NZ581353A - Novel n- (8-heteroaryltetrahydronaphtalene-2yl) or n- (5- heteroarylchromane-3-yl) carboxamide derivatives for the treatment of pain - Google Patents

Info

Publication number

NZ581353A

NZ581353A NZ581353A NZ58135308A NZ581353A NZ 581353 A NZ581353 A NZ 581353A NZ 581353 A NZ581353 A NZ 581353A NZ 58135308 A NZ58135308 A NZ 58135308A NZ 581353 A NZ581353 A NZ 581353A

Authority

NZ

New Zealand

Prior art keywords

chromen

dihydro

nicotinamide

pyridin

acid

Prior art date

2007-04-23

Links

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• 208000002193 Pain Diseases 0.000 title claims abstract description 35
• 230000036407 pain Effects 0.000 title claims abstract description 26
• 238000011282 treatment Methods 0.000 title claims abstract description 15
• 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 446
• -1 4-{ [(2R)-8-Pyridin-4-yl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamoyl} phenyl Chemical group 0.000 claims abstract description 210
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 239000003814 drug Substances 0.000 claims abstract description 6
• 238000004519 manufacturing process Methods 0.000 claims abstract description 5
• UCLANCKZRBWESY-INIZCTEOSA-N n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=CN=CC=3)C=CC=C2OC1 UCLANCKZRBWESY-INIZCTEOSA-N 0.000 claims abstract description 4
• 150000003857 carboxamides Chemical class 0.000 claims abstract 3
• 239000002253 acid Substances 0.000 claims description 305
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 129
• 235000005152 nicotinamide Nutrition 0.000 claims description 65
• 239000011570 nicotinamide Substances 0.000 claims description 65
• 229960003966 nicotinamide Drugs 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
• NGZVNONVXYLYQW-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-amine Chemical compound NCCC(F)(F)F NGZVNONVXYLYQW-UHFFFAOYSA-N 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• 238000002560 therapeutic procedure Methods 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• LEIAZUKOBVWTEH-UHFFFAOYSA-N pyridine-2,5-dicarboxamide Chemical compound NC(=O)C1=CC=C(C(N)=O)N=C1 LEIAZUKOBVWTEH-UHFFFAOYSA-N 0.000 claims description 9
• KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 claims description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 7
• LAXWLCVPJLBABV-UHFFFAOYSA-N 4,4,4-trifluorobutan-1-amine Chemical compound NCCCC(F)(F)F LAXWLCVPJLBABV-UHFFFAOYSA-N 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• XZYJNHZNHGUSNY-UHFFFAOYSA-N 2,2,2-trifluoro-n-methylethanamine Chemical compound CNCC(F)(F)F XZYJNHZNHGUSNY-UHFFFAOYSA-N 0.000 claims description 5
• ONBBNBDNLGQXIX-UHFFFAOYSA-N 3,3,3-trifluoro-n-methylpropan-1-amine Chemical compound CNCCC(F)(F)F ONBBNBDNLGQXIX-UHFFFAOYSA-N 0.000 claims description 5
• UTOXFQVLOTVLSD-UHFFFAOYSA-N 3-propoxypropan-1-amine Chemical compound CCCOCCCN UTOXFQVLOTVLSD-UHFFFAOYSA-N 0.000 claims description 5
• 208000000094 Chronic Pain Diseases 0.000 claims description 5
• QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 claims description 5
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
• ICBYIKRIEVEFCX-UHFFFAOYSA-N oxan-2-amine Chemical compound NC1CCCCO1 ICBYIKRIEVEFCX-UHFFFAOYSA-N 0.000 claims description 5
• DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 5
• 125000005494 pyridonyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 4
• LGWLUYSZXHQDEL-UHFFFAOYSA-N FC(C1CC(C(CC1)C(C)C)S(=O)(=O)O)(F)F Chemical compound FC(C1CC(C(CC1)C(C)C)S(=O)(=O)O)(F)F LGWLUYSZXHQDEL-UHFFFAOYSA-N 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 208000005298 acute pain Diseases 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 4
• LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 4
• VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 claims description 4
• GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 claims description 4
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• MYMLGBAVNHFRJS-UHFFFAOYSA-N trifluoromethanamine Chemical compound NC(F)(F)F MYMLGBAVNHFRJS-UHFFFAOYSA-N 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 4
• HKYBBQGISPGEAA-INIZCTEOSA-N 2,4-dimethoxy-n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]benzamide Chemical compound COC1=CC(OC)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=CN=CC=3)C=CC=C2OC1 HKYBBQGISPGEAA-INIZCTEOSA-N 0.000 claims description 3
• IALDWLMRPMVZQS-IBGZPJMESA-N 2-methoxy-n,n-dimethyl-5-[(3s)-3-[(6-propan-2-yloxypyridine-3-carbonyl)amino]-3,4-dihydro-2h-chromen-5-yl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)N(C)C)C(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OC(C)C)=CC=1)CO2 IALDWLMRPMVZQS-IBGZPJMESA-N 0.000 claims description 3
• QRLFIYONIBJTKV-KRWDZBQOSA-N 2-methoxy-n,n-dimethyl-5-[(3s)-3-[[6-(2,2,2-trifluoroethoxy)pyridine-3-carbonyl]amino]-3,4-dihydro-2h-chromen-5-yl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)N(C)C)C(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCC(F)(F)F)=CC=1)CO2 QRLFIYONIBJTKV-KRWDZBQOSA-N 0.000 claims description 3
• AZXQFQCJJIQAMX-FQEVSTJZSA-N 2-methoxy-n,n-dimethyl-5-[(3s)-3-[[6-(oxan-4-yloxy)pyridine-3-carbonyl]amino]-3,4-dihydro-2h-chromen-5-yl]pyridine-3-carboxamide Chemical compound C1=C(C(=O)N(C)C)C(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OC3CCOCC3)=CC=1)CO2 AZXQFQCJJIQAMX-FQEVSTJZSA-N 0.000 claims description 3
• LVGBLGDOILFKFG-SFHVURJKSA-N 2-methoxy-n-methyl-5-[(3s)-3-[(6-propan-2-yloxypyridine-3-carbonyl)amino]-3,4-dihydro-2h-chromen-5-yl]pyridine-3-carboxamide Chemical compound N1=C(OC)C(C(=O)NC)=CC(C=2C=3C[C@@H](COC=3C=CC=2)NC(=O)C=2C=NC(OC(C)C)=CC=2)=C1 LVGBLGDOILFKFG-SFHVURJKSA-N 0.000 claims description 3
• LCBLHBHJHJCOFX-IBGZPJMESA-N 2-methoxy-n-methyl-5-[(3s)-3-[[6-(oxan-4-yloxy)pyridine-3-carbonyl]amino]-3,4-dihydro-2h-chromen-5-yl]pyridine-3-carboxamide Chemical compound N1=C(OC)C(C(=O)NC)=CC(C=2C=3C[C@@H](COC=3C=CC=2)NC(=O)C=2C=NC(OC3CCOCC3)=CC=2)=C1 LCBLHBHJHJCOFX-IBGZPJMESA-N 0.000 claims description 3
• BMSFSZFBPUMOPH-IBGZPJMESA-N 2-n-(4,4-difluorocyclohexyl)-5-n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]pyridine-2,5-dicarboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NC1CCC(F)(F)CC1)CO2 BMSFSZFBPUMOPH-IBGZPJMESA-N 0.000 claims description 3
• HUSAHEFLQYVOPI-KRWDZBQOSA-N 2-n-methyl-5-n-[(3s)-5-(2-methylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(2,2,2-trifluoroethyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(C(=O)N(CC(F)(F)F)C)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=NC(C)=NC=3)C=CC=C2OC1 HUSAHEFLQYVOPI-KRWDZBQOSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• YYZMKZGRGUGDDG-FQEVSTJZSA-N 4-butoxy-n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]benzamide Chemical compound C1=CC(OCCCC)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=CN=CC=3)C=CC=C2OC1 YYZMKZGRGUGDDG-FQEVSTJZSA-N 0.000 claims description 3
• QTOSVJVQRBADEZ-ZDUSSCGKSA-N 5-methoxy-n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]pyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)N[C@H]1CC2=C(C=3C=NC(OC)=NC=3)C=CC=C2OC1 QTOSVJVQRBADEZ-ZDUSSCGKSA-N 0.000 claims description 3
