USRE44872E1 - Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient - Google Patents

Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient Download PDF

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USRE44872E1
USRE44872E1 US13/542,308 US200313542308A USRE44872E US RE44872 E1 USRE44872 E1 US RE44872E1 US 200313542308 A US200313542308 A US 200313542308A US RE44872 E USRE44872 E US RE44872E
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bladder
subject
active ingredient
overactive bladder
test
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Toshiyuki Takasu
Shuichi Sato
Masashi Ukai
Tatsuya Maruyama
Masayuki Shibasaki
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Astellas Pharma Inc
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Astellas Pharma Inc
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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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • 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
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • 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
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals

Definitions

  • This invention relates to a remedy for overactive bladder comprising (R)-2-(2-aminothiazol-4-yl)-4′-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetic acid anilide or a salt thereof as an active ingredient.
  • Bladder of mammals is under a dual control of autonomic nerve and detrusor relaxes via an adrenaline ⁇ receptor by stimulation of sympathetic nerve upon urination while, upon excretion of urine, it contracts via a muscarine receptor by stimulation of parasympathetic nerve.
  • anticholinergic agents such as propiverine hydrochloride and oxybutynin hydrochloride have been mostly used at present.
  • Example 41 of a pamphlet of International Laid-Open WO 99/20607 that (R)-2-(2-aminothiazol-4-yl)-4′-[2-[(2-hydroxy-2-phenylethyl)amino]-ethyl]acetic acid anilide dihydrochloride has both promotion action for insulin secretion and enhancing action for insulin sensitivity and further has anti-obese and anti-hyperlipemic actions whereby it is a useful compound for the treatment of diabetes mellitus but there is neither suggestion nor disclosure for the therapeutic use for overactive bladder (refer to Patent Document 1).
  • CGP-12,177A represented by the following chemical structural formula has a relaxation action for bladder (refer to Patent Document 2).
  • CGP-12,177A has been known as a selective drug having stimulating action to a ⁇ 3 -adrenaline receptor (refer to Non-Patent Documents 1 and 2)
  • R 1 is hydroxyl group, a lower alkyl group, an aralkoxy group, amino group, etc.;
  • R 2 is hydroxyl group or a lower alkyl group;
  • R 3 is hydrogen atom or halogen atom;
  • R 4 and R 5 each is hydrogen atom, halogen atom or a lower alkyl group; and
  • A is a lower alkylene group.
  • R 1 is hydrogen atom, a lower alkyl group or an aralkyl group
  • R 2 is hydrogen atom, a lower alkyl group or halogen atom
  • A is oxygen atom or imino group.
  • R 1 is hydroxyl group, etc.; one of R 2 and R 3 is hydrogen atom, halogen atom, etc. and another is hydrogen atom; and R 4 is halogen atom, etc.
  • Patent Document 1 Pamphlet of International Laid-Open WO 99/20607
  • Patent Document 2 Pamphlet of International Laid-Open WO 98/07445
  • Patent Document 3 Pamphlet of International Laid-Open WO 99/31045
  • Patent Document 4 Pamphlet of International Laid-Open WO 99/52856
  • Patent Document 5 Pamphlet of International Laid-Open WO 00/02846
  • Non-Patent Document 1 Drugs of the Future, 1993, volume 18, no. 6, page 542
  • Non-Patent Document 2 The American Society for Pharmacology and Experimental Therapeutics, 1993, volume 44, page 1100
  • the active ingredient of the present invention is useful as a remedy for diabetes mellitus and, as a result, they have found that the active ingredient of the present invention is useful as a remedy particularly for overactive bladder.
  • overactive bladder is defined as a disease by which urinary urgency is frequently resulted.
  • overactive bladder is sometimes accompanied by urinary frequency and urinary incontinence, it is not limited to the disease which is always accompanied by urinary frequency and urinary incontinence.
  • overactive bladder a patient is sensitive to the sense of wishing to urinate and frequently has a sense of wishing to urinate but, actually, he/she is able to hold his/her urine for a while.
  • QOL quality of life
  • Urinary frequency is a state where number of times of urination is more than the normal one and is said to be not less than about two times at night and not less than about 8 times during 24 hours.
