CN1255105C - Water soluble dressing materials of ziracitone and its salts and their preparation - Google Patents
Water soluble dressing materials of ziracitone and its salts and their preparation Download PDFInfo
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- CN1255105C CN1255105C CNB021551391A CN02155139A CN1255105C CN 1255105 C CN1255105 C CN 1255105C CN B021551391 A CNB021551391 A CN B021551391A CN 02155139 A CN02155139 A CN 02155139A CN 1255105 C CN1255105 C CN 1255105C
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- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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Abstract
本发明公开了一种齐拉西酮及其盐的水溶性包合物及其制备方法。本发明的齐拉西酮及其盐的水溶性包合物为一种包括治疗有效量的活性成分齐拉西酮及其盐与包合材料环糊精衍生物的水溶性包合物。本发明的水溶性包合物的制备方法包括如下步骤：将齐拉西酮或其盐投入含环糊精的有机溶媒中，加热回流1～2小时至药物完全溶解，在加热条件下真空挥干有机溶媒，即得包合物。本发明的包合物的制备方法与现有技术相比，大大缩短了制备包合物的时间，从4天缩短到2小时，为一种具有相当实用价值的包合物和技术。The invention discloses a water-soluble clathrate of ziprasidone and its salt and a preparation method thereof. The water-soluble clathrate of ziprasidone and its salt of the present invention is a water-soluble clathrate comprising therapeutically effective dose of the active ingredient ziprasidone and its salt and clathrate material cyclodextrin derivative. The preparation method of the water-soluble clathrate of the present invention comprises the following steps: putting ziprasidone or its salt into an organic solvent containing cyclodextrin, heating and refluxing for 1 to 2 hours until the drug is completely dissolved, and volatilizing under heating conditions Dry the organic solvent to obtain the clathrate. Compared with the prior art, the clathrate preparation method of the present invention greatly shortens the preparation time of the clathrate from 4 days to 2 hours, and is a clathrate and technology with considerable practical value.
Description
技术领域technical field
本发明涉及齐拉西酮及其盐的水溶性包合物及其制备方法。The invention relates to a water-soluble clathrate of ziprasidone and its salt and a preparation method thereof.
背景技术Background technique
齐拉西酮(Ziprasidone)是一种较新的非典型抗精神病药物，它是5-羟色胺和多巴胺D2受体的拮抗剂，它对精神分裂症的幻视、幻听、妄想等症状均有效。齐拉西酮的化学名为：5-(2-(4-(1，2-苯并异噻唑-3-基)-哌嗪)乙基)-6-氯-1，3-二氢-2H-吲哚-2-酮。2002年6月美国食品与药品管理局(FDA)精神药物咨询委员会批准Geodon(甲磺酸齐拉西酮的肌肉注射剂)用于急性控制和短期治疗躁动不安的病人。Ziprasidone (Ziprasidone) is a newer atypical antipsychotic drug. It is an antagonist of 5-hydroxytryptamine and dopamine D2 receptors. efficient. The chemical name of ziprasidone is: 5-(2-(4-(1,2-benzisothiazol-3-yl)-piperazine)ethyl)-6-chloro-1,3-dihydro- 2H-Indol-2-one. In June 2002, the US Food and Drug Administration (FDA) Psychotropic Drugs Advisory Committee approved Geodon (an intramuscular injection of ziprasidone mesylate) for acute control and short-term treatment of restless patients.
齐拉西酮的水溶性很低，因此在制备其注射溶液剂时必须采用增溶技术。目前采用的增溶技术为：首先将齐拉西酮制成甲磺酸盐，再使甲磺酸齐拉西酮与羟丙基-β-环糊精或磺丁基醚-β-环糊精在水溶液中形成包合物，以此来提高药物的水溶性，如中国专利CN 97194242.0所披露的技术。The water solubility of ziprasidone is very low, so solubilization technology must be used when preparing its injection solution. The solubilization technology currently used is: firstly make ziprasidone mesylate, and then make ziprasidone mesylate and hydroxypropyl-β-cyclodextrin or sulfobutyl ether-β-cyclodextrin The essence forms clathrates in aqueous solution to improve the water solubility of medicines, as disclosed in Chinese patent CN 97194242.0.
但是，上述技术仍有不足之处：由于齐拉西酮甲磺酸盐的水溶性仍很低，因此按常规的水溶液法制备包合物的工艺耗时漫长，需在室温下将齐拉西酮甲磺酸盐分散在羟丙基-β-环糊精或磺丁基醚-β-环糊精(HPBCD或SBECD)的水溶液中持续搅拌4天。But above-mentioned technology still has weak point: because the water-solubility of ziprasidone mesylate is still very low, so the process of preparing clathrate by conventional aqueous solution method takes a long time, needs to make ziprasidone at room temperature Ketone mesylate was dispersed in an aqueous solution of hydroxypropyl-β-cyclodextrin or sulfobutyl ether-β-cyclodextrin (HPBCD or SBECD) with continuous stirring for 4 days.
发明内容Contents of the invention
本发明需要解决的技术问题是公开一种齐拉西酮及其盐的水溶性包合物及其制备方法，以克服现有技术存在的上述缺陷。The technical problem to be solved in the present invention is to disclose a water-soluble clathrate of ziprasidone and its salt and its preparation method, so as to overcome the above-mentioned defects in the prior art.
本发明的技术方案：Technical scheme of the present invention:
本发明的齐拉西酮及其盐的水溶性包合物为一种包括治疗有效量的活性成分齐拉西酮及其盐与包合材料环糊精衍生物的水溶性包合物，所说的包合物不含结晶水或含有半个或多个结晶水。The water-soluble inclusion compound of ziprasidone and its salt of the present invention is a water-soluble inclusion compound comprising a therapeutically effective amount of the active ingredient ziprasidone and its salt and the inclusion material cyclodextrin derivative, so Said clathrate does not contain crystal water or contains half or more crystal water.
所说的包合物的最终应用形式为水溶液、冻干剂、片剂、胶囊、颗粒剂、胶丸、栓剂或吸入粉剂等。The final application form of said clathrate is aqueous solution, lyophilized preparation, tablet, capsule, granule, capsule, suppository or inhalation powder and the like.
优选的齐拉西酮或其盐与环糊精衍生物的摩尔比为：0.1～100∶1。The preferred molar ratio of ziprasidone or its salt to cyclodextrin derivative is: 0.1-100:1.
本发明的齐拉西酮盐包括甲磺酸盐、盐酸盐、苯磺酸盐、乙磺酸盐、酒石酸盐、萘磺酸盐、苹果酸盐、柠檬酸盐、苯甲磺酸盐或天冬氨酸盐等中的一种，上述盐可以是无水物，也可以是半水或多水合物。Ziprasidone salts of the present invention include mesylate, hydrochloride, besylate, esylate, tartrate, naphthalenesulfonate, malate, citrate, besylate or One of aspartic acid salts, etc., and the above-mentioned salts may be anhydrous, hemihydrate or polyhydrate.
所说的环糊精衍生物包括各种取代度的α-环糊精衍生物、β-环糊精衍生物、γ-环糊精衍生物，最理想的选择为羟丙基-β-环糊精、磺丁基醚-β-环糊精中的一种或一种以上。Said cyclodextrin derivatives include α-cyclodextrin derivatives, β-cyclodextrin derivatives, and γ-cyclodextrin derivatives with various degrees of substitution. The most ideal choice is hydroxypropyl-β-cyclodextrin derivatives. One or more of dextrin and sulfobutyl ether-β-cyclodextrin.
本发明的水溶性包合物的制备方法包括如下步骤：The preparation method of water-soluble clathrate of the present invention comprises the steps:
将齐拉西酮或其盐投入含环糊精的有机溶媒中，加热回流1～2小时至药物完全溶解，在加热条件下真空挥干有机溶媒，即得包合物。Put ziprasidone or its salt into the organic solvent containing cyclodextrin, heat and reflux for 1 to 2 hours until the drug is completely dissolved, evaporate the organic solvent in vacuum under heating conditions, and obtain the clathrate.
所说的有机溶媒包括但不限于：乙醇、甲醇、乙腈、丙酮、异丙醇、正丁醇、四氢呋喃等中的一种或一种以上。Said organic solvent includes, but is not limited to: one or more of ethanol, methanol, acetonitrile, acetone, isopropanol, n-butanol, tetrahydrofuran, and the like.
本发明的包合物可用于急性控制和短期治疗躁动不安的精神病人，其剂量与使用方法与常规的齐拉西酮或其盐的方法相同。本发明的包合物的制备方法与现有技术相比，大大缩短了制备包合物的时间，从4天缩短到2小时，为一种具有相当实用价值的包合物和包合技术。The clathrate of the present invention can be used for acute control and short-term treatment of restless mental patients, and its dosage and usage method are the same as those of conventional ziprasidone or its salt. Compared with the prior art, the clathrate preparation method of the present invention greatly shortens the preparation time of the clathrate from 4 days to 2 hours, and is a clathrate and clathrate technology with considerable practical value.
具体实施方式Detailed ways
实施例1Example 1
将1克甲磺酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone mesylate and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, and heat to reflux at 80°C for 2 Hours until the drug is completely dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例2Example 2
将1克盐酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone hydrochloride and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, heat and reflux at 80°C for 2 hours to The drug is all dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例3Example 3
将1克苯甲磺酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone benzylsulfonate and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, and heat to reflux at 80°C 2 hours until the drug is completely dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例4Example 4
将1克乙磺酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone ethanesulfonate and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, heat and reflux at 80°C for 2 Hours until the drug is completely dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例5Example 5
将1克酒石酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone tartrate and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, heat and reflux at 80°C for 2 hours to The drug is all dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例6Example 6
将1克苹果酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone malate and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, heat and reflux at 80°C for 2 hours until the drug is completely dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例7Example 7
将1克萘磺酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone naphthalenesulfonate and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, and heat to reflux at 80°C for 2 Hours until the drug is completely dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例8Example 8
将1克苯磺酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone besylate and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, heat and reflux at 80°C for 2 Hours until the drug is completely dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例9Example 9
将1克天冬氨酸齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone aspartate and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, and heat to reflux at 80°C 2 hours until the drug is completely dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
实施例10Example 10
将1克齐拉西酮和数克羟丙基-β-环糊精(或数克磺丁基醚-β-环糊精)与1000ml无水乙醇混和，于80℃加热回流2小时至药物全部溶解。减压浓缩至恒重，得到包合物。Mix 1 gram of ziprasidone and several grams of hydroxypropyl-β-cyclodextrin (or several grams of sulfobutyl ether-β-cyclodextrin) with 1000ml of absolute ethanol, heat and reflux at 80°C for 2 hours until the drug All dissolved. Concentrate under reduced pressure to constant weight to obtain clathrate.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021551391A CN1255105C (en) | 2002-12-17 | 2002-12-17 | Water soluble dressing materials of ziracitone and its salts and their preparation |
| AU2003303019A AU2003303019A1 (en) | 2002-12-17 | 2003-11-18 | Water-soluble clathrates of ziprasidone and its salts, and the preparation methods therefor |
| PCT/CN2003/000979 WO2004054621A1 (en) | 2002-12-17 | 2003-11-18 | Water-soluble clathrates of ziprasidone and its salts, and the preparation methods therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021551391A CN1255105C (en) | 2002-12-17 | 2002-12-17 | Water soluble dressing materials of ziracitone and its salts and their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1424037A CN1424037A (en) | 2003-06-18 |
| CN1255105C true CN1255105C (en) | 2006-05-10 |
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ID=4752571
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021551391A Expired - Fee Related CN1255105C (en) | 2002-12-17 | 2002-12-17 | Water soluble dressing materials of ziracitone and its salts and their preparation |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN1255105C (en) |
| AU (1) | AU2003303019A1 (en) |
| WO (1) | WO2004054621A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060015750A (en) | 2003-06-03 | 2006-02-20 | 테바 파마슈티컬 인더스트리즈 리미티드 | Polymorphic form of ziprasidone HCC and its manufacturing method |
| WO2005040160A2 (en) | 2003-10-24 | 2005-05-06 | Teva Pharmaceutical Industries Ltd. | Processes for preparation of ziprasidone |
| CA2500667C (en) | 2005-03-11 | 2013-01-15 | Apotex Pharmachem Inc. | Preparation of acid addition salts of ziprasidone and intermediates thereof by solid phase-gas phase reactions |
| CN100391458C (en) * | 2006-02-07 | 2008-06-04 | 上海医药工业研究院 | Preparation method of ziprasidone or its salt inclusion compound |
| CN102234273B (en) * | 2010-04-21 | 2015-08-05 | 上海医药工业研究院 | Ziprasidone mesylate semihydrate and preparation method thereof |
| WO2011148253A2 (en) | 2010-05-25 | 2011-12-01 | Aurobindo Pharma Limited | Solid dosage forms of antipsychotics |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5206366A (en) * | 1992-08-26 | 1993-04-27 | Pfizer Inc. | Process for preparing aryl piperazinyl-heterocyclic compounds |
| US5312925A (en) * | 1992-09-01 | 1994-05-17 | Pfizer Inc. | Monohydrate of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one-hydrochloride |
| PH31594A (en) * | 1993-09-30 | 1998-11-03 | Janssen Pharmaceutica Nv | Oral formulations on an antifungal. |
| UA57734C2 (en) * | 1996-05-07 | 2003-07-15 | Пфайзер Інк. | Arylheterocyclic inclusion complexes |
-
2002
- 2002-12-17 CN CNB021551391A patent/CN1255105C/en not_active Expired - Fee Related
-
2003
- 2003-11-18 WO PCT/CN2003/000979 patent/WO2004054621A1/en not_active Ceased
- 2003-11-18 AU AU2003303019A patent/AU2003303019A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1424037A (en) | 2003-06-18 |
| WO2004054621A1 (en) | 2004-07-01 |
| AU2003303019A1 (en) | 2004-07-09 |
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