DE10201550A1 - Phenoxy-Piperidine - Google Patents
Phenoxy-PiperidineInfo
- Publication number
- DE10201550A1 DE10201550A1 DE10201550A DE10201550A DE10201550A1 DE 10201550 A1 DE10201550 A1 DE 10201550A1 DE 10201550 A DE10201550 A DE 10201550A DE 10201550 A DE10201550 A DE 10201550A DE 10201550 A1 DE10201550 A1 DE 10201550A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- solvates
- compounds
- stereoisomers
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- BRUWSFUBFQYNPG-UHFFFAOYSA-N 1-phenoxypiperidine Chemical class C1CCCCN1OC1=CC=CC=C1 BRUWSFUBFQYNPG-UHFFFAOYSA-N 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 206010012289 Dementia Diseases 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 238000011321 prophylaxis Methods 0.000 claims abstract description 9
- 239000012636 effector Substances 0.000 claims abstract description 8
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 7
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 7
- 208000000323 Tourette Syndrome Diseases 0.000 claims abstract description 7
- 208000016620 Tourette disease Diseases 0.000 claims abstract description 7
- 230000036506 anxiety Effects 0.000 claims abstract description 7
- 210000004558 lewy body Anatomy 0.000 claims abstract description 7
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 6
- 206010057852 Nicotine dependence Diseases 0.000 claims abstract description 6
- 208000006011 Stroke Diseases 0.000 claims abstract description 6
- 208000025569 Tobacco Use disease Diseases 0.000 claims abstract description 6
- 230000006931 brain damage Effects 0.000 claims abstract description 6
- 231100000874 brain damage Toxicity 0.000 claims abstract description 6
- 208000029028 brain injury Diseases 0.000 claims abstract description 6
- 231100000167 toxic agent Toxicity 0.000 claims abstract description 6
- 208000023105 Huntington disease Diseases 0.000 claims abstract description 5
- -1 2-nitrophenyl-methyl Chemical group 0.000 claims description 138
- 239000012453 solvate Substances 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 9
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 9
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 9
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 230000029936 alkylation Effects 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
- 108010009685 Cholinergic Receptors Proteins 0.000 claims description 5
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000027455 binding Effects 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- OSFLKLGTGPFNRH-UHFFFAOYSA-N n-[4-(1-benzylpiperidin-4-yl)oxyphenyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C1)=CC=C1OC(CC1)CCN1CC1=CC=CC=C1 OSFLKLGTGPFNRH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- VFQMPVNESQQUJD-UHFFFAOYSA-N n-[4-(1-benzylpiperidin-4-yl)oxyphenyl]-2,2,2-trifluoroethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC(F)(F)F)=CC=C1OC1CCN(CC=2C=CC=CC=2)CC1 VFQMPVNESQQUJD-UHFFFAOYSA-N 0.000 claims description 3
- SASYTMDRFWDSHI-UHFFFAOYSA-N n-[4-(1-benzylpiperidin-4-yl)oxyphenyl]butane-1-sulfonamide Chemical compound C1=CC(NS(=O)(=O)CCCC)=CC=C1OC1CCN(CC=2C=CC=CC=2)CC1 SASYTMDRFWDSHI-UHFFFAOYSA-N 0.000 claims description 3
- QLTBEQARNQQKRW-UHFFFAOYSA-N n-[4-(1-benzylpiperidin-4-yl)oxyphenyl]propane-1-sulfonamide Chemical compound C1=CC(NS(=O)(=O)CCC)=CC=C1OC1CCN(CC=2C=CC=CC=2)CC1 QLTBEQARNQQKRW-UHFFFAOYSA-N 0.000 claims description 3
- IWQONCFXVKWUCA-UHFFFAOYSA-N n-[4-(1-benzylpiperidin-4-yl)oxyphenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1OC1CCN(CC=2C=CC=CC=2)CC1 IWQONCFXVKWUCA-UHFFFAOYSA-N 0.000 claims description 3
- 241001342895 Chorus Species 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- CFSQEWCPQOZZSO-UHFFFAOYSA-N n-[4-(1-benzylpiperidin-4-yl)oxyphenyl]-1-phenylmethanesulfonamide Chemical compound C=1C=C(OC2CCN(CC=3C=CC=CC=3)CC2)C=CC=1NS(=O)(=O)CC1=CC=CC=C1 CFSQEWCPQOZZSO-UHFFFAOYSA-N 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 102000034337 acetylcholine receptors Human genes 0.000 claims 2
- POPPVIRYGJQIOF-UHFFFAOYSA-N 2-acetyloxyethyl(trimethyl)azanium;3-(1-methylpyrrolidin-2-yl)pyridine Chemical compound CC(=O)OCC[N+](C)(C)C.CN1CCCC1C1=CC=CN=C1 POPPVIRYGJQIOF-UHFFFAOYSA-N 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical compound C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 230000006984 memory degeneration Effects 0.000 claims 1
- 208000023060 memory loss Diseases 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 abstract description 5
