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WO 2010/018484 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 18 February 2010 (18.02.2010) WO 2010/018484 Al (51) International Patent Classification: AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, A61K 31/222 (2006.01) A61P 13/10 (2006.01) CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) International Application Number: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, PCT/IB2009/053339 KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, (22) International Filing Date: ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, 31 July 2009 (3 1.07.2009) NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TJ, TM, TN, TR, TT, (25) Filing Language: English TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 61/088,866 14 August 2008 (14.08.2008) US GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, (71) Applicant (for all designated States except US): PFIZER TM), European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, LIMITED [GB/GB]; Ramsgate Road, Sandwich Kent ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, CT13 9NJ (GB). MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, (72) Inventors; and ML, MR, NE, SN, TD, TG). (75) Inventors/Applicants (for US only): MILLS, Ian, William [GB/GB]; Pfizer Global Research and Develop Declarations under Rule 4.17: ment, Ramsgate Road, Sandwich Kent CTl 3 9NJ (GB). — as to the identity of the inventor (Rule 4.17 (ϊ)) SCHOLFIELD, David, Peter [GB/GB]; Pfizer Global Research and Development, Ramsgate Road, Sandwich — of inventorship (Rule 4Λ 7(iv)) Kent CT 13 9NJ (GB). Published: (74) Agent: DROUIN, Stephane; Pfizer Global Research and — with international search report (Art. 21(3)) Development, Ramsgate Road, Sandwich Kent CT 13 9NJ (GB). — before the expiration of the time limit for amending the claims and to be republished in the event of receipt of (81) Designated States (unless otherwise indicated, for every amendments (Rule 48.2(h)) kind of national protection available): AE, AG, AL, AM, (54) Title: NEW USES OF DIISOPROPYLAMINE DERIVATIVES (57) Abstract: The invention provides a diisopropylamine derivative selected from: (a) a compound of formula I, or a pharmaceu tically acceptable salt or solvate thereof; and (b) a pharmaceutically acceptable ester prodrug of the compound of formula I, and its pharmaceutically acceptable salts and solvates; for use in the treatment of stress urinary incontinence or mixed urinary inconti nence. A preferred diisopropylamine derivative is fesoterodine, or a pharmaceutically acceptable salt thereof. New uses of diisopropylamine derivatives This invention relates to new medical uses of certain diisopropylamine derivatives, including fesoterodine, for the treatment of stress urinary incontinence and/or mixed urinary incontinence. Urinary incontinence (Ul) as defined by the International Continence Society is the complaint of any involuntary leakage of urine. It is a common and socially debilitating problem. Ul can be clinically classified as: (a) stress urinary incontinence (SUI), which is incontinence on effort, exertion, coughing or sneezing; (b) urge urinary incontinence (UUI), which is involuntary leakage of urine which is accompanied by, or immediately preceded by, urinary urgency; and (c) mixed urinary incontinence (MUI), which is a combination of SUI and UUI. The EPINCONT survey conducted in 27,936 women aged 20 years and above in Norway, revealed an overall prevalence of Ul of 25% of whom 50%, 36% and 11% had SUI, MUI and UUI, respectively. In normal continence in women the storage of urine during bladder filling is facilitated by a sympathetic nervous system reflex, which increases tension and constriction of the urinary sphincter and inhibits parasympathetic bladder efferents. During normal voiding, increases in parasympathetic transmissions to the bladder initiate detrusor contraction. Incontinence can therefore occur either as a result of an incompetent sphincter, or abnormal or involuntary detrusor contractions, or indeed a combination of the two. Urge urinary incontinence (UUI) is a condition characterized by involuntary leakage of urine which is accompanied by, or immediately preceded by, urinary urgency (defined as a sudden compelling desire to pass urine which is difficult to defer). The corresponding urodynamic observation of urge urinary incontinence is detrusor overactivity incontinence: incontinence due to an involuntary detrusor contraction. Stress urinary incontinence (SUI) is the complaint of involuntary leakage on effort or exertion or on sneezing or coughing . It is characterized by urethral underactivity/dysfunction. The corresponding urodynamic observation is the involuntary leakage of urine during increased abdominal pressure, in the absence of a detrusor contraction. Mixed urinary incontinence (MUI) is the complaint of involuntary leakage associated