CN1171108A - 稳定性优良的8-烷氧基喹诺酮羧酸水合物及其制备方法 - Google Patents
稳定性优良的8-烷氧基喹诺酮羧酸水合物及其制备方法 Download PDFInfo
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- CN1171108A CN1171108A CN95196983A CN95196983A CN1171108A CN 1171108 A CN1171108 A CN 1171108A CN 95196983 A CN95196983 A CN 95196983A CN 95196983 A CN95196983 A CN 95196983A CN 1171108 A CN1171108 A CN 1171108A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Quinoline Compounds (AREA)
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Abstract
本发明提供稳定性优良的如下式(1)所示的1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸·3/2水合物及其制备方法。
Description
技术领域
本发明涉及稳定性优良的1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸·3/2水合物及其制备方法。
技术背景
喹诺酮羧酸类抗菌剂近年来发展迅速,因具有从革兰氏阳性菌到革兰氏阴性菌的范围广泛的抗菌谱和很强的抗菌力,也可用于尿路感染以外的外科感染症,其有效性得到高度评价,在临床上作出重大贡献。
特别是1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸不仅因其优异的抗菌力,而且因其对细菌的选择性高及优异的选择毒性,而受到人们的注目。
特开昭62-252772号公报公开了式(2)所示的1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸的半水合物。
1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-吡嗪基)-4-氧代-3-喹啉羧酸因吸湿性强而易于制成水合物,从含水有机溶剂中重结晶,将经酸-碱重结晶的中和结晶法所得的结晶干燥,很容易制成半水合物。
然而,人们发现,1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸的半水合物随着湿度的升高而重量增加,而且在制片剂时崩解性和溶出性差,这样的制剂生产问题变得很明显。
发明的揭示
本发明者们以解决上述1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸半水合物的问题为目的进行研究,结果发现1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸·3/2水合物是稳定的化合物,在制剂生产上效果也好。即,1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸·3/2水合物在很宽的湿度条件下均稳定,而且片剂的崩解性和溶出性也良好。
而且,作为获得1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸·3/2水合物的手段,本发明者发现,将1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸的水悬浮液加热搅拌可高效地获得目的化合物,从而完成了本发明。
本说明书中的“水悬浮液”表示在精制阶段经酸-碱重结晶中和后的悬浮液、在分离所得的结晶中加水而成的悬浮液等,水的用量可按结晶的3-20倍加入,为使得到目的物的收率高,以用3-5倍为宜。
最好在50-100℃温度(以80-90℃为佳)搅拌10-30分钟。
水悬浮液的pH以中性附近(6.0-8.0)为佳。
此外,加热搅拌后滤取所得的目的物,将母液回至室温,可容易回收二次结晶,因此可使收率提高。
附图的简单说明
图1显示本发明物的热分析结果。
图2显示对照物的热分析结果。
图3显示本发明物的红外吸收谱。
图4显示对照物的红外吸收谱。
图5显示本发明物的X射线衍射结果。
图6显示对照物的X射线衍射结果。
图7显示本发明物的结晶结构。
实施发明的最佳方式
以下列出本发明的实施例,对本发明作更详细的说明,但本发明并不受这些实施例的任何限制。
实施例1
将1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸(85G)悬浮于水(425ml,5倍量)中,于内部温度80-85℃搅拌10分钟。在同样的温度下保温过滤后,干燥,得到目的物(84.43g),得率92.7%。
元素分析(%):C19H22FN3O4·3/2H2O
C H N 水分
计算值 56.71 6.26 10.44 6.7
实测值 56.79 6.15 10.44 7.3
(1)使用的仪器和设备
TG/DTA 理学电气(TAS-200;控制部)、
TG8101D2(测定装置)
红外分光光度计 日立制作所270-30型
X射线衍射装置 理学电气2013型
单结晶X射线衍射装置 理学电气AFC5R型
Karl Fischer湿度计 京都电子工业MKA-3P型
1)热分析(TG/DTA)
本发明物质和未经热水处理的对照物的样品各用约10mg,以α-氧化铝为对照,以5℃/分钟的升温速度从室温加热至240℃,分别测定这时的重量变化和热变化,其结果,本发明物见图1,对照物见图2。
2)红外吸收谱
本发明物和未经热水处理的对照物的各样品用KBr-透射法进行测定。其结果,本发明物和对照物分别见图3和图4。
3)粉末X射线衍射
将本发明物和对照物的各样品粉碎,用玻璃试样板进行测定,其结果,本发明物和对照物分别见图5和图6。
4)单结晶X射线衍射
X射线衍射的结果,所得结晶的结构显示于图7。
1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸·3/2水合物在通常的保存条件下保持一定量的水分,是稳定的。
将未处理物与本发明的热水处理物的热分析(TG/DTA)、红外吸收谱和粉末X射线衍射的测定数据进行比较,情况显然不同。十分明显,热水处理物与未处理物的晶型不同。
而且,从X射线衍射的结果证明了1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸·3/2水合物在单位晶格中含有1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸8分子和水12分子。
产业上利用的可能性
本发明的1-环丙基-6-氟代-1,4-二羟基-8-甲氧基-7-(3-甲基-1-哌嗪基)-4-氧代-3-喹啉羧酸·3/2水合物的崩解性和溶出性俱优,且稳定性也好,在制剂生产上是有非常用的。
Claims (2)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP33556994A JP3449658B2 (ja) | 1994-12-21 | 1994-12-21 | 安定性に優れた8−アルコキシキノロンカルボン酸水和物並びにその製造方法 |
JP335569/1994 | 1994-12-21 | ||
JP335569/94 | 1994-12-21 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1171108A true CN1171108A (zh) | 1998-01-21 |
