CN1328558A - A晶型8－氰基－1－环丙基－7－(1s,6s－2,8－二氮杂二环[4.3.0]壬烷－8－基)－6－氟－1,4－二氢－4－氧代－3－喹啉羧酸 - Google Patents

A晶型8－氰基－1－环丙基－7－(1s,6s－2,8－二氮杂二环[4.3.0]壬烷－8－基)－6－氟－1,4－二氢－4－氧代－3－喹啉羧酸 Download PDF

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CN1328558A
CN1328558A CN99813686A CN99813686A CN1328558A CN 1328558 A CN1328558 A CN 1328558A CN 99813686 A CN99813686 A CN 99813686A CN 99813686 A CN99813686 A CN 99813686A CN 1328558 A CN1328558 A CN 1328558A
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ccdc
crystal form
diazabicyclo
cyclopropyl
dihydro
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CN1135230C (zh
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T·希姆勒
W·哈伦巴赫
H·拉斯特
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract

本发明涉及具有确定晶型的式(Ⅰ)的8－氰基－1－环丙基－7－(1S,6S－2,8－二氮杂双环[4.3.0]壬烷－8－基)－6－氟－1,4－二氢－4－氧代－3－喹啉羧酸、其制备方法及其在药物制剂中的应用。该晶型可以通过其特征性的X－射线粉末衍射图和差热分析图(见说明书),区别于其它晶型的式(Ⅰ)8－氰基－1－环丙基－7－(1S,6S－2,8－二氮杂双环[4.3.0]壬烷－8－基)－6－氟－1,4－二氢－4－氧代－3－喹啉羧酸。

