JP2002523502A5 - - Google Patents

Info

Publication number

JP2002523502A5

JP2002523502A5 JP2000567525A JP2000567525A JP2002523502A5 JP 2002523502 A5 JP2002523502 A5 JP 2002523502A5 JP 2000567525 A JP2000567525 A JP 2000567525A JP 2000567525 A JP2000567525 A JP 2000567525A JP 2002523502 A5 JP2002523502 A5 JP 2002523502A5

Authority

JP

Japan

Prior art keywords

alkyl

pyridylamino

independently

compound

substituted

Prior art date

1999-08-27

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

Links

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• 150000001875 compounds Chemical class 0.000 description 22
• 125000000217 alkyl group Chemical group 0.000 description 19
• 125000003118 aryl group Chemical group 0.000 description 19
• 125000001424 substituent group Chemical group 0.000 description 19
• 230000002452 interceptive effect Effects 0.000 description 11
• 125000005843 halogen group Chemical group 0.000 description 10
• 125000001072 heteroaryl group Chemical group 0.000 description 10
• 150000003839 salts Chemical class 0.000 description 8
• 125000003342 alkenyl group Chemical group 0.000 description 7
• 125000000304 alkynyl group Chemical group 0.000 description 7
• 125000003435 aroyl group Chemical group 0.000 description 6
• 125000003710 aryl alkyl group Chemical group 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 238000000034 method Methods 0.000 description 4
• 102000004887 Transforming Growth Factor beta Human genes 0.000 description 3
• 108090001012 Transforming Growth Factor beta Proteins 0.000 description 3
• 125000002252 acyl group Chemical group 0.000 description 3
• 125000002877 alkyl aryl group Chemical group 0.000 description 3
• 230000002401 inhibitory effect Effects 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 3
• 125000001931 aliphatic group Chemical group 0.000 description 2
• 125000005251 aryl acyl group Chemical group 0.000 description 2
• 125000005842 heteroatom Chemical group 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 125000000547 substituted alkyl group Chemical group 0.000 description 2
• UKTAMAPHRYOUJF-UHFFFAOYSA-N 2-(2,6-dibromophenyl)-n-pyridin-4-ylquinazolin-4-amine Chemical compound BrC1=CC=CC(Br)=C1C1=NC(NC=2C=CN=CC=2)=C(C=CC=C2)C2=N1 UKTAMAPHRYOUJF-UHFFFAOYSA-N 0.000 description 1
• YOOMHBKQLQDQNP-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-pyridin-4-ylquinazolin-4-amine Chemical compound ClC1=CC=CC(Cl)=C1C1=NC(NC=2C=CN=CC=2)=C(C=CC=C2)C2=N1 YOOMHBKQLQDQNP-UHFFFAOYSA-N 0.000 description 1
• BFGQWKIWTVOJJZ-UHFFFAOYSA-N 2-(2,6-difluorophenyl)-n-pyridin-4-ylquinazolin-4-amine Chemical compound FC1=CC=CC(F)=C1C1=NC(NC=2C=CN=CC=2)=C(C=CC=C2)C2=N1 BFGQWKIWTVOJJZ-UHFFFAOYSA-N 0.000 description 1
• NZFSBHMJKSDUJJ-UHFFFAOYSA-N 2-(2-bromophenyl)-n-pyridin-4-ylquinazolin-4-amine Chemical compound BrC1=CC=CC=C1C1=NC(NC=2C=CN=CC=2)=C(C=CC=C2)C2=N1 NZFSBHMJKSDUJJ-UHFFFAOYSA-N 0.000 description 1
• GFAMVEXIOQUVBP-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-pyridin-4-ylquinazolin-4-amine Chemical compound ClC1=CC=CC=C1C1=NC(NC=2C=CN=CC=2)=C(C=CC=C2)C2=N1 GFAMVEXIOQUVBP-UHFFFAOYSA-N 0.000 description 1
• HVFQVBSNHDYUFU-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-n-pyridin-4-ylquinazoline-4,6-diamine Chemical compound C12=CC(N)=CC=C2N=C(C=2C(=CC=CC=2)F)N=C1NC1=CC=NC=C1 HVFQVBSNHDYUFU-UHFFFAOYSA-N 0.000 description 1
