RU2312105C9 - N-пиразинилфенилсульфонамиды и их применение при лечении опосредованных хемокинами заболеваний - Google Patents
N-пиразинилфенилсульфонамиды и их применение при лечении опосредованных хемокинами заболеваний Download PDFInfo
- Publication number
- RU2312105C9 RU2312105C9 RU2004119966/04A RU2004119966A RU2312105C9 RU 2312105 C9 RU2312105 C9 RU 2312105C9 RU 2004119966/04 A RU2004119966/04 A RU 2004119966/04A RU 2004119966 A RU2004119966 A RU 2004119966A RU 2312105 C9 RU2312105 C9 RU 2312105C9
- Authority
- RU
- Russia
- Prior art keywords
- pyrazinyl
- methoxy
- benzenesulfonamide
- dichloro
- chloro
- Prior art date
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- 201000010099 disease Diseases 0.000 title claims abstract 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract 5
- 230000001404 mediated effect Effects 0.000 title claims 2
- 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 abstract 2
- 102000019034 Chemokines Human genes 0.000 title 1
- 108010012236 Chemokines Proteins 0.000 title 1
- -1 hydroxy- Chemical class 0.000 claims abstract 37
- 150000001875 compounds Chemical class 0.000 claims abstract 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 14
- 150000003839 salts Chemical class 0.000 claims abstract 11
- 239000012453 solvate Substances 0.000 claims abstract 8
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 230000000694 effects Effects 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 208000006673 asthma Diseases 0.000 claims abstract 2
- 208000027866 inflammatory disease Diseases 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 51
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 28
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 20
- 229920006395 saturated elastomer Polymers 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000001246 bromo group Chemical group Br* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000002346 iodo group Chemical group I* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 101710149863 C-C chemokine receptor type 4 Proteins 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 102100032976 CCR4-NOT transcription complex subunit 6 Human genes 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 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
- 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
- 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
- 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
- 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
- WBSAIKZGUPAPFP-UHFFFAOYSA-N n-(5-bromo-3-phenylmethoxypyrazin-2-yl)-2,3-dichlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=NC(Br)=CN=2)OCC=2C=CC=CC=2)=C1Cl WBSAIKZGUPAPFP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- FTJXKLOHDXYXKB-UHFFFAOYSA-N n-(6-chloro-3-methoxypyrazin-2-yl)-2,3,4-trifluorobenzenesulfonamide Chemical compound COC1=NC=C(Cl)N=C1NS(=O)(=O)C1=CC=C(F)C(F)=C1F FTJXKLOHDXYXKB-UHFFFAOYSA-N 0.000 claims 1
- HMFBZXZVUQZFPX-UHFFFAOYSA-N n-[2-[[3-chloro-5-[(2,3-dichlorophenyl)sulfonylamino]-6-methoxypyrazin-2-yl]amino]ethyl]acetamide Chemical compound COC1=NC(NCCNC(C)=O)=C(Cl)N=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl HMFBZXZVUQZFPX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BZGSICRNBXLQQL-UHFFFAOYSA-N n-[3-[(3-bromophenyl)methoxy]-5-chloropyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound C=1C=CC(Br)=CC=1COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl BZGSICRNBXLQQL-UHFFFAOYSA-N 0.000 claims 1
