JP2019504901A5 - - Google Patents
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- JP2019504901A5 JP2019504901A5 JP2018561928A JP2018561928A JP2019504901A5 JP 2019504901 A5 JP2019504901 A5 JP 2019504901A5 JP 2018561928 A JP2018561928 A JP 2018561928A JP 2018561928 A JP2018561928 A JP 2018561928A JP 2019504901 A5 JP2019504901 A5 JP 2019504901A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- carboxamide
- pyridine
- thieno
- ylphenyl
- 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.)
- Pending
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- -1 6-methyl-3-pyridyl Chemical group 0.000 claims description 981
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 763
- DSARAHGYZHXMQZ-UHFFFAOYSA-N thieno[3,2-b]pyridine-5-carboxamide Chemical compound NC(=O)C1=CC=C2SC=CC2=N1 DSARAHGYZHXMQZ-UHFFFAOYSA-N 0.000 claims description 553
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 152
- MRQVGIPVJXWABP-UHFFFAOYSA-N N1C(C(=O)N)=CC=C2N=CC=C21 Chemical compound N1C(C(=O)N)=CC=C2N=CC=C21 MRQVGIPVJXWABP-UHFFFAOYSA-N 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- XWEMRIPNLSTWIU-UHFFFAOYSA-N N1C(C(=O)N)=CC=C2N=NC=C21 Chemical compound N1C(C(=O)N)=CC=C2N=NC=C21 XWEMRIPNLSTWIU-UHFFFAOYSA-N 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 208000004454 Hyperalgesia Diseases 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 8
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 208000020016 psychiatric disease Diseases 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 4
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 4
- 206010053552 allodynia Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 206010000117 Abnormal behaviour Diseases 0.000 claims description 3
- 208000012661 Dyskinesia Diseases 0.000 claims description 3
- 206010019233 Headaches Diseases 0.000 claims description 3
- 208000019022 Mood disease Diseases 0.000 claims description 3
- 230000003542 behavioural effect Effects 0.000 claims description 3
- 231100000869 headache Toxicity 0.000 claims description 3
- MOUSTVMSPZAJLI-UHFFFAOYSA-N (4-hydroxy-4-methylpiperidin-1-yl)-[7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridin-5-yl]methanone Chemical compound OC1(CCN(CC1)C(=O)C1=CC(=C2C(=N1)C=CS2)CC1=CC=C(C=C1)N1N=CC=C1)C MOUSTVMSPZAJLI-UHFFFAOYSA-N 0.000 claims description 2
- HAZYMGNMXVTOOG-UHFFFAOYSA-N (4-hydroxy-4-methylpiperidin-1-yl)-[7-[[4-(2-methyl-1,3-oxazol-4-yl)phenyl]methyl]thieno[3,2-b]pyridin-5-yl]methanone Chemical compound OC1(CCN(CC1)C(=O)C1=CC(=C2C(=N1)C=CS2)CC1=CC=C(C=C1)C=1N=C(OC=1)C)C HAZYMGNMXVTOOG-UHFFFAOYSA-N 0.000 claims description 2
- UJKNYDAANSRFNH-UHFFFAOYSA-N 1-methyl-7-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(oxan-4-yl)pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound CN1C=CC2=NC(=CC(=C21)CC1=CC=C(C=C1)C1=NN(C=C1)C)C(=O)NC1CCOCC1 UJKNYDAANSRFNH-UHFFFAOYSA-N 0.000 claims description 2
- DIOGQVZLZFMKSY-UHFFFAOYSA-N 1-methyl-7-[[6-(1-methylpyrazol-3-yl)pyridin-3-yl]methyl]-N-(oxan-4-yl)pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound CN1C=CC2=NC(=CC(=C21)CC=1C=NC(=CC=1)C1=NN(C=C1)C)C(=O)NC1CCOCC1 DIOGQVZLZFMKSY-UHFFFAOYSA-N 0.000 claims description 2
- VAEWPBCKGKWAPI-UHFFFAOYSA-N 1-methyl-7-[[6-(1-methylpyrazol-4-yl)pyridin-3-yl]methyl]-N-(oxan-4-yl)pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound CN1C=CC2=NC(=CC(=C21)CC=1C=NC(=CC=1)C=1C=NN(C=1)C)C(=O)NC1CCOCC1 VAEWPBCKGKWAPI-UHFFFAOYSA-N 0.000 claims description 2
- SONRPYGLPUWUFI-UHFFFAOYSA-N 1-methyl-N-(2-oxaspiro[3.3]heptan-6-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]pyrazolo[4,3-b]pyridine-5-carboxamide Chemical compound CN1N=CC2=NC(=CC(=C21)CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1CC2(COC2)C1 SONRPYGLPUWUFI-UHFFFAOYSA-N 0.000 claims description 2
- COOFARIMJIULGR-UHFFFAOYSA-N 1-methyl-N-(2-oxaspiro[3.3]heptan-6-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound CN1C=CC2=C1C(CC1=CC=C(C=C1)N1C=CC=N1)=CC(=N2)C(=O)NC1CC2(COC2)C1 COOFARIMJIULGR-UHFFFAOYSA-N 0.000 claims description 2
- DOFBCUVYMARYHU-UHFFFAOYSA-N 1-methyl-N-(oxetan-2-ylmethyl)-7-[(4-pyrazol-1-ylphenyl)methyl]pyrazolo[4,3-b]pyridine-5-carboxamide Chemical compound CN1N=CC2=NC(=CC(=C21)CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NCC1OCC1 DOFBCUVYMARYHU-UHFFFAOYSA-N 0.000 claims description 2
- ANANTWMZDKOVED-UHFFFAOYSA-N 2-methyl-N-(oxan-4-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CC2=NC(=CC(=C2S1)CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1CCOCC1 ANANTWMZDKOVED-UHFFFAOYSA-N 0.000 claims description 2
- LSINVHPGIKRNGM-UHFFFAOYSA-N 2-oxa-5-azabicyclo[2.2.1]heptan-5-yl-[7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridin-5-yl]methanone Chemical compound C12OCC(N(C1)C(=O)C1=CC(=C3C(=N1)C=CS3)CC1=CC=C(C=C1)N1N=CC=C1)C2 LSINVHPGIKRNGM-UHFFFAOYSA-N 0.000 claims description 2
- ZKRJFLGSAYBHEQ-UHFFFAOYSA-N 3-methyl-7-[(6-methylpyridin-3-yl)methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC=1C=NC(=CC=1)C)C(=O)NC1CCOCC1 ZKRJFLGSAYBHEQ-UHFFFAOYSA-N 0.000 claims description 2
- PNNPEYCSMSGLKG-UHFFFAOYSA-N 3-methyl-7-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)C1=NN(C=C1)C)C(=O)NC1CCOCC1 PNNPEYCSMSGLKG-UHFFFAOYSA-N 0.000 claims description 2
- SLODPRNQGNSVSO-UHFFFAOYSA-N 3-methyl-7-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(oxetan-2-ylmethyl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)C1=NN(C=C1)C)C(=O)NCC1OCC1 SLODPRNQGNSVSO-UHFFFAOYSA-N 0.000 claims description 2
- GVWJDXDPNRETDC-UHFFFAOYSA-N 3-methyl-7-[[4-(1-methylpyrazol-3-yl)phenyl]methyl]-N-(oxetan-3-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)C1=NN(C=C1)C)C(=O)NC1COC1 GVWJDXDPNRETDC-UHFFFAOYSA-N 0.000 claims description 2
- ISQFYUPMNIHHSI-UHFFFAOYSA-N 3-methyl-7-[[4-(2-methyl-1,3-oxazol-4-yl)phenyl]methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)C=1N=C(OC=1)C)C(=O)NC1CCOCC1 ISQFYUPMNIHHSI-UHFFFAOYSA-N 0.000 claims description 2
- MJCAEXVCZQFZJQ-UHFFFAOYSA-N 3-methyl-N-(2-oxaspiro[3.3]heptan-6-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1CC2(COC2)C1 MJCAEXVCZQFZJQ-UHFFFAOYSA-N 0.000 claims description 2
- ZZXDNTZMFZPPIG-UHFFFAOYSA-N 3-methyl-N-(oxan-4-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1CCOCC1 ZZXDNTZMFZPPIG-UHFFFAOYSA-N 0.000 claims description 2
- XRSRCSXADBOHMA-UHFFFAOYSA-N 3-methyl-N-(oxetan-2-ylmethyl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NCC1OCC1 XRSRCSXADBOHMA-UHFFFAOYSA-N 0.000 claims description 2
- YMDUHFWIMMAOQH-UHFFFAOYSA-N 3-methyl-N-(oxetan-3-yl)-7-[(4-pyrazol-1-ylphenyl)methyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CSC=2C1=NC(=CC=2CC1=CC=C(C=C1)N1N=CC=C1)C(=O)NC1COC1 YMDUHFWIMMAOQH-UHFFFAOYSA-N 0.000 claims description 2
- VFWXBDIAFDIYOI-UHFFFAOYSA-N 7-(6-methylpyridin-3-yl)oxy-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CC=C(C=N1)OC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 VFWXBDIAFDIYOI-UHFFFAOYSA-N 0.000 claims description 2
- QAUPZZCGMAQJHC-UHFFFAOYSA-N 7-[(2-methyl-1,3-thiazol-5-yl)methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC=1SC(=CN=1)CC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 QAUPZZCGMAQJHC-UHFFFAOYSA-N 0.000 claims description 2
- JLVMAJPIMCABSS-UHFFFAOYSA-N 7-[(2-methylpyrimidin-5-yl)methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=NC=C(C=N1)CC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 JLVMAJPIMCABSS-UHFFFAOYSA-N 0.000 claims description 2
- OTTHCDJBHRADLN-UHFFFAOYSA-N 7-[(4-pyrazol-1-ylphenyl)methyl]-N-[1-(2,2,2-trifluoroethyl)azetidin-3-yl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound N1(N=CC=C1)C1=CC=C(C=C1)CC1=C2C(=NC(=C1)C(=O)NC1CN(C1)CC(F)(F)F)C=CS2 OTTHCDJBHRADLN-UHFFFAOYSA-N 0.000 claims description 2
- WQYKQQSIHUURPZ-UHFFFAOYSA-N 7-[(6-methylpyridin-3-yl)methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound CC1=CC=C(C=N1)CC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 WQYKQQSIHUURPZ-UHFFFAOYSA-N 0.000 claims description 2
- AUYIWKJWXUGEEP-UHFFFAOYSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)NC2CCOCC2)C=CS3)C=CC(=C1)C=1C=NN(C=1)C AUYIWKJWXUGEEP-UHFFFAOYSA-N 0.000 claims description 2
- JXFVGYPQMOFXHS-RXVVDRJESA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycycloheptyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCCC2)O)C=CS3)C=CC(=C1)C=1C=NN(C=1)C JXFVGYPQMOFXHS-RXVVDRJESA-N 0.000 claims description 2
- GWCHKGFZEWYELB-PXNSSMCTSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycyclohexyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCC2)O)C=CS3)C=CC(=C1)C=1C=NN(C=1)C GWCHKGFZEWYELB-PXNSSMCTSA-N 0.000 claims description 2
- LRJODMPWAHMKAD-LPHOPBHVSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycyclopentyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCC2)O)C=CS3)C=CC(=C1)C=1C=NN(C=1)C LRJODMPWAHMKAD-LPHOPBHVSA-N 0.000 claims description 2
- CTPRLUZDNKPGGJ-AVRDEDQJSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(1S,2S)-2-methoxycyclohexyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCC2)OC)C=CS3)C=CC(=C1)C=1C=NN(C=1)C CTPRLUZDNKPGGJ-AVRDEDQJSA-N 0.000 claims description 2
- RHKDYFYFZCKMNN-KPMSDPLLSA-N 7-[2-fluoro-4-(1-methylpyrazol-4-yl)phenoxy]-N-[(2R)-2-hydroxycyclobutyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)NC2[C@@H](CC2)O)C=CS3)C=CC(=C1)C=1C=NN(C=1)C RHKDYFYFZCKMNN-KPMSDPLLSA-N 0.000 claims description 2
- MGVWLFWVJROTFO-DENIHFKCSA-N 7-[2-fluoro-4-(2-methylindazol-4-yl)phenoxy]-N-[(1R,2R)-2-hydroxycyclobutyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@H]2[C@@H](CC2)O)C=CS3)C=CC(=C1)C=1C2=CN(N=C2C=CC=1)C MGVWLFWVJROTFO-DENIHFKCSA-N 0.000 claims description 2
- AYCMUDSXHDFAKP-DHLKQENFSA-N 7-[2-fluoro-4-(2-methylindazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycycloheptyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCCC2)O)C=CS3)C=CC(=C1)C=1C2=CN(N=C2C=CC=1)C AYCMUDSXHDFAKP-DHLKQENFSA-N 0.000 claims description 2
- AKFJNWKCQBHMLB-URXFXBBRSA-N 7-[2-fluoro-4-(2-methylindazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycyclohexyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCCC2)O)C=CS3)C=CC(=C1)C=1C2=CN(N=C2C=CC=1)C AKFJNWKCQBHMLB-URXFXBBRSA-N 0.000 claims description 2
- VACOHCHHYZCWBC-REWPJTCUSA-N 7-[2-fluoro-4-(2-methylindazol-4-yl)phenoxy]-N-[(1S,2S)-2-hydroxycyclopentyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(OC2=C3C(=NC(=C2)C(=O)N[C@@H]2[C@H](CCC2)O)C=CS3)C=CC(=C1)C=1C2=CN(N=C2C=CC=1)C VACOHCHHYZCWBC-REWPJTCUSA-N 0.000 claims description 2
- VZYAMACJEIFDIA-UHFFFAOYSA-N 7-[[2,6-difluoro-4-(1,3-thiazol-4-yl)phenyl]methyl]-N-(oxan-4-yl)thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(C(=CC(=C1)C=1N=CSC=1)F)CC1=C2C(=NC(=C1)C(=O)NC1CCOCC1)C=CS2 VZYAMACJEIFDIA-UHFFFAOYSA-N 0.000 claims description 2
- STDSOKVGXHRPTD-REWPJTCUSA-N 7-[[2,6-difluoro-4-(1-methylpyrazol-4-yl)phenyl]methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(C(=CC(=C1)C=1C=NN(C=1)C)F)CC1=C2C(=NC(=C1)C(=O)N[C@@H]1[C@H](CCCC1)O)C=CS2 STDSOKVGXHRPTD-REWPJTCUSA-N 0.000 claims description 2
- IWHFGIVRLFGVMO-UGKGYDQZSA-N 7-[[2,6-difluoro-4-(1-methylpyrazol-4-yl)phenyl]methyl]-N-[(1S,2S)-2-hydroxycyclopentyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(C(=CC(=C1)C=1C=NN(C=1)C)F)CC1=C2C(=NC(=C1)C(=O)N[C@@H]1[C@H](CCC1)O)C=CS2 IWHFGIVRLFGVMO-UGKGYDQZSA-N 0.000 claims description 2
- HYEDDJIKSYAQBA-IGKIAQTJSA-N 7-[[2,6-difluoro-4-(2-methylindazol-4-yl)phenyl]methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(C(=CC(=C1)C=1C2=CN(N=C2C=CC=1)C)F)CC1=C2C(=NC(=C1)C(=O)N[C@@H]1[C@H](CCCC1)O)C=CS2 HYEDDJIKSYAQBA-IGKIAQTJSA-N 0.000 claims description 2
- CVUQCTJKBIPDDM-WIYYLYMNSA-N 7-[[2-fluoro-4-(1-methylpyrazol-4-yl)phenyl]methyl]-N-[(1R,2R)-2-hydroxycyclobutyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)C=1C=NN(C=1)C)CC1=C2C(=NC(=C1)C(=O)N[C@H]1[C@@H](CC1)O)C=CS2 CVUQCTJKBIPDDM-WIYYLYMNSA-N 0.000 claims description 2
- QZYHLNIINMOPSX-URXFXBBRSA-N 7-[[2-fluoro-4-(1-methylpyrazol-4-yl)phenyl]methyl]-N-[(1S,2S)-2-hydroxycycloheptyl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)C=1C=NN(C=1)C)CC1=C2C(=NC(=C1)C(=O)N[C@@H]1[C@H](CCCCC1)O)C=CS2 QZYHLNIINMOPSX-URXFXBBRSA-N 0.000 claims description 2
