Title:
2-BENZYLIDENE HYDRAZINOADENOSINE COMPOUNDS HAVING A2A ADENOSINE RECEPTOR AGNOSTIC ACTIVITY
Document Type and Number:
WIPO Patent Application WO/2020/253872
Kind Code:
A1
Abstract:
2-Benzylidene hydrazinoadenosine compounds having A2A adenosine receptor agonistic activity, represented by a general formula (I) and pharmaceutical compositions containing the same. The compounds and compositions may act as A2A adenosine receptor agonists to serve as medicaments. (I)
Inventors:
ZHONG WU (CN)
ZHANG MIN (CN)
ZHOU XINBO (CN)
FAN SHIYONG (CN)
LI SONG (CN)
ZHANG MIN (CN)
ZHOU XINBO (CN)
FAN SHIYONG (CN)
LI SONG (CN)
Application Number:
PCT/CN2020/097442
Publication Date:
December 24, 2020
Filing Date:
June 22, 2020
Export Citation:
Assignee:
ACAD OF MILITARY MEDICAL SCIENCES (CN)
International Classes:
C07H19/16; A61K31/7076; A61P9/00; A61P17/00; A61P37/00
Foreign References:
| EP0567094A2 | 1993-10-27 | |||
| EP0567094A2 | 1993-10-27 | |||
| CN103221535A | 2013-07-24 | |||
| CN102014959A | 2011-04-13 | |||
| CN101437526A | 2009-05-20 | |||
| CN201910542124A | 2019-06-21 | |||
| CN200980117596A | 2009-03-10 | |||
| CN200580033215A | 2005-08-02 |
Other References:
ZHANG, M. ET AL.: "Design, Synthesis and Biological Evaluation of 2-hydrazinyladenosine Derivatives as A2A Adenosine Receptor Ligands", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 179, 24 June 2019 (2019-06-24), XP085772550, DOI: 20200910162659X
EI-TAYEB, A. ET AL.: "Synthesis and Structure-Activity Relationships of 2-hydrazinyladenosine Derivatives as A2A Adenosine Receptor Ligands", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 21, 27 November 2012 (2012-11-27), XP055767108, DOI: 20200910162510X
VIZIANO, M. ET AL.: "2-[N'-(3-Arylallylidene)hydrazino]adenosines Showing A2a Adenosine Agonist Properties and Vasodilation Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, 31 December 1995 (1995-12-31), XP055767113, DOI: 20200910162907X
NIIYA, K. ET AL.: "2-(N'-aralkylidenehydrazino)adenosines: Potent and Selective Coronary Vasodilators", JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, 31 December 1992 (1992-12-31), XP000918386, DOI: 20200910163115X
EI-TAYEB, A. ET AL.: "Synthesis and Structure-Activity Relationships of 2-hydrazinyladenosine Derivatives as A2A Adenosine Receptor Ligands", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 21, 27 November 2012 (2012-11-27), XP055767108, DOI: 20200911162806X
VIZIANO, M. ET AL.: "2-[N'-(3-Arylallylidene)hydrazino]adenosines Showing A2a Adenosine Agonist Properties and Vasodilation Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, 31 December 1995 (1995-12-31), XP055767113, DOI: 20200911162808X
NIIYA, K. ET AL.: "2-(N'-aralkylidenehydrazino)adenosines: Potent and Selective Coronary Vasodilators", JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, 31 December 1992 (1992-12-31), XP000918386, DOI: 20200911162811X
HUBER J D ET AL., TRENDS NEUROSCI, vol. 24, no. 12, 2001, pages 719 - 25
CARMAN AJ ET AL., J NEUROSCI, vol. 31, no. 37, 2011, pages 13272 - 80
SOHAIL MA ET AL., HEPATOLOGY, vol. 49, no. 1, 2009, pages 185 - 94
DE LERA RUIZ M ET AL., J MED CHEM, vol. 57, no. 9, 2014, pages 3623 - 50
VARANI K ET AL., FASEB J, vol. 24, no. 4, 2010, pages 1192 - 204
HASKO G, NAT REV DRUG DISCOV, vol. 7, no. 9, 2008, pages 759 - 70
AKKARI R ET AL., CURR TOP MED CHEM, vol. 6, no. 13, 2006, pages 1375 - 99
BOSCH MP ET AL., J MED CHEM, vol. 47, no. 16, 2004, pages 4041 - 53
MULLER C E ET AL., BIOCHIM BIOPHYS ACTA, vol. 1808, no. 5, 2011, pages 1290 - 308
RIVERA-OLIVER M, LIFE SCI, vol. 101, no. 1-2, 2014, pages 1 - 9
See also references of EP 3988559A4
EI-TAYEB, A. ET AL.: "Synthesis and Structure-Activity Relationships of 2-hydrazinyladenosine Derivatives as A2A Adenosine Receptor Ligands", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 21, 27 November 2012 (2012-11-27), XP055767108, DOI: 20200910162510X
VIZIANO, M. ET AL.: "2-[N'-(3-Arylallylidene)hydrazino]adenosines Showing A2a Adenosine Agonist Properties and Vasodilation Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, 31 December 1995 (1995-12-31), XP055767113, DOI: 20200910162907X
NIIYA, K. ET AL.: "2-(N'-aralkylidenehydrazino)adenosines: Potent and Selective Coronary Vasodilators", JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, 31 December 1992 (1992-12-31), XP000918386, DOI: 20200910163115X
EI-TAYEB, A. ET AL.: "Synthesis and Structure-Activity Relationships of 2-hydrazinyladenosine Derivatives as A2A Adenosine Receptor Ligands", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 21, 27 November 2012 (2012-11-27), XP055767108, DOI: 20200911162806X
VIZIANO, M. ET AL.: "2-[N'-(3-Arylallylidene)hydrazino]adenosines Showing A2a Adenosine Agonist Properties and Vasodilation Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, 31 December 1995 (1995-12-31), XP055767113, DOI: 20200911162808X
NIIYA, K. ET AL.: "2-(N'-aralkylidenehydrazino)adenosines: Potent and Selective Coronary Vasodilators", JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, 31 December 1992 (1992-12-31), XP000918386, DOI: 20200911162811X
HUBER J D ET AL., TRENDS NEUROSCI, vol. 24, no. 12, 2001, pages 719 - 25
CARMAN AJ ET AL., J NEUROSCI, vol. 31, no. 37, 2011, pages 13272 - 80
SOHAIL MA ET AL., HEPATOLOGY, vol. 49, no. 1, 2009, pages 185 - 94
DE LERA RUIZ M ET AL., J MED CHEM, vol. 57, no. 9, 2014, pages 3623 - 50
VARANI K ET AL., FASEB J, vol. 24, no. 4, 2010, pages 1192 - 204
HASKO G, NAT REV DRUG DISCOV, vol. 7, no. 9, 2008, pages 759 - 70
AKKARI R ET AL., CURR TOP MED CHEM, vol. 6, no. 13, 2006, pages 1375 - 99
BOSCH MP ET AL., J MED CHEM, vol. 47, no. 16, 2004, pages 4041 - 53
MULLER C E ET AL., BIOCHIM BIOPHYS ACTA, vol. 1808, no. 5, 2011, pages 1290 - 308
RIVERA-OLIVER M, LIFE SCI, vol. 101, no. 1-2, 2014, pages 1 - 9
See also references of EP 3988559A4
Attorney, Agent or Firm:
CCPIT PATENT AND TRADEMARK LAW OFFICE (CN)
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