Title:
1,3-ジオキソインデン誘導体、その薬学的に許容される塩又は光学異性体、その調製方法及びそれを抗ウイルス活性成分として含有する医薬組成物
Document Type and Number:
Japanese Patent JP6373297
Kind Code:
B2
Abstract:
Disclosed are 1,3-Dioxoindene derivatives of Formula 1, pharmaceutically acceptable salts thereof or enantiomers, a preparation method thereof, and a pharmaceutical composition for the prevention or treatment of viral diseases, comprising the same as an active ingredient. The 1,3-Dioxoindene derivatives have excellent inhibitory activity against picornaviruses including coxsackie-, entero-, echo-, Polio-, and rhinoviruses, as well as exhibiting low cytotoxicity, so that they can be useful as an active ingredient of a pharmaceutical composition for the prevention or treatment of viral diseases including poliomyelitis, paralysis, acute hemorrhagic conjunctivitis, viral meningitis, hand-foot-and-mouth disease, vesicular disease, hepatitis A, myositis, myocarditis, pancreatitis, diabetes, epidemic myalgia, encephalitis, flu, herpangina, foot-and-mouth disease, asthma, chronic obstructive pulmonary disease, pneumonia, sinusitis or otitis media.
Inventors:
John Youngsik
Lee Jung Kyo
Choi Il Young
Kim hess
Kim Pirho
Hans Bonn
Nets Johann
Thibaud Hendrick Yang
Lee Jung Kyo
Choi Il Young
Kim hess
Kim Pirho
Hans Bonn
Nets Johann
Thibaud Hendrick Yang
Application Number:
JP2016099511A
Publication Date:
August 15, 2018
Filing Date:
May 18, 2016
Export Citation:
Assignee:
Corea Research Institute of Chemical Technology
Katrique Universitate Leuven K. You. Leuven Earl and Dee
Katrique Universitate Leuven K. You. Leuven Earl and Dee
International Classes:
C07C225/20; A61K31/122; A61K31/165; A61K31/17; A61K31/27; A61P3/10; A61P9/00; A61P11/02; A61P17/00; A61P21/00; A61P25/00; A61P27/16; A61P29/00; A61P31/12; A61P31/14; A61P31/16; C07C233/33; C07C233/61; C07C233/76; C07C247/14; C07C271/24; C07C271/44; C07C275/26; C07C275/64
Foreign References:
| WO2004087153A2 | ||||
| WO2010003023A2 | ||||
| GB1425295A | ||||
| WO2003082265A2 |
Other References:
Zalukaev, L. P.; Solov'ev, A. S.,Synthesis of new α-nitro-α-arylmethylenephthalides,Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya,1970年,13(10),1453-6
Sun, Fang-gang; Ye, Song,N-Heterocyclic carbene-catalyzed [4 + 1] annulation of phthalaldehyde and imines,Organic & Biomolecular Chemistry,2011年,9(10),3632-3635
Arens, A.; Mikstais, U.; Vanags, G.,Amino derivatives of 2-piperonyl-1,3-indandione,Zhurnal Obshchei Khimii,1964年,34(2),442-5
Jasinskas, L.; Vapsinskaite, I.,Synthesis of secondary amines of 4-methyl-2-phenylindandione,Lietuvos TSR Aukstuju Mokyklu Mokslo Darbai, Chem. ir Chem. Technol. ,1965年,7,77-80
Vasilev, G.; Mikhailov, V.,Synthesis, chemical structure, and biological activity of certain N-substituted 2-ureido- or thioureido-2-phenyl-1,3-indandiones,Doklady Bolgarskoi Akademii Nauk,1986年,39(2),93-6
Grinsteins, V.; Sausins, A.; Valtere, S.,Synthesis and study of thioureas. XII. Infrared spectra of 2-ary1-2-thiocarbamido-1,3-indandiones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1972年,(4),441-4
Bite, Dz.; Valtere, S.; Arens, A.,Substituted thiourea β-dicarbonyl compounds. IX. Spectroscopic study of 2-substituted N-[1,3-indandion-2-yl]thiourea and 2-(2-iminothiazolidin-3-yl]-2-substituted 1,3-indandiones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1969年,(1),109-12
Arens, A.; Lencbergs, I.,Isomerization of 2-amino-2-substituted 1,3-indandiones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1980年,(6),677-91
Rotbergs, J.; Strautina, V.; Oskaja, V.,Condensation of dicarboxylic acid anhydrides with compounds containing active methylene groups. XXVII. 2-Aryl-1,3-indandiones containing methyl groups,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija,1974年,(1),75-8
Arens, Augusts; Prikulis, A.,Reduction of aminodicarboxylic compounds. III. 2-Alkylamino-2-phenyl-3-indanon-1-ol and 2-alkylamino-2-phenyl-1,3-indandiol,Journal of ORGANIC CHEMISTRY of the USSR,1969年,5(9),2094-2097
Zalukaev, L. P.; Vnenkovskaya, D. G.,Synthesis of α-nitromethylpyridine and its derivatives,Khimiya Geterotsiklicheskikh Soedinenii ,1967年,(3),515-17
Briede, V.; Oskaja, V.; Lukina, I.,4,5-Dimethoxy-2-β-naphthyl-1,3-indandione,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1967年,(3),329-33
Arens, A.; Rode, U.; Artyukh, M. A.; Cirule, D.,2-Amino derivatives of 4,5- and 5,6-dimethoxy-2-phenylindan-1,3-diones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas,1966年,(3),342-6
Eckstein, Zygmunt; Urbanski, Tadeusz,Infrared absorption spectra of 2-nitroindandione derivatives,Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques,1960年,8(10),579-86
Zalukajevs, L.; Vanags, E.,Nitration of phthalones,Zhurnal Obshchei Khimii ,1957年,27,3278-82
Zalukaievs, L.; Vanags, E.,Preparation of 2-nitromethylquinoline and its derivatives,Zhurnal Obshchei Khimii,1956年,26,2639-42
Vegnere, V.; Stradins, J.,Adsorptive capacity of 2-amino-substituted indans on a mercury electrode,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1973年,(4),446-51
Arens, Augusts; Vanags, V.; Germane, S.; Ozolins, V.,2-Amino-2-halophenyl-1,3-indandiones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1969年,(4),446-51
Gudriniece, E.; Bruvele, N.; Ievins, A.,2-Azido-2-substituted indan-1,3-dione,Doklady Akademii Nauk SSSR,1966年,171(4),869-71
Sun, Fang-gang; Ye, Song,N-Heterocyclic carbene-catalyzed [4 + 1] annulation of phthalaldehyde and imines,Organic & Biomolecular Chemistry,2011年,9(10),3632-3635
Arens, A.; Mikstais, U.; Vanags, G.,Amino derivatives of 2-piperonyl-1,3-indandione,Zhurnal Obshchei Khimii,1964年,34(2),442-5
Jasinskas, L.; Vapsinskaite, I.,Synthesis of secondary amines of 4-methyl-2-phenylindandione,Lietuvos TSR Aukstuju Mokyklu Mokslo Darbai, Chem. ir Chem. Technol. ,1965年,7,77-80
Vasilev, G.; Mikhailov, V.,Synthesis, chemical structure, and biological activity of certain N-substituted 2-ureido- or thioureido-2-phenyl-1,3-indandiones,Doklady Bolgarskoi Akademii Nauk,1986年,39(2),93-6
Grinsteins, V.; Sausins, A.; Valtere, S.,Synthesis and study of thioureas. XII. Infrared spectra of 2-ary1-2-thiocarbamido-1,3-indandiones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1972年,(4),441-4
Bite, Dz.; Valtere, S.; Arens, A.,Substituted thiourea β-dicarbonyl compounds. IX. Spectroscopic study of 2-substituted N-[1,3-indandion-2-yl]thiourea and 2-(2-iminothiazolidin-3-yl]-2-substituted 1,3-indandiones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1969年,(1),109-12
Arens, A.; Lencbergs, I.,Isomerization of 2-amino-2-substituted 1,3-indandiones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1980年,(6),677-91
Rotbergs, J.; Strautina, V.; Oskaja, V.,Condensation of dicarboxylic acid anhydrides with compounds containing active methylene groups. XXVII. 2-Aryl-1,3-indandiones containing methyl groups,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija,1974年,(1),75-8
Arens, Augusts; Prikulis, A.,Reduction of aminodicarboxylic compounds. III. 2-Alkylamino-2-phenyl-3-indanon-1-ol and 2-alkylamino-2-phenyl-1,3-indandiol,Journal of ORGANIC CHEMISTRY of the USSR,1969年,5(9),2094-2097
Zalukaev, L. P.; Vnenkovskaya, D. G.,Synthesis of α-nitromethylpyridine and its derivatives,Khimiya Geterotsiklicheskikh Soedinenii ,1967年,(3),515-17
Briede, V.; Oskaja, V.; Lukina, I.,4,5-Dimethoxy-2-β-naphthyl-1,3-indandione,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1967年,(3),329-33
Arens, A.; Rode, U.; Artyukh, M. A.; Cirule, D.,2-Amino derivatives of 4,5- and 5,6-dimethoxy-2-phenylindan-1,3-diones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas,1966年,(3),342-6
Eckstein, Zygmunt; Urbanski, Tadeusz,Infrared absorption spectra of 2-nitroindandione derivatives,Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques,1960年,8(10),579-86
Zalukajevs, L.; Vanags, E.,Nitration of phthalones,Zhurnal Obshchei Khimii ,1957年,27,3278-82
Zalukaievs, L.; Vanags, E.,Preparation of 2-nitromethylquinoline and its derivatives,Zhurnal Obshchei Khimii,1956年,26,2639-42
Vegnere, V.; Stradins, J.,Adsorptive capacity of 2-amino-substituted indans on a mercury electrode,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1973年,(4),446-51
Arens, Augusts; Vanags, V.; Germane, S.; Ozolins, V.,2-Amino-2-halophenyl-1,3-indandiones,Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija ,1969年,(4),446-51
Gudriniece, E.; Bruvele, N.; Ievins, A.,2-Azido-2-substituted indan-1,3-dione,Doklady Akademii Nauk SSSR,1966年,171(4),869-71
Attorney, Agent or Firm:
Patent Business Corporation Saegusa International Patent Office