JP2012512255A5 - - Google Patents
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- 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
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- -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
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- 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
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- 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
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13844308P | 2008-12-17 | 2008-12-17 | |
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| WO2011058766A1 (en) * | 2009-11-16 | 2011-05-19 | 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 |
| US9029536B2 (en) * | 2010-08-04 | 2015-05-12 | 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) |
| US8975261B2 (en) | 2011-05-24 | 2015-03-10 | Merck Sharp & Dohme Corp. | Aryloxmethyl cyclopropane derivatives as PDE10 inhibitors |
| WO2013000924A1 (en) * | 2011-06-27 | 2013-01-03 | Janssen Pharmaceutica Nv | 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES |
| BR112014004310B8 (pt) * | 2011-08-25 | 2023-04-18 | Merck Sharp & Dohme | Composto de pirimidina inibidor da enzima fosfodiesterase 10, composição farmacêutica, uso de um composto |
| 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 |
| CN104379574B (zh) | 2012-05-15 | 2017-03-01 | 诺华股份有限公司 | 用于抑制abl1、abl2和bcr‑abl1的活性的苯甲酰胺衍生物 |
| WO2014001314A1 (en) * | 2012-06-26 | 2014-01-03 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 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) |
| SG11201801856XA (en) | 2015-09-18 | 2018-04-27 | Kaken Pharmaceutical Co Ltd | Biaryl derivative and medicine containing same |
| MX388576B (es) | 2016-06-07 | 2025-03-20 | Jacobio Pharmaceuticals Co Ltd | Derivados heterociclicos novedosos utiles como inhibidores de shp2. |
| JP2019534266A (ja) | 2016-10-14 | 2019-11-28 | 江蘇恒瑞医薬股▲ふん▼有限公司 | ５員ヘテロアリール環の架橋した環誘導体、その製造方法およびその医学的使用 |
| EA202190196A1 (ru) | 2017-03-23 | 2021-08-31 | Джакобио Фармасьютикалс Ко., Лтд. | Новые гетероциклические производные, применимые в качестве ингибиторов shp2 |
| EP3652165B1 (en) * | 2017-07-12 | 2021-08-25 | Bristol-Myers Squibb Company | Five membered-aminoheterocyclic 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 |
| US20210393623A1 (en) | 2018-09-26 | 2021-12-23 | Jacobio Pharmaceuticals Co., Ltd. | Novel Heterocyclic Derivatives Useful as SHP2 Inhibitors |
| US12359128B2 (en) | 2020-12-17 | 2025-07-15 | Merck Patent Gmbh | Heteroaromatic isothiocyanates |
| WO2023217156A1 (zh) * | 2022-05-09 | 2023-11-16 | 浙江同源康医药股份有限公司 | 多环类化合物及其用途 |
| WO2025024688A1 (en) * | 2023-07-25 | 2025-01-30 | The Regents Of The University Of California | Ire1alpha inhibitors and uses thereof |
| WO2025024681A1 (en) * | 2023-07-25 | 2025-01-30 | The Regents Of The University Of California | Ire1alpha inhibitors and uses thereof |
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| 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 |
| US6800651B2 (en) | 2000-02-03 | 2004-10-05 | Eli Lilly And Company | Potentiators of glutamate receptors |
| US20030176454A1 (en) * | 2000-05-15 | 2003-09-18 | Akira Yamada | N-coating heterocyclic compounds |
| NZ540891A (en) | 2003-04-04 | 2008-07-31 | Lundbeck & Co As H | 4-(2-Phenyloxyphenyl)-piperidine or -1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors |
| EP1651251A4 (en) | 2003-07-31 | 2008-06-18 | Bayer Pharmaceuticals Corp | METHOD FOR THE TREATMENT OF DIABETES AND RELATED DISEASES USING PDE 10A INHIBITORS |
| JP2007504229A (ja) * | 2003-09-02 | 2007-03-01 | メルク エンド カムパニー インコーポレーテッド | 代謝調節型グルタミン酸受容体−５のモジュレーターとしてのビピリジルアミン類およびエーテル類 |
| US20050250820A1 (en) * | 2004-03-08 | 2005-11-10 | Amgen Inc. | Therapeutic modulation of PPARgamma 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. |
| DK1984353T3 (en) | 2006-01-23 | 2016-03-14 | Amgen Inc | Aurorakinasemodulatorer and method of use |
| US7560551B2 (en) * | 2006-01-23 | 2009-07-14 | Amgen Inc. | Aurora kinase modulators and method of use |
| US20090176829A1 (en) | 2006-05-02 | 2009-07-09 | Pfizer Inc | Bicyclic heteroaryl compounds as pde10 inhibitors |
| US20080090834A1 (en) | 2006-07-06 | 2008-04-17 | Pfizer Inc | Selective azole pde10a inhibitor compounds |
| WO2008057280A1 (en) | 2006-10-27 | 2008-05-15 | Amgen Inc. | Multi-cyclic compounds and methods of use |
| WO2008079294A1 (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 |
| CA2727174A1 (en) | 2008-06-20 | 2010-01-21 | Jiangao Song | 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 |
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- 2009-12-16 WO PCT/US2009/068330 patent/WO2010077992A1/en not_active Ceased
- 2009-12-16 EP EP09793422A patent/EP2376455B1/en active Active
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- 2009-12-17 TW TW098143428A patent/TW201035051A/zh unknown
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