CN1708307A - 水可溶的美洛昔康颗粒 - Google Patents
水可溶的美洛昔康颗粒 Download PDFInfo
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- CN1708307A CN1708307A CNA2003801019791A CN200380101979A CN1708307A CN 1708307 A CN1708307 A CN 1708307A CN A2003801019791 A CNA2003801019791 A CN A2003801019791A CN 200380101979 A CN200380101979 A CN 200380101979A CN 1708307 A CN1708307 A CN 1708307A
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- Prior art keywords
- meloxicam
- granule
- meglumine
- agent
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- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 229960001929 meloxicam Drugs 0.000 title claims abstract description 74
- 239000008187 granular material Substances 0.000 title claims abstract description 42
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 229960003194 meglumine Drugs 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011230 binding agent Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 6
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 6
- 235000003599 food sweetener Nutrition 0.000 claims abstract 2
- 239000003765 sweetening agent Substances 0.000 claims abstract 2
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- 238000002360 preparation method Methods 0.000 claims description 13
- 229960001031 glucose Drugs 0.000 claims description 11
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 10
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 9
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 9
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 9
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- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 9
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- 239000013543 active substance Substances 0.000 claims description 7
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
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- 235000010355 mannitol Nutrition 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 5
- 239000011591 potassium Substances 0.000 abstract description 5
- 229910052700 potassium Inorganic materials 0.000 abstract description 5
- 239000011734 sodium Substances 0.000 abstract description 5
- 229910052708 sodium Inorganic materials 0.000 abstract description 5
- 241000124008 Mammalia Species 0.000 abstract description 3
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- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 3
- 229960003438 aspartame Drugs 0.000 description 3
- 208000004396 mastitis Diseases 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 2
