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 (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) |
| EP (2) | EP3736275B1 (cg-RX-API-DMAC7.html) |
| JP (3) | JP7187023B6 (cg-RX-API-DMAC7.html) |
| CN (2) | CN113150030A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2016263079B2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK3294287T3 (cg-RX-API-DMAC7.html) |
| ES (2) | ES2985668T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUE050177T2 (cg-RX-API-DMAC7.html) |
| IL (2) | IL255516B (cg-RX-API-DMAC7.html) |
| MX (2) | MX393461B (cg-RX-API-DMAC7.html) |
| TW (2) | TWI757720B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016186963A1 (cg-RX-API-DMAC7.html) |
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 (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2867239A4 (en) | 2012-06-29 | 2015-12-23 | Lixte Biotechnology Inc | OXABICYCLOHEPTANES AND OXABICYCLOHEPTENES FOR THE TREATMENT OF DIABETES |
| WO2014168941A1 (en) | 2013-04-09 | 2014-10-16 | 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 |
| MX393461B (es) | 2015-05-15 | 2025-03-24 | Lixte Biotechnology Inc | Farmacos precursores de oxabicicloheptanos |
| US12168008B2 (en) | 2016-12-08 | 2024-12-17 | Lixte Biotechnology, Inc. | Oxabicycloheptanes for modulation of immune response |
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 |
| EP1986619A4 (en) | 2006-02-06 | 2010-04-28 | Lixte Biotechnology Inc | USE OF PHOSPHATASES FOR THE TREATMENT OF TUMORS BY N-COR OVEREXPRESSION |
| US20090018142A9 (en) * | 2006-05-02 | 2009-01-15 | Zhengping Zhuang | Use of phosphatases to treat tumors overexpressing N-CoR |
| TWI449524B (zh) | 2006-09-07 | 2014-08-21 | Stemline Therapeutics Inc | 以斑螫酸酐（ｃａｎｔｈａｒｉｄｉｎ）及斑螫酸酐類似物進行之癌症治療 |
| US20080097561A1 (en) | 2006-10-18 | 2008-04-24 | Medcool, Inc. | Dual cycle thermal system and method of use |
| AU2007321720A1 (en) * | 2006-11-15 | 2008-05-22 | Genetic Technologies Limited | Compounds, compositions and methods for controlling invertebrate pests |
| US7998957B2 (en) | 2007-02-06 | 2011-08-16 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicylcoheptenes, their preparation and use |
| CA2718472A1 (en) | 2007-08-03 | 2009-02-12 | Lixte Biotechnology, Inc. | Use of phosphatases to treat neuroblastomas and medulloblastomas |
| ES2628748T3 (es) | 2007-10-01 | 2017-08-03 | Lixte Biotechnology, Inc. | Inhibidores de la HDAC |
| US8227473B2 (en) | 2008-08-01 | 2012-07-24 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| WO2010014220A1 (en) | 2008-08-01 | 2010-02-04 | Lixte Biotechnology, Inc. | Neuroprotective agents for the prevention and treatment of neurodegenerative diseases |
| WO2010014141A1 (en) | 2008-08-01 | 2010-02-04 | Lixte Biotechnology, Inc. | Methods for regulating cell mitosis by inhibiting serine/threonine phosphatase |
| WO2010147612A1 (en) | 2009-06-18 | 2010-12-23 | Lixte Biotechnology, Inc. | Methods of modulating cell regulation by inhibiting p53 |
| WO2011132171A1 (en) | 2010-04-23 | 2011-10-27 | Piramal Life Sciences 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 |
| EP2857385B1 (en) | 2012-06-01 | 2017-08-02 | Taisho Pharmaceutical Co., Ltd. | Prodrug of fluorine-containing amino acid |
| EP2867239A4 (en) * | 2012-06-29 | 2015-12-23 | Lixte Biotechnology Inc | OXABICYCLOHEPTANES AND OXABICYCLOHEPTENES FOR THE TREATMENT OF DIABETES |
| EP2870161B1 (en) * | 2012-06-29 | 2018-08-08 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of reperfusion injury |
| EP2964026A4 (en) | 2013-03-05 | 2016-08-17 | Lixte Biotechnology Inc | HDAC INHIBITORS FOR THE TREATMENT OF TRAUMATIC BRAIN INJURY |
| US20160009727A1 (en) | 2013-03-15 | 2016-01-14 | Lixte Biotechnology, Inc. | Sanguinarine analog pp2c inhibitors for cancer treatment |
| WO2014168941A1 (en) | 2013-04-09 | 2014-10-16 | Lixte Biotechnology, Inc. | Formulations of oxabicycloheptanes and oxabicycloheptenes |
| WO2015073802A1 (en) * | 2013-11-15 | 2015-05-21 | Lixte Biotechnology, Inc. | Protein phosphatase inhibitors that cross the blood brain barrier |
| US9051332B1 (en) | 2013-11-20 | 2015-06-09 | Transitions Optical, Inc. | Photochromic indeno-fused ring pyran compounds |
| US20170136008A1 (en) | 2014-06-20 | 2017-05-18 | 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 |
| CN107072991A (zh) * | 2014-09-12 | 2017-08-18 | 莱克斯特生物技术公司 | 磷酸酶抑制剂的人类给药 |
| 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 |
| MX393461B (es) * | 2015-05-15 | 2025-03-24 | Lixte Biotechnology Inc | Farmacos precursores de oxabicicloheptanos |
| JP6964593B2 (ja) | 2016-01-27 | 2021-11-10 | リクスト・バイオテクノロジー，インコーポレイテッド | ホスファターゼ阻害剤を使用して骨髄異形成症候群を処置するための臨床レジメン |
| US12168008B2 (en) | 2016-12-08 | 2024-12-17 | Lixte Biotechnology, Inc. | Oxabicycloheptanes for modulation of immune response |
| US20210275521A1 (en) | 2017-12-05 | 2021-09-09 | Lixte Biotechnology, Inc. | Oxabicycloheptanes for treatment of secondary acute myeloid leukemia |
-
2016
- 2016-05-12 MX MX2021012440A patent/MX393461B/es unknown
- 2016-05-12 ES ES20167812T patent/ES2985668T3/es active Active
- 2016-05-12 MX MX2017014549A patent/MX386975B/es unknown
- 2016-05-12 EP EP20167812.5A patent/EP3736275B1/en active Active
- 2016-05-12 ES ES16796978T patent/ES2795950T3/es active Active
- 2016-05-12 DK DK16796978.1T patent/DK3294287T3/da active
- 2016-05-12 AU AU2016263079A patent/AU2016263079B2/en active Active
- 2016-05-12 WO PCT/US2016/032123 patent/WO2016186963A1/en not_active Ceased
- 2016-05-12 EP EP16796978.1A patent/EP3294287B1/en active Active
- 2016-05-12 CN CN202110080437.0A patent/CN113150030A/zh active Pending
- 2016-05-12 CN CN201680032555.1A patent/CN107708686B/zh not_active Expired - Fee Related
- 2016-05-12 JP JP2018511344A patent/JP7187023B6/ja active Active
- 2016-05-12 HU HUE16796978A patent/HUE050177T2/hu unknown
- 2016-05-13 TW TW109111871A patent/TWI757720B/zh active
- 2016-05-13 US US15/154,304 patent/US9988394B2/en active Active
- 2016-05-13 TW TW105114967A patent/TWI693226B/zh 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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