WO2013180675A1 - Tablet formulation comprising dapoxetine - Google Patents

Tablet formulation comprising dapoxetine Download PDF

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Publication number
WO2013180675A1
WO2013180675A1 PCT/TR2013/000155 TR2013000155W WO2013180675A1 WO 2013180675 A1 WO2013180675 A1 WO 2013180675A1 TR 2013000155 W TR2013000155 W TR 2013000155W WO 2013180675 A1 WO2013180675 A1 WO 2013180675A1
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Prior art keywords
diluent
range
formulation
formulation according
weight
Prior art date
Application number
PCT/TR2013/000155
Other languages
French (fr)
Inventor
Mahmut Bilgic
Original Assignee
Mahmut Bilgic
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 Mahmut Bilgic filed Critical Mahmut Bilgic
Publication of WO2013180675A1 publication Critical patent/WO2013180675A1/en

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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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine

Definitions

  • the present invention is related to formulations comprising dapoxetine which is an oral selective serotonin reuptake inhibitor having rapid onset of action and short half-life.
  • the present formulations are characterized in being in tablet form.
  • the molecule shown in Formula I which has the CAS name of N,N-dimethyl-alpha-(2-(l- naphthalenyloxy)ethyl) benzenemethanamine was first disclosed in the document numbered EP0288188 (Bl). In said document, inhibitive effect of dapoxetine on serotonin reuptake was pointed out. In line with this, it was disclosed that dapoxetine can be used in the treatment of disorders such as neural system related obesity, depression, alcoholism, pain, memory loss, anxiety and smoking.
  • the first element of the present invention is tablet formulations comprising dapoxetine and/or its pharmaceutically acceptable derivatives wherein the ratio of dapoxetine to the diluent is in the range of 1 : 10 and 4: 1 by weight.
  • the active agent dapoxetine is in the forms of its solvates, hydrates, esters, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or combinations thereof.
  • a characteristic of the tablet formulations prepared according to the present invention is that said formulations can be in any of solid dosage forms of effervescent tablet, film coated tablet, enteric-coated tablet, prolonged release tablet, modified release tablet, delayed release tablet.
  • the tablet formulations of the present invention can preferably be in film coated tablet form.
  • the ratio of dapoxetine to the diluent used in the tablet formulations of the present invention can be in the range of 1 :8 and 3:1, more preferably in the range of 1 :5 and 2:1 by weight.
  • tablet formulations of the present invention comprise the active agent dapoxetine in the range of 5-80%, preferably in the range of 10-70%, more preferably in the range of 15-55% by weight in proportion to total tablet weight of the unit dose amount.
  • the tablet formulations of the present invention can comprise diluent in the range of 10-90%, preferably in the range of 20-85%, more preferably in the range of 30-75% by weight in proportion to total tablet weight of the unit dose amount.
  • the diluent used in the tablet formulation of the present invention is composed of at least two different diluents as the 1 st diluent and the 2 nd diluent is effective on producing tablets having the desired durability and dispersion characteristics.
  • a characteristic feature of the tablet formulations prepared according to the present invention is that the diluent used in the formulations is composed of at least two different diluents as the 1 st diluent and the 2 nd diluent.
  • the ratio of the 1 st diluent to the 2 nd diluent is in the range of 5: 1 and 1 :5, preferably in the range of 4: 1 and 3: 1, more preferably in the range of 3:1 and 2:1 by weight.
  • the tablet formulations of the present invention can comprise the first diluent at least at 10% in proportion to total tablet weight of the unit dose.
