PL171984B1 - Sposób wytwarzania nowych pochodnych benzotiazolo-lub benzoimidazolo-alkanopiperydyny PL PL PL PL PL - Google Patents
Sposób wytwarzania nowych pochodnych benzotiazolo-lub benzoimidazolo-alkanopiperydyny PL PL PL PL PLInfo
- Publication number
- PL171984B1 PL171984B1 PL92312751A PL31275192A PL171984B1 PL 171984 B1 PL171984 B1 PL 171984B1 PL 92312751 A PL92312751 A PL 92312751A PL 31275192 A PL31275192 A PL 31275192A PL 171984 B1 PL171984 B1 PL 171984B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- group
- compounds
- benzoimidazole
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 abstract description 4
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 3
- 206010012289 Dementia Diseases 0.000 abstract description 2
- 230000002708 enhancing effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- -1 1-ethyl-2-methyl-1H-benzimidazol-5-yl Chemical group 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 102100033639 Acetylcholinesterase Human genes 0.000 description 3
- 108010022752 Acetylcholinesterase Proteins 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 229960004373 acetylcholine Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SGIBOXBBPQRZDM-UHFFFAOYSA-N 1-benzylpiperidine-4-carbaldehyde Chemical compound C1CC(C=O)CCN1CC1=CC=CC=C1 SGIBOXBBPQRZDM-UHFFFAOYSA-N 0.000 description 2
- VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010048650 Cholinesterase inhibition Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910019020 PtO2 Inorganic materials 0.000 description 2
- 229940022698 acetylcholinesterase Drugs 0.000 description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 230000007850 degeneration Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical class C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical class CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- SDGOHAFTDRVBBQ-UHFFFAOYSA-N 1-cyclononyl-1,3-diazonan-2-one Chemical compound O=C1NCCCCCCN1C1CCCCCCCC1 SDGOHAFTDRVBBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical class NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- BCBYNNJOGHVRKP-UHFFFAOYSA-N C(C)N1C(=NC2=C1C=CC(=C2)CC(=O)CC1=CC2=C(N(C(=N2)C)CC)C=C1)C Chemical compound C(C)N1C(=NC2=C1C=CC(=C2)CC(=O)CC1=CC2=C(N(C(=N2)C)CC)C=C1)C BCBYNNJOGHVRKP-UHFFFAOYSA-N 0.000 description 1
- SNEGWDNYBGMVFP-UHFFFAOYSA-N CC=1SC2=C(N=1)C=CC(=C2)CC(=O)CC1=CC2=C(N=C(S2)C)C=C1 Chemical compound CC=1SC2=C(N=1)C=CC(=C2)CC(=O)CC1=CC2=C(N=C(S2)C)C=C1 SNEGWDNYBGMVFP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108010058699 Choline O-acetyltransferase Proteins 0.000 description 1
- 102100023460 Choline O-acetyltransferase Human genes 0.000 description 1
- 102000003914 Cholinesterases Human genes 0.000 description 1
- 108090000322 Cholinesterases Proteins 0.000 description 1
- BBVJRDDCJPBUHS-UHFFFAOYSA-N Cl.C(C)N1C(=NC2=C1C=CC(=C2)CC(CC2CCN(CC2)CC2=CC=CC=C2)=O)C Chemical compound Cl.C(C)N1C(=NC2=C1C=CC(=C2)CC(CC2CCN(CC2)CC2=CC=CC=C2)=O)C BBVJRDDCJPBUHS-UHFFFAOYSA-N 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000220304 Prunus dulcis Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 210000002932 cholinergic neuron Anatomy 0.000 description 1
- 229940048961 cholinesterase Drugs 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
