WO2013165327A1 - Pharmaceutical formulations comprising thiocolchicoside - Google Patents

Pharmaceutical formulations comprising thiocolchicoside Download PDF

Info

Publication number
WO2013165327A1
WO2013165327A1 PCT/TR2013/000129 TR2013000129W WO2013165327A1 WO 2013165327 A1 WO2013165327 A1 WO 2013165327A1 TR 2013000129 W TR2013000129 W TR 2013000129W WO 2013165327 A1 WO2013165327 A1 WO 2013165327A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
effervescent
range
acid
formulation according
Prior art date
Application number
PCT/TR2013/000129
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 WO2013165327A1 publication Critical patent/WO2013165327A1/en

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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin

Definitions

  • the present invention is related to pharmaceutical formulations comprising thiocolchicoside that shall be used in the treatment of trauma or neurologically-based cases with striated muscle tissue-related pains and spasticity and in degenerative spinal diseases such as torticollis, lombalgia, dorsalgia.
  • Formula I Thiocolchicoside is in forms of 4 mg/2 ml ampoule, combined gel, 4 mg and 8 mg capsule, 0.25% cream and pomade, 4 mg and 4 mg tablet.
  • effervescent formulations comprising thiocolchicoside which can easily be dissolved during use, can disperse in a short time, have high absorption and bioavailability and high therapeutic effect.
  • the inventors have surprisingly seen that the effervescent formulations comprising thiocolchicoside and/or its pharmaceutically acceptable derivatives dissolve easily when put into water during use, present faster dispersion in water and thus thiocolchicoside can provide an effective treatment in the case that said formulations comprise the effervescent acid at least at 30% in proportion to total tablet weight and the effervescent base at most at 50% in proportion to total tablet weight.
  • the present invention relates to pharmaceutical formulations comprising thiocolchicoside
  • the effervescent formulations comprising thiocolchicoside and/or its pharmaceutically acceptable derivatives dissolve easily, present faster dispersion in water and an effective treatment is enabled since thiocolchicoside presents high absorption and bioavailability in the case that said formulations comprise the effervescent acid at least at 30% in proportion to total tablet weight and the effervescent base at most at 50% in proportion to total tablet weight.
  • the first element of the present invention is the effervescent formulations comprising an effervescent acid at least at 30% in proportion to total tablet weight and an effervescent base at most at 50% in proportion to total tablet weight and thiocolchicoside as the active agent.
  • Thiocolchicoside used as the active agent in the formulations of the present invention 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.
  • the amount of thiocolchicoside used as the active agent is in the range of 0.05-5%, preferably in the range of 0.1-4%, more preferably in the range of 0.5-3% in proportion to total tablet weight.
  • the effervescent acid used in the formulations of the present invention is preferably in the range of 30-80%, more preferably in the range of 35-60% by weight.
  • the effervescent base used in the formulations of the present invention is preferably in the range of 10-50%, more preferably in the range of 20-45% by weight.
  • the ratio of the effervescent acid to the effervescent base used in the formulation of the present invention is in the range of 5: 1 to 1 :5, preferably in the range of 3:1 to 1 :3 by weight.
  • the effervescent acid used in the formulations of the present invention is selected from a group comprising acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, propionic acid and tartaric acid.
  • citric acid is preferably used as the effervescent acid in the formulations.
  • the effervescent base used in the formulations of the present invention is selected from a group comprising sodium bicarbonate, sodium citrate dihydrate, sodium hydroxide or combinations thereof.
  • sodium bicarbonate is preferably used as the effervescent base in the formulations.
  • the ratio of citric acid to sodium bicarbonate used in the formulations of the present invention is in the range of 5 : 1 to 1 :5, preferably in the range of 3 : 1 to 1 :3 by weight.
  • effervescent formulations of the present invention can be formulated in form of effervescent tablet, effervescent granule or effervescent powder. They are preferably in effervescent tablet form.
  • the effervescent formulations of the present invention comprise at least one pharmaceutically acceptable excipient in addition to thiocolchicoside, effervescent acid and effervescent base.
  • excipients to be used in the effervescent formulations of the present invention comprising thiocolchicoside are selected from a group comprising sweetener, filling agent, binder, flavoring agent, sweetener or combinations thereof.
  • the effervescent formulations comprise a sweetener composition comprising at least two sweeteners as the sweetener and the rate of the sweetener composition is in the range of 1-7%, preferably in the range of 2-5% in proportion to total tablet weight.
  • the ratio of the first sweetener to the second sweetener composing the sweetener composition used in the effervescent formulations of the present invention is in the range of 4:1 to 1 :4, preferably in the range of 3 : 1 to 1 :2.
  • the sweeteners composing the sweetener composition used in the effervescent formulations of the present invention are selected from a group comprising acesulfame potassium, aspartame, fructose, maltitol, xylitol, saccharine, sodium cyclamate, sucralose, sucrose.
  • the filling agent used in the effervescent formulations of the present invention 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.
  • the binder used in the effervescent formulations of the present invention is selected from a group comprising ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, sorbitol, methyl cellulose and povidone.
  • the flavoring agent used in the effervescent formulations of the present invention is selected from a group comprising menthol, menthane, anethole, methyl salicylate, eucalyptol, cinnamon, 1- methyl acetate, sage, eugenol, oxanon, lemon, orange, strawberry, blackberry or combinations thereof.
  • the amount of the flavoring agent used in the effervescent formulations of the present invention is at most 5%, preferably in the range of 0.5-4.5%, more preferably in the range of 1-4.5% in proportion to total tablet weight.
  • the effervescent formulation of the present invention comprising thiocolchicoside can comprise thiocolchicoside in the range of 0.05-5%), effervescent acid in the range of 30-80%, effervescent base in the range of 10-50%, binder in the range of 0.1 -5%, sweetener and/or taste regulating agent in the range of 1 -7%, filling agent in the range of 1-25% and flavoring agent in the range of 0.5-4.5% in proportion to total unit weight.
  • the pharmaceutical formulations of the present invention are produced by a process comprising the steps of: • preparing a granulation solution comprising the binder and the filling agent,
  • the effervescent formulations of the present invention comprising thiocolchicoside can be used in the treatment of trauma or neurologically-based cases with striated muscle tissue- related pains and spasticity and in degenerative spinal diseases such as torticollis, lombalgia, dorsalgia.
  • EXAMPLE 1 Formulation and process for preparation of effervescent formulation comprising thiocolchicoside
  • a granulation solution comprising the binder and the filling agent is prepared.
  • the active agent thiocolchicoside, filling agent, effervescent acid, effervescent base and the binder are mixed.
  • the powder mixture obtained is granulated with the granulation solution and the granules are dried.
  • the sweetener and the flavoring agent are added to the granules and they are mixed together.
  • the final mixture is compressed in tablet form.

