JP2005516936A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005516936A5 JP2005516936A5 JP2003552754A JP2003552754A JP2005516936A5 JP 2005516936 A5 JP2005516936 A5 JP 2005516936A5 JP 2003552754 A JP2003552754 A JP 2003552754A JP 2003552754 A JP2003552754 A JP 2003552754A JP 2005516936 A5 JP2005516936 A5 JP 2005516936A5
- Authority
- JP
- Japan
- Prior art keywords
- palladium
- formula
- mixtures
- heating
- compounds
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- GPCGKWMTLZDQGM-UHFFFAOYSA-N 5-chloro-n-(5-cyano-3-methoxypyrazin-2-yl)thiophene-2-sulfonamide Chemical compound COC1=NC(C#N)=CN=C1NS(=O)(=O)C1=CC=C(Cl)S1 GPCGKWMTLZDQGM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- -1 heteroaryl boronic acid Chemical compound 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0104474A SE0104474D0 (sv) | 2001-12-18 | 2001-12-18 | Novel Compounds |
| SE0202139A SE0202139D0 (sv) | 2002-07-05 | 2002-07-05 | Novel compounds |
| PCT/SE2002/002355 WO2003051870A1 (en) | 2001-12-18 | 2002-12-17 | Novel compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005516936A JP2005516936A (ja) | 2005-06-09 |
| JP2005516936A5 true JP2005516936A5 (https=) | 2006-02-09 |
Family
ID=26655646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003552754A Pending JP2005516936A (ja) | 2001-12-18 | 2002-12-17 | Ｎ−ピラジニル−チエニルスルホンアミドおよびケモカイン媒介疾患の治療におけるそれらの使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7410972B2 (https=) |
| EP (1) | EP1458715B1 (https=) |
| JP (1) | JP2005516936A (https=) |
| AT (1) | ATE312096T1 (https=) |
| AU (1) | AU2002358390A1 (https=) |
| DE (1) | DE60207890T2 (https=) |
| WO (1) | WO2003051870A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI328007B (en) | 2002-01-16 | 2010-08-01 | Astrazeneca Ab | Novel compounds |
| DE10260003A1 (de) * | 2002-12-20 | 2004-07-08 | Zf Friedrichshafen Ag | Radnabenantrieb |
| SE0301653D0 (sv) * | 2003-06-05 | 2003-06-05 | Astrazeneca Ab | Novel compounds |
| SE0302304D0 (sv) * | 2003-08-27 | 2003-08-27 | Astrazeneca Ab | Novel compounds |
| EP1661889A4 (en) * | 2003-09-05 | 2009-08-05 | Ono Pharmaceutical Co | ANTAGONIST OF THE CHEMOKINE RECEPTOR AND ITS USE FOR MEDICAL PURPOSES |
| WO2006071548A2 (en) | 2004-12-27 | 2006-07-06 | Alcon, Inc. | Aminopyrazine analogs for treating glaucoma and other rho kinase-mediated diseases |
| US7622583B2 (en) | 2005-01-14 | 2009-11-24 | Chemocentryx, Inc. | Heteroaryl sulfonamides and CCR2 |
| ES2440965T3 (es) * | 2005-01-14 | 2014-01-31 | Chemocentryx, Inc. | Heteroaril-sulfonamidas y CCR2 |
| PL1848435T3 (pl) | 2005-01-25 | 2016-08-31 | Synta Pharmaceuticals Corp | Związki przeciwko zapaleniom i zastosowania związane z odpornością |
| GB0514743D0 (en) * | 2005-07-19 | 2005-08-24 | Astrazeneca Ab | Salt |
| TW200800921A (en) * | 2005-09-19 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| WO2007063934A1 (ja) * | 2005-12-02 | 2007-06-07 | Mitsubishi Tanabe Pharma Corporation | 脂環式複素環化合物 |
| US20090182142A1 (en) * | 2005-12-02 | 2009-07-16 | Shigeru Furukubo | Aromatic Compound |
| TW200730512A (en) * | 2005-12-12 | 2007-08-16 | Astrazeneca Ab | Novel compounds |
| GB0526445D0 (en) * | 2005-12-23 | 2006-02-08 | Novartis Ag | Organic compounds |
| NZ578229A (en) * | 2007-02-22 | 2012-02-24 | Merck Serono Sa | Quinoxaline compounds and use thereof |
| PL2175859T3 (pl) | 2007-07-12 | 2012-09-28 | Chemocentryx Inc | Skondensowane heteroarylopirydylo- i fenylo-benzenosulfonamidy jako modulatory CCR2 do leczenia zapalenia |
| WO2010053182A1 (ja) | 2008-11-10 | 2010-05-14 | 協和発酵キリン株式会社 | キヌレニン産生抑制剤 |
| 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 |
| BR112013009643A2 (pt) | 2010-10-20 | 2016-07-19 | Merck Serono S A Geneva | método para preparar n-(3-amino-quinoxalin-2-il)-sulfonamidas substituídas e seus intermediários n-(3-cloo-quinoxalin-2-il)-sulfonamidas |
| JP6047497B2 (ja) | 2011-11-09 | 2016-12-21 | 協和発酵キリン株式会社 | 含窒素複素環化合物 |
| CA2912313A1 (en) * | 2013-05-14 | 2014-11-20 | Active Biotech Ab | N-(heteroaryl)-sulfonamide derivatives useful as s100-inhibitors |
| MX2021014356A (es) | 2016-11-23 | 2022-11-24 | Chemocentryx Inc | Metodo para tratar glomeruloesclerosis segmentaria focal. |
| AU2018347361A1 (en) | 2017-10-11 | 2020-04-30 | Chemocentryx, Inc. | Treatment of focal segmental glomerulosclerosis with CCR2 antagonists |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20060004010A1 (en) | 2002-07-10 | 2006-01-05 | Hiromu Habashita | Ccr4 antagonist and medical use thereof |
-
2002
- 2002-12-17 AU AU2002358390A patent/AU2002358390A1/en not_active Abandoned
- 2002-12-17 DE DE60207890T patent/DE60207890T2/de not_active Expired - Fee Related
- 2002-12-17 WO PCT/SE2002/002355 patent/WO2003051870A1/en not_active Ceased
- 2002-12-17 JP JP2003552754A patent/JP2005516936A/ja active Pending
- 2002-12-17 EP EP02792158A patent/EP1458715B1/en not_active Expired - Lifetime
- 2002-12-17 US US10/499,102 patent/US7410972B2/en not_active Expired - Fee Related
- 2002-12-17 AT AT02792158T patent/ATE312096T1/de not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005516936A5 (https=) | ||
| Chang et al. | In (OTf) 3-mediated synthesis of substituted pyridazines | |
| CN109180653A (zh) | 一种铜催化制备苯并呋喃-吡咯类化合物的方法 | |
| Li et al. | Solvent-free rhodium (III)-catalyzed synthesis of 2-aminoanilides via C− H amidation of N-nitrosoanilines under ball-milling conditions | |
| KR20060135959A (ko) | 발사르탄 및 이의 전구체의 제조방법 | |
| CN104262309B (zh) | 一种色酮类衍生物及其合成方法 | |
| CN107840819B (zh) | 一种多取代异吲哚啉酮衍生物的合成方法 | |
| CN108148069B (zh) | 一种呋喃酮并吡啶酮类化合物的合成方法 | |
| CN107188906A (zh) | 二苯并磷杂茂化合物及其合成方法和应用 | |
| CN108148070B (zh) | 一种呋喃酮并异喹啉酮类化合物的合成方法 | |
| CN101735095A (zh) | α-羰基酰胺类化合物及其衍生物和合成方法 | |
| CN110627722B (zh) | 一种7-炔基吖庚因衍生物的合成方法 | |
| CN101407474B (zh) | 一种2-溴-4,5-二甲氧基苯丙腈的制备方法 | |
| CN104327025B (zh) | 一种4-芳基萘内酯类衍生物的制备方法 | |
| JPWO2016125845A1 (ja) | クロスカップリング方法、及び該クロスカップリング方法を用いた有機化合物の製造方法 | |
| CN109251192A (zh) | 3位或4位三氟甲基取代异香豆素的制备方法 | |
| Wu et al. | One-pot synthesis of bromodifluoroacetimidoyl halides and its Suzuki coupling reactions with aryl boronic acids | |
| CN112125843B (zh) | 一种3-羟甲基-4-苯基-3,4-二氢喹啉酮化合物的制备方法 | |
| CN114105775A (zh) | 一种带有末端双键的取代碘苯的制备方法 | |
| CN113403635B (zh) | 一种制备n取代吡咯烷酮衍生物的方法 | |
| CN109232314A (zh) | 一种多取代2-环戊烯基乙酸乙酯类化合物的合成方法 | |
| CN101481327B (zh) | 酰基叠氮的制备方法 | |
| JP4334884B2 (ja) | 含フッ素芳香族化合物およびその製造方法 | |
| CN109369600B (zh) | 一种2-取代亚甲基芳环并吡喃类化合物的合成方法 | |
| JP2706554B2 (ja) | ４―トリフルオロメチルアニリン誘導体及びその製造法 |