TWI238160B - Substituted tricyclics for inhibiting sPLA2 and pharmaceutical formulation comprising the same - Google Patents

Info

Publication number

TWI238160B

TWI238160B TW088106130A TW88106130A TWI238160B TW I238160 B TWI238160 B TW I238160B TW 088106130 A TW088106130 A TW 088106130A TW 88106130 A TW88106130 A TW 88106130A TW I238160 B TWI238160 B TW I238160B

Authority

TW

Taiwan

Prior art keywords

methyl

oxyacetic acid

acid

scope

patent application

Prior art date

1998-04-17

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• 230000002401 inhibitory effect Effects 0.000 title claims abstract description 13
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• 108010031873 Secretory Phospholipases A2 Proteins 0.000 title claims abstract 6
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• 150000001875 compounds Chemical class 0.000 claims abstract description 141
• 238000011282 treatment Methods 0.000 claims abstract description 20
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• 206010040070 Septic Shock Diseases 0.000 claims abstract description 8
• 230000036303 septic shock Effects 0.000 claims abstract description 8
• -1 [( Phenyl) methyl] -5-aminomethylfluorenylcarbazole Chemical compound 0.000 claims description 175
• 239000002253 acid Substances 0.000 claims description 158
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 148
• 159000000000 sodium salts Chemical class 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
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
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• 241000282414 Homo sapiens Species 0.000 claims description 15
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• YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 13
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• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
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• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
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• 230000001404 mediated effect Effects 0.000 abstract description 2
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
• 238000006243 chemical reaction Methods 0.000 description 86
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• 235000019439 ethyl acetate Nutrition 0.000 description 71
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
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• 238000000921 elemental analysis Methods 0.000 description 61
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