PH26465A - Piperidine compounds and their use - Google Patents

Piperidine compounds and their use Download PDF

Info

Publication number: PH26465A
Authority: PH; Philippines
Prior art keywords: mmol; thiadiazol; solution; added; pyridine
Prior art date: 1989-02-22

Application number

PH40049A

Other languages

English (en)

Inventor

Per Sauerberg

Preben Houlberg Olesen

Original Assignee

Ferrosan As

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-02-22

Filing date

1990-02-14

Publication date

1992-07-27

1989-02-22 Priority claimed from DK82589A external-priority patent/DK82589A/da

1989-05-12 Priority claimed from DK231589A external-priority patent/DK231589D0/da

1990-02-14 Application filed by Ferrosan As filed Critical Ferrosan As

1992-07-27 Publication of PH26465A publication Critical patent/PH26465A/en

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
SLBKDWANFYLWFZ-UHFFFAOYSA-N 3-pentoxy-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCCCOC1=NSN=C1C1=CC=CN=C1 SLBKDWANFYLWFZ-UHFFFAOYSA-N 0.000 description 2
OFPSSSJDVAQRKC-UHFFFAOYSA-N 3-pentylsulfanyl-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CCCCCSC1=NSN=C1C1=CC=CN=C1 OFPSSSJDVAQRKC-UHFFFAOYSA-N 0.000 description 2
GOVKKWKQDSVWTF-UHFFFAOYSA-N 3-prop-2-ynoxy-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound C#CCOC1=NSN=C1C1=CC=CN=C1 GOVKKWKQDSVWTF-UHFFFAOYSA-N 0.000 description 2
WQJCDIIQFMIJME-UHFFFAOYSA-N 3-propan-2-yloxy-4-pyridin-3-yl-1,2,5-thiadiazole Chemical compound CC(C)OC1=NSN=C1C1=CC=CN=C1 WQJCDIIQFMIJME-UHFFFAOYSA-N 0.000 description 2
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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
108010009685 Cholinergic Receptors Proteins 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
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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
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
239000012085 test solution Substances 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
ZQDPJFUHLCOCRG-AATRIKPKSA-N trans-3-hexene Chemical compound CC\C=C\CC ZQDPJFUHLCOCRG-AATRIKPKSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Neurosurgery (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)

PH40049A 1989-02-22 1990-02-14 Piperidine compounds and their use PH26465A (en)

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)	EP0384285A3 (sv)
JP (2)	JPH02255680A (sv)
KR (1)	KR0163763B1 (sv)
CN (1)	CN1028105C (sv)
AR (1)	AR247565A1 (sv)
AT (1)	ATE123030T1 (sv)
AU (2)	AU629302B2 (sv)
CA (2)	CA2010579A1 (sv)
DE (1)	DE69019550T2 (sv)
DK (1)	DK0384288T3 (sv)
ES (1)	ES2072323T3 (sv)
FI (2)	FI900887A0 (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)

