JP2018515614A5 - - Google Patents
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- Publication number
- JP2018515614A5 JP2018515614A5 JP2018511344A JP2018511344A JP2018515614A5 JP 2018515614 A5 JP2018515614 A5 JP 2018515614A5 JP 2018511344 A JP2018511344 A JP 2018511344A JP 2018511344 A JP2018511344 A JP 2018511344A JP 2018515614 A5 JP2018515614 A5 JP 2018515614A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkenyl
- aryl
- heteroaryl
- alkynyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 148
- 125000003118 aryl group Chemical group 0.000 claims description 131
- 125000003342 alkenyl group Chemical group 0.000 claims description 124
- 125000000304 alkynyl group Chemical group 0.000 claims description 108
- 125000001072 heteroaryl group Chemical group 0.000 claims description 108
- 150000001875 compounds Chemical class 0.000 claims description 60
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 238000010276 construction Methods 0.000 claims description 22
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 21
- 239000002246 antineoplastic agent Substances 0.000 claims description 21
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 125000003275 alpha amino acid group Chemical group 0.000 description 9
- 238000001727 in vivo Methods 0.000 description 8
- JUQMLSGOTNKJKI-IZUQBHJASA-N (1s,4r)-2-(4-methylpiperazin-4-ium-1-carbonyl)-7-oxabicyclo[2.2.1]heptane-3-carboxylate Chemical compound C1C[NH+](C)CCN1C(=O)C1C(C([O-])=O)[C@H]2CC[C@@H]1O2 JUQMLSGOTNKJKI-IZUQBHJASA-N 0.000 description 7
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 3
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000002502 liposome Substances 0.000 description 3
- 101000741929 Caenorhabditis elegans Serine/threonine-protein phosphatase 2A catalytic subunit Proteins 0.000 description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 150000003140 primary amides Chemical class 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562162501P | 2015-05-15 | 2015-05-15 | |
| US62/162,501 | 2015-05-15 | ||
| PCT/US2016/032123 WO2016186963A1 (en) | 2015-05-15 | 2016-05-12 | Oxabicycloheptane prodrugs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020105369A Division JP2020180130A (ja) | 2015-05-15 | 2020-06-18 | オキサビシクロヘプタンプロドラッグ |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2018515614A JP2018515614A (ja) | 2018-06-14 |
| JP2018515614A5 true JP2018515614A5 (https=) | 2019-06-06 |
| JP7187023B2 JP7187023B2 (ja) | 2022-12-12 |
| JP7187023B6 JP7187023B6 (ja) | 2023-01-05 |
Family
ID=57276640
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018511344A Active JP7187023B6 (ja) | 2015-05-15 | 2016-05-12 | オキサビシクロヘプタンプロドラッグ |
| JP2020105369A Pending JP2020180130A (ja) | 2015-05-15 | 2020-06-18 | オキサビシクロヘプタンプロドラッグ |
| JP2023064829A Pending JP2023100645A (ja) | 2015-05-15 | 2023-04-12 | オキサビシクロヘプタンプロドラッグ |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020105369A Pending JP2020180130A (ja) | 2015-05-15 | 2020-06-18 | オキサビシクロヘプタンプロドラッグ |
| JP2023064829A Pending JP2023100645A (ja) | 2015-05-15 | 2023-04-12 | オキサビシクロヘプタンプロドラッグ |
Country Status (12)
| Country | Link |
|---|---|
| US (5) | US9988394B2 (https=) |
| EP (2) | EP3736275B1 (https=) |
| JP (3) | JP7187023B6 (https=) |
| CN (2) | CN107708686B (https=) |
| AU (1) | AU2016263079B2 (https=) |
| DK (1) | DK3294287T3 (https=) |
| ES (2) | ES2985668T3 (https=) |
| HU (1) | HUE050177T2 (https=) |
| IL (2) | IL255516B (https=) |
| MX (2) | MX386975B (https=) |
| TW (2) | TWI757720B (https=) |
| WO (1) | WO2016186963A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11724982B2 (en) | 2014-10-10 | 2023-08-15 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2877167A1 (en) | 2012-06-29 | 2014-01-03 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of diabetes |
