JP2020512401A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- LXNNHKUCEGGUTH-UHFFFAOYSA-N N-[2-[4-(4-chlorobenzoyl)piperazin-1-yl]-5-cyanophenyl]-2-methoxypyridine-3-carboxamide Chemical compound ClC1=CC=C(C(=O)N2CCN(CC2)C2=C(C=C(C=C2)C#N)NC(C2=C(N=CC=C2)OC)=O)C=C1 LXNNHKUCEGGUTH-UHFFFAOYSA-N 0.000 claims 1
- VUYCCCPZDOPIEM-UHFFFAOYSA-N N-[2-[4-(4-chlorobenzoyl)piperazin-1-yl]phenyl]-2-hydroxy-N-methylbenzamide Chemical compound ClC1=CC=C(C(=O)N2CCN(CC2)C2=C(C=CC=C2)N(C(C2=C(C=CC=C2)O)=O)C)C=C1 VUYCCCPZDOPIEM-UHFFFAOYSA-N 0.000 claims 1
- XMKHDQVJZVWGCR-UHFFFAOYSA-N N-[2-[4-(4-chlorobenzoyl)piperazin-1-yl]phenyl]pyrimidine-2-carboxamide Chemical compound ClC1=CC=C(C(=O)N2CCN(CC2)C2=C(C=CC=C2)NC(=O)C2=NC=CC=N2)C=C1 XMKHDQVJZVWGCR-UHFFFAOYSA-N 0.000 claims 1
- HKNHCMWYYWXIJQ-UHFFFAOYSA-N N-[2-[4-(4-chlorobenzoyl)piperazin-1-yl]phenyl]pyrimidine-4-carboxamide Chemical compound ClC1=CC=C(C(=O)N2CCN(CC2)C2=C(C=CC=C2)NC(=O)C2=NC=NC=C2)C=C1 HKNHCMWYYWXIJQ-UHFFFAOYSA-N 0.000 claims 1
- GIKIVZWLOXRDGG-UHFFFAOYSA-N N-[2-[4-(4-fluoro-2-methylbenzoyl)piperazin-1-yl]-5-methylsulfonylphenyl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=CC(=C(C(=O)N2CCN(CC2)C2=C(C=C(C=C2)S(=O)(=O)C)NC(C2=C(N=CC=C2)OC)=O)C=C1)C GIKIVZWLOXRDGG-UHFFFAOYSA-N 0.000 claims 1
- WHQSKZQTZZUTIR-UHFFFAOYSA-N N-[2-[4-(5-chloro-2-fluorobenzoyl)piperidin-1-yl]-5-cyanophenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound ClC=1C=CC(=C(C(=O)C2CCN(CC2)C2=C(C=C(C=C2)C#N)NC(=O)C=2C(N(C=CC=2)C)=O)C=1)F WHQSKZQTZZUTIR-UHFFFAOYSA-N 0.000 claims 1
- SISVQKZORNKNSC-UHFFFAOYSA-N N-[2-[4-[(2,4-difluorophenyl)methyl]piperazin-1-yl]-5-(methoxymethyl)pyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(CN2CCN(CC2)C2=NC=C(C=C2NC(C2=C(N=CC=C2)OC)=O)COC)C=CC(=C1)F SISVQKZORNKNSC-UHFFFAOYSA-N 0.000 claims 1
- WHLBONTWDBOMRJ-UHFFFAOYSA-N N-[2-[4-[(2-chloro-6-fluorophenyl)methyl]piperazin-1-yl]-5-cyanophenyl]-2-methoxypyridine-3-carboxamide Chemical compound ClC1=C(CN2CCN(CC2)C2=C(C=C(C=C2)C#N)NC(C2=C(N=CC=C2)OC)=O)C(=CC=C1)F WHLBONTWDBOMRJ-UHFFFAOYSA-N 0.000 claims 1
- IIEFPFGCKYFLDE-UHFFFAOYSA-N N-[2-[4-[(4-chloro-2,6-difluorophenyl)methyl]piperazin-1-yl]-5-cyanopyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound ClC1=CC(=C(CN2CCN(CC2)C2=NC=C(C=C2NC(=O)C=2C(=NN(C=2)C)OC)C#N)C(=C1)F)F IIEFPFGCKYFLDE-UHFFFAOYSA-N 0.000 claims 1
- OIDGUUIXPDBNON-UHFFFAOYSA-N N-[2-[4-[(4-chloro-2-fluorophenyl)methyl]piperazin-1-yl]-5-cyanopyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound ClC1=CC(=C(CN2CCN(CC2)C2=NC=C(C=C2NC(=O)C=2C(=NN(C=2)C)OC)C#N)C=C1)F OIDGUUIXPDBNON-UHFFFAOYSA-N 0.000 claims 1
- XHDBWZQEPVOTMQ-UHFFFAOYSA-N N-[2-[4-[(4-cyano-3-fluorophenyl)methyl]piperazin-1-yl]-5-methylpyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C1=C(C=C(CN2CCN(CC2)C2=NC=C(C=C2NC(=O)C=2C(=NN(C=2)C)OC)C)C=C1)F XHDBWZQEPVOTMQ-UHFFFAOYSA-N 0.000 claims 1
- CBPKIUPMYMSROI-UHFFFAOYSA-N N-[2-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-6-methylpyridin-3-yl]-5-methoxy-1-methylpyrazole-4-carboxamide Chemical compound FC1=CC=C(CN2CCN(CC2)C2=NC(=CC=C2NC(=O)C=2C=NN(C=2OC)C)C)C=C1 CBPKIUPMYMSROI-UHFFFAOYSA-N 0.000 claims 1
- URDDELFBUGUQSH-UHFFFAOYSA-N N-[2-[4-[(5-chloro-2-fluorophenyl)-difluoromethyl]piperidin-1-yl]-5-cyanophenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound ClC=1C=CC(=C(C=1)C(C1CCN(CC1)C1=C(C=C(C=C1)C#N)NC(=O)C=1C(N(C=CC=1)C)=O)(F)F)F URDDELFBUGUQSH-UHFFFAOYSA-N 0.000 claims 1
- KZZICIXMTYVSRQ-UHFFFAOYSA-N N-[2-cyano-4-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyrimidin-5-yl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound C(#N)C1=NC=C(C(=N1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(C1=C(N=C(C=C1)C)OC)=O KZZICIXMTYVSRQ-UHFFFAOYSA-N 0.000 claims 1
- FYBAOOCJLUTFGN-UHFFFAOYSA-N N-[2-cyano-5-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-4-yl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C1=NC=C(C(=C1)NC(C1=C(N=CC=C1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F FYBAOOCJLUTFGN-UHFFFAOYSA-N 0.000 claims 1
- QFWXVVLKSIJBGT-UHFFFAOYSA-N N-[2-cyano-5-[4-[(2,3,4-trifluorophenyl)methyl]piperazin-1-yl]pyridin-4-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C1=NC=C(C(=C1)NC(=O)C=1C(=NN(C=1)C)OC)N1CCN(CC1)CC1=C(C(=C(C=C1)F)F)F QFWXVVLKSIJBGT-UHFFFAOYSA-N 0.000 claims 1
- FVVMYKWREIFEMC-UHFFFAOYSA-N N-[2-cyano-5-[4-[(3,4,5-trifluorophenyl)methyl]piperazin-1-yl]pyridin-4-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C1=NC=C(C(=C1)NC(=O)C=1C(=NN(C=1)C)OC)N1CCN(CC1)CC1=CC(=C(C(=C1)F)F)F FVVMYKWREIFEMC-UHFFFAOYSA-N 0.000 claims 1
- HLDDXCRBIAMPJX-UHFFFAOYSA-N N-[4,5-dicyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C1=CC(=C(C=C1C#N)NC(C1=C(N=CC=C1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HLDDXCRBIAMPJX-UHFFFAOYSA-N 0.000 claims 1
- SMBGFNAQVSAXHV-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenoxy)piperidin-1-yl]-2-methoxypyrimidin-5-yl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=NC(=NC=C2NC(C2=C(N=C(C=C2)C)OC)=O)OC)C=CC(=C1)F SMBGFNAQVSAXHV-UHFFFAOYSA-N 0.000 claims 1
- VHHJMSXGQWIAMX-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenoxy)piperidin-1-yl]-2-methylpyrimidin-5-yl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=NC(=NC=C2NC(C2=C(N=C(C=C2)C)OC)=O)C)C=CC(=C1)F VHHJMSXGQWIAMX-UHFFFAOYSA-N 0.000 claims 1
- KKWQBCPOAMLDOS-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenoxy)piperidin-1-yl]-6-(methoxymethyl)pyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=NC(=C2)COC)NC(C2=C(N=CC=C2)OC)=O)C=CC(=C1)F KKWQBCPOAMLDOS-UHFFFAOYSA-N 0.000 claims 1
- LKHDGPNZGMDTQT-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenoxy)piperidin-1-yl]-6-methoxypyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=NC(=C2)OC)NC(C2=C(N=CC=C2)OC)=O)C=CC(=C1)F LKHDGPNZGMDTQT-UHFFFAOYSA-N 0.000 claims 1
- DGXRNGAYEFMKHW-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenoxy)piperidin-1-yl]-6-methoxypyridin-3-yl]-4-methoxypyridine-3-carboxamide Chemical compound COc1cc(N2CCC(CC2)Oc2ccc(F)cc2F)c(NC(=O)c2cnccc2OC)cn1 DGXRNGAYEFMKHW-UHFFFAOYSA-N 0.000 claims 1
