WO2012120522A1 - A taste masked chewable tablet of sildenafil - Google Patents
A taste masked chewable tablet of sildenafil Download PDFInfo
- Publication number
- WO2012120522A1 WO2012120522A1 PCT/IN2011/000138 IN2011000138W WO2012120522A1 WO 2012120522 A1 WO2012120522 A1 WO 2012120522A1 IN 2011000138 W IN2011000138 W IN 2011000138W WO 2012120522 A1 WO2012120522 A1 WO 2012120522A1
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- WIPO (PCT)
- Prior art keywords
- sildenafil
- taste masked
- chewable tablet
- tablet
- pharmaceutical excipient
- 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
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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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
Definitions
- the present invention relates to taste masked chewable tablet of sildenafil useful in the treatment of pulmonary hypertension and erectile dysfunction.
- Sildenafil is a selective inhibitor of cyclic guanosine monophosphate (cGMP)- specific phosphodiesterase type 5 (PDE5), marketed by Pfizer. Sildenafil is designated chemically as l-[[3-(6, 7-dihydro-l-methyl-7- oxo-3-propyl-l -pyrazolo[4,3-d] pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4- methyl piperazine.
- cGMP cyclic guanosine monophosphate
- PDE5 phosphodiesterase type 5
- the pharmaceutically acceptable salt of sildenafil, sildenafil citrate has a very bitter taste and hence tablets which are commercially available are film coated.
- the film coating masks any bitter taste in the mouth.
- taste masking of sildenafil by coating with polymers is already known in the art.
- United States Patent No. 6,221,402 (assigned to Pfizer referred to herein as '402 patent) discloses a rapidly releasing and taste masking pharmaceutical dosage form of sildenafil and a process of its preparation.
- the dosage form has an inner and outer coating wherein the inner coating coats the core of sildenafil citrate and low-substituted hydroxypropylcellulose and the outer coating comprises a saliva-insoluble polymer.
- PCT publication WO 2004087111 discloses oral taste masked pharmaceutical compositions that include a core having an active ingredient coated with a mixture of polymeric film forming binders and inorganic carriers. Processes for preparing the oral taste masked pharmaceutical composition are also provided.
- PCT publication WO2009074995 (assigned to M/S Ajanta Pharma Limited referred to herein as '995 publication) relates to tablets comprising sildenafil mask complex. However, the tablets comprise additional taste masking pharmaceutical excipient like monoammonium glycerrhizinate for masking the bitter taste of sildenafil citrate.
- the process for the preparation of the tablets involves wet granulation which could degrade sildenafil.
- the present invention relates to chewable tablets without additional taste masking pharmaceutical excipient and is prepared under anhydrous conditions.
- PCT Symposium on M/S Ocean, referred to herein as '626 publication relates to orodispersible tablets of phosphodiesterase -5 inhibitors including sildenafil.
- the amount of disintegrant used is more than 5% of weight of tablet.
- process for the preparation of tablets utilizes organic solvent in the moist granulation procedure.
- the present invention relates to chewable tablets which comprises less than 5% of disintegrant and is prepared under anhydrous conditions and in the absence of organic solvent.
- the object of the present invention is to provide a taste masked chewable tablet of sildenafil and the process of its preparation.
- a taste masked chewable tablet of sildenafil comprising
- the present invention provides a taste masked chewable tablet of sildenafil.
- the taste masked chewable tablet of sildenafil comprises complex of sildenafil with divinylbenzene methacrylate prepared in the absence of organic solvent and directly compressible pharmaceutical excipient(s) wherein the tablets are obtainable by method under anhydrous conditions
- Anhydrous conditions may, be selected from compaction, direct compression and dry granulation.
- the directly compressible pharmaceutical excipient may be selected from diluents, binders, lubricants, disintegrants, flavoring agents, coloring agents, stabilizers, surfactants, glidants, plasticizers, preservatives and sweeteners.
- Diluents may be selected from calcium carbonate, calcium phosphate dibasic, calcium phosphate tribasic, calcium sulfate, microcrystalline cellulose, microcrystalline silicified cellulose, powdered cellulose, dextrates, dextrose, fructose, lactitol, lactose anhydrous, lactose monohydrate, lactose dihydrate, lactose trihydrate, starch, pregelatinized starch, sucrose, talc, maltose maltodextrin.
- Binders may be selected from acacia, alginic acid, carbomer, carboxymethylcellulose calcium, carbomethylcellulose sodium, microcrystalline cellulose,powdered cellulose, ethyl cellulose, gelatin liquid glucose, guar gum, hydroxyethyl cellulos, hydroxypropyl cellulose, hydroxypropylmethyl cellulose, maltodextrin, methylcellulose, ploydextrose, polyethtylene oxide,povidone, sodium alginate, starch paste, pregelatinized starch, sucrose, tragacanth, low-substituted hydroxypropyl cellulose,glucose, sorbitol.
- Suitable fillers are preferably selected from atleast one of starch derivatives.such as com starch, potato starch or rice starch.
- starch derivatives such as com starch, potato starch or rice starch.
- Polysaccharides such as dextrins, maltodextrins, dextrates, microcrystalline cellulose, powdered cellulose, mixture of microcrystalline cellulose and guar gum, coprocessed blends of microcrystalline cellulose; and polyhydric alcohols, such as xylitol and sorbitol.
- Lubricants may be selected from magnesium stearate, stearic acid, sodium stearyl fumarate, magnesium lauryl sulphate, talc, polyethylene glycol, and glyceryl behenate.
- Disintegrants may be selected from, alginic acid, carbon dioxide, carboxymethylcellulose, calcium carboxymethylcellulose sodium, microcrystalline cellulose, powdered cellulose, croscarmelose sodium, crospovidone, sodium docusate, gaur gum, hydroxypropyl cellulose, methylcellulose, polacrilin potassium , poloxamer, povidone, sodium alginate, sodium glycine carbonate, sodium laulyl sulfate, sodium starch glycolate, starch, pregelatinized starch, low-substituted hydroxypropyl cellulose.
- the amount of disintegrant used is preferably less than 5% by weight of the tablet, more preferably 3-5% by weight of the tablet.
- Flavoring agents may be selected from natural or synthetic flavors such as strawberry flavor, wild cherry flavor, green apple flavor, spearmint flavor and peppermint flavor.
- Glidarits may be, for example, calcium silicate, powdered cellulose, starch, talc, colloidal silicon dioxide.
- Suitable sweeteners may be selected from sugars such as sucrose, lactose and glucose; cyclamate and salts thereof; saccharin and salts thereof; and aspartame.
- the directly compressible pharmaceutical excipient used in the present invention will not comprise sugar alcohol.
- the directly compressible pharmaceutical excipient used in the present invention will not comprise organic acid.
- the directly compressible pharmaceutical excipient used in the present invention will not comprise . monoammonium glycerhizinate
- the taste masked chewable tablet of sildenafil is triangular in shape.
- the dimensions of the tablets of the present invention may be as follows
- the process for the preparation of taste masked chewable tablet of sildenafil or its pharmaceutically acceptable salt is also provided.
- a process for the preparation of taste masked chewable tablet of sildenafil comprising
- the process of the present invention for preparing sildenafil complex with crosslinked polymer of divinylbenzene methacrylate is carried out in the absence of organic solvent like ethanol and the like. Further, the process of mixing sildenafil complexed with crosslinked polymer of divinylbenzene methacrylate with directly compressible pharmaceutical excipient(s) will not comprise water or an organic solvent like isopropyl alcohol.
- anhydrous conditions for step (b) may be selected from dry granulation, compaction and direct compression.
- the tablets prepated by the process of the present invention may be triangular in shape.
- the dimensions of the tablets of the present invention may be as follows
- the pH of dispersion is adjusted with addition of hydrochloric acid to pH 5 4 ⁇ 0.5 under stirring with or without heating.
- the pH of dispersion is adjusted with addition of hydrochloric acid to pH 5 4 ⁇ 0.5 under stirring with or without heating.
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Zoology (AREA)
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- Medicinal Preparation (AREA)
Abstract
A taste masked chewable tablet of sildenafil and the process of its preparation.
Description
A TASTE MASKED CHEWABLE TABLET OF SILDENAFIL
The present invention relates to taste masked chewable tablet of sildenafil useful in the treatment of pulmonary hypertension and erectile dysfunction. BACKGROUND OF THE INVENTION
Sildenafil is a selective inhibitor of cyclic guanosine monophosphate (cGMP)- specific phosphodiesterase type 5 (PDE5), marketed by Pfizer. Sildenafil is designated chemically as l-[[3-(6, 7-dihydro-l-methyl-7- oxo-3-propyl-l -pyrazolo[4,3-d] pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4- methyl piperazine.
The pharmaceutically acceptable salt of sildenafil, sildenafil citrate, has a very bitter taste and hence tablets which are commercially available are film coated. The film coating masks any bitter taste in the mouth. However, in case of chewable tablets which are usually uncoated, there is need to mask the bitter taste of sildenafil as they are chewed and remain in contact with the taste receptors in the mouth for a longer period of time. Taste masking of sildenafil by coating with polymers is already known in the art.
United States Patent No. 6,221,402 (assigned to Pfizer referred to herein as '402 patent) discloses a rapidly releasing and taste masking pharmaceutical dosage form of sildenafil and a process of its preparation. The dosage form has an inner and outer coating wherein the inner coating coats the core of sildenafil citrate and low-substituted hydroxypropylcellulose and the outer coating comprises a saliva-insoluble polymer.
PCT publication WO 2004087111 (assigned to M/S Ranbaxy referred to herein as '11 1 publication) discloses oral taste masked pharmaceutical compositions that include a core having an active ingredient coated with a mixture of polymeric film forming binders and inorganic carriers. Processes for preparing the oral taste masked pharmaceutical composition are also provided.
PCT publication WO2009074995 (assigned to M/S Ajanta Pharma Limited referred to herein as '995 publication) relates to tablets comprising sildenafil mask complex. However, the tablets comprise additional taste masking pharmaceutical excipient like monoammonium glycerrhizinate for masking the bitter taste of sildenafil citrate. The process for the preparation of the tablets involves wet granulation which could degrade sildenafil. The present invention relates to chewable tablets without additional taste masking pharmaceutical excipient and is prepared under anhydrous conditions.
PCT publicatien WO2009123626 (assigned to M/S Ocean, referred to herein as '626 publication) relates to orodispersible tablets of phosphodiesterase -5 inhibitors including sildenafil. The amount of disintegrant used is more than 5% of weight of tablet. Further, process for the preparation of tablets utilizes organic solvent in the moist granulation procedure. The present invention relates to chewable tablets which comprises less than 5% of disintegrant and is prepared under anhydrous conditions and in the absence of organic solvent.
OBJECT OF THE INVENTION
The object of the present invention is to provide a taste masked chewable tablet of sildenafil and the process of its preparation.
SUMMARY OF THE INVENTION
A taste masked chewable tablet of sildenafil comprising
(a) taste masked complex of sildenafil with crosslinked polymer of divinylbenzehe methacrylate prepared in the absence of organic solvent; and (b) directly compressible pharmaceutical excipient(s); wherein the tablets are obtainable by method under anhydrous conditions.
Also provided is a process for the preparation of chewable tablet of sildenafil complexed with crosslinked polymer of divinylbenzene methacrylate comprising
(a) preparing sildenafil complex with crosslinked polymer of divinylbenzene methacrylate in the absence of organic solvent;
(b) mixing sildenafil complexed with crosslinked polymer of divinylbenzene methacrylate with directly compressible pharmaceutical excipient(s) under anhydrous conditions; and
(c) compressing into tablets.
DESCRIPTION OF THE INVENTION The present invention provides a taste masked chewable tablet of sildenafil.
According to one embodiment of the present invention the taste masked chewable tablet of sildenafil comprises complex of sildenafil with divinylbenzene methacrylate prepared in the absence of organic solvent and directly compressible pharmaceutical excipient(s) wherein the tablets are obtainable by method under anhydrous conditions
Anhydrous conditions may, be selected from compaction, direct compression and dry granulation.
