JP4516080B2 - アミノアルカノール誘導体 - Google Patents
アミノアルカノール誘導体 Download PDFInfo
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- JP4516080B2 JP4516080B2 JP2006534686A JP2006534686A JP4516080B2 JP 4516080 B2 JP4516080 B2 JP 4516080B2 JP 2006534686 A JP2006534686 A JP 2006534686A JP 2006534686 A JP2006534686 A JP 2006534686A JP 4516080 B2 JP4516080 B2 JP 4516080B2
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- UTDJDJAORGLHGB-UHFFFAOYSA-N CCCCCCCCc1ccc(CCC)cc1 Chemical compound CCCCCCCCc1ccc(CCC)cc1 UTDJDJAORGLHGB-UHFFFAOYSA-N 0.000 description 1
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- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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Description
R2は所望によりハロゲンで置換されているC1−20−アルキルであり;
R5はHまたはC1−20−アルキルであり;そして
R6はC1−20アルキルまたは式a)
のラジカルである。〕
の化合物に関する。
本発明の一つの態様において、R6はC1−20アルキルである。他の態様において、R6は式a)のラジカルである。R5またはR6がC1−20アルキルであるとき、好ましくは14個までの炭素原子のアルキルであるのが好ましいであろう。
nは、1〜4の整数、例えば2であり;
mは、2〜4の整数、例えば2であり;
R'2はC6−14−アルキル、例えばオクチルであり;そして
R'4はHまたはC6−14−アルキル、例えばHまたはオクチルである。〕
の化合物である。
の化合物を脱保護し、得られた式Iの化合物を遊離形または塩形で回収することを含む、方法により製造し得る。
R、R'、R”、R1、R2およびR5は上記の通りであり;
R”4はR4の意味を有するか、または−CO−C1−19アルキルであり;そして
qは、0〜6の整数である。〕
の化合物の既知方法を使用した還元、例えば水素およびパラジウム触媒での還元により製造し得る。式IVの化合物はcisまたはtrans形態であり得る。
Xはハロゲノ、例えばブロモである。〕
の化合物と、式VI:
の化合物を、例えば既知の方法を使用して、例えばHeckカップリング、例えばPd(P(C6H5)3)4またはPd(II)−アセテート/P(t−Bu)3との反応により反応させることにより製造できる。
の化合物をハロゲン化、例えば臭素化剤、例えばHBr、Br2またはN−ブロモスクシンイミドで臭素化することにより製造できる。この工程で形成される、ハロゲン原子がベンゼン環の別の位置に結合している式Vの化合物の異性体を、標準法、例えばカラムクロマトグラフィーにより分離し得る。好ましくはN−ブロモスクシンイミドでの臭素化を室温で行う。
下記非限定的実施例は本発明を説明する。
NMRデータは、2個の表題化合物と調和する。
ヒトS1P受容体のHEK293細胞への一過性トランスフェクション
S1P受容体およびGiタンパク質をクローン化し、等量の4種のEDG受容体のcDNA、Gi−α、Gi−βおよびGi−γを混合し、HEK293細胞の単層をリン酸カルシウム沈殿法を使用してトランスフェクトするのに使用する(M. Wigler et al., Cell. 1977; 11; 223およびDS. Im et al., Mol. Pharmacol. 2000; 57; 753)。簡単に言うと、25μgのDNAおよび0.25M CaClを含むDNA混合物をHEPES緩衝化2mM Na2HPO4に添加する。HEK293細胞のサブコンフルエントな単層を25mM クロロキンで中毒させ、DNA沈殿を次いで細胞に適用する。4時間後、単層をリン酸緩衝化食塩水で洗浄し、培地(90%1:1 ダルベッコ改変必須培地(DMEM):F−12+10%胎児ウシ血清)を再添加した。細胞をDNAの添加48−72時間後に、氷上の10%スクロース含有HME緩衝液(mMで:20 HEPES、5 MgCl2、1 EDTA、pH7.4)にかき取ることにより回収し、Dounceホモジナイザーを使用して破壊する。800×gで遠心分離後、上清をスクロース無しのHMEで希釈し、100,000×gで1時間遠心分離する。得られたペレットを、再均質化し、100,000×gで第2回目の1時間遠心分離を行う。この粗膜ペレットをスクロース含有HMEに再懸濁し、等分し、液体窒素への浸漬により急速凍結(snap-frozen)する。膜を70℃で貯蔵する。タンパク質含量をBradfordタンパク質アッセイにより分光学的に測定する。
GTPγS結合実験を、DS. Im et al., Mol. Pharmacol. 2000; 57: 753に記載の通りに行う。G−タンパク質へのリガンド介在GTPγS結合をGTP結合緩衝液(mMで:50 HEPES、100 NaCl、10 MgCl2、pH7.5)中、一過性にトランスフェクトしたHEK293細胞からの膜調製物25μgを使用して測定する。リガンドを10μM GDPおよび0.1nM [35S]GTPγS(1200Ci/mmol)の存在下膜に添加し、30℃で30分インキュベートする。結合したGTPγSをBrandel harvester(Gaithersburg, MD)を使用して非結合物から分離し、液体シンチレーションカウンターで計数する。
式Iの化合物または媒体を、ラットに胃管栄養法により経口で投与する。血液学的モニタリングのための尾血液を、個々の基線値を得るために−1日目に、ならびに投与後2、6、24、48および72時間に得る。このアッセイにおいて、式Iの化合物は、0.03から3mg/kgの投与量で末梢血リンパ球を枯渇させる。
a)臓器または組織移植拒絶反応の処置および予防、例えば心臓、肺、複合心臓−肺、肝臓、腎臓、膵臓、皮膚または角膜移植のレシピエントの処置、および骨髄移植後に時々起こる移植片対宿主病の予防のために;特に急性または慢性同種および異種移植片移植拒絶反応の処置または、インスリン産生細胞、例えば膵臓島細胞の移植において;
