NO822041L - N-oksacyklyl-alkylpiperidinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende dem, og deres anvendelse - Google Patents
N-oksacyklyl-alkylpiperidinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende dem, og deres anvendelseInfo
- Publication number
- NO822041L NO822041L NO822041A NO822041A NO822041L NO 822041 L NO822041 L NO 822041L NO 822041 A NO822041 A NO 822041A NO 822041 A NO822041 A NO 822041A NO 822041 L NO822041 L NO 822041L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- formula
- carbon atoms
- compound
- piperidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- -1 nitro, formyl Chemical group 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000003176 neuroleptic agent Substances 0.000 claims description 3
- 230000000701 neuroleptic effect Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 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 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 125000005277 alkyl imino group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- 239000012458 free base Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000004310 dioxan-2-yl group Chemical group [H]C1([H])OC([H])([H])C([H])(*)OC1([H])[H] 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 230000033228 biological regulation Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 229940025084 amphetamine Drugs 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 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
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GWQOQQVKVOOHTI-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-3-ylmethanol Chemical compound C1=CC=C2OC(CO)COC2=C1 GWQOQQVKVOOHTI-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- QYLFKNVZIFTCIY-UHFFFAOYSA-N 3-(bromomethyl)-2,3-dihydro-1,4-benzodioxine Chemical compound C1=CC=C2OC(CBr)COC2=C1 QYLFKNVZIFTCIY-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- DOAYWDKFDPSTSV-UHFFFAOYSA-N 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2h-benzimidazol-2-one Chemical compound O=C1NC2=CC(Cl)=CC=C2N1C1CCNCC1 DOAYWDKFDPSTSV-UHFFFAOYSA-N 0.000 description 2
- QXPKJUZDMPPKPR-UHFFFAOYSA-N 6-fluoro-3-piperidin-4-yl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC(F)=CC=C2N1C1CCNCC1 QXPKJUZDMPPKPR-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
- 229960004046 apomorphine Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 230000001484 cataleptigenic effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- PPCPQDDCMQRJLS-UHFFFAOYSA-N ethyl 4-(2-amino-4-chloroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=CC=C(Cl)C=C1N PPCPQDDCMQRJLS-UHFFFAOYSA-N 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DYXGUZTVBIRZAV-UHFFFAOYSA-N (5,7-dimethyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC2=CC(C)=CC(C)=C2OC1 DYXGUZTVBIRZAV-UHFFFAOYSA-N 0.000 description 1
- PSKRYGLRLBMOEY-UHFFFAOYSA-N (5-chloro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC2=CC=CC(Cl)=C2OC1 PSKRYGLRLBMOEY-UHFFFAOYSA-N 0.000 description 1
- KFUKBJZAQWKXQR-UHFFFAOYSA-N (5-methyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC2=CC=CC(C)=C2OC1 KFUKBJZAQWKXQR-UHFFFAOYSA-N 0.000 description 1
- LXENBAQOUSPSIN-UHFFFAOYSA-N (6-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC2=CC=C([N+]([O-])=O)C=C2OC1 LXENBAQOUSPSIN-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- AYPKYQSHFKQVDL-UHFFFAOYSA-N 3-(chloromethyl)-2,3-dihydro-1,4-benzodioxine Chemical compound C1=CC=C2OC(CCl)COC2=C1 AYPKYQSHFKQVDL-UHFFFAOYSA-N 0.000 description 1
- ZRPXSXSUVACQHL-UHFFFAOYSA-N 3-(chloromethyl)-5-methyl-2,3-dihydro-1,4-benzodioxine Chemical compound O1CC(CCl)OC2=C1C=CC=C2C ZRPXSXSUVACQHL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BYNBAMHAURJNTR-UHFFFAOYSA-N 3-piperidin-4-yl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C1CCNCC1 BYNBAMHAURJNTR-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- WZVBIHCNOIJOBW-UHFFFAOYSA-N 4-chloro-3-piperidin-4-yl-1h-benzimidazol-2-one Chemical compound C1=2C(Cl)=CC=CC=2NC(=O)N1C1CCNCC1 WZVBIHCNOIJOBW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813124366 DE3124366A1 (de) | 1981-06-20 | 1981-06-20 | N-oxacyclyl-alkylpiperidin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische praeparate und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO822041L true NO822041L (no) | 1982-12-21 |
Family
ID=6135055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO822041A NO822041L (no) | 1981-06-20 | 1982-06-18 | N-oksacyklyl-alkylpiperidinderivater, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende dem, og deres anvendelse |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4470989A (ja) |
| EP (1) | EP0068261B1 (ja) |
| JP (1) | JPS58977A (ja) |
| KR (1) | KR840000540A (ja) |
| AT (1) | ATE12498T1 (ja) |
| AU (1) | AU551182B2 (ja) |
| CA (1) | CA1175432A (ja) |
| DE (2) | DE3124366A1 (ja) |
| DK (1) | DK275782A (ja) |
| ES (1) | ES513102A0 (ja) |
| FI (1) | FI822178L (ja) |
| GR (1) | GR76502B (ja) |
| HU (1) | HU190989B (ja) |
| IE (1) | IE53127B1 (ja) |
| IL (1) | IL66084A (ja) |
| NO (1) | NO822041L (ja) |
| NZ (1) | NZ201006A (ja) |
| PH (1) | PH18536A (ja) |
| PT (1) | PT75070B (ja) |
| ZA (1) | ZA824328B (ja) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101919B1 (en) * | 1982-08-05 | 1986-09-24 | Kabushiki Kaisha Toshiba | Color picture tube and method for manufacturing the same |
| US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5212170A (en) * | 1991-06-21 | 1993-05-18 | American Home Products Corporation | Psychotropic piperidinylmethyl benzodioxans |
| US5221745A (en) * | 1991-06-21 | 1993-06-22 | American Home Products Corp. | Psychotropic piperidinylmethyl benzodioxans |
| US5182292A (en) * | 1991-06-21 | 1993-01-26 | American Home Products Corporation | Psychotropic piperidinylmethyl benzodioxans |
| DE4140540A1 (de) * | 1991-12-09 | 1993-06-17 | Bayer Ag | Neue azaheterocyclylmethyl-chromane |
| GB9603457D0 (ja) * | 1996-02-19 | 1996-04-17 | Merck & Co Inc | |
| US5952351A (en) * | 1995-02-23 | 1999-09-14 | Merck & Co., Inc. | Alpha 1a adrenergic receptor antagonists |
| US6096763A (en) * | 1995-02-23 | 2000-08-01 | Merck & Co., Inc. | α1a adrenergic receptor antagonists |
| US6025355A (en) * | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| US6242198B1 (en) | 1996-07-25 | 2001-06-05 | Cambridge Neuroscience, Inc. | Methods of treatment of eye trauma and disorders |
| US6756389B2 (en) * | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| CZ20014167A3 (cs) * | 1999-06-02 | 2002-06-12 | Janssen Pharmaceutica N. V. | Pyrrolidinylem, piperidinylem nebo homopiperidinylem substituované deriváty benzodioxanu, benzofuranu nebo benzopyranu |
| HUP0201404A3 (en) | 1999-06-02 | 2005-02-28 | Janssen Pharmaceutica Nv | Aminoalkyl substituted benzodioxan, benzofuran or benzopyran derivatives, pharmaceutical compositions containing them and their use and process for their preparations |
| JO2654B1 (en) * | 2000-09-04 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Multiple aryl caroxa amides are useful as lipid - lowering agents |
| JO2409B1 (en) | 2000-11-21 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Second-phenyl carboxy amides are useful as lipid-lowering agents |
| US7244744B2 (en) * | 2001-11-01 | 2007-07-17 | Icagen, Inc. | Piperidines |
| JP5209479B2 (ja) | 2005-09-30 | 2013-06-12 | グラクソ グループ リミテッド | Ｍ１受容体にて活性を有するベンゾイミダゾロン類 |
