Myxovirus therapeutics, compounds, and uses related thereto

Patent metadata

Field	Value
Publication number	US-9676727-B2
Application number	US-201615204285-A
Country	US
Kind code	B2
Filing date	Jul 7, 2016
Priority date	Oct 24, 2011
Publication date	Jun 13, 2017
Grant date	Jun 13, 2017

Abstract

This disclosure relates to antiviral compounds disclosed herein and uses related thereto. In certain embodiments, the disclosure relates to pharmaceutical compositions. Typically, the pharmaceutical composition comprises a compound of formula I:

or salt, prodrug, or ester thereof wherein X, Y, and R 1 and R 10 to R 13 are described herein.

First claim

The invention claimed is:

1. A method of treating distemper virus comprising administering an effective amount of (S)-1-methyl-N-(4-((2-(2-morpholinoethyl)piperidin-1-yl)sulfonyl)phenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide or salt thereof to a subject in need thereof.

2. A method of treating distemper virus comprising administering an effective amount of a pharmaceutical composition to a subject in need thereof, wherein the pharmaceutical composition comprises a compound of Formula I

wherein,
X is O, S, NH, or CH 2 ;
Y is SO 2 or SO;
R 1 is dialkylamino, aryl, or heterocyclyl, optionally substituted with one or more, the same or different, R 14 ;
R 12 is 1,3-dimethyl-pyrazol-5-yl optionally substituted with one or more, the same or different, halogen on the methyl groups of the pyrazole ring;
R 10 , R 11 , and R 13 are each the same or different hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, alkanoyl, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkyl sulfonyl, aryl sulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein each R 10 , R 11 , and R 13 are optionally substituted with one or more, the same or different, R 14 ;
R 14 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, alkanoyl, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkyl sulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R 14 is optionally substituted with one or more, the same or different, R 15 ;
R 15 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, alkanoyl, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl) 2 amino, alkylsulfinyl, alkyl sulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R 15 is optionally substituted with one or more, the same or different, R 16 ; and

R 16 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methyl sulfinyl, ethyl sulfinyl, mesyl, ethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethyl sulfamoyl, N,N-di ethyl sulfamoyl, N-methyl-N-ethyl sulfamoyl, carbocyclyl, aryl, or heterocyclyl;
or salts thereof; and dimethacrylated cyclodextrin and optionally polyethylene glycol.

Assignees

• Univ Emory
• Children'S Healthcare Of Atlanta Inc

Inventors

• Plemper Richard K
• Snyder James P
• Sun Aiming

Classifications

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A61P31/12

  Antivirals · CPC title

• A61K47/40

  Cyclodextrins; Derivatives thereof · CPC title

• A61K47/10

  Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers · CPC title

• C07D231/14 Primary

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