Synthetic Sphingolipid-Like Molecules, Drugs, Methods of Their Synthesis and Methods of Treatment
AssigneesThe Regents of the University of California, Universite de Montreal
InventorsAimee L. Edinger, Stephen Hanessian
Life of this patent
Estimating the term…
Abstract
Small molecules comprised of azacyclic constrained sphingolipid-like compounds and methods of their synthesis are provided. Formulations and medicaments are also provided that are directed to the treatment of disease, such as, for example, neoplasms, cancers, and other diseases. Therapeutics are also provided containing a therapeutically effective dose of one or more small molecule compounds, present either as pharmaceutically effective salt or in pure form, including, but not limited to, formulations for oral, intravenous, or intramuscular administration.
Claims28
A compound comprising:
- wherein:
- R1 is an optional functional group selected from an alkyl chain, (CH2)nOH, (CHOH-alkyl, CHOH-alkyne, (CH2)nOMe, (CH2)nPO(OH)2 and esters thereof, CH═CHPO(OH)2 and esters thereof, (CH2CH2)nPO(OH)2 and esters thereof, and (CH2)nOPO(OH)2 and esters thereof, (CH2)nPO3 and esters thereof, wherein Me is an alkyl, alkene or alkyne;
- R2 is an aliphatic chain (C6-C14);
- R3 is a mono-, di-, tri- or tetra-aromatic substituent comprising hydrogen, halogen, alkyl, alkoxy, azide (N3), ether, NO2, or cyanide (CN);
- n is an independently selected whole integer selected from 1 to 3;
- and
- wherein the phenyl can be moved between positions 3 to 5 about the heterocycle amine.
-9. (canceled)
(canceled)
A medicament for the treatment of a human disorder comprising:
- a pharmaceutical formulation containing a therapeutically effective amount of one or more azacyclic constrained sphingolipid-like small molecule compounds comprising:
- wherein:
- R1 is an optional functional group selected from an alkyl chain, (CH2)nOH, (CHOH-alkyl, CHOH-alkyne, (CH2)nOMe, (CH2)nPO(OH)2 and esters thereof, CH═CHPO(OH)2 and esters thereof, (CH2CH2)nPO(OH)2 and esters thereof, and (CH2)nOPO(OH)2 and esters thereof, (CH2)nPO3 and esters thereof, wherein Me is an alkyl, alkene or alkyne;
- R2 is an aliphatic chain (C6-C14);
- R3 is a mono-, di-, tri- or tetra-aromatic substituent comprising hydrogen, halogen, alkyl, alkoxy, azide (N3), ether, NO2, or cyanide (CN);
- n is an independently selected whole integer selected from 1 to 3;
- and
- wherein the phenyl can be moved between positions 3 to 5 about the five heterocycle amine.
-17. (canceled)
(canceled)
-22. (canceled)
(canceled)
A method of treatment of a human disorder comprising:
- administering a pharmaceutical formulation to a human subject, the pharmaceutical formulation containing a therapeutically effective amount of one or more azacyclic constrained sphingolipid-like small molecule compounds comprising:
- wherein:
- R1 is an optional functional group selected from an alkyl chain, (CH2)nOH, (CHOH-alkyl, CHOH-alkyne, (CH2)nOMe, (CH2)nPO(OH)2 and esters thereof, CH═CHPO(OH)2 and esters thereof, (CH2CH2)nPO(OH)2 and esters thereof, and (CH2)nOPO(OH)2 and esters thereof, (CH2)nPO3 and esters thereof, wherein Me is an alkyl, alkene or alkyne;
- R2 is an aliphatic chain (C6-C14);
- R3 is a mono-, di-, tri- or tetra-aromatic substituent comprising hydrogen, halogen, alkyl, alkoxy, azide (N3), ether, NO2, or cyanide (CN);
- n is an independently selected whole integer selected from 1 to 3;
- and
- wherein the phenyl can be moved between positions 3 to 5 about the heterocycle amine.
(canceled)
-34. (canceled)
Dependencies are inferred from the claim text.