CN113260419A - 吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法 - Google Patents
吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法 Download PDFInfo
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- CN113260419A CN113260419A CN201980087234.5A CN201980087234A CN113260419A CN 113260419 A CN113260419 A CN 113260419A CN 201980087234 A CN201980087234 A CN 201980087234A CN 113260419 A CN113260419 A CN 113260419A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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Abstract
式I化合物、其组合物、其制备方法和其作为农药的用途。
Description
与相关申请的交叉引用
本申请要求2018年11月20日提交的U.S.临时申请No.62/769,850的优先权权益,其通过援引并入本文。
发明领域
本公开涉及式I或式II的吲唑基氰基乙基氨基化合物,包含该化合物的组合物,制备该化合物的方法,该化合物的用途和包括该化合物用于在动物中治疗和/或预防寄生物感染的方法。
任何前述申请以及其或在其申请过程期间引用的全部文献("申请引用文献")和在申请引用文献中引用或参考的全部文献,和本文引用或参考的全部文献("本文引用文献")和本文引用文献中引用或参考的全部文献,以及本文或通过援引并入本文的任何文献提及的任何产品的任何生产商指南、说明书、产品说明书和产品说明页,都通过援引并入本文,并且可以用于本发明的实践当中。
本申请中引用或指定任意文献并非承认该文献是本发明的现有技术。
发明背景
通过具有氰基乙基氨基的活性成分防治寄生物、特别是内寄生物已由各种专利或专利申请描述,包括国际专利公开Nos.WO 2004/024704(美国专利7,084,280)、WO 2005/044784、WO 2005/121075和WO 2006/043654以及EP 953565(美国专利6,239,077)和EP1445251,其全部通过援引并入本文。
此外,某些具有双环杂芳基组分的吲唑基氰基乙基氨基化合物是已知的。例如,芳基并吡咯-2-基-氰基乙基氨基化合物描述于PCT公开Nos.WO 2008/144275和WO2010/056999,通过援引将两者全部并入本文。然而,本发明化合物并未被特别描述。
发明概要
在一种实施方式中,本发明提供式I化合物:
和/或其药学上可接受的盐和/或其对映体。
在又一实施方式中,本发明提供式II化合物:
和/或其可接受的盐和/或其对映体。
在又一实施方式中,本发明提供农药的或杀寄生物组合物,包含式I化合物或式II化合物以及农药可接受的或杀寄生物可接受的载体。在某些实施方式中,所述组合物适于向动物口服给药。在其它实施方式中,所述组合物呈用于注射给药的形式。在其它实施方式中,所述组合物呈用于向动物局部给药的形式,包括泼浇剂或涂抹剂配制剂。
在又一实施方式中,本发明提供在哺乳动物中治疗和/或预防内寄生物感染的方法,其包括向有需要的动物给予有效量的式I或式II化合物或其药学上可接受的盐或者包含该化合物或盐的组合物。
在又一实施方式中,本发明提供式I或式II化合物或其药学上可接受的盐用于在动物中治疗或预防内寄生物感染的用途。本发明也提供式I或式II化合物或其盐制备药物的用途,所述药物用于在动物中治疗或预防内寄生物感染。
本发明的化合物、组合物、方法和用途对治疗动物包括哺乳动物、鸟和鱼是有效的。哺乳动物的实例包括但不限于人,牛,绵羊,山羊,美洲驼,羊驼,猪,马,驴,犬,猫和其它牲畜或家养哺乳动物。鸟类的实例包括火鸡,鸡,鸵鸟和其它牲畜或家养鸟类。式I和式II化合物保护反刍动物比如牛和绵羊对抗内寄生物的用途是特别有用的。
在一种实施方式中,本发明的方法和用途有效地对抗由选自下述的蠕虫引起的内寄生物感染:裸头绦虫属(Anaplocephaela(Anoplocephala)),钩口线虫属(Ancylostoma),Anecator,蛔虫属(Ascaris),布鲁属(Brugia),仰口线虫属(Bunostomum),毛细线虫属(Capillaria),夏伯特线虫属(Chabertia),古柏线虫属(Cooperia),盅口属(Cyathostomum),杯环属(Cylicocyclus),双冠属(Cylicodontophorus),杯冠属(Cylicostephanus),盆口属(Craterostomum),网尾属(Dictyocaulus),双瓣丝虫属(Dipetalonema),复孔属(Dipylidium),恶丝虫属(Dirofilaria),龙线虫属(Dracunculus),棘球属(Echinococcus),蛲虫属(Enterobius),吸虫属(Fasciola),类丝虫属(Filaroides),胃线虫属(Habronema),血矛线虫属(Haemonchus),后圆线虫属(Metastrongylus),蒙尼属(Moniezia),板口线虫属(Necator),细颈线虫属(Nematodirus),日圆线虫属(Nippostrongylus),结节线虫属(Oesophagostumum),盘尾属(Onchocerca),奥斯特线虫属(Ostertagia),尖尾线虫属(Oxyuris),副蛔虫属(Paracaris),血吸虫属(Schistosoma),圆线虫属(Strongylus),绦虫属(Taenia),弓蛔虫属(Toxocara),类圆线虫属(Strongyloides),弓蛔线虫属(Toxascaris),毛线虫属(Trichinella),鞭虫属(Trichuris),毛圆线虫属(Trichostrongylus),三齿线虫属(Triodontophorous),钩虫属(Uncinaria),吴策属(Wuchereria),及其组合。
在又一实施方式中,本发明的方法和用途有效地对抗由选自下述的蠕虫引起的内寄生物感染:捻转血矛线虫(Haemonchus contortus),环纹奥斯特线虫(Ostertagiacircumcincta),艾氏毛圆线虫(Trichostrongylus axei),透明毛圆线虫(Trichostrongylus colubriformis),短古柏线虫(Cooperia curticei)和巴特斯细颈线虫(Nematodirus battus),或其组合。
在又一实施方式中,本发明的化合物、组合物、方法和用途有效地对抗列于先前两段的内寄生物的抗性品系。
在又一实施方式中,本发明提供制备式I或式II化合物的方法。
发明详述
术语"约"如本文所用意指大约、在..的区域、大致或在...周围。在术语"约"与数值范围结合使用时,其通过拓展所描述数值的上下边界修饰该范围。通常,术语"约"在本文中用来修饰数值为所述值的上下10%偏差。在一种特定实施方式中,术语"约"或"大约"意指在20%以内。在又一实施方式中,术语"约"意指在给定值或范围的5%以内。
本文通过端点描述的数字范围包括该范围内包含的全部数字和分数(例如,1至5包括1,1.5,2,2.75,3,3.90,4和5)。还应理解,全部数字及其分数推定为通过术语"约"修饰。
本文所用的术语"动物"包括全部哺乳动物,鸟类和鱼类并且包括全部脊椎动物,包括人类。动物包括但不限于人,猫,狗,牛,鸡,牛,鹿,山羊,马,驴,美洲驼,羊驼,猪,绵羊和牦牛。鸟类的实例包括火鸡,鸡,鸵鸟和其它牲畜或家养鸟类。还包括全部发育阶段的各动物,包括胚胎和胎儿阶段。
术语"有效量"如本文所用意指,在将组合物给予动物之后,活性剂在组合物中的浓度足以引起对靶标寄生物的希望生物学应答,其测量方法是本领域已知的和/或描述于本文实施例中。在某些实施方式中,与未处理的对照相比,活性剂在组合物中的"有效量"将提供对靶标寄生物至少70%的效力。在其它实施方式中,与未处理的对照相比,活性剂的"有效量"将提供至少80%或至少85%的效力。更一般地,活性剂的"有效量"将提供对靶标寄生物至少90%,至少93%,至少95%或至少97%的效力。
在实施方式中,本发明包括式(I)化合物:
和/或其可接受的盐和/或其对映体。
在又一实施方式中,本发明提供式II化合物:
和/或其可接受的盐和/或其对映体。
在一种实施方式中,式I或式II化合物可以是对映体富集的。如本文定义,对映体富集意指式I或式II化合物是相对另一种对映体R或S对映体富集的,其比例为至少80:20重量。在其它实施方式中,式I或式II化合物是以至少90:10,95:5或97:3重量的比率对映体富集的(R或S)。在又一实施方式中,式I或式II化合物是以至少98:2或99:1重量的比率对映体富集的。在实施方式中,式I或式II化合物可以分别是式I-R、I-S、II-R和/或II-S化合物和/或其可接受的盐:
式I和/或式II化合物和/或其盐和/或对映体在体外和在体内对内寄生物高度活性的。尤其是已发现,与具有很相似的结构和取代模式的化合物相比,式I化合物对某些内寄生物(包括捻转血矛线虫(Haemonchus contortus))展示令人惊讶地有效的活性。式I化合物的改善的活性是出人意料且难以预料的。
在实施方式中,式(I)化合物可以通过下述方案制备:
式1化合物(可商购的3,4-二氯甲苯)可以根据本领域技术人员已知的方法卤化例如溴化以产生式2化合物。式3化合物可以通过金属化2的C-Br键、随后加入甲酰化剂例如N,N-二甲基甲酰胺来制备。式3化合物可以根据本领域技术人员已知的方法硝化以产生式4化合物。例如用氟化剂比如或BAST二氟化式4化合物,提供式5化合物。在本领域技术人员已知的条件下还原,提供苯胺6。苯胺6然后通过在本领域技术人员已知的标准条件下重氮化而转化为杂环7a。用卤代丙酮例如氯丙酮烷基化产生7b,随后在氯化铵中与氰化物反应,提供氨基氰8。8与4-三氟甲硫基苯甲酰氯的反应提供化合物I。
