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Generated: January 23, 2018

DrugPatentWatch Database Preview

Claims for Patent: 5,852,195

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Summary for Patent: 5,852,195
Title: Pyranone compounds useful to treat retroviral infections
Abstract:The present invention relates to compounds of formulae (I) and (II) which are pyran-2-ones, 5,6-dihydro-pyran-2-ones, 4-hydroxy-benzopyran-2-ones, 4-hydroxy-cycloalkyl[b]pyran-2-ones, and derivatives thereof, useful for inhibiting a retrovirus in a mammalian cell infected with said retrovirus, wherein R.sub.10 and R.sub.20 taken together are formulae (III) and (IV). ##STR1##
Inventor(s): Romines; Karen Rene (Paw Paw, MI), Bundy; Gordon L. (Portage, MI), Schwartz; Theresa M. (Kalamazoo, MI), Tommasi; Ruben A. (Whitehouse Station, NJ), Strohbach; Joseph W. (Mendon, MI), Turner; Steven Ronald (Kalamazoo, MI), Thaisrivongs; Suvit (Kalamazoo, MI), Aristoff; Paul Adrian (Kalamazoo, MI), Johnson; Paul D. (Portage, MI), Skulnick; Harvey Irving (Kalamazoo, MI), Skaletzky; Louis L. (Kalamazoo, MI), Anderson; David John (Kalamazoo, MI), Morris; Joel (Kalamazoo, MI), Gammill; Ronald B. (Portage, MI), Luke; George P. (Lexington, MA)
Assignee: Pharmacia & Upjohn Company (Kalamazoo, MI)
Application Number:08/809,224
Patent Claims: 1. The compound of the formula VI ##STR3## wherein R.sub.2 is a) H.sub.3 C--CH.sub.2 --, or

b) phenyl-(CH.sub.2).sub.2 --;

wherein R.sub.3 is the moiety of formula X ##STR4## wherein R.sub.6 is a) H.sub.3 C--(CH.sub.2).sub.2 --, or

b) phenyl-(CH.sub.2).sub.2 --;

wherein R.sub.7 is H.sub.3 C--CH.sub.2 --;

wherein R.sub.9 is --NHSO.sub.2 --het;

wherein het is 2-pyridinyl substituted at the 5-position by zero (0) or one (1) R.sub.10 ;

wherein R.sub.10 is

a) --CN,

b) --CF.sub.3,

c) --NH2, or

d) --CONH.sub.2 ;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 selected from the group consisting of: ##STR5##

3. The compound of claim 1 selected from the group consisting of:

5-Trifluoromethyl-N-[3-(R or S)-[1-[4-hydroxy-2-oxo-6,6-di-n-propyl-5,6-dihydro-2H-pyran-3-yl]-propyl]- phenyl]-2-pyridinesulfonamide;

5-Trifluoromethyl-N-[3-(R)-[1-[4-hydroxy-2-oxo-6,6-di-n-propyl-5,6-dihydro- 2H-pyran-3-yl]-propyl]-phenyl]-2-pyridinesulfonamide; or (3R)-N-[3-[1-(5,6-Dihydro-4-hydroxy-2-oxo-6,6-dipropyl-2H-pyran-3-yl)propy l]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

5-Trifluoromethyl-N-[3-(S)-[1-[4-hydroxy-2-oxo-6,6-di-n-propyl-5,6-dihydro- 2H-pyran-3-yl]-propyl]-phenyl]-2-pyridinesulfonamide; or (3S)-N-[3-[1-(5,6-Dihydro-4-hydroxy-2-oxo-6,6-dipropyl-2H-pyran-3-yl)propy l]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

5-Trifluoromethyl-N-[3(R or S)-[1-[5,6-dihydro-4-hydroxy-2-oxo-6(R or S)-(2-phenethyl)-6(R or S)-n-propyl-2H-pyran-3-yl]-propyl]-phenyl]-2-pyridine sulfonamide;

5-Trifluoromethyl-N-[3(R)-[1-[5,6-dihydro-4-hydroxy-2-oxo-6(R)-(2-phenethyl )-6(R)-n-propyl-2H-pyran-3-yl]-propyl]-phenyl]-2-pyridinesulfonamide; or (3R,6R)-N-[3-[1-(5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H -pyran-3-yl)propyl]-phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

5-Trifluoromethyl-N-[3(R)-[1-[5,6-dihydro-4-hydroxy-2-oxo-6(S)-(2-phenethyl )-6(S)-n-propyl-2H-pyran-3-yl]-propyl]-phenyl]-2-pyridinesulfonamide; or (3R,6S)-N-[3-[1-(5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H -pyran-3-yl)propyl]-phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

5-Trifluoromethyl-N-[3(S)-[1-[5,6-dihydro-4-hydroxy-2-oxo-6(R)-(2-phenethyl )-6(R)-n-propyl-2H-pyran-3-yl]-propyl]-phenyl]-2-pyridinesulfonamide; or (3S,6R)-N-[3-[1-[5,6,-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2 H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

5-Trifluoromethyl-N-[3(S)-[1-[5,6-dihydro-4-hydroxy-2-oxo-6(S)-(2-phenethyl )-6(S)-n-propyl-2H-pyran-3-yl]-propyl]-phenyl]-2-pyridinesulfonamide; or (3S,6S)-N-[3-[1-[5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H -pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

N-[3-[1-(S)-[5,6,-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyr an-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

(3R)-N-[3-[1-(5,6-Dihydro-4-hydroxy-2-oxo-6-propyl-6-phenethyl-2H-pyran-3-y l)propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

N-[3-{1(R or S)-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-dipropyl-2H-pyran-3-yl)-propyl}phenyl] -5-cyanopyridine-2-sulfonamide;

N-[3-{1(R)-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-dipropyl-2H-pyran-3-yl)-propyl} phenyl]-5-cyanopyridine-2-sulfonamide;

N-[3-{1(S)-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-dipropyl-2H-pyran-3-yl)-propyl} phenyl]-5-cyanopyridine-2-sulfonamide;

N-[3-{1(R or S)-(4-Hydroxy-5,6-dihydro-2-oxo-6(R or S)-phenethyl-6-propyl-2H-pyran-3-yl)propyl}phenyl]-5-cyanopyridine-2-sulfo namide;

N-[3-{1(R)-(4-Hydroxy-5,6-dihydro-2-oxo-6(R)-phenethyl-6-propyl-2H-pyran-3- yl)propyl}phenyl]-5-cyanopyridine-2-sulfonamide;

N-[3-{1(R)-(4-Hydroxy-5,6-dihydro-2-oxo-6(S)-phenethyl-6-propyl-2H-pyran-3- yl)propyl}phenyl]-5-cyanopyridine-2-sulfonamide;

N-[3-{1(S)-(4-Hydroxy-5,6-dihydro-2-oxo-6(R)-phenethyl-6-propyl-2H-pyran-3- yl)propyl}phenyl]-5-cyanopyridine-2-sulfonamide;

N-[3-{1(S)-(4-Hydroxy-5,6-dihydro-2-oxo-6(S)-phenethyl-6-propyl-2H-pyran-3- yl)propyl}phenyl]-5-cyanopyridine-2-sulfonamide;

5-Amino-N-[3(R or S)-(1-[5,6-dihydro-4-hydroxy-2-oxo-6(R or S)-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl)phenyl]-2-pyridinesulfona mide;

5-Amino-N-[3(R or S)-(1-[5,6-dihydro-4-hydroxy-2-oxo-6(R or S)-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl)phenyl]-2-pyridinesulfona mide;

5-Trifluoromethyl-N-[3-[1-[4-hydroxy-2-oxo-6,6-di-n-propyl-5,6-dihydro-2H-p yran-3-yl]-propyl]-phenyl]-2-pyridinesulfonamide;

N-[3-{1-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-bis(2-phenylethyl)-2H-pyran-3-yl)p ropyl}phenyl]-5-cyanopyridine-2-sulfonamide;

N-[3(R or S)-(1-[6,6-Bis(2-phenylethyl)-5,6-dihydro-4-hydroxy-2-oxo-2H-pyran-3-yl]pr opyl)phenyl]-5-cyano-2-pyridinesulfonamide;

N-[3(R or S)-(1-[6,6-Bis(2-phenyl-ethyl)-5,6-dihydro-4-hydroxy-2-oxo-2H-pyran-3-yl]p ropyl)phenyl]-5-cyano-2-pyridinesulfonamide;

N-[3-{1(R or S)-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-dipropyl-2H-pyran-3-yl)-propyl}phenyl] -5-aminopyridine-2-sulfonamide;

N-[3-{1(S or R)-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-dipropyl-2H-pyran-3-yl)-propyl}phenyl] -5-aminopyridine-2-sulfonamide;

5-Trifluoromethyl-N-[3-(R or S)-[1-[4-hydroxy-2-oxo-6,6-di-phenethyl-5,6-dihydro-2H-pyran-3-yl]-propyl] -phenyl]-2-pyridinesulfonamide;

5-Trifluoromethyl-N-[3-(R or S)-[1-[4-hydroxy-2-oxo-6,6-di-phenethyl-5,6-dihydro-2H-pyran-3-yl]-propyl] -phenyl]-2-pyridinesulfonamide;

N-[3-{1-(4-Hydroxy-5,6-dihydro-2-oxo-6-phenethyl-6-propyl-2H-pyran-3-yl)pro pyl}phenyl]-5-cyanopyridine-2-sulfonamide;

N-[3-{1-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-dipropyl-2H-pyran-3-yl)propyl}phen yl]-5-cyanopyridine-2-sulfonamide; and

N-[3-{1-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-dipropyl-2H-pyran-3-yl)propyl}phen yl]-5-carbamoylpyridine-2-sulfonamide.

4. The compound of claim 1 selected from the group consisting of:

(3R,6R)-N-[3-[1-(5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H- pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

(3R,6S)-N-[3-[1-(5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H- pyran-3-yl)propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

(3S,6R)-N-[3-[1-[5,6,-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H -pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

(3S,6S)-N-[3-[1-[5,6-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H- pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide;

N-[3-[1-(S)-[5,6,-Dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyr an-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide; and

(3R)-N-[3-[1-(5,6-Dihydro-4-hydroxy-2-oxo-6-propyl-6-phenethyl-2H-pyran-3-y l)propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide.

5. A compound selected from the group consisting of:

N-[3-{1-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-bis(2-phenylethyl)-2H-pyran-3-yl)m ethyl}phenyl]-5-cyanopyridine-2-sulfonamide, and

N-[3-{1-(4-Hydroxy-5,6-dihydro-2-oxo-6,6-bis(2-phenylethyl)-2H-pyran-3-yl)m ethyl}phenyl]-5-aminopyridine-2-sulfonamide.

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Serving leading biopharmaceutical companies globally:

Argus Health
Dow
Deloitte
Fish and Richardson
Boehringer Ingelheim
Colorcon
Express Scripts
Merck
Moodys

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