WO2013172339A1 - 腹圧性尿失禁予防剤及び/又は治療剤 - Google Patents
腹圧性尿失禁予防剤及び/又は治療剤 Download PDFInfo
- Publication number
- WO2013172339A1 WO2013172339A1 PCT/JP2013/063409 JP2013063409W WO2013172339A1 WO 2013172339 A1 WO2013172339 A1 WO 2013172339A1 JP 2013063409 W JP2013063409 W JP 2013063409W WO 2013172339 A1 WO2013172339 A1 WO 2013172339A1
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- Prior art keywords
- urinary incontinence
- stress urinary
- acid
- present
- agent
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4465—Non condensed piperidines, e.g. piperocaine only substituted in position 4
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
- C07D211/50—Aroyl radical
Definitions
- the present invention relates to a piperidine compound exhibiting an excellent preventive and / or therapeutic effect on stress urinary incontinence, and more particularly to 4-piperidyldiphenylpropoxyacetate or a salt thereof.
- Urinary incontinence is classified into urge (urgent) urinary incontinence, stress (tensive) urinary incontinence, overflow urinary incontinence, functional urinary incontinence, and mixed urinary incontinence.
- urge (urgent) urinary incontinence is classified into urge (urgent) urinary incontinence, stress (tensive) urinary incontinence, overflow urinary incontinence, functional urinary incontinence, and mixed urinary incontinence.
- stress (tensive) urinary incontinence is classified into urge (urgent) urinary incontinence, stress (tensive) urinary incontinence, overflow urinary incontinence, functional urinary incontinence, and mixed urinary incontinence.
- mixed urinary incontinence is associated with multiple urinary incontinences, but many are types of urinary incontinence combined with urge incontinence and stress urinary incontinence.
- Non-patent Document 2 4-Piperidyldiphenylpropoxyacetate is a known compound (Non-patent Document 2) as a metabolite that is expressed when propiverine is administered to rats, and its presence has been reported as a human metabolite although it is a trace amount. (Non-Patent Document 3).
- Patent Document 1 aims to provide a compound having a pharmaceutical action even better than O-propylbenzyl acid-1-methyl-4-piperidyl hydrochloride (propiverine), and 4-piperidyldiphenylpropoxyacetate is Disclosed is useful as a therapeutic agent for diseases such as frequent urination and nocturia that have bladder antispasmodic activity and appear as a result of cholinergic neuromuscular dysfunction of the bladder compression muscle.
- diseases such as frequent urination and nocturia that have bladder antispasmodic activity and appear as a result of cholinergic neuromuscular dysfunction of the bladder compression muscle.
- Propiverine ( ⁇ , ⁇ -diphenyl- ⁇ -n-propoxyacetic acid-1-methylpiperidyl-4-ester) is an anticholinergic drug that can effectively treat the hypertonic functional state of the bladder compression muscle It is described that it is effective for pollakiuria, nocturia, nocturnal enuresis (Patent Document 2).
- 4-piperidyldiphenylpropoxyacetate is known to be useful as a therapeutic agent for pollakiuria and nocturnal polyuria for which anticholinergic agents are effective, but no effect on stress urinary incontinence has been suggested. .
- JP 62-039567 A Japanese Patent Laid-Open No. 55-055117
- An object of the present invention is to provide an excellent prophylactic and / or therapeutic agent for stress urinary incontinence.
- the present inventors have obtained 4-piperidyldiphenylpropoxyacetate represented by the following general formula (1) (hereinafter sometimes referred to as “the present compound”) or The salt was found to have an excellent therapeutic effect on stress urinary incontinence and the present invention was completed.
- the present invention has the general formula (1)
- An agent for preventing and / or treating stress urinary incontinence containing an effective amount of 4-piperidyldiphenylpropoxyacetate represented by the formula (I) or a salt thereof and a pharmaceutical carrier.
- the present invention also provides a preventive and / or therapeutic agent for stress urinary incontinence comprising 4-piperidyldiphenylpropoxyacetate represented by the general formula (1) or a salt thereof as an active ingredient.
- the present invention includes the step of administering to a mammal a prophylactic or therapeutic effective amount of 4-piperidyldiphenylpropoxyacetate represented by the general formula (1) or a salt thereof for stress urinary incontinence.
- a method for preventing or treating incontinence is provided.
- the present invention provides use of 4-piperidyldiphenylpropoxyacetate represented by the general formula (1) or a salt thereof for producing a preventive or therapeutic agent for stress urinary incontinence.
- the present invention provides 4-piperidyldiphenylpropoxyacetate represented by the general formula (1) or a salt thereof for use in the prevention or treatment of stress urinary incontinence.
- the compound of the present invention or a salt thereof is useful as a preventive or therapeutic agent for stress urinary incontinence.
- LPP rat intraurinary bladder pressure
- 4-Piperidyldiphenylpropoxyacetate or a salt thereof of the present invention is a compound known as a metabolite found when propiverine is administered to rats and humans.
- Patent Document 1 describes a general production method thereof. Yes.
- the compound of the present invention obtained as described above can form a salt, particularly a pharmaceutically acceptable salt, by a generally known method.
- the compound of the present invention or a salt thereof can be isolated and purified by using generally known separation and purification means such as concentration, solvent extraction, filtration, recrystallization, various chromatography and the like.
- ⁇ , ⁇ -Diphenyl- ⁇ -n-propoxyacetic acid-1-methylpiperidyl-4-ester described in Patent Document 2 is different from the compound of the present invention in that a methyl group is bonded to the N atom of piperidine. , Its action is "to increase bladder capacity after bladder-and prostate surgery, to reduce intravesical pressure caused by mitechnisch in the case of overstressed bladder or to reduce bladder sensation from various painful sources And can be used for the treatment of frequent urination, nocturia and nocturia ".
- ⁇ , ⁇ -diphenyl- ⁇ -n-propoxyacetic acid-1-methylpiperidyl-4-ester is effective in increasing bladder capacity and reducing the number of urinations, especially in nocturnal polyuria It has been shown that there is. Also, it has been reported that propiverine ( ⁇ , ⁇ -diphenyl- ⁇ -n-propoxyacetic acid-1-methylpiperidyl-4-ester) is also useful for the treatment of stress urinary incontinence (for example, Acta Urol Jpn (1998) As described later, in the rat intraurinary bladder pressure (LPP) test, it was clear that the compound of the present invention significantly improved stress urinary incontinence than propiverine (see below). Example 2).
- the disease that can be treated by administering a drug containing the compound of the present invention includes stress urinary incontinence.
- most mixed urinary incontinence is a type of urinary incontinence in which stress urinary incontinence and urge urinary incontinence are combined, and can be administered to mixed urinary incontinence.
- the present invention provides a pharmaceutical composition containing an effective amount of the compound of the present invention represented by the general formula (1) or a pharmaceutically acceptable salt thereof.
- Examples of the pharmaceutically acceptable salt of the compound of the present invention include acid addition salts with organic acids or inorganic acids, and specifically include hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphorus.
- Inorganic acids such as acids, and formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, lactic acid, malic acid, citric acid, tartaric acid, carbonic acid, picric acid, methanesulfonic acid, paratoluene
- Examples thereof include acid addition salts with organic acids such as sulfonic acid and glutamic acid.
- the compound of the general formula (1) or a salt thereof of the present invention in using the compound of the general formula (1) or a salt thereof of the present invention as a medicine, it can be combined with a pharmaceutical carrier, and various administration forms can be adopted depending on the purpose of prevention or treatment.
- Oral preparations, injections, suppositories, ointments, patches and the like may be used, and oral preparations are preferably employed.
- Each of these dosage forms can be produced by a conventional formulation method known to those skilled in the art.
- a pharmaceutical carrier various organic or inorganic carrier substances commonly used as pharmaceutical materials are used. Excipients, lubricants, binders, disintegrants in solid preparations, solvents in liquid preparations, solubilizers, suspensions It is blended as an agent, isotonic agent, buffer, soothing agent and the like. In addition, formulation additives such as preservatives, antioxidants, colorants, sweeteners and the like can be used as necessary.
- excipients include lactose, sucrose, sodium chloride, glucose, starch, calcium carbonate, kaolin, microcrystalline cellulose, silicic acid
- a binder water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatin solution, carboxymethylcellulose, hydroxypropylcellulose, hydroxypropyl starch, methylcellulose, ethylcellulose, shellac, calcium phosphate, polyvinylpyrrolidone, etc.
- the disintegrating agent include dry starch, sodium alginate, agar powder, sodium hydrogen carbonate, calcium carbonate, sodium lauryl sulfate, stearic acid monoglyceride, and lactose.
- Phosphate, borax, polyethylene glycol and the like, as the colorant, titanium oxide, iron oxide, white as the flavoring agent sugar, orange peel, citric acid can be exemplified tartaric acid.
- an oral solution, a syrup, an elixir, etc. can be produced by adding a flavoring / flavoring agent, a buffer, a stabilizer and the like to the compound of the present invention by conventional methods.
- the flavoring and flavoring agents may be those listed above
- examples of the buffer include sodium citrate
- examples of the stabilizer include tragacanth, gum arabic, and gelatin.
- a pH adjuster, buffer, stabilizer, tonicity agent, local anesthetic, etc. are added to the compound of the present invention, and subcutaneous, intramuscular and intravenous injections are prepared by conventional methods.
- the pH adjuster and buffer include sodium citrate, sodium acetate, and sodium phosphate.
- the stabilizer include sodium pyrosulfite, EDTA, thioglycolic acid, thiolactic acid and the like.
- local anesthetics include procaine hydrochloride and lidocaine hydrochloride.
- isotonic agents include sodium chloride and glucose.
- a formulation carrier known in the art such as polyethylene glycol, lanolin, cocoa butter, fatty acid triglyceride and the like, and an interface such as Tween (registered trademark) as necessary are added to the compound of the present invention.
- Tween registered trademark
- bases, stabilizers, wetting agents, preservatives and the like that are usually used for the compound of the present invention are blended as necessary, and mixed and formulated by a conventional method.
- the base include liquid paraffin, white petrolatum, white beeswax, octyldodecyl alcohol, paraffin and the like.
- the preservative include methyl paraoxybenzoate, ethyl paraoxybenzoate, and propyl paraoxybenzoate.
- the ointment, cream, gel, paste or the like may be applied to a normal support by a conventional method.
- a woven fabric, non-woven fabric, soft vinyl chloride, polyethylene, polyurethane film or foam sheet made of cotton, suf, or chemical fiber is suitable.
- the amount of the compound of the present invention or a salt thereof to be incorporated in each of the above dosage unit forms is not constant depending on the symptom of the patient to which the present invention is to be applied, or the dosage form thereof. It is desirable that the dosage is about 0.01 to 1000 mg, about 0.01 to 500 mg for injections, and about 0.01 to 1000 mg for suppositories.
- the daily dose of the drug having the above dosage form varies depending on the patient's symptoms, body weight, age, sex, etc., and cannot be determined unconditionally, but is usually about 0.05 to 5000 mg per day for an adult, preferably 0.1 to The dose may be 1000 mg, and it is preferable to administer this once a day or divided into 2 to 4 times a day.
- the compound represented by General formula (1) or its salt is used individually by 1 type or in combination of multiple types.
- mammals to which the compound of the present invention is administered include humans, monkeys, mice, rats, rabbits, dogs, cats, cows, horses, pigs, sheep and the like.
- Example 1 Efficacy Evaluation in Stress Pressure Urinary Incontinence Model Eight cases per group of female rats administered intramuscularly with botulinum A toxin were used, and the abdominal subcutaneous was electrically stimulated to increase the abdominal pressure and develop urinary incontinence.
- the compound of the present invention (30 mg / kg) was orally administered to model rats, and distilled water was orally administered at 2 mL / kg to the control group and the normal group not treated with botulinum A toxin.
- the number of urinary incontinences was counted before administration, 30 minutes after administration, and 2 hours after administration, and the results are shown in Table 1.
- urinary incontinence was not observed in the normal group by electrical stimulation to the abdominal skin, but in the control group, urinary incontinence was confirmed in all cases before administration, 30 minutes and 2 hours after administration.
- urinary incontinence was observed by electrical stimulation before administration of the compound of the present invention, but the number of individuals who did not develop urinary incontinence by electrical stimulation was significantly reduced 2 hours after administration. From these results, it was confirmed that the compound of the present invention improves urinary incontinence symptoms in the stress urinary incontinence model.
- LBP Rat Urinary Leakage Intravesical Pressure
- Anesthesia was performed by intraperitoneally administering 1.2 to 7 g / kg urethane to 6 to 7 cases per group of female SD rats. Next, it was fixed in the prone position and the spinal cord between the 9th and 10th thoracic vertebrae was completely cut. After hemostasis, the patient was fixed in the supine position, and a midline incision was made in the abdomen. The bladder was exposed, the top of the head was incised, and a catheter for measuring intravesical pressure was placed. After completion of catheter placement, abdominal pressure was forcibly applied from the outside manually. At this time, the intravesical pressure at the time of urine leakage was monitored, and this was defined as LPP.
- a physiological saline solution, the compound of the present invention (3 mg / kg), and propiverine (3 mg / kg) as a control drug were administered at 1 ⁇ mL / kg from the tail vein.
- LPP was measured 5 minutes after administration, and the average value and standard error were calculated. The results are shown in FIG.
- the compound of the present invention represented by the general formula (1) or a salt thereof is useful as a prophylactic and / or therapeutic agent for stress urinary incontinence.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
本出願は、2012年5月15日に出願された、日本国特許出願第特願2012-111843号明細書(その開示全体が参照により本明細書中に援用される)に基づく優先権を主張する。本発明は、優れた腹圧性尿失禁の予防効果及び/又は治療効果を示すピペリジン化合物に関し、特に4-ピペリジルジフェニルプロポキシアセテート又はその塩に関するものである。
ボツリヌスA毒素を筋肉内投与した雌ラット1群あたり8例を使用し、腹部皮下を電気刺激することで腹圧を上昇させ尿失禁を発現させた。モデルラットに、本発明化合物(30 mg/kg)を、また対照群及びボツリヌスA毒素を処置しない正常群には蒸留水を2 mL/kgにて経口投与した。投与前、投与から30分後、及び2時間後の尿失禁の回数をカウントし、結果を表1に示した。
ラット漏出時圧(LPP)試験は、腹圧性尿失禁の治療効果を評価するin vivo試験として一般的に用いられる(Am J Physiol Renal Physiol 293: F920-F926, 2007)。
Claims (5)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201380023152.7A CN104302293B (zh) | 2012-05-15 | 2013-05-14 | 用于压力性尿失禁的预防剂和/或治疗剂 |
ES13790782.0T ES2612827T3 (es) | 2012-05-15 | 2013-05-14 | Agente profiláctico y/o agente terapéutico para incontinencia urinaria de esfuerzo |
US14/388,289 US9603845B2 (en) | 2012-05-15 | 2013-05-14 | Prophylactic agent and/or therapeutic agent for stress urinary incontinence |
JP2014515634A JP5908072B2 (ja) | 2012-05-15 | 2013-05-14 | 腹圧性尿失禁予防剤及び/又は治療剤 |
EP13790782.0A EP2851073B1 (en) | 2012-05-15 | 2013-05-14 | Prophylactic agent and/or therapeutic agent for stress urinary incontinence |
HK15103765.0A HK1203159A1 (en) | 2012-05-15 | 2015-04-17 | Prophylactic agent and or therapeutic agent for stress urinary incontinence |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012111843 | 2012-05-15 | ||
JP2012-111843 | 2012-05-15 |
Publications (1)
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WO2013172339A1 true WO2013172339A1 (ja) | 2013-11-21 |
Family
ID=49583744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2013/063409 WO2013172339A1 (ja) | 2012-05-15 | 2013-05-14 | 腹圧性尿失禁予防剤及び/又は治療剤 |
Country Status (9)
Country | Link |
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US (1) | US9603845B2 (ja) |
EP (1) | EP2851073B1 (ja) |
JP (1) | JP5908072B2 (ja) |
CN (1) | CN104302293B (ja) |
ES (1) | ES2612827T3 (ja) |
HK (1) | HK1203159A1 (ja) |
PL (1) | PL2851073T3 (ja) |
TW (1) | TWI544925B (ja) |
WO (1) | WO2013172339A1 (ja) |
Families Citing this family (3)
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EP2311962B1 (en) | 2002-03-29 | 2013-03-13 | XOMA Technology Ltd. | Multigenic vectors plasmids and methods for increasing expression of recombinant polypeptides |
EP3796908B1 (en) | 2018-11-16 | 2023-05-10 | Santa Farma Ilaç Sanayi A.S. | Controlled release propiverine formulations |
EP4251154A1 (en) | 2020-11-27 | 2023-10-04 | Santa Farma Ilac Sanayii A.S. | Sustained release formulation compositions comprising propiverine |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5555117A (en) | 1978-10-09 | 1980-04-22 | Apogepha Veb | Medicine for treating bladder in tension excess state |
JPS6239567A (ja) | 1985-08-14 | 1987-02-20 | Taiho Yakuhin Kogyo Kk | ベンジル酸−4−ピペリジルエステル誘導体 |
-
2013
- 2013-05-14 TW TW102117019A patent/TWI544925B/zh active
- 2013-05-14 JP JP2014515634A patent/JP5908072B2/ja active Active
- 2013-05-14 US US14/388,289 patent/US9603845B2/en active Active
- 2013-05-14 ES ES13790782.0T patent/ES2612827T3/es active Active
- 2013-05-14 WO PCT/JP2013/063409 patent/WO2013172339A1/ja active Application Filing
- 2013-05-14 EP EP13790782.0A patent/EP2851073B1/en active Active
- 2013-05-14 CN CN201380023152.7A patent/CN104302293B/zh active Active
- 2013-05-14 PL PL13790782T patent/PL2851073T3/pl unknown
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2015
- 2015-04-17 HK HK15103765.0A patent/HK1203159A1/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5555117A (en) | 1978-10-09 | 1980-04-22 | Apogepha Veb | Medicine for treating bladder in tension excess state |
JPS6239567A (ja) | 1985-08-14 | 1987-02-20 | Taiho Yakuhin Kogyo Kk | ベンジル酸−4−ピペリジルエステル誘導体 |
Non-Patent Citations (7)
Title |
---|
ACTA UROL JPN, vol. 44, 1998, pages 65 - 69 |
AM J PHYSIOL RENAL PHYSIOL, vol. 293, 2007, pages F920 - F926 |
EUROPEAN JOURNAL OF DRUG METABOLISM AND PHARMACOKINETICS, vol. 13, no. 2, 1988, pages 81 - 90 |
J CHROMATOGR, vol. 420, 1987, pages 43 - 52 |
OKADA, H. ET AL.: "Clinical effect of propiverine in patients with urge or stress incontinence.", ACTA UROL., vol. 44, no. 1, 1998, JPN., pages 65 - 69, XP055169182 * |
See also references of EP2851073A4 * |
WORLD J UROL, vol. 15, 1997, pages 268 - 274 |
Also Published As
Publication number | Publication date |
---|---|
PL2851073T3 (pl) | 2017-06-30 |
CN104302293A (zh) | 2015-01-21 |
ES2612827T3 (es) | 2017-05-18 |
EP2851073A4 (en) | 2015-10-28 |
JP5908072B2 (ja) | 2016-04-26 |
HK1203159A1 (en) | 2015-10-23 |
TWI544925B (zh) | 2016-08-11 |
US20150051250A1 (en) | 2015-02-19 |
TW201350118A (zh) | 2013-12-16 |
CN104302293B (zh) | 2017-03-15 |
US9603845B2 (en) | 2017-03-28 |
EP2851073A1 (en) | 2015-03-25 |
EP2851073B1 (en) | 2016-11-09 |
JPWO2013172339A1 (ja) | 2016-01-12 |
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