Title:
COMPOUND, SALT OF COMPOUND, NEUROMODULATION AGENT, METHOD FOR EVALUATING NEUROMODULATION AGENT, METHOD FOR PRODUCING COMPOUND, AND METHOD FOR PRODUCING SALT OF COMPOUND
Document Type and Number:
WIPO Patent Application WO/2020/032080
Kind Code:
A1
Abstract:
Provided is a compound represented by general formula (I), or a salt thereof. (In the formula, X1, X2, X3 and X4 are a hydrogen atom, a C1-9 alkyl group, or a C3-9 unsaturated hydrocarbon group which has 1-4 triple bonds between carbon atoms and which may have a substituent (when the unsaturated hydrocarbon group has a methylene group at the end of the bond, the methylene group may be substituted with a carbonyl group); X5 is a C2-8 unsaturated hydrocarbon group which has 1-4 triple bonds between carbon atoms and which may have a substituent; X6 is a hydrogen atom, or a C3-9 unsaturated hydrocarbon group which has 1-4 triple bonds between carbon atoms and which may have a substituent; n1 and n3 are 0 or 1; and n2 is an integer of 1-5.)
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Inventors:
NURIYA MUTSUO (JP)
ASHIKARI YOSUKE (JP)
YASUI MASATO (JP)
FUJIMOTO YUKARI (JP)
ASHIKARI YOSUKE (JP)
YASUI MASATO (JP)
FUJIMOTO YUKARI (JP)
Application Number:
PCT/JP2019/031022
Publication Date:
February 13, 2020
Filing Date:
August 07, 2019
Export Citation:
Assignee:
UNIV KEIO (JP)
International Classes:
C07C215/52; A61K31/137; A61K31/14; A61K31/36; A61P25/00; C07C213/08; C07C215/66; C07C217/60; C07C217/70; C07D209/32; C07D317/58; C12Q1/06; G01N33/52
Domestic Patent References:
| WO2012041934A1 | 2012-04-05 |
Foreign References:
| JP2007515444A | 2007-06-14 | |||
| JP2005527517A | 2005-09-15 | |||
| JPS63179871A | 1988-07-23 |
Other References:
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MAGNE, VALENTIN ET AL.: "Synthesis of Spiroindolenines via Regioselective Gold(I)-Catalyzed Cyclizations of N-Propargyl Tryptamines", ADVANCED SYNTHESIS & CATALYSIS, vol. 359, no. 22, 2017, pages 4036 - 4042, XP055685715
PEREGO, LUCA ALESSANDRO ET AL.: "Copper-Catalyzed Hydroamination of Allenes: from Mechanistic Understanding to Methodology Development", ACS CATALYSIS, vol. 7, no. 7, 2017, pages 4253 - 4264, XP055629283, DOI: 10.1021/acscatal.7b00911
DATABASE REGISTRY [online] 16 February 1990 (1990-02-16), retrieved from STN Database accession no. 125436-87-5
JAYAKUMAR, JAYACHANDRAN ET AL.: "Direct Synthesis of Protoberberine Alkaloids by Rh-Catalyzed C-H Bond Activation as the Key Ste p", CHEMISTRY - A EUROPEAN JOURNAL, vol. 22, no. 5, 2016, pages 1800 - 1804, XP055685714
ALVAREZ-PEREZ, ANDREA ET AL.: "Catalytic Cyclization of o-Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3-Benzazepines", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 54, no. 45, 2015, pages 13357 - 13361, XP055685713
CIOC, RAZVAN C. ET AL.: "One-pot synthesis of N-substituted beta -amino alcohols from aldehydes and isocyanides", CHEMISTRY - A EUROPEAN JOURNAL, vol. 21, no. 21, 2015, pages 7808 - 7813, XP055531412, DOI: 10.1002/chem.201500210
MANONI, E. ET AL.: "Organocatalytic enantioselective synthesis of 1-vinyl tetrahydroisoquinolines through allenamide activation with chiral Bronsted acids", RSC ADVANCES, vol. 5, 2015, pages 10546 - 10550, XP055685710
LIN, JASON CHING-YAO ET AL.: "Characterization of Protein Serotonylation via Bioorthogonal Labeling and Enrichment", JOURNAL OF PROTEOME RESEARCH, vol. 13, no. 8, 2014, pages 3523 - 3529, XP055685707
DATABASE REGISTRY [online] 22 June 2001 (2001-06-22), retrieved from STN Database accession no. 342880-45-9
MITACHI, KATSUHIKO ET AL.: "Synthesis and structure-activity relationship of disubstituted benzamides as a novel class of antimalarial agents", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 22, no. 14, 2012, pages 4536 - 4539, XP028504396
WANG, ZHENJUN ET AL.: "Synthesis and bioactivity of novel 1-substituted-1H-1,2,3-triazole-4-carboxamide", YOUJI HUAXUE, vol. 31, no. 3, 2011, pages 317 - 323, XP008162447
ERMOLAT'EV, DENIS S. ET AL.: "Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 49, no. 49, 2010, pages 9465 - 9468, XP055011731, DOI: 10.1002/anie.201004256
GOLDMANN, ANJA S. ET AL.: "Biomimetic Mussel Adhesive Inspired Clickable Anchors Applied to the Functionalization of Fe304 Nanoparticles", MACROMOLECULAR RAPID COMMUNICATIONS, vol. 31, no. 18, 2010, pages 1608 - 1615, XP055685698
LAMBERTH, CLEMENS ET AL.: "Synthesis and fungicidal activity of N-2-(3-methoxy-4-propargyloxy)phenethyl amides. Part 3: Stretched and heterocyclic mandelamide oomyceticides", PEST MANAGEMENT SCIENCE, vol. 63, no. 1, 2007, pages 57 - 62, XP055685692
ARCADI, ANTONIO ET AL.: "The reaction of acetylenic amines with tetraethylammonium carbonate and hydrogen carbonate", SYNTHESIS OF 5-METHYLENE-1,3-OXAZOLIDIN-2-ONES , SYNLETT, vol. 1, 2005, pages 67 - 70, XP055685687
JACKMAN, G. B. ET AL.: "Some tryptamine derivatives: 1-aryloxy-3-[(2-indol-3-ylethyl)-amino]propan-2-ols", JOURNAL OF PHARMACY AND PHARMACOLOGY, vol. 17, no. 11, 1965, pages 742 - 746
MAGNE, VALENTIN ET AL.: "Synthesis of Spiroindolenines via Regioselective Gold(I)-Catalyzed Cyclizations of N-Propargyl Tryptamines", ADVANCED SYNTHESIS & CATALYSIS, vol. 359, no. 22, 2017, pages 4036 - 4042, XP055685715
PEREGO, LUCA ALESSANDRO ET AL.: "Copper-Catalyzed Hydroamination of Allenes: from Mechanistic Understanding to Methodology Development", ACS CATALYSIS, vol. 7, no. 7, 2017, pages 4253 - 4264, XP055629283, DOI: 10.1021/acscatal.7b00911
DATABASE REGISTRY [online] 16 February 1990 (1990-02-16), retrieved from STN Database accession no. 125436-87-5
JAYAKUMAR, JAYACHANDRAN ET AL.: "Direct Synthesis of Protoberberine Alkaloids by Rh-Catalyzed C-H Bond Activation as the Key Ste p", CHEMISTRY - A EUROPEAN JOURNAL, vol. 22, no. 5, 2016, pages 1800 - 1804, XP055685714
ALVAREZ-PEREZ, ANDREA ET AL.: "Catalytic Cyclization of o-Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3-Benzazepines", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 54, no. 45, 2015, pages 13357 - 13361, XP055685713
CIOC, RAZVAN C. ET AL.: "One-pot synthesis of N-substituted beta -amino alcohols from aldehydes and isocyanides", CHEMISTRY - A EUROPEAN JOURNAL, vol. 21, no. 21, 2015, pages 7808 - 7813, XP055531412, DOI: 10.1002/chem.201500210
MANONI, E. ET AL.: "Organocatalytic enantioselective synthesis of 1-vinyl tetrahydroisoquinolines through allenamide activation with chiral Bronsted acids", RSC ADVANCES, vol. 5, 2015, pages 10546 - 10550, XP055685710
LIN, JASON CHING-YAO ET AL.: "Characterization of Protein Serotonylation via Bioorthogonal Labeling and Enrichment", JOURNAL OF PROTEOME RESEARCH, vol. 13, no. 8, 2014, pages 3523 - 3529, XP055685707
DATABASE REGISTRY [online] 22 June 2001 (2001-06-22), retrieved from STN Database accession no. 342880-45-9
MITACHI, KATSUHIKO ET AL.: "Synthesis and structure-activity relationship of disubstituted benzamides as a novel class of antimalarial agents", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 22, no. 14, 2012, pages 4536 - 4539, XP028504396
WANG, ZHENJUN ET AL.: "Synthesis and bioactivity of novel 1-substituted-1H-1,2,3-triazole-4-carboxamide", YOUJI HUAXUE, vol. 31, no. 3, 2011, pages 317 - 323, XP008162447
ERMOLAT'EV, DENIS S. ET AL.: "Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 49, no. 49, 2010, pages 9465 - 9468, XP055011731, DOI: 10.1002/anie.201004256
GOLDMANN, ANJA S. ET AL.: "Biomimetic Mussel Adhesive Inspired Clickable Anchors Applied to the Functionalization of Fe304 Nanoparticles", MACROMOLECULAR RAPID COMMUNICATIONS, vol. 31, no. 18, 2010, pages 1608 - 1615, XP055685698
LAMBERTH, CLEMENS ET AL.: "Synthesis and fungicidal activity of N-2-(3-methoxy-4-propargyloxy)phenethyl amides. Part 3: Stretched and heterocyclic mandelamide oomyceticides", PEST MANAGEMENT SCIENCE, vol. 63, no. 1, 2007, pages 57 - 62, XP055685692
ARCADI, ANTONIO ET AL.: "The reaction of acetylenic amines with tetraethylammonium carbonate and hydrogen carbonate", SYNTHESIS OF 5-METHYLENE-1,3-OXAZOLIDIN-2-ONES , SYNLETT, vol. 1, 2005, pages 67 - 70, XP055685687
JACKMAN, G. B. ET AL.: "Some tryptamine derivatives: 1-aryloxy-3-[(2-indol-3-ylethyl)-amino]propan-2-ols", JOURNAL OF PHARMACY AND PHARMACOLOGY, vol. 17, no. 11, 1965, pages 742 - 746
Attorney, Agent or Firm:
TANAI Sumio et al. (JP)
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