本发明的又一实施方式包括杀寄生物组合物,其包含式I和/或式II化合物。本公开组合物还能够呈包括但不限于口服配制剂,可注射配制剂,和局部、皮肤或皮下配制剂的各种形式。配制剂期望给予至动物,其包括但不限于哺乳动物、鸟类和鱼类。哺乳动物的实例包括但不限于人类,牛,绵羊,山羊,美洲驼,羊驼,猪,马,驴,狗,猫和其它牲畜或家养哺乳动物。鸟类的实例包括火鸡,鸡,鸵鸟和其它牲畜或家养鸟类。式I或II化合物保护伴侣动物比如犬和猫免受内寄生物影响的用途是特别有用的。
兽医学组合物:式I和式II化合物和包含该化合物的组合物用于在动物中预防和处理寄生物侵袭/感染。本发明组合物包含有效量的至少一种式I或II化合物或其兽医上可接受的盐,和与之组合的兽医上可接受的载体或稀释剂和任选的其它非活性的赋形剂。所述组合物可以呈各种固体和液体形式,其适于施用或给药至动物的各种形式。例如,包含本发明化合物的兽医学组合物可以存在于适于口服给药、可注射给药(包括皮下和肠胃外给药)、和局部给药(例如涂抹或泼浇)、皮肤或皮下给药的配制剂中。
本发明组合物可以呈适于口服使用的形式(参见,例如美国专利号4,564,631,通过援引将其全部并入本文),饵料补充剂,含锭,糖锭,咀嚼剂(包括软咀嚼组合物),片剂,硬胶囊或软胶囊,药丸,乳液,水性或油性悬浮液,水溶液或油溶液,口服浇泼配制剂,可分散粉剂或颗粒剂,预混物,糖浆剂或酏剂,肠衣配制剂或糊剂。期望用于口服用途的组合物可以根据本领域已知的制备药物组合物的任意方法制备并且所述组合物可以含有一种或多种甜味剂、苦味剂、矫味剂、着色剂和/或防腐剂以提供药学上美观和适口的制剂。
片剂可以含有活性成分,其与无毒的药学上可接受的适于制备片剂的赋形剂混合。这些赋形剂可以是例如惰性稀释剂,比如碳酸钙、碳酸钠、乳糖、磷酸钙或磷酸钠;造粒剂和崩解剂,例如玉米淀粉或藻酸;结合试剂,例如淀粉、明胶或阿拉伯胶;和润滑剂,例如硬脂酸镁、硬脂酸或滑石。片剂可以是未经包覆的或者它们可以通过已知技术包覆以延缓在胃肠道中的崩解和吸收并由此提供在更长时间段内的持续作用。例如,可以使用延时物质比如甘油单硬脂酸酯或甘油二硬脂酸酯。它们还可以通过描述于U.S.专利号4,256,108;4,166,452;和4,265,874(全部通过援引将其全部并入本文)的技术进行包覆以形成用于受控释放的渗透性治疗片剂。
口服配制剂包括硬明胶胶囊,其中将活性成分与惰性固体稀释剂例如碳酸钙、磷酸钙或高岭土混合。胶囊还可以是软明胶胶囊,其中活性成分与水或可与水混合的溶剂比如丙二醇、各种PEG和乙醇,或油介质例如花生油、液状石蜡或橄榄油混合。
在一种实施方式中,式I或II化合物可以在可咀嚼片剂组合物或软可咀嚼组合物中给予,比如描述于US 2013/0203692 A1,US 2010/0087492,US 2006/0222684,US 2004/0151759和US 7955632的那些,通过援引全部并入本文。兽医学组合物可以呈软可咀嚼配制剂("软咀嚼剂")形式,其对动物是适口的并且可接受的。除了活性成分之外,本发明软咀嚼剂还可以包括一种或多种下述组分:溶剂或溶剂混合物,一种或多种填料,一种或多种粘合剂,一种或多种表面活性剂,一种或多种保湿剂,一种或多种润滑剂,一种或多种崩解剂,一种或多种着色剂,一种或多种抗微生物剂,一种或多种抗氧化剂,一种或多种pH调节剂和一种或多种调味剂。
可以用于本发明组合物的溶剂包括但不限于,各种等级的液体聚乙二醇(PEG)包括PEG 200、PEG 300、PEG 400和PEG 540;碳酸亚丙酯;醇,包括乙醇、异丙醇和苄醇;丙二醇;甘油三酯,包括但不限于辛酸/癸酸甘油三酯、辛酸/癸酸/亚油酸甘油三酯(例如和812、辛酸/癸酸/琥珀酸甘油三酯,丙二醇二辛酸酯/二癸酸酯等;水,山梨醇溶液,甘油辛酸酯/癸酸酯和聚乙二醇化的甘油酯或其组合。
本领域已知的各种填料可以用于本发明的软可咀嚼组合物当中。填料包括但不限于玉米淀粉,预胶化玉米淀粉,大豆蛋白细粉,玉米穗轴,和玉米谷蛋白粗粉等。在某些实施方式中,两种或更多种填料的组合可以用于组合物中。
可以用于本发明组合物中的粘合剂包括但不限于,聚乙烯基吡咯烷酮(例如聚维酮),交联的聚乙烯基吡咯烷酮(交聚维酮),各种等级的聚乙二醇包括PEG 3350、PEG 4000、PEG 6000、PEG 8000和甚至PEG 20,000等;乙烯基吡咯烷酮和乙酸乙烯酯的共聚物(例如共聚维酮)比如BASF以商品名64销售的产品等;淀粉比如马铃薯淀粉,木薯淀粉或玉米淀粉;糖蜜,玉米糖浆,蜜,枫糖浆和各种类型的糖类;或两种或更多种粘合剂的组合。
组合物中可以使用的保湿剂包括但不限于甘油(本文也称为丙三醇),丙二醇,鲸蜡醇和甘油单硬脂酸酯等。各种等级的聚乙二醇还可以用作保湿剂。
表面活性剂可以存在于组合物中以改善溶解度和摄食后的吸收。表面活性剂一般以约1至10%(w/w),更一般以约1至约5%(w/w)的浓度存在。可以用于组合物中的表面活性剂的实例包括但不限于,甘油基一油酸酯,聚氧乙烯脱水山梨糖醇脂肪酸酯,脱水山梨糖醇酯包括去水山梨糖醇单油酸酯聚乙烯醇,聚山梨酸酯包括聚山梨酯20和聚山梨酯80,d-α2生育酚聚乙二醇1000琥珀酸酯(TPGS),月桂基硫酸钠,氧化乙烯和氧化丙烯的共聚物(例如泊洛沙姆比如等),聚乙二醇蓖麻油衍生物包括聚乙二醇35蓖麻油聚乙二醇40氢化蓖麻油( 40),聚乙二醇60氢化蓖麻油丙二醇单月桂酸酯甘油酯包括甘油辛酸酯/癸酸酯聚乙二醇化的甘油酯PEG 300辛酸/癸酸甘油酯PEG 400辛酸/癸酸甘油酯PEG 300油酸甘油酯PEG 300亚油酸甘油酯聚乙二醇硬脂酸酯和聚乙二醇羟基硬脂酸酯包括聚乙二醇8硬脂酸酯(PEG 400单硬脂酸酯),聚乙二醇40硬脂酸酯(PEG 1750单硬脂酸酯),等。
本发明配制剂可以含有其它惰性成分比如抗氧化剂,防腐剂,或pH稳定剂。这些化合物是制剂领域熟知的。抗氧化剂可以加入本发明组合物以抑制活性剂降解。适宜的抗氧化剂包括但不限于α生育酚,抗坏血酸,抗坏血酸棕榈酸酯,富马酸,苹果酸,抗坏血酸钠,偏硫酸氢钠,没食子酸正丙酯,BHA(丁基化的羟基茴香醚),BHT(丁基化的羟基甲苯)单硫代甘油等。
本发明组合物还可以包括一种或多种润滑剂和/或处理助剂。在某些情况下润滑剂/处理助剂还可以表现为溶剂,因此本发明组合物的某些组分可以具有双重功能。润滑剂/处理助剂包括但不限于各种分子量范围的聚乙二醇包括PEG 3350(Dow Chemical)和PEG 4000,玉米油,矿物油,氢化植物油(Stereotex或Lubritab),花生油和/或蓖麻油。
许多调味剂可以用于本发明组合物中改善口服兽医学配制剂的适口性。优选的调味剂是并非衍生自动物来源的那些。在各种实施方式中,可以使用衍生自果实,肉类(包括但不限于猪肉,牛肉,鸡,鱼,家禽等),蔬菜,奶酪,腌肉,奶酪-腌肉和/或人工调味剂的调味组分。调味组分一般基于与服食软咀嚼剂的动物有关的考虑来选择。比如说,马可以喜欢苹果调味组分,而犬可以喜欢肉类调味组分。尽管衍生自非动物来源的调味组分是优选的,但在某些实施方式中可以使用含有牛肉或肝提取物等的天然调味剂,比如煨牛肉调味剂、人工粉化的牛肉调味剂、烤牛肉调味剂和腌牛肉调味剂等。
在本发明的又一实施方式中,活性组合物可以经由浇泼给予,且可以局部或经口给予。浇泼配制剂是那些,其中本发明含液体的组合物给予至动物的口或咽喉,或者倾倒至动物的皮肤或皮毛。浇泼配制剂包括式I或式II化合物,其溶于可接受的溶剂、悬浮于可接受的媒介的或包含所述化合物的乳液。可接受的载体是本领域技术人员已知的并且包括但不限于水,油,某些液体聚合物比如聚乙二醇(PEGs)。在一种实施方式中,本发明的浇泼配制剂包含液体聚乙二醇比如PEG 300和/或PEG 400。
本发明组合物还可以是水包油或油包水乳液形式。油相可以是植物油例如橄榄油或花生油,或矿物质油例如液状石蜡,或这些的混合物。适宜的乳化剂包括天然磷脂例如大豆卵磷脂,和衍生自脂肪酸和己糖醇脱水物的酯或偏酯例如去水山梨糖醇单油酸酯,和所述偏酯与环氧乙烷的缩合产物例如聚氧乙烯去水山梨糖醇单油酸酯。所述乳液还可以含有甜味剂,苦味剂,矫味剂,和/或防腐剂。
在一种实施方式中,本发明组合物可以是微乳剂形式。微乳剂良好地适于用作液体载体媒介物。微乳剂一般是包含水相、油相、表面活性剂和助表面活性剂的四元系统。它们是半透明的和各向同性的液体。
微乳剂构成如下:水相微滴在油相中的稳定分散液,或相反地油相微滴在水相中的稳定分散液。这些微滴的尺寸可以小于200nm(对于乳液为1000至100,000nm)。界面膜可以由表面活性(SA)和共表面活性(Co-SA)分子交替构成,其通过降低界面张力使得微乳剂自发形成。
在油相的一种实施方式中,油相能够形成自矿物或植物油,形成自不饱和多糖基化甘油酯或形成自甘油三酯,或另选地形成自所述化合物的混合物。在油相的一种实施方式中,油相可以包含甘油三酯;在油相的又一实施方式中,甘油三酯是中链甘油三酯,例如C8-C10辛酸/癸酸甘油三酯。在又一实施方式中,油相可以占微乳剂的约2至约15%;约7至约10%;和约8至约9%v/v的%v/v范围。
水相可以包括例如水或乙二醇衍生物,比如丙二醇,乙二醇醚,聚乙二醇或甘油。在一种实施方式中,二醇可以是丙二醇、二甘醇单乙醚、二丙二醇单乙醚或其混合物。一般地,水相在微乳剂中将占约1至约4%v/v的比例。
用于微乳剂的表面活性剂可以包括二甘醇单乙醚,二丙二醇单甲醚,聚乙二醇化的C8-C10甘油酯或聚甘油-6二油酸酯。除了这些表面活性剂之外,共表面活性剂还可以包括短链醇比如乙醇和丙醇。
对于上文讨论的三种组分(即水相、表面活性剂和共表面活性剂)来说某些化合物是共同的。然而,从业者的技术水平足以良好地将不同化合物用于相同配制剂的各组分。在表面活性剂/助表面活性剂的量的一种实施方式中,助表面活性剂与表面活性剂的比率是约1/7至约1/2。在助表面活性剂的量的又一实施方式中,微乳剂中存在约25至约75%v/v的表面活性剂和约10至约55%v/v的助表面活性剂。
