NO328252B1 - Krystaller av hydroksynorefedrinderivat - Google Patents

Krystaller av hydroksynorefedrinderivat Download PDF

Info

Publication number: NO328252B1
Authority: NO; Norway
Prior art keywords: compound; ethyl; pollakiuria; crystals; treatment
Prior art date: 2001-09-13

Application number

NO20041060A

Other languages

English (en)

Norwegian (no)

Other versions

NO20041060L (no

Inventor

Junichi Sonehara

Satoshi Akahane

Yukihiko Hotei

Hidetoshi Lsawa

Kiyoshi Kasai

Original Assignee

Kissei Pharmaceutical Company

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-09-13

Filing date

2004-03-12

Publication date

2010-01-18

2004-03-12 Application filed by Kissei Pharmaceutical Company filed Critical Kissei Pharmaceutical Company

2004-06-11 Publication of NO20041060L publication Critical patent/NO20041060L/no

2010-01-18 Publication of NO328252B1 publication Critical patent/NO328252B1/no

Links

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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
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
238000002425 crystallisation Methods 0.000 description 6
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
238000001816 cooling Methods 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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
239000003085 diluting agent Substances 0.000 description 3
239000002552 dosage form Substances 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000000556 agonist Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
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239000000872 buffer Substances 0.000 description 2
YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
239000002270 dispersing agent Substances 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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239000012907 medicinal substance Substances 0.000 description 2
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239000003755 preservative agent Substances 0.000 description 2
201000007094 prostatitis Diseases 0.000 description 2
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229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000013112 stability test Methods 0.000 description 2
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PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 description 1
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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
OBRNDARFFFHCGE-PERKLWIXSA-N (S,S)-formoterol fumarate Chemical compound OC(=O)\C=C\C(O)=O.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1 OBRNDARFFFHCGE-PERKLWIXSA-N 0.000 description 1
SFOVDSLXFUGAIV-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-n-piperidin-4-ylbenzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1NC1CCNCC1 SFOVDSLXFUGAIV-UHFFFAOYSA-N 0.000 description 1
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
INGXCNVWWKKWOO-LJQANCHMSA-N 2-[(5r)-1-(2-chloro-4-pyrrolidin-1-ylbenzoyl)-2,3,4,5-tetrahydro-1-benzazepin-5-yl]-n-propan-2-ylacetamide Chemical compound C([C@@H](C1=CC=CC=C11)CC(=O)NC(C)C)CCN1C(=O)C(C(=C1)Cl)=CC=C1N1CCCC1 INGXCNVWWKKWOO-LJQANCHMSA-N 0.000 description 1
XRLNLENEMPYBGI-NVJCMEIXSA-N 2-[4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]-2,5-dimethylphenoxy]acetic acid;hydrochloride Chemical group Cl.N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC(C)=C(OCC(O)=O)C=C1C XRLNLENEMPYBGI-NVJCMEIXSA-N 0.000 description 1
GSAHJOWJMPIJOB-UHFFFAOYSA-N 3-[(2,4-dichloro-6-methylphenyl)methylamino]-4-(2-methylbutan-2-ylamino)cyclobut-3-ene-1,2-dione Chemical compound O=C1C(=O)C(NC(C)(C)CC)=C1NCC1=C(C)C=C(Cl)C=C1Cl GSAHJOWJMPIJOB-UHFFFAOYSA-N 0.000 description 1
WDTAYDBPNYFWDR-WOJBJXKFSA-N 3-[4-[(3ar,9br)-9-methoxy-3,3a,4,9b-tetrahydro-1h-chromeno[3,4-c]pyrrol-2-yl]butyl]-8-phenyl-1h-pyrazino[1,2]thieno[3,4-b]pyrimidine-2,4-dione Chemical compound C([C@@H]1COC=2C=CC=C(C=2[C@@H]1C1)OC)N1CCCCN(C(C=1SC2=NC=3)=O)C(=O)NC=1C2=NC=3C1=CC=CC=C1 WDTAYDBPNYFWDR-WOJBJXKFSA-N 0.000 description 1
239000003477 4 aminobutyric acid receptor stimulating agent Substances 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 description 1
102100034159 Beta-3 adrenergic receptor Human genes 0.000 description 1
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IKYCZSUNGFRBJS-UHFFFAOYSA-N Euphorbia factor RL9 = U(1) = Resiniferatoxin Natural products COC1=CC(O)=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 IKYCZSUNGFRBJS-UHFFFAOYSA-N 0.000 description 1
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WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
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RVCSYOQWLPPAOA-CVPHZBIISA-M [(5s)-spiro[8-azoniabicyclo[3.2.1]octane-8,1'-azolidin-1-ium]-3-yl] 2-hydroxy-2,2-diphenylacetate;chloride Chemical compound [Cl-].[N+]12([C@H]3CCC2CC(C3)OC(=O)C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CCCC1 RVCSYOQWLPPAOA-CVPHZBIISA-M 0.000 description 1
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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
229940035363 muscle relaxants Drugs 0.000 description 1
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
239000006186 oral dosage form Substances 0.000 description 1
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)
Emergency Medicine (AREA)
Epidemiology (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)