The directly compressible pharmaceutical excipient may be selected from diluents, binders, lubricants, disintegrants, flavoring agents, coloring agents, stabilizers, surfactants, glidants, plasticizers, preservatives and sweeteners.
Diluents may be selected from calcium carbonate, calcium phosphate dibasic, calcium phosphate tribasic, calcium sulfate, microcrystalline cellulose, microcrystalline silicified cellulose, powdered cellulose, dextrates, dextrose, fructose, lactitol, lactose anhydrous, lactose monohydrate, lactose dihydrate, lactose trihydrate, starch, pregelatinized starch, sucrose, talc, maltose maltodextrin.
Binders may be selected from acacia, alginic acid, carbomer, carboxymethylcellulose calcium, carbomethylcellulose sodium, microcrystalline cellulose,powdered cellulose, ethyl cellulose, gelatin liquid glucose, guar gum, hydroxyethyl cellulos, hydroxypropyl cellulose, hydroxypropylmethyl
cellulose, maltodextrin, methylcellulose, ploydextrose, polyethtylene oxide,povidone, sodium alginate, starch paste, pregelatinized starch, sucrose, tragacanth, low-substituted hydroxypropyl cellulose,glucose, sorbitol. Suitable fillers are preferably selected from atleast one of starch derivatives.such as com starch, potato starch or rice starch. Polysaccharides such as dextrins, maltodextrins, dextrates, microcrystalline cellulose, powdered cellulose, mixture of microcrystalline cellulose and guar gum, coprocessed blends of microcrystalline cellulose; and polyhydric alcohols, such as xylitol and sorbitol.
Lubricants may be selected from magnesium stearate, stearic acid, sodium stearyl fumarate, magnesium lauryl sulphate, talc, polyethylene glycol, and glyceryl behenate.
Disintegrants may be selected from, alginic acid, carbon dioxide, carboxymethylcellulose, calcium carboxymethylcellulose sodium, microcrystalline cellulose, powdered cellulose, croscarmelose sodium, crospovidone, sodium docusate, gaur gum, hydroxypropyl cellulose, methylcellulose, polacrilin potassium , poloxamer, povidone, sodium alginate, sodium glycine carbonate, sodium laulyl sulfate, sodium starch glycolate, starch, pregelatinized starch, low-substituted hydroxypropyl cellulose.
The amount of disintegrant used is preferably less than 5% by weight of the tablet, more preferably 3-5% by weight of the tablet.
Flavoring agents may be selected from natural or synthetic flavors such as strawberry flavor, wild cherry flavor, green apple flavor, spearmint flavor and peppermint flavor.
Glidarits may be, for example, calcium silicate, powdered cellulose, starch, talc, colloidal silicon dioxide.
Suitable sweeteners may be selected from sugars such as sucrose, lactose and glucose; cyclamate and salts thereof; saccharin and salts thereof; and aspartame.
The directly compressible pharmaceutical excipient used in the present invention will not comprise sugar alcohol.
The directly compressible pharmaceutical excipient used in the present invention will not comprise organic acid.
The directly compressible pharmaceutical excipient used in the present invention will not comprise . monoammonium glycerhizinate
According to another embodiment of the present invention the taste masked chewable tablet of sildenafil is triangular in shape. The dimensions of the tablets of the present invention may be as follows
According to yet another embodiment of the present invention the process for the preparation of taste masked chewable tablet of sildenafil or its pharmaceutically acceptable salt is also provided.
A process for the preparation of taste masked chewable tablet of sildenafil comprising
(a) preparing sildenafil complex with crosslmked polymer of divinylbenzene methacrylate in the absence of organic solvent;
(b) mixing sildenafil complexed with crosslinked polymer of divinylbenzene methacrylate with directly compressible pharmaceutical excipient(s) under anhydrous conditions; and
(c) compressing into tablets.
The process of the present invention for preparing sildenafil complex with crosslinked polymer of divinylbenzene methacrylate is carried out in the absence of organic solvent like ethanol and the like.
Further, the process of mixing sildenafil complexed with crosslinked polymer of divinylbenzene methacrylate with directly compressible pharmaceutical excipient(s) will not comprise water or an organic solvent like isopropyl alcohol.
