CN1337881A - 有机磷化合物预防或治疗感染的应用 - Google Patents
有机磷化合物预防或治疗感染的应用 Download PDFInfo
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- CN1337881A CN1337881A CN00803129A CN00803129A CN1337881A CN 1337881 A CN1337881 A CN 1337881A CN 00803129 A CN00803129 A CN 00803129A CN 00803129 A CN00803129 A CN 00803129A CN 1337881 A CN1337881 A CN 1337881A
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- virus
- antibacterial
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- alkyl
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Abstract
本发明涉及通式(I)的有机磷化合物在预防和治疗由于病毒、细菌、真菌或寄生虫引起的人和动物的感染、以及在植物中作为植物的抗真菌剂、抗菌剂和除草剂的应用:其中X是磷原子或硫原子,A是取代或未取代的C2-5烷基链。
Description
本发明涉及有机磷化合物、其盐、酯和酰胺在预防和治疗由于病毒、细菌、真菌或寄生虫引起的人和动物的感染、以及在植物中作为植物的抗真菌剂、抗菌剂和除草剂的应用。根据本发明,有机磷化合物包含膦酰基(phosphinoyl)衍生物、次膦酸衍生物以及膦酸衍生物。
为了拓宽对于人和动物治疗的选择范围,迫切需要药剂不仅具有高度活性,而且与其他药物制剂不同,还具有更低的副作用,并因此对人的健康构成更小的危险。
因此,本发明的目的是提供一种能广泛用于由病毒、细菌、真菌、和寄生虫引起的人和动物感染以及作为植物杀真菌剂、杀细菌剂和除草剂的物质,而且所述物质能满足上述要求。
令人惊奇的是,借助权利要求1中限定的物质,实现了该目的。这类物质对于病毒、某些细菌、真菌、单细胞寄生虫和多细胞寄生虫显示出抗感染作用。
用于本发明的有机磷化合物是通式(I)的化合物及其药物学上可接受的盐、酯和酰胺以及酯的盐:其中X是磷原子或硫原子,A是直链C2-9亚烷基,其可含有取代基,所述取代基是相同或不同的,它
们选自于以下组中:氢、羟基、卤素、氨基和氧代基团、C1-26烷基、
C1-26烷氧基、C1-26烷氧基-C1-26烷基或C3-8环烷基-(C0-9)烷基,
其中C1-26烷基和C1-26烷氧基各自是支链或直链的、饱和的或者具有
一个或多个双键的不饱和基团并且可被羟基、氨基、卤素和氧代基团
取代,C3-8环烷基-(C0-9)烷基中的C3-8环烷基和Co-9烷基可包含
一个或多个双键并且该环烷基的一个或两个碳原子可被氮、氧或硫置
换,并且其中该环烷基和该烷基均可被羟基、卤素、氨基、氧代基团、
支链或直链的C1-9烷基和C2-9链烯基取代,其中C1-9烷基和C2-9链
烯基可被氢、羟基、氨基、卤素和氧代基团取代,R1和R2相同或不同,并选自于以下组中:氢、取代和未取代的C1-9烷基、
取代和未取代的羟基-C1-9烷基、取代或未取代的C1-9链烯基、取代
或未取代的C1-9炔基、取代或未取代的芳基、取代或未取代的酰基、
取代和未取代的环烷基、取代和未取代的芳烷基、取代或未取代的杂
环基、卤素、OX1和OX2,其中X1和X2相同或不同,并选自于以下组中:氢、取代和未取代的C1-9烷基、
取代和未取代的羟基-C1-9烷基、取代或未取代的C1-9链烯基、取代
或未取代的C1-9炔基、取代或未取代的芳基、取代或未取代的酰基、
取代和未取代的环烷基、取代和未取代的芳烷基、取代或未取代的杂
环基,R3和R4相同或不同,并选自于以下组中:取代和未取代的C1-26烷基、羟
基-C1-26烷基、取代或未取代的芳基、取代或未取代的酰基、取代和
未取代的芳烷基、取代或未取代的C1-26链烯基、取代或未取代的
C1-26炔基、取代和未取代的环烷基、取代或未取代的杂环基、卤素、OX3
和OX4,其中X3和X4相同或不同,并选自于以下组中:氢、取代和未取代的C1-26烷基、
取代或未取代的羟基-C1-26烷基、取代或未取代的芳基、取代和未取
代的芳烷基、取代或未取代的C1-26链烯基、取代或未取代的C1-26炔
基、取代和未取代的环烷基、取代或未取代的杂环基、甲硅烷基、有
机碱和无机碱的阳离子,尤其是周期表中I、II、III主族的金属、铵、
取代的铵以及由乙二胺或氨基酸衍生的铵化合物。
X3和X4优选是周期表中I、II或III主族的金属、铵、取代的铵以及由乙二胺或氨基酸衍生的铵化合物。换言之,有机磷化合物的盐是与有机碱或无机碱形成的盐(例如,钠盐、钾盐、钙盐、铝盐、铵盐、镁盐、三乙胺盐、乙醇胺盐、二环己基胺盐、乙二胺盐、N,N′-二苄基乙二胺盐等)以及与氨基酸形成的盐(例如,精氨酸盐、谷氨酸盐等)等。
X3和X4尤其优选是相同或不同的,并选自于以下组中:氢、钠、钾、甲基、乙基。
A优选是C3-5烷基链。
特别优选的化合物是式(II)化合物:其中X、R1、R3、R4定义如上,而且R1的相邻于杂原子的碳原子优选被羟基取代;和式(III)化合物:其中X、R1、R3、R4定义如上,而且R1优选是酰基,尤其优选是甲酰基、乙酰基、丙酰基或丁酰基。
以下给出以上描述的定义以及适当实例的具体特征:
“酰基”指源于酸的取代基,如来自有机羧酸、碳酸、氨基甲酸、或者对应于以上各酸的硫代酸或亚氨基酸,或来自有机磺酸,其中每种酸的分子都包括脂肪性、芳香性和/或杂环基团以及氨基甲酰基或亚氨基甲酰基。
以下给出酰基的适当实例:
脂肪族酰基定义为来自脂肪酸的酰基残基,包括以下基团:烷酰基(例如甲酰基、乙酰基、丙酰基、丁酰基、异丁酰基、戊酰基、异戊酰基、新戊酰基等);链烯酰基(例如丙烯酰基、甲基丙烯酰基、巴豆酰基等);烷基硫代烷酰基(例如甲基硫代乙酰基、乙基硫代乙酰基等);链烷磺酰基(例如甲磺酰基、乙磺酰基、丙磺酰基等);烷氧羰基(例如甲氧羰基、乙氧羰基、丙氧羰基、异丙氧羰基、丁氧羰基、异丁氧羰基等);烷基氨基甲酰基(例如甲基氨基甲酰基等);(N-烷基)硫代氨基甲酰基(例如(N-甲基)-硫代氨基甲酰基等);烷基亚氨甲酰基(例如甲基亚氨甲酰基等);乙二酸-酰基;烷草酰基(例如甲草酰基、乙草酰基、丙草酰基等)。
上述脂肪族酰基的实例中,脂肪族烃部分,特别是烷基或烷烃残基,可以任选地有一个或多个适当的取代基,如氨基、卤素(例如氟、氯、溴等)、羟基、肟基、羧基、烷氧基(例如甲氧基、乙氧基、丙氧基等)、烷氧羰基、酰基氨基(例如苄氧羰基氨基等)、酰氧基(例如乙酰氧基、苯甲酰氧基等)等;含这些取代基的脂肪族酰基优选为例如被氨基、羧基、氨基和羧基、卤素、酰基氨基等取代的烷酰基。
芳香族酰基定义为那些来自含取代或未取代芳基的酸的酰基,其中芳基可以包括苯基、甲苯甲酰基、二甲苯基和萘基等;其适当的实例如下所示:芳酰基(例如苯甲酰基、甲苯甲酰基、二甲苯酰基、萘甲酰基和邻苯二甲酰基等);芳烷酰基(例如苯乙酰基等);芳链烯酰基(例如肉桂酰基等);芳氧烷酰基(例如苯氧乙酰基等);芳基硫代烷酰基(例如苯基硫代乙酰基等);芳基氨基烷酰基(例如N-苯基甘氨酰基等);芳烃磺酰基(例如苯磺酰基、甲苯磺酰基、二甲苯磺酰基、萘磺酰基等);芳氧羰基(例如苯氧羰基、萘氧羰基等);芳烷氧羰基(例如苄氧羰基等);芳基氨基甲酰基(例如苯基氨基甲酰基、萘基氨基甲酰基等);芳基乙醛酰基(例如苯基乙醛酰基等)。
上述芳香族酰基的实例中,芳烃部分(尤其是芳基)和/或脂肪族烃部分(特别是烷烃残基)可任选地有一个或多个适当的取代基,如那些已描述的作为烷基或烷烃残基的适当取代基的取代基。优选的含特定取代基的芳香族酰基的实例是卤素和羟基取代的芳酰基,卤素和酰氧基取代的芳酰基,羟基、肟基、二卤代烷酰氧基亚氨基取代的芳烷酰基,以及芳基硫代氨基甲酰基(例如苯基硫代氨基甲酰基等);和芳基亚氨甲酰基(例如苯基亚氨甲酰基等)。
杂环酰基表示来自含杂环基团的酸的酰基,包括:
杂环羰基,其中杂环基是含至少一个选自于氮、氧和硫的杂原子的芳香族或脂肪族五元或六元杂环(例如苯硫基、呋喃甲酰基、吡咯羰基、烟酰基(nicotinyl)等);
杂环-烷酰基,其中杂环基是含至少一个选自于氮、氧和硫的杂原子的五元或六元杂环(例如苯硫基乙酰基、呋喃基乙酰基、咪唑基丙酰基、四唑基乙酰基、2-(2-氨基-4-噻唑基)-2-甲氧基亚氨基乙酰基等)等。
上述杂环酰基的实例中,杂环和/或脂肪族烃部分可以任选地包括一个或多个适当的取代基,例如与上述烷基和烷烃基团的取代基相同的。
除非另有定义,“烷基”是含有最多26个碳原子的线性或支链烷基残基,如甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、己基等。
除非另有定义,“羟烷基”是包含至少一个羟基、优选包含一个或两个羟基基团并含有最多26个碳原子的线性或支化烷基残基。
除非另有定义,“烯基”是含有最多26个碳原子的线性或支化烯基基团,如乙烯基、丙烯基(例如1-丙烯基、2-丙烯基)、1-甲基丙烯基、2-甲基丙烯基、丁烯基、2-乙基丙烯基、戊烯基、己烯基。
除非另有定义,“炔基”是含有最多26个碳原子的线性或支化炔基基团。
环烷基优选表示选择性取代的C3-8环烷基;可能的取代基特别是烷基、烯基、炔基、烷氧基(例如甲氧基、乙氧基等)、卤素(例如氟、氯、溴等)、硝基等。
芳基是芳族烃残基,如苯基、萘基等,所述残基可以包含或不包含一个或多个合适的取代基,如烷基、烯基、炔基、烷氧基(例如甲氧基、乙氧基等)、卤素(例如氟、氯、溴等)、硝基等。
“芳烷基”包括单-、二-、三-苯基烷基,如苄基、苯乙基、二苯甲基、三苯甲基等,其中芳族部分可以包含或不包含一个或多个合适的取代基,如烷氧基(例如甲氧基、乙氧基等)、卤素(例如氟、氯、溴等)、硝基等。
可以优选地对残基X3和X4进行选择,以使酯形成在膦基基团或膦酰基基团上。根据结构式(I)-(XI)的所述酯合适的例子包括:合适的单酯和二酯,所述酯优选的例子包括:烷基酯(例如十六烷基酯、十八烷基酯等);芳烷基酯(例如苄基酯、苯乙基酯、二苯甲基酯、三苯甲基酯等);芳基酯(例如苯基酯、甲苯基酯、萘基酯等);芳酰基烷基酯(例如苯乙酰基酯等);和甲硅烷基酯(例如三烷基卤甲硅烷基酯、二烷基二卤甲硅烷基酯、烷基三卤甲硅烷基酯、二烷基芳基卤甲硅烷基酯、三烷氧基卤甲硅烷基酯、二烷基芳烷基卤甲硅烷基酯、二烷氧基二卤甲硅烷基酯、三烷氧基卤甲硅烷基酯等)等。
在上述酯中,烷和/或芳烃部分可以任选地包含至少一个合适的取代基,如卤素、烷氧基、羟基、硝基等。
根据结构式(I)-(XI),根据本发明使用的化合物可以以其质子化形式存在,如有机或无机酸的铵盐,所述酸例如是盐酸、氢溴酸、硫酸、硝酸、甲磺酸、对-甲苯磺酸、乙酸、乳酸、马来酸、富马酸、草酸、酒石酸、苯甲酸等。
根据结构式(I)-(XI),根据本发明使用的化合物,例如允许基团R1、R2、R3、R4、X1、X2、X3、X4或A包含双键,或者是手性的,存在立体异构体。根据本发明,所述化合物的用途包括所有立体异构体,不仅包括纯物质,而且包括混合物。
这些有机磷化合物特别适合治疗和预防由病毒、细菌、单细胞和多细胞寄生虫以及真菌引起的人和动物的感染。
这些化合物对单细胞寄生虫(原生动物),尤其是对诱发疟疾和昏睡病、诱发查加斯病、弓形体病、阿米巴痢疾、利什曼病、毛滴虫病、间质性浆细胞性肺炎、小袋虫病、隐孢子虫病、肉孢子虫病、棘阿米巴病(acanthamoebosis)、耐格里原虫病、球虫病、贾第虫病和兰氏鞭毛虫病的生物体有活性。
因此,这些化合物尤其适于预防疟疾和昏睡病、以及查加斯病、弓形体病、阿米巴痢疾、利什曼病、毛滴虫病、间质性浆细胞性肺炎、小袋虫病、隐孢子虫病、肉孢子虫病、棘阿米巴病、耐格里原虫病、球虫病、贾第虫病和兰氏鞭毛虫病。
本发明的活性物质特别适于抵御以下细菌:
丙酸杆菌科细菌,尤其是丙酸菌属,尤其是疮疱丙酸杆菌,放线菌科细菌,尤其是放线菌属,棒杆菌属细菌,尤其是白喉棒杆菌和假结核棒杆菌,分支杆菌科细菌,分支杆菌属细菌,尤其是麻风分支杆菌、结核分支杆菌、牛分支杆菌和鸟分支杆菌,衣原体科细菌,尤其是砂眼衣原体和鹦鹉热衣原体,利斯特氏菌属细菌,尤其是单核细胞增生利斯特氏菌,猪红斑丹毒丝菌细菌,梭菌属细菌,耶尔森氏菌属细菌,鼠疫耶尔森氏菌、假结核耶尔森氏菌、小肠结肠炎耶尔森氏菌和鲁氏耶尔森氏菌,枝原体科细菌,枝原体属和脲枝原体属细菌,尤其是肺炎枝原体,布鲁氏菌属细菌,博德特氏菌属细菌,奈瑟氏球菌科细菌,尤其是奈瑟氏球菌属和莫拉氏菌属细菌,尤其是脑膜炎奈瑟氏球菌、淋病奈瑟氏球菌和牛莫拉氏菌,弧菌科细菌,尤其是弧菌属、气单胞菌属、邻单胞菌属和发光杆菌属细菌,尤其是霍乱弧菌、鳗利斯顿氏菌和杀鲑气单胞菌,弯曲杆菌属细菌,尤其是空肠弯曲杆菌空肠亚种、大肠弯曲杆菌和胚胎弯曲杆菌,螺杆菌属细菌,尤其是幽门螺杆菌,螺旋体科和钩端螺旋体科细菌,尤其是密螺旋体属、疏螺旋体属和钩端螺旋体属细菌,尤其是布氏疏螺旋体菌,放线杆菌属细菌,军团菌科细菌,军团菌属细菌,立克次氏体科和巴尔通氏体科细菌,诺卡氏菌属和红球菌属细菌,嗜皮菌属细菌,假单胞菌科细菌,尤其是假单胞菌属和黄单胞菌属细菌,肠杆菌科细菌,尤其是埃希氏菌属、克雷伯氏菌属、变形菌属、普罗威登斯菌属、沙门氏菌属、沙雷氏菌属和志贺氏菌属细菌,巴斯德氏菌科细菌,尤其是嗜血菌属,微球菌科细菌,尤其是微球菌属和葡萄球菌属细菌,链球菌科细菌,尤其是链球菌属和肠球菌属细菌,芽孢杆菌科细菌,尤其是芽孢杆菌属和梭菌属细菌。
