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
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239000000284 extract Substances 0.000 description 25
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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
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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
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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
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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
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239000002254 cytotoxic agent Substances 0.000 description 1
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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
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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
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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
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150000004820 halides Chemical class 0.000 description 1
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HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
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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
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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
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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
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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
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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
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235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
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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
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239000012453 solvate Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
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239000001593 sorbitan monooleate Substances 0.000 description 1
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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
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235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
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125000001424 substituent group Chemical group 0.000 description 1
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239000000829 suppository Substances 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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230000002110 toxicologic effect Effects 0.000 description 1
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238000001665 trituration Methods 0.000 description 1
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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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (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)	ATE180785T1 (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)	ES2132223T3 (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
GB9316195D0 (en) *	1993-08-05	1993-09-22	Smithkline Beecham Plc	Pharmaceuticals
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
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
EP0667867A1 (fr) *	1992-11-05	1995-08-23	Smithkline Beecham Plc	Derives de piperidine utiles comme antagonistes de recepteur de 5-ht4
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
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1993
- 1993-03-10 WO PCT/GB1993/000506 patent/WO1993018036A1/fr not_active Ceased
- 1993-03-10 CZ CZ19942210A patent/CZ286194B6/cs not_active IP Right Cessation
- 1993-03-10 ES ES93905561T patent/ES2132223T3/es not_active Expired - Lifetime
- 1993-03-10 KR KR1019940703167A patent/KR100282730B1/ko not_active Expired - Fee Related
- 1993-03-10 IL IL10500393A patent/IL105003A/en not_active IP Right Cessation
- 1993-03-10 EP EP98114130A patent/EP0884319B1/fr not_active Expired - Lifetime
- 1993-03-10 ES ES98114130T patent/ES2219813T3/es not_active Expired - Lifetime
- 1993-03-10 NZ NZ249565A patent/NZ249565A/en not_active IP Right Cessation
- 1993-03-10 AP APAP/P/1993/000494A patent/AP401A/en active
- 1993-03-10 JP JP5515490A patent/JP2831467B2/ja not_active Expired - Lifetime
- 1993-03-10 SI SI9300114A patent/SI9300114B/sl active Search and Examination
- 1993-03-10 MA MA23113A patent/MA22819A1/fr unknown
- 1993-03-10 HU HU9402601A patent/HU219121B/hu unknown
- 1993-03-10 AT AT93905561T patent/ATE180785T1/de active
- 1993-03-10 CA CA2131797A patent/CA2131797C/fr not_active Expired - Fee Related
- 1993-03-10 SK SK1078-94A patent/SK281423B6/sk not_active IP Right Cessation
- 1993-03-10 PT PT98114130T patent/PT884319E/pt unknown
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- 1993-03-10 SG SG1996008846A patent/SG50693A1/en unknown
- 1993-03-10 DK DK98114130T patent/DK0884319T3/da active
- 1993-03-10 AU AU36448/93A patent/AU671102B2/en not_active Expired
- 1993-03-10 DE DE69325167T patent/DE69325167T2/de not_active Expired - Lifetime
- 1993-03-10 UA UA94095780A patent/UA41311C2/uk unknown
- 1993-03-10 RU RU94040864A patent/RU2104279C1/ru not_active IP Right Cessation
- 1993-03-10 MY MYPI93000436A patent/MY110110A/en unknown
- 1993-03-10 AT AT98114130T patent/ATE266033T1/de active
- 1993-03-10 EP EP93905561A patent/EP0630376B1/fr not_active Expired - Lifetime
- 1993-03-10 DK DK93905561T patent/DK0630376T3/da active
- 1993-03-11 MX MX9301348A patent/MX9301348A/es not_active IP Right Cessation
- 1993-03-11 CN CN93102648A patent/CN1043893C/zh not_active Expired - Fee Related
- 1993-05-22 CN CN93107234A patent/CN1085083A/zh active Pending
1994
- 1994-09-09 NO NO943348A patent/NO303638B1/no not_active IP Right Cessation
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1999
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2005
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Also Published As

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

Publication	Publication Date	Title
AP401A (en)	1995-08-29	Condensed indole derivatives as 5H4-receptor antagonists.
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
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
AU668102C (en)	1997-05-15	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
WO2000017207A1 (fr)	2000-03-30	3,4-dihydro-$i(n)-[[1-(3-hydroxybutyl)-4-piperidinyl]methyl]-2$i(h)-[1,3]oxazino[3,2-$i(a)]indole-10-carboxamide utilise comme antagoniste du recepteur 5-ht(4)