Title:
1,3-DI-OXO-INDENE DERIVATIVE, PHARMACEUTICALLY ACCEPTABLE SALT OR OPTICAL ISOMER THEREOF, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AS ANTIVIRAL ACTIVE INGREDIENT
Document Type and Number:
Japanese Patent JP2016185967
Kind Code:
A
Abstract:
PROBLEM TO BE SOLVED: To provide a 1,3-di-oxo-indene derivative, a pharmaceutically acceptable salt or optical isomer thereof, a preparation method thereof, and a pharmaceutical composition containing the same as an active ingredient and having anti-picornavirus activity.SOLUTION: The invention provides 1,3-di-oxo-indene derivative represented by the chemical formula (1), and a pharmaceutically acceptable salt or optical isomer thereof.SELECTED DRAWING: None
Inventors:
JUNG YOUNG SIK
LEE CHONG KGO
CHOI IHL YOUNG
KIM HAE SOO
KIM PILHO
HAN SOO BONG
JOHAN NEYTS
HENDRIK JAN THIBAUT
LEE CHONG KGO
CHOI IHL YOUNG
KIM HAE SOO
KIM PILHO
HAN SOO BONG
JOHAN NEYTS
HENDRIK JAN THIBAUT
Application Number:
JP2016099511A
Publication Date:
October 27, 2016
Filing Date:
May 18, 2016
Export Citation:
Assignee:
KOREA RES INST CHEMICAL TECH
KATHOLIEKE UNIV LEUVEN K U LEUVEN R & D
KATHOLIEKE UNIV LEUVEN K U LEUVEN R & D
International Classes:
C07C49/747; A61K31/122; A61K31/165; A61K31/17; A61K31/222; A61K31/27; A61K31/435; A61K31/44; A61K31/47; A61P3/10; A61P9/00; A61P11/02; A61P17/00; A61P21/00; A61P25/00; A61P27/16; A61P29/00; A61P31/12; A61P31/14; A61P31/16; C07C49/753; C07C69/16; C07C69/18; C07C69/28; C07C69/54; C07C69/618; C07C69/63; C07C69/738; C07C69/78; C07C205/45; C07C225/20; C07C225/22; C07C231/02; C07C233/33; C07C233/42; C07C233/61; C07C233/65; C07C233/76; C07C247/14; C07C271/18; C07C271/34; C07C271/44; C07C275/26; C07C275/64; C07C323/22; C07D213/65; C07D215/20; C07D221/04
Foreign References:
| WO2004087153A2 | 2004-10-14 | |||
| WO2010003023A2 | 2010-01-07 | |||
| GB1425295A | 1976-02-18 | |||
| WO2003082265A2 | 2003-10-09 |
Other References:
SUN, FANG-GANG; YE, SONG: "N-Heterocyclic carbene-catalyzed [4 + 1] annulation of phthalaldehyde and imines", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 9(10), JPN6017015561, 2011, pages 3632-3635
ARENS, A.; MIKSTAIS, U.; VANAGS, G.: "Amino derivatives of 2-piperonyl-1,3-indandione", ZHURNAL OBSHCHEI KHIMII, vol. 34(2), JPN6017015562, 1964, pages 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., vol. 7, JPN6017015564, 1965, pages 77-80
VASILEV, G.; MIKHAILOV, V.: "Synthesis, chemical structure, and biological activity of certain N-substituted 2-ureido- or thioure", DOKLADY BOLGARSKOI AKADEMII NAUK, vol. 39(2), JPN6017015566, 1986, pages 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, vol. (4), JPN6017015568, 1972, pages 441-4
BITE, DZ.; VALTERE, S.; ARENS, A.: "Substituted thiourea β-dicarbonyl compounds. IX. Spectroscopic study of 2-substituted N-[1,3-inda", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (1), JPN6017015569, 1969, pages 109-12
ARENS, A.; LENCBERGS, I.: "Isomerization of 2-amino-2-substituted 1,3-indandiones", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (6), JPN6017015571, 1980, pages 677-91
ROTBERGS, J.; STRAUTINA, V.; OSKAJA, V.: "Condensation of dicarboxylic acid anhydrides with compounds containing active methylene groups. XXV", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (1), JPN6017015572, 1974, pages 75-8
ZALUKAEV, L. P.; SOLOV'EV, A. S.: "Synthesis of new α-nitro-α-arylmethylenephthalides", IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII, KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, vol. 13(10), JPN6017015573, 1970, pages 1453-6
ARENS, AUGUSTS; PRIKULIS, A.: "Reduction of aminodicarboxylic compounds. III. 2-Alkylamino-2-phenyl-3-indanon-1-ol and 2-alkylamin", JOURNAL OF ORGANIC CHEMISTRY OF THE USSR, vol. 5(9), JPN6017015575, 1969, pages 2094-2097
ZALUKAEV, L. P.; VNENKOVSKAYA, D. G.: "Synthesis of α-nitromethylpyridine and its derivatives", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, vol. (3), JPN6017015576, 1967, pages 515-17
BRIEDE, V.; OSKAJA, V.; LUKINA, I.: "4,5-Dimethoxy-2-β-naphthyl-1,3-indandione", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (3), JPN6017015578, 1967, pages 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, vol. (3), JPN6017015580, 1966, pages 342-6
ECKSTEIN, ZYGMUNT; URBANSKI, TADEUSZ: "Infrared absorption spectra of 2-nitroindandione derivatives", BULLETIN DE L'ACADEMIE POLONAISE DES SCIENCES, SERIE DES SCIENCES CHIMIQUES, vol. 8(10), JPN6017015581, 1960, pages 579-86
ZALUKAJEVS, L.; VANAGS, E.: "Nitration of phthalones", ZHURNAL OBSHCHEI KHIMII, vol. 27, JPN6017015582, 1957, pages 3278-82
ZALUKAIEVS, L.; VANAGS, E.: "Preparation of 2-nitromethylquinoline and its derivatives", ZHURNAL OBSHCHEI KHIMII, vol. 26, JPN6017015583, 1956, pages 2639-42
VEGNERE, V.; STRADINS, J.: "Adsorptive capacity of 2-amino-substituted indans on a mercury electrode", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (4), JPN6017015584, 1973, pages 446-51
ARENS, AUGUSTS; VANAGS, V.; GERMANE, S.; OZOLINS, V.: "2-Amino-2-halophenyl-1,3-indandiones", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (4), JPN6017015585, 1969, pages 446-51
GUDRINIECE, E.; BRUVELE, N.; IEVINS, A.: "2-Azido-2-substituted indan-1,3-dione", DOKLADY AKADEMII NAUK SSSR, vol. 171(4), JPN6017015586, 1966, pages 869-71
ARENS, A.; MIKSTAIS, U.; VANAGS, G.: "Amino derivatives of 2-piperonyl-1,3-indandione", ZHURNAL OBSHCHEI KHIMII, vol. 34(2), JPN6017015562, 1964, pages 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., vol. 7, JPN6017015564, 1965, pages 77-80
VASILEV, G.; MIKHAILOV, V.: "Synthesis, chemical structure, and biological activity of certain N-substituted 2-ureido- or thioure", DOKLADY BOLGARSKOI AKADEMII NAUK, vol. 39(2), JPN6017015566, 1986, pages 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, vol. (4), JPN6017015568, 1972, pages 441-4
BITE, DZ.; VALTERE, S.; ARENS, A.: "Substituted thiourea β-dicarbonyl compounds. IX. Spectroscopic study of 2-substituted N-[1,3-inda", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (1), JPN6017015569, 1969, pages 109-12
ARENS, A.; LENCBERGS, I.: "Isomerization of 2-amino-2-substituted 1,3-indandiones", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (6), JPN6017015571, 1980, pages 677-91
ROTBERGS, J.; STRAUTINA, V.; OSKAJA, V.: "Condensation of dicarboxylic acid anhydrides with compounds containing active methylene groups. XXV", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (1), JPN6017015572, 1974, pages 75-8
ZALUKAEV, L. P.; SOLOV'EV, A. S.: "Synthesis of new α-nitro-α-arylmethylenephthalides", IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII, KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, vol. 13(10), JPN6017015573, 1970, pages 1453-6
ARENS, AUGUSTS; PRIKULIS, A.: "Reduction of aminodicarboxylic compounds. III. 2-Alkylamino-2-phenyl-3-indanon-1-ol and 2-alkylamin", JOURNAL OF ORGANIC CHEMISTRY OF THE USSR, vol. 5(9), JPN6017015575, 1969, pages 2094-2097
ZALUKAEV, L. P.; VNENKOVSKAYA, D. G.: "Synthesis of α-nitromethylpyridine and its derivatives", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, vol. (3), JPN6017015576, 1967, pages 515-17
BRIEDE, V.; OSKAJA, V.; LUKINA, I.: "4,5-Dimethoxy-2-β-naphthyl-1,3-indandione", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (3), JPN6017015578, 1967, pages 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, vol. (3), JPN6017015580, 1966, pages 342-6
ECKSTEIN, ZYGMUNT; URBANSKI, TADEUSZ: "Infrared absorption spectra of 2-nitroindandione derivatives", BULLETIN DE L'ACADEMIE POLONAISE DES SCIENCES, SERIE DES SCIENCES CHIMIQUES, vol. 8(10), JPN6017015581, 1960, pages 579-86
ZALUKAJEVS, L.; VANAGS, E.: "Nitration of phthalones", ZHURNAL OBSHCHEI KHIMII, vol. 27, JPN6017015582, 1957, pages 3278-82
ZALUKAIEVS, L.; VANAGS, E.: "Preparation of 2-nitromethylquinoline and its derivatives", ZHURNAL OBSHCHEI KHIMII, vol. 26, JPN6017015583, 1956, pages 2639-42
VEGNERE, V.; STRADINS, J.: "Adsorptive capacity of 2-amino-substituted indans on a mercury electrode", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (4), JPN6017015584, 1973, pages 446-51
ARENS, AUGUSTS; VANAGS, V.; GERMANE, S.; OZOLINS, V.: "2-Amino-2-halophenyl-1,3-indandiones", LATVIJAS PSR ZINATNU AKADEMIJAS VESTIS, KIMIJAS SERIJA, vol. (4), JPN6017015585, 1969, pages 446-51
GUDRINIECE, E.; BRUVELE, N.; IEVINS, A.: "2-Azido-2-substituted indan-1,3-dione", DOKLADY AKADEMII NAUK SSSR, vol. 171(4), JPN6017015586, 1966, pages 869-71
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