| US8288412B2 (en) | 2005-09-30 | 2012-10-16 | Glaxo Group Limited | Compounds which have activity at M1 receptor and their uses in medicine |
| DE602006019119D1 (de) | 2005-09-30 | 2011-02-03 | Glaxo Group Ltd | Verbindungen mit aktivität am m1-rezeptor und ihre verwendung in der medizin |
| GB0605784D0 (en) * | 2006-03-22 | 2006-05-03 | Glaxo Group Ltd | Compounds |
| GB0718415D0 (en) | 2007-09-20 | 2007-10-31 | Glaxo Group Ltd | Compounds |
| WO2009037294A1 (en) | 2007-09-20 | 2009-03-26 | Glaxo Group Limited | Compounds which have activity at m1 receptor and their uses in medicine |
| CN108358832A (zh) * | 2017-12-29 | 2018-08-03 | 上海艾康睿医药科技有限公司 | 一种合成4-[(2-氨基-4-氯)苯基]-氨基-n-哌啶甲酸乙酯的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910930A (en) * | 1973-01-04 | 1975-10-07 | Janssen Pharmaceutica Nv | 1-{55 1-{8 2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl{9 -4-piperidyl{56 -2-benzimidazolinones |
| US4066772A (en) * | 1975-07-21 | 1978-01-03 | Janssen Pharmaceutica N.V. | 1,3-Dihydro-1-[3-(1-piperidinyl)propyl]-2H-benzimidazol-2-ones and related compounds |
| GR71865B (ja) * | 1978-03-20 | 1983-07-07 | Ciba Geigy | |
| US4181802A (en) * | 1978-05-11 | 1980-01-01 | Janssen Pharmaceutica N.V. | 1-(Heterocyclylalkyl)-1,3-dihydro-2-H-benzimidazole-2-ones |
| US4329348A (en) * | 1979-02-26 | 1982-05-11 | Ciba-Geigy Corporation | N-Oxacyclic-alkylpiperidines as psychostimulants |
-
1981
- 1981-06-20 DE DE19813124366 patent/DE3124366A1/de not_active Withdrawn
-
1982
- 1982-06-14 EP EP82105174A patent/EP0068261B1/de not_active Expired
- 1982-06-14 DE DE8282105174T patent/DE3262861D1/de not_active Expired
- 1982-06-14 AT AT82105174T patent/ATE12498T1/de active
- 1982-06-15 ES ES513102A patent/ES513102A0/es active Granted
- 1982-06-17 FI FI822178A patent/FI822178L/fi not_active Application Discontinuation
- 1982-06-17 PT PT75070A patent/PT75070B/pt unknown
- 1982-06-18 NZ NZ201006A patent/NZ201006A/en unknown
- 1982-06-18 AU AU84992/82A patent/AU551182B2/en not_active Ceased
- 1982-06-18 IL IL66084A patent/IL66084A/xx unknown
- 1982-06-18 NO NO822041A patent/NO822041L/no unknown
- 1982-06-18 JP JP57104048A patent/JPS58977A/ja active Pending
- 1982-06-18 HU HU821992A patent/HU190989B/hu unknown
- 1982-06-18 DK DK275782A patent/DK275782A/da not_active Application Discontinuation
- 1982-06-18 IE IE1448/82A patent/IE53127B1/en unknown
- 1982-06-18 US US06/389,677 patent/US4470989A/en not_active Expired - Fee Related
- 1982-06-18 KR KR1019820002715A patent/KR840000540A/ko unknown
- 1982-06-18 ZA ZA824328A patent/ZA824328B/xx unknown
- 1982-06-18 CA CA000405525A patent/CA1175432A/en not_active Expired
- 1982-06-18 PH PH27449A patent/PH18536A/en unknown
- 1982-06-18 GR GR68474A patent/GR76502B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0068261B1 (de) | 1985-04-03 |
| US4470989A (en) | 1984-09-11 |
| ES8304974A1 (es) | 1983-03-16 |
| AU551182B2 (en) | 1986-04-17 |
| DK275782A (da) | 1982-12-21 |
| IL66084A (en) | 1986-07-31 |
| IE53127B1 (en) | 1988-07-06 |
| JPS58977A (ja) | 1983-01-06 |
| KR840000540A (ko) | 1984-02-25 |
| NZ201006A (en) | 1985-12-13 |
| ZA824328B (en) | 1983-04-27 |
| EP0068261A1 (de) | 1983-01-05 |
| IE821448L (en) | 1982-12-20 |
| PT75070A (de) | 1982-07-01 |
| AU8499282A (en) | 1983-01-06 |
| IL66084A0 (en) | 1982-09-30 |
| DE3262861D1 (en) | 1985-05-09 |
| HU190989B (en) | 1986-12-28 |
| FI822178L (fi) | 1982-12-21 |
| PH18536A (en) | 1985-08-09 |
| PT75070B (de) | 1985-01-07 |
| ATE12498T1 (de) | 1985-04-15 |
| CA1175432A (en) | 1984-10-02 |
| ES513102A0 (es) | 1983-03-16 |
| GR76502B (ja) | 1984-08-10 |
| DE3124366A1 (de) | 1982-12-30 |
| FI822178A0 (fi) | 1982-06-17 |
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