NZ577814A - Imidazo[1,2-a]pyridine amide derivatives - Google Patents

Info

Publication number

NZ577814A

NZ577814A NZ577814A NZ57781407A NZ577814A NZ 577814 A NZ577814 A NZ 577814A NZ 577814 A NZ577814 A NZ 577814A NZ 57781407 A NZ57781407 A NZ 57781407A NZ 577814 A NZ577814 A NZ 577814A

Authority

NZ

New Zealand

Prior art keywords

c6alkyl

amino

imidazo

adamantan

pyridine

Prior art date

2006-11-27

Links

• Espacenet
• Global Dossier
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• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 title description 24
• 150000001875 compounds Chemical class 0.000 claims abstract description 384
• 102100037602 P2X purinoceptor 7 Human genes 0.000 claims abstract description 139
• 101710189965 P2X purinoceptor 7 Proteins 0.000 claims abstract description 138
• 125000001424 substituent group Chemical group 0.000 claims abstract description 106
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• 230000036407 pain Effects 0.000 claims abstract description 79
• 230000000694 effects Effects 0.000 claims abstract description 66
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 61
• 150000003839 salts Chemical class 0.000 claims abstract description 53
• 125000003118 aryl group Chemical group 0.000 claims abstract description 30
• 238000011282 treatment Methods 0.000 claims abstract description 26
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
• 206010061218 Inflammation Diseases 0.000 claims abstract description 18
• 230000004054 inflammatory process Effects 0.000 claims abstract description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
• 230000001404 mediated effect Effects 0.000 claims abstract description 14
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• -1 cyano, amino Chemical group 0.000 claims description 412
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 163
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 162
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 141
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 102
• 239000000203 mixture Substances 0.000 claims description 78
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 77
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 66
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 150000002367 halogens Chemical class 0.000 claims description 65
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 65
• 125000004043 oxo group Chemical group O=* 0.000 claims description 64
• 125000000623 heterocyclic group Chemical group 0.000 claims description 57
• 125000004429 atom Chemical group 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 46
• 238000003556 assay Methods 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 33
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 29
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• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 241001465754 Metazoa Species 0.000 claims description 18
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• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 11
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• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
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• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 9
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
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• 239000006071 cream Substances 0.000 claims description 6
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
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• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
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• 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 5
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• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
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• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
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• 230000009610 hypersensitivity Effects 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
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• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
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• UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims 1
• 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 abstract 1
• 125000005156 substituted alkylene group Chemical group 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 89
• NNPRQFFDCTZUDQ-UHFFFAOYSA-N imidazo[1,2-a]pyridine-5-carboxamide Chemical compound NC(=O)C1=CC=CC2=NC=CN12 NNPRQFFDCTZUDQ-UHFFFAOYSA-N 0.000 description 78
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 73
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• KVJWHAYFTBJZKA-UHFFFAOYSA-N imidazo[1,2-a]pyridine-2,5-dicarboxamide Chemical compound NC(=O)C1=CC=CC2=NC(C(=O)N)=CN21 KVJWHAYFTBJZKA-UHFFFAOYSA-N 0.000 description 31
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• XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 description 22
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