| EP2983661B1 (en) | 2013-04-09 | 2024-05-29 | Lixte Biotechnology, Inc. | Formulations of oxabicycloheptanes and oxabicycloheptenes |
| US10071094B2 (en) | 2014-07-24 | 2018-09-11 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Protein phosphatase 2A inhibitors for treating myelodysplastic syndromes |
| AU2016219853B2 (en) | 2015-02-19 | 2019-05-16 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of depressive and stress disorders |
| DK3294287T3 (da) * | 2015-05-15 | 2020-06-08 | Lixte Biotechnology Inc | Oxabicycloheptan-prodrugs |
| MX2019006694A (es) | 2016-12-08 | 2019-08-21 | Lixte Biotechnology Inc | Oxabicicloheptanos para la modulacion de la respuesta inmunitaria. |
| CN118791500B (zh) * | 2024-06-17 | 2025-11-21 | 中国药科大学 | 7-氧杂双环[2.2.1]庚烷-2,3-二羧酸类衍生物及其制备方法和应用 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5206386A (en) | 1991-03-20 | 1993-04-27 | Isp Investments Inc. | Controlled release N-substituted pyrrolidone esters and process for the use thereof |
| US6949624B1 (en) | 1999-08-03 | 2005-09-27 | The United States Of America As Represented By The Department Of Health And Human Services | Cloning of the human nuclear receptor co-repressor gene |
| AU2001243253A1 (en) | 2000-02-24 | 2001-09-03 | Biocryst Pharmaceuticals, Inc. | Prodrugs of substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors |
| EP1463713A1 (en) | 2001-11-23 | 2004-10-06 | Eli Lilly And Company | Prodrugs of excitatory amino acids |
| WO2004087153A2 (en) * | 2003-03-28 | 2004-10-14 | Chiron Corporation | Use of organic compounds for immunopotentiation |
| CA2641308A1 (en) | 2006-02-06 | 2007-08-16 | Lixte Biotechnology Holdings, Inc. | Use of phosphatases to treat tumors overexpressing n-cor |
| US20090018142A9 (en) * | 2006-05-02 | 2009-01-15 | Zhengping Zhuang | Use of phosphatases to treat tumors overexpressing N-CoR |
| WO2008030617A2 (en) | 2006-09-07 | 2008-03-13 | Stemline Therapeutics, Inc. | Cancer therapy with cantharidin and cantharidin analogs |
| US20080097561A1 (en) | 2006-10-18 | 2008-04-24 | Medcool, Inc. | Dual cycle thermal system and method of use |
| WO2008058342A1 (en) * | 2006-11-15 | 2008-05-22 | Genetic Technologies Limited | Compounds, compositions and methods for controlling invertebrate pests |
| CA2676422C (en) | 2007-02-06 | 2018-10-16 | Lixte Biotechnology Holdings, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| US20090035292A1 (en) * | 2007-08-03 | 2009-02-05 | Kovach John S | Use of phosphatases to treat neuroblastomas and medulloblastomas |
| EA018618B1 (ru) | 2007-10-01 | 2013-09-30 | Ликсте Байотекнолоджи, Инк. | Ингибиторы hdac |
| CA2730148C (en) | 2008-08-01 | 2018-04-03 | Lixte Biotechnology, Inc. | Neuroprotective agents for the prevention and treatment of neurodegenerative diseases |
| WO2010147612A1 (en) | 2009-06-18 | 2010-12-23 | Lixte Biotechnology, Inc. | Methods of modulating cell regulation by inhibiting p53 |
| EP2309853A4 (en) | 2008-08-01 | 2012-04-25 | Lixte Biotechnology Inc | METHOD FOR CELL MITITULATING BY INHIBITION OF SERIN / THREONINE PHOSPHATASE |
| US8227473B2 (en) | 2008-08-01 | 2012-07-24 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| EP2560634A1 (en) | 2010-04-23 | 2013-02-27 | Piramal Enterprises Limited | Nitric oxide releasing prodrugs of therapeutic agents |
| US20140235649A1 (en) * | 2011-05-24 | 2014-08-21 | Lixte Biotechnology, Inc. | Use of phosphatase inhibitors or histone deacetylase inhibitors to treat diseases characterized by loss of protein function |
| WO2013180271A1 (ja) | 2012-06-01 | 2013-12-05 | 大正製薬株式会社 | 含フッ素アミノ酸のプロドラッグ |
| JP6262225B2 (ja) | 2012-06-29 | 2018-01-17 | リクスト・バイオテクノロジー，インコーポレイテッド | オキサビシクロヘプタン類、および再灌流障害の治療のためのオキサビシクロヘプタン類 |
