CN115385845A - 一种吡咯磺酸类化合物盐型制备 - Google Patents

一种吡咯磺酸类化合物盐型制备 Download PDF

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CN115385845A
CN115385845A CN202211060475.0A CN202211060475A CN115385845A CN 115385845 A CN115385845 A CN 115385845A CN 202211060475 A CN202211060475 A CN 202211060475A CN 115385845 A CN115385845 A CN 115385845A
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苏梅
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Abstract

本发明提供了一种1‑(5‑(2‑氟苯基)‑1‑3‑(3‑甲氧丙氧基)苯磺酰氯)‑1H‑吡咯‑3‑基)‑N‑甲基胺盐型,包括有机酸盐或无机酸盐。本发明主要对各种有机酸和无机酸进行筛选,得到纯度更高、稳定性更好的1‑(5‑(2‑氟苯基)‑1‑3‑(3‑甲氧丙氧基)苯磺酰氯)‑1H‑吡咯‑3‑基)‑N‑甲基胺盐酸盐和1‑(5‑(2‑氟苯基)‑1‑3‑(3‑甲氧丙氧基)苯磺酰氯)‑1H‑吡咯‑3‑基)‑N‑甲基胺富马酸盐,可用于治疗糜烂性食管炎、胃溃疡、十二指肠溃疡、幽门螺杆菌根除适应症,并治疗由于胃酸过多而引起的相关疾病。

Description

一种吡咯磺酸类化合物盐型制备
技术领域
本发明属于化合物领域,具体的涉及1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺盐型及其制备方法。
背景技术
胃酸相关性疾病是消化系统疾病中最为常见的一类疾病,是指一类由于胃酸分泌过多,或对胃酸特别敏感而引起的一类消化道疾病的总称,常见的有胃食管反流病,消化性溃疡、卓-艾综合征及非甾体类抗炎药物引起的消化系统疾病。
自1988年以来,以奥美拉唑为代表的质子泵抑制剂通过抑制胃酸分泌以治疗消化性溃疡、反流性食管炎和卓-艾综合症等在临床上得到广泛应用。长期的临床应用发现,现有质子泵抑制剂在药代动力学、药效学方面还有局限性。如:给药时间对药效的影响;夜间酸突破起效慢;酸性条件下不稳定(需要配制成肠制剂);对CYP450酶的依赖性(导致个体差异显著)等。
PPI是目前抑酸作用最强的一类药物,如奥美拉唑、兰索拉唑、泮托拉唑、雷贝拉唑等。由于PPI存在着夜间酸反跳现象,从而影响治疗效果。钾离子竞争型酸阻滞剂(P-CAB)类药物的出现很好地解决了这一问题,通过竞争型抑制剂质子泵(H+,ATPase)中的K+而起作用,临床上可明显减少夜间酸反跳的发生,此类药物包括:TAK438、瑞伐拉赞(Revaprazan)等。
钾竞争性酸阻滞剂(Potassium-Competitive Acid Blockers,P-CABs)通过直接、可逆性的过程竞争性地抑制H+/K+-ATP酶中的K+而产生作用。与传统质子泵抑制剂相比,P-CABs具有亲脂性、弱碱性、解离常数高和在低pH条件下稳定的特点。在酸性环境下,P-CABs以离子化形式与H+/K+-ATP酶结合,阻止H+运送及酸分泌到胃腔中,迅速升高胃中pH值。动物实验和临床研究表明:P-CABs具备起效迅速,在1小时内就能达到最大治疗效果;血药浓度与口服给药剂量线性相关,比较容易达到最佳抑酸效果的优势。
尽管目前已公开了一系列钾竞争性酸阻滞剂,但仍需要开发结构类型更丰富,新的可能具有更好的成药性质的化合物,经过不断努力,本发明设计具有通式所示的结构的化合物,并发现具有此类结构的化合物表现出优异的效果和作用。
发明内容
本发明目的在于,在现有的基础上,提供了一种新的胃酸分泌抑制剂,该化合物具有更好的稳定性以及生物活性。本文主要研究了该化合物的盐型,对各种有机酸和无机酸进行筛选,得到了纯度更高,稳定性更好的一种盐型。1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺盐酸盐在这一系列化合物中有着更高的纯度和稳定性,为以后的剂型研究提供了支持,从而更有效的治疗胃酸相关性疾病,满足不同的临床用药需求。
本发明的技术方案为:公布了具有下列通式的1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺有机酸盐或无机酸盐。
Figure BDA0003824825120000021
式中n为1或1/2,HA为有机酸或无机酸
其所述的有机酸为:草酸、丁二酸、乳酸、甲磺酸、L-苹果酸、枸橼酸。
其所述的无机酸为:硝酸、氢溴酸、磷酸、硫酸。
本发明提供上述有机酸盐或无机酸盐的制备方法,该方法包括以下步骤:
方法一(酸为液体):将1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺与有机溶剂搅拌下溶解(一般每克游离胺用4-8mL),在室温下,将相应的酸(游离胺与相应的酸的摩尔比为1:1.05)滴加到反应体系中,搅拌2小时,后将所得固体过滤,固体用有机溶剂洗2次(一般每克游离胺用5-6mL),并将得到的固体在真空烘箱中干燥(35℃)4小时,即制得相关的盐。
方法二(酸为固体):将1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺与有机溶剂混合,并在搅拌下溶解(一般每克游离胺用4-8mL),在室温下,将相应的酸(一般每克游离胺用3-5mL,游离胺与相应的酸的摩尔比为1:1.05),加到反应体系中,加热搅拌搅拌1小时,后将所得固体过滤,固体用有机溶剂洗2次(一般每克游离胺用5-6mL),并将得到的固体在真空烘箱中干燥(35℃)4小时,即制得相关盐。
具体实施方式
以下实施例用以说明本发明,但不作为对本发明的限制。
以下参考实施例中,所用仪器:
核磁共振仪:德国BRUKER 500MHZ
高效液相色谱仪:安捷伦1260
电子天平:Mettler XS105
真空烘箱:上海索谱仪器公司真空干燥箱DZF6021
恒温恒湿试验箱:
实施例1
1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺甲磺酸盐
在100mL单口瓶中,加入1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺(5.0g,11.6mmol)和乙酸乙酯(25mL),并在室温下(25℃)搅拌溶解,向反应体系中滴加甲磺酸(1.3g,13.9mml),在该温度下搅拌2h,有固体析出,将固体过滤出,并用乙酸乙酯洗(8mL*2次),将所得到固体在真空烘箱中干燥(35℃)4小时,得类白色固体2.8g,收率为45.9%。
1HNMR(DMSO-d6;500MHZ)δ(ppm)7.60(s,1H),7.43(m,2H),7.24(m,1H),7.21(m,2H),7.05(m,2H),6.81(s,1H),6.35(s,1H),3.86(m,2H),3.70(s,2H),3.45(m,2H),3.23(s,3H),2.82(s,3H),2.38(s,3H),1.91(m,2H)。
实施例2
1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺硝酸盐在100mL单口瓶中,加入1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺(5.0g,11.6mmol)和乙酸乙酯(25mL),并在室温下(25℃)搅拌溶解,向反应体系中滴加硝酸(0.8g,13.9mmol),在该温度下搅拌2h,有固体析出,将固体过滤出,并用乙酸乙酯洗(8mL*2次),将所得到固体在真空烘箱中干燥(35℃)4小时,得类白色固体4.8g,收率为84.2%。
1HNMR(DMSO-d6;500MHZ)δ(ppm)7.59(s,1H),7.44(m,2H),7.34(m,1H),7.28(m,2H),7.15(m,2H),6.81(s,1H),6.55(s,1H),3.84(m,2H),3.72(s,2H),3.41(m,2H),3.22(s,3H),2.38(s,3H),1.93(m,2H)。
实施例3
1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺氢溴酸盐在100mL三口瓶中,加入1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺(5.0g,11.6mmol)和甲醇(25mL),并在室温下(25℃)搅拌溶解,加入氢溴酸(3.7g,13.9mmol,30%),在该温度下搅拌2h,有固体析出,将固体过滤出,并用乙酸乙酯洗(6mL*2次),将所得到固体在真空烘箱中干燥(35℃)4小时,得到当黄色固体1.3g,收率为22%。
1HNMR(DMSO-d6;500MHZ)δ(ppm)7.62(s,1H),7.56(m,2H),7.38(m,1H),7.35(m,2H),7.19(m,2H),6.93(s,1H),6.49(s,1H),3.96(m,2H),3.83(s,2H),3.55(m,2H),3.36(s,3H),2.30(s,3H),1.98(m,2H)。
实施例4
1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺丁二酸盐
在100mL三口瓶中,加入1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺(5.0g,11.6mmol)和甲醇(25mL),并在室温下(25℃)搅拌溶解,向反应体系加热至50℃,加入丁二酸(1.6g,13.9mmol),在该温度下搅拌2h,后将温度降至室温下(25℃),并搅拌10分钟,有固体析出,将固体过滤出,并用甲醇洗(6mL*2次),将所得到固体在真空烘箱中干燥(35℃)4小时,得到当白色固体4.1g,收率为65%。
1HNMR(DMSO-d6;500MHZ)δ(ppm)7.68(s,1H),7.58(m,2H),7.35(m,1H),7.31(m,2H),7.16(m,2H),6.98(s,1H),6.49(s,1H),3.96(m,2H),3.80(s,2H),3.57(m,2H),3.36(s,3H),2.58(m,4H),2.30(s,3H),1.93(m,2H)。
实施例5
1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺草酸盐
在100mL三口瓶中,加入1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺(5.0g,11.6mmol)和甲醇(30mL),并在室温下(25℃)搅拌溶解,后将温度升至50℃,加入草酸(1.2g,13.9mmol),并搅拌2h,有固体析出,将固体过滤出,并用甲醇洗(10mL*2次),将所得到固体在真空烘箱中干燥(35℃)4小时,得类白色固体5.0g,产率为:83%。
1HNMR(DMSO-d6;500MHZ)δ(ppm)7.56(s,1H),7.41(m,2H),7.34(m,1H),7.28(m,2H),7.16(m,2H),6.81(s,1H),6.65(s,1H),3.84(m,2H),3.72(s,2H),3.41(m,2H),3.22(s,3H),2.38(s,3H),1.92(m,2H)。
本发明化合物的稳定性考察实验
1.影响因素实验:将其中1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺甲磺酸盐、1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺氢溴酸盐、1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺硝酸盐、1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺丁二酸盐、1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺草酸盐分别进行影响因素实验:高温(60℃)分别在第5天和第10天取样,对化合物性状进行研究(颜色、溶解度),用高效液相色谱仪检测有关物质与含量。
高湿(92.5%RH)分别在第5天和第10天取样,对化合物性状进行研究(颜色、溶解度),用高效液相色谱仪检测关物质与含量。
光照(4500lx)分别在第5天和第10天取样,对化合物性状进行研究(颜色、溶解度),用高效液相色谱仪检测关物质与含量。
表1盐型稳定性实验表
Figure BDA0003824825120000051

Claims (5)

1.1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺有机酸盐或无机酸盐,
Figure FDA0003824825110000011
式中n为1或1/2,HA为有机酸或无机酸;其中所述有机酸为草酸、丁二酸、乳酸、甲磺酸、L-苹果酸、枸橼酸;所述无机酸为硝酸、氢溴酸、磷酸、硫酸。
2.根据权利要求1所述的1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺有机或无机酸盐,其制备方法如下:
(1)将5-(2-氟苯基)-N-甲基-1-(3-吡啶基磺酰基)-1H-吡咯-3-甲氨溶于有机溶剂中,
(2)向反应瓶中加入有机酸或无机酸,
(3)在相应的反应温度下搅拌2h,
(4)抽滤,滤饼真空干燥。
3.根据权利要求2所述的1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺有机或无机酸盐,其特征在于,制备方法中所用的有机溶剂选自乙酸乙酯、甲醇、丙酮、乙腈、四氢呋喃。
4.根据权利要求3所述的1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺有机或无机酸盐,其特征在于,制备方法中反应温度为0℃-50℃。
5.权利要求1-4任一所述的1-(5-(2-氟苯基)-1-3-(3-甲氧丙氧基)苯磺酰氯)-1H-吡咯-3-基)-N-甲基胺有机酸盐或无机酸盐在制备治疗糜烂性食管炎、胃溃疡、十二指肠溃疡、幽门螺杆菌根除适应症、并治疗由于胃酸过多而引起的相关疾病的药物中的用途。
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