypyrimidin-5-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(OC)=NC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 UBHCRVBISXFJLC-UHFFFAOYSA-N 0.000 claims 1
- NVGZRMWZEVOUCJ-UHFFFAOYSA-N n-[4-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 NVGZRMWZEVOUCJ-UHFFFAOYSA-N 0.000 claims 1
- KLERZVPFJZYSPR-UHFFFAOYSA-N n-[4-[3-(3,4-difluorophenyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=C(F)C(F)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 KLERZVPFJZYSPR-UHFFFAOYSA-N 0.000 claims 1
- TXWKQMNKIMKSIN-UHFFFAOYSA-N n-[4-[3-(3,5-difluorophenyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC1=CC(F)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 TXWKQMNKIMKSIN-UHFFFAOYSA-N 0.000 claims 1
- LKRLWOUBDSBGSW-UHFFFAOYSA-N n-[4-[3-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1OCCC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 LKRLWOUBDSBGSW-UHFFFAOYSA-N 0.000 claims 1
- BULUPOQOGRCIHU-UHFFFAOYSA-N n-[4-[3-(3-aminophenyl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound NC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 BULUPOQOGRCIHU-UHFFFAOYSA-N 0.000 claims 1
- UZLARABOCGMYRF-UHFFFAOYSA-N n-[4-[3-(3-benzylpiperidin-1-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C=1C=CC=CC=1CC(C1)CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 UZLARABOCGMYRF-UHFFFAOYSA-N 0.000 claims 1
- RDJLMJVDLKEBCV-UHFFFAOYSA-N n-[4-[3-(3-chlorophenyl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound ClC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 RDJLMJVDLKEBCV-UHFFFAOYSA-N 0.000 claims 1
- OKUFJLFRHXRITE-UHFFFAOYSA-N n-[4-[3-(3-fluoro-4-methoxyphenyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=C(F)C(OC)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 OKUFJLFRHXRITE-UHFFFAOYSA-N 0.000 claims 1
- ZFHDKSUMFHBGGN-UHFFFAOYSA-N n-[4-[3-(3-fluorophenyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC1=CC=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 ZFHDKSUMFHBGGN-UHFFFAOYSA-N 0.000 claims 1
- UTKRXCMUVUJFQR-UHFFFAOYSA-N n-[4-[3-(3-methoxyphenyl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 UTKRXCMUVUJFQR-UHFFFAOYSA-N 0.000 claims 1
- OXPQNZRTSXRDJO-UHFFFAOYSA-N n-[4-[3-(3-methoxyphenyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=CC=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 OXPQNZRTSXRDJO-UHFFFAOYSA-N 0.000 claims 1
- DLPJCNPCQOZYSG-UHFFFAOYSA-N n-[4-[3-(3-methoxyprop-1-ynyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COCC#CC1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 DLPJCNPCQOZYSG-UHFFFAOYSA-N 0.000 claims 1
- BIJRQAJTQOQURV-UHFFFAOYSA-N n-[4-[3-(3-methoxypyrrolidin-1-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1C(OC)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 BIJRQAJTQOQURV-UHFFFAOYSA-N 0.000 claims 1
- XPXUTXOVECJRLO-UHFFFAOYSA-N n-[4-[3-(3-methylbenzimidazol-5-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=C2N(C)C=NC2=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 XPXUTXOVECJRLO-UHFFFAOYSA-N 0.000 claims 1
- HNQHCKMGLBRMHD-UHFFFAOYSA-N n-[4-[3-(3-methylbut-1-ynyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound CC(C)C#CC1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 HNQHCKMGLBRMHD-UHFFFAOYSA-N 0.000 claims 1
- BJCDASRNRFSOQH-UHFFFAOYSA-N n-[4-[3-(3-methylphenyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound CC1=CC=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 BJCDASRNRFSOQH-UHFFFAOYSA-N 0.000 claims 1
- LFAJKDIAHPIKQU-UHFFFAOYSA-N n-[4-[3-(4-aminophenyl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=CC(N)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 LFAJKDIAHPIKQU-UHFFFAOYSA-N 0.000 claims 1
- JESBZCAQJXTNOI-UHFFFAOYSA-N n-[4-[3-(4-methoxyphenyl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 JESBZCAQJXTNOI-UHFFFAOYSA-N 0.000 claims 1
- MNTYFWHTXICFST-UHFFFAOYSA-N n-[4-[3-(4-methoxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CC(OC)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MNTYFWHTXICFST-UHFFFAOYSA-N 0.000 claims 1
- RVWNRDACMZDRFF-UHFFFAOYSA-N n-[4-[3-(4-methoxypiperidin-1-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CC(OC)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 RVWNRDACMZDRFF-UHFFFAOYSA-N 0.000 claims 1
- LQHXAEDJABEEMB-UHFFFAOYSA-N n-[4-[3-(4-methylpiperazin-1-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CN(C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 LQHXAEDJABEEMB-UHFFFAOYSA-N 0.000 claims 1
- IJMZXIAUXUQOHH-UHFFFAOYSA-N n-[4-[3-(4-methylpiperazin-1-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 IJMZXIAUXUQOHH-UHFFFAOYSA-N 0.000 claims 1
- RJFNIIKGJMCONL-UHFFFAOYSA-N n-[4-[3-(4-methylsulfanylphenyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=CC(SC)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 RJFNIIKGJMCONL-UHFFFAOYSA-N 0.000 claims 1
- SYPRUTYFIWALKZ-UHFFFAOYSA-N n-[4-[3-(5-fluoropyridin-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC1=CN=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 SYPRUTYFIWALKZ-UHFFFAOYSA-N 0.000 claims 1
- NZXCUBHPNOCKLM-UHFFFAOYSA-N n-[4-[3-(5-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC1=CN=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 NZXCUBHPNOCKLM-UHFFFAOYSA-N 0.000 claims 1
- XONHAZVYOHESQX-UHFFFAOYSA-N n-[4-[3-(6-methoxypyridin-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 XONHAZVYOHESQX-UHFFFAOYSA-N 0.000 claims 1
- IHZGJAVXGFPBDV-UHFFFAOYSA-N n-[4-[3-(7-chloroquinolin-4-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C=1C=NC2=CC(Cl)=CC=C2C=1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 IHZGJAVXGFPBDV-UHFFFAOYSA-N 0.000 claims 1
- WDKPPBMVOAQLJN-UHFFFAOYSA-N n-[4-[3-(cyclohexen-1-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCCC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 WDKPPBMVOAQLJN-UHFFFAOYSA-N 0.000 claims 1
- WHDJFLOVWHDHGF-UHFFFAOYSA-N n-[4-[3-(cyclohexen-1-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCCC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 WHDJFLOVWHDHGF-UHFFFAOYSA-N 0.000 claims 1
- WEYSNSOMQDWFBM-UHFFFAOYSA-N n-[4-[3-(cyclopenten-1-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 WEYSNSOMQDWFBM-UHFFFAOYSA-N 0.000 claims 1
- BUVDJQJAMKBNLQ-UHFFFAOYSA-N n-[4-[3-(cyclopenten-1-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCC=C1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 BUVDJQJAMKBNLQ-UHFFFAOYSA-N 0.000 claims 1