- GMDCBUDFPYRFJR-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenoxy)piperidin-1-yl]-6-methylpyridin-3-yl]-4-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=NC(=C2)C)NC(C2=CN=CC=C2OC)=O)C=CC(=C1)F GMDCBUDFPYRFJR-UHFFFAOYSA-N 0.000 claims 1
- XDVQBQPCLYPNTH-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound FC1=C(OC2CCN(CC2)C2=C(C=NC=C2)NC(C2=C(N=CC=C2)OC)=O)C=CC(=C1)F XDVQBQPCLYPNTH-UHFFFAOYSA-N 0.000 claims 1
- IGISUTVXBSWMMT-UHFFFAOYSA-N N-[4-[4-(2,4-difluorophenyl)sulfonylpiperidin-1-yl]-6-methylpyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound FC1=C(C=CC(=C1)F)S(=O)(=O)C1CCN(CC1)C1=C(C=NC(=C1)C)NC(=O)C=1C(=NN(C=1)C)OC IGISUTVXBSWMMT-UHFFFAOYSA-N 0.000 claims 1
- JEGMTESECHCDTM-UHFFFAOYSA-N N-[4-[4-(4-cyano-2-fluorophenoxy)piperidin-1-yl]-6-methylpyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C1=CC(=C(OC2CCN(CC2)C2=C(C=NC(=C2)C)NC(C2=C(N=CC=C2)OC)=O)C=C1)F JEGMTESECHCDTM-UHFFFAOYSA-N 0.000 claims 1
- YMCXSBUQASBGAQ-UHFFFAOYSA-N N-[4-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-5-(dimethylcarbamoyl)phenyl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C1=CC(=C(C=C1C(N(C)C)=O)NC(C1=C(N=CC=C1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F YMCXSBUQASBGAQ-UHFFFAOYSA-N 0.000 claims 1
- REVCEICGRIRKIK-UHFFFAOYSA-N N-[4-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methoxypyridine-3-carboxamide Chemical compound C(#N)C1=CC(=C(C=C1)NC(C1=CN=CC=C1OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F REVCEICGRIRKIK-UHFFFAOYSA-N 0.000 claims 1
- FDFHYXFVAZAZSF-UHFFFAOYSA-N N-[5-cyano-2-[4-(1,3-thiazol-4-ylmethyl)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)CC=1N=CSC=1 FDFHYXFVAZAZSF-UHFFFAOYSA-N 0.000 claims 1
- RMGDCLKMBKVFSQ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,3-difluorophenoxy)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)OC1=C(C(=CC=C1)F)F RMGDCLKMBKVFSQ-UHFFFAOYSA-N 0.000 claims 1
- LWHCFTAODRDWKN-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorobenzoyl)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)C(C1=C(C=C(C=C1)F)F)=O LWHCFTAODRDWKN-UHFFFAOYSA-N 0.000 claims 1
- VWEZFKMHIMPNPG-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-4-(dimethylcarbamoyl)phenyl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C=1C(=CC(=C(C=1)NC(C1=C(N=CC=C1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)C(N(C)C)=O VWEZFKMHIMPNPG-UHFFFAOYSA-N 0.000 claims 1
- MUNCFDCOBPNWCG-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]-4-fluorophenyl]-2-methoxy-6-methylpyridine-3-carboxamide Chemical compound C(#N)C=1C(=CC(=C(C=1)NC(C1=C(N=C(C=C1)C)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)F MUNCFDCOBPNWCG-UHFFFAOYSA-N 0.000 claims 1
- ARUGJFXQTOMZQI-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,2,5-oxadiazole-3-carboxamide Chemical compound FC1=CC(F)=C(OC2CCN(CC2)C2=C(NC(=O)C3=NON=C3)C=C(C=C2)C#N)C=C1 ARUGJFXQTOMZQI-UHFFFAOYSA-N 0.000 claims 1
- QRUBVQFSWDEVLX-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,2,5-thiadiazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NSN=C1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F QRUBVQFSWDEVLX-UHFFFAOYSA-N 0.000 claims 1
- IEOZTTSQUYKZNU-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,2-oxazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NOC=C1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F IEOZTTSQUYKZNU-UHFFFAOYSA-N 0.000 claims 1
- TUKPHEJXTHIWGC-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,2-thiazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NSC=C1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F TUKPHEJXTHIWGC-UHFFFAOYSA-N 0.000 claims 1
- FFDWQOUNVTWNFW-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,3-oxazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=COC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F FFDWQOUNVTWNFW-UHFFFAOYSA-N 0.000 claims 1
- VXQKVGKXAVZJTA-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,3-thiazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=CSC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F VXQKVGKXAVZJTA-UHFFFAOYSA-N 0.000 claims 1
- GLGXHIPZDPAIQI-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,4,6-trimethyl-2-oxopyridine-3-carboxamide Chemical compound CN1C(C)=CC(C)=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(F)C=C(F)C=C2)C1=O GLGXHIPZDPAIQI-UHFFFAOYSA-N 0.000 claims 1
- JNKURFBMRFPJJU-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,5,6-trimethyl-2-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C(=C(C=1)C)C)C)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F JNKURFBMRFPJJU-UHFFFAOYSA-N 0.000 claims 1
- HGCREKLLZNLRQT-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,5-dimethylpyrazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NN(C(=C1)C)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HGCREKLLZNLRQT-UHFFFAOYSA-N 0.000 claims 1
- LMCQEUWBGXPODV-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,6-dimethyl-2-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C(=CC=1)C)C)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F LMCQEUWBGXPODV-UHFFFAOYSA-N 0.000 claims 1
- CMPWURKJWNWVAU-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1,6-dimethyl-4-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CN(C(=CC1=O)C)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F CMPWURKJWNWVAU-UHFFFAOYSA-N 0.000 claims 1
- DFUYELRRSQBNTH-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-(difluoromethyl)-2-oxopyridine-3-carboxamide Chemical compound FC(F)N1C=CC=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(F)C=C(F)C=C2)C1=O DFUYELRRSQBNTH-UHFFFAOYSA-N 0.000 claims 1
- HUMQUCBRIPNBDW-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-[2-(dimethylamino)-2-oxoethyl]-2-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C=CC=1)CC(=O)N(C)C)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HUMQUCBRIPNBDW-UHFFFAOYSA-N 0.000 claims 1
- IZNZTRMMPXEYJD-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-cyclohexyl-2-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C=CC=1)C1CCCCC1)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F IZNZTRMMPXEYJD-UHFFFAOYSA-N 0.000 claims 1
