Small molecule CD4 mimetics and uses thereof

Patent metadata

Field	Value
Publication number	US-9776963-B2
Application number	US-200913128549-A
Country	US
Kind code	B2
Filing date	Nov 10, 2009
Priority date	Nov 10, 2008
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

The invention provides for compounds of formula I: wherein Z is absent or (CR A R B ) n W; each RA and RB is independently (i) H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, haloalkyl, each of which may be optionally substituted; (ii) OH, ORc, NH2, NHR c , NR c R c , SH, S(O) m R c ; or (iii) R A and R B together form C(O); W is absent, C(O), C(O)O, C(O)NR c R c , O, S(O) m , or NR c R c ; Y is an optionally substituted heterocyclic, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted aryl, or NR X R Y ; wherein R x and R y are each independently H, alkyl or aryl; X 1 is selected from the group consisting of halogen, methyl, and hydroxyl; X2 is a halogen; each R c is independently alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, or heteroaralkyl, each of which may be optionally substituted; m is O, 1, or 2; and n is 1, 2, 3, 4, 5, or 6; and pharmaceutically acceptable salts thereof.

First claim

What is claimed is:

1. A compound of formula I:

wherein:
Z is absent;
Y is optionally substituted cycloalkyl or optionally substituted aryl;
X 1 is fluorine;
X 2 is halogen;
or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein Y is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, [3.3.0]bicyclooctane, [4.3.0]bicyclononane, [4.4.0]bicyclodecane, [2.2.2]bicyclooctane, fluorenyl, phenyl, naphthyl, indanyl, or tetrahydronaphthyl, each of which may be optionally substituted.

3. The compound of claim 1 , wherein Y is:

each of which may be optionally substituted.

4. The compound of claim 1 , that is:

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 1 , that is:

or a pharmaceutically acceptable salt thereof.

6. The compound of claim 1 that is:

7. The compound of claim 1 that is

or a pharmaceutically acceptable salt thereof.

8. The compound of claim 1 , that is:

Assignees

• Sodroski Joseph G
• Madani Navid
• Schön Arne
• Lalonde Judith M
• Courter Joel R
• Soeta Takahiro
• Ng Danny
• Freire Ernesto
• Smith Iii Amos B
• Princiotto Amy M
• Le-Khac Matthew
• Hendrickson Wayne A
• Univ Pennsylvania
• Dana Farber Cancer Inst Inc
• Univ Johns Hopkins
• Bryn Mawr College
• Univ Columbia

Inventors

• Sodroski Joseph G
• Madani Navid
• Schön Arne
• Lalonde Judith M
• Courter Joel R
• Soeta Takahiro
• Ng Danny
• Freire Ernesto
• Smith Iii Amos B
• Princiotto Amy M
• Le-Khac Matthew
• Hendrickson Wayne A

Classifications

• C07D207/16

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D473/18

  one oxygen and one nitrogen atom, e.g. guanine · CPC title

• C07D237/32

  with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring · CPC title

• C07D231/56

  Benzopyrazoles; Hydrogenated benzopyrazoles · CPC title

• A61P31/18

  for HIV · CPC title