- WWILKHSKXXLPET-UHFFFAOYSA-N n-[4-[3-(oxan-2-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound O1CCCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 WWILKHSKXXLPET-UHFFFAOYSA-N 0.000 claims 1
- ACFWAHLCVSJSCO-UHFFFAOYSA-N n-[4-[3-(oxan-3-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCOCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 ACFWAHLCVSJSCO-UHFFFAOYSA-N 0.000 claims 1
- WKCXWIVGOHAMBX-UHFFFAOYSA-N n-[4-[3-(oxan-3-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCOCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 WKCXWIVGOHAMBX-UHFFFAOYSA-N 0.000 claims 1
- CARMOOUIIUZNBC-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-5-(trifluoromethyl)pyridin-2-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 CARMOOUIIUZNBC-UHFFFAOYSA-N 0.000 claims 1
- GTWGRJLOIYHLBU-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1COCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 GTWGRJLOIYHLBU-UHFFFAOYSA-N 0.000 claims 1
- XOIHSRVBLLNXMV-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyridin-2-yl]oxyphenyl]quinolin-2-amine Chemical compound C1COCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=C(C=CC=C2)C2=N1 XOIHSRVBLLNXMV-UHFFFAOYSA-N 0.000 claims 1
- OUOCOSQUTDTFOI-UHFFFAOYSA-N n-[4-[3-(oxepan-4-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCOCCC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 OUOCOSQUTDTFOI-UHFFFAOYSA-N 0.000 claims 1
- NWENMUHTOLTNBS-UHFFFAOYSA-N n-[4-[3-(oxolan-2-yl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CCOC1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 NWENMUHTOLTNBS-UHFFFAOYSA-N 0.000 claims 1
- MIZWBKPBMVJMHT-UHFFFAOYSA-N n-[4-[3-(oxolan-3-yl)pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1OCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MIZWBKPBMVJMHT-UHFFFAOYSA-N 0.000 claims 1
- YHOXMEJFWFWHFV-UHFFFAOYSA-N n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YHOXMEJFWFWHFV-UHFFFAOYSA-N 0.000 claims 1
- NFSJLPVJPXJJDY-UHFFFAOYSA-N n-[4-[3-(trifluoromethyl)pyridin-2-yl]oxyphenyl]pyrimidin-2-amine Chemical compound FC(F)(F)C1=CC=CN=C1OC(C=C1)=CC=C1NC1=NC=CC=N1 NFSJLPVJPXJJDY-UHFFFAOYSA-N 0.000 claims 1
- AASLCDOOIGQBAC-QHCPKHFHSA-N n-[4-[3-[(2r)-2-(4-methoxyphenyl)morpholin-4-yl]pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1[C@H]1OCCN(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C1 AASLCDOOIGQBAC-QHCPKHFHSA-N 0.000 claims 1
- YUZBHYHIGQXOMZ-QGZVFWFLSA-N n-[4-[3-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC[C@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YUZBHYHIGQXOMZ-QGZVFWFLSA-N 0.000 claims 1
- AASLCDOOIGQBAC-HSZRJFAPSA-N n-[4-[3-[(2s)-2-(4-methoxyphenyl)morpholin-4-yl]pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1[C@@H]1OCCN(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)C1 AASLCDOOIGQBAC-HSZRJFAPSA-N 0.000 claims 1
- YUZBHYHIGQXOMZ-KRWDZBQOSA-N n-[4-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 YUZBHYHIGQXOMZ-KRWDZBQOSA-N 0.000 claims 1
- SSCIGRNQLSIHHI-SFHVURJKSA-N n-[4-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound COC[C@@H]1CCCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 SSCIGRNQLSIHHI-SFHVURJKSA-N 0.000 claims 1
- SYTLPGMWQNQGEQ-UHFFFAOYSA-N n-[4-[3-[2-(methylamino)pyridin-4-yl]pyridin-2-yl]oxyphenyl]quinolin-2-amine Chemical compound C1=NC(NC)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=C4C=CC=CC4=CC=3)=CC=2)=C1 SYTLPGMWQNQGEQ-UHFFFAOYSA-N 0.000 claims 1
- NEEOPVSYKMVPEJ-UHFFFAOYSA-N n-[4-[3-[2-(trifluoromethyl)pyridin-4-yl]pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1=NC(C(F)(F)F)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 NEEOPVSYKMVPEJ-UHFFFAOYSA-N 0.000 claims 1
- KPZPDJBOZMYHRI-UHFFFAOYSA-N n-[4-[3-[3-(3-methyl-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl]pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound CC1=NOC(C2CN(CC2)C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=N1 KPZPDJBOZMYHRI-UHFFFAOYSA-N 0.000 claims 1
- LYNQICKGHANHBA-UHFFFAOYSA-N n-[4-[3-[3-(aminomethyl)phenyl]pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound NCC1=CC=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 LYNQICKGHANHBA-UHFFFAOYSA-N 0.000 claims 1
- WFOYDCDUWQKBAV-UHFFFAOYSA-N n-[4-[3-[4-(methoxymethyl)piperidin-1-yl]pyridin-2-yl]oxyphenyl]pyridin-2-amine Chemical compound C1CC(COC)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 WFOYDCDUWQKBAV-UHFFFAOYSA-N 0.000 claims 1
- CYWURXTWYFEFPK-UHFFFAOYSA-N n-benzyl-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound C=1C=CC=CC=1CNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 CYWURXTWYFEFPK-UHFFFAOYSA-N 0.000 claims 1
- ZYKMGILISXSOPW-UHFFFAOYSA-N n-cyclopropyl-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound C1CC1NC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 ZYKMGILISXSOPW-UHFFFAOYSA-N 0.000 claims 1
- HEBUVSZUBXENIG-UHFFFAOYSA-N n-ethyl-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound CCNC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 HEBUVSZUBXENIG-UHFFFAOYSA-N 0.000 claims 1
- AHMOEJLZRSPLKJ-UHFFFAOYSA-N n-methyl-1-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C1=CC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 AHMOEJLZRSPLKJ-UHFFFAOYSA-N 0.000 claims 1
- NWUGKEQIQNFUOB-UHFFFAOYSA-N n-methyl-4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]pyridin-2-amine Chemical compound C1=NC(NC)=CC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 NWUGKEQIQNFUOB-UHFFFAOYSA-N 0.000 claims 1
- MIXMDQZCRHBURF-UHFFFAOYSA-N n-propan-2-yl-3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-amine Chemical compound CC(C)NC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 MIXMDQZCRHBURF-UHFFFAOYSA-N 0.000 claims 1
- FQSAIQBSJWBKQV-UHFFFAOYSA-N n-pyridin-4-yl-2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-amine Chemical compound C=1C=CC=NC=1NC(C=C1)=CC=C1OC1=NC=CC=C1NC1=CC=NC=C1 FQSAIQBSJWBKQV-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000005961 oxazepanyl group Chemical group 0.000 claims 1
- 125000003551 oxepanyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 210000002637 putamen Anatomy 0.000 claims 1
- ZMXIEURKVKVTSL-UHFFFAOYSA-N pyridin-2-yl-[4-(3-pyridin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound C=1C=CC=NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=NC=C1 ZMXIEURKVKVTSL-UHFFFAOYSA-N 0.000 claims 1
