CN1355811A - 整联蛋白受体拮抗剂 - Google Patents

整联蛋白受体拮抗剂 Download PDF

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CN1355811A
CN1355811A CN00808907A CN00808907A CN1355811A CN 1355811 A CN1355811 A CN 1355811A CN 00808907 A CN00808907 A CN 00808907A CN 00808907 A CN00808907 A CN 00808907A CN 1355811 A CN1355811 A CN 1355811A
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amino
gly
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carbonyl
bala
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A·克林
U·朗格
A·劳特巴赫
H·詹尼斯特
T·萨伯考夫斯基
J-C·采切尔
C·I·格莱夫
W·霍恩伯格
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Ebert GmbH and Co KG
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BASF SE
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Priority claimed from DE1999148269 external-priority patent/DE19948269A1/de
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Abstract

本发明涉及与整联蛋白受体结合的新的化合物,他们的制备和作为整联蛋白受体拮抗剂和治疗疾病的用途,含有该新化合物的药物制剂以及含有至少一种其它活性化合物的药物制剂。

Description

整联蛋白受体拮抗剂
本发明涉及与整联蛋白受体结合的新的化合物,它们的制备和用途。
整联蛋白为细胞表面糖蛋白受体,可介导同种细胞和不同细胞之间,以及细胞和细胞外的基质蛋白间的相互作用。它们涉及生理学过程,例如,胚胎发育,止血,创伤治愈,免疫应答,和组织结构的形成/维持。
细胞粘附分子的基因表达障碍,和受体功能的障碍可导致很多病症的发病机制,例如,肿瘤,血栓栓子,心血管病症,与肺有关的疾病,CNS病症,肾病,胃肠道病症或炎症。
整联蛋白为杂二聚体,每个由通过非供价连接的α和β透过膜亚单位构成。迄今为止,人们已经确定了16种不同的α亚单位和8种不同的β亚单位和22种不同的组合。
整联蛋白αvβ3,也被称作玻连蛋白受体,可调解与大量配体-血浆蛋白,细胞外基质蛋白,细胞表面蛋白的粘连,-它们中大多数含有氨基酸序列RGD(Cell,1986,44,517-518;Science 1987,238,491-497),例如,玻连蛋白,纤维蛋白原,纤连蛋白,冯.威利布兰德因子,血小板反应蛋白,骨桥蛋白,层粘连蛋白,胶原蛋白,凝血酶,细胞粘合素,MMP-2,骨涎蛋白II,各种病毒,寄生虫,细菌蛋白,天然整联蛋白拮抗物例如分解蛋白,神经毒素-眼镜蛇素-和水蛭蛋白-decorsin,ornatin-和一些非RGD配体,例如,Cyr-61,PECAM(L.Piali,J.Cell Biol.1995,130,451-460;Buckley,J.Cell Science 1996,109,437-445,J.Biol.Chem.1998,273,3090-3096)。
一些整联蛋白受体显示出与包含RGD主体的配体的交叉反应活性。因此,整联蛋白αIIbβ3,也叫做血小板纤维蛋白原受体,可识别粘连蛋白,玻连蛋白,血小板反应蛋白,冯.威利布兰德因子和纤维蛋白原。
整联蛋白αvβ3特别在内皮细胞,血小板,单核细胞/巨噬细胞,平滑肌细胞,一部分B细胞,成纤维细胞,破骨细胞和各种肿瘤细胞例如,黑素瘤,恶性胶质瘤,肺,乳房,前列腺和膀胱的恶性肿瘤,骨肉瘤或成神经细胞瘤上表达。
在各种病理学条件下可观察到增强的表达,例如,在前凝血酶减少(prothrombotic)状态,在血管损伤,肿块生长或转移或再灌注的情况下,和在激活细胞上,尤其在内皮细胞,平滑肌细胞或巨噬细胞上。
整联蛋白αvβ3的介入已经在特别是下文中的病理状态中被检测到:
心血管病症例如动脉粥样硬化,血管损伤后再狭窄,和血管成形术(新内膜形成,平滑肌细胞移行和增殖)(J.Vasc.Surg.1994,19,125-134;Circulation 1994,90,2203-2206),
急性肾衰竭(Kidney Int.1994,46,1050-1058;Proc.Natl.Acad.Sci.1993,90,5700-5704;Kidney Int.1995,48,1375-1385),
血管生成结合的毛细血管病,例如,糖尿患者的视网膜病变或类风湿性关节炎(Ann.Rev.Physiol 1987,49,453-464;Int.Ophthalmol.1987,11,41-50;Cell 1994,79,1157-1164;J.Biol.Chem.1992,267,10931-10934),
动脉血栓形成
中风(phase II studies with ReoPro,Centocor Inc.,8th annualEuropean Stroke Meeting),
癌症,例如,在肿瘤转移或肿瘤生长中(肿瘤诱导的血管生成)(Cell 1991,64,327-336;Nature 1989,339,58-61;Science 1995,270,1500-1502),
骨质疏松症(增生后的骨吸收,趋化作用和破骨细胞到骨基质的粘连)(FASEB J.1993,7,1475-1482;Exp.Cell Res.1991,195,368-375,Cell 1991,64,327-336),
高血压,鳞癣,甲状旁腺功能亢进,Paget’s疾病,恶性高血钙,转移的骨溶解性病损,炎症,心赃病,CHF,和用于
抗病毒的,抗寄生虫的或抗细菌的治疗和预防(粘连和内在化)。
由于其关键作用,包含低分子量整联蛋白αvβ3拮抗剂的药物制剂具有特别对所述的适应症的治疗和诊断用途。
有益的αvβ3整联蛋白受体拮抗剂可与整联蛋白αvβ3受体通过强亲和力结合。
特别有益的αvβ3整联蛋白受体拮抗剂还具有可以提高整联蛋白αvβ3的选择性,且在整联蛋白αIIbβ3上具有较小的效果,比例至少为10倍,优选至少100倍。
已经表明以下大量化合物具有整联蛋白αvβ3拮抗剂的效果,并显示出在体内的有益效果,例如抗αvβ3单细胞系抗体,含有RGD结合序列的肽,天然含RGD蛋白(例如分解蛋白)和低分子量化合物。(FEBS Letts 1991,291,50-54;J.Biol.Chem.1990,265,12267-12271;J.Biol.Chem.1994,269,20233-20238;J.Cell Biol1993,51,206-218;J.Biol.Chem.1987,262,17703-17711;Bioorg.Med.Chem.1998,6,1185-1208)。
WO 9708145描述了间胍基,尿素,硫脲或氮杂环氨基苯甲酸衍生物及其用作αvβ3整联蛋白受体拮抗剂。
本发明的一个目的是提供具有有利性质的新的整联蛋白受体拮抗剂。
我们发现此目的可通过式I的化合物实现:
                      A-E-G-L        I
其中A,E,G和L具有下面的含义:L为式IL的结构单元
Figure A0080890700151
其中:
a为0或1,
T为COOH基团或可水解为COOH的基团,
R2为氢,NHSO2R21,NHCOR21或NHCOOR22
其中
R21为支链或非支链,任选取代的C1-C6-烷基,C3-C6-环烷基,C1-C4-烷基-C3-C6-环烷基基团,C5-C12-二环烷基或C6-C18-三环烷基基团,至多三个相同或不同取代基取代的芳基,烷基芳基,杂芳基基团或3到6元饱和,不饱和或芳香杂环,该环含有至多三个相同或不同杂原子O,N,S,其中两个基团一起形成一稠和的,饱和的,不饱和的或芳香的碳环或杂环,该环含有至多三个相同或不同杂原子O,N,S,且该环可选的可被取代,或一个可选的被取代的,饱和的,不饱和的或芳香环可与该环稠和,
R22为支链或非支链的,任选取代的C1-C6-烷基或任选取代的芳基或烷基芳基基团,
R3为氢或-(CH2)b-(X)c-R31
其中
b为0,1,2或3,
c为0或1,
X为-SO2-,-S-,-O-,-CO-,-NH-SO2-,-O-CO-,-CO-O-,-NH-CO-,-CO-NH-,-CO-N(R31)-,-N(R31)-CO-,-SO2-NH-,-SO2-N(R31)-或-N(R31)-SO2-,
R31为氢,羟基,支链或非支链的,任选取代的C1-C6-烷基,C1-C4-烷氧基,-O-烷基芳基或-O-芳基,具有伯取代或可选地仲或叔取代的氨基基团,可选地被C1-C4-烷基-或芳基取代的C2-C6-炔基或C2-C6-链烯基基团,C5-C12-二环烷基,C6-C18-三环烷基基团或可被至多三个相同或不同的基团取代的,可能包含至多三个不同的或相同的杂原子O,N,S的3-到6-元饱和或不饱和的杂环,C3-C8-环烷基,芳基或杂芳基基团,其中两个基团可能一起为稠合的,饱和,不饱和的或芳香碳环或杂环,该环可能包含至多三个不同的或相同的杂原子O,N,S,并且该环可选地被取代,或者,另一个任选取代的,饱和的,不饱和的或芳香环可与该环稠合,
R4为氢,或支链或非支链的,任选取代的C1-C4-烷基,C3-C6-烯基,C3-C6-炔基或者C3-C6-环烷基基团,
G为式IG的结构单元
其中
d为0,1或2,
R5为氢,羟基,支链或非支链的,任选取代的C1-C6-烷基,C1-C4-烷氧基,-O-烷基芳基或-O-芳基,具有伯取代或可选地仲或叔取代的氨基基团,可选地被C1-C4-烷基-或芳基取代的C2-C6-炔基或C2-C6-链烯基基团,C5-C12-二环烷基,C6-C18-三环烷基基团或可被至多三个相同或不同的基团取代的,可能包含至多三个不同的或相同的杂原子O,N,S的3-到6-元饱和或不饱和的杂环,C3-C8-环烷基,芳基或杂芳基基团,其中两个基团可能一起为稠合的,饱和,不饱和的或芳香碳环或杂环,该环可能包含至多三个不同的或相同的杂原子O,N,S,并且该环可选地被取代,或者,另一个任选取代的,饱和的,不饱和的或芳香环可与该环稠合,或天然氨基酸的侧链,
R6为氢,或支链或非支链的,任选取代的C1-C4-烷基,C3-C6-链烯基,C3-C6-炔基或者C3-C6-环烷基基团,
E为式IE的结构单元
-(NH)g-(CH2)f-Q-(CH2)e-CO-       IE
其中
e为0,1或2,
f为0或1,
g为0或1,
Q为双次连接的,任选取代的杂芳基基团,其中两个取代基可以一起为一饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O,N,S,并且该环可以可选地被取代,或者,另一个任选取代的、饱和的,不饱和的或芳香环可以与该环稠合,
A为式IA 1到IA 20结构单元之一
Figure A0080890700181
其中
R10,R11各自独立地为氢,-(CH2)h-(Y)i-R101,或两个基团一起为3-到8元,任选取代的,饱和的,不饱和的或芳香N-杂环,该环可以另外包含两个其它相同的或不同的杂原子O,N或S,
其中
h为0,1,2或3,
i为0或1,
Y为-SO2-,-S-,-O-,-CO-,-NH-SO2-,-O-CO-,-CO-O-,-NH-CO-,-CO-NH-,-CO-N(R101)-,-N(R101)-CO-,-SO2-NH-,-N(R101)-SO2-或-SO2-N(R101)-且
R101为羟基,支链或非支链的,任选取代的C1-C6-烷基,C1-C4-烷氧基,-O-烷基芳基或-O-芳基,具有伯取代或可选地仲或叔取代的氨基基团,可选被C1-C4-烷基-或芳基取代的C2-C6-炔基或C2-C6-链烯基基团,C5-C12-二环烷基,C6-C18-三环烷基基团或可被至多三个相同或不同的基团取代的,可能包含至多三个不同的或相同的杂原子O,N,S的3-到6-元饱和或不饱和的杂环,C3-C8-环烷基,芳基或杂芳基基团,其中两个基团可能一起为稠合的,饱和的,不饱和的或芳香碳环或杂环,该环可能包含至多三个不同的或相同的杂原子O,N,S,并且该环可选地被取代,或者,另一个任选取代的,饱和的,不饱和的或芳香环可与该环稠合,
R12为支链或非支链的,任选取代的C1-C4-烷基,烷基芳基,C3-C6环烷基或C1-C4-烷基-C3-C6-环烷基基团或任选取代的芳基,
R13为氢,-OH,-CN,-CONH2,任选取代的支链或非支链C1-C4-烷基,C1-C4-烷氧基或-OCO-C1-C4-烷基基团,或任选取代的烷基芳基,-O-烷基芳基,-OCO-芳基,-OCO-烷基芳基或-OCO-烯丙基基团,
R14为氢,任选取代的支链或非支链的C1-C4-烷基,烷基芳基,-CO2-C1-C4-烷基,-CO2-烷基芳基,-CO2-烯丙基,-CO-C1-C4-烷基,-CO-烷基芳基或-CO--烯丙基基团,
R15为氢,任选取代的支链或非支链的C1-C4-烷基或任选取代的芳基或烷基芳基基团,
R16,R17各自独立的为-NH2,卤素或任选取代的支链或非支链的C1-C4-烷基或C1-C4-烷氧基基团或任选取代的芳基,
Z1,Z2,Z3,Z4各自独立地为CH,C-CH3,C-OCH3,C-Cl或N
和生理学可接受的盐,前体药物及对映体纯或非对映体纯和互变异构形式。
结构单元L中的T指COOH基团或可被水解成COOH的基团。可被水解成COOH的基团是指水解后可转变为COOH基团的基团。
可作为可被水解成COOH的基团T的基团的实例为
Figure A0080890700201
其中R1具有下面的含义:
a)OM,其中M可以为金属阳离子例如碱金属阳离子例如锂,钠,钾,等当量的碱土金属阳离子例如钙,镁和钡,或环境相容的有机铵离子例如叔C1-C4-烷基铵或铵离子,例如,ONa,OK或OLi,
b)可选地被卤素取代的支链或非支链的C1-C8-烷氧基基团例如,甲氧基,乙氧基,丙氧基,1-甲基乙氧基,丁氧基,1-甲基丙氧基,2-甲基丙氧基,1,1-二甲基乙氧基,优选甲氧基,乙氧基,1-甲基乙氧基,戊氧基,己氧基,庚氧基,辛氧基,二氟甲氧基,三氟甲氧基,一氯二氟甲氧基,1-氟乙氧基,2-氟乙氧基,2,2-二氟乙氧基,1,1,2,2-四氟乙氧基,2,2,2-三氟乙氧基,2-氯-1,1,2-三氟乙氧基或五氟乙氧基
c)可选地被卤素取代的支链或非支链的C1-C4-烷硫基基团例如甲硫基,乙硫基,丙硫基,1-甲基乙硫基,丁硫基,1-甲基丙硫基,2-甲基丙硫基或1,1-二甲基乙硫基基团
d)任选取代的-O-烷基芳基基团例如,-O-苄基
e)R1还可为式-(O)m-N(R18)(R19)的基团,其中m为0或1,且R18和R19,可以相同或不同,具有以下的含义:
氢,
C1-C8-烷基,例如,甲基,乙基,丙基,1-甲基乙基,丁基,1-甲基丙基,2-甲基丙基,1,1-二甲基乙基,戊基,1-甲基丁基,2-甲基丁基,1,2-二甲丙基,1,1-二甲基丙基,2,2-二甲丙基,1-乙基丙基,己基,1-甲基戊基,1,2-二甲基丁基,1,3-二甲基丁基,2,3-二甲基丁基,1,1-二甲基丁基,2,2-二甲基丁基,3,3-二甲基丁基,1,1,2-三甲基丙基,1,2,2-三甲基丙基,1-乙基丁基,2-乙基丁基,庚基或辛基,
C3-C6-烯基例如,2-丙烯基,2-丁烯基,3-丁烯基,1-甲基-2-丙烯基,2-甲基-2-丙烯基,2-戊烯基,3-戊烯基,4-戊烯基,1-甲基-2-丁烯基,2-甲基-2-丁烯基,3-甲基-2-丁烯基,1-甲基-3-丁烯基,2-甲基-3-丁烯基,3-甲基-3-丁烯基,1,1-二甲基-2-丙烯基,1,2-二甲基-2-丙烯基,1-乙基-2-丙烯基,2-己烯基,3-己烯基,4-己烯基,5-己烯基,1-甲基-2-戊烯基,2-甲基-2-戊烯基,3-甲基-2-戊烯基,4-甲基-2-戊烯基,3-甲基-3-戊烯基,4-甲基-3-戊烯基,1-甲基-4-戊烯基,2-甲基-4-戊烯基,,3-甲基-4-戊烯基,4-甲基-4-戊烯基,1,1-二甲基-2-丁烯基,1,1-二甲基-3-丁烯基,1,2-二甲基-2-丁烯基,1,2-二甲基-3-丁烯基,1,3-二甲基-2-丁烯基,1,3-二甲基-3-丁烯基,2,2-二甲基-3-丁烯基,2,3-二甲基-2-丁烯基,2,3-二甲基-3-丁烯基,1-乙基-2-丁烯基,1-乙基-3-丁烯基,2-乙基-2-丁烯基,2-乙基-3-丁烯基,1,1,2-三甲基-2-丙烯基,1-乙基-1-甲基-2-丙烯基和1-乙基-2-甲基-2-丙烯基,优选2-丙烯基,2-丁烯基,3-甲基-2-丁烯基和3-甲基-2-戊烯基,
C3-C6-炔基例如,2-丙炔基,2-丁炔基,3-丁炔基,1-甲基-2-丙炔基,2-戊炔基,3-戊炔基,4-戊炔基,1-甲基-3-丁炔基,2-甲基-3-丁炔基,1-甲基-2-丁炔基,1,1-二甲基-2-丙炔基,1-乙基-2-丙炔基,2-己炔基,3-己炔基,4-己炔基,5-己炔基,1-甲基-2-戊炔基,1-甲基-2-戊炔基,1-甲基-3-戊炔基,1-甲基-4-戊炔基,2-甲基-3-戊炔基,2-甲基-4-戊炔基,3-甲基-4-戊炔基,4-甲基-2--戊炔基,1,1-二甲基-2-丁炔基,1,1-二甲基-3-丁炔基,1,2-二甲基-3-丁炔基,2,2-二甲基-3-丁炔基,1-乙基-2-丁炔基,1-乙基-3-丁炔基,2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基,优选2-丙炔基,2-丁炔基,1-甲基-2-丙炔基和1-甲基-2-丁炔基,优选2-丙炔基,
C3-C8-环烷基,例如,环丙基,环丁基,环戊基,环己基和环庚基,环辛基,其中这些烷基,环烷基,烯基和炔基基团各自可以被取代,
可选被一或多次取代的苯基,例如,被卤素,硝基,氰基,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基,C1-C4-卤代烷氧基或C1-C4-烷硫基一到三次取代,例如,2-氟苯基,3-氯苯基,4-溴苯基,2-甲基苯基,3-硝基苯基,4-氰基苯基,2-三氟甲基苯基,3-甲氧基苯基,4-三氟乙氧基苯基,2-甲硫基苯基,2,4-二氯苯基,2-甲氧基-3-甲基苯基,2,4-二甲氧基苯基,2-硝基-5-氰基苯基,2,6-二氟苯基
或R18和R19一起形成可关闭成一个环的C4-C7-亚烷基链,该环可选的被取代,例如被C1-C4-烷基取代,且可含有选自氧,硫或氮的一组的杂原子,例如,-(CH2)4-,-(CH2)5-,-(CH2)6-,-(CH2)7-,-(CH2)2-O-(CH2)2-,-CH2-S-(CH2)3-,-(CH2)2-O-(CH2)3-,-NH-(CH2)3-,-CH2-NH-(CH2)2-,-CH2-CH=CH-CH2-,-CH=CH-(CH2)3-,-CO-(CH2)2-CO-或-CO-(CH2)3-CO-。
优选T基团为-COOH,-CO-O-C1-C8-烷基或-CO-O-苄基。
在结构单元L中对于R21的支链或非支链C1-C6-烷基基团是指,例如,甲基,乙基,丙基,1-甲基乙基,丁基,1-甲基丙基,2-甲基丙基,1,1-二甲基乙基,戊基,1-甲基丁基,2-甲基丁基,1,2-二甲丙基,1,1-二甲基丙基,2,2-二甲丙基,1-乙基丙基,己基,1-甲基戊基,1,2-二甲基丁基,1,3-二甲基丁基,2,3-二甲基丁基,1,1-二甲基丁基,2,2-二甲基丁基,3,3-二甲基丁基,1,1,2-三甲基丙基,1,2,2-三甲基丙基,1-乙基丁基,2-乙基丁基,或1-乙基-2-甲基丙基,优选甲基,乙基,丙基,丁基或异丁基。
在结构单元L中对于R21的支链或非支链C3-C6-环烷基基团是指,例如,环丙基,环丁基,环戊基或环己基。
在结构单元L中对于R21的支链或非支链C1-C4-烷基C3-C6-环烷基基团是指,上述的C3-C6-环烷基作为C1-C4-烷基基团上的一个取代基。
C1-C6-烷基基团,C3-C6-环烷基基团或C1-C4-烷基-C3-C6-环烷基基团可被至多5个相同或不同的选自卤素,芳基或杂芳基的基团取代。
对于R21的C5-C12-二环烷基是指,例如,茚满基,降冰片基或莰基,和C6-C18-三环烷基基团是指,例如金刚烷基。
在结构单元L中对于R21的用至多三个相同的或不同的基团取代的芳基,烷基芳基,烷基杂芳基基团或3到6元饱和的,不饱和的或芳香杂环,该环可包含至多三个不同的或相同的杂原子O,N,S,两个基团可以一起成为一个稠合的,饱和的,不饱和的或芳香碳环或杂环,此环可以包含至多三个不同的或相同的杂原子O,N,S,并且该环可选地被取代,或另一个任选取代的饱和的,不饱和的或芳香环可稠合到该环上,是指,例如,
芳基基团例如,苯基,1-萘基或2-萘基,
烷基芳基基团例如,苄基或苯乙基,
烷基杂芳基例如,-CH2-2-吡啶基,-CH2-3-吡啶基,-CH2-4-吡啶基,-CH2-2-噻吩基,-CH2-3-噻吩基,-CH2-2-噻唑基,-CH2-4-噻唑基,CH2-5-噻唑基,-CH2-CH2-2-吡啶基,-CH2-CH2-3-吡啶基,-CH2-CH2-4-吡啶基,-CH2-CH2-2-噻吩基,-CH2-CH2-3-噻吩基,-CH2-CH2-2-噻唑基,-CH2-CH2-4-噻唑基,或-CH2-CH2-5-噻唑基,优选-CH2-2-吡啶基,-CH2-2-噻吩基,或-CH2-2-噻唑基或
杂芳基基团例如,2-吡啶基,3-吡啶基,4-吡啶基,2-呋喃基,3-呋喃基,2-吡咯基,3-吡咯基,2-噻吩基,3-噻吩基,2-噻唑基,4-噻唑基,5-噻唑基,2-噁唑基,4-噁唑基,5-噁唑基,2-嘧啶基,4-嘧啶基,5-嘧啶基,6-嘧啶基,3-吡唑基,4-吡唑基,5-吡唑基,3-异噻唑基,4-异噻唑基,5-异噻唑基,2-咪唑基,4-咪唑基,5-咪唑基,3-哒嗪基,4-哒嗪基,5-哒嗪基或6-哒嗪基,优选2-吡啶基,3-吡啶基,4-吡啶基,2-呋喃基,3-呋喃基,2-噻吩基,3-噻吩基,2-噻唑基,4-噻唑基或5-噻唑基,
芳基,烷基芳基,烷基杂芳基和杂芳基基团可以被至多三个相同的或不同的基团取代,例如被选自下面的基团取代:
-NO2,-NH2,-OH,-CN,-COOH,-COO-C1-C4-烷基,卤素,支链或非支链,可选地被取代的C1-C4-烷基,C3-C6-环烷基,C1-C4-烷氧基,C1-C4-烷硫基,-O-CH2-COO-C1-C4-烷基,-NH-CO-C1-C4-烷基,-CO-NH-C1-C4-烷基,-NH-SO2-C1-C4-烷基,-SO2-NH-C1-C4-烷基,-N(C1-C4-烷基)2,-NH-C1-C4-烷基,或-SO2-C1-C4-烷基基团,任选取代的-NH-CO-苯基,-CO-NH-苯基,-NH-SO2-苯基,-SO2-NH-苯基,-NH-CO-苄基,-CO-NH-苄基,-NH-SO2-苄基,-SO2-NH-苄基,任选取代的基团-SO2-NT1T2或-CO-NT1T2其中两个基团T1和T2可以形式一环胺,或一个3到6元任选取代的饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O,N,S,或两个基团一起为一稠合的,饱和的,不饱和的或芳香碳环或杂环,此环可以包含至多三个不同的或相同的杂原子O,N,S,并且此环可选地被取代,或者,另一个任选取代的环可以与此环稠合。
对于R21的芳基,烷基芳基,烷基杂芳基或杂芳基基团上的优选取代基为C1-C4-烷基,C3-C6-环烷基,-COOH,-COOMe,-CF3,-CN,C1-C4-烷氧基,-SCH3,-O-CH2-COOH,苯基,-SO2CH3,-NO2,-OH,-NH2,-N-吡咯烷基,-N-哌啶基,-N-吗啉基,-N-哌嗪基,-NH-C1-C4-烷基,-N(C1-C4-烷基)2,F,Cl,Br或I。
对于R21,其中两个基团可以一起为一稠合的,饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O,N,S,并且此环可以可选地被取代,或者,另一个任选取代的环可以与此环稠合的芳基,烷基芳基基团,烷基杂芳基基团和杂芳基基团上的优选取代基为下面的双次连接的结构单元:
Figure A0080890700251
结构单元L中对于R22的支链或非支链C1-C6-烷基基团是指,例如上述对于R21的C1-C6-烷基基团,优选1,1-二甲基乙基。
结构单元L中对于R22的芳基基团的实例为苯基,1-萘基或2-萘基,优选苯基;结构单元L中对于R22的烷基芳基基团优选为苄基或苯乙基。
结构单元L中对于R22的C1-C6-烷基基团,芳基基团或烷基芳基基团上的合适的取代基为上述R21中芳基基团,烷基芳基基团,烷基杂芳基基团和杂芳基基团中提到的取代基。
在结构单元L中的基团R3中,b可为0,1,2或3,优选0,1或2,且c可为0或1。基团X为双连接基团,选自下面的组:-SO2-,-S-,-O-,-CO-,-NH-SO2-,-O-CO-,-CO-O-,-NH-CO-,-CO-NH-,-CO-N(R31)-,-N(R31)-CO-,-SO2-NH-,-SO2-N(R31)-或-N(R31)-SO2-.当基团被R31双取代的情况下,两个R31基团可以相同或不同。
结构单元L中对于R31的支链或非支链C1-C6-烷基基团是指,例如,甲基,乙基,丙基,1-甲基乙基,丁基,1-甲基丙基,2-甲基丙基,1,1-二甲基乙基,戊基,1-甲基丁基,2-甲基丁基,1,2-二甲丙基,1,1-二甲基丙基,2,2-二甲丙基,1-乙基丙基,己基,1-甲基戊基,1,2-二甲基丁基,1,3-二甲基丁基,2,3-二甲基丁基,1,1-二甲基丁基,2,2-二甲基丁基,3,3-二甲基丁基,1,1,2-三甲基丙基,1,2,2-三甲基丙基,1-乙基丁基,2-乙基丁基,或1-乙基-2-甲基丙基,优选甲基,乙基,丙基,丁基,异丙基,仲丁基和叔丁基。
结构单元L中对于R31的支链或非支链C1-C4-烷氧基基团是指,例如,甲氧基,乙氧基,丙氧基,1-甲基乙氧基,丁氧基,1-甲基丙氧基,2-甲基丙氧基或1,1-二甲基乙氧基,优选甲氧基,乙氧基或1-甲基乙氧基。
-O-烷基芳基或-O-芳基的实例为-O-苯基,-O-1-萘基,-O-2-萘基或-O-苄基。
结构单元L中对于R31的C1-C6-烷基,C1-C4-烷氧基基团可被至多五个相同或不同的选自卤素,芳基或杂芳基的一组基团取代。
取代的-O-烷基芳基或-O-芳基是指,例如上述的-O-烷基芳基或-O-芳基基团,其中芳基部分可以被至多三个相同或不同的选自下面基团的基团取代:
-NO2,-NH2,-OH,-CN,-COOH,-COO-C1-C4-烷基,卤素,支链或非支链的,任选取代的C1-C4-烷基,C3-C6-环烷基,C1-C4-烷氧基,C1-C4-烷硫基,-O-CH2-COO-C1-C4-烷基,-NH-CO-C1-C4-烷基,-CO-NH-C1-C4-烷基,-NH-SO2-C1-C4-烷基,-SO2-NH-C1-C4-烷基,-N(C1-C4-烷基)2,-NH-C1-C4-烷基,或-SO2-C1-C4-烷基基团,任选取代的-NH-CO-苯基,-CO-NH-苯基,-NH-SO2-苯基,-SO2-NH-苯基,-NH-CO-苄基,-CO-NH-苄基,-NH-SO2-苄基,-SO2-NH-苄基,任选取代的基团-SO2-NT1T2或-CO-NT1T2其中两个基团T1和T2可以形式一环胺,或一3到6元任选取代的饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O,N,S,或两个基团一起为一稠合的,饱和的,不饱和的或芳香碳环或杂环,此环可以包含至多三个不同的或相同的杂原子O,N,S,并且此环可选地被取代,或者,另一个任选取代的环可以与此环稠合。
结构单元L中对于R31的带有伯,或可选的仲或叔取代的氨基基团是指伯氨基基团-NH2,仲氨基基团-NH(R311)或叔氨基基团-N(R311)(R312),其中
R311和R312可各自独立地为上述的C1-C4-烷基或C3-C6-环烷基,任选取代的芳基,优选苯基,烷基芳基,优选苄基,-CO-C1-C4-烷基,优选-CO-CH3或-CO-芳基,优选-CO-苯基。
在c=1和X=CO的情况下,得到相应的酰胺残基。
在R31为如下所述杂环体系之一的情况下得到环状叔酰胺残基或氨基基团,它们通过环中的氮与X=CO连接,或直接连接。优选的酰胺残基-X-R31的实例为:
Figure A0080890700271
在结构单元L中对于R31的可选被C1-C4-烷基或芳基取代的C2-C6-炔基或C2-C6-烯基基团是指,例如,C2-C6-炔基基团,例如,乙炔基,2-丙炔基,2-丁炔基,3-丁炔基,1-甲基-2-丙炔基,2-戊炔基,3-戊炔基,4-戊炔基,1-甲基-3-丁炔基,2-甲基-3-丁炔基,1-甲基-2-丁炔基,1,1-二甲基-2-丙炔基,1-乙基-2-丙炔基,2-己炔基,3-己炔基,4-己炔基,5-己炔基,1-甲基-2-戊炔基,1-甲基-2-戊炔基,1-甲基-3-戊炔基,1-甲基-4-戊炔基,2-甲基-3-戊炔基,2-甲基-4-戊炔基,3-甲基-4-戊炔基,4-甲基-2--戊炔基,1,1-二甲基-2-丁炔基,1,1-二甲基-3-丁炔基,1,2-二甲基-3-丁炔基,2,2-二甲基-3-丁炔基,1-乙基-2-丁炔基,1-乙基-3-丁炔基,2-乙基-3-丁炔基或1-乙基-1-甲基-2-丙炔基,优选2-丙炔基或乙炔基,
或C2-C6-烯基基团,例如,乙烯基,2-丙烯基,2-丁烯基,3-丁烯基,1-甲基-2-丙烯基,2-甲基-2-丙烯基,2-戊烯基,3-戊烯基,4-戊烯基,1-甲基-2-丁烯基,2-甲基-2-丁烯基,3-甲基-2-丁烯基,1-甲基-3-丁烯基,2-甲基-3-丁烯基,3-甲基-3-丁烯基,1,1-二甲基-2-丙烯基,1,2-二甲基-2-丙烯基,1-乙基-2-丙烯基,2-己烯基,3-己烯基,4-己烯基,5-己烯基,1-甲基-2-戊烯基,2-甲基-2-戊烯基,3-甲基-2-戊烯基,4-甲基-2-戊烯基,3-甲基-3-戊烯基,4-甲基-3-戊烯基,1-甲基-4-戊烯基,2-甲基-4-戊烯基,,3-甲基-4-戊烯基,4-甲基-4-戊烯基,1,1-二甲基-2-丁烯基,1,1-二甲基-3-丁烯基,1,2-二甲基-2-丁烯基,1,2-二甲基-3-丁烯基,1,3-二甲基-2-丁烯基,1,3-二甲基-3-丁烯基,2,2-二甲基-3-丁烯基,2,3-二甲基-2-丁烯基,2,3-二甲基-3-丁烯基,1,1,2-三甲基--2-丙烯基,1-乙基-1-甲基-2-丙烯基或1-乙基-2-甲基-2-丙烯基,优选2-丙烯基或乙烯基
可以被任选取代的C1-C4-烷基,或如上所述的芳基,优选苯基所取代,例如,优选苯基乙炔基或苯基乙烯基。
对于R31的C5-C12-双环烷基基团是指,例如,茚满基,降冰片基或莰基,且C6-C18-三环烷基基团是指,例如金刚烷基。
在结构单元L中对于R31的被至多3个不同的或相同基团取代的3到6元饱和的或不饱和的杂环,该环可包含至多三个不同的或相同的杂原子O,N,S,C3-C8-环烷基,芳基或杂芳基基团,其中两个基团可以一起成为一个稠合的,饱和的,不饱和的或芳香碳环或杂环,此环可以包含至多三个不同的或相同的杂原子O,N,S,并且该环可选地被取代,或另一个任选取代的饱和的,不饱和的或芳香环稠合到该环上,是指,例如,
3到6元饱和的或不饱和的杂环,它们可以包含至多三个不同的或相同的杂原子O,N,S,例如N-吡咯烷基,N-哌啶基,N-六氢氮杂基,N-吗啉基或N-哌嗪基,其中带有游离的氨基质子的杂环例如,N-哌嗪基中的游离氨基质子可以被常规的氨基保护基替代,例如,甲基,苄基,Boc(叔丁氧羰基),Z(苄氧羰基),甲苯磺酰基,-SO2-C1-C4-烷基,-SO2-苯基或-SO2-苄基,
C3-C8-环烷基基团如上面对于R21的基团中所述,
芳基例如,苯基,1-萘基或2-萘基或
杂芳基基团例如,2-吡啶基,3-吡啶基,4-吡啶基,2-呋喃基,3-呋喃基,2-吡咯基,3-吡咯基,2-噻吩基,3-噻吩基,2-噻唑基,4-噻唑基,5-噻唑基,2-噁唑基,4-噁唑基,5-噁唑基,2-嘧啶基,4-嘧啶基,5-嘧啶基,6-嘧啶基,3-吡唑基,4-吡唑基,5-吡唑基,3-异噻唑基,4-异噻唑基,5-异噻唑基,2-咪唑基,4-咪唑基,5-咪唑基,3-哒嗪基,4-哒嗪基,5-哒嗪基或6-哒嗪基,优选2-吡啶基,3-吡啶基,4-吡啶基,2-呋喃基,3-呋喃基,2-噻吩基,3-噻吩基,2-噻唑基,4-噻唑基或5-噻唑基,
其中杂环基,C3-C8-环烷基,芳基和杂芳基基团可以可选地被至多三个相同的或不同的基团取代,例如被选自下面的基团取代:
-NO2,-NH2,-OH,-CN,-COOH,-COO-C1-C4-烷基,卤素,支链或非支链的,任选取代的C1-C4-烷基,C3-C6-环烷基,C1-C4-烷氧基,C1-C4-烷硫基,-O-CH2-COO-C1-C4-烷基,-NH-CO-C1-C4-烷基,-CO-NH-C1-C4-烷基,-NH-SO2-C1-C4-烷基,-SO2-NH-C1-C4-烷基,-N(C1-C4-烷基)2,-NH-C1-C4-烷基,或-SO2-C1-C4-烷基基团,任选取代的-NH-CO-苯基,-CO-NH-苯基,-NH-SO2-苯基,-SO2-NH-苯基,-NH-CO-苄基,-CO-NH-苄基,-NH-SO2-苄基,-SO2-NH-苄基,任选取代的基团-SO2-NT1T2或-CO-NT1T2其中两个基团T1和T2可以形成一环胺,或一3到6元任选取代的饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O,N,S,或两个基团一起为一稠合的,饱和的,不饱和的或芳香碳环或杂环,此环可以包含至多三个不同的或相同的杂原子O,N,S,并且此环可选地被取代,或者,另一个任选取代的环可以与此环稠合。
优选对于R31的杂环基,C3-C8-环烷基,芳基和杂芳基基团的取代基为C1-C4-烷基,-COOH,-COOMe,-CF3,-CN,C1-C4-烷氧基,-SCH3,-O-CH2-COOH,-苯基,-SO2CH3,-NO2,-OH,-NH2,-N-吡咯烷基,-N-哌啶基,-N-吗啉基,-N-哌嗪基,-NH-C1-C4-烷基,-N(C1-C4-烷基)2,F,Cl,Br或I。
对于R31,其中两个基团可以一起为一稠合的,饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O,N,S,并且此环可以可选地被取代,或者,另一个任选取代的环可以与此环稠合的杂环基,C3-C8-环烷基,芳基和杂芳基基团上的优选取代基为下面的双次连接的结构单元:
Figure A0080890700301
对于R31得到的稠合环体系的实例为,例如,相应的二氧戊环基,苯并吡咯基,苯并呋喃基,苯并噻吩基或芴基。
结构单元L中对于R4的支链或非支链任选取代的C1-C4-烷基基团是指,例如,甲基,乙基,丙基,异丙基,丁基,叔丁基或异丁基,优选甲基。
结构单元L中对于R4的支链或非支链任选取代的C3-C6-环烷基基团是指,上述的对于R21的基团,可选地被至多5个基团,例如卤素或芳基取代,优选环己基,环戊基或环丙基。
结构单元L中对于R4的C3-C6-烯基或C3-C6-炔基基团是指上述的对R18或R19所述的基团,优选烯丙基或炔丙基。
对于R4特别优选的基团为氢,甲基,环丙基,烯丙基或炔丙基,并且特别优选氢。
优选结构单元L具有a=1,以便一种β-氨基酸可代表结构单元L的优选的基本结构。特别优选结构单元L,基团R2=氢,并且基团R3可以如上所述广泛地改变,或者基团R3=氢,并且基团R2可以如上所述广泛地改变。特别优选的结构单元L具有R2=H且R3可以如上所述广泛地改变,或R3=H且R2=-NHZ,-NH-SO2-苯基或-NH-SO2-苄基,其中Z为苄氧羰基保护基。
在式IG的结构单元G中,R5是指氢,和与结构单元L中的R31无关,与上述R31中相同的基团,或天然氨基酸的另一个侧链。优选R5基团为氢,甲基,乙炔基或甲基取代的乙炔基,并且特别优选氢。
R6独立于R4指,与上述R4相同的基团。优选R6基团为氢,甲基,烯丙基,炔丙基或环丙基,并且特别优选氢。
在式IE的结构单元E中的Q是指双次连接的,可选被至多三个其它基团取代的杂芳基基团,其中适当的两个基团可以一起为一饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O、N、S,并且此环可以可选地被取代,或者,另一个任选取代地饱和的,不饱和的或芳香环可以与此环稠合。
杂芳基基团优选是指5到6元芳香杂环体系,它们可以包含至多三个不同的或相同的杂原子O,N,S,对于带有游离的氨基质子的杂环例如,咪唑基,三唑基,吡唑基或吡咯基中的游离氨基质子可以被常规的氨基保护基替代,例如,甲基,苄基,Boc(叔丁氧羰基),Z(苄氧羰基),甲苯磺酰基,-SO2-C1-C4-烷基,-SO2-苯基或-SO2-苄基。
优选杂芳基基团Q可能是下面列出的结构,其中连接点用键线显示:
Figure A0080890700311
特别优选杂芳基基团Q可能是下面列出的结构,其中连接点的固定位置用键线显示,并且此结构可以从两个方向结合:
Figure A0080890700321
更特别优选的杂芳基基团Q可能是下面列出的结构,其中连接点的固定位置用键线显示,并且此结构可以从两个方向结合:
Figure A0080890700322
如上所述,在这些优选和特别优选的结构中咪唑基,吡唑基,三唑基或吡咯基的游离胺质子还可以被常规的胺保护基替代,例如,甲基,苄基,Boc(叔丁氧羰基),Z(苄氧羰基),甲苯磺酰基,-SO2-C1-C4-烷基,-SO2-苯基或-SO2-苄基。
优选的杂芳基基团的取代基各自独立地为一或两个选自下面一组的基团,-CN,卤素,优选Cl或F,C1-C4-烷基,优选甲基,C1-C4-卤代烷基,优选三氟甲基,C1-C4-烷氧基,优选甲氧基,-NH-C1-C4-烷基或芳基,优选苯基。
结构单元A为式IA 1到IA 20中的结构单元之一
Figure A0080890700331
其中对于结构单元A,优选式IA 1,IA 2,IA 3,IA 4,IA 5,IA 8,IA 10,或IA 13的结构单元,且特别优选式IA 4的结构单元。
Figure A0080890700332
基团R10和R11,各自独立地并独立于R3,为上述结构单元L中的R3所述的基团,优选C1-C4-烷基,C3-C8-环烷基,C1-C4-烷基-C3-C8-环烷基,芳基,烷基芳基,杂芳基或烷基杂芳基,其中芳基,烷基芳基,杂芳基和烷基杂芳基可带有至多三个相同的或不同的下面一组的基团:F,Cl,Br或I,C1-C4-烷基,C3-C6-环烷基,-COOH,-COOMe,-CF3,-CN,C1-C4-烷氧基,-SCH3,-O-CH2-COOH,苯基,-SO2CH3,-NO2,-OH,-NH2,-N-吡咯烷基,-N-哌啶基,-N-吗啉基,-N-哌嗪基,-NH-C1-C4-烷基,-N(C1-C4-烷基)2,-NH-CO-C1-C4-烷基,-CO-NH-C1-C4-烷基,-NH-SO2-C1-C4-烷基,-SO2-NH-C1-C4-烷基,或-SO2-C1-C4-烷基,任选取代的-NH-CO-苯基,-CO-NH-苯基,-NH-SO2-苯基,-SO2-NH-苯基,-NH-CO-苄基,-CO-NH-苄基,-NH-SO2-苄基,-SO2-NH-苄基,任选取代的-SO2-NT1T2或-CO-NT1T2,其中两个基团T1和T2可形成一环状胺,
或两个基团R10和R11一起形成任选取代的3到8元,饱和的,不饱和的或芳香N-杂环体系,它们可以另外包含两个其它相同的或不同的杂原子O,N,或S,例如,吡咯烷基,哌啶基,六氢氮杂基,哌嗪基或吗啉基。
R12为支链或非支链,任选取代的C1-C4-烷基,烷基芳基,C3-C6-环烷基或C1-C4-烷基-C3-C6-环烷基基团或如上述R21中所述的任选取代的芳基基团。
对于R13的支链或非支链,任选取代的C1-C4-烷氧基或-O-烷基芳基是指上述对于R31的相应的基团,优选甲氧基或苄氧基。基团-OCO-C1-C4-烷基-,-OCO-芳基-,-OCO-烷基芳基-或-OCO-烯丙基-为-OCO-基团和选自上述R31下所述的-组基团:C1-C4-烷基,芳基或烷基芳基基团,或烯丙基基团。
优选R13基团为氢,-OH,-O-苄基,-OCO-苯基,-OCO-苄基,-OCO-烯丙基,-CN或-CO-NH2
类似地,对于基团R14的基团-CO2-C1-4-烷基-,-CO2-烷基芳基-,-CO2-烯丙基-,-CO-C1-C4-烷基-,-CO-烷基芳基-或-CO-烯丙基为-CO2-或-CO-和选自上述R31下所述的一组基团:C1-C4-烷基,芳基基团或烯丙基基团。对于R14优选的基团为氢,甲基,苄基,-COO-苄基,-COO-烯丙基,-CO-苄基或-CO-烯丙基。
R15为氢,支链或非支链,任选取代的C1-C4-烷基基团或任选取代的芳基或烷基芳基基团,如上述对于R21或R4所述。优选R15基团为氢,甲基,苄基或苯基。
R16,R17各自独立地为-NH2,卤素,例如Cl,Br,I或F,或支链或非支链,任选取代的C1-C4-烷基或C1-C4-烷氧基或任选取代的芳基基团,如上述对于R31所述,优选NH2,Cl,F,甲基,甲氧基或苯基。
Z1,Z2,Z3,Z4各自独立地为CH,C-CH3,C-OCH3,C-Cl或N,优选Z1和Z2或Z2和Z3或Z3和Z4不同时为N。
除非具体说明,在说明书中取代的芳基,烷基芳基,杂芳基或烷基杂芳基基团是指可被至多三个相同的或不同的基团取代的芳基,烷基芳基,杂芳基或烷基杂芳基基团,取代基团选自下面的基团:
