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EP2734299
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EP About this file: EP2734299
| EP2734299 - CATALYSTS AND PROCESSES FOR THE HYDROGENATION OF AMIDES [Right-click to bookmark this link] | Status | The application is deemed to be withdrawn Status updated on 07.06.2019 Database last updated on 02.11.2024 | |
| Former | Request for examination was made Status updated on 15.12.2016 | Most recent event Tooltip | 07.06.2019 | Application deemed to be withdrawn | published on 10.07.2019 [2019/28] | Applicant(s) | For all designated states The Governors of the University of Alberta 4000 Enterprise Square 10230 Jasper Avenue Edmonton, Alberta T5J 4P6 / CA | [N/P] |
| Former [2014/22] | For all designated states The Governors of the University of Alberta Suite 4000 10230 Jasper Avenue Edmonton, Alberta T5J 4P6 / CA | Inventor(s) | 01 /
BERGENS, Steven 14844-41 Avenue Edmonton, Alberta T6H 5N7 / CA | 02 /
JOHN, Jeremy M. 10533-71 Avenue Edmonton, Alberta T6E 0X2 / CA | [2014/22] | Representative(s) | Abel & Imray LLP Westpoint Building James Street West Bath BA1 2DA / GB | [N/P] |
| Former [2014/22] | Denness, James Edward Abel & Imray 20 Red Lion Street London WC1R 4PQ / GB | Application number, filing date | 12815389.7 | 18.07.2012 | WO2012CA50489 | Priority number, date | US201161508766P | 18.07.2011 Original published format: US 201161508766 P | [2014/22] | Filing language | EN | Procedural language | EN | Publication | Type: | A1 Application with search report | No.: | WO2013010275 | Date: | 24.01.2013 | Language: | EN | [2013/04] | Type: | A1 Application with search report | No.: | EP2734299 | Date: | 28.05.2014 | Language: | EN | The application published by WIPO in one of the EPO official languages on 24.01.2013 takes the place of the publication of the European patent application. | [2014/22] | Search report(s) | International search report - published on: | CA | 24.01.2013 | (Supplementary) European search report - dispatched on: | EP | 08.04.2016 | Classification | IPC: | B01J31/18, B01J31/24, C07B31/00 | [2016/01] | CPC: |
C07F15/0053 (EP,US);
B01J31/1805 (EP,US);
B01J31/189 (EP,US);
B01J31/2409 (EP,US);
B01J31/2452 (EP,US);
C07B31/00 (EP,US);
C07C209/50 (EP,US);
C07C213/00 (EP,US);
C07C231/08 (EP,US);
C07C29/149 (EP,US);
C07C303/40 (EP,US);
C07C41/26 (EP,US);
C07D201/02 (EP,US);
C07D295/023 (EP,US);
C07D295/027 (EP,US);
C07F15/0046 (EP,US);
B01J2231/643 (EP,US);
B01J2531/0244 (EP,US);
B01J2531/0255 (EP,US);
B01J2531/0266 (EP,US);
B01J2531/821 (EP,US);
C07B2200/07 (EP,US)
(-)
| C-Set: |
C07C209/50, C07C211/04 (EP,US);
C07C209/50, C07C211/48 (EP,US);
C07C209/50, C07C211/55 (EP,US);
C07C213/00, C07C215/08 (US,EP);
C07C213/00, C07C215/16 (US,EP);
C07C231/08, C07C233/18 (US,EP);
C07C29/149, C07C31/08 (US,EP);
C07C29/149, C07C33/22 (EP,US); |
| Former IPC [2014/22] | B01J31/00, C07B31/00 | 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 [2014/22] | Title | German: | KATALYSATOREN UND VERFAHREN ZUR HYDRIERUNG VON AMIDEN | [2014/22] | English: | CATALYSTS AND PROCESSES FOR THE HYDROGENATION OF AMIDES | [2014/22] | French: | CATALYSEURS ET PROCÉDÉS DESTINÉS À L'HYDROGÉNATION D'AMIDES | [2014/22] | Entry into regional phase | 12.02.2014 | National basic fee paid | 12.02.2014 | Search fee paid | 12.02.2014 | Designation fee(s) paid | 12.02.2014 | Examination fee paid | Examination procedure | 17.05.2012 | Request for preliminary examination filed International Preliminary Examining Authority: CA | 12.02.2014 | Examination requested [2014/22] | 27.02.2017 | Amendment by applicant (claims and/or description) | 01.02.2019 | Application deemed to be withdrawn, date of legal effect [2019/28] | 28.02.2019 | Despatch of communication that the application is deemed to be withdrawn, reason: renewal fee not paid in time [2019/28] | Request for further processing for: | The application is deemed to be withdrawn due to failure to reply to the Extended European Search Report/Written Opinion of the International Searching Authority/International Preliminary Examination Report/Supplementary international search report/Supplementary European search report | 27.02.2017 | Request for further processing filed | 27.02.2017 | Full payment received (date of receipt of payment) Request granted | 10.03.2017 | Decision despatched | Fees paid | Renewal fee | 28.07.2014 | Renewal fee patent year 03 | 10.07.2015 | Renewal fee patent year 04 | 11.07.2016 | Renewal fee patent year 05 | 12.07.2017 | Renewal fee patent year 06 | Penalty fee | Additional fee for renewal fee | 31.07.2018 | 07 M06 Not yet paid |
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| Responsibility for the accuracy, completeness or quality of the data displayed under the link provided lies entirely with the Unified Patent Court. | Documents cited: | Search | [D]WO2010073974 (TOKYO INST TECH [JP]; CENTRAL GLASS CO LTD [JP]; IKARIYA TAKAO; ITO MA) [D] * abstract * * paragraphs [0062] - [0066]; examples 1-16; table 1; compounds A-P * * paragraphs [0067] - [0070]; examples 17-23; table 2; compounds S,T,U,V * * paragraphs [0071] - [0073]; example 24 * * paragraphs [0074] - [0077]; examples 25-31; table 3; compounds V,W-Z * * paragraphs [0078] - [0081]; examples 32-37; table 4; compounds A'-C', V * * (Groups 1 and 2 inventions) *; | [XDI]WO2010145024 (UNIV ALBERTA [CA]; BERGENS STEVEN H [CA]; TAKEBAYASHI SATOSHI [CA]) [XD] 1-3,5-11,13 * claims 1-5; tables 1-3; compound 5 * [I] 12; | [X]US2010280273 (SAUDAN LIONEL [CH] ET AL) [X] 1,2,4-9,11,13 * example 4 * * (Group 2 inventions) *; | [E]WO2012102247 (UNIV NAGOYA NAT UNIV CORP [JP]; SAITO SUSUMU [JP]; NOYORI RYOJI [JP];) [E] 1,2,6-12 * paragraph [0065]; examples 2-1 - 2-24; tables 1-3 * * (Group 2 inventions) * | [ID] - Ikariya, Takao; Ito, Masato; Ootsuka, Takashi, "Practical method for reducing amides and lactams", CASREACT, CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US, Database accession no. 155:115688, URL: stn, XP002751153 [ID] 1-4,6-11 * abstract * | [ID] - MASATO ITO ET AL, "Catalytic Hydrogenation of Carboxamides and Esters by Well-Defined Cp*Ru Complexes Bearing a Protic Amine Ligand", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, US, (20110307), vol. 133, no. 12, doi:10.1021/ja1117254, ISSN 0002-7863, pages 4240 - 4242, XP055228711 [ID] 1-3,6-9,11 * figure 1; table 1; compounds 1m-1w, 4d * DOI: http://dx.doi.org/10.1021/ja1117254 | [X] - MASATO ITO ET AL, "Chemoselective Hydrogenation of Imides Catalyzed by Cp*Ru(PN) Complexes and Its Application to the Asymmetric Synthesis of Paroxetin", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 129, no. 2, doi:10.1021/JA067777Y, ISSN 0002-7863, (20070117), pages 290 - 291, (20061219), XP008149501 [X] 1,2,4,6-9,11 * the whole document * * (Group 2 inventions) * DOI: http://dx.doi.org/10.1021/ja067777y | [AD] - EKAMBARAM BALARAMAN ET AL, "Direct Hydrogenation of Amides to Alcohols and Amines under Mild Conditions", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, (20101201), vol. 132, no. 47, doi:10.1021/ja1080019, ISSN 0002-7863, pages 16756 - 16758, XP055016966 [AD] 1-12 * abstract * DOI: http://dx.doi.org/10.1021/ja1080019 | [I] - MASATO ITO ET AL, "Hydrogenation of N-Acylcarbamates and N-Acylsulfonamides Catalyzed by a Bifunctional Cp*Ru(PN) Complex", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 48, no. 7, doi:10.1002/ANIE.200805307, ISSN 1433-7851, (20090202), pages 1324 - 1327, (20090107), XP008149293 [I] 1,2,4,6-9,11 * the whole document * * (Group 2 inventions) * DOI: http://dx.doi.org/10.1002/anie.200805307 | [XP] - JEREMY M. JOHN ET AL, "A Highly Active Catalyst for the Hydrogenation of Amides to Alcohols and Amines", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, (20110826), vol. 50, no. 44, doi:10.1002/anie.201103137, ISSN 1433-7851, pages 10377 - 10380, XP055016967 [XP] 1,2,4-9,11,13 * tables 1-3; compound 5 * * (Group 2 inventions) * DOI: http://dx.doi.org/10.1002/anie.201103137 | International search | [X]CA2765607 (BERGENS, S. H. ET AL.); | [X]US2010280273 (SUDAN ET AL.); | [X]WO2010043027 (ABDUR-RASHID, K., ET AL.); | [X]EP2161251 (KURIYAMA, W. ET AL.); | [X]WO2009137932 (ABDUR-RASHID, K., ET AL.); | [X]WO2009006734 (ABDUR-RASHID, K., ET AL..); | [X]WO2006106483 (SUDAN. L.ET AL.); | [X]WO2010145024 (BERGENS, S. ET AL.); | [X] - ITO, M. ET AL., "Hydrogenation of N-acylcarbamates and N-acylsulfonamides catalyzed by a bifunctional [Cp*Ru(PN)] complex", ANGEW. CHEM. INT. ED., (2009), vol. 48, pages 1324 - 1327, XP008149293 DOI: http://dx.doi.org/10.1002/anie.200805307 | [X] - MAGRO, A., A., M. ET AL., "The synthesis of amines by the homogeneous hydrogenation of secondary and primary amides", CHEM. COMMUN., (2007), pages 3154 - 31566, XP002471049 DOI: http://dx.doi.org/10.1039/b706635j | [X] - BALARAMIN ET AL., "Direct hydrogenation of amides to alcohols and amines under mild conditions", J. AM. CHEM. SOC, (2010), vol. 132, pages 16756 - 16758, XP055016966 DOI: http://dx.doi.org/10.1021/ja1080019 | [X] - HAMILTON, R. J. ET AL., "A ruthenium-dihydrogen putative intermediate in ketone hydrogenation", J. AM. CHEM. SOC., (2005), vol. 127, pages 4152 - 4153, XP002619901 DOI: http://dx.doi.org/10.1021/ja043339k | [X] - BLAQUIERE, N. ET AL., "Ruthenium-catalyzed dehydrogenation of ammonia boranes", J. AM. CHEM. SOC., (2008), vol. 130, pages 14034 - 14035, XP055142621 DOI: http://dx.doi.org/10.1021/ja804235t | [X] - TAKEBAYASHI, S. ET AL., "Experimental investigations of a partial Ru-O bond during the metal-ligand bifunctional addition in Noyori-tppe enantioselective ketone hydrogenation", J. AM. CHEM. SOC., (2011), vol. 133, pages 9666 - 9669, XP055142622 DOI: http://dx.doi.org/10.1021/ja202732q | [X] - TAKEAYASHI, S. ET AL., "Desymmetrization of meso-cyclic imides via enantioselective monohydrogenation", J. AM. CHEM. SOC., (2010), vol. 132, pages 12832 - 12834, XP055050108 DOI: http://dx.doi.org/10.1021/ja105783u | [X] - TAKEBAYASHI, S. ET AL., "Facile bifunctional addition of lactones and esters at low temperatures. The first intermediates in lactone/ester hydrogenations.", ORGANOMETALLICS, (20090427), vol. 28, no. 8, pages 2349 - 2351, XP055142624 DOI: http://dx.doi.org/10.1021/om9002076 | [X] - HAMILTON, R. J. ET AL., "Direct observations of the metal-ligand bifunctional addition step in an enantioselective ketone hydrogenation", J. AM. CHEM. SOC, (2008), vol. 130, pages 11979 - 11987, XP008149294 DOI: http://dx.doi.org/10.1021/ja8034812 | [X] - HAMILTON, R. J. ET AL., "An unexpected possible role of base in asymmetric catalytic hydrogenations of ketones. Synthesis and characterization of several key catalytic intermediates.", J. AM. CHEM. SOC., (2006), vol. 128, pages 13700 - 13701, XP008133885 DOI: http://dx.doi.org/10.1021/ja065460s | [X] - KIRANO, M. ET AL., "Synthesis of and stereospecific hydride migration in cationic (tricyclic arene)(cyclooctadiene)ruthenium(II) complexes", ORGANOMETALLICS, (2002), vol. 21, pages 5738 - 5745, XP055142628 DOI: http://dx.doi.org/10.1021/om0205997 | [X] - WILES, J. A. ET AL., "An alternate route to the active chiral hydrogenation catalysts (Ru(bisphosphine)(H)solvent)3]+: Synthesis, characterization and catalytic evaluation", ORGANOMETALLICS, (2004), vol. 23, pages 4564 - 4568, XP001235698 DOI: http://dx.doi.org/10.1021/om049740x | [X] - WILES, J. A. ET AL., "[Ru((R-2,2`bis(diphenylphosphino)-1,1'-binaphthyl)(H)- (MeCN)(THF)2](BF4), a catalyst system for hydrosilylation of ketones and for isomerization, intramolecular hydrosilylation and hydrogenation of olefins", ORGANOMETALLICS, (1996), vol. 15, pages 3782 - 3784, XP002235306 DOI: http://dx.doi.org/10.1021/om9603979 | [A] - JOHN. J. M. ET AL., "A highly active catalyst for the hydrogenation of amides to alcohols and amines", ANGEW. CHEM. INT. ED., (2011), vol. 50, pages 10377 - 10380, XP055016967 DOI: http://dx.doi.org/10.1002/anie.201103137 |