• JSFZTUKVPUTLJW-AWEZNQCLSA-N 5-methoxy-n-[(3s)-5-pyridin-3-yl-3,4-dihydro-2h-chromen-3-yl]pyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)N[C@H]1CC2=C(C=3C=NC=CC=3)C=CC=C2OC1 JSFZTUKVPUTLJW-AWEZNQCLSA-N 0.000 claims description 3
• OBAOUMISTWGKIY-AWEZNQCLSA-N 5-methoxy-n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]pyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)N[C@H]1CC2=C(C=3C=CN=CC=3)C=CC=C2OC1 OBAOUMISTWGKIY-AWEZNQCLSA-N 0.000 claims description 3
• DVPOOPQWXFCWPA-SFHVURJKSA-N 5-n-[(3s)-5-(2-cyclopropylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(3,3,3-trifluoropropyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(C(=O)NCCC(F)(F)F)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=NC(=NC=3)C3CC3)C=CC=C2OC1 DVPOOPQWXFCWPA-SFHVURJKSA-N 0.000 claims description 3
• PPJLALVHECUNEG-KRWDZBQOSA-N 5-n-[(3s)-5-(2-ethylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(3,3,3-trifluoropropyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(CC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NCCC(F)(F)F)CO2 PPJLALVHECUNEG-KRWDZBQOSA-N 0.000 claims description 3
• IJXDVYJKSSCRBU-FQEVSTJZSA-N 5-n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n,2-n-dipropylpyridine-2,5-dicarboxamide Chemical compound C1=NC(C(=O)N(CCC)CCC)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=NC(OC)=NC=3)C=CC=C2OC1 IJXDVYJKSSCRBU-FQEVSTJZSA-N 0.000 claims description 3
• FSKUARANMRCZKP-INIZCTEOSA-N 5-n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(3,3,3-trifluoropropyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NCCC(F)(F)F)CO2 FSKUARANMRCZKP-INIZCTEOSA-N 0.000 claims description 3
• OYSHIVZVUNQXPE-IBGZPJMESA-N 5-n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(3-methylbutyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NCCC(C)C)CO2 OYSHIVZVUNQXPE-IBGZPJMESA-N 0.000 claims description 3
• NYMLZCNQVWWKMN-FQEVSTJZSA-N 5-n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(3-propan-2-yloxypropyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NCCCOC(C)C)CO2 NYMLZCNQVWWKMN-FQEVSTJZSA-N 0.000 claims description 3
• VTGNICXGXAIINI-KRWDZBQOSA-N 5-n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(4,4,4-trifluorobutyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NCCCC(F)(F)F)CO2 VTGNICXGXAIINI-KRWDZBQOSA-N 0.000 claims description 3
• ZEKVOBKHSIWXTJ-IBGZPJMESA-N 5-n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-methyl-2-n-(2-methylpropyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)N(C)CC(C)C)CO2 ZEKVOBKHSIWXTJ-IBGZPJMESA-N 0.000 claims description 3
• IUVVXDWFRONRMV-KRWDZBQOSA-N 5-n-[(3s)-5-(2-methylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(3,3,3-trifluoropropyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(C)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NCCC(F)(F)F)CO2 IUVVXDWFRONRMV-KRWDZBQOSA-N 0.000 claims description 3
• NQLOEKJKDMUAJI-NRFANRHFSA-N 5-n-[(3s)-5-(2-methylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(3-propan-2-yloxypropyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(C(=O)NCCCOC(C)C)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=NC(C)=NC=3)C=CC=C2OC1 NQLOEKJKDMUAJI-NRFANRHFSA-N 0.000 claims description 3
• JLBUGCOVYRFJIB-SFHVURJKSA-N 5-n-[(3s)-5-(2-methylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(4,4,4-trifluorobutyl)pyridine-2,5-dicarboxamide Chemical compound C1=NC(C)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NCCCC(F)(F)F)CO2 JLBUGCOVYRFJIB-SFHVURJKSA-N 0.000 claims description 3
• XMNQZAHUMGNLIV-INIZCTEOSA-N 5-n-[(3s)-5-(5-fluoro-6-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-2-n-(3,3,3-trifluoropropyl)pyridine-2,5-dicarboxamide Chemical compound C1=C(F)C(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(=CC=1)C(=O)NCCC(F)(F)F)CO2 XMNQZAHUMGNLIV-INIZCTEOSA-N 0.000 claims description 3
