WO2014149526A1 - Phenylephrine resinate particles - Google Patents

Phenylephrine resinate particles Download PDF

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Publication number
WO2014149526A1
WO2014149526A1 PCT/US2014/019301 US2014019301W WO2014149526A1 WO 2014149526 A1 WO2014149526 A1 WO 2014149526A1 US 2014019301 W US2014019301 W US 2014019301W WO 2014149526 A1 WO2014149526 A1 WO 2014149526A1
Authority
WO
WIPO (PCT)
Prior art keywords
phenylephrine
particles
μιη
hours
coated
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.)
Ceased
Application number
PCT/US2014/019301
Other languages
English (en)
French (fr)
Inventor
Der-Yang Lee
Cathy Gelotte
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.)
Kenvue Brands LLC
Original Assignee
McNeil PPC Inc
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
Priority to BR112015022975-1A priority Critical patent/BR112015022975B1/pt
Priority to NZ712317A priority patent/NZ712317B2/en
Priority to RU2015144181A priority patent/RU2675788C2/ru
Priority to HK16107941.7A priority patent/HK1219885B/en
Priority to MX2015012340A priority patent/MX383890B/es
Priority to EP14709863.6A priority patent/EP2968223B1/en
Priority to UAA201509684A priority patent/UA116372C2/uk
Priority to CA2906357A priority patent/CA2906357C/en
Priority to JP2016500489A priority patent/JP6314206B2/ja
Priority to CN201480015698.2A priority patent/CN105263483A/zh
Application filed by McNeil PPC Inc filed Critical McNeil PPC Inc
Priority to AU2014238059A priority patent/AU2014238059B2/en
Publication of WO2014149526A1 publication Critical patent/WO2014149526A1/en
Priority to IL241050A priority patent/IL241050B/en
Priority to PH12015502066A priority patent/PH12015502066A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • 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
    • 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
    • A61K47/51—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 non-active ingredient being a modifying agent
    • A61K47/56—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/58—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
    • A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0043—Nose
    • A—HUMAN NECESSITIES
    • 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
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/10—Expectorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/14—Antitussive agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
    • A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose

Definitions

  • the present invention is also directed to pharmaceutical dosage forms comprising phenylephrine particles that deliver phenylephrine or a pharmaceutically acceptable salt thereof to a subject in need thereof so as to provide a peak plasma concentration of phenylephrine at about 0.1 to about 16 hours, preferably about 0.5 to about 5 hours, more preferably about 1 to about 4.5 hours, after ingestion and wherein the phenylephrine is maintained at a level greater than about 20, about 40, about 60, about 80, about 100, about 120, about 140, about 160, about 180 or about 200, pg/mL for at least about 6, about 8, about 12, about 16, about 20 and/or about 24 hours after ingestion.
  • Figure 5 shows the mean plasma concentration profile of phenylephrine upon administration of coated ER phenylephrine resinate particles containing 15 mg phenylephrine and liquid IR phenylephrine HC1 containing 5 mg phenylephrine (the "ER-IR blend").
  • the unbroken line represents the ER-IR blend.
  • the curve for this treatment is consistent with what was seen with the resinate and the HC1 formulations.
  • the ER-IR blend there are two peaks within the first 2 hours; one mainly from the IR dose and the other from the accumulation of the IR and ER doses. The Cmax was reached faster and maintained for a longer period of time. An ER-IR blend thus appears beneficial in terms of onset of efficacy.
  • delayed release it is meant that, after administration, there is at least one period of time when an active ingredient is not being released from the dosage form, i.e., the release of the active ingredient(s) occurs at a time other than immediately following oral administration.
  • immediate release means that the dissolution characteristics of at least one active ingredient meet USP specifications for immediate release tablets containing that active ingredient.
  • An active ingredient having an immediate release property may be dissolved in the gastrointestinal contents, with no intention of delaying or prolonging the dissolution of the active ingredient.
  • the ER-IR blend containing 20 mg phenylephrine had a Cmax that was 50% of the 10 mg IR dose and an AUCinf that was 15% more than two 10 mg IR doses (20 mg).
  • the ER-IR blend containing 30 mg phenylephrine had a Cmax that was 85% of the 10 mg IR dose and an AUCinf that was 61% more than two 10 mg IR doses (20 mg).
  • the ER-IR Blend containing 20 mg phenylephrine and 1300 mg acetaminophen had a Cmax that was 80% of the 10 mg phenylephrine IR dose and an AUCinf that was 22% more than two 10 mg IR doses (20 mg).

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pulmonology (AREA)
  • Otolaryngology (AREA)
  • Emergency Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Virology (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/US2014/019301 2013-03-15 2014-02-28 Phenylephrine resinate particles Ceased WO2014149526A1 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
JP2016500489A JP6314206B2 (ja) 2013-03-15 2014-02-28 樹脂酸フェニレフリン粒子
RU2015144181A RU2675788C2 (ru) 2013-03-15 2014-02-28 Частицы резината фенилэфрина
HK16107941.7A HK1219885B (en) 2013-03-15 2014-02-28 Phenylephrine resinate particles
MX2015012340A MX383890B (es) 2013-03-15 2014-02-28 Partículas de resinato de fenilefrina.
EP14709863.6A EP2968223B1 (en) 2013-03-15 2014-02-28 Phenylephrine resinate particles
UAA201509684A UA116372C2 (uk) 2013-03-15 2014-02-28 Частинки резинату фенілефрину
CA2906357A CA2906357C (en) 2013-03-15 2014-02-28 Complexes of phenylephrine and polystyrene sulfonate resins and use of same for treatment of nasal congestion
BR112015022975-1A BR112015022975B1 (pt) 2013-03-15 2014-02-28 Usos de um complexo fármaco-resina compreendendo fenilefrina e um cátion de sulfonato de poliestireno, e formulação farmacêutica
NZ712317A NZ712317B2 (en) 2013-03-15 2014-02-28 Phenylephrine resinate particles
CN201480015698.2A CN105263483A (zh) 2013-03-15 2014-02-28 树脂酸去氧肾上腺素颗粒
AU2014238059A AU2014238059B2 (en) 2013-03-15 2014-02-28 Phenylephrine resinate particles
IL241050A IL241050B (en) 2013-03-15 2015-09-02 Particles of phenylephrine resinate
PH12015502066A PH12015502066A1 (en) 2013-03-15 2015-09-11 Phenylephrine resinate particles having good auc

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13/832,694 US20140271892A1 (en) 2013-03-15 2013-03-15 Phenylephrine resinate particles having good auc
US13/832,694 2013-03-15

Publications (1)

Publication Number Publication Date
WO2014149526A1 true WO2014149526A1 (en) 2014-09-25

Family

ID=50272778

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/019301 Ceased WO2014149526A1 (en) 2013-03-15 2014-02-28 Phenylephrine resinate particles

Country Status (13)

Country Link
US (1) US20140271892A1 (enExample)
EP (1) EP2968223B1 (enExample)
JP (1) JP6314206B2 (enExample)
CN (2) CN105263483A (enExample)
AU (1) AU2014238059B2 (enExample)
BR (1) BR112015022975B1 (enExample)
CA (1) CA2906357C (enExample)
IL (1) IL241050B (enExample)
MX (1) MX383890B (enExample)
PH (1) PH12015502066A1 (enExample)
RU (1) RU2675788C2 (enExample)
UA (1) UA116372C2 (enExample)
WO (1) WO2014149526A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115068425A (zh) * 2014-12-12 2022-09-20 强生消费者公司 制备去氧肾上腺素树脂酸盐颗粒的方法与去氧肾上腺素树脂酸盐颗粒及其在药剂中的用途

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109187832B (zh) * 2018-09-30 2021-07-30 华润三九医药股份有限公司 Lc-ms/ms测定去氧肾上腺素浓度的方法及样品的前处理方法
KR20230127266A (ko) * 2020-12-29 2023-08-31 애브비 인코포레이티드 서방형 우파다시티닙 제형
US12303604B1 (en) 2024-10-16 2025-05-20 Currax Pharmaceuticals Llc Pharmaceutical formulations comprising naltrexone and/or bupropion

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US20050266032A1 (en) * 2003-12-17 2005-12-01 Sovereign Pharmaceuticals, Ltd. Dosage form containing multiple drugs
US20060057205A1 (en) * 2004-09-14 2006-03-16 Sovereign Pharmaceuticals, Ltd. Phenylepherine containing dosage form
WO2008064192A2 (en) * 2006-11-21 2008-05-29 Mcneil-Ppc, Inc. Modified release analgesic suspensions
WO2009158368A1 (en) * 2008-06-26 2009-12-30 Mcneil-Ppc, Inc. Coated particles containing pharmaceutically active agents
WO2010115015A1 (en) * 2009-04-03 2010-10-07 Coating Place, Inc. Modified-release pharmaceutical drug composition

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WO2003020242A1 (en) * 2001-08-29 2003-03-13 Srl Technologies, Inc. Sustained release preparations
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US20050265955A1 (en) * 2004-05-28 2005-12-01 Mallinckrodt Inc. Sustained release preparations
KR101495146B1 (ko) * 2006-03-16 2015-02-24 트리스 파마 인코포레이티드 약물 - 이온교환 수지 복합체를 함유하는 변형 방출 제제
US20080064694A1 (en) * 2006-09-11 2008-03-13 Auriga Laboratories, Inc. Multi-Phase Release Methscopolamine Compositions
US8323695B2 (en) * 2007-08-13 2012-12-04 Mcneil-Ppc, Inc. Method for stabilizing phenylephrine
US20130230587A1 (en) * 2010-11-10 2013-09-05 Rubicon Research Private Limited Sustained release compositions

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US20050266032A1 (en) * 2003-12-17 2005-12-01 Sovereign Pharmaceuticals, Ltd. Dosage form containing multiple drugs
US20060057205A1 (en) * 2004-09-14 2006-03-16 Sovereign Pharmaceuticals, Ltd. Phenylepherine containing dosage form
WO2008064192A2 (en) * 2006-11-21 2008-05-29 Mcneil-Ppc, Inc. Modified release analgesic suspensions
WO2009158368A1 (en) * 2008-06-26 2009-12-30 Mcneil-Ppc, Inc. Coated particles containing pharmaceutically active agents
WO2010115015A1 (en) * 2009-04-03 2010-10-07 Coating Place, Inc. Modified-release pharmaceutical drug composition

Non-Patent Citations (1)

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Title
SANEHI PARVISH ET AL: "DESIGN AND EVALUATION OF SUSTAINED RELEASE CHITOSAN COATED PHENYLEPHRINE HYDROCHLORIDE MICROCAPSULES", INTERNATIONAL JOURNAL OF PHARMA AND BIO SCIENCES, vol. 1, no. 1, 1 January 2010 (2010-01-01), pages 1 - 10, XP055117420, ISSN: 0975-6299 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115068425A (zh) * 2014-12-12 2022-09-20 强生消费者公司 制备去氧肾上腺素树脂酸盐颗粒的方法与去氧肾上腺素树脂酸盐颗粒及其在药剂中的用途

Also Published As

Publication number Publication date
PH12015502066A1 (en) 2016-01-25
CN105263483A (zh) 2016-01-20
BR112015022975B1 (pt) 2022-11-08
IL241050B (en) 2018-07-31
US20140271892A1 (en) 2014-09-18
MX2015012340A (es) 2016-06-29
CA2906357A1 (en) 2014-09-25
JP6314206B2 (ja) 2018-04-18
JP2016512250A (ja) 2016-04-25
EP2968223A1 (en) 2016-01-20
UA116372C2 (uk) 2018-03-12
CN111658624A (zh) 2020-09-15
NZ712317A (en) 2020-09-25
AU2014238059B2 (en) 2019-01-03
BR112015022975A8 (pt) 2022-07-26
HK1219885A1 (en) 2017-04-21
MX383890B (es) 2025-03-14
IL241050A0 (en) 2015-11-30
EP2968223B1 (en) 2020-10-28
BR112015022975A2 (pt) 2017-07-18
CA2906357C (en) 2021-03-16
AU2014238059A1 (en) 2015-09-17
RU2015144181A (ru) 2017-04-21
RU2675788C2 (ru) 2018-12-25

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