PH27014A - Compounds for the treatment of urinary incontinence - Google Patents
Compounds for the treatment of urinary incontinence Download PDFInfo
- Publication number
- PH27014A PH27014A PH39454A PH39454A PH27014A PH 27014 A PH27014 A PH 27014A PH 39454 A PH39454 A PH 39454A PH 39454 A PH39454 A PH 39454A PH 27014 A PH27014 A PH 27014A
- Authority
- PH
- Philippines
- Prior art keywords
- compounds
- lower alkyl
- diphenylacetamide
- methyl
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 72
- 238000011282 treatment Methods 0.000 title abstract description 16
- 206010046543 Urinary incontinence Diseases 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 210000003932 urinary bladder Anatomy 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 150000007513 acids Chemical class 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 230000003287 optical effect Effects 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 16
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 4
- GSCHLPMNNOMSNR-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)NCCN(C(C)C)C(C)C)C1=CC=CC=C1 GSCHLPMNNOMSNR-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 208000035475 disorder Diseases 0.000 abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 229940073584 methylene chloride Drugs 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 241000282414 Homo sapiens Species 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- -1 2-cyclohexyl-2-hydroxy-2-phe- nylacetic acid 4-(diethylamino)-2-butynyl ester Chemical class 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229930003347 Atropine Natural products 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000001078 anti-cholinergic effect Effects 0.000 description 5
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 5
- 229960000396 atropine Drugs 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 210000002460 smooth muscle Anatomy 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 2
- 229960004011 methenamine Drugs 0.000 description 2
- CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 2
- DKLYDESVXZKCFI-UHFFFAOYSA-N n,n-diphenylacetamide Chemical compound C=1C=CC=CC=1N(C(=O)C)C1=CC=CC=C1 DKLYDESVXZKCFI-UHFFFAOYSA-N 0.000 description 2
- IUSXYVRFJVAVOB-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine;hydron;chloride Chemical compound Cl.CC(C)N(C(C)C)CCCl IUSXYVRFJVAVOB-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 210000003079 salivary gland Anatomy 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- UISARWKNNNHPGI-UHFFFAOYSA-N terodiline Chemical compound C=1C=CC=CC=1C(CC(C)NC(C)(C)C)C1=CC=CC=C1 UISARWKNNNHPGI-UHFFFAOYSA-N 0.000 description 2
- 229960005383 terodiline Drugs 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 206010046494 urge incontinence Diseases 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- SUPNUNXTOMHOHP-UHFFFAOYSA-N 2,2-diphenylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(=O)N)C1=CC=CC=C1 SUPNUNXTOMHOHP-UHFFFAOYSA-N 0.000 description 1
- MFKMYYPWCWXHBY-UHFFFAOYSA-N 2-hydroxyacetamide;hydrochloride Chemical compound Cl.NC(=O)CO MFKMYYPWCWXHBY-UHFFFAOYSA-N 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 1
- UYXDQUAGGZJICS-UHFFFAOYSA-N 3,3-diphenylpropanoyl chloride Chemical compound C=1C=CC=CC=1C(CC(=O)Cl)C1=CC=CC=C1 UYXDQUAGGZJICS-UHFFFAOYSA-N 0.000 description 1
- XUDYILJNWNEBBF-UHFFFAOYSA-N 3-[di(propan-2-yl)amino]propanenitrile Chemical compound CC(C)N(C(C)C)CCC#N XUDYILJNWNEBBF-UHFFFAOYSA-N 0.000 description 1
- RXYQHVMJQFHKDX-UHFFFAOYSA-N 3-chloro-n,n-di(propan-2-yl)propan-1-amine Chemical compound CC(C)N(C(C)C)CCCCl RXYQHVMJQFHKDX-UHFFFAOYSA-N 0.000 description 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- NANGQJICIOUURV-UHFFFAOYSA-N 3-phenyl-3h-1-benzofuran-2-one Chemical compound O=C1OC2=CC=CC=C2C1C1=CC=CC=C1 NANGQJICIOUURV-UHFFFAOYSA-N 0.000 description 1
- 208000000187 Abnormal Reflex Diseases 0.000 description 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FYKUBUATPBGXPV-UHFFFAOYSA-N C(C)(C)NN(NC(C)C)CCC Chemical compound C(C)(C)NN(NC(C)C)CCC FYKUBUATPBGXPV-UHFFFAOYSA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 208000008967 Enuresis Diseases 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000008454 Hyperhidrosis Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- 241000124008 Mammalia Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000002539 anti-aggressive effect Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000001022 anti-muscarinic effect Effects 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 229960004484 carbachol Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 201000003892 detrusor sphincter dyssynergia Diseases 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000037315 hyperhidrosis Effects 0.000 description 1
- 206010020745 hyperreflexia Diseases 0.000 description 1
- 230000035859 hyperreflexia Effects 0.000 description 1
- 230000030214 innervation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000002911 mydriatic effect Effects 0.000 description 1
- QPGRDTXELAFGRG-UHFFFAOYSA-N n',n'-di(propan-2-yl)propane-1,3-diamine Chemical compound CC(C)N(C(C)C)CCCN QPGRDTXELAFGRG-UHFFFAOYSA-N 0.000 description 1
- CVJLDKIKUUHTIA-UHFFFAOYSA-N n'-tert-butyl-n,n'-dimethylpropane-1,3-diamine Chemical compound CNCCCN(C)C(C)(C)C CVJLDKIKUUHTIA-UHFFFAOYSA-N 0.000 description 1
- NGRXSVVLBWDAHG-UHFFFAOYSA-N n,n-bis(propan-2-ylamino)ethanamine Chemical compound CC(C)NN(CC)NC(C)C NGRXSVVLBWDAHG-UHFFFAOYSA-N 0.000 description 1
- DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 description 1
- CWEZWUZFIMDYDQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N(CCO)C)C1=CC=CC=C1 CWEZWUZFIMDYDQ-UHFFFAOYSA-N 0.000 description 1
- ZGUQMUHCSSFERG-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]-2-(2-hydroxyphenyl)-2-phenylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=C(O)C=1C(C(=O)NCCN(C(C)C)C(C)C)C1=CC=CC=C1 ZGUQMUHCSSFERG-UHFFFAOYSA-N 0.000 description 1
- SQWLHWBNQRMCBT-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]-2-methoxy-2,2-diphenylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(=O)NCCN(C(C)C)C(C)C)(OC)C1=CC=CC=C1 SQWLHWBNQRMCBT-UHFFFAOYSA-N 0.000 description 1
- GUNXZCRBPCEOLU-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]-n-methyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N(C)CCN(C(C)C)C(C)C)C1=CC=CC=C1 GUNXZCRBPCEOLU-UHFFFAOYSA-N 0.000 description 1
- UARPOSDIKLYISH-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-n-methyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N(C)CCCN(CC)CC)C1=CC=CC=C1 UARPOSDIKLYISH-UHFFFAOYSA-N 0.000 description 1
- 238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229960005434 oxybutynin Drugs 0.000 description 1
- 210000003540 papillary muscle Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- PVGBHEUCHKGFQP-UHFFFAOYSA-N sodium;n-[5-amino-2-(4-aminophenyl)sulfonylphenyl]sulfonylacetamide Chemical compound [Na+].CC(=O)NS(=O)(=O)C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 PVGBHEUCHKGFQP-UHFFFAOYSA-N 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 208000026533 urinary bladder disease Diseases 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000001186 vagus nerve Anatomy 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
- A61K31/16—Amides, e.g. hydroxamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/40—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (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)
- Steroid Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Table Equipment (AREA)
- Finger-Pressure Massage (AREA)
- Dowels (AREA)
- Underground Structures, Protecting, Testing And Restoring Foundations (AREA)
- Measurement Of Velocity Or Position Using Acoustic Or Ultrasonic Waves (AREA)
- Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
- Medicinal Preparation (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Discharge Heating (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE8804003A SE8804003D0 (sv) | 1988-11-04 | 1988-11-04 | Compounds for the treatment of urinary incontinence |
Publications (1)
Publication Number | Publication Date |
---|---|
PH27014A true PH27014A (en) | 1993-02-01 |
Family
ID=20373858
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PH39454A PH27014A (en) | 1988-11-04 | 1989-11-03 | Compounds for the treatment of urinary incontinence |
Country Status (22)
Country | Link |
---|---|
EP (1) | EP0367040B1 (ja) |
JP (1) | JPH02218652A (ja) |
KR (1) | KR900007407A (ja) |
CN (1) | CN1043700A (ja) |
AT (1) | ATE88460T1 (ja) |
AU (1) | AU628879B2 (ja) |
CA (1) | CA2001641A1 (ja) |
DD (1) | DD289467A5 (ja) |
DE (1) | DE68906122T2 (ja) |
DK (1) | DK544689A (ja) |
ES (1) | ES2054980T3 (ja) |
FI (1) | FI895229A0 (ja) |
HU (1) | HU202828B (ja) |
IE (1) | IE63480B1 (ja) |
NO (1) | NO894384L (ja) |
NZ (1) | NZ231243A (ja) |
PH (1) | PH27014A (ja) |
PT (1) | PT92189B (ja) |
RU (1) | RU1833370C (ja) |
SE (1) | SE8804003D0 (ja) |
TW (1) | TW197944B (ja) |
ZA (1) | ZA898385B (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5066680A (en) * | 1989-02-14 | 1991-11-19 | Fujisawa Pharmaceutical Co., Ltd. | Novel substituted-acetamide compound and a process for the preparation thereof |
US5192779A (en) * | 1989-02-14 | 1993-03-09 | Fujisawa Pharmaceutical Co., Ltd. | Substituted-acetamide compound and a process for the preparation thereof |
PH30083A (en) * | 1991-02-25 | 1996-12-27 | Lilly Co Eli | Treatment of lower urinary tract disorders |
TW344661B (en) * | 1993-11-24 | 1998-11-11 | Lilly Co Eli | Pharmaceutical composition for treatment of incontinence |
GB0328060D0 (en) * | 2003-12-04 | 2004-01-07 | Sod Conseils Rech Applic | Botulinum toxin treatment |
MX368097B (es) * | 2015-04-28 | 2019-09-19 | Unilever Nv | Compuestos de n-aralquilcarbonildiamina y composiciones para el cuidado personal que comprende los mismos. |
EP3288926B1 (en) | 2015-04-28 | 2021-01-20 | Unilever PLC | N-aralkylcarbonyl-piperazine and -homopiperazine compounds and personal care compositions comprising the same |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2009144A (en) * | 1935-07-23 | Substituted amides of amphatic- | ||
US2831892A (en) * | 1956-03-22 | 1958-04-22 | Searle & Co | N-(3-isopropylaminopropyl) diphenyl-acetamide and processes |
FR2319337A1 (fr) * | 1975-07-30 | 1977-02-25 | Fabre Sa Pierre | Gem diaryles possedant une activite antiarythmique utile en therapeutique cardiovasculaire |
FR2333501A2 (fr) * | 1975-12-03 | 1977-07-01 | Science Union & Cie | Nouveaux acetamides substitues leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
FR2340724A2 (fr) * | 1976-02-13 | 1977-09-09 | Science Union & Cie | Nouveaux diarylacetamides substitues, leurs procedes de preparation et les compositions pharmaceutiques en contenant |
FR2421892A1 (fr) * | 1977-10-17 | 1979-11-02 | Fabre Sa Pierre | Procede de synthese industrielle du n(n' ethyl pyrrolidino-2 methyl) aadiphenylahydroxy acetamide |
FR2421891A1 (fr) * | 1977-10-17 | 1979-11-02 | Fabre Sa Pierre | Obtention industrielle d'amides de la pyrrolidine ethyl amine |
US5066680A (en) * | 1989-02-14 | 1991-11-19 | Fujisawa Pharmaceutical Co., Ltd. | Novel substituted-acetamide compound and a process for the preparation thereof |
-
1988
- 1988-11-04 SE SE8804003A patent/SE8804003D0/xx unknown
-
1989
- 1989-10-20 ES ES89119480T patent/ES2054980T3/es not_active Expired - Lifetime
- 1989-10-20 AT AT89119480T patent/ATE88460T1/de not_active IP Right Cessation
- 1989-10-20 IE IE339889A patent/IE63480B1/en not_active IP Right Cessation
- 1989-10-20 EP EP89119480A patent/EP0367040B1/en not_active Expired - Lifetime
- 1989-10-20 DE DE68906122T patent/DE68906122T2/de not_active Expired - Fee Related
- 1989-10-27 CA CA002001641A patent/CA2001641A1/en not_active Abandoned
- 1989-11-01 DK DK544689A patent/DK544689A/da not_active Application Discontinuation
- 1989-11-02 HU HU895648A patent/HU202828B/hu unknown
- 1989-11-02 NZ NZ231243A patent/NZ231243A/en unknown
- 1989-11-02 JP JP1285092A patent/JPH02218652A/ja active Pending
- 1989-11-03 AU AU44394/89A patent/AU628879B2/en not_active Ceased
- 1989-11-03 NO NO89894384A patent/NO894384L/no unknown
- 1989-11-03 PT PT92189A patent/PT92189B/pt not_active IP Right Cessation
- 1989-11-03 ZA ZA898385A patent/ZA898385B/xx unknown
- 1989-11-03 DD DD89334233A patent/DD289467A5/de not_active IP Right Cessation
- 1989-11-03 PH PH39454A patent/PH27014A/en unknown
- 1989-11-03 RU SU894742370A patent/RU1833370C/ru active
- 1989-11-03 FI FI895229A patent/FI895229A0/fi not_active IP Right Cessation
- 1989-11-04 CN CN89109190A patent/CN1043700A/zh active Pending
- 1989-11-04 KR KR1019890016004A patent/KR900007407A/ko not_active Application Discontinuation
- 1989-12-19 TW TW078109850A patent/TW197944B/zh active
Also Published As
Publication number | Publication date |
---|---|
PT92189B (pt) | 1995-07-18 |
EP0367040B1 (en) | 1993-04-21 |
CA2001641A1 (en) | 1990-05-04 |
HU202828B (en) | 1991-04-29 |
ZA898385B (en) | 1990-07-25 |
HU895648D0 (en) | 1990-01-28 |
NZ231243A (en) | 1994-03-25 |
DE68906122T2 (de) | 1997-05-22 |
ES2054980T3 (es) | 1994-08-16 |
DD289467A5 (de) | 1991-05-02 |
IE63480B1 (en) | 1995-05-03 |
AU4439489A (en) | 1990-05-10 |
SE8804003D0 (sv) | 1988-11-04 |
FI895229A0 (fi) | 1989-11-03 |
HUT51597A (en) | 1990-05-28 |
JPH02218652A (ja) | 1990-08-31 |
DK544689D0 (da) | 1989-11-01 |
EP0367040A1 (en) | 1990-05-09 |
KR900007407A (ko) | 1990-06-01 |
TW197944B (ja) | 1993-01-11 |
IE893398L (en) | 1990-05-04 |
NO894384L (no) | 1990-05-07 |
CN1043700A (zh) | 1990-07-11 |
ATE88460T1 (de) | 1993-05-15 |
DK544689A (da) | 1990-05-05 |
NO894384D0 (no) | 1989-11-03 |
DE68906122D1 (de) | 1993-05-27 |
AU628879B2 (en) | 1992-09-24 |
PT92189A (pt) | 1990-05-31 |
RU1833370C (en) | 1993-08-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2167152C2 (ru) | N-замещенные азагетероциклические карбоновые кислоты или их фармацевтически приемлемые соли, способ их получения, фармацевтическая композиция на их основе и способ ингибирования нейрогенного воспаления | |
US7026320B2 (en) | Serotonergic agents | |
JPS6049192B2 (ja) | 新規置換ベンズアミド、その製造方法及びこれを有効成分とする向精神薬 | |
JPH05194513A (ja) | 化学中間体 | |
US6107328A (en) | Use of 5HT1B receptor antagonist for the treatment of vascular disease | |
AT399338B (de) | Neue substituierte benzamide, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die diese benzamide enthalten | |
PL162318B1 (pl) | Sposób wytwarzania nowych pochodnych piperydyny PL PL PL | |
US5236956A (en) | Compounds for the treatment of urinary incontinence | |
PH27014A (en) | Compounds for the treatment of urinary incontinence | |
EP1611126B1 (de) | Chromenonindole | |
JPH0331279A (ja) | 新規r(―)3―キヌクリジノール誘導体類 | |
EP0306698B1 (de) | Neue kondensierte Diazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
EP0254955A2 (de) | Substituierte Pyrido-[2,3-b][1,4]benzodiazepin-6-one, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
EP0312895A2 (de) | Kondensierte Diazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
JP2021517137A (ja) | Rock阻害剤としての重水素化合物 | |
JPH04178356A (ja) | 光学活性なベンジルアルコール誘導体及びその用途 | |
EP0369286A2 (de) | Dibenzazepin-Derivate zur Behandlung von akuten und chronischen obstruktiven Atemwegserkrankungen | |
CA2120215C (en) | 2,3-dihydro-4(1h)-quinazolinones active in gastro-intestinal pathologies | |
US4766119A (en) | Antispasmodic alkylated aminothioester derivatives | |
JP4781362B2 (ja) | 4級アンモニウム基を有するキヌクリジン化合物とその調製方法、およびアセチルコリン遮断剤としての用途 | |
US4647562A (en) | Anti-spasmodic agents having three branch chains | |
US4410527A (en) | Substituted thienobenzodiazepinones and salts thereof | |
US4721722A (en) | Anti-spasmodic agents containing quaternary nitrogen | |
US7816362B2 (en) | Serotonergic agents | |
KR20030036834A (ko) | 5-페닐벤질아민 화합물, 그의 제법 및 그의 합성 중간체 |