DE60203797T2 - Benzo[d]azepin-derivative als 5-ht6-rezeptor-antagonisten - Google Patents
Benzo[d]azepin-derivative als 5-ht6-rezeptor-antagonisten Download PDFInfo
- Publication number
- DE60203797T2 DE60203797T2 DE60203797T DE60203797T DE60203797T2 DE 60203797 T2 DE60203797 T2 DE 60203797T2 DE 60203797 T DE60203797 T DE 60203797T DE 60203797 T DE60203797 T DE 60203797T DE 60203797 T2 DE60203797 T2 DE 60203797T2
- Authority
- DE
- Germany
- Prior art keywords
- benzo
- tetrahydro
- sulfonyl
- azepine
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000002464 receptor antagonist Substances 0.000 title description 2
- 229940044551 receptor antagonist Drugs 0.000 title description 2
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical class C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 title 1
- 108091005435 5-HT6 receptors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- -1 phenyloxy, benzyloxy Chemical group 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- KIMKGDISOLCZFN-UHFFFAOYSA-N 7-indol-1-ylsulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(S(=O)(=O)N3C4=CC=CC=C4C=C3)=CC=C21 KIMKGDISOLCZFN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- NMHWNKKUIRCGIB-UHFFFAOYSA-N 7-(2,3-dihydroindol-1-ylsulfonyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(S(=O)(N3C4=CC=CC=C4CC3)=O)=CC=C21 NMHWNKKUIRCGIB-UHFFFAOYSA-N 0.000 claims description 4
- NOYPAXGYMHKKCY-UHFFFAOYSA-N 7-[(5-bromo-2,3-dihydroindol-1-yl)sulfonyl]-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(S(=O)(=O)N3C4=CC=C(C=C4CC3)Br)=CC=C21 NOYPAXGYMHKKCY-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 230000007000 age related cognitive decline Effects 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
- 208000028698 Cognitive impairment Diseases 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- CHVUYBOCNPVDFI-UHFFFAOYSA-N 7-(4,6-difluoroindol-1-yl)sulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(S(=O)(=O)N3C=CC4=C(F)C=C(C=C43)F)=CC=C21 CHVUYBOCNPVDFI-UHFFFAOYSA-N 0.000 claims 1
- DLYTYTWIXFVGMN-UHFFFAOYSA-N 7-(5,6-difluoroindol-1-yl)sulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(S(=O)(=O)N3C=CC=4C=C(C(=CC=43)F)F)=CC=C21 DLYTYTWIXFVGMN-UHFFFAOYSA-N 0.000 claims 1
- NYXYOLLGVBUDFS-UHFFFAOYSA-N 7-(7-nitroindol-1-yl)sulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(S(=O)(=O)N3C=CC=4C=CC=C(C3=4)[N+](=O)[O-])=CC=C21 NYXYOLLGVBUDFS-UHFFFAOYSA-N 0.000 claims 1
- LUAWNRLPIVPOBE-UHFFFAOYSA-N 7-[6-(trifluoromethyl)indol-1-yl]sulfonyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(S(=O)(=O)N3C=CC4=CC=C(C=C43)C(F)(F)F)=CC=C21 LUAWNRLPIVPOBE-UHFFFAOYSA-N 0.000 claims 1
- NBHUTSNNBGPXAS-UHFFFAOYSA-N 9-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-ylsulfonyl)-1,2,3,4-tetrahydrocarbazole Chemical compound C1CNCCC2=CC(S(=O)(=O)N3C4=CC=CC=C4C=4CCCCC=43)=CC=C21 NBHUTSNNBGPXAS-UHFFFAOYSA-N 0.000 claims 1
- AQJRPRULCZPQFY-UHFFFAOYSA-N 9-(2,3,4,5-tetrahydro-1h-3-benzazepin-7-ylsulfonyl)carbazole Chemical compound C1CNCCC2=CC(S(=O)(=O)N3C4=CC=CC=C4C4=CC=CC=C43)=CC=C21 AQJRPRULCZPQFY-UHFFFAOYSA-N 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 11
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 150000003254 radicals Chemical class 0.000 description 22
