EA027244B1 - Алкоксипиразолы в качестве активаторов растворимой гуанилатциклазы - Google Patents

Info

Publication number

EA027244B1

EA027244B1 EA201500298A EA201500298A EA027244B1 EA 027244 B1 EA027244 B1 EA 027244B1 EA 201500298 A EA201500298 A EA 201500298A EA 201500298 A EA201500298 A EA 201500298A EA 027244 B1 EA027244 B1 EA 027244B1

Authority

EA

Eurasian Patent Office

Prior art keywords

compound

group

electrospray

mmol

mixture

Prior art date

2012-09-07

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• -1 Alkoxy pyrazoles Chemical class 0.000 title claims description 53
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• 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 title claims description 9
• 239000003119 guanylate cyclase activator Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 521
• 238000000034 method Methods 0.000 claims abstract description 208
• 150000003839 salts Chemical class 0.000 claims abstract description 51
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 16
• 239000013256 coordination polymer Substances 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
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• 208000035475 disorder Diseases 0.000 claims description 9
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• 208000017169 kidney disease Diseases 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
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• 239000012267 brine Substances 0.000 description 28
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
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• 239000000706 filtrate Substances 0.000 description 25
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
• 239000000047 product Substances 0.000 description 24
• 239000002904 solvent Substances 0.000 description 24
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
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• 229910002027 silica gel Inorganic materials 0.000 description 23
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
• HYYIVXFEEWOWBJ-UHFFFAOYSA-N tert-butyl 6-(bromomethyl)-5-methyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1C=CC(CBr)=C2C HYYIVXFEEWOWBJ-UHFFFAOYSA-N 0.000 description 19
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 16
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• 125000003118 aryl group Chemical group 0.000 description 13
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• 238000004128 high performance liquid chromatography Methods 0.000 description 13
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