- XAVOBZXZQUWQKM-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-ethyl-4,6-dimethyl-2-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C(=CC=1C)C)CC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F XAVOBZXZQUWQKM-UHFFFAOYSA-N 0.000 claims 1
- HTVWAMIPSYFMHN-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-ethyl-5-methylpyrazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NN(C(=C1)C)CC)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HTVWAMIPSYFMHN-UHFFFAOYSA-N 0.000 claims 1
- TVWISBHDAROWDB-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methyl-2-oxo-5,6,7,8-tetrahydroquinoline-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C=2CCCCC=2C=1)C)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F TVWISBHDAROWDB-UHFFFAOYSA-N 0.000 claims 1
- JERYOXAITXLMID-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methyl-2-oxo-6-propan-2-ylpyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C(=CC=1)C(C)C)C)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F JERYOXAITXLMID-UHFFFAOYSA-N 0.000 claims 1
- VUNUUQRCYMXJTA-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methyl-6-oxo-2-phenylpyrimidine-5-carboxamide Chemical compound CN1C(=O)C(=CN=C1C1=CC=CC=C1)C(=O)NC1=C(C=CC(=C1)C#N)N1CCC(CC1)OC1=C(F)C=C(F)C=C1 VUNUUQRCYMXJTA-UHFFFAOYSA-N 0.000 claims 1
- XLPYYIYYFSBIGK-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methylimidazole-2-carboxamide Chemical compound Cn1ccnc1C(=O)Nc1cc(ccc1N1CCC(CC1)Oc1ccc(F)cc1F)C#N XLPYYIYYFSBIGK-UHFFFAOYSA-N 0.000 claims 1
- CDVZJCUGEHYTOY-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methylimidazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=CN(C=1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F CDVZJCUGEHYTOY-UHFFFAOYSA-N 0.000 claims 1
- YNTSBCXCYCKXLN-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methylpyrazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NN(C=C1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F YNTSBCXCYCKXLN-UHFFFAOYSA-N 0.000 claims 1
- ITSAINWAGDYXGC-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methyltriazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=NN(C=1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F ITSAINWAGDYXGC-UHFFFAOYSA-N 0.000 claims 1
- BPNCWGAIPBSFMQ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,3-difluoro-6-methoxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C(=CC=C1OC)F)F)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F BPNCWGAIPBSFMQ-UHFFFAOYSA-N 0.000 claims 1
- SSOFCHHEZIMHAH-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,3-dihydro-1-benzofuran-7-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CC=CC=2CCOC=21)N1CCC(CC1)OC1=C(C=C(C=C1)F)F SSOFCHHEZIMHAH-UHFFFAOYSA-N 0.000 claims 1
- NNXJNANTCQTVFZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,3-dimethoxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C(=CC=C1)OC)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F NNXJNANTCQTVFZ-UHFFFAOYSA-N 0.000 claims 1
- JCQPOZNJSOYDEV-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,3-dimethyl-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(=C(S2)C)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F JCQPOZNJSOYDEV-UHFFFAOYSA-N 0.000 claims 1
- BVGHMJFNUJRQJV-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,4-dimethoxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=C(C=C1)OC)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F BVGHMJFNUJRQJV-UHFFFAOYSA-N 0.000 claims 1
- MYGHNUSUMJTASI-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,5-dimethoxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=CC(=C1)OC)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F MYGHNUSUMJTASI-UHFFFAOYSA-N 0.000 claims 1
- JBGYEECBDKGFJT-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,5-dimethyl-1,3-oxazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=C(OC=1C)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F JBGYEECBDKGFJT-UHFFFAOYSA-N 0.000 claims 1
- SESFNXAWRVTOMV-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,6-dimethoxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=CC=C1OC)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F SESFNXAWRVTOMV-UHFFFAOYSA-N 0.000 claims 1
- MPJJPFZURSBTPF-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,6-dimethoxypyridine-3-carboxamide Chemical compound COc1ccc(C(=O)Nc2cc(ccc2N2CCC(CC2)Oc2ccc(F)cc2F)C#N)c(OC)n1 MPJJPFZURSBTPF-UHFFFAOYSA-N 0.000 claims 1
- WQTIGEFQHMEUEK-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2,6-dimethylpyrimidine-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NC(=NC(=C1)C)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F WQTIGEFQHMEUEK-UHFFFAOYSA-N 0.000 claims 1
- WZTZSOJUNUWQFK-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-ethoxypyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(N=CC=C1)OCC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F WZTZSOJUNUWQFK-UHFFFAOYSA-N 0.000 claims 1
- BJFUFFXWCYTXNH-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-hydroxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=CC=C1)O)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F BJFUFFXWCYTXNH-UHFFFAOYSA-N 0.000 claims 1
- OZBVOBUHSASZDT-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxy-3,6-dimethylbenzamide Chemical compound COC1=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=C(F)C=C(F)C=C2)C(C)=CC=C1C OZBVOBUHSASZDT-UHFFFAOYSA-N 0.000 claims 1
- QUKROVCGDDFOQH-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxy-3-methylbenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C(=CC=C1)C)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F QUKROVCGDDFOQH-UHFFFAOYSA-N 0.000 claims 1
- RBQWNHCSJJAXOY-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxy-4,6-dimethylpyridine-3-carboxamide Chemical compound COC1=NC(C)=CC(C)=C1C(=O)NC1=C(C=CC(=C1)C#N)N1CCC(CC1)OC1=C(F)C=C(F)C=C1 RBQWNHCSJJAXOY-UHFFFAOYSA-N 0.000 claims 1
- PGXYDNIOSKHWPI-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxy-4-methylbenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=C(C=C1)C)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F PGXYDNIOSKHWPI-UHFFFAOYSA-N 0.000 claims 1
