CA2563466A1 - Anti-cytokine heterocyclic compounds - Google Patents

Info

Publication number

CA2563466A1

CA2563466A1 CA002563466A CA2563466A CA2563466A1 CA 2563466 A1 CA2563466 A1 CA 2563466A1 CA 002563466 A CA002563466 A CA 002563466A CA 2563466 A CA2563466 A CA 2563466A CA 2563466 A1 CA2563466 A1 CA 2563466A1

Authority

CA

Canada

Prior art keywords

alkyl

chosen

alkoxy

amino

hydrogen

Prior art date

2004-05-12

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 230000003092 anti-cytokine Effects 0.000 title description 5
• 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 93
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 53
• 201000010099 disease Diseases 0.000 claims abstract description 47
• 102000004127 Cytokines Human genes 0.000 claims abstract description 44
• 108090000695 Cytokines Proteins 0.000 claims abstract description 44
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• -1 aminocarboxyl Chemical group 0.000 claims description 90
• 125000000217 alkyl group Chemical group 0.000 claims description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 37
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
• 150000002431 hydrogen Chemical class 0.000 claims description 33
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 150000002825 nitriles Chemical class 0.000 claims description 21
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 13
• 125000002757 morpholinyl group Chemical group 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 13
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 125000004442 acylamino group Chemical group 0.000 claims description 12
• 125000004423 acyloxy group Chemical group 0.000 claims description 12
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
• 230000001404 mediated effect Effects 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
• WCNFFKHKJLERFM-UHFFFAOYSA-N thiomorpholinyl sulfone group Chemical group N1(CCSCC1)S(=O)(=O)N1CCSCC1 WCNFFKHKJLERFM-UHFFFAOYSA-N 0.000 claims description 7
• ZCAGUOCUDGWENZ-UHFFFAOYSA-N thiomorpholinyl sulfoxide group Chemical group N1(CCSCC1)S(=O)N1CCSCC1 ZCAGUOCUDGWENZ-UHFFFAOYSA-N 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
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• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
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• 125000004069 aziridinyl group Chemical group 0.000 claims description 5
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• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
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• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
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• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 3
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• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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• 125000002541 furyl group Chemical group 0.000 claims description 3
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• 125000001041 indolyl group Chemical group 0.000 claims description 3
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• 230000000771 oncological effect Effects 0.000 claims description 3
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• ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims description 3
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• NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims description 3
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