- 239000000243 solution Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- VGUXFOQQKWRUJQ-UHFFFAOYSA-N 1-(7-indol-1-ylsulfonyl-1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CN(C(=O)C)CCC2=CC=C(S(=O)(=O)N3C4=CC=CC=C4C=C3)C=C21 VGUXFOQQKWRUJQ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- UHUXURZGWYTGCJ-UHFFFAOYSA-N 1-[7-(2,3-dihydroindol-1-ylsulfonyl)-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1CN(C(=O)C)CCC2=CC=C(S(=O)(=O)N3C4=CC=CC=C4CC3)C=C21 UHUXURZGWYTGCJ-UHFFFAOYSA-N 0.000 description 4
- MNSLMHDJDVPLMJ-UHFFFAOYSA-N 1-[7-[(5-bromo-2,3-dihydroindol-1-yl)sulfonyl]-1,2,4,5-tetrahydro-3-benzazepin-3-yl]ethanone Chemical compound C1CN(C(=O)C)CCC2=CC=C(S(=O)(=O)N3C4=CC=C(Br)C=C4CC3)C=C21 MNSLMHDJDVPLMJ-UHFFFAOYSA-N 0.000 description 4
- HDYXOGXOWXWJHV-UHFFFAOYSA-N 3-acetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl chloride Chemical compound C1CN(C(=O)C)CCC2=CC=C(S(Cl)(=O)=O)C=C21 HDYXOGXOWXWJHV-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000003891 oxalate salts Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 208000015114 central nervous system disease Diseases 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical group N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- QEDCHCLHHGGYBT-UHFFFAOYSA-N 5-bromo-2,3-dihydro-1h-indole Chemical compound BrC1=CC=C2NCCC2=C1 QEDCHCLHHGGYBT-UHFFFAOYSA-N 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical class 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 150000008038 benzoazepines Chemical class 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000027288 circadian rhythm Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 208000003906 hydrocephalus Diseases 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0111186 | 2001-05-08 | ||
| GBGB0111186.3A GB0111186D0 (en) | 2001-05-08 | 2001-05-08 | Novel compounds |
| PCT/EP2002/004804 WO2002089811A1 (en) | 2001-05-08 | 2002-05-02 | Benzo[d]azepine derivatives as 5-ht6 receptor antagonists. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60203797D1 DE60203797D1 (de) | 2005-05-25 |
| DE60203797T2 true DE60203797T2 (de) | 2006-01-19 |
Family
ID=9914193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60203797T Expired - Fee Related DE60203797T2 (de) | 2001-05-08 | 2002-05-02 | Benzo[d]azepin-derivative als 5-ht6-rezeptor-antagonisten |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20040192671A1 (enExample) |
| EP (1) | EP1392316B1 (enExample) |
| JP (1) | JP2004532240A (enExample) |
| AT (1) | ATE293448T1 (enExample) |
| DE (1) | DE60203797T2 (enExample) |
| ES (1) | ES2238583T3 (enExample) |
| GB (1) | GB0111186D0 (enExample) |
| WO (1) | WO2002089811A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60304695T2 (de) * | 2002-02-13 | 2006-09-21 | Glaxo Group Ltd., Greenford | 7-arylsulfonamido-2,3,4,5-tetrahydro-1h-benzo[d]azepin-derivate mit 5-hat-6-rezeptor affinität zur behandlung von erkrankungen des zentralnervensystems |
| BRPI0308696B8 (pt) | 2002-03-27 | 2021-05-25 | Axovant Sciences Gmbh | composto derivado de quinolina, seu processo de preparação, sua composição farmacêutica e seus usos |
| MY133587A (en) | 2002-05-29 | 2007-11-30 | Glaxo Group Ltd | Aromatic sulfones and their medical use |
| BRPI0412263B1 (pt) | 2003-07-22 | 2019-10-15 | Arena Pharmaceuticals, Inc. | Derivados de diaril e aril heteroaril uréia, uso e composição farmacêutica contendo os mesmos, bem como processo para preparação da dita composição |
| GB0321475D0 (en) * | 2003-09-12 | 2003-10-15 | Glaxo Group Ltd | Novel compounds |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| WO2006026754A2 (en) * | 2004-09-03 | 2006-03-09 | Plexxikon, Inc. | Bicyclic heteroaryl pde4b inhibitors |
