JP2004531473A5 - - Google Patents
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- JP2004531473A5 JP2004531473A5 JP2002556173A JP2002556173A JP2004531473A5 JP 2004531473 A5 JP2004531473 A5 JP 2004531473A5 JP 2002556173 A JP2002556173 A JP 2002556173A JP 2002556173 A JP2002556173 A JP 2002556173A JP 2004531473 A5 JP2004531473 A5 JP 2004531473A5
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- JP
- Japan
- Prior art keywords
- optionally substituted
- phenyl
- methyl
- alkyl
- substituted
- 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.)
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- -1 —OR 7 Chemical group 0.000 claims 308
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000001424 substituent group Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 125000004076 pyridyl group Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 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 9
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 7
- 125000001544 thienyl group Chemical group 0.000 claims 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000002541 furyl group Chemical group 0.000 claims 5
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 4
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 3
- 230000033115 angiogenesis Effects 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- CBCROIPJZHJWRD-UHFFFAOYSA-N 6-chloro-n-(3-fluoro-4-methylphenyl)-2-[(4-methoxyphenyl)methylamino]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC1=NC(Cl)=CC=C1C(=O)NC1=CC=C(C)C(F)=C1 CBCROIPJZHJWRD-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 2
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 1
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 1
- KFVKYZSMMMDKRE-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethylamino)-n-(4-phenoxyphenyl)pyridine-3-carboxamide Chemical compound C=1C=CN=C(NCC=2C=C3OCOC3=CC=2)C=1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 KFVKYZSMMMDKRE-UHFFFAOYSA-N 0.000 claims 1
- ODIUWSGXFVVAKM-UHFFFAOYSA-N 2-(benzylamino)-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCC=2C=CC=CC=2)=C1 ODIUWSGXFVVAKM-UHFFFAOYSA-N 0.000 claims 1
- SYUKLOYZNHCGBC-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC1=CC=CC(CNC=2C(=CC=CN=2)C(=O)NC=2C=C(C=CC=2)C(F)(F)F)=C1F SYUKLOYZNHCGBC-UHFFFAOYSA-N 0.000 claims 1
- DYNPEMXFFWJLMJ-UHFFFAOYSA-N 2-[(2,4-difluorophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC1=CC(F)=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 DYNPEMXFFWJLMJ-UHFFFAOYSA-N 0.000 claims 1
- PWMUDLQOCMEUCU-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC1=CC=CC(F)=C1CNC1=NC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 PWMUDLQOCMEUCU-UHFFFAOYSA-N 0.000 claims 1
- KSQCHVLQEUNDEM-UHFFFAOYSA-N 2-[(2-fluorophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC1=CC=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 KSQCHVLQEUNDEM-UHFFFAOYSA-N 0.000 claims 1
- NRZKLXGUIKBKLJ-UHFFFAOYSA-N 2-[(3,4-difluorophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 NRZKLXGUIKBKLJ-UHFFFAOYSA-N 0.000 claims 1
- JACJEBUBJKACMQ-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 JACJEBUBJKACMQ-UHFFFAOYSA-N 0.000 claims 1
- GCLWSEBLZMMEHH-UHFFFAOYSA-N 2-[(3-bromophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCC=2C=C(Br)C=CC=2)=C1 GCLWSEBLZMMEHH-UHFFFAOYSA-N 0.000 claims 1
- HCSKCSKMJMETRI-UHFFFAOYSA-N 2-[(3-chlorophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCC=2C=C(Cl)C=CC=2)=C1 HCSKCSKMJMETRI-UHFFFAOYSA-N 0.000 claims 1
- RBJFLTHSDVTGBL-UHFFFAOYSA-N 2-[(3-fluorophenyl)methylamino]-n-(4-phenoxyphenyl)pyridine-3-carboxamide Chemical compound FC1=CC=CC(CNC=2C(=CC=CN=2)C(=O)NC=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 RBJFLTHSDVTGBL-UHFFFAOYSA-N 0.000 claims 1
- ZUGLOPTZPUVQOK-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methylamino]-n-(4-propan-2-ylphenyl)pyridine-3-carboxamide Chemical compound COC1=CC=CC(CNC=2C(=CC=CN=2)C(=O)NC=2C=CC(=CC=2)C(C)C)=C1 ZUGLOPTZPUVQOK-UHFFFAOYSA-N 0.000 claims 1
- NQIKQTJNGDKTGP-UHFFFAOYSA-N 2-[(4-bromophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCC=2C=CC(Br)=CC=2)=C1 NQIKQTJNGDKTGP-UHFFFAOYSA-N 0.000 claims 1
- COWAPRLHHAXZLW-UHFFFAOYSA-N 2-[(4-chlorophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2C(=NC=CC=2)NCC=2C=CC(Cl)=CC=2)=C1 COWAPRLHHAXZLW-UHFFFAOYSA-N 0.000 claims 1
- BFHOOZSXILGZME-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylamino]-n-(4-propan-2-ylphenyl)pyridine-3-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)C1=CC=CN=C1NCC1=CC=C(F)C=C1 BFHOOZSXILGZME-UHFFFAOYSA-N 0.000 claims 1
- ZILBQSNRPDGJDC-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylamino]-n-[3-(2-pyrrolidin-1-ylethoxy)-4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=C(C(F)(F)F)C(OCCN2CCCC2)=C1 ZILBQSNRPDGJDC-UHFFFAOYSA-N 0.000 claims 1
- SVVQQZYYWOJAGA-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 SVVQQZYYWOJAGA-UHFFFAOYSA-N 0.000 claims 1
- PKRWFCLGWNBHBA-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylamino]-n-[4-(1,1,2,2,2-pentafluoroethyl)-3-(pyrrolidin-2-ylmethoxy)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=C(C(F)(F)C(F)(F)F)C(OCC2NCCC2)=C1 PKRWFCLGWNBHBA-UHFFFAOYSA-N 0.000 claims 1
- VIXCSVVABRZKOU-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylamino]-n-[4-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=C(C(F)(F)F)C=C1 VIXCSVVABRZKOU-UHFFFAOYSA-N 0.000 claims 1
- LXKFMAUKOWWHOQ-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylamino]-n-[4-[2-(1-methylpiperidin-4-yl)propan-2-yl]phenyl]pyridine-3-carboxamide Chemical compound C1CN(C)CCC1C(C)(C)C(C=C1)=CC=C1NC(=O)C1=CC=CN=C1NCC1=CC=C(F)C=C1 LXKFMAUKOWWHOQ-UHFFFAOYSA-N 0.000 claims 1
- AQRDNYLHJOYURG-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC1=NC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 AQRDNYLHJOYURG-UHFFFAOYSA-N 0.000 claims 1
- NSPSEWFIMULCEX-UHFFFAOYSA-N 2-[[4-fluoro-3-(3-morpholin-4-ylprop-1-ynyl)phenyl]methylamino]-n-[3-(trifluoromethyl)phenyl]pyridine-3-carboxamide Chemical compound C1=C(C#CCN2CCOCC2)C(F)=CC=C1CNC1=NC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 NSPSEWFIMULCEX-UHFFFAOYSA-N 0.000 claims 1
- VEOYVWCLFQXJDN-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-[[3-[[4-(1,1,2,2,2-pentafluoroethyl)phenyl]carbamoyl]pyridin-2-yl]amino]propanoic acid Chemical compound C=1C=C2OCOC2=CC=1C(CC(=O)O)NC1=NC=CC=C1C(=O)NC1=CC=C(C(F)(F)C(F)(F)F)C=C1 VEOYVWCLFQXJDN-UHFFFAOYSA-N 0.000 claims 1
- WBDBXXMFTFNWOT-UHFFFAOYSA-N 3-(benzylamino)-n-(4-chlorophenyl)pyridine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=NC=CC=C1NCC1=CC=CC=C1 WBDBXXMFTFNWOT-UHFFFAOYSA-N 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- WSYHESLLOFKCFE-UHFFFAOYSA-N 6-chloro-n-(4-chlorophenyl)-2-[(4-methoxyphenyl)methylamino]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC1=NC(Cl)=CC=C1C(=O)NC1=CC=C(Cl)C=C1 WSYHESLLOFKCFE-UHFFFAOYSA-N 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- OALHLMGXOLMLJK-UHFFFAOYSA-N C1=CC(OC)=CC=C1CNC1(C(=O)NC=2C=C(F)C(C)=CC=2)C=CC=CN1 Chemical compound C1=CC(OC)=CC=C1CNC1(C(=O)NC=2C=C(F)C(C)=CC=2)C=CC=CN1 OALHLMGXOLMLJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 230000000118 anti-neoplastic effect Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 229940125697 hormonal agent Drugs 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 230000001900 immune effect Effects 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- MRTQFEVTVFYJKE-UHFFFAOYSA-N n-(2,2-dimethyl-3,4-dihydro-1,4-benzoxazin-6-yl)-2-[(4-fluorophenyl)methylamino]pyridine-3-carboxamide Chemical compound C=1C=C2OC(C)(C)CNC2=CC=1NC(=O)C1=CC=CN=C1NCC1=CC=C(F)C=C1 MRTQFEVTVFYJKE-UHFFFAOYSA-N 0.000 claims 1
- RTNDAUSNQFJLJM-UHFFFAOYSA-N n-(3,3-dimethyl-1-piperidin-4-yl-2h-indol-6-yl)-2-[(4-fluorophenyl)methylamino]pyridine-3-carboxamide Chemical compound C12=CC(NC(=O)C=3C(=NC=CC=3)NCC=3C=CC(F)=CC=3)=CC=C2C(C)(C)CN1C1CCNCC1 RTNDAUSNQFJLJM-UHFFFAOYSA-N 0.000 claims 1
- CCKNYUJCLRTAPN-UHFFFAOYSA-N n-(4,4-dimethyl-2-oxo-1,3-dihydroquinolin-7-yl)-2-[(4-fluorophenyl)methylamino]pyridine-3-carboxamide Chemical compound C=1C=C2C(C)(C)CC(=O)NC2=CC=1NC(=O)C1=CC=CN=C1NCC1=CC=C(F)C=C1 CCKNYUJCLRTAPN-UHFFFAOYSA-N 0.000 claims 1
- GGFBELLAMHBYAC-UHFFFAOYSA-N n-(4-acetyl-2,2-dimethyl-3h-1,4-benzoxazin-6-yl)-2-[(4-fluorophenyl)methylamino]pyridine-3-carboxamide Chemical compound C1=C2N(C(=O)C)CC(C)(C)OC2=CC=C1NC(=O)C1=CC=CN=C1NCC1=CC=C(F)C=C1 GGFBELLAMHBYAC-UHFFFAOYSA-N 0.000 claims 1
- CBJQNTOIJSJSGJ-UHFFFAOYSA-N n-(4-bromo-2-fluorophenyl)-2-[[3-[3-(dimethylamino)propyl]-4-fluorophenyl]methylamino]pyridine-3-carboxamide Chemical compound C1=C(F)C(CCCN(C)C)=CC(CNC=2C(=CC=CN=2)C(=O)NC=2C(=CC(Br)=CC=2)F)=C1 CBJQNTOIJSJSGJ-UHFFFAOYSA-N 0.000 claims 1
- KEQYIGIJEUDESO-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[(2-cyanophenyl)methylamino]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CN=C1NCC1=CC=CC=C1C#N KEQYIGIJEUDESO-UHFFFAOYSA-N 0.000 claims 1
- UQEYWSCFQXQKOB-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[(4-cyanophenyl)methylamino]pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CN=C1NCC1=CC=C(C#N)C=C1 UQEYWSCFQXQKOB-UHFFFAOYSA-N 0.000 claims 1
- UWOZEQLMJPPFRK-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[(4-nitrophenyl)methylamino]pyridine-2-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CNC1=CC=CN=C1C(=O)NC1=CC=C(Cl)C=C1 UWOZEQLMJPPFRK-UHFFFAOYSA-N 0.000 claims 1
