US2016362420A1PendingUtilityA1
Antiparasitic Compositions and Methods Utilizing Substituted 5,5,7,7-Tetramethyl- 4,5,6,7-Tetrahydrothieno[2,3-C]Pyridine Derivatives
Est. expiryJun 10, 2035(~8.9 yrs left)· nominal 20-yr term from priority
C07F 5/025C07D 495/04C07F 5/04
50
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Claims
Abstract
The present disclosure relates generally to systems, methods, and compounds for therapeutic use against parasitic infections. More particularly, the disclosure relates to anti-parasitic compounds, and methods for making and for using the anti-parasitic compounds, where the anti-parasitic compounds have the general formula: where X, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are defined more fully below.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An antiparasitic compound having a general formula of Formula I:
wherein X is O or N;
R 1 is a C2 to C4 alky or C2 to C4 cycloalkyl;
R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from hydrogen (H), chlorine (Cl), bromine (Br), fluorine (F), CF 3 , SF 5 , substituted or unsubstituted morpholine, substituted or unsubstituted piperazine, boronic acid (B(OH) 2 ), substituted or unsubstituted 1,3,2-dioxaborlane.
2 . The antiparasitic compound of claim 1 , wherein X is O.
3 . The antiparasitic compound of claim 2 , wherein R 1 is ethyl, propyl, iso-propyl, cyclopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
4 . The antiparasitic compound of claim 3 , wherein R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from H, F, CF 3 , SF 5 , substituted or unsubstituted morpholine, substituted or unsubstituted piperazine, boronic acid (B(OH) 2 ), substituted or unsubstituted 1,3,2-dioxaborlane.
5 . The antiparasitic compound of claim 4 , wherein R 2 and R 6 are H, and R 3 , R 4 , and R 5 are F.
6 . The antiparasitic compound of claim 4 , wherein R 2 , R 3 , R 4 , R 5 , and R 6 are fluorine.
7 . The antiparasitic compound of claim 4 , wherein R 5 is CF 3 , SF 5 , boronic acid, or 4,4,5,5-tetramethyl-1,3,2-dioxaborlane and R 2 , R 3 , R 4 , and R 6 are H.
8 . The antiparasitic compound of claim 4 , wherein R 2 , R 3 , R 5 , and R 6 are H, and R 4 is morpholine, methyl-piperazine, SF 5 , boronic acid, or 4,4,5,5-tetramethyl-1,3,2-dioxaborlane.
9 . The antiparasitic compound of claim 3 , wherein R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from H, Cl, Br, F, and CF 3 .
10 . The antiparasitic compound of claim 9 , wherein one of R 2 , R 3 , R 4 , R 5 , and R 6 is CF 3 , another of R 2 , R 3 , R 4 , R 5 , and R 6 is Cl or Br, and the remainder of R 2 , R 3 , R 4 , R 5 , and R 6 are H.
11 . The antiparasitic compound of claim 1 , wherein X is N.
12 . The antiparasitic compound of claim 11 , wherein R 1 is ethyl, propyl, iso-propyl, cyclopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
13 . The antiparasitic compound of claim 12 , wherein R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from H, F, CF 3 , SF 5 , substituted or unsubstituted morpholine, substituted or unsubstituted piperazine, boronic acid (B(OH) 2 ), substituted or unsubstituted 1,3,2-dioxaborlane.
14 . The antiparasitic compound of claim 13 , wherein R 2 and R 6 are H, and R 3 , R 4 , and R 5 are F.
15 . The antiparasitic compound of claim 13 , wherein R 2 , R 3 , R 4 , R 5 , and R 6 are fluorine.
16 . The antiparasitic compound of claim 13 , wherein R 5 is CF 3 , SF 5 , boronic acid, or 4,4,5,5-tetramethyl-1,3,2-dioxaborlane and R 2 , R 3 , R 4 , and R 6 are H.
17 . The antiparasitic compound of claim 13 , wherein R 2 , R 3 , R 5 , and R 6 are H, and R 4 is morpholine, methyl-piperazine, SF 5 , boronic acid, or 4,4,5,5-tetramethyl-1,3,2-dioxaborlane.
18 . The antiparasitic compound of claim 12 , wherein R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from H, Cl, Br, F, and CF 3 .
19 . The antiparasitic compound of claim 18 , wherein one of R 2 , R 3 , R 4 , R 5 , and R 6 is CF 3 , another of R 2 , R 3 , R 4 , R 5 , and R 6 is Cl or Br, and the remainder of R 2 , R 3 , R 4 , R 5 , and R 6 are H.
20 . A method of treating a parasitic infection comprising administering the antiparasitic compound of claim 1 to a subject in need thereof.
21 . A method of making the antiparasitic compound of claim 1 comprising a one-pot synthesis comprising:
a) mixing 2,2,6,6-tetramethylpiperidine, a 2-cyanoacetate ester comprising R 1 , and sulfur in ethanol under heat to form a reaction solution; and;
b) adding 2-R 2 , 3-R 3 , 4-R 4 —, 5-R 5 , 6-R 6 -benzoyl chloride to the reaction solution at room temperature.Join the waitlist — get patent alerts
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