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US 12,473,250 B2Granted
Molecular design of new antibiotics and antibiotic adjuvants against MCR strains
AssigneesSingapore Health Services Pte Ltd, Agency for Science, Technology and Research, Tan Tock Seng Hospital Pte Ltd
InventorsThet Tun Aung, Jianguo Li, Jun Jie Koh, Lakshminarayanan Rajamani, Roger Beuerman, Tiang Hwee Donald Tan, Mercy Halleluyah Periayah, Chandra Shekhar Verma, Swaine Chen, Timothy Barkham
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Abstract
The present invention relates to a compound comprising a hydrophobic moiety, a linker and N-containing moiety. The present invention also relates to the method of synthesizing the compound and the use of the compound as an antibiotic or an adjuvant for an antibiotic.
Claims18
A compound having the following formula (I):
- Z1-L1-A-L2-Z2 formula (I)
- wherein A is selected from the group consisting of
- and any mixture thereof;
- L1 and L2 are independently a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, alkoxycarbonyl, alkanoyloxy, carboxamido, ether, —(O—CH2—CH2—O)n—, L3, or any combination thereof, wherein L3 has the following structure:
- wherein n is an integer from 1 to 10 and R4 is an amino;
- and
- Z1 and Z2 independently have the following structure:
- R1 and R2 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aminoalkyl, guanidine, substituted or unsubstituted guanidylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, amino acid or peptide, or R1 and R2 are taken together to form a saturated or unsaturated, substituted or unsubstituted heterocyclic ring;
- and
- R3 is absent or hydrogen, or substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aminoalkyl, guanidine, substituted or unsubstituted guanidylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, amino acid or peptide,
- wherein when R3 is present, the nitrogen atom is a cationic quaternary nitrogen,
- wherein the broken bond represents where the structure attaches to the remainder of formula (I);
- wherein each substituted alkyl, substituted alkenyl, substituted alkynyl, substituted aminoalkyl, substituted guanidylalkyl, substituted aryl, substituted heteroaryl, substituted heteroarylalkyl, substituted heterocyclic ring is substituted with one or more groups independently selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkylalkenyl, heterocycloalkyl, cycloalkylheteroalkyl, cycloalkyloxy, cycloalkenyloxy, cycloamino, halo, carboxyl, haloalkyl, haloalkenyl, haloalkynyl, alkynyloxy, heteroalkyloxy, hydroxyl, hydroxyalkyl, alkoxy, alkenyloxy, nitro, amino, alkylamino, dialkylamino, alkenylamine, aminoalkyl, alkynylamino, acyl, alkyloxy, alkyloxyalkyl, alkyloxyaryl, alkyloxycarbonyl, alkyloxycycloalkyl, alkyloxyheteroaryl, alkyloxyheterocycloalkyl, acylamino, alkylsulfonyloxy, heterocyclic, heterocycloalkenyl, heterocycloalkyl, heterocycloalkylalkyl, heterocycloalkylalkenyl, heterocycloalkylheteroalkyl, heterocycloalkyloxy, heterocycloalkenyloxy, heterocycloamino, haloheterocycloalkyl, alkylsulfinyl, alkylsulfonyl, aminosulfonyl, sulfinyl, sulfinylamino, sulfonyl, sulfonylamino, aryl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylheteroalkyl, heteroarylamino, heteroaryloxy, arylalkenyl, arylalkyl, aryloxy, arylsulfonyl, cyano, cyanate, isocyanate, —C(O)NH(alkyl), and —C(O)N(alkyl)2.
10 more elements
Dependencies are inferred from the claim text.