AU2016263079B2 - Oxabicycloheptane prodrugs - Google Patents
Oxabicycloheptane prodrugs Download PDFInfo
- Publication number
- AU2016263079B2 AU2016263079B2 AU2016263079A AU2016263079A AU2016263079B2 AU 2016263079 B2 AU2016263079 B2 AU 2016263079B2 AU 2016263079 A AU2016263079 A AU 2016263079A AU 2016263079 A AU2016263079 A AU 2016263079A AU 2016263079 B2 AU2016263079 B2 AU 2016263079B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- alkenyl
- cancer
- aryl
- compound
- 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.)
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Links
- 0 CCCOC(C(*NC)N)=O Chemical compound CCCOC(C(*NC)N)=O 0.000 description 24
- JMCBXVDOSKPCPH-UHFFFAOYSA-N CC(C)C(O1)=C(C)OC1=O Chemical compound CC(C)C(O1)=C(C)OC1=O JMCBXVDOSKPCPH-UHFFFAOYSA-N 0.000 description 1
- MXSVGPZDAUAOGB-UHFFFAOYSA-N CC(OC(c1ccc(CCP(O)(O)=O)cc1)=O)I Chemical compound CC(OC(c1ccc(CCP(O)(O)=O)cc1)=O)I MXSVGPZDAUAOGB-UHFFFAOYSA-N 0.000 description 1
- ANNXPFQNCRCVPA-UHFFFAOYSA-N CCC(O1)=C(C)OS1=O Chemical compound CCC(O1)=C(C)OS1=O ANNXPFQNCRCVPA-UHFFFAOYSA-N 0.000 description 1
- VUNJARMDQHYXDL-UHFFFAOYSA-N CCC(OCOC(c1c(cc2)[o]c2c1C(N1CCN(C)CC1)=O)=O)=O Chemical compound CCC(OCOC(c1c(cc2)[o]c2c1C(N1CCN(C)CC1)=O)=O)=O VUNJARMDQHYXDL-UHFFFAOYSA-N 0.000 description 1
- MTTWKOGIBSWAOB-UHFFFAOYSA-N CCc(cc1)ccc1C(OC(C)C)=O Chemical compound CCc(cc1)ccc1C(OC(C)C)=O MTTWKOGIBSWAOB-UHFFFAOYSA-N 0.000 description 1
- ZPUKPAPWEWUPTC-UHFFFAOYSA-N CCc(cc1)ccc1C(OCC)=O Chemical compound CCc(cc1)ccc1C(OCC)=O ZPUKPAPWEWUPTC-UHFFFAOYSA-N 0.000 description 1
- JUEALNCKFUEQKZ-UHFFFAOYSA-N [O-][NH+]1OC(CI)=CO1 Chemical compound [O-][NH+]1OC(CI)=CO1 JUEALNCKFUEQKZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physiology (AREA)
- Nutrition Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2016263079A1 AU2016263079A1 (en) | 2017-12-07 |
| AU2016263079B2 true AU2016263079B2 (en) | 2019-08-15 |
Family
ID=57276640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016263079A Active AU2016263079B2 (en) | 2015-05-15 | 2016-05-12 | Oxabicycloheptane prodrugs |
Country Status (12)
| Country | Link |
|---|---|
| US (5) | US9988394B2 (enExample) |
| EP (2) | EP3294287B1 (enExample) |
| JP (3) | JP7187023B6 (enExample) |
| CN (2) | CN113150030A (enExample) |
| AU (1) | AU2016263079B2 (enExample) |
| DK (1) | DK3294287T3 (enExample) |
| ES (2) | ES2795950T3 (enExample) |
| HU (1) | HUE050177T2 (enExample) |
| IL (2) | IL255516B (enExample) |
| MX (2) | MX393461B (enExample) |
| TW (2) | TWI757720B (enExample) |
| WO (1) | WO2016186963A1 (enExample) |
Families Citing this family (8)
| 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 |
| KR20160004299A (ko) | 2013-04-09 | 2016-01-12 | 릭스트 바이오테크놀로지, 인코포레이티드 | 옥사바이시클로헵탄류 및 옥사바이시클로헵텐류의 제형 |
| WO2016014778A1 (en) | 2014-07-24 | 2016-01-28 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Protein phosphatase 2a inhibitors for treating myelodysplastic syndromes |
| WO2016057931A1 (en) | 2014-10-10 | 2016-04-14 | The Research Foundation For The State University Of New York | Trifluoromethoxylation of arenes via intramolecular trifluoromethoxy group migration |
| MX382044B (es) | 2015-02-19 | 2025-03-13 | Lixte Biotechnology Inc | Oxabicicloheptanos y oxabicicloheptenos para el tratamiento de trastornos depresivos y de estrés. |
| JP7187023B6 (ja) | 2015-05-15 | 2023-01-05 | 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プロドラッグ |
| AU2017370731B2 (en) | 2016-12-08 | 2022-06-02 | Lixte Biotechnology, Inc. | Oxabicycloheptanes for modulation of immune response |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008097561A1 (en) * | 2007-02-06 | 2008-08-14 | Lixte Biotechology Holdings, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| WO2015073802A1 (en) * | 2013-11-15 | 2015-05-21 | Lixte Biotechnology, Inc. | Protein phosphatase inhibitors that cross the blood brain barrier |
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| 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 |
| AU2002353845A1 (en) | 2001-11-23 | 2003-06-10 | 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 |
| WO2007092414A2 (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 |
| EP2086534A4 (en) * | 2006-11-15 | 2010-06-02 | Genetic Technologies Ltd | COMPOUNDS, COMPOSITIONS AND METHOD FOR CONTROLLING SWIVELY PESTS |
| US20090035292A1 (en) * | 2007-08-03 | 2009-02-05 | Kovach John S | Use of phosphatases to treat neuroblastomas and medulloblastomas |
| CA2700857C (en) | 2007-10-01 | 2016-08-02 | John S. Kovach | Hdac inhibitors |
| WO2010147612A1 (en) | 2009-06-18 | 2010-12-23 | Lixte Biotechnology, Inc. | Methods of modulating cell regulation by inhibiting p53 |
| US8227473B2 (en) | 2008-08-01 | 2012-07-24 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| WO2010014141A1 (en) | 2008-08-01 | 2010-02-04 | Lixte Biotechnology, Inc. | Methods for regulating cell mitosis by inhibiting serine/threonine phosphatase |
| WO2010014220A1 (en) | 2008-08-01 | 2010-02-04 | Lixte Biotechnology, Inc. | Neuroprotective agents for the prevention and treatment of neurodegenerative diseases |
| AU2011243947A1 (en) | 2010-04-23 | 2012-12-06 | 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 |
| 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 |
| WO2014005080A1 (en) * | 2012-06-29 | 2014-01-03 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of reperfusion injury |
| WO2014137741A1 (en) | 2013-03-05 | 2014-09-12 | Lixte Biotechnology, Inc. | Hdac inhibitors for treating traumatic brain injury |
| WO2014149494A1 (en) | 2013-03-15 | 2014-09-25 | Lixte Biotechnology, Inc. | Sanguinarine analog pp2c inhibitors for cancer treatment |
| KR20160004299A (ko) | 2013-04-09 | 2016-01-12 | 릭스트 바이오테크놀로지, 인코포레이티드 | 옥사바이시클로헵탄류 및 옥사바이시클로헵텐류의 제형 |
| 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 |
| WO2016014778A1 (en) | 2014-07-24 | 2016-01-28 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Protein phosphatase 2a inhibitors for treating myelodysplastic syndromes |
| US20160074390A1 (en) * | 2014-09-12 | 2016-03-17 | Lixte Biotechnology, Inc. | Human dosing of phosphatase inhibitor |
| US9994584B2 (en) * | 2014-10-15 | 2018-06-12 | Lixte Biotechnology, Inc. | Process of synthesizing 3-(4-methylpiperazine-1-carbonyl)-7-oxabicyclo[2.2.1] heptane-2-carboxylic acid |
| MX382044B (es) | 2015-02-19 | 2025-03-13 | Lixte Biotechnology Inc | Oxabicicloheptanos y oxabicicloheptenos para el tratamiento de trastornos depresivos y de estrés. |
| JP7187023B6 (ja) * | 2015-05-15 | 2023-01-05 | 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プロドラッグ |
| EP3407887B1 (en) | 2016-01-27 | 2021-09-01 | Lixte Biotechnology, Inc. | Clinical regimen for treating myelodysplastic syndrome with phosphatase inhibitor |
| AU2017370731B2 (en) | 2016-12-08 | 2022-06-02 | 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 JP JP2018511344A patent/JP7187023B6/ja active Active
- 2016-05-12 EP EP16796978.1A patent/EP3294287B1/en active Active
- 2016-05-12 ES ES16796978T patent/ES2795950T3/es active Active
- 2016-05-12 MX MX2021012440A patent/MX393461B/es unknown
- 2016-05-12 EP EP20167812.5A patent/EP3736275B1/en active Active
- 2016-05-12 WO PCT/US2016/032123 patent/WO2016186963A1/en not_active Ceased
- 2016-05-12 CN CN202110080437.0A patent/CN113150030A/zh active Pending
- 2016-05-12 ES ES20167812T patent/ES2985668T3/es active Active
- 2016-05-12 CN CN201680032555.1A patent/CN107708686B/zh not_active Expired - Fee Related
- 2016-05-12 MX MX2017014549A patent/MX386975B/es unknown
- 2016-05-12 DK DK16796978.1T patent/DK3294287T3/da active
- 2016-05-12 AU AU2016263079A patent/AU2016263079B2/en active Active
- 2016-05-12 HU HUE16796978A patent/HUE050177T2/hu unknown
- 2016-05-13 US US15/154,304 patent/US9988394B2/en active Active
- 2016-05-13 TW TW109111871A patent/TWI757720B/zh 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
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2019
- 2019-06-12 US US16/439,227 patent/US10618908B2/en active Active
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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
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2022
- 2022-01-27 US US17/586,548 patent/US11866444B2/en active Active
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2023
- 2023-04-12 JP JP2023064829A patent/JP2023100645A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008097561A1 (en) * | 2007-02-06 | 2008-08-14 | Lixte Biotechology Holdings, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| WO2015073802A1 (en) * | 2013-11-15 | 2015-05-21 | Lixte Biotechnology, Inc. | Protein phosphatase inhibitors that cross the blood brain barrier |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |