US20040024013A1 - Medicinal compositions containing aspirin - Google Patents

Medicinal compositions containing aspirin Download PDF

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Publication number
US20040024013A1
US20040024013A1 US10/600,266 US60026603A US2004024013A1 US 20040024013 A1 US20040024013 A1 US 20040024013A1 US 60026603 A US60026603 A US 60026603A US 2004024013 A1 US2004024013 A1 US 2004024013A1
Authority
US
United States
Prior art keywords
pharmaceutically acceptable
acceptable salt
tetrahydrothieno
cyclopropylcarbonyl
fluorobenzyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
US10/600,266
Other languages
English (en)
Inventor
Fumitoshi Asai
Atsuhiro Sugidachi
Taketoshi Ogawa
Teruhiko Inoue
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daiichi Sankyo Co Ltd
Ube Corp
Original Assignee
Sankyo Co Ltd
Ube Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=18858878&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20040024013(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Sankyo Co Ltd, Ube Industries Ltd filed Critical Sankyo Co Ltd
Assigned to SANKYO COMPANY, LIMITED, UBE INDUSTRIES, LTD. reassignment SANKYO COMPANY, LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: OGAWA, TAKETOSHI, INOUE, TERUHIKO, ASAI, FUMITOSHI, SUGIDACHI, ATSUHIRO
Publication of US20040024013A1 publication Critical patent/US20040024013A1/en
Priority to US11/520,168 priority Critical patent/US8404703B2/en
Priority to US12/006,546 priority patent/US8569325B2/en
Assigned to DAIICHI SANKYO COMPANY, LIMITED reassignment DAIICHI SANKYO COMPANY, LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SANKYO COMPANY, LIMITED
Granted legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
    • 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
    • A61K31/60—Salicylic acid; Derivatives thereof
    • 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
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
    • A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Definitions

