JP2020512401A5 - - Google Patents
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- Publication number
- JP2020512401A5 JP2020512401A5 JP2020501438A JP2020501438A JP2020512401A5 JP 2020512401 A5 JP2020512401 A5 JP 2020512401A5 JP 2020501438 A JP2020501438 A JP 2020501438A JP 2020501438 A JP2020501438 A JP 2020501438A JP 2020512401 A5 JP2020512401 A5 JP 2020512401A5
- Authority
- JP
- Japan
- Prior art keywords
- cyano
- piperidine
- phenyl
- difluorophenoxy
- carboxamide
- 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.)
- Granted
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- 125000005843 halogen group Chemical group 0.000 claims 77
- 125000000217 alkyl group Chemical group 0.000 claims 70
- -1 2-phenylthiazole-4-yl Chemical group 0.000 claims 56
- 125000001424 substituent group Chemical group 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 33
- 125000003545 alkoxy group Chemical group 0.000 claims 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 29
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 25
- 150000002431 hydrogen Chemical class 0.000 claims 23
- 125000005842 heteroatom Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000004043 oxo group Chemical group O=* 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 14
- 125000004076 pyridyl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 4
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229960004502 levodopa Drugs 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- YNJXVWIPWJKJJD-UHFFFAOYSA-N 2-methoxypyridine-3-carboxamide Chemical compound COC1=NC=CC=C1C(N)=O YNJXVWIPWJKJJD-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- WPZXKSWSISFJCB-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenoxy)piperidin-1-yl]-2-methylpyrimidin-5-yl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=NC(=NC=C2NC(C2=C(N=CC=C2)OC)=O)C)C=CC(=C1)F WPZXKSWSISFJCB-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 239000000534 dopa decarboxylase inhibitor Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- OMUQQRJCAXCTKA-UHFFFAOYSA-N 1-(2-fluoroethyl)-N-[2-[4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl]-5-methylsulfonylphenyl]-3-methoxypyrazole-4-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(=O)C=2C(=NN(C=2)CCF)OC)C=CC(=C1)OC OMUQQRJCAXCTKA-UHFFFAOYSA-N 0.000 claims 1
- XPAIRFWCKMGLAK-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-methoxytriazole-4-carboxamide Chemical compound ClC1=C(CN2N=NC(=C2OC)C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=CC=C1 XPAIRFWCKMGLAK-UHFFFAOYSA-N 0.000 claims 1
- UVXPKYWGVBRSKM-UHFFFAOYSA-N 1-benzyl-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-oxopyridine-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(C(=CC=C1)C(=O)NC1=C(C=CC(=C1)C#N)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)=O UVXPKYWGVBRSKM-UHFFFAOYSA-N 0.000 claims 1
- MLEBIJSXGXPDFN-UHFFFAOYSA-N 1-butyl-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-oxopyridine-3-carboxamide Chemical compound C(CCC)N1C(C(=CC=C1)C(=O)NC1=C(C=CC(=C1)C#N)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)=O MLEBIJSXGXPDFN-UHFFFAOYSA-N 0.000 claims 1
- GAWNOZOKPKBYKC-UHFFFAOYSA-N 2-methoxy-6-methylpyridine-3-carboxamide Chemical compound COC1=NC(C)=CC=C1C(N)=O GAWNOZOKPKBYKC-UHFFFAOYSA-N 0.000 claims 1