According to the process of the present invention the anhydrous conditions for step (b) may be selected from dry granulation, compaction and direct compression.
The tablets prepated by the process of the present invention may be triangular in shape. The dimensions of the tablets of the present invention may be as follows
EXAMPLES
Example 1 :
*Water will be removed during drying
Disperse sildenafil citrate in purified water with the aid of stirring with or without heat to form dispersion. The pH of dispersion is adjusted with addition of hydrochloric acid to pH 5 4±0.5 under stirring with or without heating. Disperse 1 part of ion exchange resin IRP88 to the
solution/dispersion with constant stirring until formation of slurry. Filter the slurry and keep the slurry for drying.
Sift complex and excipients through appropriate sieve and mix them for suitable time. Lubricate blend with magnesium stearate and compress into tablets.
Example 2:
*Water will be removed during dryin
Disperse sildenafil citrate in purified water with the aid of stirring with or without heat to form dispersion. The pH of dispersion is adjusted with addition of hydrochloric acid to pH 5 4±0.5 under stirring with or without heating. Disperse 1 part of ion exchange resin I P88 to the
solution/dispersion with constant stirring until formation of slurry. Filter the slurry and keep the slurry for drying. Sift complex and excipients through appropriate sieve and mix them for suitable time. Lubricate blend with magnesium stearate and compress into tablets.
Claims
1. A taste masked chewable tablet of sildenafil comprising
(a) taste masked complex of sildenafil with crosslinked polymer of divinylbenzene
methacrylate prepared in the absence of organic solvent; and
(b) directly compressible pharmaceutical excipient(s);
wherein the tablets are obtainable by method under anhydrous conditions.
2. A taste masked chewable tablet of sildenafil as claimed in claim 1 wherein the tablet is triangular in shape.
3. A taste masked chewable tablet as claimed in claim 1 wherein the tablet is prepared by dry granulation, compaction or direct compression.
4. A taste masked chewable tablet as claimed in claim 1 wherein the directly compressible pharmaceutical excipient is selected from fillers, diluents, disintegrants, binders, sweeteners, flavors, colors and lubricants.
5. A taste masked chewable tablet as claimed in claim 4 wherein the amount of disintegrant is less than 5% by weight of tablet.
6. A taste masked chewable tablet as claimed in claim 4 wherein the pharmaceutical
excipient is not sugar alcohol.
7. A taste masked chewable tablet as claimed in claim 4 wherein the pharmaceutical
excipient is not an organic acid.
8. A taste masked chewable tablet as claimed in claim 4 wherein the pharmaceutical
excipient is not an inorganic salt.
9. A taste masked chewable tablet as claimed in claim 4 wherein the pharmaceutical
excipient is not monoammonium glycerhizinate.
10. A taste masked chewable tablet comprising sildenafil complexed with crosslinked
polymer of divinylbenzene methacrylate, disintegrant and atleast one pharmaceutically acceptable directly compressible pharmaceutical excipient.
11. A taste masked chewable tablet as claimed in claim 6 wherein ihe amount of disintegrant is less than 5% by weight of tablet.
12. A process for the preparation of taste masked chewable tablet of sildenafil comprising
(a) preparing sildenafil complex with crosslinked polymer of divinylbenzene
methacrylate in the absence of organic solvent;
(b) mixing sildenafil complexed with crosslinked polymer of divinylbenzene
methacrylate with directly compressible pharmaceutical excipient(s) under anhydrous conditions; and
(c) compressing into tablets.
