5-(叔丁氧羰基氨基)-2-氟异烟酸甲酯 | 305371-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-(叔丁氧羰基氨基)-2-氟异烟酸甲酯
• 中文别名: (5R,13S,14S,15R)-13,15,22,24-四羟基-5-甲氧基-14,16-二甲基-2-氮杂二环[18.3.1]二十四碳-1(24),6,8,10,16,20,22-七烯-3-酮
• 英文名称: 5-tert-butoxycarbonylamino-2-fluoro-isonicotinic acid, methyl ester
• 英文别名: 5-tert-butoxycarbonylamino-2-fluoro-isonicotinic acid methyl ester；5-tert-butoxycarbonylamino-2-fluoro-isonicotinic acid,methyl ester；Methyl 5-(boc-amino)-2-fluoropyridine-4-carboxylate；methyl 2-fluoro-5-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-4-carboxylate
• CAS: 305371-15-7
• 化学式: C₁₂H₁₅FN₂O₄
• 分子量: 270.261
• InChiKey: IXYMQZDMTVQOMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-(叔丁氧羰基氨基)-2-氟异烟酸甲酯 在 正丁基锂 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-氯-6-氟-1,7-萘啶-3-甲腈
  参考文献：
  名称：

  Syntheses and EGFR kinase inhibitory activity of 6-substituted-4-anilino [1,7] and [1,8] naphthyridine-3-carbonitriles

  摘要：

  The syntheses and EGFR kinase inhibitory activity of a series of 6-substituted-4-anilino [1,7] and [1,8] naphthyridine-3carbonitriles are described. Both reversible and irreversible binding inhibitors were prepared. These series were compared with each other and with the corresponding 4-anilinoquinoline-3-carbonitriles. Compounds having a 1,7-naphthyridine core structure can retain high potency while those with a 1,8-naphthyridine core are significantly less active. These results are consistent with molecular modeling observations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.034
• 作为产物：
  描述：

  2-氟-5-氨基吡啶 在 正丁基锂 、 四甲基乙二胺 作用下， 以 甲醇 、 乙醚 、 正己烷 、 氯仿 、 叔丁醇 为溶剂， 反应 6.0h， 生成 5-(叔丁氧羰基氨基)-2-氟异烟酸甲酯
  参考文献：
  名称：

  Syntheses and EGFR kinase inhibitory activity of 6-substituted-4-anilino [1,7] and [1,8] naphthyridine-3-carbonitriles

  摘要：

  The syntheses and EGFR kinase inhibitory activity of a series of 6-substituted-4-anilino [1,7] and [1,8] naphthyridine-3carbonitriles are described. Both reversible and irreversible binding inhibitors were prepared. These series were compared with each other and with the corresponding 4-anilinoquinoline-3-carbonitriles. Compounds having a 1,7-naphthyridine core structure can retain high potency while those with a 1,8-naphthyridine core are significantly less active. These results are consistent with molecular modeling observations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.034

文献信息

• Substituted 3-cyano-[1.7],[1.5], and [1.8] naphthyridine inhibitors of tyrosine kinases
  申请人：American Cyanamid Company

  公开号：US06355636B1

  公开（公告）日：2002-03-12

  This invention provides compounds of formula I having the structure useful as inhibitors of protein tyrosine kinase.

  这项发明提供了具有结构的化合物，可作为蛋白酪氨酸激酶抑制剂。
• Substituted 3-cyano-[1.7], [1.5], and [1.8] naphthyridine inhibitors of tyrosine kinases
  申请人：American Cyanamid Company

  公开号：US20020165229A1

  公开（公告）日：2002-11-07

  This invention provides compounds of formula I having the structure 1 wherein: X is cycloalkyl of 3 to 7 carbon atoms, which may be optionally substituted with one or more alkyl of 1 to 6 carbon atom groups; or X is pyridinyl, pyrimidinyl, or Ph; or X is a bicyclic aryl or bicyclic heteroaryl ring system of 8 to 12 atoms, where the bicyclic heteroaryl ring contains 1 to 4 heteroatoms selected from N, O, and S; wherein the bicyclic aryl or bicyclic heteroaryl ring may be optionally mono-, di-, tri-, or tetra-substituted with a substituent selected from the group consisting of halogen, oxo, thio, alkyl of 1-6 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, azido, hydroxyalkyl of 1-6 carbon atoms, halomethyl, alkoxymethyl of 2-7 carbon atoms, alkanoyloxymethyl of 2-7 carbon atoms, alkoxy of 1-6 carbon atoms, alkylthio of 1-6 carbon atoms, hydroxy, trifluoromethyl, cyano, nitro, carboxy, carboalkoxy of 2-7 carbon atoms, carboalkyl of 2-7 carbon atoms, phenoxy, phenyl, thiophenoxy, benzoyl, benzyl, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 2 to 12 carbon atoms, phenylamino, benzylamino, alkanoylamino of 1-6 carbon atoms, alkenoylamino of 3-8 carbon atoms, alkynoylamino of 3-8 carbon atoms, carboxyalkyl of 2-7 carbon atoms, carboalkoxyalkyl of 3-8 carbon atoms, aminoalkyl of 1-5 carbon atoms, N-alkylaminoalkyl of 2-9 carbon atoms, N,N-dialkylaminoalkyl of 3-10 carbon atoms, N-alkylaminoalkoxy of 2-9 carbon atoms, N,N-dialkylaminoalkoxy of 3-10 carbon atoms, mercapto, methylmercapto, and benzoylamino; or X is the radical 2 ; E is pyridinyl, pyrimidinyl, or Ph; T is substituted on E at carbon and is —NH(CH 2 ) m —, —O(CH 2 ) m —, —S(CH 2 ) m —, —NR(CH 2 ) m —, —(CH 2 ) m —(CH 2 ) m NH—, —(CH 2 ) m O—, —(CH 2 ) m S—, or —(CH 2 ) m NR—; L is a Ph; or L is a 5- or 6-membered heteroaryl ring where the heteroaryl ring contains 1 to 3 heteroatoms selected from N, O, and S; wherein the heteroaryl ring may be optionally mono- or di-substituted with a substituent selected from the group consisting of halogen, oxo, thio, alkyl of 1-6 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, azido, hydroxyalkyl of 1-6 carbon atoms, halomethyl, alkoxymethyl of 2-7 carbon atoms, alkanoyloxymethyl of 2-7 carbon atoms, alkoxy of 1-6 carbon atoms, alkylthio of 1-6 carbon atoms, hydroxy, trifluoromethyl, cyano, nitro, carboxy, carboalkoxy of 2-7 carbon atoms, carboalkyl of 2-7 carbon atoms, phenoxy, phenyl, thiophenoxy, benzoyl, benzyl, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 2 to 12 carbon atoms, phenylamino, benzylamino, alkanoylamino of 1-6 carbon atoms, alkenoylamino of 3-8 carbon atoms, alkynoylamino of 3-8 carbon atoms, carboxyalkyl of 2-7 carbon atoms, carboalkoxyalkyl of 3-8 carbon atoms, aminoalkyl of 1-5 carbon atoms, N-alkylaminoalkyl of 2-9 carbon atoms, N,N-dialkylaminoalkyl of 3-10 carbon atoms, N-alkylaminoalkoxy of 2-9 carbon atoms, N,N-dialkylaminoalkoxy of 3-10 carbon atoms, mercapto, methylmercapto, and benzoylamino; Pyridinyl, pyrimidinyl, or Ph are pyridinyl, pyrimidinyl, or phenyl radicals, respectively, which may be optionally