- 229960005164 acesulfame Drugs 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229960003511 macrogol Drugs 0.000 description 2
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- LICPKMHUPOIPDE-WZTVWXICSA-N 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 LICPKMHUPOIPDE-WZTVWXICSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
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Abstract
本发明是关于迅速溶于水的美洛昔康(meloxicam)颗粒,并含有美洛昔康,形成美洛昔康的葡甲胺、钠、钾或铵盐的盐形成剂,粘合剂,糖或甜味剂,载体,视需要的一种矫味剂及视需要的其他助剂,本发明也关于制备这种颗粒的方法以及其在治疗哺乳动物呼吸或炎症疾病中的用途。
Description
本发明是关于迅速溶于水的美洛昔康(meloxicam)颗粒,其含有美洛昔康,形成美洛昔康的葡甲胺(meglumine)、钠、钾或铵盐的盐形成剂,粘合剂,糖或甜味剂,载体,视需要的矫味剂及视需要的其他助剂,制备这种颗粒的方法及其在治疗哺乳动物呼吸或炎症疾病中的用途。
先前技术
美洛昔康(4-羟基-2-甲基-N-(5-甲基-2-噻唑基)-2H-1,2-苯并噻嗪-3-羧酰胺-1,1-二氧化物)是属于NSAID(非类固醇抗炎药物)类的活性物质。美洛昔康及其钠盐和葡甲胺盐(N-甲基-D-葡糖胺盐)描述于EP-A-0002 482中。EP-A-0945 134揭示美洛昔康及其盐,即钠盐、铵盐及葡甲胺盐,在水溶液内的pH依赖性的溶解度特性。因此,美洛昔康是不易溶于水的活性物质。由EP-0 945134表1所示,美洛昔康盐,特别是其葡甲胺盐,在pH增至4及10时,呈现好的溶解性。
现已知,通过使生病的动物,特别是患发烧的动物,以饮水给予药物是简单并有效的。将药物通过食物给予动物也同样容易进行。由EP 0945134可知,美洛昔康及葡甲胺不易一起压制。本发明目的即在发展成美洛昔康的颗粒,通过在动物的饮水中混合或作为食物供给而给予。
发明内容
令人惊奇的是,美洛昔康颗粒可用流化床(fluidised bed)法生产,并迅速溶于水中通过至少48小时形成稳定的饮水溶液。同时并发现,这种颗粒可作为动物供食给予。
所以,本发明是关于水可溶的颗粒,它含美洛昔康,一种形成美洛昔康的葡甲胺盐、钠、钾或铵盐的盐的形成剂,粘合剂,糖或甜味剂,载体,视需要的一种矫味剂以及必要时的其它助剂。
本发明美洛昔康颗粒较已有的制剂是有多种优点。
患病的动物,在给予含美洛昔康的饮料时,其饮水量有明显增加。任意稀释溶解的颗粒,可获得活性物质美洛昔康的不同而准确的剂量。由于本发明美洛昔康颗粒是良好的水溶解性,美洛昔康在患病的动物体内会迅速发生效果。美洛昔康颗粒的良好口味也可使其作为食物供给而给予。此外,本发明颗粒有极好的流动性,美洛昔康含量的均匀性,几乎无尘的,其微粒大小分布较窄,为125微米至500微米。颗粒在水中的完全溶解性确保完全溶解的活性物质的光学控制,这种活性物质在加入饮水内给予进行处理时,只能以这种形式适于治疗用途。
在本发明的一个优选实施方案中,盐形成剂是葡甲胺。在一个同样的本发明优选实施方案中,粘合剂可选自羟基丙基-甲基纤维素,聚乙烯吡咯烷酮,明胶,淀粉及聚乙二醇醚,优选是羟基丙基-甲基纤维素,聚乙烯吡咯烷酮,及聚乙二醇醚,最佳是羟基丙基-甲基纤维素及聚乙烯吡咯烷酮。
于另一个发明优选实施方案中,糖或甜味剂可选自糖精钠,天冬酰苯丙氨酸甲酯(aspartame)及Sunett,优选的是糖精钠或天冬酰苯丙氨酸甲酯。
根据本发明,特别优选的本发明的美洛昔康颗粒其中矫味剂是选自香草,蜂蜜矫味剂,苹果矫味剂及康特马隆(contramarum),优选的蜂蜜矫味剂及苹果矫味剂。
另外,特别优选的是这样的美洛昔康颗粒,其中的载体是选自乳糖,葡萄糖,甘露糖,木糖醇,蔗糖及山梨糖醇,优选的葡萄糖,乳糖或山梨糖醇,更佳是葡萄糖或乳糖,最佳是葡萄糖。
特别优选的是这样的美洛昔康颗粒,其中美洛昔康含量为0.05%至4%,优选是0.1至2%,较佳是0.3%至1.5%,更佳是0.4%至1%,最佳是0.6%。此外,特佳的是这样的美洛昔康颗粒,其葡甲胺和美洛昔康的摩尔比为约9∶8至12∶8,优选是10∶8。
本发明另一个主题是制备本发明美洛昔康颗粒的方法,其中相继进行步骤a)至c):
a)制备一种含粘合剂,视需要一种糖或甜味剂,美洛昔康,葡甲胺及/或矫味剂的水性成粒液体。
b)将成粒液体用恒温50至80℃,优选是65℃的气流以顶喷流化床(topspray fluidised bed)法喷在载剂上。
c)最后以顶喷流化床法用含有粘合剂,糖或甜味剂及/或矫味剂的水性成粒液体进行涂覆过程。
在本发明的优选方法中,其中成粒液体是通过将各成分搅拌并加热至70至100℃,优选是约90℃下进行制备。
本发明美洛昔康颗粒的特点是在于其在原始包装内在室温储存时,有24个月成更多的长期稳定性。
一种极佳的美洛昔康颗粒制剂含美洛昔康,葡甲胺,羟基丙基甲基纤维素,聚乙烯吡咯烷酮(povidone)及单水合葡萄糖。
本发明再一个主题是关于美洛昔康颗粒在制备用于治疗哺乳动物的疼痛,炎症,发烧,急性乳腺炎,腹泻,麻痹,运动器械的伤害及呼吸疾病中的药物制剂的用途,特别是用于治疗急性乳腺炎,腹泻,麻痹,运动器械的伤害及呼吸疾病,较佳是急性乳腺炎,腹泻,麻痹,运动器械伤害及呼吸疾病,最佳是运动器械的伤害及呼吸疾病。这种治疗可与抗生素治疗相结合。
本发明制剂适于治疗动物,优选是哺乳动物,特别是家畜或有益动物,如猪,马,牛,狗或猫,特别是猪或马。
本发明美洛昔康颗粒的应用优选是以相当于每公斤体重0.2至1.0毫克的活性物质的剂量,优选是0.4至0.8毫克/公斤体重,较佳是0.5至0.7毫克/公斤体重,特佳是0.6毫克/公斤体重。
也优选的是本发明美洛昔康颗粒用于制备可以通过饮水槽或作为供食而给予的药物。
本发明制剂可含有作为美洛昔康盐的葡甲胺、钠、钾或铵盐,优选是美洛昔康葡甲胺盐。
在美洛昔康颗粒中葡甲胺的含量是0.035至2.8%,优选是0.07至1.4%,较佳是0.21-1.05%,更佳是0.28-0.7%毫克/克,特佳是约0.42%。钠、钾及铵的浓度也可相应计算。
粘合剂的浓度可在20-80毫克/克颗粒的范围内,优选是30-70毫克/克,更佳是40-60毫克/克,最佳是50毫克/克。
糖的浓度可在50-150毫克/克颗粒的范围内,优选是75-125毫克/克,最佳是约100毫克/克。
甜味剂的浓度可在1-10毫克/克颗粒的范围内,优选是2-5毫克/克,更佳是约3毫克/克。
载体的浓度可在800-985毫克/克颗粒的范围内,优选是900-960毫克/克,更佳是约930毫克/克。
矫味剂的浓度可在0.1-10毫克/克颗粒的范围内,优选是0.2-1.0毫克/克,更佳是约0.5毫克/克。
本发明制剂所用的包装材料可以是各种适于颗粒用的商业上惯用的材料。包括,例如,塑料容器,例如由HPPE(高压聚乙烯)制的,铝袋或有铝衬里的纸袋。
美洛昔康颗粒是按顶喷流化床方法生产。在此法中,首先通过在约70至100℃加热搅拌由下列成份构成的水性成粒溶液,这溶液含有约50至70克/公斤粘合剂,如PVP 25000,羟基丙基甲基纤维素或Macrogol 6000,优选是羟基丙基甲基纤维素及/或约1至5克/公斤甜味剂如Sunett或糖精钠,优选是Sunett,及/或约0.5至2.5克/公斤矫味剂,如香草,蜂蜜,矫味剂203180或康特马隆(contramarum),优选是蜂蜜,约10至15克美洛昔康(peg研磨的)及约7至11克葡甲胺。
然后将成粒液体以逆流法喷射在载体上,载体如乳糖,葡萄糖或山梨糖醇,优选是葡萄糖。这是用,例如,双喷嘴于恒压下在约50至80℃(优选65℃)进行。然后可用第二种成粒液体进行涂覆过程。在制备需用的溶液时,可将储液完全溶于水内。再将储液与水混合以调整到所需浓度备用。为提高使用安全性,颗粒可具有水溶性的色标。
本发明美洛昔康颗粒可通过以下实施例说明。本专业技术人员会了解此实施例仅用以说明,不应视为限制。
实施例1
0.6%美洛昔康颗粒
配方:
克/100克
美洛昔康 0.6
葡甲胺 0.42
羟基丙基甲基纤维素 3.00
聚乙烯吡咯烷酮 2.00
单水合葡萄糖 93.98
实施例2
1.2%美洛昔康颗粒
美洛昔康 1.2
葡甲胺 0.84
羟基丙基甲基纤维素 3.00
可力酮(kolidon)25 2.0
单水合葡萄糖 92.96
实施例3
0.6%美洛昔康颗粒
美洛昔康 0.6
葡甲胺 0.42
Pharmacoat 606 4.0
聚乙二醇(Macrogol)6000 1.0
双氧 噻嗪(Acesulfame)K 0.3
乳糖 93.68
实施例4
0.6%美洛昔康颗粒
美洛昔康 0.6
葡甲胺 0.42
Pharmacoat 606 4.75
聚乙二醇6000 0.25
双氧噻嗪(Acesulfame)K 0.3
液体香草矫味剂 0.05
乳糖 93.63
对应于实施例1至4的亮黄的自由流动的美洛昔康颗粒可如下制备:
将颗粒于25℃和相对湿度60%下储存3个月。观察到活性物质含量,水含量(根据Karl-Fischer),可见溶解度持性,去矿物质的水的pH,及可见的湿润性(wettability)没有明显变化。要测定可见溶解特性时,将5克颗粒于周边温度下溶于100毫升去矿物质的水内。约1分钟后即得澄清黄色溶液。
Claims (16)
1.一种水溶性美洛昔康(meloxicam)颗粒,其含有美洛昔康,粘合剂,糖或甜味剂,载体,一种形成美洛昔康的葡甲胺盐、钠盐、钾盐或铵盐的盐形成剂,视需要的矫味剂及其他视需要的助剂。
2.根据权利要求1的美洛昔康颗粒,其特征在于盐形成剂为葡甲胺。
3.根据权利要求1或2的美洛昔康颗粒,其特征在于粘合剂是选自羟基丙基-甲基纤维素,聚乙烯吡咯烷酮,明胶,淀粉及聚乙二醇醚中。
4.根据权利要求1至3中之一的美洛昔康颗粒,其特征在于糖或甜味剂是选自糖精钠,天冬酰苯丙酸甲酯及Sunett。
5.根据权利要求1至4中之一的美洛昔康颗粒,其特征在于矫味剂是选自香草,蜂蜜矫味剂,苹果矫味剂及康特马隆(contramarum)。
6.根据权利要求1至5中之一的美洛昔康颗粒,其特征在于载体是选自乳糖,葡萄糖,甘露糖醇,木糖醇,蔗糖及山梨糖醇。
7.根据权利要求1至6中之一的美洛昔康颗粒,其特征在于美洛昔康的含量是介于0.05%至4%之间。
8.根据权利要求1至7中之一的美洛昔康颗粒,其特征在于其含有9∶8至12∶8的摩尔比的葡甲胺与美洛昔康。
9.根据权利要求1至8中之一的美洛昔康颗粒,其特征在于其含有10∶8摩尔比的葡甲胺与美洛昔康。
10.一种制造权利要求1至9中之一的美洛昔康颗粒的方法,其特征在于相继进行步骤a)至c):
a)制备水性成粒液体,其含有结合剂,糖或甜味剂,美洛昔康,葡甲胺及/或矫味剂;
b)将成粒液体在恒温50至80℃的气流下以顶喷流化床(topsprayfluidised bed)法喷射在载剂上。
c)以顶喷流化床方法用含有粘合剂,糖或甘味剂及/或矫味剂的水性成粒液体进行涂覆步骤。
11.根据权利要求10的方法,其特征在于成粒液体是通过将各成分在70至100℃下搅拌及加热而制备。
12.根据权利要求1至9中之一的美洛昔康颗粒,其特征在于其在原包装中储存于环境温度时,有24个月或更长的长期稳定性。
13.根据权利要求1至9或12中之一的美洛昔康颗粒,其含一种美洛昔康、葡甲胺、羟丙基甲基纤维素、聚乙烯吡咯烷酮(povidone),及单水合葡萄糖。
14.一种根据权利要求1至9中之一或12中的美洛昔康颗粒的用途,它用于制备治疗哺乳动物的疼痛,炎症,发烧及呼吸疾病中的药物制剂。
15.一种根据权利要求13的美洛昔康颗粒的用途,其用量相当于每公斤体重0.2至1.0毫克活性物质的剂量范围。
16.一种根据权利要求12或13的美洛昔康颗粒的用途,它用于制造一种可以通过饮水槽或食物供给而给予的药物制剂。
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US6106862A (en) * | 1998-08-13 | 2000-08-22 | Andrx Corporation | Once daily analgesic tablet |