  • the diluent that shall be used in the tablet formulations prepared according to the present invention can be selected from a group comprising D-mannitol, xylitol, microcrystalline cellulose, crospovidone, dibasic calcium phosphate anhydrous, lactose, starch, maltose, dextrin, maltodextrin, magnesium carbonate, talc and combinations thereof.
  • Amount and type of the 1 st diluent used in the tablet formulations of the present invention affect characteristics of the tablet such as hardness and easy compression.
  • the inventors have observed that tablets have the required hardness and powder can be compressed during tablet compression in the case that the 1 st diluent is cellulose-based.
  • the first diluent is preferably selected from cellulose-based substances and it is more preferably microcrystalline cellulose.
  • the tablet formulations of the present invention can comprise at least one pharmaceutically acceptable excipient in addition to dapoxetine and the diluent.
  • the excipients that can be used in the formulations of the present invention can be selected from a group comprising disintegrant, anti-adhesive agent, lubricant and coating agent.
  • the disintegrant that can be used in the formulations of the present invention can be selected from a group comprising carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, microcrystalline cellulose, croscarmellose sodium, hydroxypropyl cellulose, methylcellulose or combinations thereof.
  • Another problem observed in the formulations of the present invention comprising dapoxetine is their late dissolution time.
  • the inventors have observed that having the ratio of the disintegrant to the 2 nd diluent in the range of 1 : 1 and 1 :20 by weight, preferably in the range of 1 : 1 and 1 : 15 enable production of tablets with optimum dispersion and required level of dissolution profile.
  • the ratio of the disintegrant to the 2 nd diluent used in said formulations is in the range of 1 : 1 and 1 :20, preferably in the range of 1 : 1 and 1 : 15 by weight.
  • the anti-adhesive agent of the present formulations can be selected from a group comprising silicon dioxide, talc, starch, colloidal silicate, L-leucine, sodium sulfate, stearates and/or combinations thereof.
  • the lubricant of the present formulations can be selected from a group comprising calcium stearate, magnesium stearate, sodium stearyl fumarate, polyethylene glycol, PEG 6000, polyvinyl alcohol, potassium benzoate, sodium benzoate.
  • the film coating agent in the formulations of the present invention can be selected from a group comprising titanium dioxide, polyvinyl alcohol, polyethylene glycol, talc, lecithin or a combination thereof.
  • the film coating agent marketed under the name Opadry Yellow® can be used.
  • the formulations of the present invention can comprise dapoxetine in the range of 5-80%, the diluent in the range of 10-90%, the disintegrant in the range of 1 -15%, the anti-adhesive agent in the range of 0.5-5%, the lubricant in the range of 0.5-2% and the coating agent in the range of 0.5-5% by weight in proportion to total weight of the unit dose.
  • the method used for preparation of the formulations of the present invention primarily comprises the step of mixing dapoxetine, the diluents and the disintegrant. Then, the anti- adhesive agent is added into this mixture and they are mixed again. The mixture lubricated with the lubricant is loaded to tablet compression machine and tablets are compressed. Optionally, the compressed tablets are coated with a film coating solution comprising the coating agent.
  • the formulations of the present invention can be used shortly before sexual activity for prevention, treatment or control of sexual disorders in mammals, particularly for premature ejaculation in men.
  • EXAMPLE Film coated tablet formulation comprising dapoxetine
  • dapoxetine, the diluents and the disintegrant are mixed in order to prepare the formulation given above.
  • the mixture is lubricated with the lubricant and compressed in tablet compression machine.
  • the compressed tablets are coated with the film coating solution comprising the coating agent.

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  • 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)
  • Medicinal Preparation (AREA)

Abstract

The present invention is related to formulations comprising dapoxetine which is an oral selective serotonin reuptake inhibitor having rapid onset of action and short half-life. The present formulations are characterized in being in tablet form.

Description

TABLET FORMULATION COMPRISING DAPOXETINE
The present invention is related to formulations comprising dapoxetine which is an oral selective serotonin reuptake inhibitor having rapid onset of action and short half-life. The present formulations are characterized in being in tablet form. The molecule shown in Formula I which has the CAS name of N,N-dimethyl-alpha-(2-(l- naphthalenyloxy)ethyl) benzenemethanamine was first disclosed in the document numbered EP0288188 (Bl). In said document, inhibitive effect of dapoxetine on serotonin reuptake was pointed out. In line with this, it was disclosed that dapoxetine can be used in the treatment of disorders such as neural system related obesity, depression, alcoholism, pain, memory loss, anxiety and smoking.
Figure imgf000002_0001
Formula I
There is not any product comprising dapoxetine present on Turkish pharmaceutical market. However, there is the 30 mg film coated tablet product marketed by Janssen-Cilag in the world which is expected to be marketed in Turkey.
Various problems are encountered during preparation and carrying of tablet formulations comprising dapoxetine due to the factors such as low bulk density and poor flow characteristics. Failure to attain sufficient density while formulating the formulations comprising dapoxetine in tablet form and failure to obtain a formulation with good flow characteristics lead to variations in weight and contents of the obtained tablets. Formulations with poor flow characteristics and insufficient density cause problems to producers during preparation and carrying as well as leading to an inefficient pharmacotherapy for patients due to the fact that tablets at different weights are obtained during tablet compression of the formulations with poor flow characteristics and the tablets vary in terms of dose amounts of dapoxetine. Therefore, these variations observed in weights and contents of tablet formulations comprising dapoxetine impede to attain weight and content uniformity. Consequently, failure to attain weight and content uniformity results in reduced therapeutic activity and reduced effects of drugs and this means failure to provide effective treatment. According to this, it is required to find new methods in order to develop dapoxetine tablet formulations which have proper flow characteristics, can be formulated easily, have weight and content uniformity. The inventors have surprisingly seen that tablet formulations comprising dapoxetine and/or its pharmaceutically acceptable derivatives as the active agent wherein the ratio of dapoxetine to the diluent is in the range of 1 :10 and 4: 1 have proper flow characteristics and sufficient bulk density and thus, enable to apply an efficient treatment by attaining weight and content uniformity. Accordingly, the first element of the present invention is tablet formulations comprising dapoxetine and/or its pharmaceutically acceptable derivatives wherein the ratio of dapoxetine to the diluent is in the range of 1 : 10 and 4: 1 by weight.
Another characteristic of the tablet formulations of the present invention is that the active agent dapoxetine is in the forms of its solvates, hydrates, esters, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or combinations thereof.
A characteristic of the tablet formulations prepared according to the present invention is that said formulations can be in any of solid dosage forms of effervescent tablet, film coated tablet, enteric-coated tablet, prolonged release tablet, modified release tablet, delayed release tablet.
The tablet formulations of the present invention can preferably be in film coated tablet form.
The ratio of dapoxetine to the diluent used in the tablet formulations of the present invention can be in the range of 1 :8 and 3:1, more preferably in the range of 1 :5 and 2:1 by weight.
Another characteristic feature of the tablet formulations of the present invention is that said formulations comprise the active agent dapoxetine in the range of 5-80%, preferably in the range of 10-70%, more preferably in the range of 15-55% by weight in proportion to total tablet weight of the unit dose amount. The tablet formulations of the present invention can comprise diluent in the range of 10-90%, preferably in the range of 20-85%, more preferably in the range of 30-75% by weight in proportion to total tablet weight of the unit dose amount.
It is known that physical characteristics of the tablets such as durability and dispersion are significant parameters for obtaining the desired effect of the medication and providing an efficient treatment in addition to weight and content uniformity in the tablet formulations comprising dapoxetine. As a result of the studies they conducted, the inventors have seen that the fact that the diluent used in the tablet formulation of the present invention is composed of at least two different diluents as the 1st diluent and the 2nd diluent is effective on producing tablets having the desired durability and dispersion characteristics.
According to this, a characteristic feature of the tablet formulations prepared according to the present invention is that the diluent used in the formulations is composed of at least two different diluents as the 1st diluent and the 2nd diluent.
Another characteristic feature of the formulations of the present invention is that the ratio of the 1st diluent to the 2nd diluent is in the range of 5: 1 and 1 :5, preferably in the range of 4: 1 and 3: 1, more preferably in the range of 3:1 and 2:1 by weight.
The tablet formulations of the present invention can comprise the first diluent at least at 10% in proportion to total tablet weight of the unit dose.
The diluent that shall be used in the tablet formulations prepared according to the present invention can be selected from a group comprising D-mannitol, xylitol, microcrystalline cellulose, crospovidone, dibasic calcium phosphate anhydrous, lactose, starch, maltose, dextrin, maltodextrin, magnesium carbonate, talc and combinations thereof.
Amount and type of the 1st diluent used in the tablet formulations of the present invention affect characteristics of the tablet such as hardness and easy compression. The inventors have observed that tablets have the required hardness and powder can be compressed during tablet compression in the case that the 1st diluent is cellulose-based.
According to this, another characteristic of the formulations of the present invention is that the first diluent is preferably selected from cellulose-based substances and it is more preferably microcrystalline cellulose. The tablet formulations of the present invention can comprise at least one pharmaceutically acceptable excipient in addition to dapoxetine and the diluent.
The excipients that can be used in the formulations of the present invention can be selected from a group comprising disintegrant, anti-adhesive agent, lubricant and coating agent. The disintegrant that can be used in the formulations of the present invention can be selected from a group comprising carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, microcrystalline cellulose, croscarmellose sodium, hydroxypropyl cellulose, methylcellulose or combinations thereof.
Another problem observed in the formulations of the present invention comprising dapoxetine is their late dissolution time. In the studies they conducted to avoid this problem, the inventors have observed that having the ratio of the disintegrant to the 2nd diluent in the range of 1 : 1 and 1 :20 by weight, preferably in the range of 1 : 1 and 1 : 15 enable production of tablets with optimum dispersion and required level of dissolution profile.
According to this, another characteristic of the present invention is that the ratio of the disintegrant to the 2nd diluent used in said formulations is in the range of 1 : 1 and 1 :20, preferably in the range of 1 : 1 and 1 : 15 by weight.
The anti-adhesive agent of the present formulations can be selected from a group comprising silicon dioxide, talc, starch, colloidal silicate, L-leucine, sodium sulfate, stearates and/or combinations thereof. The lubricant of the present formulations can be selected from a group comprising calcium stearate, magnesium stearate, sodium stearyl fumarate, polyethylene glycol, PEG 6000, polyvinyl alcohol, potassium benzoate, sodium benzoate.
The film coating agent in the formulations of the present invention can be selected from a group comprising titanium dioxide, polyvinyl alcohol, polyethylene glycol, talc, lecithin or a combination thereof. For example, the film coating agent marketed under the name Opadry Yellow® can be used.
The formulations of the present invention can comprise dapoxetine in the range of 5-80%, the diluent in the range of 10-90%, the disintegrant in the range of 1 -15%, the anti-adhesive agent in the range of 0.5-5%, the lubricant in the range of 0.5-2% and the coating agent in the range of 0.5-5% by weight in proportion to total weight of the unit dose. The method used for preparation of the formulations of the present invention primarily comprises the step of mixing dapoxetine, the diluents and the disintegrant. Then, the anti- adhesive agent is added into this mixture and they are mixed again. The mixture lubricated with the lubricant is loaded to tablet compression machine and tablets are compressed. Optionally, the compressed tablets are coated with a film coating solution comprising the coating agent.
The formulations of the present invention can be used shortly before sexual activity for prevention, treatment or control of sexual disorders in mammals, particularly for premature ejaculation in men.
The example below is given in order to explain the invention in more detail, yet it does not limit the invention.
EXAMPLE: Film coated tablet formulation comprising dapoxetine
Figure imgf000006_0001
Primarily; dapoxetine, the diluents and the disintegrant are mixed in order to prepare the formulation given above. The mixture is lubricated with the lubricant and compressed in tablet compression machine. Optionally, the compressed tablets are coated with the film coating solution comprising the coating agent.

