WO2003101439A1 - Medicament contenant du 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol dans differentes formulations pour traiter l'incontinence urinaire - Google Patents

Medicament contenant du 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol dans differentes formulations pour traiter l'incontinence urinaire Download PDF

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Publication number
WO2003101439A1
WO2003101439A1 PCT/EP2003/005489 EP0305489W WO03101439A1 WO 2003101439 A1 WO2003101439 A1 WO 2003101439A1 EP 0305489 W EP0305489 W EP 0305489W WO 03101439 A1 WO03101439 A1 WO 03101439A1
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WO
WIPO (PCT)
Prior art keywords
dimethylamino
acid
pentan
methyl
methoxy
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Application number
PCT/EP2003/005489
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German (de)
English (en)
Inventor
Johannes BARTHOLOMAÜS
Thomas Christoph
Original Assignee
Grünenthal GmbH
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 Grünenthal GmbH filed Critical Grünenthal GmbH
Priority to AU2003237682A priority Critical patent/AU2003237682A1/en
Publication of WO2003101439A1 publication Critical patent/WO2003101439A1/fr

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Classifications

    • 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
    • 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

Definitions

  • the invention relates to the use of 1-dimethylamino-3- (3-methoxyphenyl) -2-methyl-pentan-3-ol or one of its pharmaceutically acceptable salts in various formulations for the manufacture of medicaments for the treatment of increased urge to urinate or urinary incontinence ,
  • Urinary incontinence is the involuntary loss of urine. This occurs in an uncontrolled manner when the pressure inside the bladder exceeds the pressure necessary to close the ureter.
  • the causes can be on the one hand an increased internal bladder pressure (e.g. due to detrusor instability) with the consequence of urge incontinence and on the other hand a reduced sphincter pressure (e.g. after birth or surgical interventions) with the result of stress incontinence.
  • the detrusor is the roughly bundled multilayered bladder wall muscles, the contraction of which leads to emptying of the lungs, the sphincter the sphincter of the urethra. There are mixed forms of these types of incontinence as well as so-called excess incontinence (e.g.
  • Urge to urinate is the state of increased bladder muscle tension aimed at emptying urine (micturition) when the bladder capacity is approached (or exceeded). This tension acts as a micturition.
  • Increased urge to urinate means in particular the occurrence of premature or sometimes sometimes even painful urge to urinate, up to the so-called urge to urinate. This leads to a significantly more frequent micturition.
  • Causes can include urinary bladder infections and neurogenic bladder disorders as well as bladder tuberculosis. However, not all causes have yet been clarified.
  • Increased urge to urinate and in particular urinary incontinence are usually treated with drugs that are involved in the reflexes of the lower urinary tract (Wein, A.J., 1998, Urology 51 (Suppl. 21): 43-47). Most often, these are drugs that have an inhibitory effect on the detrusor muscle, which is responsible for internal bladder pressure.
  • These drugs are e.g. B. Parasympatholytics such as oxybutynin, propiverine or tolterodine, tricyclic antidepressants such as imipramine or muscle relaxants such as flavoxate.
  • ⁇ -adrenoreceptors such as ephedrine
  • ⁇ -adrenoreceptors such as clenbutarol
  • hormones such as estradiol.
  • Certain opioids, diarylmethylpiperazines and piperidines, are also described for this indication in WO 93/15062.
  • the invention therefore relates to the use of 1-dimethylamino-3- (3-methoxy-phenyl) -2-methyl-pentan-3-ol for the production of a medicament for the treatment of increased urge to urinate or urinary incontinence, the 1-dimethylamino 3- (3-methoxy-phenyl) -2-methyl-pentan-3-ol in a pharmaceutical formulation selected from:
  • an oral osmotically driven drug delivery system a parenteral implant, a multipore tablet, a gel matrix tablet, a transdermal application system, a local application system or a parenteral depot system.
  • the treatment of increased urge to urinate or urinary incontinence includes in particular the treatment of dangincontinence and stress incontinence.
  • 1-Dimethylamino-3- (3-methoxy-phenyl) -2-methyl-pentan-3-ol is known as an analgesic active ingredient from EP 0 693 475 B1 as well as its preparation.
  • 1-Dimethylamino-3- (3-methoxy-phenyl) -2-methyl-pentan-3-ol has two centers of asymmetry so that the compound can exist in the form of four different stereoisomers.
  • 1-dimethylamino-3- (3-methoxy-phenyl) -2-methylpentan-3-ol can be used as a mixture of all four diastereomers in any mixing ratio, but also as a mixture of two or three of the four stereoisomers or in stereoisomerically pure form.
