WO1999005090A1 - Derives d'acide aminoethylphenoxyacetique et medicaments qui reduisent la douleur et favorisent la suppression des calculs dans la lithiase urinaire - Google Patents
Derives d'acide aminoethylphenoxyacetique et medicaments qui reduisent la douleur et favorisent la suppression des calculs dans la lithiase urinaire Download PDFInfo
- Publication number
- WO1999005090A1 WO1999005090A1 PCT/JP1998/003163 JP9803163W WO9905090A1 WO 1999005090 A1 WO1999005090 A1 WO 1999005090A1 JP 9803163 W JP9803163 W JP 9803163W WO 9905090 A1 WO9905090 A1 WO 9905090A1
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- WO
- WIPO (PCT)
- Prior art keywords
- carbon atom
- acceptable salt
- acid derivative
- ethyl
- acid
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- 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
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
Definitions
- the present invention relates to an aminoethylphenoxyacetic acid derivative useful as a medicament and a pharmacologically acceptable salt thereof.
- Urolithiasis is a condition in which some urine components precipitate and crystallize in the lumen of the urinary tract from the kidney to the urethra, and these aggregate, deposit, and increase, causing stones in the urinary tract. Urinary tract obstruction due to this stone often blocks the urine flow, resulting in increased ureteral pressure and pain.
- pain is prescribed by analgesics and antispasmodics for this pain, and analgesics are only temporary symptomatic treatments for pain, and no fundamental cure can be expected.
- drugs useful for the treatment of urolithiasis such as strong ureteric relaxation, dilate the ureter and reduce pain.
- There is a demand for the development of a drug that relieves and promotes the discharge of stones (The Journal of Europe, Vol. 152, pp. 1095-1098 (1994)).
- the present invention has the general formula
- R 1 is a hydrogen atom, a lower alkyl group or an aralkyl group
- R 2 is a hydrogen atom or a halogen atom
- the carbon atom with (R) is a carbon atom in the (R) configuration
- (S) represents a carbon atom in the (S) configuration, and relates to aminoethylphenoxyacetic acid derivatives represented by the formula: and their pharmacologically acceptable salts.
- the present invention relates to a pharmaceutical composition containing the aminoethyl phenoxyacetic acid derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof.
- the present invention provides a method for relieving pain in urolithiasis, which comprises, as an active ingredient, an aminoethylphenoxyacetic acid derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof.
- the present invention relates to an excretion accelerator.
- the present invention provides a method for treating urolithiasis comprising administering an effective amount of an aminoethyl phenoxyacetic acid derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof.
- the present invention relates to a method for promoting remission and stone removal.
- the present invention provides an aminoethylphenoxyacetic acid derivative represented by the above general formula (I) or a pharmacologically acceptable derivative thereof for the manufacture of a pharmaceutical composition for treating urolithiasis. It concerns the use of salt.
- the present invention relates to the use of an aminoethylphenoxyacetic acid derivative represented by the above general formula (I) or a pharmacologically acceptable salt thereof as an agent for alleviating pain and excretion of urolithiasis. Things.
- the present invention relates to a method for treating urolithiasis, characterized by the use of an aminoethylfurunoxyacetic acid derivative represented by the above general formula (I) or a pharmacologically acceptable salt thereof as an essential component of a pharmaceutical composition.
- the present invention relates to a method for producing a pharmaceutical composition.
- lower alkyl group refers to the number of carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.
- the compound represented by the general formula (I) of the present invention can be produced as follows.
- a compound of the present invention has the formula
- R la is a lower alkyl group or an aralkyl group
- X 1 is a chlorine atom or a bromine atom
- R 2 has the same meaning as described above. It can be produced by alkylating and, if desired, hydrolyzing an ester group according to a conventional method.
- the phenylpropanolamine derivative represented by the formula (II) used as a starting material in the above production method can be produced by optically resolving a commercially available enantiomeric mixture according to an ordinary method, or by a method described in a literature. (J. Med. Chem., Volume 20, Issue 7, pages 978 to 981 (1977)). Further, the alkylating agent represented by the general formula (III) used as a starting material in the production method is represented by the general formula:
- R 2 and X 1 in the formula have the same meanings as described above, which can be produced by reacting with a halogenated acetate in the presence of a base such as carbon dioxide. it can.
