(19)
(11) EP 3 663 305 B8

(12) CORRECTED EUROPEAN PATENT SPECIFICATION
Note: Bibliography reflects the latest situation

(15) Correction information:
Corrected version no 1 (W1 B1)

(48) Corrigendum issued on:
06.12.2023 Bulletin 2023/49

(45) Mention of the grant of the patent:
30.08.2023 Bulletin 2023/35

(21) Application number: 18841947.7

(22) Date of filing: 29.05.2018
(51) International Patent Classification (IPC): 
C07F 7/18(2006.01)
C07C 405/00(2006.01)
 C07F 7/22(2006.01)
(52) Cooperative Patent Classification (CPC):
C07C 405/00; C07F 7/1804; C07F 7/2208
(86) International application number:
PCT/JP2018/020527
(87) International publication number:
WO 2019/026402 (07.02.2019 Gazette 2019/06)

(54)

METHOD FOR INTRODUCING SUBSTITUENTS INTO A CARBON AT AN ALPHA-POSITION AND A CARBON AT A BETA-POSITION OF AN ALPHA,BETA-UNSATURATED KETONE AND PROSTAGLANDIN SYNTHESIS METHOD UTILIZING SAME

VERFAHREN ZUR EINFÜHRUNG VON SUBSTITUENTEN IN EIN ALPHA,BETA UNGESÄTTIGTES KETON UND VERFAHREN ZUR SYNTHESE VON PROSTAGLANDINVERBINDUNGEN UNTER VERWENDUNG DESSELBEN

PROCÉDÉ D'INTRODUCTION DE SUBSTITUANTS DANS UNE CÉTONE ALPHA,BETA -INSATURÉE ET PROCÉDÉ DE SYNTHÈSE DE COMPOSÉ DE PROSTAGLANDINE L'UTILISANT

(84) Designated Contracting States:
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

(30) Priority: 03.08.2017 JP 2017150745

(43) Date of publication of application:
10.06.2020 Bulletin 2020/24

(73) Proprietor: National Center for Geriatrics and Gerontology
Obu City, Aichi 474-8511 (JP)

(72) Inventors:
  • SUZUKI Masaaki
    Obu City Aichi 474-8511 (JP)
  • KOYAMA Hiroko
    Gifu-shi Gifu 501-1193 (JP)

(74) Representative: Kuhnen & Wacker Patent- und Rechtsanwaltsbüro PartG mbB 
Prinz-Ludwig-Straße 40A
85354 Freising
85354 Freising (DE)


(56) References cited: : 
   
  • MASAAKF SUZUKI ET AL: "Three-component coupling synthesis of prostaglandins a simplified general procedure", TETRAHEDRON, vol. 46, no. 13-14, 1 January 1990 (1990-01-01), pages 4809-4822, XP055679011, DOI: 10.1016/S0040-4020(01)85596-4
  • MORITA YASUSHI ET AL: "An organozinc aid in alkylation and acylation of lithium enolates", JOURNAL OF ORGANIC CHEMISTRY, vol. 54, no. 8, 1 April 1989 (1989-04-01), pages 1785-1787, XP055776946, Washington ISSN: 0022-3263, DOI: 10.1021/jo00269a006
  • GOODING ET AL: "Triply convergent synthesis of 15-(phenoxymethyl) and 4,5-allenyl prostaglandins. Preparation of an individual isomer of enprostil", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, vol. 58, no. 14, 1 January 1993 (1993-01-01), pages 3681-3686, XP002120714, ISSN: 0022-3263, DOI: 10.1021/JO00066A020
  • Hui-Jun Chen ET AL: "Expeditious Entry to the Chamigrane Endoperoxide Family of Natural Products", Organic Letters, vol. 17, no. 3 12 January 2015 (2015-01-12), pages 592-595, XP55678565, DOI: 10.1021/ol503603t Retrieved from the Internet: URL:https://pubs.acs.org/doi/pdf/10.1021/o l503603t [retrieved on 2020-03-23]
  • SUZUKI, M. et al.: "Three-component coupling synthesis of prostaglandins a simplified general procedure", Tetrahedron, vol. 46, no. 13-14, 1 January 1990 (1990-01-01), pages 4809-4822, XP055679011,
  • GOODING, 0. W. et al.: "Triply Convergent Synthesis of 15-(Phenoxymethyl) and 4,5-Allenyl Prostaglandins. Preparation of an Individual Isomer of Enprostil1", The Journal of Organic Chemistry, vol. 58, 1993, pages 3681-3686, XP002386527,
  • CHEN, H. -J. et al.: "Expeditious Entry to the Chamigrane Endoperoxide Family of Natural Products", Organic Letters, vol. 17, no. 3, 2015, pages 592-595, XP055678565, DOI: 10.1021/ol503603t
  • HOLEC, C. et al.: "Chemoenzymatic Synthesis towards the Active Agent Travoprost", ChemCatChem, vol. 7, 31 August 2015 (2015-08-31), pages 3125-3130, XP055679016, ISSN: 1867-3880, DOI: 10.1002/cctc.201500587
  • LIPSHUTZ, B. H. et al.: "A Practical, General Three-Component Coupling Approach to Prostaglandin and Non-Prostaglandin-Related Skeleta", Journal of the American Chemical Society, vol. 116, no. 26, 1994, pages 11689-11702, XP055678567, DOI: 10.1021/ja00105a010
   
Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention).