AU2016219617A1 - Positively charged water-soluble prodrugs of aspirin - Google Patents
Positively charged water-soluble prodrugs of aspirinInfo
- Publication number
- AU2016219617A1 AU2016219617A1 AU2016219617A AU2016219617A AU2016219617A1 AU 2016219617 A1 AU2016219617 A1 AU 2016219617A1 AU 2016219617 A AU2016219617 A AU 2016219617A AU 2016219617 A AU2016219617 A AU 2016219617A AU 2016219617 A1 AU2016219617 A1 AU 2016219617A1
- Authority
- AU
- Australia
- Prior art keywords
- aspirin
- pro
- drugs
- positively charged
- drug
- 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
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
POSITIVELY CHARGED WATER-SOLUBLE PRODRUGS OF Abstract The novel positively charged prodrugs of acetylsalicylic acid and its analogues in the general formula (1) "Structure 1" were designed and synthesized. The compounds of the general formula (1) "Structure 1" indicated above can be prepared from functional derivatives of ASA or its analogues, (for example acid halides or mixed anhydrides), by reaction with suitable alcohols, thiols, or amines. The positively charged amino groups of these pro-drugs not only largely increases the solubility of the drugs, but also bonds to the negative charge on the phosphate head group of membranes and push the pro-drug into the cytosol. The experiment results suggest that the pro-drug, diethylaminoethyl acetylsalicylate.AcOH, diffuses through human skin ~400 times faster than acetylsalicylic acid itself and ~100 times faster than ethyl acetylsalicylate. In plasma, 80% of these pro-drugs can change back to the drug in a few minutes. The pro-drugs can be used medicinally in treating any aspirin-treatable conditions in humans or animals and be administered not only orally, but also transdermally for any kind of medical treatments and avoid most of the side effects of aspirin, most notably GI disturbances such as dyspepsia, gastroduodenal bleeding, gastric ulcerations, and gastritis. Controlled transdermal administration systems of the prodrug enables the aspirin to reach constantly optimal therapeutic blood levels to increase effectiveness and reduce the side effects of aspirin.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2016219617A AU2016219617B2 (en) | 2006-07-09 | 2016-08-24 | Positively charged water-soluble prodrugs of aspirin |
AU2018217329A AU2018217329A1 (en) | 2006-07-09 | 2018-08-17 | Positively charged water-soluble prodrugs of aspirin |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IB2006/052318 WO2008007171A1 (en) | 2006-07-09 | 2006-07-09 | Positively charged water-soluble prodrugs of aspirin |
AU2006346195 | 2006-07-09 | ||
AU2006346195A AU2006346195B2 (en) | 2006-07-09 | 2006-07-09 | Positively charged water-soluble prodrugs of aspirin |
AU2013206215A AU2013206215C9 (en) | 2006-07-09 | 2013-06-07 | Positively charged water-soluble prodrugs of aspirin |
AU2016219617A AU2016219617B2 (en) | 2006-07-09 | 2016-08-24 | Positively charged water-soluble prodrugs of aspirin |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2013206215A Division AU2013206215C9 (en) | 2006-07-09 | 2013-06-07 | Positively charged water-soluble prodrugs of aspirin |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2018217329A Division AU2018217329A1 (en) | 2006-07-09 | 2018-08-17 | Positively charged water-soluble prodrugs of aspirin |
Publications (2)
Publication Number | Publication Date |
---|---|
AU2016219617A1 true AU2016219617A1 (en) | 2016-09-15 |
AU2016219617B2 AU2016219617B2 (en) | 2018-05-17 |
Family
ID=56898946
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2016219617A Ceased AU2016219617B2 (en) | 2006-07-09 | 2016-08-24 | Positively charged water-soluble prodrugs of aspirin |
AU2018217329A Abandoned AU2018217329A1 (en) | 2006-07-09 | 2018-08-17 | Positively charged water-soluble prodrugs of aspirin |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU2018217329A Abandoned AU2018217329A1 (en) | 2006-07-09 | 2018-08-17 | Positively charged water-soluble prodrugs of aspirin |
Country Status (1)
Country | Link |
---|---|
AU (2) | AU2016219617B2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9862698B2 (en) | 2014-12-16 | 2018-01-09 | Adt Pharmaceuticals, Inc. | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
US9931315B2 (en) | 2014-12-16 | 2018-04-03 | Adt Pharmaceuticals, Inc. | Method of selectively inhibiting Ras-mediated tumor growth in humans |
US11186596B2 (en) | 2018-04-26 | 2021-11-30 | Adt Pharmaceuticals, Llc | Anticancer indenes, indanes, azaindenes, azaindanes, pharmaceutical compositions and uses |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH399486A (en) * | 1962-10-02 | 1965-09-30 | Biosedra Lab | Process for the preparation of new salicylamides |
EP0152379A3 (en) * | 1984-02-15 | 1986-10-29 | Ciba-Geigy Ag | Process for preparing pharmaceutical compositions containing unilamellar liposomes |
-
2016
- 2016-08-24 AU AU2016219617A patent/AU2016219617B2/en not_active Ceased
-
2018
- 2018-08-17 AU AU2018217329A patent/AU2018217329A1/en not_active Abandoned
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9862698B2 (en) | 2014-12-16 | 2018-01-09 | Adt Pharmaceuticals, Inc. | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
US9931315B2 (en) | 2014-12-16 | 2018-04-03 | Adt Pharmaceuticals, Inc. | Method of selectively inhibiting Ras-mediated tumor growth in humans |
US10526307B2 (en) | 2014-12-16 | 2020-01-07 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
US10975054B2 (en) | 2014-12-16 | 2021-04-13 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
US10981886B2 (en) | 2014-12-16 | 2021-04-20 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
US11104658B2 (en) | 2014-12-16 | 2021-08-31 | Adt Pharmaceuticals, Llc | Method of treating or preventing Ras-mediated diseases |
US11130744B2 (en) | 2014-12-16 | 2021-09-28 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
US11198679B2 (en) | 2014-12-16 | 2021-12-14 | Adt Pharmaceuticals, Llc | Method of treating or preventing Ras-mediated diseases |
US11407727B2 (en) | 2014-12-16 | 2022-08-09 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
US11186596B2 (en) | 2018-04-26 | 2021-11-30 | Adt Pharmaceuticals, Llc | Anticancer indenes, indanes, azaindenes, azaindanes, pharmaceutical compositions and uses |
US11680073B2 (en) | 2018-04-26 | 2023-06-20 | Adt Pharmaceuticals, Llc | Anticancer indenes, indanes, azaindenes, azaindanes, pharmaceutical compositions and uses |
Also Published As
Publication number | Publication date |
---|---|
AU2018217329A1 (en) | 2018-09-06 |
AU2016219617B2 (en) | 2018-05-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FGA | Letters patent sealed or granted (standard patent) | ||
MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |