JP4504021B2 - N−ピラジニル−フェニルスルホンアミド、およびケモカイン介在疾患の処置におけるそれらの使用 - Google Patents
N−ピラジニル−フェニルスルホンアミド、およびケモカイン介在疾患の処置におけるそれらの使用 Download PDFInfo
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- JP4504021B2 JP4504021B2 JP2003559997A JP2003559997A JP4504021B2 JP 4504021 B2 JP4504021 B2 JP 4504021B2 JP 2003559997 A JP2003559997 A JP 2003559997A JP 2003559997 A JP2003559997 A JP 2003559997A JP 4504021 B2 JP4504021 B2 JP 4504021B2
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- JP
- Japan
- Prior art keywords
- pyrazinyl
- methoxy
- dichloro
- benzenesulfonamide
- chloro
- Prior art date
- 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.)
- Expired - Fee Related
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 20
- 201000010099 disease Diseases 0.000 title claims description 18
- 238000011282 treatment Methods 0.000 title claims description 6
- 230000001404 mediated effect Effects 0.000 title claims description 4
- 102000019034 Chemokines Human genes 0.000 title description 11
- 108010012236 Chemokines Proteins 0.000 title description 11
- KAPFAVLCJMCLFV-UHFFFAOYSA-N n-pyrazin-2-ylbenzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NC1=CN=CC=N1 KAPFAVLCJMCLFV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 197
- -1 C 1-6 alkyl-OH Chemical group 0.000 claims description 157
- 238000000034 method Methods 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 59
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 35
- 229920006395 saturated elastomer Polymers 0.000 claims description 34
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 31
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000001246 bromo group Chemical group Br* 0.000 claims description 17
- 208000006673 asthma Diseases 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 239000001301 oxygen Chemical group 0.000 claims description 15
- 239000011593 sulfur Chemical group 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000000565 sulfonamide group Chemical group 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 101710149863 C-C chemokine receptor type 4 Proteins 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000002346 iodo group Chemical group I* 0.000 claims description 6
- XNDDKEJNTJWGJT-UHFFFAOYSA-N methyl 5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazine-2-carboxylate Chemical compound COC1=NC(C(=O)OC)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl XNDDKEJNTJWGJT-UHFFFAOYSA-N 0.000 claims description 6
- XVTJKPNVWSMCAN-UHFFFAOYSA-N methyl 6-[(2,3-dichlorophenyl)sulfonylamino]-5-methoxypyrazine-2-carboxylate Chemical compound COC(=O)C1=CN=C(OC)C(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=N1 XVTJKPNVWSMCAN-UHFFFAOYSA-N 0.000 claims description 6
- JAICZFJVUOTYPC-UHFFFAOYSA-N n-(5-bromo-6-chloro-3-methoxypyrazin-2-yl)-2,3-dichlorobenzenesulfonamide Chemical compound COC1=NC(Br)=C(Cl)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl JAICZFJVUOTYPC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- UHMIMYXJGIJBSP-UHFFFAOYSA-N methyl 5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxy-3-methylpyrazine-2-carboxylate Chemical compound N1=C(C)C(C(=O)OC)=NC(OC)=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl UHMIMYXJGIJBSP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- LJDABEKXGZUMJD-UHFFFAOYSA-N n-[5,6-bis(hydroxymethyl)-3-methoxypyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound COC1=NC(CO)=C(CO)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl LJDABEKXGZUMJD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- FLSMVCMSUNISFK-UHFFFAOYSA-N 2,3-dichloro-n-(3-methoxypyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl FLSMVCMSUNISFK-UHFFFAOYSA-N 0.000 claims description 3