• NGQVMTFXGYWDMO-INIZCTEOSA-N 5-propan-2-yloxy-n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]pyrazine-2-carboxamide Chemical compound C1=NC(OC(C)C)=CN=C1C(=O)N[C@H]1CC2=C(C=3C=CN=CC=3)C=CC=C2OC1 NGQVMTFXGYWDMO-INIZCTEOSA-N 0.000 claims description 3
• RUCLWVHPZZKUOY-IBGZPJMESA-N 6-(2-methylpropoxy)-n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]pyridine-3-carboxamide Chemical compound C1=NC(OCC(C)C)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=CN=CC=3)C=CC=C2OC1 RUCLWVHPZZKUOY-IBGZPJMESA-N 0.000 claims description 3
• ZKFLYYPEJDMXGP-IBGZPJMESA-N 6-(oxan-4-yloxy)-n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]pyridine-3-carboxamide Chemical compound C([C@H](CC1=2)NC(=O)C=3C=NC(OC4CCOCC4)=CC=3)OC1=CC=CC=2C1=CC=NC=C1 ZKFLYYPEJDMXGP-IBGZPJMESA-N 0.000 claims description 3
• SRTCQCUXMHMLCN-HNNXBMFYSA-N 6-chloro-n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]pyridine-3-carboxamide Chemical compound C1=NC(Cl)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=CN=CC=3)C=CC=C2OC1 SRTCQCUXMHMLCN-HNNXBMFYSA-N 0.000 claims description 3
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• KZLBPSPIIQPNNA-KRWDZBQOSA-N 6-ethoxy-n-[(3s)-5-pyridin-4-yl-3,4-dihydro-2h-chromen-3-yl]pyridine-3-carboxamide Chemical compound C1=NC(OCC)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=CN=CC=3)C=CC=C2OC1 KZLBPSPIIQPNNA-KRWDZBQOSA-N 0.000 claims description 3
• BJENZLHEMPSXJB-SFHVURJKSA-N 6-propan-2-yloxy-n-[(3s)-5-pyridin-3-yl-3,4-dihydro-2h-chromen-3-yl]pyridine-3-carboxamide Chemical compound C1=NC(OC(C)C)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=NC=CC=3)C=CC=C2OC1 BJENZLHEMPSXJB-SFHVURJKSA-N 0.000 claims description 3
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• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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• GYHQDLFHPFCAMZ-KRWDZBQOSA-N n-[(3s)-5-(2-fluoropyridin-4-yl)-3,4-dihydro-2h-chromen-3-yl]-6-propan-2-yloxypyridine-3-carboxamide Chemical compound C1=NC(OC(C)C)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=C(F)N=CC=3)C=CC=C2OC1 GYHQDLFHPFCAMZ-KRWDZBQOSA-N 0.000 claims description 3
• VIQQIYMCHUBNAE-INIZCTEOSA-N n-[(3s)-5-(2-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide Chemical compound COC1=NC=CC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCC(F)(F)F)=CC=1)CO2 VIQQIYMCHUBNAE-INIZCTEOSA-N 0.000 claims description 3
• ROWDZJZWOQWQKD-KRWDZBQOSA-N n-[(3s)-5-(2-methoxypyridin-4-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide Chemical compound C1=NC(OC)=CC(C=2C=3C[C@@H](COC=3C=CC=2)NC(=O)C=2C=NC(OCCC(F)(F)F)=CC=2)=C1 ROWDZJZWOQWQKD-KRWDZBQOSA-N 0.000 claims description 3
• GDYRXDIVDVSUOX-HNNXBMFYSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-(3,3,3-trifluoropropylamino)pyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(NCCC(F)(F)F)=NC=1)CO2 GDYRXDIVDVSUOX-HNNXBMFYSA-N 0.000 claims description 3
• KXXUNPVJWFBHMW-KRWDZBQOSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-2-[2-(2,2,2-trifluoroethoxy)ethoxy]pyridine-4-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=C(OCCOCC(F)(F)F)N=CC=1)CO2 KXXUNPVJWFBHMW-KRWDZBQOSA-N 0.000 claims description 3
• NJPJBJRUOPSFOM-AWEZNQCLSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-4-methyl-2-(2,2,2-trifluoroethoxy)pyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C(=NC(OCC(F)(F)F)=NC=1)C)CO2 NJPJBJRUOPSFOM-AWEZNQCLSA-N 0.000 claims description 3