  • This invention relates to pharmaceutical compositions containing 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or a pharmaceutically acceptable salt thereof, and aspirin, as active ingredients [particularly pharmaceutical compositions for prevention or treatment (particularly for treatment) of diseases caused by thrombus or embolus]; to the use of 2-acetoxy-5- ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or a pharmaceutically acceptable salt thereof and aspirin for the manufacture of pharmaceutical compositions for prevention or treatment (particularly for treatment) of diseases caused by thrombus or embolus; and to methods for the prevention or treatment (particularly to methods for the treatment) of diseases caused by thrombus or embolus by administration of an effective amount of 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)
  • the present inventors have studied therapeutic agents with low toxicity that exert inhibitory activity against platelet aggregation and have found that the problems described above are solved by using pharmaceutical compositions comprising 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or a pharmaceutically acceptable salt thereof and aspirin.
  • the present invention provides pharmaceutical compositions containing 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or a pharmaceutically acceptable salt thereof and aspirin as active ingredients [particularly pharmaceutical compositions for prevention or treatment (particularly for treatment) of diseases caused by thrombus or embolus]; the use of 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or a pharmaceutically acceptable salt thereof, and aspirin, for the manufacture of pharmaceutical compositions [particularly pharmaceutical compositions for prevention or treatment (particularly for treatment) of diseases caused by thrombus or embolus]; and methods for the prevention or treatment (particularly methods for treatment) of diseases caused by thrombus or embolus by administration of an effective amount of 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluor
  • the pharmaceutically acceptable salts of 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine may be, for example, hydrohalogenic acid salts such as hydrofluoride, hydrochloride, hydrobromide or hydroiodide; nitrate; perchlorate; sulfate; phosphate; C 1 -C 4 alkanesulfonates optionally substituted by halogens such as methanesulfonate, trifluoromethanesulfonate, ethanesulfonate; C 6 -C 10 arylsulfonates optionally substituted by C 1 -C 4 alkyl groups such as benzenesulfonate or p-toluenesulfonate; C 1 -C 6 aliphatic acid salts such as acetate, malate, fumarate, succinate, citrate
  • one of the active ingredients of the present invention may absorb some kinds of organic solvents and may form solvates in some cases, and these solvates are also included in the present invention.
  • the other active ingredient, aspirin, is a well-known compound, as an analgesic antipyretic.
  • compositions of the present invention which contain 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or a pharmaceutically acceptable salt thereof, and aspirin, as active ingredients, possess excellent inhibitory activity against platelet aggregation and thrombogenesis with short onset latency and low toxicity.
  • compositions of the present invention are useful as preventative or therapeutic agents (particularly as therapeutic agents) against diseases caused by thrombus or embolus, for example, diseases induced by platelet aggregation, including stable or unstable angina pectoris and so forth; cardiovascular or cerebrovascular disorders, e.g., thromboembolism, associated with atherosclerosis or diabetes mellitus, such as unstable angina pectoris, cerebral ischemic insult or restenosis due to angioplasty, endarterectomy or stent therapy; or thromboembolism caused by thromboembolization such as recurrent embolism after degradation of the original thrombus, embolism, ischemia-induced dementia, peripheral arteriopathy, thromboembolization associated with hemodialysis or atrial fibrillation, or thromboembolization in the vascular prosthesis, or in the bypass between the aorta and the coronary artery.
  • the therapeutic agent of the present invention is administered to warm-blooded animals (particularly
  • the use in combination of 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or a pharmaceutically acceptable salt thereof, and aspirin results in more potent effectiveness than the use of each component alone. Furthermore, plasma levels of these agents do not have to be maintained at a certain level and higher during the same period, in order to produce their effects. It is believed that these 2 agents reach the receptors, at which they act in vivo, and turn on switches at the receptors to induce the effects.
  • the plasma level of one component of the pharmaceutical composition is too low to induce the effects with increasing time after the agent was administered, the switches at the receptors have already been turned on.
  • the preventative or therapeutic efficacy of the agent is expected by inhibiting thrombogenesis or embolization.
  • the route for administration of 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or a pharmaceutically acceptable salt thereof, and aspirin, which is employed in the present invention is generally the oral route.
  • other routes for example, intravenous administration, can be used.
  • the 2 components can be prepared respectively as separate formulations, or can be mixed physically to form a single formulation for administration.
  • the single formulations of the mixed components are, for example, powders, granules, tablets, capsules and so forth, and can be prepared by regular formulation techniques, as described below.
  • excipients for example, sugar derivatives such as lactose, sucrose, glucose, mannitol or sorbitol; starch derivatives such as corn starch, potato starch, ⁇ -starch or dextrin; cellulose derivatives such as crystalline cellulose; gum arabic; dextran; or pullulan; and inorganic excipients, for example, silicate derivatives such as light silicic acid anhydride, synthetic aluminum silicate, calcium silicate or magnesium aluminate metasilicate; phosphate derivatives such as calcium hydrogenphosphate; carbonates such as calcium carbonate; or sulfates such as calcium sulfate), lubricants (for example, stearic acid; metal stearate derivatives such as calcium stearate or magnesium stearate; talc; waxes such as beeswax or spermaceti; boric acid; adipic acid;
  • excipients for example, sugar derivatives such as lactose, sucrose
  • the dose and the dose ratio of 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or pharmaceutically acceptable salt thereof, and aspirin, can be widely altered based on several factors such as activity of each compound, and the symptoms, age and body weight of the patients.
  • the lower limit of the oral dose is 0.1 mg (preferably, 1 mg) per time, while the upper limit is 1,000 mg (preferably, 500 mg) per time.
  • the lower and upper limits of intravenous injection are 0.01 mg (preferably, 0.1 mg) and 500 mg (preferably, 250 mg), respectively. They are administered to the adult from 1 to 7 times a day based on the symptoms of the patient, simultaneously or sequentially.
  • the dose ratio of 2-acetoxy-5-( ⁇ -cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine or pharmaceutically acceptable salt thereof, and aspirin is from 1:500 to 500:1 as their weight ratio.
  • test animals male Sprague Dawley rats of 7 weeks old were purchased from SLC Japan and 6 rats per group were used.
  • the shunt tube was prepared as follows; i.e., both sides of a medical silicon tube of 12 cm length [inner diameter: 1.5 mm, outer diameter: 2.5 mm, purchased from KANEKA Medix Co., Ltd] were connected each to a polyethylene tube of 7 cm length [inner diameter: 0.5 mm, outer diameter: 1.0 mm, purchased from Natsume Seisakusho Co., Ltd.] covered with silicon via a medical silicon tube of 0.7 cm length [inner diameter: 1.0 mm, outer diameter: 1.5 mm, KANEKA Medix Co., Ltd] as connector. A surgical suture of 10 cm length was placed in the silicon tube of 12 cm length.
  • the animal was anesthetized with an intraperitoneal injection of 40 mg/kg of pentobarbital sodium (purchased from Abbott Laboratories Inc.), and the jugular of one side and the carotid of the other side were exposed.
  • the arteriovenous shunt was made by cannulation of a shunt tube filled with heparin solution [30 units/kg, purchased from Fuso Pharmaceutical Co., Ltd] into the carotid and the jugular which had been previously exposed.
  • the powders in the formula described in the above table are mixed, compressed with a tableting machine and formulated as a tablet containing 250 mg in total.
  • the tablet can be coated with film or sugar, when necessary.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
US10/600,266 2000-12-25 2003-06-20 Medicinal compositions containing aspirin Granted US20040024013A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US11/520,168 US8404703B2 (en) 2000-12-25 2006-09-13 Medicinal compositions containing aspirin
US12/006,546 US8569325B2 (en) 2000-12-25 2008-01-03 Method of treatment with coadministration of aspirin and prasugrel

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2000392983 2000-12-25
JP2000-392983 2000-12-25
PCT/JP2001/011201 WO2002051412A1 (fr) 2000-12-25 2001-12-20 Compositions medicales contenant de l'aspirine

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2001/011201 Continuation WO2002051412A1 (fr) 2000-12-25 2001-12-20 Compositions medicales contenant de l'aspirine

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US11/520,168 Division US8404703B2 (en) 2000-12-25 2006-09-13 Medicinal compositions containing aspirin
US12/006,546 Division US8569325B2 (en) 2000-12-25 2008-01-03 Method of treatment with coadministration of aspirin and prasugrel

Publications (1)

Publication Number Publication Date
US20040024013A1 true US20040024013A1 (en) 2004-02-05

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ID=18858878

Family Applications (3)

Application Number Title Priority Date Filing Date
US10/600,266 Granted US20040024013A1 (en) 2000-12-25 2003-06-20 Medicinal compositions containing aspirin
US11/520,168 Expired - Fee Related US8404703B2 (en) 2000-12-25 2006-09-13 Medicinal compositions containing aspirin
US12/006,546 Expired - Fee Related US8569325B2 (en) 2000-12-25 2008-01-03 Method of treatment with coadministration of aspirin and prasugrel

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Application Number Title Priority Date Filing Date
US11/520,168 Expired - Fee Related US8404703B2 (en) 2000-12-25 2006-09-13 Medicinal compositions containing aspirin
US12/006,546 Expired - Fee Related US8569325B2 (en) 2000-12-25 2008-01-03 Method of treatment with coadministration of aspirin and prasugrel

Country Status (25)

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US (3) US20040024013A1 (cs)
EP (1) EP1350511B1 (cs)
KR (1) KR100692934B1 (cs)
CN (1) CN100341506C (cs)
AT (1) ATE407675T1 (cs)
AU (1) AU2002217464B2 (cs)
BR (1) BR0116531A (cs)
CA (1) CA2432644C (cs)
CY (1) CY1108626T1 (cs)
CZ (1) CZ297570B6 (cs)
DE (1) DE60135780D1 (cs)
DK (1) DK1350511T3 (cs)
ES (1) ES2311498T3 (cs)
HU (1) HUP0400644A3 (cs)
IL (2) IL156456A0 (cs)
MX (1) MXPA03005770A (cs)
NO (1) NO20032902D0 (cs)
NZ (1) NZ526540A (cs)
PL (1) PL206138B1 (cs)
PT (1) PT1350511E (cs)
RU (1) RU2262933C2 (cs)
SK (1) SK287972B6 (cs)
TW (1) TWI293249B (cs)
WO (1) WO2002051412A1 (cs)
ZA (1) ZA200304878B (cs)