Description

A晶型8-氰基-1-环丙基-7-(1S，6S-2，8-二氮杂二环 [4.3.0]壬烷-8-基)-6-氟-1，4-二氢-4-氧代-3-喹啉羧酸
本发明涉及具有确定晶型的8-氰基-1-环丙基-7-(1S，6S-2，8-二氮杂双环[4.3.0]壬烷-8-基)-6-氟-1，4-二氢-4-氧代-3-喹啉羧酸、其制备方法及其在药物制剂中的应用。
在下文中，式(I)的8-氰基-1-环丙基-7-(1S，6S-2，8-二氮杂双环[4.3.0]壬烷-8-基)-6-氟-1，4-二氢-4-氧代-3-喹啉羧酸称作CCDC。
CCDC在DE-A 19 633 805或PCT申请号97 903 260.4中是已知的，根据这些出版物，它是在助剂碱的存在下，在二甲基甲酰胺和乙腈的混合物中，将7-氯-8-氰基-1-环丙基-6-氟-1，4-二氢-4-氧代-3-喹啉羧酸与(1S，6S)-2，8-二氮杂双环[4.3.0]壬烷反应来制备的。将水加入到混合物中，然后用二氯甲烷从水中萃取CCDC，除去萃取剂将其分离。这样得到的粉末，其晶型是不明确的。更确切地说，该粉末多半是无定形的，且可能含有不同晶型的混合物。即使偶然形成了单一的晶型，但怎样进行萃取并能够获得确定的形式，是不清楚的。然而，制备药剂的前提是，对于存在不同晶型的活性化合物，用来制剂的是哪一种晶型，事先一定要清楚。
此外，按照上述制备方法获得的部分无定形的粉末是吸湿性的。无定形固体，特别是吸湿性固体，例如由于其松散而密度低，比较差的流动性能，所以进行药物加工时难以处理。另外，考虑到所生产的固体制剂中活性化合物的含量或稳定性，吸湿性固体的处理需要特殊的加工技术和设备，以实现可重现的结果。
因此，本发明的目的是制备具有确定晶型的CCDC，由于它的物理特性，特别是晶体性能和对水的特性，因而在药物制剂中易于加工处理。
本发明通过新的CCDC晶型达到了这一目的，以下该晶型称作A晶型。
因此，本发明提供了A晶型的CCDC，通过X-射线粉末衍射图对其进行了表征，具有高强度和中强度(＞30％相对强度)的反射信号(2θ)，列于下表1中。
表1：
A晶型的粉末-X射线衍射图
                        2θ
                        6.70
                        8.92
                        12.44
                        13.66
                        15.96
                        17.60
                        21.42
                        21.78
                        28.97
A晶型特征性的粉末-X射线衍射图还表示在附图1中。
此外，本发明CCDC的A晶型的另外一些性质，也不同于CCDC的其它形式，这些性质本身或者和其它参量一起，可用于表征本发明CCDC的A晶型。
特别地，用差热分析(DTA)测定的熔点249-252℃表征了A晶型的CCDC。特征性的差热分析图表示在附图2中。
还用在KBr中所测定的红外光谱表征了A晶型的CCDC，如附图3所示。
此外，A晶型的CCDC可以通过以下给出的制备方法获得，由此对其予以表征：将未知晶型的或无定形的CCDC溶解于热水或热的醇/水混合物中，随后加入醇，冷却至室温后，分离出沉淀的固体。
在优选的实施方案中，所用的醇是乙醇或异丙醇。
A晶型的CCDC出人意料地稳定，并且即使较长时间储存，也不转变为其它晶型或无定形形式。此外，与无定形CCDC相比较，A晶型在大气中吸收水分少得多。鉴于此，它非常适于制备片剂或其它固体制剂。由于其稳定性，使得这些制剂具有所期望的长期储存稳定性。因此，采用A晶型，可以按照明确指定的方式来制备稳定的CCDC固体制剂。
在人药和兽药领域，A晶型的CCDC对致病菌是高活性的，其应用范围之广与CCDC相一致。
用于表征CCDC的A晶型的X-射线粉末衍射图，是采用由Stoe公司生产的、具有位置敏感探测器(ortsempfindlichemDetektor)(PSD2)的透射衍射计(Transmissions diffraktometer)STADI-P测得的。
差热分析的熔点是采用由Mettler-Toledo公司生产的DSC 820设备测得的。将A晶型的CCDC样品于铝坩埚中暴露在大气下以10K/min的速率加热。
IR光谱是采用由Biorad公司生产的FTS 60A设备在KBr中测得的。
以下的实施例是对本发明的阐明而不是限定。下述实施例所用的稀释剂/碱体系是特别优选的。对比实施例
将3.07g7-氯-8-氰基-1-环丙基-6-氟-1，4-二氢-4-氧代-3-喹啉羧酸、1.39g(1S，6S)-2，8-二氮杂双环[4.3.0]壬烷、2.24g1，4-二氮杂双环[2.2.2]辛烷(DABCO)、29.5ml二甲基甲酰胺和29.5ml乙腈组成的混合物在室温下搅拌16小时。用旋转蒸发器将反应混合物在60℃浴温下浓缩，并将残留物置移至10ml水中，所得溶液用稀盐酸调节至pH7并滤去固体，将滤液振荡萃取三次，每次用二氯甲烷20ml。有机相用硫酸钠干燥并过滤，滤液用旋转蒸发器在60℃浴温下浓缩，得到2.4g浅棕色固体，其X-射线粉末衍射图如附图4所示，因此主要是无定形的。
在95％的大气相对温度(采用水中沉积有Na2HPO4×12H2O饱和溶液形成)下，按照该方法所获得的固体，在一天内吸收大约17％重量的水。
实施例1
将617g任意晶型的CCDC溶于6170ml氯仿中，加入100g硫酸钠，将混合物搅拌5分钟，然后经50g硅藻土过滤，随后用100ml氯仿洗涤，在低达10mbar的剩余压力下，于旋转蒸发器上蒸去溶剂，得到玻璃状的残留物。将740ml水和740ml乙醇加入到该残留物，并将混合物与60℃加热，直到残留物全部溶解，将该溶液加入到17升沸腾的乙醇中，该混合物再沸腾5分钟，然后在1小时时间内冷却至35℃，抽滤出所沉淀的晶体，并于20℃干燥约16小时，然后在30℃减压条件下干燥直至恒重。
得到530g固体，其X-射线粉末衍射图如附图1所示，差热分析图如附图2所示，IR光谱如附图3所示。
在95％的大气相对湿度(采用水中沉积有Na2HPO4×12H2O的饱和溶液形成)下，按照该方法所获得的固体，在一天内吸收大约3％重量的水。
实施例2
将2g未知晶型的CCDC溶于4ml水中，加入4ml异丙醇，搅拌下将反应混合物缓慢加热，然后再加入32ml异丙醇。将所得透明溶液加热至沸腾，溶液变得浑浊，片刻内晶体析出。回流3分钟后，停止加热，在没有搅拌的情况下，令沉淀物静置3-4小时。然后抽滤出固体，用异丙醇洗涤，并在大气中干燥直至恒重。得到1.54g固体，其X-射线粉末衍射图如附图1所示，差热分析图如附图2所示，IR光谱如附图3所示。

Claims (8)

1.A晶型的8-氰基-1-环丙基-7-(1S，6S-2，8-二氮杂双环[4.3.0]壬烷-8-基)-6-氟-1，4-二氢-4-氧代-3-喹啉羧酸(CCDC)，其特征在于它的X-射线粉末衍射图具有以下高强度和中强度的反射信号(2θ)：
                        2θ
                        6.70
                        8.92
                        12.44
                        13.66
                        15.96
                        17.60
                        21.42
                        21.78
                        28.97
2.A晶型的8-氰基-1-环丙基-7-(1S，6S-2，8-二氮杂双环[4.3.0]壬烷-8-基)-6-氟-1，4-二氢-4-氧代-3-喹啉羧酸(CCDC)，其特征在于它的X-射线粉末衍射图具有以下高强度和中强度的反射信号(2θ)：
                        2θ
                        6.70
                        8.92
                        12.44
                        13.66
                        15.96
                        17.60
                        21.42
                        21.78
                        28.97
并具有通过DTA测定的249-252℃熔点。
3.A晶型的8-氰基-1-环丙基-7-(1S，6S-2，8-二氮杂双环[4.3.0]壬烷-8-基)-6-氟-1，4-二氢-4-氧代-3-喹啉羧酸(CCDC)，它是通过将未知晶型的CCDC或无定形CCDC溶于水或水/醇混合物，然后加入醇进行热沉淀而获得的。
4.制备权利要求1的A晶型CCDC的方法，其特征在于将未知晶型的CCDC或无定形CCDC溶于水或水/醇混合物，加入醇后进行热沉淀。
5.根据权利要求4的制备A晶型的CCDC的方法，其特征在于所用的醇为乙醇或异丙醇。
6.药物，其特征在于：除了常规的辅剂和载体以外，它还包括权利要求1-3任一项的A晶型CCDC。
7.权利要求1-3任一项的A晶型CCDC在制备药物中的用途。
8.权利要求1-3任一项的A晶型CCDC在抗菌组合物中的用途。
CNB998136867A 1998-11-25 1999-11-15 A晶型8-氰基-1-环丙基-7-(1s,6s-2,8-二氮杂二环[4.3.0]壬烷-8-基)-6-氟-1,4-二氢-4-氧代-3-喹啉羧酸 Expired - Fee Related CN1135230C (zh)

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DE19854355A1 (de) 1998-11-25 2000-05-31 Bayer Ag Kristallmodifikation B von 8-Cyan-1-cyclopropyl-7-(1S, 6S-2,8-diazabicyclo-/4.3.O/nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure
DE19908449A1 (de) 1999-02-26 2000-08-31 Bayer Ag Kristallmodifikation C von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicylo-[4.3.0]nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chino/incarbonsäure
DE19908448A1 (de) 1999-02-26 2000-08-31 Bayer Ag Kristallmodifikation D von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicylo[4.3.0)nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chino incarbonsäure

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AR031216A1 (es) 2003-09-17
HUP0104465A2 (hu) 2002-04-29
RU2247122C2 (ru) 2005-02-27
EP1133496B1 (de) 2004-04-21
KR100740947B1 (ko) 2007-07-19
NZ511861A (en) 2002-12-20
CA2351712C (en) 2011-07-12
NO20012460D0 (no) 2001-05-18
ATE264858T1 (de) 2004-05-15
HUP0104465A3 (en) 2002-12-28
ES2217843T3 (es) 2004-11-01
DK1133496T3 (da) 2004-08-09
AU1553300A (en) 2000-06-13
IL142696A (en) 2006-04-10
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JP2002530406A (ja) 2002-09-17
BRPI9915669A (pt) 2001-08-14
BRPI9915669B8 (pt) 2021-07-06
PL347786A1 (en) 2002-04-22
NO318066B1 (no) 2005-01-31
NO20012460L (no) 2001-05-18
AU763883B2 (en) 2003-07-31
IL142696A0 (en) 2002-03-10
CA2351712A1 (en) 2000-06-02
PT1133496E (pt) 2004-08-31
HK1042703A1 (zh) 2002-08-23
DE59909262D1 (de) 2004-05-27
EP1133496A1 (de) 2001-09-19
KR20010080926A (ko) 2001-08-25
UA67874C2 (uk) 2004-07-15
TW576835B (en) 2004-02-21
TR200101438T2 (tr) 2001-10-22
WO2000031075A1 (de) 2000-06-02
US6436955B1 (en) 2002-08-20
HK1042703B (zh) 2004-12-03
SK6822001A3 (en) 2001-12-03
BRPI9915669B1 (pt) 2017-07-04
DE19854356A1 (de) 2000-05-31
CZ300016B6 (cs) 2009-01-14
CN1135230C (zh) 2004-01-21

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