CN1137890C CN1137890C (zh) | 2004-02-11 |
Family
ID=18290056
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB951969838A Expired - Lifetime CN1137890C (zh) | 1994-12-21 | 1995-12-05 | 稳定性优良的8-烷氧基喹诺酮羧酸水合物及其制备方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US5880283A (zh) |
EP (1) | EP0805156B1 (zh) |
JP (1) | JP3449658B2 (zh) |
KR (1) | KR100381644B1 (zh) |
CN (1) | CN1137890C (zh) |
AT (1) | ATE216381T1 (zh) |
AU (1) | AU694946B2 (zh) |
CA (1) | CA2208704C (zh) |
DE (1) | DE69526453T2 (zh) |
DK (1) | DK0805156T3 (zh) |
ES (1) | ES2173982T3 (zh) |
HU (1) | HU227795B1 (zh) |
PT (1) | PT805156E (zh) |
TW (1) | TW393479B (zh) |
WO (1) | WO1996019472A1 (zh) |
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GB9920919D0 (en) | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel compound |
GB9920917D0 (en) | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel process |
TWI287987B (en) * | 2000-08-14 | 2007-10-11 | Senju Pharma Co | Cytokine inhibitor |
US6413969B1 (en) * | 2000-09-13 | 2002-07-02 | Bristol-Myers Squibb Company | Gatifloxacin pentahydrate |
JP2002363172A (ja) * | 2001-06-05 | 2002-12-18 | Showa Denko Kk | 5−アルキルオキサゾリジン−2,4−ジオンの製造方法 |
US6589955B2 (en) | 2001-06-20 | 2003-07-08 | Bristol-Myers Squibb Company | Pediatric formulation of gatifloxacin |
KR100517638B1 (ko) | 2002-04-08 | 2005-09-28 | 주식회사 엘지생명과학 | 게미플록사신 산염의 새로운 제조방법 |
AU2003230831A1 (en) * | 2002-04-08 | 2003-10-27 | Dr. Reddy's Laboratories Limited | ANHYDROUS CRYSTALLINE FORMS I AND II OF 1-CYCLOPROPYL-6-FLUORO-8-METHOXY-7-(3-METHYL-1-PIPERAZINYL) 4-OXO-l, 4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID (GATIFLOXACIN) |
EP1503762A2 (en) * | 2002-05-10 | 2005-02-09 | Teva Pharmaceutical Industries Ltd. | Novel crystalline forms of gatifloxacin |
US7423153B2 (en) * | 2002-05-10 | 2008-09-09 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of gatifloxacin |
EP1645274A1 (en) * | 2002-05-10 | 2006-04-12 | Teva Pharmaceutical Industries Ltd. | Process for making gatifloxacin form omega |
CA2489377A1 (en) * | 2002-06-14 | 2003-12-24 | Valerie Niddam-Hildesheim | Novel crystalline forms of gatifloxacin |
CA2494518A1 (en) | 2002-08-06 | 2004-02-12 | Teva Pharmaceutical Industries Ltd. | Novel crystalline forms of gatifloxacin |
WO2004069825A1 (en) * | 2002-08-14 | 2004-08-19 | Teva Pharmaceutical Industries Ltd. | Synthesis of gatifloxacin |
WO2004054583A1 (en) * | 2002-12-12 | 2004-07-01 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of gatifloxacin and processes for preparation |
US20050085640A1 (en) * | 2003-04-02 | 2005-04-21 | Hetero Drugs Limited | Novel crystalline forms of gatifloxacin |
WO2004101547A1 (en) * | 2003-05-19 | 2004-11-25 | Hetero Drugs Limited | Purification methods of gatifloxacin and a novel form of gatifloxacin |
WO2005021000A1 (en) * | 2003-08-28 | 2005-03-10 | Ranbaxy Laboratories Limited | Solid oral dosage forms of gatifloxacin |
ES2232310B1 (es) * | 2003-11-13 | 2006-08-01 | Quimica Sintetica, S.A. | Formula cristalina no higroscopica de gatifloxacino. |
ES2232311B1 (es) * | 2003-11-13 | 2006-08-01 | Quimica Sintetica, S.A. | Forma cristalina de gatifloxacino. |
US7781585B2 (en) | 2004-06-04 | 2010-08-24 | Matrix Laboratories Ltd | Crystalline forms of Gatifloxacin |