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| WO2019241467A1 (en) * | 2018-06-13 | 2019-12-19 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor m1 |
| US11970483B2 (en) | 2018-09-28 | 2024-04-30 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| US12162864B2 (en) | 2018-09-28 | 2024-12-10 | Takeda Pharmaceutical Company Limited | Condensed-cyclic compound |
| EP3643711A1 (en) | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
| WO2020086864A1 (en) | 2018-10-24 | 2020-04-30 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor m1 |
| JP7572734B2 (ja) | 2019-10-04 | 2024-10-24 | ヴァンダービルト ユニバーシティー | ムスカリン性アセチルコリン受容体ｍ４のアンタゴニスト |
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| US4608079A (en) | 1983-08-02 | 1986-08-26 | American Cyanamid Company | Imidazolidinones, and imidazolidinethiones, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| DE4129603A1 (de) * | 1991-09-06 | 1993-03-11 | Thomae Gmbh Dr K | Kondensierte 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| KR20010102543A (ko) | 1999-03-09 | 2001-11-15 | 로렌스 티. 마이젠헬더 | 항바이러스제로서의4-옥소-4,7-디히드로-티에노[2,3-ｂ]피리딘-5-카르복스아미드 |
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| BR112012014180A2 (pt) * | 2009-12-17 | 2015-09-15 | Merck Sharp & Dohme | composto, composição farmacêutica, uso da composição farmacêutica, e, método para tratar uma doença ou em distúrbio. |
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| EP2709621B1 (en) * | 2011-05-17 | 2016-11-02 | Merck Sharp & Dohme Corp. | N-linked quinolineamide m1 receptor positive allosteric modulators |
| US20160200733A1 (en) | 2013-08-23 | 2016-07-14 | Vanderbilt University | Substituted thieno[2,3-b]pyridine-2-carboxamide analogs as positive allosteric modulators of the muscarinic acetylcholine receptor m4 |
| TW201512197A (zh) | 2013-08-30 | 2015-04-01 | Hoffmann La Roche | 吡咯并吡啶或吡唑并吡啶衍生物 |
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2017
- 2017-02-16 EP EP17753822.0A patent/EP3416639B1/en active Active
- 2017-02-16 AU AU2017221404A patent/AU2017221404A1/en not_active Abandoned
- 2017-02-16 BR BR112018016689A patent/BR112018016689A2/pt not_active IP Right Cessation
- 2017-02-16 MX MX2018009952A patent/MX385975B/es unknown
- 2017-02-16 CA CA3014791A patent/CA3014791A1/en active Pending
- 2017-02-16 EA EA201891854A patent/EA201891854A1/ru unknown
- 2017-02-16 US US15/998,899 patent/US11111251B2/en active Active
- 2017-02-16 WO PCT/US2017/018140 patent/WO2017143041A1/en not_active Ceased
- 2017-02-16 JP JP2018561928A patent/JP2019504901A/ja active Pending
- 2017-02-16 KR KR1020187026643A patent/KR20180110132A/ko not_active Withdrawn
- 2017-02-16 MA MA044253A patent/MA44253A/fr unknown
- 2017-02-16 CN CN201780023438.3A patent/CN109069491A/zh active Pending
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2018
- 2018-08-08 IL IL261058A patent/IL261058A/en unknown
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