Title:
NECROSIS INHIBITORS
Document Type and Number:
WIPO Patent Application WO/2016/101885
Kind Code:
A1
Abstract:
The invention provides amides that inhibit cellular necrosis and/or human receptor interacting protein 1 kinase (RIP1), including corresponding sulfonamides, and pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.
Inventors:
ZHANG ZHIYUAN (CN)
WANG XIAODONG (CN)
LEI XIAOGUANG (CN)
SU YANING (CN)
HE SUDAN (CN)
RUAN HANYING (CN)
SUN LIMING (CN)
WANG XIAODONG (CN)
LEI XIAOGUANG (CN)
SU YANING (CN)
HE SUDAN (CN)
RUAN HANYING (CN)
SUN LIMING (CN)
Application Number:
PCT/CN2015/098367
Publication Date:
June 30, 2016
Filing Date:
December 23, 2015
Export Citation:
Assignee:
NAT INST OF BIOLOG SCIENCES BEIJING (CN)
International Classes:
C07C233/05; A61K31/16; C07C235/06; C07C275/06; C07C311/03; C07D213/06; C07D215/12; C07D233/64; C07D277/20; C07D333/06; A61P31/00
Domestic Patent References:
| WO2008116620A1 | 2008-10-02 | |||
| WO2014160185A2 | 2014-10-02 | |||
| WO2012125544A2 | 2012-09-20 | |||
| WO2009023272A1 | 2009-02-19 | |||
| WO2010075290A1 | 2010-07-01 | |||
| WO2010075561A1 | 2010-07-01 | |||
| WO2012125544A2 | 2012-09-20 |
Foreign References:
| US20150266834A1 | 2015-09-24 | |||
| US20100216787A1 | 2010-08-26 | |||
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| CN102617259A | 2012-08-01 | |||
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| US4957533A | 1990-09-18 | |||
| CN102503860A | 2012-06-20 | |||
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| US8278344B2 | 2012-10-02 | |||
| US20120122889A1 | 2012-05-17 | |||
| US20090099242A1 | 2009-04-16 | |||
| US20100317701A1 | 2010-12-16 | |||
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Other References:
ZHANG, MEIHUI ET AL.: "Synthesis and activity of tetrapeptidic HTLV-I protease inhibitors possessing different P3-cap moieties", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 16, no. 10, 31 December 2008 (2008-12-31), XP022673161
TSUNODA, TETSUTO ET AL.: "An efficient method for hydrolysis of N-monosubstituted amides. Utilization of intramolecular nitrogen-oxygen acyl migration in hydroxypivalimides", TETRAHEDRON, vol. 47, no. 24, 31 December 1991 (1991-12-31), pages 3928, XP008144044
ZHOU, LIHONG ET AL.: "Palladium-Catalyzed beta-Acyloxylation of Simple Amide via sp3 C-H Activation", ORGANIC LETTERS, vol. 16, no. 2, 27 December 2013 (2013-12-27), XP055393823
BIRCHALL, J. M. ET AL.: "Polyfluoroarenes. IV. 2, 3, 4, 5, 6-Pentafluorotoluene and related compounds", JOURNAL OF THE CHEMICAL SOCIETY, 31 December 1961 (1961-12-31), XP002187941
KHALAFI-NEZHAD ALI ET AL.: "Silica boron-sulfuric acid nanoparticles (SBSANs): preparation, characterization and their catalytic application in the Ritter reaction for the synthesis of amide derivatives", JOURNAL OF MATERIALS CHEMISTRY, vol. 21, no. 34, 31 December 2011 (2011-12-31), XP055393828
ZHU, MINGWEN ET AL.: "Aerobic Oxidative Amidation of Aromatic and Cinnamic Aldehydes with Secondary Amines by CuI/2-Pyridonate Catalytic System", JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 20, 25 September 2012 (2012-09-25), XP055102501
GEFFKEN, DETLEF ET AL.: "The reaction of 2, 2-disubstituted 3-hydroxypropionic acids with N- monosubstituted hydroxylammonium chlorides and dicyclohexylcarbodiimide", ARCHIV DER PHARMAZIE, vol. 309, no. 5, 31 December 1976 (1976-12-31), XP000951547
KRETOV, A. E. ET AL.: "N-Arylsulfonamide derivatives of monoethanolamine", ZHURNAL OBSHCHEI KHIMII, vol. 29, 31 December 1959 (1959-12-31), XP008185261
VELAVAN, A. ET AL.: "Unsymmetrical tetrasubstituted ureas from tertiary carbamoylimidazole: activation by AlMe3", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 10, no. 31, 31 December 2012 (2012-12-31), pages 6423, XP055269907, DOI: doi:10.1039/c2ob25412c
VANDI, ANTONIO ET AL.: "Syntheses and properties of some N-substituted sulfamides", JOURNAL OF ORGANIC CHEMISTRY, vol. 26, 1 May 1961 (1961-05-01), XP002474071, DOI: doi:10.1021/jo01063a039
TERAUCHI, HIROMI ET AL.: "Reaction of N-haloamide. XVI. Reaction of N, N- dichlorophenylacetamide with aliphatic secondary amines", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 20, no. 11, 31 December 1972 (1972-12-31), pages 2478, XP003032463
S OMASEKHARA, S. ET AL.: "Chlorobenzenesulfonamides & some related benzothiadiazines", INDIAN JOURNAL OF CHEMISTRY, vol. 6, no. 1, 31 January 1968 (1968-01-31), XP001012823
SAHU, BASANT ET AL.: "UV spectral study of some N-acyl derivatives of N-benzyl hydroxylamine", ACTA CIENCIA INDICA, CHEMISTRY, vol. 16 C, no. 2, 31 December 1990 (1990-12-31), pages 3628, XP008185262
HOLLER ET AL., NAT IMMUNOL, vol. 1, 2000, pages 489 - 495
DEGTEREV ET AL., NAT CHEM BIOL, vol. 4, 2008, pages 313 - 321
DUNAI ET AL., PATHOL. ONCOL. RES.: POR, vol. 17, no. 4, December 2011 (2011-12-01), pages 791 - 800
DEGTEREV ET AL., NAT CHEM BIOL, vol. 1, 2005, pages 112 - 119
"The Practice of Medicinal Chemistry", 1996, ACADEMIC PRESS, pages: 203
"Remington's Pharmaceutical Science", 1991, MACK PUBLISHING CO
See also references of EP 3224237A4
TSUNODA, TETSUTO ET AL.: "An efficient method for hydrolysis of N-monosubstituted amides. Utilization of intramolecular nitrogen-oxygen acyl migration in hydroxypivalimides", TETRAHEDRON, vol. 47, no. 24, 31 December 1991 (1991-12-31), pages 3928, XP008144044
ZHOU, LIHONG ET AL.: "Palladium-Catalyzed beta-Acyloxylation of Simple Amide via sp3 C-H Activation", ORGANIC LETTERS, vol. 16, no. 2, 27 December 2013 (2013-12-27), XP055393823
BIRCHALL, J. M. ET AL.: "Polyfluoroarenes. IV. 2, 3, 4, 5, 6-Pentafluorotoluene and related compounds", JOURNAL OF THE CHEMICAL SOCIETY, 31 December 1961 (1961-12-31), XP002187941
KHALAFI-NEZHAD ALI ET AL.: "Silica boron-sulfuric acid nanoparticles (SBSANs): preparation, characterization and their catalytic application in the Ritter reaction for the synthesis of amide derivatives", JOURNAL OF MATERIALS CHEMISTRY, vol. 21, no. 34, 31 December 2011 (2011-12-31), XP055393828
ZHU, MINGWEN ET AL.: "Aerobic Oxidative Amidation of Aromatic and Cinnamic Aldehydes with Secondary Amines by CuI/2-Pyridonate Catalytic System", JOURNAL OF ORGANIC CHEMISTRY, vol. 77, no. 20, 25 September 2012 (2012-09-25), XP055102501
GEFFKEN, DETLEF ET AL.: "The reaction of 2, 2-disubstituted 3-hydroxypropionic acids with N- monosubstituted hydroxylammonium chlorides and dicyclohexylcarbodiimide", ARCHIV DER PHARMAZIE, vol. 309, no. 5, 31 December 1976 (1976-12-31), XP000951547
KRETOV, A. E. ET AL.: "N-Arylsulfonamide derivatives of monoethanolamine", ZHURNAL OBSHCHEI KHIMII, vol. 29, 31 December 1959 (1959-12-31), XP008185261
VELAVAN, A. ET AL.: "Unsymmetrical tetrasubstituted ureas from tertiary carbamoylimidazole: activation by AlMe3", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 10, no. 31, 31 December 2012 (2012-12-31), pages 6423, XP055269907, DOI: doi:10.1039/c2ob25412c
VANDI, ANTONIO ET AL.: "Syntheses and properties of some N-substituted sulfamides", JOURNAL OF ORGANIC CHEMISTRY, vol. 26, 1 May 1961 (1961-05-01), XP002474071, DOI: doi:10.1021/jo01063a039
TERAUCHI, HIROMI ET AL.: "Reaction of N-haloamide. XVI. Reaction of N, N- dichlorophenylacetamide with aliphatic secondary amines", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 20, no. 11, 31 December 1972 (1972-12-31), pages 2478, XP003032463
S OMASEKHARA, S. ET AL.: "Chlorobenzenesulfonamides & some related benzothiadiazines", INDIAN JOURNAL OF CHEMISTRY, vol. 6, no. 1, 31 January 1968 (1968-01-31), XP001012823
SAHU, BASANT ET AL.: "UV spectral study of some N-acyl derivatives of N-benzyl hydroxylamine", ACTA CIENCIA INDICA, CHEMISTRY, vol. 16 C, no. 2, 31 December 1990 (1990-12-31), pages 3628, XP008185262
HOLLER ET AL., NAT IMMUNOL, vol. 1, 2000, pages 489 - 495
DEGTEREV ET AL., NAT CHEM BIOL, vol. 4, 2008, pages 313 - 321
DUNAI ET AL., PATHOL. ONCOL. RES.: POR, vol. 17, no. 4, December 2011 (2011-12-01), pages 791 - 800
DEGTEREV ET AL., NAT CHEM BIOL, vol. 1, 2005, pages 112 - 119
"The Practice of Medicinal Chemistry", 1996, ACADEMIC PRESS, pages: 203
"Remington's Pharmaceutical Science", 1991, MACK PUBLISHING CO
See also references of EP 3224237A4
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