PT2298768E - Derivados de 5-amino-2,4,7-trioxo-3,4,7,8-tetra-hidro-2hpirido[ 2,3-d]pirimidina e compostos relacionados para o tratamento do cancro - Google Patents

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Publication number

PT2298768E

PT2298768E PT100130558T PT10013055T PT2298768E PT 2298768 E PT2298768 E PT 2298768E PT 100130558 T PT100130558 T PT 100130558T PT 10013055 T PT10013055 T PT 10013055T PT 2298768 E PT2298768 E PT 2298768E

Authority

PT

Portugal

Prior art keywords

group

alkyl group

hydrogen atom

atom

compound

Prior art date

2004-06-11

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 308
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• 238000011282 treatment Methods 0.000 title claims abstract description 16
• 201000011510 cancer Diseases 0.000 title abstract description 15
• FKJJWLKXDSASLR-UHFFFAOYSA-N 5-amino-1,8-dihydropyrido[2,3-d]pyrimidine-2,4,7-trione Chemical class N1C(=O)NC(=O)C2=C1NC(=O)C=C2N FKJJWLKXDSASLR-UHFFFAOYSA-N 0.000 title description 2
• -1 pyrimidine compound Chemical class 0.000 claims abstract description 630
• 150000003839 salts Chemical class 0.000 claims abstract description 38
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• 201000010099 disease Diseases 0.000 claims abstract description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 230000004663 cell proliferation Effects 0.000 claims abstract description 16
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 202
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 153
• 125000000623 heterocyclic group Chemical group 0.000 claims description 116
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• 125000001424 substituent group Chemical group 0.000 claims description 72
• 238000004519 manufacturing process Methods 0.000 claims description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
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• 239000012453 solvate Substances 0.000 claims description 29
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• 125000005842 heteroatom Chemical group 0.000 claims description 24
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• 125000004430 oxygen atom Chemical group O* 0.000 claims description 22
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
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• 125000000217 alkyl group Chemical group 0.000 claims description 16
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• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
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• 229910052717 sulfur Inorganic materials 0.000 claims 21
• 125000004434 sulfur atom Chemical group 0.000 claims 21
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• 238000005481 NMR spectroscopy Methods 0.000 description 412
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 322
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• 238000003756 stirring Methods 0.000 description 44
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 36
• 239000002904 solvent Substances 0.000 description 36
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
• 239000011541 reaction mixture Substances 0.000 description 34
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
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• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
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• 235000018102 proteins Nutrition 0.000 description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
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• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 19
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
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• 239000000706 filtrate Substances 0.000 description 16
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• 238000010992 reflux Methods 0.000 description 16
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• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 13
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• 230000000694 effects Effects 0.000 description 12
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