IP Library Granted Patent US 9,023,869
Granted Patent B2
US 9,023,869 · App. 13/685,013 · Granted May 5, 2015

Substituted phenylcarbamoyl alkylamino arene compounds and N,N'-BIS-arylurea compounds

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 9,023,869
App. No.
13/685,013
Granted
May 5, 2015
Kind
B2
Abstract

Substituted phenylcarbamoyl alkylamino arenes; substituted phenylthiocarbamyl alkylamino arenes; substituted phenylcarbamoyl alkylamino heteroarenes; substituted phenylthiocarbamyl alkylamino heteroarenes; N-substituted aryl, N′-substituted aryl urea compounds; N-substituted aryl, N′-substituted heteroaryl urea compounds; N-substituted aryl, N′-substituted aryl thiourea compounds and N-substituted aryl, N′-substituted heteroaryl thiourea compounds are provided and may find use as androgen receptor modulators. The compounds may find particular use in treating prostate cancer, including castration-resistant prostate cancer and/or hormone-sensitive prostate cancer.

Claims (54)

1. A compound of formula (I):

wherein, in formula (I):

W 1 is CN, NO 2 or SO 2 R 4 ;

W 2 is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl or halogen;

Z is S, O or NR 5 ;

Y 1 and Y 2 are independently hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaralkyl, heterocyclyl, substituted heterocyclyl or Y 1 and Y 2 are taken together with the carbon to which they are attached to form a cycle which can be heterocyclic, substituted heterocyclic, cycloalkyl, substituted cycloalkyl;

T is carbon or nitrogen and can be at any position in the ring;

R 1 is —C 1 -C 8 alkyl-NR a R b , —O—C 1 -C 8 alkyl-NR c R d or —C(O)NR e R f ,

wherein:

R a is a C 1 -C 12 alkyl and R b is H or a C 1 -C 12 alkyl or R a and R b are taken together with the N to which they are attached to form a heterocyclic ring;

R c is a C 1 -C 12 alkyl and R d is H or a C 1 -C 12 alkyl or R c and R d are taken together with the N to which they are attached to form a heterocyclic ring;

R e is a C 1 -C 12 alkyl and R f is H or a C 1 -C 12 alkyl, or R e and R f are taken together with the N to which they are attached to form a heterocyclic ring;

R 2 is hydrogen, halo, nitro, alkyl or substituted alkyl; and

R 4 and R 5 are independently H, alkyl, substituted alkyl, aryl or substituted aryl, or a pharmaceutically acceptable salt thereof

2. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein:

(a) R 1 is —C 1 -C 8 alkyl-NR a R b ;

(b) R 1 is —C 1 -C 8 alkyl-NR a R b and R 2 is halo; or

(b) R 1 is —C 1 -C 8 alkyl-NR a R b , R 2 is halo, and at least one of (i)-(v) applies:

(i) W 1 is CN;

(ii) W 2 is perhaloalkyl;

(iii) Z is O;

(iv) Y 1 and Y 2 are both methyl; and

(v) T is C.

3. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein;

(a) R 1 is —O—C 1 -C 8 alkyl-NR c R;

(b) R 1 is —O—C 1 -C 8 alkyl-NR c R and R 2 is hydrogen; or

(c) R 1 is —O—C 1 -C 8 alkyl-NR c R, R 2 is hydrogen, and at least one of (i)-(v) applies:

(i) W 1 is CN;

(ii) W 2 is perhaloalkyl;

(iii) Z is O;

(iv) Y 1 and Y 2 are both methyl and

(v) T is C.

4. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein:

(a) R 1 is —C(O)NR e R f ;

(b) R 1 is —C(O)NR e R f and R 2 is halo; or

(c) R 1 is —C(O)NR e R f , R 2 is halo, and at least one of (i)-(v) applies:

(i) W 1 is CN;

(ii) W 2 is perhaloalkyl;

(iii) Z is O;

(iv) Y 1 and Y 2 are both methyl and

(v) T is C.

5. The compound of claim 4 or a pharmaceutically acceptable salt thereof, wherein R 1 is —C(O)NR e R f , R 2 is halo, and at least one of (i)-(v) applies:

(i) W 1 is CN;

(ii) W 2 is perhaloalkyl;

(iii) Z is O;

(iv) Y 1 and Y 2 are both methyl and

(v) T is C: and

R e is a methyl and R f is H; or

R e is a C 1 -C 12 alkyl and R f is C 1 -C 12 alkyl or;

R e and R f are taken together with the N to which they are attached to form a heterocyclic ring.

6. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

7. A method of treating prostate cancer in an individual in need thereof comprising administering to the individual an effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.

8. The method of claim 7 , wherein the individual has castration-resistant prostate cancer.

9. The method of claim 7 , wherein the individual has hormone- sensitive prostate cancer.

Assignments (6)
ASSIGNEE ADDRESS CORRECTION Recorded Mar 30, 2023
From: MEDIVATION TECHNOLOGIES LLC
To: MEDIVATION TECHNOLOGIES LLC
Reel/Frame 063190/0349 →
CHANGE OF NAME Recorded Oct 10, 2017
From: MEDIVATION TECHNOLOGIES, INC.
To: MEDIVATION TECHNOLOGIES LLC
Reel/Frame 044169/0001 →
RELEASE OF SECURITY INTEREST Recorded Sep 28, 2016
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MEDIVATION PROSTATE THERAPEUTICS, INC.; MEDIVATION TECHNOLOGIES, INC.
Reel/Frame 040181/0177 →
CONFIRMATORY GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS Recorded Sep 4, 2015
From: MEDIVATION TECHNOLOGIES, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 036553/0925 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 27, 2012
From: CHAKRAVARTY, SARVAJIT; JAIN, RAJENDRA PARASMAL
To: MEDIVATION PROSTATE THERAPEUTICS, INC.
Reel/Frame 029354/0966 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 27, 2012
From: MEDIVATION PROSTATE THERAPEUTICS, INC.
To: MEDIVATION TECHNOLOGIES, INC.
Reel/Frame 029355/0030 →