DE19859636A1 (de) * | 1998-12-23 | 2000-06-29 | Hexal Ag | Kontrolliert freisetzende pharmazeutische Zusammensetzung mit Tilidinmesylat als Wirkstoff |
US6685928B2 (en) * | 1999-12-07 | 2004-02-03 | Rutgers, The State University Of New Jersey | Therapeutic compositions and methods |
WO2001097812A1 (fr) * | 2000-06-20 | 2001-12-27 | Fujisawa Pharmaceutical Co., Ltd. | Preparations pharmaceutiques contenant des composes tetracycliques |
DE10030345A1 (de) * | 2000-06-20 | 2002-01-10 | Boehringer Ingelheim Vetmed | Hochkonzentrierte stabile Meloxicamlösungen |
DE10250081A1 (de) * | 2002-10-25 | 2004-05-13 | Boehringer Ingelheim Vetmedica Gmbh | Wasserlösliche Meloxicam Granulate |
-
2002
- 2002-10-25 DE DE10250081A patent/DE10250081A1/de not_active Withdrawn
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2003
- 2003-10-23 PE PE2003001075A patent/PE20040495A1/es not_active Application Discontinuation
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- 2003-10-24 JP JP2004545974A patent/JP4856377B2/ja not_active Expired - Lifetime
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- 2003-10-24 DE DE50308863T patent/DE50308863D1/de not_active Expired - Lifetime
- 2003-10-24 CA CA2503396A patent/CA2503396C/en not_active Expired - Lifetime
- 2003-10-24 UY UY28039A patent/UY28039A1/es not_active Application Discontinuation
- 2003-10-24 AT AT03809321T patent/ATE381337T1/de active
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2005
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- 2005-04-22 HR HRP20050366AA patent/HRP20050366B1/hr not_active IP Right Cessation
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2006
- 2006-04-28 HK HK06105083.1A patent/HK1084878A1/xx not_active IP Right Cessation
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2008
- 2008-03-07 CY CY20081100265T patent/CY1107298T1/el unknown
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2011
- 2011-06-21 JP JP2011137557A patent/JP5579132B2/ja not_active Expired - Lifetime
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2012
- 2012-09-05 US US13/604,266 patent/US20130005714A1/en not_active Abandoned
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103705479A (zh) * | 2012-09-29 | 2014-04-09 | 瑞普(天津)生物药业有限公司 | 一种宠物用美洛昔康缓释片及其制备方法 |
CN103705479B (zh) * | 2012-09-29 | 2017-11-28 | 瑞普(天津)生物药业有限公司 | 一种宠物用美洛昔康缓释片及其制备方法 |
CN107073010A (zh) * | 2014-06-09 | 2017-08-18 | 伊休蒂卡有限公司 | 新型美洛昔康制剂 |
CN109983013A (zh) * | 2016-11-18 | 2019-07-05 | 帕西拉制药有限公司 | 美洛昔康锌复合物微粒多囊脂质体制剂及其制备方法 |
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