CN1348363A - 新的药物盐形式 - Google Patents
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Abstract
合成的非生物碱药用有机碱的糖精盐提供了一种具有改善的感官性质及溶解度降低的新盐形式。
Description
本申请享有1998年8月27日提出的USSN 60/098,154临时申请的优先权。
本发明涉及一些药理活性有机碱的新颖盐形式及它们的制剂。这类化合物可用丁螺环酮琥珀酸盐(一种有用的抗焦虑剂)来举例。
已知当许多有机碱可作为有用的药用制剂时,其盐类形式却少有用作药物,这是由于其溶解性提高,容易化合以及稳定性的问题。一般认为药物的口服剂型是优选的给药形式。然而大多数有机碱具有非常苦的味道,口服难以接受。其需要用各种制药配方中熟知的方法进行包裹,例如甜味剂、芳香剂、感官增强剂等。
一般认为大多数碱的强烈苦味可以用药物活性制剂的盐形式例如盐酸盐取代药物配方中的碱来减轻一些。在降低药物制剂令人不快的味道方面,药物的一些盐形式比其它形式更为有效。已知患者遵从医嘱坚持药物治疗通常要受到药物产品中令人不快味道的负面影响,尤其是当患者的病情伴随有食欲丧失、恶心和呕吐症状时。
在U.S.4,362,730中,Rader等人公开并对长春胺(一种药理活性生物碱)的糖精盐进行了要求。据描述,长春胺糖精盐具有改善的溶解度和改善的味道特征。长春胺糖精盐更大的溶解度不同于在本发明常规中所看到的糖精盐的溶解度降低现象。
本发明涉及非生物碱药用有机碱的新盐类形式,其使得通常苦味的药物变得更加可口,因此方便了其药物制剂经口服途径给药,因为在那里药物的味道会开始发挥作用,例如液体悬浮液、锭剂、口嚼片、香口胶等等。当应用于合成有机碱药物时,与生物碱相反,与更标准的药用盐类比较(例如卤化物、硫酸盐等),这类盐的溶解度通常更小一些。
一些非生物碱有机碱的糖精盐类提供了一种具有改善的传入感官性质的新盐形式。对于一些药物来说,糖精盐还凭籍着与更标准的药物盐类(例如卤化物、硫酸盐、磷酸盐等)比较具有降低的水溶解度特点提供了使药物缓释的手段。通过使糖精钠溶液与酸加成盐(例如药用有机碱的盐酸盐)混合进行盐交换,可以方便地制备得到糖精盐。也可以采用其它制药领域内熟知的盐形成反应。
欲将各种类型的口服活性非生物碱合成药用有机碱应用到本发明中。这些药用碱中的一部分被归入下列医用目录中;
●抗感染药,例如红霉素
●瘤细胞溶解剂;
●止痛剂,例如可待因,哌替啶、镇痛新、环丁羟吗喃、叔丁啡;
●精神药理制剂
●神经病制剂
●麻醉剂
●呼吸制剂
●心血管/心-肾制剂
●内分泌制剂
●代谢制剂
●胃肠道制剂
●抗过敏制剂
●免疫制剂
精神药理制剂还可以细分为:
●抗焦虑剂;例如苯并二氮杂类,例如三唑安定、氮杂吡隆(azapirones)类,如丁螺环酮;
●抗精神病制剂;例如吩噻嗪类,如氯吡胺和甲硫哒嗪,哌嗪类,如氟奋乃静,噻吨类,如氨砜噻吨,丁酰苯类,如氟哌啶醇,二苯并氧氮类(dibenzoxapines),如克塞平,二氢吲哚酮类,如吗啉吲酮;以及
●作用于失调的制剂,例如丙咪嗪、氯哌三唑酮、萘发唑酮、氟苯氧丙胺、舍曲林等,右旋苯丙胺以及哌醋甲酯(methylphenidate)。
神经病制剂可由开马君、双环哌丙醇、金刚烷胺和丙炔苯丙胺;麦角胺和美舍吉特(methylsergide);东莨菪碱、苯甲嗪、羟嗪等作为代表。
麻醉剂可由苯佐卡因、地布卡因、利多卡因、普卡因等作为代表。
呼吸剂可由肾上腺素、苯福林、苯并胺醇和假麻黄碱;异丙肾上腺素和叔丁喘宁作为代表。
心血管制剂可再细分为:
●心肌收缩制剂,例如多巴酚丁胺
●抗心律失常制剂,例如胺酰醋苯胺、丙吡胺;
●β-阻断剂,例如心得安、氨酰心安、萘羟心安;
●钙阻断剂,例如硫氮酮、硝苯吡啶和硝苯吡酯;
●血管舒张制剂,例如罂粟碱和苯氧丙酚胺;
●抗高血压制剂,例如肼苯哒嗪;和
●利尿剂,例如氨苯喋啶和氨氯吡脒,
内分泌制剂有溴麦角环肽和克罗米芬;代谢制剂有苯乙双胍胃肠道制剂有米他克酰胺或西米替丁。
本发明涉及可以口服给药的药用碱的稳定结晶性糖精盐。糖精(化学名为1,2-苯并异噻唑-3(2H)-酮1,1二氧化物)可用作甜味剂,通常以其钠盐的二水合水物形式存在。当其在制药领域中用作甜味剂时,它的用途是作为混合物的一种组分。当糖精在稀释水溶液中提供甜味时,其甜味约为蔗糖的500倍,即使在1∶100,000的稀释溶液中也仍然能检测到其甜味的存在。尽管这样,糖精具有滞后的苦金属味道。由于糖精的味道在稀释的溶液中是最令人愉快的,在对糖精固体进行制剂时需要多加小心,这是因为其固体形式具有非常令人不快的味道。
对比而言,本发明涉及实际的盐形式,与混合物相反,其包含有机碱的阳离子以及糖精盐阴离子。在这种形式下,药物具有令人愉快的感官性质,甚至是在它的盐形式下。在这种情况下,糖精盐为药物配方提供了潜力,因为其不需要大量的其它感官增强剂,例如甜味剂、芳香剂等,而在通常情况下需要这些物质使药用碱更加可口。糖精盐的优点在配制口服悬浮液、口嚼片、锭剂和快速熔化的剂型方面特别明显。
本发明的另一个方面涉及,与药用碱的常用酸加成盐(例如盐酸盐、硫酸盐、磷酸盐等)相比,非生物碱的药用碱糖精盐的溶解度普遍降低。随着溶解度的降低,药物的释放放缓并且通常释放期延长。因此,糖精盐为一些药物的缓释剂型提供了一种方法。
下列实施例将进一步说明本发明,但不限制本发明。实施例1-丁螺环酮糖精盐
在搅拌下,将丁螺环酮盐酸盐(8-4[4-(2-嘧啶基)-1-哌嗪基])丁基]-8-氮杂螺-[4.5]癸-7,9-二酮盐酸盐4.22g,10mmol)溶于最少量的水中,向其中加入糖精钠的浓溶液(2.05g,10mmol)。冷却混合物,从溶于二氯甲烷中的重油层中倾析出上清的水层。用水洗涤二氯甲烷层,硫酸镁干燥。过滤干燥的溶液,真空浓缩至清澈油状物。用乙醚研制得到浅黄色糖精盐m.p.142-145℃。
分析:
理论值:C21H31N5O2·C7H5NO3S:C,59.14;H,6.38;N,14.78;S,5.64
实测值:C,59.14;H,6.46;N,14.89;S,5.51
实施例2-味道实验
在单盲条件下,采用三个小玻璃平皿进行味道实验。#1平皿含有丁螺环酮盐酸盐。#2平皿含有丁螺环酮糖精盐,#3平皿含有1∶1摩尔等当量的丁螺环酮盐酸盐和糖精钠的物理混合物。要求品味志愿者品尝每一个样品并给出他们的感受。所有的志愿者均选择2#平皿(丁螺环酮糖精盐)为味道最好的样品。相反,志愿者认为#1平皿和#3平皿的味道令人不快或高度令人不快。
Claims (14)
1.能够形成酸加成盐的非生物碱有机药用碱的糖精盐。
2.权利要求1中所述的盐类,其中的碱为有用的非生物碱口服活性制剂,所述制剂选自精神药理制剂、止痛剂、神经病制剂、麻醉剂、呼吸制剂、心血管-肾制剂、血液制剂、内分泌制剂和代谢制剂、胃肠道制剂、皮肤制剂、抗炎症制剂、抗过敏制剂、免疫制剂、瘤细胞溶解制剂以及抗感染制剂。
3.权利要求2中所述的盐类,其中的碱是有用的口服活性抗感染制剂。
4.权利要求2中所述的盐类,其中的碱是有用的口服活性止痛制剂。
5.权利要求2中所述的盐类,其中的碱是有用的口服活性心血管-肾制剂。
6.权利要求2中所述的盐类,其中的碱是有用的口服活性胃肠道制剂。
7.权利要求2中所述的盐类,其中的碱是有用的口服活性神经病制剂。
8.权利要求2中所述的盐类,其中的碱是有用的口服活性精神药理制剂。
9.权利要求8中所述的精神药理制剂,其可用于治疗抑郁。
10.权利要求8中所述的精神药理制剂,其可用于治疗焦虑。
11.权利要求10中所述的精神药理制剂,其为氮杂吡隆。
12.权利要求11中所述的氮杂吡隆,其选自丁螺环酮和吉吡隆。
13.权利要求11中所述的氮杂吡隆为丁螺环酮糖精盐。
14.制备糖精盐的方法,其包括将药用碱酸加成盐溶液和糖精钠溶液进行混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9815498P | 1998-08-27 | 1998-08-27 | |
US60/098,154 | 1998-08-27 |
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CN1348363A true CN1348363A (zh) | 2002-05-08 |
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CN99810139A Pending CN1348363A (zh) | 1998-08-27 | 1999-08-26 | 新的药物盐形式 |
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EP (1) | EP1107738A4 (zh) |
JP (1) | JP2003525855A (zh) |
CN (1) | CN1348363A (zh) |
AU (1) | AU6021199A (zh) |
CA (1) | CA2341522A1 (zh) |
WO (1) | WO2000012067A1 (zh) |
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DE202010001237U1 (de) | 2010-01-21 | 2010-04-01 | Grünenthal GmbH | Kombination aus Tramadol und Acetaminophen als Brausetablette |
EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
TW201617343A (zh) | 2014-09-26 | 2016-05-16 | 阿爾米雷爾有限公司 | 具有β2腎上腺素促效劑及M3蕈毒拮抗劑活性之新穎雙環衍生物 |
NL2031332B1 (en) * | 2022-03-18 | 2023-09-29 | Plethora Therapeutics B V | Transmucosal delivery of psychoactive compounds |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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FR1288002A (fr) * | 1954-06-14 | 1962-03-24 | Pfizer & Co C | Perfectionnements apportés aux procédés de fabrication de composés d'imidazoline |
ES271829A1 (es) * | 1960-12-19 | 1962-03-01 | Tanabe Seiyaku Co | Un procedimiento para preparar una sal comestible de acido benzofenoma-2-carboxilico y 1-metil-3-(di-2-tienilmetilen) piperidina |
US4711784A (en) * | 1986-01-07 | 1987-12-08 | Warner-Lambert Company | Encapsulation composition for use with chewing gum and edible products |
US5837277A (en) * | 1992-06-04 | 1998-11-17 | Smithkline Beecham Corporation | Palatable pharmaceutical compositions |
-
1999
- 1999-08-26 CN CN99810139A patent/CN1348363A/zh active Pending
- 1999-08-26 CA CA002341522A patent/CA2341522A1/en not_active Abandoned
- 1999-08-26 WO PCT/US1999/019575 patent/WO2000012067A1/en not_active Application Discontinuation
- 1999-08-26 JP JP2000567187A patent/JP2003525855A/ja active Pending
- 1999-08-26 AU AU60211/99A patent/AU6021199A/en not_active Abandoned
- 1999-08-26 EP EP99968215A patent/EP1107738A4/en not_active Withdrawn
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105407890A (zh) * | 2013-07-25 | 2016-03-16 | 阿尔米雷尔有限公司 | 包含maba化合物和皮质类固醇的结合物 |
CN105407890B (zh) * | 2013-07-25 | 2019-06-07 | 阿尔米雷尔有限公司 | 包含maba化合物和皮质类固醇的结合物 |
CN107868117A (zh) * | 2016-09-28 | 2018-04-03 | 中国科学院苏州纳米技术与纳米仿生研究所 | 司坦唑醇糖精盐及其制备方法和应用 |
CN107868117B (zh) * | 2016-09-28 | 2021-04-23 | 中国科学院苏州纳米技术与纳米仿生研究所 | 司坦唑醇糖精盐及其制备方法和应用 |
Also Published As
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EP1107738A4 (en) | 2003-01-22 |
CA2341522A1 (en) | 2000-03-09 |
EP1107738A1 (en) | 2001-06-20 |
AU6021199A (en) | 2000-03-21 |
WO2000012067A1 (en) | 2000-03-09 |
JP2003525855A (ja) | 2003-09-02 |
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