CN1384109A - 一种有抗生育作用的化合物及制备方法 - Google Patents

一种有抗生育作用的化合物及制备方法 Download PDF

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CN1384109A
CN1384109A CN 01112795 CN01112795A CN1384109A CN 1384109 A CN1384109 A CN 1384109A CN 01112795 CN01112795 CN 01112795 CN 01112795 A CN01112795 A CN 01112795A CN 1384109 A CN1384109 A CN 1384109A
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CN1172950C (zh
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李瑞麟
卢琦华
倪志刚
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Shanghai Academy Of Science & Technology
Shanghai Institute of Planned Parenthood Research
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Shanghai Institute of Planned Parenthood Research
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Abstract

本发明提供了一种具有抗生育作用的化合物,该化合物结构是2α,17α－双乙炔基,A－失碳,5α－雄甾烷,2β,17β－双羟基酯。该化合物经动物试验证明有很好的抗生育作用,可制成口服避孕药。

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一种有抗生育作用的化合物及制备方法
本发明属化学合成，具体涉及一种有抗生育作用的化合物及制备方法。
目前，国内外应用的口服避孕药种类较多，例如1号口服避孕药(炔诺酮)、2号口服避孕药(甲地孕酮)、18-甲基炔诺酮以及近期的第三代口服避孕药敏定偶(孕二烯酮)等，它们均需与少量雌激素配合。服法：在来月经的第7天开始连续服用21-22天，停药后等待下月来经后再照上法服用，但由于一般工作人员较为繁忙，以及出差等任务原因，易于疏忽遗忘漏服，造成中途出血或避孕失败。
此外53号口服探亲避孕药双炔失碳酯(Anordrin)，我国已推广应用20余年，主要作用为抗着床，但有少数人服用后有轻度恶心，思吐等暂时性副作用，且目前我国夫妇分居两地者逐渐减少。
因此，人们期望能寻找一种较为简便的、副作用小的口服避孕药。
本发明目的在于克服现有避孕药的缺点，提供一种效果好、副作用小的口服避孕药。
本发明人经过长期研究，提供了一种有抗生育作用的化合物，该化合物为2α，17α-双乙炔基，A-失碳，5α-雄甾烷，2β，17β-双羟基衍生物，具有下式结构[I]：
Figure A0111279500031
分子结构式[I]其中  Ia R1＝R2＝H
Figure A0111279500033
Figure A0111279500035
Figure A0111279500041
上述化合物经质谱测定证明其分子量符合上述结构。
上述化合物经动物试验证明有很好的抗生育作用。
动物试验结果：
实验方法：雌雄鼠(2∶1)合笼过夜，次日晨阴道涂片，镜检如发现精子定为妊娠第1天，每组取10只妊娠雌鼠，当即口服给药一次，至妊娠第16天处死妊鼠剖腹检查着床点，如未发现活胎仔，即为该化合物有抗生育作用。实验结果如下表：
    化合物代号     剂量   抗生育有效率
    OCD-01     2.5mg/kg     14％
    OCD-02     1.4mg/kg     100％
    OCD-03     0.7mg/kg     100％
    OCD-04     1.4mg/kg     100％
从以上结果说明这类化合物具有较好的避孕效果。
本发明的另一目的是提供了上述化合物的制备方法，该方法是将α，17α-双乙炔基，A-Nor，5α-雄甾烷，2β，17β-双羟基化合物与相应的酯进行酯化反应得到相应的2α，17α-双乙炔基，A-Nor，5α-雄甾烷，2β，17β-双羟基化合物的酯衍生物。
Figure A0111279500042
其中R1、R2同上述定义
本发明的化合物在低剂量下，每月仅需服用一次即达到避孕目的，服用方法比较简便。
实施例1
2α，17α-双乙炔基，A-Nor，5α-雄甾烷，2β，17β-双羟基双三氯醋酸酯(OCD-02)
5g(Ia)加12mlACOH加热溶解后，冷水冷却，加8g三氯醋酐室温搅拌反应1小时，加水稀释，析出固体，滤去，溶于乙醇，用活性炭脱色浓缩至固体析出，冷后析出颗粒透明结晶得1.8g mp.108-9℃。
实施例2
2α，17α-双乙炔基，A-Nor，5α-雄甾烷，2β，17β-双羟基2β-单琥珀酸酯(OCD-03)
2g(Ia)加10ml吡啶和4g琥珀酸酐、0.2g醋酸钠，搅拌回流反应3小时，加水50℃保温搅拌2小时，冷后用乙醇提取，水洗至中性，浓缩，室温放置徐徐析出固体，滤出用CH3OH-H2O重结晶得1gmp.217-219℃[α]D24.88°(乙醇)。
实施例3
2α，17α-双乙炔基，A-Nor，5α-雄甾烷，2β，17β-双羟基双琥珀酸酯(OCD-04)
10g(Ia)加40ml吡啶和30g琥珀酸酐，1g P.T.S.搅拌回流10小时，加水50℃保温2小时，用乙醇提取，水洗至中性，浓缩，室温放置，徐徐析出固体，滤出，用乙醇重结晶得3g mp.220-221℃[α]D24.6°(氯仿)。
实施例4
2α，17α-双乙炔基，A-Nor，5α-雄甾烷，2β，17β-双羟基双丁酸酯(OCD-05)
1.5g(Ia)加30ml丁酸酐，0.5g P.T.S.100℃搅拌反应1小时，加水放置过夜析出长针状结晶2.1g，以95％乙醇重结晶mp.145-147℃。

Claims (2)

1.一种具有抗生育作用的化合物，其特征在于该化合物由下式表示：
Figure A0111279500021
分子结构式[I]
   Ia  R1＝R2＝H
Figure A0111279500024
Figure A0111279500026
2.一种如权利要求1所述的一种具有抗生育作用的化合物的制备方法，其特征在于该方法将α，17α-双乙炔基，A-Nor，5α-雄甾烷，2β，17β-双羟基化合物与相应的酯进行酯化反应得到相应的2α，17α-双乙炔基，A-Nor，5α-雄甾烷，2β，17β-双羟基化合物的酯衍生物。
Figure A0111279500027
其中R1、R2同上述定义
CNB011127953A 2001-04-29 2001-04-29 一种有抗生育作用的化合物及制备方法 Expired - Lifetime CN1172950C (zh)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102218069A (zh) * 2011-04-08 2011-10-19 上海奥奇医药科技有限公司 A-失碳-5α-雄甾烷化合物在制备抗恶性肿瘤药物中的应用
CN102872026A (zh) * 2011-07-15 2013-01-16 上海科学院 一种化合物的新用途
WO2014062625A1 (en) * 2012-10-15 2014-04-24 Iowa State University Research Foundation, Inc. Tackifier compounds and methods of using the same
US10077257B2 (en) 2015-04-06 2018-09-18 Iowa State University Research Foundation, Inc. Aziridinated triglycerides and polymers formed therefrom
US10081638B2 (en) 2011-09-09 2018-09-25 Iowa State University Research Foundation, Inc. Polyisocyanates from fused bicyclic polyols and polyurethanes therefrom
US10392471B2 (en) 2015-05-14 2019-08-27 Iowa State University Research Foundation, Inc. Polymers and methods of making the same

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102218069B (zh) * 2011-04-08 2012-09-26 上海奥奇医药科技有限公司 A-失碳-5α-雄甾烷化合物在制备抗恶性肿瘤药物中的应用
CN102218069A (zh) * 2011-04-08 2011-10-19 上海奥奇医药科技有限公司 A-失碳-5α-雄甾烷化合物在制备抗恶性肿瘤药物中的应用
CN102872026A (zh) * 2011-07-15 2013-01-16 上海科学院 一种化合物的新用途
US10081638B2 (en) 2011-09-09 2018-09-25 Iowa State University Research Foundation, Inc. Polyisocyanates from fused bicyclic polyols and polyurethanes therefrom
WO2014062625A1 (en) * 2012-10-15 2014-04-24 Iowa State University Research Foundation, Inc. Tackifier compounds and methods of using the same
US9556293B2 (en) 2012-10-15 2017-01-31 Iowa State University Research Foundation, Inc. Polyisocyanates from fused bicyclic polyols and polyurethanes therefrom
US9688794B2 (en) 2012-10-15 2017-06-27 Iowa State University Research Foundation, Inc. Tackifier compounds and methods of using the same
US9920145B2 (en) 2012-10-15 2018-03-20 Iowa State University Research Foundation, Inc. Tackifier compounds and methods of using the same
WO2014062631A1 (en) * 2012-10-15 2014-04-24 Iowa State University Research Foundation, Inc. Polyisocyanates from fused bicyclic polyols and polyurethanes therefrom
US10280241B2 (en) 2012-10-15 2019-05-07 Iowa State University Research Foundation, Inc. Tackifier compounds and methods of using the same
US10550210B2 (en) 2012-10-15 2020-02-04 Iowa State University Research Foundation, Inc. Polyisocyanates from fused bicyclic polyols and polyurethanes therefrom
US10077257B2 (en) 2015-04-06 2018-09-18 Iowa State University Research Foundation, Inc. Aziridinated triglycerides and polymers formed therefrom
US10501448B2 (en) 2015-04-06 2019-12-10 Iowa State University Research Foundation, Inc. Aziridinated triglycerides and polymers formed therefrom
US10392471B2 (en) 2015-05-14 2019-08-27 Iowa State University Research Foundation, Inc. Polymers and methods of making the same

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