JP2005521650A5 - - Google Patents
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- Publication number
- JP2005521650A5 JP2005521650A5 JP2003559997A JP2003559997A JP2005521650A5 JP 2005521650 A5 JP2005521650 A5 JP 2005521650A5 JP 2003559997 A JP2003559997 A JP 2003559997A JP 2003559997 A JP2003559997 A JP 2003559997A JP 2005521650 A5 JP2005521650 A5 JP 2005521650A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazinyl
- methoxy
- benzenesulfonamide
- dichloro
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 22
- -1 C 1-6 alkyl-OH Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 45
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 229920006395 saturated elastomer Polymers 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 14
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 13
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 239000001301 oxygen Chemical group 0.000 claims 6
- 125000000565 sulfonamide group Chemical group 0.000 claims 6
- 239000011593 sulfur Chemical group 0.000 claims 6
- 125000001246 bromo group Chemical group Br* 0.000 claims 5
- 102000009410 Chemokine receptor Human genes 0.000 claims 4
- 108050000299 Chemokine receptor Proteins 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 102000019034 Chemokines Human genes 0.000 claims 2
- 108010012236 Chemokines Proteins 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 235000019000 fluorine Nutrition 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- LLWYTTSVRALNCB-UHFFFAOYSA-N 2,3-dichloro-n-(3-methoxy-5-methylpyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC(C)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl LLWYTTSVRALNCB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- ISDQXMJMZOBNOA-UHFFFAOYSA-N 2,3-dichloro-n-[5-chloro-3-[[5-[(cyclopropylamino)methyl]furan-2-yl]methoxy]pyrazin-2-yl]benzenesulfonamide Chemical compound C=1C=C(CNC2CC2)OC=1COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl ISDQXMJMZOBNOA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- PJCXOTBHXRREQN-UHFFFAOYSA-N 2-[5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazin-2-yl]sulfanylacetic acid Chemical compound COC1=NC(SCC(O)=O)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl PJCXOTBHXRREQN-UHFFFAOYSA-N 0.000 claims 1
- GKCQCYDQKNZYMS-UHFFFAOYSA-N 2-chloro-n-(5-chloro-3-methoxypyrazin-2-yl)-3-fluorobenzenesulfonamide Chemical compound COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(F)=C1Cl GKCQCYDQKNZYMS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- DVKHWICOXREYGU-UHFFFAOYSA-N 2-iodo-n-(3-methoxy-5-methylpyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1I DVKHWICOXREYGU-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 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 1
- VGZKJDWZVMCUBU-UHFFFAOYSA-N 3-[[6-chloro-3-[(2,3-dichlorophenyl)sulfonylamino]pyrazin-2-yl]oxymethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(COC=2C(=NC=C(Cl)N=2)NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1 VGZKJDWZVMCUBU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- NGTJHOCCPZVWNX-UHFFFAOYSA-N 4-[5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazin-2-yl]oxybenzoic acid Chemical compound C=1N=C(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)C(OC)=NC=1OC1=CC=C(C(O)=O)C=C1 NGTJHOCCPZVWNX-UHFFFAOYSA-N 0.000 claims 1
- YZWYKWZNHHWJJP-UHFFFAOYSA-N 5-[(2,3-dichlorophenyl)sulfonylamino]-6-(pyridin-3-ylmethoxy)pyrazine-2-carboxamide Chemical compound C=1C=CN=CC=1COC1=NC(C(=O)N)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl YZWYKWZNHHWJJP-UHFFFAOYSA-N 0.000 claims 1
- 102000004498 CCR4 Receptors Human genes 0.000 claims 1
- 108010017317 CCR4 Receptors Proteins 0.000 claims 1
- 150000001543 aryl boronic acids Chemical class 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- DVUJUSGVWPWOTM-UHFFFAOYSA-N methyl 3-[[6-chloro-3-[(2,3-dichlorophenyl)sulfonylamino]pyrazin-2-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C(=NC=C(Cl)N=2)NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1 DVUJUSGVWPWOTM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HWDRBUSTZAMVJD-UHFFFAOYSA-N methyl 5-[(2,3-dichlorophenyl)sulfonylamino]-6-(pyridin-3-ylmethoxy)pyrazine-2-carboxylate Chemical compound C=1C=CN=CC=1COC1=NC(C(=O)OC)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl HWDRBUSTZAMVJD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- DOBVQSOAXDKWQU-UHFFFAOYSA-N n-(3-butoxy-5-chloropyrazin-2-yl)-2,3-dichlorobenzenesulfonamide Chemical compound CCCCOC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl DOBVQSOAXDKWQU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- LNQFJAGIZQJIMC-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-2-(trifluoromethoxy)benzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F LNQFJAGIZQJIMC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- NMSRPAYNDQYIQS-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-3-chlorobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1 NMSRPAYNDQYIQS-UHFFFAOYSA-N 0.000 claims 1
- XOJBRGMLSMEWQQ-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)-4-chlorobenzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 XOJBRGMLSMEWQQ-UHFFFAOYSA-N 0.000 claims 1
- OFPUUWQRPOXEQY-UHFFFAOYSA-N n-(5-bromo-3-methoxypyrazin-2-yl)benzenesulfonamide Chemical compound COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC=C1 OFPUUWQRPOXEQY-UHFFFAOYSA-N 0.000 claims 1
- RLEVKHKYSDRCIL-UHFFFAOYSA-N n-(5-bromo-3-pentoxypyrazin-2-yl)-2,3-dichlorobenzenesulfonamide Chemical compound CCCCCOC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl RLEVKHKYSDRCIL-UHFFFAOYSA-N 0.000 claims 1
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| SE0201857A SE0201857D0 (sv) | 2002-06-17 | 2002-06-17 | Novel compounds |
| PCT/SE2003/000041 WO2003059893A1 (en) | 2002-01-16 | 2003-01-14 | N-pyrazinyl-phenylsulphonamides and their use in the treatment of chemokine mediated diseases |
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|---|---|---|---|---|
| AU2003252478A1 (en) * | 2002-07-10 | 2004-02-02 | Ono Pharmaceutical Co., Ltd. | Ccr4 antagonist and medicinal use thereof |
| GB0217431D0 (en) | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
| WO2004018435A1 (en) | 2002-08-24 | 2004-03-04 | Astrazeneca Ab | Pyrimidine derivatives as modulators of chemokine receptor activity |
| SE0301653D0 (sv) * | 2003-06-05 | 2003-06-05 | Astrazeneca Ab | Novel compounds |
| SE0302304D0 (sv) * | 2003-08-27 | 2003-08-27 | Astrazeneca Ab | Novel compounds |
| WO2005023771A1 (ja) * | 2003-09-05 | 2005-03-17 | Ono Pharmaceutical Co., Ltd. | ケモカインレセプターアンタゴニストおよびその医薬用途 |
| GB0401269D0 (en) * | 2004-01-21 | 2004-02-25 | Astrazeneca Ab | Compounds |
| AU2005272786B2 (en) * | 2004-08-12 | 2011-12-22 | Amgen Inc. | Bisaryl-sulfonamides |
| SI1809624T1 (sl) | 2004-08-28 | 2014-02-28 | Astrazeneca Ab | Derivati pirimidinsulfonamida kot modulatorji receptorja kemokina |
| TW200800921A (en) * | 2005-09-19 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| EP1956009A1 (en) * | 2005-12-02 | 2008-08-13 | Mitsubishi Tanabe Pharma Corporation | Aromatic compound |
| US20090182140A1 (en) * | 2005-12-02 | 2009-07-16 | Mitsubishi Tanabe Pharma Corporation | Alicyclic Heterocyclic Compound |
| TW200730512A (en) * | 2005-12-12 | 2007-08-16 | Astrazeneca Ab | Novel compounds |
| GB0526255D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| BRPI0813244B8 (pt) | 2007-06-27 | 2021-05-25 | Astrazeneca Ab | compostos derivados de pirazinona, composições compreendendo ditos compostos, uso dos compostos no tratamento de doenças de pulmão e composto intermediário |
| JP5492189B2 (ja) * | 2008-04-09 | 2014-05-14 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１０アンタゴニストである２−スルホニルアミノ−４−ヘテロアリールブチロアミド |
| WO2010053182A1 (ja) | 2008-11-10 | 2010-05-14 | 協和発酵キリン株式会社 | キヌレニン産生抑制剤 |
| TW201041583A (en) * | 2009-04-22 | 2010-12-01 | Axikin Pharmaceuticals Inc | 2,5-disubstituted arylsulfonamide CCR3 antagonists |
| TWI535442B (zh) | 2010-05-10 | 2016-06-01 | Kyowa Hakko Kirin Co Ltd | A nitrogen-containing heterocyclic compound having an action of inhibiting the production of canine erythritine |
| 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 |
| ES2651484T3 (es) | 2011-11-09 | 2018-01-26 | Kyowa Hakko Kirin Co., Ltd. | Compuesto heterocíclico que contiene nitrógeno |
| 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 |
| PL3743418T3 (pl) * | 2018-01-26 | 2024-11-25 | Rapt Therapeutics, Inc. | Modulatory receptorów chemokinowych i ich zastosowania |
| 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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| US143024A (en) * | 1873-09-23 | Improvement in clothes-pins | ||
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| GB9504854D0 (en) * | 1994-03-31 | 1995-04-26 | Zeneca Ltd | Nitrogen derivatives |
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| GB2295616A (en) * | 1994-12-01 | 1996-06-05 | Zeneca Ltd | N-Diazine-benzenesulphonamide derivatives as endothelin receptor antagonists |
| GB9512697D0 (en) * | 1995-06-22 | 1995-08-23 | Zeneca Ltd | Heterocyclic compounds |
| US6638937B2 (en) | 1998-07-06 | 2003-10-28 | Bristol-Myers Squibb Co. | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
| ES2318899T3 (es) | 1998-07-06 | 2009-05-01 | Bristol-Myers Squibb Company | Bifenil sulfonamidas como antagonistas duales de los receptores de angiotensina y endotelina. |
| EP1741713A3 (en) | 1999-12-15 | 2009-09-09 | Bristol-Myers Squibb Company | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
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| AU2003252478A1 (en) | 2002-07-10 | 2004-02-02 | Ono Pharmaceutical Co., Ltd. | Ccr4 antagonist and medicinal use thereof |
| SE0301650D0 (sv) | 2003-06-04 | 2003-06-04 | Astrazeneca Ab | Novel compounds |
| SE0301653D0 (sv) * | 2003-06-05 | 2003-06-05 | Astrazeneca Ab | Novel compounds |
| SE0301654D0 (sv) | 2003-06-05 | 2003-06-05 | Astrazeneca Ab | Novel compounds |
| SE0302304D0 (sv) | 2003-08-27 | 2003-08-27 | Astrazeneca Ab | Novel compounds |
| TW200800921A (en) | 2005-09-19 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| TW200730512A (en) | 2005-12-12 | 2007-08-16 | Astrazeneca Ab | Novel compounds |
-
2003
- 2003-01-07 TW TW092100237A patent/TWI328007B/zh active
- 2003-01-14 CN CNB038044811A patent/CN100357275C/zh not_active Expired - Fee Related
- 2003-01-14 IL IL16267803A patent/IL162678A0/xx unknown
- 2003-01-14 KR KR10-2004-7010982A patent/KR20040073566A/ko not_active Ceased
- 2003-01-14 US US10/501,510 patent/US7662825B2/en not_active Expired - Fee Related
- 2003-01-14 AT AT03700655T patent/ATE534635T1/de active
- 2003-01-14 NZ NZ533750A patent/NZ533750A/xx unknown
- 2003-01-14 AU AU2003201802A patent/AU2003201802A1/en not_active Abandoned
- 2003-01-14 CA CA002472204A patent/CA2472204A1/en not_active Abandoned
- 2003-01-14 WO PCT/SE2003/000041 patent/WO2003059893A1/en not_active Ceased
- 2003-01-14 RU RU2004119966/04A patent/RU2312105C9/ru not_active IP Right Cessation
- 2003-01-14 ES ES03700655T patent/ES2375107T3/es not_active Expired - Lifetime
- 2003-01-14 JP JP2003559997A patent/JP4504021B2/ja not_active Expired - Fee Related
- 2003-01-14 MX MXPA04006806A patent/MXPA04006806A/es active IP Right Grant
- 2003-01-14 EP EP03700655A patent/EP1467976B1/en not_active Expired - Lifetime
- 2003-01-14 BR BR0306922-2A patent/BR0306922A/pt not_active IP Right Cessation
- 2003-01-14 PL PL03371432A patent/PL371432A1/xx not_active Application Discontinuation
- 2003-01-16 AR ARP030100126A patent/AR038179A1/es unknown
-
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
-
2009
- 2009-05-05 US US12/435,864 patent/US20100081670A1/en not_active Abandoned