- the aminoethylphenoxyacetic acid derivative represented by the above general formula (I) of the present invention obtained by the above production method can be obtained by a fractional recrystallization method which is a conventional separation means, a column chromatography. It can be easily isolated and purified by a purification method using chromatography, a solvent extraction method, or the like.
- the aminoethyl phenoxyacetic acid derivative represented by the general formula (I) of the present invention can be converted into a pharmacologically acceptable salt thereof by a conventional method.
- salts include acid addition salts with mineral acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, formic acid, acetic acid, propionic acid, citric acid, tartaric acid, and fumaric acid.
- Acids with organic acids such as acid, butyric acid, oxalic acid, succinic acid, malonic acid, maleic acid, lactic acid, malic acid, carbonic acid, glutamic acid, aspartic acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid
- Inorganic base salts such as addition salts, sodium salts, potassium salts, calcium salts, and ammonium salts; and salts with organic bases such as triethylamine, piperidine, morpholine, pyridine, lysine, and the like.
- the compound represented by the general formula (I) of the present invention also includes a solvate with a pharmaceutically acceptable solvent such as water or ethanol.
- the ⁇ 2 -adrenoceptor stimulating action of the compound of the general formula (I) of the present invention can be measured using the uterus of a pregnant rat.
- the / 3 3 of the compounds of general formula (I) of the present invention - adrenoceptor stimulating effects can be measured using a ureter Fere' bets, for example, 2- [4 one [2- [[
- the compound represented by the general formula (I) of the present invention is a compound having both potent 2- adrenergic receptor stimulating action and ⁇ 3 -adrenergic receptor stimulating action, It is useful as an agent for relieving pain, promoting natural stone removal, and stone removal after lithotripsy.
- Adrenergic receptor stimulatory effects are attenuated 2 and / 3 3 —Adrenergic receptor stimulants.
- Examples of such compounds include those of the general formula
- more preferred compounds include 2- [4- [2-[[(1S, 2R) -12-hydroxy-2- (4-hydroxyphenyl) -11-methylethyl] amino] ethyl] [Phenoxy] acetic acid, 2- [3-fluoro-41- [2-[[((1S, 2R) -2-hydroxy-l- (4-hydroxyphenyl) -l-methylethyl] amino] ethyl] phenoxy] acetic acid And pharmacologically acceptable salts thereof.
- the compound represented by the general formula (I) of the present invention is a compound having extremely high safety.
- 2- (4_ [2 — [[( 1S, 2R) —2-Hydroxy-2- (4-hydroxyphenyl) -1-methylethyl] amino] ethyl] phenoxy] Acetic acid did not cause any death even at a dose of 100 Omg / kg.
- the compounds of the formula and acceptable salts thereof pharmacological so represented by (I) of the present invention, powerful and very useful ⁇ 2 and; 5 3 - adrenergic receptor stimulated action It has.
- a suitable pharmaceutical composition for example, It is orally or parenterally administered as tablets, powders, fine granules, granules, capsules, injections and the like.
- These pharmaceutical compositions can be prepared by the pharmaceutical methods used in general preparations, by using carriers, excipients and other additives commonly used for pharmaceuticals.
- the dose is determined as appropriate depending on the gender, age, weight, degree of symptoms, etc. of the target patient.For oral administration, generally 1 to 100 mg / day for adults and generally for parenteral administration For adults, the dosage is 0.01 to 10 mg / day, in single or divided doses.
- [Eta - Hokusatsu R (CDC1 3) 5ppm: 0.95 (3H, d, J 6.3Hz), 2.75-3.05 (5H, m), 4.5
- the uterus of an SD pregnant rat (day 2 of pregnancy) was excised, avoiding the placenta attachment, preparing a specimen of about 5 mm in width and about 15 in length in the longitudinal muscle direction, and using the Magnus method.
- the experiment was performed according to the test. Specimens were suspended at 37 ° C in Locke-Ringer solution that had been aerated with a mixture of 95% oxygen and 5% carbon dioxide and loaded with 1 g. Uterine motility was derived isometrically via a tension transducer and recorded by rectograph. Drugs were added cumulatively into Magnus tubes every 5 minutes.
- the drug efficacy was evaluated by taking the sum of the uterine contraction height for 5 minutes before drug addition as 100% and comparing it with the sum of uterine contraction height for 5 minutes after drug addition at each concentration. EC 5 . It was evaluated as a value. The results are as shown in the table below. Test example 2
- the drug efficacy was evaluated by comparing the sum of ureteral contraction height for 3 minutes before addition of the drug with 100% and the sum of ureteral contraction height for 3 minutes after addition of the drug at each concentration to 50%. EC 5 concentration. The value was evaluated. The results are as shown in the table below. Test example 3
- the atrium of a male SD rat (body weight 350-400 g) was excised, and an experiment was performed according to the Magnus method. Specimens were suspended in Krebs-Heseleit solution aerated with a mixture of 95% oxygen and 5% carbon dioxide at 37 ° C and loaded with 1 g. The systolic force was derived isometrically via a tension transducer and self-registered by lectrograph. Drug was added to assess the drug concentration in increasing per minute 2 0 times the heart rate as EC delta 2 0 value. The results are as shown in the table below.
- Formula aminoethyl Tilia Roh carboxy acid derivatives and acceptable salts thereof pharmacologically represented by the general formula (I), beta 2 and 3 3 of the present invention - adrenoceptor compound having both a stimulation effect And has a powerful relaxing effect on ureteral smooth muscle, and is a very useful compound as a pharmaceutical for amelioration of pain in urolithiasis and lithotripsy.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Claims
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020007000694A KR100545473B1 (ko) | 1997-07-25 | 1998-07-15 | 아미노에틸페녹시 아세트산 유도체 및 요로 결석증의 동통완해 및 배석촉진제 |
DE69827137T DE69827137T2 (de) | 1997-07-25 | 1998-07-15 | Aminoethylphenoxyessigsäure-derivate und medikamente zur schmerzlinderung und förderung der entfernung von konkrementen bei urolithiasis |
IL13386398A IL133863A0 (en) | 1997-07-25 | 1998-07-15 | Aminoethylphenoxyacetic acid derivatives and drugs for pain remission and calculi removal promotion in urinary lithiasis |
AU82419/98A AU754579B2 (en) | 1997-07-25 | 1998-07-15 | Aminoethylphenoxyacetic acid derivatives and drugs for pain remission and calculi removal promotion in urinary lithiasis |
EP98932517A EP1002791B1 (en) | 1997-07-25 | 1998-07-15 | Aminoethylphenoxyacetic acid derivatives and drugs for pain remission and calculi removal promotion in urinary lithiasis |
AT98932517T ATE280146T1 (de) | 1997-07-25 | 1998-07-15 | Aminoethylphenoxyessigsäure-derivate und medikamente zur schmerzlinderung und förderung der entfernung von konkrementen bei urolithiasis |
JP2000504092A JP4002391B2 (ja) | 1997-07-25 | 1998-07-15 | アミノエチルフェノキシ酢酸誘導体および尿路結石症の疼痛緩解および排石促進剤 |
CA002298493A CA2298493C (en) | 1997-07-25 | 1998-07-15 | Aminoethylphenoxyacetic acid derivatives and drugs for pain remission and calculi removal promotion in urinary lithiasis |
DK98932517T DK1002791T3 (da) | 1998-07-15 | 1998-07-15 | Aminoethylphenoxyeddikesyrederivater og medikamenter til smertelindring og fremme fjernelse af sten i urinvejssten |
