ZA200403206B - Compounds and method for the treatment of overactive bladder. - Google Patents
Compounds and method for the treatment of overactive bladder. Download PDFInfo
- Publication number
- ZA200403206B ZA200403206B ZA200403206A ZA200403206A ZA200403206B ZA 200403206 B ZA200403206 B ZA 200403206B ZA 200403206 A ZA200403206 A ZA 200403206A ZA 200403206 A ZA200403206 A ZA 200403206A ZA 200403206 B ZA200403206 B ZA 200403206B
- Authority
- ZA
- South Africa
- Prior art keywords
- butyl
- compound
- dichlorophenyl
- piperidino
- piperidin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 99
- 238000000034 method Methods 0.000 title claims abstract description 39
- 206010020853 Hypertonic bladder Diseases 0.000 title claims description 7
- 208000009722 Overactive Urinary Bladder Diseases 0.000 title claims description 7
- 208000020629 overactive bladder Diseases 0.000 title claims description 7
- 238000011282 treatment Methods 0.000 title abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 238000010586 diagram Methods 0.000 claims abstract description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 239000000695 adrenergic alpha-agonist Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000262 estrogen Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 239000002876 beta blocker Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 230000001072 progestational effect Effects 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000037406 food intake Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- YXNCBDQUAFZRPM-HSZRJFAPSA-N n-[(2s)-2-(3,4-dichlorophenyl)-4-[4-(2-oxopiperidin-1-yl)piperidin-1-yl]butyl]-n-methylbenzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=CC=CC=1)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1N1CCCCC1=O YXNCBDQUAFZRPM-HSZRJFAPSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 3
- 229960001860 salicylate Drugs 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
- 229940095064 tartrate Drugs 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 230000000699 topical effect Effects 0.000 claims description 3
- 108010009685 Cholinergic Receptors Proteins 0.000 claims description 2
- 102000034337 acetylcholine receptors Human genes 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- ONVSREMZMCCOQT-JOCHJYFZSA-N n-[(2s)-2-(3,4-dichlorophenyl)-4-[4-(2-oxopiperidin-1-yl)piperidin-1-yl]butyl]-3-fluoro-n-methylbenzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=C(F)C=CC=1)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1N1CCCCC1=O ONVSREMZMCCOQT-JOCHJYFZSA-N 0.000 claims description 2
- KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 claims 2
- SKECORKXMSUSHJ-OAQYLSRUSA-N n-[(2s)-2-(3,4-dichlorophenyl)-4-[4-(2-oxopiperidin-1-yl)piperidin-1-yl]butyl]-2-fluoro-n-methylbenzamide Chemical compound C([C@H](CN(C)C(=O)C=1C(=CC=CC=1)F)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1N1CCCCC1=O SKECORKXMSUSHJ-OAQYLSRUSA-N 0.000 claims 2
- KLTPVIXNKQDFCI-RUZDIDTESA-N 2-[1-[(3s)-4-[benzoyl(methyl)amino]-3-(3,4-dichlorophenyl)butyl]-4-(2-oxopiperidin-1-yl)piperidin-4-yl]ethylcarbamic acid Chemical compound C([C@H](CN(C)C(=O)C=1C=CC=CC=1)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1(CCNC(O)=O)N1CCCCC1=O KLTPVIXNKQDFCI-RUZDIDTESA-N 0.000 claims 1
- VIBSFSXCEIXVDQ-JOCHJYFZSA-N n-[(2s)-2-(3,4-dichlorophenyl)-4-[4-(2-oxopiperidin-1-yl)piperidin-1-yl]butyl]-4-fluoro-n-methylbenzamide Chemical compound C([C@H](CN(C)C(=O)C=1C=CC(F)=CC=1)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1N1CCCCC1=O VIBSFSXCEIXVDQ-JOCHJYFZSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 abstract description 16
