TW201130821A - Benzimidazole inhibitors of leukotriene production - Google Patents

Info

Publication number

TW201130821A

TW201130821A TW099142221A TW99142221A TW201130821A TW 201130821 A TW201130821 A TW 201130821A TW 099142221 A TW099142221 A TW 099142221A TW 99142221 A TW99142221 A TW 99142221A TW 201130821 A TW201130821 A TW 201130821A

Authority

TW

Taiwan

Prior art keywords

butyl

phenyl

pyrimidin

ylamine

benzimidazol

Prior art date

2009-12-04

Links

• Espacenet
• Global Dossier
• Discuss

• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims description 21
• 150000002617 leukotrienes Chemical class 0.000 title claims description 8
• 239000003112 inhibitor Substances 0.000 title description 11
• 238000004519 manufacturing process Methods 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 138
• 238000000034 method Methods 0.000 claims abstract description 58
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 130
• -1 [1,2,4]oxadiazolyl Chemical group 0.000 claims description 122
• 125000000217 alkyl group Chemical group 0.000 claims description 85
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 46
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 38
• 238000006243 chemical reaction Methods 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 239000002253 acid Substances 0.000 claims description 28
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
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• 201000010099 disease Diseases 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
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• 150000002367 halogens Chemical class 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
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• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 8
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• 150000002923 oximes Chemical class 0.000 claims description 7
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• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 4
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 4
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• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
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• 125000005605 benzo group Chemical group 0.000 claims description 3
• ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 235000009566 rice Nutrition 0.000 claims description 3
• 238000012360 testing method Methods 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• 150000003573 thiols Chemical class 0.000 claims description 3
• 125000001425 triazolyl group Chemical group 0.000 claims description 3
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 2
• BCQLUGMLCFKISL-UHFFFAOYSA-N 5-[1-tert-butyl-2-[2-(3-methyl-1,2,4-thiadiazol-5-yl)phenyl]benzimidazol-5-yl]pyrimidin-2-amine Chemical compound CC1=NSC(C=2C(=CC=CC=2)C=2N(C3=CC=C(C=C3N=2)C=2C=NC(N)=NC=2)C(C)(C)C)=N1 BCQLUGMLCFKISL-UHFFFAOYSA-N 0.000 claims description 2
• SPJUQMQMYYNLBV-UHFFFAOYSA-N 5-[2-[5-bromo-2-(1,2,4-triazol-1-yl)phenyl]-1-tert-butylbenzimidazol-5-yl]pyrimidin-2-amine Chemical compound C=1C=C2N(C(C)(C)C)C(C=3C(=CC=C(Br)C=3)N3N=CN=C3)=NC2=CC=1C1=CN=C(N)N=C1 SPJUQMQMYYNLBV-UHFFFAOYSA-N 0.000 claims description 2
• APRJFNLVTJWEPP-UHFFFAOYSA-N Diethylcarbamic acid Chemical compound CCN(CC)C(O)=O APRJFNLVTJWEPP-UHFFFAOYSA-N 0.000 claims description 2
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
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