JP2014513045A - N−保護ビス−3,6−(4−アミノアルキル)−2,5,ジケトピペラジンの生成 - Google Patents
N−保護ビス−3,6−(4−アミノアルキル)−2,5,ジケトピペラジンの生成 Download PDFInfo
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- JP2014513045A JP2014513045A JP2013553494A JP2013553494A JP2014513045A JP 2014513045 A JP2014513045 A JP 2014513045A JP 2013553494 A JP2013553494 A JP 2013553494A JP 2013553494 A JP2013553494 A JP 2013553494A JP 2014513045 A JP2014513045 A JP 2014513045A
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- lysine
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0257—Phosphorus acids or phosphorus acid esters
- B01J31/0258—Phosphoric acid mono-, di- or triesters ((RO)(R'O)2P=O), i.e. R= C, R'= C, H
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0257—Phosphorus acids or phosphorus acid esters
- B01J31/0259—Phosphorus acids or phosphorus acid esters comprising phosphorous acid (-ester) groups ((RO)P(OR')2) or the isomeric phosphonic acid (-ester) groups (R(R'O)2P=O), i.e. R= C, R'= C, H
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (20)
- nが好ましくは1から7である、請求項1に記載の方法。
- nが3に等しい、請求項1に記載の方法。
- nが2に等しい、請求項1に記載の方法。
- PGがアミド形成保護基である、請求項1に記載の方法。
- 保護基がトリフルオロアセチルである、請求項1に記載の方法。
- PGがカルバメート形成保護基である、請求項1に記載の方法。
- 保護基がCbzである、請求項1に記載の方法。
- 溶媒が実質的に水混和性である、請求項1に記載の方法。
- 溶媒がN−メチル−2−ピロリドンである、請求項1に記載の方法。
- アミノ酸がε−トリフルオロアセチル−L−リシンである、請求項1に記載の方法。
- アミノ酸がε−Cbz−L−リシンである、請求項1に記載の方法。
- アミノ酸がγ−トリフルオロアセチル−オルニチンである、請求項1に記載の方法。
- アミノ酸がγ−Cbz−オルニチンである、請求項1に記載の方法。
- 触媒が五酸化リンである、請求項1に記載の方法。
- 五酸化リンの濃度がアミノ酸の濃度の10%から約50%である、請求項16に記載の方法。
- 混合物を水でクエンチするステップをさらに含む、請求項1に記載の方法。
- 3,6−ビス−[N−保護アミノブチル]−2,5−ジケトピペラジンを合成する方法であって、
N−保護リシンの混合物を有機溶媒中で触媒の存在下において110℃から175℃の間の温度まで0.25時間から5時間の間加熱するステップを含み、
前記触媒が、硫酸、リン酸および五酸化リンからなる群から選択され、触媒の濃度がリシンの濃度の約5%から約50%であり、
前記溶媒が、ジメチルアセトアミド、N−メチル−2−ピロリドン、ジグライム、エチルグライム、プログライム、エチルジグライム、m−クレゾール、p−クレゾール、o−クレゾール、キシレン、エチレングリコールおよびフェノールからなる群から選択される方法。 - 3,6−ビス−4−(N−トリフルオロアセチル)アミノブチル−2,5−ジケトピペラジンを合成する方法であって、
ε−トリフルオロアセチル−L−リシンの混合物をN−メチル−2−ピロリドン中で五酸化リンの存在下において150℃から175℃の間の温度まで0.25時間から5時間の間加熱するステップであり、五酸化リンの濃度がリシンの濃度の約10%から約40%であるステップ、および
前記混合物を第2の溶媒でクエンチするステップ
を含む、方法。 - リシンに対する五酸化リンの濃度が20%から35%の間であり、混合物を水でクエンチする、請求項19に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161441525P | 2011-02-10 | 2011-02-10 | |
US61/441,525 | 2011-02-10 | ||
PCT/US2012/024160 WO2012109256A2 (en) | 2011-02-10 | 2012-02-07 | Formation of n-protected bis-3,6-(4-aminoalkyl) -2,5,diketopiperazine |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014513045A true JP2014513045A (ja) | 2014-05-29 |
JP6018586B2 JP6018586B2 (ja) | 2016-11-02 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2013553494A Active JP6018586B2 (ja) | 2011-02-10 | 2012-02-07 | N−保護ビス−3,6−(4−アミノアルキル)−2,5,ジケトピペラジンの生成 |
Country Status (13)
Country | Link |
---|---|
US (6) | US8912328B2 (ja) |
EP (1) | EP2673265B1 (ja) |
JP (1) | JP6018586B2 (ja) |
KR (1) | KR20140027937A (ja) |
CN (2) | CN105884700A (ja) |
AU (2) | AU2012214592B2 (ja) |
BR (1) | BR112013020514B1 (ja) |
CA (1) | CA2826973C (ja) |
IL (1) | IL227904A (ja) |
MX (1) | MX346331B (ja) |
RU (1) | RU2606624C2 (ja) |
SG (3) | SG10201802008TA (ja) |
WO (1) | WO2012109256A2 (ja) |
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DE60318938T2 (de) | 2002-03-20 | 2009-01-22 | Mannkind Corp., Valencia | Inhalationsgerät |
DK1786784T3 (da) | 2004-08-20 | 2011-02-14 | Mannkind Corp | Katalyse af diketopiperazinsyntese |
JP4990142B2 (ja) | 2004-08-23 | 2012-08-01 | マンカインド コーポレイション | 薬物送達のためのジケトピペラジン塩、ジケトモルホリン塩、又はジケトジオキサン塩 |
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ES2904623T3 (es) | 2008-06-20 | 2022-04-05 | Mannkind Corp | Aparato interactivo para establecer un perfil en tiempo real de esfuerzos de inhalación |
TWI532497B (zh) | 2008-08-11 | 2016-05-11 | 曼凱公司 | 超快起作用胰島素之用途 |
US8314106B2 (en) | 2008-12-29 | 2012-11-20 | Mannkind Corporation | Substituted diketopiperazine analogs for use as drug delivery agents |
EP2405963B1 (en) | 2009-03-11 | 2013-11-06 | MannKind Corporation | Apparatus, system and method for measuring resistance of an inhaler |
WO2010144789A2 (en) | 2009-06-12 | 2010-12-16 | Mannkind Corporation | Diketopiperazine microparticles with defined specific surface areas |
WO2011056889A1 (en) | 2009-11-03 | 2011-05-12 | Mannkind Corporation | An apparatus and method for simulating inhalation efforts |
KR20130117755A (ko) | 2010-06-21 | 2013-10-28 | 맨카인드 코포레이션 | 건조 분말 약물 운반 시스템 및 방법 |
SG10201802008TA (en) * | 2011-02-10 | 2018-04-27 | Mannkind Corp | Formation of n-protected bis-3,6-(4-aminoalkyl) -2,5,diketopiperazine |
CN105667994B (zh) | 2011-04-01 | 2018-04-06 | 曼金德公司 | 用于药物药盒的泡罩包装 |
WO2012174472A1 (en) | 2011-06-17 | 2012-12-20 | Mannkind Corporation | High capacity diketopiperazine microparticles |
WO2013063160A1 (en) | 2011-10-24 | 2013-05-02 | Mannkind Corporation | Methods and compositions for treating pain |
WO2013142969A1 (en) * | 2012-03-28 | 2013-10-03 | Jian Ping Gao | Urethanes and ureas and processes |
SG11201406970QA (en) | 2012-04-27 | 2014-11-27 | Mannkind Corp | Methods for the synthesis of ethylfumarates and their use as intermediates |
CN108057154B (zh) | 2012-07-12 | 2021-04-16 | 曼金德公司 | 干粉药物输送***和方法 |
US10159644B2 (en) | 2012-10-26 | 2018-12-25 | Mannkind Corporation | Inhalable vaccine compositions and methods |
KR20150131356A (ko) * | 2013-03-15 | 2015-11-24 | 맨카인드 코포레이션 | 사이클릭 알파-n-보호된 아미노 에스테르를 통한 n-보호된 비스-3,6-(4-아미노부틸)-2,5-디케토피페라진의 형성 |
JP6523247B2 (ja) | 2013-03-15 | 2019-05-29 | マンカインド コーポレイション | 微結晶性ジケトピペラジン粒子の製造方法および乾燥粉末組成物の製造方法 |
EP3021834A1 (en) | 2013-07-18 | 2016-05-25 | MannKind Corporation | Heat-stable dry powder pharmaceutical compositions and methods |
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CN106795174B (zh) * | 2015-08-10 | 2020-04-28 | 扬州蓝色生物医药科技有限公司 | 一种抗病毒活性双氮氧杂环螺二酮哌嗪生物碱衍生物及其制备方法 |
TWI750188B (zh) | 2016-06-20 | 2021-12-21 | 日商鹽野義製藥股份有限公司 | 用於製備經取代多環吡啶酮衍生物之方法及其結晶 |
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- 2012-02-07 KR KR1020137023801A patent/KR20140027937A/ko not_active Application Discontinuation
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