TW200524928A - Substituted naphthyridine derivatives as inhibitors of macrophage migration inhibitory factor and their use in the treatment of human diseases - Google Patents

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Publication number

TW200524928A

TW200524928A TW093124762A TW93124762A TW200524928A TW 200524928 A TW200524928 A TW 200524928A TW 093124762 A TW093124762 A TW 093124762A TW 93124762 A TW93124762 A TW 93124762A TW 200524928 A TW200524928 A TW 200524928A

Authority

TW

Taiwan

Prior art keywords

substituted

compound

item

formula

patent application

Prior art date

2003-08-22

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• 239000003112 inhibitor Substances 0.000 title claims abstract description 104
• 238000011282 treatment Methods 0.000 title claims abstract description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 29
• 108010048043 Macrophage Migration-Inhibitory Factors Proteins 0.000 title claims description 28
• 201000010099 disease Diseases 0.000 title claims description 26
• 102000009073 Macrophage Migration-Inhibitory Factors Human genes 0.000 title claims description 9
• 150000005054 naphthyridines Chemical class 0.000 title description 3
• 238000000034 method Methods 0.000 claims abstract description 188
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• 229940002612 prodrug Drugs 0.000 claims abstract description 85
• 239000000651 prodrug Substances 0.000 claims abstract description 85
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• 229910052739 hydrogen Inorganic materials 0.000 claims description 174
• 125000000623 heterocyclic group Chemical group 0.000 claims description 172
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• -1 -NO Chemical group 0.000 claims description 139
• 239000000126 substance Substances 0.000 claims description 115
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 103
• 125000003118 aryl group Chemical group 0.000 claims description 103
• 125000000217 alkyl group Chemical group 0.000 claims description 102
• 150000002431 hydrogen Chemical class 0.000 claims description 102
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 81
• 125000001424 substituent group Chemical group 0.000 claims description 77
• 125000003107 substituted aryl group Chemical group 0.000 claims description 74
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• 210000002540 macrophage Anatomy 0.000 claims description 58
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 58
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• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 40
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 34
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 33
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 32
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• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 28
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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 7
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• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
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• 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
• 229910052716 thallium Inorganic materials 0.000 claims description 2
• BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
• 102100037791 Macrophage migration inhibitory factor Human genes 0.000 claims 19
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 2
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• MKCPZCBJTCEQFQ-FQEVSTJZSA-N 5-[[5-[[(2s)-1-carboxy-4-[(2-chlorophenyl)methylsulfanyl]-3-oxobutan-2-yl]carbamoyl]thiophen-2-yl]methyl-methylsulfamoyl]-2-hydroxybenzoic acid Chemical compound O=C([C@H](CC(O)=O)NC(=O)C1=CC=C(S1)CN(C)S(=O)(=O)C=1C=C(C(O)=CC=1)C(O)=O)CSCC1=CC=CC=C1Cl MKCPZCBJTCEQFQ-FQEVSTJZSA-N 0.000 claims 1
• VEDTXTNSFWUXGQ-UHFFFAOYSA-N Carbophenothion Chemical group CCOP(=S)(OCC)SCSC1=CC=C(Cl)C=C1 VEDTXTNSFWUXGQ-UHFFFAOYSA-N 0.000 claims 1
• 150000001336 alkenes Chemical group 0.000 claims 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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• 125000004354 sulfur functional group Chemical group 0.000 claims 1
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 abstract description 29
• 230000001575 pathological effect Effects 0.000 abstract description 7
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 192
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• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 44
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