NO328252B1 - Krystaller av hydroksynorefedrinderivat - Google Patents
Krystaller av hydroksynorefedrinderivat Download PDFInfo
- Publication number
- NO328252B1 NO328252B1 NO20041060A NO20041060A NO328252B1 NO 328252 B1 NO328252 B1 NO 328252B1 NO 20041060 A NO20041060 A NO 20041060A NO 20041060 A NO20041060 A NO 20041060A NO 328252 B1 NO328252 B1 NO 328252B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- ethyl
- pollakiuria
- crystals
- treatment
- Prior art date
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- 239000013078 crystal Substances 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 49
- 206010036018 Pollakiuria Diseases 0.000 claims description 13
- 206010046543 Urinary incontinence Diseases 0.000 claims description 12
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- -1 GW-515524 Chemical compound 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 230000008025 crystallization Effects 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
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- 239000012044 organic layer Substances 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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- 238000000034 method Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000004936 stimulating effect Effects 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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- SDZAMDXEQUMDBE-DQFHVVJASA-N ethyl 2-[4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]-2,5-dimethylphenoxy]acetate;hydrochloride Chemical compound Cl.C1=C(C)C(OCC(=O)OCC)=CC(C)=C1CCN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 SDZAMDXEQUMDBE-DQFHVVJASA-N 0.000 description 2
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
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- LDXQLWNPGRANTO-GOSISDBHSA-N (9r)-7-[[3,5-bis(trifluoromethyl)phenyl]methyl]-9-methyl-5-(4-methylphenyl)-8,9,10,11-tetrahydro-[1,4]diazocino[2,1-g][1,7]naphthyridine-6,13-dione Chemical compound C([C@H](CN(CC=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C1=O)C)CN(C(C2=NC=CC=C22)=O)C1=C2C1=CC=C(C)C=C1 LDXQLWNPGRANTO-GOSISDBHSA-N 0.000 description 1
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- 229950004964 fiduxosin Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- XOEVKNFZUQEERE-UHFFFAOYSA-N flavoxate hydrochloride Chemical compound Cl.C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCN1CCCCC1 XOEVKNFZUQEERE-UHFFFAOYSA-N 0.000 description 1
- 229960003064 flavoxate hydrochloride Drugs 0.000 description 1
- 229960000193 formoterol fumarate Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- SQKXYSGRELMAAU-UHFFFAOYSA-N imidafenacin Chemical compound CC1=NC=CN1CCC(C(N)=O)(C=1C=CC=CC=1)C1=CC=CC=C1 SQKXYSGRELMAAU-UHFFFAOYSA-N 0.000 description 1
- 229950005396 imidafenacin Drugs 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960002728 midodrine hydrochloride Drugs 0.000 description 1
- MGCQZNBCJBRZDT-UHFFFAOYSA-N midodrine hydrochloride Chemical compound [H+].[Cl-].COC1=CC=C(OC)C(C(O)CNC(=O)CN)=C1 MGCQZNBCJBRZDT-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
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- 239000003158 myorelaxant agent Substances 0.000 description 1
- HWMFFWCDLWDYGX-UHFFFAOYSA-N n-(4-aminophenyl)furan-2-carboxamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CO1 HWMFFWCDLWDYGX-UHFFFAOYSA-N 0.000 description 1
- HVMKWKIPLGPYAR-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-(2-nitrophenyl)cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2C(=CC=CC=2)[N+]([O-])=O)CC1 HVMKWKIPLGPYAR-UHFFFAOYSA-N 0.000 description 1
- ROUIPNDCVDWYEH-UHFFFAOYSA-N n-[3-(1h-imidazol-5-ylmethyl)phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(CC=2N=CNC=2)=C1 ROUIPNDCVDWYEH-UHFFFAOYSA-N 0.000 description 1
- 229950005705 naftopidil Drugs 0.000 description 1
- DLWSRGHNJVLJAH-UHFFFAOYSA-N nitroflurbiprofen Chemical compound FC1=CC(C(C(=O)OCCCCO[N+]([O-])=O)C)=CC=C1C1=CC=CC=C1 DLWSRGHNJVLJAH-UHFFFAOYSA-N 0.000 description 1
- 206010029446 nocturia Diseases 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
