US 7,022,850 B2Granted

Bicyclicpyrimidones and their use to treat diseases

AssigneeBristol-Myers Squibb Company

InventorsKyoung S. Kim, Songfeng Lu, X. Christopher Sheng, Alvin Donald Crews

Life of this patent

Estimating the term…

Abstract

The present invention is directed to dihydropyrimidones having formula I or II and methods of using them to induce mitotic arrest, thereby making them useful as anti-cancer agents and other diseases that can be treated by inducing mitotic arrest.

Claims16

Dependent claims

A compound of formula I or II:

wherein:
X is O, or S
Y1 is H, alkyl, substituted alkyl, aryl, substituted aryl, cycloalkyl or substituted cycloalkyl;
Z is O or S;
R1 is H, or alkyl,
R2 and R3 are, independently, H alkyl, cycloalkyl or halogen or R2 and R3 may be taken together to form a C3 to C7 cycloalkyl;
n is 1 or 2;
A is N;
R4 is H, C(═O)R9, C(═O)OR10, C(═O)NR11R12, or S(O)2R13,
R9, R10, R11, R12, R13 are independently H, alkyl optionally substituted with alkoxy, alkyl, halo, alkylthio, hydroxyl, cyano, carboxy, amino, amido, carbamoyl, urea or thiol;
cycloalkyl, optionally substituted with halogen, alkyl, alkoxy, hydroxyl, amino, amido, carbamoyl, urea, nitro, cyano, thiol;
o, aryl, optionally substituted with alkyl, alkcoxy, halo, cyano, hydroxyl, carboxy, carbamoyl, alkyoxycarbonyl, nitro, alkenyloxy, trifluoromethyl, amino, cycloalkyl, aryl, heteroaryl, cyano, alkyl, sulfoxyl, sulfonyl, or thiol;
or heteroaryl, optionally substituted with halo, alkyl, alkenyl, alkynyl, aryl, nitro, cyano, hydroxyl, alkoxy, thioalkyl, carboxy, carbonyl, phenyl, benzyl, phenylethyl, phenoxy, phenylthio, cycloalkyl, heterocycloalkyl, heteroaryl, amion, amido, heteroaryl, amino or amido;
and
R5 is H, or alkyl, optionally substituted with alkoxy, alkyl, halo, alkylthio, hydroxyl, cyano, carboxy, amino, amido, carbamoyl, urea or thiol.

12 more elements

A compound selected from the group consisting of

(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-methyl-benzamide
(±)-3-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propylamino]-propionitrile
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-methyl-N-(3-morpholin-4-yl-propyl)-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(3-methoxy-propyl)-4-methyl-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-methyl-N-phenethyl-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-4-methyl-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-4-methyl-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(3-imidazol-1-yl-propyl)-4-methyl-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-2-methoxy-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-3-fluoro-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-3,4-dichloro-N-(2-cyano-ethyl)-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-2-methyl-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-4-fluoro-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-chloro-N-(2-cyano-ethyl)-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]4-tert-butyl-N-(2-cyano-ethyl)-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-cyano-N-(2-cyano-ethyl)-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-isonicotinamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-nicotinamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-benzenesulfonamide
(±)-3-{[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-[2-(4-chloro-phenyl)-2-oxo-ethyl]-amino}-propionitrile
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-chloro-N-(2-cyano-ethyl)-benzenesulfonamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-4-methoxy-benzenesulfonamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-tert-butyl-N-(2-cyano-ethyl)-benzenesulfonamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-3-niethyl-benzenesulfonamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-4-trifluoromethyl-benzamide
(±)-Quinoline-2-carboxylic acid [1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolol[5,4-d]pyrimidin-6-yl)-propyl]-(2-cyano-ethyl)-amide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolol[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-4-methyl-benzenesulfonamide
(±)-5-Methyl-isoxazole-3-carboxylic acid [1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(2-cyano-ethyl)-amide
(±)-Cyclobutanecarboxylic acid [1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(2-cyano-ethyl)-amide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-cyano-ethyl)-3-methyl-butyramide
(±)-Cyclohexanecarboxylic acid [1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolol[5,4-d]pyrimidin-6-yl)-propyl]-(2-cyano-ethyl)-amide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(2-cyano-ethyl)-acetamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(2-cyano-ethyl)-2-methoxy-acetamide
(±)-2,2,2-Trifluoro-ethanesulfonic acid [1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(2-cyano-ethyl)-amide
(±)-Propane-1-sulfonic acid [1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(2-cyano-ethyl)-amide
(±)-3-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propylamino]-propionamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-3-fluoro-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-3,4-dichloro-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-4-methoxy-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-2-methyl-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-3-methyl-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-4-fluoro-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-4-chloro-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-3-trifluoromethyl-benzamde
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-tert-butyl-N-(2-carbamoyl-ethyl)-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-4-cyano-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolol[5,4-d]pyrimidin-6-yl)-propyl]-N-(2-carbamoyl-ethyl)-3-cyano-benzamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-butyl-N-(2-carbamoyl-ethyl)-nicotinamide
(±)-3-{[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-[2-(4-chloro-phenyl)-2-oxo-ethyl]-amino}-propionamide
(±)-3-[[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)propyl]-(toluene-3-sulfonyl)-amino]-propionamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-butyl-N-(2-carbamoyl-ethyl)-4-trifluoromethyl-benzamide
(±)-Quinoline-2-carboxylic acid [1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-butyl-N-(2-carbamoyl-ethyl)-amide
(±)-3-[[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(1-methyl 1H-imidazole-4-sulfonyl)-amino]-propionamide
(±)-5-methyl-isoxazole-3-carboxylic acid [1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(1-methyl-1H-imidazole-4-sulfonyl)-amino]-amide
(±)-Cyclobutanecarboxylic acid [1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-amide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-butyl-N-(2-carbaxnoyl-ethyl)-isobutyramide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-butyl-N-(2-carbamoyl-ethyl)-3-methyl-butyramide
(±)-3-{Acetyl-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-amino}-propionamide
(±)-3-[[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(2-methoxy-aeetyl)-amino]-propionamide
(±)-3-[[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-(2,2,2-trifluoro-ethanesulfonyl)-amino]-propionamide
(±)-N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-bromo-N-(2-caibamoyl-ethyl)-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-2-methoxy-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-3-fluoro-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-3,4-dichloro-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-3-propyl-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-2-methyl-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-3-methyl-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzy-1-3-methyl-4-oxo-4,5-dihydro-isoxazo[5,4-d]pyrimidin-6-yl)-propyl]-4-chloro-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-isonicotinamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-benzenesulfonamide
(±)-Biphenyl-4-carboxylic acid (3-amino-propyl)-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-amide
(±)-N-(3Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-ethyl-benzamide
(±)-6-(1-{(3-Amino-propyl)-[2-(4-chloro-phenyl)-2-oxo-ethyl]-amino}-propyl)-5-benzyl-3-methyl-5H-isoxazolo[5,4-d]pyrimidin-4-one
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-trifluoromethoxy-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazalo[5,4-d]pyrimidin-6-yl)-propyl]-4-chloro-benzenesulfonamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-nitro-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-tert-butyl-benzenesulfonamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-3-methyl-benzenesulfonamide
(±)-Quinoline-2-carboxylic acid (3-amino-propyl)-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-amide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-]pyrimidin-6-yl)-propyl]-4-methyl-benzenesulfonamide
(±)-4-{(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-carbamoyl}-benzenesulfonyl fluoride
(±)-5-methyl-isoxazole-3-carboxylic acid (3-amino-propyl)-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-amide
(±)-Cyclobutanecarboxylic acid (3-amino-propyl)-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-amide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isaxazolol[5,4-d]pyrimidin-6-yl)-propyl]-isobutyramide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-3-methyl-butyramide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-acetamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-2-methoxy-acetamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-trifluoromethylsulfanyl-benzenesulfonamide
(±)-2,2,2-Trifluoro-ethanesulfonic acid (3-Amino-propyl)-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-amide
(±)-4-Acetylamino-N-(3-amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-benzamide
(±)-4-{(3-Amino-propyl)-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-sulfamoyl}-benzoic acid methyl ester
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-bromo-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-4-oxo-3-trifluoromethyl-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-bromo-benzamide
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-4-oxo-3-phenyl-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-methyl-benzamide
(±)-N-(3-Aminopropyl)-N-[1-(5-benzyl-3-isopropyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-methylbenzamide Hydrochloride
(±)-N-(3-Aminopropyl)-N-{1-[5-(4-chlorobenzyl)-3-isopropyl-4-oxo-4,5-dihydroisoxazolo[5,4-d]pyrimidin-6-yl]-propyl}-4-methylbenzamide Hydrochloride
(±)-N-(3-Amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isothiazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-chloro-benzamide;
and
(±)-N-(3-Amino-3-methyl-butyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydroisothiazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-chloro-benzamide.

99 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/848,089Filed 18 May 2004 · us provisional application
Priority: 22 May 2003
Published: US 2004/0242596 A12 Dec 2004
Granted: 4 Apr 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61K 31/519
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with heterocyclic rings
A61P 35/00
Antineoplastic agents
C07D 513/04
In which the condensed system contains two hetero rings: ortho-condensed systems

Family

Application60/472,880Us provisional application · filed 22 May 2003
US 2004/0242596 A1Pre-grant publication · published 2 Dec 2004
US 7,022,850 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Facts

Application

10/848,089Filed 18 May 2004 · us provisional application

Priority

22 May 2003

Published

US 2004/0242596 A12 Dec 2004

Granted

4 Apr 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61K 31/519
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with heterocyclic rings
A61P 35/00
Antineoplastic agents
C07D 513/04
In which the condensed system contains two hetero rings: ortho-condensed systems