mono- di-, or tri-substituted with a substituent selected from the group consisting of halogen, alkyl of 1-6 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, azido, hydroxyalkyl of 1-6 carbon atoms, halomethyl, alkoxymethyl of 2-7 carbon atoms, alkanoyloxymethyl of 2-7 carbon atoms, alkoxy of 1-6 carbon atoms, alkylthio of 1-6 carbon atoms, hydroxy, trifluoromethyl, cyano, nitro, carboxy, carboalkoxy of 2-7 carbon atoms, carboalkyl of 2-7 carbon atoms, benzoyl, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 2 to 12 carbon atoms, alkanoylamino of 1-6 carbon atoms, alkenoylamino of 3-8 carbon atoms, alkynoylamino of 3-8 carbon atoms, carboxyalkyl of 2-7 carbon atoms, carboalkoxyalkyl of 3-8 carbon atoms, aminoalkyl of 1-5 carbon atoms, N-alkylaminoalkyl of 2-9 carbon atoms, N,N-dialkylaminoalkyl of 3-10 carbon atoms, N-alkylaminoalkoxy of 2-9 carbon atoms, N,N-dialkylaminoalkoxy of 3-10 carbon atoms, mercapto, methylmercapto, and benzoylamino; Z is —NH—, —O—, —S—, or —NR—; R is alkyl of 1-6 carbon atoms, or carboalkyl of 2-7 carbon atoms; A″ is a diavalent moiety selected from the group 3 G 1 , G 2 , G 3 , and G 4 are each, independently, hydrogen, halogen, alkyl of 1-6 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, alkenyloxy of 2-6 carbon atoms, alkynyloxy of 2-6 carbon atoms, hydroxymethyl, halomethyl, alkanoyloxy of 2-6 carbon atoms, alkenoyloxy of 3-8 carbon atoms, alkynoyloxy of 3-8 carbon atoms, alkanoyloxymethyl of 2-7 carbon atoms, alkenoyloxymethyl of 49 carbon atoms, alkynoyloxymethyl of 49 carbon atoms, alkoxymethyl of 2-7 carbon atoms, alkoxy of 1-6 carbon atoms, alkylthio of 1-6 carbon atoms, alkylsulphinyl of 1-6 carbon atoms, alkylsulphonyl of 1-6 carbon atoms, alkylsulfonamido of 1-6 carbon atoms, alkenylsulfonamido of 2-6 carbon atoms, alkynylsulfonamido of 2-6 carbon atoms, hydroxy, trifluoromethyl, trifluoromethoxy, cyano, nitro, carboxy, carboalkoxy of 2-7 carbon atoms, carboalkyl of 2-7 carbon atoms, phenoxy, phenyl, thiophenoxy, benzyl, amino, hydroxyamino, alkoxyamino of 1-4 carbon atoms, alkylamino of 1-6 carbon atoms, dialkylamino of 2 to 12 carbon atoms, N-alkylcarbamoyl, N,N-dialkylcarbamoyl, N-alkyl-N-alkenylamino of 4 to 12 carbon atoms, N,N-dialkenylamino of 6-12 carbon atoms, phenylamino, benzylamino, R 2 NH, 4 R 7 —(C(R 6 ) 2 ) g —Y—, R 7 —(C(R 6 ) 2 ) p —M—(C(R 6 ) 2 ) k —Y—, Het-(C(R 6 ) 2 ) q —W—(C(R 6 ) 2 ) k —Y—, with the proviso that G 3 and G 4 are not R 2 NH; Y is a divalent radical selected from the group consisting of 5 R 7 is —NR 6 R 6 , —OR 6 , —J, —N(R 6 ) 3 + , or —NR 6 (OR 6 ); M is >NR 6 , —O—, >N—(C(R 6 ) 2 ) p NR 6 R 6 , or >N—(C(R 6 ) 2 ) p —OR 6 ; W is >NR 6 , —O— or is a bond; Het is a heterocyclic radical selected from the group consisting of morpholine, thiomorpholine, thiomorpholine S-oxide, thiomorpholine S,S-dioxide, piperidine, pyrrolidine, aziridine, pyridine, imidazole, 1,2,3-triazole, 1,2,4-triazole, thiazole, thiazolidine, tetrazole, piperazine, furan, thiophene, tetrahydrothiophene, tetrahydrofuran, dioxane, 1,3-dioxolane, tetrahydropyran, and 6 which may be optionally mono- or di-substituted on carbon with R 6 , hydroxy, —N(R 6 ) 2 , —OR 6 —(C(R 6 ) 2 ) s OR 6 or —(C(R 6 ) 2 ) s N(R 6 ) 2 ; optionally mono-substituted on nitrogen with R 6 ; and optionally mono or di-substituted on a saturated carbon with divalent radicals —O— or —O(C(R 6 ) 2 ) s O—; R 6 is hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cycloalkyl of 1-6 carbon atoms, carboalkyl of 2-7 carbon atoms, carboxyalkyl 2-7 carbon atoms, phenyl, or phenyl optionally substituted with one or more halogen, alkoxy of 1-6 carbon atoms, trifluoromethyl, amino, alkylamino of 1-3 carbon atoms, dialkylamino of 2-6 carbon atoms, nitro, cyano, azido, halomethyl, alkoxymethyl of 2-7 carbon atoms, alkanoyloxymethyl of 2-7 carbon atoms, alkylthio of 1-6 carbon atoms, hydroxy, carboxyl, carboalkoxy of 2-7 carbon atoms, phenoxy, phenyl, thiophenoxy, benzoyl, benzyl, phenylamino, benzylamino, alkanoylamino of 1-6 carbon atoms, or alkyl of 1-6 carbon atoms; with the proviso that the alkenyl or alkynyl moiety is bound to a nitrogen or oxygen atom through a saturated carbon atom; R 2 , is selected from the group consisting of 7 R 3 is hydrogen, alkyl of 1-6 carbon atoms, carboxy, carboalkoxy of 1-6 carbon atoms, phenyl, carboalkyl of 2-7 carbon atoms, 8 , R 7 —(C(R) 2 ) s —, R 7 —(C(R 6 ) 2 ) p —M—(C(R 6 ) 2 ) r —, R 8 R 9 —CH—M(C(R 6 ) 2 ) r —, or Het-(C(R 6 ) 2 ) q —W—C(R 6 ) 2 ) r —; R 5 is hydrogen, alkyl of 1-6 carbon atoms, carboxy, carboalkoxy of 1-6 carbon atoms, phenyl, carboalkyl of 2-7 carbon atoms, 9 , R 7 —(C(R 6 ) 2 ) s —, R 7 —(C(R 6 ) 2 ) p —M—(C(R 6 ) 2 ) r —, R 8 R 9 —CH—M—(C(R 6 ) 2 ) r —, or Het-(C(R 6 ) 2 ) q —W—(C(R 6 ) 2 ) r —; R 8 , and R 9 are each, independently, —(C(R 6 ) 2 ) r NR 6 R 6 , or —(C(R 6 ) 2 ) r OR 6 ; J is independently hydrogen, chlorine, fluorine, or bromine; Q is alkyl of 1-6 carbon atoms or hydrogen; a=0-1; g=1-6; k=0-4; n is 0-1; m is 0-3; p=2-4; q=0-4; r=1-4; s=1-6; u=0-4 and v=0-4, wherein the sum of u+v is 2-4; or a pharmaceutically acceptable salt thereof, provided that when R 6 is alkenyl of 2-7 carbon atoms or alynyl of 2-7 carbon atoms, such alkenyl or alynyl moiety is bound to a nitrogen or oxygen atom through a saturated carbon atom; and provided that when R 3 is bound to sulfur, it cannot be hydrogen, carboxy, carboalkoxy, or carboalkyl; and provided that when Y is —NR 6 — and R 7 is —NR 6 R 6 , —N(R 6 ) 3 + , or —NR 6 (OR 6 ), then g=2-6; when M is —O— and R 7 is —OR 6 then p=1-4; when Y is —NR 6 — then k=2-4; when Y is —O— and M or W is —O— then k=1-4 when W is not a bond with Het bonded through a nitrogen atom then q=2-4 and when W is a bond with Het bonded through a nitrogen atom and Y is —O— or —NR6— then k=2-4; and finally provided that when A″ is the moiety 10 n=0, Z is NH, G 1 is hydrogen, halogen, alkyl, alkoxy, hydroxy, alkanoyloxy of 2-6 carbon atoms, or phenoxy, and G 2 is hydrogen, halogen, alkyl, hydroxy, carboxyalkyl, carboalkoxyalkyl, hydroxyalkyl, alkoxy,halomethyl, carboxyl, carboalkoxy, alkanoylamino, or alkenoylamino, then X can not be a pyridinyl, pyrimidinyl, or phenyl ring that is substituted with a hydroxy or alkoxy group, which are useful as inhibitors of protein tyrosine kinase.