  • Preferred stereoisomers here are (+) - (2R, 3R) -1-dimethylamino-3- (3-methoxyphenyl) -2-methylpentan-3-ol and (-) - (1 S, 2S) -1 -Dimethylamino-3- (3-methoxy-phenyl) -2-methyl-pentan-3-ol, which can be present in the formulation according to the invention as a mixture, in particular as a 1: 1 mixture (racemate), or particularly preferably in isomerically pure form ,
  • active ingredient 1 is therefore 1-dimethylamino-3- (3-methoxyphenyl) -2-methylpentan-3-ol as a mixture of various of its stereoisomers or as one of its pure stereoisomers, in each case as free Base or in the form of a pharmaceutically acceptable salt, and accordingly the use according to the invention comprises the use of 1-dimethylamino-3- (3-methoxyphenyl) -2
  • 1-Dimethylamino-3- (3-methoxy-phenyl) -2-methyl-pentan-3-ol can be present as a base or in the form of a salt and optionally also a solvate. Accordingly, the use according to the invention comprises the use of 1-dimethylamino-3- (3-methoxy-phenyl) -2-methyl-pentan-3-ol in the form of its base or in the form of a salt, in particular the physiologically tolerable salts, or in the form their solvates, especially hydrates.
  • salt is to be understood to mean any form of the active substance according to the invention in which it takes on an ionic form or is charged and is coupled to a counterion (a cation or anion) or is in solution.
  • This also includes complexes of the active ingredient with other molecules and ions, in particular complexes that are complexed via ionic interactions.
  • physiologically compatible salts in particular physiologically compatible salts with cations or bases and physiologically compatible salts with anions or acids or also a salt formed with a physiologically compatible acid or a physiologically compatible cation ,
  • physiologically compatible salt with anions or acids is understood to mean at least salts in the sense of this invention one of the compounds according to the invention - mostly protonated, for example on nitrogen - as a cation with at least one anion which are physiologically compatible - in particular when used in humans and / or mammals.
  • this is understood in particular to mean the salt formed with a physiologically compatible acid, namely salts of the respective active ingredient with inorganic or organic acids which are physiologically compatible, in particular when used in humans and / or mammals.
  • physiologically acceptable salts of certain acids are salts of: hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, formic acid, acetic acid, oxalic acid, succinic acid, malic acid, tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid, glutamic acid, 1, 1-dioxo-1, 2 -dihydro1b6- benzo [d] isothiazol-3-one (saccharic acid), monomethylsebacic acid, 5-oxo-proline, hexane-1-sulfonic acid, nicotinic acid, 2-, 3- or 4-aminobenzoic acid, 2,4,6-trimethyl- benzoic acid, a-lipoic acid, acetylglycine, acetylsalicylic acid, hippuric acid and / or aspartic acid.
  • the hydrochloride salt is particularly preferred.
  • the term of the salt formed with a physiologically compatible acid is understood in the context of this invention to be salts of respective active ingredient with inorganic or organic acids that are physiologically compatible - especially when used in humans and / or mammals.
  • the hydrochloride is particularly preferred.
  • physiologically compatible acids are: hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, formic acid, acetic acid, oxalic acid, succinic acid, tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid, glutamic acid, 1, 1-dioxo-1, 2-dihydro1 ⁇ 6 - benzo [ d] isothiazol-3-one (saccharic acid), monomethylsebacic acid, 5-oxo-proline, hexane-1-sulfonic acid, nicotinic acid, 2-, 3- or 4-aminobenzoic acid, 2,4,6-trimethyl-benzoic acid, ⁇ -lipoic acid , Acetylglycine, acetylsalicylic acid, hippuric acid and / or aspartic acid.
  • physiologically compatible salt with cations or bases is understood to mean at least salts in the sense of this invention one of the compounds according to the invention - usually a (deprotonated) acid - as an anion with at least one, preferably inorganic, cation, which are physiologically compatible, in particular when used in humans and / or mammals.
  • the salts of the alkali and alkaline earth metals are also particularly preferred, however, with NH + , but in particular (mono-) or (di-) sodium, (mono-) or (di-) potassium, magnesium or calcium salts.
  • salt formed with a physiologically compatible cation is understood to mean at least salts in the sense of this invention one of the respective compounds as an anion with at least one inorganic cation which is physiologically compatible - in particular when used in humans and / or mammals.
  • the salts of the alkali and alkaline earth metals but also NH 4 + are particularly preferred, but in particular (mono-) or (di-) sodium, (mono-) or (di-) potassium, magnesium or calcium salts.
