WO2014092661A1 - Particulate formulations of tadalafil in effervescent form - Google Patents

Particulate formulations of tadalafil in effervescent form Download PDF

Info

Publication number
WO2014092661A1
WO2014092661A1 PCT/TR2013/000035 TR2013000035W WO2014092661A1 WO 2014092661 A1 WO2014092661 A1 WO 2014092661A1 TR 2013000035 W TR2013000035 W TR 2013000035W WO 2014092661 A1 WO2014092661 A1 WO 2014092661A1
Authority
WO
WIPO (PCT)
Prior art keywords
effervescent
formulation
range
tadalafil
agent
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/TR2013/000035
Other languages
French (fr)
Inventor
Mahmut Bilgic
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of WO2014092661A1 publication Critical patent/WO2014092661A1/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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0007—Effervescent
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems

Definitions

  • the present invention relates to pharmaceutical effervescent formulations comprising tadalafil for use in the treatment of erectile dysfunction.
  • Tadalafil was first disclosed in the application numbered W09519978. Use of tadalafil for the treatment of erectile dysfunction is disclosed in said document.
  • Tadalafil is available in 5 mg, 10 mg and 20 mg tablet forms on the market.
  • Particle size of the active agent is of great importance for the effervescent tablet forms. It generally affects the granule formulation, the solubility and bioavailability of the active agent and overall the dissolution of the effervescent tablet forms.
  • dio:d 50 ratio of the active agent tadalafil is in the range of 1 : 1.1 to 1 :15 and d 50 :d 9 o ratio of the active agent tadalafil is in the range of 1 :1.1 to 1 :5, said formulations dissolve easily in water and thus high absorption and bioavailability of active agent tadalafil, and effective treatment can be provided.
  • the present invention relates to the effervescent formulations comprising tadalafil wherein di 0 :d 50 ratio of the active agent tadalafil is in the range of 1 : 1.1 to 1 : 15 and d 50 :d9 0 ratio of the active agent tadalafil is in the range of 1 :1.1 to 1 :5.
  • di 0 :d 50 ratio of the active agent tadalafil is preferably in the range of 1 :5 to 1 :10 and d 5 o:d9 0 ratio of the active agent tadalafil is preferably in the range of 1 :2 to 1 :4.
  • d 50 used herein signifies that half of the said substance by volume has a particle size below the value stated with d 50 and the other half of the substance by volume has a particle size over the value stated with d 50 .
  • di 0 used herein signifies that 10 % of the said substance by volume has a particle size below the value stated with dio and the rest of the substance has a particle size over the value stated with d] 0 .
  • d 90 used herein signifies that 90 % of the said substance by volume has a particle size below the value stated with d 90 and the rest of the substance has a particle size over the value stated with d 90 .
  • d 50 , dio, d 90 values can be measured by one of the known measuring devices, for instance with a device which measures particle distribution by laser diffraction (for instance, Malvern Mastersizer etc.).
  • effervescent formulations of the present invention comprise tadalafil in the range of 0.01-10 %, preferably in the range of 0.05-5 %, more preferably in the range of 0.1-3 % by weight of the total amount of formulation.
  • Tadalafil that is comprised in the formulations of the present invention is in the form of its pharmaceutically acceptable salts, hydrates, solvates, esters, enantiomers, diastereomers or combinations thereof in terms of chemical structure; in amorphous or crystalline form or a combination thereof in terms of polymorphic structure.
  • effervescent formulations of the present invention comprise at least one pharmaceutically acceptable excipient along with tadalafil.
  • the pharmaceutically acceptable excipients that can be used in the effervescent formulations of the present invention can be selected from a group comprising effervescent acid, effervescent base, binder, sweetener and/or taste modifying agent, flavouring agent, lubricant, coloring agent and anti-foaming agent.
  • the effervescent acid that can be used in the effervescent formulations of the present invention and comprising tadalafil can be selected from a group comprising acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, propionic acid and tartaric acid or a combination thereof.
  • the effervescent base that can be used in the effervescent formulations of the present invention and comprising tadalafil can be selected from a group comprising sodium bicarbonate, sodium citrate dihydrate, sodium hydroxide or combinations thereof.