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 abstract description 3
- 229960004373 acetylcholine Drugs 0.000 abstract 1
- 230000006735 deficit Effects 0.000 abstract 1
- 230000003551 muscarinic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
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- 239000003826 tablet Substances 0.000 description 5
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- PWMGGDQMZHIGDQ-UHFFFAOYSA-N 4-(1-benzylpiperidin-4-yl)oxyaniline Chemical compound C1=CC(N)=CC=C1OC1CCN(CC=2C=CC=CC=2)CC1 PWMGGDQMZHIGDQ-UHFFFAOYSA-N 0.000 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 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 102000009660 Cholinergic Receptors Human genes 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 239000011737 fluorine Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
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- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 2
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10201550A DE10201550A1 (de) | 2002-01-17 | 2002-01-17 | Phenoxy-Piperidine |
| EP02793045A EP1465868A1 (de) | 2002-01-17 | 2002-12-17 | Phenoxy-piperidine zur behandlung von erkrankungen wie schizophrenie und depression |
| JP2003559986A JP4727925B2 (ja) | 2002-01-17 | 2002-12-17 | 統合失調症およびうつ病等の疾患を処置するためのフェノキシピペリジン |
| CA2473409A CA2473409C (en) | 2002-01-17 | 2002-12-17 | Phenoxy-piperidines for the treatment of diseases such as schizophrenia and depression |
| AU2002358735A AU2002358735B9 (en) | 2002-01-17 | 2002-12-17 | Phenoxy piperidines for treating diseases such as schizophrenia and depression |
| HU0500497A HUP0500497A2 (hu) | 2002-01-17 | 2002-12-17 | Fenoxi-piperidin-származékok, ezeket hatóanyagként tartalmazó gyógyszerkészítmények és eljárás előállításukra |
| US10/501,763 US20050131021A1 (en) | 2002-01-17 | 2002-12-17 | Phenoxy piperidines for treating diseases such as schizophrenia and depression |
| PL02373946A PL373946A1 (en) | 2002-01-17 | 2002-12-17 | Phenoxy piperidines for treating diseases such as schizophrenia and depression |
| CNA028272544A CN1615297A (zh) | 2002-01-17 | 2002-12-17 | 治疗精神分裂症和抑郁等疾病的苯氧基－哌啶 |
| PCT/EP2002/014389 WO2003059882A1 (de) | 2002-01-17 | 2002-12-17 | Phenoxy-piperidine zur behandlung von erkrankungen wie schizophenie und depression |
| ZA200406504A ZA200406504B (en) | 2002-01-17 | 2004-08-16 | Phenoxy-piperidines for the treatment of diseases such as schizophrenia and depression. |
| US12/393,480 US20090247584A1 (en) | 2002-01-17 | 2009-02-26 | Phenoxy-piperidines for the treatment of diseases such as schizophrenia and depression |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10201550A DE10201550A1 (de) | 2002-01-17 | 2002-01-17 | Phenoxy-Piperidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10201550A1 true DE10201550A1 (de) | 2003-07-31 |
Family
ID=7712334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10201550A Withdrawn DE10201550A1 (de) | 2002-01-17 | 2002-01-17 | Phenoxy-Piperidine |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20050131021A1 (https=) |
| EP (1) | EP1465868A1 (https=) |
| JP (1) | JP4727925B2 (https=) |
| CN (1) | CN1615297A (https=) |
| AU (1) | AU2002358735B9 (https=) |
| CA (1) | CA2473409C (https=) |
| DE (1) | DE10201550A1 (https=) |
| HU (1) | HUP0500497A2 (https=) |
| PL (1) | PL373946A1 (https=) |
| WO (1) | WO2003059882A1 (https=) |
| ZA (1) | ZA200406504B (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20050861A1 (es) * | 2003-12-03 | 2005-12-10 | Glaxo Group Ltd | Derivados de sales ciclicas de amonio cuaternario como antagonistas del receptor muscarinico de acetilcolina |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| US8787440B2 (en) * | 2008-07-25 | 2014-07-22 | Qualcomm Incorporated | Determination of receive data values |
| RU2014121984A (ru) | 2011-10-31 | 2015-12-10 | Ксенон Фармасьютикалз Инк. | Бензолсульфонамидные соединения и их применение в качестве терапевтических средств |
| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドＸｅｎｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| CN104718188B (zh) | 2012-05-22 | 2018-08-21 | 基因泰克公司 | N-取代的苯甲酰胺类及其在治疗疼痛中的用途 |
| KR101663436B1 (ko) | 2012-07-06 | 2016-10-06 | 제넨테크, 인크. | N-치환된 벤즈아미드 및 이의 사용 방법 |
| RU2015143906A (ru) | 2013-03-14 | 2017-04-18 | Дженентек, Инк. | Замещенные триазолопиридины и способы их применения |
| BR112015023397A2 (pt) | 2013-03-15 | 2017-07-18 | Genentech Inc | benzoxazois substituídos e métodos de uso dos mesmos |
