Title:
METHOD FOR PREPARARING HETEROCYCLIC COMPOUND AND SALTS THEREOF
Document Type and Number:
WIPO Patent Application WO/2020/056553
Kind Code:
A1
Abstract:
The invention belongs to the field of organic chemistry, and particularly relates to a method for preparing a heterocyclic compound represented by formula I and salts thereof. Compared with the prior art, the invention avoids the use of cyanide, which is a highly toxic substance, and leaves no residual cyano group ion in reaction products and reaction waste, thereby greatly reducing the environmental burden. Moreover, the raw materials of the reaction in the invention have a low cost, a simple preparation method, a high yield, and are suitable for mass production. In addition, the inventors unexpectedly discovered that by using the method of Scheme 4, such as using a reducing agent and reacting under acidic conditions, the compound VIII can be reacted in one step and achieve deprotection, alkylation, and cyano group ion reduction simultaneously to obtain a target product. The disadvantages of the prior art that require multi-step reactions are thus greatly reduced.
Inventors:
CAI YAN (CN)
YANG SHAOQIANG (CN)
WU JIAPENG (CN)
LI HUAIXIN (CN)
ZHOU GUANG (CN)
XU BENQUAN (CN)
YANG SHAOQIANG (CN)
WU JIAPENG (CN)
LI HUAIXIN (CN)
ZHOU GUANG (CN)
XU BENQUAN (CN)
Application Number:
PCT/CN2018/105997
Publication Date:
March 26, 2020
Filing Date:
September 17, 2018
Export Citation:
Assignee:
BTC PHARMACEUTICAL CO LTD (CN)
UNIV NANKAI (CN)
UNIV NANKAI (CN)
International Classes:
C07D309/08; C07D205/04; C07D307/04
Domestic Patent References:
| WO2015095258A1 | 2015-06-25 | |||
| WO2011051282A1 | 2011-05-05 | |||
| WO2018005678A1 | 2018-01-04 | |||
| WO2017115329A1 | 2017-07-06 | |||
| WO2013052394A1 | 2013-04-11 |
Foreign References:
| CN103958477A | 2014-07-30 | |||
| CN105992765A | 2016-10-05 | |||
| US5646167A | 1997-07-08 | |||
| US3655692A | 1972-04-11 | |||
| CN104245671A | 2014-12-24 | |||
| CN102803235A | 2012-11-28 |
Other References:
YANG, D. ET AL.: "Serotoninergic properties of new conformationaily restricted benzamides", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 31, no. 3, 31 December 1996 (1996-12-31), pages 231 - 239, XP004040111, DOI: 10.1016/0223-5234(96)89139-2
SUMMA, V. ET AL.: "Discovery of Raltegravir, a Potent, Selective Orally Bioavailable HIV- Integrase Inhibitor for the Treatment of HIV-AIDS Infection", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 18, 9 March 2008 (2008-03-09), pages 5843 - 5855, XP002615638
DATABASE Registry 20 June 2016 (2016-06-20), Database accession no. 1935017-85-8
DATABASE Registry 30 April 2007 (2007-04-30), Database accession no. 933700-99-3
DATABASE Registry 8 June 2009 (2009-06-08), Database accession no. 1153971-30-2
DATABASE Registry 3 June 2015 (2015-06-03), Database accession no. 1782565-06-3
DATABASE Registry 15 June 2015 (2015-06-15), Database accession no. 1780498-07-8
DATABASE Registry 18 June 2015 (2015-06-18), Database accession no. 1783662-71-4
DATABASE Registry 30 April 2007 (2007-04-30), Database accession no. 933700-87-9
DATABASE Registry 17 June 2009 (2009-06-17), Database accession no. 1158792-81-4
DATABASE Registry 1 July 2010 (2010-07-01), Database accession no. 1228950-00-2
DATABASE Registry 17 January 2014 (2014-01-17), Database accession no. 1523606-33-8
DATABASE Registry 26 March 2018 (2018-03-26), Database accession no. 2199214-48-5
DATABASE Registry 2 November 2016 (2016-11-02), Database accession no. 2023809-00-7
DATABASE Registry 31 October 2016 (2016-10-31), Database accession no. 2021752-76-9
DATABASE Registry 3 October 2016 (2016-10-03), Database accession no. 2004393-93-3
DATABASE Registry 20 September 2016 (2016-09-20), Database accession no. 1996201-33-2
DATABASE Registry 26 February 2016 (2016-02-26), Database accession no. 1874677-59-4
DATABASE Registry 11 February 2016 (2016-02-11), Database accession no. 1864445-50-0
DATABASE Registry 11 February 2016 (2016-02-11), Database accession no. 1864215-72-4
DATABASE Registry 1 February 2016 (2016-02-01), Database accession no. 1856606-72-8
DATABASE Registry 21 January 2016 (2016-01-21), Database accession no. 1850376-56-5
DATABASE Registry 11 February 2010 (2010-02-11), Database accession no. 1205751-20-7
DATABASE Registry 11 February 2010 (2010-02-11), Database accession no. 1205749-53-6
DATABASE Registry 11 February 2010 (2010-02-11), Database accession no. 1205749-05-8
DATABASE Registry 11 February 2010 (2010-02-11), Database accession no. 1205749-01-4
DATABASE Registry 21 June 2016 (2016-06-21), Database accession no. 1935950-89-2
DATABASE Registry 27 January 2014 (2014-01-27), Database accession no. 1531313-58-2
DATABASE Registry 31 December 2013 (2013-12-31), Database accession no. 1507743-86-3
DATABASE Registry 28 June 2007 (2007-06-28), Database accession no. 939776-24-6
DATABASE Registry 16 November 1984 (1984-11-16), Database accession no. 50289-05-9
DATABASE Registry 11 November 2016 (2016-11-11), Database accession no. 2029755-73-3
DATABASE Registry 10 November 2016 (2016-11-10), Database accession no. 2028431-19-6
DATABASE Registry 2 November 2016 (2016-11-02), Database accession no. 2023269-53-4
DATABASE Registry 31 October 2016 (2016-10-31), Database accession no. 2021991-38-6
DATABASE Registry 31 October 2016 (2016-10-31), Database accession no. 2021682-44-8
DATABASE Registry 16 October 2016 (2016-10-16), Database accession no. 2012738-80-4
DATABASE Registry 3 October 2016 (2016-10-03), Database accession no. 2004666-75-3
DATABASE Registry 26 September 2016 (2016-09-26), Database accession no. 1999576-05-4
SUMMA, V. ET AL.: "Discovery of Raltegravir, a Potent, Selective Orally Bioavailable HIV- Integrase Inhibitor for the Treatment of HIV-AIDS Infection", JOURNAL OF MEDICINAL CHEMISTRY, vol. 51, no. 18, 9 March 2008 (2008-03-09), pages 5843 - 5855, XP002615638
DATABASE Registry 20 June 2016 (2016-06-20), Database accession no. 1935017-85-8
DATABASE Registry 30 April 2007 (2007-04-30), Database accession no. 933700-99-3
DATABASE Registry 8 June 2009 (2009-06-08), Database accession no. 1153971-30-2
DATABASE Registry 3 June 2015 (2015-06-03), Database accession no. 1782565-06-3
DATABASE Registry 15 June 2015 (2015-06-15), Database accession no. 1780498-07-8
DATABASE Registry 18 June 2015 (2015-06-18), Database accession no. 1783662-71-4
DATABASE Registry 30 April 2007 (2007-04-30), Database accession no. 933700-87-9
DATABASE Registry 17 June 2009 (2009-06-17), Database accession no. 1158792-81-4
DATABASE Registry 1 July 2010 (2010-07-01), Database accession no. 1228950-00-2
DATABASE Registry 17 January 2014 (2014-01-17), Database accession no. 1523606-33-8
DATABASE Registry 26 March 2018 (2018-03-26), Database accession no. 2199214-48-5
DATABASE Registry 2 November 2016 (2016-11-02), Database accession no. 2023809-00-7
DATABASE Registry 31 October 2016 (2016-10-31), Database accession no. 2021752-76-9
DATABASE Registry 3 October 2016 (2016-10-03), Database accession no. 2004393-93-3
DATABASE Registry 20 September 2016 (2016-09-20), Database accession no. 1996201-33-2
DATABASE Registry 26 February 2016 (2016-02-26), Database accession no. 1874677-59-4
DATABASE Registry 11 February 2016 (2016-02-11), Database accession no. 1864445-50-0
DATABASE Registry 11 February 2016 (2016-02-11), Database accession no. 1864215-72-4
DATABASE Registry 1 February 2016 (2016-02-01), Database accession no. 1856606-72-8
DATABASE Registry 21 January 2016 (2016-01-21), Database accession no. 1850376-56-5
DATABASE Registry 11 February 2010 (2010-02-11), Database accession no. 1205751-20-7
DATABASE Registry 11 February 2010 (2010-02-11), Database accession no. 1205749-53-6
DATABASE Registry 11 February 2010 (2010-02-11), Database accession no. 1205749-05-8
DATABASE Registry 11 February 2010 (2010-02-11), Database accession no. 1205749-01-4
DATABASE Registry 21 June 2016 (2016-06-21), Database accession no. 1935950-89-2
DATABASE Registry 27 January 2014 (2014-01-27), Database accession no. 1531313-58-2
DATABASE Registry 31 December 2013 (2013-12-31), Database accession no. 1507743-86-3
DATABASE Registry 28 June 2007 (2007-06-28), Database accession no. 939776-24-6
DATABASE Registry 16 November 1984 (1984-11-16), Database accession no. 50289-05-9
DATABASE Registry 11 November 2016 (2016-11-11), Database accession no. 2029755-73-3
DATABASE Registry 10 November 2016 (2016-11-10), Database accession no. 2028431-19-6
DATABASE Registry 2 November 2016 (2016-11-02), Database accession no. 2023269-53-4
DATABASE Registry 31 October 2016 (2016-10-31), Database accession no. 2021991-38-6
DATABASE Registry 31 October 2016 (2016-10-31), Database accession no. 2021682-44-8
DATABASE Registry 16 October 2016 (2016-10-16), Database accession no. 2012738-80-4
DATABASE Registry 3 October 2016 (2016-10-03), Database accession no. 2004666-75-3
DATABASE Registry 26 September 2016 (2016-09-26), Database accession no. 1999576-05-4
Attorney, Agent or Firm:
BEIJING ORIGINTELLIGENCE IP LAW FIRM (CN)
Download PDF:
Previous Patent: APPARATUS, METHOD AND COMPUTER PROGRAM
Next Patent: FEEDBACK TIMING DETERMINATION METHOD, TERMINAL DEVICE, AND NETWORK DEVICE
Next Patent: FEEDBACK TIMING DETERMINATION METHOD, TERMINAL DEVICE, AND NETWORK DEVICE