  • binders that can be used in the effervescent formulations of the present invention and comprising tadalafil can be selected from a group comprising ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, sorbitol, methylcellulose, povidone or a combination thereof.
  • solubility characteristics of the granules which are obtained during the preparation of the formulation. Granules having low flow characteristics may cause deviations in the tablet weight uniformity which results in unevenly distributed dose of the active agent.
  • An optimal binder composition is of a significant importance for obtaining granules with desired flow characteristics.
  • the inventors have surprisingly found that using a binder combination of two binding agents shows significant improvement in the problems known in the prior art and helps the granules to have desired flow characteristics.
  • the binder combination comprises the first binding agent and the second binding agent.
  • the first binding agent of the binder combination is preferably povidone and the second binding agent of the binder combination is preferably sorbitol.
  • the inventors have also surprisingly found that in the case that the ratio of the first binding agent to the second binding agent is between 1 :10 and 10:1, preferably between 1 :5 and 5:1, the granules having proper flow and high solubility can be provided.
  • another embodiment of the present invention is the effervescent formulation comprising tadalafil wherein said formulation comprises a binder combination comprising the first binding agent and the second binding agent and wherein the ratio of the first binding agent to the second binding is in the range of 1 :10 to 10:1, preferably 1 :5 to 5:1 by weight.
  • the sweetener and/or taste modifying agent that can be used in the effervescent formulations of the present invention can be selected from a group comprising acesulfame potassium, aspartame, fructose, maltitol, xylitol, saccharin, sodium cyclamate, sucralose, sucrose, sodium chloride.
  • the flavouring agent that can be used in the effervescent formulations of the present invention can be selected from menthol, methane, anethole, methyl salicylate, eucalyptol,' cinnamon, 1 - methyl acetate, sage, eugenol, oxanone, lemon, orange, strawberry, blackberry or combinations thereof.
  • the colouring agent that can be used in the effervescent formulations of the present invention can be selected from titanium dioxide, chlorophyl, yellow iron oxide, other synthetic iron oxides, beta-carotene or combinations thereof.
  • the lubricant that can be used in the effervescent formulations of the present invention can be selected from calcium stearate, magnesium stearate, talc, polyethylene glycol, PEG 6000, sodium benzoate, potassium benzoate, sodium lauryl sulphate, stearic acid, zinc stearate or combinations thereof.
  • the anti-foaming agent that can be used in the effervescent formulations of the present invention can be selected from polydimethylsiloxane, simethicone, other silicones, stearates, alcohols, glycols or combinations thereof.
  • the effervescent formulations of the present invention comprising tadalafil are characterized in that the amount of the active agent is in the range of 0.01-10 %, effervescent acid in the range of 1-80 %, effervescent base in the range of 1-70 %, binder in the range of 1-30 %, sweetener and/or taste modifying agent in the range of 1-30 %, lubricant in the range of 0.1-5 %, flavouring agent in the range of 0.1-10 %, colouring agent in the range of 0.01-10 %, anti- foaming agent in the range of 0.001-2 % in proportion to total weight of the formulation.
  • the method for preparation of the effervescent formulations of the present invention comprising tadalafil can be composed of the following steps: I. Tadalafil, a solvent and effervescent acid are mixed and the granulation solution is obtained.
  • flavouring agent the colouring agent, and the taste modifying agent are added into the granules obtained in the step III and the final mixture is obtained.
  • step IV The final mixture obtained in step IV is compressed into tablet form.
  • the pharmaceutical formulation according to the present invention can be used in prevention and treatment of erectile dysfunction.
  • Example 1 Formulation and process for preparation of tadalafil effervescent tablet
  • flavouring agent the colouring agent, and the taste modifying agent are added into the granules obtained in the step III and the final mixture is obtained.
  • step IV The final mixture obtained in step IV is compressed into tablet form.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Preparation (AREA)

Abstract

The present invention relates to pharmaceutical formulations in effervescent form comprising tadalafil for use in the treatment of erectile dysfunction.

Description

PARTICULATE FORMULATIONS OF TADALAFIL IN
EFFERVESCENT
The present invention relates to pharmaceutical effervescent formulations comprising tadalafil for use in the treatment of erectile dysfunction.
Tadalafil was first disclosed in the application numbered W09519978. Use of tadalafil for the treatment of erectile dysfunction is disclosed in said document.
Figure imgf000002_0001
Tadalafil is available in 5 mg, 10 mg and 20 mg tablet forms on the market.
However, currently available dosage forms have some disadvantages, especially for geriatric patients and for those who have swallowing difficulties. Therefore, they are not preferred by most of the patients. Considering the fact that an effective treatment mostly requires systematic use of the drugs, this may cause a serious problem. This problem could be solved by formulating the pharmaceutical composition in effervescent form.
Particle size of the active agent is of great importance for the effervescent tablet forms. It generally affects the granule formulation, the solubility and bioavailability of the active agent and overall the dissolution of the effervescent tablet forms.
Since good solubility is an essential feature for the effervescent tablets and tadalafil is known to have low solubility in water, there is a need for new approaches and solutions for development of effervescent tablet formulations comprising tadalafil which dissolve easily in water.
The inventors have surprisingly found that in the case where dio:d50 ratio of the active agent tadalafil is in the range of 1 : 1.1 to 1 :15 and d50:d9o ratio of the active agent tadalafil is in the range of 1 :1.1 to 1 :5, said formulations dissolve easily in water and thus high absorption and bioavailability of active agent tadalafil, and effective treatment can be provided. The present invention relates to the effervescent formulations comprising tadalafil wherein di0:d50 ratio of the active agent tadalafil is in the range of 1 : 1.1 to 1 : 15 and d50:d90 ratio of the active agent tadalafil is in the range of 1 :1.1 to 1 :5.
In a preferred embodiment of the present invention, di0:d50 ratio of the active agent tadalafil is preferably in the range of 1 :5 to 1 :10 and d5o:d90 ratio of the active agent tadalafil is preferably in the range of 1 :2 to 1 :4.
The term "d50" used herein signifies that half of the said substance by volume has a particle size below the value stated with d50 and the other half of the substance by volume has a particle size over the value stated with d50.
The term di0 used herein signifies that 10 % of the said substance by volume has a particle size below the value stated with dio and the rest of the substance has a particle size over the value stated with d]0.
The term d90 used herein signifies that 90 % of the said substance by volume has a particle size below the value stated with d90 and the rest of the substance has a particle size over the value stated with d90. d50, dio, d90 values can be measured by one of the known measuring devices, for instance with a device which measures particle distribution by laser diffraction (for instance, Malvern Mastersizer etc.).
Another characteristic feature of the effervescent formulations of the present invention is that said formulations comprise tadalafil in the range of 0.01-10 %, preferably in the range of 0.05-5 %, more preferably in the range of 0.1-3 % by weight of the total amount of formulation.
Tadalafil that is comprised in the formulations of the present invention is in the form of its pharmaceutically acceptable salts, hydrates, solvates, esters, enantiomers, diastereomers or combinations thereof in terms of chemical structure; in amorphous or crystalline form or a combination thereof in terms of polymorphic structure.
Another characteristic feature of the effervescent formulations of the present invention is that said formulations comprise at least one pharmaceutically acceptable excipient along with tadalafil. The pharmaceutically acceptable excipients that can be used in the effervescent formulations of the present invention can be selected from a group comprising effervescent acid, effervescent base, binder, sweetener and/or taste modifying agent, flavouring agent, lubricant, coloring agent and anti-foaming agent.
The effervescent acid that can be used in the effervescent formulations of the present invention and comprising tadalafil can be selected from a group comprising acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, propionic acid and tartaric acid or a combination thereof.
The effervescent base that can be used in the effervescent formulations of the present invention and comprising tadalafil can be selected from a group comprising sodium bicarbonate, sodium citrate dihydrate, sodium hydroxide or combinations thereof.
The binders that can be used in the effervescent formulations of the present invention and comprising tadalafil can be selected from a group comprising ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, sorbitol, methylcellulose, povidone or a combination thereof.
Another important factor affecting solubility of effervescent formulations is the solubility characteristics of the granules which are obtained during the preparation of the formulation. Granules having low flow characteristics may cause deviations in the tablet weight uniformity which results in unevenly distributed dose of the active agent. An optimal binder composition is of a significant importance for obtaining granules with desired flow characteristics.
The inventors have surprisingly found that using a binder combination of two binding agents shows significant improvement in the problems known in the prior art and helps the granules to have desired flow characteristics. The binder combination comprises the first binding agent and the second binding agent.
The first binding agent of the binder combination is preferably povidone and the second binding agent of the binder combination is preferably sorbitol.
The inventors have also surprisingly found that in the case that the ratio of the first binding agent to the second binding agent is between 1 :10 and 10:1, preferably between 1 :5 and 5:1, the granules having proper flow and high solubility can be provided. Accordingly, another embodiment of the present invention is the effervescent formulation comprising tadalafil wherein said formulation comprises a binder combination comprising the first binding agent and the second binding agent and wherein the ratio of the first binding agent to the second binding is in the range of 1 :10 to 10:1, preferably 1 :5 to 5:1 by weight.
The sweetener and/or taste modifying agent that can be used in the effervescent formulations of the present invention can be selected from a group comprising acesulfame potassium, aspartame, fructose, maltitol, xylitol, saccharin, sodium cyclamate, sucralose, sucrose, sodium chloride.
The flavouring agent that can be used in the effervescent formulations of the present invention can be selected from menthol, methane, anethole, methyl salicylate, eucalyptol,' cinnamon, 1 - methyl acetate, sage, eugenol, oxanone, lemon, orange, strawberry, blackberry or combinations thereof.
The colouring agent that can be used in the effervescent formulations of the present invention can be selected from titanium dioxide, chlorophyl, yellow iron oxide, other synthetic iron oxides, beta-carotene or combinations thereof.
The lubricant that can be used in the effervescent formulations of the present invention can be selected from calcium stearate, magnesium stearate, talc, polyethylene glycol, PEG 6000, sodium benzoate, potassium benzoate, sodium lauryl sulphate, stearic acid, zinc stearate or combinations thereof.
The anti-foaming agent that can be used in the effervescent formulations of the present invention can be selected from polydimethylsiloxane, simethicone, other silicones, stearates, alcohols, glycols or combinations thereof.
The effervescent formulations of the present invention comprising tadalafil are characterized in that the amount of the active agent is in the range of 0.01-10 %, effervescent acid in the range of 1-80 %, effervescent base in the range of 1-70 %, binder in the range of 1-30 %, sweetener and/or taste modifying agent in the range of 1-30 %, lubricant in the range of 0.1-5 %, flavouring agent in the range of 0.1-10 %, colouring agent in the range of 0.01-10 %, anti- foaming agent in the range of 0.001-2 % in proportion to total weight of the formulation.
The method for preparation of the effervescent formulations of the present invention comprising tadalafil can be composed of the following steps: I. Tadalafil, a solvent and effervescent acid are mixed and the granulation solution is obtained.
II. The effervescent acid, the effervescent base, the binder combination, the sweetener and the anti foaming agent are granulated with the granulation solution obtained in Step I.
III. The granules obtained in the step II are dried and sieved.
IV. The flavouring agent, the colouring agent, and the taste modifying agent are added into the granules obtained in the step III and the final mixture is obtained.
V. The final mixture obtained in step IV is compressed into tablet form.
The pharmaceutical formulation according to the present invention can be used in prevention and treatment of erectile dysfunction.
EXAMPLES
Example 1: Formulation and process for preparation of tadalafil effervescent tablet
Figure imgf000006_0001
I. Tadalafil, a solvent and effervescent acid are mixed and the granulation solution is obtained.
II. The effervescent acid, the effervescent base, the binder combination, the sweetener and the anti foaming agent are granulated with the granulation solution obtained in Step I.
III. The granules obtained in the step II are dried and sieved.
IV. The flavouring agent, the colouring agent, and the taste modifying agent are added into the granules obtained in the step III and the final mixture is obtained.
V. The final mixture obtained in step IV is compressed into tablet form.

Claims

1. A pharmaceutical formulation in effervescent form comprising tadalafil in the amount of 0.01-10 %, characterized in that d10:d5o ratio of tadalafil is in the range of 1 :1,1 to 1 :15 and ds0:d9o ratio of tadalafil is in the range of 1 : 1 , 1 to 1 :5.
2. The formulation according to claim 1, characterized in that d10:d5o ratio of tadalafil is in the range of 1 : 5 to 1 : 10, and d5o'.d9o ratio of tadalafil is in the range of 1 :2 to 1 :4.
3. The formulation according to claims 1-2, characterized in that said formulation is in form of effervescent tablet, effervescent granule and effervescent powder.
4. The formulation according to claim 3, characterized in that said formulation is in effervescent tablet form.
5. The formulation according to any preceding claims, characterized in that the active agent tadalafil is in the form of its pharmaceutically acceptable salts, hydrates, solvates, esters, enantiomers, diastereomers or combinations thereof in terms of chemical structure; in amorphous or crystalline form or a combination thereof in terms of polymorphic structure.
6. The formulation according to any preceding claims, characterized in that said formulation comprises at least one pharmaceutically acceptable excipient in addition to tadalafil.
7. The formulation according to claim 6, characterized in that said excipients that can be comprised in the formulation are selected from a group comprising effervescent acid, effervescent base, binder, sweetener and/or taste modifying agent, lubricant, flavouring agent, colouring agent and anti-foaming agent or combinations thereof.
8. The formulation according to claim 7, characterized in that the effervescent acid that is comprised in the formulation is selected from a group comprising acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, propionic acid and tartaric acid or a combination thereof.
9. The formulation according to claim 7, characterized in that the effervescent base that is comprised in the formulation is selected from a group comprising sodium bicarbonate, sodium citrate dihydrate, sodium hydroxide or combinations thereof.
10. The formulation according to claim 7, characterized in that the binder combination that is comprised in the formulation is selected from a group comprising ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, sorbitol, methyl cellulose, povidone.
11. The formulation according to any preceding claims, characterized in that it contains a binder combination comprising a first binding agent and a second binding agent.
12. The formulation according to claim 11, characterized that the first binding agent of the binder combination is povidone and the second binding agent of the binder combination is sorbitol.
13. The formulation according to claim 11-12, characterized in that the weight ratio of the first binder to second binder is between 1 :10 and 10: 1.
14. The formulation according to claim 11-13, characterized in that the weight ratio of the first binder to second binder is between 1 :5 and 5: 1.
15. The effervescent formulation according to any preceding claims, characterized in that the amount of the active agent is in the range of 0.01-10 %, effervescent acid in the range of 1-80 %, effervescent base in the range of 1-70 %, binder in the range of 1-30 %, sweetener and/or taste modifying agent in the range of 1-30 %, lubricant in the range of 0.1-5 %, flavouring agent in the range of 0.1-10 %, colouring agent in the range of 0.01-10 %, anti-foaming agent in the range of 0.001-2 % in proportion to total weight of formulation.
16. The production method of the effervescent formulation comprising tadalafil according to any preceding claims, wherein said method comprises the following steps:
I. Tadalafil, a solvent and effervescent acid are mixed and the granulation solution is obtained.
II. The effervescent acid, the effervescent base, the binder combination, the sweetener and the anti foaming agent are granulated with the granulation solution obtained in Step I.
III. The granules obtained in the step II are dried and sieved.
IV. The flavouring agent, the colouring agent, and the taste modifying agent are added into the granules obtained in the step III and the final mixture is obtained.
V. The final mixture obtained in step IV is compressed into tablet form.
PCT/TR2013/000035 2012-01-18 2013-01-18 Particulate formulations of tadalafil in effervescent form Ceased WO2014092661A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR201200601 2012-01-18
TR2012/00601 2012-01-18

Publications (1)

Publication Number Publication Date
WO2014092661A1 true WO2014092661A1 (en) 2014-06-19

Family

ID=48083586

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/TR2013/000035 Ceased WO2014092661A1 (en) 2012-01-18 2013-01-18 Particulate formulations of tadalafil in effervescent form
PCT/TR2013/000043 Ceased WO2013109230A1 (en) 2012-01-18 2013-01-18 Pharmaceutical compositions comprising tadalafil

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/TR2013/000043 Ceased WO2013109230A1 (en) 2012-01-18 2013-01-18 Pharmaceutical compositions comprising tadalafil

Country Status (1)

Country Link
WO (2) WO2014092661A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN2013MU01177A (en) * 2013-03-28 2015-04-17 Astron Res Ltd
MX379254B (en) * 2016-02-26 2025-03-10 Apotex Inc Novel pharmaceutical formulations comprising a pds5 inhibitor
WO2025004098A1 (en) * 2023-06-25 2025-01-02 Zenvision Pharma Llp Pharmaceutical composition comprising oyster peptide and pde5 inhibitor(s) or salts thereof"

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995019978A1 (en) 1994-01-21 1995-07-27 Laboratoires Glaxo Wellcome S.A. Tetracyclic derivatives, process of preparation and use
US6821975B1 (en) * 1999-08-03 2004-11-23 Lilly Icos Llc Beta-carboline drug products
US20060286166A1 (en) * 2005-02-25 2006-12-21 Inbal Ornan Tadalafil having a large particle size and a process for preparation thereof
US20070098804A1 (en) * 2005-08-29 2007-05-03 Judith Aronhime Solid particulate tadalafil having a bimodal particle size distribution
US20070104792A1 (en) * 2005-09-13 2007-05-10 Elan Pharma International, Limited Nanoparticulate tadalafil formulations
EP1985310A1 (en) * 2007-04-25 2008-10-29 Teva Pharmaceutical Industries Ltd. Solid dosage forms

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2214478A1 (en) * 2007-10-19 2010-08-11 Innozen, Inc. Composition for administering an active ingredient and method for making and using the same
WO2011030351A2 (en) * 2009-09-03 2011-03-17 Rubicon Research Private Limited Taste - masked pharmaceutical compositions
US20110263606A1 (en) * 2010-04-26 2011-10-27 Horst Zerbe Solid oral dosage forms comprising tadalafil

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995019978A1 (en) 1994-01-21 1995-07-27 Laboratoires Glaxo Wellcome S.A. Tetracyclic derivatives, process of preparation and use
US6821975B1 (en) * 1999-08-03 2004-11-23 Lilly Icos Llc Beta-carboline drug products
US20060286166A1 (en) * 2005-02-25 2006-12-21 Inbal Ornan Tadalafil having a large particle size and a process for preparation thereof
US20070098804A1 (en) * 2005-08-29 2007-05-03 Judith Aronhime Solid particulate tadalafil having a bimodal particle size distribution
US20070104792A1 (en) * 2005-09-13 2007-05-10 Elan Pharma International, Limited Nanoparticulate tadalafil formulations
EP1985310A1 (en) * 2007-04-25 2008-10-29 Teva Pharmaceutical Industries Ltd. Solid dosage forms

Also Published As

Publication number Publication date
WO2013109230A1 (en) 2013-07-25

Similar Documents

Publication Publication Date Title
KR102051132B1 (en) Pharmaceutical composition for controlled release comprising Mirabegron or its salts
CA2599617C (en) Drug formulations having improved pharmacokinetic properties
US12350377B2 (en) Preparation containing 6,7-unsaturated-7-carbamoyl morphinan derivatives
KR101320058B1 (en) Fast dissolving film comprising drug and method for manufacture thereof
EP2563340A2 (en) Water soluble pharmaceutical composition
KR20150002453A (en) Chewable tablet formulation comprising tadalafil or a pharmaceutically acceptable salt thereof
TW201713343A (en) Pharmaceutical composition for oral administration
WO2013109223A1 (en) Particulate formulations of tadalafil in effervescent form
EP3233064A1 (en) Pharmaceutical composition comprising gefifinib
Mohammed-Kadhum et al. Development and characterization of furosemide-loaded binary amorphous solid dispersion to enhance solubility and dissolution for pediatric oral administration
KR20150145730A (en) A pharmaceutical preparation comprising entecavir as an active ingredient and the method for preparing the same
JP2015040206A (en) Oral fast-disintegrating tablet containing irritative (astringency, acidity, bitterness) drug and method for producing the same
KR101304343B1 (en) Fast dissolving oral formulation of pde-5 inhibitors
KR101453320B1 (en) Oral Formulation and Preparation Method thereof
EP2243468A1 (en) Orally Disintegrating Dimebolin Compositions
WO2011139252A2 (en) Efervescent formulations comprising cefdinir
TW200304807A (en) Sleeping medicine formed by coating solid
WO2013109230A1 (en) Pharmaceutical compositions comprising tadalafil
EP2528593A2 (en) Effervescent formulations comprising cefprozil as active agent
WO2014104989A1 (en) Pharmaceutical compositions comprising aripiprazole
EP3068376A1 (en) Ondansetron sublingual spray formulation
WO2013100878A1 (en) Pharmaceutical formulations comprising aripiprazole
ES2665868T3 (en) Tablet containing composite material with cyclodextrin
WO2013109221A1 (en) New effervescent formulations comprising sweetener composition
WO2013100871A1 (en) Effervescent rivastigmine formulations

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13720144

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 13720144

Country of ref document: EP

Kind code of ref document: A1