TW442481B - Imidazole compounds having an action of inhibiting cytokine, a process for the preparation thereof, and a pharmaceutical composition comprising them - Google Patents

Info

Publication number

TW442481B

TW442481B TW085106749A TW85106749A TW442481B TW 442481 B TW442481 B TW 442481B TW 085106749 A TW085106749 A TW 085106749A TW 85106749 A TW85106749 A TW 85106749A TW 442481 B TW442481 B TW 442481B

Authority

TW

Taiwan

Prior art keywords

formula

alkyl

group

fluorophenyl

substituted

Prior art date

1995-06-07

Links

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• 102000004127 Cytokines Human genes 0.000 title claims abstract description 55
• 108090000695 Cytokines Proteins 0.000 title claims abstract description 55
• 150000002460 imidazoles Chemical class 0.000 title claims abstract description 11
• 238000000034 method Methods 0.000 title claims description 93
• 230000002401 inhibitory effect Effects 0.000 title claims description 31
• 238000002360 preparation method Methods 0.000 title claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
• 230000009471 action Effects 0.000 title claims description 5
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• 239000000203 mixture Chemical class 0.000 claims abstract description 35
• 239000003112 inhibitor Substances 0.000 claims abstract description 12
• 238000002560 therapeutic procedure Methods 0.000 claims abstract 2
• 150000001875 compounds Chemical class 0.000 claims description 235
• 125000000217 alkyl group Chemical group 0.000 claims description 170
• -1 hexahydropyridinylamino Chemical group 0.000 claims description 165
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 162
• 238000011049 filling Methods 0.000 claims description 87
• 125000003118 aryl group Chemical group 0.000 claims description 84
• 125000000623 heterocyclic group Chemical group 0.000 claims description 57
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 51
• 201000010099 disease Diseases 0.000 claims description 51
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
• 150000001412 amines Chemical class 0.000 claims description 46
• 230000002079 cooperative effect Effects 0.000 claims description 46
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 44
• 239000002904 solvent Substances 0.000 claims description 41
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 40
• 238000006243 chemical reaction Methods 0.000 claims description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 38
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
• 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• 230000000875 corresponding effect Effects 0.000 claims description 23
• 150000002466 imines Chemical class 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
• 230000001404 mediated effect Effects 0.000 claims description 16
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
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• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 6
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• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
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• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
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• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
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• JJTIYVQQGRYBCG-UHFFFAOYSA-N 4-(1h-imidazol-2-yl)-1-methylpiperidine Chemical compound C1CN(C)CCC1C1=NC=CN1 JJTIYVQQGRYBCG-UHFFFAOYSA-N 0.000 claims description 2
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