WO2007085729A3 - Nouvelle methode de synthese de l,4-morpholine-2,5-diones - Google Patents

Nouvelle methode de synthese de l,4-morpholine-2,5-diones Download PDF

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Publication number
WO2007085729A3
WO2007085729A3 PCT/FR2007/000135 FR2007000135W WO2007085729A3 WO 2007085729 A3 WO2007085729 A3 WO 2007085729A3 FR 2007000135 W FR2007000135 W FR 2007000135W WO 2007085729 A3 WO2007085729 A3 WO 2007085729A3
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WO
WIPO (PCT)
Prior art keywords
diones
morpholine
synthesis
novel method
formula
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.)
Ceased
Application number
PCT/FR2007/000135
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English (en)
Other versions
WO2007085729A2 (fr
Inventor
Didier Bourissou
Blaca Martin-Vaca
Sylvie Moebs-Sanchez
Coralie Ivens
Roland Cherif-Cheikh
Sousa Delgado Anne-Paula De
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.)
Ipsen Pharma SAS
Original Assignee
Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS
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 Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS filed Critical Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS
Priority to EP07730853A priority Critical patent/EP1981861A2/fr
Priority to US12/162,334 priority patent/US20100036120A1/en
Priority to CA002640031A priority patent/CA2640031A1/fr
Priority to JP2008551822A priority patent/JP2009528982A/ja
Publication of WO2007085729A2 publication Critical patent/WO2007085729A2/fr
Publication of WO2007085729A3 publication Critical patent/WO2007085729A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne une nouvelle méthode de synthèse de 1,4-morpholine- 2 5-diones de formule (I), dans laquelle R, R1, R2, R3 et R4 représentent, indépendamment, divers radicaux, par oxydation de la fonction cétone d'un composé cyclique de formule (II).
PCT/FR2007/000135 2006-01-25 2007-01-24 Nouvelle methode de synthese de l,4-morpholine-2,5-diones Ceased WO2007085729A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP07730853A EP1981861A2 (fr) 2006-01-25 2007-01-24 Nouvelle methode de synthese de l,4-morpholine-2,5-diones
US12/162,334 US20100036120A1 (en) 2006-01-25 2007-01-24 Novel method for synthesis of 1,4-morpholine-2,5-diones
CA002640031A CA2640031A1 (fr) 2006-01-25 2007-01-24 Nouvelle methode de synthese de l,4-morpholine-2,5-diones
JP2008551822A JP2009528982A (ja) 2006-01-25 2007-01-24 １，４−モルホリン−２，５−ジオンの新規の合成方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0600662A FR2896502B1 (fr) 2006-01-25 2006-01-25 Nouvelle methode de synthese de 1,4-morpholine-2,5-diones
FR06/00662 2006-01-25

Publications (2)

Publication Number Publication Date
WO2007085729A2 WO2007085729A2 (fr) 2007-08-02
WO2007085729A3 true WO2007085729A3 (fr) 2008-04-24

Family

ID=36636457

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2007/000135 Ceased WO2007085729A2 (fr) 2006-01-25 2007-01-24 Nouvelle methode de synthese de l,4-morpholine-2,5-diones

Country Status (8)

Country Link
US (1) US20100036120A1 (fr)
EP (1) EP1981861A2 (fr)
JP (1) JP2009528982A (fr)
CN (1) CN101374822A (fr)
CA (1) CA2640031A1 (fr)
FR (1) FR2896502B1 (fr)
RU (1) RU2008134461A (fr)
WO (1) WO2007085729A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103012238A (zh) * 2013-01-11 2013-04-03 华东理工大学 一种n-取代-1h-吡咯的制备方法
EP3829601B1 (fr) 2018-08-01 2024-05-29 Edix-O Sarl Compositions injectables à durée d'action prolongée pour leur utilisation dans le traitement de maladies de l'ongle
EP3603650A1 (fr) 2018-08-01 2020-02-05 Edix O Sarl Compositions injectables et a duree d'action prolongee pour leur utilisation dans le traitement de maladies de l'ongle et/ou pour accelerer la croissance de l'ongle

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3392169A (en) * 1965-09-02 1968-07-09 Monsanto Co 3, 6-dioxo-2-morpholine acetic acids and process for making them
DE4440193A1 (de) * 1994-11-10 1996-05-15 Bayer Ag Verwendung von Dioxomorpholinen zur Bekämpfung von Endoparasiten, neue Dioxomorpholine und Verfahren zur ihrer Herstellung
WO1996040202A1 (fr) * 1995-06-07 1996-12-19 Chiron Corporation Synthese d'oligomeres n-substitues

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3392169A (en) * 1965-09-02 1968-07-09 Monsanto Co 3, 6-dioxo-2-morpholine acetic acids and process for making them
DE4440193A1 (de) * 1994-11-10 1996-05-15 Bayer Ag Verwendung von Dioxomorpholinen zur Bekämpfung von Endoparasiten, neue Dioxomorpholine und Verfahren zur ihrer Herstellung
WO1996040202A1 (fr) * 1995-06-07 1996-12-19 Chiron Corporation Synthese d'oligomeres n-substitues

Non-Patent Citations (19)

* Cited by examiner, † Cited by third party
Title
ARCELLI, ANTONIO ET AL: "Chiral 1,4-morpholine-2,5-dione derivatives as .alpha.-glucosidase inhibitors: Part 2", TETRAHEDRON: ASYMMETRY , 16(8), 1495-1501 CODEN: TASYE3; ISSN: 0957-4166, 2005, XP004842441 *
ARCELLI, ANTONIO ET AL: "Chiral 1,4-morpholine-2,5-diones. Synthesis and evaluation as glucosidase inhibitors", MONATSHEFTE FUER CHEMIE , 135(8), 951-958 CODEN: MOCMB7; ISSN: 0026-9247, 2004, XP002469417 *
CARLONI, ARMANDO ET AL: "Stereoselective synthesis of uncommon .alpha.',.alpha.'-dialkyl-.alpha.- amino acids. Part 1", TETRAHEDRON: ASYMMETRY , 9(17), 2987-2998 CODEN: TASYE3; ISSN: 0957-4166, 1998, XP004138976 *
CINGOLANI G M ET AL: "Synthesis of l-(+)-3-(3-hydroxy-4-pivaloyloxybenzyl)-2,5-diketomorph oline as potential prodrug of l-dopa", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, OXFORD, GB, vol. 10, no. 12, June 2000 (2000-06-01), pages 1385 - 1388, XP004207011, ISSN: 0960-894X *
CRANE, SHELDON N. ET AL: "A Novel Enantioselective Synthetic Route to Omuralide Analogues with the Potential for Species Selectivity in Proteasome Inhibition", ORGANIC LETTERS , 3(9), 1395-1397 CODEN: ORLEF7; ISSN: 1523-7060, 2001, XP008038134 *
DI FELICE, PINA ET AL: "A new stereoselective approach to .beta.-hydroxy-.alpha.-amino acids and dipeptides", TETRAHEDRON: ASYMMETRY , 10(11), 2191-2201 CODEN: TASYE3; ISSN: 0957-4166, 1999, XP004174102 *
DIJKSTRA P J ET AL: "SYNTHETIC PATHWAYS TO POLYDEPSIPEPTIDES", MACROMOLECULAR SYMPOSIA, WILEY VCH VERLAG, WEINHEIM, DE, no. 153, March 2000 (2000-03-01), pages 67 - 76, XP000991927, ISSN: 1022-1360 *
FENG, YAKAI ET AL: "Lipase-catalyzed ring-opening polymerization of 3(S)-sec-butylmorpholine- 2,5-dione", MACROMOLECULAR BIOSCIENCE , 1(2), 66-74 PUBLISHED IN: MACROMOL. CHEM. PHYS., 202(5) CODEN: MBAIBU; ISSN: 1616-5187, 2001, XP002396670 *
GERONA-NAVARRO, GUILLERMO ET AL: "Entry to New Conformationally Constrained Amino Acids. First Synthesis of 3-Unsubstituted 4-Alkyl-4-carboxy-2-azetidinone Derivatives via an Intramolecular N.alpha.-C.alpha.-Cyclization Strategy", JOURNAL OF ORGANIC CHEMISTRY , 66(10), 3538-3547 CODEN: JOCEAH; ISSN: 0022-3263, 2001, XP002469416 *
GRAZIANI, LUCIA ET AL: "An improved procedure for the enantioselective synthesis of (+)- and (-)-cis-4-hydroxyprolines and bulgecinines", TETRAHEDRON: ASYMMETRY , 7(5), 1341-1346 CODEN: TASYE3; ISSN: 0957-4166, 1996, XP004047693 *
HUANG, XUEFEI ET AL: "Absolute Configurational Assignments of Secondary Amines by CD-Sensitive Dimeric Zinc Porphyrin Host", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY , 124(35), 10320-10335 CODEN: JACSAT; ISSN: 0002-7863, 2002, XP002396669 *
IN'T VELD P J A ET AL: "SYNTHESIS OF BIODEGRADABLE POLYESTERAMIDES WITH PENDANT FUNCTIONAL GROUPS", MAKROMOLEKULARE CHEMIE, MACROMOLECULAR CHEMISTRY AND PHYSICS, HUTHIG UND WEPF VERLAG, BASEL, CH, vol. 193, no. 11, 1 November 1992 (1992-11-01), pages 2713 - 2730, XP000311432, ISSN: 0025-116X *
KOCH, CLAUS-JURGEN ET AL: "Asymmetric synthesis with 6-tert-butyl-5-methoxy-6-methyl-3,6-dihydro-2H- 1,4-oxazin-2-one as a new chiral glycine equivalent: preparation of enantiomerically pure .alpha.-tertiary and .alpha.-quaternary .alpha.-amino acids", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY , (7), 1244-1263 CODEN: EJOCFK; ISSN: 1434-193X, 2003, XP002396668 *
L.A. PAQUETTE, S. BRAND AND C. BEHRENS: "an enantioselective ring expansion route leading to furanose and pyranose nucleosides featuring spirodiketopiperazines at anomeric position", JOURNAL OF ORGANIC CHEMISTRY, vol. 64, no. 6, 1999, pages 2010 - 2025, XP002396695 *
PORZI, GIANNI ET AL: "A new stereoselective synthesis of sterically constrained uncommon .alpha.,.alpha.'-dialkylated .alpha.-amino acids. Part 2", TETRAHEDRON: ASYMMETRY , 9(19), 3411-3420 CODEN: TASYE3; ISSN: 0957-4166, 1998, XP004339196 *
PORZI, GIANNI ET AL: "Enantioselective synthesis of (R)- and (S)-.alpha.-amino acids using (6S)- and (6R)-6-methyl-morpholine-2,5-dione derivatives", TETRAHEDRON: ASYMMETRY , 7(1), 189-96 CODEN: TASYE3; ISSN: 0957-4166, 1996, XP004047913 *
SHIRAHAMA H ET AL: "SYNTHESIS AND BIODEGRADABILITY OF DEPSIPEPTIDE COPOLYMERS - EFFECT OF AMINO ACID UNIT", KOBUNSHI RONBUNSHU (JAPANESE POLYMER SCIENCE AND TECHNOLOGY), SOCIETY OF POLYMER SCIENCE, TOKYO, JP, vol. 55, no. 6, 1 June 1998 (1998-06-01), pages 359 - 366, XP000779572, ISSN: 0386-2186 *
SHIRAHAMA H ET AL: "SYNTHESIS AND BIODEGRADATION OF CYCLIC DEPSIPEPTIDE/EPSILON- CAPROLACTONE COPOLYMERS - EFFECT OF HYDROXY ACID UNIT -", KOBUNSHI RONBUNSHU (JAPANESE POLYMER SCIENCE AND TECHNOLOGY), SOCIETY OF POLYMER SCIENCE, TOKYO, JP, vol. 56, no. 2, February 1999 (1999-02-01), pages 77 - 85, XP000804328, ISSN: 0386-2186 *
WEE ET AL: "Dirhodium tetraacetate catalyzed carbon-hydrogen insertion reaction in N-substituted.alpha.-carbomethoxy-.alpha.-diazoacetanilides and structural analogs. Substituent and conformational effects", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 57, no. 16, 1992, pages 4404 - 4414, XP002177360, ISSN: 0022-3263 *

Also Published As

Publication number Publication date
CN101374822A (zh) 2009-02-25
CA2640031A1 (fr) 2007-08-02
FR2896502A1 (fr) 2007-07-27
FR2896502B1 (fr) 2010-09-24
JP2009528982A (ja) 2009-08-13
EP1981861A2 (fr) 2008-10-22
WO2007085729A2 (fr) 2007-08-02
RU2008134461A (ru) 2010-02-27
US20100036120A1 (en) 2010-02-11

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