-NO2,-NH2,-OH,-CN,-COOH,-O-CH2-COOH,-COO-C1-C4-烷基,卤素,支链或非支链,任选取代的C1-C4-烷基,C3-C6-环烷基,C1-C4-烷氧基,C1-C4-烷硫基,-O-CH2-COO-C1-C4-烷基,-NH-CO-C1-C4-烷基,-CO-NH-C1-C4-烷基,-NH-SO2-C1-C4-烷基,-SO2-NH-C1-C4-烷基,-N(C1-C4-烷基)2,-NH-C1-C4-烷基,或-SO2-C1-C4-烷基基团,任选取代的-NH-CO-苯基,-CO-NH-苯基,-NH-SO2-苯基,-SO2-NH-苯基,-NH-CO-苄基,-CO-NH-苄基,-NH-SO2-苄基,-SO2-NH-苄基,任选取代的基团-SO2-NT1T2或-CO-NT1T2其中两个基团T1和T2可以形式一环胺,或一3到6元任选取代的饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O,N,S,或两个基团一起为一稠合的,饱和的,不饱和的或芳香碳环或杂环,此环可以包含至多三个不同的或相同的杂原子O,N,S,并且此环可选地被取代,或者,另一个任选取代的环可以与此环稠合。
通式I的化合物以及用于制备它们的中间体可能具有一个或多个不对称的取代的碳原子。这些化合物可能为纯对映体或纯非对映体或它们的混合物形式。优选使用对映体纯化合物作为活性组分。
通式I的化合物还可以是生理学可接受的盐的形式。
通式I的化合物还可以是前体药物形式,其中通式I的化合物在生理条件下可被释放出来。在这里可参照结构单元L中基团T的例子,它们有时候包含可以在生理条件下水解成游离羧基的基团。可在生理条件下释放出结构单元A的衍生的结构单元A也是适宜的实例。
在通式I的化合物的优选实施方案中,可选择下标a,e,f和g和杂环Q以使基团T和结构单元A之间的距离沿着分子主链可能的最短的路线为10到14个原子键,优选为11到13原子键。
更优选的式I化合物具有式IA 1,IA 2,IA 3,IA 4,IA 5,IA 8,IA 10或IA 13的优选的结构单元A,同时结构单元E,G,和L可如上所述广泛的变化。
更优选的式I化合物具有式IA 4的优选的结构单元A,同时结构单元E,G,和L可如上所述广泛的变化。
特别优选的式I化合物具有式IA 1,IA 2,IA 3,IA 4,IA 5,IA 8,IA 10或IA 13的优选的结构单元A和结构单元L的优选区域,同时结构单元E和G可如上所述广泛的变化。
更特别优选的式I化合物具有式IA 4的特别优选的结构单元A和结构单元L的优选区域,同时结构单元E和G可如上所述广泛的变化。
更特别优选的式I化合物具有式IA 4的特别优选的结构单元A和结构单元E的优选区域,同时结构单元L和G可如上所述广泛的变化。
更特别优选的式I化合物具有式IA 4的优选的结构单元A,结构单元E的优选区域和结构单元L的优选区域,同时结构单元G可如上所述广泛的变化。
进一步更特别优选的式I化合物具有结构单元A的优选区域,结构单元E的优选区域和结构单元G的优选区域,同时结构单元L可如上所述广泛的变化。
格外优选的式I化合物具有式IA 4的特别优选的结构单元A和结构单元E,G和L的优选区域。
极优选的通式I的化合物列于下面的表中,其中“化合物编号”代表式I的各不相同的化合物A-E-G-L的编号,化合物编号和相应的化合物用冒号分开,结构单元A-E-G-L缩写的含义在表后说明。化合物编号:A-E-G-L1:bhs-25thiaz-nmgly-betaoxaz2:phhs-24thiaz-bala-betabph3:bhs-25thiaz-ser-betapy4:thazep-24thiaz-gly-beta13bendi5:bim-24thiaz-gly-betatrif6:bhs-24thioph-gly-betapyee7:bhs-me25thioph-ala-beta34meoph8:tolhs-24thioph-gly-betafbph9:tolhs-24thioph-gly-betameph10:bim-me24thiaz-bala-betaph11:bhs-me25thioph-leu-beta34meoph12:ibhs-24thioph-gly-betathiome13:bhs-nme35pyr-gly-betabthioph14:tolhs-nme35pyr-gly-betafu215:bhs-ithiadiaz-gly-betahmofu16:phhs-nme35pyr-bala-betacph17:impy-24thiaz-bala-betafu318:tolhs-25methiaz-bala-psdaptb19:sabhs-25thiaz-gly-psdap20:bhs-24thioph-gly-betadcphtb21:2py-nme35pyr-leu-psdap22:bhs-nme35pyr-gly-aspbzla23:phhs-me24thiaz-gly-zdap24:bhs-25thiaz-bala-betameph25:phhs-me24thiaz-ala-beta34meoph26:tolhs-25methiaz-gly-beta34meoph27:ibhs-ithiadiaz-gly-betafbph28:tolhs-ithiadiaz-bala-asppha29:phhs-ithiadiaz-bala-betaamibe30:tolhs-24thioph-bala-betabmph31:phhs-25methiaz-bala-betaol32:bhs-25oxaz-bala-betamethi33:ibhs-24thiaz-bala-betahni34:gua-24thiaz-gly-betaftrif35:bhs-24thiaz-gly-betafphe36:tolhs-oxadiaz-gly-psdaptb37:phhs-25methiaz-bala-betatbuph38:bhs-24thiaz-nmgly-betathio339:phhs-24thioph-gly-betatos40:2py-thiadiaz-leu-psdap41:dhim-35py-gly-betameph42:bhs-ithiadiaz-gly-aspaba43:phhs-oxadiaz-gly-beta4bph44:bhs-25thiaz-gly-csdap45:ibhs-25thiaz-gly-betahph46:phhs-25methiaz-gly-betahdbph47:bim-me25thioph-gly-betaph48:ibhs-ithiadiaz-bala-beta3quin49:tolhs-oxadiaz-gly-betadhbfu50:bhs-oxadiaz-leu-psdap51:impy-24thioph-bala-betainyl52:bhs-25methiaz-ala-beta23meoph53:phhs-24thiaz-gly-betabnaphth54:impy-42nmeim-bala-betathiome55:bim-35thioph-ala-betadcph56:2py-me24thiaz-gly-betapy57:phhs-24thioph-bala-betaimid58:phhs-24thioph-gly-betadhbfu59:phhs-nme35pyr-bala-betaibph60:bhs-25thiaz-ser-betameph61:tolhs-25thiaz-bala-zdap62:bim-25thiaz-gly-betadcph63:2pmhs-42nmeim-gly-betaamibe64:2py-24thioph-gly-beta3quin65:bhs-25methiaz-gly-betamethioph66:tolhs-ithiadiaz-gly-betafbph67:phhs-25methiaz-gly-betamethi68:ibhs-24thiaz-gly-betadtrif69:bhs-24thioph-gly-betabthioph70:tolhs-25oxaz-gly-betabmph71:ibhs-ithiadiaz-bala-suabu72:bhs-42oxaz-gly-betapy73:tolhs-ithiadiaz-gly-betapyr74:2py-24im-gly-psdap75:thpy-24thiaz-gly-betadcph76:phhs-24thiaz-gly-betampy77:bhs-25methiaz-bala-betadito78:phhs-25methiaz-bala-suabu79:bhs-25thiaz-bala-beta23meoph80:bhs-oxadiaz-leu-betapy81:tolhs-25oxaz-gly-betabnaphth82:dhim-25thiaz-ala-zdap83:tolhs-ithiadiaz-gly-betaimid84:bhs-ithiadiaz-bala-betaoxaz85:bim-25thioph-ala-betameph86:phhs-25oxaz-bala-beta4bph87:bhs-nme35pyr-nmgly-betainyl88:phhs-24thiaz-bala-betacbph89:bhs-25oxaz-bala-betaet90:bhs-24thioph-bala-betabmph91:bhs-25oxaz-ala-betaanaphth92:ibhs-ithiadiaz-gly-betathiobe93:bhs-25thiaz-bala-betadito94:2py-nme35pyr-bala-betapy95:tolhs-25oxaz-bala-beta3quin96:bhs-25thiaz-gly-beta23meoph97:2py-25methiaz-gly-betadito98:ibhs-nme35pyr-bala-betahni99:tolhs-nme35pyr-gly-betadmph100:ibhs-ithiadiaz-bala-betabdimo101:2py-24thiaz-gly-aspibua102:ibhs-nme35pyr-bala-betacbph103:bhs-24thiazme-gly-zdap104:bhs-24thioph-bala-betaol105:2py-24im-gly-zdap106:tolhs-25methiaz-gly-betapytb107:tolhs-ithiadiaz-gly-psdap108:phhs-25thiaz-bala-betabthioph109:bhs-nme35pyr-gly-betafph110:bhs-25methiaz-ala-betadhbfu111:bim-25fur-ala-psdap112:2pmhs-24thiaz-gly-betapy113:bhs-24thiaz-bala-betaphethio114:bhs-25methiaz-bala-betapytb115:bhs-25methiaz-bala-betambiph116:ibhs-25thiaz-gly-betainyl117:phhs-nme35pyr-bala-betabthioph118:bhs-25thiaz-bala-betacph119:bim-26py-ala-betadcph120:phhs-24thioph-gly-betaphethio121:gua-24thiaz-gly-betabthioph122:phhs-24thioph-bala-betaph123:bhs-25thiaz-gly-betaibph124:ibhs-nme35pyr-bala-betathio3125:tolhs-oxadiaz-gly-betapy126:tolhs-nme35pyr-bala-beta4bph127:2py-me24oxaz-gly-betadcph128:tolhs-25methiaz-bala-psdapee129:bhs-ithiadiaz-gly-suabu130:ibhs-25methiaz-bala-beta3quin131:phhs-25oxaz-gly-betaipr132:bim-53pyrazo-ala-betadcph133:tolhs-25oxaz-gly-betapym134:phhs-25oxaz-gly-betathiobe135:phhs-me24thioph-ala-betaph136:tolhs-me25thiaz-leu-betapy137:hs-25thiaz-bala-betapy138:bim-42nmeim-leu-betapy139:tolhs-nme35pyr-bala-betampy140:bhs-24thioph-gly-betahdcph141:ibhs-25oxaz-gly-betaimid142:bhs-oxadiaz-gly-csdap143:ibhs-25oxaz-gly-betadtrif144:2py-53pyrazo-ala-betapy145:phhs-nme35pyr-gly-betahdbph146:tolhs-oxadiaz-bala-zdapch147:phhs-oxadiaz-bala-betapych148:bim-24thioph-gly-betatrif149:tolhs-25methiaz-bala-betapyr150:2py-24thiaz-ala-betapy151:bhs-25thiaz-gly-betapytb152:tolhs-25oxaz-gly-zdapch153:bhs-25methiaz-ala-betadcph154:ibhs-25methiaz-gly-betatos155:tolhs-25thiaz-gly-beta35dbph156:bim-me24thioph-leu-betadcph157:bim-nme35pyr-gly-aspbzla158:ibhs-24thioph-bala-ibsdap159:gua-24thiaz-gly-beta13bendi160:2py-25methiaz-gly-psdap161:2py-24thiaz-bala-asppha162:ibhs-ithiadiaz-bala-betaanaphth163:bhs-nme35pyr-ala-betameph164:tolhs-oxadiaz-gly-betapym165:phhs-ithiadiaz-gly-betaph166:phhs-25methiaz-bala-betadcphtb167:2pmhs-24thiaz-gly-betaph168:gua-24oxaz-gly-betafbph169:bhs-25oxaz-phg-betapy170: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521:tolhs-25methiaz-bala-betacbph9522:tolhs-25methiaz-gly-betaheph9523:phhs-25thiaz-gly-beta34dcph9524:impy-25methiaz-nmgly-psdap9525:bhs-oxadiaz-nmgly-betabpy9526:bhs-25thiaz-bala-zdap9527:tolhs-24thiaz-gly-busu2be9528:2py-24thiaz-leu-psdap9529:bhs-nme35pyr-gly-betadmoph9530:ibhs-25thiaz-bala-betafluo9531:tolhs-nme35pyr-gly-betahmph9532:tolhs-oxadiaz-gly-betahb9533:bhs-ithiadiaz-gly-betaheph9534:phhs-oxadiaz-bala-betaomebendi9535:bhs-oxadiaz-gly-zdap9536:bhs-25methiaz-gly-betahdcph9537:ibhs-25thiaz-bala-zdap9538:tolhs-25methiaz-bala-betathiome9539:phhs-ithiadiaz-bala-betaimid9540:phhs-24thiaz-gly-betapyee9541:tolhs-ithiadiaz-bala-betaphethioa9542:ibhs-24thiaz-bala-zdap9543:phhs-25thiaz-gly-betaomebendi9544:bhs-25oxaz-bala-psdaptb9545:bhs-25oxaz-gly-betaph9546:ibhs-25methiaz-gly-betahc9547:tolhs-25methiaz-bala-betab9548:tolhs-nme35pyr-bala-betadcphch9549:gua-25thioph-gly-betamesu9550:tolhs-24thioph-bala-betadcphee9551:bhs-oxadiaz-ala-betaoxaz9552:ibhs-25oxaz-gly-betathio39553:phhs-24thioph-gly-betafluo9554:bim-25oxaz-gly-betameph9555:bim-25methiaz-gly-aspibua9556:bim-me25oxaz-bala-psdap9557:ibhs-oxadiaz-gly-zdapch9558:2py-oxadiaz-bala-aspaba9559:bhs-oxadiaz-nmgly-betainyl9560:tolhs-25methiaz-bala-betaipro9561:bhs-25fur-gly-betapy9562:bhs-25thioph-ala-psdap9563:ibhs-oxadiaz-gly-betadcphch9564:phhs-25oxaz-bala-betafluo9565:phhs-25oxaz-bala-betadbph9566:ibhs-oxadiaz-gly-betaomebendi9567:ibhs-nme35pyr-gly-betaphethio9568:bhs-25oxaz-bala-betabpy9569:phhs-25thiaz-bala-betaipro9570:2py-nme35pyr-ala-betapy9571:ibhs-24thiaz-bala-betahb9572:bhs-24thioph-gly-betaimid9573:bhs-25methiaz-bala-betaoxope9574:ibhs-ithiadiaz-bala-betahmph9575:2py-24thiaz-leu-zdap9576:bhs-25methiaz-gly-betapym9577:bhs-ithiadiaz-ala-betaoxaz9578:ibhs-24thioph-bala-betaimid9579:ibhs-24thioph-gly-beta23meoph9580:bim-me24oxaz-gly-zdap9581:tolhs-nme35pyr-gly-betahc9582:bhs-25thiophme-gly-betapy9583:bhs-25oxaz-gly-betambiph9584:phhs-25oxaz-bala-betadito9585:phhs-25methiaz-gly-betatbuph9586:tolhs-24thiaz-bala-betapytb9587:impy-25thiaz-bala-betah35dc9588:bhs-nme35pyr-bala-zdaptb9589:2py-26py-ser-zdap9590:dhim-42pym-gly-betadcph9591:2py-me25thioph-bala-betadcph9592:tolhs-oxadiaz-bala-betathiobe9593:ibhs-24thiaz-bala-betaipr9594:phhs-nme35pyr-bala-betahcbph9595:gua-24thiaz-gly-betaipro9596:tolhs-oxadiaz-bala-betatos9597:phhs-24thiaz-bala-betatrif9598:tolhs-ithiadiaz-gly-betadhbfu9599:2pmhs-25methiaz-bala-zdap9600:gua-24oxaz-gly-betabmph9601:bhs-oxadiaz-bala-zdaptb9602:bhs-oxadiaz-nmgly-betadhbfu9603:phhs-25thiaz-gly-betahmo9604:phhs-ithiadiaz-gly-betamethioph9605:bhs-ithiadiaz-leu-zdap9606:tolhs-24thiaz-gly-betapytb9607:ibhs-24thioph-gly-betaet9608:phhs-25thiaz-gly-betainyl9609:tolhs-oxadiaz-bala-betathio39610:bhs-25oxaz-ala-betabnaphth9611:bim-nme35pyr-gly-zdap9612:2py-25thioph-gly-betadcph9613:phhs-24thioph-gly-betadcphee9614:ibhs-24thioph-gly-beta13bendi9615:bhs-42pym-gly-zdap9616:2py-24im-bala-betapy9617:phhs-25methiaz-gly-psdapee9618:bhs-24im-leu-betadcph9619:phhs-24thiaz-bala-betafphe9620:tolhs-24thiaz-bala-psdap9621:bhs-nme35pyr-bala-betapy9622:impy-42nmeim-gly-beta13bendi9623:phhs-25thiaz-bala-betadhbfu9624:ibhs-24thiaz-bala-betabpy9625:phhs-oxadiaz-bala-aspibua9626:ibhs-nme35pyr-gly-betafu29627:2pmhs-42nmeim-bala-ibsdap9628:bhs-25thiaz-gly-betahc9629:bim-42pym-gly-betainyl9630:bim-me25thiaz-gly-psdap9631:phhs-ithiadiaz-bala-betafu39632:bhs-24thioph-nmgly-betathioph9633:bim-42pym-gly-zdap9634:ibhs-24thiaz-gly-betabmph9635:phhs-24thioph-gly-beta23meoph9636:phhs-24thiaz-gly-betadito9637:phhs-25oxaz-gly-beta3quin9638:bim-nme35pyr-gly-aspibua9639:bim-oxadiaz-gly-aspibua9640:tolhs-25thiaz-gly-betahcbh9641:ibhs-ithiadiaz-gly-asppha9642:impy-25oxaz-met-psdap9643:ibhs-nme35pyr-bala-betahc9644:2py-25fur-gly-betadcph9645:tolhs-24thioph-bala-betaomebendi9646:gua-24thiaz-gly-betahmofu9647:ibhs-25methiaz-bala-zdapch9648:2py-24thiaz-bala-zdap9649:bhs-24thiaz-gly-beta4bph9650:phhs-24thioph-gly-betahdcph9651:bhs-42nmeim-bala-psdap9652:phhs-25thiaz-gly-aspbzla9653:2py-24thioph-ala-betadcph9654:bhs-24thiaz-ala-betahmph9655:bhs-triaz-leu-zdap9656:tolhs-nme35pyr-bala-betaftrif9657:bhs-ithiadiaz-bala-beta13bendi9658:ibhs-25methiaz-gly-betahmo9659:ibhs-24thioph-gly-betahmofu9660:bhs-25oxaz-bala-asppha9661:tolhs-25methiaz-gly-betaftrif9662:bhs-oxadiaz-gly-betacph9663:phhs-25oxaz-gly-betabenfu9664:dhim-24oxaz-ala-betadcph9665:tolhs-25oxaz-bala-aspaba9666:bhs-25thiaz-bala-psdaptb9667:bhs-25oxaz-nmala-psdap9668:4pmhs-24thioph-bala-betameph9669:bhs-nme35pyr-bala-betahmo9670:ibhs-nme35pyr-gly-betaanaphth9671:dhim-52thiaz-ala-betapy9672:bim-52thiaz-gly-psdap
上述表中冒号后用连字符分开的缩写在每种情况下各自代表结构单元A,E,G和L,其中的缩写具有下面的含义:
Figure A0080890703721
Figure A0080890703731
Figure A0080890703741
Figure A0080890703751
Figure A0080890703771
Figure A0080890703781
Figure A0080890703791
Figure A0080890703801
Figure A0080890703811
Figure A0080890703821
Figure A0080890703831
在表中,Et代表乙基,iPr代表异丙基。
通式I的化合物和用于制备它们的起始原料一般可以通过为技术人员所知的有机化学方法制备,如权威著作中所述,例如,Houben-Weyl,”Methoden der Organischen Chemie”,Thieme-Verlag,Stuttgart,或March”Advanced Organic Chemistry”,4th Edition,Wiley & Sons。
式I的化合物既可以通过“传统”方法在溶液中通过在溶液中每个单独的结构单元加以片断缩合进行,也可以在聚合载体上进行,在每种情况下使用已知的和适合于各具体反应的反应条件。也可以使用本身已知,但在这里没有提到的其它方法。
单独的片段的偶合和保护基的除去可以按照类似于著名文献所述的肽合成方法通过已知的步骤进行,例如,Bodanszky“The Practiceof Peptide Synthesis”,2nd Edition,Springer-Verlag 1994,andBodanszky”Principles of Peptide Synthesis”,Springer-Verlag1984。用于固相合成的方法和应用在下文中描述,例如,J.Am.Chem.Soc.1972,94,3102 et seq.,Int.J.Peptide Protein Res.1990,35,161-214;Angew.Chem.1992,375-391,J.Med.Chem.1994,37,1233,J.Med.Chem.1994,37,1385,and Angew.Chem.1996,108,2437-2488。肽合成的常规方法的综述和适宜的试剂的目录还可在下文中找到:NOVABIOCHEM 1999“Catalog and Peptide SynthesisHandbook”。
式I的化合物的一般合成在反应路线1-8中描述。除非另外指出,所有起始原料和试剂是可以购得的或通过常规方法由可以购买的前体化合物制备。
反应路线1-3描述了式I的化合物的一般合成方法。合成大体上可以从结构单元II通过N-末端延伸进行(反应路线1)。用III和II偶合得到IV,除去保护基SG3得到V,且重新与VI偶合得到VII。
做为选择,I类型的化合物还可以从结构单元VI开始通过C-末端延伸制备。与VIII偶合得到IX,除去保护基SG2,且重新与II偶合得到VII(反应路线2)。
在除去VII中的保护基SG1之后最终得到通式I的化合物(反应路线3)。为使说明更详细,合成路线中表明羧酸衍生物基团例如,基团-CO-R1,基团Z的一种优选实施方案,代替了基团T。用相应的基团Z的合成类似地进行。在基团R2,R3,R4,R5,R6,Q或A包含妨碍所述的结构单元的连接的官能团的情况下,这件官能团同样地通过适宜的保护基阻断。
所述的偶合可以借助于常规的偶合试剂利用适当地保护的氨基和羧酸衍生物进行(式III和VI中Y=OH)。其它的方法包含使用预活化的羧酸衍生物,优选酰基卤化物,对称的或混合酸酐,或所谓的活性酯(Y=卤化物,活性酯,酸酐;在式III和VI中),它们通常被用来酰化胺类化合物。这些活化的羧酸衍生物还可以原位制备。
偶合通常可以在惰性溶剂中在酸结合剂,优选有机碱,例如,三乙胺,吡啶,二异丙基乙胺,N-甲基吗啉,喹啉的存在下进行;还可优选加入碱金属或碱土金属氢氧化物,碳酸盐或碳酸氢盐或碱金属或碱土金属的其它弱酸盐,优选钾,钠,钙或铯盐。反应时间取决于所用的条件,在几分钟和14天之间,反应温度在-40℃和140℃之间,优选在-20℃和100℃之间。
适宜的惰性溶剂的实例为碳氢化合物例如己烷,庚烷,石油醚,甲苯,苯或二甲苯;氯化烃类例如三氯乙烯,1,2-二氯乙烷,四氯甲烷,氯仿,二氯甲烷;醇类例如甲醇,乙醇,异丙醇,正丙醇,正丁醇或叔丁醇;醚类例如乙醚,甲基叔丁基醚,二异丙醚,四氢呋喃,二氧六环;二醇醚例如乙二醇单甲醚或乙二醇一乙基醚,乙二醇二甲醚;酮类例如丙酮,丁酮;酰胺例如二甲基甲酰胺(DMF),二甲基乙酰胺或乙酰胺;腈类例如乙腈;亚砜例如二甲亚砜;羧酸类例如甲酸或乙酸;硝基化合物例如硝基甲烷或硝基苯;酯例如乙酸乙酯;水;或所述溶剂的混合物。
可以使用的保护基SG为专业技术人员所知的肽合成的所有常规保护基,并且在上述著名文献中也有所描述。除去保护基得到式V,X和I的化合物也可在技术人员所知的条件下进行,且如文献所描述,例如,Greene and Wuts in“Protective Groups in OrganicSynthesis”,2nd Edition,& Sons,1991。
SG3和SG5是所谓的N-末端氨基保护基;优选为Boc,Fmoc,苄氧羰基(Z),乙酰基,Mtr。
SG1,SG2和SG4是适宜的C-末端羟基保护基,优选C1-C4-烷基例如,甲基,乙基,叔丁基,或苄基或三苯甲基或其它—特别用于SG1—,聚合物-键合保护基是以可商购的聚苯乙烯树脂的形式,例如,2-氯三苯甲基氯化物树脂或王氏树脂(来自Bachem或Novabiochem公司)。
除去酸不稳定的保护基(例如Boc,叔丁基,Mtr,三苯甲基)可以如下进行—取决于所用的保护基—使用有机酸例如三氟乙酸(TFA),三氯乙酸,三氟乙醇或其它无机酸例如高氯酸,盐酸或硫酸,磺酸例如苯磺酸或对甲苯磺酸,这些酸一般地过量使用。在三苯甲基的情况下,加入硫醇例如,苯甲硫醚,乙二硫醇或苯硫酚是有利的。可以存在另外的惰性溶剂然而并非总是必要的。适宜的和优选的惰性溶剂为有机溶剂,例如羧酸类例如乙酸;醚类例如THF或二氧六环;酰胺例如DMF或二甲基乙酰胺;卤代烃例如二氯甲烷;醇类例如甲醇,异丙醇;或水。所述溶剂的混合物也是适宜的。反应温度在-10℃和50℃之间,优选在0℃和30℃的范围之间。
碱不稳定的保护基例如Fmoc是用有机胺例如二甲胺,二乙胺,吗啉,哌啶在CH2Cl2或DMF的5-50%溶液中处理加以除去。这些反应温度在-10℃和50℃之间,优选在0℃和30℃的范围之间。
酸保护基例如甲基或乙基优选通过在惰性溶剂中碱性水解除去。所用的碱优选碱金属或碱土金属氢氧化物,优选NaOH,KOH或LiOH;所用的溶剂全部是常规的惰性溶剂例如,碳氢化合物例如己烷,庚烷,石油醚,甲苯,苯或二甲苯;氯化烃类例如三氯乙烯,1,2-二氯乙烷,四氯甲烷,氯仿,二氯甲烷;醇类例如甲醇,乙醇,异丙醇,正丙醇,正丁醇或叔丁醇;醚类例如乙醚,甲基叔丁基醚,二异丙醚,四氢呋喃,二氧六环;乙二醇醚例如乙二醇单甲醚或乙二醇一乙基醚,乙二醇二甲醚;酮类例如丙酮,丁酮;酰胺例如二甲基甲酰胺(DMF),二甲基乙酰胺或乙酰胺;腈类例如乙腈;亚砜例如二甲亚砜;硝基化合物例如硝基甲烷或硝基苯;水或所述溶剂的混合物。加入相转移催化剂可能是有利的,取决于所用的溶剂或溶剂混合物。这些反应的温度一般在-10℃和100℃之间。
可以通过氢解除去的保护基例如苄氧羰基(Z)或苄基,可以通过例如在催化剂(例如在用作载体的活性炭上的贵金属催化剂)的存在下氢解除去。适宜的溶剂如上所述,优选醇类例如甲醇,乙醇;酰胺例如DMF或二甲基乙酰胺;酯例如乙酸乙酯。氢解通常在压力1-200bar和温度0℃和100℃之间进行;加入酸例如,乙酸或盐酸可能是有利的。催化剂优选使用在活性炭上的5-10%Pd。
Figure A0080890703881
反应路线2:
Figure A0080890703891
反应路线3:
Figure A0080890703901
式II,III和VIII的化合物和用于制备它们的起始原料可以是购买的或者是通过已知方法制备的。
因此,例如,β-芳基和杂芳基氨基酸可以通过下面的方法,Johnsonet al.,J.Am.Chem.Soc.299,1936,或Edwards et al.,J.Org.Chem.1979,44,3136-3140,由芳基或杂芳基醛,丙二酸和乙酸铵合成。
Cole在Tetrahedron 1994,50,9517-9582中描述β-氨基酸的通常的合成方法。用于对映体选择合成β-氨基酸的方法在以下文献中描述,例如,Enders,Angew.Chem.Int.Ed.Engl.,1995,34,455-457。对映体纯的3-吡啶基-β-丙氨酸的制备在Rico et al.,J.Org.Chem.,1993,58,7948-7951中描述。3-乙炔基-β-丙氨酸可以通过Zablockiet al.,J.Med.Chem.1995,38,2378-2394的方法制备。适宜的二氨基丙酸衍生物可以同样地是购买的或可以简单地如WO97/37655中所述制备。
游离的β-氨基酸或二氨基丙酸衍生物到相应的N-或C-末端保护衍生物的转化可以通过有机化学的常规方法进行,例如,如Bodanszky或Greene在著名文献中所述。
下面通式的氨基杂芳基羧酸和氨基杂芳基羧酸酯:
Figure A0080890703912
Figure A0080890703913
它们被用作合成式I的化合物的起始原料,可以是购买的或者是按照下面的实例制备的:
2-氨基-1,3-噻唑-5-羧酸乙酯的合成见Kushner et al.,J.Org.Chem.1948,13,834及以下页;2-氨基-4-吡啶羧酸甲酯的合成见Podany et al.,J.Org.Chem.1986,51,2988-2994;5-氨基-3-吡啶羧酸甲酯的合成见Hawkins et al.,J.Org.Chem.1949,14,328-332;4-氨基-2-嘧啶羧酸甲酯的合成见DE 2848912,6-氨基-4-嘧啶羧酸甲酯的合成见Zh.Org.Khim.1981,17,312-317;5-氨基-1,3-噻唑-2-羧酸乙酯的合成见Adams et al.,J.Chem.Soc.1956,1870-1873;4-(氨甲基)-2-噻吩羧酸甲酯的合成见Peschke et al.,Bioorg.Med.Chem.Lett.1997,7,1969-1972;2-氨基-1,3-噁唑-4-羧酸的合成见Foulis et al.,J.Med.Chem.1971,14,1075-1077;4-氨基吡啶-2-羧酸甲酯的合成见Mostieret al.,J.Org.Chem.1955,20,283-285;2-氨基嘧啶-3-羧酸甲酯的合成见Liebigs Ann.Chem.1965,209-211;5-氨基-1,3,4-噻二唑-5-羧酸的合成见Liebigs Ann.Chem.1963,3;5-氨基-1,3,4-三唑-5-羧酸的合成见US3023210;4-氨基吡咯-2-羧酸的合成见J.Med.Chem.1983,26,1042;i-甲基-3-氨基吡唑-5-羧酸的合成见Acta Chem.Scand.1990,44,74;1-甲基-5-氨基-3-羧酸的合成见Lee et al.,J.Org.Chem.1989,54,428。
将下面通式的氨基杂芳基羧酸或氨基杂芳基羧酸酯:
Figure A0080890703921
Figure A0080890703922
转化为下面通式的化合物:
Figure A0080890703923
可以通过技术人员所知的方法进行,例如WO97/08145中所述的方法。这些结构单元可直接地反应(在相应的游离羧酸的情况下),或者在除去保护基SG4之后进行,用通式V的化合物得到VII(反应路线1)或者用VIII得到IX(当Y=OH,化合物VI相当于化合物XIII)。
反应路线4-7通过举例描述了许多引入A的方法,在每种情况下所用的反应条件是技术人员已知的,且适合于这些特殊的反应。也可以使用本身已知,但在这里没有提到的其它方法。
脲和硫脲(AE-1到AE-3)可以通过有机化学的常规方法制备,例如,如反应路线4中所描述,通过异氰酸酯或异硫氰酸盐与胺类反应,任选地在惰性溶剂中在升温下进行(Houben-weyl Band VIII,157ff)。
反应路线5通过举例表示了AE-4类型的化合物的制备,例如,通过如下面文献中描述的方法:Blakemoore et al.Eur.J.Med.Chem.1987(22),2,91-100,或Misra et al.Bioorg.Med.Chem.Lett.1994,4(18),2165-2170。
通式AE-5和AE-6的未取代或环状的胍衍生物可以使用购买的或容易得到的试剂制备,例如,在Synlett 1990,745,J.Org.Chem.1992,57,2497,Bioorg.Med.Chem.1996,6,1185-1208;Bioorg.Med.Chem.1998,1185,或Synth.Comm.1998,28,741-746中所描述。
通式AE-7的化合物可以按照类似于US3,202,660的方法制备,且式AE-9,AE-10,AE-11和AE-12的化合物可以按照类似于WO97/08145的方法制备。式AE-8的化合物可以如反应路线6所示制备,例如通过Perkins等人在Tetrahedron Lett.1999,40,1103-1106中所述的方法制备。反应路线6给出了所述的化合物的合成综述。
通式AE-13的化合物可以按照Froeyen等人在Phosphorus SulfurSilicon Relat.Elem.1991,63,283-293中的方法制备。且AE-14按照类似于Yoneda et al.,Heterocycles 1998,15,No.1,Spec.Issue,341-344的方法制备,如反应路线7中所描述。相应的化合物还可以按照类似于WO97/36859的方法制备。
如反应路线8所示,还可以将通式IX的化合物与XV反应得到通式XVI的化合物,然后在除去其保护基SG5后,通过WO97/08145和反应路线2-5中所示的方法转变为类型VIII的化合物。在R1为C1-C4-烷氧基或苄氧基的情况下,通式VIII的化合物直接相当于类型I的化合物。反应路线4反应路线5
Figure A0080890703961
反应路线6:
Figure A0080890703971
反应路线6(续)
Figure A0080890703981
反应路线6(续)
Figure A0080890703991
反应路线7:
Figure A0080890704001
反应路线8:
本发明还涉及用于口服的和肠胃外的药物制剂,包含至少一种式I的化合物以及常规的药物赋形剂。
根据本发明的化合物可以以常规的方式口服给药或胃肠外(皮下地,静脉内,肌肉的,腹膜内的)给药。给药还可以通过鼻咽部位蒸气或喷雾的方式进行。
剂量取决于病人的年龄,条件和体重以及所给药的方式。活性组分的日剂量口服通常在体重的约0.5和50毫克/公斤之间,肠胃外给药在体重的约0.1和10毫克/公斤之间。
该新的化合物可以常规的固体或液体药物应用形式使用,例如以裸露的或(薄膜)包衣的片剂,胶囊,粉末,颗粒,栓剂,溶液,油膏,乳剂或喷雾剂使用。这些是用常规的方式制造的。用于此目的的活性组分可以用传统的药物赋形剂加工,例如片剂粘合剂,填充剂,防腐剂,片剂崩解剂,流动调节剂,增塑剂,润湿剂,分散剂,乳化剂,溶剂,缓释剂,抗氧化剂和/或气雾剂的挥发剂(参照:H.Suckeret al.:Pharmazeutische Technologie,Thieme-Verlag,Stuttgart,1991)。用这种方法得到的给药形式通常包含按重量计算0.1到90%量的活性组分。
本发明还涉及式I的化合物在制造用于治疗疾病的药物中的用途。本发明的式I化合物可用于治疗人类和动物的疾病。式I的化合物与整联蛋白受体结合,因此可用作整联蛋白受体拮抗剂并用于制造治疗涉及整联蛋白受体的疾病的药物。
式I的化合物优选与αvβ3整联蛋白受体结合,因此可优选用作αvβ3整联蛋白受体拮抗剂并用于治疗涉及αvβ3整联蛋白受体的疾病。
式I的化合物还可优选被用来治疗下面的疾病:心血管病症例如动脉粥样硬化,血管损伤后再狭窄,和血管成形术(新内膜形成,平滑肌细胞移行和增殖),急性肾衰竭,与血管生成有关的微血管病例如,糖尿病患者血管病或视网膜病或类风湿性关节炎,由血小板介导的血管闭塞,动脉血栓形成,中风,心肌梗塞或中风后再灌注损伤,癌症例如,在肿瘤转移或肿瘤生长中(肿瘤诱导的血管生成)骨质疏松症(趋化作用后骨吸收和破骨细胞到骨基质的粘连),高血压,牛皮癣,甲状旁腺机能亢进,Paget’s疾病,恶性高钙血症,移性溶骨病变,炎症,创伤愈合,心功能不全,充血性心力衰竭CHF,和用于抗病毒的,抗寄生物的或抗菌的治疗和预防(粘连和内在化)。
式I的化合物可优选与至少一种其它化合物结合给药以改善对于许多适应症的疗效。这些其它化合物可能与式I化合物具有相同或不同的作用机理。
因此药物制剂可以包含,除式I化合物和常规的药物赋形剂之外,至少一种其它化合物,取决于适应症,每种情况选自下面10组的化合物。第1组:血小板粘连,活化作用或聚集作用抑制剂,例如,乙酰水杨酸,赖氨酸乙酰水杨酸酯,吡乙酰胺,双嘧哌胺醇,abciximab,血栓素拮抗剂,纤维蛋白原拮抗剂,例如tirofiban,或ADP诱导的聚集作用抑制剂例如,氯苄噻哌啶或氯吡格雷,防止凝血酶活性或形成的抗凝血剂,例如,IIa,Xa,XIa,IXa或VIIa抑制剂,血小板活化化合物的拮抗剂和选择蛋白拮抗剂用于治疗血小板介导的血管闭塞或血栓形成,或第2组:血小板活化作用或聚集作用的抑制剂,例如,GPIIb/IIIa拮抗剂,凝血抑制因子或因子Xa抑制剂或ADP受体拮抗体,丝氨酸蛋白酶抑制剂,纤维蛋白原减少的化合物,选择蛋白拮抗剂,ICAM-1或VCAM-1拮抗剂白细胞粘连抑制剂血管壁移行抑制剂,纤维蛋白溶解-调制化合物例如,链激酶,tPA,血纤维蛋白溶酶原活化兴奋剂,TAFI抑制剂,XIa抑制剂或PAI-1拮抗剂,补体因子抑制剂,内皮素受体拮抗体,酪氨酸激酶抑制剂,抗氧化剂和白细胞间介素8拮抗剂用于治疗心肌梗塞或中风,或第3组:内皮素拮抗剂,ACE抑制剂,血管紧张素受体拮抗剂,肽链内切酶抑制剂,beta阻断剂钙通道阻断剂磷酸二酯酶抑制剂和caspase抑制剂用于治疗充血性心力衰竭,或第4组:凝血酶抑制剂,因子Xa抑制剂,导致凝血酶形成的凝结通道抑制剂,例如,肝素或低分子量肝素,血小板粘连,活化或聚集作用的抑制剂,例如,GPIIb-IIIa拮抗剂或由vWF或GPIb介导的血小板粘连和活化的拮抗剂,内皮素受体拮抗剂,氧化氮合酶抑制剂,CD44拮抗剂,选择蛋白拮抗剂,MCP-1拮抗剂,增殖细胞中信号转导抑制剂,由EGF,PDGF,VEGF或bFGF介导的细胞响应拮抗剂,和抗氧化剂用于治疗脉管损伤或斯坦特固定模植入后再狭窄,或第5组:由EGF,PDGF,VEGF或bFGF介导的细胞响应拮抗剂,肝素或低分子量肝素或其它GAGs,MMPs抑制剂,选择蛋白拮抗剂,内皮素拮抗剂,ACE抑制剂,血管紧张素受体拮抗剂和糖基化作用抑制剂或AGE形成抑制剂和它们的受体拮抗剂,例如,RAGE,用于治疗糖尿病患者血管病,或第6组:脂质降低的化合物,选择蛋白拮抗剂,ICAM-1或VCAM-1拮抗剂肝素或低分子量肝素或其它GAGs,MMPs抑制剂,内皮素拮抗剂,脱脂蛋白A1拮抗剂,胆固醇拮抗剂,HMG-CoA还原酶抑制剂,ACAT抑制剂,ACE抑制剂,血管紧张素受体拮抗剂,酪氨酸激酶抑制剂,蛋白激酶C抑制剂,钙通道阻断剂,LDL受体功能兴奋剂,抗氧化剂和自由基清除剂用于治疗动脉粥样硬化,或第7组:抑制细胞生长的或抗肿瘤的化合物,抑制增殖的化合物,例如,激酶抑制剂和肝素或低分子量肝素或其它GAGs,用于治疗癌症,优选用于抑制肿瘤生长或转移,或第8组:用于抗吸收治疗的化合物,用于激素替补治疗的化合物,例如,雌激素或黄体酮拮抗剂,重组体人生长激素,二膦酸盐例如,二膦酸盐用于降钙素治疗的化合物,降钙素兴奋剂,钙通道阻断剂,骨形成兴奋剂,例如,生长因子拮抗剂,白细胞间介素-6拮抗剂和Src酪氨酸激酶抑制剂用于治疗骨质疏松症,或第9组:TNF拮抗剂,VLA-4或VCAM-1拮抗剂LFA-1,Mac-1或ICAMs拮抗剂,补体抑制剂,免疫抑制剂,白细胞间介素-1,-5或-8拮抗剂和二氢叶酸还原酶抑制剂用于治疗类风湿性关节炎,或第10组:胶原酶,PDGF拮抗剂和MMPs用于改善创伤愈合。
一种药物制剂包含至少一种式I化合物,其中适当的药物赋形剂和至少一种其它化合物,取决于适应症,每种情况选自上述组之一,是指至少一种式I化合物,与至少一种其它化合物,每种情况选自如上所述的组之一和,其中适当的药物赋形剂一起合并给药。
合并给药可以通过物质的混合物进行,混合物包含至少一种式I化合物,其中适当的药物赋形剂和至少一种其它化合物,取决于适应症,每种情况选自上述组之一,而且可以在空间和/或时间上分开地进行。
在空间上和/或时间上分开给药方面,是对药物制剂的组分,式I的化合物和选自上述的组的化合物空间上和/或时间上分开给药的。
对于脉管损伤或斯坦特固定后再狭窄的治疗,式I的化合物可以单独或与选自第4组的化合物结合在感染位置局部给药。还可以优选将这些化合物涂敷在斯坦特固定模上。
对于骨质疏松症的治疗,将式I化合物与一种抗吸收的或激素替补治疗结合给药可能是有利的。
因此本发明还涉及上述的药物制剂的化合物在制造用于治疗疾病的药物中的用途。
在一优选实施方案中,本发明涉及上述的联合药物制剂的化合物在制造用于治疗下面的疾病的药物中的用途:血小板-介导的血管闭塞或血栓形成使用第1组的化合物,心肌梗塞或中风使用第2组的化合物,充血性心力衰竭使用第3组的化合物,脉管损伤后再狭窄使用第4组的化合物,糖尿病患者血管病使用第5组的化合物,动脉粥样硬化使用第6组的化合物,癌症使用第7组的化合物,骨质疏松症使用第8组的化合物,类风湿性关节炎使用第9组的化合物,创伤愈合使用第10组的化合物。
下面的实施例用于说明本发明,这些实施例的选择是非限制性的。I.合成实施例I.A前体结构单元L的制备3-(4-甲基苯基)-β-丙氨酸
向500毫升乙醇中加入4-甲基苯甲醛(30克,0.25mol),而后加入丙二酸(25.9g,0.25mol)和乙酸铵(28.8g,0.374mol),混合物回流8小时。反应完全后,冷却到5℃,得到的沉淀抽滤滤出,用冷的乙醇和乙醚洗涤,并在烘箱中在40℃下干燥。19.9g;ESI-MS[M+H+]=180Fmoc-(4-甲基苯基)-β-丙氨酸
3-(4-甲基苯基)-β-丙氨酸1(7g,39.6mmol)溶于160毫升10%Na2CO3水溶液和50毫升THF的混合物。然后加入Fmoc-Cl(10.31g,39.8mmol)溶于40毫升THF的溶液,混合物在室温下搅拌过夜。反应混合物用浓HCl调节至pH值为2并用乙醚提取两次。合并有机相然后干燥(Na2SO4)并浓缩,残余物用乙醚/环己烷结晶并干燥。用这种方法得到14克白色固体。ESI-MS[M+H+]=402结构单元A-E的制备2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-羧酸乙酯
2-氨基-1,3-噻唑羧酸乙酯(1.6g,9.82mmol)和异氰酸苄酯(1.31g,9.83mmol)在10毫升CH2Cl2中回流7小时。反应完全后,混合物浓缩。得到的残余物在硅胶柱上色层分离(CH2Cl2/CH3OH 2%)得到2.4克标题化合物。2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-羧酸
2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-羧酸乙酯(2.4g,7.86mmol)悬浮在10毫升CH3OH和1毫升H2O中,加入LiOH(0.18g,7.86mmol)后,在室温下搅拌18小时。反应完全后,加入20毫升H2O,溶液用浓缩HCl调节pH值至1,抽滤滤出得到的固体并干燥。1.3g;ESI-MS[M+H+]=2782-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基}乙酸乙酯
反应按照类似的方法用2-氨基-1,3-噻唑-4-基乙酸乙酯(1.25g,9.39mmol)进行。色层分离后得到2.8克标题化合物。(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酸
反应按照类似的方法从2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酸乙酯(2.8g,8.77mmol)进行,且得到1.9克白色固体的标题化合物;ESI-MS[M+H+]=292.2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-5-羧酸a)将氯乙酸甲酯(32.6g,0.30mol)和甲酸甲酯(25.2g,0.42mol)溶于乙醚(300ml),滴加加入到乙醇钾(29.9g,0.32mol)在80毫升乙醇冷却的(0-10℃)溶液中。得到的悬浮液在5℃下搅拌1.5小时并在室温下搅拌12小时。滤出得到的盐并用乙醚洗涤。残余物溶于H2O,用HCl(10N)在4℃酸化至pH值3,并用乙醚提取。合并的有机部份干燥,过滤并蒸干;12.7g。b)甲酰氯乙酸乙酯(10.0g,66.42mmol)和尿素(4.4g,73.97mmol)在60毫升H2O中回流3.5小时。反应完全后,混合物过滤,滤液浓缩。得到的残余物用色层分离(MPLC,RP,Chromasil 100 C18,梯度1-11%乙腈)得到0.66g标题化合物。c)2-氨基-1,3-噁唑-5-羧酸乙酯(0.3g,1.92mmol)和异氰酸苄酯(0.26g,9.83mmol)在15ml甲苯中回流8小时。反应完全后,混合物用水(15ml)洗涤,用5%柠檬酸(2×15ml)提取并用H2O摇动。有机相干燥并浓缩。苄胺,二苄基脲和所要的产品(25%纯度)的混合物(1.27g)从乙酸乙酯中沉淀出来,且用于反应而不必进一步提纯。d)将2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-5-羧酸乙酯(0.35g,25%纯度)悬浮在20毫升CH3OH和20ml H2O中,加入NaOH(1N,2.56mmol)后,在35℃下搅拌6小时。反应完全后,混合物浓缩,水相用HCl(2N)酸化至pH值2,并用乙酸乙酯彻底提取。合并的有机相干燥,过滤并浓缩。在乙腈中搅拌得到136mg标题化合物;ESI-MS[M+H+]=262.052-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-羧酸a)丙酮酸溴甲酯(59.7g,0.306mol)和尿素(27.6g,0.46mol)在220毫升乙醇中回流24小时。混合物蒸发,残余物与20毫升H2O混合,用1N氢氧化钠溶液调节pH值为10,并用CH2Cl2提取。有机相浓缩,残余物用乙醚研制得到12.3克游离碱;
ESI-MS[M+H+]=157.05.在10℃下向母液中加入醚制的HCl。这样将进一步得到以盐酸盐形式存在的11.4克目标酯。b)4克2-氨基-1,3-噁唑-4-羧酸乙酯与异氰苄基酸酯(3.75g;0.13mmol)和3.3g二异丙基乙胺在60毫升甲苯中回流1小时。反应完全后,混合物蒸发,残余物在二氯甲烷中处理,用1N HCl和饱和NaCl溶液洗涤。有机相干燥,浓缩,残余物在甲基叔丁基醚中研制得到4.6克白色固体;
ESI-MS[M+H+]=290.05.c)4.3克2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-羧酸乙酯在120ml 2∶1二氧六环/H2O中与1.4克KOH回流2小时。混合物浓缩并用2N HCl酸化得到白色沉淀,抽滤滤出沉淀,用丙酮并干燥。
3.38g;ESI-MS[M+H+]=262.05.4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-羧酸4-氨基-1-甲基吡咯-2-羧酸甲酯(4g,26mmol)悬浮在40毫升甲苯和70毫升THF中,向其中加入1当量的异氰酸苄酯在10毫升四氢呋喃中的溶液。混合物搅拌过夜,滤出得到的沉淀。母液浓缩,残余油状物与乙醚混合,并用抽滤滤出得到的沉淀。合并沉淀得到5.16g;ESI-MS:M+H+=2887.18克(25mmol)该甲酯溶于150毫升四氢呋喃,加入溶于水的2当量LiOH。混合物在室温下搅拌3小时。然后中和,浓缩和用HCl酸化,并用抽滤滤出白色沉淀。用水洗涤并用约100毫升乙醇结晶得到3.90克;ESI-MS:M+H+=274.0。5-{[(苄基氨基)羰基]氨基}噻吩-2-羧酸a)在0℃下向85毫升甲醇中滴加7.76毫升亚硫酰氯。向此混合物中以分批加入的方式加入16.8克(97mmol)2-硝基噻吩-5-羧酸,然后在室温下搅拌5小时。然后在40℃下搅拌6小时。冷却后,混合物与冰水混合,抽滤滤出沉淀,用水洗涤并处理于乙酸乙酯中。分出该相,有机相用水洗涤4次,用Na2SO4干燥并浓缩(16.45g)。b)9.2克(49mmol)2-硝基噻吩-5-羧酸甲酯溶于600毫升冰醋酸中,且在40℃分批加入27.45克铁粉(默克公司,还原铁)。几个小时后,抽滤滤出固体,用冰醋酸,乙酸乙酯和二氯甲烷洗涤。滤液合并,用Na2SO4干燥并浓缩。油状残余物在乙醚中处理,用6N异丙醇化的HCl将盐酸盐沉淀出来。抽滤过滤并干燥得到5.80克。c)将5.80克(30mmol)氨基噻吩引入到含有10.2毫升二异丙基乙胺的50毫升甲苯和85ml四氢呋喃中。加入1当量的异氰酸苄酯后,混合物搅拌过夜,而后回流约13小时,此黑色溶液浓缩,在乙酸乙酯中处理,用1N HCl,水和饱和NaHCO3溶液提取。丢弃水溶液相。滤出得到的沉淀,母液用Na2SO4干燥并浓缩至20毫升。滤出得到的沉淀并用冷的乙酸乙酯洗涤。6.70g;ESI-MS:M+H+=291.0.d)6.6克(22.8mmol)该甲酯溶于150毫升四氢呋喃,并加入溶于水的1.1克LiOH。3小时后,进一步加入0.55克LiOH,混合物在60℃搅拌16小时。浓缩后残余物用乙酸乙酯提取,水相用活性碳脱色并用HCl酸化,滤出沉淀的产品。干燥后残余4.5克;ESI-MS:M+H+=277.0.5-{[(苄基氨基)羰基]氨基}-4H-1,2,4-三唑-3-羧酸a)100毫升甲醇与10.9毫升亚硫酰氯在0℃混合,而后在室温下加入12.81克(100mmol)1,2,4-三唑-5-羧酸半水化合物。反应混合物在室温下搅拌16小时,浓缩并与100毫升饱和NaHCO3溶液混合。抽滤滤出大量的沉淀,在真空中除去乙酸乙酯并用200毫升水重结晶。10.51g;ESI-MS:M+H+=143.0.b)10.35克(72.9mmol)该氨基三唑溶于350毫升甲苯,16ml二异丙基乙胺和85毫升THF,加入1.11当量的异氰酸苄酯后,混合物回流5小时。溶液浓缩并在乙酸乙酯中处理,有机相用用1N HCl,水(2x),饱和NaHCO3溶液和水(2x)提取。有机相用Na2SO4干燥并浓缩,残余物用乙醚研磨。15.7g;ESI-MS[M+H+]=276.1.c)15.42克(56.1mmol)该三唑羧酸甲酯溶于360毫升四氢呋喃,而后加入溶于250毫升水的2.55克LiOH。4小时后,混合物浓缩,与乙酸乙酯混合,用1N HCl酸化,有机相用水,饱和NaHCO3溶液和水提取。抽滤滤出沉淀的产品并干燥。1.50g;
ESI-MS[M+H+]=262.0.4-{[(苄基氨基)羰基]氨基}噻吩-2-羧酸a)在0℃下向160毫升甲醇中滴加19.24克亚硫酰氯,而后分批加入25.45克(147mmol)2-硝基噻吩-4-羧酸。混合物在45℃下搅拌4.5小时。冷却后,加入160毫升水,并用抽滤滤出得到的沉淀。26.75g.b)向1.4升冰醋酸中加入21.5克(115mmol)该硝基噻吩,且加热至40℃,分批加入10当量的铁粉(默克公司,还原制备)。几个小时后,抽滤滤出固体,用冰醋酸,乙酸乙酯和二氯甲烷洗涤,母液与两倍量的水混合,用二氯甲烷提取4x,合并的有机相用Na2SO4干燥并浓缩。残余物在乙醚中处理,用6N异丙醇的HCl溶液转变为盐酸盐。抽滤过滤并干燥得到13.3克。
1H-NMR(d6-DMSO)d(ppm)=3.75(s,3H,OCH3),6.75,7.70(各为s,1H,Ar-H))c)将20.4克(105.3mmol)氨基噻吩引入到含27.2克二异丙基乙胺的530毫升甲苯和85ml四氢呋喃中。然后加入14.0克异氰酸苄酯,混合物在室温下搅拌16小时,而后回流3小时。黑色溶液浓缩,在乙酸乙酯中处理,用1N HCl,水和饱和NaHCO3溶液提取。有机相用Na2SO4干燥并浓缩,残余物用乙醚搅拌;21.0克。d)28克(96.2mmol)该噻吩甲酯溶于600毫升四氢呋喃,而后加入溶于350毫升水的4.62克LiOH。在60℃3小时后,真空除去四氢呋喃,含水残余物用乙酸乙酯提取2x。水相用盐酸酸化,抽滤滤出沉淀的产品。在NaOH溶液处理,用活性碳处理并通过硅藻土抽滤滤出加以提纯。用HCl酸化,抽滤过滤并干燥,得到20.0克;ESI-MS:[M+H+]=277.0。5-{[(苄基氨基)羰基]氨基}-2-呋喃羧酸a)将10克(70.86mmol)5-氨基呋喃-2羧酸甲酯溶于200毫升四氢呋喃中,加入10.07克hünig碱,而后滴加18.87克(141.7mmol)异氰酸苄酯。得到的溶液在30℃下搅拌6小时而后在高真空下浓缩,残余物在乙酸乙酯中处理。用1NHCl,水和饱和NaCl溶液洗涤。有机相干燥并浓缩。残余物与少量甲醇混合,略略煮沸并冰浴中冷却。抽滤滤出固体,用少量冷的甲醇洗涤并干燥(14.0克)。
ESI-MS[M+H+]=408.15b)10.50克(25.77mmol)5-{双[(苄基氨基)羰基〕氨基-2-呋喃酸酸甲酯悬浮在100毫升四氢呋喃中,而后加入溶于100毫升水的18.5克(773mmol)的LiOH。悬浮液在室温下搅动20小时。向混合物中加入乙酸乙酯和水,分出水相并用乙酸乙酯洗涤两次。用10% HCl调节pH值至1,滤出沉淀的固体,用水洗涤并干燥(5.92克)。
ESI-MS[M+H+]=261.05实施例I.B式I(A-E-G-L)的化合物的合成实施例1N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)-羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸(1)1.1 H-[3-(4-甲基苯基)-β-丙氨酸]三苯甲基-树脂
3.0克Cl-三苯甲基-树脂悬浮在二氯甲烷中,加入二异丙基乙胺(1.64毫升,9mmol)和3-(4-甲基苯基)-β-丙氨酸(1.45g,3.6mmol)后,在室温摇动过夜。然后进一步加入1.5毫升二异丙基乙胺和9毫升甲醇,混合物进一步摇动30分钟。抽滤滤出树脂,依次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤。为了除去Fmoc保护基,将树脂在1∶1哌啶/CH2Cl2中在室温摇动20分钟,抽滤滤出并用CH2Cl2洗涤5次。保护基的解离总共进行二次。然后再次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤树脂,并在烘箱中在室温过夜干燥。最后重量为3.44克(负载:0.896克/mmol)。1.2 H-Gly-[3-(4-甲基苯基)-β-丙氨酸]-三苯甲基-树脂
H-[3-(4-甲基苯基)-β-丙氨酸]-三苯甲基-树脂(111.6mg,0.1mmol)悬浮在二甲基甲酰胺中,加入Fmoc-Gly-OH(59.5mg,0.2mmol),二异丙基乙胺(34.4ml,0.2mmol)和TBTU(64.4mg,0.2mmol)后,在室温下摇动48小时。然后抽滤滤出树脂,依次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤。为了除去Fmoc保护基,将树脂在1∶1哌啶/CH2Cl2中在室温摇动20分钟,抽滤滤出并用CH2Cl2洗涤5次。保护基的解离总共进行二次。然后再次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤树脂,并在烘箱中在室温过夜干燥。1.3 N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)-羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸(1)
0.03mmolH-Gly-[3-(4-甲基苯基)-β-丙氨酸]-三苯甲基-树脂悬浮在二甲基甲酰胺中,加入2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-羧酸(17.5mg,0.06mmol),二异丙基乙胺(10.32ml,0.06mmol)和TBTU(19.32mg,0.06mmol)后,在室温下摇动过夜。然后抽滤滤出树脂,依次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤。然后,为解离树脂,加入1.5毫升1∶1∶3三氟乙醇/乙酸/CH2Cl2混合物,且混合物在室温下再次摇动1小时。将解离的溶液蒸发,向残余物中加入2毫升乙酸并冷冻干燥得到5毫克所需产品,ESI-MS[M+H+]=496。实施例2N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸(2)0.03mmolH-Gly-[3-(4-甲基苯基)-β-丙氨酸]-三苯甲基-树脂悬浮在二甲基甲酰胺中,加入2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酸(17.5mg,0.06mmol),二异丙基乙胺(10.32ml,0.06mmol)和TBTU(19.32mg,0.06mmol)后,在室温下摇动过夜。然后抽滤滤出树脂,依次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤。然后,为解离树脂,加入1.5毫升1∶1∶3三氟乙醇/乙酸/CH2Cl2混合物,且混合物在室温下再次摇动1小时。将解离的溶液蒸发,向残余物中加入2毫升乙酸并冷冻干燥得到8毫克所需产品,ESI-MS[M+H+]=510。然后蒸干解离溶液,残余物在乙酸乙酯中处理,并冷冻干燥。实施例3N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)-3-(3-吡啶基)-β-丙氨酸(3)3.1 H-[3-(3-吡啶基)-β-丙氨酸]-三苯甲基-树脂
按照类似于H-Gly-[3-(4-甲基苯基)-β-丙氨酸]-三苯甲基-树脂的方法制备。
H-Gly-[3-(3-吡啶基)-β-丙氨酸]-三苯甲基-树脂
H-[3-(3-吡啶基)-β-丙氨酸]-三苯甲基-树脂(106.4mg,0.1mmol)悬浮在二甲基甲酰胺中,加入Fmoc-Gly-OH(59.5mg,0.2mmol),二异丙基乙胺(33.3ml,0.2mmol)和TBTU(63.3mg,0.2mmol)后,在室温下摇动48小时。抽滤滤出树脂,依次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤。为了除去Fmoc保护基,将树脂在1∶1哌啶/CH2Cl2中在室温摇动20分钟,抽滤滤出并用CH2Cl2洗涤5次。保护基的解离总共进行二次。然后再次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤树脂,并在烘箱中在室温过夜干燥。3.2 N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)-3-(3-吡啶基)-β-丙氨酸(3)
0.03mmolH-Gly-[3-(3-吡啶基)-β-丙氨酸]-三苯甲基-树脂悬浮在二甲基甲酰胺中,加入2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-羧酸4(17.5mg,0.06mmol),二异丙基乙胺(10.32ml,0.06mmol)和TBTU(19.32mg,0.06mmol)后,在室温下摇动过夜。然后抽滤滤出树脂,依次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤。然后,为解离树脂,加入1.5毫升1∶1∶3三氟乙醇/乙酸/CH2Cl2混合物,且混合物在室温下再次摇动1小时。将解离的溶液蒸发,向残余物中加入2毫升乙酸并冷冻干燥得到8毫克所需产品,ESI-MS[M+H+]=483。实施例4N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)-3-(3-吡啶基)-β-丙氨酸(4)0.03mmolH-Gly-[3-(3-吡啶基)-β-丙氨酸]-三苯甲基-树脂悬浮在二甲基甲酰胺中,加入2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酸(17.5mg,0.06mmol),二异丙基乙胺(10.32ml,0.06mmol)和TBTU(19.32mg,0.06mmol)后,在室温下摇动过夜。然后抽滤滤出树脂,依次用二甲基甲酰胺,CH2Cl2,CH3OH和CH2Cl2洗涤。然后,为解离树脂,加入1.5毫升1∶1∶3三氟乙醇/乙酸/CH2Cl2混合物,且混合物在室温下再次摇动1小时。将解离的溶液蒸发,向残余物中加入2毫升乙酸并冷冻干燥得到10毫克所需产品,ESI-MS[M+H+]=497。下面的实施例类似地制备:N-({[(2-({[苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(5)21mg;ESI-MS[M+H+]=550.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)-3-(2-萘基)-β-丙氨酸(6)15mg;ESI-MS[M+H+]=532.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)-3-[联苯-4-基]-β-丙氨酸(7)22mg;ESI-MS[M+H+]=560.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)-3-(2,3-二甲氧基苯基)-β-丙氨酸(8)18mg;ESI-MS[M+H+]=542.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)-3-(1-萘基)-β-丙氨酸(9)19mg;ESI-MS[M+H+]=532.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(10)42mg;ESI-MS[M+H+]=565.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)-3-(2-萘基)-β-丙氨酸(11)44mg;ESI-MS[M+H+]=546.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)-3-[联苯-4-基]丙氨酸(12)7mg;ESI-MS[M+H+]=572.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)-3-(2,3-二甲氧基苯基)-β-丙氨酸(13)30mg;ESI-MS[M+H+]=556.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)-3-(1-萘基)-β-丙氨酸(14)37mg;ESI-MS[M+H+]=546.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(15)24mg;ESI-MS[M+H+]=579.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(3-吡啶基)-β-丙氨酸(16)7.1mg;ESI-MS[M+H+]=511.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(2-萘基)-β-丙氨酸(17)17mg;ESI-MS[M+H+]=560.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-[联苯-4-基]-β-丙氨酸(18)20mg;ESI-MS[M+H+]=586.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(2,3-二甲氧基苯基)-β-丙氨酸(19)16mg;ESI-MS[M+H+]=570.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(1-萘基)-β-丙氨酸(20)16mg;ESI-MS[M+H+]=560.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(4-甲基苯基)-β-丙氨酸(21)19mg;ESI-MS[M+H+]=524.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(22)18.5mg;ESI-MS[M+H+]=565.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-(3-吡啶基)-β-丙氨酸(23)4.8mg;ESI-MS[M+H+]=497.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-(2-萘基)-β-丙氨酸(24)18.4mg;ESI-MS[M+H+]=546.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-[联苯-4-基]-β-丙氨酸(25)16mg;ESI-MS[M+H+]=572.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-(2,3-二甲氧基苯基)-β-丙氨酸(26)15 mg;ESI-MS[M+H+]=556.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-(1-萘基)-β-丙氨酸(27)13mg;ESI-MS[M+H+]=546.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-(4-甲基苯基)-β-丙氨酸(28)18mg;ESI-MS[M+H+]=510.N-((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(4-甲基苯基)-β-丙氨酸(29)17.2mg;ESI-MS[M+H+]=510.(2S)-3-[((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(30)11.1mg;ESI-MS[M+H+]=583.(2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(31)14.9mg;ESI-MS[M+H+]=569.(2S)-3-[((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(32)6.5mg;ESI-MS[M+H+]=569.(2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(33)5.9mg;ESI-MS[M+H+]=555.N-{[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基](甲基)氨基]乙酰基}-3-(3-吡啶基)-β-丙氨酸(34)15mg;[M+H+]=512.N-{[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基](甲基)氨基]乙酰基}-3-(3,5-二氯苯基)-β-丙氨酸(35)18mg;[M+H+]=579.(2R)-3-({[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基](甲基)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸(36)14mg;[M+H+]=583.(2R)-3-({[(3-{[(苄基氨基)羰基]氨基}苯甲酰基)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸(37)10mg;[M+H+]=548.(2R)-3-({(2S)-2-[(3-{[(苄基氨基)羰基]氨基}苯甲酰基)氨基]丙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸(38)4mg;[M+H+]=562.N-{[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基](甲基)氨基]乙酰基}-3-(3,5-二氯苯基)-β-丙氨酸(39)16mg;[M+H+]=564.N-{[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基](甲基)氨基]乙酰基}-3-(3-吡啶基)-β-丙氨酸(40)18mg;[M+H+]=497.(2R)-3-({[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基](甲基)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸(41)15mg;[M+H+]=569.N-((2R)-2-{[(2-{[苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(3-吡啶基)-β-丙氨酸(42)18mg;ESI-MS[M+H+]=511.N-((2R)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(43)20mg;ESI-MS[M+H+]=579.N-((2R)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(44)16mg;ESI-MS[M+H+]=565.N-((2R)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)-3-(3-吡啶基)-β-丙氨酸(45)10mg;ESI-MS[M+H+]=497.(2S)-3-[((2R)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(46)12mg;ESI-MS[M+H+]=569.(2S)-3-[((2R)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(47)17mg;ESI-MS[M+H+]=583.N-{[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基](甲基)氨基]乙酰基}-3-环己基-β-丙氨酸(48)12mg;ESI-MS[M+H+]=502.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)-3-环己基-β-丙氨酸(49)10mg;ESI-MS[M+H+]=488.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-5-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸(50);ESI-MS[M+H+]=483.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸(51);ESI-MS[M+H+]=467.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-5-基)羰基]氨基}乙酰基)-3-(2,5-二甲氧基苯基)-β-丙氨酸(52);ESI-MS[M+H+]=542.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-基)羰基]氨基}乙酰基)-3-(2-萘基)-β-丙氨酸(53);ESI-MS[M+H+]=516.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-基)羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸(54);ESI-MS[M+H+]=480.(2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(55);ESI-MS[M+H+]=539.3-{1-[({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)氨基]-2-羧乙基}吡啶乙酸盐(56);ESI-MS[M+H+]=479.N-({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)-3-(2-萘基)-β-丙氨酸(57);ESI-MS[M+H+]=528.(2S)-3-[({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(58);ESI-MS[M+H+]=551.N-({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)-3-[联苯-4-基]-β-丙氨酸(59);ESI-MS[M+H+]=554.N-({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸(60);ESI-MS[M+H+]=492.N-({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)-3-环己基-β-丙氨酸(61);ESI-MS[M+H+]=484.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-环己基-β-丙氨酸(62);ESI-MS[M+H+]=498.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-(3,4-二甲氧基苯基)-β-丙氨酸(63);ESI-MS[M+H+]=552.N-(3-{[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}丙酰基)-3-吡啶-3-基-β-丙氨酸(64);ESI-MS[M+H+]=493.N-(3-{[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}丙酰基)-3-(2,5-二甲氧基苯基)-β-丙氨酸(65);ESI-MS[M+H+]=552.N-((2R)-2-{[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}丙酰基)-3-(4-叔丁基苯基)-β-丙氨酸(66);ESI-MS[M+H+]=548.N-((2R)-2-{[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}丙酰基)-3-(3,4-二甲氧基苯基)-β-丙氨酸(67);ESI-MS[M+H+]=552.(2S)-3-[({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}-丙酸(68);ESI-MS[M+H+]=554.N-({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(69);ESI-MS[M+H+]=546.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸(70);ESI-MS[M+H+]=482.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(71);ESI-MS[M+H+]=549.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸(72);ESI-MS[M+H+]=495.(2S)-3-[({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)氨基]-2-[(苯磺酰)氨基]丙酸(73);ESI-MS[M+H+]=560.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-(4-叔丁基苯基)-β-丙氨酸(74);ESI-MS[M+H+]=537.4-[({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)氨基]-3-{[(苄氧基)羰基]氨基}丁酸(75);ESI-MS[M+H+]=568.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-环己基-β-丙氨酸(76);ESI-MS[M+H+]=487.N-{[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}-3-[联苯-4-基]-β-丙氨酸(77);ESI-MS[M+H+]=571.N-{[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}-3-(2,5-二甲氧基苯基)-β-丙氨酸(78);ESI-MS[M+H+]=555.N-{[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}-3-(4-甲基苯基)-β-丙氨酸(79);ESI-MS[M+H+]=509.(2S)-3-({[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸(80);ESI-MS[M+H+]=568.N-{[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}-3-环己基-β-丙氨酸(81);ESI-MS[M+H+]=501.N-{[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}-3-(3,4-二甲氧基苯基)-β-丙氨酸(82);ESI-MS[M+H+]=555.4-({[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}氨基)-3-{[(苄氧基)羰基]氨基}丁酸(83);ESI-MS[M+H+]=582.N-(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-吡啶-3-基-β-丙氨酸(84);ESI-MS[M+H+]=496.N-(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(2,5-二甲氧基苯基)-β-丙氨酸(85);ESI-MS[M+H+]=555.(2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(86);ESI-MS[M+H+]=568.N-(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-环己基-β-丙氨酸(87);ESI-MS[M+H+]=501.(2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)氨基]-2-[(苯磺酰)氨基]丙酸(88);ESI-MS[M+H+]=574.N-(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(4-叔丁基苯基)-β-丙氨酸(89);ESI-MS[M+H+]=551.N-(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(3,4-二甲氧基苯基)-β-丙氨酸(90);ESI-MS[M+H+]=555.N-(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(3,4-二甲氧基苯基)-β-丙氨酸(91);ESI-MS[M+H+]=582.N-((2S)-2-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(4-叔丁基苯基)-β-丙氨酸(92);ESI-MS[M+H+]=551.N-((2S)-2-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(3,4-二甲氧基苯基)-β-丙氨酸(93);ESI-MS[M+H+]=555.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-(2,5-二甲氧基苯基)-β-丙氨酸(94);ESI-MS[M+H+]=541.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-(1-萘基)-β-丙氨酸(95);ESI-MS[M+H+]=531.N-({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)-3-(3,4-二甲氧基苯基)-β-丙氨酸(96);ESI-MS[M+H+]=538.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-(3,5-二氯苯基)-β-丙氨酸(97);ESI-MS[M+H+]=560.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-吡啶-3-基-β-丙氨酸(98);ESI-MS[M+H+]=493.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-(2-萘基)-β-丙氨酸(99);ESI-MS[M+H+]=542.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-[联苯-4-基]-β-丙氨酸(100);ESI-MS[M+H+]=568.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-(2,5-二甲氧基苯基)-β-丙氨酸(101);ESI-MS[M+H+]=552.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-(1-萘基)-β-丙氨酸(102);ESI-MS[M+H+]=542.N-{[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}-3-(4-甲基苯基)-β-丙氨酸(103);ESI-MS[M+H+]=506.(2S)-3-({[[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸(104);ESI-MS[M+H+]=565.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-(3,4-二甲氧基苯基)-β-丙氨酸(105);ESI-MS[M+H+]=541.N-{[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}-3-吡啶-3-基-β-丙氨酸(106);ESI-MS[M+H+]=496.N-(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(1-萘基)-β-丙氨酸(107);ESI-MS[M+H+]=545.N-(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(4-甲基苯基)-β-丙氨酸(108);ESI-MS[M+H+]=509.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸(109);ESI-MS[M+H+]=482.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(110);ESI-MS[M+H+]=549.N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸(111);ESI-MS[M+H+]=495.(2S)-3-[({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(112);ESI-MS[M+H+]=554.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-5-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸(113);ESI-MS[M+H+]=467.N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-5-基)羰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸(114);ESI-MS[M+H+]=534.(2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-5-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸(115);ESI-MS[M+H+]=539.N-((2R)-2-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(3,4-二甲氧基苯基)-β-丙氨酸(116);ESI-MS[M+H+]=555.N-((2R)-2-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)-3-(4-叔丁基苯基)-β-丙氨酸(117);ESI-MS[M+H+]=551.
实施例 ESI-MS[M+H+] 量[mg]
118 (2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}乙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 575 4
119 (2S)-3-[((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 589 7
120 (2S)-3-[((2R)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 589 5
121 (2S)-3-[(3-{[(2-[[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)乙酰基]氨基}丙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 589 2
122 (2S)-3-({[[(2-{[(苄基氨基)羰基]氨 589 3
实施例 ESI-MS[M+H+] 量[mg]
基}-1,3-噻唑-4-基)乙酰基](甲基)氨基]乙酰基}氨基)-2-[(苯磺酰)氨基]丙酸
123 (2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基)乙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 561 6
124 (2S)-3-[((2S)-2-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}丙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 575 6
125 (2S)-3-[((2R)-2-[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基)丙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 575 8
126 (2S)-3-[(3-{[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基)丙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 575 4
127 (2S)-3-({[[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基](甲基)氨基]乙酰基}氨基)-2-[(苯磺酰)氨基]丙酸 575 9
128 (2S)-3-({[[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基](甲基)氨基]乙酰基}氨基)-2-[(苯磺酰)氨基]丙酸 574 2
129 (2S)-3-[({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)-氨基]-2-{[(苄氧基)羰基]氨基}丙酸 554 1
130 (2S)-3-[({[(2-{[(苄基氨基)羰基]氨基)-4-甲基-1,3-噻唑-5-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 569 1
实施例 ESI-MS[M+H+] 量[mg]
131 (2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-4-甲基-1,3-噻唑-5-基)羰基]氨基}乙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 575 2
132 (2S)-3-[({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 560 1
133 (2S)-3-({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基](甲基)氨基]乙酰基}氨基)-2-[(苯磺酰)氨基]丙酸 574 16
134 (2S)-3-({[[(5-{[(苄基氨基)羰基]氨基)噻吩-3-基)羰基](甲基)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸 568 8
135 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 568 6
136 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-[(苯磺酰)氨基]丙酸 574 2
137 (2S)-3-({[[(5-{[(苄基氨基)羰基]氨基}-1H-1,2,4-三唑-3-基)羰基](甲基)氨基]乙酰基}氨基)-2-[(苯磺酰)氨基]丙酸 559 2
138 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}-1H-1,2,4-三唑-3-基)羰基]氨基}丙酰基)氨基-2-[(苯磺酰)氨基]丙酸 559 6
139 (2S)-3-[({[(5-{[(苄基氨基)羰基]氨基}-1H-1,2,4-三唑-3-基)羰基]氨基}乙酰基) 539 7
实施例 ESI-MS[M+H+] 量[mg]
氨基]-2-{[(苄氧基)羰基]氨基}丙酸
140 (2S)-3-({[[(5-{[(苄基氨基)羰基]氨基}-1H-1,2,4-三唑-3-基)羰基](甲基)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸 553 2
141 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}-1H-1,2,4-三唑-3-基)羰基]氨基}丙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 553 9
142 (2S)-3-({[(5-{[(苄基氨基)羰基]氨基}-2-呋喃甲酰)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸 538 14
143 (2S)-3-({[(5-{[(苄基氨基)羰基]氨基}2-呋喃甲酰)(甲基)氨基]乙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸 552 8
144 (2S)-3-({3-[(5-{[(苄基氨基)羰基]氨基}-2-呋喃甲酰)氨基]丙酰基}氨基)-2-{[(苄氧基)羰基]氨基}丙酸 552 17
145 (2S)-3-({3-[(5-{[(苄基氨基)羰基]氨基]-2-呋喃甲酰)氨基]丙酰基}氨基)-2-[(苯磺酰)氨基]丙酸 558 4
146 (2S)-3-[((2S)-2-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}-3-甲基丁酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 596 16
147 (2S)-3-[({[(5-{[(苄基氨基)羰基]氨基}-1,3-噻唑-2-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 555 6
148 (3R)-4-({[[(4-{[(苄基氨基)羰基]氨 579 6
实施例 ESI-MS[M+H+] 量[mg]
基}-1-甲基-1H-吡咯-2-基)羰基](甲基)氨基]乙酰基}氨基)-3-{[(苄氧基)羰基]氨基}丁酸
149 (3R)-4-[(3-{[4-{[(苄基氨基)羰基)氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}丙酰基)氨基]-3-{[(苄氧基)羰基]氨基}丁酸 579 2
150 (3R)-4-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}丙酰基)氨基-3-{[(苄氧基)羰基]氨基}丁酸 582 18
151 (3R)-4-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-4-基)羰基]氨基}乙酰基)氨基]-3-{[(苄氧基)羰基]氨基}丁酸 569 9
152 (3R)-4-[({[(5-{[(苄基氨基)羰基]氨基)噻吩-3-基)羰基]氨基}乙酰基)氨基]-3-{[(苄氧基)羰基]氨基}丁酸 568 8
153 (3R)-4-({[[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基](甲基)氨基]乙酰基}氨基)-3-{[(苄氧基)羰基]氨基}丁酸 582 1
154 (3R)-4-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-3-{[(苄氧基)羰基]氨基}丁酸 582 14
155 (3R)-4-[({[(5-{[(苄基氨基)羰基]氨基}-1H-1,2,4-三唑-3-基)羰基]氨基}乙酰基)氨基]-3-{[(苄氧基)羰基)氨基}丁酸 553 19
156 (3R)-4-({[[(5-{[(苄基氨基)羰基]氨基}-1H-1,2,4-三唑-3-基)羰基](甲基)氨基]乙酰基}氨基)-3-{[(苄氧基)羰基]氨基}丁酸 567 22
实施例 ESI-MS[M+H+] 量[mg]
157 (3R)-4-[(3-{[(5-{[(苄基氨基)羰基]氨基}-1H-1,2,4-三唑-3-基)羰基]氨基}丙酰基)氨基]-3-{[(苄氧基)羰基]氨基}丁酸 567 22
158 (3R)-4-({[(5-{[(苄基氨基)羰基]氨基}-2-呋喃甲酰)氨基]乙酰基}氨基)-3-{[(苄氧基)羰基]氨基}丁酸 552 2
159 (3R)-4-({[(5-{[(苄基氨基)羰基]氨基}-2-呋喃甲酰)(甲基)氨基]乙酰基}氨基)-3-{[(苄氧基)羰基]氨基}丁酸 566 2
160 (3R)-4-({3-[(5-{[(苄基氨基)羰基]氨基}-2-呋喃甲酰)氨基]丙酰基}氨基)-3-{[(苄氧基)羰基]氨基}丁酸 566 23
161 (3R)-4-[({[(5-{[(苄基氨基)羰基]氨基}-1,3-噻唑-2-基)羰基]氨基}乙酰基)氨基]-3-{[(苄氧基)羰基]氨基}丁酸 569 16
合成羧酸的α位的N取代基可通过下面的反应广泛的变换:
α-N-Fmoc-β-N-Aloc-二氨基丙酸(4.52g)与5克王氏树脂如P.Sieber(Tetrahedron Lett.28(1987)6147)所述偶合。而后用20毫升10%DBU,2%吡啶和88%DMF的混合物在3分钟将Fmoc基团除去。抽滤滤出树脂,用DMF,CH2Cl2和二乙基醚洗涤数次,并干燥。担载约1.15mmol/g。
可通过加入3当量的羧酸,并用HATU或TBTU通过常用的标准方法在4小时内活化在α位引入酰基。磺酰基基团如下引入:将0.145g担载的树脂悬浮在1ml CH2Cl2中,加入0.4当量的DMAP,4当量的甲氧基(三甲基甲硅烷氧基)二甲基乙烯酮缩二乙醇(MTDA)和2当量的磺酰氯在1.5ml CH2Cl2中的溶液。(见M.Gude et al.,TetrahedronLett.37(1996)8589)。8小时后,抽滤滤出树脂,并用CH2Cl2洗涤10次,DMF洗涤5次,CH2Cl2洗涤5次。
Aloc基团通过如下方法除去:用N2吹洗聚合物而后加入24当量的苯基硅烷在无氧CH2Cl2中的溶液(见N.Thieriet et al.,Tetrahedron Lett.38(1997)7275)。加入溶于CH2Cl2的0.1当量Pd(PPh3)4,混合物反应约90分钟。
而后用通常的标准方法将在DMF中的3当量Fmoc-氨基酸用TBTU活化,并与游离氨基基团偶合8小时。Fmoc基团如上所述除去。最后与N-(3-羧基噻吩-5-基)-N’-苄基尿素的偶合按照类似于上述的方法偶合2天。
树脂用DMF和CH2Cl2彻底洗涤,而后加入1.5ml 95%TFA和5%水的混合物。45分钟后,滤出树脂,用少量CH2Cl2洗涤。滤液合并并浓缩。残余物根据测试目的用下面的一种或多种方法提纯:1.溶于少量甲醇,加入水进行沉淀。抽滤滤出沉淀并干燥。2.残余物溶于乙酸乙酯中,溶液用水提取。而后浓缩并用乙醚搅拌。抽滤滤出沉淀并干燥。3.残余物在硅胶柱上柱层析。
实施例 ESI-MS[M+H+] 量[mg]
162 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-{[(2-氯苯基)磺酰基]氨基}丙酸 608.15和610.15 9.1
163 (2S)-3-[(3-{[(5-{[(苄基氨基]羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-[(丁基磺酰基)氨基]丙酸 554.15 1.8
实施例 ESI-MS[M+H+] 量[mg]
164 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-[(苄基磺酰基)氨基]丙酸 588.15 21.2
165 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-[(1-萘基磺酰基)氨基]丙酸 624.15 16.3
166 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-[(2-萘基磺酰基)氨基]丙酸 624.15 19.2