- HFCBVQYBMOWFTL-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxy-5-methylbenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=CC(=C1)C)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HFCBVQYBMOWFTL-UHFFFAOYSA-N 0.000 claims 1
- HEKCTMZDYZMYBE-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxy-5-morpholin-4-ylbenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=CC(=C1)N1CCOCC1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HEKCTMZDYZMYBE-UHFFFAOYSA-N 0.000 claims 1
- QTQLBIPFABIRED-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxy-6-methylbenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=CC=C1C)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F QTQLBIPFABIRED-UHFFFAOYSA-N 0.000 claims 1
- BHKRQXCACVFJOS-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methoxypyrimidine-4-carboxamide Chemical compound COc1nccc(n1)C(=O)Nc1cc(ccc1N1CCC(CC1)Oc1ccc(F)cc1F)C#N BHKRQXCACVFJOS-UHFFFAOYSA-N 0.000 claims 1
- CAUAJUDKMQSKKZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=C(OC=1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F CAUAJUDKMQSKKZ-UHFFFAOYSA-N 0.000 claims 1
- VEMQXARBPOGVDR-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=C(SC=1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F VEMQXARBPOGVDR-UHFFFAOYSA-N 0.000 claims 1
- SGABXNSUMISYJS-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-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=C(S2)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F SGABXNSUMISYJS-UHFFFAOYSA-N 0.000 claims 1
- UGEWLLXMHRIHRS-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-methylpyrimidine-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NC(=NC=C1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F UGEWLLXMHRIHRS-UHFFFAOYSA-N 0.000 claims 1
- NWCJRHAKZUCGTN-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-oxo-1-(pyridin-2-ylmethyl)pyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(N(C=CC=1)CC1=NC=CC=C1)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F NWCJRHAKZUCGTN-UHFFFAOYSA-N 0.000 claims 1
- JCMOCENFFULVGB-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-oxo-1-propan-2-ylpyridine-3-carboxamide Chemical compound CC(C)n1cccc(C(=O)Nc2cc(ccc2N2CCC(CC2)Oc2ccc(F)cc2F)C#N)c1=O JCMOCENFFULVGB-UHFFFAOYSA-N 0.000 claims 1
- KRDZTQJNZSBDLE-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-2-oxo-1H-pyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(NC=CC=1)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F KRDZTQJNZSBDLE-UHFFFAOYSA-N 0.000 claims 1
- LXRMEIANEQVGTQ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3,4-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 LXRMEIANEQVGTQ-UHFFFAOYSA-N 0.000 claims 1
- VUFIITZXANUSIC-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3,5-difluoro-2-methoxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C(=CC(=C1)F)F)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F VUFIITZXANUSIC-UHFFFAOYSA-N 0.000 claims 1
- JZPCETJMMYVSSD-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3,5-difluoropyridine-2-carboxamide Chemical compound Fc1ccc(OC2CCN(CC2)c2ccc(cc2NC(=O)c2ncc(F)cc2F)C#N)c(F)c1 JZPCETJMMYVSSD-UHFFFAOYSA-N 0.000 claims 1
- LUKPBHSFDLYBBY-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3,5-dimethylpyrazine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NC=C(N=C1C)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F LUKPBHSFDLYBBY-UHFFFAOYSA-N 0.000 claims 1
- NJNLOIFWOCYWFL-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3-fluoropyridine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=NC=CC=C1F)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F NJNLOIFWOCYWFL-UHFFFAOYSA-N 0.000 claims 1
- MFVXJBYLKWIMJD-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3-methoxypyridine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=NC=CC=C1OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F MFVXJBYLKWIMJD-UHFFFAOYSA-N 0.000 claims 1
- WWUVAOUORYZTRI-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3-methoxypyridine-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=NC=C1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F WWUVAOUORYZTRI-UHFFFAOYSA-N 0.000 claims 1
- IUWNOVUCSMMOOK-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3-methoxythiophene-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1SC=CC=1OC)N1CCC(CC1)OC1=C(C=C(C=C1)F)F IUWNOVUCSMMOOK-UHFFFAOYSA-N 0.000 claims 1
- 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
- CWEJLPPCQUIFLR-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-3-methylpyrazine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NC=CN=C1C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F CWEJLPPCQUIFLR-UHFFFAOYSA-N 0.000 claims 1
- 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
- INEHMKWQRUJBHV-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4,5-dimethyl-1,2-oxazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NOC(=C1C)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F INEHMKWQRUJBHV-UHFFFAOYSA-N 0.000 claims 1
- OZVVYVJNDWQWHU-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-(dimethylamino)-2-methoxybenzamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(C=C(C=C1)N(C)C)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F OZVVYVJNDWQWHU-UHFFFAOYSA-N 0.000 claims 1
- KNWGXUWHIZRAMG-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methoxy-1-phenylpyrazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NN(C=C1OC)C1=CC=CC=C1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F KNWGXUWHIZRAMG-UHFFFAOYSA-N 0.000 claims 1
- 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
- KKHQYBCZMHTINI-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methoxypyrimidine-5-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(=NC=NC=1)OC)N1CCC(CC1)OC1=C(C=C(C=C1)F)F KKHQYBCZMHTINI-UHFFFAOYSA-N 0.000 claims 1
- HICWBAKMRQEWQM-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-methoxythiophene-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CSC=C1OC)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HICWBAKMRQEWQM-UHFFFAOYSA-N 0.000 claims 1
- 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
