JP2010511728A5 - - Google Patents
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- Publication number
- JP2010511728A5 JP2010511728A5 JP2009540442A JP2009540442A JP2010511728A5 JP 2010511728 A5 JP2010511728 A5 JP 2010511728A5 JP 2009540442 A JP2009540442 A JP 2009540442A JP 2009540442 A JP2009540442 A JP 2009540442A JP 2010511728 A5 JP2010511728 A5 JP 2010511728A5
- Authority
- JP
- Japan
- Prior art keywords
- thiadiazol
- sulfonyl
- benzamide
- fluoro
- ethylamino
- 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.)
- Withdrawn
Links
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 68
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 34
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 27
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- -1 1-methyl-1-phenylethyl Chemical group 0.000 claims 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 3
- 102000019034 Chemokines Human genes 0.000 claims 3
- 108010012236 Chemokines Proteins 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000006308 propyl amino group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- AFEMEFAXKSZWOZ-UHFFFAOYSA-N 2,3-dichloro-n-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]-5-sulfamoylbenzamide Chemical compound NS(=O)(=O)C1=CC(Cl)=C(Cl)C(C(=O)NC=2SC(=NN=2)C=2C=CC(F)=CC=2)=C1 AFEMEFAXKSZWOZ-UHFFFAOYSA-N 0.000 claims 1
- CZMBBLFKJWKXON-UHFFFAOYSA-N 2-chloro-n-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-5-sulfamoylbenzamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C(C(=O)NC=2SC(=NN=2)C2CCCCC2)=C1 CZMBBLFKJWKXON-UHFFFAOYSA-N 0.000 claims 1
- HQKYIRVPMTZOQR-UHFFFAOYSA-N 2-chloro-n-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]-5-sulfamoylbenzamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C(C(=O)NC=2SC(=NN=2)C=2C=CC(F)=CC=2)=C1 HQKYIRVPMTZOQR-UHFFFAOYSA-N 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 claims 1
- SDMYKGWZCNUGDR-UHFFFAOYSA-N 3-chloro-5-(ethylsulfamoyl)-2-fluoro-n-[5-(2-phenylpropan-2-yl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CCNS(=O)(=O)C1=CC(Cl)=C(F)C(C(=O)NC=2SC(=NN=2)C(C)(C)C=2C=CC=CC=2)=C1 SDMYKGWZCNUGDR-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- VABTYZFLSRDMNV-UHFFFAOYSA-N 5-(cyclopropylmethylsulfamoyl)-n-[5-(2,5-dimethylfuran-3-yl)-1,3,4-thiadiazol-2-yl]-2-fluorobenzamide Chemical compound O1C(C)=CC(C=2SC(NC(=O)C=3C(=CC=C(C=3)S(=O)(=O)NCC3CC3)F)=NN=2)=C1C VABTYZFLSRDMNV-UHFFFAOYSA-N 0.000 claims 1
- HCTRJUXXNUOXNW-UHFFFAOYSA-N 5-(cyclopropylmethylsulfamoyl)-n-[5-[1-(2,4-difluorophenyl)cyclobutyl]-1,3,4-thiadiazol-2-yl]-2-fluorobenzamide Chemical compound FC1=CC(F)=CC=C1C1(C=2SC(NC(=O)C=3C(=CC=C(C=3)S(=O)(=O)NCC3CC3)F)=NN=2)CCC1 HCTRJUXXNUOXNW-UHFFFAOYSA-N 0.000 claims 1
- PCGUMWRXTCKSCQ-UHFFFAOYSA-N 5-(cyclopropylsulfamoyl)-2-fluoro-n-[5-(2-methyl-1-phenylpropan-2-yl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound N=1N=C(NC(=O)C=2C(=CC=C(C=2)S(=O)(=O)NC2CC2)F)SC=1C(C)(C)CC1=CC=CC=C1 PCGUMWRXTCKSCQ-UHFFFAOYSA-N 0.000 claims 1
- WBJJWRWZBFYIOL-UHFFFAOYSA-N 5-(ethylsulfamoyl)-2,3-difluoro-n-[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CCNS(=O)(=O)C1=CC(F)=C(F)C(C(=O)NC=2SC(=NN=2)C=2C=CC(F)=CC=2)=C1 WBJJWRWZBFYIOL-UHFFFAOYSA-N 0.000 claims 1
- JOFHDDWDYUTOBG-UHFFFAOYSA-N 5-(ethylsulfamoyl)-2-fluoro-n-[5-(2-methyl-1-phenylpropan-2-yl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CCNS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C(C)(C)CC=2C=CC=CC=2)=C1 JOFHDDWDYUTOBG-UHFFFAOYSA-N 0.000 claims 1
- IHTHRSGOWDLRKO-UHFFFAOYSA-N 5-(ethylsulfamoyl)-2-fluoro-n-[5-(2-phenylpropan-2-yl)-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CCNS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C(C)(C)C=2C=CC=CC=2)=C1 IHTHRSGOWDLRKO-UHFFFAOYSA-N 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims 1
- 125000006309 butyl amino group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- IMXYTMQVTROOPF-UHFFFAOYSA-N n-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-2-fluoro-5-sulfamoylbenzamide Chemical compound NS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C2CCCC2)=C1 IMXYTMQVTROOPF-UHFFFAOYSA-N 0.000 claims 1
- PMCZZMPBFWVOGV-UHFFFAOYSA-N n-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-5-(ethylsulfamoyl)-2,4-difluorobenzamide Chemical compound C1=C(F)C(S(=O)(=O)NCC)=CC(C(=O)NC=2SC(=NN=2)C2CCCC2)=C1F PMCZZMPBFWVOGV-UHFFFAOYSA-N 0.000 claims 1
- NSHYKZOFKZRXMU-UHFFFAOYSA-N n-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-5-(ethylsulfamoyl)-2-fluorobenzamide Chemical compound CCNS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C2CCCC2)=C1 NSHYKZOFKZRXMU-UHFFFAOYSA-N 0.000 claims 1
- QKQWEACNLPXNHY-UHFFFAOYSA-N n-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2-fluoro-5-sulfamoylbenzamide Chemical compound S1C(C(C)(C)C)=NN=C1NC(=O)C1=CC(S(N)(=O)=O)=CC=C1F QKQWEACNLPXNHY-UHFFFAOYSA-N 0.000 claims 1
- OEAKEHAWPNEVFL-UHFFFAOYSA-N n-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-chloro-5-(ethylsulfamoyl)-2,4-difluorobenzamide Chemical compound ClC1=C(F)C(S(=O)(=O)NCC)=CC(C(=O)NC=2SC(=NN=2)C(C)(C)C)=C1F OEAKEHAWPNEVFL-UHFFFAOYSA-N 0.000 claims 1
- DSQHVORBYGJWAQ-UHFFFAOYSA-N n-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-chloro-5-(ethylsulfamoyl)-2-fluorobenzamide Chemical compound CCNS(=O)(=O)C1=CC(Cl)=C(F)C(C(=O)NC=2SC(=NN=2)C(C)(C)C)=C1 DSQHVORBYGJWAQ-UHFFFAOYSA-N 0.000 claims 1
- WFSMWUQJRWIDTF-UHFFFAOYSA-N n-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-5-(cyclopropylsulfamoyl)-2-fluorobenzamide Chemical compound S1C(C(C)(C)C)=NN=C1NC(=O)C1=CC(S(=O)(=O)NC2CC2)=CC=C1F WFSMWUQJRWIDTF-UHFFFAOYSA-N 0.000 claims 1
- FHUNRMPYAHFSOM-UHFFFAOYSA-N n-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-5-(ethylsulfamoyl)-2,3-difluorobenzamide Chemical compound CCNS(=O)(=O)C1=CC(F)=C(F)C(C(=O)NC=2SC(=NN=2)C(C)(C)C)=C1 FHUNRMPYAHFSOM-UHFFFAOYSA-N 0.000 claims 1
