PH26465A - Piperidine compounds and their use - Google Patents
Piperidine compounds and their use Download PDFInfo
- Publication number
- PH26465A PH26465A PH40049A PH40049A PH26465A PH 26465 A PH26465 A PH 26465A PH 40049 A PH40049 A PH 40049A PH 40049 A PH40049 A PH 40049A PH 26465 A PH26465 A PH 26465A
- Authority
- PH
- Philippines
- Prior art keywords
- mmol
- thiadiazol
- solution
- added
- pyridine
- Prior art date
Links
- 150000003053 piperidines Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 207
- -1 cyclopropylmethoxy, benzyloxy, morpholino Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 230000003920 cognitive function Effects 0.000 claims description 9
- 210000001320 hippocampus Anatomy 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 210000004129 prosencephalon Anatomy 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000004936 stimulating effect Effects 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 5
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 230000000638 stimulation Effects 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- JJWIFEIHNQNTLK-UHFFFAOYSA-N 3-(1-methyl-3,6-dihydro-2h-pyridin-5-yl)-4-pentoxy-1,2,5-thiadiazole Chemical compound CCCCCOC1=NSN=C1C1=CCCN(C)C1 JJWIFEIHNQNTLK-UHFFFAOYSA-N 0.000 claims 1
- LRTWCQHCJKYNPS-UHFFFAOYSA-N 3-(1-methyl-3,6-dihydro-2h-pyridin-5-yl)-4-pentylsulfanyl-1,2,5-thiadiazole Chemical compound CCCCCSC1=NSN=C1C1=CCCN(C)C1 LRTWCQHCJKYNPS-UHFFFAOYSA-N 0.000 claims 1
- SFXHHGRYNXLPKT-UHFFFAOYSA-N 3-butylsulfanyl-4-(1-methyl-3,6-dihydro-2h-pyridin-5-yl)-1,2,5-thiadiazole Chemical compound CCCCSC1=NSN=C1C1=CCCN(C)C1 SFXHHGRYNXLPKT-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 348
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 345
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 224
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
- 239000000243 solution Substances 0.000 description 207
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 153
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 124
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 122
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 118
- 239000011541 reaction mixture Substances 0.000 description 107
- 239000000203 mixture Substances 0.000 description 98
- 239000012074 organic phase Substances 0.000 description 65
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 64
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 62
- 238000004440 column chromatography Methods 0.000 description 61
- 239000003480 eluent Substances 0.000 description 61
- 150000003891 oxalate salts Chemical class 0.000 description 57
- 238000001704 evaporation Methods 0.000 description 55
- 230000008020 evaporation Effects 0.000 description 55
- 239000012071 phase Substances 0.000 description 55
- 239000012279 sodium borohydride Substances 0.000 description 55
- 229910000033 sodium borohydride Inorganic materials 0.000 description 55
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 54
- 238000001914 filtration Methods 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 26
- CMPNWGQBNRHIQZ-UHFFFAOYSA-N 3-chloro-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound ClC1=NSN=C1C1=CC=CN=C1 CMPNWGQBNRHIQZ-UHFFFAOYSA-N 0.000 description 24
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 24
- 239000012312 sodium hydride Substances 0.000 description 24
- 229910000104 sodium hydride Inorganic materials 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 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 17
- 239000011734 sodium Substances 0.000 description 17
- 229910052708 sodium Inorganic materials 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- HLNJFEXZDGURGZ-UHFFFAOYSA-M 1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1 HLNJFEXZDGURGZ-UHFFFAOYSA-M 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 7
- 239000000872 buffer Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 230000003551 muscarinic effect Effects 0.000 description 6
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 230000009870 specific binding Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 description 5
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000472 muscarinic agonist Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- ODEHKVYXWLXRRR-UHFFFAOYSA-N hex-3-yn-1-ol Chemical compound CCC#CCCO ODEHKVYXWLXRRR-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- LJRUNDMAZGRYRB-UHFFFAOYSA-N 2-methylpyridine;oxalic acid Chemical compound OC(=O)C(O)=O.CC1=CC=CC=N1 LJRUNDMAZGRYRB-UHFFFAOYSA-N 0.000 description 3
- KCHCATPDSQWTCN-UHFFFAOYSA-N 3-chloro-4-pyridin-3-yl-1,2,5-oxadiazole Chemical compound ClC1=NON=C1C1=CC=CN=C1 KCHCATPDSQWTCN-UHFFFAOYSA-N 0.000 description 3
- GJHZFNVGXYFFAU-UHFFFAOYSA-N 3-ethoxy-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCOC1=NSN=C1C1=CC=CN=C1 GJHZFNVGXYFFAU-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000001270 agonistic effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- ZCHHRLHTBGRGOT-SNAWJCMRSA-N (E)-hex-2-en-1-ol Chemical compound CCC\C=C\CO ZCHHRLHTBGRGOT-SNAWJCMRSA-N 0.000 description 2
- ZCHHRLHTBGRGOT-PLNGDYQASA-N (z)-hex-2-en-1-ol Chemical compound CCC\C=C/CO ZCHHRLHTBGRGOT-PLNGDYQASA-N 0.000 description 2
- UCPZTWDNVJKOEQ-UHFFFAOYSA-N 1-methyl-3,6-dihydro-2H-pyridine oxalic acid Chemical compound OC(=O)C(O)=O.CN1CCC=CC1 UCPZTWDNVJKOEQ-UHFFFAOYSA-N 0.000 description 2
- BOKWMAAFRMIAMM-UHFFFAOYSA-N 1-methylpiperidine;oxalic acid Chemical compound OC(=O)C(O)=O.CN1CCCCC1 BOKWMAAFRMIAMM-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- OIPHWUPMXHQWLR-UHFFFAOYSA-N 2-pyridin-3-ylacetonitrile Chemical compound N#CCC1=CC=CN=C1 OIPHWUPMXHQWLR-UHFFFAOYSA-N 0.000 description 2
- UUNSVQMTHPONTR-UHFFFAOYSA-M 3-(1-methylpyridin-1-ium-3-yl)-4-pent-3-ynoxy-1,2,5-thiadiazole;iodide Chemical compound [I-].CC#CCCOC1=NSN=C1C1=CC=C[N+](C)=C1 UUNSVQMTHPONTR-UHFFFAOYSA-M 0.000 description 2
- CZIAAGBLEUVHOD-UHFFFAOYSA-M 3-(1-methylpyridin-1-ium-3-yl)-4-pentoxy-1,2,5-thiadiazole;iodide Chemical compound [I-].CCCCCOC1=NSN=C1C1=CC=C[N+](C)=C1 CZIAAGBLEUVHOD-UHFFFAOYSA-M 0.000 description 2
- VZCIVLUQXBASLW-UHFFFAOYSA-M 3-(1-methylpyridin-1-ium-3-yl)-4-phenylmethoxy-1,2,5-thiadiazole;iodide Chemical compound [I-].C[N+]1=CC=CC(C=2C(=NSN=2)OCC=2C=CC=CC=2)=C1 VZCIVLUQXBASLW-UHFFFAOYSA-M 0.000 description 2
- GBBSFWMXZBFUIU-UHFFFAOYSA-M 3-(1-methylpyridin-1-ium-3-yl)-4-propoxy-1,2,5-thiadiazole;iodide Chemical compound [I-].CCCOC1=NSN=C1C1=CC=C[N+](C)=C1 GBBSFWMXZBFUIU-UHFFFAOYSA-M 0.000 description 2
- RMYMEBGDPPJISP-UHFFFAOYSA-M 3-(3-methylbutoxy)-4-(1-methylpyridin-1-ium-3-yl)-1,2,5-thiadiazole;iodide Chemical compound [I-].CC(C)CCOC1=NSN=C1C1=CC=C[N+](C)=C1 RMYMEBGDPPJISP-UHFFFAOYSA-M 0.000 description 2
- LVOFKNONKRQOFG-UHFFFAOYSA-N 3-(3-methylbutoxy)-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CC(C)CCOC1=NSN=C1C1=CC=CN=C1 LVOFKNONKRQOFG-UHFFFAOYSA-N 0.000 description 2