NZ502366A NZ502366A (en) | 1997-07-25 | 1998-07-15 | Aminoethylphenoxyacetic acid derivatives and drugs for pain remission and calculi removal promotion in urinary lithiasis |
BRPI9811483-2A BR9811483B1 (pt) | 1997-07-25 | 1998-07-15 | derivados do Ácido amino-etil-fenàxi-acÉtico e fÁrmacos para a remissço da dor e promover a remoÇço de cÁlculos na litÍase urinÁria. |
PL338234A PL191864B1 (pl) | 1997-07-25 | 1998-07-15 | Pochodna kwasu aminoetylofenoksyoctowego, kompozycja farmaceutyczna zawierająca tą pochodną oraz jej zastosowanie |
HU0004055A HUP0004055A3 (en) | 1997-07-25 | 1998-07-15 | Aminoethylphenoxyacetic acid derivatives for pain remission and calculi removal promotion in urinary lithiasis |
US09/463,432 US6399660B1 (en) | 1997-07-25 | 1999-05-21 | Aminoethylphenoxyacetic acid derivatives and drugs for pain remission and calculi removal promotion in urinary lithiasis |
NO20000371A NO315422B1 (no) | 1997-07-25 | 2000-01-25 | Aminoetylfenoksyeddiksyrederivater og legemidler for smertereduksjon og kalksteinfjerningsfremming i urin lithiasis |
HK00107213A HK1028016A1 (en) | 1997-07-25 | 2000-11-13 | Aminoethylphenoxyacetic acid derivatives and drugs for pain remission and calculi removal promotion in urinary lithiasis |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23323997 | 1997-07-25 | ||
JP9/233239 | 1997-07-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999005090A1 true WO1999005090A1 (fr) | 1999-02-04 |
Family
ID=16951956
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1998/003163 WO1999005090A1 (fr) | 1997-07-25 | 1998-07-15 | Derives d'acide aminoethylphenoxyacetique et medicaments qui reduisent la douleur et favorisent la suppression des calculs dans la lithiase urinaire |
Country Status (29)
Country | Link |
---|---|
US (1) | US6399660B1 (ja) |
EP (1) | EP1002791B1 (ja) |
JP (1) | JP4002391B2 (ja) |
KR (1) | KR100545473B1 (ja) |
CN (1) | CN1137877C (ja) |
AR (1) | AR013241A1 (ja) |
AT (1) | ATE280146T1 (ja) |
AU (1) | AU754579B2 (ja) |
BR (1) | BR9811483B1 (ja) |
CA (1) | CA2298493C (ja) |
CO (1) | CO4970779A1 (ja) |
CZ (1) | CZ300389B6 (ja) |
DE (1) | DE69827137T2 (ja) |
ES (1) | ES2231996T3 (ja) |
HK (1) | HK1028016A1 (ja) |
HU (1) | HUP0004055A3 (ja) |
ID (1) | ID24062A (ja) |
IL (1) | IL133863A0 (ja) |
MY (1) | MY126743A (ja) |
NO (1) | NO315422B1 (ja) |
NZ (1) | NZ502366A (ja) |
PE (1) | PE99899A1 (ja) |
PL (1) | PL191864B1 (ja) |
PT (1) | PT1002791E (ja) |
RU (1) | RU2196130C2 (ja) |
SA (1) | SA98190661B1 (ja) |
TW (1) | TW418184B (ja) |
WO (1) | WO1999005090A1 (ja) |
ZA (1) | ZA986580B (ja) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999052856A1 (fr) * | 1998-04-14 | 1999-10-21 | Kissei Pharmaceutical Co., Ltd. | Derives de l'acide 2-methylpropionique et compositions medicinale correspondantes |
WO2000002846A1 (en) * | 1998-07-08 | 2000-01-20 | Kissei Pharmaceutical Co., Ltd. | Phenoxyacetic acid derivatives and medicinal compositions containing the same |
WO2000043350A1 (fr) * | 1999-01-21 | 2000-07-27 | Kissei Pharmaceutical Co., Ltd. | Polymorphisme cristallin de derive d'acide aminoethylphenoxyacetique |
WO2005077355A1 (ja) * | 2004-02-12 | 2005-08-25 | Kissei Pharmaceutical Co., Ltd. | 食道の運動障害を伴う疾患の予防または治療用医薬組成物 |
