HRP20040250A2 - Crystals of hydroxynorephedrine derivative - Google Patents
Crystals of hydroxynorephedrine derivative Download PDFInfo
- Publication number
- HRP20040250A2 HRP20040250A2 HR20040250A HRP20040250A HRP20040250A2 HR P20040250 A2 HRP20040250 A2 HR P20040250A2 HR 20040250 A HR20040250 A HR 20040250A HR P20040250 A HRP20040250 A HR P20040250A HR P20040250 A2 HRP20040250 A2 HR P20040250A2
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- pollakiuria
- urinary incontinence
- ethyl
- fact
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims description 31
- WXFIGDLSSYIKKV-RCOVLWMOSA-N L-Metaraminol Chemical class C[C@H](N)[C@H](O)C1=CC=CC(O)=C1 WXFIGDLSSYIKKV-RCOVLWMOSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 52
- 206010036018 Pollakiuria Diseases 0.000 claims description 15
- 206010046543 Urinary incontinence Diseases 0.000 claims description 14
- 238000002441 X-ray diffraction Methods 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 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 12
- 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
- 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
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 102000016959 beta-3 Adrenergic Receptors Human genes 0.000 description 5
- 108010014502 beta-3 Adrenergic Receptors Proteins 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003860 storage Methods 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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- SLXOKVKOBXCWCK-SBUREZEXSA-N ethyl 2-[4-[2-[[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]-2,5-dimethylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC(C)=C1CCN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 SLXOKVKOBXCWCK-SBUREZEXSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000002904 solvent Substances 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
- -1 GW-515524 Chemical compound 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
- 206010013990 dysuria Diseases 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 229940121891 Dopamine receptor antagonist Drugs 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
- 102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 2
- 108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 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
- 239000000969 carrier Substances 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
- 239000003210 dopamine receptor blocking agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007951 isotonicity adjuster Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000012907 medicinal substance Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 201000007094 prostatitis Diseases 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 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
- 238000013112 stability test Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000003932 urinary bladder Anatomy 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 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
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- RUVMMEREJMHLOS-LBPRGKRZSA-N 3-[(4s)-5-oxo-2-(trifluoromethyl)-4,6,7,8-tetrahydro-1h-quinolin-4-yl]benzonitrile Chemical compound C1([C@@H]2C=C(NC3=C2C(CCC3)=O)C(F)(F)F)=CC=CC(C#N)=C1 RUVMMEREJMHLOS-LBPRGKRZSA-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
- 239000003148 4 aminobutyric acid receptor blocking 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
- 229940082496 Adrenoreceptor antagonist Drugs 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
- 206010063057 Cystitis noninfective Diseases 0.000 description 1
- 108010000437 Deamino Arginine Vasopressin Proteins 0.000 description 1
- XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 1
- 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
- 229940098788 GABA receptor antagonist Drugs 0.000 description 1
- 229940122236 Histamine receptor antagonist Drugs 0.000 description 1
- 206010020853 Hypertonic bladder Diseases 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 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
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- HRRBJVNMSRJFHQ-UHFFFAOYSA-N Naftopidil Chemical compound COC1=CC=CC=C1N1CCN(CC(O)COC=2C3=CC=CC=C3C=CC=2)CC1 HRRBJVNMSRJFHQ-UHFFFAOYSA-N 0.000 description 1
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 description 1
- 206010029279 Neurogenic bladder Diseases 0.000 description 1
- 102000009493 Neurokinin receptors Human genes 0.000 description 1
- 108050000302 Neurokinin receptors Proteins 0.000 description 1
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 1
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 1
- 229940127315 Potassium Channel Openers Drugs 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- RXZMMZZRUPYENV-VROPFNGYSA-N Solifenacin succinate Chemical compound OC(=O)CCC(O)=O.C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 RXZMMZZRUPYENV-VROPFNGYSA-N 0.000 description 1
- DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 description 1
- ICMGLRUYEQNHPF-UHFFFAOYSA-N Uraprene Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2)C)CC1 ICMGLRUYEQNHPF-UHFFFAOYSA-N 0.000 description 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 1
- 108010004977 Vasopressins Proteins 0.000 description 1
- 102000002852 Vasopressins Human genes 0.000 description 1
- 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
- IRAVYHIRJICKRS-UHFFFAOYSA-N acetic acid;hypochlorous acid Chemical compound ClO.CC(O)=O IRAVYHIRJICKRS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 201000005661 acute cystitis Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229960004607 alfuzosin Drugs 0.000 description 1
- WNMJYKCGWZFFKR-UHFFFAOYSA-N alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
- 229960000794 baclofen Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229960002504 capsaicin Drugs 0.000 description 1
- 235000017663 capsaicin Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003576 central nervous system agent Substances 0.000 description 1
- 229940125693 central nervous system agent Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 201000003139 chronic cystitis Diseases 0.000 description 1
- 208000013507 chronic prostatitis Diseases 0.000 description 1
- OPXKTCUYRHXSBK-UHFFFAOYSA-N clenbuterol hydrochloride Chemical group Cl.CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 OPXKTCUYRHXSBK-UHFFFAOYSA-N 0.000 description 1
- 229960001399 clenbuterol hydrochloride Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940035811 conjugated estrogen Drugs 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 229960002677 darifenacin Drugs 0.000 description 1
- HXGBXQDTNZMWGS-RUZDIDTESA-N darifenacin Chemical compound C=1C=CC=CC=1C([C@H]1CN(CCC=2C=C3CCOC3=CC=2)CC1)(C(=O)N)C1=CC=CC=C1 HXGBXQDTNZMWGS-RUZDIDTESA-N 0.000 description 1
- 229960004281 desmopressin Drugs 0.000 description 1
- NFLWUMRGJYTJIN-NXBWRCJVSA-N desmopressin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSCCC(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(N)=O)=O)CCC(=O)N)C1=CC=CC=C1 NFLWUMRGJYTJIN-NXBWRCJVSA-N 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
- HDRXZJPWHTXQRI-BHDTVMLSSA-N diltiazem hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CC[NH+](C)C)C2=CC=CC=C2S1 HDRXZJPWHTXQRI-BHDTVMLSSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- QTTMOCOWZLSYSV-QWAPEVOJSA-M equilin sodium sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 QTTMOCOWZLSYSV-QWAPEVOJSA-M 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 description 1
- 229960001348 estriol Drugs 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 229960002978 fesoterodine Drugs 0.000 description 1
- DCCSDBARQIPTGU-HSZRJFAPSA-N fesoterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CO)C=2)OC(=O)C(C)C)=CC=CC=C1 DCCSDBARQIPTGU-HSZRJFAPSA-N 0.000 description 1
- 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
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 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
- 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
- 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
- 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
- 238000002360 preparation method Methods 0.000 description 1
- 229960001187 propiverine hydrochloride Drugs 0.000 description 1
- 210000002307 prostate Anatomy 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
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 229960003855 solifenacin Drugs 0.000 description 1
- 239000000126 substance Substances 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
- 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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 (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040250A2 true HRP20040250A2 (en) | 2005-02-28 |
Family
ID=19101883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040250A HRP20040250A2 (en) | 2001-09-13 | 2004-03-12 | Crystals of hydroxynorephedrine derivative |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US7208520B2 (de) |
| EP (1) | EP1426355B1 (de) |
| JP (1) | JP4157036B2 (de) |
| KR (2) | KR20080098691A (de) |
| CN (1) | CN1275936C (de) |
| AT (1) | ATE411276T1 (de) |
| AU (1) | AU2002330453B2 (de) |
| BR (1) | BR0212494A (de) |
| CA (1) | CA2458544C (de) |
| CO (1) | CO5560555A2 (de) |
| CY (1) | CY1109409T1 (de) |
| DE (1) | DE60229404D1 (de) |
| DK (1) | DK1426355T3 (de) |
| EA (1) | EA006022B1 (de) |
| EC (1) | ECSP045017A (de) |
| ES (1) | ES2314092T3 (de) |
| HK (1) | HK1070051A1 (de) |
| HR (1) | HRP20040250A2 (de) |
| HU (1) | HUP0401694A3 (de) |
| IL (2) | IL160681A0 (de) |
| MX (1) | MXPA04002449A (de) |
| NO (1) | NO328252B1 (de) |
| NZ (1) | NZ531602A (de) |
| PL (1) | PL206246B1 (de) |
| PT (1) | PT1426355E (de) |
| SI (1) | SI1426355T1 (de) |
| UA (1) | UA77000C2 (de) |