- ULWUNIJJUSLRPS-UHFFFAOYSA-N pyridin-2-yl-[4-(3-pyrimidin-5-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound C=1C=CC=NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CN=CN=C1 ULWUNIJJUSLRPS-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- DATJETPTDKFEEF-UHFFFAOYSA-N pyrrolidine-3-carbonitrile Chemical compound N#CC1CCNC1 DATJETPTDKFEEF-UHFFFAOYSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- XBQNGYUURPYTRZ-UHFFFAOYSA-N tert-butyl 2-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]acetate Chemical compound CC(C)(C)OC(=O)CC1=NC=CN=C1OC(C=C1)=CC=C1NC1=CC=CC=N1 XBQNGYUURPYTRZ-UHFFFAOYSA-N 0.000 claims 1
- YRYQQFKZKHRAJZ-UHFFFAOYSA-N tert-butyl 4-[2-[4-(pyridin-2-ylamino)phenoxy]pyridin-3-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C(=NC=CC=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 YRYQQFKZKHRAJZ-UHFFFAOYSA-N 0.000 claims 1
- ZJJZCXFYRDWULU-UHFFFAOYSA-N tert-butyl 4-[2-[4-[(5-methylpyridin-2-yl)amino]phenoxy]pyridin-3-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound N1=CC(C)=CC=C1NC(C=C1)=CC=C1OC1=NC=CC=C1C1=CCN(C(=O)OC(C)(C)C)CC1 ZJJZCXFYRDWULU-UHFFFAOYSA-N 0.000 claims 1
- SZGYRYCRPSFSBT-UHFFFAOYSA-N tert-butyl 4-[3-[4-(pyridin-2-ylamino)phenoxy]pyrazin-2-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C(=NC=CN=2)OC=2C=CC(NC=3N=CC=CC=3)=CC=2)=C1 SZGYRYCRPSFSBT-UHFFFAOYSA-N 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13843408P | 2008-12-17 | 2008-12-17 | |
| US13844308P | 2008-12-17 | 2008-12-17 | |
| US61/138,443 | 2008-12-17 | ||
| US61/138,434 | 2008-12-17 | ||
| PCT/US2009/068330 WO2010077992A1 (en) | 2008-12-17 | 2009-12-16 | Aminopyridine and carboxypyridine compounds as phosphodiesterase 10 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012512255A JP2012512255A (ja) | 2012-05-31 |
| JP2012512255A5 true JP2012512255A5 (enExample) | 2013-02-14 |
Family
ID=41718257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011542411A Ceased JP2012512255A (ja) | 2008-12-17 | 2009-12-16 | ホスホジエステラーゼ１０阻害剤としてのアミノピリジンおよびカルボキシピリジン化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8637500B2 (enExample) |
| EP (1) | EP2376455B1 (enExample) |
| JP (1) | JP2012512255A (enExample) |
| AR (1) | AR074775A1 (enExample) |
| AU (1) | AU2009333214B2 (enExample) |
| CA (1) | CA2746307C (enExample) |
| ES (1) | ES2397934T3 (enExample) |
| MX (1) | MX2011006575A (enExample) |
| TW (1) | TW201035051A (enExample) |
| WO (1) | WO2010077992A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9051296B2 (en) | 2009-11-16 | 2015-06-09 | Raqualia Pharma Inc. | Aryl carboxamide derivatives as TTX-S blockers |
| US8470820B2 (en) * | 2010-01-22 | 2013-06-25 | Hoffman-La Roche Inc. | Nitrogen-containing heteroaryl derivatives |
| WO2012018909A1 (en) * | 2010-08-04 | 2012-02-09 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds |
| CA2827724A1 (en) | 2011-02-18 | 2012-08-23 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinolinol derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| WO2012162213A1 (en) * | 2011-05-24 | 2012-11-29 | Merck Sharp & Dohme Corp. | Aryloxymethyl cyclopropane derivatives as pde10 inhibitors |
| MX344600B (es) * | 2011-06-27 | 2016-12-20 | Janssen Pharmaceutica Nv | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxalina. |
