Title:
PIM KINASE INHIBITOR
Document Type and Number:
WIPO Patent Application WO/2022/166860
Kind Code:
A1
Abstract:
A compound having a structure as shown in general formula (I), a deuterated compound, a stereoisomer, or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising same, and use thereof. The compound has a good PIM kinase inhibitory effect, is a novel and ideal PIM inhibitor having high activity and low toxicity, and can be used for treating and/or preventing hematoma such as acute myeloid leukemia, bone marrow fibrosis and chronic lymphocytic leukemia, solid tumors such as gastric cancer and prostate cancer, and other diseases.
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Inventors:
YANG XIN (CN)
CUI RONG (CN)
YIN JIANMING (CN)
ZHENG MEI (CN)
CHEN NANYU (CN)
LV YUBIN (CN)
CUI RONG (CN)
YIN JIANMING (CN)
ZHENG MEI (CN)
CHEN NANYU (CN)
LV YUBIN (CN)
Application Number:
PCT/CN2022/074876
Publication Date:
August 11, 2022
Filing Date:
January 29, 2022
Export Citation:
Assignee:
HANGZHOU BANGSHUN PHARMACEUTICAL CO LTD (CN)
International Classes:
C07D487/04; A61K31/5025; A61P35/00; A61P35/02
Domestic Patent References:
| WO2016161248A1 | 2016-10-06 | |||
| WO2013013188A1 | 2013-01-24 | |||
| WO2013013188A1 | 2013-01-24 |
Foreign References:
| CN101600718A | 2009-12-09 | |||
| US20120058997A1 | 2012-03-08 | |||
| CN101594909A | 2009-12-02 |
Other References:
DATABASE REGISTRY 13 November 2020 (2020-11-13), "Imidazo[1,2-b]pyridazin-6-amine, N-[(1-methyl-4-piperidinyl)methyl]-3-[4- (trifluoromethoxy)phenyl]- (CA INDEX NAME)", XP055960448, retrieved from STN Database accession no. 2514698-66-7
DATABASE Registry 12 November 2020 (2020-11-12), "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3- (trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]- (CA INDEX NAME)", XP055961248, retrieved from STN Database accession no. 2512208-19-2
DATABASE Registry 9 September 2020 (2020-09-09), "2476264-12-5 Registry -INDEX NA055961248 ME NOT YET ASSIGNED", XP055961251, retrieved from STN Database accession no. 2476264-12-5
DATABASE Registry "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3- (trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]-, trans-, methanesulfonate (1:1) (CA INDEX NAME)", XP055961254, retrieved from STN Database accession no. 2476264-08-9
DATABASE Registry 1 April 2014 (2014-04-01), "Cyclohexanol, 4-[[3-(3-thienyl)imidazo[1,2-b]pyridazin-6-yl]amino]-, trans- (CA INDEX NAME)", XP055961255, retrieved from STN Database accession no. 1627730-21-5
DATABASE Registry 13 November 2013 (2013-11-13), "1,4-Cyclohexanediamine, N1-[3-(1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6- yl]-, trans- (CA INDEX NAME)", XP055961259, retrieved from STN Database accession no. 1469884-30-7
DATABASE Registry 12 November 2020 (2020-11-12), "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]- (CA INDEX NAME)", XP055961261, retrieved from STN Database accession no. 2512208-19-2
DATABASE Registry "2476264-12-5 Registry", XP055961264, retrieved from STN Database accession no. 2476264-12-5
DATABASE Registry 9 September 2020 (2020-09-09), "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3- (trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]-, trans-, methanesulfonate (1:1) (CA INDEX NAME)", XP055961266, retrieved from STN Database accession no. 2476264-08-9
DATABASE Registry 4 February 2013 (2013-02-04), "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3- (trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]-, hydrochloride (1:1), trans- (CA INDEX NAME)", XP055961260, retrieved from STN Database accession no. 1418143-09-5
DATABASE Registry 3 October 2008 (2008-10-03), "Imidazo[1,2-b]pyridazin-6-amine, N-cycloheptyl-3-(4-pyridinyl)-(CA INDEX NAME)", XP055961267, retrieved from STN Database accession no. 1056557-65-3
DATABASE Registry 4 February 2013 (2013-02-04), "Cyclohexanol, 4-[[3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6- yl]amino]-, hydrochloride (1:1), trans- (CA INDEX NAME)", XP055961268, retrieved from STN Database accession no. 1418143-08-4
DATABASE Registry 3 October 2008 (2008-10-03), "Imidazo[1,2-b]pyridazin-6-amine, N-cycloheptyl-3-(4-pyridinyl)-(CA INDEX NAME)", XP055961274, retrieved from STN Database accession no. 1056557-65-3
PASTOR, J. ET AL.: "Hit to lead evaluation of 1, 2, 3-triazolo[4, 5-b]pyridines as PIM kinase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 22, 5 January 2012 (2012-01-05), pages 1591 - 1597, XP028398221, DOI: 10.1016/j.bmcl.2011.12.130