* Cited by examiner, † Cited by third party
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
US5043345A (en) *	1989-02-22	1991-08-27	Novo Nordisk A/S	Piperidine compounds and their preparation and use
US5264444A (en) *	1989-02-22	1993-11-23	Novo Nordisk A/S	Piperidine compounds 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
DK198590D0 (da) *	1990-08-21	1990-08-21	Novo Nordisk As	Heterocykliske forbindelser, deres fremstilling og anvendelse
US5376668A (en) *	1990-08-21	1994-12-27	Novo Nordisk A/S	Heterocyclic compounds
US5527813A (en) *	1990-08-21	1996-06-18	Novo Nordisk A/S	Heterocyclic compounds and their preparation and use
DK198390D0 (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
US5418240A (en) *	1990-08-21	1995-05-23	Novo Nordisk A/S	Heterocyclic compounds and their preparation and use
USRE35822E (en) *	1990-08-21	1998-06-09	Novo Nordisk A/S	Heterocyclic compounds
EP0561913B1 (en) *	1990-11-29	1998-04-01	Allergan, Inc.	Use of pyridine derivatives in the treatment of ocular hypertension
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
CA2146019A1 (en) *	1992-10-23	1994-05-11	Howard B. Broughton	Dopamine receptor subtype ligands
DE69426021T2 (de) *	1993-06-04	2001-05-17	Novo Nordisk A/S, Bagsvaerd	Xamonelin-Tartrat
CA2169839C (en) *	1993-08-19	2002-06-11	Franklin Porter Bymaster	Antipsychotic method
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
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
US5998404A (en) *	1994-10-24	1999-12-07	Eli Lilly And Company	Heterocyclic compounds and their 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
US5726193A (en) *	1994-10-31	1998-03-10	Eli Lilly And Company	Method for treating anxiety
US5574028A (en) *	1994-10-31	1996-11-12	Eli Lilly And Company	Method for treating anxiety
WO1996013167A1 (en) *	1994-10-31	1996-05-09	Eli Lilly And Company	Method for treating anxiety
US5612351A (en) *	1994-11-08	1997-03-18	Novo Nordisk A/S	Method of treating urinary bladder dysfunctions
US5565475A (en) *	1994-11-08	1996-10-15	Muhlhauser; Mark A.	Method of treating urinary bladder dysfunctions with 3-tetrahydropyridine derivatives
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
US5998434A (en) *	1995-12-06	1999-12-07	Eli Lilly And Company	Composition for treating pain
PL327144A1 (en) *	1995-12-07	1998-11-23	Lilly Co Eli	Method of relieving paints
GB9603755D0 (en) *	1996-02-22	1996-04-24	Pfizer Ltd	Therapeutic agents
AU2991397A (en) *	1996-04-23	1997-11-12	Eli Lilly And Company	Heterocyclic compounds
CA2252573A1 (en) *	1996-04-23	1997-10-30	Celia Ann Whitesitt	Heterocyclic compounds
EP0910566B1 (en) *	1996-04-24	2003-09-17	Novo Nordisk A/S	Heterocyclic compounds and their preparation and use
PT821955E (pt) *	1996-08-01	2002-07-31	Lilly Co Eli	Uso de 3-(4-hexiloxi-1,2,5-tiadiazol-3-il)-1,2,5,6-tetrahidro-1-metilpiridina (xanomelina) para o tratamento da doenca bipolar
EP0821954A1 (en) *	1996-08-01	1998-02-04	Eli Lilly And Company	Method for treating mental retardation
EP0821956A1 (en) *	1996-08-01	1998-02-04	Eli Lilly And Company	Method for treating disruptive behavior disorders
US6043258A (en) *	1996-08-01	2000-03-28	Eli Lilly And Company	Method for treating disruptive behavior disorders with xanomeline
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
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
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
US6117890A (en) *	1996-08-01	2000-09-12	Eli Lilly And Company	Method for treating bipolar disorder
CA2269506A1 (en) *	1996-10-23	1998-04-30	Eli Lilly And Company	Method for treating dementia due to aids
EP1014974B1 (en)	1997-05-29	2004-08-11	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
US6096767A (en)	1999-01-22	2000-08-01	The University Of Toledo	Muscarinic receptor agonists
US6376675B2 (en) *	1999-01-22	2002-04-23	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
CA2620333A1 (en)	2005-08-26	2007-03-01	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation
EP2258357A3 (en)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenesis with acetylcholinesterase inhibitor
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
WO2007047978A2 (en)	2005-10-21	2007-04-26	Braincells, Inc.	Modulation of neurogenesis by pde inhibition
EP2314289A1 (en)	2005-10-31	2011-04-27	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
JP2009521531A (ja) *	2005-12-27	2009-06-04	ザ・ユニバーシティ・オブ・トレド	ムスカリンアゴニスト及びその使用方法
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
US7678808B2 (en)	2006-05-09	2010-03-16	Braincells, Inc.	5 HT receptor mediated neurogenesis
CA2651813A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
EP2068872A1 (en)	2006-09-08	2009-06-17	Braincells, Inc.	Combinations containing a 4-acylaminopyridine derivative
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
EP2296471A4 (en)	2008-05-15	2012-03-14	Univ Toledo	MUSCARIC ACID AGONISTS AS COGNITIVE ENHANCERS
WO2010099217A1 (en)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
US10265311B2 (en)	2009-07-22	2019-04-23	PureTech Health LLC	Methods and compositions for treatment of disorders ameliorated by muscarinic receptor activation
ES2742728T3 (es)	2009-07-22	2020-02-17	PureTech Health LLC	Composiciones para el tratamiento de trastornos mejorados por la activación del receptor muscarínico
NO3034079T3 (sv)	2010-11-15	2018-06-09
WO2012149524A1 (en)	2011-04-29	2012-11-01	The University Of Toledo	Muscarinic agonists as enhancers of working memory and cognitive flexibility
CA2934553C (en)	2013-12-20	2023-10-31	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
BR112020026062B1 (pt)	2018-06-19	2023-04-04	Agenebio, Inc	Compostos derivados de benzodiazepina ou um sal farmaceuticamente aceitavel, isômero ou combinação dos mesmos, composição farmacêutica compreendendo os mesmos e usos dos mesmos para o tratamento de comprometimento cognitivo, câncer cerebral e psicose da doença de parkinson
WO2020069301A1 (en)	2018-09-28	2020-04-02	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
CN115974863B (zh) *	2021-10-14	2024-12-31	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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
US5043345A (en) *	1989-02-22	1991-08-27	Novo Nordisk A/S	Piperidine compounds and their preparation and use
US5264444A (en) *	1989-02-22	1993-11-23	Novo Nordisk A/S	Piperidine compounds and use
US5328925A (en) *	1989-02-22	1994-07-12	Novo Nordisk A/S	Piperidine compounds and their use
US5260311A (en) *	1989-02-22	1993-11-09	Novo Nordisk A/S	Piperidine compounds and their 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 PH PH40049A patent/PH26465A/en unknown
- 1990-02-14 ES ES90102913T patent/ES2072323T3/es not_active Expired - Lifetime
- 1990-02-14 AT AT90102913T patent/ATE123030T1/de not_active IP Right Cessation
- 1990-02-14 DK DK90102913.2T patent/DK0384288T3/da active
- 1990-02-14 EP EP19900102889 patent/EP0384285A3/en not_active Withdrawn
- 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
- 1990-02-16 IL IL93423A patent/IL93423A0/xx unknown
- 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 AU AU49996/90A patent/AU4999690A/en not_active Abandoned
- 1990-02-20 NZ NZ232615A patent/NZ232615A/en unknown
- 1990-02-21 HU HU9000884A patent/HU221623B1/hu not_active IP Right Cessation
- 1990-02-21 AR AR90316209A patent/AR247565A1/es active
- 1990-02-21 RU SU904743296A patent/RU2042676C1/ru not_active IP Right Cessation
- 1990-02-21 NO NO90900831A patent/NO900831L/no unknown
- 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
- 1990-02-22 PT PT93241A patent/PT93241B/pt not_active IP Right Cessation
- 1990-02-22 CN CN90100873A patent/CN1028105C/zh not_active Expired - Fee Related
- 1990-02-22 JP JP2039900A patent/JPH02255680A/ja active Pending
- 1990-02-22 FI FI900887A patent/FI900887A0/fi 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 PT PT93242A patent/PT93242A/pt not_active Application Discontinuation
1991
- 1991-08-15 US US07/745,568 patent/US5284859A/en not_active Expired - Lifetime
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

