AP401A - Condensed indole derivatives as 5H4-receptor antagonists. - Google Patents

Condensed indole derivatives as 5H4-receptor antagonists. Download PDF

Info

Publication number: AP401A
Authority: AP; ARIPO
Prior art keywords: indole; alkyl; compound according; hydrogen; treated
Prior art date: 1992-03-12

Application number

APAP/P/1993/000494A

Other languages

English (en)

Other versions

AP9300494A0 (en

Inventor

Laramie Mary Gaster

Paul Adrian Wyman

Original Assignee

Smithkline Beecham Plc

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.)

1992-03-12

Filing date

1993-03-10

Publication date

1995-08-29

1992-03-12 Priority claimed from GB929205428A external-priority patent/GB9205428D0/en

1992-09-05 Priority claimed from GB929218846A external-priority patent/GB9218846D0/en

1992-12-29 Priority claimed from GB929227045A external-priority patent/GB9227045D0/en

1993-03-10 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

1993-04-30 Publication of AP9300494A0 publication Critical patent/AP9300494A0/xx

1995-08-29 Application granted granted Critical

1995-08-29 Publication of AP401A publication Critical patent/AP401A/en

Links

229940054051 antipsychotic indole derivative Drugs 0.000 title description 4
150000002475 indoles Chemical class 0.000 title description 4
229940044551 receptor antagonist Drugs 0.000 title description 4
239000002464 receptor antagonist Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 126
150000003839 salts Chemical class 0.000 claims abstract description 15
-1 polymethylene chain Polymers 0.000 claims description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
125000000217 alkyl group Chemical group 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 14
239000003523 serotonin 4 antagonist Substances 0.000 claims description 12
230000000694 effects Effects 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
150000002431 hydrogen Chemical group 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
208000015114 central nervous system disease Diseases 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 3
150000001412 amines Chemical class 0.000 claims 1
230000002526 effect on cardiovascular system Effects 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 124
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 99
239000000243 solution Substances 0.000 description 95
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
239000007787 solid Substances 0.000 description 87
238000005160 1H NMR spectroscopy Methods 0.000 description 76
238000000034 method Methods 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
239000003921 oil Substances 0.000 description 58
235000019198 oils Nutrition 0.000 description 58
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 52
239000000203 mixture Substances 0.000 description 46
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
239000000741 silica gel Substances 0.000 description 41
229910002027 silica gel Inorganic materials 0.000 description 41
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 36
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000000284 extract Substances 0.000 description 25
229910000027 potassium carbonate Inorganic materials 0.000 description 25
235000011181 potassium carbonates Nutrition 0.000 description 23
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000543 intermediate Substances 0.000 description 18
238000010992 reflux Methods 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
235000019441 ethanol Nutrition 0.000 description 17
150000003891 oxalate salts Chemical class 0.000 description 17
239000000725 suspension Substances 0.000 description 17
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 16
238000004587 chromatography analysis Methods 0.000 description 15
239000012043 crude product Substances 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
229910000029 sodium carbonate Inorganic materials 0.000 description 15
LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
239000012458 free base Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
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 9
235000019502 Orange oil Nutrition 0.000 description 9
239000010502 orange oil Substances 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000003981 vehicle Substances 0.000 description 9
HBQIITMSFPSBAF-UHFFFAOYSA-N 1,2-dihydro-[1,3]thiazolo[3,2-a]indole-4-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=C2N1CCS2 HBQIITMSFPSBAF-UHFFFAOYSA-N 0.000 description 8
UNFSNTCNFIQMSM-UHFFFAOYSA-N 3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxamide Chemical compound C12=CC=CC=C2C(C(=O)N)=C2N1CCCO2 UNFSNTCNFIQMSM-UHFFFAOYSA-N 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
KBSNNUAQCDKOLL-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]indole-4-carboxylic acid Chemical compound C1=CC=C2N(C=CS3)C3=C(C(=O)O)C2=C1 KBSNNUAQCDKOLL-UHFFFAOYSA-N 0.000 description 8
150000007942 carboxylates Chemical class 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
208000002551 irritable bowel syndrome Diseases 0.000 description 7
XCEAESKIYSJHOH-UHFFFAOYSA-N n-(piperidin-4-ylmethyl)-3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxamide Chemical compound C=12OCCCN2C2=CC=CC=C2C=1C(=O)NCC1CCNCC1 XCEAESKIYSJHOH-UHFFFAOYSA-N 0.000 description 7
DEWPDCSLWTYBEZ-UHFFFAOYSA-N (1-butylpiperidin-4-yl)methyl 1h-indole-3-carboxylate Chemical compound C1CN(CCCC)CCC1COC(=O)C1=CNC2=CC=CC=C12 DEWPDCSLWTYBEZ-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
208000019695 Migraine disease Diseases 0.000 description 6
241000700159 Rattus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
206010027599 migraine Diseases 0.000 description 6
238000012360 testing method Methods 0.000 description 6
MKGIQRNAGSSHRV-UHFFFAOYSA-N 1,1-dimethyl-4-phenylpiperazin-1-ium Chemical compound C1C[N+](C)(C)CCN1C1=CC=CC=C1 MKGIQRNAGSSHRV-UHFFFAOYSA-N 0.000 description 5
108091005482 5-HT4 receptors Proteins 0.000 description 5