- BVIQAFHUZXUCOE-UHFFFAOYSA-N 3-(4-methylpiperidin-1-yl)-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound C1CC(C)CCN1C1=NSN=C1C1=CC=CN=C1 BVIQAFHUZXUCOE-UHFFFAOYSA-N 0.000 description 2
- KCUKULAEWROPEB-UHFFFAOYSA-N 3-(cyclopropylmethoxy)-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound C1CC1COC1=NSN=C1C1=CC=CN=C1 KCUKULAEWROPEB-UHFFFAOYSA-N 0.000 description 2
- BJLQJZBYVSCITP-UHFFFAOYSA-M 3-but-2-ynoxy-4-(1-methylpyridin-1-ium-3-yl)-1,2,5-thiadiazole;iodide Chemical compound [I-].CC#CCOC1=NSN=C1C1=CC=C[N+](C)=C1 BJLQJZBYVSCITP-UHFFFAOYSA-M 0.000 description 2
- OKTWHVBSBNCONO-UHFFFAOYSA-M 3-butoxy-4-(1-methylpyridin-1-ium-3-yl)-1,2,5-thiadiazole;iodide Chemical compound [I-].CCCCOC1=NSN=C1C1=CC=C[N+](C)=C1 OKTWHVBSBNCONO-UHFFFAOYSA-M 0.000 description 2
- YHMWTFGQYMKBLO-UHFFFAOYSA-N 3-butoxy-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCCOC1=NSN=C1C1=CC=CN=C1 YHMWTFGQYMKBLO-UHFFFAOYSA-N 0.000 description 2
- WWRQHNYMYVIDAR-UHFFFAOYSA-N 3-butylsulfanyl-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCCSC1=NSN=C1C1=CC=CN=C1 WWRQHNYMYVIDAR-UHFFFAOYSA-N 0.000 description 2
- SIERESLMVMKVCT-UHFFFAOYSA-N 3-chloro-1,2,5-thiadiazole Chemical compound ClC=1C=NSN=1 SIERESLMVMKVCT-UHFFFAOYSA-N 0.000 description 2
- GHSRKHUQMJRXQN-UHFFFAOYSA-N 3-chloro-4-(1-methyl-3,6-dihydro-2h-pyridin-5-yl)-1,2,5-thiadiazole Chemical compound C1N(C)CCC=C1C1=NSN=C1Cl GHSRKHUQMJRXQN-UHFFFAOYSA-N 0.000 description 2
- RLVYVDSZOYOCLP-UHFFFAOYSA-M 3-ethoxy-4-(1-methylpyridin-1-ium-3-yl)-1,2,5-thiadiazole;iodide Chemical compound [I-].CCOC1=NSN=C1C1=CC=C[N+](C)=C1 RLVYVDSZOYOCLP-UHFFFAOYSA-M 0.000 description 2
- WXCVSGPFGTZUMI-UHFFFAOYSA-N 3-ethylsulfanyl-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCSC1=NSN=C1C1=CC=CN=C1 WXCVSGPFGTZUMI-UHFFFAOYSA-N 0.000 description 2
- IWJSLHYWUABOAZ-UHFFFAOYSA-N 3-hex-3-ynoxy-4-pyridin-3-yl-1,2,5-oxadiazole Chemical compound CCC#CCCOC1=NON=C1C1=CC=CN=C1 IWJSLHYWUABOAZ-UHFFFAOYSA-N 0.000 description 2
- VJUYUCDQCJLBOZ-UHFFFAOYSA-N 3-hexoxy-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCCCCOC1=NSN=C1C1=CC=CN=C1 VJUYUCDQCJLBOZ-UHFFFAOYSA-N 0.000 description 2
- KLHMNPRNRXOKHJ-UHFFFAOYSA-N 3-hexylsulfanyl-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCCCCSC1=NSN=C1C1=CC=CN=C1 KLHMNPRNRXOKHJ-UHFFFAOYSA-N 0.000 description 2
- CWBOCZDAKBHZCF-UHFFFAOYSA-N 3-methoxy-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound COC1=NSN=C1C1=CC=CN=C1 CWBOCZDAKBHZCF-UHFFFAOYSA-N 0.000 description 2
- NQCSWMGUOOALOC-UHFFFAOYSA-N 3-octylsulfanyl-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCCCCCCSC1=NSN=C1C1=CC=CN=C1 NQCSWMGUOOALOC-UHFFFAOYSA-N 0.000 description 2
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- VTSXYLPJMYSJEM-UHFFFAOYSA-N 3-propoxy-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCOC1=NSN=C1C1=CC=CN=C1 VTSXYLPJMYSJEM-UHFFFAOYSA-N 0.000 description 2
- JJXFRFDBQFOQNF-UHFFFAOYSA-N 3-propylsulfanyl-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCSC1=NSN=C1C1=CC=CN=C1 JJXFRFDBQFOQNF-UHFFFAOYSA-N 0.000 description 2
- VGUMETYVXAZFPT-UHFFFAOYSA-N 3-pyridin-3-yl-1,2,5-oxadiazole Chemical compound C1=NON=C1C1=CC=CN=C1 VGUMETYVXAZFPT-UHFFFAOYSA-N 0.000 description 2
- IWYDMESNVBOFQG-UHFFFAOYSA-N 4-(4-pyridin-3-yl-1,2,5-thiadiazol-3-yl)morpholine Chemical compound C1COCCN1C1=NSN=C1C1=CC=CN=C1 IWYDMESNVBOFQG-UHFFFAOYSA-N 0.000 description 2
- IDKLWXXQSRRTKW-UHFFFAOYSA-M 4-[4-(1-methylpyridin-1-ium-3-yl)-1,2,5-thiadiazol-3-yl]morpholine;iodide Chemical compound [I-].C[N+]1=CC=CC(C=2C(=NSN=2)N2CCOCC2)=C1 IDKLWXXQSRRTKW-UHFFFAOYSA-M 0.000 description 2
- PPUBDHWJUIFECR-UHFFFAOYSA-N 4-pyridin-3-yl-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1=CC=CN=C1 PPUBDHWJUIFECR-UHFFFAOYSA-N 0.000 description 2
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- VXWFEQQIKVSOMK-UHFFFAOYSA-N oxalic acid;pyridine Chemical compound C1=CC=NC=C1.OC(=O)C(O)=O VXWFEQQIKVSOMK-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- IDYNOORNKYEHHO-UHFFFAOYSA-N pent-3-yn-1-ol Chemical compound CC#CCCO IDYNOORNKYEHHO-UHFFFAOYSA-N 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 210000002442 prefrontal cortex Anatomy 0.000 description 1
- DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
- 229960003857 proglumide Drugs 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000004057 substantia innominata Anatomy 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
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- ZQDPJFUHLCOCRG-AATRIKPKSA-N trans-3-hexene Chemical compound CC\C=C\CC ZQDPJFUHLCOCRG-AATRIKPKSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK82589A DK82589A (da) | 1989-02-22 | 1989-02-22 | Piperidinforbindelser, deres fremstilling og anvendelse |
| DK231589A DK231589D0 (da) | 1989-05-12 | 1989-05-12 | Piperidinforbindelser og deres fremstilling og anvendelse |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26465A true PH26465A (en) | 1992-07-27 |
Family
ID=26064725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH40049A PH26465A (en) | 1989-02-22 | 1990-02-14 | Piperidine compounds and their use |
Country Status (22)
| Country | Link |
|---|---|
| US (5) | US5043345A (sv) |
| EP (2) | EP0384288B1 (sv) |
| JP (2) | JPH02255680A (sv) |
| KR (1) | KR0163763B1 (sv) |
| CN (1) | CN1028105C (sv) |
| AR (1) | AR247565A1 (sv) |
| AT (1) | ATE123030T1 (sv) |
| AU (2) | AU4999690A (sv) |
| CA (2) | CA2010579A1 (sv) |
| DE (1) | DE69019550T2 (sv) |
| DK (1) | DK0384288T3 (sv) |
| ES (1) | ES2072323T3 (sv) |
| FI (2) | FI95704C (sv) |
| GR (1) | GR3017062T3 (sv) |
| HU (2) | HU221623B1 (sv) |
| IE (1) | IE69672B1 (sv) |
| IL (2) | IL93352A (sv) |
| NO (2) | NO900831L (sv) |
| NZ (1) | NZ232615A (sv) |
| PH (1) | PH26465A (sv) |
| PT (2) | PT93241B (sv) |
| RU (1) | RU2042676C1 (sv) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0372125A1 (en) * | 1988-11-08 | 1990-06-13 | Akzo N.V. | Oxazole and thiazole derivatives |
| US5260311A (en) * | 1989-02-22 | 1993-11-09 | Novo Nordisk A/S | Piperidine compounds and their use |
| US5264444A (en) * | 1989-02-22 | 1993-11-23 | Novo Nordisk A/S | Piperidine compounds and use |
| US5043345A (en) * | 1989-02-22 | 1991-08-27 | Novo Nordisk A/S | Piperidine compounds and their preparation and use |
| US5328925A (en) * | 1989-02-22 | 1994-07-12 | Novo Nordisk A/S | Piperidine compounds and their use |
| EP0459568A3 (en) * | 1990-05-31 | 1992-09-30 | Merck Sharp & Dohme Ltd. | Substituted oxadiazoles and thiadiazoles for use in the treatment of glaucoma and novel compounds having such use |
| US5376668A (en) * | 1990-08-21 | 1994-12-27 | Novo Nordisk A/S | Heterocyclic compounds |
| DK198390D0 (da) * | 1990-08-21 | 1990-08-21 | Novo Nordisk As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| USRE35822E (en) * | 1990-08-21 | 1998-06-09 | Novo Nordisk A/S | Heterocyclic compounds |
| DK198590D0 (da) * | 1990-08-21 | 1990-08-21 | Novo Nordisk As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| DK198490D0 (da) * | 1990-08-21 | 1990-08-21 | Novo Nordisk As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| US5527813A (en) * | 1990-08-21 | 1996-06-18 | Novo Nordisk A/S | Heterocyclic compounds and their preparation and use |
| US5418240A (en) * | 1990-08-21 | 1995-05-23 | Novo Nordisk A/S | Heterocyclic compounds and their preparation and use |
| ES2113939T3 (es) * | 1990-11-29 | 1998-05-16 | Allergan Inc | Uso de derivados de piridina en el tratamiento de la hipertension ocular. |
| EP0492903A1 (en) * | 1990-12-21 | 1992-07-01 | MERCK SHARP & DOHME LTD. | Substituted pyrazines, pyrimidines and pyridazines for use in the treatment of glaucoma |
| IE922270A1 (en) * | 1991-07-26 | 1993-01-27 | Akzo Nv | Pyrazole derivatives |
| US5641791A (en) * | 1991-08-13 | 1997-06-24 | Novo Nordisk A.S | Heterocyclic compounds and their preparation and use |
| US5175166A (en) * | 1991-08-27 | 1992-12-29 | The University Of Toledo | Muscarinic agonists |
| WO1993014089A1 (en) * | 1992-01-13 | 1993-07-22 | Novo Nordisk A/S | Heterocyclic compounds and their preparation and use |
| US5244906A (en) * | 1992-01-23 | 1993-09-14 | Dowelanco | Insect control with substituted oxadiazole and thiadiazole compounds |
| DE69325662T2 (de) * | 1992-10-23 | 2000-02-10 | Merck Sharp & Dohme Ltd., Hoddesdon | Dopamin rezeptor subtyp liganden |
| SK281980B6 (sk) * | 1993-06-04 | 2001-09-11 | Novo Nordisk A/S | Kryštallický (+)l-hydrogenvínan, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a jeho použitie |
| ATE218864T1 (de) * | 1993-08-19 | 2002-06-15 | Novo Nordisk As | Verwendung von piperidin-derivaten in der behandlung von schizophrenie |
| US5753683A (en) * | 1993-08-19 | 1998-05-19 | Novo Nordisk A/S | Antipsychotic method |
| US5545638A (en) * | 1993-12-21 | 1996-08-13 | Novo Nordisk A/S | Method of treating gastrointestinal motility disorders |
| IL112024A (en) * | 1993-12-21 | 1999-07-14 | Novo Nordisk As | Pharmaceutical compositions comprising tetrahydropyridine derivatives substituted with oxadiazole or thiadiazole for treating gastrointestinal motility disorders |
| US5998404A (en) * | 1994-10-24 | 1999-12-07 | Eli Lilly And Company | Heterocyclic compounds and their use |
| US5605908A (en) * | 1994-10-24 | 1997-02-25 | Eli Lilly And Company | Heterocyclic compounds and their use |
| US5672709A (en) * | 1994-10-24 | 1997-09-30 | Eli Lilly And Company | Heterocyclic compounds and their preparation and use |
| US5484794A (en) * | 1994-11-09 | 1996-01-16 | Eli Lilly And Company | Method for treating anxiety |
| US5488056A (en) * | 1994-10-31 | 1996-01-30 | Eli Lilly And Company | Method for treating anxiety |
| US5574028A (en) * | 1994-10-31 | 1996-11-12 | Eli Lilly And Company | Method for treating anxiety |
| US5726193A (en) * | 1994-10-31 | 1998-03-10 | Eli Lilly And Company | Method for treating anxiety |
| JPH10508028A (ja) * | 1994-10-31 | 1998-08-04 | イーライ・リリー・アンド・カンパニー | 不安を治療する方法 |
| US5565475A (en) * | 1994-11-08 | 1996-10-15 | Muhlhauser; Mark A. | Method of treating urinary bladder dysfunctions with 3-tetrahydropyridine derivatives |
| US5612351A (en) * | 1994-11-08 | 1997-03-18 | Novo Nordisk A/S | Method of treating urinary bladder dysfunctions |
| TW304167B (sv) * | 1995-01-30 | 1997-05-01 | Lilly Co Eli | |
| US5605701A (en) * | 1995-02-17 | 1997-02-25 | Eli Lilly And Company | Transdermal formulation |
| US5852037A (en) * | 1995-11-13 | 1998-12-22 | Eli Lilly And Company | Method for treating anxiety |
| US5763457A (en) | 1995-11-13 | 1998-06-09 | Eli Lilly And Company | Method for treating anxiety |
| WO1997020819A1 (en) * | 1995-12-06 | 1997-06-12 | Eli Lilly And Company | Composition for treating pain |
| AU715645B2 (en) * | 1995-12-07 | 2000-02-10 | Eli Lilly And Company | Method for treating pain |
| GB9603755D0 (en) * | 1996-02-22 | 1996-04-24 | Pfizer Ltd | Therapeutic agents |
| EP0912183A4 (en) * | 1996-04-23 | 1999-08-04 | Lilly Co Eli | HETEROCYCLIC COMPOSITIONS |
| WO1997040016A1 (en) * | 1996-04-23 | 1997-10-30 | Eli Lilly And Company | Heterocyclic compounds |
| WO1997040045A1 (en) * | 1996-04-24 | 1997-10-30 | Novo Nordisk A/S | Heterocyclic compounds and their preparation and use |
| EP0821959A3 (en) * | 1996-08-01 | 1998-09-16 | Eli Lilly And Company | Use of 3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine for treating nicotine withdrawal |
| US6117890A (en) * | 1996-08-01 | 2000-09-12 | Eli Lilly And Company | Method for treating bipolar disorder |
| US6090829A (en) * | 1996-08-01 | 2000-07-18 | Eli Lilly And Company | Method for treating excessive aggression |
| EP0821957A3 (en) * | 1996-08-01 | 1998-04-22 | Eli Lilly And Company | Use of 3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine (xanomeline) for treating substance abuse |
| EP0821954A1 (en) * | 1996-08-01 | 1998-02-04 | Eli Lilly And Company | Method for treating mental retardation |
| US6043258A (en) * | 1996-08-01 | 2000-03-28 | Eli Lilly And Company | Method for treating disruptive behavior disorders with xanomeline |
| EP0821956A1 (en) * | 1996-08-01 | 1998-02-04 | Eli Lilly And Company | Method for treating disruptive behavior disorders |
| EP0821958A3 (en) * | 1996-08-01 | 1998-07-08 | Eli Lilly And Company | Use of 3-(4-hexyloxy-1,2,5-thiadiazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine (xanomeline) for treating excessive aggression |
| DE69710526T2 (de) * | 1996-08-01 | 2002-10-02 | Eli Lilly And Co., Indianapolis | Verwendung von 3-(4-Hexyloxy-1,2,5-Thiadiazol-3-yl)-1,2,5,6-Tetrahydro-1-Methylpyridin (Xanomelin) zur Behandlung von bipolaren Störungen |
| WO1998017214A1 (en) * | 1996-10-23 | 1998-04-30 | Eli Lilly And Company | Method for treating dementia due to aids |
| US6297262B1 (en) | 1997-05-29 | 2001-10-02 | H. Lundbeck A/S | Treatment of schizophrenia and psychosis |
| US6034108A (en) * | 1997-07-28 | 2000-03-07 | Eli Lilly And Company | Method for treating mental retardation |
| US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
| US6376675B2 (en) * | 1999-01-22 | 2002-04-23 | The University Of Toledo | Muscarinic receptor agonists |
| US6096767A (en) | 1999-01-22 | 2000-08-01 | The University Of Toledo | Muscarinic receptor agonists |
| US6211204B1 (en) | 1999-01-22 | 2001-04-03 | University Of Toledo | Muscarinic receptor agonists |
| US20040023951A1 (en) * | 2001-06-18 | 2004-02-05 | Bymaster Franklin Porter | Combination therapy for treatment of psychoses |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| WO2007025177A2 (en) * | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| CN1821243B (zh) * | 2005-08-30 | 2010-12-08 | 北京大学 | 取代的吡啶类m1受体激动剂、其制备方法及其用途 |
