Title:
ESTER NITRATES DERIVATIVES OF AROMATIC ALDEHYDES WITH MULTIPLE PHARMALOGIC PROPERTIES TO TREAT SICKLE CELL DISEASE
Document Type and Number:
WIPO Patent Application WO/2015/027067
Kind Code:
A3
Abstract:
The invention provides new aromatic aldehyde compounds that have greater potency in increasing the affinity of Hb for oxygen, greater potency for preventing sickling, and additional pharmacologic properties that ameliorate other symptoms of SCD. The invention further provides methods for treating SCD by providing a subject having SCD with a compound according to the invention.
Inventors:
SAFO MARTIN (US)
VENITZ JURGEN (US)
DANSO-DANQUAH RICHMOND (US)
DESPANDE TANVI (US)
ZHANG YAN (US)
VENITZ JURGEN (US)
DANSO-DANQUAH RICHMOND (US)
DESPANDE TANVI (US)
ZHANG YAN (US)
Application Number:
PCT/US2014/052099
Publication Date:
May 07, 2015
Filing Date:
August 21, 2014
Export Citation:
Assignee:
UNIV VIRGINIA COMMONWEALTH (US)
International Classes:
C07D213/30; A61K31/11; A61K31/115; A61K31/44; C07C47/54; C07C47/575
Domestic Patent References:
| WO2013102142A1 | 2013-07-04 | |||
| WO2004050030A2 | 2004-06-17 | |||
| WO2014141175A1 | 2014-09-18 | |||
| WO2014021281A1 | 2014-02-06 | |||
| WO2013059437A1 | 2013-04-25 | |||
| WO2012076435A1 | 2012-06-14 | |||
| WO2012037782A1 | 2012-03-29 | |||
| WO2011093524A1 | 2011-08-04 | |||
| WO2010029300A1 | 2010-03-18 | |||
| WO2009077357A1 | 2009-06-25 | |||
| WO2008142706A2 | 2008-11-27 | |||
| WO2005047249A1 | 2005-05-26 | |||
| WO2005037836A2 | 2005-04-28 | |||
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Other References:
NNAMANI, IJEOMA N. ET AL: "Pyridyl derivatives of benzaldehyde as potential antisickling agents", CHEMISTRY & BIODIVERSITY, vol. 5, no. 9, 2008, pages 1762 - 1769, XP002732217, DOI: 10.1002/CBDV.200890165
OKPALA, IHEANYI: "Investigational agents for sickle cell disease", EXPERT OPINION ON INVESTIGATIONAL DRUGS, vol. 15, no. 8, 2006, pages 833 - 842, XP002732218, DOI: 10.1517/13543784.15.8.833
OSHEIZA Y. ABDULMALIK ET AL: "In Vitro Antisickling Effects of Novel Pyridyl Derivatives with Enhanced Potency", BLOOD, vol. 106, no. 11, 16 November 2005 (2005-11-16) - 13 December 2005 (2005-12-13), US, pages 666a, XP055151739, ISSN: 0006-4971
MILLER M R ET AL: "Recent developments in nitric oxide donor drugs", BRITISH JOURNAL OF PHARMACOLOGY, vol. 151, no. 3, 1 June 2007 (2007-06-01), NATURE PUBLISHING GROUP, BASINGSTOKE, HANTS; GB, pages 305 - 321, XP002520652, ISSN: 0007-1188, [retrieved on 20070402], DOI: 10.1038/SJ.BJP.0707224
MACK, A. KYLE ET AL: "Sickle cell disease and nitric oxide: A paradigm shift?", INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, vol. 38, 2006, pages 1237 - 1243, XP002732219, DOI: 10.1016/J.BIOCEL.2006.01.010
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; BUSCATO, ESTELLA ET AL: "Structure-activity relationship and in vitro pharmacological evaluation of imidazo[1,2-a]pyridine-based inhibitors of 5-LO", XP002732220, retrieved from STN Database accession no. 2013:785255
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; RUDENKO, M. G. ET AL: "Synthesis and conversions of some p- and p,p'-derivatives of diphenyl oxide", XP002732221, retrieved from STN Database accession no. 1965:423848
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1997, OOTSUKA, SHUNICHI ET AL: "Preparation of .alpha.-hydroxyphenylacetic acid derivatives as agricultural bactericides", XP002732222, retrieved from STN Database accession no. 1997:371871
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KITAJIMA, HIROSHI ET AL: "Preparation of 3-Aromatic-substituted propionic acid or acrylic acid derivatives as antidiabetics", XP002732223, retrieved from STN Database accession no. 2000:873308
PATEL, NAVIN B. ET AL: "Design and synthesis of new imidazolinone derivatives as potential antifungal agents", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 48, 2011, pages 373 - 380, XP002732224, DOI: 10.1002/JHET.588
TANIS, STEVEN P. ET AL: "Synthesis and Biological Activity of Metabolites of the Antidiabetic, Antihyperglycemic Agent Pioglitazone", JOURNAL OF MEDICINAL CHEMISTRY, vol. 39, no. 26, 1996, pages 5053 - 5063, XP002732225, DOI: 10.1021/JM9605694
MOMOSE, YU ET AL: "Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 39, no. 6, 1991, pages 1440 - 1445, XP002732226, DOI: 10.1248/CPB.39.1440
CROWDER, J. R. ET AL: "Bisbenzylisoquinolines. IV. The preparation of diarylethers from diaryliodonium salts", JOURNAL OF THE CHEMICAL SOCIETY, vol. sept., 1963, pages 4578 - 4585, XP002732227, DOI: 10.1039/JR9630004578
PROFFT, E. ET AL: "2- and 6-substituted 4-methylpyrimidines", ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESELLSCHAFT, vol. 295, 1962, pages 649 - 662, XP002732228
BUU-HOI, NG. PH. ET AL: "Thiosemicarbazones and 4-oxo-2-thiazolin-2-ylhydrazones", JOURNAL OF THE CHEMICAL SOCIETY, 1956, pages 713 - 716, XP002732229
BUU-HOI, NG. PH. ET AL: "Some new tuberculostatic thiosemicarbazones", JOURNAL OF ORGANIC CHEMISTRY, vol. 18, 1953, pages 121 - 126, XP002732230, DOI: 10.1021/JO01130A001
OKPALA, IHEANYI: "Investigational agents for sickle cell disease", EXPERT OPINION ON INVESTIGATIONAL DRUGS, vol. 15, no. 8, 2006, pages 833 - 842, XP002732218, DOI: 10.1517/13543784.15.8.833
OSHEIZA Y. ABDULMALIK ET AL: "In Vitro Antisickling Effects of Novel Pyridyl Derivatives with Enhanced Potency", BLOOD, vol. 106, no. 11, 16 November 2005 (2005-11-16) - 13 December 2005 (2005-12-13), US, pages 666a, XP055151739, ISSN: 0006-4971
MILLER M R ET AL: "Recent developments in nitric oxide donor drugs", BRITISH JOURNAL OF PHARMACOLOGY, vol. 151, no. 3, 1 June 2007 (2007-06-01), NATURE PUBLISHING GROUP, BASINGSTOKE, HANTS; GB, pages 305 - 321, XP002520652, ISSN: 0007-1188, [retrieved on 20070402], DOI: 10.1038/SJ.BJP.0707224
MACK, A. KYLE ET AL: "Sickle cell disease and nitric oxide: A paradigm shift?", INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, vol. 38, 2006, pages 1237 - 1243, XP002732219, DOI: 10.1016/J.BIOCEL.2006.01.010
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; BUSCATO, ESTELLA ET AL: "Structure-activity relationship and in vitro pharmacological evaluation of imidazo[1,2-a]pyridine-based inhibitors of 5-LO", XP002732220, retrieved from STN Database accession no. 2013:785255
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; RUDENKO, M. G. ET AL: "Synthesis and conversions of some p- and p,p'-derivatives of diphenyl oxide", XP002732221, retrieved from STN Database accession no. 1965:423848
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1997, OOTSUKA, SHUNICHI ET AL: "Preparation of .alpha.-hydroxyphenylacetic acid derivatives as agricultural bactericides", XP002732222, retrieved from STN Database accession no. 1997:371871
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KITAJIMA, HIROSHI ET AL: "Preparation of 3-Aromatic-substituted propionic acid or acrylic acid derivatives as antidiabetics", XP002732223, retrieved from STN Database accession no. 2000:873308
PATEL, NAVIN B. ET AL: "Design and synthesis of new imidazolinone derivatives as potential antifungal agents", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 48, 2011, pages 373 - 380, XP002732224, DOI: 10.1002/JHET.588
TANIS, STEVEN P. ET AL: "Synthesis and Biological Activity of Metabolites of the Antidiabetic, Antihyperglycemic Agent Pioglitazone", JOURNAL OF MEDICINAL CHEMISTRY, vol. 39, no. 26, 1996, pages 5053 - 5063, XP002732225, DOI: 10.1021/JM9605694
MOMOSE, YU ET AL: "Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 39, no. 6, 1991, pages 1440 - 1445, XP002732226, DOI: 10.1248/CPB.39.1440
CROWDER, J. R. ET AL: "Bisbenzylisoquinolines. IV. The preparation of diarylethers from diaryliodonium salts", JOURNAL OF THE CHEMICAL SOCIETY, vol. sept., 1963, pages 4578 - 4585, XP002732227, DOI: 10.1039/JR9630004578
PROFFT, E. ET AL: "2- and 6-substituted 4-methylpyrimidines", ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESELLSCHAFT, vol. 295, 1962, pages 649 - 662, XP002732228
BUU-HOI, NG. PH. ET AL: "Thiosemicarbazones and 4-oxo-2-thiazolin-2-ylhydrazones", JOURNAL OF THE CHEMICAL SOCIETY, 1956, pages 713 - 716, XP002732229
BUU-HOI, NG. PH. ET AL: "Some new tuberculostatic thiosemicarbazones", JOURNAL OF ORGANIC CHEMISTRY, vol. 18, 1953, pages 121 - 126, XP002732230, DOI: 10.1021/JO01130A001
Attorney, Agent or Firm:
KEOWN, Wayne, A. (One Portland SquarePortland, ME, US)
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