- LVORKAJGPXPUAK-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-4-oxopyrido[1,2-a]pyrimidine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CN=C2N(C1=O)C=CC=C2)N1CCC(CC1)OC1=C(C=C(C=C1)F)F LVORKAJGPXPUAK-UHFFFAOYSA-N 0.000 claims 1
- JYYJJTDBAQQRNF-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C=C2N(N=1)CCC2)N1CCC(CC1)OC1=C(C=C(C=C1)F)F JYYJJTDBAQQRNF-UHFFFAOYSA-N 0.000 claims 1
- OJSULHMCUCDFLD-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-cyclopropyl-1,2-oxazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NOC(=C1)C1CC1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F OJSULHMCUCDFLD-UHFFFAOYSA-N 0.000 claims 1
- YYWIRKIDSGZWOJ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-cyclopropyl-1,3-oxazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=COC=1C1CC1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F YYWIRKIDSGZWOJ-UHFFFAOYSA-N 0.000 claims 1
- ULAXWKZQOFMMDF-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-ethyl-1,2-oxazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NOC(=C1)CC)N1CCC(CC1)OC1=C(C=C(C=C1)F)F ULAXWKZQOFMMDF-UHFFFAOYSA-N 0.000 claims 1
- LRSFETHZDZDMOZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-fluoro-2-methoxybenzamide Chemical compound COc1ccc(F)cc1C(=O)Nc1cc(ccc1N1CCC(CC1)Oc1ccc(F)cc1F)C#N LRSFETHZDZDMOZ-UHFFFAOYSA-N 0.000 claims 1
- QKXOTBITOVSPLA-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-fluoro-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=C(N=CC(=C1)F)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F QKXOTBITOVSPLA-UHFFFAOYSA-N 0.000 claims 1
- ITZGBKIILNGMDE-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-fluoro-6-methylpyridine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=NC(=C(C=C1)F)C)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F ITZGBKIILNGMDE-UHFFFAOYSA-N 0.000 claims 1
- MLKYORIAENTJBJ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-fluoropyridine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=NC=C(C=C1)F)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F MLKYORIAENTJBJ-UHFFFAOYSA-N 0.000 claims 1
- AVQPKSWTZAPSDD-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-methoxypyridine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=NC=C(C=C1)OC)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F AVQPKSWTZAPSDD-UHFFFAOYSA-N 0.000 claims 1
- MOWAKEXNVMZTDR-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-methyl-1,2,4-oxadiazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NOC(=N1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F MOWAKEXNVMZTDR-UHFFFAOYSA-N 0.000 claims 1
- MGKDQLOPGSOSJX-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NOC(=C1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F MGKDQLOPGSOSJX-UHFFFAOYSA-N 0.000 claims 1
- HOUMYAKMQSDUGU-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-methyl-1,3,4-oxadiazole-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1OC(=NN=1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HOUMYAKMQSDUGU-UHFFFAOYSA-N 0.000 claims 1
- DXENBDAZLWPLFV-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-methyl-1,3-oxazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=COC=1C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F DXENBDAZLWPLFV-UHFFFAOYSA-N 0.000 claims 1
- BEZMIDWUECFRFS-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-methylpyrazine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NC=C(N=C1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F BEZMIDWUECFRFS-UHFFFAOYSA-N 0.000 claims 1
- XVNSZIDLFBVXQN-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-5-methylpyridine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(C1=NC=C(C=C1)C)=O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F XVNSZIDLFBVXQN-UHFFFAOYSA-N 0.000 claims 1
- UHXVOSYDVISZRW-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-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)N1CCC(CC1)OC1=C(C=C(C=C1)F)F UHXVOSYDVISZRW-UHFFFAOYSA-N 0.000 claims 1
- TXODBDFYRVKZCU-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C=NN2C=1OCCC2)N1CCC(CC1)OC1=C(C=C(C=C1)F)F TXODBDFYRVKZCU-UHFFFAOYSA-N 0.000 claims 1
- HNIYTOBAYKMWES-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-6-methoxypyridazine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=NC(=CC=1)OC)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HNIYTOBAYKMWES-UHFFFAOYSA-N 0.000 claims 1
- PIYMXOFICQHOSH-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-6-methoxypyridine-2-carboxamide Chemical compound COc1cccc(n1)C(=O)Nc1cc(ccc1N1CCC(CC1)Oc1ccc(F)cc1F)C#N PIYMXOFICQHOSH-UHFFFAOYSA-N 0.000 claims 1
- LGCGSEHWSIBQRM-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-6-methyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CN=C2N(C1=O)C(=CC=C2)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F LGCGSEHWSIBQRM-UHFFFAOYSA-N 0.000 claims 1
- XCSGIPWKXXMTFZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-6-methylpyridazine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=NC(=CC=1)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F XCSGIPWKXXMTFZ-UHFFFAOYSA-N 0.000 claims 1
- XKVFKVBSXSFODW-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-6-oxo-1H-pyridazine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=NC(=CC=1)O)N1CCC(CC1)OC1=C(C=C(C=C1)F)F XKVFKVBSXSFODW-UHFFFAOYSA-N 0.000 claims 1
- BVFCAEVHDWPPDT-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-7-methyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CN=C2N(C1=O)C=C(C=C2)C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F BVFCAEVHDWPPDT-UHFFFAOYSA-N 0.000 claims 1
- HWFDWYNUWIFBTL-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]-9-methyl-4-oxopyrido[1,2-a]pyrimidine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CN=C2N(C1=O)C=CC=C2C)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HWFDWYNUWIFBTL-UHFFFAOYSA-N 0.000 claims 1
- PQMGREWKWXGOQK-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]pyrazine-2-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=NC=CN=C1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F PQMGREWKWXGOQK-UHFFFAOYSA-N 0.000 claims 1
- MSYQIMZPJYWMIF-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]pyridazine-3-carboxamide Chemical compound Fc1ccc(OC2CCN(CC2)c2ccc(cc2NC(=O)c2cccnn2)C#N)c(F)c1 MSYQIMZPJYWMIF-UHFFFAOYSA-N 0.000 claims 1
- VQQZUROVQPHFTG-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]pyrrolo[1,2-c]pyrimidine-3-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C1=CC=2N(C=N1)C=CC=2)N1CCC(CC1)OC1=C(C=C(C=C1)F)F VQQZUROVQPHFTG-UHFFFAOYSA-N 0.000 claims 1
- HXINQZBIJJXBLZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]phenyl]thiadiazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1N=NSC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F HXINQZBIJJXBLZ-UHFFFAOYSA-N 0.000 claims 1
- ZBHSOIJMGMFYNW-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-1-ethyl-5-methoxypyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(=O)C=1C=NN(C=1OC)CC ZBHSOIJMGMFYNW-UHFFFAOYSA-N 0.000 claims 1
- SYQKHVVTJCBJJX-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(=O)C=1C(N(C=CC=1)C)=O SYQKHVVTJCBJJX-UHFFFAOYSA-N 0.000 claims 1
- WVMUJFXJQWNKHX-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(C1=C(N=CC=C1)OC)=O WVMUJFXJQWNKHX-UHFFFAOYSA-N 0.000 claims 1
- XTXPJTWWWSYAQF-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-3-fluoro-6-methylpyridine-2-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(C1=NC(=CC=C1F)C)=O XTXPJTWWWSYAQF-UHFFFAOYSA-N 0.000 claims 1
- GPXFCKBVWRCMRZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(=O)C=1C(=NN(C=1)C)OC GPXFCKBVWRCMRZ-UHFFFAOYSA-N 0.000 claims 1
- PDHKZRXRONGAPC-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-3-methylpyridine-2-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(C1=NC=CC=C1C)=O PDHKZRXRONGAPC-UHFFFAOYSA-N 0.000 claims 1
- DPXXREVVCJAWMV-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-4-fluoro-2-methoxybenzamide Chemical compound COc1cc(F)ccc1C(=O)Nc1cc(cnc1N1CCC(CC1)Oc1ccc(F)cc1F)C#N DPXXREVVCJAWMV-UHFFFAOYSA-N 0.000 claims 1
- SRHNADGGKHSQLU-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-4-oxo-1H-pyridine-3-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(C1=CN=CC=C1O)=O SRHNADGGKHSQLU-UHFFFAOYSA-N 0.000 claims 1
- OISJZZMHILMWNI-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-5-ethoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(=O)C=1C=NN(C=1OCC)C OISJZZMHILMWNI-UHFFFAOYSA-N 0.000 claims 1
- SJFAHLSVYKAYEJ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,4-difluorophenoxy)piperidin-1-yl]pyridin-3-yl]-6-methylpyridine-2-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCC(CC1)OC1=C(C=C(C=C1)F)F)NC(C1=NC(=CC=C1)C)=O SJFAHLSVYKAYEJ-UHFFFAOYSA-N 0.000 claims 1
- QJRSAJGSRYATDC-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,5-difluorobenzoyl)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(C1=C(C=CC(=C1)F)F)=O QJRSAJGSRYATDC-UHFFFAOYSA-N 0.000 claims 1
- YBPAEEBXJLDZJZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,5-difluorophenoxy)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)OC1=C(C=CC(=C1)F)F YBPAEEBXJLDZJZ-UHFFFAOYSA-N 0.000 claims 1
- NKJUPWYORGQCGL-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,5-difluoropyridin-3-yl)oxypiperidin-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)OC=1C(=NC=C(C=1)F)F NKJUPWYORGQCGL-UHFFFAOYSA-N 0.000 claims 1
- KTHQVVYVIFZDCB-UHFFFAOYSA-N N-[5-cyano-2-[4-(2,6-difluorophenoxy)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)OC1=C(C=CC=C1F)F KTHQVVYVIFZDCB-UHFFFAOYSA-N 0.000 claims 1
- IORQQDMSBXAXOX-UHFFFAOYSA-N N-[5-cyano-2-[4-(2-fluoro-4-methoxybenzoyl)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)C(C1=C(C=C(C=C1)OC)F)=O IORQQDMSBXAXOX-UHFFFAOYSA-N 0.000 claims 1
- DRPAFBGDFSPXRD-UHFFFAOYSA-N N-[5-cyano-2-[4-(2-fluoro-4-methoxybenzoyl)piperidin-1-yl]phenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound COC1=CC(F)=C(C=C1)C(=O)C1CCN(CC1)C1=C(NC(=O)C2=CC=CN(C)C2=O)C=C(C=C1)C#N DRPAFBGDFSPXRD-UHFFFAOYSA-N 0.000 claims 1
- MKZNIKDMUSGBLB-UHFFFAOYSA-N N-[5-cyano-2-[4-(2-fluoro-4-methoxyphenoxy)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)OC1=C(C=C(C=C1)OC)F MKZNIKDMUSGBLB-UHFFFAOYSA-N 0.000 claims 1
- WMMMIZSEBIZSNN-UHFFFAOYSA-N N-[5-cyano-2-[4-(2-fluorophenoxy)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)OC1=C(C=CC=C1)F WMMMIZSEBIZSNN-UHFFFAOYSA-N 0.000 claims 1
- DNCKZXUGUPQLDL-UHFFFAOYSA-N N-[5-cyano-2-[4-(3,4-difluorophenoxy)piperidin-1-yl]phenyl]-1-methyl-2-oxopyridine-3-carboxamide Chemical compound CN1C=CC=C(C(=O)NC2=C(C=CC(=C2)C#N)N2CCC(CC2)OC2=CC(F)=C(F)C=C2)C1=O DNCKZXUGUPQLDL-UHFFFAOYSA-N 0.000 claims 1
- XADUSHGAQNQPCG-UHFFFAOYSA-N N-[5-cyano-2-[4-(3,5-difluorophenoxy)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)OC1=CC(=CC(=C1)F)F XADUSHGAQNQPCG-UHFFFAOYSA-N 0.000 claims 1
- MEHJZLUYPBCCIB-UHFFFAOYSA-N N-[5-cyano-2-[4-(3-fluorophenoxy)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)OC1=CC(=CC=C1)F MEHJZLUYPBCCIB-UHFFFAOYSA-N 0.000 claims 1
- AOBVTAYDTPJUBO-UHFFFAOYSA-N N-[5-cyano-2-[4-(3-fluorophenyl)sulfonylpiperidin-1-yl]phenyl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(=NN(C=1)C)OC)N1CCC(CC1)S(=O)(=O)C1=CC(=CC=C1)F AOBVTAYDTPJUBO-UHFFFAOYSA-N 0.000 claims 1
- CLQKZPNHUSGORT-UHFFFAOYSA-N N-[5-cyano-2-[4-(3-methoxyphenyl)sulfonylpiperidin-1-yl]phenyl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound C(#N)C=1C=CC(=C(C=1)NC(=O)C=1C(=NN(C=1)C)OC)N1CCC(CC1)S(=O)(=O)C1=CC(=CC=C1)OC CLQKZPNHUSGORT-UHFFFAOYSA-N 0.000 claims 1
- QXKXMUDVPGSQNQ-UHFFFAOYSA-N N-[5-cyano-2-[4-(4-fluorobenzoyl)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)C(C1=CC=C(C=C1)F)=O QXKXMUDVPGSQNQ-UHFFFAOYSA-N 0.000 claims 1
- XWEIGIRSDZGKOT-UHFFFAOYSA-N N-[5-cyano-2-[4-(4-fluorophenoxy)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)OC1=CC=C(C=C1)F XWEIGIRSDZGKOT-UHFFFAOYSA-N 0.000 claims 1
- ZOGYBGGZOZDOAX-UHFFFAOYSA-N N-[5-cyano-2-[4-(4-fluorophenyl)sulfonylpiperazin-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)S(=O)(=O)C1=CC=C(C=C1)F ZOGYBGGZOZDOAX-UHFFFAOYSA-N 0.000 claims 1
- DMNPTAJHPPWDFZ-UHFFFAOYSA-N N-[5-cyano-2-[4-(thiophen-2-ylmethyl)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)CC=1SC=CC=1 DMNPTAJHPPWDFZ-UHFFFAOYSA-N 0.000 claims 1
- UVAABSBJENDPPA-UHFFFAOYSA-N N-[5-cyano-2-[4-(thiophen-3-ylmethyl)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=CSC=C1 UVAABSBJENDPPA-UHFFFAOYSA-N 0.000 claims 1
- TWUYIMACDIFJPK-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2,3-difluorophenyl)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=C(C(=CC=C1)F)F TWUYIMACDIFJPK-UHFFFAOYSA-N 0.000 claims 1
- ZGPCSGMXQJWYGB-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2,4,6-trifluoro-3-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=C(C(=C(C=C1F)F)OC)F)NC(=O)C=1C(=NN(C=1)C)OC ZGPCSGMXQJWYGB-UHFFFAOYSA-N 0.000 claims 1
- 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
- FSPQJQSZCZJPBZ-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2,4-difluorophenyl)-difluoromethyl]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(F)(F)C1=C(C=C(C=C1)F)F FSPQJQSZCZJPBZ-UHFFFAOYSA-N 0.000 claims 1
- HKTGABZFPPVTFS-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2,5-difluorophenyl)-difluoromethyl]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(F)(F)C1=C(C=CC(=C1)F)F HKTGABZFPPVTFS-UHFFFAOYSA-N 0.000 claims 1
- FDRIUMFJBSBUGD-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2,5-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(F)C1=C(C=CC(=C1)F)F FDRIUMFJBSBUGD-UHFFFAOYSA-N 0.000 claims 1
- IFTXAFRXFPDKBL-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2,6-difluorophenyl)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=C(C=CC=C1F)F IFTXAFRXFPDKBL-UHFFFAOYSA-N 0.000 claims 1
- KHXYOKPQSATSJO-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2-cyano-4-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=C(C=C(C=C1)F)C#N KHXYOKPQSATSJO-UHFFFAOYSA-N 0.000 claims 1
- AYYMLSBNGSVPBZ-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2-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=C(C=CC=C1)C#N AYYMLSBNGSVPBZ-UHFFFAOYSA-N 0.000 claims 1
- WJGUMFFYUNWXDC-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2-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=C(C=C(C=C1)OC)F)NC(=O)C=1C(=NN(C=1)C)OC WJGUMFFYUNWXDC-UHFFFAOYSA-N 0.000 claims 1
- FWTCEKKTSFCBSH-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2-fluoro-4-methoxyphenyl)methyl]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)CC1=C(C=C(C=C1)OC)F FWTCEKKTSFCBSH-UHFFFAOYSA-N 0.000 claims 1
- SSPUJIPXPHRZGJ-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2-fluoro-5-methoxyphenyl)methyl]piperazin-1-yl]phenyl]-2-methoxypyridine-3-carboxamide Chemical compound COc1ccc(F)c(CN2CCN(CC2)c2ccc(cc2NC(=O)c2cccnc2OC)C#N)c1 SSPUJIPXPHRZGJ-UHFFFAOYSA-N 0.000 claims 1
- SUQMTBWOTDLSQB-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2-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=C(C=CC=C1)F SUQMTBWOTDLSQB-UHFFFAOYSA-N 0.000 claims 1
- FCHNHBDROJNRKM-UHFFFAOYSA-N N-[5-cyano-2-[4-[(2-methoxyphenyl)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=C(C=CC=C1)OC FCHNHBDROJNRKM-UHFFFAOYSA-N 0.000 claims 1
- MVTXWYHQFDIORX-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3,4-difluorophenyl)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(=C(C=C1)F)F MVTXWYHQFDIORX-UHFFFAOYSA-N 0.000 claims 1
- FPCYCGRYRFBIBO-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3,5-difluorophenyl)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)F)F)NC(=O)C=1C(=NN(C=1)C)OC FPCYCGRYRFBIBO-UHFFFAOYSA-N 0.000 claims 1
- VKFCEVJGWZOKPZ-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3,5-difluoropyridin-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=C1F)F VKFCEVJGWZOKPZ-UHFFFAOYSA-N 0.000 claims 1
- QPURIALVNICVRU-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3-cyano-4-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=CC(=C(C=C1)F)C#N)NC(=O)C=1C(=NN(C=1)C)OC QPURIALVNICVRU-UHFFFAOYSA-N 0.000 claims 1
- 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
- XHEVQXMGJGSFMH-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3-fluoro-2-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=C(C(=CC=C1)F)OC)NC(=O)C=1C(=NN(C=1)C)OC XHEVQXMGJGSFMH-UHFFFAOYSA-N 0.000 claims 1
- 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
- MZLKRVBKBPADRG-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3-fluoro-5-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(=CC(=C1)OC)F)NC(=O)C=1C(=NN(C=1)C)OC MZLKRVBKBPADRG-UHFFFAOYSA-N 0.000 claims 1
- 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
- ZBUNPENCXIVEHT-UHFFFAOYSA-N N-[5-cyano-2-[4-[(3-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(=CC=C1)OC)NC(=O)C=1C(=NN(C=1)C)OC ZBUNPENCXIVEHT-UHFFFAOYSA-N 0.000 claims 1
- XQVXWYUYTHNFEO-UHFFFAOYSA-N N-[5-cyano-2-[4-[(4,5-difluoro-2-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=C(C=C(C(=C1)F)F)OC)NC(=O)C=1C(=NN(C=1)C)OC XQVXWYUYTHNFEO-UHFFFAOYSA-N 0.000 claims 1
- 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
- ZXHXJDIIYXTVLB-UHFFFAOYSA-N N-[5-cyano-2-[4-[(4-fluoro-2-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=C(C=C(C=C1)F)OC)NC(=O)C=1C(=NN(C=1)C)OC ZXHXJDIIYXTVLB-UHFFFAOYSA-N 0.000 claims 1
- DYBMXARNJLVPCH-UHFFFAOYSA-N N-[5-cyano-2-[4-[(4-fluoro-3-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)F)OC)NC(=O)C=1C(=NN(C=1)C)OC DYBMXARNJLVPCH-UHFFFAOYSA-N 0.000 claims 1
- XKPGFGZRQXWZBZ-UHFFFAOYSA-N N-[5-cyano-2-[4-[(4-fluorophenyl)-methoxymethyl]piperidin-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)N1CCC(CC1)C(OC)C1=CC=C(C=C1)F XKPGFGZRQXWZBZ-UHFFFAOYSA-N 0.000 claims 1
- SJZNNTPPLVTDCU-UHFFFAOYSA-N N-[5-cyano-2-[4-[(4-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=C(C=C1)F SJZNNTPPLVTDCU-UHFFFAOYSA-N 0.000 claims 1
- MVNZNRPLXGNATD-UHFFFAOYSA-N N-[5-cyano-2-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]pyridin-3-yl]-2-methoxypyridine-3-carboxamide Chemical compound C(#N)C=1C=C(C(=NC=1)N1CCN(CC1)CC1=CC=C(C=C1)F)NC(C1=C(N=CC=C1)OC)=O MVNZNRPLXGNATD-UHFFFAOYSA-N 0.000 claims 1
- PGJDVRVVVYLVPB-UHFFFAOYSA-N N-[5-cyano-2-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]pyridin-3-yl]-3-methoxy-1-methylpyrazole-4-carboxamide Chemical compound COc1nn(C)cc1C(=O)Nc1cc(cnc1N1CCN(Cc2ccc(OC)cc2)CC1)C#N PGJDVRVVVYLVPB-UHFFFAOYSA-N 0.000 claims 1
- 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
- JRGFLUDTPJJIQZ-UHFFFAOYSA-N N-[5-cyano-2-[4-[1-(4-fluorophenyl)ethyl]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)C(C)C1=CC=C(C=C1)F JRGFLUDTPJJIQZ-UHFFFAOYSA-N 0.000 claims 1
- NKWFHFGKQUKSHL-UHFFFAOYSA-N N-[5-cyano-2-[4-[[2-(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=C(C=CC=C1)OC(F)F)NC(=O)C=1C(=NN(C=1)C)OC NKWFHFGKQUKSHL-UHFFFAOYSA-N 0.000 claims 1
- 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
- 125000001544 thienyl group Chemical group 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762476846P | 2017-03-26 | 2017-03-26 | |
| US201762476786P | 2017-03-26 | 2017-03-26 | |
| US62/476,786 | 2017-03-26 | ||
| US62/476,846 | 2017-03-26 | ||
| PCT/US2018/024249 WO2018183145A1 (en) | 2017-03-26 | 2018-03-26 | Piperidinyl- and piperazinyl-substituted heteroaromatic carboxamides as modulators of gpr6 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020512401A JP2020512401A (ja) | 2020-04-23 |
| JP2020512401A5 true JP2020512401A5 (https=) | 2021-05-06 |
| JP7142675B2 JP7142675B2 (ja) | 2022-09-27 |
Family
ID=63676658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020501438A Active JP7142675B2 (ja) | 2017-03-26 | 2018-03-26 | Ｇｐｒ６のモジュレーターとしてのピペリジニルおよびピペラジニル置換された複素芳香族カルボキサミド |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US11426397B2 (https=) |
| EP (1) | EP3600312B1 (https=) |
| JP (1) | JP7142675B2 (https=) |
| CN (1) | CN110520127B (https=) |
| AU (1) | AU2018244211B2 (https=) |
| CA (1) | CA3054945A1 (https=) |
| DK (1) | DK3600312T3 (https=) |
| FI (1) | FI3600312T3 (https=) |
| IL (1) | IL269189B2 (https=) |
| MX (1) | MX390512B (https=) |
| WO (1) | WO2018183145A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2021005688A (es) * | 2018-11-14 | 2021-07-07 | Allinky Biopharma | Compuestos de piridina sulfonamida para el tratamiento contra afecciones relacionadas con interleucina 1 beta. |
| WO2021035257A1 (en) * | 2019-08-21 | 2021-02-25 | The Scripps Research Institute | Monocyclic agonists of stimulator of interferon genes sting |
| IL293340A (en) | 2019-12-02 | 2022-07-01 | Storm Therapeutics Ltd | Polyheterocyclic compounds as mettl3 inhibitors |
| CA3188340A1 (en) | 2020-08-13 | 2022-02-17 | Boehringer Ingelheim International Gmbh | Treatment of cognitive impairement associated with schizophrenia |
| CA3195702A1 (en) | 2020-10-13 | 2022-04-21 | Boehringer Ingelheim International Gmbh | Process of reworking |
| WO2022240992A1 (en) * | 2021-05-12 | 2022-11-17 | Libra Therapeutics, Inc. | Heterocyclic trpml1 agonists and uses thereof |
| EP4646263A1 (en) * | 2023-01-20 | 2025-11-12 | Allianthera (Suzhou) Biopharmaceutical Co., Ltd. | Sprk1 inhibitors and methods of use |
| WO2025165967A2 (en) * | 2024-02-02 | 2025-08-07 | Maplight Therapeutics, Inc. | Gpr6 inverse agonists |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| PT1397351E (pt) | 2001-06-01 | 2010-01-04 | Hoffmann La Roche | Derivados de pirimidina, triazina e pirazina como receptores de glutamato |
| CN1321115C (zh) | 2001-11-30 | 2007-06-13 | 霍夫曼-拉罗奇有限公司 | 作为哮喘治疗中的ccr－3受体拮抗剂的哌嗪衍生物 |
| US20040034019A1 (en) | 2002-08-08 | 2004-02-19 | Ronald Tomlinson | Piperazine and piperidine derivatives |
| JP5182088B2 (ja) * | 2006-04-19 | 2013-04-10 | アステラス製薬株式会社 | アゾールカルボキサミド誘導体 |
| CA2668210C (en) | 2006-10-31 | 2013-03-12 | Schering Corporation | Anilinopiperazine derivatives and methods of use thereof |
| PE20091576A1 (es) | 2008-02-19 | 2009-11-05 | Sanofi Aventis | DERIVADOS DE 3-(AMIDO O SULFAMIDO)-4-(4-AZINIL SUSTITUIDO)BENZAMIDA COMO INHIBIDORES DEL RECEPTOR DE QUIMIOQUINAS CxCR3 |
| WO2014028479A1 (en) * | 2012-08-13 | 2014-02-20 | Envoy Therapeutics, Inc. | Quinoxaline derivatives as gpr6 modulators |
| KR20160122215A (ko) * | 2014-02-14 | 2016-10-21 | 다케다 야쿠힌 고교 가부시키가이샤 | Gpr6의 피라진 조절제 |
| GB201406956D0 (en) | 2014-04-17 | 2014-06-04 | Univ Nottingham | Compounds |
-
2018
- 2018-03-26 MX MX2019011286A patent/MX390512B/es unknown
- 2018-03-26 DK DK18775397.5T patent/DK3600312T3/da active
- 2018-03-26 CA CA3054945A patent/CA3054945A1/en active Pending
- 2018-03-26 WO PCT/US2018/024249 patent/WO2018183145A1/en not_active Ceased
- 2018-03-26 CN CN201880024073.0A patent/CN110520127B/zh active Active
- 2018-03-26 EP EP18775397.5A patent/EP3600312B1/en active Active
- 2018-03-26 US US16/497,967 patent/US11426397B2/en active Active
- 2018-03-26 JP JP2020501438A patent/JP7142675B2/ja active Active
- 2018-03-26 AU AU2018244211A patent/AU2018244211B2/en active Active
- 2018-03-26 FI FIEP18775397.5T patent/FI3600312T3/fi active
-
2019
- 2019-09-08 IL IL269189A patent/IL269189B2/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2020512401A5 (https=) | ||
| FI3600312T3 (fi) | Piperidinyyli- ja piperatsinyylisubstituoituja heteroaromaattisia karboksamideja gpr6:n modulaattoreina | |
| HRP20251479T1 (hr) | Pesticidno aktivni kondenzirani biciklički heteroaromatski spojevi | |
| RU2417994C2 (ru) | Производные пиразина, полезные в качестве антагонистов аденозинового рецептора | |
| JP2016522246A5 (https=) | ||
| RU2008141761A (ru) | ИНГИБИТОРЫ с-МЕТ ПРОТЕИНКИНАЗЫ | |
| RU2016102137A (ru) | Первичные карбоксамиды в качестве ингибиторов bik | |
| JP2013528591A5 (https=) | ||
| JP2016523911A5 (https=) | ||
| HRP20201469T1 (hr) | Derivati tetrahidroizokinolina | |
| JP2007510689A5 (https=) | ||
| JP2013515032A5 (https=) | ||
| RU2012126989A (ru) | 2-амино-5,5-дифтор-5,6-дигидро-4н-оксазины в качестве ингибиторов васе 1 и(или) васе 2 | |
| JP2011503166A5 (https=) | ||
| JP2010513444A5 (https=) | ||
| RU2018123779A (ru) | Новые соединения | |
| RU2010137114A (ru) | Амидные производные как позитивные аллостерические модуляторы и способы их применения | |
| JP2019504009A5 (https=) | ||
| RU2017124425A (ru) | Производные 2,4-диоксо-хиназолин-6-сульфонамида в качестве ингибиторов parg | |
| JP2010514677A5 (https=) | ||
| RU2017125520A (ru) | Соединения, ингибирующие parg | |
| JP2010513304A5 (https=) | ||
| RU2018138047A (ru) | Гетероциклические вещества - агонисты gpr119 | |
| JP2009525978A5 (https=) | ||
| JP2009519967A5 (https=) |