JP2005519024A5 - - Google Patents
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- JP2005519024A5 JP2005519024A5 JP2003526406A JP2003526406A JP2005519024A5 JP 2005519024 A5 JP2005519024 A5 JP 2005519024A5 JP 2003526406 A JP2003526406 A JP 2003526406A JP 2003526406 A JP2003526406 A JP 2003526406A JP 2005519024 A5 JP2005519024 A5 JP 2005519024A5
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- JP
- Japan
- Prior art keywords
- branched
- hydrogen
- ring
- alkyl
- straight
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims description 116
- 239000001257 hydrogen Substances 0.000 claims description 116
- 150000002431 hydrogen Chemical class 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000002367 halogens Chemical class 0.000 claims description 51
- -1 cyano, carboxy Chemical group 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 229920006395 saturated elastomer Polymers 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 31
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 11
- 125000001153 fluoro group Chemical group F* 0.000 claims 11
- 208000035475 disorder Diseases 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 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 5
- 239000003814 drug Substances 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- SNNMYKHACBYNPF-SFHVURJKSA-N (2s)-1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-2-(pyrrolidin-1-ylmethyl)pyrrolidine Chemical compound N1([C@@H](CCC1)CN1CCCC1)S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 SNNMYKHACBYNPF-SFHVURJKSA-N 0.000 claims 3
- CXMDVJPSBFHFAZ-UHFFFAOYSA-N 1-[2-(3,5-dibromophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Br)=CC(Br)=C1 CXMDVJPSBFHFAZ-UHFFFAOYSA-N 0.000 claims 3
- MWURPJRFLFHBRA-UHFFFAOYSA-N 1-[2-(3,5-dichloro-2-fluorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1F MWURPJRFLFHBRA-UHFFFAOYSA-N 0.000 claims 3
- YOUXJSFJQJOEAR-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-1,4-diazepane Chemical compound C1CCNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 YOUXJSFJQJOEAR-UHFFFAOYSA-N 0.000 claims 3
- PZXBCZDWOYKAFB-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-3,5-dimethylpiperazine Chemical compound C1C(C)NC(C)CN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 PZXBCZDWOYKAFB-UHFFFAOYSA-N 0.000 claims 3
- LPTOUQBSQLGFOP-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-3-pyrrolidin-1-ylpyrrolidine Chemical compound C1CC(N2CCCC2)CN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 LPTOUQBSQLGFOP-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- DJXLHVLRWFRMAX-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonyl-n,n-diethylpyrrolidin-3-amine Chemical compound C1C(N(CC)CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 DJXLHVLRWFRMAX-UHFFFAOYSA-N 0.000 claims 3
- GKHAHZQMENAZHG-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC(Cl)=CC(Cl)=C1 GKHAHZQMENAZHG-UHFFFAOYSA-N 0.000 claims 3
- UZEKJXMJLMPEHG-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenoxy)-5-nitrophenyl]sulfonylpiperazine-2-carboxylic acid Chemical compound OC(=O)C1CNCCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 UZEKJXMJLMPEHG-UHFFFAOYSA-N 0.000 claims 3
- UNTKZXYTPPOUHO-UHFFFAOYSA-N 1-[2-(3,5-dichlorophenyl)sulfanyl-5-nitrophenyl]sulfonyl-4-pyrrolidin-1-ylpiperidine Chemical compound C1CC(N2CCCC2)CCN1S(=O)(=O)C1=CC([N+](=O)[O-])=CC=C1SC1=CC(Cl)=CC(Cl)=C1 UNTKZXYTPPOUHO-UHFFFAOYSA-N 0.000 claims 3
- UGKSLSUMQNVYAW-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-1,4-diazepane Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)[N+]([O-])=O)S(=O)(=O)N2CCNCCC2)=C1 UGKSLSUMQNVYAW-UHFFFAOYSA-N 0.000 claims 3
- POXBXXTZUWRVJJ-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-ethylpiperazine Chemical group C1CN(CC)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 POXBXXTZUWRVJJ-UHFFFAOYSA-N 0.000 claims 3
- LCDFCOUDXRXGBN-UHFFFAOYSA-N 1-[2-(3,5-dimethylphenoxy)-5-nitrophenyl]sulfonyl-4-propan-2-ylpiperazine Chemical compound C1CN(C(C)C)CCN1S(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1OC1=CC(C)=CC(C)=C1 LCDFCOUDXRXGBN-UHFFFAOYSA-N 0.000 claims 3
- FLIQFYMILMDSAW-UHFFFAOYSA-N 1-[5-chloro-2-(3,5-dimethylphenoxy)phenyl]sulfonyl-4-ethylpiperazine Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC(C)=CC(C)=C1 FLIQFYMILMDSAW-UHFFFAOYSA-N 0.000 claims 3
- QAAQMEREUWOLCE-UHFFFAOYSA-N 1-[5-cyano-2-(3,5-dichlorophenoxy)phenyl]sulfonylpiperazine-2-carboxylic acid Chemical compound OC(=O)C1CNCCN1S(=O)(=O)C1=CC(C#N)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 QAAQMEREUWOLCE-UHFFFAOYSA-N 0.000 claims 3
- WRKKDSRZODVOKL-UHFFFAOYSA-N 3-(1,4-diazepan-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCCC2)=C1 WRKKDSRZODVOKL-UHFFFAOYSA-N 0.000 claims 3
- SYVJNCBQBAPSCK-UHFFFAOYSA-N 3-(1,4-diazepan-1-ylsulfonyl)-4-(3,5-dichlorophenyl)sulfanylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCCC2)=C1 SYVJNCBQBAPSCK-UHFFFAOYSA-N 0.000 claims 3
- OCNYKXUWFGVIJA-UHFFFAOYSA-N 3-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CC3CCCN3CC2)=C1 OCNYKXUWFGVIJA-UHFFFAOYSA-N 0.000 claims 3
- YGJRGROVYIAAEF-KDOFPFPSSA-N 3-[[(4ar,7ar)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]sulfonyl]-4-(3,5-dichlorophenoxy)benzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2C[C@@H]3NCCC[C@@H]3C2)=C1 YGJRGROVYIAAEF-KDOFPFPSSA-N 0.000 claims 3
- JFVOTMZEFSIFQC-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-3-(3-pyrrolidin-1-ylpyrrolidin-1-yl)sulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CC(CC2)N2CCCC2)=C1 JFVOTMZEFSIFQC-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 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 3
- QBWFIHQVXQNTKR-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(SC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 QBWFIHQVXQNTKR-UHFFFAOYSA-N 0.000 claims 3
- FQQMTRHHBWAIOR-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfinyl-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound ClC1=CC(Cl)=CC(S(=O)C=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 FQQMTRHHBWAIOR-UHFFFAOYSA-N 0.000 claims 3
- GLOJZOGSKZSTGZ-UHFFFAOYSA-N 4-(3,5-dimethylphenoxy)-3-piperazin-1-ylsulfonylbenzonitrile Chemical compound CC1=CC(C)=CC(OC=2C(=CC(=CC=2)C#N)S(=O)(=O)N2CCNCC2)=C1 GLOJZOGSKZSTGZ-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 208000023328 Basedow disease Diseases 0.000 claims 3
- 208000015023 Graves' disease Diseases 0.000 claims 3
- 206010037391 Pulmonary granuloma Diseases 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 208000026935 allergic disease Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 230000001363 autoimmune Effects 0.000 claims 3
- 230000007170 pathology Effects 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 206010039083 rhinitis Diseases 0.000 claims 3
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 claims 2
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 2
- 230000004957 immunoregulator effect Effects 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 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
- 125000003368 amide group Chemical group 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 0 C*1C(C)(C)CC(C)(C)[C@@](C)C(C)(C)N(C)C(C)(C)CC2(C)CC1(*)C2 Chemical compound C*1C(C)(C)CC(C)(C)[C@@](C)C(C)(C)N(C)C(C)(C)CC2(C)CC1(*)C2 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
Applications Claiming Priority (2)
| 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 |
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005519024A JP2005519024A (ja) | 2005-06-30 |
| JP2005519024A5 true JP2005519024A5 (enExample) | 2006-01-12 |
| JP4517047B2 JP4517047B2 (ja) | 2010-08-04 |
Family
ID=19097717
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001272327A Pending JP2003081937A (ja) | 2001-09-07 | 2001-09-07 | ベンゼンスルホンアミド誘導体 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US7700586B2 (enExample) |
| EP (2) | EP1849469B1 (enExample) |
| JP (2) | JP2003081937A (enExample) |
| AR (1) | AR037235A1 (enExample) |
| CA (1) | CA2459432C (enExample) |
| DE (2) | DE60221569T2 (enExample) |
| ES (2) | ES2354378T3 (enExample) |
| GT (1) | GT200200178A (enExample) |
| HN (1) | HN2002000247A (enExample) |
| MY (1) | MY133303A (enExample) |
| PE (1) | PE20030440A1 (enExample) |
| SV (1) | SV2004001225A (enExample) |
| TW (1) | TWI262187B (enExample) |
| WO (1) | WO2003022277A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003081937A (ja) | 2001-09-07 | 2003-03-19 | Bayer Ag | ベンゼンスルホンアミド誘導体 |
| SE0200843D0 (sv) | 2002-03-19 | 2002-03-19 | Astrazeneca Ab | Chemical compounds |
| SE0203754D0 (sv) * | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| AU2012238285B2 (en) * | 2003-03-24 | 2015-07-02 | Axikin Pharmaceuticals, Inc. | Benzenesulfonamide derivatives |
| RU2380356C2 (ru) * | 2003-03-24 | 2010-01-27 | Актимис Фармасьютикалз, Инк. | Производные 2-фенокси и 2-фенилсульфонамида с ссr3 антагонистической активностью для лечения астмы и других воспалительных или иммунологических заболеваний |
| SE0300957D0 (sv) | 2003-04-01 | 2003-04-01 | Astrazeneca Ab | Chemical compounds |
| TW200630337A (en) | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| KR20080037655A (ko) | 2005-07-21 | 2008-04-30 | 아스트라제네카 아베 | 신규 피페리딘 유도체 |
| WO2007110449A1 (en) | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
| TW200812963A (en) | 2006-04-13 | 2008-03-16 | Euro Celtique Sa | Benzenesulfonamide compounds and the use thereof |
| WO2007118853A1 (en) | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| CA2649636A1 (en) | 2006-04-20 | 2007-11-01 | F. Hoffmann-La Roche Ag | Diazepan derivatives modulators of chemokine receptors |
| WO2008124118A1 (en) | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use therof |
| WO2008130718A1 (en) * | 2007-04-23 | 2008-10-30 | Atherogenics, Inc. | Sulfonamide containing compounds for treatment of inflammatory disorders |
| WO2009040659A2 (en) | 2007-09-28 | 2009-04-02 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| GEP20135992B (en) | 2009-01-12 | 2013-12-25 | Icagen Inc | Sulfonamide derivatives |
| TW201036941A (en) * | 2009-03-30 | 2010-10-16 | Sumitomo Chemical Co | Method for producing sulfonamide compound |
| CN102448951B (zh) | 2009-04-06 | 2017-05-10 | 安吉奥斯医药品有限公司 | 丙酮酸激酶m2调节剂、治疗组合物和相关使用方法 |
| TW201041583A (en) * | 2009-04-22 | 2010-12-01 | Axikin Pharmaceuticals Inc | 2,5-disubstituted arylsulfonamide CCR3 antagonists |
| SG175277A1 (en) * | 2009-04-22 | 2011-11-28 | Axikin Pharmaceuticals Inc | Arylsulfonamide ccr3 antagonists |
| NZ595823A (en) | 2009-04-22 | 2014-03-28 | Axikin Pharmaceuticals Inc | 2,5-disubstituted arylsulfonamide ccr3 antagonists |
| WO2010129351A1 (en) | 2009-04-28 | 2010-11-11 | Schepens Eye Research Institute | Method to identify and treat age-related macular degeneration |
| EP2448581B1 (en) * | 2009-06-29 | 2016-12-07 | Agios Pharmaceuticals, Inc. | Therapeutic compositions and related methods of use |
| PT2448582T (pt) | 2009-06-29 | 2017-07-10 | Agios Pharmaceuticals Inc | Compostos e composições terapêuticas |
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| US2275354A (en) * | 1937-11-29 | 1942-03-03 | May & Baker Ltd | Preparation of new therapeutically useful heterocyclic compounds |
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| US5041498A (en) * | 1990-01-02 | 1991-08-20 | The Dow Chemical Company | Trimodal ABS compositions having good gloss and reduced gloss sensitivity |
| DE4404749A1 (de) * | 1994-02-15 | 1995-08-17 | Bayer Ag | ABS-Polymer-Zusammensetzungen mit gleichmäßiger matter Oberfläche |
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| DE19518025A1 (de) * | 1995-05-17 | 1996-11-21 | Bayer Ag | Thermoplastische ABS-Formmassen |
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-
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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 US US10/489,029 patent/US7700586B2/en not_active Expired - Fee Related
- 2002-09-04 EP EP07013793A patent/EP1849469B1/en not_active Expired - Lifetime
- 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 JP JP2003526406A patent/JP4517047B2/ja not_active Expired - Fee Related
- 2002-09-04 ES ES07013793T patent/ES2354378T3/es not_active Expired - Lifetime
- 2002-09-04 EP EP02772265A patent/EP1461038B9/en not_active Expired - Lifetime
- 2002-09-04 WO PCT/EP2002/009873 patent/WO2003022277A1/en not_active Ceased
- 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 GT GT200200178A patent/GT200200178A/es unknown
- 2002-09-05 TW TW091120389A patent/TWI262187B/zh not_active IP Right Cessation
- 2002-09-06 MY MYPI20023349A patent/MY133303A/en unknown
- 2002-09-06 HN HN2002000247A patent/HN2002000247A/es unknown
- 2002-09-06 PE PE2002000882A patent/PE20030440A1/es not_active Application Discontinuation
- 2002-09-06 SV SV2002001225A patent/SV2004001225A/es not_active Application Discontinuation
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2010
- 2010-04-19 US US12/763,072 patent/US8242118B2/en not_active Expired - Fee Related
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