WO2007004639A1 (ja) * | 2005-07-06 | 2007-01-11 | Daiichi Fine Chemical Co., Ltd. | 光学活性エリスロ-β-アミノアルコールの製法 |
WO2007026630A1 (ja) | 2005-08-29 | 2007-03-08 | Kissei Pharmaceutical Co., Ltd. | 涙液の減少に伴う疾患の予防又は治療剤 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2479254A1 (en) * | 2002-03-22 | 2003-10-02 | Kissei Pharmaceutical Co., Ltd. | Preventive or therapeutic agent for renal disease |
EP1424079A1 (en) * | 2002-11-27 | 2004-06-02 | Boehringer Ingelheim International GmbH | Combination of a beta-3-receptor agonist and of a reuptake inhibitor of serotonin and/or norepinephrine |
DE10333569A1 (de) * | 2003-07-23 | 2005-02-17 | Z & J Technologies Gmbh | Einrichtung zur Verteilung von Schüttgut in wenigstens zwei oberhalb der Gicht eines Hochofens angeordnete Bunker |
EP1769792A1 (de) * | 2005-09-30 | 2007-04-04 | Boehringer Ingelheim Pharma GmbH & Co.KG | Verwendung eines beta-3-Adrenozeptor-Agonisten zur Behandlung von Nieren- und Blasenbeschwerden |
ES2302447B1 (es) * | 2006-10-20 | 2009-06-12 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998013333A1 (fr) * | 1996-09-26 | 1998-04-02 | Kissei Pharmaceutical Co., Ltd. | Derives de 2-amino-1-(4-hydroxy-2-methylphenyl)propanol |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3061334D1 (en) * | 1979-06-16 | 1983-01-20 | Beecham Group Plc | Ethanamine derivatives, their preparation and use in pharmaceutical compositions |
US5776983A (en) * | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
ES2195021T3 (es) * | 1995-11-30 | 2003-12-01 | Kissei Pharmaceutical | Medicamento para aliviar el dolor y favorecer la eliminacion de calculos en la urolitiasis. |
-
1997
- 1997-07-25 ID IDW20000131A patent/ID24062A/id unknown
-
1998
- 1998-07-15 CZ CZ20000272A patent/CZ300389B6/cs not_active IP Right Cessation
- 1998-07-15 CA CA002298493A patent/CA2298493C/en not_active Expired - Fee Related
- 1998-07-15 DE DE69827137T patent/DE69827137T2/de not_active Expired - Lifetime
- 1998-07-15 JP JP2000504092A patent/JP4002391B2/ja not_active Expired - Fee Related
- 1998-07-15 NZ NZ502366A patent/NZ502366A/xx not_active IP Right Cessation
- 1998-07-15 PT PT98932517T patent/PT1002791E/pt unknown
- 1998-07-15 WO PCT/JP1998/003163 patent/WO1999005090A1/ja active IP Right Grant
- 1998-07-15 IL IL13386398A patent/IL133863A0/xx not_active IP Right Cessation
- 1998-07-15 CN CNB988075482A patent/CN1137877C/zh not_active Expired - Fee Related
- 1998-07-15 HU HU0004055A patent/HUP0004055A3/hu unknown
- 1998-07-15 BR BRPI9811483-2A patent/BR9811483B1/pt not_active IP Right Cessation
- 1998-07-15 PL PL338234A patent/PL191864B1/pl not_active IP Right Cessation
- 1998-07-15 KR KR1020007000694A patent/KR100545473B1/ko not_active IP Right Cessation
- 1998-07-15 EP EP98932517A patent/EP1002791B1/en not_active Expired - Lifetime
- 1998-07-15 AU AU82419/98A patent/AU754579B2/en not_active Ceased
- 1998-07-15 AT AT98932517T patent/ATE280146T1/de active
- 1998-07-15 ES ES98932517T patent/ES2231996T3/es not_active Expired - Lifetime
- 1998-07-15 RU RU2000101840/04A patent/RU2196130C2/ru not_active IP Right Cessation
- 1998-07-16 MY MYPI98003263A patent/MY126743A/en unknown
- 1998-07-20 TW TW087111774A patent/TW418184B/zh not_active IP Right Cessation
- 1998-07-22 AR ARP980103575A patent/AR013241A1/es active IP Right Grant
- 1998-07-22 PE PE1998000659A patent/PE99899A1/es not_active Application Discontinuation
- 1998-07-23 CO CO98041910A patent/CO4970779A1/es unknown
- 1998-07-23 ZA ZA986580A patent/ZA986580B/xx unknown
- 1998-10-19 SA SA98190661A patent/SA98190661B1/ar unknown
-
1999
- 1999-05-21 US US09/463,432 patent/US6399660B1/en not_active Expired - Lifetime
-
2000
- 2000-01-25 NO NO20000371A patent/NO315422B1/no not_active IP Right Cessation
- 2000-11-13 HK HK00107213A patent/HK1028016A1/xx not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998013333A1 (fr) * | 1996-09-26 | 1998-04-02 | Kissei Pharmaceutical Co., Ltd. | Derives de 2-amino-1-(4-hydroxy-2-methylphenyl)propanol |
Non-Patent Citations (2)
Title |
---|
HALMEKOSKI J, MAUKONEN L: "SELECTIVE ACETYLATIONS OF TERBUTALINE AND RITODRINE", FARMASEUTTINEN AIKAKAUSLEHTI, SUOMEN FARMASEUTTINEN YHDISTYS, FI, vol. 82, no. 07/08, 1 January 1973 (1973-01-01), FI, pages 111 - 115, XP002917855, ISSN: 0367-259X * |
MARTIN C A E, ET AL.: "EFFECTS OF TWO BETA3-ADRENOCEPTOR AGONINSTS, SR 58611A AND BRL 37344, AND SALBUTAMOL ON CHOLINERGIC AND NANC NEURAL CONTRACTION IN GUINEA-PIG MAIN BRONCHI IN VITRO", BRITISH JOURNAL OF PHARMACOLOGY, NATURE PUBLISHING GROUP, BASINGSTOKE, HANTS; GB, vol. 110, no. 04, 1 January 1993 (1993-01-01), BASINGSTOKE, HANTS; GB, pages 1311 - 1316, XP002917856, ISSN: 0007-1188 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6790865B2 (en) | 1998-04-14 | 2004-09-14 | Kissei Pharmaceutical Co., Ltd. | 2-methylpropionic acid derivatives and pharmaceutical compositions comprising the same |
WO1999052856A1 (fr) * | 1998-04-14 | 1999-10-21 | Kissei Pharmaceutical Co., Ltd. | Derives de l'acide 2-methylpropionique et compositions medicinale correspondantes |
US6696489B1 (en) | 1998-04-14 | 2004-02-24 | Kissei Pharmaceutical Co., Ltd. | 2-Methylpropionic acid derivatives and medicinal compositions containing the same |
AU771200B2 (en) * | 1998-07-08 | 2004-03-18 | Kissei Pharmaceutical Co. Ltd. | Phenoxyacetic acid derivatives and medicinal compositions containing the same |
WO2000002846A1 (en) * | 1998-07-08 | 2000-01-20 | Kissei Pharmaceutical Co., Ltd. | Phenoxyacetic acid derivatives and medicinal compositions containing the same |
US6538152B1 (en) | 1998-07-08 | 2003-03-25 | Kissei Pharmaceutical Co., Ltd. | Phenoxyacetic acid derivatives and medicinal compositions containing the same |
US6376707B1 (en) * | 1999-01-21 | 2002-04-23 | Kissei Pharmaceutical Co., Ltd. | Crystal polymorphism of aminoethylphenoxyacetic acid derivative |
WO2000043350A1 (fr) * | 1999-01-21 | 2000-07-27 | Kissei Pharmaceutical Co., Ltd. | Polymorphisme cristallin de derive d'acide aminoethylphenoxyacetique |
WO2005077355A1 (ja) * | 2004-02-12 | 2005-08-25 | Kissei Pharmaceutical Co., Ltd. | 食道の運動障害を伴う疾患の予防または治療用医薬組成物 |
JP4843313B2 (ja) * | 2004-02-12 | 2011-12-21 | キッセイ薬品工業株式会社 | 食道の運動障害を伴う疾患の予防または治療用医薬組成物 |
WO2007004639A1 (ja) * | 2005-07-06 | 2007-01-11 | Daiichi Fine Chemical Co., Ltd. | 光学活性エリスロ-β-アミノアルコールの製法 |
JP5156377B2 (ja) * | 2005-07-06 | 2013-03-06 | 第一ファインケミカル株式会社 | 光学活性エリスロ−β−アミノアルコールの製法 |
WO2007026630A1 (ja) | 2005-08-29 | 2007-03-08 | Kissei Pharmaceutical Co., Ltd. | 涙液の減少に伴う疾患の予防又は治療剤 |
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