| WO (1) | WO2003024916A1 (de) |
| ZA (1) | ZA200401757B (de) |
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 |
| PT1620085E (pt) * | 2003-05-05 | 2008-08-07 | Kissei Pharmaceutical | Utilização de derivados de ácido fenoxiacético para tratamento de bexiga hiperactiva |
| 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 |
| 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 |
| 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 |
| DK1612203T3 (da) * | 2004-06-28 | 2007-12-03 | Gruenenthal Gmbh | Krystallinske former af (-)-(1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenolhydrochlorid |
| EP1804778A1 (de) * | 2004-10-18 | 2007-07-11 | 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 |
| US20090247781A1 (en) | 2004-10-26 | 2009-10-01 | 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 |
| WO2006118087A1 (ja) * | 2005-04-26 | 2006-11-09 | Kissei Pharmaceutical Co., Ltd. | ヒドロキシノルエフェドリン誘導体塩酸塩・１／４水和物の結晶 |
| 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 |
| 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 |
| AU2008283929B2 (en) | 2007-08-06 | 2013-10-10 | Serenity Pharmaceuticals, Llc | Methods and devices for desmopressin drug delivery |
| US20100286045A1 (en) | 2008-05-21 | 2010-11-11 | Bjarke Mirner Klein | Methods comprising desmopressin |
| EP2712622B1 (de) | 2008-05-21 | 2016-07-13 | Ferring B.V. | Orodispersibles Desmopressin zur Erhöhung der nicht durch Nykturie gestörten Anfangsschlafperiode |
| US11963995B2 (en) | 2008-05-21 | 2024-04-23 | Ferring B.V. | Methods comprising desmopressin |
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 |
| 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 |
| 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 EP EP02765352A patent/EP1426355B1/de not_active Expired - Lifetime
- 2002-08-27 PT PT02765352T patent/PT1426355E/pt unknown
- 2002-08-27 EA EA200400311A patent/EA006022B1/ru not_active IP Right Cessation
- 2002-08-27 BR BR0212494-7A patent/BR0212494A/pt not_active IP Right Cessation
- 2002-08-27 WO PCT/JP2002/008596 patent/WO2003024916A1/ja active IP Right Grant
- 2002-08-27 DE DE60229404T patent/DE60229404D1/de not_active Expired - Lifetime
- 2002-08-27 US US10/489,343 patent/US7208520B2/en not_active Expired - Fee Related
- 2002-08-27 AU AU2002330453A patent/AU2002330453B2/en not_active Ceased
- 2002-08-27 KR KR1020087026126A patent/KR20080098691A/ko not_active Application Discontinuation
- 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 KR KR1020047003545A patent/KR100874952B1/ko not_active IP Right Cessation
- 2002-08-27 PL PL367874A patent/PL206246B1/pl 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
- 2002-08-27 MX MXPA04002449A patent/MXPA04002449A/es active IP Right Grant
- 2002-08-27 DK DK02765352T patent/DK1426355T3/da active
- 2002-08-27 SI SI200230775T patent/SI1426355T1/sl unknown
- 2002-08-27 JP JP2003528764A patent/JP4157036B2/ja not_active Expired - Fee Related
- 2002-08-27 AT AT02765352T patent/ATE411276T1/de active
- 2002-08-27 ES ES02765352T patent/ES2314092T3/es not_active Expired - Lifetime
- 2002-08-27 UA UA2004031852A patent/UA77000C2/uk unknown
-
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 EC EC2004005017A patent/ECSP045017A/es unknown
- 2004-03-12 HR HR20040250A patent/HRP20040250A2/hr not_active Application Discontinuation
- 2004-03-12 CO CO04022925A patent/CO5560555A2/es not_active Application Discontinuation
- 2004-03-12 NO NO20041060A patent/NO328252B1/no not_active IP Right Cessation
-
2005
- 2005-04-04 HK HK05102803A patent/HK1070051A1/xx not_active IP Right Cessation
-
2009
- 2009-01-14 CY CY20091100027T patent/CY1109409T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20040250A2 (en) | Crystals of hydroxynorephedrine derivative | |
| US10399920B2 (en) | Crystalline form of cannabidiol | |
| EP1991523B1 (de) | Selektive androgenrezeptormodulatoren | |
| US9029420B2 (en) | Agomelatine and pharmaceutical compositions thereof | |
| JP4054366B2 (ja) | 疾患の治療のために有用な化合物 | |
| JP2022500395A (ja) | ファルネソイドｘ受容体アゴニストの結晶形態 | |
| EP2690088B1 (de) | Mischkristall-agomelatin der form viii, herstellungsverfahren dafür und verwendung davon sowie pharmazeutische zusammensetzung damit | |
| US7763654B2 (en) | Crystal polymorph of hydroxynorephedrin derivative hydrochloride | |
| RU2761213C2 (ru) | Соль и полиморф фенил-пиримидонового соединения, их фармацевтическая композиция и применение | |
| JP2023528450A (ja) | ベータアドレナリンアゴニストの形態及び組成物 | |
| TW202120471A (zh) | 作為Kv7鉀通道開放劑的醇衍生物 | |
| TW201904954A (zh) | 一種苯并哌啶類衍生物的鹽、其晶型及鹽、其晶型的製備方法 | |
| US8003694B2 (en) | Crystal of hydroxynorephedrin derivative hydrochloride ¼ hydrate | |
| TW202412741A (zh) | 一種製備２－羥乙基胺基己酸酯類化合物方法及其應用 | |
| EP1954260A2 (de) | Isocystein-derivate zur behandlung von schmerzen | |
| CN103360276A (zh) | 阿戈美拉汀的晶型、制备方法和用途、以及药物组合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20110701 Year of fee payment: 10 |
|
| OBST | Application withdrawn |