JP2005519876A5 - - Google Patents
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- Publication number
- JP2005519876A5 JP2005519876A5 JP2003546818A JP2003546818A JP2005519876A5 JP 2005519876 A5 JP2005519876 A5 JP 2005519876A5 JP 2003546818 A JP2003546818 A JP 2003546818A JP 2003546818 A JP2003546818 A JP 2003546818A JP 2005519876 A5 JP2005519876 A5 JP 2005519876A5
- Authority
- JP
- Japan
- Prior art keywords
- quinolin
- phenyl
- trifluoromethyl
- alkyl
- propanamide
- 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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- -1 perfluoro Chemical group 0.000 claims 140
- 125000000217 alkyl group Chemical group 0.000 claims 138
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 74
- 125000003118 aryl group Chemical group 0.000 claims 67
- 125000000753 cycloalkyl group Chemical group 0.000 claims 61
- 125000001072 heteroaryl group Chemical group 0.000 claims 59
- 125000001424 substituent group Chemical group 0.000 claims 51
- 125000003342 alkenyl group Chemical group 0.000 claims 38
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 33
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 21
- 150000002367 halogens Chemical class 0.000 claims 20
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000001041 indolyl group Chemical group 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000003386 piperidinyl group Chemical group 0.000 claims 9
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims 9
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 239000011593 sulfur Substances 0.000 claims 8
- 125000004434 sulfur atom Chemical group 0.000 claims 8
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 6
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 125000002393 azetidinyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims 3
- DORAXMIGARNAFQ-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.1]heptan-3-yl)quinolin-6-yl]-3-(4-ethylphenyl)urea Chemical compound C1=CC(CC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(C4)C3)C2=C1 DORAXMIGARNAFQ-UHFFFAOYSA-N 0.000 claims 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000004586 dihydrobenzopyranyl group Chemical group O1C(CCC2=C1C=CC=C2)* 0.000 claims 3
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 125000004306 triazinyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- XDBVPFWZNHAVPO-UHFFFAOYSA-N 1-(3-methyl-2-pyrrolidin-1-ylquinolin-6-yl)-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C2N=C(N3CCCC3)C(C)=CC2=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 XDBVPFWZNHAVPO-UHFFFAOYSA-N 0.000 claims 2
- CIPWGKDCOQROBT-UHFFFAOYSA-N 1-(4-ethylphenyl)-3-[2-[3-(methanesulfonamido)pyrrolidin-1-yl]quinolin-6-yl]urea Chemical compound C1=CC(CC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3CC(CC3)NS(C)(=O)=O)C2=C1 CIPWGKDCOQROBT-UHFFFAOYSA-N 0.000 claims 2
- VXYZZBVPRRDDSE-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.1]heptan-3-yl)-3-methylquinolin-6-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C=1C=C2N=C(N3C4CCC(C4)C3)C(C)=CC2=CC=1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 VXYZZBVPRRDDSE-UHFFFAOYSA-N 0.000 claims 2
- FUDFMTZNTSVLBF-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.1]heptan-3-yl)-3-methylquinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C2N=C(N3C4CCC(C4)C3)C(C)=CC2=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 FUDFMTZNTSVLBF-UHFFFAOYSA-N 0.000 claims 2
- CKMKAFVCVGPNHO-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.1]heptan-3-yl)quinolin-6-yl]-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(C4)C3)C2=C1 CKMKAFVCVGPNHO-UHFFFAOYSA-N 0.000 claims 2
- FGDIAVYHCXJFGL-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.1]heptan-3-yl)quinolin-6-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(C4)C3)C2=C1 FGDIAVYHCXJFGL-UHFFFAOYSA-N 0.000 claims 2
- UKMHTSLPNIFCIX-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.1]heptan-3-yl)quinolin-6-yl]-3-[4-(trifluoromethylsulfanyl)phenyl]urea Chemical compound C1=CC(SC(F)(F)F)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(C4)C3)C2=C1 UKMHTSLPNIFCIX-UHFFFAOYSA-N 0.000 claims 2
- JXRZGOJHZRKZGO-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-(2,3-dihydro-1h-inden-5-yl)urea Chemical compound C1C(CC2)CCC2N1C(C=CC1=C2)=NC1=CC=C2NC(=O)NC1=CC=C(CCC2)C2=C1 JXRZGOJHZRKZGO-UHFFFAOYSA-N 0.000 claims 2
- PDTZPOBINUFFFR-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-(4-ethylphenyl)urea Chemical compound C1=CC(CC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 PDTZPOBINUFFFR-UHFFFAOYSA-N 0.000 claims 2
- YVGVCXVVOVLSAQ-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 YVGVCXVVOVLSAQ-UHFFFAOYSA-N 0.000 claims 2
- OHIFSGGFIFNZQP-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 OHIFSGGFIFNZQP-UHFFFAOYSA-N 0.000 claims 2
- TZRMMIFOLYEGIV-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-(4-propan-2-ylphenyl)urea Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 TZRMMIFOLYEGIV-UHFFFAOYSA-N 0.000 claims 2
- QKDYWVVDKPTIFR-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-(4-propylphenyl)urea Chemical compound C1=CC(CCC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 QKDYWVVDKPTIFR-UHFFFAOYSA-N 0.000 claims 2
- JVCFWDKCXLEIDB-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-(6-ethylpyridin-3-yl)urea Chemical compound C1=NC(CC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 JVCFWDKCXLEIDB-UHFFFAOYSA-N 0.000 claims 2
- ARVMCHWYTLVASN-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 ARVMCHWYTLVASN-UHFFFAOYSA-N 0.000 claims 2
- MFWZVDXDRVFVGJ-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 MFWZVDXDRVFVGJ-UHFFFAOYSA-N 0.000 claims 2
- UZJXCZYUORXHLN-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-[4-(trifluoromethylsulfanyl)phenyl]urea Chemical compound C1=CC(SC(F)(F)F)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 UZJXCZYUORXHLN-UHFFFAOYSA-N 0.000 claims 2
- KJMLMNBMXORBLZ-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-[6-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C1=NC(C(F)(F)F)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3C4CCC(CC4)C3)C2=C1 KJMLMNBMXORBLZ-UHFFFAOYSA-N 0.000 claims 2
- LAABGEUEWIBXNZ-UHFFFAOYSA-N 1-[2-(azetidin-1-yl)-3-methylquinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C=1C=C2N=C(N3CCC3)C(C)=CC2=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 LAABGEUEWIBXNZ-UHFFFAOYSA-N 0.000 claims 2
- CCXVJJQINLSHRU-UHFFFAOYSA-N 1-[2-(dimethylamino)quinolin-6-yl]-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N(C)C)C2=C1 CCXVJJQINLSHRU-UHFFFAOYSA-N 0.000 claims 2
- UCLWQHYGGNRXJO-UHFFFAOYSA-N 1-[2-[3-(dimethylamino)pyrrolidin-1-yl]quinolin-6-yl]-3-(4-ethylphenyl)urea Chemical compound C1=CC(CC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N3CC(CC3)N(C)C)C2=C1 UCLWQHYGGNRXJO-UHFFFAOYSA-N 0.000 claims 2
- CTHWQLPMNDVWJE-UHFFFAOYSA-N 1-[2-[3-(dimethylamino)pyrrolidin-1-yl]quinolin-6-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1C(N(C)C)CCN1C1=CC=C(C=C(NC(=O)NC=2C=CC(OC(F)(F)F)=CC=2)C=C2)C2=N1 CTHWQLPMNDVWJE-UHFFFAOYSA-N 0.000 claims 2
- UGVWNYGDOHEDOR-UHFFFAOYSA-N 1-[2-[3-(dimethylamino)pyrrolidin-1-yl]quinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1C(N(C)C)CCN1C1=CC=C(C=C(NC(=O)NC=2C=CC(=CC=2)C(F)(F)F)C=C2)C2=N1 UGVWNYGDOHEDOR-UHFFFAOYSA-N 0.000 claims 2
- XJHWOIAORLHDPQ-UHFFFAOYSA-N 1-[2-[methyl(propan-2-yl)amino]quinolin-6-yl]-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)NC1=CC=C(N=C(C=C2)N(C)C(C)C)C2=C1 XJHWOIAORLHDPQ-UHFFFAOYSA-N 0.000 claims 2
- UAWXGZXXXLFCOJ-UHFFFAOYSA-N 1-[2-[methyl(propan-2-yl)amino]quinolin-6-yl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC2=NC(N(C)C(C)C)=CC=C2C=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 UAWXGZXXXLFCOJ-UHFFFAOYSA-N 0.000 claims 2
- TUHDERHVLZQEOC-UHFFFAOYSA-N 1-[2-[methyl(propan-2-yl)amino]quinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC2=NC(N(C)C(C)C)=CC=C2C=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 TUHDERHVLZQEOC-UHFFFAOYSA-N 0.000 claims 2
- YRRKNSNFIGZLKU-UHFFFAOYSA-N 2,2-dimethyl-n-[1-[6-[5-[2-[4-(trifluoromethyl)phenyl]ethyl]-1,2,4-oxadiazol-3-yl]quinolin-2-yl]pyrrolidin-3-yl]propanamide Chemical compound C1C(NC(=O)C(C)(C)C)CCN1C1=CC=C(C=C(C=C2)C=3N=C(CCC=4C=CC(=CC=4)C(F)(F)F)ON=3)C2=N1 YRRKNSNFIGZLKU-UHFFFAOYSA-N 0.000 claims 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- MVQARQYRYGFFIV-UHFFFAOYSA-N n-(2-pyrrolidin-1-ylquinolin-6-yl)-3-[4-(trifluoromethyl)phenyl]propanamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CCC(=O)NC1=CC=C(N=C(C=C2)N3CCCC3)C2=C1 MVQARQYRYGFFIV-UHFFFAOYSA-N 0.000 claims 2
- NYBVSXSOCHHSFH-UHFFFAOYSA-N n-[1-[6-[3-[4-(trifluoromethyl)phenyl]propanoylamino]quinolin-2-yl]pyrrolidin-3-yl]cyclohexanecarboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CCC(=O)NC1=CC=C(N=C(C=C2)N3CC(CC3)NC(=O)C3CCCCC3)C2=C1 NYBVSXSOCHHSFH-UHFFFAOYSA-N 0.000 claims 2
- NYCODFSKZHVBEP-UHFFFAOYSA-N n-[1-[6-[5-[2-[4-(trifluoromethyl)phenyl]ethyl]-1,2,4-oxadiazol-3-yl]quinolin-2-yl]pyrrolidin-3-yl]propanamide Chemical compound C1C(NC(=O)CC)CCN1C1=CC=C(C=C(C=C2)C=3N=C(CCC=4C=CC(=CC=4)C(F)(F)F)ON=3)C2=N1 NYCODFSKZHVBEP-UHFFFAOYSA-N 0.000 claims 2
- KHHJLWFCLVTIRA-UHFFFAOYSA-N n-[2-(2-methylpyrrolidin-1-yl)quinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]propanamide Chemical compound CC1CCCN1C1=CC=C(C=C(NC(=O)CCC=2C=CC(=CC=2)C(F)(F)F)C=C2)C2=N1 KHHJLWFCLVTIRA-UHFFFAOYSA-N 0.000 claims 2
- HFFFJRURGASIEY-UHFFFAOYSA-N n-[2-(3-azabicyclo[2.2.1]heptan-3-yl)-4-(dimethylamino)quinolin-6-yl]-4-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C2C(N(C)C)=CC(N3C4CCC(C4)C3)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 HFFFJRURGASIEY-UHFFFAOYSA-N 0.000 claims 2
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- BXBSQWKMHIDBOF-UHFFFAOYSA-N n-[2-(cyclopentylamino)quinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]propanamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CCC(=O)NC1=CC=C(N=C(NC2CCCC2)C=C2)C2=C1 BXBSQWKMHIDBOF-UHFFFAOYSA-N 0.000 claims 2
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- MPLZJJHETRKHRI-UHFFFAOYSA-N n-[2-[methyl(propan-2-yl)amino]quinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]propanamide Chemical compound C1=CC2=NC(N(C)C(C)C)=CC=C2C=C1NC(=O)CCC1=CC=C(C(F)(F)F)C=C1 MPLZJJHETRKHRI-UHFFFAOYSA-N 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
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- XZVANCZWPZKLIU-UHFFFAOYSA-N 1-[2-(3-azabicyclo[2.2.2]octan-3-yl)quinolin-6-yl]-3-(2,2-difluoro-1,3-benzodioxol-5-yl)urea Chemical compound C1C(CC2)CCC2N1C(C=CC1=C2)=NC1=CC=C2NC(=O)NC1=CC=C2OC(F)(F)OC2=C1 XZVANCZWPZKLIU-UHFFFAOYSA-N 0.000 claims 1
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- KLLSOXKAHCKEGO-UHFFFAOYSA-N n-[2-[cyclobutyl(methyl)amino]quinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C2C=C(NC(=O)CCC=3C=CC(=CC=3)C(F)(F)F)C=CC2=NC=1N(C)C1CCC1 KLLSOXKAHCKEGO-UHFFFAOYSA-N 0.000 claims 1
- HBEKVKPZNKSMOE-UHFFFAOYSA-N n-[2-[ethyl(methyl)amino]quinolin-6-yl]-3-[4-(trifluoromethyl)phenyl]propanamide Chemical compound C1=CC2=NC(N(C)CC)=CC=C2C=C1NC(=O)CCC1=CC=C(C(F)(F)F)C=C1 HBEKVKPZNKSMOE-UHFFFAOYSA-N 0.000 claims 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
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- 2002-11-22 US US10/496,615 patent/US7084156B2/en not_active Expired - Fee Related
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