• KWBWEHKATKLMFL-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-n-pyridin-4-ylquinazoline-4,7-diamine Chemical compound N=1C(C=2C(=CC=CC=2)F)=NC2=CC(N)=CC=C2C=1NC1=CC=NC=C1 KWBWEHKATKLMFL-UHFFFAOYSA-N 0.000 description 1
• URDICAFRQWPDGT-UHFFFAOYSA-N 2-(2-fluorophenyl)-6,7-dimethoxy-n-pyridin-4-ylquinazolin-4-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C=2C(=CC=CC=2)F)=NC=1NC1=CC=NC=C1 URDICAFRQWPDGT-UHFFFAOYSA-N 0.000 description 1
• FREPRBGKBRCENL-UHFFFAOYSA-N 2-(2-fluorophenyl)-6-n-[(3-methoxyphenyl)methyl]-4-n-pyridin-4-ylquinazoline-4,6-diamine Chemical compound COC1=CC=CC(CNC=2C=C3C(NC=4C=CN=CC=4)=NC(=NC3=CC=2)C=2C(=CC=CC=2)F)=C1 FREPRBGKBRCENL-UHFFFAOYSA-N 0.000 description 1
• VZEZHGMMOHNBQJ-UHFFFAOYSA-N 2-(2-fluorophenyl)-6-n-[(4-methoxyphenyl)methyl]-4-n-pyridin-4-ylquinazoline-4,6-diamine Chemical compound C1=CC(OC)=CC=C1CNC1=CC=C(N=C(N=C2NC=3C=CN=CC=3)C=3C(=CC=CC=3)F)C2=C1 VZEZHGMMOHNBQJ-UHFFFAOYSA-N 0.000 description 1
• VSDBMQKTNZZXMO-UHFFFAOYSA-N 2-(2-fluorophenyl)-6-n-[(4-methylsulfanylphenyl)methyl]-4-n-pyridin-4-ylquinazoline-4,6-diamine Chemical compound C1=CC(SC)=CC=C1CNC1=CC=C(N=C(N=C2NC=3C=CN=CC=3)C=3C(=CC=CC=3)F)C2=C1 VSDBMQKTNZZXMO-UHFFFAOYSA-N 0.000 description 1
• KSKHCZVMECBGRS-UHFFFAOYSA-N 2-(2-fluorophenyl)-6-nitro-n-pyridin-4-ylquinazolin-4-amine Chemical compound C12=CC([N+](=O)[O-])=CC=C2N=C(C=2C(=CC=CC=2)F)N=C1NC1=CC=NC=C1 KSKHCZVMECBGRS-UHFFFAOYSA-N 0.000 description 1
• ZVGAQVAHOPFEJQ-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-pyridin-4-ylquinazolin-4-amine Chemical compound FC1=CC=CC=C1C1=NC(NC=2C=CN=CC=2)=C(C=CC=C2)C2=N1 ZVGAQVAHOPFEJQ-UHFFFAOYSA-N 0.000 description 1
• KGRMJQMDCWZCHR-UHFFFAOYSA-N 2-(2-methylphenyl)-n-pyridin-4-ylquinazolin-4-amine Chemical compound CC1=CC=CC=C1C1=NC(NC=2C=CN=CC=2)=C(C=CC=C2)C2=N1 KGRMJQMDCWZCHR-UHFFFAOYSA-N 0.000 description 1
• XXNHDCHEEOWSPP-UHFFFAOYSA-N 2-(4-fluorophenyl)-6,7-dimethoxy-n-pyridin-4-ylquinazolin-4-amine Chemical compound C=12C=C(OC)C(OC)=CC2=NC(C=2C=CC(F)=CC=2)=NC=1NC1=CC=NC=C1 XXNHDCHEEOWSPP-UHFFFAOYSA-N 0.000 description 1
• ISVKZMKGDXSOHM-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-pyridin-4-ylquinazolin-4-amine Chemical compound C1=CC(F)=CC=C1C1=NC(NC=2C=CN=CC=2)=C(C=CC=C2)C2=N1 ISVKZMKGDXSOHM-UHFFFAOYSA-N 0.000 description 1
• QGWNGFYEPGNYNY-UHFFFAOYSA-N 2-phenyl-n-pyridin-4-ylquinazolin-4-amine Chemical compound N=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1NC1=CC=NC=C1 QGWNGFYEPGNYNY-UHFFFAOYSA-N 0.000 description 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• -1 4-pyrimidyl Chemical group 0.000 description 1
• JPAHDAHEAVKDGT-UHFFFAOYSA-N 6-n-tert-butyl-2-(2-fluorophenyl)-4-n-pyridin-4-ylquinazoline-4,6-diamine Chemical compound C12=CC(NC(C)(C)C)=CC=C2N=C(C=2C(=CC=CC=2)F)N=C1NC1=CC=NC=C1 JPAHDAHEAVKDGT-UHFFFAOYSA-N 0.000 description 1
• 0 CC1=NC(*)=*C(*)C1N*INN Chemical compound CC1=NC(*)=*C(*)C1N*INN 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 125000004404 heteroalkyl group Chemical group 0.000 description 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 125000001183 hydrocarbyl group Chemical group 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 239000008194 pharmaceutical composition Substances 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1