Title:
MAGL INHIBITOR, PREPARATION METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/042911
Kind Code:
A1
Abstract:
The present invention relates to the field of medicines, and relates to a compound represented by formula (I) and acting as a MAGL inhibitor and a pharmaceutically acceptable salt thereof, a preparation method therefor, use thereof, and an intermediate for preparing same.
Inventors:
ZHANG GUIMIN (CN)
WANG JINXIN (CN)
YAO JINGCHUN (CN)
ZHAO GUIFANG (CN)
WANG JINXIN (CN)
YAO JINGCHUN (CN)
ZHAO GUIFANG (CN)
Application Number:
PCT/CN2020/104989
Publication Date:
March 11, 2021
Filing Date:
July 27, 2020
Export Citation:
Assignee:
LUNAN PHARMACEUTICAL GROUP CORP (CN)
International Classes:
C07D211/62; A61K31/445; A61P1/00; A61P1/02; A61P1/08; A61P1/14; A61P1/16; A61P3/04; A61P3/10; A61P9/00; A61P11/02; A61P13/08; A61P13/10; A61P13/12; A61P15/00; A61P17/00; A61P17/02; A61P17/10; A61P19/02; A61P25/00; A61P25/04; A61P25/08; A61P25/14; A61P25/16; A61P25/18; A61P25/20; A61P25/22; A61P25/24; A61P25/28; A61P25/32; A61P29/00; A61P31/12; A61P35/00; A61P35/02; A61P37/06; A61P37/08
Domestic Patent References:
| WO2012170098A2 | 2012-12-13 | |||
| WO2017049295A1 | 2017-03-23 |
Foreign References:
| CN109593089A | 2019-04-09 | |||
| CN101128427A | 2008-02-20 | |||
| CN105916841A | 2016-08-31 | |||
| US20180079756A1 | 2018-03-22 | |||
| CN109311868A | 2019-02-05 | |||
| US20160214951A1 | 2016-07-28 |
Other References:
ZHI ZHUOER, ZHANG WENTING, YAO JINGCHUN, SHANG YANGUO, HAO QINGJING, LIU ZHONG, REN YUSHAN, LI JIE, ZHANG GUIMIN, WANG JINXIN: "Discovery of Aryl Formyl Piperidine Derivatives as Potent, Reversible, and Selective Monoacylglycerol Lipase Inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 63, no. 11, 11 June 2020 (2020-06-11), pages 5783 - 5796, XP055788363, ISSN: 0022-2623, DOI: 10.1021/acs.jmedchem.9b02137
DATABASE Registry 20 June 2019 (2019-06-20), ..: "-4-Piperidinecarboxamide, N-(3-chlorophenyl)-1-(1H-indol-2-ylcarbonyl)-", XP055788395, retrieved from STN Database accession no. 2340481-37-8
DATABASE Registry 28 June 2019 (2019-06-28), ..: "-4-Piperidinecarboxamide, N-(3,5-dimethylphenyl)-1-(1H-indol-2-ylcarbonyl)-", XP055788407, retrieved from STN Database accession no. 2347870-36-2
DATABASE REGISTRY 24 June 2019 (2019-06-24), .: "4-Piperidinecarboxamide, 1-(1H-indol-2-ylcarbonyl)-N-(3-methoxyphenyl)", XP55788418, retrieved from STN Database accession no. 2344310-62-7
DATABASE REGISTRY 23 June 2019 (2019-06-23), .: "4-Piperidinecarboxamide, N-(3,4-dichlorophenyl)-1-(1H-indol-2-ylcarbonyl)", XP055788480, retrieved from STN Database accession no. 2343019-98-5
DATABASE REGISTRY 18 June 2019 (2019-06-18), . .: "4-Piperidinecarboxamide, N-(3,5-dichlorophenyl)-1-(1H-indol-2-ylcarbonyl)", XP055788475, retrieved from STN Database accession no. 2338189-38-9
DATABASE REGISTRY 22 April 2018 (2018-04-22), .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3- chlorophenyl)", XP055788467, retrieved from STN Database accession no. 2217201-40-4
DATABASE REGISTRY 22 April 2018 (2018-04-22), .: "4-Piperidinecarboxamide, N-(3,4-dichlorophenyl)-1-(3-methoxybenzoyl)", XP055789045, retrieved from STN Database accession no. 2217030-90-3
DATABASE REGISTRY 22 April 2018 (2018-04-22), .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3- methoxyphenyl)", XP055789054, retrieved from STN Database accession no. 2217274-23-0
DATABASE REGISTRY 22 April 2018 (2018-04-22), ..: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3,4- dichlorophenyl)", XP055789067, retrieved from STN Database accession no. 2217251-42-6
DATABASE REGISTRY .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3,5- dichlorophenyl)", XP055789075, retrieved from STN