  • urinary incontinence there is an involuntary leakage of urine and that is defined as a state where there is a problem socially or hygienically and is classified into stress urinary incontinence which occurs when abdominal pressure is applied such as cough and sneeze, urinary urge incontinence where a desire to urinate suddenly occurs and urine leaks before arriving at the toilet and urinary incontinence of a mixed type where both stress urinary incontinence and urinary urge incontinence are present.
  • the characteristic feature of the present invention is that the active ingredient of the present invention mitigates especially the frequent occurrence of urinary urgency of a patient and number of times of urination and state of urination are made into a more normal state.
  • overactive bladder in the present invention includes not only that as a result of benign prostatic hyperplasia but also that accompanied with urinary urgency, urinary incontinence and pollakiuria.
  • the active ingredient of the present invention is useful, in addition to treatment of diabetes, as an agent for prevention and treatment of other diseases where an improvement in symptom is able to be achieved by reducing the symptom of obesity and hyperlipemia such as arteriosclerosis, ischemic cardiac disease such as cardiac infarction and angina pectoris, brain artery sclerosis such as cerebral infarction, aneurysm, etc.
  • arteriosclerosis ischemic cardiac disease
  • angina pectoris ischemic cardiac disease
  • brain artery sclerosis such as cerebral infarction, aneurysm, etc.
  • the active ingredient of the present invention is useful as a remedy for overactive bladder.
  • Patent Document 2 use for overactive bladder is not mentioned as well.
  • CGP-12,177A has a relaxation action to bladder as a compound having a selective stimulating action to a ⁇ 3 -adrenaline receptor.
  • the active ingredient of the present invention has far stronger relaxation action for bladder.
  • Patent Document 2 there is no description for in vivo tests showing the usefulness for the treatment of overactive bladder such as “rat rhythmic bladder contraction measurement test” and “urination function measurement test on cyclophosphamide-induced overactive bladder model rat”.
  • Patent Documents 3 to 5 use for overactive bladder is not mentioned in Patent Documents 3 to 5 as well.
  • Compounds mentioned in Patent Documents 3 to 5 and the active ingredient of the present invention are different in their fundamental structures in such respects that the compounds mentioned in the documents always have a phenol ring but have no thiazole ring and also have no amide bond.
  • Patent Documents 3 to 5 there is no description for in vivo tests showing the usefulness for the treatment of over active bladder such as “rat rhythmic bladder contraction measurement test” and “urination function measurement test on cyclophosphamide-induced overactive bladder model rat”.
  • (R)-2-(2-aminothiazol-4-yl)-4′-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetic acid anilide or a salt thereof is an active ingredient.
  • the characteristic feature of the present invention is that the active ingredient of the present invention has been found to be useful as a remedy for overactive bladder which is a new use.
  • the active ingredient of the present invention is a free substance having no salt.
  • it may form a salt with an acid and examples of the salt are acid addition salts with a mineral acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid and phosphoric acid and an organic acid such as 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, ethanesulfonic acid and glutamic acid.
  • a mineral acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid and phosphoric acid
  • an organic acid such as formic acid, acetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid,
  • the active ingredient of the present invention having a salt may be easily manufactured from a free substance by a common salt-forming reaction.
  • the active ingredient of the present invention further includes hydrate, solvate and polymorphism.
  • the active ingredient of the present invention still further includes pharmacologically acceptable prodrug.
  • a group for forming the prodrug that mentioned in Prog. Med. 5, 2157-2161 (1985) and “Iyakuhin no Kaihatsu” (Development of Drugs) (Hirokawa Shoten, 1990), volume 7, Molecule Design, 163-198 may be exemplified.
  • the drug containing the active ingredient of the present invention may be in any of forms of oral administration by tablets, pills, capsules, granules, diluted powder, etc. and parenteral administration by inhalant, etc.