Also Published As

Publication number	Publication date
GR3017062T3 (en)	1995-11-30
FI95704B (sv)	1995-11-30
JPH02255679A (ja)	1990-10-16
FI95704C (sv)	1996-03-11
FI900886A0 (sv)	1990-02-22
CN1045104A (zh)	1990-09-05
EP0384288B1 (en)	1995-05-24
FI900887A0 (fi)	1990-02-22
DE69019550D1 (de)	1995-06-29
KR0163763B1 (ko)	1998-12-01
NO900830L (no)	1990-08-23
JPH02255680A (ja)	1990-10-16
DE69019550T2 (de)	1995-10-05
PT93241B (pt)	1996-01-31
IL93352A (en)	1994-08-26
CA2010578C (en)	2000-05-23
AR247565A1 (es)	1995-01-31
NZ232615A (en)	1992-06-25
US5284859A (en)	1994-02-08
EP0384285A3 (en)	1991-04-24
IL93423A0 (en)	1990-11-29
US5041455A (en)	1991-08-20
DK0384288T3 (da)	1995-10-02
HUT58326A (en)	1992-02-28
KR910015569A (ko)	1991-09-30
IL93352A0 (en)	1990-11-29
NO900831L (no)	1990-08-23
IE69672B1 (en)	1996-10-02
HU900884D0 (en)	1990-05-28
ATE123030T1 (de)	1995-06-15
JP2921578B2 (ja)	1999-07-19
CA2010578A1 (en)	1990-08-22
NO900830D0 (no)	1990-02-21
RU2042676C1 (ru)	1995-08-27
NO900831D0 (no)	1990-02-21
AU629302B2 (en)	1992-10-01
HU211705A9 (en)	1995-12-28
NO179639C (no)	1996-11-20
AU4999690A (en)	1990-08-30
PT93241A (pt)	1990-08-31
HU221623B1 (hu)	2002-12-28
EP0384288A2 (en)	1990-08-29
PT93242A (pt)	1990-08-31
CN1028105C (zh)	1995-04-05
CA2010579A1 (en)	1990-08-22
US5043345A (en)	1991-08-27
ES2072323T3 (es)	1995-07-16
AU4999790A (en)	1990-08-30
EP0384288A3 (en)	1991-04-10
US5559138A (en)	1996-09-24
IE900504L (en)	1990-08-22
NO179639B (no)	1996-08-12
US5712297A (en)	1998-01-27
EP0384285A2 (en)	1990-08-29

Publication	Publication Date	Title
PH26465A (en)	1992-07-27	Piperidine compounds and their use
US5559136A (en)	1996-09-24	Treatment of Alzheimer's disease using azacyclic compounds
EP0544756B1 (en)	1997-11-05	1,2,5,6-tetrahydro-1-methylpyridines, their preparation and use
US5328925A (en)	1994-07-12	Piperidine compounds and their use
US5260311A (en)	1993-11-09	Piperidine compounds and their use
US5264444A (en)	1993-11-23	Piperidine compounds and use
USRE35822E (en)	1998-06-09	Heterocyclic compounds