JP2016530334A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016530334A5 JP2016530334A5 JP2016543299A JP2016543299A JP2016530334A5 JP 2016530334 A5 JP2016530334 A5 JP 2016530334A5 JP 2016543299 A JP2016543299 A JP 2016543299A JP 2016543299 A JP2016543299 A JP 2016543299A JP 2016530334 A5 JP2016530334 A5 JP 2016530334A5
- Authority
- JP
- Japan
- Prior art keywords
- minutes
- plasma
- centrifuged
- rpm
- mixture
- 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
Links
- 239000000203 mixture Substances 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000005712 crystallization Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 210000002381 Plasma Anatomy 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- LGCMKPRGGJRYGM-UHFFFAOYSA-N 2-hydroxy-N-(4-hydroxyphenyl)benzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=CC=C1O LGCMKPRGGJRYGM-UHFFFAOYSA-N 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 229950011258 osalmid Drugs 0.000 description 3
- 210000004369 Blood Anatomy 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- ZFGMDIBRIDKWMY-PASTXAENSA-N Heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
採取した血液サンプルをヘパリンナトリウム(約10μL、1000IU/mL)が入ったEPチューブに入れ、次に速やかに氷水に入れ、4500rpm、低温(4℃)で5分間にわたって遠心分離した。血漿を迅速に単離し、分析する時まで−20℃で保管した。
血液中の各化合物の濃度をLC−MS/MS−001(Q−trap−3200)により、オサルミド(osalmide)を内部標準物質として使用し、以下のように測定した。24μLのブランク血漿を6μLの血漿サンプル(希釈5倍)に添加し、次に150μLの内部標準物質(オサルミド、100μg/mL)を含有するアセトニトリルの溶液を添加した。混合物を5分間にわたって振り混ぜ、次に14000rpmで5分間にわたって遠心分離した。分析のために、得られたサンプル2μLをLC−MS/MSに装填した。希釈していない血漿サンプルについては、30μLを、150μLの内部標準物質(オサルミド、100μg/mL)を含有しているアセトニトリルの溶液に添加した。混合物を5分間にわたって振り混ぜ、次に14000rpmで5分間にわたって遠心分離した。分析のために、得られたサンプル2μLをLC−MS/MSに装填した。
Claims (1)
- 利用する前記結晶化溶媒はメタノールと水との混合物である、請求項12に記載の合成方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310433018.6A CN103450171B (zh) | 2013-09-22 | 2013-09-22 | 一种免疫调节化合物、其用途和包含其的药物组合物 |
CN201310433018.6 | 2013-09-22 | ||
PCT/CN2014/086538 WO2015039587A1 (zh) | 2013-09-22 | 2014-09-15 | 一种免疫调节新型化合物、其用途和包含其的药物组合物 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2016530334A JP2016530334A (ja) | 2016-09-29 |
JP2016530334A5 true JP2016530334A5 (ja) | 2019-01-17 |
JP6470757B2 JP6470757B2 (ja) | 2019-02-13 |
Family
ID=49733057
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016543299A Active JP6470757B2 (ja) | 2013-09-22 | 2014-09-15 | 免疫調節のための化合物及びその使用及びそれを含む医薬組成物 |
Country Status (9)
Country | Link |
---|---|
US (1) | US10280158B2 (ja) |
EP (1) | EP3048103B1 (ja) |
JP (1) | JP6470757B2 (ja) |
KR (1) | KR102372201B1 (ja) |
CN (1) | CN103450171B (ja) |
AU (1) | AU2014323822B2 (ja) |
CA (1) | CA2928300C (ja) |
ES (1) | ES2802977T3 (ja) |
WO (1) | WO2015039587A1 (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103450171B (zh) | 2013-09-22 | 2015-07-08 | 苏州康乃德生物医药有限公司 | 一种免疫调节化合物、其用途和包含其的药物组合物 |
CN105315266B (zh) * | 2014-08-01 | 2019-10-01 | 苏州康乃德生物医药有限公司 | 1-{2-氟-4-[5-(4-异丁基苯基)-1,2,4-噁二唑-3-基]-苄基}-3-吖丁啶羧酸的晶型 |
CN105348276B (zh) * | 2014-08-22 | 2020-05-26 | 苏州康乃德生物医药有限公司 | 1-{2-氟-4-[5-(4-异丁基苯基)-1,2,4-噁二唑-3-基]-苄基}-3-吖丁啶羧酸的合成方法 |
CN115772166A (zh) * | 2017-01-11 | 2023-03-10 | 苏州康乃德生物医药有限公司 | 一种s1p1受体激动剂的加成盐及其晶型和药物组合物 |
CN109956912B (zh) * | 2017-12-26 | 2021-10-22 | 中国医学科学院药物研究所 | 含二苯基噁二唑的羧酸类化合物、其制备方法及医药用途 |
JP7275253B2 (ja) * | 2018-05-04 | 2023-05-17 | スーチョウ・コネクト・バイオファーマシューティカルズ・リミテッド | S1p1受容体アゴニストの付加塩およびその結晶形態、ならびに薬学的組成物 |
CN113072474A (zh) * | 2018-12-06 | 2021-07-06 | 上海济煜医药科技有限公司 | 作为免疫调节剂的化合物及其制备方法和应用 |
US20230398099A1 (en) * | 2020-11-09 | 2023-12-14 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the s1p1 receptor |
CN113480410A (zh) * | 2021-07-07 | 2021-10-08 | 南京伊派森化学科技有限公司 | 一种2,4-二溴苯甲醇的合成方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2488117A1 (en) * | 2002-06-17 | 2003-12-24 | Merck & Co., Inc. | 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylates and 1-((5-aryl-1,2,4-oxadiazol-3-yl)benzyl)pyrrolidine-3-carboxylates as edg receptor agonists |