  • a solid composition for oral administration tablets, diluted powder, granules, etc. are used.
  • one or more active ingredient(s) is/are mixed with at least one inert excipient such as lactose, mannitol, glucose, hydroxypropyl cellulose, microcrystalline cellulose, starch, polyvinylpyrrolidone and magnesium metasilicate aluminate.
  • the composition may contain an inert additive such as lubricant (e.g., magnesium stearate), disintegrating agent (e.g., carboxymethyl starch sodium), solubilizing agent, etc. by a common method.
  • Tablets and pills may, if necessary, be coated with sugar coat or with an intragastric or enteric coating agent. Dose may be appropriately decided for each case taking symptom, age and sex of the subject to be administered, etc. into consideration. Usually, it is about 0.01 mg/kg to 100 mg/kg per day for an adult in the case of oral administration and is administered either at one time or by dividing into two to four.
  • the active ingredient of the present invention is able to be easily manufactured by a method mentioned in Patent Document 1 but, since method for the manufacture of a free substance which is preferred as the active ingredient of the present invention is not specifically mentioned therein, such a manufacturing method is shown in Manufacturing Examples. Route for the manufacture is illustrated as follows.
  • the organic layer was successively washed with 60 liters of 1M aqueous hydrochloric acid, 60 liters of 20% aqueous solution of potassium carbonate and water (60 liters, 60 liters) and concentrated in vacuo at 10 to 19° C.
  • the residue was dissolved in 35 liters of toluene with heating at 87° C., cooled and stirred at 20° C. throughout one night.
  • the resulting crystals were filtered and washed with 10 liters of toluene. This was dried in vacuo to give 7.66 kg of (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide as light yellow crystals.
  • EDC 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride
  • the compound A which is the active ingredient of the present invention showed a strong relaxation action in antagonism test to contraction by carbachol and antagonism test to contraction by potassium chloride in an isolated rat bladder smooth muscle relaxation test.
  • the compound A showed a significantly strong relaxation action as compared with CGP-12,177A (control compound).
  • Relaxation rates to drug concentration of the compound A which is the active ingredient of the present invention and the control compound are shown in FIG. 1 (antagonism test to contraction by carbachol) and FIG. 2 (antagonism test to contraction by potassium chloride), respectively. Further, EC 50 and maximum relaxation rate of the test drug in the antagonism test to contraction by carbachol are shown in Table 1 while concentration comparison of the compound A expressing the maximum relaxation rate of CGP-12,177A is shown in Table 2. The compound A showed an action strength of 270-fold as compared with the CGP-12,177A (control compound).
  • EC 50 and maximum relaxation rate of the test drug in the antagonism test to contraction by potassium chloride are shown in Table 3 while concentration comparison of the compound A expressing the maximum relaxation rate of CGP-12,177A is shown in Table 4.
  • the compound A showed an action strength of 383-fold as compared with the CGP-12,177A (control compound).
  • Female rats (225 to 290 g) of Wistar strain was used for the test. Under anesthetization with urethane, right and left ureters were ligated and cut and, after that, a polyethylene cannula was inserted from external urinary meatus and fixed. One end of the fixed cannula was connected to a pressure transducer via a three-way cock and pressure in the bladder was measured. Another end thereof was connected to a syringe pump and a physiological saline solution was continuously infused at a constant rate into bladder whereupon rhythmic bladder contraction was induced. The continuous infusion of a physiological saline solution was stopped after a rhythmic bladder contraction was noted. After the rhythmic bladder contraction was stabilized, drug or vehicle was administered from a catheter for administration of drug inserted into femoral vein.
  • the compound A was intravenously administered in increased doses where the ratio was 3 (0.03, 0.1, 0.3, 1 and 3 mg/kg).
  • a group to which vehicle was administered was used as a control group.