| WO2015078374A1 (en) | 2013-11-27 | 2015-06-04 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| JP2017525677A (ja) | 2014-07-07 | 2017-09-07 | ジェネンテック， インコーポレイテッド | 治療用化合物及びその使用方法 |
| HK1252567A1 (zh) | 2015-05-22 | 2019-05-31 | 基因泰克公司 | 被取代的苯甲酰胺和其使用方法 |
| JP2018526371A (ja) | 2015-08-27 | 2018-09-13 | ジェネンテック， インコーポレイテッド | 治療化合物及びその使用方法 |
| CA2999769A1 (en) | 2015-09-28 | 2017-04-06 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| EP3380466A1 (en) | 2015-11-25 | 2018-10-03 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3436432B1 (en) | 2016-03-30 | 2021-01-27 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| PE20190980A1 (es) | 2016-10-17 | 2019-07-09 | Genentech Inc | Compuestos terapeuticos y metodos para utilizarlos |
| WO2018112842A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor |
| WO2018112840A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6, 5-fused heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2018112843A1 (en) * | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| JP2020511511A (ja) | 2017-03-24 | 2020-04-16 | ジェネンテック， インコーポレイテッド | ナトリウムチャネル阻害剤としての４−ピペリジン−ｎ−（ピリミジン−４−イル）クロマン−７−スルホンアミド誘導体 |
| AR114263A1 (es) | 2018-02-26 | 2020-08-12 | Genentech Inc | Compuestos terapéuticos y métodos para utilizarlos |
| US10947251B2 (en) | 2018-03-30 | 2021-03-16 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776293A (en) * | 1950-08-09 | 1957-01-01 | Nopco Chem Co | Improved hydrogenation process |
| US4216218A (en) * | 1979-02-23 | 1980-08-05 | American Hoechst Corporation | Antidepressant and analgesic 4-aryloxy- and 4-arylthio-3-phenylpiperidines |
| EG18188A (en) * | 1986-05-01 | 1992-09-30 | Pfizer Ltd | Process for preparation anti-arhythmia agents |
| US5093341A (en) * | 1987-12-17 | 1992-03-03 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine derivatives useful as antithrombolytic agents |
| US5169855A (en) * | 1990-03-28 | 1992-12-08 | Du Pont Merck Pharmaceutical Company | Piperidine ether derivatives as psychotropic drugs or plant fungicides |
| US5202346A (en) * | 1992-02-25 | 1993-04-13 | American Home Products Corporation | Piperidinyl and piperazinyl derivatives |
| IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| ZA9610741B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Substituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| IL128524A0 (en) * | 1996-08-15 | 2000-01-31 | Schering Corp | Ether muscarinic antagonists |
| GB9725541D0 (en) * | 1997-12-02 | 1998-02-04 | Pharmacia & Upjohn Spa | Amino-benzothiazole derivatives |
| DE10000739A1 (de) * | 2000-01-11 | 2001-07-12 | Merck Patent Gmbh | Piperidin- und Piperazinderivate |
| JP2002363159A (ja) * | 2001-04-05 | 2002-12-18 | Sankyo Co Ltd | ベンズアミジン誘導体 |
| AU2003248571A1 (en) * | 2002-05-24 | 2003-12-12 | Neurion Pharmaceuticals, Inc. | Methods of determining precise herg interactions and altering compounds based on said interactions |
-
2002
- 2002-01-17 DE DE10201550A patent/DE10201550A1/de not_active Withdrawn
- 2002-12-17 CA CA2473409A patent/CA2473409C/en not_active Expired - Fee Related
- 2002-12-17 JP JP2003559986A patent/JP4727925B2/ja not_active Expired - Fee Related
- 2002-12-17 WO PCT/EP2002/014389 patent/WO2003059882A1/de not_active Ceased
- 2002-12-17 CN CNA028272544A patent/CN1615297A/zh active Pending
- 2002-12-17 US US10/501,763 patent/US20050131021A1/en not_active Abandoned
- 2002-12-17 HU HU0500497A patent/HUP0500497A2/hu unknown
- 2002-12-17 EP EP02793045A patent/EP1465868A1/de not_active Withdrawn
- 2002-12-17 PL PL02373946A patent/PL373946A1/xx unknown
- 2002-12-17 AU AU2002358735A patent/AU2002358735B9/en not_active Ceased
-
2004
- 2004-08-16 ZA ZA200406504A patent/ZA200406504B/en unknown
-
2009
- 2009-02-26 US US12/393,480 patent/US20090247584A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002358735A1 (en) | 2003-07-30 |
| AU2002358735B2 (en) | 2009-03-12 |
| JP2005514457A (ja) | 2005-05-19 |
| JP4727925B2 (ja) | 2011-07-20 |
| AU2002358735B9 (en) | 2009-04-09 |
| US20090247584A1 (en) | 2009-10-01 |
| CA2473409C (en) | 2011-09-27 |
| CN1615297A (zh) | 2005-05-11 |
| PL373946A1 (en) | 2005-09-19 |
| HUP0500497A2 (hu) | 2005-08-29 |
| CA2473409A1 (en) | 2003-07-24 |
| US20050131021A1 (en) | 2005-06-16 |
| ZA200406504B (en) | 2005-09-15 |
| EP1465868A1 (de) | 2004-10-13 |
| WO2003059882A1 (de) | 2003-07-24 |
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| 8139 | Disposal/non-payment of the annual fee |