CA2116024A1 - Antagonistes des recepteurs 5-ht4 - Google Patents

Antagonistes des recepteurs 5-ht4

Info

Publication number: CA2116024A1
Authority: CA; Canada
Prior art keywords: butyl; piperidyl; nmr; water; added
Prior art date: 1991-08-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002116024A

Other languages

English (en)

Inventor

Francis David King

Laramie Mary Gaster

Graham Francis Joiner

Shirley Katherine Rahman

Gareth John Sanger

Kay Alison Wardle

Gordon Smith Baxter

Guy Anthony Kennett

Rodney Christopher Young

Mythily Vimal

Alberto Julio Kaumann

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SmithKline Beecham Ltd

Original Assignee

Individual

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.)

1991-08-20

Filing date

1992-08-18

Publication date

1993-03-04

1991-08-20 Priority claimed from GB919117943A external-priority patent/GB9117943D0/en

1991-09-14 Priority claimed from GB919119692A external-priority patent/GB9119692D0/en

1992-01-23 Priority claimed from GB929201414A external-priority patent/GB9201414D0/en

1992-02-25 Priority claimed from GB929203977A external-priority patent/GB9203977D0/en

1992-04-15 Priority claimed from GB929208321A external-priority patent/GB9208321D0/en

1992-08-18 Application filed by Individual filed Critical Individual

1993-03-04 Publication of CA2116024A1 publication Critical patent/CA2116024A1/fr

Status Abandoned legal-status Critical Current

Links

229940044551 receptor antagonist Drugs 0.000 title description 10
239000002464 receptor antagonist Substances 0.000 title description 10
108091005482 5-HT4 receptors Proteins 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 88
238000011282 treatment Methods 0.000 claims abstract description 22
208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 6
208000015114 central nervous system disease Diseases 0.000 claims abstract description 5
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 4
-1 2-piperidinoethyl 1H-indole-3-carboxylate Chemical compound 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 13
208000002551 irritable bowel syndrome Diseases 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
238000010992 reflux Methods 0.000 claims description 8
239000003523 serotonin 4 antagonist Substances 0.000 claims description 8
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206010027599 migraine Diseases 0.000 claims description 7
206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
201000006549 dyspepsia Diseases 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
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238000004519 manufacturing process Methods 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
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238000005481 NMR spectroscopy Methods 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 37
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238000000034 method Methods 0.000 description 33
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101150041968 CDC13 gene Proteins 0.000 description 23
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
125000000217 alkyl group Chemical group 0.000 description 22
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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239000000377 silicon dioxide Substances 0.000 description 8
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
UVMHZXOYSWLKCG-UHFFFAOYSA-N (1-butylpyrrolidin-3-yl)methanol Chemical compound CCCCN1CCC(CO)C1 UVMHZXOYSWLKCG-UHFFFAOYSA-N 0.000 description 5
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
MWROMYZOULPPDZ-UHFFFAOYSA-N 1-(1-butylpiperidin-3-yl)ethanol Chemical compound CCCCN1CCCC(C(C)O)C1 MWROMYZOULPPDZ-UHFFFAOYSA-N 0.000 description 5
102000035037 5-HT3 receptors Human genes 0.000 description 5
108091005477 5-HT3 receptors Proteins 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
229940093499 ethyl acetate Drugs 0.000 description 5
239000010410 layer Substances 0.000 description 5
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229910000027 potassium carbonate Inorganic materials 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
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 4
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 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
208000006011 Stroke Diseases 0.000 description 4
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HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
238000004821 distillation Methods 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 4
230000001965 increasing effect Effects 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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239000002002 slurry Substances 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
FZOTXQDXAUHHEV-UHFFFAOYSA-N 2-(1-pentylpyrrolidin-3-yl)ethanol Chemical compound CCCCCN1CCC(CCO)C1 FZOTXQDXAUHHEV-UHFFFAOYSA-N 0.000 description 3
IYIBFRGWVKSJKP-UHFFFAOYSA-N 3-(chloromethyl)-1-pentylpyrrolidine Chemical compound CCCCCN1CCC(CCl)C1 IYIBFRGWVKSJKP-UHFFFAOYSA-N 0.000 description 3
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
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 2
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical group 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
230000035807 sensation Effects 0.000 description 1
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
230000003997 social interaction Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 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
238000010561 standard procedure Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease 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
125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
208000009935 visceral pain Diseases 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- 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
- 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
- A61K31/47—Quinolines; Isoquinolines
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material 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)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)
Indole Compounds (AREA)

