US20090281132A1 - Pharmaceutical formulation for use in hiv therapy - Google Patents

Pharmaceutical formulation for use in hiv therapy Download PDF

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Publication number
US20090281132A1
US20090281132A1 US12/310,693 US31069307A US2009281132A1 US 20090281132 A1 US20090281132 A1 US 20090281132A1 US 31069307 A US31069307 A US 31069307A US 2009281132 A1 US2009281132 A1 US 2009281132A1
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United States
Prior art keywords
ritonavir
process according
closure
lopinavir
granules
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.)
Abandoned
Application number
US12/310,693
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English (en)
Inventor
Kiran Kumar Narsaiah Velaveni
Sanjay Deshraj Verma
Akhilesh Ashok Dixit
Abhijit Mukund Deshmukh
Sanjeev Meharchand Sethi
Sourav Dilipkumar Mitra
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.)
Mylan Laboratories Ltd
Original Assignee
Matrix Laboratories 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
Application filed by Matrix Laboratories Ltd filed Critical Matrix Laboratories Ltd
Assigned to MATRIX LABORATORIES LIMITED reassignment MATRIX LABORATORIES LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DESHMUKH, ABHIJIT MUKUND, DIXIT, AKHILESH ASHOK, MITRA, SOURAV DILIPKUMAR, SETHI, SANJEEV MEHARCHAND, VELAVENI, KIRAN KUMAR NARSAIAH, VERMA, SANJAY DESHRAJ
Publication of US20090281132A1 publication Critical patent/US20090281132A1/en
Abandoned legal-status Critical Current

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    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2009—Inorganic compounds
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2027—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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • 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
    • A61P31/18—Antivirals for RNA viruses for HIV

Definitions

  • the present invention relates to a pharmaceutical formulation and in particular to pharmaceutical formulations for use in HIV therapy. It also discloses the processes to make the same.
  • the invention has been developed primarily for use as a formulation to be used for treatment in HIV therapy and will be described hereinafter with reference to this application. Also disclosed is an improved bottle pack for storing the formulations. However, it will be appreciated that the invention is not limited to this particular field of use.
  • Ritonavir NDVIR soft gelatin capsule
  • the active substance Ritonavir is characterized by low aqueous solubility, a lack of bioavailability when given in the solid state, instability once in solution under ambient conditions and a metallic taste.
  • 5,484,801 discloses a formulation wherein Ritonavir formulation has been optimized with respect to the vehicle, which essentially is a solvent comprising a mixture of (1) (a) a solvent selected from propylene glycol and polyethylene glycol or (b) a solvent selected from polyoxyethyleneglycerol triricinoleate, polyethylene glycol 40 hydrogenated castor oil, fractionated coconut oil, polyoxyethylene (20) sorbitan monooleate and 2-(2-ethoxyethoxy) ethanol or (c) a mixture thereof and (2) ethanol or propylene glycol to improve the bioavailability.
  • a solvent comprising a mixture of (1) (a) a solvent selected from propylene glycol and polyethylene glycol or (b) a solvent selected from polyoxyethyleneglycerol triricinoleate, polyethylene glycol 40 hydrogenated castor oil, fractionated coconut oil, polyoxyethylene (20) sorbitan monooleate and 2-(2-ethoxyethoxy) ethanol or (c) a mixture thereof and (2)
  • Kaletra® is a formulation of two HIV protease inhibitors [Lopinavir and Ritonavir] in a single formulation. Till recently, this formulation was available in a soft gel capsule, embodied in the patent U.S. Pat. No. 6,458,818 granted to Abbott. The patent covers a solution of Lopinavir and Ritonavir in a long chain fatty acid organic solvent. This soft gel formulation has been criticized due to stability problems and need for keeping the formulation in refrigerated condition. Abbott has now introduced a new tablet formulation for combined administration of Lopinavir and Ritonavir, instead of the previously known soft gel formulation. It has also filed patent applications related to this tablet formulation. For instance, WO2005039551 covers a combination of Lopinavir and Ritonavir in a water soluble polymer and surfactant wherein the tablet is formulated by melt extrusion process. Specifically, the disclosed process comprises following steps:
  • HIV therapy formulations need to be made in the most economical manner thereby reducing the final prices for AIDS patients across the world, especially in third world and developing countries.
  • the above formulation and related melt extrusion process on account of its requiring expensive extrusion machinery & use of multiple surfactants [N Vinyl pyrrolidone and Sorbitan monolaureate or polyoxyethyleneglycerol oxystearate] may not necessarily result in an economical formulation. Also, since the disclosed process requires heating the drug constituents to high temperatures [exceeding 100° C.] it may possibly result in degradation of the drug constituents.
  • a pharmaceutical formulation for use in HIV therapy According to one aspect of the invention there is also provided a process to make the same.
  • the invention provides a process to make a pharmaceutical formulation comprising the following steps:
  • Another aspect of the invention provides for a pharmaceutical formulation prepared by a process disclosed above.
  • the invention provides a process to make a pharmaceutical formulation comprising the following steps:
  • Another aspect of the invention provides for a pharmaceutical formulation prepared by a process disclosed above.
  • Another aspect of the invention provides for process to make pharmaceutical formulation comprising the steps of:
  • Another aspect of the invention provides for a pharmaceutical formulation prepared by a process described above.
  • FIG. 1 is a cross section view of a closure of the bottle pack according to the invention, while FIG. 1A shows a cross section view of an alternative closure of the bottle pack.
  • closure [ 2 ] has a receptacle [ 3 ] for holding a desiccant [ 4 ] within closure itself.
  • the receptacle [ 3 ] is a distinct part that is attached/fixed to the closure [ 2 ].
  • the receptacle [ 3 ] is molded within the closure [ 2 ] itself such that it is a permanent part of the closure body.
  • the bioavailability of drugs is directly related to their dissolution in the gastrointestinal fluids.
  • the anti retro viral drug may be selected from HIV protease inhibitor[s] such as Lopinavir, Ritonavir, Saquinavir, Nelfinavir, Atazanavir, Indinavir, Tipranavir, Palinavir, Amprenavir, Fosemaprenavir & Darunavir etc.
  • HIV protease inhibitor[s] such as Lopinavir, Ritonavir, Saquinavir, Nelfinavir, Atazanavir, Indinavir, Tipranavir, Palinavir, Amprenavir, Fosemaprenavir & Darunavir etc.
  • other anti-retro viral drugs such as Nucleoside Reverse Transcriptase Inhibitors [NRTIs] or Non-Nucleoside Reverse Transcriptase Inhibitors [NNRTIs] can be effectively employed without undue experimentation in the present invention to render
  • Nucleoside Reverse Transcriptase Inhibitors could be selected from Abacavir, Didanosine, Emtricitabine, Lamivudine, Stavudine, Zidovudine & Zalcitabine.
  • NNRTIs could be selected from Nevirapine, Delavirdine or Efavirenz.
  • Nucleotide Reverse Transcriptase Inhibitors such as Tenofovir could also be employed. The preferred single drug is Ritonavir.
  • any of the above anti-retro viral drugs and at least one pharmaceutically acceptable additive granulated in an organic solvent subsequently milled, and subsequently processed to pharmaceutical formulations such as tablets or capsules would also come within the ambit of the process of present invention.
  • the preferred drug combination is Lopinavir:Ritonavir in a proportion of 4:1.
  • Formulation methods such as melt extrusion, spray drying and solvent evaporation with melt extrusion have been suggested to make tablet formulations of Lopinavir and Ritonavir combination. These methods need specialized equipment and heating at high temperatures.
  • the present invention avoids factors such as use of specialised melt extrusion equipment, processing at high temperatures and provides a stable, solid pharmaceutical dosage form comprising at least one protease inhibitor admixed with pharmaceutical additives, granulated in an organic solvent, milled and finally processing the milled product into pharmaceutical formulations such as tablets or capsules.
  • a novel, stable and economical formulation for delivering at least one anti-retro viral drug is disclosed.
  • the formulation may also consist of a plurality of HIV protease inhibitors.
  • the process of granulation is carried out in presence of an organic solvent.
  • the process sequence consists broadly of:
  • steps [a] and [b] can be combined, such that all the items are mixed in the organic solvent to form a paste.
  • more than one drug can also be mixed in step [a].
  • the process may be is carried out in a Nitrogen atmosphere. Examples have been provided that will clarify the above general process steps.
  • the solvents to be used are organic solvents such as methanol, dichloromethane, ethanol, acetone, ethyl acetate, isopropyl alcohol, preferably, dichloromethane.
  • pharmaceutically acceptable additive includes ‘pharmaceutically acceptable excipient’ within its ambit and the singular term includes plural as well.
  • Pharmaceutically acceptable additives such as a solubilizing agent or a combination of solubilizing agents, pharmaceutically acceptable excipients having muco-adhesive properties, a glidant, a lubricant and a disintegrating agent can be added to further enhance the properties of the formulation.
  • the solubilizing agent may be either a pharmaceutically acceptable polymer or a pharmaceutically acceptable copolymer or any pharmaceutically acceptable fatty acid ester, used singly or in combination and should ideally be dispersible or soluble in organic solvent selected.
  • solubilizing agents examples include glyceryl mono-oleate, polyethylene-polypropylene glycol copolymer [Poloaxamer], sorbitan esters, polyoxyl castor oil, polyoxyethylene stearates.
  • Commercially available substances such as Poloaxamer 124/407 can also serve as the solubilizing agent.
  • the pharmaceutically acceptable excipient having muco-adhesive properties include cellulose ethers, polyacrylic acid, polymethacrylates, poloxamer, polydextrose, copovidone, polyvinyl alcohol, chitosan, guar gum, sodium alginate, dextrin, polyethylene glycol etc.
  • An e.g. for excipient having muco-adhesive property is Hydroxypropylmethyl cellulose [HPMC, commercially available as Hypromellose].
  • Glidants improve the flowability of the powder making up the tablet during production.
  • Glidants can be selected from selected from the group consisting of: silicon dioxide, colloidal silicon dioxide, fumed silicon dioxide, sodium aluminosilicate, calcium silicate, powdered cellulose, microcrystalline cellulose, corn starch, sodium benzoate, calcium carbonate, magnesium carbonate, asbestos free talc, metallic stearates, calcium stearate, magnesium stearate, zinc stearate, stearowet C, starch, starch 1500, magnesium lauryl sulfate, or magnesium oxide, where colloidal silicon dioxide is the preferred glidant.
  • Lubricants may be selected from the group of magnesium stearate, calcium stearate, sodium stearyl fumarate, stearic acid, hydrogenated cottonseed oil, sodium benzoate, sodium lauryl sulfate etc.
  • the pharmaceutical dosage form comprises:
  • the milled product post granulation is processed further, for e.g. it can be compressed to form tablets or filled into capsules, using standard machines/processes, known to persons skilled in the art.
  • the formulations of the present invention can be stored in ordinary HDPE/plastic bottles.
  • an improved bottle pack for storing such formulations Normal bottles have a closure with a cavity that closes around the bottle's neck such that the neck of the bottle fits within the closure's cavity.
  • a desiccant is also added to absorb moisture. But this practice means an additional processing step on the packing line as also the risk that some patients may ingest the desiccant confusing it with medicine.
  • Our improved bottle pack consists of a bottle and a closure that has a receptacle within its cavity such that the receptacle holds the desiccant.
  • the closure is fitted by the bottle pack supplier with a desiccant within the receptacle and hence there is no need for putting in a desiccant at the time of filling the medicines.
  • the receptacle may be formed as a part of the closure itself or it may be attached/added inside the closure.
  • the receptacle may fixed within the closure or it may be removably fixed within the closure.
  • FIG. 1 illustrates a closure where the receptacle is added inside the closure
  • FIG. 1A illustrates a closure where the receptacle is a part of the closure body itself.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Biophysics (AREA)
  • Inorganic Chemistry (AREA)
  • AIDS & HIV (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US12/310,693 2006-09-04 2007-08-31 Pharmaceutical formulation for use in hiv therapy Abandoned US20090281132A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN1597/CHE/2006 2006-09-04
IN1597CH2006 2006-09-04
PCT/IN2007/000382 WO2008029417A2 (en) 2006-09-04 2007-08-31 Pharmaceutical formulation for use in hiv therapy

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2007/000382 A-371-Of-International WO2008029417A2 (en) 2006-09-04 2007-08-31 Pharmaceutical formulation for use in hiv therapy

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/157,579 Continuation US8367080B2 (en) 2006-09-04 2011-06-10 Pharmaceutical formulation for use in HIV therapy

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US13/157,579 Active US8367080B2 (en) 2006-09-04 2011-06-10 Pharmaceutical formulation for use in HIV therapy

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US (2) US20090281132A1 (de)
EP (1) EP2063862A2 (de)
WO (1) WO2008029417A2 (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012164575A3 (en) * 2011-05-27 2013-02-07 Hetero Research Foundation Amorphous ritonavir co-precipitated
WO2012120541A3 (en) * 2011-03-07 2013-03-14 Hetero Research Foundation Amorphous form of lopinavir and ritonavir mixture
WO2013024494A3 (en) * 2011-08-18 2013-04-25 Hetero Research Foundation Amorphous mixture of lopinavir and ritonavir co-precipitated on copovidone
CN103945817A (zh) * 2011-12-26 2014-07-23 黄载日 用于药瓶的日期显示盖
US20220332483A1 (en) * 2021-04-16 2022-10-20 Tsang-Hung Hsu Elastic stretchable lid capable of absorbing moisture

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2009008935A (es) 2007-02-23 2009-11-02 Gilead Sciences Inc Moduladores de las propiedades farmacocineticas de productos terapeuticos.
MX2010011963A (es) * 2008-05-02 2010-12-06 Gilead Sciences Inc Uso de particulas trasportadoras solidas para mejorar la capacidad de procesamiento de un agente farmaceutico.
WO2009153654A1 (en) * 2008-06-17 2009-12-23 Aurobindo Pharma Limited Solid dosage forms of antiretrovirals

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050143404A1 (en) * 2003-08-28 2005-06-30 Joerg Rosenberg Solid pharmaceutical dosage formulation
US20060121106A1 (en) * 2003-02-21 2006-06-08 Janez Kerc Therapeutic system comprising amoxicillin and clavulanic acid
US20070163917A1 (en) * 2004-07-16 2007-07-19 Pfizer Inc. Package and device for simultaneously maintaining low moisture and low oxygen levels

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3458622A (en) * 1967-04-07 1969-07-29 Squibb & Sons Inc Controlled release tablet
US20050031696A1 (en) * 2003-04-22 2005-02-10 Dr. Reddy's Laboratories Limited Oral pharmaceutical formulations of acid-labile active ingredients and process for making same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060121106A1 (en) * 2003-02-21 2006-06-08 Janez Kerc Therapeutic system comprising amoxicillin and clavulanic acid
US20050143404A1 (en) * 2003-08-28 2005-06-30 Joerg Rosenberg Solid pharmaceutical dosage formulation
US20070163917A1 (en) * 2004-07-16 2007-07-19 Pfizer Inc. Package and device for simultaneously maintaining low moisture and low oxygen levels

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012120541A3 (en) * 2011-03-07 2013-03-14 Hetero Research Foundation Amorphous form of lopinavir and ritonavir mixture
US20150080420A1 (en) * 2011-03-07 2015-03-19 Hetero Research Foundation Amorphous form of lopinavir and ritonavir mixture
WO2012164575A3 (en) * 2011-05-27 2013-02-07 Hetero Research Foundation Amorphous ritonavir co-precipitated
US9096556B2 (en) 2011-05-27 2015-08-04 Hetero Research Foundation Amorphous ritonavir co-precipitated
WO2013024494A3 (en) * 2011-08-18 2013-04-25 Hetero Research Foundation Amorphous mixture of lopinavir and ritonavir co-precipitated on copovidone
CN103945817A (zh) * 2011-12-26 2014-07-23 黄载日 用于药瓶的日期显示盖
US20140202978A1 (en) * 2011-12-26 2014-07-24 Jae Il Hwang Date display cap for medicine bottle
EP2740460A4 (de) * 2011-12-26 2015-04-08 Jae Il Hwang Verschlusskappe mit datumsanzeige für eine medikamentenflasche
CN103945817B (zh) * 2011-12-26 2016-07-13 黄载日 用于药瓶的日期显示盖
US20220332483A1 (en) * 2021-04-16 2022-10-20 Tsang-Hung Hsu Elastic stretchable lid capable of absorbing moisture
US20230039575A1 (en) * 2021-04-16 2023-02-09 Tsang-Hung Hsu Elastic stretchable lid capable of absorbing moisture

Also Published As

Publication number Publication date
US20110262533A1 (en) 2011-10-27
WO2008029417A2 (en) 2008-03-13
EP2063862A2 (de) 2009-06-03
US8367080B2 (en) 2013-02-05
WO2008029417A3 (en) 2009-04-16

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AS Assignment

Owner name: MATRIX LABORATORIES LIMITED, INDIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:VELAVENI, KIRAN KUMAR NARSAIAH;VERMA, SANJAY DESHRAJ;DIXIT, AKHILESH ASHOK;AND OTHERS;REEL/FRAME:022377/0056

Effective date: 20090223

STCB Information on status: application discontinuation

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