with urgency and also with exertion, effort, sneezing or coughing. The ICS do not define a specific corresponding urodynamic observation and, for reasons described below, it is incorrect to conclude that both detrusor overactivity and urodynamic stress incontinence be present for a urodynamic diagnosis of MUI to be made. Ul affects approximately 13 million Americans and is at least as prevalent as other chronic diseases including asthma and peptic ulcer disease. Although not life threatening, it results in a significant detrimental effect on health related quality of life and has a considerable health economic impact. The direct medical costs for the management of urinary incontinence are estimated to be $ 10-1 6 billion per annum. Urinary incontinence is associated with significant morbidity and is correlated with an increased risk of hospitalization and admission to a nursing home. Of the subtypes of urinary incontinence MUI is the most bothersome. This symptom burden is thought to be due to the unpredictability of incontinence episodes resulting in a perception of lack of 'bladder control'. The greater perceived severity of MUI reported by women may be due to the presence of 2 co-existent pathologies, one bladder, and one urethral or may simply be due to the presence of more severe stress incontinence. The absence of a strong correlation between reported symptoms and urodynamic observations, particularly the absence of detrusor overactivity, provides supporting evidence for the latter hypothesis. It has been observed that incontinence episode frequency observed in women with MUI is higher than in those women reporting SUI alone. There are currently no approved drugs for the treatment of SUI or MUI in the US. Duloxetine, a serotonin-norepinephrine reuptake inhibitor (SNRI), has been shown to be effective in the treatment of women who have stress-predominant urinary incontinence (SUI), and also more recently in the treatment of women with symptoms of bladder overactivity. However it has a significant adverse event burden that may limits its clinical utility. Therefore, SUI is a largely under diagnosed and under treated disease. An unmet medical need exists for a pharmacotherapy that is efficacious and well tolerated for the treatment of SUI. Drug treatment of UUI with antimuscarinic (anticholinergic) agents only addresses one component of MUI. There are currently no approved drugs for the treatment of MUI. Treatment is typically determined by the most bothersome presenting condition. Thus a patient with urge predominant MUI may be started on a treatment for UUI, e.g. anticholinergic therapy. However it is clear that this only addresses part of their symptom complex leaving the other component inadequately addressed. Moreover recent evidence suggests that SUI and MUI may share a common, urethral pathology insofar as leakage in SUI and MUI may occur as a result of a reduced ability to increase intra-urethral pressure during bladder filling. This may result in a breakthrough of urethral relaxation leading to a detrusor contraction and subsequent leakage. If this event is associated with the sensation of urgency, a diagnosis of UUI or MUI is commonly made albeit that the primary pathology is arising not from the bladder but, like SUI, actually from a dysfunctional urethra. Thus there is clearly an unmet medical need for an effective, well tolerated treatment for SUI and MUI. WO 89/06644 (and its equivalent EP-A-325571 ) disclose a group of diisopropylamine derivatives, including tolterodine [R-(+)-Λ/, Λ/-diisopropyl-3-(2- hydroxy-5-methylphenyl)-3-phenylpropylamine, see Example 22 and claim 7]: The compounds of WO 89/06644 are indicated in the treatment of "cholin- mediated disorders" such as urinary incontinence. Tolterodine is a muscarinic receptor antagonist and was developed for the treatment of overactive bladder. It gained its first marketing approval (as the tartrate salt) in 1997 and was launched in many markets in the following years under the trade marks DETROL and DETRUSITOL. WO 94/1 1337 discloses a further group of diisopropylamine derivatives, including R-(+)-Λ/, Λ/-diisopropyl-3-(2-hydroxy-5-hydroxymethylphenyl)-3-phenylpropylamine (see Example 1) : This compound is also formed in the body by metabolism of tolterodine. The compounds of WO 94/1 1337 are indicated in the treatment of "acetylcholine- mediated disorders", such as urinary incontinence. WO 99/58478 (and its priority document EP-A-0957073) discloses a further group of diisopropylamine derivatives, including fesoterodine [R-(+)-isobutyric acid 2-(3-diisopropylamino-1 -phenylpropyl)-4-hydroxymethylphenyl ester, see page 62 lines 15-1 6 of WO 99/58478]: The compounds of WO 99/58478 are indicated to be useful as prodrugs for treatment of urinary incontinence and other spasmogenic conditions that are caused by muscarinic mechanisms.
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