CA2254972C - Process for the preparation of 1-alkoxycarbonyl-3-phenylpropyl derivatives - Google Patents

Process for the preparation of 1-alkoxycarbonyl-3-phenylpropyl derivatives Download PDF

Info

Publication number
CA2254972C
CA2254972C CA002254972A CA2254972A CA2254972C CA 2254972 C CA2254972 C CA 2254972C CA 002254972 A CA002254972 A CA 002254972A CA 2254972 A CA2254972 A CA 2254972A CA 2254972 C CA2254972 C CA 2254972C
Authority
CA
Canada
Prior art keywords
phenylpropyl
alanine
ethoxycarbonyl
alkoxycarbonyl
reaction
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.)
Expired - Fee Related
Application number
CA002254972A
Other languages
English (en)
French (fr)
Other versions
CA2254972A1 (en
Inventor
Yasuyoshi Ueda
Akira Matsumoto
Hajime Manabe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kaneka Corp
Original Assignee
Kaneka 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 Kaneka Corp filed Critical Kaneka Corp
Publication of CA2254972A1 publication Critical patent/CA2254972A1/en
Application granted granted Critical
Publication of CA2254972C publication Critical patent/CA2254972C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/38—Separation; Purification; Stabilisation; Use of additives
    • C07C227/40—Separation; Purification
    • C07C227/42—Crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Indole Compounds (AREA)
  • Catalysts (AREA)
  • Quinoline Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA002254972A 1996-05-10 1997-05-08 Process for the preparation of 1-alkoxycarbonyl-3-phenylpropyl derivatives Expired - Fee Related CA2254972C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP11654596A JP3792777B2 (ja) 1996-05-10 1996-05-10 １−アルコキシカルボニル−３−フェニルプロピル誘導体の製造方法
JP8/116545 1996-05-10
PCT/JP1997/001543 WO1997043246A1 (fr) 1996-05-10 1997-05-08 Procede de preparation de derives de 1-alcoxycarbonyl-3-phenylpropyle

Publications (2)

Publication Number Publication Date
CA2254972A1 CA2254972A1 (en) 1997-11-20
CA2254972C true CA2254972C (en) 2005-08-02

Family

ID=14689775

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002254972A Expired - Fee Related CA2254972C (en) 1996-05-10 1997-05-08 Process for the preparation of 1-alkoxycarbonyl-3-phenylpropyl derivatives

Country Status (13)

Country Link
US (1) US6118010A (OSRAM)
EP (2) EP0903337B1 (OSRAM)
JP (1) JP3792777B2 (OSRAM)
KR (1) KR100382633B1 (OSRAM)
CN (1) CN1159286C (OSRAM)
AT (1) ATE481378T1 (OSRAM)
CA (1) CA2254972C (OSRAM)
DE (2) DE69739998D1 (OSRAM)
ES (2) ES2353151T3 (OSRAM)
HU (1) HU227430B1 (OSRAM)
IN (2) IN183558B (OSRAM)
SI (1) SI9720039B (OSRAM)
WO (1) WO1997043246A1 (OSRAM)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ292494B6 (cs) * 1998-09-22 2003-10-15 Kaneka Corporation Způsob výroby N2-(1(S)-karboxy-3-fenylpropyl)-L-lysyl-L-prolinu
AU2000239828A1 (en) * 2000-04-18 2001-10-30 Scinopharm Singapore Pte Ltd Process for preparation of 3-((1'-(alkoxycarbonyl)-3'-phenylpropyl)amino)-2-oxo-(1)- benzazepine and its derivatives
AR033048A1 (es) 2001-03-19 2003-12-03 Kaneka Corp Metodo para la purificacion de la n-(1(s)-etoxicarbonil-3-fenilpropil) -l-alanina
JP2003026644A (ja) * 2001-07-11 2003-01-29 Kanegafuchi Chem Ind Co Ltd Ｎ２−（１（ｓ）−エトキシカルボニル−３−フェニルプロピル）−ｎ６−トリフルオロアセチル−ｌ−リジンの精製方法
SI21101A (sl) * 2001-11-26 2003-06-30 LEK farmacevtska dru�ba d.d. Koncentriranje vodnih frakcij lisinoprila z reverzno osmozo
WO2004000874A1 (en) * 2002-06-19 2003-12-31 Eos Eczacibasi Ozgun Kimyasal Urunler Sanyi Ve Ti Caret A.S. Process for the production of lisinopril
JP4744979B2 (ja) * 2005-08-24 2011-08-10 独立行政法人理化学研究所 ゼオライトを用いたタンパク質結晶化方法
PL2118123T3 (pl) 2007-01-31 2016-06-30 Dana Farber Cancer Inst Inc Stabilizowane peptydy p53 i ich zastosowania
JP5631201B2 (ja) 2007-03-28 2014-11-26 プレジデント アンド フェローズ オブ ハーバード カレッジ ステッチングされたポリペプチド
CN101239923B (zh) * 2007-12-31 2010-09-15 浙江工业大学 (s,s)n-(1-乙氧羰基-3-苯丙基)-l-氨基酸衍生物的制备方法与精制方法
KR102104762B1 (ko) 2010-08-13 2020-04-24 에일러론 테라퓨틱스 인코포레이티드 펩티도미메틱 거대고리
CN101973904B (zh) * 2010-09-28 2014-01-01 雅本化学股份有限公司 一种具有高光学纯度的n2-[1-(s)-乙氧羰基-3-苯丙基]-n6-三氟乙酰基-l-赖氨酸的制备方法
EP2768518A4 (en) 2011-10-18 2015-05-27 Aileron Therapeutics Inc PEPTIDOMIMETIC MACROCYCLES
RU2642299C2 (ru) 2012-02-15 2018-01-24 Эйлерон Терапьютикс, Инк. P53 пептидомиметические макроциклы
CA2864120A1 (en) 2012-02-15 2013-08-22 Aileron Therapeutics, Inc. Triazole-crosslinked and thioether-crosslinked peptidomimetic macrocycles
BR112015009470A2 (pt) 2012-11-01 2019-12-17 Aileron Therapeutics Inc aminoácidos dissubstituídos e seus métodos de preparação e uso
CN105294827A (zh) * 2014-07-21 2016-02-03 常州制药厂有限公司 一种马来酸依那普利的制备方法
CN107106642B (zh) 2014-09-24 2021-02-26 艾瑞朗医疗公司 拟肽大环化合物及其制剂
EP3197478A4 (en) 2014-09-24 2018-05-30 Aileron Therapeutics, Inc. Peptidomimetic macrocycles and uses thereof
JP2018516844A (ja) 2015-03-20 2018-06-28 エルロン・セラピューティクス・インコーポレイテッドＡｉｌｅｒｏｎ Ｔｈｅｒａｐｅｕｔｉｃｓ，Ｉｎｃ． ペプチド模倣大環状分子およびその使用
CN106220545B (zh) * 2016-07-21 2019-08-13 成都摩尔生物医药有限公司 一种acei药物环己基杂质的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1327787A3 (ru) * 1981-11-05 1987-07-30 Хехст Аг (Фирма) Способ получени цис,эндо-2-азабицикло-/3,3,0/-октан-3-карбоновых кислот или их кислотно-аддитивных солей
DE3246503A1 (de) * 1982-12-16 1984-06-20 Hoechst Ag, 6230 Frankfurt Derivate der cis, endo-2-azabicyclo-(5.3.0)-decan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung
EP0190687B1 (en) * 1985-02-04 1988-10-05 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Process for preparing ethyl-alpha-(1-carboxyethyl)-amino-gamma-oxo-gamma-phenylbutyrate
ES2028812T3 (es) * 1986-03-27 1992-07-16 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Un procedimiento para la preparacion de un derivado de n2-(1-carboxi-3-oxo-3-fenilpropil)-l-lisina.
JPH01104034A (ja) * 1986-03-27 1989-04-21 Kanegafuchi Chem Ind Co Ltd Ｎ↑２−（１−カルボキシ−３−フエニルプロピル）−ｌ−リジン誘導体の製造法
JPS62239062A (ja) * 1986-04-11 1987-10-19 Matsushita Electric Ind Co Ltd 交差コイル式メ−タの駆動回路
JPH03115254A (ja) * 1990-09-12 1991-05-16 Kanegafuchi Chem Ind Co Ltd α―（１―カルボキシエチル）アミノ―γ―フエニル酪酸エチルの製造法
JPH06336495A (ja) * 1993-05-28 1994-12-06 Kyowa Hakko Kogyo Co Ltd Ｌ−アラニル−ｌ−プロリン誘導体の製造法

Also Published As

Publication number Publication date
JP3792777B2 (ja) 2006-07-05
ES2257775T3 (es) 2006-08-01
KR100382633B1 (ko) 2003-07-12
DE69739998D1 (de) 2010-10-28
EP0903337B1 (en) 2006-04-12
EP1679303B1 (en) 2010-09-15
IN183558B (OSRAM) 2000-02-12
SI9720039B (sl) 2002-02-28
CA2254972A1 (en) 1997-11-20
ATE481378T1 (de) 2010-10-15
SI9720039A (sl) 1999-08-31
EP0903337A1 (en) 1999-03-24
EP0903337A4 (en) 2001-02-28
WO1997043246A1 (fr) 1997-11-20
ES2353151T3 (es) 2011-02-25
EP1679303A1 (en) 2006-07-12
IN187140B (OSRAM) 2002-02-09
HUP9903214A3 (en) 2002-12-28
HU227430B1 (hu) 2011-06-28
DE69735667D1 (de) 2006-05-24
US6118010A (en) 2000-09-12
JPH09301938A (ja) 1997-11-25
DE69735667T2 (de) 2007-04-26
CN1218454A (zh) 1999-06-02
KR20000010840A (ko) 2000-02-25
CN1159286C (zh) 2004-07-28

Similar Documents

Publication Publication Date Title
US6118010A (en) Process for the preparation of 1-alkoxycarbonyl-3-phenylpropyl derivatives
US4436925A (en) Addition compound of dipeptide derivative and amino acid derivative
EP0092933B1 (en) Process for producing alpha-l-aspartyl-l-phenylalanine methyl ester or its hydrochloride
US6335461B1 (en) Process for purification of aspartame derivative
US20010023301A1 (en) Process for the preparation of neotame
BE863245A (fr) Nouveaux composes d'addition d'un derive de dipeptide et d'un derive d'amino-acide, et leur procede de preparation et de decomposition
CA1243668A (en) Aspartame synthesis
EP0256812B1 (en) Process for separation of n-protected alpha-l-aspartyl-l-phenylalanines
US4656304A (en) Aspartame synthesis
JP2662287B2 (ja) α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの分離方法
EP1380570A1 (en) Process for producing n-formylamino acid and utilization thereof
JP4548756B2 (ja) アミノ酸アミドの精製法
JPH07637B2 (ja) α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルまたはその塩酸塩を製造する方法
JP3178092B2 (ja) α−Ｌ−アスパルチル−Ｌ−フェニルアラニンメチルエステル塩酸塩の製造方法
JPS6022918B2 (ja) Ｎ−ベンジルオキシカルボニル−ｌ−アスパルチル−ｌ−フェニルアラニンメチル−エステルとフェニルアラニンメチルエステルとの付加化合物の製造方法
CH508590A (fr) Procédé de préparation des esters d'alcoyle inférieurs de l'a-L-aspartyl-L-phénylalanine
JPH07639B2 (ja) α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルまたはその塩酸塩の製法
MXPA00003292A (es) Proceso para la purificacion de derivado de aspartame
MXPA01002565A (en) Process for the preparation of neotame
JPS63141993A (ja) α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルのハロゲン化水素酸塩の製造方法
JPH0463080B2 (OSRAM)
JPS6256857B2 (OSRAM)

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20130508