Benzathine analogs

Patent metadata

Field	Value
Publication number	US-10159674-B2
Application number	US-201615138137-A
Country	US
Kind code	B2
Filing date	Apr 25, 2016
Priority date	Jun 8, 2012
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

A compound, or a pharmaceutically acceptable salt or ester thereof, having a structure of:

wherein X is a divalent linking moiety; and
R 1 -R 10 are each individually H, optionally-substituted alkyl, optionally-substituted alkoxy, optionally-substituted aryl, optionally-substituted cycloalkyl, optionally-substituted heterocyclic, halogen, amino, or hydroxy, provided that at least one of R 3 or R 8 is an optionally-substituted alkyl, a substituted alkoxy, optionally-substituted aryl, optionally-substituted cycloalkyl, optionally-substituted heterocyclic, or halogen.

First claim

The invention claimed is:

1. A compound, or a pharmaceutically acceptable salt thereof, having a structure of formula II:

wherein X is an optionally-substituted cycloalkanediyl; and
R 1 -R 10 are each individually H, optionally-substituted alkyl, optionally-substituted alkoxy, optionally-substituted aryl, optionally-substituted cycloalkyl, optionally-substituted heterocyclic, halogen, amino, or hydroxy, provided that at least one of R 3 or R 8 is an optionally-substituted N-heterocycle selected from pyrrolyl, H-pyrrolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, oxadiazolyl, isoxazolyl, furazanyl, isothiazolyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, tetrazolyl, dithiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, or triazinyl.

2. The compound of claim 1 , wherein at least one of R 3 or R 8 is an optionally-substituted N-heterocycle selected from pyrrolyl, H-pyrrolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, oxadiazolyl, isoxazolyl, furazanyl, isothiazolyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, tetrazolyl, or dithiazolyl.

3. The compound of claim 1 , wherein R 3 and R 8 are each an optionally-substituted N-heterocycle.

4. A pharmaceutical composition comprising at least one compound of claim 1 , and at least one pharmaceutically acceptable additive.

5. The compound of claim 1 , wherein X is cyclohexanediyl.

6. The compound of claim 2 , wherein X is cyclohexanediyl.

7. The compound of claim 1 , wherein R 3 and R 8 are each pyrrolidinyl.

8. The compound of claim 5 , wherein R 3 and R 8 are each pyrrolidinyl.

9. A compound, or a pharmaceutically acceptable salt thereof, having a structure of formula II:

wherein X is an optionally-substituted cycloalkanediyl; and
R 1 -R 10 are each individually H, optionally-substituted alkyl, optionally-substituted alkoxy, optionally-substituted aryl, optionally-substituted cycloalkyl, optionally-substituted heterocyclic, halogen, amino, or hydroxy, provided that R 3 and R 8 are each an optionally-substituted N-heterocycle selected from pyrrolyl, H-pyrrolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, oxadiazolyl, isoxazolyl, furazanyl, isothiazolyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, tetrazolyl, dithiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, or triazinyl.

10. The compound of claim 9 , wherein X is cyclohexanediyl.

11. The compound of claim 10 , wherein R 3 and R 8 are each pyrrolidinyl.

Assignees

• Univ Of Pittsburgh—Of The Commonwealth System Of Higher Education
• Us Veterans Affairs

Inventors

• Chen Beibei
• Mallampalli Rama K

Classifications

• A61P19/00

  Drugs for skeletal disorders · CPC title

• A61P11/06

  Antiasthmatics · CPC title

• C07D239/26

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title

• C07D265/30

  not condensed with other rings · CPC title