b)自己免疫疾患または炎症状態、例えばリウマチ性関節炎、全身性エリテマトーデス、橋本甲状腺炎、多発性硬化症、重症筋無力症、I型またはII型糖尿病およびそれらの合併症、脈管炎、悪性貧血、シェーグレン症候群、ブドウ膜炎、乾癬、グレーブス眼病、円形脱毛症およびその他、アレルギー性疾患、例えばアレルギー性喘息、アトピー性皮膚炎、アレルギー性鼻炎/結膜炎、アレルギー性接触性皮膚炎、所望により根底の異常反応を伴う炎症疾患、例えば炎症性腸疾患、クローン病または潰瘍性大腸炎、内因性喘息、炎症性肺傷害、炎症性肝臓傷害、炎症性糸球体傷害、アテローム性動脈硬化症、骨関節症、刺激性接触性皮膚炎およびさらなる湿疹性皮膚炎、脂漏性皮膚炎、免疫介在疾患の皮膚発現、炎症性眼病、角結膜炎、心筋炎または肝炎の処置および予防。
1. 対象に有効量の式Iの化合物またはその薬学的に許容される塩を投与することを含む、臓器または組織移植拒絶反応を処置または予防する方法。
Claims (4)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0324210.4A GB0324210D0 (en) | 2003-10-15 | 2003-10-15 | Organic compounds |
PCT/EP2004/011567 WO2005040091A1 (en) | 2003-10-15 | 2004-10-14 | Aminoalkanol derivatives |
Publications (2)
Publication Number | Publication Date |
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JP2007509046A JP2007509046A (ja) | 2007-04-12 |
JP4516080B2 true JP4516080B2 (ja) | 2010-08-04 |
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Application Number | Title | Priority Date | Filing Date |
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JP2006534686A Expired - Fee Related JP4516080B2 (ja) | 2003-10-15 | 2004-10-14 | アミノアルカノール誘導体 |
Country Status (15)
Country | Link |
---|---|
US (2) | US20080161410A1 (ja) |
EP (2) | EP1675817B1 (ja) |
JP (1) | JP4516080B2 (ja) |
CN (2) | CN100422139C (ja) |
AU (2) | AU2004283844B2 (ja) |
BR (1) | BRPI0415285A (ja) |
CA (1) | CA2539277C (ja) |
ES (1) | ES2556930T3 (ja) |
GB (1) | GB0324210D0 (ja) |
HK (1) | HK1093061A1 (ja) |
MX (1) | MXPA06004058A (ja) |
PL (1) | PL1675817T3 (ja) |
PT (1) | PT1675817E (ja) |
SI (1) | SI1675817T1 (ja) |
WO (1) | WO2005040091A1 (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BRPI0513110A (pt) * | 2004-07-16 | 2008-04-29 | Kyorin Seiyaku Kk | medicamento compreendendo composto sulfeto diaril ou composto éter diaril tendo uma estrutura 2-amina-1, 3-propanediol tendo uma atividade de redução de linfócitos perifericamente circulante, em combinação com um agente imunosupressivo e/ou um agente antiinflamatório e método de expressão de prevenção do efeito secundário |
CA2583846C (en) | 2004-10-12 | 2013-10-01 | Kyorin Pharmaceutical Co., Ltd. | Process for producing 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride or hydrates thereof, and intermediates in the production thereof |
CA2624909C (en) * | 2005-10-07 | 2013-10-01 | Kyorin Pharmaceutical Co., Ltd. | Therapeutic agent for treating liver disease containing 2-amino-1,3-propanediol derivative as active ingredient, and method for treating liver disease |
TWI389683B (zh) * | 2006-02-06 | 2013-03-21 | Kyorin Seiyaku Kk | A therapeutic agent for an inflammatory bowel disease or an inflammatory bowel disease treatment using a 2-amino-1,3-propanediol derivative as an active ingredient |
NZ574012A (en) | 2006-08-08 | 2012-02-24 | Kyorin Seiyaku Kk | Aminoalcohol derivative and immunosuppressant containing the same as active ingredient |
KR101339976B1 (ko) * | 2006-08-08 | 2013-12-10 | 교린 세이야꾸 가부시키 가이샤 | 아미노인산에스테르 유도체 및 그들을 유효성분으로 하는 s1p 수용체 조절제 |
WO2009099174A1 (ja) | 2008-02-07 | 2009-08-13 | Kyorin Pharmaceutical Co., Ltd. | アミノアルコール誘導体を有効成分とする炎症性腸疾患の治療剤又は予防剤 |
KR20110044893A (ko) * | 2008-08-12 | 2011-05-02 | 알러간, 인코포레이티드 | 스핑고신-1-포스페이트 (s1p) 수용체 길항제 및 이의 사용 방법 |