因此,有机磷化合物及其衍生物适于治疗白喉、寻常痤疮、利斯特菌病,动物的猪丹毒,人和动物的气性坏疽,人和动物的恶性水肿,人和动物的结核,人和动物的麻疯以及进一步的分支杆菌病,动物的类结核、鼠疫,人和动物的肠系膜淋巴结炎和假结核病、霍乱、军团病,人和动物的疏螺旋体病,人和动物的钩端螺旋体病、梅毒,人和动物的弯曲杆菌属小肠炎感染,动物的莫拉菌属角膜结膜炎和浆膜炎,人和动物的布氏菌病,人和动物的炭疽,人和动物的放线菌病、链丝菌病,动物的鹦鹉热/鸟疫、Q热和埃利希菌病。
这些化合物还对根除胃肠道溃疡中的螺杆菌有效。
这些化合物也可以与其它抗生素组合使用治疗上述疾病。异烟肼、利福平、乙胺丁醇、吡嗪酰胺、链霉素、丙硫异烟胺和氨苯砜特别适合与其他抗感染药组合制剂用于治疗结核。
根据本发明的活性试剂还可以另外用于特别是下列病毒的感染:细小病毒:细小病毒、依赖病毒、浓核病毒;腺病毒科:腺病毒、mastadeno病毒、禽腺病毒;乳多空病毒:乳多空病毒病毒,特别是乳头瘤病毒(所谓的瘤病毒)、多瘤病毒,特别是JC病毒、BK病毒,以及miopapova病毒;疱疹病毒:所有疱疹病毒,特别是单纯疱疹病毒、varizella-zoster病毒、人巨细胞病毒、Epstein-Barr病毒、所有人疱疹病毒病毒、人疱疹病毒6、人疱疹病毒7、人疱疹病毒8;痘病毒:痘病毒、正痘病毒、副痘病毒、软疣触染性病毒、禽痘病毒、山羊痘病毒、野兔痘病毒;所有主要嗜肝病毒、肝炎病毒:甲型肝炎病毒、乙型肝炎B病毒、丙型肝炎病毒、丁型肝炎病毒、戊型肝炎病毒、己型肝炎病毒、庚型肝炎病毒;嗜肝DNA病毒:所有肝炎病毒、乙型肝炎病毒、丁型肝炎病毒;小RNA病毒:微小RNA病毒、所有肠道病毒、所有脊髓灰质炎病毒、所有柯萨奇病毒、所有艾可病毒、所有鼻病毒、甲型肝炎病毒、口疮病毒;嗜钙病毒:戊型肝炎病毒;呼肠病毒:呼肠病毒、环状病毒、轮状病毒;披膜病毒科:披膜病毒、甲病毒、锈红病毒、鼠疫病毒、风疹病毒;黄病毒科:黄病毒、FSME病毒、丙型肝炎病毒;正粘病毒科:所有流感病毒;副粘病毒科:副粘病毒、麻疹病毒、肺病毒、风疹病毒、流行性腮腺炎病毒;棒状病毒科:棒状病毒、狂犬病病毒、狂犬病病毒、粘血管口腔炎病毒;冠形病毒科:冠形病毒;布尼奥罗病毒科:布尼奥罗病毒、纳伊罗病毒、白蛉病毒、乌库病毒、汉坦病毒;沙粒病毒:沙粒病毒,淋巴细胞脉络丛脑膜炎病毒;逆转录病毒:逆转录病毒、所有HTL病毒、人T细胞白血病病毒、致癌RNA病毒、spuma病毒、慢病毒、所有HI病毒;丝状嗜菌体:Marburg和Ebola病毒;慢病毒感染,朊病毒;肿瘤病毒,白血病病毒。
因此,根据本发明的有机磷化合物适于抗下列病毒感染:
消除乳头瘤病毒以防止肿瘤,特别是在人的由乳头瘤病毒引起的生殖器官肿瘤,消除JC病毒和BK病毒,消除疱疹病毒,消除人疱疹病毒8以治疗卡波济氏肉瘤,在移植前消除巨细胞病毒,在移植前消除Eppstein-Barr病毒并预防与Eppstein-Barr病毒有关的肿瘤,消除肝炎病毒以治疗慢性肝疾病并预防肝脏的肿瘤和肝硬化,消除心肌病患者的柯萨奇病毒,消除糖尿病患者的柯萨奇病毒,消除人和动物免疫缺损病毒,治疗AIDS患者的二次感染,治疗呼吸道病毒性感染(喉炎,增生,鼻炎,咽炎,支气管炎,肺炎)、感觉器官病毒性感染(角膜结膜炎)、神经系统的病毒性感染(脊髓炎,脑膜炎,脑炎,亚急性硬化性全脑炎SSPE,进行性多病灶脑白质病,淋巴细胞脉络丛脑膜炎)、胃肠道(口腔炎,龈口炎,食管炎,胃炎,肠胃炎,腹泻引起的疾病)、肝胆膀胱系统病毒性感染(肝炎,胆管炎,肝细胞癌)、淋巴组织病毒性感染(单核细胞病,淋巴腺炎),造血系统病毒性感染、性器官病毒性感染(流行性腮腺炎睾丸炎)、皮肤病毒性感染(疣,皮炎,唇疱疹,热蠕动波,带状疱疹,带状疱疹(shingles))、粘膜病毒性感染(乳头瘤,结膜乳头瘤,增生,发育不良)、治疗心脏/血管系统病毒性感染(动脉炎,心肌炎,心内膜炎,心包炎)、肾/尿道系统病毒性感染,性器官病毒性感染(肛生殖索损伤,疣,生殖器疣,急性湿疣,发育不良,乳头瘤,子宫颈发育异常,湿疣,疣状表皮发育不良)、运动器官病毒性感染(肌炎,肌痛),治疗裂蹄动物的足和口腔疾病、科罗拉多蜱热、登革热、出血热、治疗夏初脑膜脑炎(FSME)及黄热病。
所描述的化合物,即式(I)-(XI)的有机磷化合物及其在膦基团上的酯和酰胺以及它们的盐对单细胞和多细胞寄生虫显示出强的细胞毒活性,尤其是对诱发疟疾和昏睡病的微生物。因此根据本发明所用的化合物有助于治疗由病毒、细菌、寄生虫和真菌引起的人和动物的感染疾病。这些化合物也适合于预防由病毒、细菌、寄生虫和真菌引起的疾病,特别是适用于防治疟疾和昏睡病。
根据本发明所用的有机磷化合物,通常包括为此目的的药学可接受的盐、酰胺、酯和酯的盐或给药后以代谢物或降解产物给出本发明的化合物的化合物(也称为“前药”),它们可以以与已知的具有抗感染作用的药剂类似的方式(与无毒、药学可接受的赋形剂混合)配方以给药。
这些化合物的药学可接受的盐包括本发明式(I)-(XI)化合物的质子化形式所形成的有机酸或无机酸的铵盐,例如盐酸、硫酸、柠檬酸、马来酸、富马酸、酒石酸、对甲苯磺酸的铵盐。
药学特别适合的盐还可以是通过适当地选择X3和X4而形成的盐,如钠盐、钾盐、钙盐、铵盐、乙醇胺盐、三乙胺盐、二环己胺盐和氨基酸的盐,例如精氨酸盐、天冬氨酸盐、谷氨酸盐。
使用测试系统确定物质的活性。该系统基于体外测定对细菌、寄生虫、真菌或植物生长的抑制。对本领域技术人员已知的方法可部分地用于此目的。
例如,通过测定对血液培养物中疟疾寄生虫生长的抑制来确定抗疟疾活性。抗菌活性根据对细菌在营养培养基和液体培养基上的生长的抑制而确定。抗病毒活性根据病毒元素在细胞培养基上的形成来确定。抗真菌活性根据对真菌在营养培养基和液体培养基上生长的抑制而确定。
一些要研究的微生物只能在动物模型中研究。在这种情况中,将使用合适的模型。
在体外测量系统中显示活性的物质然后进一步在体内模型中研究。在合适的动物模型中进一步评价抗寄生虫、抗病毒、杀真菌或抗菌活性。
除草活性的筛选通过海藻体系和在标准条件下植物的异戊二烯释放来确定。
具有药学活性的药剂可以制成单元剂量的药物制剂。这意味着制剂可以是单独组份的形式,例如片剂、包衣片剂、胶囊剂、丸剂、栓剂和安瓿剂,其活性物质的含量等于单独剂量的一部分或几倍。剂量单元可以含有单独剂量的1、2、3或4倍,或者单独剂量的1/2、1/3或1/4。单独剂量优选含有一次给药量的活性物质,通常为每日剂量的全部、一半、三分之一或四分之一。
无毒、惰性的药学适合的赋形剂指固体、半固体或液体稀释剂、填料和各种配方助剂。
优选的药物制剂是片剂、包衣片剂、胶囊剂、丸剂、颗粒剂、栓剂、溶液剂、混悬剂和乳剂、糊剂、软膏剂、凝胶、乳膏、洗剂、散剂和喷雾剂。片剂、包衣片剂、胶囊剂、丸剂和颗粒剂可以含有活性物质和常规赋形剂,例如(a)填料和增量剂,例如淀粉、乳糖、蔗糖、葡萄糖、甘露糖醇和二氧化硅,(b)粘合剂,例如羧甲基纤维素、藻酸盐、明胶、聚乙烯基吡咯烷酮,(c)保湿剂,例如甘油,(d)悬浮剂,例如琼脂、碳酸钙和碳酸钠,(e)溶出阻滞剂,如石蜡,和(f)吸收促进剂,如季铵化合物,(g)湿润剂,如鲸蜡醇、甘油单硬脂酸酯,(h)吸附剂,如高岭土和膨润土,和(i)润滑剂,如滑石粉、硬脂酸钙和硬脂酸镁和固体聚乙二醇,或者以上(a)到(i)中所描述的物质的混合物。
片剂、包衣片剂、胶囊剂、丸剂和颗粒剂可以具有常规包衣和壳,所述包衣和壳任选地含有遮光剂,也可以这样构成以使其延迟释放或优先在肠道的特定部位释放活性物质,其中可以使用例如聚合物或蜡作为基质。
活性物质任选地与一种或多种上述赋形剂,也可以以微胶囊的形式存在。
栓剂除活性物质之外还可以含有常规水溶性或水不溶性赋形剂,例如聚乙二醇,脂肪,例如可可脂和高级酯(例如C14醇和C16脂肪酸的酯),或这些物质的混合物。
除活性物质之外,软膏剂、糊剂、乳膏和凝胶还可以含有常规赋形剂,例如动物和植物脂肪、蜡、石蜡、淀粉、黄蓍胶、纤维素衍生物、聚乙二醇、硅氧烷、膨润土、二氧化硅、滑石粉和氧化锌或这些物质的混合物。
散剂和喷雾剂除活性物质之外还可以含有常规赋形剂,如乳糖、滑石粉、二氧化硅、氢氧化铝、硅酸钙和聚酰胺粉末或这些物质的混合物。喷雾剂还可以另外含有常规推进剂,如含氯氟烃。
溶液剂和乳剂除活性物质之外还可以含有常规赋形剂,如溶剂、增溶剂和乳化剂,例如水、乙醇、异丙醇、碳酸乙酯、乙酸乙酯、苄醇、苯甲酸苄酯、丙二醇、1,3-丁二醇、二甲基甲酰胺、油,尤其是棉籽油、花生油、玉米油、橄榄油、蓖麻籽油和芝麻油,甘油、环亚甲基甘油醚、四氢糠醇、聚乙二醇和脱水山梨糖醇脂肪酸酯,或这些物质的混合物。
对于非肠胃给药的溶液剂或乳剂也可以以无菌、等渗形式存在。
混悬剂除活性物质之外可以含有常规赋形剂,如液体稀释剂,例如水、乙醇、丙二醇,悬浮剂,例如乙氧基化异十八烷醇、聚氧乙烯山梨糖醇和脱水山梨醇酯、微晶纤维素、偏氢氧化铝、膨润土、琼脂和黄蓍胶,或这些物质的混合物。
上述制剂还可以含有着色剂、防腐剂和改善口味和气味的添加剂,例如薄荷油和桉树油,和甜味剂,例如糖精。
在上述药物制剂中,通式(I)-(XI)的活性物质的浓度优选为约全部混合物的O.1-99.5重量%,优选占全部混合物的0.5-95重量%。
除去通式(I)-(XI)的活性物质之外,药物制剂还可以含有其它药学活性物质。
这些化合物可以与此前已描述的具有抗菌、抗病毒、抗霉菌和抗寄生虫性质的物质一起使用。这些物质特别包括在治疗中已经有所应用或者仍在被使用的化合物。列于Red List或Simon/Stille,临床和实践中的抗生素治疗(Antibiokia-Therapie in Klinik und Praxis),第9版,1998,SchatauerVerlag,或者在英特网上http://www.customs.treasgov/imp-exp/rulings/harmoniz/hrm129.html的物质是特别适于此目的的。具体地说,所述衍生物可以特别地与以下药物一起存在:青霉素类,苄基青霉素(青霉素G)、苯氧基青霉素、异恶唑基青霉素、氨基青霉素、氨苄青霉素、阿莫西林、巴氨西林、羧基青霉素、替卡西林、它莫西林、酰氨基青霉素、阿洛西林、美洛西林、哌拉西林、阿帕西林、美西林,头孢菌素类,头孢唑啉类,头孢呋辛类,头孢西丁类,头孢西丁、头孢替坦、头孢美唑、拉氧头孢、氟氧头孢、头孢噻肟类、cefazidime,头孢他啶类,头孢他啶、头孢比隆、头孢吡肟,常规头孢菌素类,头孢黄啶、头孢哌酮、头孢氨苄类的口服头孢菌素类,氯拉卡比、头孢罗齐,新的广谱口服头孢菌素类,头孢克肟、头孢泊肟丙酯、头孢呋肟酯、头孢他美、头孢替安己酯、头孢地平、头孢布坦,其它β-内酰胺抗生素类,carbapenem、亚胺培南/西司他丁、美罗倍南、比阿培南、氨曲南,β-内酰胺酶抑制剂,棒酸/阿莫西林、棒酸/替卡西林、舒巴坦/阿莫西林、唑巴坦/哌拉西林,四环素类,四环素、硝酸吡甲四环素、多西环素、米诺环素、氯霉素、氨基苷类,庆大霉素、妥布霉素、奈替米星、丁胺卡那霉素、壮观霉素,大环内酯类,红霉素、克拉霉素、罗红霉素、阿齐诺霉素、地红霉素、螺旋霉素、交沙霉素,林可酰胺类,克林霉素、夫西地酸,糖肽抗生素类,万古霉素、太可菌素,原始霉素衍生物类,磷霉素,抗菌叶酸拮抗剂,磺胺类,co-trimoxazole、甲氧苄啶,其它二氨基嘧啶磺胺组合,硝基呋喃、硝基呋喃妥英、硝呋醛,回旋酶抑制剂(喹诺酮类),诺氟沙星、环丙沙星、氧氟沙星、西洛沙星、依诺沙星、氟罗沙星、培氟沙星、洛美沙星,Bay Y3118,硝基咪唑类,抗分支杆菌试剂,异烟肼、利福平、利福布丁、吡嗪酰胺、链霉素、缠霉素、丙硫异烟胺、苯环丝氨酸、达普宋、氯法齐明,局部用抗生素,杆菌肽、短杆菌素、多粘菌素、新霉素、卡那霉素、巴龙霉素、百多邦,抗病毒试剂,阿昔洛韦、更昔洛韦、叠氮胸苷、地达诺新、扎西他宾、噻胞苷、司他夫定、利巴韦林、碘苷、曲氟尿苷、膦卡萘替、金刚烷胺、干扰素类,tibol衍生物,蛋白酶抑制剂,抗霉菌素,聚烯类,两性霉素B、制霉素、那他霉素,唑系,脓毒病治疗的唑系,咪康唑、酮康唑、依他康唑、氟康唑、UK-109496,局部应用的唑系,克霉唑、益康唑、异康唑、奥昔康唑、联苯苄唑、氟胞嘧啶、灰黄霉素、环吡酮胺、托萘酯、纳夫替芬、特比萘芬、阿莫罗芬,蒽醌类,桦木酸、半蒽醌类,氧杂蒽酮类,萘醌类,芳氨基醇类,奎宁,喹宁丁类,甲氟喹、氯氟菲醇、氯奎、阿莫地喹、吖啶、苯并萘啶、麦帕克林、萘洛啶、胺苯砜,磺胺类,磺胺多辛、磺胺林、甲氧苄啶、氯胍、氯丙胍,二氨基嘧啶类,乙胺嘧啶、伯氨喹,氨基喹啉类,WR238,605、四环素、多西环素、克林霉素、诺氟沙星、环丙沙星、氧氟沙星、青蒿素、二氢青蒿素、10b蒿甲醚、蒿甲醚、atresunate、阿托夸酮、苏拉明、美拉胂醇、硝呋莫司、葡萄糖酸锑钠、戊双脒、两性霉素B、甲硝唑、氯碘喹啉、甲苯咪唑、氯硝柳胺、吡喹酮、噻嘧啶、噻唑咪唑、二乙碳酰嗪、伊维菌素、硫二氯酚、羟氨喹、敌百虫、驱蛔灵、双羟萘酸盐。
此外,有机磷化合物可以与磺胺、磺胺多辛、青蒿素、阿托夸酮、奎宁、氯奎、羟氯奎、甲氟喹、氯氟菲醇、乙胺嘧啶、armesin、四环素、多西环素、氯胍、甲硝唑、吡喹酮、氯硝柳胺、甲苯咪唑、噻嘧啶、噻唑咪唑、乙胺嗪、哌嗪、扑蛲灵、敌百虫、羟氨喹、硫氯酚或苏拉明或两种或多种这些物质组合存在于药物制剂中。
使用已知的方法用常规方式制备上述药物制剂,例如把赋形剂和活性物质混合。
上述制剂可以经口服、直肠、非肠胃(静脉内、肌内、皮下)、脑池内、阴道内、腹膜内、局部使用(散剂、软膏剂、滴剂)给药于人或动物,并用于腔、体腔内感染的治疗。可以考虑的合适的制剂是注射液、口服治疗的溶液剂和混悬剂、凝胶、浸剂、乳剂、软膏剂或滴剂。局部治疗可以使用眼科和皮肤科配方,银和其它盐,滴耳剂、眼用软膏剂,散剂或溶液剂。还可以通过饲料或饮用水将适当的配方给药于动物。对人和动物可以使用凝胶、粉末状配方、散剂、片剂、控释片剂、预混合剂、浓缩物、颗粒剂、丸剂、片剂、boli、胶囊剂、气雾剂、喷剂、吸入配方。根据本发明所用的化合物还可以将其它载体加入其中,例如塑料(用于局部治疗的塑料链),胶原或骨粘固粉。
已证实向人和动物给药通式(I)-(XI)的活性物质的总量为每24小时0.05-600毫克/千克体重,优选为0.5-200毫克/千克体重是有利的,为达到所希望的结果,任选地分两次或多次给药。每次单独使用的剂量优选含活性物质约1-200毫克/千克体重,优选1-60毫克/千克体重。但是根据进行治疗的患者的特点和体重,疾病的特性和严重程度,制剂的特点和药物制剂的给药途径以及给药周期,可能需要偏离上述剂量。
在一些情况中,活性物质的用量少于上述的剂量就足够了,而在另外一些情况中则必需使用多于上述的量的活性物质。本领域的技术人员对于特定的情况将根据自己的技能确定最优的剂量与给药途径。根据本发明所用的化合物可以以常规浓度和制剂形式与饲料、饲料制剂或饮用水一起给药动物。
根据本发明所用的化合物还可很好地用作植物的杀细菌剂、杀真菌剂和除草剂。
Claims (13)
1、通式(I)的有机磷化合物及其药物学上可接受的盐、酯和酰胺以及酯的盐在预防和治疗由于病毒、细菌、真菌或寄生虫引起的人和动物的感染、以及在植物中作为植物的抗真菌剂、抗菌剂和除草剂的应用:其中X是磷原子或硫原子,A是C2-9亚烷基链,其可含有取代基,所述取代基是相同或不同的,它们
选自于以下组中:氢、羟基、卤素、氨基和氧代基团、C1-26烷基、
C1-26烷氧基、C1-26烷氧基-C1-26烷基或C3-8环烷基-(C0-9)烷基,
其中C1-26烷基和C1-26烷氧基各自是支链或直链的、饱和的或者具有
一个或多个双键的不饱和基团并且可被羟基、氨基、卤素和氧代基团
取代,C3-8环烷基-(C0-9)烷基中的C3-8环烷基和C0-9烷基可包含
一个或多个双键并且该环烷基的一个或两个碳原子可被氮、氧或硫置
换,并且其中该环烷基和该烷基均可被羟基、卤素、氨基、氧代基团、
支链或直链的C1-9烷基和C2-9链烯基取代,其中C1-9烷基和C2-9链
烯基可被氢、羟基、氨基、卤素和氧代基团取代,R1和R2相同或不同,并选自于以下组中:氢、取代和未取代的C1-9烷基、
取代和未取代的羟基-C1-9烷基、取代或未取代的C1-9链烯基、取代
或未取代的C1-9炔基、取代或未取代的芳基、取代或未取代的酰基、
取代和未取代的环烷基、取代和未取代的芳烷基、取代或未取代的杂
环基、卤素、OX1和OX2,其中X1和X2相同或不同,并选自于以下组中:氢、取代和未取代的C1-9烷基、
取代和未取代的羟基-C1-9烷基、取代或未取代的C1-9链烯基、取代
或未取代的C1-9炔基、取代或未取代的芳基、取代或未取代的酰基、
取代和未取代的环烷基、取代和未取代的芳烷基、取代或未取代的杂
环基,R3和R4相同或不同,并选自于以下组中:取代和未取代的C1-26烷基、羟
基-C1-26烷基、取代或未取代的芳基、取代或未取代的酰基、取代和
未取代的芳烷基、取代或未取代的C1-26链烯基、取代或未取代的
C1-26炔基、取代和未取代的环烷基、取代或未取代的杂环基、卤素、OX3
和OX4,其中X3和X4相同或不同,并选自于以下组中:氢、取代和未取代的C1-26烷基、
取代或未取代的羟基-C1-26烷基、取代或未取代的芳基、取代和未取
代的芳烷基、取代或未取代的C1-26链烯基、取代或未取代的C1-26炔
基、取代和未取代的环烷基、取代或未取代的杂环基、甲硅烷基、有
机碱和无机碱的阳离子,尤其是周期表中I、II、III主族的金属、铵、
取代的铵以及由乙二胺或氨基酸衍生的铵化合物。
2、如权利要求1所述的应用,其特征在于,A是带有取代基的C3-5烷基,所述取代基选自于以下组中:氢、羟基、卤素、氨基和氧代基团、C1-26烷基、C1-26烷氧基、C1-26烷氧基-C1-26烷基或C3-8环烷基-(C0-9)烷基,其中C1-26烷基和C1-26烷氧基各自是支链或直链的、饱和的或者具有一个或多个双键的不饱和基团并且可被羟基、氨基、卤素和氧代基团取代,C3-8环烷基-(C0-9)烷基中的C3-8环烷基和C0-9烷基可包含一个或多个双键并且该环烷基的一个或两个碳原子可被氮、氧或硫置换,并且该环烷基和该烷基均可被羟基、卤素、氨基、氧代基团、支链或直链的C1-9烷基和C2-9链烯基取代,其中C1-9烷基和C2-9链烯基可被氢、羟基、氨基、卤素和氧代基团取代
3、如权利要求1或2所述的应用,其特征在于,有机磷化合物相应于式(II):其中X、R1、R3、R4如权利要求1所定义,而且R1的相邻于杂原子的碳原子优选被羟基取代;
6、如权利要求1-5之一所述的应用,其是用于治疗由细菌、病毒、真菌或者单细胞或多细胞寄生虫导致的感染。
7、如权利要求6所述的应用,其是用于治疗由选自于以下组中的细菌导致的感染:丙酸杆菌科细菌,尤其是丙酸菌属,尤其是疮疱丙酸杆菌,放线菌科细菌,尤其是放线菌属,棒杆菌属细菌,尤其是白喉棒杆菌和假结核棒杆菌,分支杆菌科细菌,分支杆菌属细菌,尤其是麻风分支杆菌、结核分支杆菌、牛分支杆菌和鸟分支杆菌,衣原体科细菌,尤其是砂眼衣原体和鹦鹉热衣原体,利斯特氏菌属细菌,尤其是单核细胞增生利斯特氏菌,猪红斑丹毒丝菌细菌,梭菌属细菌,耶尔森氏菌属细菌,鼠疫耶尔森氏菌、假结核耶尔森氏菌、小肠结肠炎耶尔森氏菌和鲁氏耶尔森氏菌,枝原体科细菌,枝原体属和脲枝原体属细菌,尤其是肺炎枝原体,布鲁氏菌属细菌,博德特氏菌属细菌,奈瑟氏球菌科细菌,尤其是奈瑟氏球菌属和莫拉氏菌属细菌,尤其是脑膜炎奈瑟氏球菌、淋病奈瑟氏球菌和牛莫拉氏菌,弧菌科细菌,尤其是弧菌属、气单胞菌属、邻单胞菌属和发光杆菌属细菌,尤其是霍乱弧菌、鳗利斯顿氏菌和杀鲑气单胞菌,弯曲杆菌属细菌,尤其是空肠弯曲杆菌空肠亚种、大肠弯曲杆菌和胚胎弯曲杆菌,螺杆菌属细菌,尤其是幽门螺杆菌,螺旋体科和钩端螺旋体科细菌,尤其是密螺旋体属、疏螺旋体属和钩端螺旋体属细菌,尤其是布氏疏螺旋体菌,放线杆菌属细菌,军团菌科细菌,军团菌属细菌,立克次氏体科和巴尔通氏体科细菌,诺卡氏菌属和红球菌属细菌,嗜皮菌属细菌,假单胞菌科细菌,尤其是假单胞菌属和黄单胞菌属细菌,肠杆菌科细菌,尤其是埃希氏菌属、克雷伯氏菌属、变形菌属、普罗威登斯菌属、沙门氏菌属、沙雷氏菌属和志贺氏菌属细菌,巴斯德氏菌科细菌,尤其是嗜血菌属,微球菌科细菌,尤其是微球菌属和葡萄球菌属细菌,链球菌科细菌,尤其是链球菌属和肠球菌属细菌,芽孢杆菌科细菌,尤其是芽孢杆菌属和梭菌属细菌,以及根除胃肠道溃疡中的螺杆菌。
8、如权利要求6所述的应用,其治疗由选自于以下组中的病毒导致的感染:细小病毒:细小病毒、依赖病毒、浓核病毒;腺病毒科:腺病毒、mastadeno病毒、禽腺病毒;乳多空病毒:乳多空病毒病毒,特别是乳头瘤病毒(所谓的瘤病毒)、多瘤病毒,特别是JC病毒、BK病毒,以及miopapova病毒;疱疹病毒:所有疱疹病毒,特别是单纯疱疹病毒、varizella-zoster病毒、人巨细胞病毒、Epstein-Barr病毒、所有人疱疹病毒病毒、人疱疹病毒6、人疱疹病毒7、人疱疹病毒8;痘病毒:痘病毒、正痘病毒、副痘病毒、软疣触染性病毒、禽痘病毒、山羊痘病毒、野兔痘病毒;所有主要嗜肝病毒、肝炎病毒:甲型肝炎病毒、乙型肝炎B病毒、丙型肝炎病毒、丁型肝炎病毒、戊型肝炎病毒、己型肝炎病毒、庚型肝炎病毒;嗜肝DNA病毒:所有肝炎病毒、乙型肝炎病毒、丁型肝炎病毒;小RNA病毒:微小RNA病毒、所有肠道病毒、所有脊髓灰质炎病毒、所有柯萨奇病毒、所有艾可病毒、所有鼻病毒、甲型肝炎病毒、口疮病毒;嗜钙病毒:戊型肝炎病毒;呼肠病毒:呼肠病毒、环状病毒、轮状病毒;披膜病毒科:披膜病毒、甲病毒、锈红病毒、鼠疫病毒、风疹病毒;黄病毒科:黄病毒、FSME病毒、丙型肝炎病毒;正粘病毒科:所有流感病毒;副粘病毒科:副粘病毒、麻疹病毒、肺病毒、风疹病毒、流行性腮腺炎病毒;棒状病毒科:棒状病毒、狂犬病病毒、狂犬病病毒、粘血管口腔炎病毒;冠形病毒科:冠形病毒;布尼奥罗病毒科:布尼奥罗病毒、纳伊罗病毒、白蛉病毒、乌库病毒、汉坦病毒;沙粒病毒:沙粒病毒,淋巴细胞脉络丛脑膜炎病毒;逆转录病毒:逆转录病毒、所有HTL病毒、人T细胞白血病病毒、致癌RNA病毒、spuma病毒、慢病毒、所有HI病毒;丝状嗜菌体:Marburg和Ebola病毒;慢病毒感染,朊病毒;肿瘤病毒,白血病病毒。
9、如权利要求6所述的应用,其是用于治疗由单细胞寄生虫导致的感染,即、疟疾和昏睡病、以及查加斯病、弓形体病、阿米巴痢疾、利什曼病、毛滴虫病、间质性浆细胞性肺炎、小袋虫病、隐孢子虫病、肉孢子虫病、棘阿米巴病、耐格里原虫病、球虫病、贾第虫病和兰氏鞭毛虫病。
10、如权利要求1-9之一所述的应用,其是以药物制剂的形式进行,其中该药物制剂包含活性量的至少一种如权利要求1-5之一所述的有机磷化合物以及药物学上可接受的载体。
11、如权利要求10所述的应用,其特征在于,药物制剂包含至少一种其他药物活性物质。
12、如权利要求10或11所述的应用,其特征在于,药物制剂包含一种或多种选自于以下组中的成分:磺胺、磺胺多辛、青蒿素、阿托夸酮、奎宁、氯奎、羟氯奎、甲氟喹、氯氟菲醇、乙胺嘧啶、armesin、四环素、多西环素、氯胍、甲硝唑、吡喹酮、氯硝柳胺、甲苯咪唑、噻嘧啶、噻唑咪唑、乙胺嗪、哌嗪、扑蛲灵、敌百虫、羟氨喹、硫氯酚或苏拉明。
13、如权利要求11或12所述的应用,其特征在于,药物制剂包含一种或多种选自于以下组中的成分:青霉素类,苄基青霉素(青霉素G)、苯氧基青霉素、异恶唑基青霉素、氨基青霉素、氨苄青霉素、阿莫西林、巴氨西林、羧基青霉素、替卡西林、它莫西林、酰氨基青霉素、阿洛西林、美洛西林、哌拉西林、阿帕西林、美西林,头孢菌素类,头孢唑啉类,头孢呋辛类,头孢西丁类,头孢西丁、头孢替坦、头孢美唑、拉氧头孢、氟氧头孢、头孢噻肟类、cefazidine,头孢他啶类,头孢他啶、头孢比隆、头孢吡肟,常规头孢菌素类,头孢黄啶、头孢哌酮、头孢氨苄类的口服头孢菌素类,氯拉卡比、头孢罗齐,新的广谱口服头孢菌素类,头孢克肟、头孢泊肟丙酯、头孢呋肟酯、头孢他美、头孢替安己酯、头孢地平、头孢布坦,其它β-内酰胺抗生素类,carbapenem、亚胺培南/西司他丁、美罗倍南、比阿培南、氨曲南,β-内酰胺酶抑制剂,棒酸/阿莫西林、棒酸/替卡西林、舒巴坦/阿莫西林、唑巴坦/哌拉西林,四环素类,四环素、硝酸吡甲四环素、多西环素、米诺环素、氯霉素、氨基苷类,庆大霉素、妥布霉素、奈替米星、丁胺卡那霉素、壮观霉素,大环内酯类,红霉素、克拉霉素、罗红霉素、阿齐诺霉素、地红霉素、螺旋霉素、交沙霉素,林可酰胺类,克林霉素、夫西地酸,糖肽抗生素类,万古霉素、太可菌素,原始霉素衍生物类,磷霉素,抗菌叶酸拮抗剂,磺胺类,co-trimoxazole、甲氧苄啶,其它二氨基嘧啶磺胺组合,硝基呋喃、硝基呋喃妥英、硝呋醛,回旋酶抑制剂(喹诺酮类),诺氟沙星、环丙沙星、氧氟沙星、西洛沙星、依诺沙星、氟罗沙星、培氟沙星、洛美沙星,Bay Y3118,硝基咪唑类,抗分支杆菌试剂,异烟肼、利福平、利福布丁、吡嗪酰胺、链霉素、缠霉素、丙硫异烟胺、苯环丝氨酸、达普宋、氯法齐明,局部用抗生素,杆菌肽、短杆菌素、多粘菌素、新霉素、卡那霉素、巴龙霉素、百多邦,抗病毒试剂,阿昔洛韦、更昔洛韦、叠氮胸苷、地达诺新、扎西他宾、噻胞苷、司他夫定、利巴韦林、碘苷、曲氟尿苷、膦卡萘替、金刚烷胺、干扰素类,tibol衍生物,蛋白酶抑制剂,抗霉菌素,聚烯类,两性霉素B、制霉素、那他霉素,唑系,脓毒病治疗的唑系,咪康唑、酮康唑、依他康唑、氟康唑、UK-109496,局部应用的唑系,克霉唑、益康唑、异康唑、奥昔康唑、联苯苄唑、氟胞嘧啶、灰黄霉素、环吡酮胺、托萘酯、纳夫替芬、特比萘芬、阿莫罗芬,蒽醌类,桦木酸、半蒽醌类,氧杂蒽酮类,萘醌类,芳氨基醇类,奎宁,喹宁丁类,甲氟喹、氯氟菲醇、氯奎、阿莫地喹、吖啶、苯并萘啶、麦帕克林、萘洛啶、胺苯砜,磺胺类,磺胺多辛、磺胺林、甲氧苄啶、氯胍、氯丙胍,二氨基嘧啶类,乙胺嘧啶、伯氨喹,氨基喹啉类,WR238,605、四环素、多西环素、克林霉素、诺氟沙星、环丙沙星、氧氟沙星、青蒿素、二氢青蒿素、10b蒿甲醚、蒿甲醚、atresunate、阿托夸酮、苏拉明、美拉胂醇、硝呋莫司、葡萄糖酸锑钠、戊双脒、两性霉素B、甲硝唑、氯碘喹啉、甲苯咪唑、氯硝柳胺、吡喹酮、噻嘧啶、噻唑咪唑、二乙碳酰嗪、伊维菌素、硫二氯酚、羟氨喹、敌百虫、驱蛔灵、双羟萘酸盐。
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DE19902924A DE19902924A1 (de) | 1999-01-26 | 1999-01-26 | Verwendung von phosphororganischen Verbindungen zur prophylaktischen und therapeutischen Behandlung von Infektionen |
DE19902924.5 | 1999-01-26 |
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CN1337881A true CN1337881A (zh) | 2002-02-27 |
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CN00803129A Pending CN1337881A (zh) | 1999-01-26 | 2000-01-25 | 有机磷化合物预防或治疗感染的应用 |
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EP (1) | EP1146880A2 (zh) |
JP (1) | JP2002535354A (zh) |
CN (1) | CN1337881A (zh) |
AU (1) | AU2439900A (zh) |
CA (1) | CA2360661A1 (zh) |
CZ (1) | CZ20012584A3 (zh) |
DE (1) | DE19902924A1 (zh) |
HU (1) | HUP0105310A3 (zh) |
IL (1) | IL144115A0 (zh) |
NO (1) | NO20013651L (zh) |
PL (1) | PL349910A1 (zh) |
SK (1) | SK10552001A3 (zh) |
TR (1) | TR200102151T2 (zh) |
WO (1) | WO2000044358A2 (zh) |
Cited By (2)
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CN104026151A (zh) * | 2014-06-19 | 2014-09-10 | 南京麦思德餐饮管理有限公司 | 一种紫花苜蓿浸种剂 |
CN105403221A (zh) * | 2015-10-27 | 2016-03-16 | 广东欧珀移动通信有限公司 | 一种导航路线的生成方法及移动终端 |
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US7842719B2 (en) * | 2002-10-31 | 2010-11-30 | Kemin Foods, L.C. | Use of endoperoxides for the treatment of infections caused by flaviviridae, including hepatitis C, bovine viral diarrhea and classical swine fever virus |
WO2004085448A2 (en) * | 2003-03-19 | 2004-10-07 | Genzyme Corporation | Unsaturated phosphinyl-phosphonate phosphate transport inhibitors |
JP2012521365A (ja) * | 2009-03-20 | 2012-09-13 | ユニバーシティー オブ アイオワ リサーチ ファウンデーション | 抗結核剤としてのプレニル化ビスホスホネート |
ES2970434T3 (es) | 2014-09-12 | 2024-05-28 | Union Therapeutics As | Uso antibacteriano de salicilanilidas halogenadas |
GB201509326D0 (en) | 2015-05-29 | 2015-07-15 | Antibio Tx Aps | Novel use |
US11419834B2 (en) | 2019-02-25 | 2022-08-23 | Rhode Island Hospital | Methods for treating diseases or infections caused by or associated with H. pylori using a halogenated salicylanilide |
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US3170944A (en) * | 1962-11-20 | 1965-02-23 | Stauffer Chemical Co | Haloacetonyl phosphonates and a method of preparing them |
US3372209A (en) * | 1964-08-24 | 1968-03-05 | Monsanto Co | Diphosphorus ester hydrocarbon diols |
BE687874A (zh) * | 1965-10-06 | 1967-04-06 | ||
US3532774A (en) * | 1966-09-29 | 1970-10-06 | Monsanto Co | Phosphinites,phosphine oxides and process for preparing |
JPS4861259A (zh) * | 1971-12-02 | 1973-08-28 | ||
US4254114A (en) * | 1979-01-02 | 1981-03-03 | The Proctor & Gamble Company | Control of pyrophosphate microorganisms with organophosphonates |
JPS5655394A (en) * | 1979-10-12 | 1981-05-15 | Otsuka Chem Co Ltd | 1,2-di alkoxycarbonylmethylamino ethylene-1,2-disulfonic acid phenyl ester derivative, its preparation, and herbicide containing said compound |
DE3208600A1 (de) * | 1982-03-10 | 1983-09-22 | Henkel KGaA, 4000 Düsseldorf | Amidinodiphosphonsaeuren |
CH664158A5 (fr) * | 1984-07-18 | 1988-02-15 | Symphar Sa | Derives propylidenediphosphonates-1,3 substitues en position 2, leur procede de preparation et compositions pharmaceutiques les contenant. |
US4820698A (en) * | 1985-11-04 | 1989-04-11 | The Procter & Gamble Company | Antimicrobial agents and process for their manufacture |
US5196409A (en) * | 1989-08-20 | 1993-03-23 | Yissum, Research Development Company Of The Hebrew University Of Jerusalem | Bisphosphonates, pharmaceutical compositions, and process for the treatment of irregularities in calcium metabolism |
DE4336099A1 (de) * | 1993-10-22 | 1995-04-27 | Boehringer Mannheim Gmbh | Neue 2.4-Diphosphonoglutarsäurederivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
WO1996016629A2 (en) * | 1994-11-18 | 1996-06-06 | Amira Inc | Phosphinic creatine compounds having antiviral activity |
DE19532235A1 (de) * | 1995-08-31 | 1997-03-06 | Keppler Bernhard K Priv Doz Dr | An Phosphonsäuren gekoppelte antibakteriell wirksame Verbindungen zur Therapie von Infektionen im Bereich des Knochens |
GB9613637D0 (en) * | 1996-06-28 | 1996-08-28 | Agrevo Uk Ltd | Fungicidal compositions |
EP0944635A4 (en) * | 1996-10-09 | 2000-07-05 | Elizanor Biopharmaceuticals In | THERAPEUTIC DIPHOSPHONATE COMPOUNDS |
-
1999
- 1999-01-26 DE DE19902924A patent/DE19902924A1/de not_active Ceased
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2000
- 2000-01-25 CN CN00803129A patent/CN1337881A/zh active Pending
- 2000-01-25 SK SK1055-2001A patent/SK10552001A3/sk unknown
- 2000-01-25 AU AU24399/00A patent/AU2439900A/en not_active Abandoned
- 2000-01-25 HU HU0105310A patent/HUP0105310A3/hu unknown
- 2000-01-25 TR TR2001/02151T patent/TR200102151T2/xx unknown
- 2000-01-25 WO PCT/EP2000/000542 patent/WO2000044358A2/de not_active Application Discontinuation
- 2000-01-25 CA CA002360661A patent/CA2360661A1/en not_active Abandoned
- 2000-01-25 CZ CZ20012584A patent/CZ20012584A3/cs unknown
- 2000-01-25 JP JP2000595662A patent/JP2002535354A/ja active Pending
- 2000-01-25 IL IL14411500A patent/IL144115A0/xx unknown
- 2000-01-25 PL PL00349910A patent/PL349910A1/xx not_active Application Discontinuation
- 2000-01-25 EP EP00902630A patent/EP1146880A2/de not_active Withdrawn
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104026151A (zh) * | 2014-06-19 | 2014-09-10 | 南京麦思德餐饮管理有限公司 | 一种紫花苜蓿浸种剂 |
CN105403221A (zh) * | 2015-10-27 | 2016-03-16 | 广东欧珀移动通信有限公司 | 一种导航路线的生成方法及移动终端 |
Also Published As
Publication number | Publication date |
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WO2000044358A3 (de) | 2001-03-15 |
EP1146880A2 (de) | 2001-10-24 |
PL349910A1 (en) | 2002-10-07 |
NO20013651L (no) | 2001-09-18 |
AU2439900A (en) | 2000-08-18 |
HUP0105310A2 (en) | 2002-06-29 |
CA2360661A1 (en) | 2000-08-03 |
WO2000044358A2 (de) | 2000-08-03 |
SK10552001A3 (sk) | 2001-12-03 |
DE19902924A1 (de) | 2000-08-03 |
TR200102151T2 (tr) | 2002-05-21 |
HUP0105310A3 (en) | 2002-08-28 |
NO20013651D0 (no) | 2001-07-25 |
CZ20012584A3 (cs) | 2002-01-16 |
JP2002535354A (ja) | 2002-10-22 |
IL144115A0 (en) | 2002-05-23 |
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