| EP2377530A3 (en) | 2005-10-21 | 2012-06-20 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| CN101374836A (zh) * | 2005-12-27 | 2009-02-25 | 托莱多大学 | 毒蕈碱激动剂及其使用方法 |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2377531A2 (en) | 2006-05-09 | 2011-10-19 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| MX2009002496A (es) | 2006-09-08 | 2009-07-10 | Braincells Inc | Combinaciones que contienen un derivado de 4-acilaminopiridina. |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| WO2009140483A1 (en) | 2008-05-15 | 2009-11-19 | University Of Toledo | Muscarinic agonists as cognitive enhancers |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| PL3061821T3 (pl) | 2009-07-22 | 2020-01-31 | PureTech Health LLC | Kompozycje do leczenia zaburzeń łagodzonych przez aktywację receptora muskarynowego |
| US10265311B2 (en) | 2009-07-22 | 2019-04-23 | PureTech Health LLC | Methods and compositions for treatment of disorders ameliorated by muscarinic receptor activation |
| MX346185B (es) | 2010-11-15 | 2017-03-10 | Agenebio Inc | Derivados de piridazina, composiciones y metodos para tratar deterioro cognitivo. |
| US9549928B2 (en) | 2011-04-29 | 2017-01-24 | The University Of Toledo | Muscarinic agonists as enhancers of cognitive flexibility |
| US10329301B2 (en) | 2013-12-20 | 2019-06-25 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US10815242B2 (en) | 2015-06-19 | 2020-10-27 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| EP4019018A1 (en) | 2015-09-11 | 2022-06-29 | Chase Pharmaceuticals Corporation | Muscarinic combination and its use for combating hypocholinergic disorders of the central nervous system |
| US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US11505555B2 (en) | 2016-12-19 | 2022-11-22 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| WO2019246300A1 (en) | 2018-06-19 | 2019-12-26 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| EP3856182A4 (en) | 2018-09-28 | 2022-06-29 | Karuna Therapeutics, Inc. | Compositions and methods for treating disorders ameliorated by muscarnic receptor activation |
| WO2021097427A1 (en) | 2019-11-15 | 2021-05-20 | Karuna Therapeutics, Inc. | Xanomeline derivatives and methods for treating neurological disorders |
| WO2023061372A1 (zh) * | 2021-10-14 | 2023-04-20 | 南京迈诺威医药科技有限公司 | 占诺美林衍生物的苹果酸盐、a晶型及其制备方法和用途 |
| US20240132513A1 (en) | 2022-08-19 | 2024-04-25 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
Family Cites Families (15)
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| NZ219646A (en) * | 1986-03-27 | 1990-10-26 | Merck Sharp & Dohme | Oxadiazole derivatives of azacyclics for treating cns disorders |
| IL83275A (en) * | 1986-09-08 | 1994-02-27 | Novo Nordisk As | Compounds 1,2, 4-Oxadiazolyl Pipridine Transformed, their preparation and pharmaceutical preparations containing them |
| US5017618A (en) * | 1987-03-16 | 1991-05-21 | University Of Florida | Labile derivatives of ketone analogs of 3-substituted-1-alkylamino-2-propanols and their use as beta-adrenergic blockers |
| GB8714789D0 (en) * | 1987-06-24 | 1987-07-29 | Lundbeck & Co As H | Heterocyclic compounds |
| NZ225999A (en) * | 1987-09-10 | 1992-04-28 | Merck Sharp & Dohme | Azacyclic- or azabicyclic-substituted thiadiazole derivatives and pharmaceutical compositions |
| IE63906B1 (en) * | 1987-11-13 | 1995-06-14 | Novo Nordisk As | Azabicyclic compounds and their preparation and use |
| NZ227841A (en) * | 1988-02-12 | 1991-08-27 | Merck Sharp & Dohme | Heterocyclic compounds with at least two non-condensed five membered rings and pharmaceutical compositions |
| DK162892C (da) * | 1988-07-04 | 1992-05-11 | Novo Nordisk As | 1,2,5,6-tetrahydropyridinforbindelser, deres fremstilling og farmaceutiske praeparater indeholdende disse |
