TW200533348A - Indazole-carboxamide compounds as 5-ht4 receptor agonists - Google Patents

Info

Publication number

TW200533348A

TW200533348A TW094104343A TW94104343A TW200533348A TW 200533348 A TW200533348 A TW 200533348A TW 094104343 A TW094104343 A TW 094104343A TW 94104343 A TW94104343 A TW 94104343A TW 200533348 A TW200533348 A TW 200533348A

Authority

TW

Taiwan

Prior art keywords

ethyl

isopropyl

azabicyclo

carboxylic acid

oct

Prior art date

2004-02-18

Links

• Espacenet
• Global Dossier
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• 108091005482 5-HT4 receptors Proteins 0.000 title abstract description 22
• 239000000018 receptor agonist Substances 0.000 title abstract description 17
• 229940044601 receptor agonist Drugs 0.000 title abstract description 17
• DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical class C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 196
• 238000000034 method Methods 0.000 claims abstract description 71
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• 230000000694 effects Effects 0.000 claims abstract description 22
• 201000010099 disease Diseases 0.000 claims abstract description 16
• -1 tetrahydrofuran-2-carbonyl Chemical group 0.000 claims description 145
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 120
• 239000002253 acid Substances 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 32
• CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 claims description 23
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 20
• 208000024891 symptom Diseases 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 150000001412 amines Chemical class 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• FHUPHXAYPNYFIU-UHFFFAOYSA-N 1-propan-2-ylindazole-3-carboxylic acid Chemical compound C1=CC=C2N(C(C)C)N=C(C(O)=O)C2=C1 FHUPHXAYPNYFIU-UHFFFAOYSA-N 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 239000012453 solvate Substances 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
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• 239000002904 solvent Chemical class 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 11
• DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims description 10
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
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• 238000005859 coupling reaction Methods 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
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• 229910052723 transition metal Inorganic materials 0.000 claims description 3
• 150000003624 transition metals Chemical class 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
• ABZPQPREPTZBMO-UHFFFAOYSA-N 9h-fluorene-1-carboxamide Chemical compound C1C2=CC=CC=C2C2=C1C(C(=O)N)=CC=C2 ABZPQPREPTZBMO-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001475 halogen functional group Chemical group 0.000 claims 3
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• KNMDCBDADOEMFU-UHFFFAOYSA-N 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylic acid Chemical compound C1C(=O)CC2CCC1N2C(=O)O KNMDCBDADOEMFU-UHFFFAOYSA-N 0.000 claims 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000002619 bicyclic group Chemical group 0.000 claims 1
• 125000004222 fluoren-1-yl group Chemical group [H]C1=C([H])C2=C(C([H])=C1[H])C([H])([H])C1=C(*)C([H])=C([H])C([H])=C21 0.000 claims 1
• 229940124530 sulfonamide Drugs 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 53
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• DDMSOGRHSPMSLW-UHFFFAOYSA-N indazole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)N=CC2=C1 DDMSOGRHSPMSLW-UHFFFAOYSA-N 0.000 abstract 1
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