| WO2009074607A1 (en) | 2007-12-12 | 2009-06-18 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| WO2009123714A2 (en) | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| PH12015501678B1 (en) | 2009-06-17 | 2022-07-06 | Vertex Pharma | Inhibitors of influenza viruses replication |
| US9365521B2 (en) * | 2010-09-01 | 2016-06-14 | Arena Pharmaceuticals, Inc. | Non-hygroscopic salts of 5-HT2C agonists |
| JP2013536858A (ja) * | 2010-09-01 | 2013-09-26 | アリーナ ファーマシューティカルズ, インコーポレイテッド | 5−ht2cアゴニストの速く溶解する剤形 |
| WO2012030938A1 (en) * | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Salts of lorcaserin with optically active acids |
| AU2011343642A1 (en) | 2010-12-16 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| KR20150027267A (ko) | 2012-06-29 | 2015-03-11 | 화이자 인코포레이티드 | LRRK2 억제제로서의 4-(치환된-아미노)-7H-피롤로[2,3-d]피리미딘 |
| US9475816B2 (en) | 2012-09-07 | 2016-10-25 | Takeda Pharmaceutical Company Limited | Substituted-1,4-dihydropyrazolo[4,3-b]indoles |
| AU2014348752C1 (en) | 2013-11-13 | 2019-11-21 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| JP6615755B2 (ja) | 2013-11-13 | 2019-12-04 | バーテックス ファーマシューティカルズ インコーポレイテッド | インフルエンザウイルスの複製の阻害剤 |
| US9695171B2 (en) | 2013-12-17 | 2017-07-04 | Pfizer Inc. | 3,4-disubstituted-1 H-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7H-pyrrolo[2,3-c]pyridazines as LRRK2 inhibitors |
| JP6704416B2 (ja) | 2015-05-13 | 2020-06-03 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | インフルエンザウイルスの複製の阻害剤を調製する方法 |
| WO2016183120A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| EP4119141A1 (en) | 2015-06-12 | 2023-01-18 | Axovant Sciences GmbH | Nelotanserin for the prophylaxis and treatment of rem sleep behavior disorder |
| EP3322415A4 (en) | 2015-07-15 | 2019-03-13 | Axovant Sciences GmbH | DIARYL AND ARYLHETEROARYL UREA DERIVATIVES AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR FOR PROPHYLAXIS AND TREATMENT OF HALLUCINATIONS RELATED TO A NEUROGENERATIVE DISEASE |
| JP6873980B2 (ja) | 2015-09-14 | 2021-05-19 | ファイザー・インク | LRRK2阻害薬としての新規のイミダゾ[4,5−c]キノリンおよびイミダゾ[4,5−c][1,5]ナフチリジン誘導体 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462257A (en) * | 1965-09-13 | 1969-08-19 | Scott & Sons Co O M | Turf management with azauracils plus fertilizer |
| US4013444A (en) * | 1973-02-12 | 1977-03-22 | Minnesota Mining And Manufacturing Company | Inhibiting grass growth with 5-acetamido-2,4-dimethyltrifluoromethanesulfonanilide |
| US4002628A (en) * | 1973-06-18 | 1977-01-11 | Eli Lilly And Company | Novel fluoroalkoxyphenyl-substituted nitrogen heterocycles |
| IE45765B1 (en) * | 1976-08-19 | 1982-11-17 | Ici Ltd | Triazoles and imidazoles useful as plant fungicides and growth regulating agents |
| EP0126713B1 (de) * | 1983-05-18 | 1989-01-18 | Ciba-Geigy Ag | Cyclohexandion-carbonsäurederivate mit herbizider und das Pflanzenwachstum regulierender Wirkung |
| US4704160A (en) * | 1984-04-02 | 1987-11-03 | The O. M. Scott & Sons Company | Combination fertilizer composition |
| US5123951A (en) * | 1986-03-31 | 1992-06-23 | Rhone-Poulenc Nederland B.V. | Synergistic plant growth regulator compositions |
| CA2199959A1 (en) * | 1994-09-14 | 1996-03-21 | Tsuyoshi Watanabe | Epoxycyclohexane derivative and plant growth regulator |
| US5627134A (en) * | 1995-06-05 | 1997-05-06 | Basf Corporation | Plant growth regulating compositions and methods |
