IP Library Granted Patent US 7,101,873
Granted Patent B2
US 7,101,873 · App. 10/409,153 · Granted Sep 5, 2006

Pyrimidinedione derivatives

Assignee: Bexel Pharmaceuticals Inc.
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,101,873
App. No.
10/409,153
Granted
Sep 5, 2006
Kind
B2
Abstract

Pyrimidinedione derivatives of the general formula (I), their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them are useful for the treatment of inflammation and immunological diseases

Claims (45)

1. Novel pyrimidinedione derivatives of the formula (I)

their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their solvates, their pharmaceutically acceptable salts and their pharmaceutically acceptable compositions, wherein X and Y may be same or different and independently represent oxygen, sulfur or NR, wherein R represents hydrogen, hydroxyl, acyl, alkyl, alkoxy, aryl, amino, hydroxylamino, alkylamino, arylamino, acylamino, alkoxyamino group; the rings represented by A and B are selected from aryl or heteroaryl; R 1 and R 3 may be same or different and independently represent SR 7 , wherein R 7 represents alkyl or aryl, or S(O) p R 8 , wherein R 8 represents alkyl, amino or aryl group and p represents an integer of 1 or 2; R 2 and R 4 may be same or different and independently represent hydrogen, halogen, hydroxyl, nitro, cyano, azido, nitroso, amino, formyl, alkyl, haloalkyl, acyl, alkoxy, monoalkylamino, dialkylamino, acylamino, alkoxycarbonyl, alkylsulfonyl, alkylsulfinyl, alkylsulfanyl, sulfamoyl, alkoxyalkyl groups or carboxylic acids or its derivatives; R 5 and R 6 may be same or different and independently represent hydrogen, halogen, hydroxyl, formyl, cyano, nitro, nitroso, amino, alkyl, acyl, monoalkylamino, dialkylamino, arylamino, acylamino, alkoxyalkyl or COR 9 , wherein R 9 represents hydroxyl, amino, halogen, alkoxy, aryloxy, monoalkylamino, dialkylamino, arylamino, groups; m is an integer and is in the range of 0 to 2; n is an integer and is in the range of 0 to 2.

2. Novel pyrimidinedione derivatives as claimed in claim 1 , wherein the ring systems represented by A and B are selected from phenyl, naphthyl, pyrrolidinyl, morpholinyl, thiomorpholinyl, piperidinyl, piperazinyl, pyridyl, thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, pyrimidinyl, benzopyranyl, benzofuranyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzopyrolyl, benzoxadiazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, benzothienyl, benzofuranyl or indolyl.

3. Novel pyrimidinedione derivatives as claimed in claim 1 , which are selected from:

1-(4-Methylsulfanyl-phenyl)-6-phenyl-pyrimidin-2,4-(1H)-dione;

6-(4-Methylphenyl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Ethylphenyl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

1-(4-Methylphenyl)-6-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

1-(4-Bromophenyl)-6-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Chlorophenyl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Chloro-3-methylphenyl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(3-Chloro-4-methylphenyl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Fluoro-3-methylphenyl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Fluorophenyl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Methylsulfanyl-phenyl)-1-phenyl-pyrimidin-2,4-(1H)-dione;

6-(4-Methylphenyl)-1-(3-chloro-4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Methoxy-3-methylphenyl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Methylphenyl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Ethylphenyl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Chlorophenyl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Chloro-3-methylphenyl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Chlorophenyl)-1-(3-methoxy-4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(3-Chloro-4-methylphenyl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Fluorophenyl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

1-(4-Methylsulfonyl-phenyl)-6-phenyl-pyrimidin-2,4-(1H)-dione;

1-(4-Methylsulfanyl-phenyl)-6-(pyridin-2-yl)-pyrimidin-2,4-(1H)-dione;

6-(4-Methylpyridin-2-yl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Chloropyridin-2-yl)-1-(4-methylsulfanyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Methylsulfanyl-phenyl)-1-(pyridin-2-yl)-pyrimidin-2,4-(1H)-dione;

1-(4-Methylsulfonyl-phenyl)-6-(pyridin-2-yl)-pyrimidin-2,4-(1H)-dione;

6-(4-Methylpyridin-2-yl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

6-(4-Chloropyridin-2-yl)-1-(4-methylsulfonyl-phenyl)-pyrimidin-2,4-(1H)-dione;

4-(2,4-Dioxo-6-(4-methylphenyl)-3,4-dihydro-2H-pyrimidin-1-yl)-benzenesulfonamide;

4-(2,4-Dioxo-6-phenyl-3,4-dihydro-2H-pyrimidin-1-yl)-benzenesulfonamide;

4-[6-(4-Bromo-phenyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-benzenesulfonamide;

4-(2,6-Dioxo-3-phenyl-1,2,3,6-tetrahydro-pyrimidin-4-yl)-benzenesulfonamide;

4-(2,6-Dioxo-3-(4-methylsulfanyl-phenyl)-1,2,3,6-tetrahydro-pyrimidin-4-yl)-benzenesulfonamide and

4-[3-(4-Chloro-phenyl)-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl]-benzenesulfonamide.

4. A compound of formula (Ic)

their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their solvates, their pharmaceutically acceptable salts and their pharmaceutically acceptable compositions, wherein X and Y may be same or different and independently represent oxygen, sulfur or NR, wherein R represents hydrogen, hydroxyl, acyl, alkyl, alkoxy, aryl, amino, hydroxylamino, alkylamino, arylamino, acylamino, alkoxyamino group; the rings represented by A and B are selected from aryl or heteroaryl; R 1 and R 3 may be same or different and independently represent SR 7 , wherein R 7 represents alkyl or aryl, or S(O) p R 8 , wherein R 8 represents alkyl, amino or aryl group and p represents an integer of 1 or 2; R 2 and R 4 may be same or different and independently represent hydrogen, halogen, hydroxyl, nitro, cyano, azido, nitroso, amino, formyl, alkyl, haloalkyl, acyl, alkoxy, monoalkylamino, dialkylamino, acylamino, alkoxycarbonyl, alkylsulfonyl, alkylsulfinyl, alkylsulfanyl, sulfamoyl, alkoxyalkyl groups or carboxylic acids or its derivatives; R 5 and R 6 may be same or different and independently represent hydrogen, halogen, hydroxyl, formyl, cyano, nitro, nitroso, amino, alkyl, acyl, monoalkylamino, dialkylamino, arylamino, acylamino, alkoxyalkyl or COR 9 , wherein R 9 represents hydroxyl, amino, halogen, alkoxy, aryloxy, monoalkylamino, dialkylamino, arylamino, groups; m is an integer and is in the range of 0 to 2; n is an integer and is in the range of 0 to 2.

5. A pharmaceutical composition which comprises a compound of formula (I)

as defined in claim 1 and a pharmaceutically acceptable carrier, diluent, excipient or solvate.

6. A pharmaceutical composition as claimed in claim 5 , in the form of a tablet, capsule, powder, syrup, solution or suspension.

7. A pharmaceutical composition which comprises a compound as claimed in claim 3 and a pharmaceutically acceptable carrier, diluent, excipient or solvate.

8. A pharmaceutical composition as claimed in claim 7 , in the form of a tablet, capsule, powder, syrup, solution or suspension.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 3, 2008
From: BEXEL PHARMACEUTICALS INC.
To: ORCHID RESEARCH LABORATORIES
Reel/Frame 021194/0419 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2006
From: ORCHID RESEARCH LABORATORIES LTD.
To: BEXEL PHARMACEUTICALS INC.
Reel/Frame 017330/0759 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2006
From: ORCHID CHEMICALS & PHARMACEUTICALS, LTD.
To: ORCHID RESEARCH LABORATORIES LTD.
Reel/Frame 017330/0816 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2003
From: AGARWAL, SHIV KUMAR; TADIPARTHI, RAVIKUMAR; AGGARWAL, PAWAN; SHIVAKUMAR, SAVITHIRI
To: ORCHID CHEMICALS & PHARMACEUTICALS LIMITED
Reel/Frame 013856/0897 →
Priority Claims (1)
IN 266/MAS/2002 · Apr 10, 2002 · national
Continuity (1)
Related Publication 20040009975A1 · Jan 15, 2004