206010003130 Arrhythmia supraventricular Diseases 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
MRNUPCOLNBGBQY-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]indole-4-carboxamide Chemical compound C1=CC=C2N(C=CS3)C3=C(C(=O)N)C2=C1 MRNUPCOLNBGBQY-UHFFFAOYSA-N 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
IMKKVSYOKTZVBO-UHFFFAOYSA-N methyl pyrimido[1,2-a]indole-10-carboxylate Chemical compound C1=CC=NC2=C(C(=O)OC)C3=CC=CC=C3N21 IMKKVSYOKTZVBO-UHFFFAOYSA-N 0.000 description 5
FXCLGAGFIKPOQS-UHFFFAOYSA-N n-[(1-butylpiperidin-4-yl)methyl]-1h-indole-3-carboxamide Chemical compound C1CN(CCCC)CCC1CNC(=O)C1=CNC2=CC=CC=C12 FXCLGAGFIKPOQS-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 5
FLQPYEOKVZYXRL-UHFFFAOYSA-N (1-benzylpiperidin-4-yl)methanol Chemical compound C1CC(CO)CCN1CC1=CC=CC=C1 FLQPYEOKVZYXRL-UHFFFAOYSA-N 0.000 description 4
IIJFYTVJRDKVCI-UHFFFAOYSA-N 1h-indole-3-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CNC2=C1 IIJFYTVJRDKVCI-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
208000006011 Stroke Diseases 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
UELJXCRPLCATAK-UHFFFAOYSA-N ethyl 2-(2-aminophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1N UELJXCRPLCATAK-UHFFFAOYSA-N 0.000 description 4
230000001965 increasing effect Effects 0.000 description 4
KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
SXSSVNBOMMHRRB-UHFFFAOYSA-N (1-butylpiperidin-4-yl)methanamine Chemical compound CCCCN1CCC(CN)CC1 SXSSVNBOMMHRRB-UHFFFAOYSA-N 0.000 description 3
WBJOIIUQZHTVOG-UHFFFAOYSA-N (1-butylpiperidin-4-yl)methanol Chemical compound CCCCN1CCC(CO)CC1 WBJOIIUQZHTVOG-UHFFFAOYSA-N 0.000 description 3
YVKMYGATFMWSKH-UHFFFAOYSA-N 1,2-dihydro-[1,3]thiazolo[3,2-a]indole-4-carboxamide Chemical compound C12=CC=CC=C2C(C(=O)N)=C2N1CCS2 YVKMYGATFMWSKH-UHFFFAOYSA-N 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 3
WJOIMBFFFBIKMN-UHFFFAOYSA-N 6,7-dihydropyrido[1,2-a]indole-10-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=C2N1CCC=C2 WJOIMBFFFBIKMN-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
206010003658 Atrial Fibrillation Diseases 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
238000010171 animal model Methods 0.000 description 3
230000000949 anxiolytic effect Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000008602 contraction Effects 0.000 description 3
239000000945 filler Substances 0.000 description 3
238000011049 filling Methods 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
150000003840 hydrochlorides Chemical class 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
YODYXZOJWGXFSQ-UHFFFAOYSA-N methyl 2-chloro-1h-indole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(Cl)NC2=C1 YODYXZOJWGXFSQ-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
230000004044 response Effects 0.000 description 3
230000003997 social interaction Effects 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
KNUKUWNSGVICSX-UHFFFAOYSA-N (1-benzylpiperidin-4-yl)methanamine Chemical compound C1CC(CN)CCN1CC1=CC=CC=C1 KNUKUWNSGVICSX-UHFFFAOYSA-N 0.000 description 2
HXZJJPILPZILKZ-UHFFFAOYSA-N (1-benzylpiperidin-4-yl)methyl 1h-indole-3-carboxylate Chemical compound C=1NC2=CC=CC=C2C=1C(=O)OCC(CC1)CCN1CC1=CC=CC=C1 HXZJJPILPZILKZ-UHFFFAOYSA-N 0.000 description 2
MPEUCZGCMAPFTF-UHFFFAOYSA-N 1,2-dihydro-[1,3]thiazolo[3,2-a]indole Chemical compound C1=CC=C2N3CCSC3=CC2=C1 MPEUCZGCMAPFTF-UHFFFAOYSA-N 0.000 description 2
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
150000008578 1H-indole-3-carboxylates Chemical class 0.000 description 2
YGKPIROTKVQCCU-UHFFFAOYSA-N 1H-indole-3-carboxylic acid 2-(1-piperidinyl)ethyl ester Chemical compound C=1NC2=CC=CC=C2C=1C(=O)OCCN1CCCCC1 YGKPIROTKVQCCU-UHFFFAOYSA-N 0.000 description 2
PASJVWQAHRQSLY-UHFFFAOYSA-N 2,2,2-trifluoro-1-([1,3]thiazolo[3,2-a]indol-4-yl)ethanone Chemical compound C1=CC=C2N(C=CS3)C3=C(C(=O)C(F)(F)F)C2=C1 PASJVWQAHRQSLY-UHFFFAOYSA-N 0.000 description 2
XQSBNCPFMSWWID-UHFFFAOYSA-N 2-(2,2-diethoxyethylsulfanyl)-1h-indole Chemical compound C1=CC=C2NC(SCC(OCC)OCC)=CC2=C1 XQSBNCPFMSWWID-UHFFFAOYSA-N 0.000 description 2
DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 description 2
HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 description 2
229940113081 5 Hydroxytryptamine 3 receptor antagonist Drugs 0.000 description 2
SWMKEKWSYNCILC-UHFFFAOYSA-N 5-fluoro-1h-indole-3-carbonyl chloride Chemical compound FC1=CC=C2NC=C(C(Cl)=O)C2=C1 SWMKEKWSYNCILC-UHFFFAOYSA-N 0.000 description 2
GXSNICHQWUUDOK-UHFFFAOYSA-N 5-fluoro-1h-indole-3-carboxamide Chemical compound C1=C(F)C=C2C(C(=O)N)=CNC2=C1 GXSNICHQWUUDOK-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
RGYQRAMBURVZSX-UHFFFAOYSA-N CC1=CN2C3=CC=CC=C3C(=C2N=C1C)C(=O)O Chemical compound CC1=CN2C3=CC=CC=C3C(=C2N=C1C)C(=O)O RGYQRAMBURVZSX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
239000004150 EU approved colour Substances 0.000 description 2
208000005189 Embolism Diseases 0.000 description 2
AMEPLSYBMNTGDJ-UHFFFAOYSA-N FC1=CC=2C(=C3N(C=2C=C1)CCCO3)C(=O)N Chemical compound FC1=CC=2C(=C3N(C=2C=C1)CCCO3)C(=O)N AMEPLSYBMNTGDJ-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
206010019233 Headaches Diseases 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
150000001204 N-oxides Chemical class 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
VWCSKOOKIFHMPC-UHFFFAOYSA-N OC(C1=C(CCCC2)N2C2=C1CCC=C2)=O Chemical compound OC(C1=C(CCCC2)N2C2=C1CCC=C2)=O VWCSKOOKIFHMPC-UHFFFAOYSA-N 0.000 description 2
229920005439 Perspex® Polymers 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
230000003474 anti-emetic effect Effects 0.000 description 2
230000036506 anxiety Effects 0.000 description 2
239000002249 anxiolytic agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
239000003795 chemical substances by application 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
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229940095074 cyclic amp Drugs 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
201000006549 dyspepsia Diseases 0.000 description 2
239000008157 edible vegetable oil Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
RCLYBAMOARZBSN-UHFFFAOYSA-N ethyl 1,2,6,7,8,9-hexahydropyrido[1,2-a]indole-10-carboxylate Chemical compound N12CCCCC2=C(C(=O)OCC)C2=C1C=CCC2 RCLYBAMOARZBSN-UHFFFAOYSA-N 0.000 description 2
JDMCKRPUEOBJHJ-UHFFFAOYSA-N ethyl 2,3-dihydro-1h-pyrrolo[1,2-a]indole-4-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OCC)=C2N1CCC2 JDMCKRPUEOBJHJ-UHFFFAOYSA-N 0.000 description 2
LWXUARDMALWDAO-UHFFFAOYSA-N ethyl 2-[2-(4-chlorobutanoylamino)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC=C1NC(=O)CCCCl LWXUARDMALWDAO-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
239000000499 gel Substances 0.000 description 2
230000010243 gut motility Effects 0.000 description 2
231100000869 headache Toxicity 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
XPOFELVXMSSKQL-UHFFFAOYSA-N methyl 2-amino-1h-indole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(N)NC2=C1 XPOFELVXMSSKQL-UHFFFAOYSA-N 0.000 description 2
FVCOPMDCKPXHDZ-UHFFFAOYSA-N methyl 5-fluoro-1h-indole-3-carboxylate Chemical compound C1=C(F)C=C2C(C(=O)OC)=CNC2=C1 FVCOPMDCKPXHDZ-UHFFFAOYSA-N 0.000 description 2
QXAUTQFAWKKNLM-UHFFFAOYSA-N methyl indole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=CNC2=C1 QXAUTQFAWKKNLM-UHFFFAOYSA-N 0.000 description 2
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000004899 motility Effects 0.000 description 2
210000004400 mucous membrane Anatomy 0.000 description 2
BXVCFLARGCBLEP-UHFFFAOYSA-N n-(2-bromoethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCBr BXVCFLARGCBLEP-UHFFFAOYSA-N 0.000 description 2
QBQNECQABSHBMX-UHFFFAOYSA-N n-[(1-benzylpiperidin-4-yl)methyl]-1h-indole-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C=1C(=O)NCC(CC1)CCN1CC1=CC=CC=C1 QBQNECQABSHBMX-UHFFFAOYSA-N 0.000 description 2
JDCHIBIXWGFOBR-UHFFFAOYSA-N n-[(1-butylpiperidin-4-yl)methyl]-2-chloro-1h-indole-3-carboxamide Chemical compound C1CN(CCCC)CCC1CNC(=O)C1=C(Cl)NC2=CC=CC=C12 JDCHIBIXWGFOBR-UHFFFAOYSA-N 0.000 description 2
239000002687 nonaqueous vehicle Substances 0.000 description 2
239000004533 oil dispersion Substances 0.000 description 2
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
229940049953 phenylacetate Drugs 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
239000004926 polymethyl methacrylate Substances 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
XUGQMJOUKXSKPZ-UHFFFAOYSA-N pyrimido[1,2-a]indole-10-carboxylic acid Chemical compound C1=CC=NC2=C(C(=O)O)C3=CC=CC=C3N21 XUGQMJOUKXSKPZ-UHFFFAOYSA-N 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000003826 tablet Substances 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
239000008096 xylene Substances 0.000 description 2
ODURYXPRTQCSGE-UHFFFAOYSA-N (1-butylpiperidin-4-yl)methyl 2-(3-chloropropylsulfanyl)-1h-indole-3-carboxylate Chemical compound C1CN(CCCC)CCC1COC(=O)C1=C(SCCCCl)NC2=CC=CC=C12 ODURYXPRTQCSGE-UHFFFAOYSA-N 0.000 description 1
XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
MGCWCUBVCXHCBZ-UHFFFAOYSA-N 1-(1,2-dihydro-[1,3]thiazolo[3,2-a]indol-4-yl)-2,2,2-trifluoroethanone Chemical compound C12=CC=CC=C2C(C(=O)C(F)(F)F)=C2N1CCS2 MGCWCUBVCXHCBZ-UHFFFAOYSA-N 0.000 description 1
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
ZNRGQMMCGHDTEI-UHFFFAOYSA-N 1H-indole-3-carboxylic acid (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) ester Chemical compound C1=CC=C2C(C(=O)OC3CC4CCC(C3)N4C)=CNC2=C1 ZNRGQMMCGHDTEI-UHFFFAOYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
LNDMOIIJTXMMMB-UHFFFAOYSA-N 2,2,2-trifluoro-1-(1-methyl-[1,3]thiazolo[3,2-a]indol-4-yl)ethanone Chemical compound C1=CC=C2N3C(C)=CSC3=C(C(=O)C(F)(F)F)C2=C1 LNDMOIIJTXMMMB-UHFFFAOYSA-N 0.000 description 1
RIPCDSAZUUSSJZ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[1,2-a]indole-4-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=C2N1CCC2 RIPCDSAZUUSSJZ-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
RRFOKZBJARGPQS-UHFFFAOYSA-N 2-(4-chlorobutoxy)-1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=C(OCCCCCl)NC2=C1 RRFOKZBJARGPQS-UHFFFAOYSA-N 0.000 description 1
KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
WJAXXWSZNSFVNG-UHFFFAOYSA-N 2-bromoethanamine;hydron;bromide Chemical compound [Br-].[NH3+]CCBr WJAXXWSZNSFVNG-UHFFFAOYSA-N 0.000 description 1
SXIIAHIAZAMFPW-UHFFFAOYSA-N 2-chloro-1h-indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(Cl)NC2=C1 SXIIAHIAZAMFPW-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 1
POJULWUAFBTVCQ-UHFFFAOYSA-N 3,4-dihydro-2h-[1,3]thiazino[3,2-a]indole-10-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=C2N1CCCS2 POJULWUAFBTVCQ-UHFFFAOYSA-N 0.000 description 1
KQOQXYPZBYTICM-UHFFFAOYSA-N 3-bromo-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CBr KQOQXYPZBYTICM-UHFFFAOYSA-N 0.000 description 1
ZTGQZSKPSJUEBU-UHFFFAOYSA-N 3-bromopropan-1-amine Chemical compound NCCCBr ZTGQZSKPSJUEBU-UHFFFAOYSA-N 0.000 description 1
RMVOXEVCGLDIKU-UHFFFAOYSA-N 3-chloro-1-n,1-n'-dimethylpropane-1,1-diamine Chemical compound CNC(NC)CCCl RMVOXEVCGLDIKU-UHFFFAOYSA-N 0.000 description 1
BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
TZCFWOHAWRIQGF-UHFFFAOYSA-N 3-chloropropane-1-thiol Chemical compound SCCCCl TZCFWOHAWRIQGF-UHFFFAOYSA-N 0.000 description 1
GZSKEXSLDPEFPT-HZMBPMFUSA-N 4-amino-n-[(4s,5s)-1-azabicyclo[3.3.1]nonan-4-yl]-5-chloro-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)N[C@@H]1[C@H](C2)CCCN2CC1 GZSKEXSLDPEFPT-HZMBPMFUSA-N 0.000 description 1
102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
108091005479 5-HT2 receptors Proteins 0.000 description 1
102000035037 5-HT3 receptors Human genes 0.000 description 1
108091005477 5-HT3 receptors Proteins 0.000 description 1
SVNNWKWHLOJLOK-UHFFFAOYSA-N 5-chloropentanoyl chloride Chemical compound ClCCCCC(Cl)=O SVNNWKWHLOJLOK-UHFFFAOYSA-N 0.000 description 1
