JP2011516546A5 - - Google Patents
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- JP2011516546A5 JP2011516546A5 JP2011503949A JP2011503949A JP2011516546A5 JP 2011516546 A5 JP2011516546 A5 JP 2011516546A5 JP 2011503949 A JP2011503949 A JP 2011503949A JP 2011503949 A JP2011503949 A JP 2011503949A JP 2011516546 A5 JP2011516546 A5 JP 2011516546A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxo
- amino
- ethyl
- hydropyridino
- 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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- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 188
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 128
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 124
- -1 CF 3 Chemical group 0.000 claims description 111
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 102
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 94
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 22
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- BHHMPZQRVWVAAR-UHFFFAOYSA-N 7-bromo-8-methylpyrido[2,3-b]pyrazine Chemical compound C1=CN=C2C(C)=C(Br)C=NC2=N1 BHHMPZQRVWVAAR-UHFFFAOYSA-N 0.000 claims description 10
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 10
- 125000001475 halogen functional group Chemical group 0.000 claims description 10
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- LAQJGAKLLZAETL-UHFFFAOYSA-N 2h-pyrazin-3-one Chemical compound O=C1CN=CC=N1 LAQJGAKLLZAETL-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 108010087894 Fatty acid desaturases Proteins 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims description 3
- VZQUYZBJYXLPLQ-CQSZACIVSA-N (2r)-2-hydroxy-n-[2-[3-methyl-2-oxo-7-[[3-(trifluoromethyl)phenyl]methylamino]quinoxalin-1-yl]ethyl]propanamide Chemical compound C=1C=C2N=C(C)C(=O)N(CCNC(=O)[C@H](O)C)C2=CC=1NCC1=CC=CC(C(F)(F)F)=C1 VZQUYZBJYXLPLQ-CQSZACIVSA-N 0.000 claims description 2
- VZQUYZBJYXLPLQ-AWEZNQCLSA-N (2s)-2-hydroxy-n-[2-[3-methyl-2-oxo-7-[[3-(trifluoromethyl)phenyl]methylamino]quinoxalin-1-yl]ethyl]propanamide Chemical compound C=1C=C2N=C(C)C(=O)N(CCNC(=O)[C@@H](O)C)C2=CC=1NCC1=CC=CC(C(F)(F)F)=C1 VZQUYZBJYXLPLQ-AWEZNQCLSA-N 0.000 claims description 2
- MTMGWUJFNDKEFG-UHFFFAOYSA-N 1-(2-acetamidoethyl)-n-[(3,4-dichlorophenyl)methyl]-3-(4-methoxyphenyl)-2-oxoquinoxaline-6-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(C(=O)NCC=3C=C(Cl)C(Cl)=CC=3)=CC=C2N(CCNC(C)=O)C1=O MTMGWUJFNDKEFG-UHFFFAOYSA-N 0.000 claims description 2
- APYONNMRNATNGB-UHFFFAOYSA-N 2-[3-methyl-2-oxo-7-[[3-(trifluoromethyl)phenyl]methylamino]quinoxalin-1-yl]ethylurea Chemical group C1=C2N(CCNC(N)=O)C(=O)C(C)=NC2=CC=C1NCC1=CC=CC(C(F)(F)F)=C1 APYONNMRNATNGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- OPWMHRPIBJVJTC-UHFFFAOYSA-N 3-hydroxy-n-[2-[3-methyl-2-oxo-7-[[3-(trifluoromethyl)phenyl]methylamino]quinoxalin-1-yl]ethyl]propanamide Chemical compound C1=C2N(CCNC(=O)CCO)C(=O)C(C)=NC2=CC=C1NCC1=CC=CC(C(F)(F)F)=C1 OPWMHRPIBJVJTC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- JWSWKNZAKWPCIZ-UHFFFAOYSA-N C(C)(=O)NN1CC=NC=C1 Chemical compound C(C)(=O)NN1CC=NC=C1 JWSWKNZAKWPCIZ-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- RMRDBXLTNLYWON-UHFFFAOYSA-N benzyl n-[1-(2-acetamidoethyl)-3-(3,4-dichlorophenyl)-2-oxoquinoxalin-6-yl]carbamate Chemical compound C1=C2N=C(C=3C=C(Cl)C(Cl)=CC=3)C(=O)N(CCNC(=O)C)C2=CC=C1NC(=O)OCC1=CC=CC=C1 RMRDBXLTNLYWON-UHFFFAOYSA-N 0.000 claims description 2
- PECASCCOCBSCNN-UHFFFAOYSA-N benzyl n-[1-(2-acetamidoethyl)-3-(4-methoxyphenyl)-2-oxoquinoxalin-6-yl]carbamate Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(NC(=O)OCC=3C=CC=CC=3)=CC=C2N(CCNC(C)=O)C1=O PECASCCOCBSCNN-UHFFFAOYSA-N 0.000 claims description 2
- RMUZJCKZFYPSDO-UHFFFAOYSA-N benzyl n-[4-(2-acetamidoethyl)-2-methyl-3-oxo-1,2-dihydropyrido[2,3-b]pyrazin-7-yl]carbamate Chemical compound C=1N=C2N(CCNC(C)=O)C(=O)C(C)NC2=CC=1NC(=O)OCC1=CC=CC=C1 RMUZJCKZFYPSDO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical group CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- PNTFZUUBGCDWBF-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-[3-methyl-2-oxo-7-[[3-(trifluoromethyl)phenyl]methylamino]quinoxalin-1-yl]propanamide Chemical compound C1=C2N(CCC(=O)NCCO)C(=O)C(C)=NC2=CC=C1NCC1=CC=CC(C(F)(F)F)=C1 PNTFZUUBGCDWBF-UHFFFAOYSA-N 0.000 claims description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
- QJXVUGMMRSPJTG-UHFFFAOYSA-N n-[2-[2-(3,4-dichlorophenyl)-7-[(3,4-dichlorophenyl)methylamino]-3-oxopyrido[2,3-b]pyrazin-4-yl]ethyl]acetamide Chemical compound C1=C2N=C(C=3C=C(Cl)C(Cl)=CC=3)C(=O)N(CCNC(=O)C)C2=NC=C1NCC1=CC=C(Cl)C(Cl)=C1 QJXVUGMMRSPJTG-UHFFFAOYSA-N 0.000 claims description 2
- HLSLHEWIZKFZTP-UHFFFAOYSA-N n-[2-[2-(4-methoxyphenyl)-7-[(4-methoxyphenyl)methylamino]-3-oxopyrido[2,3-b]pyrazin-4-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1CNC1=CN=C(N(CCNC(C)=O)C(=O)C(=N2)C=3C=CC(OC)=CC=3)C2=C1 HLSLHEWIZKFZTP-UHFFFAOYSA-N 0.000 claims description 2
- HUYPGJIKHOQUMM-UHFFFAOYSA-N n-[2-[3-(4-methoxyphenyl)-2-oxo-7-[[4-(trifluoromethyl)pyridin-2-yl]methylamino]quinoxalin-1-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(N(CCNC(C)=O)C1=C2)=O)=NC1=CC=C2NCC1=CC(C(F)(F)F)=CC=N1 HUYPGJIKHOQUMM-UHFFFAOYSA-N 0.000 claims description 2
- ZVDNSERVQXIYPJ-UHFFFAOYSA-N n-[2-[3-(4-methoxyphenyl)-7-[(3-methylphenyl)methylamino]-2-oxoquinoxalin-1-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(N(CCNC(C)=O)C1=C2)=O)=NC1=CC=C2NCC1=CC=CC(C)=C1 ZVDNSERVQXIYPJ-UHFFFAOYSA-N 0.000 claims description 2
- LXSJTXGBHUBLGP-UHFFFAOYSA-N n-[2-[3-methyl-2-oxo-7-[[3-(trifluoromethyl)phenyl]methylamino]quinoxalin-1-yl]ethyl]thiophene-3-carboxamide Chemical compound C1=C2N(CCNC(=O)C3=CSC=C3)C(=O)C(C)=NC2=CC=C1NCC1=CC=CC(C(F)(F)F)=C1 LXSJTXGBHUBLGP-UHFFFAOYSA-N 0.000 claims description 2
- NDCVRWXYSAVFBF-UHFFFAOYSA-N n-[2-[7-(benzylamino)-2-methyl-3-oxopyrido[2,3-b]pyrazin-4-yl]ethyl]acetamide Chemical compound C1=C2N=C(C)C(=O)N(CCNC(=O)C)C2=NC=C1NCC1=CC=CC=C1 NDCVRWXYSAVFBF-UHFFFAOYSA-N 0.000 claims description 2
- QKGSSBJCIRWSPU-UHFFFAOYSA-N n-[2-[7-[(3,4-dichlorophenyl)methylamino]-2-(4-methoxyphenyl)-3-oxopyrido[2,3-b]pyrazin-4-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(NCC=3C=C(Cl)C(Cl)=CC=3)=CN=C2N(CCNC(C)=O)C1=O QKGSSBJCIRWSPU-UHFFFAOYSA-N 0.000 claims description 2
- JRNCYLBRLNFWGF-UHFFFAOYSA-N n-[2-[7-[(3,4-dichlorophenyl)methylamino]-3-oxo-2-pyridin-3-ylpyrido[2,3-b]pyrazin-4-yl]ethyl]acetamide Chemical compound C1=C2N=C(C=3C=NC=CC=3)C(=O)N(CCNC(=O)C)C2=NC=C1NCC1=CC=C(Cl)C(Cl)=C1 JRNCYLBRLNFWGF-UHFFFAOYSA-N 0.000 claims description 2
- ITRSXXVLXWPSCR-UHFFFAOYSA-N n-[2-[7-[(3,4-dimethylphenyl)methylamino]-3-(4-methoxyphenyl)-2-oxoquinoxalin-1-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(N(CCNC(C)=O)C1=C2)=O)=NC1=CC=C2NCC1=CC=C(C)C(C)=C1 ITRSXXVLXWPSCR-UHFFFAOYSA-N 0.000 claims description 2
- FWPIWLQAPAHJHW-UHFFFAOYSA-N n-[2-[7-[(3-chlorophenyl)methylamino]-2-(4-methoxyphenyl)-3-oxopyrido[2,3-b]pyrazin-4-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(NCC=3C=C(Cl)C=CC=3)=CN=C2N(CCNC(C)=O)C1=O FWPIWLQAPAHJHW-UHFFFAOYSA-N 0.000 claims description 2
- DJVYKNSSXZJQBQ-UHFFFAOYSA-N n-[2-[7-[(4-chlorophenyl)methylamino]-2-(4-methoxyphenyl)-3-oxopyrido[2,3-b]pyrazin-4-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(NCC=3C=CC(Cl)=CC=3)=CN=C2N(CCNC(C)=O)C1=O DJVYKNSSXZJQBQ-UHFFFAOYSA-N 0.000 claims description 2
- HISJLSXOXJASNK-UHFFFAOYSA-N n-[2-[7-[(4-fluoro-3-methylphenyl)methylamino]-3-(4-methoxyphenyl)-2-oxoquinoxalin-1-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(N(CCNC(C)=O)C1=C2)=O)=NC1=CC=C2NCC1=CC=C(F)C(C)=C1 HISJLSXOXJASNK-UHFFFAOYSA-N 0.000 claims description 2
- LWQHYXWNNUMNRP-UHFFFAOYSA-N n-[2-[7-[2-(2-chlorophenoxy)ethylamino]-3-(4-methoxyphenyl)-2-oxoquinoxalin-1-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(N(CCNC(C)=O)C1=C2)=O)=NC1=CC=C2NCCOC1=CC=CC=C1Cl LWQHYXWNNUMNRP-UHFFFAOYSA-N 0.000 claims description 2
- ZNWFXAUKPLNCOH-UHFFFAOYSA-N n-[2-[7-[2-(3,4-dichlorophenyl)ethylamino]-2-(4-methoxyphenyl)-3-oxopyrido[2,3-b]pyrazin-4-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(NCCC=3C=C(Cl)C(Cl)=CC=3)=CN=C2N(CCNC(C)=O)C1=O ZNWFXAUKPLNCOH-UHFFFAOYSA-N 0.000 claims description 2
- VNGUXYAVBLCMGD-UHFFFAOYSA-N n-[2-[7-[2-(3-chlorophenyl)ethylamino]-3-(4-methoxyphenyl)-2-oxoquinoxalin-1-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(N(CCNC(C)=O)C1=C2)=O)=NC1=CC=C2NCCC1=CC=CC(Cl)=C1 VNGUXYAVBLCMGD-UHFFFAOYSA-N 0.000 claims description 2
- HBNUDNGIQMHVDM-UHFFFAOYSA-N n-[2-[7-[2-(4-chlorophenyl)ethylamino]-3-(4-methoxyphenyl)-2-oxoquinoxalin-1-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(N(CCNC(C)=O)C1=C2)=O)=NC1=CC=C2NCCC1=CC=C(Cl)C=C1 HBNUDNGIQMHVDM-UHFFFAOYSA-N 0.000 claims description 2
- KDRGWBDOBCLUSE-UHFFFAOYSA-N n-[2-[7-[[4-chloro-3-(trifluoromethyl)phenyl]methylamino]-3-(4-methoxyphenyl)-2-oxoquinoxalin-1-yl]ethyl]acetamide Chemical compound C1=CC(OC)=CC=C1C(C(N(CCNC(C)=O)C1=C2)=O)=NC1=CC=C2NCC1=CC=C(Cl)C(C(F)(F)F)=C1 KDRGWBDOBCLUSE-UHFFFAOYSA-N 0.000 claims description 2
- RSIPQHOWTCNEBI-UHFFFAOYSA-N n-hydroxypropanamide Chemical compound CCC(=O)NO RSIPQHOWTCNEBI-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims description 2
- 101100240528 Caenorhabditis elegans nhr-23 gene Proteins 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2008/004631 WO2009126123A1 (en) | 2008-04-10 | 2008-04-10 | Bicyclic nitrogen containing heterocyclic compounds for use as stearoyl coa desaturase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011516546A JP2011516546A (ja) | 2011-05-26 |
| JP2011516546A5 true JP2011516546A5 (https=) | 2012-05-10 |
Family
ID=39710225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011503949A Pending JP2011516546A (ja) | 2008-04-10 | 2008-04-10 | ステアロイル−ＣｏＡデサチュラーゼのインヒビターとして使用するための二環式窒素含有複素環化合物 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP2276748A1 (https=) |
| JP (1) | JP2011516546A (https=) |
| CA (1) | CA2719650A1 (https=) |
| WO (1) | WO2009126123A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2012324015A1 (en) | 2011-12-01 | 2013-06-20 | Purdue Pharma L.P. | Azetidine-substituted quinoxaline-type piperidine compounds and uses thererof |
| MX2023005747A (es) | 2020-11-18 | 2023-07-28 | Deciphera Pharmaceuticals Llc | Inhibidores de gcn2 y perk quinasas y metodos de uso de los mismos. |
| KR20240113496A (ko) | 2021-12-03 | 2024-07-22 | 데시페라 파마슈티칼스, 엘엘씨. | Gcn2 및 perk 키나아제 억제제로서의 헤테로고리 화합물 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2319554C (en) * | 1998-03-31 | 2005-06-28 | Warner-Lambert Company | Quinoxalinones as serine protease inhibitors such as factor xa and thrombin |
| WO2002076954A1 (en) * | 2001-03-23 | 2002-10-03 | Smithkline Beecham Corporation | Compounds useful as kinase inhibitors for the treatment of hyperproliferative diseases |
| US7196090B2 (en) * | 2002-07-25 | 2007-03-27 | Warner-Lambert Company | Kinase inhibitors |
| CN101522676A (zh) * | 2006-10-05 | 2009-09-02 | Cv医药有限公司 | 用作硬脂酰-CoA脱氢酶抑制剂的双环含氮杂环化合物 |
| EP2131844A1 (en) * | 2007-04-09 | 2009-12-16 | CV Therapeutics Inc. | PTERIDINONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
-
2008
- 2008-04-10 WO PCT/US2008/004631 patent/WO2009126123A1/en not_active Ceased
- 2008-04-10 JP JP2011503949A patent/JP2011516546A/ja active Pending
- 2008-04-10 CA CA2719650A patent/CA2719650A1/en not_active Abandoned
- 2008-04-10 EP EP08742724A patent/EP2276748A1/en not_active Withdrawn
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