• UHWLMTBESYAWAT-INIZCTEOSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-4-methyl-2-propan-2-yloxypyrimidine-5-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C(=NC(OC(C)C)=NC=1)C)CO2 UHWLMTBESYAWAT-INIZCTEOSA-N 0.000 claims description 3
• BEZZRZYETXKPJS-HNNXBMFYSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCC(F)(F)F)=CC=1)CO2 BEZZRZYETXKPJS-HNNXBMFYSA-N 0.000 claims description 3
• VOINGHQJWLVWMC-KRWDZBQOSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(2,2,2-trifluoroethoxymethyl)pyridine-3-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(COCC(F)(F)F)=CC=1)CO2 VOINGHQJWLVWMC-KRWDZBQOSA-N 0.000 claims description 3
• NLLYXEPGGVAVHY-INIZCTEOSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCC(F)(F)F)=CC=1)CO2 NLLYXEPGGVAVHY-INIZCTEOSA-N 0.000 claims description 3
• QTYJJHMCZUUWRI-XJDOXCRVSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(oxan-2-ylmethoxy)pyridine-3-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCC3OCCCC3)=CC=1)CO2 QTYJJHMCZUUWRI-XJDOXCRVSA-N 0.000 claims description 3
• HCURPKYNYNHIEE-OYKVQYDMSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(oxan-3-yloxy)pyridine-3-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OC3COCCC3)=CC=1)CO2 HCURPKYNYNHIEE-OYKVQYDMSA-N 0.000 claims description 3
• ZNECSSZPXNNPAB-OYKVQYDMSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(oxolan-2-ylmethoxy)pyridine-3-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCC3OCCC3)=CC=1)CO2 ZNECSSZPXNNPAB-OYKVQYDMSA-N 0.000 claims description 3
• LFITVGQHPHAAMW-ZENAZSQFSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(oxolan-3-yloxy)pyridine-3-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OC3COCC3)=CC=1)CO2 LFITVGQHPHAAMW-ZENAZSQFSA-N 0.000 claims description 3
• JESJRZKWPVQWSL-KRWDZBQOSA-N n-[(3s)-5-(2-methoxypyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-[2-(2,2,2-trifluoroethoxy)ethoxy]pyridine-3-carboxamide Chemical compound C1=NC(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCOCC(F)(F)F)=CC=1)CO2 JESJRZKWPVQWSL-KRWDZBQOSA-N 0.000 claims description 3
• AXIVJHFHJBRASG-SFHVURJKSA-N n-[(3s)-5-(2-methylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(2,2,2-trifluoroethoxymethyl)pyridine-3-carboxamide Chemical compound C1=NC(C)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(COCC(F)(F)F)=CC=1)CO2 AXIVJHFHJBRASG-SFHVURJKSA-N 0.000 claims description 3
• CXSWKIKEXSGCCJ-KRWDZBQOSA-N n-[(3s)-5-(2-methylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide Chemical compound C1=NC(C)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCC(F)(F)F)=CC=1)CO2 CXSWKIKEXSGCCJ-KRWDZBQOSA-N 0.000 claims description 3
• OCDRCJCFKJHXNS-IBGZPJMESA-N n-[(3s)-5-(2-methylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(oxan-4-yloxy)pyridine-3-carboxamide Chemical compound C1=NC(C)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OC3CCOCC3)=CC=1)CO2 OCDRCJCFKJHXNS-IBGZPJMESA-N 0.000 claims description 3
• GPFSVHDNBQACLO-SFHVURJKSA-N n-[(3s)-5-(2-methylpyrimidin-5-yl)-3,4-dihydro-2h-chromen-3-yl]-6-[2-(2,2,2-trifluoroethoxy)ethoxy]pyridine-3-carboxamide Chemical compound C1=NC(C)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCOCC(F)(F)F)=CC=1)CO2 GPFSVHDNBQACLO-SFHVURJKSA-N 0.000 claims description 3
• DQUDATULPSRZRL-AWEZNQCLSA-N n-[(3s)-5-(3,6-dimethoxypyridazin-4-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound N1=NC(OC)=CC(C=2C=3C[C@@H](COC=3C=CC=2)NC(=O)C=2C=NC(OCC(F)(F)F)=CC=2)=C1OC DQUDATULPSRZRL-AWEZNQCLSA-N 0.000 claims description 3
• VANQLJZFZBZHEH-KRWDZBQOSA-N n-[(3s)-5-(3-methylpyridin-4-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide Chemical compound CC1=CN=CC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCC(F)(F)F)=CC=1)CO2 VANQLJZFZBZHEH-KRWDZBQOSA-N 0.000 claims description 3