CA002116024A 1991-08-20 1992-08-18 Antagonistes des recepteurs 5-ht4 Abandoned CA2116024A1 (fr)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date	Title
GB919117943A GB9117943D0 (en)	1991-08-20	1991-08-20	Medicaments
GB9117943.2		1991-08-20
GB919119692A GB9119692D0 (en)	1991-09-14	1991-09-14	Pharmaceuticals
GB9119692.3		1991-09-14
GB929201414A GB9201414D0 (en)	1992-01-23	1992-01-23	Medicaments
GB9201414.1		1992-01-23
GB9203977.5		1992-02-25
GB929203977A GB9203977D0 (en)	1992-02-25	1992-02-25	Pharmaceuticals
GB9208321.1		1992-04-15
GB929208321A GB9208321D0 (en)	1992-04-15	1992-04-15	Pharmaceuticals

Publications (1)

Publication Number	Publication Date
CA2116024A1 true CA2116024A1 (fr)	1993-03-04

Family

ID=27517068

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002116024A Abandoned CA2116024A1 (fr)	1991-08-20	1992-08-18	Antagonistes des recepteurs 5-ht4

Country Status (8)

Country	Link
EP (1)	EP0600955A1 (fr)
JP (1)	JPH06510283A (fr)
AU (2)	AU2435092A (fr)
CA (1)	CA2116024A1 (fr)
MX (1)	MX9204786A (fr)
NZ (1)	NZ243993A (fr)
PT (1)	PT100785A (fr)
WO (1)	WO1993003725A1 (fr)

