NZ545787A - 2-Propynyl adenosine analogs having A2A agonist activity and compositions thereof - Google Patents

Info

Publication number

NZ545787A

NZ545787A NZ545787A NZ54578702A NZ545787A NZ 545787 A NZ545787 A NZ 545787A NZ 545787 A NZ545787 A NZ 545787A NZ 54578702 A NZ54578702 A NZ 54578702A NZ 545787 A NZ545787 A NZ 545787A

Authority

NZ

New Zealand

Prior art keywords

compound

aryl

hydrogen

alkylene

rac

Prior art date

2001-10-01

Links

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• 230000000694 effects Effects 0.000 title claims abstract description 28
• 239000000203 mixture Substances 0.000 title claims description 36
• 239000000556 agonist Substances 0.000 title description 25
• UBWAYMVIDZVHHG-ZRFIDHNTSA-N (2r,3r,4s,5r)-2-(6-amino-2-prop-1-ynylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical class C12=NC(C#CC)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O UBWAYMVIDZVHHG-ZRFIDHNTSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 161
• 230000028709 inflammatory response Effects 0.000 claims abstract description 20
• 101150051188 Adora2a gene Proteins 0.000 claims abstract description 15
• 229910003827 NRaRb Inorganic materials 0.000 claims abstract description 15
• 150000003839 salts Chemical class 0.000 claims abstract description 14
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• 241000124008 Mammalia Species 0.000 claims abstract description 9
• 238000004519 manufacturing process Methods 0.000 claims abstract description 9
• -1 pyrrolidino, piperidino, morpholino Chemical group 0.000 claims description 81
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 66
• 239000001257 hydrogen Substances 0.000 claims description 63
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 125000001072 heteroaryl group Chemical group 0.000 claims description 40
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
• 125000002947 alkylene group Chemical group 0.000 claims description 38
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 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 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
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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 14
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
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• 125000006413 ring segment Chemical group 0.000 claims description 11
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
• 208000024891 symptom Diseases 0.000 claims description 4
• OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 3
• QYMGRIFMUQCAJW-UHFFFAOYSA-N 1,2-dihydropyrazine Chemical compound C1NC=CN=C1 QYMGRIFMUQCAJW-UHFFFAOYSA-N 0.000 claims description 3
• DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 3
• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 3
• LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims description 3
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 3
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 3
• QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 3
• 239000000443 aerosol Substances 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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• KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims description 2
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• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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