  • the oral osmotically driven active ingredient delivery system is to be understood in particular as the OROS-SYSTEM from AIza, a system in tablet form with a delivery opening, an osmotic one
  • Drug core a semi-permeable membrane and a polymeric part that exerts pressure.
  • a parenteral implant is understood to mean any form of non-biodegradable implant that slowly releases active substance over a longer period of time.
  • DUROS SYSTEM from ALZA, as described for example in WO 00/54745 and which consists of an inert tube, a semipermeable membrane, an "osmotic engine", a stamp, a dispensing opening and a depot for receiving the dispensable (Usually highly concentrated) active ingredient solution Suitable examples are described in the patents US4612008, US4765989, US4783337, US5264446, US4519801, US4612008, US4783337 and US5082668.
  • Another example is based on non-biodegradable polymers based on ethylene-vinyl acetate copolymers, as described for example for contraceptives by De Nijs et al (US4,957,119, US5,088,505)
  • Examples of a multipore tablet are the products developed by Gacell, Andrx, Elan (for example under Modas, Sodas). Suitable examples can be found in EP 122077 A2, EP360562 B1, EP 320097 A1 and US 499276.
  • Examples of a gel matrix tablet are the products developed by Penwest Pharmaceuticals (for example under TimeRX). Suitable examples can be found in US 5,330,761, US 5,399,362, US 5,472,711 and US 5,455,046.
  • a transdermal application system is understood to be systems which - if appropriate using penetration aids such as plasticizers and penetration accelerators - are applied to the skin and release the active ingredient through the skin into the body.
  • penetration aids such as plasticizers and penetration accelerators - are applied to the skin and release the active ingredient through the skin into the body. Examples that can all be used here include described in DE 10033853, US 5,411,740, EP 767659, AT185694E, DE 69326848T2. Further examples transferred directly in the formulation are the suitable plasters from EP 0 430 019 B1, WO 98/36728 or WO96 / 19975.
  • a local application system is understood to mean, in particular in the urogenital tract, for example pharmaceutical forms to be applied to mucous membranes, with the active ingredient being released more slowly in most cases.
  • An example is the vaginal ring from Enhance Pharmaceuticals as well as the system (vaginal ring) described in WO 01/70154.
  • a parenteral depot system means in particular depot systems based on slowly disintegrating or biodegradable polymers. Examples are polylactide polymers or
  • Polyglycolide polymers or in particular polylactide / polyglycolide copolymers are manufactured by Alkermes or Medisorb, and in particular for Takeda enantones and trenantones. This term also includes sprayable gels, especially those that solidify in situ and slowly release the active ingredient dissolved in them.
  • Examples are the Atrigel technology and other systems from Atrix (US5,278,201, US5,739,176, US6,143,314), in which PLGA polymers and active ingredients are mixed with pharmaceutically acceptable solvents which, after being introduced into the body, form an implant solidify, and the SABER technology from DURECT, which uses a three to four component system with sucrose acteate Isobutyrate (SAIB), a pharmaceutically acceptable solvent such as ethanol and one or more additives, and of course the active ingredient.
  • SABER technology from DURECT, which uses a three to four component system with sucrose acteate Isobutyrate (SAIB), a pharmaceutically acceptable solvent such as ethanol and one or more additives, and of course the active ingredient.
  • SABER technology from DURECT, which uses a three to four component system with sucrose acteate Isobutyrate (SAIB), a pharmaceutically acceptable solvent such as ethanol and one or more additives, and of course the active ingredient.
  • Example 8 Test system cystometry on the awake naive rat
  • threshold pressure threshold pressure TP, bladder pressure immediately before micturition
  • ICI Inter-contraction interval
  • TP threshold pressure
  • ICI inter-contraction interval
  • test substances 1 1.0 mg / kg
  • 2 0.1, 0.3 and 0.5 mg / kg
  • 21 0.5 mg / kg
  • the mean of 3 micturition cycles was determined at the effective maximum and presented as a percentage change compared to the previous value (Table 1).
  • Table 1 Influence of the cystometric parameters by the test substances (change from previous value [%]); n corresponds to the number of test animals; Significance (Student T-Test): * p ⁇ 0.05; ** p ⁇ 0.01; *** p ⁇ 0.001.
  • the investigated substances show a positive effect on bladder regulation and are therefore suitable for the treatment of urinary incontinence.
  • the (+) enantiomer compound 2
  • the (+) enantiomer compound 2
  • the (+) enantiomer compound 21
  • the (-) enantiomer compound 21