  • a suppressive effect for contraction frequency by the compound A is presumed to be due to an increase in bladder volume by stimulation of the compound A for a ⁇ 3 receptor existing in the bladder. It has been believed that an increase in functional bladder volume showing the urine volume which is able to be stored in the bladder is clinically useful for the treatment of patients suffering from overactive bladder and, therefore, the compound A is believed to be clinically effective as a remedy for overactive bladder.
  • Overactive bladder model rats induced by cyclophosphamide were prepared by referring to British Journal of Pharmacology, 2000, volume 130, page 331 and the following test was conducted.
  • mice Female rats (220 to 230 g) of Wistar strain were used for the test. Under anesthetization with pentobarbital sodium, a catheter for infusion of physiological saline solution and for measurement of pressure in bladder was inserted into bladder from the top of the bladder and fixed while a catheter for administration of a drug was inserted into carotid vein and fixed. Cyclophosphamide (CYP) was administered into abdominal cavity and, after being recovered, the rats were returned to a feeding cage. On the next day of the operation, one end of the catheter inserted into bladder of the rat was connected to a syringe pump via a three-way cock and a physiological saline solution was continuously infused whereby micturition reflex was induced. Another end was connected to a pressure transducer and pressure in the bladder was measured. After the micturition reflex was stabilized, 1 mg/kg of the compound A was administered from a catheter for administration of drug which was inserted into carotid vein.
  • Cyclophosphamide CY
  • the active ingredient of the present invention shows a strong bladder relaxation action in “isolated rat bladder smooth muscle relaxation test”, decreases the contraction frequency of rhythmic bladder contraction on a dose-depending manner in “rat rhythmic bladder contraction measurement test” and prolongs the micturition interval in “micturition function measurement test on cyclophosphamide-induced overactive bladder model rat” whereby it is clinically useful as a remedy for overactive bladder.
  • overactive bladder as a result of benign prostatic hyperplasia, it is also able to be used as a remedy for overactive bladder accompanied with urinary urgency, urinary incontinence and pollakiuria.
  • the active ingredient of the present invention (200.0 g) and 399.0 g of lactose were mixed in a polyethylene bag.
  • the mixture was mixed and disintegrated in a sample mill (manufactured by Hosokawa Micron).
  • the disintegrated mixture 450.0 g) and 60.1 g of corn starch were uniformly mixed in a fluidized granulation coating apparatus (manufactured by Ogawara Seisakusho).
  • a 10% hydroxypropyl cellulose solution (192 g) was sprayed thereon to granulate.
  • (R)-2-(2-aminothiazol-4-yl)-4′-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetic acid anilide or a salt thereof which is an active ingredient of the present invention showed a significantly strong relaxation action as compared with the control compound in “isolated rat bladder smooth muscle relaxation test”. Further, it decreased the contraction frequency of rhythmic bladder contraction on a dose-dependent manner in “rat rhythmic bladder contraction measurement test”. Still further, it prolonged the micturition interval of cyclophosphamide-induced overactive bladder model rat in “micturition function measurement test on cyclophosphamide-induced overactive bladder model rat”.
  • (R)-2-(2-Aminothiazol-4-yl)-4′-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetic acid anilide or a salt thereof which is an active ingredient of the present invention is able to be used as a remedy for overactive bladder.
  • overactive bladder as a result of benign prostatic hyperplasia, it is also able to be used as a remedy for overactive bladder accompanied with urinary urgency, urinary incontinence and pollakiuria.
  • FIG. 1 Effects of the compound A and the control compound to isolated rat bladder smooth muscle relaxation test (antagonism test to contraction by carbachol)
  • FIG. 2 Effects of the compound A and the control compound to isolated rat bladder smooth muscle relaxation test (antagonism test to contraction by potassium chloride)
  • FIG. 3 Effect of the compound A to rat rhythmic bladder contraction (effect to contraction frequency ( ⁇ : p ⁇ 0.05))
  • FIG. 4 Effect of the compound A to rat rhythmic bladder contraction (effect to contraction pressure)
  • FIG. 5 Effect of the compound A to micturition function of cyclophosphamide-induced overactive bladder model rat (showing the urination interval after administration of a drug where the urination interval before administration of the drug was defined as 100%)

