TW200804366A - Carbamate compounds as 5-HT4 receptor agonists - Google Patents

Info

Publication number

TW200804366A

TW200804366A TW095142293A TW95142293A TW200804366A TW 200804366 A TW200804366 A TW 200804366A TW 095142293 A TW095142293 A TW 095142293A TW 95142293 A TW95142293 A TW 95142293A TW 200804366 A TW200804366 A TW 200804366A

Authority

TW

Taiwan

Prior art keywords

compound

formula

isopropyl

acid

doc

Prior art date

2005-11-22

Links

• Espacenet
• Global Dossier
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• 108091005482 5-HT4 receptors Proteins 0.000 title claims abstract description 25
• 239000000018 receptor agonist Substances 0.000 title abstract description 18
• 229940044601 receptor agonist Drugs 0.000 title abstract description 18
• 150000004657 carbamic acid derivatives Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 202
• 238000000034 method Methods 0.000 claims abstract description 71
• 230000000694 effects Effects 0.000 claims abstract description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 27
• 230000008569 process Effects 0.000 claims abstract description 12
• 239000000203 mixture Substances 0.000 claims description 64
• -1 C 3 alkyl Substances 0.000 claims description 50
• 238000002360 preparation method Methods 0.000 claims description 38
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 229910003827 NRaRb Inorganic materials 0.000 claims description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 239000002904 solvent Substances 0.000 claims description 21
• 239000002253 acid Substances 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 235000021419 vinegar Nutrition 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 239000000052 vinegar Substances 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
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• 239000003937 drug carrier Substances 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 206010021518 Impaired gastric emptying Diseases 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
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• 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 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 208000001288 gastroparesis Diseases 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 229910052702 rhenium Inorganic materials 0.000 claims description 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
• VHIPTEOOLYCIDA-UHFFFAOYSA-N S(=O)(=O)=C1N(CCNC1)C(=O)O Chemical compound S(=O)(=O)=C1N(CCNC1)C(=O)O VHIPTEOOLYCIDA-UHFFFAOYSA-N 0.000 claims 1
• 229960005370 atorvastatin Drugs 0.000 claims 1
• 229910052736 halogen Inorganic materials 0.000 claims 1
• 150000002367 halogens Chemical class 0.000 claims 1
• YDZJZFVJRMXZOQ-UHFFFAOYSA-N methylamino carbamate Chemical compound CNOC(N)=O YDZJZFVJRMXZOQ-UHFFFAOYSA-N 0.000 claims 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
• 230000002269 spontaneous effect Effects 0.000 claims 1
• XICAMVNHDMHQHG-UHFFFAOYSA-N thiomorpholine-4-carboxylic acid Chemical compound OC(=O)N1CCSCC1 XICAMVNHDMHQHG-UHFFFAOYSA-N 0.000 claims 1
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• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
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• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 10
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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