| MY157301A (en) * | 2011-08-25 | 2016-05-31 | Merck Sharp & Dohme | Pyrimidine pde10 inhibitors |
| US8470884B2 (en) | 2011-11-09 | 2013-06-25 | Hoffmann-La Roche Inc. | Alkenyl naphthylacetic acids |
| WO2013148537A1 (en) * | 2012-03-29 | 2013-10-03 | Ning Xi | Substituted spirobicyclic compounds and methods of use |
| WO2013171640A1 (en) | 2012-05-15 | 2013-11-21 | Novartis Ag | Benzamide derivatives for inhibiting the activity of abl1, abl2 and bcr-abl1 |
| HK1206250A1 (en) | 2012-06-26 | 2016-01-08 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| KR20180052635A (ko) | 2015-09-18 | 2018-05-18 | 가켄 세이야쿠 가부시키가이샤 | 바이아릴 유도체 및 이를 포함하는 약제 |
| EA202092442A3 (ru) | 2016-06-07 | 2021-08-31 | Джакобио Фармасьютикалс Ко., Лтд. | Новые гетероциклические производные, применимые в качестве ингибиторов shp2 |
| CN108779115B (zh) | 2016-10-14 | 2021-02-26 | 江苏恒瑞医药股份有限公司 | 五元杂芳环并桥环类衍生物、其制备方法及其在医药上的应用 |
| KR102317480B1 (ko) | 2017-03-23 | 2021-10-25 | 자코바이오 파마슈티칼스 컴퍼니 리미티드 | Shp2 억제제로서 유용한 신규한 헤테로환형 유도체 |
| US11299488B2 (en) * | 2017-07-12 | 2022-04-12 | Bristol-Myers Squibb Company | Five membered-aminoheterocycle and 5,6-or 6,6-membered bicyclic aminoheterocyclic inhibitors of rock for the treatment of heart failure |
| CN108997230B (zh) * | 2018-07-26 | 2020-08-04 | 山东大学 | 具有基质金属蛋白酶抑制活性的喹喔啉衍生物及其制备方法和应用 |
| WO2020063760A1 (en) | 2018-09-26 | 2020-04-02 | Jacobio Pharmaceuticals Co., Ltd. | Novel heterocyclic derivatives useful as shp2 inhibitors |
| US12359128B2 (en) | 2020-12-17 | 2025-07-15 | Merck Patent Gmbh | Heteroaromatic isothiocyanates |
| CN117024405A (zh) * | 2022-05-09 | 2023-11-10 | 浙江同源康医药股份有限公司 | 多环类化合物及其用途 |
| WO2025024681A1 (en) * | 2023-07-25 | 2025-01-30 | The Regents Of The University Of California | Ire1alpha inhibitors and uses thereof |
| WO2025024688A1 (en) * | 2023-07-25 | 2025-01-30 | The Regents Of The University Of California | Ire1alpha inhibitors and uses thereof |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107288A (en) | 1974-09-18 | 1978-08-15 | Pharmaceutical Society Of Victoria | Injectable compositions, nanoparticles useful therein, and process of manufacturing same |
| US4198417A (en) * | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Phenoxyphenylpiperidines |
| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| EP1255735A2 (en) * | 2000-02-03 | 2002-11-13 | Eli Lilly And Company | Pyridine derivatives as potentiators of glutamate receptors |
| WO2001087845A2 (en) * | 2000-05-15 | 2001-11-22 | Fujisawa Pharmaceutical Co., Ltd. | N-containing heterocyclic compounds and their use as 5-ht antagonists |
| EP1635828B1 (en) | 2003-04-04 | 2008-04-23 | H. Lundbeck A/S | 4-(2-phenyloxyphenyl)-piperidine or -1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors |
| JP2007508241A (ja) | 2003-07-31 | 2007-04-05 | バイエル・フアーマシユーチカルズ・コーポレーシヨン | Ｐｄｅ１０ａ阻害剤を用いる糖尿病および関連障害の処置方法 |
| CN1845915A (zh) * | 2003-09-02 | 2006-10-11 | 默克公司 | 作为亲代谢谷氨酸受体－5的调节剂的联吡啶胺和醚类化合物 |
| AU2005221140A1 (en) * | 2004-03-08 | 2005-09-22 | Amgen Inc. | Therapeutic modulation of PPAR (gamma) activity |
| US20060019975A1 (en) | 2004-07-23 | 2006-01-26 | Pfizer Inc | Novel piperidyl derivatives of quinazoline and isoquinoline |
| NL2000397C2 (nl) * | 2006-01-05 | 2007-10-30 | Pfizer Prod Inc | Bicyclische heteroarylverbindingen als PDE10 inhibitoren. |
| US7560551B2 (en) * | 2006-01-23 | 2009-07-14 | Amgen Inc. | Aurora kinase modulators and method of use |
| MY161884A (en) | 2006-01-23 | 2017-05-15 | Amgen Inc | Aurora kinase modulators and method of use |
| WO2007129183A2 (en) | 2006-05-02 | 2007-11-15 | Pfizer Products Inc. | Bicyclic heteroaryl compounds as pde10 inhibitors |
| US20080090834A1 (en) * | 2006-07-06 | 2008-04-17 | Pfizer Inc | Selective azole pde10a inhibitor compounds |
| US8236823B2 (en) | 2006-10-27 | 2012-08-07 | Amgen Inc. | Multi-cyclic compounds and methods of use |
| CA2672440A1 (en) | 2006-12-20 | 2008-07-03 | Amgen Inc. | Substituted heterocycles and methods of use |
| WO2009081259A1 (en) | 2007-12-21 | 2009-07-02 | Pfizer Inc. | Phenoxy-pyridyl derivatives |
| AU2009271414A1 (en) | 2008-06-20 | 2010-01-21 | Metabolex, Inc. | Aryl GPR119 agonists and uses thereof |
| TWI396689B (zh) * | 2008-11-14 | 2013-05-21 | Amgen Inc | 作為磷酸二酯酶１０抑制劑之吡衍生物 |
-
2009
- 2009-12-16 AU AU2009333214A patent/AU2009333214B2/en not_active Ceased
- 2009-12-16 ES ES09793422T patent/ES2397934T3/es active Active
- 2009-12-16 CA CA2746307A patent/CA2746307C/en not_active Expired - Fee Related
- 2009-12-16 WO PCT/US2009/068330 patent/WO2010077992A1/en not_active Ceased
- 2009-12-16 JP JP2011542411A patent/JP2012512255A/ja not_active Ceased
- 2009-12-16 US US12/639,931 patent/US8637500B2/en active Active
- 2009-12-16 MX MX2011006575A patent/MX2011006575A/es active IP Right Grant
- 2009-12-16 EP EP09793422A patent/EP2376455B1/en active Active
- 2009-12-17 AR ARP090104944A patent/AR074775A1/es unknown
- 2009-12-17 TW TW098143428A patent/TW201035051A/zh unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012512255A5 (enExample) | ||
| JP7028861B2 (ja) | ピリジル置換のインドール化合物 | |
| JP6348891B2 (ja) | Ｃｘｃｒ４受容体アンタゴニスト | |
| JP5650735B2 (ja) | タンパク質キナーゼ調節剤としてのピリジンおよびピラジン誘導体 | |
| KR101677778B1 (ko) | 아미노피라진 유도체 및 의약 | |
| US20110130380A1 (en) | Heteroaryl Kinase Inhibitors | |
| US20120157433A1 (en) | Heteroaryl Compounds as Kinase Inhibitors | |
| JP2016535003A5 (enExample) | ||
| US20120165306A1 (en) | Pyrazinylpyridines useful for the treatment of proliferative diseases | |
| JP2013537180A (ja) | トリアジン−オキサジアゾール類 | |
| US20130303507A1 (en) | Substituted hetero-biaryl compounds and their uses | |
| WO2012101064A1 (en) | N-acyl pyrimidine biaryl compounds as protein kinase inhibitors | |
| JP2012512255A (ja) | ホスホジエステラーゼ１０阻害剤としてのアミノピリジンおよびカルボキシピリジン化合物 | |
| WO2012101063A1 (en) | N-acyl pyridine biaryl compounds and their uses | |
| JP2014501269A5 (enExample) | ||
| SI2790705T1 (en) | Use of activity inhibitors or PI3K function | |
| JP2009544626A (ja) | Ｉｔｐｋｂ阻害剤としての化合物および組成物 | |
| JPWO2012020786A1 (ja) | 医薬組成物 | |
| JP5668756B2 (ja) | 悪性リンパ腫治療剤 | |
| WO2012005299A1 (ja) | Ｒｏｓチロシンキナーゼ阻害剤 | |
| WO2007089031A1 (en) | Piperidine derivatives as tachykinin receptor antagonists | |
| AU2010209825A1 (en) | Piperidine derivatives as NK3 receptor antagonists | |
| WO2023176972A1 (ja) | 高リスク骨髄線維症の治療剤 |