CN100364540C - Pharmaceutical use of (2s-cis)-(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H)-one for treating hepatitis - Google Patents
Pharmaceutical use of (2s-cis)-(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H)-one for treating hepatitis Download PDFInfo
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- 208000006454 hepatitis Diseases 0.000 title claims abstract description 12
- 231100000283 hepatitis Toxicity 0.000 title claims abstract description 11
- LHBHZALHFIQJGJ-CABCVRRESA-N (2s,3s)-3-hydroxy-2-(4-methoxyphenyl)-3,5-dihydro-2h-1,5-benzothiazepin-4-one Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](O)C(=O)NC2=CC=CC=C2S1 LHBHZALHFIQJGJ-CABCVRRESA-N 0.000 title description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 18
- 229960003920 cocaine Drugs 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 150000002576 ketones Chemical class 0.000 claims abstract 3
- 208000005374 Poisoning Diseases 0.000 claims description 3
- 231100000572 poisoning Toxicity 0.000 claims description 3
- 230000000607 poisoning effect Effects 0.000 claims description 3
- 208000001378 Carbon Tetrachloride Poisoning Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract description 10
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 abstract description 8
- 238000011282 treatment Methods 0.000 abstract description 5
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 4
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 208000019423 liver disease Diseases 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 102000004357 Transferases Human genes 0.000 description 2
- 108090000992 Transferases Proteins 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 238000013245 carbon tetrachloride model Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 208000007848 Alcoholism Diseases 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 241000251569 Ciona Species 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
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- 208000010706 fatty liver disease Diseases 0.000 description 1
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- 201000007270 liver cancer Diseases 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- -1 penetrants Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
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Abstract
本发明公开了(2S-顺)-(+)-2，3-二氢-3-羟基-2-(4-甲氧苯基)-1，5-苯并硫氮杂-4(5H)-酮(简称为顺内)在制备治疗肝炎的药物中的新用途。以顺内为活性成分的药物可有效地治疗可卡因中毒性肝炎和四氯化碳中毒性肝炎。The invention discloses (2S-cis)-(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H ) - A new use of ketone (abbreviated as cisne) in the preparation of drugs for the treatment of hepatitis. Drugs with cisner as the active ingredient can effectively treat cocaine toxic hepatitis and carbon tetrachloride toxic hepatitis.
Description
技术领域Technical field
本发明涉及一种化合物在医药中的用途，具体地说，是(2S-顺)-(+)-2，3-二氢-3-羟基-2-(4-甲氧苯基)-1，5-苯并硫氮杂-4(5H)-酮(简称为顺内)在制备治疗肝炎的药物中的用途。The present invention relates to the use of a compound in medicine, specifically (2S-cis)-(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1 , the use of 5-benzothiazepine-4(5H)-one (abbreviated as cisne) in the preparation of drugs for the treatment of hepatitis.
背景技术Background technique
在消化道的疾病当中，肝病是严重危害人民健康的病种。我国目前约有1.2亿乙肝病毒终身携带者，其中3000万人会转变成慢性肝炎、肝硬化、肝癌，每年因肝病而死亡的人约有30万人。近年来，随着人民生活水平的不断提高，由嗜酒和其他一些因素而引起的脂肪肝，也日趋增多。在对健康造成损伤的同时，我国每年用于治疗肝病的费用高达400亿元人民币，对国民经济和社会发展也造成了很大的影响。由于目前尚缺乏特效治疗肝炎的方法，所以开发治疗肝病的新药非常迫切和重要。Among the diseases of the digestive tract, liver disease is a disease that seriously endangers people's health. There are currently about 120 million lifelong carriers of hepatitis B virus in my country, 30 million of whom will develop chronic hepatitis, cirrhosis, and liver cancer. About 300,000 people die from liver disease every year. In recent years, with the continuous improvement of people's living standards, fatty liver disease caused by alcoholism and other factors has also increased. While causing damage to health, my country's annual cost of treating liver disease is as high as 40 billion yuan, which has also had a great impact on the national economy and social development. Since there is currently a lack of specific treatments for hepatitis, it is very urgent and important to develop new drugs to treat liver diseases.
(2S-顺)-(+)-2，3-二氢-3-羟基-2-(4-甲氧苯基)-1，5-苯并硫氮杂-4(5H)-酮(简称为顺内)是我们最新筛选到的一种化合物，尚无人发现它的药用价值。(2S-cis)-(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H)-one ( (abbreviated as Shunei) is a compound we have recently screened, and no one has discovered its medicinal value yet.
发明内容Contents of the invention
本发明的目的是提供顺内的新用途，即在制备治疗肝炎的药物中的新应用。The purpose of the present invention is to provide a new use of cisner, that is, a new application in the preparation of medicines for treating hepatitis.
本发明的另一目的是提供一种治疗肝炎的药物。Another object of the present invention is to provide a medicine for treating hepatitis.
发明人按照《新药临床前研究指导原则》(1993年，国家药监局)等的保肝药方法对顺内进行了药理和病理研究。The inventor conducted pharmacological and pathological studies on Shunnei in accordance with the hepatoprotective drug methods such as "Guiding Principles for Preclinical Research of New Drugs" (1993, State Food and Drug Administration).
发明人发现，以顺内进行腹腔注射和口服给药，都有明显的效果，血清功能指标和病理指标都有明显的改善。The inventor found that both intraperitoneal injection and oral administration had obvious effects, and serum functional indicators and pathological indicators were significantly improved.
以顺内进行治疗时，它可以以粉剂、粒剂、片剂、胶囊、丸剂和液体药剂等形式口服给药；也可以以注射液、栓剂、经皮制剂、吸入剂等形式非经肠给药。顺内的有效药剂，是通过与适当的药用掺混物，如赋形剂、粘合剂、渗透剂、润滑剂等混合而配制成的。When treated internally, it can be administered orally in the form of powders, granules, tablets, capsules, pills and liquid pharmaceuticals; it can also be administered parenterally in the form of injections, suppositories, transdermal preparations, inhalants, etc. medicine. The effective pharmaceutical agents of Shunnei are formulated by mixing with appropriate pharmaceutical admixtures such as excipients, binders, penetrants, lubricants, etc.
给药剂量随患者的病情、给药途径、患者的年龄和体重而改变。在口服给药情况下，剂量通常为成年人100～1000mg/kg/天，优选为250～500mg/kg/天。The dosage varies with the patient's condition, route of administration, patient's age and weight. In the case of oral administration, the dosage is usually 100 to 1000 mg/kg/day for adults, preferably 250 to 500 mg/kg/day.
本发明的优点是：顺内可以治疗可卡因中毒性肝炎研究的化合物。可卡因是一种世界范围内流行的毒品。在2002年底我国就发生了100公斤可卡因走私的毒品大案。肝炎是可卡因中毒致死的一个重要原因。目前国际上还没有治疗可卡因中毒性肝炎的公认药物。顺内的抗毒品可卡因的作用在国内和国际上都是首次发现。顺内的抗四氯化碳中毒性肝炎的作用在国内和国际上也是首次发现。The advantage of the present invention is that the compound studied can be used to treat cocaine poisoning hepatitis. Cocaine is a popular drug worldwide. At the end of 2002, a major drug case involving the smuggling of 100 kilograms of cocaine occurred in our country. Hepatitis is an important cause of death from cocaine poisoning. There is currently no internationally recognized drug for the treatment of cocaine-induced hepatitis. The anti-drug effects of cocaine in Shunnei were discovered for the first time both domestically and internationally. The effect of Shunnei against carbon tetrachloride toxic hepatitis was discovered for the first time domestically and internationally.
顺内是一种市场上有销售的化合物。Ciona is a commercially available compound.
顺内的英文名字为：Shun Nei’s English name is:
(2S-cis)-(+)-2，3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1，5-benzothiazepin-4(5H)-one。(2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one.
分子式：C16H15NO3SMolecular formula: C 16 H 15 NO 3 S
分子量：301.36Molecular weight: 301.36
CAS登记号：42399-49-5CAS registration number: 42399-49-5
中文名字：(2S-顺)-(+)-2，3-二氢-3-羟基-2-(4-甲氧苯基)-1，5-苯并硫氮杂-4(5H)-酮。Chinese name: (2S-cis)-(+)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepine-4(5H) -ketone.
其它名称：顺内(简称为顺内)。Other names: Shun Nei (referred to as Shun Nei).
化学结构为：The chemical structure is:
具体实施方式Detailed ways
下面提供的实施例用于进一步阐明本发明，而不构成对本发明范围的限制。The examples provided below are used to further illustrate the present invention and are not intended to limit the scope of the present invention.
1.材料1.Materials
实施例所用顺内由化学试剂Acros Organics公司(美国)提供，含量98％。The cisplatin used in the examples was provided by the chemical reagent Acros Organics Company (USA), with a content of 98%.
其它的药品、试剂和实验动物，都能方便地市购。Other drugs, reagents and experimental animals can be easily purchased commercially.
2.制备方法例2. Preparation method example
取顺内100g，羟乙基纤维素10g，压片制成片剂，放在常温干燥的器皿中备用。Take 100g of Shunnei and 10g of hydroxyethyl cellulose, press them into tablets, and place them in a dry container at room temperature for later use.
3.试验方法3.Test method
实验动物为小鼠，体重为22～26g，由北京大学医学部实验动物中心提供。试验期间提供足量的自来水及普通饲料，动物室保持22℃，自动通风。动物的分组与处理将小鼠按体重随机分组。中毒性肝炎造模组前3天不给予任何处理，第4天皮下注射造模化合物(可卡因或四氯化碳)。顺内+造模化合物组分别以不同剂量顺内灌胃4天，每天1次。第4天灌胃给药后30分钟，皮下注射造模化合物溶液。造模化合物染毒24小时后，所有动物内眦取血，断髓处死，立刻留取肝脏，称重，将最大叶浸于10％的福尔马林中固定，进行肝脏大体的观察和留取肝脏标本，HE染色观察肝脏病理变化程度。利用7170A自动分析仪，采用酶联-紫外连续检测法，测定血清中肝功酶丙氨酸转移酶(ALT)、天冬氨酸转移酶(AST)和乳酸脱氢酶(LDH)的活性。统计分析方法实验数据以均数±标准差表示。应用SPSS11.5统计软件对实验结果采用方差分析、t检验等方法分析处理，p＜0.05认为组间差异具有显著性，p＜0.01认为组间差异具有高度显著性。The experimental animals were mice, weighing 22 to 26 g, and were provided by the Experimental Animal Center of Peking University School of Medicine. During the experiment, sufficient tap water and ordinary feed were provided, and the animal room was maintained at 22°C and automatically ventilated. Grouping and handling of animals Mice were randomly grouped according to body weight. The toxic hepatitis modeling group was not given any treatment for the first 3 days, and the modeling compound (cocaine or carbon tetrachloride) was injected subcutaneously on the 4th day. The rats in the intragastric + modeling compound group were intragastrically administered with different doses for 4 days, once a day. On the fourth day, 30 minutes after intragastric administration, the modeling compound solution was injected subcutaneously. After 24 hours of exposure to the modeling compound, blood was taken from the inner canthus of all animals, and the marrow was cut off and sacrificed. The livers were immediately collected and weighed. The largest lobe was immersed in 10% formalin and fixed. The liver was grossly observed and the livers were collected. Specimens were stained with HE to observe the degree of pathological changes in the liver. The activities of liver function enzymes alanine transferase (ALT), aspartate transferase (AST) and lactate dehydrogenase (LDH) in serum were measured using the 7170A automatic analyzer and the enzyme-linked-UV continuous detection method. Statistical analysis methods Experimental data are expressed as mean ± standard deviation. SPSS11.5 statistical software was used to analyze and process the experimental results using analysis of variance, t test and other methods. p<0.05 was considered to be significant, and p<0.01 was considered to be highly significant.
4.试验结果：4.Test results:
(1)顺内抗可卡因小鼠中毒性肝炎的效果可参见表1。(1) The effects of cisternal resistance to toxic hepatitis in cocaine-resistant mice can be seen in Table 1.
表1顺内抗可卡因中毒性肝炎的作用(血清生化指标)(
与可卡因模型组比较，*p＜0.05，**p＜0.01(n＝8)Compared with the cocaine model group, * p<0.05, ** p<0.01 (n=8)
(2)顺内抗四氯化碳小鼠中毒性肝炎的效果可参见表2。(2) The effect of synergism against toxic hepatitis in mice treated with carbon tetrachloride can be seen in Table 2.
表2顺内抗四氯化碳中毒性肝炎的作用(血清生化指标)(
与四氯化碳模型组比较，*p＜0.05，**p＜0.01(n＝8)Compared with the carbon tetrachloride model group, * p<0.05, ** p<0.01 (n=8)
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5102999A (en) * | 1989-12-06 | 1992-04-07 | Zambon Group S.P.A. | Process for the preparation of an intermediate of diltiazem |
| CN1160713A (en) * | 1996-02-23 | 1997-10-01 | 田边制药株式会社 | Process for the preparation of 1, 5-benzothiazepine * derivatives |
| WO1998036733A2 (en) * | 1997-02-24 | 1998-08-27 | Michael Albert Kamm | Topical pharmaceutical composition comprising a cholinergic agent or a calcium channel blocker |
| WO2002049603A1 (en) * | 2000-12-20 | 2002-06-27 | Lg Household & Health Care Ltd. | Compositions for prevention and alleviation of skin wrinkles |
-
2006
- 2006-03-14 CN CNB2006100575358A patent/CN100364540C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5102999A (en) * | 1989-12-06 | 1992-04-07 | Zambon Group S.P.A. | Process for the preparation of an intermediate of diltiazem |
| CN1160713A (en) * | 1996-02-23 | 1997-10-01 | 田边制药株式会社 | Process for the preparation of 1, 5-benzothiazepine * derivatives |
| WO1998036733A2 (en) * | 1997-02-24 | 1998-08-27 | Michael Albert Kamm | Topical pharmaceutical composition comprising a cholinergic agent or a calcium channel blocker |
| WO2002049603A1 (en) * | 2000-12-20 | 2002-06-27 | Lg Household & Health Care Ltd. | Compositions for prevention and alleviation of skin wrinkles |
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| CN1850088A (en) | 2006-10-25 |
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