Title:
NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID
Document Type and Number:
WIPO Patent Application WO/2007/148755
Kind Code:
A1
Abstract:
Disclosed is a compound having affinity for amyloid and satisfactorily rapid clearance from a normal tissue and reduced in toxicity including mutagenicity. Specifically disclosed are: a compound represented by the formula (1) and a salt thereof; and a low-toxic diagnostic agent for Alzheimer's disease comprising the compound or the salt thereof. (1) wherein R1 represents a group selected from a hydrogen, a hydroxyl group, a carboxyl group, a sulfate group, an amino group, a nitro group, a cyano group, an alkyl substituent group having 1 to 4 carbon atoms and an alkoxy substituent group having 1 to 4 carbon atoms; R2 represents a radioactive halogen substituent group; and m represents an integer ranging from 0 to 2.
Inventors:
TANIFUJI SHIGEYUKI (JP)
HAYASHI AKIO (JP)
NAKAMURA DAISAKU (JP)
TAKASAKI SHINYA (JP)
STOREY ANTHONY EAMON (GB)
BOUVET DENIS RAYMOND CHRISTOPH (GB)
HAYASHI AKIO (JP)
NAKAMURA DAISAKU (JP)
TAKASAKI SHINYA (JP)
STOREY ANTHONY EAMON (GB)
BOUVET DENIS RAYMOND CHRISTOPH (GB)
Application Number:
PCT/JP2007/062503
Publication Date:
December 27, 2007
Filing Date:
June 21, 2007
Export Citation:
Assignee:
NIHON MEDIPHYSICS CO LTD (JP)
GE HEALTHCARE LTD (GB)
TANIFUJI SHIGEYUKI (JP)
HAYASHI AKIO (JP)
NAKAMURA DAISAKU (JP)
TAKASAKI SHINYA (JP)
STOREY ANTHONY EAMON (GB)
BOUVET DENIS RAYMOND CHRISTOPH (GB)
GE HEALTHCARE LTD (GB)
TANIFUJI SHIGEYUKI (JP)
HAYASHI AKIO (JP)
NAKAMURA DAISAKU (JP)
TAKASAKI SHINYA (JP)
STOREY ANTHONY EAMON (GB)
BOUVET DENIS RAYMOND CHRISTOPH (GB)
International Classes:
C07D471/04; A61K51/00; G01T1/161
Domestic Patent References:
| WO2001074815A2 | 2001-10-11 | |||
| WO2001074813A2 | 2001-10-11 | |||
| WO2003106439A1 | 2003-12-24 |
Foreign References:
| JPS6391391A | 1988-04-22 | |||
| JP2005526749A | 2005-09-08 | |||
| JP2004506633A | 2004-03-04 | |||
| JP2004506723A | 2004-03-04 | |||
| JP2005504055A | 2005-02-10 | |||
| JP2005512945A | 2005-05-12 | |||
| JP2002523383A | 2002-07-30 |
Other References:
SHAH C. ET AL.: "Novel Human Histamine H3 Receptor Antagonists", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 22, 2002, pages 3309 - 3312, XP002353596
SANFILIPPO P.J. ET AL.: "Synthesis of (Aryloxy) alkylamides. 2. Novel Imidazo-fused Heterocycles with Calcium Channel Blocking and Local Anesthetic Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 31, no. 11, 1988, pages 2221 - 2227, XP002182515
J. A. HARDY; G. A. HIGGINS: "Alzheimer's Disease: The Amyloid Cascade Hypothesis", SCIENCE, vol. 256, 1992, pages 184 - 185
G. MCKHANN ET AL.: "Clinical diagnosis of Alzheimer's disease: Report of the NINLDS-ADRDA Work Group under the auspices of Department of Health and Human Services Task Force on Alzheimer's Disease", NEUROLOGY, vol. 34, 1984, pages 939 - 944, XP000671871
Z.-P. ZHUANG ET AL.: "Radioiodinated Styrylbenzenes and Thioflavins as Probes for Amyloid Aggregates", J. MED. CHEM., vol. 44, 2001, pages 1905 - 1914, XP002410969, DOI: doi:10.1021/jm010045q
MASAHIRO ONO ET AL.: "11C-labeled stilbene derivatives as Aß-aggregate-specific PET imaging agents for Alzheimer's disease", NUCLEAR MEDICINE AND BIOLOGY, vol. 30, 2003, pages 565 - 571, XP004444174, DOI: doi:10.1016/S0969-8051(03)00049-0
H. F. KUNG ET AL.: "Novel Stilbenes as Probes for amyloid plaques", J. AMERICAN CHEMICAL SOCIETY, vol. 123, 2001, pages 12740 - 12741
ZHI-PING ZHUANG ET AL.: "IBOX(2-(4' -dimethylaminophenyl)-6-iodobenzoxazole): a ligand for imaging amyloid plaques in the brain", NUCLEAR MEDICINE AND BIOLOGY, vol. 28, 2001, pages 887 - 894, XP002386398
FURUMOTO Y ET AL.: "11c] BF-227: A New 11C-Labeled 2-Ethenylbenzoxazole Derivative for Amyloid-ß Plaques Imaging", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 32, no. 1, 2005, pages 759
ERIC D. AGDEPPA ET AL.: "2-Dialkylamino-6-Acylmalononitrile Substituted Naphthalenes (DDNP Analogs): Novel Diagnostic and Therapeutic Tools in Alzheimer's Disease.", MOLECULAR IMAGING AND BIOLOGY, vol. 5, 2003, pages 404 - 417
ZHI-PING ZHUANG ET AL.: "Structure-Activity Relationship of Imidazo[1,2- a]pyridines as Ligands for Detecting ß-Amyloid Plaques in the Brain", J. MED. CHEM, vol. 46, 2003, pages 237 - 243, XP002446716, DOI: doi:10.1021/jm020351j
W. E. KLUNK ET AL.: "Imaging brain amyloid in Alzheumer's disease with Pittsburgh Compound-B.", ANN. NEUROL., vol. 55, 2004, pages 306 - 319, XP008031485, DOI: doi:10.1002/ana.20009
NICOLAAS P. L. G. VERHOEFF ET AL.: "In-Vivo Imaging of Alzheimer Disease ß-Amyloid With [11C]SB-13 PET.", AMERICAN JOURNAL OF GERIATRIC PSYCHIATRY, vol. 12, 2004, pages 584 - 595, XP009121906
ZHI-PING ZHUANG ET AL., NUCLEAR MEDICINE AND BIOLOGY, vol. 28, 2001, pages 887 - 894
H. F. KUNG ET AL., J. AM. CHEM. SOC., vol. 123, 2001, pages 12740 - 12741
MASAHIRO ONO ET AL., NUCLEAR MEDICINE AND BIOLOGY, vol. 30, 2003, pages 565 - 571
JOSEPH G. LOMBARDINO, JOURNAL OF MEDICINAL CHEMISTRY, vol. 24, 1981, pages 39 - 42
KING, L. CARROLL; OSTRUM, G. KENNETH, JOURNAL OF ORGANIC CHEMISTRY, vol. 29, no. 12, 1964, pages 3459 - 3461
ABDERRAHIM BOUZIDE; GILLES SAUVE, ORGANIC LETTERS, vol. 4, no. 14, 2002, pages 2329 - 2332
ZHI-PING ZHUANG ET AL., J. MED. CHEM., vol. 46, 2003, pages 237 - 243
NAIKI, H. ET AL., LABORATORY INVESTIGATION, vol. 74, 1996, pages 374 - 383
WANG, Y. ET AL., J. LABELLED COMPOUNDS RADIOPHARMACEUT., vol. 44, 2001, pages 239
WANG. Y. ET AL., J. LABELLED COMPOUNDS RADIOPHARMACEUT., vol. 44, 2001, pages 239
ZHUANG, Z. P. ET AL., J. MED. CHEM., vol. 46, 2003, pages 237
DOUGLAS D. DISCHINO ET AL., J. NUCL. MED., vol. 24, 1983, pages 1030 - 1038
FRANCO LOMBARDO ET AL., J. MED. CHEM., vol. 43, 2000, pages 2922 - 2927
See also references of EP 2042501A4
SANFILIPPO P.J. ET AL.: "Synthesis of (Aryloxy) alkylamides. 2. Novel Imidazo-fused Heterocycles with Calcium Channel Blocking and Local Anesthetic Activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 31, no. 11, 1988, pages 2221 - 2227, XP002182515
J. A. HARDY; G. A. HIGGINS: "Alzheimer's Disease: The Amyloid Cascade Hypothesis", SCIENCE, vol. 256, 1992, pages 184 - 185
G. MCKHANN ET AL.: "Clinical diagnosis of Alzheimer's disease: Report of the NINLDS-ADRDA Work Group under the auspices of Department of Health and Human Services Task Force on Alzheimer's Disease", NEUROLOGY, vol. 34, 1984, pages 939 - 944, XP000671871
Z.-P. ZHUANG ET AL.: "Radioiodinated Styrylbenzenes and Thioflavins as Probes for Amyloid Aggregates", J. MED. CHEM., vol. 44, 2001, pages 1905 - 1914, XP002410969, DOI: doi:10.1021/jm010045q
MASAHIRO ONO ET AL.: "11C-labeled stilbene derivatives as Aß-aggregate-specific PET imaging agents for Alzheimer's disease", NUCLEAR MEDICINE AND BIOLOGY, vol. 30, 2003, pages 565 - 571, XP004444174, DOI: doi:10.1016/S0969-8051(03)00049-0
H. F. KUNG ET AL.: "Novel Stilbenes as Probes for amyloid plaques", J. AMERICAN CHEMICAL SOCIETY, vol. 123, 2001, pages 12740 - 12741
ZHI-PING ZHUANG ET AL.: "IBOX(2-(4' -dimethylaminophenyl)-6-iodobenzoxazole): a ligand for imaging amyloid plaques in the brain", NUCLEAR MEDICINE AND BIOLOGY, vol. 28, 2001, pages 887 - 894, XP002386398
FURUMOTO Y ET AL.: "11c] BF-227: A New 11C-Labeled 2-Ethenylbenzoxazole Derivative for Amyloid-ß Plaques Imaging", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 32, no. 1, 2005, pages 759
ERIC D. AGDEPPA ET AL.: "2-Dialkylamino-6-Acylmalononitrile Substituted Naphthalenes (DDNP Analogs): Novel Diagnostic and Therapeutic Tools in Alzheimer's Disease.", MOLECULAR IMAGING AND BIOLOGY, vol. 5, 2003, pages 404 - 417
ZHI-PING ZHUANG ET AL.: "Structure-Activity Relationship of Imidazo[1,2- a]pyridines as Ligands for Detecting ß-Amyloid Plaques in the Brain", J. MED. CHEM, vol. 46, 2003, pages 237 - 243, XP002446716, DOI: doi:10.1021/jm020351j
W. E. KLUNK ET AL.: "Imaging brain amyloid in Alzheumer's disease with Pittsburgh Compound-B.", ANN. NEUROL., vol. 55, 2004, pages 306 - 319, XP008031485, DOI: doi:10.1002/ana.20009
NICOLAAS P. L. G. VERHOEFF ET AL.: "In-Vivo Imaging of Alzheimer Disease ß-Amyloid With [11C]SB-13 PET.", AMERICAN JOURNAL OF GERIATRIC PSYCHIATRY, vol. 12, 2004, pages 584 - 595, XP009121906
ZHI-PING ZHUANG ET AL., NUCLEAR MEDICINE AND BIOLOGY, vol. 28, 2001, pages 887 - 894
H. F. KUNG ET AL., J. AM. CHEM. SOC., vol. 123, 2001, pages 12740 - 12741
MASAHIRO ONO ET AL., NUCLEAR MEDICINE AND BIOLOGY, vol. 30, 2003, pages 565 - 571
JOSEPH G. LOMBARDINO, JOURNAL OF MEDICINAL CHEMISTRY, vol. 24, 1981, pages 39 - 42
KING, L. CARROLL; OSTRUM, G. KENNETH, JOURNAL OF ORGANIC CHEMISTRY, vol. 29, no. 12, 1964, pages 3459 - 3461
ABDERRAHIM BOUZIDE; GILLES SAUVE, ORGANIC LETTERS, vol. 4, no. 14, 2002, pages 2329 - 2332
ZHI-PING ZHUANG ET AL., J. MED. CHEM., vol. 46, 2003, pages 237 - 243
NAIKI, H. ET AL., LABORATORY INVESTIGATION, vol. 74, 1996, pages 374 - 383
WANG, Y. ET AL., J. LABELLED COMPOUNDS RADIOPHARMACEUT., vol. 44, 2001, pages 239
WANG. Y. ET AL., J. LABELLED COMPOUNDS RADIOPHARMACEUT., vol. 44, 2001, pages 239
ZHUANG, Z. P. ET AL., J. MED. CHEM., vol. 46, 2003, pages 237
DOUGLAS D. DISCHINO ET AL., J. NUCL. MED., vol. 24, 1983, pages 1030 - 1038
FRANCO LOMBARDO ET AL., J. MED. CHEM., vol. 43, 2000, pages 2922 - 2927
See also references of EP 2042501A4
Attorney, Agent or Firm:
IDE, Masatake et al. (9F Gobancho Grand Bldg.,3-1, Gobanch, Chiyoda-ku Tokyo 76, JP)
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