Nitrogen-containing heterocycles

• US 6,927,294 B1
• Filed: 03/10/2003
• Issued: 08/09/2005
• Est. Priority Date: 03/08/2002
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Yao, Xin, Petasis, Nicos A., Raber, Jeffrey C.
• Primary Examiner(s): Wilson, James O.
• Assistant Examiner(s): Tucker, Zachary C.
• Application Number:
  US10/386,389
• Time in Patent Office: 883 Days
• Field of Search: 546/183, 546/219, 546/220, 546/242
• US Class Current: 546/183
• CPC Class Codes: C07D 211/40 Oxygen atoms
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 471/04 Ortho-condensed systems

Abstract

Functionalized nitrogen heterocyclic compounds, including benzodiazepines and azasugars, and synthetic methods for preparing such compounds. Nitrogen-containing heterocycles are prepared by reacting amino-carbonyl compounds that contain an amine moiety connected via a linker to a carbonyl moiety with an organoboron derivative.

Claims

1. A compound of formula

wherein:

R¹ is hydrogen, alkyl, aryl, heteroaryl, hydroxy, or alkoxy;

R³ is aryl, heteroaryl, alkenyl, or alkynyl, or

R¹ and R³ can be joined to form a ring of 5 to 10 atoms;

R⁴ is hydrogen, alkyl, aryl, heteroaryl, alkenyl, alkynyl, acyl, carboxy, or carboxamido.

2. The compound of claim 1, wherein:

the compound has a formula selected from the following;

wherein R¹ is hydrogen, alkyl, aryl, heteroaryl, hydroxy, or alkoxy;

R³ is aryl, heteroaryl, alkenyl or alkynyl; and

R⁴ is hydrogen, alkyl, aryl, heteroaryl, alkenyl, alkynyl, acyl, carboxy, or carboxamido.

3. The compound of claim 1, wherein:

R³ is aryl, heteroaryl, or alkenyl, and

R⁴ is hydrogen.