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US20020128172A1 (en)	1991-12-21	2002-09-12	Smithkline Beecham Plc	Use of 5-HT4 modulators for the manufacture of a medicament for the treatment of the bladder diseases
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
WO1993024117A2 (fr) *	1992-05-23	1993-12-09	Smithkline Beecham Plc	Medicaments pour le traitement de l'anxiete
AU4350493A (en) *	1992-06-27	1994-01-24	Smithkline Beecham Plc	Medicaments containing 5-ht4 receptor antagonists
US5726187A (en) *	1992-10-16	1998-03-10	Smithkline Beecham Plc	N-alkylpiperidinyl-4-methyl carboxylic esters/amides of condensed ring systems as 5-HT4 receptor antagonists
ES2056728B1 (es) *	1992-10-28	1995-05-01	Smithkline Beecham Plc	Nuevos derivados de piperidilo y aminoalquilo con actividad antagonista del receptor 5-ht4
NZ257545A (en) *	1992-11-05	1997-01-29	Smithkline Beecham Plc	Heterocyclic (especially piperidine) derivatives and pharmaceutical compositions
US6127379A (en) *	1993-02-01	2000-10-03	Smithkline Beecham P.L.C.	Benzopyran, benzothiopyran and benzofuran derivatives as 5-HT4 antagonists
GB9310582D0 (en) *	1993-05-22	1993-07-07	Smithkline Beecham Plc	Pharmaceuticals
GB9312348D0 (en) *	1993-06-16	1993-07-28	Smithkline Beecham Plc	Pharmaceuticals
AU2075295A (en) *	1994-03-14	1995-10-03	Sanofi	Use of 4-amino-5-chloro-2-methoxybenzoic esters as 5-ht4 agonists
FR2717174B1 (fr) *	1994-03-14	1996-05-31	Sanofi Sa	Utilisation de pipéridinoéthyl esters de l'acide 4-amino-5-chloro-2-méthoxybenzoïque comme 5-HT4 agonistes.
EP0683161A1 (fr) *	1994-05-17	1995-11-22	MIDY S.p.A.	Nouvel ester de l'acide 4-amino-5-chloro-2-méthoxybenzoique, procédé pour sa préparation et compositions pharmaceutiques le contenant
WO1996005166A1 (fr) *	1994-08-11	1996-02-22	Yamanouchi Pharmaceutical Co., Ltd.	Derive d'amine substitue et composition medicamenteuse le contenant
WO1996010027A1 (fr) *	1994-09-27	1996-04-04	Janssen Pharmaceutica N.V.	Derives benzoates bicycliques de piperidinyle n-substitue
US5872131A (en) *	1994-09-27	1999-02-16	Janssen Pharmaceutica, N.V.	Phenyl-oxo-alkyl-(4-piperidinyl)benzoate derivatives
US5654320A (en) *	1995-03-16	1997-08-05	Eli Lilly And Company	Indazolecarboxamides
IL117438A (en) *	1995-03-16	2001-12-23	Lilly Co Eli	Indazolecarboxamides, their preparation and pharmaceutical compositions containing them
EP0829474B1 (fr) *	1995-05-31	2003-04-09	Nisshin Seifun Group Inc.	Derives de l'indazole a groupe amino monocyclique
FR2741069B1 (fr) *	1995-11-09	1997-12-12	Synthelabo	Derives de 5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3h) -one, leur preparation et leur application en therapeutique
AU707325B2 (en) *	1995-11-09	1999-07-08	Sanofi-Aventis	5-phenyl-3-(piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one derivatives for use as 5-HT4 or H3 receptor ligands
TW445263B (en)	1996-02-29	2001-07-11	Janssen Pharmaceutica Nv	Novel esters of 1,4-disubstituted piperidine derivatives
IT1291569B1 (it) *	1997-04-15	1999-01-11	Angelini Ricerche Spa	Indazolammidi come agenti serotoninergici
TW548103B (en)	1997-07-11	2003-08-21	Janssen Pharmaceutica Nv	Bicyclic benzamides of 3- or 4-substituted 4-(aminomethyl)-piperidine derivatives
FR2766484B1 (fr) *	1997-07-25	1999-09-17	Logeais Labor Jacques	Nouveaux derives benzamides stimulants de la motricite gastrointestinale haute et basse
US6069152A (en) *	1997-10-07	2000-05-30	Eli Lilly And Company	5-HT4 agonists and antagonists
AU758807B2 (en) *	1998-09-10	2003-03-27	F. Hoffmann-La Roche Ag	Dihydrobenzodioxine carboxamide and ketone derivatives as 5-HT4 receptor antagonists
TR200101398T2 (tr) *	1998-11-20	2001-09-21	F.Hoffmann-La Roche Ag	Pirolidin türevleri-CCR-3 reseptörü antagonistleri.
TW570920B (en)	1998-12-22	2004-01-11	Janssen Pharmaceutica Nv	4-(aminomethyl)-piperidine benzamides for treating gastrointestinal disorders
FR2821356A1 (fr) *	2001-02-23	2002-08-30	Cerep	Nouveaux derives d'arylcarbamates et d'arylurees, preparations et utilisations
GB0211230D0 (en)	2002-05-16	2002-06-26	Medinnova Sf	Treatment of heart failure
ITMI20031468A1 (it) *	2003-07-18	2005-01-19	Acraf	Farmaco ativo nel dolore neuropatico
TW200533348A (en)	2004-02-18	2005-10-16	Theravance Inc	Indazole-carboxamide compounds as 5-ht4 receptor agonists
TWI351282B (en)	2004-04-07	2011-11-01	Theravance Inc	Quinolinone-carboxamide compounds as 5-ht4 recepto
US7728006B2 (en)	2004-04-07	2010-06-01	Theravance, Inc.	Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
US8309575B2 (en)	2004-04-07	2012-11-13	Theravance, Inc.	Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
US7399862B2 (en)	2004-11-05	2008-07-15	Theravance, Inc.	5-HT4 receptor agonist compounds
WO2006052889A2 (fr)	2004-11-05	2006-05-18	Theravance, Inc.	Composes de quinolinone-carboxamide
CA2588037A1 (fr)	2004-12-22	2006-06-29	Theravance, Inc.	Composes d'indazole-carboxamide
CN101163701A (zh)	2005-03-02	2008-04-16	施万制药	作为5-ht4受体激动剂的喹啉酮化合物
FR3006686A1 (fr) *	2013-06-05	2014-12-12	Univ Caen	Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant
GB201511382D0 (en)	2015-06-29	2015-08-12	Imp Innovations Ltd	Novel compounds and their use in therapy
JP2025530213A (ja)	2022-09-09	2025-09-11	ミリックスファーマリミテッド	Ｎｍｔ阻害剤を含む抗体薬物コンジュゲート及びその使用

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EP0189002B1 (fr) *	1984-12-20	1993-03-03	Sandoz Ag	Traitement de maladies gastro-intestinales utilisant des 5-HT3 antagonistes
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CA2030051C (fr) *	1989-11-17	2001-08-07	Haruhiko Kikuchi	Derives indole

1992
- 1992-08-18 CA CA002116024A patent/CA2116024A1/fr not_active Abandoned
- 1992-08-18 NZ NZ243993A patent/NZ243993A/en unknown
- 1992-08-18 AU AU24350/92A patent/AU2435092A/en not_active Abandoned
- 1992-08-18 JP JP5504191A patent/JPH06510283A/ja active Pending
- 1992-08-18 WO PCT/GB1992/001519 patent/WO1993003725A1/fr not_active Ceased
- 1992-08-18 EP EP92917490A patent/EP0600955A1/fr not_active Withdrawn
- 1992-08-18 PT PT100785A patent/PT100785A/pt not_active Application Discontinuation
- 1992-08-19 MX MX9204786A patent/MX9204786A/es unknown
1996
- 1996-04-29 AU AU51944/96A patent/AU5194496A/en not_active Abandoned

Also Published As

Publication number	Publication date
AU5194496A (en)	1996-07-18
WO1993003725A1 (fr)	1993-03-04
JPH06510283A (ja)	1994-11-17
MX9204786A (es)	1993-04-01
NZ243993A (en)	1994-10-26
PT100785A (pt)	1994-04-29
EP0600955A1 (fr)	1994-06-15
AU2435092A (en)	1993-03-16

Legal Events

Date	Code	Title	Description
1998-08-18	FZDE	Discontinued

Publication	Publication Date	Title
CA2116024A1 (fr)	1993-03-04	Antagonistes des recepteurs 5-ht4
EP0604494B1 (fr)	1999-07-28	Antagonistes de recepteurs 5-hydroxytriptamine 4
EP0884319B1 (fr)	2004-05-06	N- (1-nButyl-4-piperidyl)methyl -3,4-dihydro-2H- 1,3 oxazino 3,2-a indole-10-carboxamide ou un de ses sels pharmaceutiquement acceptables
KR100263414B1 (ko)	2001-04-02	티에노 [3,2-b] 피리딘 유도체
ES2277330T3 (es)	2007-07-01	Antagonistas del receptor 5-ht4.
US5556851A (en)	1996-09-17	Cinnoline-3-carboxylic acid derivatives
US5786372A (en)	1998-07-28	Heteroaryl compounds used as pharmaceuticals
JPH08502273A (ja)	1996-03-12	５−ｈｔ▲下４▼レセプターアンタゴニスト用複素環式エステルまたはアミド
TWI423967B (zh)	2014-01-21	醯胺衍生物及含有其之醫藥組合物
WO1994029298A1 (fr)	1994-12-22	Acide 8-amino-7-chloro-1,4-benzodioxane-5-carboxylique, ester de -1-butyl-4-piperidinyle utilise en tant qu'antagoniste du recepteur de 5-ht4
WO1994017071A1 (fr)	1994-08-04	Composes heterocycliques tricycliques comme inhibiteurs des recepteurs 5-ht4
AP373A (en)	1994-12-07	Compounds having 5TH4 receptor antagonist activity.
WO1994000113A2 (fr)	1994-01-06	Medicaments renfermant des antagonistes du recepteur de 5-ht¿4?
JPH07507290A (ja)	1995-08-10	不安症の治療のための医薬
NZ271972A (en)	1997-07-27	Condensed indole derivatives and medicaments
EP0684947A1 (fr)	1995-12-06	Composes d'amide a activite pharmacologique
AU668102C (en)	1997-05-15	5-HT4 receptor antagonists
TW396158B (en)	2000-07-01	Compound having 5-HT4 receptor antagonist activity, process for preparation the same and its use
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
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