JP2008504363A - Ｐ２ｘ７受容体のベンズアミド阻害剤を利用する併用療法 - Google Patents

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Publication number

JP2008504363A

JP2008504363A JP2007518739A JP2007518739A JP2008504363A JP 2008504363 A JP2008504363 A JP 2008504363A JP 2007518739 A JP2007518739 A JP 2007518739A JP 2007518739 A JP2007518739 A JP 2007518739A JP 2008504363 A JP2008504363 A JP 2008504363A

Authority

JP

Japan

Prior art keywords

hydroxy

alkyl

chloro

benzamide

dioxo

Prior art date

2004-06-29

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.)

Withdrawn

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• 239000003112 inhibitor Substances 0.000 title claims abstract description 25
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title claims abstract description 11
• 102100037602 P2X purinoceptor 7 Human genes 0.000 title description 2
• 101710189965 P2X purinoceptor 7 Proteins 0.000 title description 2
• 238000002648 combination therapy Methods 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 66
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
• NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims abstract description 19
• 102000051628 Interleukin-1 receptor antagonist Human genes 0.000 claims abstract description 18
• 108700021006 Interleukin-1 receptor antagonist Proteins 0.000 claims abstract description 18
• UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims abstract description 18
• 229960001940 sulfasalazine Drugs 0.000 claims abstract description 18
• NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 claims abstract description 18
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 15
• 108010046938 Macrophage Colony-Stimulating Factor Proteins 0.000 claims abstract description 14
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• HMLGSIZOMSVISS-ONJSNURVSA-N (7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2,2-dimethylpropanoyloxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N([C@@H]1C(N2C(=C(C=C)CSC21)C(O)=O)=O)C(=O)\C(=N/OCOC(=O)C(C)(C)C)C1=CSC(N)=N1 HMLGSIZOMSVISS-ONJSNURVSA-N 0.000 claims abstract description 11
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• 230000001404 mediated effect Effects 0.000 claims abstract description 10
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• 150000001875 compounds Chemical class 0.000 claims description 183
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 149
• -1 hydroxy, amino Chemical group 0.000 claims description 94
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 92
• 229910052736 halogen Inorganic materials 0.000 claims description 67
• 150000002367 halogens Chemical class 0.000 claims description 67
• 125000000623 heterocyclic group Chemical group 0.000 claims description 62
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 45
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 37
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
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• 125000001424 substituent group Chemical group 0.000 claims description 35
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• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 7
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• LMVZQBQXTHCTDI-UHFFFAOYSA-N 2-chloro-5-[4-(2,3-dihydroxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycyclohexyl)methyl]benzamide Chemical compound O=C1N(CC(O)CO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCC2)=C1 LMVZQBQXTHCTDI-UHFFFAOYSA-N 0.000 claims description 6
• FUCKCIVGBCBZNP-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 FUCKCIVGBCBZNP-UHFFFAOYSA-N 0.000 claims description 6
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• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• JMVYKXHUTCCANK-UHFFFAOYSA-N 2-chloro-5-[4-(2,3-dihydroxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CC(O)CO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 JMVYKXHUTCCANK-UHFFFAOYSA-N 0.000 claims description 5
• RGFRMICGIFODJR-UHFFFAOYSA-N 5-[4-(2,3-dihydroxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]-2-methylbenzamide Chemical compound CC1=CC=C(N2C(N(CC(O)CO)C(=O)C=N2)=O)C=C1C(=O)NCC1(O)CCCCCC1 RGFRMICGIFODJR-UHFFFAOYSA-N 0.000 claims description 5
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• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• SKHOFKQIJDWTCL-UHFFFAOYSA-N 2-chloro-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-(2-hydroxy-2-phenylethyl)benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC(O)C=2C=CC=CC=2)=C1 SKHOFKQIJDWTCL-UHFFFAOYSA-N 0.000 claims description 4
• OAEZUGNBLUMOLY-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-2-phenylethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound C=1C=CC=CC=1C(O)CN(C1=O)C(=O)C=NN1C(C=1)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 OAEZUGNBLUMOLY-UHFFFAOYSA-N 0.000 claims description 4
• NAVAMNWMBLWSNC-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycyclooctyl)methyl]-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCCC2)=C1 NAVAMNWMBLWSNC-UHFFFAOYSA-N 0.000 claims description 4
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• KJPZROKEPKPKNY-UHFFFAOYSA-N 2-chloro-5-[3,5-dioxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound O=C1N(CC(O)C(F)(F)F)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 KJPZROKEPKPKNY-UHFFFAOYSA-N 0.000 claims description 3
• JBSOMXMDEHIYEI-UHFFFAOYSA-N 2-chloro-5-[4-(2-cyanoethyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[(1-hydroxycycloheptyl)methyl]benzamide Chemical compound C=1C(N2C(N(CCC#N)C(=O)C=N2)=O)=CC=C(Cl)C=1C(=O)NCC1(O)CCCCCC1 JBSOMXMDEHIYEI-UHFFFAOYSA-N 0.000 claims description 3
• GELUSLDHFNHTJQ-UHFFFAOYSA-N 2-chloro-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]-n-[[1-(hydroxymethyl)cycloheptyl]methyl]benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(CO)CCCCCC2)=C1 GELUSLDHFNHTJQ-UHFFFAOYSA-N 0.000 claims description 3
• CMDPHTPJKKJNDM-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxy-2-methylpropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(C)(O)C)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 CMDPHTPJKKJNDM-UHFFFAOYSA-N 0.000 claims description 3
• KMQUFVMVCXCGKB-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycycloheptyl)methyl]-5-[4-(2-hydroxyethyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CCO)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCCC2)=C1 KMQUFVMVCXCGKB-UHFFFAOYSA-N 0.000 claims description 3
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• UTVQECIXWCMQOC-UHFFFAOYSA-N 2-chloro-n-[(1-hydroxycyclohexyl)methyl]-5-[4-(2-hydroxy-3-methoxypropyl)-3,5-dioxo-1,2,4-triazin-2-yl]benzamide Chemical compound O=C1N(CC(O)COC)C(=O)C=NN1C1=CC=C(Cl)C(C(=O)NCC2(O)CCCCC2)=C1 UTVQECIXWCMQOC-UHFFFAOYSA-N 0.000 claims description 3
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