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- 229960005434 oxybutynin Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229960001187 propiverine hydrochloride Drugs 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- DSDNAKHZNJAGHN-UHFFFAOYSA-N resinferatoxin Natural products C1=C(O)C(OC)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-UHFFFAOYSA-N 0.000 description 1
- DSDNAKHZNJAGHN-MXTYGGKSSA-N resiniferatoxin Chemical compound C1=C(O)C(OC)=CC(CC(=O)OCC=2C[C@]3(O)C(=O)C(C)=C[C@H]3[C@@]34[C@H](C)C[C@@]5(O[C@@](O4)(CC=4C=CC=CC=4)O[C@@H]5[C@@H]3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-MXTYGGKSSA-N 0.000 description 1
- 229940073454 resiniferatoxin Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940121356 serotonin receptor antagonist Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960003855 solifenacin Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960002613 tamsulosin Drugs 0.000 description 1
- 229960001693 terazosin Drugs 0.000 description 1
- VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960004045 tolterodine Drugs 0.000 description 1
- OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 1
- 229950004288 tosilate Drugs 0.000 description 1
- 229960001530 trospium chloride Drugs 0.000 description 1
- 229960001130 urapidil Drugs 0.000 description 1
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
- 239000000105 vanilloid receptor agonist Substances 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001277345 | 2001-09-13 | ||
| PCT/JP2002/008596 WO2003024916A1 (fr) | 2001-09-13 | 2002-08-27 | Cristaux d'un derive d'hydroxynorephedrine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20041060L NO20041060L (no) | 2004-06-11 |
| NO328252B1 true NO328252B1 (no) | 2010-01-18 |
Family
ID=19101883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20041060A NO328252B1 (no) | 2001-09-13 | 2004-03-12 | Krystaller av hydroksynorefedrinderivat |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US7208520B2 (zh) |
| EP (1) | EP1426355B1 (zh) |
| JP (1) | JP4157036B2 (zh) |
| KR (2) | KR20080098691A (zh) |
| CN (1) | CN1275936C (zh) |
| AT (1) | ATE411276T1 (zh) |
| AU (1) | AU2002330453B2 (zh) |
| BR (1) | BR0212494A (zh) |
| CA (1) | CA2458544C (zh) |
| CO (1) | CO5560555A2 (zh) |
| CY (1) | CY1109409T1 (zh) |
| DE (1) | DE60229404D1 (zh) |
| DK (1) | DK1426355T3 (zh) |
| EA (1) | EA006022B1 (zh) |
| EC (1) | ECSP045017A (zh) |
| ES (1) | ES2314092T3 (zh) |
| HK (1) | HK1070051A1 (zh) |
| HR (1) | HRP20040250A2 (zh) |
| HU (1) | HUP0401694A3 (zh) |
| IL (2) | IL160681A0 (zh) |
| MX (1) | MXPA04002449A (zh) |
| NO (1) | NO328252B1 (zh) |
| NZ (1) | NZ531602A (zh) |
| PL (1) | PL206246B1 (zh) |
| PT (1) | PT1426355E (zh) |
| SI (1) | SI1426355T1 (zh) |
| UA (1) | UA77000C2 (zh) |
| WO (1) | WO2003024916A1 (zh) |
| ZA (1) | ZA200401757B (zh) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0210397D0 (en) | 2002-05-07 | 2002-06-12 | Ferring Bv | Pharmaceutical formulations |
| DE602004015272D1 (de) * | 2003-05-05 | 2008-09-04 | Kissei Pharmaceutical | Verwendung von phenoxyessigsäurederivaten zur behandlung der hyperaktiven blase |
| DE10351271A1 (de) * | 2003-10-31 | 2005-06-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmazeutische Zusammensetzung zur Behandlung der Stressinkontinenz und/oder Mischinkontinenz |
| RU2006119331A (ru) * | 2003-11-03 | 2007-12-27 | БЕРИНГЕР ИНГЕЛЬХАЙМ ИНТЕРНАЦИОНАЛЬ ГмбХ (DE) | ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СОДЕРЖАЩАЯ АГОНИСТ β3-АДРЕНОРЕЦЕПТОРА, α-АНТАГОНИСТ И/ИЛИ ИНГИБИТОР 5α-РЕДУКТАЗЫ |
| DE10352132A1 (de) * | 2003-11-04 | 2005-06-09 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmazeutische Zusammensetzung aus einem Beta-3-Adrenozeptor-Agonisten und einem Alpha Agonisten |
| WO2005092321A1 (ja) * | 2004-03-24 | 2005-10-06 | Kissei Pharmaceutical Co., Ltd. | 頻尿または尿失禁の予防または治療用医薬組成物 |
| JP4808613B2 (ja) * | 2004-03-24 | 2011-11-02 | キッセイ薬品工業株式会社 | 頻尿または尿失禁の予防または治療用医薬 |
| EP1612203B1 (en) * | 2004-06-28 | 2007-08-01 | Grünenthal GmbH | Crystalline forms of (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol hydrochloride |
| WO2006042679A1 (de) * | 2004-10-18 | 2006-04-27 | Boehringer Ingelheim International Gmbh | Verwendung eines beta-3-agonisten zur behandlung von beschwerden der prostata und des unteren urogenitaltrakts |