含油悬浮液可以这样配制:将活性成分悬浮于植物油例如花生油、橄榄油、芝麻油或椰子油中,或于矿物质油比如液状石蜡中。含油悬浮液可以含有增稠剂例如蜂蜡,硬石蜡或鲸蜡醇。可以加入甜味剂比如蔗糖、糖精或阿司帕坦,苦味剂和矫味剂以提供适口的口服制剂。这些组合物可以通过加入抗氧化剂比如维生素C或其它已知防腐剂得以保藏。
含水悬浮液可以含有活性物质和与之混合的适于制备含水悬浮液的赋形剂。所述赋形剂包括助悬剂例如羧甲纤维素钠,甲基纤维素,羟基-丙基甲基纤维素,藻酸钠,聚乙烯基吡咯烷酮,黄蓍胶和阿拉伯胶;分散或润湿剂包括天然磷脂,例如卵磷脂,或烯烃氧化物与脂肪酸的缩合产物例如聚氧乙烯硬脂酸酯,或环氧乙烷与长链脂族醇的缩合产物例如十七亚乙基氧基鲸蜡醇,或环氧乙烷与衍生自脂肪酸和己糖醇的偏酯的缩合产物比如聚氧乙烯山梨醇单油酸酯,或环氧乙烷与衍生自脂肪酸和己糖醇脱水物的偏酯的缩合产物例如聚乙烯去水山梨糖醇单油酸酯。含水悬浮液还可以含有一种或多种防腐剂例如对-羟基苯甲酸酯乙酯或对-羟基苯甲酸酯正丙酯,一种或多种着色剂,一种或多种矫味剂,和一种或多种甜味剂和/或苦味剂,比如上文描述的那些。
适于通过加水制备含水悬浮液的可分散粉剂和颗粒剂可以提供活性成分和与之混合的分散或润湿剂、助悬剂和一种或多种防腐剂。适宜的分散或润湿剂和助悬剂诸如上文已经提及的那些。还可以存在额外的赋形剂例如甜味剂、苦味剂、矫味剂和着色剂。
糖浆剂和酏剂可以用甜味剂例如甘油、丙二醇、山梨醇或蔗糖进行配制。所述配制剂还可以含有缓和剂、防腐剂、矫味剂和/或着色剂。
在本发明的又一实施方式中,所述组合物可以是糊剂形式。糊剂形式实施方式的实例包括但不限于美国专利号6,787,342和7,001,889(将其各自通过援引并入本文)中描述的那些。除了本发明化合物之外,糊剂还可以进一步含有锻制二氧化硅;粘度调节剂;载体;任选地,吸收剂;和任选地,着色剂、稳定剂、表面活性剂或防腐剂。
在配制剂的一种实施方式中,所述配制剂可以是糊剂,其含有本发明化合物,锻制二氧化硅,粘度调节剂,吸收剂,着色剂;和亲水载体,其是三乙酸甘油酯,一甘油酯,甘油二酯或甘油三酯。
糊剂也可以包括粘度调节剂。适宜的粘度调节剂包括但不限于聚乙二醇(PEG),包括但不限于,PEG 200,PEG 300,PEG 400,PEG 600;一乙醇胺,三乙醇胺,甘油,丙二醇,聚氧乙烯(20)去水山梨糖醇一油酸酯(聚山梨酸酯80或吐温80),或泊洛沙姆(例如普流罗尼克L81);吸收剂比如碳酸镁,碳酸钙,淀粉和纤维素及其衍生物;以及着色剂,包括但不限于二氧化钛,铁的氧化物,或FD&C蓝#1铝色料。
在某些实施方式中,组合物可以是无菌可注射的含水或油性悬浮液形式。该悬浮液可以根据已知技术用上文提及的那些适宜的分散或润湿剂和助悬剂来配制。无菌可注射的制剂还可以是在无毒的经肠胃外-可接受的稀释剂或溶剂中的无菌可注射的溶液或悬浮液,例如是1,3-丁二醇中的溶液。在可使用的可接受的媒介物和溶剂中尤其提及水,林格溶液和等渗氯化钠溶液。还可以使用共溶剂比如乙醇,丙二醇,环亚甲基甘油醚或聚乙二醇。可以使用防腐剂,比如苯酚或苯甲醇。
此外,无菌、非挥发油可以常规地用作溶剂或悬浮介质。出于该意图,可以使用任意温和非挥发油,包括合成的甘油单酯或二酯。此外,脂肪酸比如油酸可用于制备可注射剂。
局部、皮肤和皮下配制剂作为非限制性实例可以包括乳液,霜剂,软膏剂,凝胶,糊剂,粉末,香波,泼浇配制剂,即用配制剂,涂抹剂溶液和悬浮液,滴剂和喷雾剂。本发明化合物或在活性剂中包括至少一种本发明化合物的组合物以涂抹剂、喷雾剂或泼浇剂组合物局部施用,可以使得本发明组合物经过皮肤吸收以实现全身性水平,通过皮脂腺或在皮肤表面分布以实现整个皮毛中的水平。在化合物经过皮脂腺分布的情况下,它们可以充当储库,而此时可以具有长期持续效果(多至数月)。涂抹配制剂一般施用在局部区域,其是指并非整个动物的区域。在一种实施方式中,所述位置可以是双肩之间。在又一实施方式中,其可以是带状,例如动物头部至尾部的施用带。
泼浇配制剂描述于美国专利号6,010,710,也通过援引并入本文。泼浇配制剂可以有利地是油性的,且一般包含活性成分的稀释剂或媒介物,如果活性成分在稀释剂中不可溶,则还包括溶剂(例如有机溶剂)。
本发明中可用的有机溶剂包括但不限于乙酰基三丁基柠檬酸酯,脂肪酸酯比如己二酸二甲酯,己二酸二异丁酯,丙酮,乙腈,苄醇,乙醇,丁基二甘醇,二甲基乙酰胺,二甲基甲酰胺,二甲亚砜,二丙二醇正丁基醚,乙醇,异丙醇,甲醇,乙二醇一乙基醚,乙二醇一甲基醚,一甲基乙酰胺,二丙二醇一甲基醚,液体聚氧化乙二醇,丙二醇,2-吡咯烷酮(例如N-甲基吡咯烷酮),碳酸亚丙酯,二甘醇一乙基醚,乙二醇,三乙酸甘油酯,羧酸的C1-C10酯比如乙酸丁酯或辛酯,和邻苯二甲酸二乙酯,或这些溶剂中至少两种的混合物。
溶剂与活性剂化合物及其在该溶剂中的溶解度成比例地使用。应努力实现尽可能小的体积。用媒介物将差异补足至100%。
配制剂所用的媒介物或稀释剂可以包括二甲亚砜(DMSO),二醇衍生物例如丙二醇、乙二醇醚、聚乙二醇或甘油。作为媒介物或稀释剂,还可以提及植物油比如但不限于大豆油,花生油,蓖麻油,玉米油,棉花油,橄榄油,葡萄籽油,向日葵油等;矿物质油比如但不限于矿脂,石蜡,有机硅等;脂族或环状烃或另选地例如中链(比如C8至C12)甘油三酯。
在本发明的又一实施方式中,可以加入软化剂和/或铺展和/或成膜剂。在一种实施方式中,软化剂和/或铺展剂和/或成膜剂可以是:
聚乙烯基吡咯烷酮,聚乙烯醇,乙酸乙烯酯和乙烯基吡咯烷酮的共聚物,聚乙二醇,苯甲醇,甘露醇,甘油,山梨醇,聚氧基亚乙基化的去水山梨糖醇酯;卵磷脂,羧甲纤维素钠,硅油,聚二有机硅氧烷油(比如聚二甲基硅氧烷(PDMS)油),例如含有硅烷醇官能的那些,或45V2油,
阴离子表面活性剂比如碱性硬脂酸盐,硬脂酸钠、硬脂酸钾或硬脂酸铵;硬脂酸钙,硬脂酸三乙醇胺盐;松香酸钠;硫酸烷基酯的盐(例如硫酸月桂基酯的钠盐和硫酸鲸蜡基酯的钠盐);十二烷基苯磺酸钠,二辛基磺基琥珀酸钠;脂肪酸(例如衍生自椰子油的那些),
阳离子表面活性剂包括水可溶的式N+R'R"R"'R"",Y-季铵盐,其中残基R是任选羟基化的烃残基而Y-是强酸的阴离子比如卤化物、硫酸和磺酸阴离子;十六烷基三甲基溴化铵属于可以使用的阳离子表面活性剂,
(a)式N+HR'R"R'"胺盐,其中残基R是任选羟基化的烃残基;十八烷基胺盐酸盐属于可以使用的阳离子表面活性剂,
(b)非离子表面活性剂比如去水山梨糖醇酯,其是任选地聚氧基亚乙基化的(例如聚山梨酯80),聚氧基亚乙基化的烷基醚;聚氧基丙基化的脂肪醇比如聚氧丙烯-苯乙烯醚;聚乙二醇硬脂酸酯,蓖麻油的聚氧基亚乙基化的衍生物,聚甘油酯,聚氧基亚乙基化的脂肪醇,聚氧基亚乙基化的脂肪酸,环氧乙烷和环氧丙烷的共聚物,
(c)两性表面活性剂比如甜菜碱的取代的月桂基化合物;或
(d)这些试剂中至少两种的混合物。
在软化剂的量的一种实施方式中,所用软化剂比例可以是约0.1至50%或0.25至5%体积。在又一实施方式中,所用软化剂比例可以是约0.1%至约30%,约1%至约30%,约1%至约20%,或约5%至约20%体积。
在本发明的又一实施方式中,组合物可以是即用溶液形式,其描述于美国专利号6,395,765,通过援引并入本文。除了本发明化合物之外,即用溶液还可以含有结晶抑制剂和有机溶剂或有机溶剂的混合物。在某些实施方式中,水可以包括有机溶剂。
在本发明的各种实施方式中,组合物可以包括结晶抑制剂的量为按配制剂总重量计约1至约50%(w/v)或约5至约40%(w/v)。在其它实施方式中,本发明配制剂中的结晶抑制剂的量可以是约1%至约30%,约5%至约20%,约1%至约15%,或约1%至约10%(w/w)。本发明配制剂中所用的结晶抑制剂的类型不受限制,只要其有效抑制活性剂或无活性剂自配制剂结晶。例如,在本发明的某些实施方式中,配制剂的溶剂或共溶剂还可以充当结晶抑制剂,如果在给予配制剂的情况下其充分抑制晶体随时间形成。
可用于本发明的结晶抑制剂包括但不限于:
聚乙烯基吡咯烷酮,聚乙烯醇,乙酸乙烯酯和乙烯基吡咯烷酮的共聚物,聚乙二醇,苄醇,二甲基甲酰胺,二甲基乙酰胺,二甲亚砜,2-吡咯烷酮,N-甲基吡咯烷酮,甘露醇,甘油,山梨糖醇或去水山梨糖醇的聚氧基亚乙基化酯;卵磷脂或羧甲基纤维素钠;或丙烯酸衍生物,比如丙烯酸类或甲基丙烯酸类或其聚合物或共聚物,聚乙二醇(PEG)或含有聚乙二醇的聚合物,比如四氢呋喃聚乙二醇醚(glycofurol)等;
阴离子表面活性剂,比如碱性硬脂酸盐(例如硬脂酸钠、钾或铵);硬脂酸钙或硬脂酸三乙醇胺盐;松香酸钠;硫酸烷基酯的盐,其包括但不限于硫酸月桂基酯的钠盐和硫酸鲸蜡基酯的钠盐;十二烷基苯磺酸钠或二辛基磺基琥珀酸钠;或脂肪酸(例如椰子油);
阳离子表面活性剂,比如水可溶的式N+R'R”R'"R""Yˉ季铵盐,其中R残基是相同或不同的任选羟基化的烃残基而Yˉ是强酸的阴离子,比如卤化物,硫酸和磺酸阴离子;十六烷基三甲基溴化铵是可以使用的阳离子表面活性剂之一;
式N+HR'R”R'"胺盐,其中R残基是相同或不同的任选羟基化的烃残基;十八烷基胺盐酸盐是可以使用的阳离子表面活性剂之一;
非离子表面活性剂,比如去水山梨糖醇的任选聚氧基亚乙基化的酯,例如聚山梨酯80,或聚氧基亚乙基化的烷基醚;聚乙二醇硬脂酸酯,蓖麻油的聚氧基亚乙基化的衍生物,聚甘油酯,聚氧基亚乙基化的脂肪醇,聚氧基亚乙基化的脂肪酸或环氧乙烷和环氧丙烷的共聚物;
两性表面活性剂,比如内铵盐的月桂基取代化合物;
上述(a)-(f)所列的化合物中至少两种的混合物;或者
在配制剂给予之后抑制晶体或无定形固体形成的有机溶剂或溶剂的混合物。
在结晶抑制剂的一种实施方式中,将使用结晶抑制剂配对。上述配对包括,例如高分子类型成膜剂和表面活性剂的组合。这些试剂将选自上文作为结晶抑制剂提及的化合物。
在某些实施方式中,有机溶剂可以具有约10至约35或约20至约30的介电常数。在其它实施方式中,有机溶剂可以具有约10至约40或约20至约30的介电常数。该有机溶剂或溶剂混合物在总组合物中的含量不受限制并将以足以溶解希望组分至希望浓度的量存在。如上文所讨论,有机溶剂还可以充当配制剂中的结晶抑制剂。
在某些实施方式中,有机溶剂中的一种或多种可以具有小于约100℃或小于约80℃的沸点。在其它实施方式中,有机溶剂可以具有小于约300℃,小于约250℃,小于约230℃,小于约210℃或小于约200℃的沸点。
在存在溶剂混合物也即溶剂和共溶剂的某些实施方式中,溶剂可以以约1/50至约1/1的重量/重量(W/W)比率存在于组合物中。一般来说,溶剂的比率是约1/30至约1/1,约1/20至约1/1,或约1/15至约1/1重量。优选,两种溶剂以约1/15至约1/2的重量/重量比存在。在某些实施方式中,存在的溶剂中的至少一种可以改善活性剂的溶解度或充当干燥促进剂。在特别的实施方式中,溶剂中的至少一种可与水混合。
配制剂还可以包含抗氧化剂以期望抑制在空气中氧化,该试剂可以以约0.005至约1%(w/v),约0.01至约0.1%,或约0.01至约0.05%的比例存在。
在成膜剂的一种实施方式中,所述试剂是高分子类型,其包括但不限于各种等级的聚乙烯基吡咯烷酮,聚乙烯醇,和乙酸乙烯酯与乙烯基吡咯烷酮的共聚物。
在表面活性剂的一种实施方式中,所述试剂包括但不限于由非离子表面活性剂构成的那些;在表面活性剂的又一实施方式中,所述试剂是去水山梨糖醇的聚氧基亚乙基化的酯,而在表面活性剂的又一实施方式中,所述试剂包括各种等级的聚山梨醇,例如聚山梨酯80。
在本发明的又一实施方式中,成膜剂和表面活性剂能够在别处提及的结晶抑制剂总量的限制范围内以相似或相同量加入。
结晶抑制剂抑制晶体在皮毛上形成,并改善皮肤或兽皮的美容外观的保持;也即不存在粘附倾向或粘性外观倾向,尽管活性物质浓度高。可以将文中并未提及的那些物质用作本发明中的结晶抑制剂。在一种实施方式中,结晶抑制剂的有效性可以通过试验展示,根据该试验于20℃将0.3mL溶液置于载玻片上24小时,所述溶液包含在如前文所定义的适当溶剂中的10%(w/v)活性剂和10%(w/v)充当结晶抑制剂的化合物,在这之后,肉眼观察到载玻片上存在少于10个晶体,优选少于0个晶体。
在抗氧化剂的一种实施方式中,所述试剂是本领域常规的那些且包括但不限于丁基化羟基茴香醚,丁基化羟基甲苯,抗坏血酸,焦亚硫酸钠,没食子酸丙酯,硫代硫酸钠或具有抗氧化特性的至少两种化合物的混合物。
上文讨论的配制助剂是本领域从业者所熟知的并且可以商业购得或通过已知技术获得。这些浓缩组合物一般通过简单混合如前文所定义的组分来制备;有利地,起始点是将活性物质混入主要溶剂中,然后加入其它成分或助剂。
施用的配制剂体积将取决于动物类型和动物大小以及配制剂强度和活性剂的效能。在一种实施方式中,可以将约0.1至约20ml的量的配制剂施用至动物。在体积的其它实施方式中,所述体积可以是约0.1至约10ml,约0.1至约5ml,约0.5ml至约10ml,或约0.3至约3ml。
在本发明的又一实施方式中,在将溶液施用至哺乳动物或鸟类的情况下,施用根据本发明的涂抹配制剂还能够提供长期持续的和广谱的效力。涂抹配制剂提供将浓缩溶液、悬浮液、微乳剂或乳液局部给药用于间歇施用至动物上的位点,一般在两肩之间(涂抹剂类型溶液)。
对于涂抹配制剂,载体可以是描述于U.S.专利号6,426,333(通过援引并入本文)的液态载体媒介物,其在涂抹配制剂的一种实施方式中可以包含溶剂或溶剂混合物,包括但不限于,丙酮,脂族醇比如甲醇,乙醇,丙醇,丁醇,异丙醇,戊醇,己醇,庚醇,辛醇,壬醇,环戊醇,环己醇,乙二醇,丙二醇等;芳族醇比如苯酚,甲酚,萘酚,苄醇等;乙腈,丁基二甘醇,有机酰胺比如二甲基乙酰胺,二甲基甲酰胺,一甲基乙酰胺,2-吡咯烷酮,N-甲基吡咯烷酮,乙烯基吡咯烷酮等;碳酸亚丙基酯或碳酸亚乙基酯,二甲亚砜(DMSO),二醇聚合物或其醚,比如各种等级的聚乙二醇(PEG),各种等级的聚丙二醇,二丙二醇正-丁基醚,乙二醇一乙基醚,乙二醇一甲基醚,二丙二醇一甲基醚,二甘醇一乙基醚,乙二醇,邻苯二甲酸二乙酯脂肪酸酯,比如己二酸二乙酯或己二酸二异丁酯,或这些溶剂中至少两种的混合物。
液体载体媒介物可以任选地含有结晶抑制剂包括但不限于上文(a)至(h)描述的那些,或者可以充当溶剂和结晶抑制剂的化合物(如前文所定义),或者这些结晶抑制剂的混合物。
涂抹配制剂可以通过将活性成分溶于药学上或兽医学可接受的媒介物来制备。另选地,涂抹配制剂能够通过将活性成分包囊来制备从而将治疗剂的残余物遗留在动物表面。取决于待治疗的宿主动物的种类,感染的严重性和类型和宿主的体重,这些配制剂将随组合中的治疗剂重量而变化。
各剂型可以一般地含有约0.1mg至约5g的活性剂。在其它实施方式中,所述剂型可以含有约0.5mg至约5g的活性剂。在剂型的一种实施方式中,所述剂量可以含有约1mg至约500mg活性剂,一般为约25mg,约50mg,约100mg,约200mg,约300mg,约400mg,约500mg,约600mg,约800mg,或约1000mg。
在本发明的一种实施方式中,式I或式II化合物可以在配制剂中以约0.05至约10%重量/体积的浓度存在。在一种实施方式中,化合物以约2至约5%(w/v)的浓度存在。在又一实施方式中,化合物以约3至约6%(w/v)的浓度存在。在本发明的又一实施方式中,活性剂可以在配制剂中以约0.1至约2%重量/体积的浓度存在。在本发明的又一实施方式中,活性剂可以在配制剂中以约0.25至约1.5%重量/体积的浓度存在。在本发明的又一实施方式中,活性剂可以在配制剂中以约1%重量/体积的浓度存在。
在一种实施方式中,组合物包含对映体实质上富集的式I或式II化合物。术语"实质上富集的"意指其中重量:重量比是至少约1.5:1或更高,有利于希望对映体。在又一实施方式中,延长释放的可注射组合物包含(S)-对映体实质上富集的式I或式II化合物。在又一实施方式中,延长释放的可注射组合物包含(R)-对映体实质上富集的式I或式II化合物。
在又一实施方式中,组合物包含(S)-对映体富集的式I或式II化合物,其(S)与(R)的重量:重量比是至少约2:1或更高。在又一实施方式中,组合物包含(S)-对映体富集的式I或II化合物,其(S)与(R)的重量:重量比是至少约5:1或更高。在又一实施方式中,本发明组合物包含(S)-对映体富集的式I或式II化合物,其(S)与(R)的重量:重量比是至少约10:1或更高。在又一实施方式中,组合物包含式I或式II化合物,其实质上是纯的(S)-对映体。
在又一实施方式中,组合物包含(R)-对映体富集的式I或式II化合物,其(R)与(S)的重量:重量比是至少大约2:1或更高。在又一实施方式中,本发明组合物包含(R)-对映体富集的式I或式II化合物,其(R)与(S)的重量:重量比是至少约5:1或更高。在又一实施方式中,本发明组合物包含(R)-对映体富集的式I或式II化合物,其(R)与(S)的重量:重量比是至少约10:1或更高。在又一实施方式中,本发明组合物包含式I或式II化合物,其实质上是纯的R-对映体。
兽医学方法和用途
本公开的又一实施方式涉及在有需要的哺乳动物中治疗内寄生物感染的方法,其包括给药有效量的本公开化合物。
在治疗内寄生物感染的一种实施方式中,蠕虫选自但不限于裸头绦虫属(Anaplocephaela(Anoplocephala)),钩口线虫属(Ancylostoma),Anecator,蛔虫属(Ascaris),布鲁属(Brugia),仰口线虫属(Bunostomum),毛细线虫属(Capillaria),夏伯特线虫属(Chabertia),古柏线虫属(Cooperia),盅口属(Cyathostomum),杯环属(Cylicocyclus),双冠属(Cylicodontophorus),杯冠属(Cylicostephanus),盆口属(Craterostomum),网尾属(Dictyocaulus),双瓣丝虫属(Dipetalonema),复孔属(Dipylidium),恶丝虫属(Dirofilaria),龙线虫属(Dracunculus),棘球属(Echinococcus),蛲虫属(Enterobius),吸虫属(Fasciola),类丝虫属(Filaroides),胃线虫属(Habronema),血矛线虫属(Haemonchus),后圆线虫属(Metastrongylus),蒙尼属(Moniezia),板口线虫属(Necator),细颈线虫属(Nematodirus),日圆线虫属(Nippostrongylus),结节线虫属(Oesophagostumum),盘尾属(Onchocerca),奥斯特线虫属(Ostertagia),尖尾线虫属(Oxyuris),副蛔虫属(Paracaris),血吸虫属(Schistosoma),圆线虫属(Strongylus),绦虫属(Taenia),弓蛔虫属(Toxocara),类圆线虫属(Strongyloides),弓蛔线虫属(Toxascaris),毛线虫属(Trichinella),鞭虫属(Trichuris),毛圆线虫属(Trichostrongylus),三齿线虫属(Triodontophorous),钩虫属(Uncinaria),吴策属(Wuchereria),及其组合。
在本公开的又一实施方式中,蠕虫是捻转血矛线虫(Haemonchus contortus),环纹奥斯特线虫(Ostertagia circumcincta),艾氏毛圆线虫(Trichostrongylus axei),透明毛圆线虫(Trichostrongylus colubriformis),短古柏线虫(Cooperia curticei),巴特斯细颈线虫(Nematodirus battus)及其组合。
在一种实施方式中,根据本公开可以防治上述有机体的抗性品系。在实施方式中,本发明的方法和用途有效地对抗通过大环内酯比如阿维菌素类(avermectins)和密比霉素类(milbemycins)并未有效防治的内寄生物。在又一实施方式中,本发明的方法和用途有效地对抗对苯并咪唑活性剂有抗性的内寄生物。
本公开的又一实施方式涉及在有需要的哺乳动物中治疗外寄生物感染的方法,其包括给予有效量的本公开化合物。
在治疗外寄生物感染的一种实施方式中,感染物选自但不限于蚤,蜱,螨,蚊,蝇,虱,丽蝇及其组合。
在又一实施方式中,包含式I和/或II化合物的组合物还可以包括其它兽医学治疗剂。可以包括在本发明组合物中的兽医学药剂是本领域熟知的(参见例如Plumb’Veterinary Drug Handbook,5th Edition,ed.Donald C.Plumb,Blackwell Publishing,(2005)或The Merck Veterinary Manual,9th Edition,(January 2005))并且包括但不限于阿卡波糖,乙酰丙嗪马来酸酯,对乙酰氨基酚,乙酰唑胺,乙酰唑胺钠,乙酸,醋羟胺酸,乙酰半胱氨酸,阿维A,阿昔洛韦,阿苯达唑,沙丁胺醇硫酸酯,阿芬太尼,别嘌醇,阿普唑仑,烯丙孕素,金刚烷胺,阿米卡星硫酸盐,氨基己酸,氨戊酰胺氢硫酸盐,氨茶碱/茶碱,胺碘酮,阿米替林,苯磺酸氨氯地平,氯化铵,钼酸铵,阿莫西林,克拉维酸钾,两性霉素B脱氧胆酸盐,基于脂质的两性霉素B,氨苄西林,安普罗铵,抗酸剂(口服),抗蛇毒血清,阿扑吗啡,安普霉素硫酸盐,维生素C,天冬酰胺酶,阿司匹林,阿替洛尔,阿替美唑,苯磺阿曲库铵,阿托品硫酸盐,金诺芬(aurnofin),金硫葡糖,阿扎哌隆,硫唑嘌呤,阿奇霉素,巴氯芬,巴比妥酸盐,贝那普利,倍他米松,氯贝胆碱,比沙可啶,碱式水杨酸铋,博来霉素硫酸盐,十一烯酸勃地酮,溴化物,甲磺酸溴隐亭,budenoside,盐酸丁丙诺啡,盐酸丁螺环酮,白消安,酒石酸布托啡诺,卡麦角林,鲑鱼降钙素,骨化三醇,钙盐,卡托普利,卡茚西林钠,卡比马唑,卡铂,卡尼汀,卡洛芬,卡维地洛,头孢羟氨苄,头孢唑林钠,头孢克肟,clorsulon,头孢哌酮钠,头孢噻肟钠,头孢替坦二钠,头孢西丁钠,头孢泊肟酯,头孢他啶,头孢噻呋钠,头孢噻呋,头孢三嗪钠,头孢氨苄,头孢菌素,头孢匹林,炭(活性炭),苯丁酸氮芥,氯霉素,氯氮氯氮+/-克利溴铵,氯噻嗪,马来酸氯苯那敏,盐酸氯丙嗪,氯磺丙脲,金霉素,绒促性素(HCG),铬,西咪替丁,环丙沙星,西沙必利,顺铂,柠檬酸盐,克拉霉素,氯马斯汀富马酸盐,克仑特罗,克林霉素,氯法齐明,盐酸氯米帕明,氯硝西泮,可乐定,氯前列醇钠,氯氮二钾,clorsulon,氯唑西林,可待因磷酸盐,秋水仙碱,促皮质激素(ACTH),替可克肽,环磷酰胺,环胞素,赛庚啶,阿糖胞苷,达卡巴嗪,放线菌素D/放线菌素D,达肝素钠,达那唑,丹曲林钠,氨苯砜,地考喹酯,去铁胺甲磺酸盐,地拉考昔,地洛瑞林乙酸盐,去氨加压素乙酸盐,去氧皮质酮特戊酸盐,地托咪定,地塞米松,右泛醇,右雷佐生,右旋糖酐,地西泮,二氮嗪(口服),双氯非那胺,双氯芬酸钠,双氯西林,枸橼酸乙胺嗪,己烯雌酚(DES),二氟沙星,地高辛,双氢速甾醇(DHT),地尔硫茶苯海明,二巯丙醇/BAL,二甲亚砜,地诺前列素氨丁三醇,二苯基羟基胺,丙吡胺磷酸盐,盐酸多巴酚丁胺,多库酯/DSS,甲磺酸多拉司琼,多潘立酮,盐酸多巴胺,多拉克丁,盐酸多沙普仑,盐酸多塞平,盐酸多柔比星,多西环素,依地酸盐钙二钠,乙二胺四乙酸钙,依酚氯铵,依那普利/依那普利拉,依诺肝素钠,恩氟沙星,硫酸麻黄碱,肾上腺素,依泊汀/红细胞生成素,依立诺克丁,依西太尔,红霉素,盐酸艾司洛尔,环戊丙酸雌二醇,依他尼酸/依他尼酸钠,乙醇(乙醇),依替膦酸钠,依托度酸,依托咪酯,安乐死剂w/戊巴比妥,法莫替丁,脂肪酸(必需/omega),非尔氨酯,芬太尼,硫酸亚铁,非格司亭,非那雄胺,氟虫腈,氟苯尼考,氟康唑,氟胞嘧啶,氟氢可的松乙酸盐,氟马西尼,氟米松,氟尼辛葡甲胺,氟尿嘧啶(5-FU),氟西汀,丙醋氟替卡松,氟伏沙明马来酸盐,甲吡唑(4-MP),呋喃唑酮,呋塞米,加巴喷丁,吉西他滨HCL,庆大霉素硫酸盐,格列美脲,格列吡嗪,高血糖素,糖皮质类固醇试剂,氨基葡萄糖/软骨素硫酸盐,谷氨酰胺,格列本脲,甘油(口服),格隆溴铵,戈那瑞林,灰黄霉素,愈创甘油醚,氟烷,谷他血红蛋白-200肝素,羟乙基淀粉,透明质酸钠,肼苯哒嗪,氢氯噻嗪,氢可酮重酒石酸盐,氢化可的松,氢吗啡酮,羟基脲,羟嗪,异环磷酰胺,吡虫啉,咪多卡二丙酸盐,亚胺硫霉素-西司他丁钠,丙米嗪,氨力农乳酸盐,胰岛素,干扰素alfa-2a(人类重组),碘化物(钠/钾),吐根(糖浆),碘泊酸钠,右旋糖酐铁,异氟烷,异丙肾上腺素,异维A酸,异克舒令,伊曲康唑,依维菌素,白陶土/果胶,氯胺酮,酮康唑,酮洛芬,酮咯酸氨丁三醇,乳果糖,亮丙立德,保松噻,左乙拉西坦,左甲状腺素钠,利多卡因,林可霉素,碘塞罗宁钠,赖诺普利,洛莫司汀(CCNU),虱螨脲,赖氨酸,镁,甘露醇,马波沙星,氮芥,美克洛嗪,甲氯芬那酸,美托咪定,中链甘油三酯,醋酸甲羟孕酮,甲地孕酮乙酸盐,美拉索明,褪黑激素,美洛昔康,美法仑,麦啶,巯嘌呤,美罗培南,二甲双胍,美沙酮,醋甲唑胺,乌洛托品扁桃酸盐/马尿酸盐,甲巯咪唑,甲硫氨酸,美索巴莫,美索比妥钠,甲氨蝶呤,甲氧氟烷,亚甲蓝,哌甲酯,甲泼尼龙,甲氧氯普胺,美托洛尔,metronidaxole,美西律,米勃酮,咪达唑仑,密比霉素肟,矿物质油,米诺环素,米索前列醇,米托坦,米托蒽醌,吗啡硫酸盐,莫昔克丁(moxidectin),纳洛酮,癸酸诺龙,萘普生,麻醉药(鸦片)激动剂镇痛药,新霉素硫酸盐,新斯的明,烟酰胺,硝唑尼特,烯啶虫胺,呋喃妥因,硝酸甘油,硝普钠,尼扎替丁,新生霉素钠,制霉菌素,奥曲肽乙酸盐,奥沙拉秦钠,奥美拉唑,昂丹司琼,鸦片止泻药,奥比沙星,苯唑西林钠,奥沙西泮,奥昔布宁氯化物,羟吗啡酮,氧四环素,缩宫素,帕米膦酸二钠,pancreplipase,泮库溴铵,巴龙霉素硫酸盐,parozetine,青霉胺,青霉素类包括青霉素、青霉素V钾,喷他佐辛,戊巴比妥钠,木聚硫钠,己酮可可碱,培高利特甲磺酸酯,苯巴比妥,酚苄明,保泰松,去氧肾上腺素,苯基丙醇胺,苯妥英钠,信息素类,非经肠道磷酸,维生素K1/维生素K-1,匹莫苯,哌嗪,吡利霉素,吡罗昔康,聚硫酸化的糖胺聚糖,泊那珠利,氯化钾,氯解磷定,哌唑嗪,泼尼松龙/泼尼松,扑米酮,普鲁卡因胺,丙卡巴肼,丙氯拉嗪,溴丙胺太林,疮疱丙酸杆菌(propionibacterium acnes)注射剂,丙泊酚,普萘洛尔,硫酸鱼精蛋白,伪麻黄碱,欧车前亲水胶,溴吡斯的明,美吡拉敏马来酸盐,乙胺嘧啶,米帕林,奎尼丁,雷尼替丁,利福平,s-腺苷基-甲硫氨酸(SAMe),盐水/高渗性泻药,司拉克丁(selamectin),司来吉兰/l-得普尼林,舍曲林,司维拉姆,七氟烷,水飞蓟素/水飞蓟,碳酸氢钠,聚磺苯乙烯钠,葡萄糖酸锑钠,硫酸钠,硫代硫酸钠,垂体生长激素,索他洛尔,大观霉素,螺内酯,司坦唑醇,链激酶,链佐星,二巯丁二酸,琥珀酰氯化胆碱,硫糖铝,舒芬太尼柠檬酸盐,磺胺氯达嗪钠,磺胺嘧啶/trimethroprim,磺胺甲噁唑/甲氧苄啶,磺胺地索辛(sulfadimentoxine),磺胺地索辛/奥美普林,柳氮磺吡啶,牛磺酸,替泊沙林,terbinafline,特布他林硫酸盐,睾酮,四环素,硫胂胺钠,维生素B1,硫鸟嘌呤,硫喷妥钠,thiotepa,促甲状腺素,硫姆林,替卡西林二钠,替来他明/唑拉西泮,tilmocsin,硫普罗宁,妥布霉素硫酸盐,妥卡尼,妥拉唑林,托芬那酸,托吡酯,曲马多,曲安奈德,曲恩汀,曲洛司坦,阿利马嗪酒石酸盐w/泼尼松龙,曲吡那敏,泰洛星,urdosiol,丙戊酸,钒,万古霉素,加压素,维库溴铵,维拉帕米,长春碱硫酸盐,长春新碱硫酸盐,维生素E/硒,杀鼠灵钠,赛拉嗪,育亨宾,扎鲁司特,齐多夫定(AZT),乙酸锌/硫酸锌,唑尼沙胺及其混合物。
在本发明的一种实施方式中,芳基吡唑化合物比如苯基吡唑可以包括在本发明兽医学组合物中。芳基吡唑化合物是本领域已知的并且适于在本发明组合物中与式I或式II化合物组合。所述芳基吡唑化合物的实例包括但不限于描述于U.S.专利号6,001,384;6,010,710;6,083,519;6,096,329;6,174,540;6,685,954,6,998,131和7,759,381中的那些(通过援引将其全部并入本文)。特别优选的芳基吡唑活性剂是氟虫腈。
在本发明的又一实施方式中,充当杀螨剂、驱虫剂和/或杀昆虫剂的一种或多种大环内酯或内酰胺能够与式I或II化合物组合包括在本发明组合物中。为了避免疑问,术语"大环内酯"如本文所用包括天然和合成的或半合成的阿维菌素类(avermectin)和密比霉素类(milbemycin)化合物。已发现式I或式II化合物与阿维菌素类或密比霉素类活性剂的组合特别有效地防治单独用阿维菌素类或密比霉素类难以防治的内寄生物。
可以用于本发明组合物的大环内酯包括但不限于天然产生的阿维菌素类(例如包括指定为A1a、A1b、A2a、A2b、B1a、B1b、B2a和B2b的组分)和密比霉素类化合物,半合成的阿维菌素类和密比霉素类,阿维菌素类单糖化合物和阿维菌素类配糖基化合物。可以用于组合物的大环内酯化合物的实例包括但不限于阿维菌素,地马待克丁,多拉克丁,甲氨基阿维菌素,依立诺克丁,依维菌素,拉替菌素(latidectin),雷皮菌素(lepimectin),司拉克丁(selamectin),ML-1,694,554和密比霉素类(milbemycins),包括但不限于弥拜菌素(milbemectin),密比霉素D,密比霉素A3,密比霉素A4,密比霉素肟,莫昔克丁(moxidectin)和奈马克丁(nemadectin)。还包括的是所述阿维菌素类和密比霉素类的5-氧代和5-肟衍生物。
大环内酯化合物是本领域已知的并且能够容易地商购获得或通过本领域已知的合成技术获得。可参见广泛存在的技术和商业文献。对于阿维菌素类,依维菌素和阿维菌素可以参见例如Springer Verlag.出版的M.H.Fischer和H.Mrozik,William C.Campbell的"Ivermectin and Abamectin",1989或Albers-等人(1981)的"AvermectinsStructure Determination",J.Am.Chem.Soc.,103,4216-4221。对于多拉克丁,可以参见"Veterinary Parasitology",vol.49,No.1,1993年7月,5-15。对于密比霉素类,可以尤其参见Davies H.G.等人,1986,“Avermectins and Milbemycins”,Nat.Prod.Rep.,3,87-121,Mrozik H.等人,1983,Synthesis of Milbemycins from Avermectins,TetrahedronLett.,24,5333-5336,美国专利号4,134,973和EP 0 677 054。
大环内酯是天然产物或其半合成的衍生物。阿维菌素类和密比霉素类的结构是密切相关的,例如都具有复杂的16-元大环内酯环。天然产品阿维菌素类公开于U.S.专利号4,310,519而22,23-二氢阿维菌素化合物公开于U.S.专利号4,199,569(均通过援引并入本文)。还尤其提及U.S.专利号4,468,390,5,824,653,EP 0 007 812 A1,U.K.专利说明书1390 336,EP 0 002 916,和新西兰专利号237 086(都通过援引并入)。天然密比霉素类描述于U.S.专利号3,950,360(援引加入)以及"The Merck Index"12th ed.,S.Budavari,Ed.,Merck&Co.,Inc.Whitehouse Station,New Jersey(1996)引用的各种参考文献中。拉替待克丁描述于“International Nonproprietary Names for Pharmaceutical Substances(INN)”,WHO Drug Information,第17卷,第4期,263-286页,(2003)。这些类别化合物的半合成衍生物是本领域熟知的并描述于例如U.S.专利号5,077,308,4,859,657,4,963,582,4,855,317,4,871,719,4,874,749,4,427,663,4,310,519,4,199,569,5,055,596,4,973,711,4,978,677,4,920,148和EP 0 667 054(全部通过援引并入本文)。
在又一实施方式中,化合物I或化合物II可以与称为昆虫生长调节剂(IGRs)的一类化合物组合。属于该类的化合物是从业者熟知的并且涵盖宽范围的不同化学类别。这些化合物全都通过干扰昆虫病虫害的发育或生长起作用。昆虫生长调节剂描述于例如U.S.专利号3,748,356,3,818,047,4,225,598,4,798,837,4,751,225,EP 0 179 022或U.K.2 140010以及U.S.专利号6,096,329和6,685,954(全部通过援引并入本文)。
在一种实施方式中,IGR是模拟保幼激素的化合物。保幼激素模拟物的实例包括印楝素,苯虫醚,苯氧威,烯虫乙酯,烯虫炔酯,烯虫酯,吡丙醚,四氢印楝素和4-氯-2(2-氯-2-甲基-丙基)-5-(6-碘-3-吡啶基甲氧基)哒嗪-3(2H)-酮。
在又一实施方式中,IGR化合物是壳多糖合成抑制剂。壳多糖合成抑制剂包括抑太保,灭蝇胺,除虫脲,啶蜱脲,氟环脲,氟虫脲,氟铃脲,虱螨脲,虫酰肼,氟苯脲,杀铃脲,氟酰脲,1-(2,6-二氟苯甲酰基)-3-(2-氟-4-(三氟甲基)苯脲,1-(2,6-二氟-苯甲酰基)-3-(2-氟-4-(1,1,2,2-四氟乙氧基)-苯脲和1-(2,6-二氟苯甲酰基)-3-(2-氟-4-三氟甲基)苯脲。
在本发明的又一实施方式中,杀成虫剂杀昆虫剂和杀螨剂还能够与化合物I或化合物II组合。这些包括除虫菊素(其包括瓜叶菊素I、瓜叶菊素Ⅱ、茉酮菊素I、茉酮菊素Ⅱ、除虫菊素I、除虫菊素Ⅱ及其混合物)和拟除虫菊酯(包括氯菊酯、氯氟氰菊酯、氯氰菊酯、溴氰菊酯、氰戊菊酯、氟氰戊菊酯),和氨基甲酸酯类,其包括但不限于苯菌灵、氯苯虫威(carbanolate)、甲萘威、克百威、甲硫威、速灭威、蜱虱威、残杀威、涕灭威、丁酮威、杀线威、氰乙肟威(thiocarboxime)和久效威。
在某些实施方式中,化合物I或化合物II可以与一种或多种抗线虫剂组合,包括但不限于苯并咪唑、咪唑并噻唑、四氢嘧啶、有机磷酸酯化合物类别中的活性剂。在某些实施方式中,组合物中可以包括苯并咪唑,包括但不限于,噻菌灵,噻苯咪唑酯,丁苯咪酯,丙氧苯唑,甲苯咪唑,氟苯哒唑,硫苯唑,硫氧苯唑,丙硫多菌灵,环苯达唑,苯硫氨酯,硫菌灵及其o,o-二甲基类似物。
在其它实施方式中,化合物I或化合物II可以与咪唑并噻唑化合物组合,包括但不限于驱虫净、保松噻和丁咪唑。在其它实施方式中,本发明异噁唑啉化合物可以与四氢嘧啶活性剂组合,包括但不限于噻嘧啶、间酚嘧啶和噻烯氢嘧啶。适宜的有机磷酸酯活性剂包括但不限于蝇毒磷,敌百虫,皮虫磷,萘肽磷和敌敌畏,庚烯磷,速灭磷,久效磷,TEPP,和杀虫畏。
在其它实施方式中,化合物I或化合物II可以与下述组合:作为中性化合物及其各种盐形式的抗线虫化合物吩噻嗪和哌嗪,乙胺嗪,酚类比如二碘硝基酚,含砷制剂比如硫乙胂氨酸,乙醇胺比如苄酚宁,氯苯磺酸噻苯氧铵,和甲氧乙吡啶;菁类染料包括氯化扑蛲灵,双羟萘酸扑蛲灵和碘二噻宁;异硫氰酸酯包括对双异硫氰基苯,苏拉明钠,酞己炔酯,和各种天然产品,包括但不限于潮霉素B,α-茴蒿素和红藻氨酸。
在其他实施方式中,化合物I或化合物II可以与抗吸虫剂组合。适宜的抗吸虫剂包括但不限于米来西类比如米来西D和mirasan;吡喹酮,氯硝安定及其3-甲基衍生物,吡噻硫酮,胺甲硫蒽酮,羟胺硫蒽酮,羟氨喹,硝硫氰胺,硝噻哒唑,硝羟碘苄腈,本领域已知的各种双酚化合物包括毒菌酚,硫氯酚,硫氯酚亚砜和联硝氯酚;各种防霉胺(salicylanilide)化合物包括三溴柳苯胺,羟氯柳苯胺,氯碘酰胺,雷复沙奈(rafoxanide),溴硫柳酰胺,溴氟硝柳胺和氯生太尔;三氯苯咪唑,双醋氨苯氧乙醚,clorsulon,海妥林和吐根碱。
驱绦虫化合物还可以有利地与化合物I或化合物II组合,包括但不限于各种盐形式的槟榔碱,丁萘脒,杀螺胺,硝硫氰酯,巴龙霉素和巴龙霉素II。
在其它实施方式中,化合物I或化合物II可以与有效对抗节肢动物寄生物的其它活性剂组合。适宜的活性剂包括但不限于溴西克林,氯丹,滴滴涕,硫丹,林丹,甲氧滴滴涕,毒杀芬,溴硫磷,乙基溴硫磷,三硫磷,毒虫畏,毒死蜱,巴毒磷,畜蜱磷,二嗪磷,除线磷,,乐果,敌噁磷,乙硫磷,伐灭磷,杀螟硫磷,倍硫磷,磷吡酯(fospirate),碘硫磷,马拉硫磷,二溴磷,伏杀硫磷,亚胺硫磷,辛硫磷,胺丙畏,皮蝇磷,stirofos,烯丙菊酯,氯氟氰菊酯,氯氰菊酯,溴氰菊酯,氰戊菊酯,氟氰戊菊酯,氯菊酯,苯醚菊酯,除虫菊素,苄呋菊酯,苯甲酸苄酯,二硫化碳,克罗米通,除虫脲,二苯胺,双硫仑,异冰片基氰硫基乙酸酯,烯虫酯,舒非仑,pirenonylbutoxide,鱼藤酮,乙酸三苯基锡,氢氧化三苯基锡,避蚊胺,避蚊酯,和化合物1,5a,6,9,9a,9b-六氢-4a(4H)-二苯并呋喃甲醛(MGK-11),2-(2-乙基己基)-3a,4,7,7a-四氢-4,7-桥亚甲基-1H-异吲哚-1,3(2H)二酮(MGK-264),二丙基-2,5-吡啶二羧酸酯(MGK-326)和2-(辛硫基)乙醇(MGK-874)。
在又一实施方式中,化合物I或化合物II可以与拟除虫菊酯活性剂组合,包括但不限于氯菊酯,溴氰菊酯,氯氰菊酯,苯醚氰菊酯,醚菊酯,氰戊菊酯和氟氯氰菊酯。
能与化合物I或化合物II组合的又一抗寄生物剂包括生物学上活性的肽或蛋白质包括但不限于缩肽,其通过刺激属于分泌素受体家族的突触前受体在神经肌肉接点起作用引起寄生物的麻痹和死亡。在一种实施方式中,所述缩肽是艾莫德斯(emodepside)(参见Willson等人,Parasitology,Jan.2003,126(Pt 1):79-86)。
在又一实施方式中,化合物I或化合物II可以与新烟碱类类型农药的活性剂组合。新烟碱类结合并抑制昆虫特异性的烟酸乙酰胆碱受体。在一种实施方式中,新烟碱类杀昆虫剂是吡虫啉。吡虫啉是熟知的新烟碱类活性剂并且是局部杀寄生物剂产品Bayer AnimalHealth销售的K9和K9中的关键活性成分。该类试剂描述于例如U.S.专利号4,742,060或EP 0 892 060(通过援引并入本文)。
在又一实施方式中,新烟碱类活性剂是烯啶虫胺。烯啶虫胺是Novartis AnimalHealth销售的口服产品CAPSTARTM片剂中的活性成分。
在每日作为口服片剂提供的情况下,烯啶虫胺对成虫蚤有活性。烯啶虫胺通过干扰正常神经传播起作用并且导致昆虫死亡。烯啶虫胺具有对蚤很快速的起效。例如,CAPSTARTM片剂早在给药30分钟之后就对蚤开始起效,并且指示每天使用。
在某些实施方式中,能够与化合物I或化合物II组合的杀虫剂是缩氨脲比如氰氟虫腙。
在又一实施方式中,化合物I或化合物II可以有利地与本领域已知的异噁唑啉化合物组合。异噁唑啉活性剂是全身性起作用的活性剂,其高度有效地对抗外寄生物。这些活性剂描述于US 7,964,204,US 8,410,153,US 2011/0152312,US 2010/0254960 A1,US2011/0159107,US2012/0309620,US2012/0030841,US2010/0069247,WO 2007/125984,WO2012/086462,US 8,318,757,US 2011/0144349,US 8,053,452;US 2010/0137612,US2010/0254959,US 2011/152081,WO 2012/089623,WO 2012/089622,US 8,119,671;US 7,947,715;WO 2102/120135,WO 2012/107533,WO 2011/157748,US 2011/0245274,US 2011/0245239,US 2012/0232026,US 2012/0077765,US 2012/0035122,US 2011/0251247,WO2011/154433,WO 2011/154434,US 2012/0238517,US 2011/0166193,WO 2011/104088,WO2011/104087,WO 2011/104089,US 2012/015946,US 2009/0143410,WO 2007/123855 A2,US 2011/0118212,US7951828&US7662972,US 2010/0137372 A1,US 2010/0179194 A2,US2011/0086886 A2,US 2011/0059988 A1,US 2010/0179195 A1,US 7,897,630,U.S.7,951,828和US 7,662,972,通过援引将其全部并入本文。
在本发明的又一实施方式中,结袍酸(nodulisporic acid)及其衍生物(一类已知的杀螨、驱蠕虫、抗寄生物和杀昆虫剂)可以与化合物I或化合物II组合。这些化合物用来治疗或预防人类和动物中的感染且描述于例如U.S.专利号5,399,582,5,962,499,6,221,894和6,399,786,通过援引将其全部并入本文。
在又一实施方式中,氨基乙腈类(AAD)化合物比如monepantel(Zolvix)等的驱蠕虫化合物可以与化合物I或化合物II组合。这些化合物描述于例如WO 2004/024704和U.S.专利号7,084,280(通过援引并入);Sager等人,Veterinary Parasitology,2009,159,49-54;Kaminsky等人,Nature vol.452,2008年3月13日,176-181。
本发明化合物还可以与其他芳基并吡咯-2-基氰基乙基氨基化合物相组合,比如描述于Soll等人US专利号8,088,801的那些,通过援引将其并入本文,和这些化合物的硫代酰胺衍生物,描述于U.S.专利号7,964,621,也通过援引并入本文。
化合物I或化合物II还可以与副梅花状青霉酰胺(paraherquamide)化合物和这些化合物的衍生物相组合,包括derquantel(参见Ostlind等人,Research in VeterinaryScience,1990,48,260-61;和Ostlind等人,Medical and Veterinary Entomology,1997,11,407-408)。副梅花状青霉酰胺类化合物是已知类别的具有对抗某些寄生物的活性的化合物,其包括螺二氧杂环庚二烯并吲哚核心(参见Tet.Lett.1981,22,135;J.Antibiotics1990,43,1380,和J.Antibiotics 1991,44,492)。此外,结构上有关的marcfortine类化合物比如marcfortines A-C,也是已知的并且可以与本发明配制剂相组合(参见J.Chem.Soc.-Chem.Comm.1980,601和Tet.Lett.1981,22,1977)。副梅花状青霉酰胺衍生物的其他描述可以参见例如WO 91/09961,WO 92/22555,WO 97/03988,WO 01/076370,WO 09/004432,美国专利5,703,078和美国专利5,750,695,通过援引将其全部并入本文。
在本发明的又一实施方式中,化合物I或化合物II可以与土壤放线菌刺糖多孢菌(Saccharopolyspora spinosa)产生的多杀霉素(spinosyn)活性剂(参见例如SalgadoV.L.和Sparks T.C.,"The Spinosyns:Chemistry,Biochemistry,Mode of Action,andResistance,"Comprehensive Molecular Insect Science,vol.6,pp.137-173,2005)或半合成的类多杀霉素(spinosoid)活性剂组合。多杀霉素类(spinosyns)一般地称为因子或组分A、B、C、D、E、F、G、H、J、K、L、M、N、0、P、Q、R、S、T、U、V、W或Y,而这些组分中任意种或其组合可以用于本发明组合物中。多杀霉素化合物可以是稠合至12-元大环内酯的5,6,5-三环环系,中性糖(鼠李糖),和氨基糖(forosamine)。这些和其它天然多杀霉素化合物(包括可以用于本发明组合物中的Saccharopolyspora pagona产生的21-丁烯基多杀霉素)可以经由本领域已知的常规技术发酵来产生。可以用于本发明组合物中的其它多杀霉素化合物公开于U.S.专利号5,496,931;5,670,364;5,591,606;5,571,901;5,202,242;5,767,253;5,840,861;5,670,486;5,631,155和6,001,981,全部通过援引整体并入本文。多杀霉素化合物可以包括但不限于多杀霉素A,多杀霉素D,多杀霉素,乙基多杀菌素,或其组合。多杀霉素是多杀霉素A和多杀霉素D的组合,而乙基多杀菌素是3’-乙氧基-5,6-二氢多杀霉素J和3’-乙氧基多杀霉素L的组合。
通常,组合物中包括的额外活性剂的量是约0.1μg至约1000mg。更一般地,额外活性剂可以以约10μg至约500mg,约1mg至约300mg,约10mg至约200mg或约10mg至约100mg的量包括。
在本发明的其它实施方式中,额外活性剂可以包括在组合物中以递送约5μg/kg至约50mg/kg动物体重的剂量。在其它实施方式中,额外活性剂可以以足以递送约0.01mg/kg至约30mg/kg、约0.1mg/kg至约20mg/kg、或约0.1mg/kg至约10mg/kg动物体重的剂量的量存在。在其它实施方式中,额外活性剂可以以约5μg/kg至约200μg/kg或约0.1mg/kg至约1mg/kg动物体重的剂量存在。在本发明的又一实施方式中,包括的额外活性剂的剂量是约0.5mg/kg至约50mg/kg。
实施例1:制备化合物2,2-溴-4,5-二氯甲苯
将3,4-二氯甲苯(100g,1当量(eq.))和三溴化铁(55.1g)加至500mL二氯甲烷和冷却至约-5℃。将溴(99.2g)稀释在100mL(1体积(vol.))二氯甲烷中并滴加至混合物,在约-5℃搅拌所得混合物。反应混合物用12.5%NaHSO3水溶液(500mL)在20℃处理和搅拌30分钟。让两相分离,分开的有机层用饱和NaHCO3水溶液(600mL,6vol.)、盐水(500mL,5vol.)洗涤,然后减压浓缩至约4-5vol。加甲醇倍增体积,过滤所得的固体,用甲醇洗涤,和干燥,提供120g的化合物2,纯度为99.7%。
实施例2:制备化合物3,2-甲酰基-3,4-二氯甲苯。
在约-40至-50℃在氮气下将N-丁基锂(31.2mL,2.4M,2.0当量)加至无水四氢呋喃(20mL)。将所得溶液冷却至约-70℃。滴加化合物2(10g,1当量)的无水四氢呋喃(20mL)溶液,在约-70℃至约-80℃搅拌2小时。加入N,N-二甲基甲酰胺(9.1g,3当量),让温度温热至约10℃。随后,加入盐酸水溶液(64mL,2.6M),和加入乙酸异丙酯(30mL)。分开有机层,用盐水(50mL)洗涤两次,在≤约40℃减压缩减体积。加N-庚烷使体积达到三倍然后减压浓缩,然后重复3次直至THF和乙酸异丙酯的含量测定为小于3%重量。在约-5℃至0℃搅拌混合物2小时,过滤所得沉淀和用n-庚烷洗涤。获得化合物3(6.1g,99.7%纯度),是米白色固体。
实施例3:制备化合物4,3,4-二氯-5-甲酰基-2-硝基甲苯。
在-5℃至0℃将化合物3(37.8g,1当量)分批加至浓硫酸(189mL,5vol.)。在15分钟内将发烟硝酸(25mL,2.8当量)滴加至反应混合物,将反应在-5℃至0℃保持3小时。加入冰水(1L),将所得混合物搅拌2小时并让其升至环境温度。收集所得固体,用水(12ml,3vol.)冲洗两次。所得滤饼用饱和NaHCO3水溶液(120mL)处理,过滤所得固体,提供43g粗制化合物4(92.7%纯度)。
实施例4:制备化合物5,3,4-二氯-5-二氟甲基-2-硝基甲苯。将化合物4(100g,1当量)加至1升(10vol.)二氯甲烷,将所得溶液冷却至约0℃。将二(2-甲氧基乙基)氨基硫三氟化物("BAST",113.4g,1.2当量)滴加至混合物和在约0℃搅拌。在约5℃加水(400mL),用15%Na2CO3溶液(约600mL)将混合物调节至pH 7-8。分离有机相和用盐水洗涤(500mL),减压浓缩至约3vol。所得残余物与n-庚烷(3vol.)混合并再次减压浓缩。在约0℃搅拌混合物2小时,过滤收集固体。所得滤饼用n-庚烷(100mL x 2)洗涤和干燥,提供化合物5(86g,90.1%纯度),是浅黄色固体。
实施例5:制备化合物6,2,3-二氯-5-二氟甲基-6-甲基苯胺。将化合物5(50g,1当量)加至甲醇(250mL,5体积)和加入钯/碳(5g,50%,在水中,0.10w/w)。在40-45℃用于10atm的氢气处理反应混合物。给反应降压,将混合物过滤通过硅藻土,于40±5℃将浓缩滤液至约2-3体积。将乙酸乙酯(3vol.)加至混合物,在小于45℃减压浓缩所得混合物至约2-3体积。将N-庚烷(3vol.)加至所得残余物,然后在小于45℃减压浓缩混合物至约2-3vol。在约-5至0℃搅拌n-庚烷混合物2小时,收集所得沉淀,用庚烷(2x 50mL)洗涤,提供化合物6(35.6g,95.5%纯度),是黄色固体。
实施例6:制备化合物7a。
将冰乙酸(3.1L,8vol.)和化合物6(385g,1当量)混合和搅拌30分钟,将所得混合物冷却至约0°-10℃。将亚硝酸钠(130g,1.1当量)的65mL水溶液分批加入以便保持温度在约0°-10℃。将混合物分批倾至20L冰水以保持温度在约0°-15℃。收集所得沉淀,用水(2L)、庚烷(1.2L)洗涤,减压干燥,提供粗制产品。粗制产品在庚烷中制,再过滤,干燥,获得化合物7a,(327g,95.8%纯度)。
实施例7:制备化合物7b。
将化合物7a(800g,1当量)加至二氯甲烷(32L)。加入碳酸钠(716g,2当量)/水(8L),随后四丁基溴化铵(217g)。将混合物冷却至0-5℃,和加入氯丙酮(375g,1.2当量)。将混合物温热至15-20℃和搅拌24小时。分开有机层,用水(4L,5vol.)和盐水(4L)洗涤,在小于40℃减压浓缩。将所得液体加热至35-40℃和搅拌1小时,然后冷却至0-5℃和搅拌2小时。收集所得沉淀,用二氯甲烷:n-庚烷的1:1v/v混合物(共1.6L)洗涤和干燥,获得化合物7b,是褐色固体(497g,97.9%纯度)。
实施例8:制备化合物8。
将化合物7b(2.0kg,1当量)与N,N-二甲基甲酰胺(10L,5vol.)混合,和将氯化铵(730g,2当量)加至混合物。加入氢氧化铵(4.88L,7M,5当量),将所得混合物冷却至10-15℃。加入三甲基甲硅烷基氰化物(1.36kg,2当量)同时保持温度在约10-15℃。将反应加热至40-45℃持续24小时,然后在水(40L,20vol.)中稀释,搅拌所得混合物2小时。收集所得沉淀,用水洗涤(3x 2L),和在50-55℃干燥16小时,提供化合物8,是浅黄色固体(2.05kg,97.4%纯度)。
实施例9:制备化合物I.
将化合物8(3.5kg,1当量)加至四氢呋喃(35L,10vol.)和冷却至0-5℃。加入三乙胺(1.67kg,1.5当量)、随后4-(三氟甲硫基)苯甲酰氯(2.80kg,1.05当量)同时保持温度在0-5℃。搅拌反应混合物2小时,在40℃浓缩至2-3体积。加入二氯甲烷(17.5L,5vol.),在约40℃或更低减压浓缩混合物至2-3体积。加入二氯甲烷(52.5L),有机相用盐酸水溶液(17.5L,0.5M)、饱和NaHCO3水溶液(17.5L)、水(17.5L)和盐水(17.5L)洗涤。有机相在40℃浓缩至约2-3体积,然后冷却至0-5℃和搅拌2小时。收集所得沉淀,滤液用二氯甲烷(3x3.5L)洗涤。将粗制产品(4.66kg)加至二氯甲烷(7L,2vol.),将混合物加热至40℃,和搅拌2小时。将混合物冷却至0-5℃和搅拌2小时。收集所得固体,用二氯甲烷(7L)洗涤和干燥,获得化合物I,是浅褐色固体(4.15kg,99.7%纯度,72.3%收率)。通过在甲醇中重结晶实现将化合物I纯化至99.9%纯度。
实施例10:在体外对捻转血矛线虫(Haemonchus contortus)幼虫测试来自专利公开No.WO2010/056999(‘999App)的3种化合物、化合物I和化合物II以确定化合物抑制90%幼虫运动性的最小浓度(MIC90)。用下述程序来进行研究:将20头L1捻转血矛线虫幼虫加至微滴定板孔,其含有DMSO中的试验化合物和营养素培养基。可微滴定板在27℃和97%相对湿度保持4天时间段。在这些条件下,所加的幼虫发展至L3阶段。基于所得L3幼虫的运动性且与仅用DMSO处理的对照孔的运动性相比来确定化合物效力。
各化合物的MIC90如下表1中所示:
表1
化合物 | MIC<sub>90</sub>(ppm) |
I | 0.0003 |
‘999App,2.038 | 0.0024 |
‘999App,2.041 | 0.0024 |
‘999App,2.049 | 0.0012 |
II | 0.0012 |
化合物2.038是
化合物2.041是
化合物2.049是
实施例11:化合物I单独和与阿维菌素类组合的体内效力
在作为口服溶液口服给予的情况下研究化合物I对牛中的寄生胃肠道线虫的效力。在实验中,用寄生线虫感染30只大约8至12周龄的雄性去势乳牛犊。牛犊在第-33天接种帕氏血矛线虫(Haemonchus placei)和奥氏奥斯特线虫(Ostertagia ostertagi)和在第-21天点状古柏线虫(Cooperia punctata)和肿孔古柏线虫(Cooperia oncophora)。将牛犊分配至6个处理组之一。处理组1的牛犊是未处理的。处理组2-6的牛犊在第0天如下表2所示用配制剂处理,其含有载体中的5%(w/v)化合物I,所述载体包含50%(v/v)PEG 400以及其余的(QS至130mL)PEG 300。
表2
处理组 | 活性剂 | 剂量 |
1 | 未处理 | NA |
2 | 化合物I | 2mg/kg |
3 | 依立诺克丁 | 0.075mg/kg |
4 | 依维菌素 | 0.150mg/kg |
5 | 化合物I+依立诺克丁 | 2mg/kg+0.075mg/kg |
6 | 化合物I+依维菌素 | 2mg/kg+0.150mg/kg |
在第16天将全部牛犊安乐死,从各牛犊回收皱胃和小肠并为了寄生物回收进行处理。在未处理组中的全部5只牛犊都具有充分感染的帕氏血矛线虫,奥氏奥斯特线虫,点状古柏线虫和肿孔古柏线虫。各处理组相对对照组的效力示于下表3:
如表3所示,与依立诺克丁(组3)或依维菌素(组4)相比,化合物I显著更加有效地对抗肿孔古柏线虫雄性和古柏线虫属雌性蠕虫。此外,尽管依维菌素单独并未有效对抗肿孔古柏线虫雄性蠕虫,化合物I和依维菌素的组合提供几乎100%效力。这些结果展示化合物I对胃肠道线虫(包括更不易受阿维菌素类处理影响的那些)的出人意料的效力。化合物I对不易受大环内酯治疗影响的线虫品系展示的效力是出人意料且难以预料的。此外,化合物I和大环内酯的组合对这些线虫展示的效力也是出人意料且难以预料的。
Claims (19)
2.权利要求1的化合物,其中所述化合物是对映体富集的。
3.权利要求2的化合物,其中所述化合物是(R)-对映体富集的。
4.权利要求2的化合物,其中所述化合物是以至少95:5重量的比率(R)-对映体富集的。
5.杀寄生物组合物,包含权利要求1的式I化合物或其盐以及药学上可接受的载体。
6.权利要求5的组合物,其中所述组合物配制用于口服施用、局部施用或注射施用。
7.权利要求5或6的组合物,还包含一种或多种额外的杀寄生物活性剂。
8.权利要求5至7中任一项的组合物,其中所述额外的杀寄生物活性剂选自一种或多种大环内酯,一种或多种多杀霉素化合物,一种或多种类多杀霉素化合物,一种或多种环状缩肽,一种或多种苯并咪唑类,保松噻,噻嘧啶,莫仑太尔,吡喹酮,氯生太尔,氯舒隆,一种或多种氨基乙腈活性剂,一种或多种昆虫生长调节剂,一种或多种拟除虫菊酯,一种或多种苯基吡唑,一种或多种新烟碱类和一种或多种不同的芳基并吡咯-2-基氰基乙基氨基活性剂,或其组合。
9.权利要求8的组合物,其中额外的活性剂是大环内酯。
10.权利要求9的组合物,其中大环内酯是阿维菌素类或密比霉素类,其选自阿维菌素、地马待克丁、多拉克丁、甲氨基阿维菌素、依立诺克丁、依维菌素、拉替菌素、雷皮菌素、司拉克丁、弥拜菌素、密比霉素D、密比霉素A3、密比霉素A4、密比霉素肟、莫昔克丁和奈马克丁。
11.权利要求10的组合物,其中大环内酯是依维菌素,依立诺克丁,司拉克丁,密比霉素肟或莫昔克丁。
12.权利要求6至11中任一项的组合物,其中所述组合物是可咀嚼组合物。
13.权利要求6至11中任一项的组合物,其中所述组合物是口部顿服组合物。
14.权利要求6至11中任一项的组合物,其中所述组合物是泼浇剂组合物。
15.权利要求6至11中任一项的组合物,其中所述组合物是涂抹剂组合物。
16.在哺乳动物中治疗或预防内寄生物感染的方法,其包括向动物给予有效量的权利要求1的式I化合物或权利要求2的杀寄生物组合物。
17.权利要求16的方法,其中内寄生物感染是由选自下述的内寄生物引起的:裸头绦虫属(Anaplocephaela(Anoplocephala)),钩口线虫属(Ancylostoma),Anecator,蛔虫属(Ascaris),布鲁属(Brugia),仰口线虫属(Bunostomum),毛细线虫属(Capillaria),夏伯特线虫属(Chabertia),古柏线虫属(Cooperia),盅口属(Cyathostomum),杯环属(Cylicocyclus),双冠属(Cylicodontophorus),杯冠属(Cylicostephanus),盆口属(Craterostomum),网尾属(Dictyocaulus),双瓣丝虫属(Dipetalonema),复孔属(Dipylidium),恶丝虫属(Dirofilaria),龙线虫属(Dracunculus),棘球属(Echinococcus),蛲虫属(Enterobius),吸虫属(Fasciola),类丝虫属(Filaroides),胃线虫属(Habronema),血矛线虫属(Haemonchus),后圆线虫属(Metastrongylus),蒙尼属(Moniezia),板口线虫属(Necator),细颈线虫属(Nematodirus),日圆线虫属(Nippostrongylus),结节线虫属(Oesophagostumum),盘尾属(Onchocerca),奥斯特线虫属(Ostertagia),尖尾线虫属(Oxyuris),副蛔虫属(Paracaris),血吸虫属(Schistosoma),圆线虫属(Strongylus),绦虫属(Taenia),弓蛔虫属(Toxocara),类圆线虫属(Strongyloides),弓蛔线虫属(Toxascaris),毛线虫属(Trichinella),鞭虫属(Trichuris),毛圆线虫属(Trichostrongylus),三齿线虫属(Triodontophorous),钩虫属(Uncinaria),吴策属(Wuchereria),及其组合。
18.权利要求17的方法,其中内寄生物是捻转血矛线虫(Haemonchus contortus),环纹奥斯特线虫(Ostertagia circumcincta),艾氏毛圆线虫(Trichostrongylus axei),透明毛圆线虫(Trichostrongylus colubriformis),短古柏线虫(Cooperia curticei),巴特斯细颈线虫(Nematodirus battus),及其组合。
19.权利要求16至18中任一项的方法,其中内寄生物对阿维菌素类或密比霉素类治疗有抗性。
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US11773066B2 (en) | 2023-10-03 |
EP3883648A1 (en) | 2021-09-29 |
US20220017473A1 (en) | 2022-01-20 |
UY38482A (es) | 2020-05-29 |
WO2020112374A1 (en) | 2020-06-04 |
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