AU2016219617A1 - Positively charged water-soluble prodrugs of aspirin - Google Patents

Positively charged water-soluble prodrugs of aspirin

Info

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
Application number
AU2016219617A
Other versions
AU2016219617B2 (en
Inventor
Lina Xu
Chongxi Yu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Techfields Biochem Co Ltd
Original Assignee
Techfields Biochem Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from PCT/IB2006/052318 external-priority patent/WO2008007171A1/en
Priority claimed from AU2013206215A external-priority patent/AU2013206215C9/en
Application filed by Techfields Biochem Co Ltd filed Critical Techfields Biochem Co Ltd
Priority to AU2016219617A priority Critical patent/AU2016219617B2/en
Publication of AU2016219617A1 publication Critical patent/AU2016219617A1/en
Application granted granted Critical
Publication of AU2016219617B2 publication Critical patent/AU2016219617B2/en
Priority to AU2018217329A priority patent/AU2018217329A1/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

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  • 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.
AU2016219617A 2006-07-09 2016-08-24 Positively charged water-soluble prodrugs of aspirin Ceased AU2016219617B2 (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (11)

* Cited by examiner, † Cited by third party
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