- FCZOUUVHBZBFNI-UHFFFAOYSA-N n-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-5-(ethylsulfamoyl)-2-iodobenzamide Chemical compound CCNS(=O)(=O)C1=CC=C(I)C(C(=O)NC=2SC(=NN=2)C(C)(C)C)=C1 FCZOUUVHBZBFNI-UHFFFAOYSA-N 0.000 claims 1
- CCVMJHSMDUQYNC-UHFFFAOYSA-N n-[5-(2,5-dimethylfuran-3-yl)-1,3,4-thiadiazol-2-yl]-5-(ethylsulfamoyl)-2-fluorobenzamide Chemical compound CCNS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C2=C(OC(C)=C2)C)=C1 CCVMJHSMDUQYNC-UHFFFAOYSA-N 0.000 claims 1
- XJUIXEUKJRQPLG-UHFFFAOYSA-N n-[5-(2-chloro-4-fluorophenyl)-1,3,4-thiadiazol-2-yl]-2-fluoro-5-sulfamoylbenzamide Chemical compound NS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C=2C(=CC(F)=CC=2)Cl)=C1 XJUIXEUKJRQPLG-UHFFFAOYSA-N 0.000 claims 1
- LHPCPOVAUCMAHZ-UHFFFAOYSA-N n-[5-(2-chloro-4-fluorophenyl)-1,3,4-thiadiazol-2-yl]-5-(cyclopropylmethylsulfamoyl)-2-fluorobenzamide Chemical compound ClC1=CC(F)=CC=C1C(S1)=NN=C1NC(=O)C1=CC(S(=O)(=O)NCC2CC2)=CC=C1F LHPCPOVAUCMAHZ-UHFFFAOYSA-N 0.000 claims 1
- VLRQZYRWSTXALE-UHFFFAOYSA-N n-[5-(4,4-difluorocyclohexyl)-1,3,4-thiadiazol-2-yl]-5-(ethylsulfamoyl)-2-fluorobenzamide Chemical compound CCNS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C2CCC(F)(F)CC2)=C1 VLRQZYRWSTXALE-UHFFFAOYSA-N 0.000 claims 1
- IWKDHTYKWVEXFU-UHFFFAOYSA-N n-[5-(4-chloro-2-fluorophenyl)-1,3,4-thiadiazol-2-yl]-5-(cyclopropylmethylsulfamoyl)-2-fluorobenzamide Chemical compound FC1=CC=C(S(=O)(=O)NCC2CC2)C=C1C(=O)NC(S1)=NN=C1C1=CC=C(Cl)C=C1F IWKDHTYKWVEXFU-UHFFFAOYSA-N 0.000 claims 1
- RRCSCCGJEMMTGD-UHFFFAOYSA-N n-[5-[1-(2,4-difluorophenyl)cyclobutyl]-1,3,4-thiadiazol-2-yl]-2-fluoro-5-sulfamoylbenzamide Chemical compound NS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C2(CCC2)C=2C(=CC(F)=CC=2)F)=C1 RRCSCCGJEMMTGD-UHFFFAOYSA-N 0.000 claims 1
- LEHOVFBHPUAXOB-UHFFFAOYSA-N n-[5-[1-(4-chlorophenyl)cyclobutyl]-1,3,4-thiadiazol-2-yl]-5-(ethylsulfamoyl)-2-fluorobenzamide Chemical compound CCNS(=O)(=O)C1=CC=C(F)C(C(=O)NC=2SC(=NN=2)C2(CCC2)C=2C=CC(Cl)=CC=2)=C1 LEHOVFBHPUAXOB-UHFFFAOYSA-N 0.000 claims 1
- RXXPUVSUXDXUOK-UHFFFAOYSA-N n-[5-[2-(4-bromophenyl)propan-2-yl]-1,3,4-thiadiazol-2-yl]-2-fluoro-5-sulfamoylbenzamide Chemical compound C=1C=C(Br)C=CC=1C(C)(C)C(S1)=NN=C1NC(=O)C1=CC(S(N)(=O)=O)=CC=C1F RXXPUVSUXDXUOK-UHFFFAOYSA-N 0.000 claims 1
- YDGHQPRASHPLDZ-UHFFFAOYSA-N n-[5-[2-(4-bromophenyl)propan-2-yl]-1,3,4-thiadiazol-2-yl]-5-(cyclopropylmethylsulfamoyl)-2-fluorobenzamide Chemical compound C=1C=C(Br)C=CC=1C(C)(C)C(S1)=NN=C1NC(=O)C(C(=CC=1)F)=CC=1S(=O)(=O)NCC1CC1 YDGHQPRASHPLDZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 CC#*NS(C1=C*(*)C=C(*)C(C(Nc2nnc(*)[s]2)=O)=C1)(=O)=O Chemical compound CC#*NS(C1=C*(*)C=C(*)C(C(Nc2nnc(*)[s]2)=O)=C1)(=O)=O 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86859906P | 2006-12-05 | 2006-12-05 | |
| PCT/US2007/086473 WO2008070707A1 (en) | 2006-12-05 | 2007-12-05 | Il-8 receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010511728A JP2010511728A (ja) | 2010-04-15 |
| JP2010511728A5 true JP2010511728A5 (enExample) | 2011-01-27 |
Family
ID=39492621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009540442A Withdrawn JP2010511728A (ja) | 2006-12-05 | 2007-12-05 | Ｉｌ−８受容体アンタゴニスト |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8044075B2 (enExample) |
| EP (1) | EP2099300A4 (enExample) |
| JP (1) | JP2010511728A (enExample) |
| WO (1) | WO2008070707A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200418812A (en) | 2002-10-29 | 2004-10-01 | Smithkline Beecham Corp | IL-8 receptor antagonists |
| WO2007124423A2 (en) | 2006-04-21 | 2007-11-01 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| MY145810A (en) | 2006-04-21 | 2012-04-30 | Smithkline Beecham Corp | Il-8 receptor antagonists |
| CA2761876C (en) | 2009-05-12 | 2017-01-03 | Romark Laboratories L.C. | Haloalkyl heteroaryl benzamide compounds |
| KR20180032689A (ko) | 2009-06-26 | 2018-03-30 | 로마크 레버러토리즈, 엘.씨. | 인플루엔자를 치료하기 위한 화합물 및 방법 |
| EP2305660A1 (en) * | 2009-09-25 | 2011-04-06 | Almirall, S.A. | New thiadiazole derivatives |
| CN102757405B (zh) * | 2012-07-25 | 2014-04-16 | 山东理工大学 | 含噻二唑的香兰素衍生物、其制备方法及其用途 |
| EP2938338A4 (en) * | 2012-12-27 | 2016-11-23 | Univ Drexel | NOVEL ANTIVIRAL AGENTS AGAINST HBV INFECTION |
| CN106565467B (zh) * | 2016-11-04 | 2017-12-01 | 杭州励德生物科技有限公司 | 一种抗过敏药比拉斯汀中间体的制备方法 |
| WO2018145620A1 (en) * | 2017-02-07 | 2018-08-16 | Janssen Pharmaceutica Nv | Sulphamoylaryl derivatives and use thereof as medicaments for the treatment of liver fibrosis |
| JP2020525490A (ja) | 2017-06-27 | 2020-08-27 | ヤンセン ファーマシューティカ エヌ．ベー． | ヘテロアリールジヒドロピリミジン誘導体及びｂ型肝炎感染を治療する方法 |
| US11053235B2 (en) | 2018-08-09 | 2021-07-06 | Janssen Sciences Ireland Unlimited Company | Substituted 1,4-dihydropyrimidines for the treatment of HBV infection or HBV-induced diseases |
| CN111689881B (zh) * | 2020-06-12 | 2022-04-01 | 苏州华道生物药业股份有限公司 | 一种阿佐塞米中间体的合成方法 |
| WO2023175184A1 (en) | 2022-03-17 | 2023-09-21 | Forx Therapeutics Ag | 2,4-dioxo-1,4-dihydroquinazoline derivatives as parg inhibitors for the treatment of cancer |
| WO2023175185A1 (en) | 2022-03-17 | 2023-09-21 | Forx Therapeutics Ag | 2,4-dioxo-1,4-dihydroquinazoline derivatives as parg inhibitors for the treatment of cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050143384A1 (en) * | 2003-10-30 | 2005-06-30 | Eric Sartori | Amide thiadiazole inhibitors of plasminogen activator inhibitor-1 |
| PE20061093A1 (es) * | 2005-02-16 | 2006-11-10 | Schering Corp | Piperazinas sustituidas con heterociclos con actividad antagonista de cxcr3 |
-
2007
- 2007-12-05 JP JP2009540442A patent/JP2010511728A/ja not_active Withdrawn
- 2007-12-05 WO PCT/US2007/086473 patent/WO2008070707A1/en not_active Ceased
- 2007-12-05 EP EP07865212A patent/EP2099300A4/en not_active Withdrawn
- 2007-12-05 US US12/517,878 patent/US8044075B2/en not_active Expired - Fee Related
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