BR112021000050A2 - Inibidores de triazol glicolato oxidase - Google Patents

Info

Publication number

BR112021000050A2

BR112021000050A2 BR112021000050-0A BR112021000050A BR112021000050A2 BR 112021000050 A2 BR112021000050 A2 BR 112021000050A2 BR 112021000050 A BR112021000050 A BR 112021000050A BR 112021000050 A2 BR112021000050 A2 BR 112021000050A2

Authority

BR

Brazil

Prior art keywords

group

alkyl

pharmaceutically acceptable

acceptable salt

triazole

Prior art date

2018-07-06

Links

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• 102100038837 2-Hydroxyacid oxidase 1 Human genes 0.000 title claims abstract description 63
• 108010062584 glycollate oxidase Proteins 0.000 title claims abstract description 61
• 239000003112 inhibitor Substances 0.000 title abstract description 24
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 280
• -1 triazole carboxylic acids Chemical class 0.000 claims abstract description 152
• 150000003839 salts Chemical class 0.000 claims abstract description 98
• 238000000034 method Methods 0.000 claims abstract description 52
• 208000000913 Kidney Calculi Diseases 0.000 claims abstract description 28
• 206010029148 Nephrolithiasis Diseases 0.000 claims abstract description 28
• 208000004777 Primary Hyperoxaluria Diseases 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 68
• 150000002367 halogens Chemical class 0.000 claims description 68
• 125000001072 heteroaryl group Chemical group 0.000 claims description 61
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 58
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 54
• 125000000623 heterocyclic group Chemical group 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 125000003118 aryl group Chemical group 0.000 claims description 35
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• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
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• 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 23
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• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 21
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
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• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000004474 heteroalkylene group Chemical group 0.000 claims description 11
• 235000010290 biphenyl Nutrition 0.000 claims description 10
• 239000004305 biphenyl Chemical group 0.000 claims description 10
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 229910003813 NRa Inorganic materials 0.000 claims description 8
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• 239000000243 solution Substances 0.000 description 34
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• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 31
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
• HZDUEESPNHBGSE-UHFFFAOYSA-N methyl 5-chloro-1-[(4-methoxyphenyl)methyl]triazole-4-carboxylate Chemical compound ClC1=C(N=NN1CC1=CC=C(C=C1)OC)C(=O)OC HZDUEESPNHBGSE-UHFFFAOYSA-N 0.000 description 29
• 238000006243 chemical reaction Methods 0.000 description 27
• 239000007787 solid Substances 0.000 description 27
• 101000629622 Homo sapiens Serine-pyruvate aminotransferase Proteins 0.000 description 26
• 102100026842 Serine-pyruvate aminotransferase Human genes 0.000 description 26
• 208000000891 primary hyperoxaluria type 1 Diseases 0.000 description 26
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 239000011541 reaction mixture Substances 0.000 description 23
• 125000005842 heteroatom Chemical group 0.000 description 22
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
• QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 20
• HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 20
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
• 239000000741 silica gel Substances 0.000 description 20
• 229910002027 silica gel Inorganic materials 0.000 description 20
• 229910052938 sodium sulfate Inorganic materials 0.000 description 20
• 235000011152 sodium sulphate Nutrition 0.000 description 20
• 239000007858 starting material Substances 0.000 description 20
• 239000002253 acid Substances 0.000 description 19
• 229910000024 caesium carbonate Inorganic materials 0.000 description 18
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 17
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• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 15
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