TW201043620A - Isoxazolines as inhibitors of fatty acid amide hydrolase - Google Patents

Info

Publication number

TW201043620A

TW201043620A TW099115796A TW99115796A TW201043620A TW 201043620 A TW201043620 A TW 201043620A TW 099115796 A TW099115796 A TW 099115796A TW 99115796 A TW99115796 A TW 99115796A TW 201043620 A TW201043620 A TW 201043620A

Authority

TW

Taiwan

Prior art keywords

alkyl

group

aryl

several embodiments

compound

Prior art date

2009-05-18

Links

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• 239000003112 inhibitor Substances 0.000 title description 5
• 108010046094 fatty-acid amide hydrolase Proteins 0.000 title description 3
• 102100029111 Fatty-acid amide hydrolase 1 Human genes 0.000 title 1
• 150000002547 isoxazolines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 260
• 238000000034 method Methods 0.000 claims abstract description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 10
• 101000937693 Homo sapiens Fatty acid 2-hydroxylase Proteins 0.000 claims abstract description 3
• 101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 claims abstract description 3
• 102100027297 Fatty acid 2-hydroxylase Human genes 0.000 claims abstract 2
• 125000000217 alkyl group Chemical group 0.000 claims description 673
• 125000000623 heterocyclic group Chemical group 0.000 claims description 263
• 125000003118 aryl group Chemical group 0.000 claims description 241
• 125000001072 heteroaryl group Chemical group 0.000 claims description 200
• -1 alkenyl hydrazine Chemical compound 0.000 claims description 180
• 125000000304 alkynyl group Chemical group 0.000 claims description 152
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 143
• 125000003342 alkenyl group Chemical group 0.000 claims description 132
• 125000001246 bromo group Chemical group Br* 0.000 claims description 104
• 125000002837 carbocyclic group Chemical group 0.000 claims description 104
• 208000002193 Pain Diseases 0.000 claims description 95
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 92
• 230000036407 pain Effects 0.000 claims description 90
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 78
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 70
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• 229910052757 nitrogen Inorganic materials 0.000 claims description 54
• 125000005842 heteroatom Chemical group 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 239000000460 chlorine Substances 0.000 claims description 40
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 39
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 125000004076 pyridyl group Chemical group 0.000 claims description 35
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
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• 239000007789 gas Substances 0.000 claims description 28
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 27
• 238000006467 substitution reaction Methods 0.000 claims description 27
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
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• 229910052760 oxygen Inorganic materials 0.000 claims description 24
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• 239000001301 oxygen Substances 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000004122 cyclic group Chemical group 0.000 claims description 20
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• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 16
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• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
• XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 14
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• 230000036506 anxiety Effects 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 229910052705 radium Inorganic materials 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
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• 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 claims description 5
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• IMQLKJBTEOYOSI-UHFFFAOYSA-N Diphosphoinositol tetrakisphosphate Chemical compound OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims description 3
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