• PNWCXXSZYISFFM-BHWOMJMDSA-N n-[(3s)-5-(5-fluoro-6-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-2-(oxolan-3-yloxy)pyrimidine-5-carboxamide Chemical compound C1=C(F)C(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OC3COCC3)=NC=1)CO2 PNWCXXSZYISFFM-BHWOMJMDSA-N 0.000 claims description 3
• ZMUHUMOGKYNCCW-ZDUSSCGKSA-N n-[(3s)-5-(5-fluoro-6-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)N[C@H]1CC2=C(C=3C=C(F)C(OC)=NC=3)C=CC=C2OC1 ZMUHUMOGKYNCCW-ZDUSSCGKSA-N 0.000 claims description 3
• ZTCPMSPMGABOTJ-HNNXBMFYSA-N n-[(3s)-5-(5-fluoro-6-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1=C(F)C(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCC(F)(F)F)=CC=1)CO2 ZTCPMSPMGABOTJ-HNNXBMFYSA-N 0.000 claims description 3
• SJMCHXMJULZDQX-INIZCTEOSA-N n-[(3s)-5-(5-fluoro-6-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide Chemical compound C1=C(F)C(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCC(F)(F)F)=CC=1)CO2 SJMCHXMJULZDQX-INIZCTEOSA-N 0.000 claims description 3
• PQBMHHNDXVEWQM-KRWDZBQOSA-N n-[(3s)-5-(5-fluoro-6-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-[2-(2,2,2-trifluoroethoxy)ethoxy]pyridine-3-carboxamide Chemical compound C1=C(F)C(OC)=NC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCOCC(F)(F)F)=CC=1)CO2 PQBMHHNDXVEWQM-KRWDZBQOSA-N 0.000 claims description 3
• GNOVSBXMWJTRKL-IBGZPJMESA-N n-[(3s)-5-(6-cyanopyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-[2-(2,2,2-trifluoroethoxy)ethoxy]pyridine-3-carboxamide Chemical compound C1=NC(OCCOCC(F)(F)F)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=NC(=CC=3)C#N)C=CC=C2OC1 GNOVSBXMWJTRKL-IBGZPJMESA-N 0.000 claims description 3
• ICNPFARNLBLFQI-OYKVQYDMSA-N n-[(3s)-5-(6-fluoro-5-methylpyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-2-(oxan-3-yloxy)pyrimidine-5-carboxamide Chemical compound N1=C(F)C(C)=CC(C=2C=3C[C@@H](COC=3C=CC=2)NC(=O)C=2C=NC(OC3COCCC3)=NC=2)=C1 ICNPFARNLBLFQI-OYKVQYDMSA-N 0.000 claims description 3
• NRCAWVYWNJRUGC-KRWDZBQOSA-N n-[(3s)-5-(6-fluoropyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(2-methoxyethoxy)pyridine-3-carboxamide Chemical compound C1=NC(OCCOC)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=NC(F)=CC=3)C=CC=C2OC1 NRCAWVYWNJRUGC-KRWDZBQOSA-N 0.000 claims description 3
• YQRNZTGKCTXBKF-INIZCTEOSA-N n-[(3s)-5-(6-fluoropyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide Chemical compound C1=NC(F)=CC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCC(F)(F)F)=CC=1)CO2 YQRNZTGKCTXBKF-INIZCTEOSA-N 0.000 claims description 3
• NXNQSQZBBFZJQN-KRWDZBQOSA-N n-[(3s)-5-(6-fluoropyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-propan-2-yloxypyridine-3-carboxamide Chemical compound C1=NC(OC(C)C)=CC=C1C(=O)N[C@H]1CC2=C(C=3C=NC(F)=CC=3)C=CC=C2OC1 NXNQSQZBBFZJQN-KRWDZBQOSA-N 0.000 claims description 3
• XSIHSODFWOZWDV-HNNXBMFYSA-N n-[(3s)-5-(6-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-5-(3,3,3-trifluoropropoxy)pyrazine-2-carboxamide Chemical compound C1=NC(OC)=CC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1N=CC(OCCC(F)(F)F)=NC=1)CO2 XSIHSODFWOZWDV-HNNXBMFYSA-N 0.000 claims description 3
• UTHZRKCPIZOYPZ-KRWDZBQOSA-N n-[(3s)-5-(6-methoxypyridin-3-yl)-3,4-dihydro-2h-chromen-3-yl]-6-(3,3,3-trifluoropropoxy)pyridine-3-carboxamide Chemical compound C1=NC(OC)=CC=C1C1=CC=CC2=C1C[C@H](NC(=O)C=1C=NC(OCCC(F)(F)F)=CC=1)CO2 UTHZRKCPIZOYPZ-KRWDZBQOSA-N 0.000 claims description 3
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