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  • Organic Chemistry (AREA)
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  • Pharmacology & Pharmacy (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Urology & Nephrology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
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US13/542,308 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient Expired - Lifetime USRE44872E1 (en)

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Application Number Priority Date Filing Date Title
US13/542,308 USRE44872E1 (en) 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2002-323792 2002-11-07
JP2002323792 2002-11-07
PCT/JP2003/014065 WO2004041276A1 (ja) 2002-11-07 2003-11-04 酢酸アニリド誘導体を有効成分とする過活動膀胱治療剤
US13/542,308 USRE44872E1 (en) 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US10/534,290 US20060115540A1 (en) 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient

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USRE44872E1 true USRE44872E1 (en) 2014-04-29

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US13/542,308 Expired - Lifetime USRE44872E1 (en) 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US10/534,290 Ceased US7750029B2 (en) 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US10/534,290 Granted US20060115540A1 (en) 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US12/333,357 Abandoned US20090093529A1 (en) 2002-11-07 2008-12-12 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US13/117,638 Expired - Lifetime US8835474B2 (en) 2002-11-07 2011-05-27 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient

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US10/534,290 Ceased US7750029B2 (en) 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US10/534,290 Granted US20060115540A1 (en) 2002-11-07 2003-11-04 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US12/333,357 Abandoned US20090093529A1 (en) 2002-11-07 2008-12-12 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US13/117,638 Expired - Lifetime US8835474B2 (en) 2002-11-07 2011-05-27 Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient

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US (5) USRE44872E1 (ja)
EP (1) EP1559427B1 (ja)
JP (1) JP3815496B2 (ja)
KR (1) KR100967070B1 (ja)
CN (1) CN100406011C (ja)
AT (1) ATE500827T1 (ja)
AU (1) AU2003284700B2 (ja)
BE (1) BE2013C040I2 (ja)
BR (1) BR0316080A (ja)
CA (1) CA2503570C (ja)
CY (2) CY1111399T1 (ja)
DE (1) DE60336334D1 (ja)
DK (1) DK1559427T3 (ja)
ES (1) ES2360353T3 (ja)
FR (1) FR13C0032I2 (ja)
HU (1) HUS1300027I1 (ja)
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NL (1) NL300599I2 (ja)
NO (2) NO334948B1 (ja)
NZ (1) NZ539577A (ja)
PL (1) PL211687B1 (ja)
PT (1) PT1559427E (ja)
RU (1) RU2321401C2 (ja)
SI (1) SI1559427T1 (ja)
WO (1) WO2004041276A1 (ja)
ZA (1) ZA200503510B (ja)

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EP2709993A4 (en) 2011-05-18 2015-02-25 Reddys Lab Ltd Dr AMORPHIC MIRABEGRON AND METHOD FOR CRYSTALLINE FORMS OF MIRABEGRON
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EP2832730A4 (en) 2012-03-30 2015-09-09 Astellas Pharma Inc MIRABEGRAPHIC PHARMACEUTICAL COMPOSITION
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IL168121A (en) 2011-12-29
JP3815496B2 (ja) 2006-08-30
CY2013023I2 (el) 2015-10-07
US7750029B2 (en) 2010-07-06
US20090093529A1 (en) 2009-04-09
CY2013023I1 (el) 2015-10-07
DK1559427T3 (da) 2011-04-26
SI1559427T1 (sl) 2011-06-30
ATE500827T1 (de) 2011-03-15
US20110230530A1 (en) 2011-09-22
MXPA05004925A (es) 2005-08-18
US20060115540A1 (en) 2006-06-01
NZ539577A (en) 2007-06-29
CA2503570C (en) 2011-04-19
ES2360353T3 (es) 2011-06-03

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