| DE102004050952A1 (de) * | 2004-10-18 | 2006-04-20 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmazeutische Zusammensetzung zur Behandlung von Beschwerden, die mit krankhaften Veränderungen oder Irritationen der Prostata verbunden sind |
| CA2585037A1 (en) | 2004-10-26 | 2006-05-04 | Kissei Pharmaceutical Co., Ltd. | Synthesis of phenoxyacetic acid derivatives |
| TWI356699B (en) * | 2004-11-10 | 2012-01-21 | Kissei Pharmaceutical | Agent for treating interstitial cystitis and agent |
| US8003694B2 (en) | 2005-04-26 | 2011-08-23 | Kissei Pharmaceutical Co., Ltd. | Crystal of hydroxynorephedrin derivative hydrochloride ¼ hydrate |
| CA2605337A1 (en) | 2005-04-26 | 2006-11-23 | Kissei Pharmaceutical Co., Ltd. | Crystal polymorph of hydroxynorephedrin derivative hydrochloride |
| 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 |
| EP2197532A1 (en) | 2007-08-06 | 2010-06-23 | Serenity Pharmaceuticals Corporation | Methods and devices for desmopressin drug delivery |
| US20100286045A1 (en) | 2008-05-21 | 2010-11-11 | Bjarke Mirner Klein | Methods comprising desmopressin |
| US11963995B2 (en) | 2008-05-21 | 2024-04-23 | Ferring B.V. | Methods comprising desmopressin |
| WO2009143356A1 (en) | 2008-05-21 | 2009-11-26 | Ferring International Center S.A. | Orodispersible desmopressin for increasing initial period of sleep undisturbed by nocturia |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY126489A (en) * | 1998-07-08 | 2006-10-31 | Kissei Pharmaceutical | Phenoxyacetic acid derivatives and medicinal compositions containing the same |
| JP4005731B2 (ja) * | 1999-01-21 | 2007-11-14 | キッセイ薬品工業株式会社 | アミノエチルフェノキシ酢酸誘導体の結晶多形 |
| JP4005730B2 (ja) * | 1999-01-21 | 2007-11-14 | キッセイ薬品工業株式会社 | アミノエチルフェノキシ酢酸誘導体二水和物の結晶多形 |
| JP4005729B2 (ja) * | 1999-01-21 | 2007-11-14 | キッセイ薬品工業株式会社 | アミノエチルフェノキシ酢酸誘導体二水和物の結晶多形 |
-
2002
- 2002-08-27 DE DE60229404T patent/DE60229404D1/de not_active Expired - Lifetime
- 2002-08-27 JP JP2003528764A patent/JP4157036B2/ja not_active Expired - Fee Related
- 2002-08-27 BR BR0212494-7A patent/BR0212494A/pt not_active IP Right Cessation
- 2002-08-27 AU AU2002330453A patent/AU2002330453B2/en not_active Ceased
- 2002-08-27 UA UA2004031852A patent/UA77000C2/uk unknown
- 2002-08-27 ES ES02765352T patent/ES2314092T3/es not_active Expired - Lifetime
- 2002-08-27 PL PL367874A patent/PL206246B1/pl not_active IP Right Cessation
- 2002-08-27 SI SI200230775T patent/SI1426355T1/sl unknown
- 2002-08-27 PT PT02765352T patent/PT1426355E/pt unknown
- 2002-08-27 WO PCT/JP2002/008596 patent/WO2003024916A1/ja active IP Right Grant
- 2002-08-27 MX MXPA04002449A patent/MXPA04002449A/es active IP Right Grant
- 2002-08-27 US US10/489,343 patent/US7208520B2/en not_active Expired - Fee Related
- 2002-08-27 KR KR1020087026126A patent/KR20080098691A/ko not_active Application Discontinuation
- 2002-08-27 AT AT02765352T patent/ATE411276T1/de active
- 2002-08-27 EP EP02765352A patent/EP1426355B1/en not_active Expired - Lifetime
- 2002-08-27 DK DK02765352T patent/DK1426355T3/da active
- 2002-08-27 CN CNB028175964A patent/CN1275936C/zh not_active Expired - Fee Related
- 2002-08-27 KR KR1020047003545A patent/KR100874952B1/ko not_active IP Right Cessation
- 2002-08-27 HU HU0401694A patent/HUP0401694A3/hu unknown
- 2002-08-27 EA EA200400311A patent/EA006022B1/ru not_active IP Right Cessation
- 2002-08-27 IL IL16068102A patent/IL160681A0/xx unknown
- 2002-08-27 CA CA2458544A patent/CA2458544C/en not_active Expired - Fee Related
-
2003
- 2003-08-27 NZ NZ531602A patent/NZ531602A/en not_active IP Right Cessation
-
2004
- 2004-03-02 IL IL160681A patent/IL160681A/en not_active IP Right Cessation
- 2004-03-03 ZA ZA200401757A patent/ZA200401757B/en unknown
- 2004-03-12 CO CO04022925A patent/CO5560555A2/es not_active Application Discontinuation
- 2004-03-12 HR HR20040250A patent/HRP20040250A2/hr not_active Application Discontinuation
- 2004-03-12 NO NO20041060A patent/NO328252B1/no not_active IP Right Cessation
- 2004-03-12 EC EC2004005017A patent/ECSP045017A/es unknown
-
2005
- 2005-04-04 HK HK05102803A patent/HK1070051A1/xx not_active IP Right Cessation
-
2009
- 2009-01-14 CY CY20091100027T patent/CY1109409T1/el unknown
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Legal Events
| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |