MX346331B - Formación de bis-3, 6-(4-aminoalquil) - 2, 5-dicetopiperazina con n protegido. - Google Patents

Formación de bis-3, 6-(4-aminoalquil) - 2, 5-dicetopiperazina con n protegido.

Info

Publication number
MX346331B
MX346331B MX2013009260A MX2013009260A MX346331B MX 346331 B MX346331 B MX 346331B MX 2013009260 A MX2013009260 A MX 2013009260A MX 2013009260 A MX2013009260 A MX 2013009260A MX 346331 B MX346331 B MX 346331B
Authority
MX
Mexico
Prior art keywords
acid
aminoalkyl
protected
cresol
diketopiperazine
Prior art date
Application number
MX2013009260A
Other languages
English (en)
Other versions
MX2013009260A (es
Inventor
J Freeman John
Stamper Adrienne
Heitmann Melissa
Original Assignee
Mannkind Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mannkind Corp filed Critical Mannkind Corp
Publication of MX2013009260A publication Critical patent/MX2013009260A/es
Publication of MX346331B publication Critical patent/MX346331B/es

Links

Classifications

    • 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
    • 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
    • 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
    • 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

Landscapes

  • 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

Las modalidades descritas detallan métodos mejorados para la síntesis de dicetopiperazinas derivadas de aminoácidos. En particular, métodos mejorados para la ciclocondensación y purificación de 3,6- (aminoalquil)-2,5-dicetopiperazinas con N protegido derivadas de aminoácidos con N protegido. Las modalidades descritas describen métodos para la síntesis de 3,6-bis[aminoalquil con N protegido]-2,5- dicetopiperazina que comprende calentar una mezcla de un aminoácido en presencia de un catalizador en un solvente orgánico. El catalizador se selecciona a partir del grupo que comprende ácido sulfúrico, ácido fosfórico, ácido p-toluenosulfónico, anhídrido cíclico de ácido 1-propilfosfónico, fosfato de tributilo, ácido fenilfosfónico y pentóxido de fósforo entre otros. El solvente se selecciona a partir del grupo que incluye: dimetilacetamida, N-metil-2-pirrolidona, éter dimetilico de dietilenglicol, éter dietílico de etilenglicol, éter dimetílico de dipropilenglicol, éter dietílico de dietilenglicol, m-cresol, p-cresol, o-cresol, xilenos, etilenglicol y fenol entre otros.
MX2013009260A 2011-02-10 2012-02-07 Formación de bis-3, 6-(4-aminoalquil) - 2, 5-dicetopiperazina con n protegido. MX346331B (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161441525P 2011-02-10 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
MX2013009260A MX2013009260A (es) 2014-08-21
MX346331B true MX346331B (es) 2017-03-15

Family

ID=46639161

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2013009260A MX346331B (es) 2011-02-10 2012-02-07 Formación de bis-3, 6-(4-aminoalquil) - 2, 5-dicetopiperazina con n protegido.

Country Status (13)

Country Link
US (8) US8912328B2 (es)
EP (1) EP2673265B1 (es)
JP (1) JP6018586B2 (es)
KR (1) KR20140027937A (es)
CN (2) CN105884700A (es)
AU (2) AU2012214592B2 (es)
BR (1) BR112013020514B1 (es)
CA (1) CA2826973C (es)
IL (1) IL227904A (es)
MX (1) MX346331B (es)
RU (1) RU2606624C2 (es)
SG (3) SG10201802008TA (es)
WO (1) WO2012109256A2 (es)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9006175B2 (en) 1999-06-29 2015-04-14 Mannkind Corporation Potentiation of glucose elimination
EP1494732B1 (en) 2002-03-20 2008-01-30 MannKind Corporation Inhalation apparatus
DK1786784T3 (da) * 2004-08-20 2011-02-14 Mannkind Corp Katalyse af diketopiperazinsyntese
CN104436170B (zh) 2004-08-23 2018-02-23 曼金德公司 用于药物输送的二酮哌嗪盐
AU2006290227B2 (en) 2005-09-14 2012-08-02 Mannkind Corporation Method of drug formulation based on increasing the affinity of crystalline microparticle surfaces for active agents
KR20080096809A (ko) 2006-02-22 2008-11-03 맨카인드 코포레이션 디케토피페라진 및 활성제를 포함하는 마이크로입자의 약학특성의 개선 방법
SG10201507036TA (en) 2008-06-13 2015-10-29 Mannkind Corp A dry powder inhaler and system for drug delivery
US8485180B2 (en) 2008-06-13 2013-07-16 Mannkind Corporation Dry powder drug delivery system
EP2609954B1 (en) 2008-06-20 2021-12-29 MannKind Corporation An interactive apparatus for real-time profiling of inhalation efforts
TWI614024B (zh) 2008-08-11 2018-02-11 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
MX2011009512A (es) 2009-03-11 2011-11-29 Mannkind Corp Aparato, sistema y metodo para medir la resistencia de un inhalador.
MY157166A (en) 2009-06-12 2016-05-13 Mankind Corp Diketopiperazine microparticles with defined specific surface areas
CA2778698A1 (en) 2009-11-03 2011-05-12 Mannkind Corporation An apparatus and method for simulating inhalation efforts
IL223742A (en) 2010-06-21 2016-06-30 Mannkind Corp A dry powder inhaler and preparation for it
JP6018586B2 (ja) * 2011-02-10 2016-11-02 マンカインド・コーポレイシヨン 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
EP2694402B1 (en) 2011-04-01 2017-03-22 MannKind Corporation Blister package for pharmaceutical cartridges
WO2012174472A1 (en) 2011-06-17 2012-12-20 Mannkind Corporation High capacity diketopiperazine microparticles
HK1200318A1 (en) 2011-10-24 2015-08-07 曼金德公司 Methods and compositions for treating pain
CN104284918B (zh) * 2012-03-28 2017-03-29 高剑萍 氨酯型和脲酯型化合物及其制备方法
EP2841422B1 (en) 2012-04-27 2019-08-28 MannKind Corporation Methods for the synthesis of ethylfumarates and their use as intermediates
EP2872205B1 (en) 2012-07-12 2017-02-08 MannKind Corporation Dry powder drug delivery systems
US10159644B2 (en) 2012-10-26 2018-12-25 Mannkind Corporation Inhalable vaccine compositions and methods
WO2014144895A1 (en) 2013-03-15 2014-09-18 Mannkind Corporation Microcrystalline diketopiperazine compositions and methods
CN107935942B (zh) * 2013-03-15 2021-06-15 麦康公司 环状α-N-保护氨基酯形成N-保护双-3,6-(4-氨基丁基)-2,5-哌嗪二酮
KR102465025B1 (ko) 2013-07-18 2022-11-09 맨카인드 코포레이션 열-안정성 건조 분말 약제학적 조성물 및 방법
EP3030294B1 (en) 2013-08-05 2020-10-07 MannKind Corporation Insufflation apparatus
CN105254576A (zh) * 2014-02-26 2016-01-20 中国科学院长春应用化学研究所 一种谷氨酸二酮哌嗪的制备方法
US10307464B2 (en) 2014-03-28 2019-06-04 Mannkind Corporation Use of ultrarapid acting insulin
US10561806B2 (en) 2014-10-02 2020-02-18 Mannkind Corporation Mouthpiece cover for an inhaler
WO2017025031A1 (zh) * 2015-08-10 2017-02-16 于跃 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
SG11201810655QA (en) 2016-06-20 2019-01-30 Shionogi & Co Method for producing substituted polycyclic pyridone derivative and crystal of same
CN108997168B (zh) * 2018-07-14 2021-09-28 上海应用技术大学 一种含氟非天然赖氨酸衍生物的通用合成方法
CN118994038B (zh) * 2024-07-31 2025-09-26 三峡大学 一种甘氨酸合成甘氨酸酐的方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5352461A (en) * 1992-03-11 1994-10-04 Pharmaceutical Discovery Corporation Self assembling diketopiperazine drug delivery system
GB9217331D0 (en) * 1992-08-14 1992-09-30 Xenova Ltd Pharmaceutical compounds
JPH06321916A (ja) * 1993-05-14 1994-11-22 Mitsui Toatsu Chem Inc ３，６−ビス［（４−ヒドロキシフェニル）メチル］−２，５−ジケトピペラジンの製造方法。
US6153753A (en) * 1997-02-13 2000-11-28 Monsanto Company Method of preparing amino carboxylic acids
US6337678B1 (en) * 1999-07-21 2002-01-08 Tactiva Incorporated Force feedback computer input and output device with coordinated haptic elements
US6590993B2 (en) * 1999-09-06 2003-07-08 Koninklijke Philips Electronics N.V. Panel-shaped loudspeaker
DE10019879A1 (de) * 2000-04-20 2001-10-25 Degussa Verfahren zur Herstellung von 2,5-Diketopiperazinen, neue 2,5-Diketopiperazine und deren Verwendung
DK1786784T3 (da) * 2004-08-20 2011-02-14 Mannkind Corp Katalyse af diketopiperazinsyntese
JP4968848B2 (ja) * 2008-01-30 2012-07-04 株式会社Ａｄｅｋａ ポリオレフィン樹脂組成物
CN101851213A (zh) * 2010-06-21 2010-10-06 于清 3，6-双(4-双反丁烯二酰基氨丁基)-2，5-二酮哌嗪及其盐取代物的合成方法
CN101914032B (zh) * 2010-07-15 2013-06-05 启东市沪东化工有限公司 (s)-n-三氟乙酰基-对甲氧基苯乙胺的合成方法
JP6018586B2 (ja) * 2011-02-10 2016-11-02 マンカインド・コーポレイシヨン 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

Also Published As

Publication number Publication date
AU2012214592A1 (en) 2013-08-29
CN103534242A (zh) 2014-01-22
US20130012710A1 (en) 2013-01-10
JP2014513045A (ja) 2014-05-29
MX2013009260A (es) 2014-08-21
SG10201600967VA (en) 2016-03-30
US20250163003A1 (en) 2025-05-22
US20260042739A1 (en) 2026-02-12
US10196366B2 (en) 2019-02-05
US20200262797A1 (en) 2020-08-20
US20160347721A1 (en) 2016-12-01
AU2017203860B2 (en) 2020-02-20
WO2012109256A3 (en) 2013-01-24
CA2826973C (en) 2020-03-24
BR112013020514A2 (pt) 2016-07-12
KR20140027937A (ko) 2014-03-07
US20230034201A1 (en) 2023-02-02
WO2012109256A2 (en) 2012-08-16
CA2826973A1 (en) 2012-08-16
AU2017203860A1 (en) 2017-06-22
SG10201802008TA (en) 2018-04-27
US10640471B2 (en) 2020-05-05
CN105884700A (zh) 2016-08-24
AU2012214592B2 (en) 2017-03-09
BR112013020514B1 (pt) 2020-12-08
EP2673265A2 (en) 2013-12-18
US8912328B2 (en) 2014-12-16
EP2673265A4 (en) 2014-08-06
US9416113B2 (en) 2016-08-16
JP6018586B2 (ja) 2016-11-02
IL227904A (en) 2016-12-29
SG192708A1 (en) 2013-09-30
IL227904A0 (en) 2013-09-30
EP2673265B1 (en) 2016-10-19
US20150073149A1 (en) 2015-03-12
RU2013138609A (ru) 2015-03-20
RU2606624C2 (ru) 2017-01-10
US12459903B2 (en) 2025-11-04
US11440891B2 (en) 2022-09-13
CN103534242B (zh) 2016-04-20
US20190169135A1 (en) 2019-06-06

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