DATABASE REGISTRY 8 July 2021 (2021-07-08), "Imidazo[1,2-b]pyridazin-6-amine, N-[(1-methyl-4-piperidinyl)methyl]-3-[3- (trifluoromethoxy)phenyl]-, sulfate (1:1) (CA INDEX NAME)", XP055960455, retrieved from STN Database accession no. 2650928-85-9
DATABASE Registry 6 July 2021 (2021-07-06), "Cyclopentanemethanol, 3-[[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]-.alpha.,.alpha.-dimethyl-, (1R,3R)-rel- (CA INDEX NAME)", XP055961293, retrieved from STN Database accession no. 2649585-63-5
XING QIYI ET AL., BASIC ORGANIC CHEMISTRY, vol. 1, pages 104 - 105
PAC, vol. 68, 1996, pages 2193
BLOOD., vol. 115, no. 15, 2010, pages 3109 - 3117
DATABASE Registry 12 November 2020 (2020-11-12), "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3- (trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]- (CA INDEX NAME)", XP055961248, retrieved from STN Database accession no. 2512208-19-2
DATABASE Registry 9 September 2020 (2020-09-09), "2476264-12-5 Registry -INDEX NA055961248 ME NOT YET ASSIGNED", XP055961251, retrieved from STN Database accession no. 2476264-12-5
DATABASE Registry "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3- (trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]-, trans-, methanesulfonate (1:1) (CA INDEX NAME)", XP055961254, retrieved from STN Database accession no. 2476264-08-9
DATABASE Registry 1 April 2014 (2014-04-01), "Cyclohexanol, 4-[[3-(3-thienyl)imidazo[1,2-b]pyridazin-6-yl]amino]-, trans- (CA INDEX NAME)", XP055961255, retrieved from STN Database accession no. 1627730-21-5
DATABASE Registry 13 November 2013 (2013-11-13), "1,4-Cyclohexanediamine, N1-[3-(1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6- yl]-, trans- (CA INDEX NAME)", XP055961259, retrieved from STN Database accession no. 1469884-30-7
DATABASE Registry 12 November 2020 (2020-11-12), "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]- (CA INDEX NAME)", XP055961261, retrieved from STN Database accession no. 2512208-19-2
DATABASE Registry "2476264-12-5 Registry", XP055961264, retrieved from STN Database accession no. 2476264-12-5
DATABASE Registry 9 September 2020 (2020-09-09), "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3- (trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]-, trans-, methanesulfonate (1:1) (CA INDEX NAME)", XP055961266, retrieved from STN Database accession no. 2476264-08-9
DATABASE Registry 4 February 2013 (2013-02-04), "Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-[[3-[3- (trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]amino]-, hydrochloride (1:1), trans- (CA INDEX NAME)", XP055961260, retrieved from STN Database accession no. 1418143-09-5
DATABASE Registry 3 October 2008 (2008-10-03), "Imidazo[1,2-b]pyridazin-6-amine, N-cycloheptyl-3-(4-pyridinyl)-(CA INDEX NAME)", XP055961267, retrieved from STN Database accession no. 1056557-65-3
DATABASE Registry 4 February 2013 (2013-02-04), "Cyclohexanol, 4-[[3-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-6- yl]amino]-, hydrochloride (1:1), trans- (CA INDEX NAME)", XP055961268, retrieved from STN Database accession no. 1418143-08-4
DATABASE Registry 3 October 2008 (2008-10-03), "Imidazo[1,2-b]pyridazin-6-amine, N-cycloheptyl-3-(4-pyridinyl)-(CA INDEX NAME)", XP055961274, retrieved from STN Database accession no. 1056557-65-3
PASTOR, J. ET AL.: "Hit to lead evaluation of 1, 2, 3-triazolo[4, 5-b]pyridines as PIM kinase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 22, 5 January 2012 (2012-01-05), pages 1591 - 1597, XP028398221, DOI: 10.1016/j.bmcl.2011.12.130
DATABASE REGISTRY 8 July 2021 (2021-07-08), "Imidazo[1,2-b]pyridazin-6-amine, N-[(1-methyl-4-piperidinyl)methyl]-3-[3- (trifluoromethoxy)phenyl]-, sulfate (1:1) (CA INDEX NAME)", XP055960455, retrieved from STN Database accession no. 2650928-85-9
DATABASE Registry 6 July 2021 (2021-07-06), "Cyclopentanemethanol, 3-[[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]-.alpha.,.alpha.-dimethyl-, (1R,3R)-rel- (CA INDEX NAME)", XP055961293, retrieved from STN Database accession no. 2649585-63-5
XING QIYI ET AL., BASIC ORGANIC CHEMISTRY, vol. 1, pages 104 - 105
PAC, vol. 68, 1996, pages 2193
BLOOD., vol. 115, no. 15, 2010, pages 3109 - 3117
Attorney, Agent or Firm:
SINO-CREATIVITY INTELLECTUAL PROPERTY LAW FIRM (CN)
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