NZ543416A - Xanthine derivatives as A2B adenosine receptor antagonists suitable for treating conditions such as asthma and diarrhoea - Google Patents

Info

Publication number

NZ543416A

NZ543416A NZ543416A NZ54341603A NZ543416A NZ 543416 A NZ543416 A NZ 543416A NZ 543416 A NZ543416 A NZ 543416A NZ 54341603 A NZ54341603 A NZ 54341603A NZ 543416 A NZ543416 A NZ 543416A

Authority

NZ

New Zealand

Prior art keywords

dione

trihydropurine

alkyl

substituted

optionally substituted

Prior art date

2003-05-06

Links

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• Global Dossier
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• 101150078577 Adora2b gene Proteins 0.000 title claims abstract description 23
• 208000006673 asthma Diseases 0.000 title claims abstract description 13
• 206010012735 Diarrhoea Diseases 0.000 title claims abstract description 8
• 229940121359 adenosine receptor antagonist Drugs 0.000 title abstract description 6
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 title abstract description 6
• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title description 3
• 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 423
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• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 5
• 230000033115 angiogenesis Effects 0.000 claims abstract description 5
• 201000011510 cancer Diseases 0.000 claims abstract description 5
• 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 5
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 5
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
• 206010039966 Senile dementia Diseases 0.000 claims abstract description 4
• -1 amino, aminocarbonyl Chemical group 0.000 claims description 185
• 238000002360 preparation method Methods 0.000 claims description 135
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• 238000006243 chemical reaction Methods 0.000 claims description 115
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• 239000001257 hydrogen Substances 0.000 claims description 91
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• 239000000203 mixture Substances 0.000 claims description 83
• 125000001072 heteroaryl group Chemical group 0.000 claims description 76
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• 125000001424 substituent group Chemical group 0.000 claims description 67
• 125000003118 aryl group Chemical group 0.000 claims description 66
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
• 125000003545 alkoxy group Chemical group 0.000 claims description 49
• 229910052736 halogen Inorganic materials 0.000 claims description 40
• 150000002367 halogens Chemical group 0.000 claims description 40
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 38
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 34
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• 125000000304 alkynyl group Chemical group 0.000 claims description 25
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
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• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
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• 125000004470 heterocyclooxy group Chemical group 0.000 claims description 14
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• 238000006467 substitution reaction Methods 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 239000011593 sulfur Substances 0.000 claims description 9
• 239000005557 antagonist Substances 0.000 claims description 8
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• 101150046889 ADORA3 gene Proteins 0.000 claims description 4
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• 102000055025 Adenosine deaminases Human genes 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
• SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 3
• SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 102000005962 receptors Human genes 0.000 claims description 3
• 108020003175 receptors Proteins 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• HEHWDTREEVPBPD-UHFFFAOYSA-N 8-[1-[[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]methyl]pyrazol-4-yl]-3-ethyl-1-propyl-7h-purine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)N(CC)C=2N=C1C(=C1)C=NN1CC(ON=1)=NC=1C1=CC=C(Cl)C=C1 HEHWDTREEVPBPD-UHFFFAOYSA-N 0.000 claims description 2
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• 239000000556 agonist Substances 0.000 claims 4
• 230000001593 cAMP accumulation Effects 0.000 claims 4
• HUJXGQILHAUCCV-MOROJQBDSA-N 3-iodobenzyl-5'-N-methylcarboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NC)O[C@H]1N1C2=NC=NC(NCC=3C=C(I)C=CC=3)=C2N=C1 HUJXGQILHAUCCV-MOROJQBDSA-N 0.000 claims 2
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 claims 2
• OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 claims 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
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