- BPKZMQDTAXKPRY-UHFFFAOYSA-N n-[3-[(5-bromopyridin-3-yl)methoxy]-5-chloropyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound C=1N=CC(Br)=CC=1COC1=NC(Cl)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl BPKZMQDTAXKPRY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HKQSUOKDAPBGDB-UHFFFAOYSA-N n-[3-[[5-(aminomethyl)furan-2-yl]methoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound O1C(CN)=CC=C1COC1=NC=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl HKQSUOKDAPBGDB-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
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- VUJWMBNFPYKRCZ-UHFFFAOYSA-N n-[5-bromo-3-(2-phenoxyethoxy)pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=NC(Br)=CN=2)OCCOC=2C=CC=CC=2)=C1Cl VUJWMBNFPYKRCZ-UHFFFAOYSA-N 0.000 claims 1
- QHXVWJBIGJSJCA-UHFFFAOYSA-N n-[5-bromo-3-(3-phenoxypropoxy)pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=NC(Br)=CN=2)OCCCOC=2C=CC=CC=2)=C1Cl QHXVWJBIGJSJCA-UHFFFAOYSA-N 0.000 claims 1
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- GOTOXPADOVDQIS-UHFFFAOYSA-N n-[5-bromo-3-(cyclopropylmethoxy)pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=NC(Br)=CN=2)OCC2CC2)=C1Cl GOTOXPADOVDQIS-UHFFFAOYSA-N 0.000 claims 1
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- KVLXPYVGRRKZQW-UHFFFAOYSA-N n-[5-bromo-3-(pyridin-3-ylmethoxy)pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=NC(Br)=CN=2)OCC=2C=NC=CC=2)=C1Cl KVLXPYVGRRKZQW-UHFFFAOYSA-N 0.000 claims 1
- DOCYGIZOHFMAOG-UHFFFAOYSA-N n-[5-bromo-3-(pyrimidin-5-ylmethoxy)pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=NC(Br)=CN=2)OCC=2C=NC=NC=2)=C1Cl DOCYGIZOHFMAOG-UHFFFAOYSA-N 0.000 claims 1
- MGMARBNJOADPBI-UHFFFAOYSA-N n-[5-bromo-3-(thiophen-3-ylmethoxy)pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=NC(Br)=CN=2)OCC2=CSC=C2)=C1Cl MGMARBNJOADPBI-UHFFFAOYSA-N 0.000 claims 1
- CAPUGIDKBSUYTC-UHFFFAOYSA-N n-[5-bromo-3-[(1-methyl-6-oxopyridin-3-yl)methoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound C1=CC(=O)N(C)C=C1COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl CAPUGIDKBSUYTC-UHFFFAOYSA-N 0.000 claims 1
- LKMIQPPMIFMNLL-UHFFFAOYSA-N n-[5-bromo-3-[(2-methylfuran-3-yl)methoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound O1C=CC(COC=2C(=NC=C(Br)N=2)NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1C LKMIQPPMIFMNLL-UHFFFAOYSA-N 0.000 claims 1
- ZHPPFHDYXXQSJJ-UHFFFAOYSA-N n-[5-bromo-3-[(3-fluorophenyl)methoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound FC1=CC=CC(COC=2C(=NC=C(Br)N=2)NS(=O)(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1 ZHPPFHDYXXQSJJ-UHFFFAOYSA-N 0.000 claims 1
- HVENQKASIYZAPX-UHFFFAOYSA-N n-[5-bromo-3-[(4-fluorophenyl)methoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound C1=CC(F)=CC=C1COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl HVENQKASIYZAPX-UHFFFAOYSA-N 0.000 claims 1
- RAYXDCNKWXBCFO-UHFFFAOYSA-N n-[5-bromo-3-[2-(methylamino)ethoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound CNCCOC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl RAYXDCNKWXBCFO-UHFFFAOYSA-N 0.000 claims 1
- RHHHVKKSGFKEAI-VIFPVBQESA-N n-[5-bromo-3-[[(2s)-pyrrolidin-2-yl]methoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=NC(Br)=CN=2)OC[C@H]2NCCC2)=C1Cl RHHHVKKSGFKEAI-VIFPVBQESA-N 0.000 claims 1