Claims

1. A pharmaceutical formulation that can be formulated in tablet form, characterized in that;
• said formulation comprises dapoxetine and/or its pharmaceutically acceptable derivatives as the active agent,
• the ratio of dapoxetine to the diluent is in the range of 1 : 10 and 4: 1 by weight.
2. The formulation according to claim 1, characterized in that the active agent dapoxetine used in said formulation is in the form of its solvates, hydrates, esters, enantiomers, racemates, organic salts, inorganic salts, polymorphs, crystalline and amorphous forms or free form and/or a combination thereof. .
3. The formulation according to claims 1-2, characterized in that the formulations can be in the form of any of effervescent tablet, film coated tablet, enteric-coated tablet, prolonged release tablet, modified release tablet, delayed release tablet solid dosage forms.
4. The formulation according to claim 3, characterized in that the formulations are in film coated tablet form.
5. The formulation according to any preceding claims, characterized in that the ratio of dapoxetine to the diluent used in said formulation is in the range of 1 :8 and 3: 1 by weight.
6. The formulation according to claim 5, characterized in that the ratio of dapoxetine to the diluent used in said formulation is in the range of 1 :5 and 2: 1 by weight.
7. The formulation according to any preceding claims, characterized in that said formulation comprises the active agent dapoxetine in the range of 5-80% in proportion to total tablet weight of unit dose amount.
8. The formulation according to any preceding claims, characterized in that said formulation comprises the diluent in the range of 10-90% in proportion to total tablet weight of unit dose amount.
9. The formulation according to claim 8, characterized in that said formulation comprises the diluent in the range of 20-85% in proportion to total tablet weight of unit dose amount.
10. The formulation according to claim 9, characterized in that said formulation comprises the diluent in the range of 30-75% in proportion to total tablet weight of unit dose amount.
1 1. The formulation according to any preceding claims, characterized in that the diluent used in said formulations is composed of at least two different diluents as the 1st diluent and the 2nd diluent.
12. The formulation according to claim 1 1, characterized in that the ratio of the 1st diluent to the 2nd diluent is in the range of 5: 1 and 1 :5 by weight.
13. The formulation according to any preceding claims, characterized in that said formulation comprises the 1st diluent at least at 10% in proportion to total tablet weight of unit dose amount.
14. The formulation according to any preceding claims, characterized in that the diluent that shall be used in said formulations is selected from a group comprising D- mannitol, xylitol, microcrystalline cellulose, crospovidone, dibasic calcium phosphate anhydrous, lactose, starch, maltose, dextrin, maltodextrin, magnesium carbonate, talc and combinations thereof.
15. The formulation according to any preceding claims, characterized in that the 1st diluent is selected from cellulose-based substances.
16. The formulation according to claims 14-15, characterized in that the 1st diluent is microcrystalline cellulose.
17. The formulation according to any preceding claims, characterized in that the pharmaceutically acceptable excipients that can be used in said formulation are selected from a group comprising disintegrant, anti-adhesive agent, lubricant and coating agent.
18. The formulation according to claim 17, characterized in that the disintegrant that can be used in said formulation is selected from a group comprising carboxymethyl cellulose calcium, carboxymethyl cellulose sodium, microcrystalline cellulose, croscarmellose sodium, hydroxypropyl cellulose, methylcellulose or combinations thereof.
19. The formulation according to any preceding claims, characterized in that the ratio of the disintegrant to the 2nd diluent used in said formulations is in the range of 1 : 1 and 1 :20 by weight.
20. The formulation according to claim 19, characterized in that the ratio of the disintegrant to the 2nd diluent used in said formulations is in the range of 1 : 1 and 1 : 15 by weight.
21. The formulation according to any preceding claims, characterized in that said formulation comprises dapoxetine in the range of 5-80%, the diluent in the range of 10-90%, the disintegrant in the range of 1-15%, the anti-adhesive agent in the range of 0.5-5%, the lubricant in the range of 0.5-2% and the coating agent in the range of 0.5- 5% by weight in proportion to total weight of the unit dose.
22. The formulation according to any preceding claims, characterized in that the method used for preparation of said formulation comprises the steps of
• mixing dapoxetine, the diluents and the disintegrant,
• adding the anti-adhesive agent into this mixture,
• lubricating this mixture with the lubricant and compressing it in tablet form
• optionally, coating the compressed tablets with a film coating solution comprising the coating agent.
PCT/TR2013/000155 2012-05-28 2013-05-23 Tablet formulation comprising dapoxetine WO2013180675A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR201206208 2012-05-28
TR2012/06208 2012-05-28

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WO2013180675A1 true WO2013180675A1 (en) 2013-12-05

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105232503A (en) * 2015-11-20 2016-01-13 南京正科医药股份有限公司 Hydrochloric acid dapoxetine tablet

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0288188B1 (en) 1987-04-09 1991-10-16 Eli Lilly And Company 1-phenyl-3-naphthalenyloxy-propanamines
DE102009015702A1 (en) * 2009-03-31 2010-10-07 Ratiopharm Gmbh Tablets containing dapoxetine and dry processing for their preparation
WO2011072839A1 (en) * 2009-12-15 2011-06-23 Ratiopharm Gmbh Orodispersible tablet, containing dapoxetine
EP2591773A2 (en) * 2010-07-06 2013-05-15 Navipharm Co, Ltd Time-delayed sustained release pharmaceutical composition comprising dapoxetine for oral administration

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0288188B1 (en) 1987-04-09 1991-10-16 Eli Lilly And Company 1-phenyl-3-naphthalenyloxy-propanamines
DE102009015702A1 (en) * 2009-03-31 2010-10-07 Ratiopharm Gmbh Tablets containing dapoxetine and dry processing for their preparation
WO2011072839A1 (en) * 2009-12-15 2011-06-23 Ratiopharm Gmbh Orodispersible tablet, containing dapoxetine
EP2591773A2 (en) * 2010-07-06 2013-05-15 Navipharm Co, Ltd Time-delayed sustained release pharmaceutical composition comprising dapoxetine for oral administration

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105232503A (en) * 2015-11-20 2016-01-13 南京正科医药股份有限公司 Hydrochloric acid dapoxetine tablet

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