CA2898408C - Enhanced stability of novel liquid compositions - Google Patents

Enhanced stability of novel liquid compositions Download PDF

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Publication number
CA2898408C
CA2898408C CA2898408A CA2898408A CA2898408C CA 2898408 C CA2898408 C CA 2898408C CA 2898408 A CA2898408 A CA 2898408A CA 2898408 A CA2898408 A CA 2898408A CA 2898408 C CA2898408 C CA 2898408C
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CA
Canada
Prior art keywords
composition
phenylephrine
guaifenesin
polyvinylpyrrolidone
precipitation
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.)
Active
Application number
CA2898408A
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English (en)
French (fr)
Other versions
CA2898408A1 (en
Inventor
Gary Robert Agisim
Robert Alan FRIEDLINE
Shivangi Vijaykumar PATEL
Cesar Ivan Sertzen
Vanessa Rose SHEPPERSON
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.)
Haleon US Holdings LLC
Original Assignee
Pfizer Inc
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Publication date
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Application filed by Pfizer Inc filed Critical Pfizer Inc
Publication of CA2898408A1 publication Critical patent/CA2898408A1/en
Application granted granted Critical
Publication of CA2898408C publication Critical patent/CA2898408C/en
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Classifications

    • 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
    • A61K9/08—Solutions
    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
    • 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
    • A61K31/33—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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/485—Morphinan derivatives, e.g. morphine, codeine
    • 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
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K9/10—Dispersions; Emulsions
    • 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
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4866—Organic macromolecular compounds
    • 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
    • A61P11/14—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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Virology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pain & Pain Management (AREA)
  • Molecular Biology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Dispersion Chemistry (AREA)
  • Biochemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Rheumatology (AREA)
  • Immunology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2898408A 2013-02-28 2014-02-13 Enhanced stability of novel liquid compositions Active CA2898408C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361770988P 2013-02-28 2013-02-28
US61/770,988 2013-02-28
PCT/IB2014/058978 WO2014132163A1 (en) 2013-02-28 2014-02-13 Enhanced stability of novel liquid compositions

Publications (2)

Publication Number Publication Date
CA2898408A1 CA2898408A1 (en) 2014-09-04
CA2898408C true CA2898408C (en) 2018-01-02

Family

ID=50193557

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2898408A Active CA2898408C (en) 2013-02-28 2014-02-13 Enhanced stability of novel liquid compositions

Country Status (20)

Country Link
US (3) US9308166B2 (enExample)
EP (1) EP2961377B1 (enExample)
JP (2) JP6067892B2 (enExample)
KR (3) KR101695580B1 (enExample)
CN (2) CN108187054B (enExample)
AU (2) AU2014222418B2 (enExample)
BR (1) BR112015018838B1 (enExample)
CA (1) CA2898408C (enExample)
ES (1) ES2792082T3 (enExample)
HK (1) HK1255605A1 (enExample)
IL (2) IL240080A (enExample)
MX (1) MX345183B (enExample)
NZ (2) NZ709958A (enExample)
PH (1) PH12015501753B1 (enExample)
PL (1) PL2961377T3 (enExample)
RU (1) RU2015137145A (enExample)
SG (1) SG11201505607SA (enExample)
TW (1) TWI531385B (enExample)
WO (1) WO2014132163A1 (enExample)
ZA (1) ZA201505058B (enExample)

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NZ709958A (en) * 2013-02-28 2018-03-23 Pfizer Enhanced stability of novel liquid compositions
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US20180263916A1 (en) 2015-09-28 2018-09-20 Puracap Pharmaceutical Llc Soft gelatin capsules containing a mixture of analgesics and decongestants, expectorants, antitussives and/or antihistamines
US9549907B1 (en) * 2015-11-13 2017-01-24 Sovereign Pharmaceuticals, Llc Immediate release oral guaifenesin solution
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AU2018284247B2 (en) 2017-06-14 2020-04-30 Crititech Inc. Methods for treating lung disorders
CA3076919A1 (en) 2017-10-03 2019-04-11 Crititech, Inc. Local delivery of antineoplastic particles in combination with systemic delivery of immunotherapeutic agents for the treatment of cancer
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CN109125257B (zh) * 2018-10-18 2020-12-01 云南大唐汉方制药股份有限公司 氨酚愈创肾素口服液及其制备方法
CN109044968B (zh) * 2018-10-18 2020-12-01 云南大唐汉方制药股份有限公司 氨酚右美肾素口服液及其制备方法
CN109045003B (zh) * 2018-10-18 2020-12-01 云南大唐汉方制药股份有限公司 氨酚拉明肾素口服液及其制备方法
TWI850346B (zh) * 2019-03-11 2024-08-01 美商Ｒ Ｐ 先靈爾科技公司 於軟凝膠中改善api穩定性
SG11202111251SA (en) 2019-04-11 2021-11-29 R P Scherer Technologies Llc Formulation for oral delivery of proteins, peptides and small molecules with poor permeability
CN110302149A (zh) * 2019-08-07 2019-10-08 北京博达绿洲医药科技研究有限公司 一种适合4-11岁儿童服用抗感冒药物及其制备方法
CN110279695B (zh) * 2019-08-07 2022-04-08 北京博智绿洲医药科技有限公司 一种治疗流涕、鼻塞等感冒症状的药物组合物及其制备方法和用途
CN110507607A (zh) * 2019-09-27 2019-11-29 葵花药业集团北京药物研究院有限公司 苯海拉明肾素口服液及其制备方法和用途
RS65089B1 (sr) * 2019-12-23 2024-02-29 Nutra Essential Otc S L Tečna kompozicija koja sadrži ibuprofen i fenilefrin
CN121361865A (zh) * 2025-09-08 2026-01-20 海南中远海运环保科技有限公司 一种醇溶性破乳药剂的制备方法

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Also Published As

Publication number Publication date
EP2961377A1 (en) 2016-01-06
JP2016510019A (ja) 2016-04-04
SG11201505607SA (en) 2015-09-29
CA2898408A1 (en) 2014-09-04
BR112015018838B1 (pt) 2020-12-15
US9744133B2 (en) 2017-08-29
IL240080A (en) 2016-08-31
WO2014132163A1 (en) 2014-09-04
KR20150111358A (ko) 2015-10-05
IL246985B (en) 2021-04-29
KR20160148723A (ko) 2016-12-26
TW201446284A (zh) 2014-12-16
JP2017078084A (ja) 2017-04-27
KR101695580B1 (ko) 2017-01-13
CN108187054A (zh) 2018-06-22
RU2015137145A (ru) 2017-04-03
AU2014222418A1 (en) 2015-07-30
JP6067892B2 (ja) 2017-01-25
NZ709958A (en) 2018-03-23
TWI531385B (zh) 2016-05-01
AU2014222418B2 (en) 2016-06-23
BR112015018838A2 (pt) 2017-07-18
KR20190136139A (ko) 2019-12-09
PL2961377T3 (pl) 2020-11-02
HK1215685A1 (zh) 2016-09-09
AU2016208390B2 (en) 2017-04-13
US20160151280A1 (en) 2016-06-02
US9308166B2 (en) 2016-04-12
ES2792082T3 (es) 2020-11-10
HK1255605A1 (zh) 2019-08-23
KR102218334B1 (ko) 2021-02-19
PH12015501753A1 (en) 2015-11-09
IL246985A0 (en) 2016-09-29
ZA201505058B (en) 2017-05-31
AU2016208390A1 (en) 2016-08-18
CN108187054B (zh) 2021-07-13
CN105007891A (zh) 2015-10-28
MX2015011207A (es) 2015-10-29
IL240080A0 (en) 2015-08-31
PH12015501753B1 (en) 2022-09-30
CN105007891B (zh) 2018-01-16
US20170319479A1 (en) 2017-11-09
EP2961377B1 (en) 2020-03-18
MX345183B (es) 2017-01-05
NZ739588A (en) 2019-03-29
US20140243364A1 (en) 2014-08-28

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