NZ532062A - 2-propynyl adenosine analogues having A2 adenosine recepter agonist activity and compositions thereof to treat inflammatory responses - Google Patents

Info

Publication number

NZ532062A

NZ532062A NZ532062A NZ53206202A NZ532062A NZ 532062 A NZ532062 A NZ 532062A NZ 532062 A NZ532062 A NZ 532062A NZ 53206202 A NZ53206202 A NZ 53206202A NZ 532062 A NZ532062 A NZ 532062A

Authority

NZ

New Zealand

Prior art keywords

compound

carboxylic acid

aryl

piperidine

alkylene

Prior art date

2001-10-01

Links

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• 230000000694 effects Effects 0.000 title claims abstract description 27
• 239000000203 mixture Substances 0.000 title claims description 36
• 230000028709 inflammatory response Effects 0.000 title claims description 23
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 title description 25
• 239000000556 agonist Substances 0.000 title description 17
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• 229960005305 adenosine Drugs 0.000 title description 16
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• 150000001875 compounds Chemical class 0.000 claims abstract description 168
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
• 239000001257 hydrogen Substances 0.000 claims abstract description 69
• 125000003118 aryl group Chemical group 0.000 claims abstract description 64
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• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 45
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• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 33
• 125000004429 atom Chemical group 0.000 claims abstract description 20
• 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 17
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 14
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• -1 pyrrolidino, piperidino, morpholino Chemical group 0.000 claims description 82
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
• 125000000217 alkyl group Chemical group 0.000 claims description 50
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 24
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 16
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• 239000003814 drug Substances 0.000 claims description 13
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• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
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• 125000006413 ring segment Chemical group 0.000 claims description 11
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• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
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• QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 8
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• 125000001424 substituent group Chemical group 0.000 claims description 6
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• 230000001363 autoimmune Effects 0.000 claims description 5
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• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
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• FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical group FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 claims description 3
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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• 125000005505 thiomorpholino group Chemical group 0.000 claims description 3
• OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims description 2
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