  本发明提供了具有以下结构的公式I的化合物：其中：X是3到7个碳原子的环烷基，可以选择地用1到6个碳原子的烷基取代；或者X是吡啶基、嘧啶基或苯基；或者X是8到12个原子的双环芳基或双环杂芳基环系，其中双环杂芳基环含有1到4个从N、O和S中选择的杂原子；其中双环芳基或双环杂芳基环可以选择地单、双、三或四取代，取代基选择自卤素、氧代、硫代、1-6个碳原子的烷基、2-6个碳原子的烯基、2-6个碳原子的炔基、偶氮基、1-6个碳原子的羟基烷基、卤代甲基、2-7个碳原子的烷氧甲基、2-7个碳原子的烷酰氧甲基、1-6个碳原子的烷氧基、1-6个碳原子的烷硫基、羟基、三氟甲基、氰基、硝基、羧基、2-7个碳原子的羧酸酯基、2-7个碳原子的羧基烷基、苯氧基、苯基、噻吩氧基、苯甲酰基、苄基、氨基、1-6个碳原子的烷基氨基、2到12个碳原子的二烷基氨基、苯基氨基、苄基氨基、1-6个碳原子的烷酰氨基、3-8个碳原子的烯酰氨基、3-8个碳原子的炔酰氨基、2-7个碳原子的羧基烷基、3-8个碳原子的羧酸酯基烷基、1-5个碳原子的氨基烷基、2-9个碳原子的N-烷基氨基烷基、3-10个碳原子的N,N-二烷基氨基烷基、2-9个碳原子的N-烷基氨基烷氧基、3-10个碳原子的N,N-二烷基氨基烷氧基、巯基、甲硫基和苯甲酰氨基；或者X是基团2；E是吡啶基、嘧啶基或苯基；T在碳上被取代，为—NH(CH2)m—、—O(CH2)m—、—S(CH2)m—、—NR(CH2)m—、—(CH2)m—(CH2)mNH—、—(CH2)mO—、—(CH2)mS—或—(CH2)mNR—；L是苯基；或者L是一个5或6元杂芳基环，其中杂芳基环含有1到3个从N、O和S中选择的杂原子；其中杂芳基环可以选择地单取代或双取代，取代基选择自卤素、氧代、硫代、1-6个碳原子的烷基、2-6个碳原子的烯基、2-6个碳原子的炔基、偶氮基、1-6个碳原子的羟基烷基、卤代甲基、2-7个碳原子的烷氧甲基、2-7个碳原子的烷酰氧甲基、1-6个碳原子的烷氧基、1-6个碳原子的烷硫基、羟基、三氟甲基、氰基、硝基、羧基、2-7个碳原子的羧酸酯基、2-7个碳原子的羧基烷基、苯氧基、苯基、噻吩氧基、苯甲酰基、苄基、氨基、1-6个碳原子的烷基氨基、2到12个碳原子的二烷基氨基、苯基氨基、苄基氨基、1-6个碳原子的烷酰氨基、3-8个碳原子的烯酰氨基、3-8个碳原子的炔酰氨基、2-7个碳原子的羧基烷基、3-8个碳原子的羧酸酯基烷基、1-5个碳原子的氨基烷基、2-9个碳原子的N-烷基氨基烷基、3-10个碳原子的N,N-二烷基氨基烷基、2-9个碳原子的N-烷基氨基烷氧基、3-10个碳原子的N,N-二烷基氨基烷氧基、巯基、甲硫基和苯甲酰氨基；Pyridinyl、pyrimidinyl或Ph分别是吡啶基、嘧啶基或苯基基团，可以选择地单、双或三取代，取代基选择自卤素、1-6个碳原子的烷基、2-6个碳原子的烯基、2-6个碳原子的炔基、偶氮基、1-6个碳原子的羟基烷基、卤代甲基、2-7个碳原子的烷氧甲基、2-7个碳原子的烷酰氧甲基、1-6个碳原子的烷氧基、1-6个碳原子的烷硫基、羟基、三氟甲基、氰基、硝基、羧基、2-7个碳原子的羧酸酯基、2-7个碳原子的羧基烷基、苯甲酰基、氨基、1-6个碳原子的烷基氨基、2到12个碳原子的二烷基氨基、1-6个碳原子的烷酰氨基、3-8个碳原子的烯酰氨基、3-8个碳原子的炔酰氨基、2-7个碳原子的羧基烷基、3-8个碳原子的羧酸酯基烷基、1-5个碳原子的氨基烷基、2-9个碳原子的N-烷基氨基烷基、3-10个碳原子的N,N-二烷基氨基烷基、2-9个碳原子的N-烷基氨基烷氧基、3-10个碳原子的N,N-二烷基氨基烷氧基、巯基、甲硫基和苯甲酰氨基；Z是—NH—、—O—、—S—或—NR—；R是1-6个碳原子的烷基或2-7个碳原子的羧基烷基；A″是从群体3中选择的二价基团，G1、G2、G3和G4分别独立地是氢、卤素、1-6个碳原子的烷基、2-6个碳原子的烯基、2-6个碳原子的炔基、2-6个碳原子的烯氧基、2-6个碳原子的炔氧基、羟甲基、卤代甲基、2-6个碳原子的烷酰氧基、3-8个碳原子的烯酰氧基、3-8个碳原子的炔酰氧基、2-7个碳原子的烷酰氧甲基、3-8个碳原子的烯酰氧甲基、3-8个碳原子的炔酰氧甲基、2-7个碳原子的烷氧甲基、1-6个碳原子的烷氧基、1-6个碳原子的烷硫基、1-6个碳原子的烷磺酰基、1-6个碳原子的烷磺酰胺基、2-6个碳原子的烯磺酰胺基、2-6个碳原子的炔磺酰胺基、羟基、三氟甲基、三氟甲氧基、氰基、硝基、羧基、2-7个碳原子的羧酸酯基、2-7个碳原子的羧基烷基、苯氧基、苯基、噻吩氧基、苄基、氨基、1-4个碳原子的烷氧基、1-6个碳原子的烷基氨基、2到12个碳原子的二烷基氨基、N-烷基氨基烷基、N,N-二烷基氨基烷基、4到12个碳原子的N-烷基-N-烯基氨基、6-12个碳原子的N,N-二烯基氨基、苯基氨基、苄基氨基、R2NH、R7—(C(R6)2)g—Y—、R7—(C(R6)2)p—M—(C(R6)2)k—Y—、Het-(C(R6)2)q—W—(C(R6)2)k—；但是当R6为2-7个碳原子的烯基或炔基时，该烯基或炔基通过饱和碳原子与氮或氧原子结合；当R3与硫结合时，它不能是氢、羧基、羧酸酯基或羧基烷基；当Y是—NR6—且R7是—NR6R6、—N(R6)3+或—NR6(OR6)时，g=2-6；当M是—O—且R7是—OR6时，p=1-4；当Y是—NR6—时，k=2-4；当Y是—O—且M或W是—O—时，k=1-4；当W不是与Het通过氮原子结合的键时，q=2-4；当W是与Het通过氮原子结合的键且Y是—O—或—NR6—时，k=2-4；最后，当A″是基团10时，n=0，Z是NH，G1是氢、卤素、烷基、烷氧基、羟基、2-6个碳原子的烷酰氧基或苯氧基，G2是氢、卤素、烷基、羟基、烷基羧酸、烷氧基、卤代甲基、羧基、羧酸酯基、1-6个碳原子的烷基酰胺基或3-8个碳原子的烯基酰胺基时，X不能是带有氢氧基或烷氧基取代的吡啶基、嘧啶基或苯基环，这些化合物可用作蛋白酪氨酸激酶的抑制剂。
• Substituted 3-cyano-[1.7], [1.5], and [1.8] naphthyridine inhibitors of tyrosine kinases
  申请人：American Cyanamid Company

  公开号：US06548496B2

  公开（公告）日：2003-04-15

  This invention provides compounds of formula I having the structure Wherein substitutions at A″, Z, n, and X are set forth in the specification.

  该发明提供了具有以下结构的I型化合物，其中A″，Z，n和X的取代基在规范中列出。
• SUBSTITUTED-3-CYANO-[1.7],[1.5], AND [1.8]-NAPHTHYRIDINE INHIBITORS OF TYROSINE KINASES
  申请人：Wyeth Holdings Corporation

  公开号：EP1171440B1

  公开（公告）日：2004-04-14
• US7432279B2
  申请人：——

  公开号：US7432279B2

  公开（公告）日：2008-10-07