US9352003B1 (en) | 2010-05-14 | 2016-05-31 | Musculoskeletal Transplant Foundation | Tissue-derived tissuegenic implants, and methods of fabricating and using same |
US10130736B1 (en) | 2010-05-14 | 2018-11-20 | Musculoskeletal Transplant Foundation | Tissue-derived tissuegenic implants, and methods of fabricating and using same |
US8883210B1 (en) | 2010-05-14 | 2014-11-11 | Musculoskeletal Transplant Foundation | Tissue-derived tissuegenic implants, and methods of fabricating and using same |
WO2016187413A1 (en) | 2015-05-21 | 2016-11-24 | Musculoskeletal Transplant Foundation | Modified demineralized cortical bone fibers |
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ATE172711T1 (de) * | 1992-10-21 | 1998-11-15 | Yoshitomi Pharmaceutical | 2-amino-1, 3- propandiolverbindung und immunosuppressium |
AU705320B2 (en) | 1995-12-28 | 1999-05-20 | Welfide Corporation | 2-amino-2-(2-(4-octylphenyl)ethyl)propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof for use in the preparation of a non-oral medicament, and for treatment of diseases and disorders |
JPH10147587A (ja) * | 1996-11-19 | 1998-06-02 | Fujisawa Pharmaceut Co Ltd | 2−アミノ−1,3−プロパンジオール誘導体およびその医薬用途 |
DE69825056T2 (de) * | 1997-04-04 | 2005-08-25 | Mitsubishi Pharma Corp. | 2-aminopropan-1,3-diol-verbindungen, ihre medizinische anwendung und zwischenprodukte zu ihrer synthese |
JPH1180026A (ja) * | 1997-09-02 | 1999-03-23 | Yoshitomi Pharmaceut Ind Ltd | 新規免疫抑制剤、その使用方法およびその同定方法 |
US7001494B2 (en) | 2001-08-14 | 2006-02-21 | 3-One-2, Llc | Electrolytic cell and electrodes for use in electrochemical processes |
DE60235900D1 (de) | 2001-09-27 | 2010-05-20 | Kyorin Seiyaku Kk | Osuppressivum |
DK1431284T3 (da) * | 2001-09-27 | 2008-02-18 | Kyorin Seiyaku Kk | Diarylsulfidderivat, additionssalt deraf samt immunundertrykkende middel |
JP2004307439A (ja) * | 2003-04-10 | 2004-11-04 | Kyorin Pharmaceut Co Ltd | アミノジオール誘導体とその付加塩及び免疫抑制剤 |
JP2004307440A (ja) * | 2003-04-10 | 2004-11-04 | Kyorin Pharmaceut Co Ltd | 2−アミノ‐1,3‐プロパンジオール誘導体とその付加塩 |
GB0313612D0 (en) * | 2003-06-12 | 2003-07-16 | Novartis Ag | Organic compounds |
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EP1675817B1 (en) | 2015-10-14 |
EP1675817A1 (en) | 2006-07-05 |
CA2539277C (en) | 2013-04-23 |
CN101260050A (zh) | 2008-09-10 |
AU2004283844A1 (en) | 2005-05-06 |
US20080161410A1 (en) | 2008-07-03 |
AU2004283844B2 (en) | 2009-03-26 |
AU2009200915B2 (en) | 2012-03-01 |
EP3018121A1 (en) | 2016-05-11 |
JP2007509046A (ja) | 2007-04-12 |
US20130289127A1 (en) | 2013-10-31 |
HK1093061A1 (en) | 2007-02-23 |
GB0324210D0 (en) | 2003-11-19 |
ES2556930T3 (es) | 2016-01-21 |
PT1675817E (pt) | 2016-02-11 |
BRPI0415285A (pt) | 2006-12-19 |
CN1856464A (zh) | 2006-11-01 |
AU2009200915A1 (en) | 2009-03-26 |
CN100422139C (zh) | 2008-10-01 |
SI1675817T1 (sl) | 2016-03-31 |
CA2539277A1 (en) | 2005-05-06 |
MXPA06004058A (es) | 2006-06-28 |
PL1675817T3 (pl) | 2016-03-31 |
WO2005040091A1 (en) | 2005-05-06 |
US9415024B2 (en) | 2016-08-16 |
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