JP2003081937A - ベンゼンスルホンアミド誘導体 - Google Patents
ベンゼンスルホンアミド誘導体Info
- Publication number
- JP2003081937A JP2003081937A JP2001272327A JP2001272327A JP2003081937A JP 2003081937 A JP2003081937 A JP 2003081937A JP 2001272327 A JP2001272327 A JP 2001272327A JP 2001272327 A JP2001272327 A JP 2001272327A JP 2003081937 A JP2003081937 A JP 2003081937A
- Authority
- JP
- Japan
- Prior art keywords
- branched
- hydrogen
- alkyl
- straight
- ring
- 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.)
- Pending
Links
- 150000008331 benzenesulfonamides Chemical class 0.000 title claims abstract description 19
- 239000004480 active ingredient Substances 0.000 claims abstract description 13
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 208000006673 asthma Diseases 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- 239000001257 hydrogen Substances 0.000 claims description 88
- -1 chloro, iodo Chemical group 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 65
- 150000002431 hydrogen Chemical class 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 23
- UOTCXIMRODXHSV-UHFFFAOYSA-N [2,3-dihydroxy-4-(2-methylsulfonyloxyethylazaniumyl)butyl]-(2-methylsulfonyloxyethyl)azanium;dichloride Chemical compound [Cl-].[Cl-].CS(=O)(=O)OCC[NH2+]CC(O)C(O)C[NH2+]CCOS(C)(=O)=O UOTCXIMRODXHSV-UHFFFAOYSA-N 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 206010020850 Hyperthyroidism Diseases 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 206010039083 rhinitis Diseases 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- VRFKGWJBBLGBDV-UHFFFAOYSA-N 1-[2-(2,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC=C1Cl VRFKGWJBBLGBDV-UHFFFAOYSA-N 0.000 claims description 2
- SWZVWZBDHFNTLD-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-4-pyrrolidin-1-ylpiperidine Chemical compound C1CC(N2CCCC2)CCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 SWZVWZBDHFNTLD-UHFFFAOYSA-N 0.000 claims description 2
- POXBXXTZUWRVJJ-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 POXBXXTZUWRVJJ-UHFFFAOYSA-N 0.000 claims description 2
- QMYALZOMMNFABZ-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-methylpiperazine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 QMYALZOMMNFABZ-UHFFFAOYSA-N 0.000 claims description 2
- ZWAXHPFRFWAHJH-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCC2)=C1 ZWAXHPFRFWAHJH-UHFFFAOYSA-N 0.000 claims description 2
- QUKOYWSWDYFCSC-UHFFFAOYSA-N 1-cyclohexyl-4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C2CCCCC2)=C1 QUKOYWSWDYFCSC-UHFFFAOYSA-N 0.000 claims description 2
- BXBXBZDVLVEBBP-UHFFFAOYSA-N 2-[4-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonylpiperazin-1-yl]ethanol Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CCO)CC2)=C1 BXBXBZDVLVEBBP-UHFFFAOYSA-N 0.000 claims description 2
- SVJZYRLXAFKAGE-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-(4-pyrrolidin-1-ylpiperidin-1-yl)sulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCC(CC2)N2CCCC2)=C1 SVJZYRLXAFKAGE-UHFFFAOYSA-N 0.000 claims description 2
- FCRPFAFVEWSZBJ-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 FCRPFAFVEWSZBJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 2
- NDZYPHLNJZSQJY-QNWVGRARSA-N 1-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-3-[(1r,2s)-2-[[(3s)-3-[(4-fluorophenyl)methyl]piperidin-1-yl]methyl]cyclohexyl]urea Chemical compound CC1=C(C(=O)C)SC(NC(=O)N[C@H]2[C@@H](CCCC2)CN2C[C@H](CC=3C=CC(F)=CC=3)CCC2)=N1 NDZYPHLNJZSQJY-QNWVGRARSA-N 0.000 claims 1
- 206010037391 Pulmonary granuloma Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 33
- 230000003042 antagnostic effect Effects 0.000 abstract description 6
- 230000002757 inflammatory effect Effects 0.000 abstract description 6
- 206010039085 Rhinitis allergic Diseases 0.000 abstract description 3
- 201000010105 allergic rhinitis Diseases 0.000 abstract description 3
- 101150004010 CXCR3 gene Proteins 0.000 abstract description 2
- 206010012438 Dermatitis atopic Diseases 0.000 abstract description 2
- 201000008937 atopic dermatitis Diseases 0.000 abstract description 2
- 208000026278 immune system disease Diseases 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 93
- 239000000203 mixture Substances 0.000 description 85
- 239000000243 solution Substances 0.000 description 40
- 210000004027 cell Anatomy 0.000 description 38
- 239000002904 solvent Substances 0.000 description 36