- 102100037342 Substance-K receptor Human genes 0.000 abstract description 12
- 101000600912 Homo sapiens Substance-K receptor Proteins 0.000 abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 8
- 241000124008 Mammalia Species 0.000 abstract description 5
- 230000027455 binding Effects 0.000 abstract description 5
- 239000002831 pharmacologic agent Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 71
- 239000000243 solution Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 230000008602 contraction Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 241000282412 Homo Species 0.000 description 5
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- 206010021639 Incontinence Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- -1 napsylate Chemical compound 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 210000003708 urethra Anatomy 0.000 description 4
- 206010046494 urge incontinence Diseases 0.000 description 4
- KYYKWYPDPQOFDS-QGZVFWFLSA-N 1-[1-[(3s)-3-(3,4-dichlorophenyl)-4-(methylamino)butyl]piperidin-4-yl]piperidin-2-one Chemical compound C([C@H](CNC)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1N1CCCCC1=O KYYKWYPDPQOFDS-QGZVFWFLSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 description 3
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000011067 equilibration Methods 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- LEEARGALTPRPLU-OAHLLOKOSA-N n-[(2s)-2-(3,4-dichlorophenyl)-4-oxobutyl]-n-methylbenzamide Chemical compound C1([C@H](CC=O)CN(C)C(=O)C=2C=CC=CC=2)=CC=C(Cl)C(Cl)=C1 LEEARGALTPRPLU-OAHLLOKOSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- FCGOUOJEQGSCEI-UHFFFAOYSA-N 1-piperidin-4-ylpiperidin-2-one Chemical compound O=C1CCCCN1C1CCNCC1 FCGOUOJEQGSCEI-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- 102100024304 Protachykinin-1 Human genes 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010066218 Stress Urinary Incontinence Diseases 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- XFJXSXBJGWRZOR-UHFFFAOYSA-N benzyl 4-(5-chloropentanoylamino)piperidine-1-carboxylate Chemical compound C1CC(NC(=O)CCCCCl)CCN1C(=O)OCC1=CC=CC=C1 XFJXSXBJGWRZOR-UHFFFAOYSA-N 0.000 description 2
- 210000005068 bladder tissue Anatomy 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 230000001713 cholinergic effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 230000003340 mental effect Effects 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 229940127242 parasympathomimetic drug Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 208000022170 stress incontinence Diseases 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- GKWHADZLLZJSEA-GFCCVEGCSA-N tert-butyl n-[(2s)-2-(3,4-dichlorophenyl)-4-hydroxybutyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C[C@@H](CCO)C1=CC=C(Cl)C(Cl)=C1 GKWHADZLLZJSEA-GFCCVEGCSA-N 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 239000011534 wash buffer Substances 0.000 description 2
- PMKXGAWLBDGCRM-UHFFFAOYSA-N 1-piperidin-4-ylpiperidine-2-thione Chemical compound S=C1CCCCN1C1CCNCC1 PMKXGAWLBDGCRM-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- BRIZVRFVUVROQJ-UHFFFAOYSA-N 4-(2-oxopiperidin-1-yl)-1-phenylmethoxycarbonylpiperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)(N2C(CCCC2)=O)CCN1C(=O)OCC1=CC=CC=C1 BRIZVRFVUVROQJ-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 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
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
- 206010013774 Dry eye Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010027566 Micturition urgency Diseases 0.000 description 1
- 229940122694 Muscarinic M3 receptor antagonist Drugs 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 102000003729 Neprilysin Human genes 0.000 description 1
- 108090000028 Neprilysin Proteins 0.000 description 1
- 108090000189 Neuropeptides Proteins 0.000 description 1
- 206010036018 Pollakiuria Diseases 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QPCVHQBVMYCJOM-UHFFFAOYSA-N Propiverine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(=O)OC1CCN(C)CC1 QPCVHQBVMYCJOM-UHFFFAOYSA-N 0.000 description 1
- 101710151387 Serine protease 1 Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 108010072901 Tachykinin Receptors Proteins 0.000 description 1
- 102000007124 Tachykinin Receptors Human genes 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 108010036928 Thiorphan Proteins 0.000 description 1
- 229940122618 Trypsin inhibitor Drugs 0.000 description 1
- 101710162629 Trypsin inhibitor Proteins 0.000 description 1
- 101710119665 Trypsin-1 Proteins 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- YPFPFQHGAVKSPV-UHFFFAOYSA-N benzyl 4-(2-sulfanylidenepiperidin-1-yl)piperidine-1-carboxylate Chemical compound C1CC(N2C(CCCC2)=S)CCN1C(=O)OCC1=CC=CC=C1 YPFPFQHGAVKSPV-UHFFFAOYSA-N 0.000 description 1
- YYIQGSYCCNQAGV-UHFFFAOYSA-N benzyl 4-aminopiperidine-1-carboxylate Chemical compound C1CC(N)CCN1C(=O)OCC1=CC=CC=C1 YYIQGSYCCNQAGV-UHFFFAOYSA-N 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 230000009989 contractile response Effects 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 206010013781 dry mouth Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960000855 flavoxate Drugs 0.000 description 1
- SPIUTQOUKAMGCX-UHFFFAOYSA-N flavoxate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCN1CCCCC1 SPIUTQOUKAMGCX-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 238000000670 ligand binding assay Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003681 muscarinic M3 receptor antagonist Substances 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- WBLYPMDGNCCKLM-HSZRJFAPSA-N n-[(2s)-2-(3,4-dichlorophenyl)-4-[4-(2-oxo-1,3-diazinan-1-yl)piperidin-1-yl]butyl]-n-ethylbenzamide Chemical compound C([C@H](CN(CC)C(=O)C=1C=CC=CC=1)C=1C=C(Cl)C(Cl)=CC=1)CN(CC1)CCC1N1CCCNC1=O WBLYPMDGNCCKLM-HSZRJFAPSA-N 0.000 description 1
- NOWASWVSADZBSZ-OAHLLOKOSA-N n-[(2s)-2-(3,4-dichlorophenyl)-4-hydroxybutyl]-n-methylbenzamide Chemical compound C1([C@H](CCO)CN(C)C(=O)C=2C=CC=CC=2)=CC=C(Cl)C(Cl)=C1 NOWASWVSADZBSZ-OAHLLOKOSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000011165 process development Methods 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 229960003510 propiverine Drugs 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- IXSRSYZHKFLVEK-GFCCVEGCSA-N tert-butyl n-[(2s)-2-(3,4-dichlorophenyl)-4-oxobutyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C[C@@H](CC=O)C1=CC=C(Cl)C(Cl)=C1 IXSRSYZHKFLVEK-GFCCVEGCSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- LJJKNPQAGWVLDQ-SNVBAGLBSA-N thiorphan Chemical compound OC(=O)CNC(=O)[C@@H](CS)CC1=CC=CC=C1 LJJKNPQAGWVLDQ-SNVBAGLBSA-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
- 238000011200 topical administration Methods 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 208000022934 urinary frequency Diseases 0.000 description 1