- FUEGDGQHJRMBGX-UHFFFAOYSA-N n-(4-phenoxyphenyl)-n-[2-[[3-(trifluoromethyl)phenyl]methylamino]pyridin-3-yl]formamide Chemical compound FC(F)(F)C1=CC=CC(CNC=2C(=CC=CN=2)N(C=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 FUEGDGQHJRMBGX-UHFFFAOYSA-N 0.000 claims 1
- NHVOUMAHIHKFOA-UHFFFAOYSA-N n-(4-phenoxyphenyl)-n-[2-[[4-(trifluoromethoxy)phenyl]methylamino]pyridin-3-yl]formamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1CNC1=NC=CC=C1N(C=O)C(C=C1)=CC=C1OC1=CC=CC=C1 NHVOUMAHIHKFOA-UHFFFAOYSA-N 0.000 claims 1
- XRVMPVGAKDAVEB-UHFFFAOYSA-N n-(4-phenoxyphenyl)-n-[2-[[4-(trifluoromethyl)phenyl]methylamino]pyridin-3-yl]formamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC1=NC=CC=C1N(C=O)C(C=C1)=CC=C1OC1=CC=CC=C1 XRVMPVGAKDAVEB-UHFFFAOYSA-N 0.000 claims 1
- XOEQGZQGQYFXCM-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-[[3-[3-(dimethylamino)propyl]-4-fluorophenyl]methylamino]pyridine-3-carboxamide Chemical compound C1=C(F)C(CCCN(C)C)=CC(CNC=2C(=CC=CN=2)C(=O)NC=2C=CC(=CC=2)C(C)(C)C)=C1 XOEQGZQGQYFXCM-UHFFFAOYSA-N 0.000 claims 1
- FKISBQPOTDRBAG-UHFFFAOYSA-N n-[3-[3-(dimethylamino)propyl]-5-(trifluoromethyl)phenyl]-2-[(4-fluorophenyl)methylamino]pyridine-3-carboxamide Chemical compound FC(F)(F)C1=CC(CCCN(C)C)=CC(NC(=O)C=2C(=NC=CC=2)NCC=2C=CC(F)=CC=2)=C1 FKISBQPOTDRBAG-UHFFFAOYSA-N 0.000 claims 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- GQPUELDQOSKACF-UHFFFAOYSA-N tert-butyl 2-[[5-[[2-[(4-fluorophenyl)methylamino]pyridine-3-carbonyl]amino]-2-(1,1,2,2,2-pentafluoroethyl)phenoxy]methyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1COC1=CC(NC(=O)C=2C(=NC=CC=2)NCC=2C=CC(F)=CC=2)=CC=C1C(F)(F)C(F)(F)F GQPUELDQOSKACF-UHFFFAOYSA-N 0.000 claims 1
- RWGXNDGNHTUYSJ-UHFFFAOYSA-N tert-butyl 4-[[2-tert-butyl-5-[[2-[(4-fluorophenyl)methylamino]pyridine-3-carbonyl]amino]phenoxy]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1COC1=CC(NC(=O)C=2C(=NC=CC=2)NCC=2C=CC(F)=CC=2)=CC=C1C(C)(C)C RWGXNDGNHTUYSJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9824579D0 (en) * | 1998-11-10 | 1999-01-06 | Novartis Ag | Organic compounds |
| UA71587C2 (uk) * | 1998-11-10 | 2004-12-15 | Шерінг Акцієнгезелльшафт | Аміди антранілової кислоти та їхнє застосування як лікарських засобів |
| MY123528A (en) * | 1999-09-16 | 2006-05-31 | Mitsubihsi Tanabe Pharma Corp | Aromatic nitrogen-containing 6-membered cyclic compounds. |
| GB0001930D0 (en) * | 2000-01-27 | 2000-03-22 | Novartis Ag | Organic compounds |
| DE10023492A1 (de) * | 2000-05-09 | 2001-11-22 | Schering Ag | Aza- und Polyazanthranylamide und deren Verwendung als Arzneimittel |
| PE20020870A1 (es) * | 2001-02-13 | 2002-11-18 | Aventis Pharma Gmbh | 6,7,8,9-tetrahidro-5h-benzocicloheptenil aminas aciladas |
-
2002
- 2002-01-10 US US10/046,526 patent/US20020147198A1/en not_active Abandoned
- 2002-01-11 EP EP02717324A patent/EP1358161A2/en not_active Withdrawn
- 2002-01-11 AU AU2002248339A patent/AU2002248339B2/en not_active Ceased
- 2002-01-11 MX MXPA03006010A patent/MXPA03006010A/es unknown
- 2002-01-11 CA CA002434274A patent/CA2434274A1/en not_active Abandoned
- 2002-01-11 WO PCT/US2002/000742 patent/WO2002055501A2/en not_active Ceased
- 2002-01-11 JP JP2002556173A patent/JP2004531473A/ja not_active Withdrawn
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