Title:
IODINE ATOM-CONTAINING CYCLIC COMPOUND
Document Type and Number:
WIPO Patent Application WO/2023/195546
Kind Code:
A1
Abstract:
This compound is represented by formula (1): (in the formula: RG is a group that includes at least one cyclic structure; I is an iodine atom; R1 moieties may be the same as, or different from, each other, and are each a monovalent functional group having 0-30 carbon atoms and not containing a polymerizable unsaturated bond; n is an integer between 1 and 5; and m is an integer between 1 and 5).
Inventors:
MATSUMOTO MASAHIRO (JP)
IINUMA MASATAKA (JP)
OMATSU TADASHI (JP)
SATO TAKASHI (JP)
ECHIGO MASATOSHI (JP)
IINUMA MASATAKA (JP)
OMATSU TADASHI (JP)
SATO TAKASHI (JP)
ECHIGO MASATOSHI (JP)
Application Number:
PCT/JP2023/015256
Publication Date:
October 12, 2023
Filing Date:
April 10, 2023
Export Citation:
Assignee:
MITSUBISHI GAS CHEMICAL CO (JP)
International Classes:
C07C43/23; C07C35/52; C07C69/94; G03F7/004; G03F7/039
Domestic Patent References:
| WO2015152128A1 | 2015-10-08 | |||
| WO2021230300A1 | 2021-11-18 | |||
| WO2021157551A1 | 2021-08-12 |
Foreign References:
| JP2021188041A | 2021-12-13 | |||
| JP2016533394A | 2016-10-27 | |||
| JP2009513620A | 2009-04-02 | |||
| JP2022164584A | 2022-10-27 | |||
| JP2022141598A | 2022-09-29 | |||
| JP2022135974A | 2022-09-15 |
Other References:
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TAKASHI IKAWA, AKIRA TAKAGI, YURIO KURITA, KOZUMO SAITO, KENJI AZECHI, MASAHIRO EGI, KEISUKE KAKIGUCHI, YASUYUKI KITA, SHUJI AKAI: "Preparation and Regioselective Diels-Alder Reactions of Borylbenzynes: Synthesis of Functionalized Arylboronates", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, ¬VERLAG CHEMIE| :, vol. 49, no. 32, 26 July 2010 (2010-07-26), pages 5563 - 5566, XP055017375, ISSN: 14337851, DOI: 10.1002/anie.201002191
LE BOURDONNEC BERTRAND, WINDH ROLF T., LEISTER LARA K., ZHOU Q. JEAN, AJELLO CHRISTOPHER W., GU MINGHUA, CHU GUO-HUA, TUTHILL PAUL: "Spirocyclic Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of N , N -Diethyl-3-hydroxy-4-(spiro[chromene-2,4′-piperidine]-4-yl) Benzamide (ADL5747)", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 52, no. 18, 24 September 2009 (2009-09-24), US , pages 5685 - 5702, XP093097887, ISSN: 0022-2623, DOI: 10.1021/jm900773n
YUKI OHISHI; HAJIME ABE; MASAHIKO INOUYE: "Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine–Phenol Alternating Oligomer", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2017, no. 46, 14 December 2017 (2017-12-14), DE , pages 6975 - 6979, XP072123038, ISSN: 1434-193X, DOI: 10.1002/ejoc.201701522
DEFRANCQ ERIC, TABACCHI RAFFAELE: "The synthesis of [ 14 C] labelled Eutypine", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 31, no. 12, 1 December 1992 (1992-12-01), GB , pages 1057 - 1063, XP093097888, ISSN: 0362-4803, DOI: 10.1002/jlcr.2580311214
AL HUSSAINY RANA, VERBEEK JOOST, VAN DER BORN DION, BRAKER ANTON H., LEYSEN JOSÉE E., KNOL REMCO J., BOOIJ JAN, HERSCHEID J. (KOOS: "Design, Synthesis, Radiolabeling, and in Vitro and in Vivo Evaluation of Bridgehead Iodinated Analogues of N -{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}- N -(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635) as Potential SPECT Ligands for the 5-HT 1A Receptor", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 54, no. 10, 26 May 2011 (2011-05-26), US , pages 3480 - 3491, XP093097924, ISSN: 0022-2623, DOI: 10.1021/jm1009956
FRIDMAN A L; SIVKOVA M P; ZALESOV V S; DOLBILKIN K V; MOISEEV I K; DOROSHENKO R I; MANZHELEVSKAYA E V: "SYNTHESIS AND BIOLOGICAL ACTIVITY OF ADAMANTANE DERIVATIVES", KHIMIKO-FARMATSEVTICHESKII ZHURNAL, IZDATEL'STVO FOLIUM, RU, vol. 13, no. 12, 1 January 1979 (1979-01-01), RU , pages 24 - 31, XP009147275, ISSN: 0023-1134
DATABASE REGISTRY ANONYMOUS : "-Benzoic acid, 4-iodo-3-(1-methoxyethoxy)-(CA INDEX NAME) ", XP093097936, retrieved from STN
FEATHERSTON AARON L., KWON YONGSEOK, POMPEO MATTHEW M., ENGL OLIVER D., LEAHY DAVID K., MILLER SCOTT J.: "Catalytic asymmetric and stereodivergent oligonucleotide synthesis", SCIENCE, AMERICAN ASSOCIATION FOR THE ADVANCEMENT OF SCIENCE, US, vol. 371, no. 6530, 12 February 2021 (2021-02-12), US , pages 702 - 707, XP093097929, ISSN: 0036-8075, DOI: 10.1126/science.abf4359
YUSAKU NOMURA; FRÉDÉRIC THUAUD; DAISUKE SEKINE; AKIHIRO ITO; SATOKO MAEDA; HIROYUKI KOSHINO; DAISUKE HASHIZUME; ATSUYA MURANAKA; T: "Synthesis of All Stereoisomers of Monomeric Spectomycin A1/A2 and Evaluation of Their Protein SUMOylation‐Inhibitory Activity", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 25, no. 35, 20 May 2019 (2019-05-20), DE, pages 8387 - 8392, XP071849040, ISSN: 0947-6539, DOI: 10.1002/chem.201901093
LIU YAN, ZHANG SHUWEI, MIAO QIAN, ZHENG LIFEI, ZONG LILI, CHENG YIXIANG: "Fluorescent Chemosensory Conjugated Polymers Based on Optically Active Polybinaphthyls and 2,2‘-Bipyridyl Units", MACROMOLECULES, 40, 1 July 2007 (2007-07-01), pages 4839 - 4847, XP055933924, Retrieved from the Internet [retrieved on 20220621], DOI: 10.1021/ma0701437
KANG, D.W. RYU, H. LEE, J. LANG, K.A. PAVLYUKOVETS, V.A. PEARCE, L.V. IKEDA, T. LAZAR, J. BLUMBERG, P.M.: "Halogenation of 4-hydroxy-3-methoxybenzyl thiourea TRPV1 agonists showed enhanced antagonism to capsaicin", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 17, no. 1, 22 December 2006 (2006-12-22), Amsterdam NL , pages 214 - 219, XP005812145, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2006.09.059
GAO Y, ET AL.: "Utilization of a peptide lead for the discovery of a novel PTP1B-binding motif", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 44, no. 18, 1 January 2001 (2001-01-01), US , pages 2869 - 2878, XP002982270, ISSN: 0022-2623, DOI: 10.1021/jm010020r
DATABASE REGISTRY ANONYMOUS : "- Benzenemethanol, 3-iodo-5-methoxy-4-[3-[(tetrahydro-2H-pyran-2- yl)methoxy]propoxy]- (CA INDEX NAME)", XP093097934, retrieved from STN
TAKASHI IKAWA, AKIRA TAKAGI, YURIO KURITA, KOZUMO SAITO, KENJI AZECHI, MASAHIRO EGI, KEISUKE KAKIGUCHI, YASUYUKI KITA, SHUJI AKAI: "Preparation and Regioselective Diels-Alder Reactions of Borylbenzynes: Synthesis of Functionalized Arylboronates", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, ¬VERLAG CHEMIE| :, vol. 49, no. 32, 26 July 2010 (2010-07-26), pages 5563 - 5566, XP055017375, ISSN: 14337851, DOI: 10.1002/anie.201002191
LE BOURDONNEC BERTRAND, WINDH ROLF T., LEISTER LARA K., ZHOU Q. JEAN, AJELLO CHRISTOPHER W., GU MINGHUA, CHU GUO-HUA, TUTHILL PAUL: "Spirocyclic Delta Opioid Receptor Agonists for the Treatment of Pain: Discovery of N , N -Diethyl-3-hydroxy-4-(spiro[chromene-2,4′-piperidine]-4-yl) Benzamide (ADL5747)", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 52, no. 18, 24 September 2009 (2009-09-24), US , pages 5685 - 5702, XP093097887, ISSN: 0022-2623, DOI: 10.1021/jm900773n
YUKI OHISHI; HAJIME ABE; MASAHIKO INOUYE: "Saccharide Recognition and Helix Formation in Water with an Amphiphilic Pyridine–Phenol Alternating Oligomer", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2017, no. 46, 14 December 2017 (2017-12-14), DE , pages 6975 - 6979, XP072123038, ISSN: 1434-193X, DOI: 10.1002/ejoc.201701522
DEFRANCQ ERIC, TABACCHI RAFFAELE: "The synthesis of [ 14 C] labelled Eutypine", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 31, no. 12, 1 December 1992 (1992-12-01), GB , pages 1057 - 1063, XP093097888, ISSN: 0362-4803, DOI: 10.1002/jlcr.2580311214
AL HUSSAINY RANA, VERBEEK JOOST, VAN DER BORN DION, BRAKER ANTON H., LEYSEN JOSÉE E., KNOL REMCO J., BOOIJ JAN, HERSCHEID J. (KOOS: "Design, Synthesis, Radiolabeling, and in Vitro and in Vivo Evaluation of Bridgehead Iodinated Analogues of N -{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}- N -(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635) as Potential SPECT Ligands for the 5-HT 1A Receptor", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 54, no. 10, 26 May 2011 (2011-05-26), US , pages 3480 - 3491, XP093097924, ISSN: 0022-2623, DOI: 10.1021/jm1009956
FRIDMAN A L; SIVKOVA M P; ZALESOV V S; DOLBILKIN K V; MOISEEV I K; DOROSHENKO R I; MANZHELEVSKAYA E V: "SYNTHESIS AND BIOLOGICAL ACTIVITY OF ADAMANTANE DERIVATIVES", KHIMIKO-FARMATSEVTICHESKII ZHURNAL, IZDATEL'STVO FOLIUM, RU, vol. 13, no. 12, 1 January 1979 (1979-01-01), RU , pages 24 - 31, XP009147275, ISSN: 0023-1134
DATABASE REGISTRY ANONYMOUS : "-Benzoic acid, 4-iodo-3-(1-methoxyethoxy)-(CA INDEX NAME) ", XP093097936, retrieved from STN
FEATHERSTON AARON L., KWON YONGSEOK, POMPEO MATTHEW M., ENGL OLIVER D., LEAHY DAVID K., MILLER SCOTT J.: "Catalytic asymmetric and stereodivergent oligonucleotide synthesis", SCIENCE, AMERICAN ASSOCIATION FOR THE ADVANCEMENT OF SCIENCE, US, vol. 371, no. 6530, 12 February 2021 (2021-02-12), US , pages 702 - 707, XP093097929, ISSN: 0036-8075, DOI: 10.1126/science.abf4359
YUSAKU NOMURA; FRÉDÉRIC THUAUD; DAISUKE SEKINE; AKIHIRO ITO; SATOKO MAEDA; HIROYUKI KOSHINO; DAISUKE HASHIZUME; ATSUYA MURANAKA; T: "Synthesis of All Stereoisomers of Monomeric Spectomycin A1/A2 and Evaluation of Their Protein SUMOylation‐Inhibitory Activity", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 25, no. 35, 20 May 2019 (2019-05-20), DE, pages 8387 - 8392, XP071849040, ISSN: 0947-6539, DOI: 10.1002/chem.201901093
LIU YAN, ZHANG SHUWEI, MIAO QIAN, ZHENG LIFEI, ZONG LILI, CHENG YIXIANG: "Fluorescent Chemosensory Conjugated Polymers Based on Optically Active Polybinaphthyls and 2,2‘-Bipyridyl Units", MACROMOLECULES, 40, 1 July 2007 (2007-07-01), pages 4839 - 4847, XP055933924, Retrieved from the Internet
KANG, D.W. RYU, H. LEE, J. LANG, K.A. PAVLYUKOVETS, V.A. PEARCE, L.V. IKEDA, T. LAZAR, J. BLUMBERG, P.M.: "Halogenation of 4-hydroxy-3-methoxybenzyl thiourea TRPV1 agonists showed enhanced antagonism to capsaicin", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 17, no. 1, 22 December 2006 (2006-12-22), Amsterdam NL , pages 214 - 219, XP005812145, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2006.09.059
GAO Y, ET AL.: "Utilization of a peptide lead for the discovery of a novel PTP1B-binding motif", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 44, no. 18, 1 January 2001 (2001-01-01), US , pages 2869 - 2878, XP002982270, ISSN: 0022-2623, DOI: 10.1021/jm010020r
DATABASE REGISTRY ANONYMOUS : "- Benzenemethanol, 3-iodo-5-methoxy-4-[3-[(tetrahydro-2H-pyran-2- yl)methoxy]propoxy]- (CA INDEX NAME)", XP093097934, retrieved from STN
Attorney, Agent or Firm:
INABA, Yoshiyuki et al. (JP)
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