167 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-{[(2,4,5-三氯苯基)磺酰基)氨基}丙酸 676.05;677.95;680.0;682.0 6.5
168 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-{[(2,6-二氯苯基)磺酰基]氨基}丙酸 642.15;644.05 13.1
169 (2S)-3-[(3-{[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}丙酰基)氨基]-2-{[(2,5-二甲氧基苯基)磺酰基]氨基}丙酸 634.15 3.3
II. 生物学实施例实施例1整联蛋白αvβ3试验
使用基于天然整联蛋白αvβ3配体玻连蛋白和用于与结合到固定相上的整联蛋白αvβ3结合起来的测试物质之间的竞争作用的测试系统进行整联蛋白αvβ3拮抗剂识别和评定。方法-用250ng/ml整联蛋白-αvβ3在0.05M NaHCO3pH9.2的溶液涂敷微量滴定板;0.1ml/井;-用1%奶粉/试验缓冲液饱和;0.3ml/井;0.5h/RT-用0.05%Tween20/试验缓冲液洗涤3次-测试物质,在0.1%奶粉/测试缓冲液中,50μl/井+0μg/ml或2μg/ml人类玻连蛋白(Boehringer Ingelheim T007)0.1%奶粉/测试缓冲液,50μl/井;1h/RT-用0.05%Tween20/试验缓冲液洗涤3次-1μg/ml抗人类玻连蛋白抗体与过氧化酶(Kordia SAVN-APHRP)在0.1%奶粉试验缓冲液中偶合;0.1ml/井;1h/RT-用0.05%Tween20/试验缓冲液洗涤3次-0.1ml/井过氧化酶底物-用0.1ml/井2M H2SO4停止反应-测量在450nm的吸收整联蛋白αvβ3:人类胎盘用诺乃洗涤剂溶解,将整联蛋白αvβ3在GRGDSPK-基质上进行亲合性-纯化(用EDTA洗脱)。用阴离子交换色谱法除去整联蛋白αIIbβ3和人血清白蛋白,以及洗涤剂和EDTA的沾污。试验缓冲液:50mM Tris pH7.5;100mM NaCl;1mM CaCl2;1mMMgCl2;10μM MnCl2过氧化酶底物:将0.1毫升TMB溶液(42mM TMB在DMSO中)和10毫升底物缓冲液(0,1M乙酸钠pH4.9)混合,而后加入14.7μl的3%H2O2
在试验中使用不同的稀释度的测试物质,进行IC50值的测定(替换50%配体的拮抗剂的浓度)。下表显示所选取实施例的IC50值。
化合物 IC50αvβ3[μM]
N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噻唑-5-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸 10
N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸 0.0138
N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-基)羰基]氨基}乙酰基)-3-(2-萘基)-β-丙氨酸 0.048
N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-基)羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸 0.040
(2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-4-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 0.1
3-{1-[({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)氨基]-2-羧乙基}吡啶乙酸盐 0.016
N-({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)-3-(2-萘基)-β-丙氨酸 0.043
(2S)-3-[({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 0.26
N-({[(4-{[(苄基氨基)羰基]氨基}-1-甲基-1H-吡咯-2-基)羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸 0.039
N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸 1
N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸 10
N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-2-基)羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸 10
N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸 0.0005
N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸 0.0047
N-({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)-3-(4-甲基苯基)-β-丙氨酸 0.0021
(2S)-3-[({[(5-{[(苄基氨基)羰基]氨基}噻吩-3-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 0.0118
N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-5-基)羰基]氨基}乙酰基)-3-吡啶-3-基-β-丙氨酸 0.00028
N-({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-5-基)羰基]氨基}乙酰基)-3-(3,5-二氯苯基)-β-丙氨酸 0.00038
(2S)-3-[({[(2-{[(苄基氨基)羰基]氨基}-1,3-噁唑-5-基)羰基]氨基}乙酰基)氨基]-2-{[(苄氧基)羰基]氨基}丙酸 0.0018
实施例2整联蛋白αIIbβ3试验
该试验基于天然整联蛋白αIIbβ3配体纤维蛋白原和用于与整联蛋白αIIbβ3结合的测试物质之间的竞争作用。方法:-用10μg/ml纤维蛋白原(Calbiochem 341578)在0.05 M NaHCO3 pH9.2的溶液涂敷微量滴定板;0.1ml/井;-用1%BSA/PBS饱和;0.3ml/井;30min/RT-用0.05%Tween 20/PBS洗涤3次-测试物质在0.1%BSA/PBS中;50μl/井+200μg/ml整联蛋白αIIbβ3(Kordia)在0.1%BSA/PBS中;50μl/井;2-4h/RT-如上洗涤3次-生物素化的抗整联蛋白αIIbβ3抗体(Dianova CBL 130 B);1∶1000在0.1%BSA/PBS中;0.1ml/井;2-4h/RT-如上洗涤3次-抗生蛋白链菌素-过氧化酶复合体(B.M.1089153)1∶10000在0.1%BSA/PBS中;0.1ml/井;30min/RT-如上洗涤3次-0.1ml/井过氧化酶底物-用0.1ml/井2M H2SO4终止反应-测量在450nm的吸收过氧化酶底物:将0.1毫升TMB溶液(42mM TMB在DMSO中)和10毫升底物缓冲液(0.1M乙酸钠pH4.9)混合,而后加入14.7μl 3%H2O2
在试验中使用不同的稀释度的测试物质,进行IC50值的测定(替换50%配体的拮抗剂的浓度)。
物质的选择性可以通过比较整联蛋白αIIbβ3和整联蛋白αvβ3测试的IC50值确定。实施例3CAM试验
CAM(绒膜尿囊)试验为评定整联蛋白αvβ3拮抗剂体内活性公认的模型。它基于肿瘤组织的血管生成和新血管化的抑制(Am.J.Pathol.1975,79,597-618;Cancer Res.1980,40,2300-2309;Nature 1987,329,630)。该方法类似于先有技术。可以容易地进行小鸡胚胎血管和移植的肿瘤组织的生长和评定。实施例4兔眼试验
在整联蛋白αvβ3拮抗剂的存在下血管生成和新血管化的抑制可以按照类似于实施例3的方法在此体内模型进行和评定。该模型为公认的,基于从兔眼的边缘开始到角膜的血管生长(Proc.Natl.Acad.Sci.USA.1994,91,4082-4085;Science 1976,193,70-72).该方法类似于先有技术。

Claims (28)

1.式I的化合物和生理学可接受的盐,前体药物及对映体纯或非对映体纯和互变异构形式:
                   A-E-G-L       I
其中A,E,G和L具有下面的含义:
L为式IL的结构单元
其中:
a  为0或1,
T  为COOH基团或可水解为COOH的基团,
R2 为氢,NHSO2R21,NHCOR21或NHCOOR22
其中
R21为支链或非支链,任选取代的C1-C6-烷基,C3-C6-环烷基,C1-C4-烷基-C3-C6-环烷基基团,C5-C12-二环烷基或C6-C18-三环烷基基团至多三个相同或不同基团取代的芳基,烷基芳基,杂芳基基团或3到6元饱和,不饱和或芳香杂环,该环含有至多三个相同或不同杂原子O,N,S,其中两个基团一起形成一稠和的,饱和的,不饱和的或芳香的碳环或杂环,该环含有至多三个相同或不同杂原子O,N,S,且该环可选地被取代,或另一个可选被取代的,饱和的,不饱和的或芳香环可与该环稠和,
R22为支链或非支链的,任选取代的C1-C6-烷基或任选取代的芳基或烷基芳香基基团,
R3为氢或-(CH2)b-(X)c-R31
其中
b  为0,1,2或3,
c  为0或1,
X  为-SO2-,-S-,-O-,-CO-,-NH-SO2-,-O-CO-,-CO-O-,-NH-CO-,-CO-NH-,-CO-N(R31)-,-N(R31)-CO-,-SO2-NH-,-SO2-N(R31)-或-N(R31)-SO2-,
R31为氢,羟基,支链或非支链的,任选取代的C1-C6-烷基,C1-C4-烷氧基,-O-烷基芳香基或-O-芳基,具有伯取代或可选地仲或叔取代的氨基基团,可选地被C1-C4-烷基-或芳基取代的C2-C6-炔基或C2-C6-链烯基基团,C5-C12-二环烷基,C6-C18-三环烷基基团或可被至多三个相同或不同的基团取代的,可能包含至多三个不同的或相同的杂原子O,N,S的3-到6-元饱和或不饱和的杂环,C3-C8-环烷基,芳基或杂芳基基团,其中两个基团可能一起为稠合的,饱和,不饱和的或芳香碳环或杂环,该环可能包含至多三个不同的或相同的杂原子O,N,S,并且该环可选地被取代,或者,另一个任选取代的,饱和的,不饱和的或芳香环可与该环稠合,
R4为氢,或支链或非支链的,任选取代地C1-C4-烷基,C3-C6-烯基,C3-C6-炔基或者C3-C6-环烷基基团,
G  为结构单元IG
Figure A0080890700031
其中
d   为0,1或2,
R5 为氢,羟基,支链或非支链的,任选取代的C1-C6-烷基,C1-C4-烷氧基,-O-烷基芳基或-O-芳基,伯取代或可选地仲或叔取代的氨基基团,可选地C1-C4-烷基-或芳基取代的C2-C6-炔基或C2-C6-链烯基基团,C5-C12-二环烷基,C6-C18-三环烷基基团或可被至多三个相同或不同的基团取代的,可能包含至多三个不同的或相同的杂原子O,N,S的3-到6-元饱和或不饱和的杂环,C3-C8-环烷基,芳基或杂芳基基团,其中两个基团可能一起为稠合的,饱和,不饱和的或芳香碳环或杂环,该环可能包含至多三个不同的或相同的杂原子O,N,S,并且该环可选地被取代,或者,另一个任选取代的,饱和的,不饱和的或芳香环可与该环稠合,或天然氨基酸的侧链,
R6为氢,或支链或非支链的,任选取代的C1-C4-烷基,C3-C6-烯基,C3-C6-炔基或者C3-C6-环烷基基团,
E  为式IE的结构单元
-(NH)g-(CH2)f-Q-(CH2)e-CO-  IE
其中
e  为0,1或2,
f  为0或1,
g  为0或1,
Q  为双次连接的,任选取代的杂芳基基团,两个取代基可以一起为一饱和的,不饱和的或芳香碳环或杂环,其中可以包含至多三个不同的或相同的杂原子O,N,S,并且该环可以可选地被取代,或者,另一个任选取代地饱和的,不饱和的或芳香环可以与该环稠合,
A  为式IA 1到IA 20的结构单元之一
Figure A0080890700051
其中
R10,R11各自独立地为氢,-(CH2)h-(Y)i-R101,或两个基团一起为3-到8元,任选取代的,饱和的,不饱和的或芳香N-杂环,该环可以另外包含两个其它相同的或不同的杂原子O,N或S,
其中
h  为0,1,2或3,
i  为0或1,
Y  为-SO2-,-S-,-O-,-CO-,-NH-SO2-,-O-CO-,-CO-O-,-NH-CO-,-CO-NH-,-CO-N(R101)-,-N(R101)-CO-,-SO2-NH-,-N(R101)-SO2-或-SO2-N(R101)-且
R101为羟基,支链或非支链的,任选取代的C1-C6-烷基,C1-C4-烷氧基,-O-烷基芳基或-O-芳基,伯取代或可选地仲或叔取代的氨基基团,可选地C1-C4-烷基-或芳基取代的C2-C6-炔基或C2-C6-链烯基基团,C5-C12-二环烷基,C6-C18-三环烷基基团或可被至多三个相同或不同的基团取代的,可能包含至多三个不同的或相同的杂原子O,N,S的3-到6-元饱和或不饱和的杂环,C3-C8-环烷基,芳基或杂芳基基团,其中两个基团可能一起为稠合的,饱和的,不饱和的或芳香碳环或杂环,该环可能包含至多三个不同的或相同的杂原子O,N,S,并且该环可选地被取代,或者,另一个任选取代的,饱和的,不饱和的或芳香环可与该环稠合,
R12为支链或非支链的,任选取代的C1-C4-烷基,烷基芳基,C3-C6环烷基或C1-C4-烷基-C3-C6-环烷基基团或任选取代的芳基,
R13为氢,-OH,-CN,-CONH2,任选取代的支链或非支链C1-C4-烷基,C1-C4-烷氧基或-OCO-C1-C4-烷基基团,或任选取代的烷基芳基,-O-烷基芳基,-OCO-芳基,-OCO-烷基芳基或-OCO-烯丙基基团,
R14为氢,任选取代的支链或非支链的C1-C4-烷基,烷基芳基,-CO2-C1-C4-烷基,-CO2-烷基芳基,-CO2-烯丙基,-CO-C1-C4-烷基,-CO-烷基芳基或-CO-烯丙基基团,
R15为氢,任选取代的支链或非支链的C1-C4-烷基或任选取代的芳基或烷基芳基基团,
R16,R17各自独立的为-NH2,卤素或任选取代的支链或非支链的C1-C4-烷基或C1-C4-烷氧基基团或任选取代的芳基,
Z1,Z2,Z3,Z4各自独立地为CH,C-CH3,C-OCH3,C-Cl或N。
2.一种用于口服或肠胃外给药的药物制剂,包含至少一种如权利要求1中的化合物和常规的药物赋形剂。
3.如权利要求1中所要求保护的化合物在制造用于治疗疾病的药物中的用途。
4.权利要求3中的权利要求1所要求保护的化合物作为整联蛋白受体拮抗剂的用途。
5.权利要求4中的权利要求1中所要求保护的化合物作为αvβ3整联蛋白受体拮抗剂的用途。
6.如权利要求1中所要求保护的化合物在制造用于治疗涉及整联蛋白受体的疾病的药物中的用途。
7.如权利要求6中的权利要求1所要求保护的化合物在制造用于治疗涉及αvβ3整联蛋白受体的疾病的药物中的用途。
8.权利要求7中的权利要求1要求保护的化合物用于治疗动脉粥样硬化,类风湿性关节炎,脉管损伤后再狭窄,血管成形术,急性肾衰竭,与血管生成有关的微血管病,糖尿病患者血管病,血小板介导的血管闭塞,动脉血栓形成,充血性心力衰竭,心肌梗塞,中风,癌症,骨质疏松症,高血压,牛皮癣或病毒性,寄生虫的或细菌性疾病,炎症,创伤愈合,甲状旁腺机能亢进,阴囊炎性癌,恶性高钙血症或转移性的溶骨病变的用途。
9.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
血小板粘连,活化或聚集作用抑制剂,
防止凝血酶活性或形成的抗凝血剂,
血小板活化化合物的拮抗剂或
选择蛋白拮抗剂。
10.如权利要求9中所要求保护的药物制剂在制造用于治疗血小板介导的血管闭塞或血栓形成的药物中的用途。
11.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
血小板活化或聚集作用抑制剂,
丝氨酸蛋白酶抑制剂,
纤维蛋白原减少的化合物,
选择蛋白拮抗剂,
ICAM-1或VCAM-1拮抗剂
白细胞粘连抑制剂
血管壁移行抑制剂,
调节纤维蛋白溶解的化合物,
补体因子抑制剂,
内皮素受体拮抗剂,
酪氨酸激酶抑制剂,
抗氧化剂或
白细胞间介素8拮抗剂。
12.如权利要求11中所要求保护的药物制剂在制造用于治疗心肌梗塞或中风的药物中的用途。
13.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
内皮素拮抗剂,
ACE抑制剂,
血管紧张素受体拮抗剂,
肽链内切酶抑制剂,
beta阻断剂
钙通道阻断剂,
磷酸二酯酶抑制剂或
caspase抑制剂
14.如权利要求13中所要求保护的药物制剂在制造用于治疗充血性心力衰竭的药物中的用途。
15.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
凝血抑制因子,
因子Xa抑制剂,
导致凝血酶形成的凝结通道抑制剂,
血小板粘连,活化或聚集作用抑制剂,
内皮素受体拮抗剂,
氧化氮合酶抑制剂,
CD44拮抗剂,
选择蛋白拮抗剂,
MCP-1拮抗剂,
增殖细胞中信号转导抑制剂,
由EGF,PDGF,VEGF或bFGF介导的细胞响应拮抗剂,或
抗氧化剂。
16.如权利要求15中所要求保护的该药物制剂在制造用于治疗再狭窄后脉管损伤或斯坦特固定模植入的药物中的用途。
17.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
由EGF,PDGF,VEGF或bFGF介导的细胞响应拮抗剂,
肝素或低分子量肝素或其它GAGs,
MMPs抑制剂,
选择蛋白拮抗剂,
内皮素拮抗剂,
ACE抑制剂,
血管紧张素受体拮抗剂,
糖基化作用抑制剂或
AGE形成抑制剂或它们的受体拮抗剂。
18.如权利要求17中所要求保护的药物制剂在制造用于治疗糖尿病患者血管病的药物中的用途。
19.一种药物制剂,包含至少一种如权利要求1中的化合物,其中适当的药物赋形剂和至少一种选自下面一组的其它化合物:
脂质降低的化合物,
选择蛋白拮抗剂,
ICAM-1或VCAM-1拮抗剂
肝素或低分子量肝素或其它GAGs,
MMPs抑制剂,
内皮素拮抗剂,
脱脂蛋白A1拮抗剂,
胆固醇拮抗剂,
HMG-CoA还原酶抑制剂,
ACAT抑制剂,
ACE抑制剂,
血管紧张素受体拮抗剂,
酪氨酸激酶抑制剂,
蛋白激酶C抑制剂,
钙通道阻断剂,
LDL受体功能兴奋剂,
抗氧化剂或
自由基清除剂。
20.如权利要求19中所要求保护的药物制剂在制造用于治疗动脉粥样硬化的药物中的用途。
21.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
抑制细胞生长的或抗肿瘤的化合物,
抑制增殖的化合物或
肝素或低分子量肝素或其它GAGs。
22.如权利要求21中所要求保护的药物制剂在制造用于治疗癌症的药物中的用途。
23.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
用于抗吸收治疗的化合物,
用于激素替补治疗的化合物,
重组体人生长激素,
二膦酸盐,
用于降钙素治疗的化合物,
降钙素兴奋剂,
钙通道阻断剂,
骨形成兴奋剂,
白细胞间介素-6拮抗剂或
Src酪氨酸激酶抑制剂。
24.如权利要求23中所要求保护的药物制剂在制造用于治疗骨质疏松症的药物中的用途。
25.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
TNF拮抗剂,
VLA-4或VCAM-1拮抗剂
LFA-1,Mac-1或ICAMs拮抗剂,
补体抑制剂,
免疫抑制剂,
白细胞间介素-1,-5或-8拮抗剂或
二氢叶酸还原酶抑制剂
26.如权利要求25中所要求保护的药物制剂在制造用于治疗类风湿性关节炎的药物中的用途。
27.一种药物制剂,包含至少一种如权利要求1中的化合物,选择性的药物赋形剂和至少一种选自下面一组的其它化合物:
胶原酶,
PDGF拮抗剂或
MMPs。
28.如权利要求27中所要求保护的药物制剂在制造用于改善创伤愈合的药物中的用途。
CN00808907A 1999-04-28 2000-04-17 整联蛋白受体拮抗剂 Pending CN1355811A (zh)

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