| US5328925A (en) * | 1989-02-22 | 1994-07-12 | Novo Nordisk A/S | Piperidine compounds and their use |
| US5043345A (en) * | 1989-02-22 | 1991-08-27 | Novo Nordisk A/S | Piperidine compounds and their preparation and use |
| US5260311A (en) * | 1989-02-22 | 1993-11-09 | Novo Nordisk A/S | Piperidine compounds and their use |
| US5264444A (en) * | 1989-02-22 | 1993-11-23 | Novo Nordisk A/S | Piperidine compounds and use |
| DK198490D0 (da) * | 1990-08-21 | 1990-08-21 | Novo Nordisk As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| DK198390D0 (da) * | 1990-08-21 | 1990-08-21 | Novo Nordisk As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| US5175166A (en) * | 1991-08-27 | 1992-12-29 | The University Of Toledo | Muscarinic agonists |
-
1989
- 1989-08-31 US US07/401,370 patent/US5043345A/en not_active Expired - Lifetime
-
1990
- 1990-02-12 IL IL9335290A patent/IL93352A/en not_active IP Right Cessation
- 1990-02-13 IE IE50490A patent/IE69672B1/en not_active IP Right Cessation
- 1990-02-14 AT AT90102913T patent/ATE123030T1/de not_active IP Right Cessation
- 1990-02-14 DE DE69019550T patent/DE69019550T2/de not_active Expired - Fee Related
- 1990-02-14 EP EP90102913A patent/EP0384288B1/en not_active Expired - Lifetime
- 1990-02-14 EP EP19900102889 patent/EP0384285A3/en not_active Withdrawn
- 1990-02-14 ES ES90102913T patent/ES2072323T3/es not_active Expired - Lifetime
- 1990-02-14 PH PH40049A patent/PH26465A/en unknown
- 1990-02-14 DK DK90102913.2T patent/DK0384288T3/da active
- 1990-02-16 IL IL93423A patent/IL93423A0/xx unknown
- 1990-02-20 AU AU49996/90A patent/AU4999690A/en not_active Abandoned
- 1990-02-20 AU AU49997/90A patent/AU629302B2/en not_active Ceased
- 1990-02-20 US US07/482,272 patent/US5041455A/en not_active Expired - Lifetime
- 1990-02-20 NZ NZ232615A patent/NZ232615A/en unknown
- 1990-02-21 NO NO90900831A patent/NO900831L/no unknown
- 1990-02-21 RU SU904743296A patent/RU2042676C1/ru not_active IP Right Cessation
- 1990-02-21 HU HU9000884A patent/HU221623B1/hu not_active IP Right Cessation
- 1990-02-21 CA CA002010579A patent/CA2010579A1/en not_active Abandoned
- 1990-02-21 NO NO900830A patent/NO179639C/no not_active IP Right Cessation
- 1990-02-21 KR KR1019900002108A patent/KR0163763B1/ko not_active IP Right Cessation
- 1990-02-21 CA CA002010578A patent/CA2010578C/en not_active Expired - Lifetime
- 1990-02-21 AR AR90316209A patent/AR247565A1/es active
- 1990-02-22 JP JP2039900A patent/JPH02255680A/ja active Pending
- 1990-02-22 PT PT93241A patent/PT93241B/pt not_active IP Right Cessation
- 1990-02-22 PT PT93242A patent/PT93242A/pt not_active Application Discontinuation
- 1990-02-22 FI FI900886A patent/FI95704C/sv active IP Right Grant
- 1990-02-22 JP JP2039899A patent/JP2921578B2/ja not_active Expired - Fee Related
- 1990-02-22 CN CN90100873A patent/CN1028105C/zh not_active Expired - Fee Related
- 1990-02-22 FI FI900887A patent/FI900887A0/fi not_active Application Discontinuation
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1991
- 1991-08-15 US US07/745,568 patent/US5284859A/en not_active Expired - Lifetime
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1995
- 1995-06-07 US US08/472,356 patent/US5559138A/en not_active Expired - Lifetime
- 1995-06-29 HU HU95P/P00607P patent/HU211705A9/hu unknown
- 1995-08-09 GR GR950402188T patent/GR3017062T3/el unknown
-
1996
- 1996-09-23 US US08/717,647 patent/US5712297A/en not_active Expired - Lifetime
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