HUE033114T2 - Muscarin M1 receptor agonists - Google Patents

Info

Publication number

HUE033114T2

HUE033114T2 HUE12794751A HUE12794751A HUE033114T2 HU E033114 T2 HUE033114 T2 HU E033114T2 HU E12794751 A HUE12794751 A HU E12794751A HU E12794751 A HUE12794751 A HU E12794751A HU E033114 T2 HUE033114 T2 HU E033114T2

Authority

HU

Hungary

Prior art keywords

carboxylate

ethyl

azepane

carbamoyl

piperidin

Prior art date

2011-11-18

Links

• Espacenet
• Global Dossier
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• 239000000359 muscarinic M1 receptor agonist Substances 0.000 title description 10
• 150000001875 compounds Chemical class 0.000 claims description 235
• -1 2-methyl-hutyl Chemical group 0.000 claims description 152
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 100
• 150000003839 salts Chemical class 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 45
• 238000011282 treatment Methods 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
• 125000000217 alkyl group Chemical group 0.000 claims description 30
• 125000001153 fluoro group Chemical group F* 0.000 claims description 30
• 208000010877 cognitive disease Diseases 0.000 claims description 25
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 24
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 24
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 22
• 239000011737 fluorine Substances 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 150000002430 hydrocarbons Chemical class 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
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• 230000001154 acute effect Effects 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 208000028017 Psychotic disease Diseases 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 7
• 150000007942 carboxylates Chemical class 0.000 claims description 7
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 7
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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 claims description 2
• MEOZFUYXLCDYGA-UHFFFAOYSA-N azepane-1-carboxylic acid Chemical compound OC(=O)N1CCCCCC1 MEOZFUYXLCDYGA-UHFFFAOYSA-N 0.000 claims 14
• KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 3
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• 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
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• YWRXDGYUFPGSDH-MDZDMXLPSA-N (e)-n-methyl-n-[(1-methylindol-2-yl)methyl]-3-(5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)prop-2-enamide Chemical compound N1CCCC2=CC(/C=C/C(=O)N(CC=3N(C4=CC=CC=C4C=3)C)C)=CN=C21 YWRXDGYUFPGSDH-MDZDMXLPSA-N 0.000 claims 1
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• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
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• 125000003725 azepanyl group Chemical group 0.000 claims 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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• 125000000913 palmityl 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])C([H])([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 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
• 239000000018 receptor agonist Substances 0.000 claims 1
• 229940044601 receptor agonist Drugs 0.000 claims 1
• 125000001424 substituent group Chemical group 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
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• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
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