PL432085A1 - Amino acid derivative of non-steroid anti-inflammatory drug and method of obtaining amino acid derivative of non-steroid anti-inflammatory drug - Google Patents

Amino acid derivative of non-steroid anti-inflammatory drug and method of obtaining amino acid derivative of non-steroid anti-inflammatory drug

Info

Publication number
PL432085A1
PL432085A1 PL432085A PL43208519A PL432085A1 PL 432085 A1 PL432085 A1 PL 432085A1 PL 432085 A PL432085 A PL 432085A PL 43208519 A PL43208519 A PL 43208519A PL 432085 A1 PL432085 A1 PL 432085A1
Authority
PL
Poland
Prior art keywords
amino acid
inflammatory drug
acid derivative
steroid anti
propane
Prior art date
Application number
PL432085A
Other languages
Polish (pl)
Other versions
PL241669B1 (en
Inventor
Paula Ossowicz
Ewa Janus
Ewelina Świątek
Original Assignee
Zachodniopomorski Uniwersytet Technologiczny W Szczecinie
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
Application filed by Zachodniopomorski Uniwersytet Technologiczny W Szczecinie filed Critical Zachodniopomorski Uniwersytet Technologiczny W Szczecinie
Priority to PL432085A priority Critical patent/PL241669B1/en
Publication of PL432085A1 publication Critical patent/PL432085A1/en
Publication of PL241669B1 publication Critical patent/PL241669B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Przedmiotem zgłoszenia jest aminokwasowa pochodna niesteroidowego leku przeciwzapalnego, która charakteryzuje się tym, że ma postać o wzorze przedstawionym na rysunku, gdzie część anionową stanowi anion ibuprofenianowy, naproksenianowy lub ketoprofenianowy, a część kationową stanowi ester alkilowy L-leucyny, zaś łańcuch alkilowy R stanowi łańcuch etylowy, izopropylowy, propylowy, butylowy lub heksylowy. Przedmiotem zgłoszenia jest także sposób wytwarzania aminokwasowej pochodnej niesteroidowego leku przeciwzapalnego, polegający na reakcji równomolowej estru alkilowego aminokwasu z kwasem arylopropionowym w środowisku rozpuszczalnika organicznego, charakteryzuje się tym, że ester alkilowy L-leucyny poddaje się reakcji z kwasem (RS)-2-[4-(2-metylopropylo)fenylo]propanowym lub (2S)-2-(6-metoksynaftalen-2-ylo)propanowym lub (RS)-2-(3-benzoilofenylo)propanowym w temperaturze od 25°C do 45°C w czasie od 5 do 45 minut wytwarzając pochodną o wzorze przedstawionym na rysunku.The subject of the application is an amino acid derivative of a non-steroidal anti-inflammatory drug, which is characterized in that it has the form shown in the figure, where the anionic part is an ibuprofenate, naproxenate or ketoprophenate anion, and the cationic part is an L-leucine alkyl ester, and the R alkyl chain is the chain. ethyl, isopropyl, propyl, butyl or hexyl. The subject of the application is also a method for the preparation of an amino acid derivative of a non-steroidal anti-inflammatory drug, which consists in the equimolar reaction of an amino acid alkyl ester with arylpropionic acid in an organic solvent, characterized in that the L-leucine alkyl ester is reacted with the acid (RS) -2- [4 - (2-methylpropyl) phenyl] propane or (2S) -2- (6-methoxynaphthalen-2-yl) propane or (RS) -2- (3-benzoylphenyl) propane at 25 ° C to 45 ° C at 5 to 45 minutes to generate the derivative of formula shown in the figure.

PL432085A 2019-12-05 2019-12-05 Amino acid derivative of non-steroid anti-inflammatory drug and method of obtaining amino acid derivative of non-steroid anti-inflammatory drug PL241669B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL432085A PL241669B1 (en) 2019-12-05 2019-12-05 Amino acid derivative of non-steroid anti-inflammatory drug and method of obtaining amino acid derivative of non-steroid anti-inflammatory drug

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL432085A PL241669B1 (en) 2019-12-05 2019-12-05 Amino acid derivative of non-steroid anti-inflammatory drug and method of obtaining amino acid derivative of non-steroid anti-inflammatory drug

Publications (2)

Publication Number Publication Date
PL432085A1 true PL432085A1 (en) 2021-06-14
PL241669B1 PL241669B1 (en) 2022-11-14

Family

ID=76321226

Family Applications (1)

Application Number Title Priority Date Filing Date
PL432085A PL241669B1 (en) 2019-12-05 2019-12-05 Amino acid derivative of non-steroid anti-inflammatory drug and method of obtaining amino acid derivative of non-steroid anti-inflammatory drug

Country Status (1)

Country Link
PL (1) PL241669B1 (en)

Also Published As

Publication number Publication date
PL241669B1 (en) 2022-11-14

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PL432085A1 (en) Amino acid derivative of non-steroid anti-inflammatory drug and method of obtaining amino acid derivative of non-steroid anti-inflammatory drug