US20090156577A1 (en) * | 2004-09-09 | 2009-06-18 | Benjamin Davis | 7-amino alkylidenyl-heterocyclic quinolones and naphthyridones |
US20060247255A1 (en) * | 2005-05-02 | 2006-11-02 | Patel Satishkumar A | Method for preparing a stable gatifloxacin composition |
US20080139574A1 (en) | 2006-11-30 | 2008-06-12 | Cadila Healthcare Limited | Novel quinoline derivatives |
CA2621616A1 (en) * | 2007-02-19 | 2008-08-19 | Alcon Research, Ltd. | Topical gatifloxacin formulations |
US7902227B2 (en) | 2007-07-27 | 2011-03-08 | Janssen Pharmaceutica Nv. | C-7 isoxazolinyl quinolone / naphthyridine derivatives useful as antibacterial agents |
US7884099B2 (en) * | 2007-11-16 | 2011-02-08 | Cumbre Ip Ventures, L.P. | Quinolone carboxylic acid-substituted rifamycin derivatives |
JP2013510097A (ja) * | 2009-11-03 | 2013-03-21 | リウ、リー | タンシノンiiaスルホン酸ナトリウム水和物、並びにその調製方法及び使用 |
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JPS57134482A (en) * | 1981-02-13 | 1982-08-19 | Dainippon Pharmaceut Co Ltd | 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation |
DE3248506A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(alkyl-1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
JPH089597B2 (ja) * | 1986-01-21 | 1996-01-31 | 杏林製薬株式会社 | 選択毒性に優れた8‐アルコキシキノロンカルボン酸およびその塩並びにその製造方法 |
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-
1994
- 1994-12-21 JP JP33556994A patent/JP3449658B2/ja not_active Expired - Lifetime
-
1995
- 1995-12-05 US US08/860,325 patent/US5880283A/en not_active Expired - Lifetime
- 1995-12-05 DE DE69526453T patent/DE69526453T2/de not_active Expired - Lifetime
- 1995-12-05 KR KR1019970704228A patent/KR100381644B1/ko not_active IP Right Cessation
- 1995-12-05 AT AT95938644T patent/ATE216381T1/de active
- 1995-12-05 AU AU39946/95A patent/AU694946B2/en not_active Expired
- 1995-12-05 HU HU9800908A patent/HU227795B1/hu unknown
- 1995-12-05 DK DK95938644T patent/DK0805156T3/da active
- 1995-12-05 WO PCT/JP1995/002477 patent/WO1996019472A1/ja active IP Right Grant
- 1995-12-05 CN CNB951969838A patent/CN1137890C/zh not_active Expired - Lifetime
- 1995-12-05 EP EP95938644A patent/EP0805156B1/en not_active Expired - Lifetime
- 1995-12-05 CA CA002208704A patent/CA2208704C/en not_active Expired - Lifetime
- 1995-12-05 PT PT95938644T patent/PT805156E/pt unknown
- 1995-12-05 ES ES95938644T patent/ES2173982T3/es not_active Expired - Lifetime
- 1995-12-11 TW TW084113176A patent/TW393479B/zh not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102757419A (zh) * | 2012-08-08 | 2012-10-31 | 四川百利药业有限责任公司 | 一种加替沙星的纯化方法 |
Also Published As
Publication number | Publication date |
---|---|
HU227795B1 (en) | 2012-03-28 |
CA2208704A1 (en) | 1996-06-27 |
JPH08176143A (ja) | 1996-07-09 |
US5880283A (en) | 1999-03-09 |
TW393479B (en) | 2000-06-11 |
AU694946B2 (en) | 1998-08-06 |
ATE216381T1 (de) | 2002-05-15 |
DE69526453T2 (de) | 2002-12-12 |
DE69526453D1 (de) | 2002-05-23 |
KR100381644B1 (ko) | 2003-08-30 |
CN1137890C (zh) | 2004-02-11 |
AU3994695A (en) | 1996-07-10 |
EP0805156A4 (en) | 1998-04-15 |
EP0805156A1 (en) | 1997-11-05 |
EP0805156B1 (en) | 2002-04-17 |
DK0805156T3 (da) | 2002-05-06 |
ES2173982T3 (es) | 2002-11-01 |
PT805156E (pt) | 2002-09-30 |
JP3449658B2 (ja) | 2003-09-22 |
HUT77945A (hu) | 1998-12-28 |
CA2208704C (en) | 2005-05-03 |
WO1996019472A1 (fr) | 1996-06-27 |
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