- CNZYJEOGKYBMJJ-UHFFFAOYSA-N n-[5-bromo-3-[[5-[(dimethylamino)methyl]furan-2-yl]methoxy]pyrazin-2-yl]-2,3-dichlorobenzenesulfonamide Chemical compound O1C(CN(C)C)=CC=C1COC1=NC(Br)=CN=C1NS(=O)(=O)C1=CC=CC(Cl)=C1Cl CNZYJEOGKYBMJJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
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- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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| SE0200119-6 | 2002-01-16 | ||
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| SE0201857A SE0201857D0 (sv) | 2002-06-17 | 2002-06-17 | Novel compounds |
| SE0201857-0 | 2002-06-17 |
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| RU2004119966A RU2004119966A (ru) | 2005-06-10 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2532515C2 (ru) * | 2009-04-22 | 2014-11-10 | Аксикин Фармасьютикалз, Инк. | 2,5-дизамещенные арилсульфонамидные антагонисты ccr3 |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1541563A4 (en) * | 2002-07-10 | 2007-11-07 | Ono Pharmaceutical Co | ANTAGONIST OF CCR4 AND CORRESPONDING MEDICINAL USE |
| GB0217431D0 (en) | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
| DE60318219T2 (de) | 2002-08-24 | 2009-01-15 | Astrazeneca Ab | PYRIMIDINDERIVATE ALS MODULATOREN DER AKTIVITuT VON CHEMOKINREZEPTOREN |
| SE0301653D0 (sv) * | 2003-06-05 | 2003-06-05 | Astrazeneca Ab | Novel compounds |
| SE0302304D0 (sv) * | 2003-08-27 | 2003-08-27 | Astrazeneca Ab | Novel compounds |
| US7732442B2 (en) | 2003-09-05 | 2010-06-08 | Ono Pharmaceutical Co., Ltd. | Chemokine receptor antagonist and medical use thereof |
| GB0401269D0 (en) * | 2004-01-21 | 2004-02-25 | Astrazeneca Ab | Compounds |
| DE602005020313D1 (de) | 2004-08-12 | 2010-05-12 | Amgen Inc | Bisaryl-sulfonamide |
| BRPI0514735B8 (pt) | 2004-08-28 | 2021-05-25 | Astrazeneca Ab | derivados de pirimidino sulfonamida como moduladores do receptor de quimiocina. |
| TW200800921A (en) * | 2005-09-19 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| EP1970373A1 (en) * | 2005-12-02 | 2008-09-17 | Mitsubishi Tanabe Pharma Corporation | Alicyclic heterocyclic compound |
| WO2007063935A1 (ja) * | 2005-12-02 | 2007-06-07 | Mitsubishi Tanabe Pharma Corporation | 芳香族化合物 |
| TW200730512A (en) * | 2005-12-12 | 2007-08-16 | Astrazeneca Ab | Novel compounds |
| GB0526255D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| JP5140154B2 (ja) | 2007-06-27 | 2013-02-06 | アストラゼネカ・アクチエボラーグ | ピラジノン誘導体および肺疾患の処置におけるそれらの使用 |
| WO2009126675A1 (en) * | 2008-04-09 | 2009-10-15 | Boehringer Ingelheim International Gmbh | 2-sulfonylamino-4-heteroaryl butyramide antagonists of ccr10 |
| PT2374802E (pt) | 2008-11-10 | 2014-07-10 | Kyowa Hakko Kirin Co Ltd | Inibidor de produção de quinurenina |
| 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 |
| EP2955173B1 (en) * | 2010-12-16 | 2017-10-04 | Allergan, Inc. | 1,2-bis-sulfonamide derivatives as chemokine receptor modulators |
| ES2903205T3 (es) | 2011-11-09 | 2022-03-31 | Kyowa Kirin Co Ltd | Compuestos heterocíclicos que contienen 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 |
| HUE069276T2 (hu) * | 2018-01-26 | 2025-02-28 | Rapt Therapeutics Inc | Kemokin receptor modulátorok és azok felhasználása |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995026957A1 (en) * | 1994-03-31 | 1995-10-12 | Zeneca Limited | N-heterocyclyl sulphonamide derivatives and their use as endothelin antagonists |
| GB2295616A (en) * | 1994-12-01 | 1996-06-05 | Zeneca Ltd | N-Diazine-benzenesulphonamide derivatives as endothelin receptor antagonists |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US143024A (en) * | 1873-09-23 | Improvement in clothes-pins | ||
| US5962490A (en) | 1987-09-25 | 1999-10-05 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| CA2162630C (en) | 1994-11-25 | 2007-05-01 | Volker Breu | Sulfonamides |
| 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 |
| KR20010083092A (ko) * | 1998-07-06 | 2001-08-31 | 스티븐 비. 데이비스 | 이중 안지오텐신 엔도텔린 수용체 길항제로서의 비페닐술폰아미드 |
| EP1237888B1 (en) | 1999-12-15 | 2006-09-13 | Bristol-Myers Squibb Company | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
| EP1458715B1 (en) | 2001-12-18 | 2005-12-07 | AstraZeneca AB | Novel compounds |
| EP1541563A4 (en) | 2002-07-10 | 2007-11-07 | Ono Pharmaceutical Co | ANTAGONIST OF CCR4 AND CORRESPONDING MEDICINAL USE |
| SE0301650D0 (sv) | 2003-06-04 | 2003-06-04 | Astrazeneca Ab | Novel compounds |
| SE0301654D0 (sv) | 2003-06-05 | 2003-06-05 | Astrazeneca Ab | Novel compounds |
| SE0301653D0 (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 |
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- 2003-01-14 WO PCT/SE2003/000041 patent/WO2003059893A1/en not_active Ceased
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- 2003-01-14 BR BR0306922-2A patent/BR0306922A/pt not_active IP Right Cessation
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- 2003-01-14 CN CNB038044811A patent/CN100357275C/zh not_active Expired - Fee Related
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- 2004-08-13 NO NO20043370A patent/NO20043370L/no not_active Application Discontinuation
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995026957A1 (en) * | 1994-03-31 | 1995-10-12 | Zeneca Limited | N-heterocyclyl sulphonamide derivatives and their use as endothelin antagonists |
| GB2295616A (en) * | 1994-12-01 | 1996-06-05 | Zeneca Ltd | N-Diazine-benzenesulphonamide derivatives as endothelin receptor antagonists |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2532515C2 (ru) * | 2009-04-22 | 2014-11-10 | Аксикин Фармасьютикалз, Инк. | 2,5-дизамещенные арилсульфонамидные антагонисты ccr3 |
Also Published As
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| TW200303308A (en) | 2003-09-01 |
| RU2004119966A (ru) | 2005-06-10 |
| US20060025423A1 (en) | 2006-02-02 |
| US7662825B2 (en) | 2010-02-16 |
| CN100357275C (zh) | 2007-12-26 |
| WO2003059893A1 (en) | 2003-07-24 |
| JP2005521650A (ja) | 2005-07-21 |
| CO5640137A2 (es) | 2006-05-31 |
| RU2312105C2 (ru) | 2007-12-10 |
| HK1068885A1 (en) | 2005-05-06 |
| JP4504021B2 (ja) | 2010-07-14 |
| KR20040073566A (ko) | 2004-08-19 |
| AR038179A1 (es) | 2005-01-05 |
| PL371432A1 (en) | 2005-06-13 |
| CN1639132A (zh) | 2005-07-13 |
| TWI328007B (en) | 2010-08-01 |
| ES2375107T3 (es) | 2012-02-24 |
| CA2472204A1 (en) | 2003-07-24 |
| BR0306922A (pt) | 2004-11-09 |
| ATE534635T1 (de) | 2011-12-15 |
| NZ533750A (en) | 2006-03-31 |
| IS7348A (is) | 2004-07-08 |
| MXPA04006806A (es) | 2004-12-06 |
| AU2003201802A1 (en) | 2003-07-30 |
| IL162678A0 (en) | 2005-11-20 |
| US20100081670A1 (en) | 2010-04-01 |
| EP1467976B1 (en) | 2011-11-23 |
| EP1467976A1 (en) | 2004-10-20 |
| NO20043370L (no) | 2004-09-28 |
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