JP2002523502A - 医薬としてのキナゾリン誘導体 - Google Patents
医薬としてのキナゾリン誘導体Info
- Publication number
- JP2002523502A JP2002523502A JP2000567525A JP2000567525A JP2002523502A JP 2002523502 A JP2002523502 A JP 2002523502A JP 2000567525 A JP2000567525 A JP 2000567525A JP 2000567525 A JP2000567525 A JP 2000567525A JP 2002523502 A JP2002523502 A JP 2002523502A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyridylamino
- independently
- quinazoline
- compound
- 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
Links
- 239000003814 drug Substances 0.000 title claims description 8
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 125000001424 substituent group Chemical group 0.000 claims abstract description 66
- 125000003118 aryl group Chemical group 0.000 claims abstract description 44
- 102000004887 Transforming Growth Factor beta Human genes 0.000 claims abstract description 40
- 108090001012 Transforming Growth Factor beta Proteins 0.000 claims abstract description 40
- 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 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 22
- 230000002452 interceptive effect Effects 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 230000000694 effects Effects 0.000 claims description 40
- -1 4-pyrimidyl Chemical group 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000003435 aroyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 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 claims description 3
- 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 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 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 claims description 2
- 125000005251 aryl acyl group Chemical group 0.000 claims description 2
- 101000687448 Homo sapiens REST corepressor 1 Proteins 0.000 claims 2
- 102100024864 REST corepressor 1 Human genes 0.000 claims 2
- 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 1
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- NWUSZGRNRYCQJE-UHFFFAOYSA-N n-pyridin-2-ylquinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC1=CC=CC=N1 NWUSZGRNRYCQJE-UHFFFAOYSA-N 0.000 claims 1
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/141,916 US6184226B1 (en) | 1998-08-28 | 1998-08-28 | Quinazoline derivatives as inhibitors of P-38 α |
| US09/141,916 | 1998-08-28 | ||
| PCT/US1999/019846 WO2000012497A2 (en) | 1998-08-28 | 1999-08-27 | Quinazoline derivatives as medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002523502A true JP2002523502A (ja) | 2002-07-30 |
| JP2002523502A5 JP2002523502A5 (enExample) | 2006-10-05 |
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| BR (1) | BR9913648A (enExample) |
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| JP2001526273A (ja) * | 1997-12-18 | 2001-12-18 | アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 置換された２−アリール−４−アミノキナゾリン、それらの製造方法及び医薬としての使用 |
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| JP2013510103A (ja) * | 2009-11-07 | 2013-03-21 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | ＴＧＦ−β受容体キナーゼ阻害剤としてのヘテロアリールアミノキノリン |
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| JP2015533822A (ja) * | 2012-09-28 | 2015-11-26 | イグニタ、インク． | 非定型プロテインキナーゼｃのアザキナゾリン阻害薬 |
| JP2017505288A (ja) * | 2013-12-09 | 2017-02-16 | ユーシービー バイオファルマ エスピーアールエル | Ｔｎｆ活性のモジュレーターとしての縮合二環式ヘテロ芳香族誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL141723A0 (en) | 2002-03-10 |
| CN1333757A (zh) | 2002-01-30 |
| US6903096B2 (en) | 2005-06-07 |
| KR20010083874A (ko) | 2001-09-03 |
| CN1152867C (zh) | 2004-06-09 |
| DE69933573D1 (de) | 2006-11-23 |
| ES2274642T3 (es) | 2007-05-16 |
| US20020161010A1 (en) | 2002-10-31 |
| BR9913648A (pt) | 2002-01-02 |
| AU6241399A (en) | 2000-03-21 |
| US6277989B1 (en) | 2001-08-21 |
| WO2000012497A3 (en) | 2000-06-29 |
| DE69933573T2 (de) | 2007-05-03 |
| WO2000012497B1 (en) | 2000-09-08 |
| EP1107959B1 (en) | 2006-10-11 |
| US6476031B1 (en) | 2002-11-05 |
| EP1107959A2 (en) | 2001-06-20 |
| ATE342256T1 (de) | 2006-11-15 |
| AU771947B2 (en) | 2004-04-08 |
| US6184226B1 (en) | 2001-02-06 |
| US20050220784A1 (en) | 2005-10-06 |
| US7345045B2 (en) | 2008-03-18 |
| MXPA01002175A (es) | 2003-07-14 |
| CA2342250A1 (en) | 2000-03-09 |
| HK1035897A1 (en) | 2001-12-14 |
| US20030069248A1 (en) | 2003-04-10 |
| WO2000012497A2 (en) | 2000-03-09 |
| US20050171123A1 (en) | 2005-08-04 |
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