- IJJHYDKPEOJCJN-UHFFFAOYSA-N 3,5-dichloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound ClC=1C(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=C(C=1)Cl)OC IJJHYDKPEOJCJN-UHFFFAOYSA-N 0.000 claims 1
- ZIBKECPMPJMQLE-UHFFFAOYSA-N 3,6-dichloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound ClC=1C(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C(=CC=1)Cl)OC ZIBKECPMPJMQLE-UHFFFAOYSA-N 0.000 claims 1
- VXUIVESBOOONBI-UHFFFAOYSA-N 3-chloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,6-dimethoxybenzamide Chemical compound ClC=1C(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C(=CC=1)OC)OC VXUIVESBOOONBI-UHFFFAOYSA-N 0.000 claims 1
- HSMKIJAAZFFORD-UHFFFAOYSA-N 3-chloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound COc1c(Cl)cccc1C(=O)Nc1cc(ccc1N1CCC(CC1)Oc1ccc(F)cc1F)C#N HSMKIJAAZFFORD-UHFFFAOYSA-N 0.000 claims 1
- NZURINXWXNYEMF-UHFFFAOYSA-N 4,5-dichloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound ClC1=CC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=C1Cl)OC NZURINXWXNYEMF-UHFFFAOYSA-N 0.000 claims 1
- ZTLVFYQYNNAWIL-UHFFFAOYSA-N 4-bromo-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound BrC1=CC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=C1)OC ZTLVFYQYNNAWIL-UHFFFAOYSA-N 0.000 claims 1
- RDIWFGMBVKRNRL-UHFFFAOYSA-N 4-chloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound ClC1=CC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=C1)OC RDIWFGMBVKRNRL-UHFFFAOYSA-N 0.000 claims 1
- JPLSWHSGTJWKKE-UHFFFAOYSA-N 4-chloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound ClC1=CC=NC(=C1C(=O)NC1=C(C=CC(=C1)C#N)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)OC JPLSWHSGTJWKKE-UHFFFAOYSA-N 0.000 claims 1
- NXQLBCIJYNCZKC-UHFFFAOYSA-N 4-methoxypyridine-3-carboxamide Chemical compound COC1=CC=NC=C1C(N)=O NXQLBCIJYNCZKC-UHFFFAOYSA-N 0.000 claims 1
- ONBIVBVXGNLCTG-UHFFFAOYSA-N 4-tert-butyl-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=C1)OC ONBIVBVXGNLCTG-UHFFFAOYSA-N 0.000 claims 1
- ZMWHSFRHKNELAF-UHFFFAOYSA-N 5-bromo-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound BrC=1C=CC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=1)OC ZMWHSFRHKNELAF-UHFFFAOYSA-N 0.000 claims 1
- GPCJEEIYRRTCTG-UHFFFAOYSA-N 5-bromo-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-oxo-1-propan-2-ylpyridine-3-carboxamide Chemical compound BrC=1C=C(C(N(C=1)C(C)C)=O)C(=O)NC1=C(C=CC(=C1)C#N)N1CCC(CC1)OC1=C(C=C(C=C1)F)F GPCJEEIYRRTCTG-UHFFFAOYSA-N 0.000 claims 1
- BHWJDMMQTKBOGM-UHFFFAOYSA-N 5-chloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxy-3-methylbenzamide Chemical compound ClC=1C=C(C(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=1)OC)C BHWJDMMQTKBOGM-UHFFFAOYSA-N 0.000 claims 1
- AYJJPMHHUOXLRH-UHFFFAOYSA-N 5-chloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound ClC=1C=CC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=1)OC AYJJPMHHUOXLRH-UHFFFAOYSA-N 0.000 claims 1
- CYZPAHBXJQKHQH-UHFFFAOYSA-N 5-chloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound ClC=1C=NC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=1)OC CYZPAHBXJQKHQH-UHFFFAOYSA-N 0.000 claims 1
- ZJSXAKHCOKVOMJ-UHFFFAOYSA-N 5-fluoro-2-methoxypyridine-3-carboxamide Chemical compound COC1=NC=C(F)C=C1C(N)=O ZJSXAKHCOKVOMJ-UHFFFAOYSA-N 0.000 claims 1
