MXPA04004388A - Antagonistas del receptor a2b de adenosina. - Google Patents

Info

Publication number

MXPA04004388A

MXPA04004388A MXPA04004388A MXPA04004388A MXPA04004388A MX PA04004388 A MXPA04004388 A MX PA04004388A MX PA04004388 A MXPA04004388 A MX PA04004388A MX PA04004388 A MXPA04004388 A MX PA04004388A MX PA04004388 A MXPA04004388 A MX PA04004388A

Authority

MX

Mexico

Prior art keywords

optionally substituted

dione

formula

compound

trihydropurine

Prior art date

2001-11-09

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims abstract description 414
• 101150078577 Adora2b gene Proteins 0.000 claims abstract description 19
• 201000010099 disease Diseases 0.000 claims abstract description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
• 208000006673 asthma Diseases 0.000 claims abstract description 12
• 206010012735 Diarrhoea Diseases 0.000 claims abstract description 7
• 229940121359 adenosine receptor antagonist Drugs 0.000 claims abstract description 4
• 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims abstract description 4
• -1 3-trifluoromethylphenyl Chemical group 0.000 claims description 215
• 238000002360 preparation method Methods 0.000 claims description 129
• 238000006243 chemical reaction Methods 0.000 claims description 112
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 88
• 239000001257 hydrogen Substances 0.000 claims description 83
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• 238000000034 method Methods 0.000 claims description 77
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 69
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 47
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 40
• 125000003545 alkoxy group Chemical group 0.000 claims description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims description 34
• 125000002947 alkylene group Chemical group 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 150000002431 hydrogen Chemical group 0.000 claims description 21
• OYODOQNYJLSLJE-UHFFFAOYSA-N pyrazol-4-one Chemical compound O=C1C=NN=C1 OYODOQNYJLSLJE-UHFFFAOYSA-N 0.000 claims description 21
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 21
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 14
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
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• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
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• 238000006467 substitution reaction Methods 0.000 claims description 7
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• 125000005549 heteroarylene group Chemical group 0.000 claims description 6
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• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
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• 201000011510 cancer Diseases 0.000 claims description 4
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
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• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
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• 206010039966 Senile dementia Diseases 0.000 claims description 3
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• KAYVCWBEIZTVCN-UHFFFAOYSA-N 8-(1-benzylpyrazol-4-yl)-1-propyl-3,7-dihydropurine-2,6-dione Chemical compound N1C=2C(=O)N(CCC)C(=O)NC=2N=C1C(=C1)C=NN1CC1=CC=CC=C1 KAYVCWBEIZTVCN-UHFFFAOYSA-N 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
• NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-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
• 230000004968 inflammatory condition Effects 0.000 claims 2
• 230000000926 neurological effect Effects 0.000 claims 2
• IVDPFMFNQXHGNX-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=CC(F)=C1 IVDPFMFNQXHGNX-UHFFFAOYSA-N 0.000 claims 1
• 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
• 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims 1
• 229940125961 compound 24 Drugs 0.000 claims 1
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
• 239000000203 mixture Substances 0.000 description 74
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
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• 239000002904 solvent Substances 0.000 description 50
• 125000001424 substituent group Chemical group 0.000 description 45
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 44
• 239000000243 solution Substances 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
• 239000000047 product Substances 0.000 description 34
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• 239000004480 active ingredient Substances 0.000 description 27
• 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 description 26
• 229910052736 halogen Inorganic materials 0.000 description 24
• 150000002367 halogens Chemical class 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 23
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 22
• 125000004181 carboxyalkyl group Chemical group 0.000 description 22
• 125000004093 cyano group Chemical group *C#N 0.000 description 22
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
• 125000003118 aryl group Chemical group 0.000 description 21
• 239000003826 tablet Substances 0.000 description 21
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• 125000003342 alkenyl group Chemical group 0.000 description 19
• 235000019439 ethyl acetate Nutrition 0.000 description 19
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 19
• 229920002554 vinyl polymer Polymers 0.000 description 19
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
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• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 17
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• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 17
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• 125000000392 cycloalkenyl group Chemical group 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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• 229960005305 adenosine Drugs 0.000 description 13
• 125000000304 alkynyl group Chemical group 0.000 description 13
• FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
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• 125000004414 alkyl thio group Chemical group 0.000 description 10
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
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• 150000003839 salts Chemical class 0.000 description 10
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• WDVYWEYJVBNHLX-UHFFFAOYSA-N 6-amino-1-benzyl-5-nitrosopyrimidine-2,4-dione Chemical compound NC1=C(N=O)C(=O)NC(=O)N1CC1=CC=CC=C1 WDVYWEYJVBNHLX-UHFFFAOYSA-N 0.000 description 4
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• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
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