NO20041060A 2001-09-13 2004-03-12 Krystaller av hydroksynorefedrinderivat NO328252B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2001277345		2001-09-13
PCT/JP2002/008596 WO2003024916A1 (en)	2001-09-13	2002-08-27	Crystals of hydroxynorephedrine derivative

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 (28)

Country	Link
US (1)	US7208520B2 (da)
EP (1)	EP1426355B1 (da)
JP (1)	JP4157036B2 (da)
KR (2)	KR20080098691A (da)
CN (1)	CN1275936C (da)
AT (1)	ATE411276T1 (da)
AU (1)	AU2002330453B2 (da)
BR (1)	BR0212494A (da)
CA (1)	CA2458544C (da)
CO (1)	CO5560555A2 (da)
CY (1)	CY1109409T1 (da)
DE (1)	DE60229404D1 (da)
DK (1)	DK1426355T3 (da)
EA (1)	EA006022B1 (da)
EC (1)	ECSP045017A (da)
ES (1)	ES2314092T3 (da)
HR (1)	HRP20040250A2 (da)
HU (1)	HUP0401694A3 (da)
IL (2)	IL160681A0 (da)
MX (1)	MXPA04002449A (da)
NO (1)	NO328252B1 (da)
NZ (1)	NZ531602A (da)
PL (1)	PL206246B1 (da)
PT (1)	PT1426355E (da)
SI (1)	SI1426355T1 (da)
UA (1)	UA77000C2 (da)
WO (1)	WO2003024916A1 (da)
ZA (1)	ZA200401757B (da)

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Publication number	Priority date	Publication date	Assignee	Title
GB0210397D0 (en)	2002-05-07	2002-06-12	Ferring Bv	Pharmaceutical formulations
CA2524023C (en) *	2003-05-05	2011-11-22	Kissei Pharmaceutical Co., Ltd.	Use of phenoxyacetic acid derivatives for treating hyperactive bladder
DE10351271A1 (de) *	2003-10-31	2005-06-02	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Pharmazeutische Zusammensetzung zur Behandlung der Stressinkontinenz und/oder Mischinkontinenz
WO2005042021A2 (de) *	2003-11-03	2005-05-12	Boehringer Ingelheim International Gmbh	Pharmazeutische zusammensetzung enthaltend einen beta-3-adrenozeptor-agonisten und einen alpha antagonisten und/oder einen 5-alpha reduktase-hemmer
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
ES2291780T3 (es) *	2004-06-28	2008-03-01	Grunenthal Gmbh	Formas cristalinas del clorhidrato de (-)-(1r,2r)-3-(3-dimetilamino-1-etil-2-metilpropil)fenol.
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
JP2008516909A (ja) *	2004-10-18	2008-05-22	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	前立腺及び下部泌尿生殖路の病気を治療するためのβ−３アゴニストの使用
EP1809591A1 (en)	2004-10-26	2007-07-25	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
JPWO2006123517A1 (ja) *	2005-04-26	2008-12-25	キッセイ薬品工業株式会社	ヒドロキシノルエフェドリン誘導体塩酸塩の結晶多形
US8003694B2 (en)	2005-04-26	2011-08-23	Kissei Pharmaceutical Co., Ltd.	Crystal of hydroxynorephedrin derivative hydrochloride ¼ hydrate
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
WO2009021007A1 (en)	2007-08-06	2009-02-12	Serenity Pharmaceuticals Corporation	Methods and devices for desmopressin drug delivery
NO3085381T3 (da)	2008-05-21	2018-09-15
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

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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
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
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
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

2002
- 2002-08-27 KR KR1020087026126A patent/KR20080098691A/ko not_active Ceased
- 2002-08-27 BR BR0212494-7A patent/BR0212494A/pt not_active IP Right Cessation
- 2002-08-27 PT PT02765352T patent/PT1426355E/pt unknown
- 2002-08-27 KR KR1020047003545A patent/KR100874952B1/ko not_active Expired - Fee Related
- 2002-08-27 MX MXPA04002449A patent/MXPA04002449A/es active IP Right Grant
- 2002-08-27 EP EP02765352A patent/EP1426355B1/en not_active Expired - Lifetime
- 2002-08-27 UA UA2004031852A patent/UA77000C2/uk unknown
- 2002-08-27 WO PCT/JP2002/008596 patent/WO2003024916A1/ja not_active Ceased
- 2002-08-27 HR HR20040250A patent/HRP20040250A2/hr not_active Application Discontinuation
- 2002-08-27 SI SI200230775T patent/SI1426355T1/sl unknown
- 2002-08-27 AT AT02765352T patent/ATE411276T1/de active
- 2002-08-27 CA CA2458544A patent/CA2458544C/en not_active Expired - Fee Related
- 2002-08-27 IL IL16068102A patent/IL160681A0/xx unknown
- 2002-08-27 US US10/489,343 patent/US7208520B2/en not_active Expired - Fee Related
- 2002-08-27 CN CNB028175964A patent/CN1275936C/zh not_active Expired - Fee Related
- 2002-08-27 HU HU0401694A patent/HUP0401694A3/hu unknown
- 2002-08-27 AU AU2002330453A patent/AU2002330453B2/en not_active Ceased
- 2002-08-27 DK DK02765352T patent/DK1426355T3/da active
- 2002-08-27 PL PL367874A patent/PL206246B1/pl not_active IP Right Cessation
- 2002-08-27 DE DE60229404T patent/DE60229404D1/de not_active Expired - Lifetime
- 2002-08-27 ES ES02765352T patent/ES2314092T3/es not_active Expired - Lifetime
- 2002-08-27 EA EA200400311A patent/EA006022B1/ru not_active IP Right Cessation
- 2002-08-27 JP JP2003528764A patent/JP4157036B2/ja 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 EC EC2004005017A patent/ECSP045017A/es unknown
- 2004-03-12 NO NO20041060A patent/NO328252B1/no not_active IP Right Cessation
2009
- 2009-01-14 CY CY20091100027T patent/CY1109409T1/el unknown

Also Published As

Publication number	Publication date
CY1109409T1 (el)	2014-07-02
HUP0401694A3 (en)	2008-03-28
PL206246B1 (pl)	2010-07-30
EP1426355B1 (en)	2008-10-15
KR20080098691A (ko)	2008-11-11
AU2002330453B2 (en)	2008-04-17
IL160681A (en)	2010-06-16
ECSP045017A (es)	2004-09-27
NO20041060L (no)	2004-06-11
JPWO2003024916A1 (ja)	2004-12-24
CO5560555A2 (es)	2005-09-30
JP4157036B2 (ja)	2008-09-24
ATE411276T1 (de)	2008-10-15
DK1426355T3 (da)	2009-02-23
EA200400311A1 (ru)	2004-08-26
HK1070051A1 (en)	2005-06-10
BR0212494A (pt)	2004-08-24
CN1553890A (zh)	2004-12-08
DE60229404D1 (de)	2008-11-27
NZ531602A (en)	2006-01-27
HRP20040250A2 (en)	2005-02-28
UA77000C2 (en)	2006-10-16
EA006022B1 (ru)	2005-08-25
HUP0401694A2 (hu)	2004-11-29
CA2458544A1 (en)	2003-03-27
US20040242686A1 (en)	2004-12-02
CN1275936C (zh)	2006-09-20
PL367874A1 (en)	2005-03-07
EP1426355A4 (en)	2006-03-29
ZA200401757B (en)	2005-03-03
US7208520B2 (en)	2007-04-24
KR20040044881A (ko)	2004-05-31
EP1426355A1 (en)	2004-06-09
CA2458544C (en)	2010-08-17
SI1426355T1 (sl)	2009-02-28
ES2314092T3 (es)	2009-03-16
MXPA04002449A (es)	2004-07-23
PT1426355E (pt)	2008-11-03
WO2003024916A1 (en)	2003-03-27
IL160681A0 (en)	2004-08-31
KR100874952B1 (ko)	2008-12-19

Legal Events

Date	Code	Title	Description
2013-03-25	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US7208520B2 (en)	2007-04-24	Crystals of hydroxynorephedrine derivative
TWI344952B (en)	2011-07-11	Process for the preparation of and crystalline forms of optical enantiomers of modafinil
US9029420B2 (en)	2015-05-12	Agomelatine and pharmaceutical compositions thereof
JP2021513975A (ja)	2021-06-03	塩、結晶形態、およびその製造方法
TW200530165A (en)	2005-09-16	Sulfonamide derivatives for the treatment of diseases
TWI858104B (zh)	2024-10-11	作為Kv7鉀通道開放劑的醇衍生物
EP2690088B1 (en)	2017-02-22	Mixed crystal agomelatine (form-viii), preparation method and use thereof and pharmaceutical composition containing same
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