JPWO2019145726A5 - - Google Patents
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- JPWO2019145726A5 JPWO2019145726A5 JP2020560615A JP2020560615A JPWO2019145726A5 JP WO2019145726 A5 JPWO2019145726 A5 JP WO2019145726A5 JP 2020560615 A JP2020560615 A JP 2020560615A JP 2020560615 A JP2020560615 A JP 2020560615A JP WO2019145726 A5 JPWO2019145726 A5 JP WO2019145726A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- amino
- carboxamide
- acetyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 description 796
- -1 methoxy, ethoxy Chemical group 0.000 description 533
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 521
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 447
- 125000003277 amino group Chemical compound 0.000 description 436
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 150
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 55
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 49
- 125000000217 alkyl group Chemical group 0.000 description 47
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 125000001424 substituent group Chemical group 0.000 description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 21
- 125000005843 halogen group Chemical group 0.000 description 21
- 150000003936 benzamides Chemical compound 0.000 description 18
- 239000000126 substance Substances 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- 201000010099 disease Diseases 0.000 description 13
- 125000004029 hydroxymethyl group Chemical compound [H]OC([H])([H])* 0.000 description 11
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 8
- VZIHTQKMHLOIII-UHFFFAOYSA-N 3,5-dihydro-2H-furan Chemical compound [CH]1CCOC1 VZIHTQKMHLOIII-UHFFFAOYSA-N 0.000 description 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 8
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 7
- 125000003917 carbamoyl group Chemical compound [H]N([H])C(*)=O 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- 102000003787 Anoctamin-1 Human genes 0.000 description 6
- 108090000160 Anoctamin-1 Proteins 0.000 description 6
- 125000003236 benzoyl group Chemical compound [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- 125000001951 carbamoylamino group Chemical compound C(N)(=O)N* 0.000 description 6
- 125000004432 carbon atoms Chemical group C* 0.000 description 6
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 6
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 206010038683 Respiratory disease Diseases 0.000 description 5
- 125000002837 carbocyclic group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 125000004066 1-hydroxyethyl group Chemical compound [H]OC([H])([*])C([H])([H])[H] 0.000 description 4
- BRXDADWFUXOZAJ-UHFFFAOYSA-N 2-(5-chloro-2-hydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC(Cl)=CC=C1O BRXDADWFUXOZAJ-UHFFFAOYSA-N 0.000 description 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 4
- VGPYDKSJYTXYFO-UHFFFAOYSA-N BrC=1C(=C(C=C(C=1)Cl)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C)O Chemical compound BrC=1C(=C(C=C(C=1)Cl)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C)O VGPYDKSJYTXYFO-UHFFFAOYSA-N 0.000 description 4
- CEPVGHGTXVKIAM-UHFFFAOYSA-N C(C)(C)(C)NC(=O)C1=NC=C(C(=C1)NC(CC1=C(C=CC(=C1)Cl)O)=O)F Chemical compound C(C)(C)(C)NC(=O)C1=NC=C(C(=C1)NC(CC1=C(C=CC(=C1)Cl)O)=O)F CEPVGHGTXVKIAM-UHFFFAOYSA-N 0.000 description 4
- JYNLGWPCZOXRSQ-UHFFFAOYSA-N C(C)(C)(C)NC(=O)C1=NC=CC(=C1)NC(CC=1C=C(C(=O)OC)C=CC=1O)=O Chemical compound C(C)(C)(C)NC(=O)C1=NC=CC(=C1)NC(CC=1C=C(C(=O)OC)C=CC=1O)=O JYNLGWPCZOXRSQ-UHFFFAOYSA-N 0.000 description 4
- PEZFQUNMGCXABE-UHFFFAOYSA-N C(C)(C)(C)NC(C1=C(C=CC(=C1)NC(CC1=C(C=CC(=C1)Cl)O)=O)F)=O Chemical compound C(C)(C)(C)NC(C1=C(C=CC(=C1)NC(CC1=C(C=CC(=C1)Cl)O)=O)F)=O PEZFQUNMGCXABE-UHFFFAOYSA-N 0.000 description 4
- NRDWFVYRSWLEHD-UHFFFAOYSA-N C(C)(C)(C)NC(C1=C(C=CC(=C1)NC(CC1=C(C=CC(=C1)Cl)O)=O)O)=O Chemical compound C(C)(C)(C)NC(C1=C(C=CC(=C1)NC(CC1=C(C=CC(=C1)Cl)O)=O)O)=O NRDWFVYRSWLEHD-UHFFFAOYSA-N 0.000 description 4
- MJJJSCCVGDNTQE-UHFFFAOYSA-N C(C)(C)(C)NC(C1=CC(=C(C=C1)F)NC(CC1=C(C=CC(=C1)Cl)O)=O)=O Chemical compound C(C)(C)(C)NC(C1=CC(=C(C=C1)F)NC(CC1=C(C=CC(=C1)Cl)O)=O)=O MJJJSCCVGDNTQE-UHFFFAOYSA-N 0.000 description 4
- FWSZWEJAHFAFGK-UHFFFAOYSA-N C(C)(C)(C)NC(C1=CC(=C(C=C1)O)NC(CC1=C(C=CC(=C1)Cl)O)=O)=O Chemical compound C(C)(C)(C)NC(C1=CC(=C(C=C1)O)NC(CC1=C(C=CC(=C1)Cl)O)=O)=O FWSZWEJAHFAFGK-UHFFFAOYSA-N 0.000 description 4
- RMSTVRMUSWRYHX-UHFFFAOYSA-N C(C)(C)(C)NC(C1=CC(=C(C=C1)OC)NC(CC1=C(C=CC(=C1)Cl)O)=O)=O Chemical compound C(C)(C)(C)NC(C1=CC(=C(C=C1)OC)NC(CC1=C(C=CC(=C1)Cl)O)=O)=O RMSTVRMUSWRYHX-UHFFFAOYSA-N 0.000 description 4
- CHINRINRGDKHGR-UHFFFAOYSA-N C(C)(C)(C)NC(C1=CC(=CC(=C1)F)NC(CC1=C(C=CC(=C1)Cl)O)=O)=O Chemical compound C(C)(C)(C)NC(C1=CC(=CC(=C1)F)NC(CC1=C(C=CC(=C1)Cl)O)=O)=O CHINRINRGDKHGR-UHFFFAOYSA-N 0.000 description 4
- VVRXQDVZJBQJEE-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C Chemical compound C(C1=CC=CC=C1)NC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C VVRXQDVZJBQJEE-UHFFFAOYSA-N 0.000 description 4
- 206010013781 Dry mouth Diseases 0.000 description 4
- NGRGOQOEAQPOSS-UHFFFAOYSA-N N1=CC=CC2=CC(=CC=C12)CC(=O)NC1=CC(=NC=C1)C(=O)NC1CCOCC1 Chemical compound N1=CC=CC2=CC(=CC=C12)CC(=O)NC1=CC(=NC=C1)C(=O)NC1CCOCC1 NGRGOQOEAQPOSS-UHFFFAOYSA-N 0.000 description 4
- VMFGYVSINRYPTH-UHFFFAOYSA-N NC1=C(C=CC(=C1)C(C)(C)C)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C Chemical compound NC1=C(C=CC(=C1)C(C)(C)C)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C VMFGYVSINRYPTH-UHFFFAOYSA-N 0.000 description 4
- ZJAGBRRCQVZDSL-UHFFFAOYSA-N NC=1C=C(C=CC=1C(C)(C)C)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C Chemical compound NC=1C=C(C=CC=1C(C)(C)C)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C ZJAGBRRCQVZDSL-UHFFFAOYSA-N 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000001064 morpholinomethyl group Chemical compound [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 4
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical compound [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- 125000006318 tert-butyl amino group Chemical compound [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 3
- 125000001960 7 membered carbocyclic group Chemical group 0.000 description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004452 carbocyclyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 125000005842 heteroatoms Chemical group 0.000 description 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- NLOLSXYRJFEOTA-OWOJBTEDSA-N (E)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C\C(F)(F)F NLOLSXYRJFEOTA-OWOJBTEDSA-N 0.000 description 2
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-Ethyl Chemical compound C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical compound [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000001622 2-naphthyl group Chemical compound [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- ZGRFBTFRUGAJRA-UHFFFAOYSA-N 3,3-difluoro-1$l^{2}-azolidine Chemical compound FC1(F)CC[N]C1 ZGRFBTFRUGAJRA-UHFFFAOYSA-N 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- 125000004211 3,5-difluorophenyl group Chemical compound [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical compound [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical compound [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N 4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- MBNOBRSQXQXRJI-UHFFFAOYSA-N BrC1=C(C=CC=C1)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C Chemical compound BrC1=C(C=CC=C1)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C MBNOBRSQXQXRJI-UHFFFAOYSA-N 0.000 description 2
- FDRTWBIJXRIBSI-UHFFFAOYSA-N BrC1=CC(=C(C=C1Cl)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C)O Chemical compound BrC1=CC(=C(C=C1Cl)CC(=O)NC1=CC(=NC=C1)C(=O)NC(C)(C)C)O FDRTWBIJXRIBSI-UHFFFAOYSA-N 0.000 description 2
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| CA3145120A1 (en) * | 2019-07-24 | 2021-01-28 | Tmem16A Limited | Pyridine derivatives as tmem16a modulators for use in the treatment of respiratory conditions |
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| WO2022150174A1 (en) | 2021-01-06 | 2022-07-14 | AbbVie Global Enterprises Ltd. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
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