IP Library Granted Patent US 9,925,269
Granted Patent B2
US 9,925,269 · App. 14/934,203 · Granted Mar 27, 2018

Phospholipid ether analogs as cancer-targeting drug vehicles

Inventors: Jamey P. Weichert (Fitchburg, WI); Anatoly Pinchuk (Fitchburg, WI); Kevin Kozak (Madison, WI); Marc Longino (Verona, WI); Joseph Grudzinski (Madison, WI); Benjamin Titz (Madison, WI); Chorom Pak (Madison, WI); Nathan Stehle (Madison, WI)
Assignee: CELLECTAR BIOSCIENCES, INC.
A61K47/48053A61K31/00A61K31/337A61K31/395A61K31/537A61K31/665A61K47/544A61K47/548
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,925,269
App. No.
14/934,203
Granted
Mar 27, 2018
Kind
B2
Abstract

The present invention is directed to therapeutic compounds capable of targeting cancer cells and cancer stem cells. The present invention is further directed to compositions comprising these therapeutic compounds and methods of treating cancer comprising administering these therapeutic compounds.

Claims (37)

1. A therapeutic compound comprising the formula A-B-D wherein:

A is at least one compound of formula (I),

(I), at least one compound of formula (II),

(II), at least one compound of formula (III)

(III), or a combination thereof,

wherein W is selected from the group consisting of an aryl, a C 1 -C 6 alkyl, an alkenyl, an optionally substituted C 3 -C 6 cycloalkyl an optionally substituted C 3 -C 6 heterocycloalkyl,

wherein R is H or an alkyl and wherein m is an integer from 12 to 24;

B is a linker compound selected from a bond and a compound of formula (IV),

Y—(CH 2 ) n —Z  (IV),

wherein:

Y is bound to A;

Z is bound to D;

Y is selected from the group consisting of a bond, O, NH, C═O, NHSO 2 O, and OC(═O)O;

Z is selected from the group consisting of O, NH, C═O, C(═O)O, C(═O)NH, SO 2 , OC(═O)OCH 2 ; and

n is an integer from 0 to 6; and

D is an anti-cancer drug selected from the group consisting of paclitaxel, irinotecan, topotecan, gemcitabine, cisplatin, geldanamycin, and mertansine.

2. The therapeutic compound of claim 1 wherein:

A is a compound of formula (I), wherein W is

and m is 18;

B is a compound of formula (IV), wherein Y is C═O and Z is C═O, C(═O)NH or C(═O)O and n is 3 or 4; and

D is paclitaxel.

3. The therapeutic compound of claim 1 wherein:

A is a compound of formula (I), wherein W is

and m is 18;

B is a bond or a compound of formula (IV), wherein Y is C═O, Z is NH and n is 1 or 3; and

D is geldanamycin.

4. The therapeutic compound of claim 1 wherein:

A is a compound of formula (I), wherein W is

and m is 18;

B is a bond; and

D is mertansine.

5. A therapeutic compound selected from the group consisting of:

wherein n is an integer from 0 to 6 and X is O or NH.

6. A pharmaceutical composition comprising a therapeutic compound of claim 1 or 5 and one or more pharmaceutically acceptable carriers.

7. A method of reducing, suppressing, or inhibiting cancer progression or recurrence comprising administering an effective amount of a therapeutic compound of claim 1 or 5 to a subject with cancer wherein the cancer is selected from breast cancer, lung cancer, pancreatic cancer, colorectal cancer, or prostate cancer.

8. The method of claim 7 wherein the cancer comprises cancer stem cells.

9. The method of claim 7 wherein the cancer is recurrent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2017
From: WEICHERT, JAMEY P.; PINCHUK, ANATOLY; KOZAK, KEVIN; LONGINO, MARC; GRUDZINSKI, JOSEPH; TITZ, BENJAMIN; PAK, CHOROM; STEHLE, NATHAN
To: CELLECTAR BIOSCIENCES, INC.
Reel/Frame 043915/0001 →
Continuity (2)
Provisional Application 62080436 · Nov 17, 2014
Related Publication 20160136290A1 · May 19, 2016