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
HBPVGJGBRWIVSX-UHFFFAOYSA-N 6-bromohexanoyl chloride Chemical compound ClC(=O)CCCCCBr HBPVGJGBRWIVSX-UHFFFAOYSA-N 0.000 description 1
235000019489 Almond oil Nutrition 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000282465 Canis Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
206010008088 Cerebral artery embolism Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
208000032382 Ischaemic stroke Diseases 0.000 description 1
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 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
RLJFTICUTYVZDG-UHFFFAOYSA-N Methiothepine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2CC1N1CCN(C)CC1 RLJFTICUTYVZDG-UHFFFAOYSA-N 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
206010046543 Urinary incontinence Diseases 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
NKEGHPOGONHAJP-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]indole Chemical compound C1=CC=C2N3C=CSC3=CC2=C1 NKEGHPOGONHAJP-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
229940008309 acetone / ethanol Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000005529 alkyleneoxy group Chemical group 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229940125683 antiemetic agent Drugs 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
125000002393 azetidinyl group Chemical group 0.000 description 1
238000003287 bathing Methods 0.000 description 1
238000010009 beating Methods 0.000 description 1
230000006399 behavior Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
UNSCWVXFEJEHEZ-UHFFFAOYSA-N benzyl pyrimido[1,2-a]indole-10-carboxylate Chemical compound C12=CC=CC=C2N2C=CC=NC2=C1C(=O)OCC1=CC=CC=C1 UNSCWVXFEJEHEZ-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
229960004484 carbachol Drugs 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
210000001175 cerebrospinal fluid Anatomy 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
230000009194 climbing Effects 0.000 description 1
229960003920 cocaine Drugs 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
238000012505 colouration Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
239000002254 cytotoxic agent Substances 0.000 description 1
231100000599 cytotoxic agent Toxicity 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
210000004921 distal colon Anatomy 0.000 description 1
238000004821 distillation Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
230000003073 embolic effect Effects 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
210000005216 enteric neuron Anatomy 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
CJHXMQCYEILGFT-UHFFFAOYSA-N ethyl 2-(2-nitrophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1[N+]([O-])=O CJHXMQCYEILGFT-UHFFFAOYSA-N 0.000 description 1
OEKWLWGLAKDLIY-UHFFFAOYSA-N ethyl 2-[2-(5-chloropentanoylamino)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC=C1NC(=O)CCCCCl OEKWLWGLAKDLIY-UHFFFAOYSA-N 0.000 description 1
ZFKINOAANMPSCQ-UHFFFAOYSA-N ethyl 2-[2-(6-chlorohexanoylamino)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC=C1NC(=O)CCCCCCl ZFKINOAANMPSCQ-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 1
230000000763 evoking effect Effects 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
230000005176 gastrointestinal motility Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
MFWNKCLOYSRHCJ-BTTYYORXSA-N granisetron Chemical compound C1=CC=C2C(C(=O)N[C@H]3C[C@H]4CCC[C@@H](C3)N4C)=NN(C)C2=C1 MFWNKCLOYSRHCJ-BTTYYORXSA-N 0.000 description 1
229960003727 granisetron Drugs 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000003370 grooming effect Effects 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
210000001320 hippocampus Anatomy 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
201000010849 intracranial embolism Diseases 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
HSLDUAFBCXHBHM-UHFFFAOYSA-N methyl 1-methyl-3,4-dihydro-2h-pyrimido[1,2-a]indole-10-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OC)=C2N1CCCN2C HSLDUAFBCXHBHM-UHFFFAOYSA-N 0.000 description 1
CVLQVYGGVIIUDI-UHFFFAOYSA-N methyl 2,4-dimethylpyrimido[1,2-a]indole-10-carboxylate Chemical compound CC1=CC(C)=NC2=C(C(=O)OC)C3=CC=CC=C3N21 CVLQVYGGVIIUDI-UHFFFAOYSA-N 0.000 description 1
JOPOHNNCBFYVIM-UHFFFAOYSA-N methyl 3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OC)=C2N1CCCO2 JOPOHNNCBFYVIM-UHFFFAOYSA-N 0.000 description 1
FPAAYSLTBWGWJE-UHFFFAOYSA-N methyl 6,7-dihydropyrido[1,2-a]indole-10-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OC)=C2N1CCC=C2 FPAAYSLTBWGWJE-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
BTVLHRJXWYIQLD-UHFFFAOYSA-N n-(2-piperidin-1-ylethyl)-1h-indole-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C=1C(=O)NCCN1CCCCC1 BTVLHRJXWYIQLD-UHFFFAOYSA-N 0.000 description 1
DSPZACYWELKKEB-UHFFFAOYSA-N n-(piperidin-4-ylmethyl)butan-1-amine Chemical compound CCCCNCC1CCNCC1 DSPZACYWELKKEB-UHFFFAOYSA-N 0.000 description 1
NIYNWNTYCWPIAV-UHFFFAOYSA-N n-[(1-benzylpiperidin-4-yl)methyl]-3,4-dihydro-2h-[1,3]oxazino[3,2-a]indole-10-carboxamide;oxalic acid Chemical compound OC(=O)C(O)=O.C=12OCCCN2C2=CC=CC=C2C=1C(=O)NCC(CC1)CCN1CC1=CC=CC=C1 NIYNWNTYCWPIAV-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
230000008693 nausea Effects 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
150000002825 nitriles Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000001253 polyvinylpolypyrrolidone Substances 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
239000002325 prokinetic agent Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229960005335 propanol Drugs 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007789 sealing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000759 toxicological effect Toxicity 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/452—Piperidinium derivatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Cardiology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)

APAP/P/1993/000494A 1992-03-12 1993-03-10 Condensed indole derivatives as 5H4-receptor antagonists. AP401A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB929205428A GB9205428D0 (en)	1992-03-12	1992-03-12	Pharmaceuticals
GB929218846A GB9218846D0 (en)	1992-09-05	1992-09-05	Pharmaceuticals
GB929227045A GB9227045D0 (en)	1992-12-29	1992-12-29	Pharmaceuticals

Publications (2)

Publication Number	Publication Date
AP9300494A0 AP9300494A0 (en)	1993-04-30
AP401A true AP401A (en)	1995-08-29

Family

ID=27266092

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1993/000494A AP401A (en)	1992-03-12	1993-03-10	Condensed indole derivatives as 5H4-receptor antagonists.

Country Status (29)

Country	Link
EP (2)	EP0884319B1 (fr)
JP (1)	JP2831467B2 (fr)
KR (1)	KR100282730B1 (fr)
CN (2)	CN1043893C (fr)
AP (1)	AP401A (fr)
AT (2)	ATE266033T1 (fr)
AU (1)	AU671102B2 (fr)
CA (1)	CA2131797C (fr)
CY (1)	CY2510B1 (fr)
CZ (1)	CZ286194B6 (fr)
DE (2)	DE69333504T2 (fr)
DK (2)	DK0884319T3 (fr)
ES (2)	ES2219813T3 (fr)
FI (1)	FI107158B (fr)
GR (1)	GR3030668T3 (fr)
HU (1)	HU219121B (fr)
IL (1)	IL105003A (fr)
MA (1)	MA22819A1 (fr)
MX (1)	MX9301348A (fr)
MY (1)	MY110110A (fr)
NO (1)	NO303638B1 (fr)
NZ (1)	NZ249565A (fr)
PT (1)	PT884319E (fr)
RU (1)	RU2104279C1 (fr)
SG (1)	SG50693A1 (fr)
SI (1)	SI9300114B (fr)
SK (1)	SK281423B6 (fr)
UA (1)	UA41311C2 (fr)
WO (1)	WO1993018036A1 (fr)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5998409A (en) *	1992-03-12	1999-12-07	Smithkline Beecham Plc	Condensed indole derivatives as 5HT4 -receptor antagonists
US5852014A (en) *	1992-03-12	1998-12-22	Smithkline Beecham P.L.C.	Condensed indole derivatives as 5HT4 -receptor antagonists
GB9316195D0 (en) *	1993-08-05	1993-09-22	Smithkline Beecham Plc	Pharmaceuticals
MX9305947A (es) *	1992-09-29	1994-06-30	Smithkline Beecham Plc	Compuestos antagonistas del receptor 5-ht4, procedimiento para su preparacion y composiciones farmaceuticas que las contienen.
WO1994008965A1 (fr) *	1992-10-16	1994-04-28	Smithkline Beecham Plc	Esters/amides n-alkylpiperidinyl-4-methyl carboxyliques des systemes de cycles condenses en tant qu'inhibiteurs de recepteurs 5-ht4
US5705498A (en) *	1992-11-05	1998-01-06	Smithkline Beecham Plc.	Piperidine derivatives as 5-HT4 receptor antagonists
FR2699921B1 (fr) *	1992-12-30	1995-02-10	Synthelabo	Dérivés d'acide 2-(thien-2-yl)imidazo[2,1-b]benzothiazole-3-acétique, leur préparation et leur application en thérapeutique.
GB9303340D0 (en) *	1993-02-19	1993-04-07	Smithkline Beecham Plc	Pharmaceuticals
GB9310582D0 (en) *	1993-05-22	1993-07-07	Smithkline Beecham Plc	Pharmaceuticals
GB9312348D0 (en) *	1993-06-16	1993-07-28	Smithkline Beecham Plc	Pharmaceuticals
KR100219922B1 (ko) *	1996-05-16	1999-09-01	이서봉	신규한 항바이러스성 6-아릴옥시 및 6-아릴카르보닐 2,4-피리미딘디온 유도체 및 그의 제조 방법
US6013666A (en) *	1996-07-02	2000-01-11	Sang Sup Jew	Oxirane carboxylic acid derivative and its manufacturing method
US6100397A (en) *	1996-08-16	2000-08-08	Smithkline Beecham Plc	Process for the preparation of N-[(1-n butyl-4-piperidyl)methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-a] indole-10-carboxamide and salts and intermediates in the process
WO1998007728A1 (fr) *	1996-08-16	1998-02-26	Smithkline Beecham Plc	PROCEDE POUR LA PREPARATION DE N-[(1-nBUTYL-4-PIPERIDYL)METHYLE] -3,4-DIHYDRO -2H-[1,3] OXAZINO[3,2-A] INDOLE-10-CARBOXAMIDE ET SELS ET INTERMEDIAIRES UTILISES DANS CE PROCEDE
GB9618967D0 (en) *	1996-09-11	1996-10-23	Smithkline Beecham Plc	Pharmaceuticals
GB9725933D0 (en) *	1997-12-05	1998-02-04	Smithkline Beecham Plc	Pharmaceuticals
US6277870B1 (en) *	1998-05-04	2001-08-21	Astra Ab	Use
US6251893B1 (en) *	1998-06-15	2001-06-26	Nps Allelix Corp.	Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity
US20020091271A1 (en)	1998-07-16	2002-07-11	Smithkline Beecham Plc	Process for the preparation of an indole derivative
GB9819035D0 (en) *	1998-09-01	1998-10-28	Cerebrus Res Ltd	Chemical compounds VII
JP3366323B2 (ja) *	1998-09-10	2003-01-14	エフ．ホフマン−ラロシュアーゲー	５−ｈｔ４受容体アンタゴニストとしてのジヒドロベンゾジオキシンカルボキサミド及びケトン誘導体
GB9820294D0 (en) *	1998-09-17	1998-11-11	Smithkline Beecham Plc	Pharmaceuticals
US6545004B1 (en)	1999-10-27	2003-04-08	Cytokinetics, Inc.	Methods and compositions utilizing quinazolinones
US7230000B1 (en)	1999-10-27	2007-06-12	Cytokinetics, Incorporated	Methods and compositions utilizing quinazolinones
AU2005203196B9 (en) *	2000-08-07	2009-04-09	Glaxo Group Limited	The use of 5HT4 receptor antagonists in the prophylaxis or treatment of certain cardiovascular conditions
AU782863C (en) *	2000-08-07	2006-08-31	Glaxo Group Limited	The use of 5HT4 receptor antagonists in the prophylaxis or treatment of certain cardiovascular conditions
MXPA03001210A (es) *	2000-08-07	2004-08-12	Smithkline Beecham Corp	Uso de antagonista del receptor 5-ht4 en la fabricacion de un medicamento para la profilaxis o tratamiento de fibrilacion atrial.
AU782870C (en) *	2000-08-07	2007-03-15	Glaxo Group Limited	The use of 5HT4 receptor antagonists in the prophylaxis or treatment of certain cardiovascular conditions
NZ535261A (en)	2000-08-08	2004-12-24	Smithkline Beecham P	A tablet comprising the hydrochloride salt of N-(1-nbutyl-4-piperidinyl)methyl]-3,4-[1,3]oxazino[3,2-a] indole-10-carboxamide
CA2418921C (fr) *	2000-08-08	2010-10-26	Smithkline Beecham P.L.C.	Nouvelle composition
BR0307666A (pt) *	2002-02-14	2005-01-11	Glaxo Group Ltd	Composição farmacêutica compreendendo n-[(1-n-butil-4-piperidinil)metil]-3,4-diidro-2h[1-3]oxazi no(3,2-a) indol-10-carboxamida ou sal e processo para esta compreendendo granulação seca
US7009049B2 (en)	2002-02-15	2006-03-07	Cytokinetics, Inc.	Syntheses of quinazolinones
AU2003270015A1 (en)	2002-05-09	2003-12-02	Cytokinetics, Inc.	Compounds, compositions, and methods
US7166595B2 (en)	2002-05-09	2007-01-23	Cytokinetics, Inc.	Compounds, methods and compositions
GB0211230D0 (en)	2002-05-16	2002-06-26	Medinnova Sf	Treatment of heart failure
WO2003103575A2 (fr)	2002-05-23	2003-12-18	Cytokinetics, Inc.	Composes, compositions et procedes
CA2489367A1 (fr)	2002-06-14	2003-12-24	Cytokinetics, Inc.	Composes, compositions et procedes
WO2004009036A2 (fr)	2002-07-23	2004-01-29	Cytokinetics, Inc.	Composes, compositions et procedes
WO2004034972A2 (fr)	2002-09-30	2004-04-29	Cytokinetics, Inc.	Composes, compositions, et procedes
ITMI20031468A1 (it)	2003-07-18	2005-01-19	Acraf	Farmaco ativo nel dolore neuropatico
ITMI20031467A1 (it) *	2003-07-18	2005-01-19	Acraf	Farmaco attivo nel dolore neuropatico
EP1692112A4 (fr)	2003-12-08	2008-09-24	Cytokinetics Inc	Composes, compositions, et methodes associees
WO2005061483A2 (fr)	2003-12-23	2005-07-07	Bio-Medisinsk Innovasjon As	Modulateurs de recepteurs peripheriques 5-ht
JP4612301B2 (ja) *	2003-12-26	2011-01-12	広栄化学工業株式会社	１−アルキル−４−アミノメチルピペリジンの製造法
RU2401257C2 (ru) *	2004-12-07	2010-10-10	Янссен Фармацевтика Н.В.	Новые замещенные тетрациклические производные тетрагидрофурана, пирролидина и тетрагидротиофена
RU2320662C1 (ru) *	2006-08-24	2008-03-27	Андрей Александрович Иващенко	ЗАМЕЩЕННЫЕ ПИРРОЛО[4,3-b]ИНДОЛЫ, КОМБИНАТОРНАЯ И ФОКУСИРОВАННАЯ БИБЛИОТЕКИ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ
CN101801937A (zh)	2007-06-22	2010-08-11	艾科尔公司	喹唑啉酮化合物及其使用方法
GB0905641D0 (en) *	2009-04-01	2009-05-13	Serodus As	Compounds
WO2021116487A1 (fr)	2019-12-13	2021-06-17	Som Innovation Biotech, S.A.	Composés destinés à être utilisés dans le traitement d'une maladie de niemann-pick de type c
WO2025077825A1 (fr) *	2023-10-13	2025-04-17	Fauna Bio Incorporated	Méthodes et compositions pour le traitement de troubles cardio-pulmonaires

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1566307A (en) *	1975-12-19	1980-04-30	Hoechst Ag	Indole derivatives of amides and amino esters and process for their manufacture
EP0429984A2 (fr) *	1989-11-17	1991-06-05	Nisshin Flour Milling Co., Ltd.	Dérivés d'indole
EP0485962A2 (fr) *	1990-11-16	1992-05-20	Syntex (U.S.A.) Inc.	Composés tricycliques

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU622330B2 (en) *	1989-06-23	1992-04-02	Takeda Chemical Industries Ltd.	Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides
GB9103862D0 (en) *	1991-02-25	1991-04-10	Glaxo Group Ltd	Chemical compounds
US5206382A (en) *	1991-06-27	1993-04-27	Fidia Georgetown Institute For The Neurosciences	Indole derivatives, pharmaceutical compositions and methods of treating neurological and psychiatric disorders

1993
- 1993-03-10 RU RU94040864A patent/RU2104279C1/ru not_active IP Right Cessation
- 1993-03-10 WO PCT/GB1993/000506 patent/WO1993018036A1/fr not_active Ceased
- 1993-03-10 KR KR1019940703167A patent/KR100282730B1/ko not_active Expired - Fee Related
- 1993-03-10 EP EP98114130A patent/EP0884319B1/fr not_active Expired - Lifetime
- 1993-03-10 PT PT98114130T patent/PT884319E/pt unknown
- 1993-03-10 DE DE69333504T patent/DE69333504T2/de not_active Expired - Lifetime
- 1993-03-10 DK DK98114130T patent/DK0884319T3/da active
- 1993-03-10 EP EP93905561A patent/EP0630376B1/fr not_active Expired - Lifetime
- 1993-03-10 NZ NZ249565A patent/NZ249565A/en not_active IP Right Cessation
- 1993-03-10 DE DE69325167T patent/DE69325167T2/de not_active Expired - Lifetime
- 1993-03-10 JP JP5515490A patent/JP2831467B2/ja not_active Expired - Lifetime
- 1993-03-10 MY MYPI93000436A patent/MY110110A/en unknown
- 1993-03-10 AT AT98114130T patent/ATE266033T1/de active
- 1993-03-10 DK DK93905561T patent/DK0630376T3/da active
- 1993-03-10 SK SK1078-94A patent/SK281423B6/sk not_active IP Right Cessation
- 1993-03-10 AU AU36448/93A patent/AU671102B2/en not_active Expired
- 1993-03-10 UA UA94095780A patent/UA41311C2/uk unknown
- 1993-03-10 ES ES98114130T patent/ES2219813T3/es not_active Expired - Lifetime
- 1993-03-10 CZ CZ19942210A patent/CZ286194B6/cs not_active IP Right Cessation
- 1993-03-10 MA MA23113A patent/MA22819A1/fr unknown
- 1993-03-10 AP APAP/P/1993/000494A patent/AP401A/en active
- 1993-03-10 CA CA2131797A patent/CA2131797C/fr not_active Expired - Fee Related
- 1993-03-10 HU HU9402601A patent/HU219121B/hu unknown
- 1993-03-10 SG SG1996008846A patent/SG50693A1/en unknown
- 1993-03-10 IL IL10500393A patent/IL105003A/en not_active IP Right Cessation
- 1993-03-10 SI SI9300114A patent/SI9300114B/sl active Search and Examination
- 1993-03-10 ES ES93905561T patent/ES2132223T3/es not_active Expired - Lifetime
- 1993-03-10 AT AT93905561T patent/ATE180785T1/de active
- 1993-03-11 CN CN93102648A patent/CN1043893C/zh not_active Expired - Fee Related
- 1993-03-11 MX MX9301348A patent/MX9301348A/es not_active IP Right Cessation
- 1993-05-22 CN CN93107234A patent/CN1085083A/zh active Pending
1994
- 1994-09-09 NO NO943348A patent/NO303638B1/no not_active IP Right Cessation
- 1994-09-12 FI FI944204A patent/FI107158B/fi not_active IP Right Cessation
1999
- 1999-06-30 GR GR990401755T patent/GR3030668T3/el unknown
2005
- 2005-04-12 CY CY0500021A patent/CY2510B1/xx unknown

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1566307A (en) *	1975-12-19	1980-04-30	Hoechst Ag	Indole derivatives of amides and amino esters and process for their manufacture
EP0429984A2 (fr) *	1989-11-17	1991-06-05	Nisshin Flour Milling Co., Ltd.	Dérivés d'indole
EP0485962A2 (fr) *	1990-11-16	1992-05-20	Syntex (U.S.A.) Inc.	Composés tricycliques

Also Published As

Publication number	Publication date
MX9301348A (es)	1993-09-01
FI944204A0 (fi)	1994-09-12
SG50693A1 (en)	1998-07-20
WO1993018036A1 (fr)	1993-09-16
SK107894A3 (en)	1995-04-12
HUT71121A (en)	1995-11-28
CZ286194B6 (cs)	2000-02-16
KR100282730B1 (ko)	2001-02-15
FI107158B (fi)	2001-06-15
NO303638B1 (no)	1998-08-10
DK0630376T3 (da)	1999-06-23
HU9402601D0 (en)	1994-12-28
JPH07504433A (ja)	1995-05-18
CN1043893C (zh)	1999-06-30
CN1085083A (zh)	1994-04-13
JP2831467B2 (ja)	1998-12-02
DE69333504D1 (de)	2004-06-09
PT884319E (pt)	2004-09-30
ES2132223T3 (es)	1999-08-16
NO943348D0 (no)	1994-09-09
CA2131797C (fr)	2010-05-18
RU2104279C1 (ru)	1998-02-10
RU94040864A (ru)	1996-07-20
ATE266033T1 (de)	2004-05-15
AU671102B2 (en)	1996-08-15
DE69333504T2 (de)	2005-05-12
CN1078471A (zh)	1993-11-17
NO943348L (no)	1994-11-09
NZ249565A (en)	1997-07-27
MA22819A1 (fr)	1993-10-01
FI944204L (fi)	1994-09-12
SI9300114A (sl)	1993-12-31
GR3030668T3 (en)	1999-10-29
SI9300114B (sl)	2006-08-31
EP0884319A3 (fr)	1999-02-10
EP0630376A1 (fr)	1994-12-28
DE69325167D1 (de)	1999-07-08
SK281423B6 (sk)	2001-03-12
KR950700304A (ko)	1995-01-16
MY110110A (en)	1998-01-27
AP9300494A0 (en)	1993-04-30
IL105003A (en)	1996-09-12
HK1012352A1 (en)	1999-07-30
AU3644893A (en)	1993-10-05
CY2510B1 (en)	2005-12-23
IL105003A0 (en)	1993-07-08
DE69325167T2 (de)	2000-01-20
EP0884319B1 (fr)	2004-05-06
ES2219813T3 (es)	2004-12-01
EP0630376B1 (fr)	1999-06-02
UA41311C2 (uk)	2001-09-17
ATE180785T1 (de)	1999-06-15
CA2131797A1 (fr)	1993-09-16
HU219121B (hu)	2001-02-28
EP0884319A2 (fr)	1998-12-16
CZ221094A3 (en)	1995-09-13
DK0884319T3 (da)	2004-08-30

Publication	Publication Date	Title
EP0630376B1 (fr)	1999-06-02	Derives condenses d'indoles en tant qu'antagonistes du recepteur 5-ht4
JP3294611B2 (ja)	2002-06-24	５−ｈｔ４レセプター・アンタゴニスト
BRPI1101193A2 (pt)	2014-02-25	Lâmina vibratória, vibrador, oscilador, e dispositivo eletrônico
NZ243993A (en)	1994-10-26	Pharmaceutical compositions having 5-ht4 receptor antagonist activity and selected compounds having such activity
US5726187A (en)	1998-03-10	N-alkylpiperidinyl-4-methyl carboxylic esters/amides of condensed ring systems as 5-HT4 receptor antagonists
US5852014A (en)	1998-12-22	Condensed indole derivatives as 5HT4 -receptor antagonists
EP0629198A1 (fr)	1994-12-21	Composes azotes heterocycliques utiles comme medicaments
US5998409A (en)	1999-12-07	Condensed indole derivatives as 5HT4 -receptor antagonists
EP0712406B1 (fr)	1998-10-28	Derives condenses d'indoles en tant qu'antagonistes du recepteur de 5-ht 4
AP373A (en)	1994-12-07	Compounds having 5TH4 receptor antagonist activity.
HK1012352B (en)	2000-06-23	Condensed indole derivatives as 5-ht4-receptor antagonists
PL172692B1 (pl)	1997-11-28	Skondensowane pochodne indolu PL
HK1023560A1 (en)	2000-09-15	N-(1-nbutyl-4-piperidyl)methyl-3,4-dihydro-2h-1,3 oxazino 3,2-a indole-10-carboxamide or a pharmaceutically acceptable salt thereof
HK1023560B (en)	2005-03-04	N-(1-nbutyl-4-piperidyl)methyl-3,4-dihydro-2h-1,3 oxazino 3,2-a indole-10-carboxamide or a pharmaceutically acceptable salt thereof
HK1012347B (en)	2000-05-12	Condensed indole derivatives as 5-ht 4-receptor antagonists