Title:
SUBSTITUTED 3-FLUOROBENZENEPROPANOATE COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITIONS, AND USES
Document Type and Number:
WIPO Patent Application WO/2024/078387
Kind Code:
A1
Abstract:
A substituted 3-fluorobenzenepropanoate compound represented by formula (I), an optical isomer thereof, a pharmaceutically acceptable salt thereof, a solvate (such as a hydrate) thereof, a clathrate thereof, a racemate thereof, a co-crystal thereof, an isotopic label thereof, or a nitrogen oxide thereof, as well as pharmaceutical compositions and uses thereof. The compound has significantly elevated drug activity, and can effectively treat and/or prevent inflammation, pain, fever, cancer, or senile dementia.
Inventors:
GAO QINGZHI (CN)
LIU SHENGNAN (CN)
SUN ZIRU (CN)
LIU YANG (CN)
DU JINPING (CN)
HAN JIANBIN (CN)
LI YANG (CN)
ZHANG SHUNJIE (CN)
ZHAO FUPING (CN)
GAO XIANGQIAN (CN)
LIU SHENGNAN (CN)
SUN ZIRU (CN)
LIU YANG (CN)
DU JINPING (CN)
HAN JIANBIN (CN)
LI YANG (CN)
ZHANG SHUNJIE (CN)
ZHAO FUPING (CN)
GAO XIANGQIAN (CN)
Application Number:
PCT/CN2023/123222
Publication Date:
April 18, 2024
Filing Date:
October 07, 2023
Export Citation:
Assignee:
TIANJIN GUDUI BIO PHARM CO LTD (CN)
International Classes:
C07D295/205; A61K31/265; A61K31/27; A61P25/00; A61P29/00; C07C69/96
Domestic Patent References:
| WO2007095383A2 | 2007-08-23 | |||
| WO1988001615A1 | 1988-03-10 |
Foreign References:
| CN115677507A | 2023-02-03 | |||
| CN111635430A | 2020-09-08 |
Other References:
LIANG GE: "Photoredox-catalyzed C–C bond cleavage of cyclopropanes for the formation of C(sp3)–heteroatom bonds", NATURE COMMUNICATIONS, NATURE PUBLISHING GROUP, UK, vol. 13, no. 1, 8 October 2022 (2022-10-08), UK, pages 5938, XP093158681, ISSN: 2041-1723, DOI: 10.1038/s41467-022-33602-4
ZHANG YU, SAHOO PRAKASH KUMAR, REN PENG, QIN YUMAN, CAUWENBERGH ROBIN, NIMMEGEERS PHILIPPE, SIVARAMAN GANDHI, VAN PASSEL STEVEN, G: "Transition metal-free approach for late-stage benzylic C(sp 3 )–H etherifications and esterifications", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 58, no. 81, 11 October 2022 (2022-10-11), UK , pages 11454 - 11457, XP093158683, ISSN: 1359-7345, DOI: 10.1039/D2CC02661A
BRANDON D. EDEN: "Microwave-assisted synthesis and in vitro stability of N-benzylamide non-steroidal anti-inflammatory drug conjugates for CNS delivery", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 29, no. 12, 1 June 2019 (2019-06-01), Amsterdam NL , pages 1487 - 1491, XP093158684, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2019.04.016
ROSARIO PIGNATELLO: "Flurbiprofen Derivatives in Alzheimer’s Disease: Synthesis, Pharmacokinetic and Biological Assessment of Lipoamino Acid Prodrugs", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 19, no. 1, 1 January 2008 (2008-01-01), US , pages 349 - 357, XP093158685, ISSN: 1043-1802, DOI: 10.1021/bc700312y
ALESSANDRA AMMAZZALORSO; ROSA AMOROSO; GIANCARLO BETTONI; BARBARA DE FILIPPIS; MARIALUIGIA FANTACUZZI; LETIZIA GIAMPIETRO; CRISTIN: "Asymmetric Synthesis of Arylpropionic Acids and Aryloxy Acids by Using Lactamides as Chiral Auxiliaries", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2006, no. 18, 3 August 2006 (2006-08-03), DE , pages 4088 - 4091, XP072115910, ISSN: 1434-193X, DOI: 10.1002/ejoc.200600484
DATABASE Registry 8 July 2021 (2021-07-08), ANONYMOUS: "[1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, 2-(dimethylamino)-2-oxoethyl ester, (αR)- (CA INDEX NAME)", XP093158748, retrieved from STNext Database accession no. 2650910-05-5
ZHANG YU, SAHOO PRAKASH KUMAR, REN PENG, QIN YUMAN, CAUWENBERGH ROBIN, NIMMEGEERS PHILIPPE, SIVARAMAN GANDHI, VAN PASSEL STEVEN, G: "Transition metal-free approach for late-stage benzylic C(sp 3 )–H etherifications and esterifications", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 58, no. 81, 11 October 2022 (2022-10-11), UK , pages 11454 - 11457, XP093158683, ISSN: 1359-7345, DOI: 10.1039/D2CC02661A
BRANDON D. EDEN: "Microwave-assisted synthesis and in vitro stability of N-benzylamide non-steroidal anti-inflammatory drug conjugates for CNS delivery", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 29, no. 12, 1 June 2019 (2019-06-01), Amsterdam NL , pages 1487 - 1491, XP093158684, ISSN: 0960-894X, DOI: 10.1016/j.bmcl.2019.04.016
ROSARIO PIGNATELLO: "Flurbiprofen Derivatives in Alzheimer’s Disease: Synthesis, Pharmacokinetic and Biological Assessment of Lipoamino Acid Prodrugs", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 19, no. 1, 1 January 2008 (2008-01-01), US , pages 349 - 357, XP093158685, ISSN: 1043-1802, DOI: 10.1021/bc700312y
ALESSANDRA AMMAZZALORSO; ROSA AMOROSO; GIANCARLO BETTONI; BARBARA DE FILIPPIS; MARIALUIGIA FANTACUZZI; LETIZIA GIAMPIETRO; CRISTIN: "Asymmetric Synthesis of Arylpropionic Acids and Aryloxy Acids by Using Lactamides as Chiral Auxiliaries", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2006, no. 18, 3 August 2006 (2006-08-03), DE , pages 4088 - 4091, XP072115910, ISSN: 1434-193X, DOI: 10.1002/ejoc.200600484
DATABASE Registry 8 July 2021 (2021-07-08), ANONYMOUS: "[1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, 2-(dimethylamino)-2-oxoethyl ester, (αR)- (CA INDEX NAME)", XP093158748, retrieved from STNext Database accession no. 2650910-05-5
Attorney, Agent or Firm:
BEIJING TANLULAI PATENT AGENT LTD (CN)
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