- 238000003828 vacuum filtration Methods 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
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P13/10—Drugs for disorders of the urinary system of the bladder
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Urology & Nephrology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Pretreatment Of Seeds And Plants (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0103795A SE0103795D0 (sv) | 2001-11-02 | 2001-11-02 | Compounds and method for the treatment of överactive bladder |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200403206B true ZA200403206B (en) | 2005-02-22 |
Family
ID=20285984
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200403206A ZA200403206B (en) | 2001-11-02 | 2004-04-28 | Compounds and method for the treatment of overactive bladder. |
Country Status (16)
Country | Link |
---|---|
US (1) | US7368461B2 (ko) |
EP (1) | EP1444220B1 (ko) |
JP (1) | JP2005511571A (ko) |
KR (1) | KR20040053239A (ko) |
CN (1) | CN1610676A (ko) |
AT (1) | ATE353886T1 (ko) |
BR (1) | BR0213832A (ko) |
CA (1) | CA2465429A1 (ko) |
DE (1) | DE60218203T2 (ko) |
ES (1) | ES2282491T3 (ko) |
IL (1) | IL161600A0 (ko) |
MX (1) | MXPA04004075A (ko) |
NO (1) | NO20042138L (ko) |
SE (1) | SE0103795D0 (ko) |
WO (1) | WO2003037889A1 (ko) |
ZA (1) | ZA200403206B (ko) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200508221A (en) | 2003-06-13 | 2005-03-01 | Astrazeneca Ab | New azetidine compounds |
DE102004001873A1 (de) * | 2004-01-14 | 2005-09-29 | Bayer Healthcare Ag | Cyanopyrimidinone |
WO2006121389A1 (en) * | 2005-05-10 | 2006-11-16 | Astrazeneca Ab | Use of a neurokinin-2 receptor antagonist for treating or preventing detrusor overactivity |
AR057828A1 (es) | 2005-09-29 | 2007-12-19 | Astrazeneca Ab | Compuestos derivados de azetidina, su preparacion y composicion farmaceuutica |
US8106208B2 (en) | 2006-05-18 | 2012-01-31 | Albireo Ab | Benzamide compounds that act as NK receptor antagonists |
TWI404721B (zh) | 2009-01-26 | 2013-08-11 | Pfizer | 胺基-雜環化合物 |
CN112915266B (zh) * | 2021-02-05 | 2021-11-09 | 武汉磁济科技有限公司 | 一种人工膀胱铁磁复合体及其制备方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9321557D0 (en) * | 1992-11-03 | 1993-12-08 | Zeneca Ltd | Carboxamide derivatives |
GB9310713D0 (en) | 1993-05-24 | 1993-07-07 | Zeneca Ltd | Aryl substituted heterocycles |
GB9317104D0 (en) * | 1993-08-17 | 1993-09-29 | Zeneca Ltd | Therapeutic heterocycles |
GB9322643D0 (en) * | 1993-11-03 | 1993-12-22 | Zeneca Ltd | Lactam derivatives |
US6008223A (en) | 1994-10-27 | 1999-12-28 | Zeneca Limited | Therapeutic compounds |
GB9421709D0 (en) * | 1994-10-27 | 1994-12-14 | Zeneca Ltd | Therapeutic compounds |
GB9505084D0 (en) | 1995-03-14 | 1995-05-03 | Pfizer Ltd | Benzamide derivative |
GB9922519D0 (en) | 1998-10-07 | 1999-11-24 | Zeneca Ltd | Compounds |
GB9924141D0 (en) | 1998-10-30 | 1999-12-15 | Zeneca Ltd | Treatment of gastric asthma |
WO2000034234A1 (fr) * | 1998-12-04 | 2000-06-15 | Rimma Iliinichna Ashkinazi | Aryl- et heteroarylamides d'acides carboalcoxysulfaniliques |
GB9826941D0 (en) | 1998-12-09 | 1999-02-03 | Zeneca Pharmaceuticals | Compounds |
GB0015246D0 (en) | 2000-06-22 | 2000-08-16 | Astrazeneca Ab | Method for the treatment of urinary incontinence |
-
2001
- 2001-11-02 SE SE0103795A patent/SE0103795D0/xx unknown
-
2002
- 2002-11-01 US US10/494,195 patent/US7368461B2/en not_active Expired - Fee Related
- 2002-11-01 DE DE60218203T patent/DE60218203T2/de not_active Expired - Fee Related
- 2002-11-01 WO PCT/SE2002/001991 patent/WO2003037889A1/en active IP Right Grant
- 2002-11-01 JP JP2003540170A patent/JP2005511571A/ja active Pending
- 2002-11-01 EP EP02783904A patent/EP1444220B1/en not_active Expired - Lifetime
- 2002-11-01 BR BR0213832-8A patent/BR0213832A/pt not_active IP Right Cessation
- 2002-11-01 CN CNA028265696A patent/CN1610676A/zh active Pending
- 2002-11-01 IL IL16160002A patent/IL161600A0/xx unknown
- 2002-11-01 CA CA002465429A patent/CA2465429A1/en not_active Abandoned
- 2002-11-01 KR KR10-2004-7006520A patent/KR20040053239A/ko not_active Application Discontinuation
- 2002-11-01 AT AT02783904T patent/ATE353886T1/de not_active IP Right Cessation
- 2002-11-01 MX MXPA04004075A patent/MXPA04004075A/es unknown
- 2002-11-01 ES ES02783904T patent/ES2282491T3/es not_active Expired - Lifetime
-
2004
- 2004-04-28 ZA ZA200403206A patent/ZA200403206B/en unknown
- 2004-05-25 NO NO20042138A patent/NO20042138L/no unknown
Also Published As
Publication number | Publication date |
---|---|
SE0103795D0 (sv) | 2001-11-02 |
DE60218203D1 (de) | 2007-03-29 |
JP2005511571A (ja) | 2005-04-28 |
NO20042138L (no) | 2004-05-25 |
ATE353886T1 (de) | 2007-03-15 |
KR20040053239A (ko) | 2004-06-23 |
DE60218203T2 (de) | 2008-01-03 |
CA2465429A1 (en) | 2003-05-08 |
IL161600A0 (en) | 2004-09-27 |
ES2282491T3 (es) | 2007-10-16 |
WO2003037889A8 (en) | 2004-05-06 |
CN1610676A (zh) | 2005-04-27 |
WO2003037889A1 (en) | 2003-05-08 |
EP1444220B1 (en) | 2007-02-14 |
BR0213832A (pt) | 2004-08-31 |
MXPA04004075A (es) | 2004-07-23 |
US7368461B2 (en) | 2008-05-06 |
EP1444220A1 (en) | 2004-08-11 |
US20050203113A1 (en) | 2005-09-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EA009455B1 (ru) | Ингибирующие mtp арилпиперидины или пиперазины, замещенные 5-членными гетероциклами | |
SK61399A3 (en) | HETEROCYCLE DERIVATIVES WHICH INHIBIT FACTOR Xa | |
EA010852B1 (ru) | Пиперидиновые соединения и фармацевтические композиции, их содержащие | |
RU2193557C2 (ru) | Бензоциклогептатиофеновые соединения, способы профилактики или лечения, фармацевтическая композиция | |
TW200825072A (en) | Soluble epoxide hydrolase inhibitors | |
WO2008040974A1 (en) | Indoles for use as dpp-iv inhibitors | |
US5578611A (en) | Use of α-1C specific compounds to treat benign prostatic hyperplasia | |
US20080234280A1 (en) | Use of Mc4 Receptor Agonist Compounds | |
AU2003228991B2 (en) | Compositions and methods for combating lower urinary tract dysfunctions with delta opioid receptor agonists | |
CN101466726A (zh) | 用作治疗心血管障碍的药物的雄甾烷和雄甾烯的氮杂环衍生物 | |
EP1444220B1 (en) | Compounds and method for the treatment of overactive bladder | |
US5508306A (en) | Aromatic amine derivatives | |
EP1602645A1 (en) | Nitrogenous heterocyclic derivative having 2,6-disubstituted styryl | |
US5032614A (en) | Serotonin antagonist | |
WO2022084930A2 (en) | Cancer therapy using a combination of cdk7 inhibitor with an anti-microtubule agent | |
EP1307202B1 (en) | Method for the treatment of overactive bladder | |
EP4275687A1 (en) | Uses of melanocortin-4 receptor agonist | |
US5244895A (en) | Anti-ulcer agent | |
AU2002347709A1 (en) | Compounds and method for the treatment of overactive bladder | |
US20040248914A1 (en) | Method for the treatment of overactive bladder | |
AU2002347708A1 (en) | Method for the treatment of overactive bladder | |
EP0104053A1 (en) | Benzodiazepines for treating panic disorders | |
JPH11503128A (ja) | 新規複素環式化合物 | |
WO2024072794A1 (en) | Pyridine carboxamide compounds and their use in treating medical conditions |