| CA2877167A1 (en) | 2012-06-29 | 2014-01-03 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of diabetes |
| WO2014137741A1 (en) | 2013-03-05 | 2014-09-12 | Lixte Biotechnology, Inc. | Hdac inhibitors for treating traumatic brain injury |
| EP2968279A4 (en) | 2013-03-15 | 2016-09-28 | Lixte Biotechnology Inc | SANGUINARIN ANALOG PPC2 HEMMER FOR CANCER TREATMENT |
| EP2983661B1 (en) * | 2013-04-09 | 2024-05-29 | Lixte Biotechnology, Inc. | Formulations of oxabicycloheptanes and oxabicycloheptenes |
| JP2016538281A (ja) * | 2013-11-15 | 2016-12-08 | リクスト・バイオテクノロジー，インコーポレイテッド | 血液脳関門を通過するタンパク質ホスファターゼ阻害剤 |
| US9051332B1 (en) | 2013-11-20 | 2015-06-09 | Transitions Optical, Inc. | Photochromic indeno-fused ring pyran compounds |
| WO2015196073A1 (en) | 2014-06-20 | 2015-12-23 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of ovarian cancer |
| US10071094B2 (en) | 2014-07-24 | 2018-09-11 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Protein phosphatase 2A inhibitors for treating myelodysplastic syndromes |
| WO2016040877A1 (en) | 2014-09-12 | 2016-03-17 | Lixte Biotechnology, Inc. | Human dosing of phosphatase inhibitor |
| WO2016061193A1 (en) | 2014-10-15 | 2016-04-21 | Lixte Biotechnology, Inc. | Process of synthesizing 3-(4-methylpiperazine-1-carbonyl)-7-oxabicyclo[2.2.1] heptane-2-carboxylic acid |
| AU2016219853B2 (en) | 2015-02-19 | 2019-05-16 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of depressive and stress disorders |
| DK3294287T3 (da) | 2015-05-15 | 2020-06-08 | Lixte Biotechnology Inc | Oxabicycloheptan-prodrugs |
| EP3407887B1 (en) | 2016-01-27 | 2021-09-01 | Lixte Biotechnology, Inc. | Clinical regimen for treating myelodysplastic syndrome with phosphatase inhibitor |
| MX2019006694A (es) | 2016-12-08 | 2019-08-21 | Lixte Biotechnology Inc | Oxabicicloheptanos para la modulacion de la respuesta inmunitaria. |
| US20210275521A1 (en) | 2017-12-05 | 2021-09-09 | Lixte Biotechnology, Inc. | Oxabicycloheptanes for treatment of secondary acute myeloid leukemia |
-
2016
- 2016-05-12 DK DK16796978.1T patent/DK3294287T3/da active
- 2016-05-12 CN CN201680032555.1A patent/CN107708686B/zh not_active Expired - Fee Related
- 2016-05-12 AU AU2016263079A patent/AU2016263079B2/en active Active
- 2016-05-12 ES ES20167812T patent/ES2985668T3/es active Active
- 2016-05-12 HU HUE16796978A patent/HUE050177T2/hu unknown
- 2016-05-12 MX MX2017014549A patent/MX386975B/es unknown
- 2016-05-12 ES ES16796978T patent/ES2795950T3/es active Active
- 2016-05-12 EP EP20167812.5A patent/EP3736275B1/en active Active
- 2016-05-12 JP JP2018511344A patent/JP7187023B6/ja active Active
- 2016-05-12 CN CN202110080437.0A patent/CN113150030A/zh active Pending
- 2016-05-12 EP EP16796978.1A patent/EP3294287B1/en active Active
- 2016-05-12 MX MX2021012440A patent/MX393461B/es unknown
- 2016-05-12 WO PCT/US2016/032123 patent/WO2016186963A1/en not_active Ceased
- 2016-05-13 TW TW109111871A patent/TWI757720B/zh active
- 2016-05-13 TW TW105114967A patent/TWI693226B/zh active
- 2016-05-13 US US15/154,304 patent/US9988394B2/en active Active
-
2017
- 2017-11-08 IL IL255516A patent/IL255516B/en active IP Right Grant
-
2018
- 2018-05-01 US US15/968,462 patent/US10364252B2/en active Active
-
2019
- 2019-06-12 US US16/439,227 patent/US10618908B2/en active Active
-
2020
- 2020-01-14 IL IL272027A patent/IL272027B/en unknown
- 2020-02-05 US US16/782,970 patent/US11236102B2/en active Active
- 2020-06-18 JP JP2020105369A patent/JP2020180130A/ja active Pending
-
2022
- 2022-01-27 US US17/586,548 patent/US11866444B2/en active Active
-
2023
- 2023-04-12 JP JP2023064829A patent/JP2023100645A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11724982B2 (en) | 2014-10-10 | 2023-08-15 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
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