- OHQLYLRYQSZVLV-UHFFFAOYSA-N dioxopalladium Chemical compound O=[Pd]=O OHQLYLRYQSZVLV-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- YHOBGCSGTGDMLF-UHFFFAOYSA-N sodium;di(propan-2-yl)azanide Chemical compound [Na+].CC(C)[N-]C(C)C YHOBGCSGTGDMLF-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Control Of Indicators Other Than Cathode Ray Tubes (AREA)
- Control Of El Displays (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77128391A | 1991-10-03 | 1991-10-03 | |
| PCT/US1992/007230 WO1993007140A1 (en) | 1991-10-03 | 1992-08-31 | Heteroaryl amines as novel acetyl cholinesterase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL171984B1 true PL171984B1 (pl) | 1997-07-31 |
Family
ID=25091318
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL92312751A PL171984B1 (pl) | 1991-10-03 | 1992-08-31 | Sposób wytwarzania nowych pochodnych benzotiazolo-lub benzoimidazolo-alkanopiperydyny PL PL PL PL PL |
| PL92312752A PL171693B1 (pl) | 1991-10-03 | 1992-08-31 | Sposób wytwarzania nowych pochodnych benzotiazoloalkanonopiperydyny PL PL PL PL PL |
| PL92303096A PL171669B1 (en) | 1991-10-03 | 1992-08-31 | Method of obtaining novel derivatives of heteroarylamine |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL92312752A PL171693B1 (pl) | 1991-10-03 | 1992-08-31 | Sposób wytwarzania nowych pochodnych benzotiazoloalkanonopiperydyny PL PL PL PL PL |
| PL92303096A PL171669B1 (en) | 1991-10-03 | 1992-08-31 | Method of obtaining novel derivatives of heteroarylamine |
Country Status (36)
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5620973A (en) * | 1993-11-30 | 1997-04-15 | Takeda Chemical Industries, Ltd. | Tetracyclic condensed heterocyclic compounds and their use |
| EP0976404A3 (en) * | 1998-07-30 | 2001-06-27 | Pfizer Products Inc. | A pharmaceutical composition for the prevention and treatment of diseases of cognitive dysfunction in a mammal |
| US6218383B1 (en) | 1998-08-07 | 2001-04-17 | Targacept, Inc. | Pharmaceutical compositions for the prevention and treatment of central nervous system disorders |
| HUP0104493A3 (en) | 1998-09-30 | 2002-12-28 | Takeda Pharmaceutical | Drugs for improving vesical excretory strength |
| SE9902268D0 (sv) * | 1999-06-16 | 1999-06-16 | Astra Ab | Pharmaceutically active compounds |
| CN1317276C (zh) * | 2000-09-29 | 2007-05-23 | 中国科学院上海药物研究所 | 一类吲哚基哌啶类化合物及其制备方法和用途 |
| KR100823908B1 (ko) * | 2000-10-20 | 2008-04-21 | 바이오비트럼 에이비(피유비엘) | 2-, 3-, 4-, 또는 5-치환-ｎ1-(벤젠술포닐)인돌 및 이의치료 용도 |
| JP2006505571A (ja) * | 2002-10-15 | 2006-02-16 | リゲル ファーマシューテイカルズ、インコーポレイテッド | 置換されたインドール及びｈｃｖ阻害剤としてのその使用 |
| US20060014801A1 (en) * | 2002-11-22 | 2006-01-19 | The Johns Hopkins University | Prevention and treatment of cognitive impairment using (R)-(-)-5-methyl-1-nicotynoyl-2-pyrazoline (MNP) and analogs |
| CA2566204A1 (en) * | 2004-05-14 | 2005-12-01 | The Johns Hopkins University | Method for improving cognitive function by co-administration of a gabab receptor antagonist and an acetylcholinesterase inhibitor |
| EP1600447A1 (en) * | 2004-05-28 | 2005-11-30 | Neuropharma S.A.U. | Butyrylcholinesterase selective inhibitors |
| DK1753764T3 (da) | 2004-06-09 | 2009-02-16 | Glaxo Group Ltd | Pyrrolopyridin-derivater |
| EP2425846A1 (en) * | 2004-12-23 | 2012-03-07 | Voyager Pharmaceutical Corporation | Acetylcholinesterase Inhibitors and leuprolide acetate for the treatment of Alzheimer's disease |
| CN1808106B (zh) * | 2005-01-21 | 2010-11-24 | 中国科学院上海药物研究所 | 一种用核磁共振筛选乙酰胆碱酯酶抑制剂的方法 |
| KR20160127181A (ko) | 2008-08-12 | 2016-11-02 | 진판델 파마슈티컬스 인코포레이티드 | 질환 위험 인자의 식별 방법 |
| US8846315B2 (en) | 2008-08-12 | 2014-09-30 | Zinfandel Pharmaceuticals, Inc. | Disease risk factors and methods of use |
| CN101503414B (zh) * | 2009-03-04 | 2013-10-30 | 沈阳药科大学 | 噻唑并[3,2-b]-1,2,4-三嗪衍生物及其应用 |
| CN103772312B (zh) | 2009-10-02 | 2016-08-17 | 埃维克辛公司 | 抗炎症的2-羰基噻唑和2-羰基恶唑 |
| EP2533645B1 (en) | 2010-02-09 | 2016-07-27 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| CN107362165A (zh) | 2011-01-10 | 2017-11-21 | 金帆德尔制药股份有限公司 | 用于治疗阿尔茨海默病的方法和药物产品 |
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| US20150376161A1 (en) | 2013-01-29 | 2015-12-31 | Avexxin As | Antiiflammatory and antitumor 2-oxothiazoles abd 2-oxothiophenes compounds |
| CA2904767C (en) | 2013-03-15 | 2022-06-21 | Agenebio, Inc. | Methods and compositions for improving cognitive function |
| US10806717B2 (en) | 2013-03-15 | 2020-10-20 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| CN103333163A (zh) * | 2013-07-09 | 2013-10-02 | 广州中医药大学 | 一种苯并呋喃类衍生物及其制备方法和应用 |
| GB201413695D0 (en) | 2014-08-01 | 2014-09-17 | Avexxin As | Compound |
| EA034167B8 (ru) | 2015-05-22 | 2021-04-27 | Эйджинбайо, Инк. | Фармацевтические композиции леветирацетама пролонгированного высвобождения |
| GB201604318D0 (en) | 2016-03-14 | 2016-04-27 | Avexxin As | Combination therapy |
| CN107141266B (zh) * | 2017-06-28 | 2019-04-09 | 佳木斯大学附属第一医院 | 一种用于治疗阿尔茨海默病的杂环化合物及其制备方法 |
| CN115466211B (zh) * | 2022-06-09 | 2024-02-23 | 中国人民解放军空军军医大学 | 一种n-苯基喹啉-4-胺类化合物及其应用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1068259B (enExample) * | 1954-04-28 | 1959-11-05 | ||
| FR2334358A1 (fr) * | 1975-12-12 | 1977-07-08 | Sogeras | Nouveaux medicaments derives de l'indole |
| US4122265A (en) * | 1976-05-21 | 1978-10-24 | Hoffmann-La Roche Inc. | Derivatives of 3-phenylisoindole-1-carboxylic acid |
| ZA815541B (en) * | 1980-08-12 | 1983-03-30 | Glaxo Group Ltd | Heterocyclic compounds |
| GB8615562D0 (en) * | 1986-06-25 | 1986-07-30 | Maggioni Farma | Aminoalcohols |
| KR910006138B1 (ko) * | 1986-09-30 | 1991-08-16 | 에자이 가부시끼가이샤 | 환상아민 유도체 |
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| IT1226100B (it) * | 1988-07-07 | 1990-12-10 | Dompe Farmaceutici Spa | Derivati benzimidazolici farmacologicamente attivi. |
| FR2640266B2 (fr) * | 1988-07-12 | 1992-07-10 | Synthelabo | Derives de (hydroxy-1 piperidinyl-2 alkyl) indolones-2, quinoleinones-2, benzo(b)azepinones-2 et benzimidazolones-2, leur preparation et leur application en therapeutique |
| US4908372A (en) * | 1988-10-13 | 1990-03-13 | Merrell Dow Pharmaceuticals Inc. | Antihistaminic piperidinyl benzimidazoles |
| JP2969359B2 (ja) * | 1989-01-13 | 1999-11-02 | 武田薬品工業株式会社 | 環状アミン化合物 |
| US5064840A (en) * | 1989-08-03 | 1991-11-12 | Merrell Dow Pharmaceuticals | Anti-psychotic piperidylbenzimidazole compounds |
| TW197442B (enExample) * | 1990-02-08 | 1993-01-01 | Pfizer | |
| US5116846A (en) * | 1990-03-28 | 1992-05-26 | Du Pont Merck Pharmaceutical Company | N-aralkyl piperidine derivatives as psychotropic drugs |
| TW197435B (enExample) * | 1990-11-22 | 1993-01-01 | Takeda Pharm Industry Co Ltd | |
| NZ243065A (en) * | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| DE69330823T2 (de) * | 1992-02-13 | 2002-05-02 | Merrell Pharmaceuticals Inc., Cincinnati | Thiacyclische piperidinylderivate |
| CA2092112A1 (en) * | 1992-03-23 | 1993-09-24 | Nobuyoshi Iwata | Indole and indazole derivatives, for the treatment and prophylaxis of cerebral disorders, their preparation and their use |
-
1992
- 1992-08-29 TW TW081106843A patent/TW263504B/zh active
- 1992-08-31 EP EP92918761A patent/EP0606248B1/en not_active Expired - Lifetime
- 1992-08-31 DK DK92918761T patent/DK0606248T3/da active
- 1992-08-31 RU RU9494019972A patent/RU2100357C1/ru not_active IP Right Cessation
- 1992-08-31 HU HU9400952A patent/HU225049B1/hu unknown
- 1992-08-31 DE DE69232976T patent/DE69232976T2/de not_active Expired - Fee Related
- 1992-08-31 PL PL92312751A patent/PL171984B1/pl not_active IP Right Cessation
- 1992-08-31 BR BR9206577A patent/BR9206577A/pt not_active Application Discontinuation
- 1992-08-31 WO PCT/US1992/007230 patent/WO1993007140A1/en not_active Ceased
- 1992-08-31 CA CA002119647A patent/CA2119647C/en not_active Expired - Fee Related
- 1992-08-31 AU AU25196/92A patent/AU667053B2/en not_active Ceased
- 1992-08-31 RO RO94-00533A patent/RO112868B1/ro unknown
- 1992-08-31 UA UA94005424A patent/UA41290C2/uk unknown
- 1992-08-31 CZ CZ1994785A patent/CZ290807B6/cs not_active IP Right Cessation
- 1992-08-31 US US08/211,044 patent/US5574046A/en not_active Expired - Lifetime
- 1992-08-31 JP JP5506442A patent/JP2546785B2/ja not_active Expired - Fee Related
- 1992-08-31 KR KR1019940701066A patent/KR0170458B1/ko not_active Expired - Fee Related
- 1992-08-31 ES ES92918761T patent/ES2193137T3/es not_active Expired - Lifetime
- 1992-08-31 PL PL92312752A patent/PL171693B1/pl not_active IP Right Cessation
- 1992-08-31 SG SG1996006904A patent/SG52618A1/en unknown
- 1992-08-31 PL PL92303096A patent/PL171669B1/pl not_active IP Right Cessation
- 1992-08-31 DE DE9290112U patent/DE9290112U1/de not_active Expired - Lifetime
- 1992-08-31 AT AT92918761T patent/ATE235490T1/de not_active IP Right Cessation
- 1992-09-07 AP APAP/P/1992/000421A patent/AP314A/en active
- 1992-09-15 PH PH44935A patent/PH31290A/en unknown
- 1992-09-24 IL IL10327492A patent/IL103274A/en not_active IP Right Cessation
- 1992-09-25 IS IS3919A patent/IS1745B/is unknown
- 1992-09-30 EG EG58192A patent/EG21481A/xx active
- 1992-09-30 CN CN92112079A patent/CN1035615C/zh not_active Expired - Fee Related
- 1992-10-01 PT PT100917A patent/PT100917B/pt not_active IP Right Cessation
- 1992-10-02 ZA ZA927589A patent/ZA927589B/xx unknown
- 1992-10-02 NZ NZ244601A patent/NZ244601A/en not_active IP Right Cessation
- 1992-10-02 MX MX9205678A patent/MX9205678A/es unknown
- 1992-10-02 UY UY23484A patent/UY23484A1/es not_active IP Right Cessation
- 1992-10-02 MA MA22956A patent/MA22672A1/fr unknown
-
1994
- 1994-03-18 OA OA60484A patent/OA09895A/en unknown
- 1994-03-30 NO NO941179A patent/NO308533B1/no unknown
- 1994-03-31 FI FI941518A patent/FI116939B/fi active IP Right Grant
- 1994-03-31 BG BG98689A patent/BG61727B1/bg unknown
-
1997
- 1997-10-24 US US08/957,639 patent/US6124321A/en not_active Expired - Fee Related
-
1999
- 1999-11-11 US US09/438,712 patent/US6303633B1/en not_active Expired - Fee Related
-
2001
- 2001-08-23 US US09/935,903 patent/US20020049210A1/en not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
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| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20080831 |