Abstract

The present invention is related to pharmaceutical formulations comprising thiocolchicoside that shall be used in the treatment of trauma or neurologically-based cases with striated muscle tissue-related pains and spasticity and in degenerative spinal diseases such as torticollis, lombalgia, dorsalgia.

Description

PHARMACEUTICAL FORMULATIONS COMPRISING THIOCOLCHICOSIDE
The present invention is related to pharmaceutical formulations comprising thiocolchicoside that shall be used in the treatment of trauma or neurologically-based cases with striated muscle tissue-related pains and spasticity and in degenerative spinal diseases such as torticollis, lombalgia, dorsalgia.
The molecule thiocolchicoside shown in formula I was first disclosed in the application numbered US2820029.
Figure imgf000002_0001
Formula I Thiocolchicoside is in forms of 4 mg/2 ml ampoule, combined gel, 4 mg and 8 mg capsule, 0.25% cream and pomade, 4 mg and 4 mg tablet.
It is seen that it takes long to dissolve for effervescent formulations comprising thiocolchicoside when put into water and some part of the formulation comprising the active agent remain undissolved in the glass. In this case, the sufficient active agent amount required for an effective treatment cannot be taken in the body. Since sufficient amount of the active agent thiocolchicoside is not taken in the body, absorption and thus bioavailability of thiocolchicoside decrease. In conclusion, low absorption and bioavailability of thiocolchicoside which are considered to be consequences of failure to take the sufficient amount of thiocolchicoside required for an effective treatment in the body cause decrease in efficiency and effectiveness of the treatment.
According to this, in line with the problems existing in the prior art, there is need for new approaches to develop effervescent formulations comprising thiocolchicoside which can easily be dissolved during use, can disperse in a short time, have high absorption and bioavailability and high therapeutic effect. The inventors have surprisingly seen that the effervescent formulations comprising thiocolchicoside and/or its pharmaceutically acceptable derivatives dissolve easily when put into water during use, present faster dispersion in water and thus thiocolchicoside can provide an effective treatment in the case that said formulations comprise the effervescent acid at least at 30% in proportion to total tablet weight and the effervescent base at most at 50% in proportion to total tablet weight. Description of the Invention
The present invention relates to pharmaceutical formulations comprising thiocolchicoside, As a result of the studies they conducted in line with this need, the inventors have seen that the effervescent formulations comprising thiocolchicoside and/or its pharmaceutically acceptable derivatives dissolve easily, present faster dispersion in water and an effective treatment is enabled since thiocolchicoside presents high absorption and bioavailability in the case that said formulations comprise the effervescent acid at least at 30% in proportion to total tablet weight and the effervescent base at most at 50% in proportion to total tablet weight.
According to this, the first element of the present invention is the effervescent formulations comprising an effervescent acid at least at 30% in proportion to total tablet weight and an effervescent base at most at 50% in proportion to total tablet weight and thiocolchicoside as the active agent.
Thiocolchicoside used as the active agent in the formulations of the present invention 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. In the formulations of the present invention, the amount of thiocolchicoside used as the active agent is in the range of 0.05-5%, preferably in the range of 0.1-4%, more preferably in the range of 0.5-3% in proportion to total tablet weight.
The effervescent acid used in the formulations of the present invention is preferably in the range of 30-80%, more preferably in the range of 35-60% by weight. The effervescent base used in the formulations of the present invention is preferably in the range of 10-50%, more preferably in the range of 20-45% by weight.
The ratio of the effervescent acid to the effervescent base used in the formulation of the present invention is in the range of 5: 1 to 1 :5, preferably in the range of 3:1 to 1 :3 by weight. The effervescent acid used in the formulations of the present invention is selected from a group comprising acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, propionic acid and tartaric acid.
In a preferred embodiment of the present invention, citric acid is preferably used as the effervescent acid in the formulations.
The effervescent base used in the formulations of the present invention is selected from a group comprising sodium bicarbonate, sodium citrate dihydrate, sodium hydroxide or combinations thereof.
In a preferred embodiment of the present invention, sodium bicarbonate is preferably used as the effervescent base in the formulations.