- RDWOITQWHFQRAR-UHFFFAOYSA-N 5-fluoro-N-[2-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-6-methylpyridin-3-yl]-2-oxo-1H-pyridine-3-carboxamide Chemical compound FC=1C=NC(=C(C(=O)NC=2C(=NC(=CC=2)C)N2CCN(CC2)CC2=CC=C(C=C2)F)C=1)O RDWOITQWHFQRAR-UHFFFAOYSA-N 0.000 claims 1
- QLULFDYIRVQWRX-UHFFFAOYSA-N 5-tert-butyl-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxybenzamide Chemical compound C(C)(C)(C)C=1C=CC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=1)OC QLULFDYIRVQWRX-UHFFFAOYSA-N 0.000 claims 1
- WVTUZXKXQDQTAU-UHFFFAOYSA-N 6-chloro-N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound ClC1=NC(=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(C=C(C=C2)F)F)C=C1)OC WVTUZXKXQDQTAU-UHFFFAOYSA-N 0.000 claims 1
- 101100449538 Arabidopsis thaliana GRP16 gene Proteins 0.000 claims 1
- 229940081615 DOPA decarboxylase inhibitor Drugs 0.000 claims 1
- VZSVYNXXSRKAEI-UHFFFAOYSA-N FC1=CC=C(CN2CCN(CC2)C2=NC(=CC=C2NC(=O)C=2C=NN(C=2O)C)C)C=C1 Chemical compound FC1=CC=C(CN2CCN(CC2)C2=NC(=CC=C2NC(=O)C=2C=NN(C=2O)C)C)C=C1 VZSVYNXXSRKAEI-UHFFFAOYSA-N 0.000 claims 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- AOQWGIPHWGFCHF-UHFFFAOYSA-N N-[2-(4-benzoylpiperidin-1-yl)-5-cyanophenyl]-2-methoxypyridine-3-carboxamide Chemical compound C(C1=CC=CC=C1)(=O)C1CCN(CC1)C1=C(C=C(C=C1)C#N)NC(C1=C(N=CC=C1)OC)=O AOQWGIPHWGFCHF-UHFFFAOYSA-N 0.000 claims 1
- FSMJDIMCCFEAIW-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-4-methylsulfonylphenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound Cn1cccc(C(=O)Nc2ccc(cc2N2CCC(CC2)Oc2ccc(F)cc2F)S(C)(=O)=O)c1=O FSMJDIMCCFEAIW-UHFFFAOYSA-N 0.000 claims 1
- KXUKEETVRUKABG-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-(dimethylcarbamoyl)phenyl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)C(N(C)C)=O)NC(C2=C(N=CC=C2)OC)=O)C=CC(=C1)F KXUKEETVRUKABG-UHFFFAOYSA-N 0.000 claims 1
- SDWJHBWXUPTXHV-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-(hydroxymethyl)pyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=NC=C(C=C2NC(C2=C(N=CC=C2)OC)=O)CO)C=CC(=C1)F SDWJHBWXUPTXHV-UHFFFAOYSA-N 0.000 claims 1
- VADCYSRNCZOBNR-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-(methoxymethyl)pyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=NC=C(C=C2NC(C2=C(N=CC=C2)OC)=O)COC)C=CC(=C1)F VADCYSRNCZOBNR-UHFFFAOYSA-N 0.000 claims 1
- JOSREYSUAGVAIK-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-methylpyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound COc1nn(C)cc1C(=O)Nc1cc(C)cnc1N1CCC(CC1)Oc1ccc(F)cc1F JOSREYSUAGVAIK-UHFFFAOYSA-N 0.000 claims 1
- CCVTZNREFJTXRC-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-methylpyridin-3-yl]-4-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=NC=C(C=C2NC(C2=CN=CC=C2OC)=O)C)C=CC(=C1)F CCVTZNREFJTXRC-UHFFFAOYSA-N 0.000 claims 1
- FRWRUBLLRVFDRZ-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-methylsulfonylphenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(=O)C=2C(N(C=CC=2)C)=O)C=CC(=C1)F FRWRUBLLRVFDRZ-UHFFFAOYSA-N 0.000 claims 1
- OQVVAEQWZXYLRF-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-methylsulfonylphenyl]-2-fluoro-6-methoxybenzamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(C2=C(C=CC=C2OC)F)=O)C=CC(=C1)F OQVVAEQWZXYLRF-UHFFFAOYSA-N 0.000 claims 1
- MFHYKRDJUIURSF-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-methylsulfonylphenyl]-2-methoxybenzamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(C2=C(C=CC=C2)OC)=O)C=CC(=C1)F MFHYKRDJUIURSF-UHFFFAOYSA-N 0.000 claims 1
- BVKYNYHBJUMZSM-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-methylsulfonylphenyl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(C2=C(N=CC=C2)OC)=O)C=CC(=C1)F BVKYNYHBJUMZSM-UHFFFAOYSA-N 0.000 claims 1
- OPOOLIHXTIRCLG-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-methylsulfonylphenyl]-3-fluoro-2-methoxybenzamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(C2=C(C(=CC=C2)F)OC)=O)C=CC(=C1)F OPOOLIHXTIRCLG-UHFFFAOYSA-N 0.000 claims 1
- FLCQYBCPMCKPEE-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-methylsulfonylphenyl]-4-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(C2=CN=CC=C2OC)=O)C=CC(=C1)F FLCQYBCPMCKPEE-UHFFFAOYSA-N 0.000 claims 1
- JNDCKUUUOCECMW-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-morpholin-4-ylsulfonylpyridin-3-yl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=NC=C(C=C2NC(=O)C=2C(N(C=CC=2)C)=O)S(=O)(=O)N2CCOCC2)C=CC(=C1)F JNDCKUUUOCECMW-UHFFFAOYSA-N 0.000 claims 1
- TUSHMIKBWCCXKD-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-6-methylpyridin-3-yl]-4-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=NC(=CC=C2NC(C2=CN=CC=C2OC)=O)C)C=CC(=C1)F TUSHMIKBWCCXKD-UHFFFAOYSA-N 0.000 claims 1
- ANNJNWZZQUDRNW-UHFFFAOYSA-N N-[2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=CC=C2)NC(=O)C=2C(N(C=CC=2)C)=O)C=CC(=C1)F ANNJNWZZQUDRNW-UHFFFAOYSA-N 0.000 claims 1
- WERHNYIZJGCTCH-UHFFFAOYSA-N N-[2-[4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl]-5-methylsulfonylphenyl]-1-(fluoromethyl)-3-methoxypyrazole-4-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(=O)C=2C(=NN(C=2)CF)OC)C=CC(=C1)OC WERHNYIZJGCTCH-UHFFFAOYSA-N 0.000 claims 1
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- YABOLCIAWXTJIO-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3-methyl-5-oxo-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CN=C2N(C1=O)C(=CS2)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F YABOLCIAWXTJIO-UHFFFAOYSA-N 0.000 claims 1
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- QDXCQSCJYNYMQM-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4,5-difluoro-2-methoxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=C(C(=C1)F)F)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F QDXCQSCJYNYMQM-UHFFFAOYSA-N 0.000 claims 1
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- GJBQDORVHNRGTQ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methoxy-2-methylpyrimidine-5-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(=NC(=NC=1)C)OC)N1CCC(CC1)OC1=C(C=C(C=C1)F)F GJBQDORVHNRGTQ-UHFFFAOYSA-N 0.000 claims 1
- ZJKUEMVHIRLIDV-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methoxypyridine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=NC=CC(=C1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F ZJKUEMVHIRLIDV-UHFFFAOYSA-N 0.000 claims 1
- UVCSMPSNQBFZPZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methoxypyrimidine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NC=CC(=N1)OC)N1CCC(CC1)OC1=C(C=C(C=C1)F)F UVCSMPSNQBFZPZ-UHFFFAOYSA-N 0.000 claims 1
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- RMRCDAWNFMASNL-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methyl-1,2,5-oxadiazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NON=C1C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F RMRCDAWNFMASNL-UHFFFAOYSA-N 0.000 claims 1
- CYRGWISERIJZRL-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methyl-1,3-thiazole-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1SC=C(N=1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F CYRGWISERIJZRL-UHFFFAOYSA-N 0.000 claims 1
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- NFNDENVYLRBLMY-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2,4,6-trifluorophenyl)methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=C(C=C(C=C1F)F)F)NC(=O)C=1C(=NN(C=1)C)OC NFNDENVYLRBLMY-UHFFFAOYSA-N 0.000 claims 1
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- YFPBJAFHEUPVTA-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3-cyanophenyl)methyl]piperazin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(N=CC=C1)OC)=O)N1CCN(CC1)CC1=CC(=CC=C1)C#N YFPBJAFHEUPVTA-UHFFFAOYSA-N 0.000 claims 1
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- IGWPCPKZDZIEGM-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3-fluoro-4-methoxyphenyl)methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=CC(=C(C=C1)OC)F)NC(=O)C=1C(=NN(C=1)C)OC IGWPCPKZDZIEGM-UHFFFAOYSA-N 0.000 claims 1
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- SJFZSDOYKSCSRD-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3-fluorophenyl)methyl]piperazin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(N=CC=C1)OC)=O)N1CCN(CC1)CC1=CC(=CC=C1)F SJFZSDOYKSCSRD-UHFFFAOYSA-N 0.000 claims 1
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- SLZLQYOSRFDLIJ-UHFFFAOYSA-N N-[5-cyano-2-[4-[(4-cyanophenyl)methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound COC1=NN(C)C=C1C(=O)NC1=CC(=CN=C1N1CCN(CC2=CC=C(C=C2)C#N)CC1)C#N SLZLQYOSRFDLIJ-UHFFFAOYSA-N 0.000 claims 1
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- KJKUDTIUWYEPIP-UHFFFAOYSA-N N-[5-cyano-2-[4-[(5-cyano-2-fluorophenyl)methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=C(C=CC(=C1)C#N)F)NC(=O)C=1C(=NN(C=1)C)OC KJKUDTIUWYEPIP-UHFFFAOYSA-N 0.000 claims 1
- NDKNLBLPPDXBDC-UHFFFAOYSA-N N-[5-cyano-2-[4-[(5-fluoropyridin-2-yl)methyl]piperazin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(N=CC=C1)OC)=O)N1CCN(CC1)CC1=NC=C(C=C1)F NDKNLBLPPDXBDC-UHFFFAOYSA-N 0.000 claims 1
- XPXQEYCHUBUXLM-UHFFFAOYSA-N N-[5-cyano-2-[4-[(5-methoxypyridin-2-yl)methyl]piperazin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(N=CC=C1)OC)=O)N1CCN(CC1)CC1=NC=C(C=C1)OC XPXQEYCHUBUXLM-UHFFFAOYSA-N 0.000 claims 1
- PHTSHQMHHUAHJP-XMMPIXPASA-N N-[5-cyano-2-[4-[(R)-(2,4-difluorophenyl)-fluoromethyl]piperidin-1-yl]phenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C=CC=1)C)=O)N1CCC(CC1)[C@@H](F)C1=C(C=C(C=C1)F)F PHTSHQMHHUAHJP-XMMPIXPASA-N 0.000 claims 1
- PHTSHQMHHUAHJP-DEOSSOPVSA-N N-[5-cyano-2-[4-[(S)-(2,4-difluorophenyl)-fluoromethyl]piperidin-1-yl]phenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C=CC=1)C)=O)N1CCC(CC1)[C@H](F)C1=C(C=C(C=C1)F)F PHTSHQMHHUAHJP-DEOSSOPVSA-N 0.000 claims 1
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- KTDKUQWPVCYUDL-UHFFFAOYSA-N N-[5-cyano-2-[4-[[2-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=C(C=CC=C1)OC(F)(F)F)NC(=O)C=1C(=NN(C=1)C)OC KTDKUQWPVCYUDL-UHFFFAOYSA-N 0.000 claims 1
- ARNBGJIPAMJRDG-UHFFFAOYSA-N N-[5-cyano-2-[4-[[3-(difluoromethoxy)phenyl]methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=CC(=CC=C1)OC(F)F)NC(=O)C=1C(=NN(C=1)C)OC ARNBGJIPAMJRDG-UHFFFAOYSA-N 0.000 claims 1
- JRPGMFMGMWNZJE-UHFFFAOYSA-N N-[5-cyano-2-[4-[[3-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=CC(=CC=C1)OC(F)(F)F)NC(=O)C=1C(=NN(C=1)C)OC JRPGMFMGMWNZJE-UHFFFAOYSA-N 0.000 claims 1
- UPUXORPCNKWLDZ-UHFFFAOYSA-N N-[5-cyano-2-[4-[[4-(difluoromethoxy)phenyl]methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=CC=C(C=C1)OC(F)F)NC(=O)C=1C(=NN(C=1)C)OC UPUXORPCNKWLDZ-UHFFFAOYSA-N 0.000 claims 1
- FSRNAKVFXLXIAZ-UHFFFAOYSA-N N-[5-cyano-2-[4-[[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=CC=C(C=C1)OC(F)(F)F)NC(=O)C=1C(=NN(C=1)C)OC FSRNAKVFXLXIAZ-UHFFFAOYSA-N 0.000 claims 1
- WXBSTDUYOMFSDV-UHFFFAOYSA-N N-[6-chloro-4-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound ClC1=CC(=C(C=N1)NC(=O)C=1C(N(C=CC=1)C)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F WXBSTDUYOMFSDV-UHFFFAOYSA-N 0.000 claims 1
- CFWMIONBVWEMII-UHFFFAOYSA-N N-[6-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-5-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C1=CC=C(C(=N1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(=O)C=1C=NN(C=1OC)C CFWMIONBVWEMII-UHFFFAOYSA-N 0.000 claims 1
- UUXDEWKYOZDRLB-UHFFFAOYSA-N N-[6-cyano-3-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridazin-4-yl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C1=CC(=C(N=N1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(C1=C(N=CC=C1)OC)=O UUXDEWKYOZDRLB-UHFFFAOYSA-N 0.000 claims 1
- IAGUZQKXCMWUEQ-UHFFFAOYSA-N N-[6-cyano-4-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C1=CC(=C(C=N1)NC(C1=C(N=CC=C1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F IAGUZQKXCMWUEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 229940052760 dopamine agonists Drugs 0.000 claims 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- MNYDYOPMALMZPZ-UHFFFAOYSA-N oxazepine-3-carboxamide Chemical compound NC(=O)C1=NOC=CC=C1 MNYDYOPMALMZPZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
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| WO2021035257A1 (en) * | 2019-08-21 | 2021-02-25 | The Scripps Research Institute | Monocyclic agonists of stimulator of interferon genes sting |
| CN115151540A (zh) | 2019-12-02 | 2022-10-04 | 风暴治疗有限公司 | 作为mettl3抑制剂的多杂环化合物 |
| EP4196118A1 (en) | 2020-08-13 | 2023-06-21 | Boehringer Ingelheim International GmbH | Treatment of cognitive impairement associated with schizophrenia |
| CN117567449A (zh) | 2020-10-13 | 2024-02-20 | 勃林格殷格翰国际有限公司 | 再加工方法 |
| WO2022240992A1 (en) * | 2021-05-12 | 2022-11-17 | Libra Therapeutics, Inc. | Heterocyclic trpml1 agonists and uses thereof |
| CN120917015A (zh) * | 2023-01-20 | 2025-11-07 | 元启(苏州)生物制药有限公司 | Srpk1抑制剂和使用方法 |
| WO2025165967A2 (en) * | 2024-02-02 | 2025-08-07 | Maplight Therapeutics, Inc. | Gpr6 inverse agonists |
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| US20040034019A1 (en) * | 2002-08-08 | 2004-02-19 | Ronald Tomlinson | Piperazine and piperidine derivatives |
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| EP3105216B1 (en) * | 2014-02-14 | 2018-10-10 | Takeda Pharmaceutical Company Limited | Pyrazine modulators of gpr6 |
| GB201406956D0 (en) * | 2014-04-17 | 2014-06-04 | Univ Nottingham | Compounds |
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