DATABASE REGISTRY 17 April 2018 (2018-04-17), .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3,5- dimethylphenyl)", XP055788465, retrieved from STN Database accession no. 2214031-19-1
DATABASE REGISTRY 21 February 2018 (2018-02-21), "4-Piperidinecarboxamide, 1-[(5-fluoro-1H-indol-2-yl)carbonyl]-N-phenyl", XP055788462, retrieved from STN Database accession no. 2177530-54-8
DATABASE REGISTRY 12 September 2016 (2016-09-12), .: "4-Piperidinecarboxamide, 1-(3-methoxybenzoyl)-N-(2-methoxyphenyl)", XP055788443, retrieved from STN Database accession no. 1991951-96-2
DATABASE REGISTRY 8 September 2016 (2016-09-08), .: "4-Piperidinecarboxamide, N-(4-chlorophenyl)-1-(3-methoxybenzoyl)", XP055788504, retrieved from STN Database accession no. 1989422-30-1
DATABASE REGISTRY 29 August 2016 (2016-08-29), .: "4-Piperidinecarboxamide, N-(3-fluorophenyl)-1-(3-methoxybenzoyl)", XP055788513, retrieved from STN Database accession no. 1981837-69-7
DATABASE REGISTRY .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(3-methoxyphenyl)", XP055789081, retrieved from STN Database accession no. 905172-72-7
DATABASE REGISTRY 22 September 2014 (2014-09-22), .: "4-Piperidinecarboxamide, 1-(2-naphthalenylcarbonyl)-N-phenyl", XP055788526, retrieved from STN Database accession no. 1624146-19-5
DATABASE REGISTRY 22 September 2014 (2014-09-22), .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-phenyl", XP055789086, retrieved from STN Database accession no. 1624126-48-2
DATABASE REGISTRY 31 August 2011 (2011-08-31), .: "4-Piperidinecarboxamide, 1-(1H-indol-2-ylcarbonyl)-N-phenyl", XP055788530, retrieved from STN Database accession no. 1325844-20-9
DATABASE REGISTRY 18 May 2011 (2011-05-18), .: "4-Piperidinecarboxamide, 1-(2-hydroxybenzoyl)-N-(2-methoxyphenyl)", XP055788540, retrieved from STN Database accession no. 1296587-93-3
DATABASE REGISTRY 29 August 2006 (2006-08-29), .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(3,4-dichlorophenyl)", XP055788542, retrieved from STN Database accession no. 905172-26-1
DATABASE REGISTRY .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(3,5-dichlorophenyl)", XP055789098, retrieved from STN Database accession no. 905171-41-7
DATABASE REGISTRY 10 October 2005 (2005-10-10), .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(3-fluorophenyl)", XP055788548, retrieved from STN Database accession no. 864842-41-1
DATABASE REGISTRY .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(4-chlorophenyl)", XP055789111, retrieved from STN Database accession no. 864840-27-7
DATABASE REGISTRY 1 May 2003 (2003-05-01), .: "4-Piperidinecarboxamide, N-(3,5-dichlorophenyl)-1-(3-methoxybenzoyl)", XP055788552, retrieved from STN Database accession no. 508188-51-0
DATABASE REGISTRY ANONYMOUS: "4-Piperidinecarboxamide, N-(3-chlorophenyl)-1-(3-methoxybenzoyl)", XP055789116, retrieved from STN Database accession no. 508188-16-7
DATABASE REGISTRY 26 June 2002 (2002-06-26), .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(2-methoxyphenyl)", XP055788564, retrieved from STN Database accession no. 433952-89-7
DATABASE REGISTRY 9 February 2016 (2016-02-09), .: "4-Piperidinecarboxamide, 1-(3-methoxybenzoyl)-N-(3-methoxyphenyl)", XP055788575, retrieved from STN Database accession no. 1985280-62-3
DATABASE REGISTRY 31 October 2010 (2010-10-31), .: "4-Piperidinecarboxamide, N-(3-hydroxyphenyl)", XP055788569, retrieved from STN Database accession no. 1249010-19-2
DATABASE REGISTRY 7 June 2009 (2009-06-07), .: "4-Piperidinecarboxamide, N-(4-chloro-3-fluorophenyl)", XP055788580, retrieved from STN Database accession no. 1153189-42-4
DATABASE REGISTRY 23 April 2008 (2008-04-23), .: "4-Piperidinecarboxamide, N-(3-fluorophenyl)", XP55788587, retrieved from STN Database accession no. 1016532-14-1
DATABASE REGISTRY 23 April 2008 (2008-04-23), .: "4-Piperidinecarboxamide, N-(3-chlorophenyl)-", XP055788585, retrieved from STN Database accession no. 1016748-08-5
DATABASE REGISTRY 23 April 2008 (2008-04-23), .: "4-Piperidinecarboxamide, N-(3,5-dichlorophenyl)", XP055788591, retrieved from STN Database accession no. 1016530-58-7
CAREYSUNDBERG: "ADVANCED ORGANIC CHEMISTRY", vol. A, B, 2000, PLENUM PRESS
"VOGEL'S ENCYCLOPEDIA OF PRACTICAL ORGANIC CHEMISTRY", 1991, LONGMAN SCIENTIFIC AND TECHNICAL LTD., pages: 809 - 816
HELLER, ACC. CHEM. RES., vol. 23, 1990, pages 128
GOODMANGILMAN: "The Pharmacological Basis of Therapeutics", 1985, MACK PUBLISHING COMPANY, pages: 1418
JOURNAL OF PHARMACEUTICAL SCIENCE, vol. 66, 1977, pages 2
PORSOLT R DLE PICHON MJALFRE M: "Depression: a new animal model sensitive to antidepressant treatments", NATURE, vol. 266, no. 5604, 1977, pages 730 - 732
DATABASE Registry 20 June 2019 (2019-06-20), ..: "-4-Piperidinecarboxamide, N-(3-chlorophenyl)-1-(1H-indol-2-ylcarbonyl)-", XP055788395, retrieved from STN Database accession no. 2340481-37-8
DATABASE Registry 28 June 2019 (2019-06-28), ..: "-4-Piperidinecarboxamide, N-(3,5-dimethylphenyl)-1-(1H-indol-2-ylcarbonyl)-", XP055788407, retrieved from STN Database accession no. 2347870-36-2
DATABASE REGISTRY 24 June 2019 (2019-06-24), .: "4-Piperidinecarboxamide, 1-(1H-indol-2-ylcarbonyl)-N-(3-methoxyphenyl)", XP55788418, retrieved from STN Database accession no. 2344310-62-7
DATABASE REGISTRY 23 June 2019 (2019-06-23), .: "4-Piperidinecarboxamide, N-(3,4-dichlorophenyl)-1-(1H-indol-2-ylcarbonyl)", XP055788480, retrieved from STN Database accession no. 2343019-98-5
DATABASE REGISTRY 18 June 2019 (2019-06-18), . .: "4-Piperidinecarboxamide, N-(3,5-dichlorophenyl)-1-(1H-indol-2-ylcarbonyl)", XP055788475, retrieved from STN Database accession no. 2338189-38-9
DATABASE REGISTRY 22 April 2018 (2018-04-22), .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3- chlorophenyl)", XP055788467, retrieved from STN Database accession no. 2217201-40-4
DATABASE REGISTRY 22 April 2018 (2018-04-22), .: "4-Piperidinecarboxamide, N-(3,4-dichlorophenyl)-1-(3-methoxybenzoyl)", XP055789045, retrieved from STN Database accession no. 2217030-90-3
DATABASE REGISTRY 22 April 2018 (2018-04-22), .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3- methoxyphenyl)", XP055789054, retrieved from STN Database accession no. 2217274-23-0
DATABASE REGISTRY 22 April 2018 (2018-04-22), ..: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3,4- dichlorophenyl)", XP055789067, retrieved from STN Database accession no. 2217251-42-6
DATABASE REGISTRY .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3,5- dichlorophenyl)", XP055789075, retrieved from STN
DATABASE REGISTRY 17 April 2018 (2018-04-17), .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-(3,5- dimethylphenyl)", XP055788465, retrieved from STN Database accession no. 2214031-19-1
DATABASE REGISTRY 21 February 2018 (2018-02-21), "4-Piperidinecarboxamide, 1-[(5-fluoro-1H-indol-2-yl)carbonyl]-N-phenyl", XP055788462, retrieved from STN Database accession no. 2177530-54-8
DATABASE REGISTRY 12 September 2016 (2016-09-12), .: "4-Piperidinecarboxamide, 1-(3-methoxybenzoyl)-N-(2-methoxyphenyl)", XP055788443, retrieved from STN Database accession no. 1991951-96-2
DATABASE REGISTRY 8 September 2016 (2016-09-08), .: "4-Piperidinecarboxamide, N-(4-chlorophenyl)-1-(3-methoxybenzoyl)", XP055788504, retrieved from STN Database accession no. 1989422-30-1
DATABASE REGISTRY 29 August 2016 (2016-08-29), .: "4-Piperidinecarboxamide, N-(3-fluorophenyl)-1-(3-methoxybenzoyl)", XP055788513, retrieved from STN Database accession no. 1981837-69-7