13. A process as claimed in claim 13 wherein the tablet is triangular in shape.
14. A process for the preparation of taste masked chewable tablet of sildenafil comprising
(a) preparing sildenafil complex with crosslinked polymer of divinylbenzene
methacrylate in the absence of organic solvent;
(b) mixing sildenafil complexed with crosslinked polymer of divinylbenzene methacrylate with disintegrant, directly compressible pharmaceutical excipient(s) under anhydrous conditions; and
(c) compressing into tablets.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2011/000138 WO2012120522A1 (en) | 2011-03-04 | 2011-03-04 | A taste masked chewable tablet of sildenafil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2011/000138 WO2012120522A1 (en) | 2011-03-04 | 2011-03-04 | A taste masked chewable tablet of sildenafil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2012120522A1 true WO2012120522A1 (en) | 2012-09-13 |
Family
ID=46797563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2011/000138 Ceased WO2012120522A1 (en) | 2011-03-04 | 2011-03-04 | A taste masked chewable tablet of sildenafil |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2012120522A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140077658A (en) * | 2012-12-14 | 2014-06-24 | 한미약품 주식회사 | Chewable tablet comprising a phosphodiesterase-5 inhibitor |
| WO2014209022A1 (en) * | 2013-06-28 | 2014-12-31 | Hanmi Pharm. Co., Ltd. | Chewable tablet formulation comprising tadalafil or a pharmaceutically acceptable salt thereof |
| CN104248625A (en) * | 2013-06-25 | 2014-12-31 | 北大方正集团有限公司 | Avanafil effervescent dry suspension and preparation method thereof |
| CN113271949A (en) * | 2018-10-26 | 2021-08-17 | 阿尔特罗亚公司 | Sildenafil for the treatment of osteoarthritis |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060127479A1 (en) * | 2004-10-08 | 2006-06-15 | Natrajan Kumaraperumal | Solvent free taste masked pharmaceutical compositions |
| WO2009123626A1 (en) * | 2008-04-01 | 2009-10-08 | Ocean 1 806, Llc | Orodispersable formulations of phosphodiesterase-5 (pde-5) inhibitors |
| WO2010115576A1 (en) * | 2009-04-06 | 2010-10-14 | Ratiopharm Gmbh | Melting tablet containing a sildenafil salt |
| EP2338474A1 (en) * | 2009-12-23 | 2011-06-29 | Ratiopharm GmbH | Fusion tablet containing compacted sildenafil base |
-
2011
- 2011-03-04 WO PCT/IN2011/000138 patent/WO2012120522A1/en not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060127479A1 (en) * | 2004-10-08 | 2006-06-15 | Natrajan Kumaraperumal | Solvent free taste masked pharmaceutical compositions |
| WO2009123626A1 (en) * | 2008-04-01 | 2009-10-08 | Ocean 1 806, Llc | Orodispersable formulations of phosphodiesterase-5 (pde-5) inhibitors |
| WO2010115576A1 (en) * | 2009-04-06 | 2010-10-14 | Ratiopharm Gmbh | Melting tablet containing a sildenafil salt |
| EP2338474A1 (en) * | 2009-12-23 | 2011-06-29 | Ratiopharm GmbH | Fusion tablet containing compacted sildenafil base |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140077658A (en) * | 2012-12-14 | 2014-06-24 | 한미약품 주식회사 | Chewable tablet comprising a phosphodiesterase-5 inhibitor |
| KR101953735B1 (en) * | 2012-12-14 | 2019-03-04 | 한미약품 주식회사 | Chewable tablet comprising a phosphodiesterase-5 inhibitor |
| CN104248625A (en) * | 2013-06-25 | 2014-12-31 | 北大方正集团有限公司 | Avanafil effervescent dry suspension and preparation method thereof |
| CN104248625B (en) * | 2013-06-25 | 2016-12-28 | 北大方正集团有限公司 | Avanaphil effervescent dry-mixed suspension agent and preparation method thereof |
| WO2014209022A1 (en) * | 2013-06-28 | 2014-12-31 | Hanmi Pharm. Co., Ltd. | Chewable tablet formulation comprising tadalafil or a pharmaceutically acceptable salt thereof |
| KR20150002453A (en) * | 2013-06-28 | 2015-01-07 | 한미약품 주식회사 | Chewable tablet formulation comprising tadalafil or a pharmaceutically acceptable salt thereof |
| KR102239291B1 (en) | 2013-06-28 | 2021-04-14 | 한미약품 주식회사 | Chewable tablet formulation comprising tadalafil or a pharmaceutically acceptable salt thereof |
| CN113271949A (en) * | 2018-10-26 | 2021-08-17 | 阿尔特罗亚公司 | Sildenafil for the treatment of osteoarthritis |
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