- 239000000460 chlorine Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 238000011156 evaluation Methods 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 239000011575 calcium Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000001525 receptor binding assay Methods 0.000 description 20
- 102100023688 Eotaxin Human genes 0.000 description 19
- 101710139422 Eotaxin Proteins 0.000 description 19
- 239000012267 brine Substances 0.000 description 19
- 238000001914 filtration Methods 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 235000002639 sodium chloride Nutrition 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 230000035605 chemotaxis Effects 0.000 description 14
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 210000003979 eosinophil Anatomy 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 230000014509 gene expression Effects 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 229910052791 calcium Inorganic materials 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 7
- 229960002329 methacholine Drugs 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 6
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 6
- 108010012236 Chemokines Proteins 0.000 description 6
- 102000019034 Chemokines Human genes 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 101000980744 Homo sapiens C-C chemokine receptor type 3 Proteins 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 6
- 102000043445 human CCR3 Human genes 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 238000009739 binding Methods 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 210000004072 lung Anatomy 0.000 description 5
- 238000010232 migration assay Methods 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000007995 HEPES buffer Substances 0.000 description 4
- 239000012981 Hank's balanced salt solution Substances 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000006285 cell suspension Substances 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- 231100000673 dose–response relationship Toxicity 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 210000004969 inflammatory cell Anatomy 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 230000000241 respiratory effect Effects 0.000 description 4
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
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- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- YQCPBTFUGBLXMR-UHFFFAOYSA-N tert-butyl 4-(5-bromo-2-hydroxyphenyl)sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CC(Br)=CC=C1O YQCPBTFUGBLXMR-UHFFFAOYSA-N 0.000 description 1
- JIBQUVFMGQWASR-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dichlorophenoxy)-5-(dimethylcarbamoyl)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CC(C(=O)N(C)C)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 JIBQUVFMGQWASR-UHFFFAOYSA-N 0.000 description 1
- OVDRXPLCRIMKLT-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylanilino)-5-nitrophenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(NC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 OVDRXPLCRIMKLT-UHFFFAOYSA-N 0.000 description 1
- SSLSSQQAQXHHHX-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenoxy)-4-methyl-5-nitrophenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=C(C)C=2)[N+]([O-])=O)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 SSLSSQQAQXHHHX-UHFFFAOYSA-N 0.000 description 1
- XEQZIQWYGXIVOQ-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenoxy)-5-hydroxyphenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(O)=CC=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 XEQZIQWYGXIVOQ-UHFFFAOYSA-N 0.000 description 1
- NWYDOGZDEAFZBS-UHFFFAOYSA-N tert-butyl 4-[2-(3,5-dimethylphenoxy)-5-methoxyphenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CC(OC)=CC=C1OC1=CC(C)=CC(C)=C1 NWYDOGZDEAFZBS-UHFFFAOYSA-N 0.000 description 1
- MITJDYLEIWTXNE-UHFFFAOYSA-N tert-butyl 4-[5-amino-2-(3,5-dimethylphenoxy)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(N)=CC=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 MITJDYLEIWTXNE-UHFFFAOYSA-N 0.000 description 1
- FWWFCBQFHPJSAV-UHFFFAOYSA-N tert-butyl 4-[5-bromo-2-(3,5-dimethylphenoxy)phenyl]sulfonylpiperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC(Br)=CC=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 FWWFCBQFHPJSAV-UHFFFAOYSA-N 0.000 description 1
- JECGTFYIDZAKOE-UHFFFAOYSA-N tert-butyl 4-[[5-(3,5-dimethylphenoxy)-1h-indol-6-yl]sulfonyl]piperazine-1-carboxylate Chemical compound CC1=CC(C)=CC(OC=2C(=CC=3NC=CC=3C=2)S(=O)(=O)N2CCN(CC2)C(=O)OC(C)(C)C)=C1 JECGTFYIDZAKOE-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001272327A JP2003081937A (ja) | 2001-09-07 | 2001-09-07 | ベンゼンスルホンアミド誘導体 |
| ARP020103259A AR037235A1 (es) | 2001-09-07 | 2002-08-29 | Derivados de sulfonamida, medicamentos que los contienen y el uso de dichos derivados para la preparacion de medicamentos |
| ES07013793T ES2354378T3 (es) | 2001-09-07 | 2002-09-04 | Derivados de arilsulfonamida para usar como antagonistas de ccr3 en el tratamiento de trastornos inflamatorios e inmunológicos. |
| DE60238149T DE60238149D1 (de) | 2001-09-07 | 2002-09-04 | Arylsulfonamid-Derivate zur Verwendung als CCR3-Antagonisten bei der Behandlung von inflammatorischen und immunologischen Erkrankungen |
| CA002459432A CA2459432C (en) | 2001-09-07 | 2002-09-04 | Arylsulfonamide derivatives for use as ccr3 antagonists in the treatment of inflammatory and immunological disorders |
| EP02772265A EP1461038B9 (en) | 2001-09-07 | 2002-09-04 | Arylsulfonamide derivatives for use as ccr3 antagonists in the treatment of inflammatory and immunological disorders |
| US10/489,029 US7700586B2 (en) | 2001-09-07 | 2002-09-04 | Arylsulfonamide derivatives for use as ccr3 antagonists in the treatment of inflammatory and immunological disorders |
| PCT/EP2002/009873 WO2003022277A1 (en) | 2001-09-07 | 2002-09-04 | Arylsulfonamide derivatives for use as ccr3 antagonists in the treatment of inflammatory and immunological disorders |
| DE60221569T DE60221569T2 (de) | 2001-09-07 | 2002-09-04 | Acrylsulfonamidderivate zur verwendung als ccr3-antagonisten bei der behandlung von inflammatorischen und immunologischen erkrankungen |
| JP2003526406A JP4517047B2 (ja) | 2001-09-07 | 2002-09-04 | スルホンアミド誘導体 |
| EP07013793A EP1849469B1 (en) | 2001-09-07 | 2002-09-04 | Arylsulfonamide derivatives for use as CCR3 antagonists in the treatment of inflammatory and immunological disorders |
| ES02772265T ES2294167T3 (es) | 2001-09-07 | 2002-09-04 | Derivados de arilsufonamida para utilizar como antagonistas del ccr3 en el tratamiento de desordenes inflamatorios e inmunologicos. |
| GT200200178A GT200200178A (es) | 2001-09-07 | 2002-09-05 | Derivados de sulfonamida |
| TW091120389A TWI262187B (en) | 2001-09-07 | 2002-09-05 | Sulfonamide derivatives |
| HN2002000247A HN2002000247A (es) | 2001-09-07 | 2002-09-06 | Derivados de sulfonamida |
| PE2002000882A PE20030440A1 (es) | 2001-09-07 | 2002-09-06 | Fenilsulfonamidas como antagonistas de ccr3 |
| SV2002001225A SV2004001225A (es) | 2001-09-07 | 2002-09-06 | Derivados de sulfonamida ref.rck 00014-sv |
| MYPI20023349A MY133303A (en) | 2001-09-07 | 2002-09-06 | Arylsulfonamide derivatives for use as ccr3 antagonists in the treatment of inflammatory and immunological disorders |
| HK08104092.1A HK1109867B (en) | 2001-09-07 | 2008-04-11 | Arylsulfonamide derivatives for use as ccr3 antagonists in the treatment of inflammatory and immunological disorders |
| US12/763,072 US8242118B2 (en) | 2001-09-07 | 2010-04-19 | Arylsulfonamide derivatives for use as CCR3 antagonists in the treatment of inflammatory and immunological disorders |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| JP2001272327A JP2003081937A (ja) | 2001-09-07 | 2001-09-07 | ベンゼンスルホンアミド誘導体 |
Publications (1)
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| JP2003081937A true JP2003081937A (ja) | 2003-03-19 |
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| JP2001272327A Pending JP2003081937A (ja) | 2001-09-07 | 2001-09-07 | ベンゼンスルホンアミド誘導体 |
| JP2003526406A Expired - Fee Related JP4517047B2 (ja) | 2001-09-07 | 2002-09-04 | スルホンアミド誘導体 |
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| JP2003526406A Expired - Fee Related JP4517047B2 (ja) | 2001-09-07 | 2002-09-04 | スルホンアミド誘導体 |
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| EP (2) | EP1849469B1 (enExample) |
| JP (2) | JP2003081937A (enExample) |
| AR (1) | AR037235A1 (enExample) |
| CA (1) | CA2459432C (enExample) |
| DE (2) | DE60221569T2 (enExample) |
| ES (2) | ES2354378T3 (enExample) |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006523627A (ja) * | 2003-03-24 | 2006-10-19 | アクチミス ファーマシューティカルズ インコーポレーテッド | ベンゼンスルホンアミド誘導体 |
| US20110218207A1 (en) * | 2010-03-02 | 2011-09-08 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide ccr3 antagonists |
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| SE0300957D0 (sv) | 2003-04-01 | 2003-04-01 | Astrazeneca Ab | Chemical compounds |
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| TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| PH12017501176B1 (en) | 2011-05-03 | 2023-03-08 | Agios Pharmaceuticals Inc | Pyruvate kinase activators for use in therapy |
| US9181231B2 (en) | 2011-05-03 | 2015-11-10 | Agios Pharmaceuticals, Inc | Pyruvate kinase activators for use for increasing lifetime of the red blood cells and treating anemia |
| WO2014139144A1 (en) | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
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| US12221463B2 (en) | 2020-08-07 | 2025-02-11 | The Board Of Regents Of The University Of Oklahoma | Method of promoting wound healing by inhibiting CCR3 |
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- 2001-09-07 JP JP2001272327A patent/JP2003081937A/ja active Pending
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2002
- 2002-08-29 AR ARP020103259A patent/AR037235A1/es not_active Application Discontinuation
- 2002-09-04 EP EP07013793A patent/EP1849469B1/en not_active Expired - Lifetime
- 2002-09-04 EP EP02772265A patent/EP1461038B9/en not_active Expired - Lifetime
- 2002-09-04 JP JP2003526406A patent/JP4517047B2/ja not_active Expired - Fee Related
- 2002-09-04 US US10/489,029 patent/US7700586B2/en not_active Expired - Fee Related
- 2002-09-04 DE DE60221569T patent/DE60221569T2/de not_active Expired - Lifetime
- 2002-09-04 CA CA002459432A patent/CA2459432C/en not_active Expired - Fee Related
- 2002-09-04 WO PCT/EP2002/009873 patent/WO2003022277A1/en not_active Ceased
- 2002-09-04 ES ES07013793T patent/ES2354378T3/es not_active Expired - Lifetime
- 2002-09-04 DE DE60238149T patent/DE60238149D1/de not_active Expired - Lifetime
- 2002-09-04 ES ES02772265T patent/ES2294167T3/es not_active Expired - Lifetime
- 2002-09-05 TW TW091120389A patent/TWI262187B/zh not_active IP Right Cessation
- 2002-09-05 GT GT200200178A patent/GT200200178A/es unknown
- 2002-09-06 MY MYPI20023349A patent/MY133303A/en unknown
- 2002-09-06 SV SV2002001225A patent/SV2004001225A/es not_active Application Discontinuation
- 2002-09-06 HN HN2002000247A patent/HN2002000247A/es unknown
- 2002-09-06 PE PE2002000882A patent/PE20030440A1/es not_active Application Discontinuation
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- 2010-04-19 US US12/763,072 patent/US8242118B2/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006523627A (ja) * | 2003-03-24 | 2006-10-19 | アクチミス ファーマシューティカルズ インコーポレーテッド | ベンゼンスルホンアミド誘導体 |
| US9206186B2 (en) | 2003-03-24 | 2015-12-08 | Axikin Pharmaceuticals, Inc. | 2-phenoxy- and 2-phenylsulfonamide derivatives with CCR3 antagonistic activity for the treatment of inflammatory or immunological disorders |
| US9187425B2 (en) | 2009-04-22 | 2015-11-17 | Axikin Pharmaceuticals, Inc. | 2,5-disubstituted arylsulfonamide CCR3 antagonists |
| US20110218207A1 (en) * | 2010-03-02 | 2011-09-08 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide ccr3 antagonists |
| US8999995B2 (en) * | 2010-03-02 | 2015-04-07 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide CCR3 antagonists |
| JP2013543512A (ja) * | 2010-10-11 | 2013-12-05 | アクシキン ファーマシューティカルズ インコーポレーテッド | アリールスルホンアミドccr3アンタゴニストの塩 |
| US9156799B2 (en) | 2012-09-07 | 2015-10-13 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide CCR3 antagonists |
| US9637460B2 (en) | 2012-09-07 | 2017-05-02 | Axikin Pharmaceuticals, Inc. | Isotopically enriched arylsulfonamide CCR3 antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2294167T3 (es) | 2008-04-01 |
| MY133303A (en) | 2007-11-30 |
| ES2354378T3 (es) | 2011-03-14 |
| HK1109867A1 (en) | 2008-06-27 |
| TWI262187B (en) | 2006-09-21 |
| GT200200178A (es) | 2003-05-23 |
| US8242118B2 (en) | 2012-08-14 |
| WO2003022277A1 (en) | 2003-03-20 |
| EP1461038A1 (en) | 2004-09-29 |
| JP2005519024A (ja) | 2005-06-30 |
| DE60221569D1 (de) | 2007-09-13 |
| EP1461038B9 (en) | 2009-09-23 |
| SV2004001225A (es) | 2004-02-24 |
| CA2459432A1 (en) | 2003-03-20 |
| PE20030440A1 (es) | 2003-06-26 |
| US7700586B2 (en) | 2010-04-20 |
| US20100204213A1 (en) | 2010-08-12 |
| JP4517047B2 (ja) | 2010-08-04 |
| AR037235A1 (es) | 2004-11-03 |
| US20050070582A1 (en) | 2005-03-31 |
| EP1461038B1 (en) | 2007-08-01 |
| DE60238149D1 (de) | 2010-12-09 |
| HN2002000247A (es) | 2003-11-24 |
| DE60221569T2 (de) | 2008-04-30 |
| EP1849469B1 (en) | 2010-10-27 |
| CA2459432C (en) | 2009-05-26 |
| EP1849469A1 (en) | 2007-10-31 |
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