DATABASE REGISTRY .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(3-methoxyphenyl)", XP055789081, retrieved from STN Database accession no. 905172-72-7
DATABASE REGISTRY 22 September 2014 (2014-09-22), .: "4-Piperidinecarboxamide, 1-(2-naphthalenylcarbonyl)-N-phenyl", XP055788526, retrieved from STN Database accession no. 1624146-19-5
DATABASE REGISTRY 22 September 2014 (2014-09-22), .: "4-Piperidinecarboxamide, 1-([1,1'-biphenyl]-4-ylcarbonyl)-N-phenyl", XP055789086, retrieved from STN Database accession no. 1624126-48-2
DATABASE REGISTRY 31 August 2011 (2011-08-31), .: "4-Piperidinecarboxamide, 1-(1H-indol-2-ylcarbonyl)-N-phenyl", XP055788530, retrieved from STN Database accession no. 1325844-20-9
DATABASE REGISTRY 18 May 2011 (2011-05-18), .: "4-Piperidinecarboxamide, 1-(2-hydroxybenzoyl)-N-(2-methoxyphenyl)", XP055788540, retrieved from STN Database accession no. 1296587-93-3
DATABASE REGISTRY 29 August 2006 (2006-08-29), .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(3,4-dichlorophenyl)", XP055788542, retrieved from STN Database accession no. 905172-26-1
DATABASE REGISTRY .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(3,5-dichlorophenyl)", XP055789098, retrieved from STN Database accession no. 905171-41-7
DATABASE REGISTRY 10 October 2005 (2005-10-10), .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(3-fluorophenyl)", XP055788548, retrieved from STN Database accession no. 864842-41-1
DATABASE REGISTRY .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(4-chlorophenyl)", XP055789111, retrieved from STN Database accession no. 864840-27-7
DATABASE REGISTRY 1 May 2003 (2003-05-01), .: "4-Piperidinecarboxamide, N-(3,5-dichlorophenyl)-1-(3-methoxybenzoyl)", XP055788552, retrieved from STN Database accession no. 508188-51-0
DATABASE REGISTRY ANONYMOUS: "4-Piperidinecarboxamide, N-(3-chlorophenyl)-1-(3-methoxybenzoyl)", XP055789116, retrieved from STN Database accession no. 508188-16-7
DATABASE REGISTRY 26 June 2002 (2002-06-26), .: "4-Piperidinecarboxamide, 1-(4-chlorobenzoyl)-N-(2-methoxyphenyl)", XP055788564, retrieved from STN Database accession no. 433952-89-7
DATABASE REGISTRY 9 February 2016 (2016-02-09), .: "4-Piperidinecarboxamide, 1-(3-methoxybenzoyl)-N-(3-methoxyphenyl)", XP055788575, retrieved from STN Database accession no. 1985280-62-3
DATABASE REGISTRY 31 October 2010 (2010-10-31), .: "4-Piperidinecarboxamide, N-(3-hydroxyphenyl)", XP055788569, retrieved from STN Database accession no. 1249010-19-2
DATABASE REGISTRY 7 June 2009 (2009-06-07), .: "4-Piperidinecarboxamide, N-(4-chloro-3-fluorophenyl)", XP055788580, retrieved from STN Database accession no. 1153189-42-4
DATABASE REGISTRY 23 April 2008 (2008-04-23), .: "4-Piperidinecarboxamide, N-(3-fluorophenyl)", XP55788587, retrieved from STN Database accession no. 1016532-14-1
DATABASE REGISTRY 23 April 2008 (2008-04-23), .: "4-Piperidinecarboxamide, N-(3-chlorophenyl)-", XP055788585, retrieved from STN Database accession no. 1016748-08-5
DATABASE REGISTRY 23 April 2008 (2008-04-23), .: "4-Piperidinecarboxamide, N-(3,5-dichlorophenyl)", XP055788591, retrieved from STN Database accession no. 1016530-58-7
CAREYSUNDBERG: "ADVANCED ORGANIC CHEMISTRY", vol. A, B, 2000, PLENUM PRESS
"VOGEL'S ENCYCLOPEDIA OF PRACTICAL ORGANIC CHEMISTRY", 1991, LONGMAN SCIENTIFIC AND TECHNICAL LTD., pages: 809 - 816
HELLER, ACC. CHEM. RES., vol. 23, 1990, pages 128
GOODMANGILMAN: "The Pharmacological Basis of Therapeutics", 1985, MACK PUBLISHING COMPANY, pages: 1418
JOURNAL OF PHARMACEUTICAL SCIENCE, vol. 66, 1977, pages 2
PORSOLT R DLE PICHON MJALFRE M: "Depression: a new animal model sensitive to antidepressant treatments", NATURE, vol. 266, no. 5604, 1977, pages 730 - 732
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