Cited By (11)

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Publication number Priority date Publication date Assignee Title
DE102005029612A1 (de) * 2005-06-23 2007-01-04 Hochschule Bremen Vorrichtung zum Erzeugen eines Panoramabildes
US20080040815A1 (en) * 2005-01-19 2008-02-14 Huawei Technologies Co., Ltd. Method and system for processing multicast services
US20090156632A1 (en) * 2005-06-17 2009-06-18 John Thomas Brandt Dosage regimen for prasugrel
US20090281136A1 (en) * 2008-05-08 2009-11-12 Sandeep Mhetre Prasugrel pharmaceutical formulations
US20100004279A1 (en) * 2006-12-07 2010-01-07 Tomoyuki Watanabe Solid medicinal preparation containing mannitol or lactose
WO2010015144A1 (zh) 2008-08-02 2010-02-11 鲁南制药集团股份有限公司 普拉格雷硫酸氢盐及其药物组合物和应用
US20100093786A1 (en) * 2006-12-07 2010-04-15 Tomoyuki Watanabe Pharmaceutical composition containing low-substituted hydroxypropyl cellulose
US20100094013A1 (en) * 2007-03-02 2010-04-15 Hiroyuki Miyata Process for production of prasugrel hydrochloride having high purity
US20110124675A1 (en) * 2007-12-11 2011-05-26 Zhiquan Zhao The hydrosulfate of prasugrel, its pharmaceutical combination and use thereof
US20110201814A1 (en) * 2006-12-07 2011-08-18 Daiichi Sankyo Company Limited Method for producing solid preparation
US20180064890A1 (en) * 2012-12-20 2018-03-08 Otitopic Inc. Dry powder inhaler and methods of use

Families Citing this family (14)

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Publication number Priority date Publication date Assignee Title
AU2001267916B2 (en) * 2000-07-06 2004-09-09 Daiichi Sankyo Company, Limited Hydropyridine derivative acid addition salts
PT1350511E (pt) 2000-12-25 2008-10-28 Ube Industries Composições medicinais contendo aspirina
US20060217351A1 (en) * 2003-05-05 2006-09-28 Brandt John T Method for treating cardiovascular diseases
EP1940399A2 (en) * 2005-08-19 2008-07-09 Eli Lilly & Company Use of par-i/par- 4 inhibitors for treating or preventing vascular diseases
AU2007264030B2 (en) * 2006-06-27 2012-04-05 Sandoz Ag New method for salt preparation
TWI488657B (zh) * 2006-12-07 2015-06-21 Daiichi Sankyo Co Ltd 貯藏安定性經改善之醫藥組成物及改善醫藥組成物之貯藏安定性的方法
WO2008069262A1 (ja) * 2006-12-07 2008-06-12 Daiichi Sankyo Company, Limited 安定性が改善されたフィルムコーティング製剤
SI2152078T1 (sl) 2007-04-27 2021-08-31 Cydex Pharmaceuticals, Inc. Formulacije, ki vsebujejo klopidogrel in sulfoalkilni eter ciklodekstrina in metode uporabe
KR101743591B1 (ko) * 2009-05-13 2017-06-20 사이덱스 파마슈티칼스, 인크. 프라수그렐 및 사이클로덱스트린 유도체를 포함하는 약학 조성물 및 그의 제조 및 사용 방법
CN102228691A (zh) * 2011-06-29 2011-11-02 北京阜康仁生物制药科技有限公司 阿司匹林和一种抗血小板药物的药物组合物
US9757395B2 (en) * 2012-12-20 2017-09-12 Otitopic Inc. Dry powder inhaler and methods of use
HK1218720A1 (zh) 2013-04-30 2017-03-10 欧缇托匹克公司 干粉制剂及使用方法
US9993488B2 (en) 2014-02-20 2018-06-12 Otitopic Inc. Dry powder formulations for inhalation
WO2016122421A1 (en) 2015-01-29 2016-08-04 Pharmactive Ilaç Sanayi Ve Ticaret A.Ş. Stable pharmaceutical compositions containing prasugrel base

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