AU2003279915A1 (en) | 2002-10-15 | 2004-05-04 | Merck And Co., Inc. | Process for making azetidine-3-carboxylic acid |
EP2382212B1 (en) * | 2009-01-23 | 2014-07-16 | Bristol-Myers Squibb Company | Substituted oxadiazole derivatives as s1p agonists in the treatment of autoimmune and inflammatory diseases |
EP2241558A1 (en) * | 2009-04-03 | 2010-10-20 | Merck Serono SA | Oxadiazole derivatives |
CN103480171A (zh) * | 2013-08-27 | 2014-01-01 | 仙桃市康化科技有限公司 | 一种对苯醌汽提塔顶部除泥装置 |
CN103450171B (zh) | 2013-09-22 | 2015-07-08 | 苏州康乃德生物医药有限公司 | 一种免疫调节化合物、其用途和包含其的药物组合物 |
-
2013
- 2013-09-22 CN CN201310433018.6A patent/CN103450171B/zh active Active
-
2014
- 2014-09-15 ES ES14846294T patent/ES2802977T3/es active Active
- 2014-09-15 US US15/023,246 patent/US10280158B2/en active Active
- 2014-09-15 JP JP2016543299A patent/JP6470757B2/ja active Active
- 2014-09-15 AU AU2014323822A patent/AU2014323822B2/en active Active
- 2014-09-15 WO PCT/CN2014/086538 patent/WO2015039587A1/zh active Application Filing
- 2014-09-15 EP EP14846294.8A patent/EP3048103B1/en active Active
- 2014-09-15 CA CA2928300A patent/CA2928300C/en active Active
- 2014-09-15 KR KR1020167010722A patent/KR102372201B1/ko active IP Right Grant
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2016530334A5 (ja) | ||
Jansson et al. | Quantitative analysis of colistin A and colistin B in plasma and culture medium using a simple precipitation step followed by LC/MS/MS | |
Hényková et al. | Stable isotope dilution ultra-high performance liquid chromatography–tandem mass spectrometry quantitative profiling of tryptophan-related neuroactive substances in human serum and cerebrospinal fluid | |
WO2012162165A3 (en) | Antibodies to 25-hydroxyvitamin d2 and d3 and uses thereof | |
EP3269849A4 (en) | POROUS COMPOUND MONOCRYSTAL, PROCESS FOR EVALUATING MONOCRYSTAL QUALITY, PROCESS FOR PREPARING SOLUTION COMPRISING COMPOUND FOR ANALYZING, PROCESS FOR PRODUCING CRYSTALLINE STRUCTURE ANALYSIS SAMPLE, AND PROCESS FOR DETERMINING MOLECULAR STRUCTURE OF COMPOUND ANALYZE | |
WO2007120248A3 (en) | Nanoporous substrates for analytical methods | |
CN106458967A (zh) | 四环化合物的新结晶 | |
CN104634897A (zh) | 一种检测卷烟主流烟气中晚期糖基化终末产物的方法 | |
WO2019143943A3 (en) | Composition and method for concentration and enrichment of nucleic acids | |
WO2015123192A3 (en) | Universal system, method and solution for the acceleration of the process of fixing, dehydrating and clearing the structure of biological tissue | |
KR20120014736A (ko) | 액체크로마토그래피-질량분석기를 이용한 혈장 중의 아스피린의 분석방법 | |
RU2014106990A (ru) | Способы выделения 4-хлор-2-фтор-3-замещенных-фенилбороновых кислот | |
Liu et al. | Determination of efonidipine in human plasma by LC–MS/MS for pharmacokinetic applications | |
Ren et al. | Determination of lomerizine in human plasma by liquid chromatography/tandem mass spectrometry and its application to a pharmacokinetic study | |
RU2013129619A (ru) | Способ пробоподготовки водных объектов для определения углеводородных примесей | |
RU2276784C1 (ru) | Способ селективного определения тирозина и фенилаланина в водном растворе | |
JP2017000049A5 (ja) | ||
Pradhan et al. | Liquid chromatography–tandem mass spectrometric method for the estimation of R‐bicalutamide in human plasma | |
RU2305832C1 (ru) | Способ раздельного определения триптофана и тирозина в водном растворе | |
RU2009107447A (ru) | Способ определения водорастворимых витаминов в премиксах | |
Aygul et al. | Comparative characteristics of methodics for the quantitative determination of small concentrations of citric acid | |
CA2951859A1 (en) | Reagents for potentiometric magnesium ion selective electrode sensors and methods of production and use thereof | |
RU2517127C1 (ru) | Способ экстракции новокаина из водных сред смесью фенетола и этилацетата | |
RU2574766C2 (ru) | Сорбент для газохроматографического разделения энантиомеров (варианты) и способ его использования | |
RU2620190C2 (ru) | Равномерномеченный дейтерием и тритием 3-(1-метилпирролидин-2-ил)пиридин |