UA63875C2 - Substituted imidazoles, a process for the preparation thereof, a pharmaceutical composition based thereon and a method for treatment - Google Patents

Info

Publication number

UA63875C2

UA63875C2 UA96010110A UA96010110A UA63875C2 UA 63875 C2 UA63875 C2 UA 63875C2 UA 96010110 A UA96010110 A UA 96010110A UA 96010110 A UA96010110 A UA 96010110A UA 63875 C2 UA63875 C2 UA 63875C2

Authority

UA

Ukraine

Prior art keywords

imidazole

fluorophenyl

pyridyl

alkyl

propyl

Prior art date

1993-07-16

Links

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• Global Dossier
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• 150000002460 imidazoles Chemical class 0.000 title claims abstract description 220
• 238000000034 method Methods 0.000 title claims abstract description 190
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
• 238000002360 preparation method Methods 0.000 title abstract description 23
• 230000008569 process Effects 0.000 title abstract description 6
• 201000010099 disease Diseases 0.000 claims abstract description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
• 230000001404 mediated effect Effects 0.000 claims abstract description 16
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 457
• 150000001875 compounds Chemical class 0.000 claims description 317
• -1 1-imidazolyl Chemical group 0.000 claims description 89
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 83
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
• 125000003118 aryl group Chemical group 0.000 claims description 42
• 102000004127 Cytokines Human genes 0.000 claims description 40
• 108090000695 Cytokines Proteins 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 239000001257 hydrogen Substances 0.000 claims description 39
• 108090001007 Interleukin-8 Proteins 0.000 claims description 38
• 108010002352 Interleukin-1 Proteins 0.000 claims description 37
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 22
• 241000124008 Mammalia Species 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 239000011593 sulfur Chemical group 0.000 claims description 18
• 108090001005 Interleukin-6 Proteins 0.000 claims description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 15
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
• 230000002401 inhibitory effect Effects 0.000 claims description 15
• 230000005764 inhibitory process Effects 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000003107 substituted aryl group Chemical group 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 10
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 9
• 206010040070 Septic Shock Diseases 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 7
• 206010040047 Sepsis Diseases 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000000945 filler Substances 0.000 claims description 6
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
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• 125000004429 atom Chemical group 0.000 claims description 5
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
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• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
• ROKOFZNQCIIJMI-UHFFFAOYSA-N 4-(4-fluorophenyl)-1-cycloropropylmethyl-5-(4-pyridyl)-imidazole Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CC2CC2)C=N1 ROKOFZNQCIIJMI-UHFFFAOYSA-N 0.000 claims description 4
• VXSHGJJXHHEQII-UHFFFAOYSA-N 4-[3-cyclopropyl-5-(4-fluorophenyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(C2CC2)C=N1 VXSHGJJXHHEQII-UHFFFAOYSA-N 0.000 claims description 4
• ZXAWHDKYRBFPMS-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-propan-2-ylimidazol-4-yl]pyridine Chemical compound CC(C)N1C=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 ZXAWHDKYRBFPMS-UHFFFAOYSA-N 0.000 claims description 4
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• 125000003277 amino group Chemical group 0.000 claims description 4
• 230000036031 hyperthermia Effects 0.000 claims description 4
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• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• BWDVVDQAECUHAD-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5-pyridin-4-ylimidazol-1-yl]acetaldehyde Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CC=O)C=N1 BWDVVDQAECUHAD-UHFFFAOYSA-N 0.000 claims description 3
• CIFYBLVHQQNVPW-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-5-pyridin-4-ylimidazol-1-yl]acetonitrile Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CC#N)C=N1 CIFYBLVHQQNVPW-UHFFFAOYSA-N 0.000 claims description 3
• IYFMAQVLNAMSDV-UHFFFAOYSA-N 4-[3-(3-azidopropyl)-5-(4-fluorophenyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCN=[N+]=[N-])C=N1 IYFMAQVLNAMSDV-UHFFFAOYSA-N 0.000 claims description 3
• SVRAGOOKTLUHES-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-(1-methylpiperidin-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1N1C(C=2N=C(N)N=CC=2)=C(C=2C=CC(F)=CC=2)N=C1 SVRAGOOKTLUHES-UHFFFAOYSA-N 0.000 claims description 3
• PGUXJVJYJAXTTL-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-(3-phenoxypropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCOC=2C=CC=CC=2)C=N1 PGUXJVJYJAXTTL-UHFFFAOYSA-N 0.000 claims description 3
• BDVINPAMNZCFRJ-BIIKFXOESA-N 4-[5-(4-fluorophenyl)-3-[(e)-prop-1-enyl]imidazol-4-yl]pyridine Chemical compound C\C=C\N1C=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 BDVINPAMNZCFRJ-BIIKFXOESA-N 0.000 claims description 3
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
• 241000894006 Bacteria Species 0.000 claims description 3
• 206010063094 Cerebral malaria Diseases 0.000 claims description 3
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 206010018634 Gouty Arthritis Diseases 0.000 claims description 3
• 206010035664 Pneumonia Diseases 0.000 claims description 3
• VSPFURGQAYMVAN-UHFFFAOYSA-N SB220025 Chemical compound NC1=NC=CC(C=2N(C=NC=2C=2C=CC(F)=CC=2)C2CCNCC2)=N1 VSPFURGQAYMVAN-UHFFFAOYSA-N 0.000 claims description 3
• 201000010001 Silicosis Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• 125000003435 aroyl group Chemical group 0.000 claims description 3
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• 208000006673 asthma Diseases 0.000 claims description 3
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• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 2
• NMUTXDVDNPBAKU-UHFFFAOYSA-N 4-(4-phenyl-1h-imidazol-5-yl)pyridine Chemical compound N1C=NC(C=2C=CN=CC=2)=C1C1=CC=CC=C1 NMUTXDVDNPBAKU-UHFFFAOYSA-N 0.000 claims description 2
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• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 2
• 125000005493 quinolyl group Chemical group 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
• BKDMXVREWXKZLB-UHFFFAOYSA-N 3-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCCNC1 BKDMXVREWXKZLB-UHFFFAOYSA-N 0.000 claims 1
• JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims 1
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