The ratio of citric acid to sodium bicarbonate used in the formulations of the present invention is in the range of 5 : 1 to 1 :5, preferably in the range of 3 : 1 to 1 :3 by weight.
The effervescent formulations of the present invention can be formulated in form of effervescent tablet, effervescent granule or effervescent powder. They are preferably in effervescent tablet form.
The effervescent formulations of the present invention comprise at least one pharmaceutically acceptable excipient in addition to thiocolchicoside, effervescent acid and effervescent base.
The excipients to be used in the effervescent formulations of the present invention comprising thiocolchicoside are selected from a group comprising sweetener, filling agent, binder, flavoring agent, sweetener or combinations thereof.
The solution obtained by dissolving the effervescent formulations comprising the active agent thiocolchicoside known to have a bitter taste has an unpleasant, bad taste which disturbs the patients and this causes difficulty in use of the effervescent forms obtained by formulating the formulations of the present invention. As a result of the studies they conducted in line with this need, the inventors have seen that this problem is overcome to a large extent by using a composition comprising two different sweeteners as the sweetener and/or the taste regulating agent.
According to this, another element of the present of the present invention is that the effervescent formulations comprise a sweetener composition comprising at least two sweeteners as the sweetener and the rate of the sweetener composition is in the range of 1-7%, preferably in the range of 2-5% in proportion to total tablet weight.
The ratio of the first sweetener to the second sweetener composing the sweetener composition used in the effervescent formulations of the present invention is in the range of 4:1 to 1 :4, preferably in the range of 3 : 1 to 1 :2.
The sweeteners composing the sweetener composition used in the effervescent formulations of the present invention are selected from a group comprising acesulfame potassium, aspartame, fructose, maltitol, xylitol, saccharine, sodium cyclamate, sucralose, sucrose.
The filling agent used in the effervescent formulations of the present invention 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.
The binder used in the effervescent formulations of the present invention is selected from a group comprising ethyl cellulose, gelatine, hydroxyethyl cellulose, hydroxymethyl cellulose, hydroxypropyl cellulose, hypromellose, magnesium aluminium silicate, sorbitol, methyl cellulose and povidone.
The flavoring agent used in the effervescent formulations of the present invention is selected from a group comprising menthol, menthane, anethole, methyl salicylate, eucalyptol, cinnamon, 1- methyl acetate, sage, eugenol, oxanon, lemon, orange, strawberry, blackberry or combinations thereof.
The amount of the flavoring agent used in the effervescent formulations of the present invention is at most 5%, preferably in the range of 0.5-4.5%, more preferably in the range of 1-4.5% in proportion to total tablet weight.
The effervescent formulation of the present invention comprising thiocolchicoside can comprise thiocolchicoside in the range of 0.05-5%), effervescent acid in the range of 30-80%, effervescent base in the range of 10-50%, binder in the range of 0.1 -5%, sweetener and/or taste regulating agent in the range of 1 -7%, filling agent in the range of 1-25% and flavoring agent in the range of 0.5-4.5% in proportion to total unit weight.
The pharmaceutical formulations of the present invention are produced by a process comprising the steps of: • preparing a granulation solution comprising the binder and the filling agent,
• mixing thiocolchicoside, filling agent, effervescent acid, effervescent base and the binder,
• granulating the obtained powder mixture with the granulation solution and drying the granules afterwards,
• adding the sweetener and the flavoring agent into the granules and obtaining the final mixture;
• compressing the final mixture in tablet form or filling it into suitable sachets.
The effervescent formulations of the present invention comprising thiocolchicoside can be used in the treatment of trauma or neurologically-based cases with striated muscle tissue- related pains and spasticity and in degenerative spinal diseases such as torticollis, lombalgia, dorsalgia.
EXAMPLE 1 : Formulation and process for preparation of effervescent formulation comprising thiocolchicoside
Figure imgf000006_0001
For obtaining the formulation to be used in the present invention, a granulation solution comprising the binder and the filling agent is prepared. The active agent thiocolchicoside, filling agent, effervescent acid, effervescent base and the binder are mixed. The powder mixture obtained is granulated with the granulation solution and the granules are dried. The sweetener and the flavoring agent are added to the granules and they are mixed together. The final mixture is compressed in tablet form.

Claims

1. Effervescent formulations comprising thiocolchicoside and/or pharmaceutically acceptable derivatives thereof, characterized in that
• the effervescent acid in said formulation is at least at the rate of 30% in proportion to total tablet weight and
• the effervescent base in said formulation is at most at the rate of 50% in proportion to total tablet weight.
2. The formulation according to claim 1, characterized in that the active agent thiocolchicoside 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 and 2, characterized in that the amount of the active agent thiocolchicoside is in the range of 0.05-5% in proportion to total tablet weight.
4. The formulation according to claims 1-3, characterized in that the amount of the effervescent acid used in said formulation is in the range of 30-80% by weight.
5. The formulation according to claim 4, characterized in that the rate of the effervescent acid used in said formulation is in the range of 35-60% by weight.
6. The formulation according to claims 1-5, characterized in that the rate of the effervescent base used in said formulation is in the range of 10-50% by weight.
7. The formulation according to claim 6, characterized in that the rate of the effervescent base used in said formulation is in the range of 20-45% by weight.
8. The formulation according to any preceding claims, characterized in that the ratio of the effervescent acid to the effervescent base used in the formulation is in the range of 5:1 to 1 :5 by weight.
9. The formulation according to any preceding claims, characterized in that the effervescent acid used in said formulation is selected from a group comprising acetic acid, citric acid, lactic acid, malic acid, phosphoric acid, propionic acid and tartaric acid.
10. The formulation according to claim 9, characterized in that citric acid is used as the effervescent acid in said formulation.
11. The formulation according to any preceding claims, characterized in that the effervescent base used in said formulation is selected from a group comprising sodium bicarbonate, sodium citrate dihydrate, sodium hydroxide or combinations thereof.
12. The formulation according to claim 1 1, characterized in that sodium bicarbonate is used as the effervescent base in said formulation.
13. The formulation according to any preceding claims, characterized in that said formulation comprises at least one pharmaceutically acceptable excipient in addition to the active agent thiocolchicoside, effervescent acid and the effervescent base.
14. The formulation according to claim 13, characterized in that the excipients to be used in the formulations are selected from a group comprising the sweetener, filling agent, binder, flavoring agent, sweetener or combinations thereof.
15. The formulation according to claim 14, characterized in that said formulation comprises a sweetener composition composed of at least two sweeteners as the sweetener and the sweetener composition is in the range of 1 -7% in proportion to total tablet weight.
16. The formulation according to claim 15, characterized in that the ratio of the first sweetener to the second sweetener composing the sweetener composition is in the range of 4:1 to 1:4.
17. The formulation according to claims 15-16, characterized in that the sweeteners comprised in the sweetener composition are selected from a group comprising acesulfame potassium, aspartame, fructose, maltitol, xylitol, saccharine, sodium cyclamate, sucralose, sucrose.
18. The formulation according to claim 14, characterized in that the flavoring agent used in said formulation is at most at 5% in proportion to total tablet weight.
19. The formulation according to any preceding claims, characterized in that said formulation comprises thiocolchicoside in the range of 0.05-5%, effervescent acid in the range of 30-80%, effervescent base in the range of 10-50%, binder in the range of 0.1-5%, sweetener and or taste regulating agent in the range of 1-7%, filling agent in the range of 1-25% and flavoring agent in the range of 0.5-4.5% by weight.
20. A process for preparation of a formulation comprising thiocolchicoside according to any preceding claims, characterized in that said process comprises the steps of;
• preparing the granulation solution comprising the binder and the filling agent,
• mixing thiocolchicoside, filling agent, effervescent acid, effervescent base and the binder, • granulating the obtained powder mixture with the granulation solution and drying the granules afterwards,
• adding the sweetener and the flavoring agent into the granules and obtaining the final mixture,
• compressing the final mixture in tablet form or filling it into suitable sachets.
PCT/TR2013/000129 2012-04-30 2013-04-29 Pharmaceutical formulations comprising thiocolchicoside WO2013165327A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2012/05010 2012-04-30
TR201205010 2012-04-30

Publications (1)

Publication Number Publication Date
WO2013165327A1 true WO2013165327A1 (en) 2013-11-07

Family

ID=48746105

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/TR2013/000129 WO2013165327A1 (en) 2012-04-30 2013-04-29 Pharmaceutical formulations comprising thiocolchicoside

Country Status (1)

Country Link
WO (1) WO2013165327A1 (en)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2725134A1 (en) * 1994-10-04 1996-04-05 Lederle Lab Pharmaceutical compsn. of ibuprofen and thiocolchicoside
WO2010138670A2 (en) * 2009-05-27 2010-12-02 Mutual Pharmaceutical Company, Inc. Thiocolchicine derivatives, method of making and methods of use thereof
WO2011130440A1 (en) * 2010-04-13 2011-10-20 Amerilab Technologies, Inc. Effervescent tablets comprising an oil component
WO2013006146A1 (en) * 2011-05-18 2013-01-10 Mahmut Bilgic Effervescent formulations comprising dexketoprofen
WO2013109222A1 (en) * 2012-01-18 2013-07-25 Mahmut Bilgic Formulations comprising diclofenac as the active agent

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2725134A1 (en) * 1994-10-04 1996-04-05 Lederle Lab Pharmaceutical compsn. of ibuprofen and thiocolchicoside
WO2010138670A2 (en) * 2009-05-27 2010-12-02 Mutual Pharmaceutical Company, Inc. Thiocolchicine derivatives, method of making and methods of use thereof
WO2011130440A1 (en) * 2010-04-13 2011-10-20 Amerilab Technologies, Inc. Effervescent tablets comprising an oil component
WO2013006146A1 (en) * 2011-05-18 2013-01-10 Mahmut Bilgic Effervescent formulations comprising dexketoprofen
WO2013109222A1 (en) * 2012-01-18 2013-07-25 Mahmut Bilgic Formulations comprising diclofenac as the active agent

Similar Documents

Publication Publication Date Title
ES2384378T3 (en) Oral pharmaceutical form containing a PDE 4 inhibitor as active ingredient and polyvinylpyrrolidone as an excipient
ES2326529T3 (en) PHARMACEUTICAL COMPOSITION CONTAINING A STABILIZED AMORPHY FORM OF DONEPEZIL CHLORHYDRATE.
KR102241643B1 (en) Suspension for oral administration comprising amorphous tolvaptan
WO2011093833A2 (en) Effervescent formulations comprising second generation cephalosporin
EP3492466B1 (en) Oral solid preparation and use thereof
EP2661252A1 (en) Water soluble dosage forms
WO2011136751A2 (en) Water soluble pharmaceutical composition
WO2011139249A2 (en) Pharmaceutical composition comprising cefdinir
WO2013052019A1 (en) Production method for effervescent formulations comprising diclofenac
EP2515849A1 (en) Effervescent tablet and granule formulation comprising cefixime
US9717692B2 (en) Effervescent formulations comprising dexketoprofen
CN110404079B (en) Pharmaceutical composition of quinoline derivative or salt thereof containing no carbonate and low genotoxic impurity content
WO2011129792A1 (en) Water dispersible formulations comprising cefpodoxime proxetil
WO2011139253A2 (en) Pharmaceutical compositions comprising ceftibuten
WO2011093828A2 (en) Solid dosage forms comprising cefprozil
JP2020518611A (en) Compositions with improved water solubility and bioavailability
WO2013109223A1 (en) Particulate formulations of tadalafil in effervescent form
WO2013165327A1 (en) Pharmaceutical formulations comprising thiocolchicoside
WO2013100878A1 (en) Pharmaceutical formulations comprising aripiprazole
WO2014104989A1 (en) Pharmaceutical compositions comprising aripiprazole
JP2010111630A (en) Azulenesulfonate-containing particle, process for producing the same and pharmaceutical preparation containing the same
EP2804594A1 (en) Formulations comprising diclofenac as the active agent
EP2793856B1 (en) Orally-disintegrating formulations of flurbiprofen
US20190125678A1 (en) Sustained-Release Oral Dosage Forms for Low Aqueous Solubility Compounds
EP2566450A2 (en) Pharmaceutical compositions comprising cefetamet

Legal Events

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

Ref document number: 13733473

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13733473

Country of ref document: EP

Kind code of ref document: A1