ZA200605526B - Substituted azole derivatives, compositions and methods of use - Google Patents

Info

Publication number

ZA200605526B

ZA200605526B ZA200605526A ZA200605526A ZA200605526B ZA 200605526 B ZA200605526 B ZA 200605526B ZA 200605526 A ZA200605526 A ZA 200605526A ZA 200605526 A ZA200605526 A ZA 200605526A ZA 200605526 B ZA200605526 B ZA 200605526B

Authority

ZA

South Africa

Prior art keywords

phenyl

alkyl

alkylene

dichloro

imidazol

Prior art date

2004-02-12

Links

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• 238000000034 method Methods 0.000 title claims description 665
• 239000000203 mixture Chemical class 0.000 title description 62
• 150000007980 azole derivatives Chemical class 0.000 title description 6
• 229920002554 vinyl polymer Polymers 0.000 claims description 557
• 239000005711 Benzoic acid Substances 0.000 claims description 441
• -1 DMARD Substances 0.000 claims description 275
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 247
• 150000001875 compounds Chemical class 0.000 claims description 202
• 125000000217 alkyl group Chemical group 0.000 claims description 163
• 235000010233 benzoic acid Nutrition 0.000 claims description 140
• 239000002253 acid Substances 0.000 claims description 87
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 70
• 229910052739 hydrogen Inorganic materials 0.000 claims description 63
• 125000001424 substituent group Chemical group 0.000 claims description 62
• 150000002148 esters Chemical class 0.000 claims description 58
• 239000001257 hydrogen Substances 0.000 claims description 50
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• 108020000494 protein-tyrosine phosphatase Proteins 0.000 claims description 43
• 239000008194 pharmaceutical composition Substances 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
• 239000003937 drug carrier Substances 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 28
• 201000010099 disease Diseases 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 21
• 125000002947 alkylene group Chemical group 0.000 claims description 20
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 19
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• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 6
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• XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 4
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• XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 claims description 4
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• WXRWCAWGXBJYOV-UHFFFAOYSA-N 1-phenoxybiphenylene Chemical group C=1C=CC=2C3=CC=CC=C3C=2C=1OC1=CC=CC=C1 WXRWCAWGXBJYOV-UHFFFAOYSA-N 0.000 claims description 2
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• 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 claims 4
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• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 2
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• UWCUVELSBUQQHY-UHFFFAOYSA-N 4-[2-[[4-(4-tert-butylphenyl)phenyl]methyl]-4-(2,4-dichlorophenyl)imidazol-1-yl]-2-(methanesulfonamido)benzoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=C1)=CC=C1CC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CN1C1=CC=C(C(O)=O)C(NS(C)(=O)=O)=C1 UWCUVELSBUQQHY-UHFFFAOYSA-N 0.000 claims 1
• YFVOJKKUAIYPDX-FRKPEAEDSA-N 4-[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-(3-methylsulfonylphenyl)phenyl]ethenyl]imidazol-1-yl]benzoic acid Chemical compound CS(=O)(=O)C1=CC=CC(C=2C=CC(\C=C\C=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)C=3C=CC(=CC=3)C(O)=O)=CC=2)=C1 YFVOJKKUAIYPDX-FRKPEAEDSA-N 0.000 claims 1
• YNNMQGQBYKTMKE-GIDUJCDVSA-N 4-[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[3-(2,2,2-trifluoroethylsulfonylamino)phenyl]phenyl]ethenyl]imidazol-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(\C=C\C=2C=CC(=CC=2)C=2C=C(NS(=O)(=O)CC(F)(F)F)C=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 YNNMQGQBYKTMKE-GIDUJCDVSA-N 0.000 claims 1
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• JZXANCNVSMINKC-CAOOACKPSA-N 4-[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[3-(propan-2-ylsulfonylamino)phenyl]phenyl]ethenyl]imidazol-1-yl]benzoic acid Chemical compound CC(C)S(=O)(=O)NC1=CC=CC(C=2C=CC(\C=C\C=3N(C=C(N=3)C=3C(=CC(Cl)=CC=3)Cl)C=3C=CC(=CC=3)C(O)=O)=CC=2)=C1 JZXANCNVSMINKC-CAOOACKPSA-N 0.000 claims 1
• RHTHUJCIFOLOPL-GIDUJCDVSA-N 4-[4-(2,4-dichlorophenyl)-2-[(e)-2-[4-[3-(trifluoromethyl)phenyl]phenyl]ethenyl]imidazol-1-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1C(\C=C\C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 RHTHUJCIFOLOPL-GIDUJCDVSA-N 0.000 claims 1
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• OFFGENNAHJGXEY-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenyl)-2-[[4-(4-hydroxyphenyl)phenyl]methyl]imidazol-1-yl]-2-(methanesulfonamido)benzoic acid Chemical compound C1=C(C(O)=O)C(NS(=O)(=O)C)=CC(N2C(=NC(=C2)C=2C(=CC(Cl)=CC=2)Cl)CC=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 OFFGENNAHJGXEY-UHFFFAOYSA-N 0.000 claims 1
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• YNDCQYGBAGAFIE-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenyl)-2-[[4-[4-[3-(trifluoromethyl)phenoxy]phenyl]phenyl]methyl]imidazol-1-yl]-n-methylsulfonylbenzamide Chemical compound C1=CC(C(=O)NS(=O)(=O)C)=CC=C1N1C(CC=2C=CC(=CC=2)C=2C=CC(OC=3C=C(C=CC=3)C(F)(F)F)=CC=2)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 YNDCQYGBAGAFIE-UHFFFAOYSA-N 0.000 claims 1
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