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  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Urology & Nephrology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne l'utilisation de 1-diméthylamino-3-(3-méthoxy-phényl)-2-méthyl-pentan-3-ol ou un de ses sels pharmaceutiquement acceptables dans différentes formulations pour produire des médicaments servant à traiter les besoins urinaires accrus ou l'incontinence urinaire.
PCT/EP2003/005489 2002-05-31 2003-05-26 Medicament contenant du 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol dans differentes formulations pour traiter l'incontinence urinaire WO2003101439A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003237682A AU2003237682A1 (en) 2002-05-31 2003-05-26 Medicament containing 1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol in different formulations for treating urinary incontinence

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10224556.8 2002-05-31
DE10224556A DE10224556A1 (de) 2002-05-31 2002-05-31 1-Dimethylamino- 3-(3-methoxy-phenyl)2-methyl-pentan-3-ol entaltendes Arzneimittel in verschiedenen Formulierungen

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WO2003101439A1 true WO2003101439A1 (fr) 2003-12-11

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4783337A (en) * 1983-05-11 1988-11-08 Alza Corporation Osmotic system comprising plurality of members for dispensing drug
US5411740A (en) * 1992-05-13 1995-05-02 Alza Corporation Transdermal administration of oxybutynin
EP0693475A1 (fr) * 1994-07-23 1996-01-24 Grünenthal GmbH Dérivés propane 1-phényl-3-diméthylamino à activité pharmocologique
EP1005861A1 (fr) * 1997-04-11 2000-06-07 Nippon Shinyaku Co., Ltd. Traitements des mictions frequentes et de l'incontinence urinaire
WO2001024783A2 (fr) * 1999-10-05 2001-04-12 Grünenthal GmbH Utilisation de (+)-tramadol, de o-demethyltramadol ou de (+)-o-demethyltramadol, de o-desmethyle-n-mono-desmethyl-tramadol ou de (+)o-desmethyl-n-mono-desmethyl-tramadol pour traiter l'incontinence urinaire
WO2001034139A1 (fr) * 1999-11-11 2001-05-17 Pharmacia Ab Formulation pharmaceutique contenant de la tolterodine et son utilisation
WO2001070154A1 (fr) * 2000-03-21 2001-09-27 Enhance Pharmaceuticals, Inc. Dispositif et procede de traitement de l'incontinence urinaire chez les femmes
WO2001098279A2 (fr) * 2000-06-20 2001-12-27 Pharmacia & Upjohn Company Bis-arylsulfones
WO2002043715A2 (fr) * 2000-11-30 2002-06-06 Grünenthal GmbH Utilisation de composes 1-phenyl-3-dimethylamino-propane pour traiter l'incontinence urinaire
WO2002067916A2 (fr) * 2001-02-28 2002-09-06 Grünenthal GmbH Sels pharmaceutiques
WO2003024444A1 (fr) * 2001-09-18 2003-03-27 Grünenthal GmbH Combinaison d'opioides selectionnes et d'antagonistes de muscarine destinee a traiter l'incontinence urinaire

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2150427T3 (es) * 1992-06-02 2000-12-01 Bard Inc C R Procedimiento y dispositivo de implante para el suministro de farmacos a largo plazo.

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4783337A (en) * 1983-05-11 1988-11-08 Alza Corporation Osmotic system comprising plurality of members for dispensing drug
US5411740A (en) * 1992-05-13 1995-05-02 Alza Corporation Transdermal administration of oxybutynin
EP0693475A1 (fr) * 1994-07-23 1996-01-24 Grünenthal GmbH Dérivés propane 1-phényl-3-diméthylamino à activité pharmocologique
EP1005861A1 (fr) * 1997-04-11 2000-06-07 Nippon Shinyaku Co., Ltd. Traitements des mictions frequentes et de l'incontinence urinaire
WO2001024783A2 (fr) * 1999-10-05 2001-04-12 Grünenthal GmbH Utilisation de (+)-tramadol, de o-demethyltramadol ou de (+)-o-demethyltramadol, de o-desmethyle-n-mono-desmethyl-tramadol ou de (+)o-desmethyl-n-mono-desmethyl-tramadol pour traiter l'incontinence urinaire
WO2001034139A1 (fr) * 1999-11-11 2001-05-17 Pharmacia Ab Formulation pharmaceutique contenant de la tolterodine et son utilisation
WO2001070154A1 (fr) * 2000-03-21 2001-09-27 Enhance Pharmaceuticals, Inc. Dispositif et procede de traitement de l'incontinence urinaire chez les femmes
WO2001098279A2 (fr) * 2000-06-20 2001-12-27 Pharmacia & Upjohn Company Bis-arylsulfones
WO2002043715A2 (fr) * 2000-11-30 2002-06-06 Grünenthal GmbH Utilisation de composes 1-phenyl-3-dimethylamino-propane pour traiter l'incontinence urinaire
WO2002067916A2 (fr) * 2001-02-28 2002-09-06 Grünenthal GmbH Sels pharmaceutiques
WO2003024444A1 (fr) * 2001-09-18 2003-03-27 Grünenthal GmbH Combinaison d'opioides selectionnes et d'antagonistes de muscarine destinee a traiter l'incontinence urinaire

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AU2003237682A1 (en) 2003-12-19
DE10224556A1 (de) 2004-01-08

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