| DZ2376A1 (fr) * | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
| EP1091741A4 (en) * | 1998-06-30 | 2002-12-18 | Lilly Co Eli | AZEPINE DERIVATIVES PLAYING A ROLE IN SEROTONIN ASSOCIATED SYSTEMS |
-
2001
- 2001-05-08 GB GBGB0111186.3A patent/GB0111186D0/en not_active Ceased
-
2002
- 2002-05-02 WO PCT/EP2002/004804 patent/WO2002089811A1/en not_active Ceased
- 2002-05-02 JP JP2002586946A patent/JP2004532240A/ja active Pending
- 2002-05-02 EP EP02750872A patent/EP1392316B1/en not_active Expired - Lifetime
- 2002-05-02 US US10/476,902 patent/US20040192671A1/en not_active Abandoned
- 2002-05-02 DE DE60203797T patent/DE60203797T2/de not_active Expired - Fee Related
- 2002-05-02 AT AT02750872T patent/ATE293448T1/de not_active IP Right Cessation
- 2002-05-02 ES ES02750872T patent/ES2238583T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1392316A1 (en) | 2004-03-03 |
| DE60203797D1 (de) | 2005-05-25 |
| ES2238583T3 (es) | 2005-09-01 |
| WO2002089811A1 (en) | 2002-11-14 |
| ATE293448T1 (de) | 2005-05-15 |
| GB0111186D0 (en) | 2001-06-27 |
| EP1392316B1 (en) | 2005-04-20 |
| JP2004532240A (ja) | 2004-10-21 |
| US20040192671A1 (en) | 2004-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60203797T2 (de) | Benzo[d]azepin-derivative als 5-ht6-rezeptor-antagonisten | |
| DE60122767T2 (de) | Indoly-lsulphonyl-verbindungen zur behandlung von störungen des zns | |
| DE69209290T2 (de) | Perhydroisoindolderivate, ihre herstellung und diese enthaltende arzneimittel | |
| DE68920482T2 (de) | 1-Indolylalkyl-4-(substituierte Pyridinyl)-Piperazine. | |
| DE69413542T2 (de) | Perhydroisoindolderivate als substanz p antagonisten | |
| DE69925571T2 (de) | Sulphonamid-derivate zur behandlung von störungen des zentralnervensystems | |
| DE3687080T2 (de) | Azabicyclononyl-indazol-carboxamid mit 5-ht-antagonistischer wirkung. | |
| DE69008012T2 (de) | 4-Fluorbenzolderivate, Herstellungsverfahren und diese enthaltende pharmazeutische Zusammensetzungen. | |
| DE69425736T2 (de) | Formyl- oder Cyano- substituierte Indolderivate mit dopaminergischer Wirkung | |
| DE69106237T2 (de) | Antimigräne Alkoxypyrimidinderivate. | |
| DE69108461T2 (de) | 1-Indolylalkyl-4-(alkoxy-pyrimidinyl)piperazine. | |
| DE69213276T2 (de) | Substituierte Piperidimylmethyl-Ester von 3-Indolcarbonsäure | |
| EP0144986B1 (en) | Indole-3-carboxamide derivatives | |
| DE69105659T2 (de) | 3-Arylindol- und 3-Arylindazolderivate. | |
| DE69617995T2 (de) | Indolalkylderivate von benzodioxanmenthylamin als 5-ht1a rezeptor liganden | |
| DE69806141T2 (de) | Indazoleamid-verbindungen als serotoninergene mittel | |
| JPS63146874A (ja) | インドール誘導体 | |
| DE60304695T2 (de) | 7-arylsulfonamido-2,3,4,5-tetrahydro-1h-benzo[d]azepin-derivate mit 5-hat-6-rezeptor affinität zur behandlung von erkrankungen des zentralnervensystems | |
| DE69819903T2 (de) | Bicyclische verbindungen als liganden der 5-ht1 rezeptoren | |
| US5556851A (en) | Cinnoline-3-carboxylic acid derivatives | |
| DE3878371T2 (de) | Psychotropische bizyklische imide. | |
| DE69733427T2 (de) | Tetrahydrobezindol derivate | |
| DE69414855T2 (de) | N-(piperidinyl-1-alkyl)-substituierte cyclohexancarbonsäureamide als 5ht1a rezeptor antagonisten | |
| DE69324212T2 (de) | Indol-7-carboxamide Derivate als Analgetika | |
| DE68924751T2 (de) | Azacyclische Verbindungen, verwendbar als Arzneimittel. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |