NO- AND H2S- RELEASING COMPOUNDS

• US 20170260124A1
• Filed: 05/25/2017
• Published: 09/14/2017
• Est. Priority Date: 08/15/2011
• Status: Active Grant

• Current Assignee: City College of New York
• Original Assignee: City College of New York
• Inventors: Kashfi, Khosrow, Kodela, Ravinder
• Granted Patent: US 10,450,260 B2
• Time in Patent Office: Days
• CPC Class Codes: A61K 31/655 Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: C07C 203/04 having nitrate groups bound to acyclic carbon atoms
• CPC Class Codes: C07C 327/48 having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 331/28 having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07D 271/08 1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
• CPC Class Codes: C07D 339/04 having the hetero atoms in positions 1 and 2, e.g. lipoic acid
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07F 9/65583 each of the hetero rings containing nitrogen as ring hetero atom
• CPC Class Codes: C07F 9/6578 having phosphorus and sulfur atoms with or without oxygen atoms, as ring hetero atoms

Abstract

This disclosure relates to compounds containing both an NO-releasing moiety and an H₂S-releasing moiety and the use of such compounds in treating inflammatory diseases, including cancers.

Claims

1-71. -71. (canceled)

72. A compound comprising a NO-releasing moiety, a H₂S-releasing moiety, and a core, wherein the core comprises

73. The compound of claim 72, wherein the NO-releasing moiety is —

NO, —

C(O)—

(CH₂)_n—

ONO₂, —

O—

(CH₂)_n—

ONO₂, —

(CH₂)_n—

ONO₂, —

C(O)—

CH₂—

C(CH₃)₂—

SNO, —

NH—

CH₂—

C(CH₃)₂—

SNO, —

CH₂—

C(CH₃)₂—

SNO,

74. The compound of claim 72, wherein the compound is of formula (II):

75. The compound of claim 74, wherein R₁, R₂, R₃, R₄, R₅, and R₆ is H;

and R₇ is CH₃.

76. The compound of claim 72 selected from the group consisting of

77. A method of treating an inflammatory disease, comprising administering to a subject in need thereof an effective amount of a compound of claim 72.

79. A pharmaceutical composition comprising a compound according to claim 72 and a pharmaceutically acceptable excipient.

78. The method of claim 89, wherein the inflammatory disease is cancer, rheumatoid arthritis, intestine inflammation, stomach ulcer, a cardiovascular disease, or a neurodegenerative disease.