WO2004084864A1 - Formulations contenant de la tolterodine et de la poudre de cacao et leur utilisation - Google Patents

Formulations contenant de la tolterodine et de la poudre de cacao et leur utilisation Download PDF

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Publication number
WO2004084864A1
WO2004084864A1 PCT/IB2004/000859 IB2004000859W WO2004084864A1 WO 2004084864 A1 WO2004084864 A1 WO 2004084864A1 IB 2004000859 W IB2004000859 W IB 2004000859W WO 2004084864 A1 WO2004084864 A1 WO 2004084864A1
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Prior art keywords
formulation according
tolterodine
oil
administration
cocoa butter
Prior art date
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PCT/IB2004/000859
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English (en)
Inventor
Nils-Olof Lindberg
Katarina Eva Anette Lindell
Alice C. Martino
Fredrik Per Nicklasson
Kristina Maarit Thyresson
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Pfizer Health Ab
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Publication date
Application filed by Pfizer Health Ab filed Critical Pfizer Health Ab
Priority to MXPA05010314A priority Critical patent/MXPA05010314A/es
Priority to CA002519119A priority patent/CA2519119A1/fr
Priority to AU2004224556A priority patent/AU2004224556A1/en
Priority to EP04720944A priority patent/EP1605920A1/fr
Priority to BRPI0408743-7A priority patent/BRPI0408743A/pt
Priority to JP2006506376A priority patent/JP2006521347A/ja
Publication of WO2004084864A1 publication Critical patent/WO2004084864A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/22—Anacardiaceae (Sumac family), e.g. smoketree, sumac or poison oak
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/31—Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/38—Clusiaceae, Hypericaceae or Guttiferae (Hypericum or Mangosteen family), e.g. common St. Johnswort
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/63—Oleaceae (Olive family), e.g. jasmine, lilac or ash tree
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/889—Arecaceae, Palmae or Palmaceae (Palm family), e.g. date or coconut palm or palmetto
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/899—Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
    • 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
    • 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
    • A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2068—Compounds of unknown constitution, e.g. material from plants or animals

Definitions

  • This invention relates to novel orally administered pharmaceutical formulations of tolterodine, optionally comprising salts, complexes, prodrugs and metabolites thereof, to the use of tolterodine, optionally comprising salts, prodrugs and metabolites thereof, for the manufacturing of a medicament to be administered orally for achieving an effect against overactive bladder, and to methods of treating overactive bladder by oral administration of tolterodine, optionally comprising salts, prodrugs and metabolites thereof.
  • Tolterodine is an effective and safe compound for treatment of overactive bladder.
  • the synthesis of tolterodine and its utility for the treatment of overactive bladder is disclosed in US 5,382,600 (Pharmacia & Upjohn AB).
  • An optimal efficacy/side effect profile is obtained at an oral dosage of 1 or 2 mg twice daily.
  • Tolterodine has a molecular weight of 325.0 and 475.6 as the tartrate salt.
  • the enantiomeric purity is > 99 %.
  • the pK a value is 9.87 and the solubility in water is about 11 mg/ml at room temperature.
  • the partition coefficient (Log P) between n-octanol and phosphate buffer at pH 7.32 is 1.83.
  • Tolterodine, PNU-200583 N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3- phenylpropanamine.
  • the major metabolic pathway for the metabolism of tolterodine is mediated by cytochrome P4502D6 leading to the formation of a 5-HM metabolite, (R)-N,N- diisopropyl-3-(2-hydroxy-5-hydroxymethylphenyl)-3-phenylpropanamine.
  • This metabolite has a similar pharmacological profile as tolterodine - see Nilvebrant L, Gillberg P-G, Sparf B. "Antimuscarinic potency and bladder selectivity of PNU-200577, a major metabolite of tolterodine.” Phannacol. Toxicol. (1997) 81 : 195-207.
  • N-dealkylated metabolite is mediated by CYP3 A and may be further metabolized to a N-dealkylated 5-hydroxymetabolite. See the below scheme.
  • One further metabolite is formed when a carboxylic acid group is formed at the CH2OH group of the 5-HM metabolite. Still one further metabolite is formed when a carboxylic acid group is fo ⁇ ned at the CH 2 OH group of the N-dealkylated 5-HM metabolite.
  • Tolterodine of the present invention encompasses the R-isomer, the S-isomer and the racemic mixture as well as salts, complexes, prodrugs and metabolites thereof.
  • Major effects are obtained from the R-isomer and the racemic mixture as well as from salts, complexes, prodrugs and metabolites thereof.
  • salts are tolterodine 1- tartrate and tolterodine mesylate.
  • Examples of complexes are complexes between tolterodine and beta-cyclodextrine and tolterodine and ion exchange compositions, such as ion exchange resinates.
  • Prior Art Above-mentioned US 5,382,600 does not disclose any formulation similar to the ones of the present invention.
  • WO 98/03067 discloses transdermal administration of the S-isomer of tolterodine.
  • WO 00/12070 discloses transdermal administration of the R-isomer and of the racemate of tolterodine. No prior art on tolterodine-containing formulations similar to the ones of the present invention has been found.
  • Chocolate which is different from cocoa powder as such, is very rarely used as an ingredient in pharmaceutical products, hitherto only in laxatives.
  • Ex- Lax ® being chocolated laxative pieces marketed by Novartis comprising sennosides. Purex, a laxative wherein phenolphthalein was formulated with chocolate, was marketed in the 1950s. It is not known any compositions comprising tolterodine and chocolate.
  • die present invention as further described below, is both new and inventive.
  • the present invention provides an orally administered pharmaceutical formu- lation of tolterodine, optionally comprising salts, prodrugs and metabolites thereof for achieving an effect against overactive bladder, comprising detrusor instability, detrusor hyperreflexia, urinary frequency, urinary urgency and urge incontinence.
  • the administration can be to a human being or to an animal.
  • the administration may be accomplished without the addition of liquid.
  • Admini- stration without added liquid is a big advantage in all those situations where e g clean water or other suitable liquid is not available, such as on travel.
  • the administration is discreet being a big advantage e g at lectures and on the theatre.
  • use of the present formulation, which should melt in the mouth rather than be swallowed, is of a great advantage to all those persons having difficulties in swallowing a traditional tablet.
  • a particularly useful dosage form of the present invention is thus a formulation that disintegrates or melts in the mouth without need for drinking water or other fluid.
  • the formulation is a dosage form comprising a therapeutically effective amount of tolterodine.
  • a “therapeutically effective amount” herein is an amount sufficient to achieve an effect against overactive bladder, comprising detrusor instability, detrusor hyperreflexia, urinary frequency, urinary urgency and urge incontinence.
  • urinary frequency is primarily meant a need to urinate more than 8 times over 24 hours or more than 2 times per night.
  • urinary urgency is primarily meant frequent, strong and sudden needs to urinate.
  • urge incontinence is primarily meant involuntary urination after a sudden need to urinate.
  • the amount of tolterodine be lower than an amount causing significant side effects.
  • the invention is adapted for discreet self-administration.
  • discreet self-administration herein is meant self-administration that does not draw attention to the existence of a need for therapy.
  • An object of the invention is to provide novel orally administered pharmaceutical formulations of tolterodine comprising cocoa powder.
  • a second object of the invention is to provide methods for preparing said formulations.
  • a third object of the invention is methods for using said fo ⁇ nulations therapy for treating overactive bladder.
  • the formulation provides for discreet self-administration
  • the formulation does not give an immediate patient-perceived association with medicines, as do traditional tablets. 6) The formulation may provide for rapid transmucosal absorption, especially when buffering agents are added.
  • tolterodine- containing formulation for transmucousal delivery, that mainly disintegrates and/or melts in the oral cavity with or without the aid of salivary fluid or mechanical erosion, or a combination thereof, after which the formulation may show adhesiveness towards tissues in the oral cavity.
  • the formulation is such that it does not require addition of liquid at the time of administration.
  • the formulation does not increase the need for therapy, as there is no increase in the urinary burden - in comparison with conventional tablets being administered together with liquid. No additional urine is produced.
  • buffering agents provides for a transient change in local pH of the saliva. Thereby a higher fraction of tolterodine is transformed into its less ionized form. Thereupon the transmucousal permeation is facilitated, which enhances the absorption of the active agent.
  • the choice of the buffering system is dependent on the one or more pK a s of the active agent.
  • cocoa powder acts as taste masker and texturizer.
  • Cocoa powder is defined as cocoa nib with some fat removed and ground into a powder. Cocoa nib is defined as cocoa beans with the shell removed. Cocoa butter is defined as fat expelled from the center (kernels or nib) of cocoa beans.
  • Cocoa powder is prepared from roasted cocoa beans. It is a complex compound, which consists of starch, cocoa butter, amino acids, proteins, xanthines, amines, mono- and polysaccharides, phospholipids, flavonoids, pyrazines, etc.
  • a preferred embodiment is a formulation, weighing around 400 mg, having the following preferred formulation (w/w):
  • a formulation weighing around 400 mg, is prepared with the following preferred composition (w/w):
  • Cocoa powder may be used in a non-alkalized form and in an alkalized form. Both are useful in the present formulations. Alkalized cocoa powder is preferred when a somewhat milder taste is desirable. A part of the hydrogenated soybean oil is melted. The solid components, i e tolterodine 1-tartrate, cocoa powder, mannitol, maize starch, aspartame, acesulfame-K, titanium dioxide, monosodium glutamate and the flavoring agents if solid, are added and mixed. A reduction of particle size of the solid components is performed by milling in a roll-refiner.
  • Example 2 In essentially the same way as in Example 1 are manufactured formulations with a weight from around 200 mg to around 1000 mg having the below composition (w/w):
  • the cocoa powder may be used in its non-alkalized form, its alkalized form or in a mixture thereof.
  • the diluents may be selected from one or more of the compounds sucrose, fruc- tose, glucose, galactose, lactose, maltose, invert sugar, a pharmaceutically acceptable polyol such as xylitol, sorbitol, maltitol, mannitol, isomalt and glycerol, or polydex- trose, or starch, or any mixture thereof, but only to such an extent that the taste-masking effect of the cocoa-powder remains sufficient.
  • a pharmaceutically acceptable polyol such as xylitol, sorbitol, maltitol, mannitol, isomalt and glycerol, or polydex- trose, or starch, or any mixture thereof, but only to such an extent that the taste-masking effect of the cocoa-powder remains sufficient.
  • the lipid ingredient being fatty components, may be chosen from one or more of the following compounds:
  • cocoa butter and cocoa butter alternatives including cocoa butter equivalents (CBE), cocoa butter substitutes (CBS), cocoa butter replacers (CBR) and cocoa butter improvers (CBI),
  • - corn oil sunflower oil, hybrid sunflower oil, soybean oil, rapeseed oil, canola oil, olive oil, ricebran oil, cottonseed oil, arachis (peanut, groundnut) oil and other oils characterized by being predominantly based on oleic, linoleic and linolenic acids and hydrogenated to a suitable melting point, - fish oil, tallow, lard, butterfat and other animal derived fats, and
  • the optional buffering agent/s may be selected from one or more of carbonates, bicarbonates, acetates, gluconates, glycerophosphates, phosphates or glycinates of sodium, potassium or ammonium, or mixtures thereof. Most phosphates are though less suitable because their taste usually is disagreeable and difficult to mask. Addition of buffering agents/s may increase the uptake through the buccal mucosa.
  • the sweetener may selected from one or more artificial sweeteners, such as sucrose, aspartame, acesulfame potassium, saccharine, sodium saccharine, cyclamate, glycyrrhizine, thaumatin (talin), sucralose, dihydrochalcone (neohesperidin dihydrochalcone), alitame, miraculin (miracle fruit), monellin (serendipity berry), stevside and/or salts thereof.
  • artificial sweeteners such as sucrose, aspartame, acesulfame potassium, saccharine, sodium saccharine, cyclamate, glycyrrhizine, thaumatin (talin), sucralose, dihydrochalcone (neohesperidin dihydrochalcone), alitame, miraculin (miracle fruit), monellin (serendipity berry), stevside and/or salts thereof.
  • the emulsifier is preferably soy lecithin and/or egg lecithin, but may be exchanged for - a nonionic surfactant, such as poloxamer, polyoxyethylene alkyl ether, poly- oxyethylene castor oil derivative, polyoxyethylene sorbitan fatty acid ester, monoglyce- ride, diglyceride and esther thereof, polyoxyethylene stearate, polyglycerolester of fatty acids, including polyglycerolpolyricinoleic acid (PGPR), sorbitan fatty acid ester,
  • PGPR polyglycerolpolyricinoleic acid
  • an anionic surfactant such as fatty acid, soap of fatty acid, lactylate, especially sodium and/or calcium stearoyllactylate, sodium lauryl sulfate and latanol,
  • zwitterionic surfactant such as zwitterionic phospholipid, such as phosphati- dylcholine and phosphatidylethanolamine, or mixtures, fractions or derivatives thereof or with lecithin.
  • Formulations according to the present inventions primarily constitute meltable and/or suckable oral tablets, but also include other suitable dosage forms for oral administration such as buccal patches, buccal paste and buccal sprays.
  • the present invention also encompasses tolterodine-containing formulations further comprising one or more other active agents having an effect against overactive bladder, such as oxobutynin, emepromium, trospium, propanetheline and darifenacin.
  • active agents having an effect against overactive bladder, such as oxobutynin, emepromium, trospium, propanetheline and darifenacin.
  • the present invention encompasses treating overactive bladder in a subject through administration to a subject of a tolterodine-containing orally administered pharmaceutical formulation as presented above, optionally together with one or more other agents having an effect against overactive bladder, and further optionally concomitantly with administration of agents for treating overactive bladder through one or more other routes of administration, such as through transdermal administration, peroral administration, administration by inhalation, administration by creams, salves and vagitories, and/or administration by injection.

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Abstract

Formulation pharmaceutique qui contient de la toltérodine et de la poudre de cacao, procédé de préparation de la formulation et utilisation de la préparation pour traiter l'hyperactivité de la vessie.
PCT/IB2004/000859 2003-03-26 2004-03-16 Formulations contenant de la tolterodine et de la poudre de cacao et leur utilisation WO2004084864A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
MXPA05010314A MXPA05010314A (es) 2003-03-26 2004-03-16 Nuevas formulaciones y su uso.
CA002519119A CA2519119A1 (fr) 2003-03-26 2004-03-16 Formulations contenant de la tolterodine et de la poudre de cacao et leur utilisation
AU2004224556A AU2004224556A1 (en) 2003-03-26 2004-03-16 Formulations comprising tolterodine and cocoa powder and use thereof
EP04720944A EP1605920A1 (fr) 2003-03-26 2004-03-16 Formulations contenant de la tolterodine et de la poudre de cacao et leur utilisation
BRPI0408743-7A BRPI0408743A (pt) 2003-03-26 2004-03-16 formulações compreendendo tolterodina e cacau em pó e sua utilização
JP2006506376A JP2006521347A (ja) 2003-03-26 2004-03-16 トルテロジン及びココアパウダーを含有する製剤及びその使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE0300830A SE0300830D0 (sv) 2003-03-26 2003-03-26 New formulations and use thereof
SE0300830-7 2003-03-26

Publications (1)

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WO2004084864A1 true WO2004084864A1 (fr) 2004-10-07

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EP (1) EP1605920A1 (fr)
JP (1) JP2006521347A (fr)
CN (1) CN1764441A (fr)
AR (1) AR043773A1 (fr)
AU (1) AU2004224556A1 (fr)
BR (1) BRPI0408743A (fr)
CA (1) CA2519119A1 (fr)
CL (1) CL2004000625A1 (fr)
MX (1) MXPA05010314A (fr)
SE (1) SE0300830D0 (fr)
WO (1) WO2004084864A1 (fr)
ZA (1) ZA200506710B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8802239B2 (en) 2009-10-16 2014-08-12 Dow Corning Toray Co., Ltd. Treatment composition for wipe paper
US8900645B2 (en) 2007-06-13 2014-12-02 Otsuka Pharmaceuticals Co., Ltd. Equol-containing extract, method for production thereof, method for extraction of equol, and equol-containing food

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1907136B (zh) * 2006-07-28 2010-08-25 张新生 植物保健乳及其加工方法

Citations (4)

* Cited by examiner, † Cited by third party
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GB918955A (en) * 1960-05-19 1963-02-20 Thomae Gmbh Dr K Pharmaceutical laxative compositions comprising 4,4-dihydroxy-2-amino triphenylmethane
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WO2000030641A1 (fr) * 1998-11-23 2000-06-02 Pharmacia & Upjohn Ab Compositions pharmaceutiques a base de nicotine permettant l'absorption transmucosale rapide
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US8900645B2 (en) 2007-06-13 2014-12-02 Otsuka Pharmaceuticals Co., Ltd. Equol-containing extract, method for production thereof, method for extraction of equol, and equol-containing food
US8993014B2 (en) 2007-06-13 2015-03-31 Otsuka Pharmaceutical Co., Ltd. Equol-containing extract, method for production thereof, method for extraction of equol, and equol-containing food
US9192185B2 (en) 2007-06-13 2015-11-24 Otsuka Pharmaceutical Co., Ltd. Equol-containing extract, method for production thereof, method for extraction of equol, and equol-containing food
US10681930B2 (en) 2007-06-13 2020-06-16 Otsuka Pharmaceutical Co., Ltd. Equol-containing extract, method for production thereof, method for extraction of equol, and equol-containing food
US8802239B2 (en) 2009-10-16 2014-08-12 Dow Corning Toray Co., Ltd. Treatment composition for wipe paper

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AR043773A1 (es) 2005-08-10
JP2006521347A (ja) 2006-09-21
SE0300830D0 (sv) 2003-03-26
CA2519119A1 (fr) 2004-10-07
AU2004224556A1 (en) 2004-10-07
CL2004000625A1 (es) 2005-01-07
BRPI0408743A (pt) 2006-03-28
ZA200506710B (en) 2006-11-29
MXPA05010314A (es) 2006-05-19
EP1605920A1 (fr) 2005-12-21

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