- NGOIQYFFFYXUMM-UHFFFAOYSA-N 2,3-dichloro-n-[6-chloro-5-(hydroxymethyl)-3-methoxypyrazin-2-yl]benzenesulfonamide Chemical compound COC1=NC(CO)=C(Cl)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl NGOIQYFFFYXUMM-UHFFFAOYSA-N 0.000 claims description 3
- DFXCUYHMELLMRC-UHFFFAOYSA-N 3,4-dichloro-n-(6-chloro-3-methoxypyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC=C(Cl)N=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 DFXCUYHMELLMRC-UHFFFAOYSA-N 0.000 claims description 3
- ZPRWDRAGOKIYTD-UHFFFAOYSA-N 3-chloro-n-[5-chloro-3-(pyridin-3-ylmethoxy)pyrazin-2-yl]-2-methylbenzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC=C(Cl)N=C1OCC1=CC=CN=C1 ZPRWDRAGOKIYTD-UHFFFAOYSA-N 0.000 claims description 3
- 235000019000 fluorine Nutrition 0.000 claims description 3
- ORVBKAIISVAIKO-UHFFFAOYSA-N methyl 3-[5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazin-2-yl]sulfanylpropanoate Chemical compound COC1=NC(SCCC(=O)OC)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl ORVBKAIISVAIKO-UHFFFAOYSA-N 0.000 claims description 3
- OCZLUPURNBYDPZ-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-2,3-dichloro-4-fluorobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=C(F)C(Cl)=C1Cl OCZLUPURNBYDPZ-UHFFFAOYSA-N 0.000 claims description 3
- AMJJZGRYGJXVBI-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-2,3-dichlorobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl AMJJZGRYGJXVBI-UHFFFAOYSA-N 0.000 claims description 3
- AHBMLDRMXWBGNT-UHFFFAOYSA-N n-(5-bromo-3-propoxypyrazin-2-yl)-2,3-dichlorobenzenesulfonamide Chemical compound CCCOC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl AHBMLDRMXWBGNT-UHFFFAOYSA-N 0.000 claims description 3
- LOTOAEQYZJAQAS-UHFFFAOYSA-N n-[3-[(2-amino-1,3-oxazol-4-yl)methoxy]-5-chloropyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound O1C(N)=NC(COC=2C(=NC=C(Cl)N=2)NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1 LOTOAEQYZJAQAS-UHFFFAOYSA-N 0.000 claims description 3
- NNTCWJRSPFQPBC-UHFFFAOYSA-N n-[3-[[5-(aminomethyl)furan-2-yl]methoxy]-5-chloropyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound O1C(CN)=CC=C1COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl NNTCWJRSPFQPBC-UHFFFAOYSA-N 0.000 claims description 3
- LOFZVNMTEQLWRJ-UHFFFAOYSA-N n-[5-(2-aminoethoxy)-3-methoxypyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound COC1=NC(OCCN)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl LOFZVNMTEQLWRJ-UHFFFAOYSA-N 0.000 claims description 3
- XLWRRJQUFFSGGS-UHFFFAOYSA-N n-[5-(2-aminoethylsulfanyl)-3-(pyridin-2-ylmethoxy)pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound C=1C=CC=NC=1COC1=NC(SCCN)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl XLWRRJQUFFSGGS-UHFFFAOYSA-N 0.000 claims description 3
- BUZWVYPPUNMIGZ-UHFFFAOYSA-N n-[5-(2-aminoethylsulfanyl)-3-methoxypyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound COC1=NC(SCCN)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl BUZWVYPPUNMIGZ-UHFFFAOYSA-N 0.000 claims description 3
- ZTCRULQYAZGHGP-UHFFFAOYSA-N n-[5-(2-aminoethylsulfanyl)-6-chloro-3-methoxypyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound COC1=NC(SCCN)=C(Cl)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl ZTCRULQYAZGHGP-UHFFFAOYSA-N 0.000 claims description 3
- HUNHGMOTJKCXTA-UHFFFAOYSA-N n-[5-bromo-3-[3-(4-hydroxyphenyl)propoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound C1=CC(O)=CC=C1CCCOC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl HUNHGMOTJKCXTA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- LBKOCZWOYDHIMH-PPHPATTJSA-N 2,3-dichloro-n-[3-methoxy-5-[[(2s)-pyrrolidin-2-yl]methoxy]pyrazin-2-yl]benzenesulfonamide;hydrochloride Chemical compound Cl.C=1N=C(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)C(OC)=NC=1OC[C@@H]1CCCN1 LBKOCZWOYDHIMH-PPHPATTJSA-N 0.000 claims description 2
- HGBIIVXXEICSKN-UHFFFAOYSA-N 2,3-dichloro-n-[5-chloro-3-(pyridin-3-ylmethoxy)pyrazin-2-yl]benzenesulfonamide Chemical compound C=1C=CN=CC=1COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl HGBIIVXXEICSKN-UHFFFAOYSA-N 0.000 claims description 2
- GDHDULCZBXCQBR-UHFFFAOYSA-N 2,3-dichloro-n-[5-chloro-3-(pyrimidin-5-ylmethoxy)pyrazin-2-yl]benzenesulfonamide Chemical compound C=1N=CN=CC=1COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl GDHDULCZBXCQBR-UHFFFAOYSA-N 0.000 claims description 2
- CALYXUCWWNOBFK-UHFFFAOYSA-N 2,4-dichloro-n-(5-chloro-3-methoxypyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=C(Cl)C=C1Cl CALYXUCWWNOBFK-UHFFFAOYSA-N 0.000 claims description 2
- UVRGVXJHZXIJTR-UHFFFAOYSA-N 2,4-dichloro-n-(6-chloro-3-methoxypyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC=C(Cl)N=C1NS(=O)(=O)C1=CC=C(Cl)C=C1Cl UVRGVXJHZXIJTR-UHFFFAOYSA-N 0.000 claims description 2
- VENYJIJQEBQVRC-UHFFFAOYSA-N 2-[5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazin-2-yl]oxy-n,n-diethylacetamide Chemical compound COC1=NC(OCC(=O)N(CC)CC)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl VENYJIJQEBQVRC-UHFFFAOYSA-N 0.000 claims description 2
- HDYIEMFBVHPHAI-UHFFFAOYSA-N 2-[5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazin-2-yl]sulfanyl-n-methylacetamide Chemical compound COC1=NC(SCC(=O)NC)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl HDYIEMFBVHPHAI-UHFFFAOYSA-N 0.000 claims description 2
- SITANBKBOGBGEL-UHFFFAOYSA-N 2-cyano-n-(3-methoxy-5-methylpyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1C#N SITANBKBOGBGEL-UHFFFAOYSA-N 0.000 claims description 2
- NRMGWWVLQSAWLX-UHFFFAOYSA-N 2-fluoro-n-(3-methoxy-5-methylpyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1F NRMGWWVLQSAWLX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- KGQCMJDTKKPCNT-UHFFFAOYSA-N 3-chloro-n-(3-methoxy-5-methylpyrazin-2-yl)-2-methylbenzenesulfonamide Chemical compound COC1=NC(C)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C KGQCMJDTKKPCNT-UHFFFAOYSA-N 0.000 claims description 2
- CZQYOMKNOFNTSV-UHFFFAOYSA-N 3-chloro-n-(5,6-dichloro-3-methoxypyrazin-2-yl)-2-methylbenzenesulfonamide Chemical compound COC1=NC(Cl)=C(Cl)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C CZQYOMKNOFNTSV-UHFFFAOYSA-N 0.000 claims description 2
- LCBKYPGZLSAFPP-UHFFFAOYSA-N 3-chloro-n-(5-chloro-3-methoxypyrazin-2-yl)-2-fluorobenzenesulfonamide Chemical compound COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1F LCBKYPGZLSAFPP-UHFFFAOYSA-N 0.000 claims description 2
- WTUNXNFOUIUOOC-UHFFFAOYSA-N 3-chloro-n-(5-chloro-3-methoxypyrazin-2-yl)-2-methylbenzenesulfonamide Chemical compound COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C WTUNXNFOUIUOOC-UHFFFAOYSA-N 0.000 claims description 2
- NGXBSWMIRJRADL-UHFFFAOYSA-N 3-chloro-n-(6-chloro-3-methoxypyrazin-2-yl)-2-methylbenzenesulfonamide Chemical compound COC1=NC=C(Cl)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1C NGXBSWMIRJRADL-UHFFFAOYSA-N 0.000 claims description 2
- VBTIMGWSKZTTJH-UHFFFAOYSA-N 3-chloro-n-[5-chloro-3-(pyridin-3-ylmethoxy)pyrazin-2-yl]-2-fluorobenzenesulfonamide Chemical compound FC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC=C(Cl)N=C1OCC1=CC=CN=C1 VBTIMGWSKZTTJH-UHFFFAOYSA-N 0.000 claims description 2
- VXSWEXVOKUJHGJ-UHFFFAOYSA-N 3-fluoro-n-(3-methoxy-5-methylpyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC(C)=CN=C1NS(=O)(=O)C1=CC=CC(F)=C1 VXSWEXVOKUJHGJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 150000001543 aryl boronic acids Chemical class 0.000 claims description 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- CUHHLWIXFOLWOX-UHFFFAOYSA-N methyl 2-[5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazin-2-yl]oxyacetate Chemical compound COC1=NC(OCC(=O)OC)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl CUHHLWIXFOLWOX-UHFFFAOYSA-N 0.000 claims description 2
- PARCGEBZYFCVQZ-UHFFFAOYSA-N methyl 2-[5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazin-2-yl]sulfanylacetate Chemical compound COC1=NC(SCC(=O)OC)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl PARCGEBZYFCVQZ-UHFFFAOYSA-N 0.000 claims description 2
- AXRXUGZSSSEQKO-UHFFFAOYSA-N methyl 3-[(2,3-dichlorophenyl)sulfonylamino]pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl AXRXUGZSSSEQKO-UHFFFAOYSA-N 0.000 claims description 2
- RMLWVHAPXYEVII-UHFFFAOYSA-N methyl 3-chloro-5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazine-2-carboxylate Chemical compound N1=C(Cl)C(C(=O)OC)=NC(OC)=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl RMLWVHAPXYEVII-UHFFFAOYSA-N 0.000 claims description 2
- ORHJLSZLNMRRCI-UHFFFAOYSA-N n-(3-methoxy-5-methylpyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1 ORHJLSZLNMRRCI-UHFFFAOYSA-N 0.000 claims description 2
- PCUSGNBFVWJYOM-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-2,4-dichlorobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=C(Cl)C=C1Cl PCUSGNBFVWJYOM-UHFFFAOYSA-N 0.000 claims description 2
- GLRFOWWCTLYBIT-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-2,5-dichlorobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC(Cl)=CC=C1Cl GLRFOWWCTLYBIT-UHFFFAOYSA-N 0.000 claims description 2
- MRSKFHAXDKTQGO-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-2-cyanobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC=C1C#N MRSKFHAXDKTQGO-UHFFFAOYSA-N 0.000 claims description 2
- JWJUXVQDOYDQOT-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-2-iodobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC=C1I JWJUXVQDOYDQOT-UHFFFAOYSA-N 0.000 claims description 2
- XNLRPWBHTAAVBQ-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-3,4-dichlorobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 XNLRPWBHTAAVBQ-UHFFFAOYSA-N 0.000 claims description 2
- ZFPLJZKWRIHEGH-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-3,5-dichlorobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 ZFPLJZKWRIHEGH-UHFFFAOYSA-N 0.000 claims description 2
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| US7544702B2 (en) | 2004-08-12 | 2009-06-09 | Amgen Inc. | Bisaryl-sulfonamides |
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| US8586748B2 (en) * | 2008-04-09 | 2013-11-19 | Boehringer Ingelheim International Gmbh | 2-sulfonylamino-4-heteroaryl butyramide antagonists of CCR10 |
| US8673908B2 (en) | 2008-11-10 | 2014-03-18 | Kyowa Hakko Kirin Co., Ltd. | Kynurenine production inhibitor |
| TW201041583A (en) * | 2009-04-22 | 2010-12-01 | Axikin Pharmaceuticals Inc | 2,5-disubstituted arylsulfonamide CCR3 antagonists |
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| CN108383828A (zh) * | 2010-12-16 | 2018-08-10 | 阿勒根公司 | 作为趋化因子受体调节剂的新的1,2-双-磺酰胺衍生物 |
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| JP6327803B2 (ja) * | 2013-07-09 | 2018-05-23 | 久慶 ▲ふく▼楊 | 大出力高効率単相多極発電機 |
| CN106008418A (zh) * | 2016-05-20 | 2016-10-12 | 厦门大学 | 一种5-氨甲基-2-呋喃甲醇的合成方法 |
| IL276295B2 (en) * | 2018-01-26 | 2024-02-01 | Rapt Therapeutics Inc | Modulators of chemokine receptors and their uses |
| CN113069446B (zh) * | 2021-03-01 | 2022-12-02 | 中山亿维迪科技有限公司 | El102在制备治疗新型冠状病毒所致疾病的药物中的应用 |
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| GB9504854D0 (en) * | 1994-03-31 | 1995-04-26 | Zeneca Ltd | Nitrogen derivatives |
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- 2003-01-14 CA CA002472204A patent/CA2472204A1/en not_active Abandoned
- 2003-01-14 RU RU2004119966/04A patent/RU2312105C9/ru not_active IP Right Cessation
- 2003-01-14 BR BR0306922-2A patent/BR0306922A/pt not_active IP Right Cessation
- 2003-01-14 NZ NZ533750A patent/NZ533750A/xx unknown
- 2003-01-14 ES ES03700655T patent/ES2375107T3/es not_active Expired - Lifetime
- 2003-01-16 AR ARP030100126A patent/AR038179A1/es unknown
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2004
- 2004-07-08 IS IS7348A patent/IS7348A/is unknown
- 2004-07-15 CO CO04067437A patent/CO5640137A2/es not_active Application Discontinuation
- 2004-08-13 NO NO20043370A patent/NO20043370L/no not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| US7662825B2 (en) | 2010-02-16 |
| IS7348A (is) | 2004-07-08 |
| BR0306922A (pt) | 2004-11-09 |
| ATE534635T1 (de) | 2011-12-15 |
| AU2003201802A1 (en) | 2003-07-30 |
| JP2005521650A (ja) | 2005-07-21 |
| WO2003059893A1 (en) | 2003-07-24 |
| HK1068885A1 (en) | 2005-05-06 |
| NZ533750A (en) | 2006-03-31 |
| RU2312105C2 (ru) | 2007-12-10 |
| CN100357275C (zh) | 2007-12-26 |
| US20100081670A1 (en) | 2010-04-01 |
| KR20040073566A (ko) | 2004-08-19 |
| IL162678A0 (en) | 2005-11-20 |
| MXPA04006806A (es) | 2004-12-06 |
| CN1639132A (zh) | 2005-07-13 |
| CO5640137A2 (es) | 2006-05-31 |
| RU2312105C9 (ru) | 2008-06-10 |
| TWI328007B (en) | 2010-08-01 |
| US20060025423A1 (en) | 2006-02-02 |
| TW200303308A (en) | 2003-09-01 |
| RU2004119966A (ru) | 2005-06-10 |
| AR038179A1 (es) | 2005-01-05 |
| EP1467976A1 (en) | 2004-10-20 |
| NO20043370L (no) | 2004-09-28 |
| EP1467976B1 (en) | 2011-11-23 |
| CA2472204A1 (en) | 2003-07-24 |
| PL371432A1 (en) | 2005-06-13 |
| ES2375107T3 (es) | 2012-02-24 |
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