IP Library Granted Patent US 9,085,570
Granted Patent B2
US 9,085,570 · App. 13/878,682 · Granted Jul 21, 2015

Substituted benzamides and their uses

Inventors: Amato Giaccia (Palo Alto, CA); Edwin Lai (Menlo Park, CA); Olga Razorenova (Menlo Park, CA); Denise Chan (San Francisco, CA); Michael Patrick Hay (Auckland, NZ); Muriel Bonnet (Auckland, NZ); Connie Sun (Palo Alto, CA); Ray Tabibiazar (Portola Valley, CA); Po-wai Yuen (Ann Arbor, MI)
Assignees: The Board of Trustees of the Leland Stanford Junior University; Auckland UniServices Limited; Ruga Corporation
C07D413/12C07D213/75C07D263/32C07D401/12C07D405/12C07D409/12C07D413/14C07D417/12
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 9,085,570
App. No.
13/878,682
Granted
Jul 21, 2015
Kind
B2
Abstract

Provided herein are Substituted Benzamides, compositions, and method of their manufacture and use.

Claims (35)

1. A compound of Formula Va:

or a pharmaceutically acceptable salt, hydrate, solvate, enantiomer, or stereoisomer thereof;

wherein:

F is a heteroaryl selected from pyridine, pyrazine, pyridazine, pyrimidine, 1,2,4-triazine or 1,3,5-triazine, optionally substituted with halogen, hydroxyl group, —CF3 group, C1-C6 alkoxy group, C1-C6 straight chain alkyl, C3-C6 branched chain alkyl or C3-C6 cycloalkyl group, wherein the number of substituents does not exceed the number of available C—H bonds of the heteroaryl; with multiple substitutions, each substituent on the heteroaryl is independent of the other substituents;

m is an integer ranging from 0 to 3;

p is an integer ranging from 1 to 5;

H is selected from —S(O)n-(CH2)q-, —O—(CH2)q-, or —C(O)—(CH2)q-;

n is an integer ranging from 0 to 2;

q is an integer ranging from 0 to 5;

K is selected from (i) C3-C7 cycloalkyl optionally substituted with two or more of R14, R15, and R16, (ii) C1-C6 straight or branched alkyl optionally substitiuted with one or more of R14, R15 and R16, and (iii)

R13 is selected from H, C1-C6 straight chain alkyl, C3-C6 branched chain alkyl or C3-C6 cycloalkyl;

R20 is selected from H, —CF3, C1-C6 straight chain alkyl, C3-C6 branched chain alkyl or C3-C6 cycloalkyl;

R14, R15 and R16 can independently be H, C1-C6 straight chain alkyl, C3-C6 branched chain alkyl, C1-C6 hydroxyalkyl, C1-C6 alkoxy, alkoxyalkyl in which the alkoxy and alkyl portions each independently contain from 1 to 6 carbon atoms, alkoxyalkoxy in which the alkoxy portions each independently contain from 1 to 6 carbon atoms, halogen, —OH, —NH 2 , —CF3, C1-C6 monoalkylamino, C1-C6 dialkylamino, and nitrogen containing heterocycles optionally substituted with one or more of R17 and R18; or

wherein X can be a bond, O, S or NR 19 ;

R17, R18 and R19 are independently selected from H, C1-C6 straight chain alkyl, C3-C6 branched chain alkyl, C3-C6 cycloalkyl, C1-C6 hydroxyalkyl, alkoxyalkyl in which the alkoxy and alkyl portions each independently contain from 1 to 6 carbon atoms, —CF3, or —C(O)O—, or R17 and R18 can be taken together to form a 4 to 7 membered monocycloalkyl ring or 8-14 bicycloalkyl ring, each optionally containing between 1-3 heteroatoms selected from N, O or S, or;

r is an integer ranging from 0 to 3;

t is an integer ranging from 1 to 2; and

u is an integer ranging from 1 to 6.

2. The compound according to claim 1 , wherein F is selected from the group consisting 2-pyrazinyl, 2-pyrimidinyl, 2-pyridinyl, 3-pyridinyl, and 4-pyridinyl, each of which is optionally substituted.

3. The compound according to claim 2 , wherein F is selected from 2-pyridinyl, 3-pyridinyl, and 4-pyridinyl.

4. The compound according to claim 1 , wherein H is —SO 2 —.

5. The compound according to claim 1 , wherein R13 is hydrogen or C1-C6 straight chain alkyl.

6. The compound according to claim 1 , wherein K is

7. A pharmaceutical composition comprising a compound of claim 1 , and pharmaceutically acceptable carrier.

8. The compound of claim 1 , which is

wherein, in Formula Va:

F is pyridin-3-yl;

m is 1;

p is 1;

H is—S(O)n-(CH2)q-, wherein n is 2 and q is 0;

K is,

wherein r is 2, R14 and R15 are both H, and R17 is isobutyl to give 1-isobutylpiperidin-4-yl;

R13 is H; and

R20 is methyl.

9. A pharmaceutical composition comprising the compound of claim 8 , and a pharmaceutically acceptable carrier.

Assignments (5)
CHANGE OF NAME Recorded Nov 17, 2016
From: RUGA CORPORATION
To: ARAVIVE BIOLOGICS, INC.
Reel/Frame 040645/0147 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2013
From: HAY, MICHAEL PATRICK; BONNET, MURIEL
To: AUCKLAND UNISERVICES LIMITED
Reel/Frame 031742/0677 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2013
From: GIACCIA, AMATO; LAI, EDWIN; RAZORENOVA, OLGA; CHAN, DENISE
To: THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY
Reel/Frame 031742/0969 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2013
From: SUN, CONNIE L.; TABIBIAZAR, RAY; YUEN, PO-WAI
To: RUGA CORPORATION
Reel/Frame 031785/0408 →
CONFIRMATORY LICENSE Recorded May 1, 2013
From: THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 030324/0567 →
Continuity (4)
Provisional Application 61475549 · Apr 14, 2011
Provisional Application 61434976 · Jan 21, 2011
Provisional Application 61391958 · Oct 11, 2010
Related Publication 20140024649A1 · Jan 23, 2014