Substituted pyrimidinones bearing acidic functional groups as angiotensin II antagonists
First Claim
Patent Images
1. A compound of the Formula (I) ##STR115## wherein:
- A--B--C together with the pyrimidinone to which it is attached form a member selected from the group;
##STR116## Y is O, or S;
R1 is(a) --SO2 N(R24)--OR24,(b) --SO2 NHSO2 R23, ##STR117## (e) --SO2 NHCN, (f) --SO2 NHCO2 R23, ##STR118## wherein Y1 is O or S;
R2a and R2b are each independently(a) H,(b) Cl, Br, I, or F,(c) NO2,(d) NH2,(e) C1 -C4 -alkylamino,(f) di(C1 -C4 -alkyl)amino,(g) SO2 NHR9,(h) CF3,(i) C1 -C6 -alkyl,(j) C1 -C6 -alkoxy,(k) C1 -C6 -alkyl-S-,(l) C2 -C6 -alkenyl,(m) C2 -C6 -alkynyl,(n) aryl,(o) aryl(C1 -C4 -alkyl), or(p) C3 -C7 -cycloalkyl;
R3a is(a) H,(b) Cl, Br, I, or F,(c) C1 -C6 -alkyl,(d) C1 -C6 -alkoxy, or(e) C1 -C6 -alkoxyalkyl;
R3b is(a) H,(b) Cl, Br, I, or F,(c) NO2,(d) C1 -C6 -alkyl,(e) C1 -C6 -acyloxy,(f) C3 -C7 -cycloalkyl,(g) C1 -C6 -alkoxy,(h) --NHSO2 R4,(i) hydroxy(C1 -C4 -alkyl),(j) aryl(C1 -C4 -alkyl),(k) C1 -C4 -alkylthio,(l) C1 -C4 -alkyl sulfinyl,(m) C1 -C4 -alkyl sulfonyl,(n) NH2,(o) C1 -C4 -alkylamino,(p) di(C1 -C4 -alkyl)amino,(q) fluoro-C1 -C4 -alkyl-,(r) --SO2 --NHR9,(s) aryl,(t) furyl,(u) CF3,(v) C2 -C6 -alkenyl, or(w) C2 -C6 -alkynyl;
wherein aryl is phenyl or naphthyl or substituted phenyl or naphthyl with one or two substituents selected from the group consisting of Cl, Br, I, F, N(R4)2, CO2 R4, C1 -C4 -alkyl, C1 -C4 -alkoxy, NO2, CF3, C1 -C4 -alkylthio, --SO2 NR9 R10, C3 -C7 -cycloalkyl, C3 -C10 -alkenyl, or OH;
R4 is H, aryl as defined hereinabove, C1 -C6 alkyl, or substituted C1 -C6 alkyl with an aryl or heteroaryl substituent, wherein heteroaryl is an unsubstituted, monosubstituted or disubstituted heteroaromatic 5 or 6 membered cyclic which contains one to three heteratoms selected from the group consisting of N, O and S, and wherein the substituents are members selected from the group consisting of --OH, --SH, C1 -C4 -alkyl, C1 -C4 -alkoxy, --CF3, Cl, Br, I, F, and NO2 ;
R4a is aryl, C1 -C6 alkyl, or aryl-C1 -C6 -alkyl;
##STR119## E is a single bond, --NR13 (CH2)s --, --S(O)x (CH2)s -- where x is 0 to 2 and s is 0 to 5, --CH(OH)--, --O--, CO--;
R6 is(a) aryl,(b) C1 -C6 -alkyl, C2 -C5 -alkenyl or C2 -C5 -alkynyl or substituted C1 -C6 -alkyl, C2 -C5 -alkenyl or C2 -C5 -alkynyl substituted with a substituent selected from the group consisting of aryl, C3 -C7 -cycloalkyl, Cl, Br, I, F, CF3, CF2 CF3, --NH2, --NH(C1 -C4 -alkyl), --OR4 --N(C1 -C4 -alkyl)2, --NH--SO2 R4, --COOR4, or --SO2 NHR9,(c) heteroaryl as defined hereinabove,(d) C3 -C7 -cycloalkyl,(e) perfluoro-C1 -C4 -alkyl, or(f) H;
R7 is;
(a) H,(b) C1 -C6 -alkyl, C2 -C6 -alkenyl or C2 -C6 -alkynyl or substituted C1 -C6 -alkyl, C2 -C6 -alkenyl or C2 -C6 -alkynyl substituted with a substituent selected from the group consisting of C3 -C7 -cycloalkyl, Cl, Br, I, F, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 alkyl)2, --NHSO2 R4, --COOR4, C1 -C4 -alkoxyl, C1 -C4 -alkylthio, --CONH2, --COR4, or --SO2 R4, --NR4 COR22, --NR4 CO2 R22, --NR4 CONR4 R22, or --CO-heteroaryl,(c) --COR4,(d) phenyl or naphthyl or substituted phenyl or naphthyl with one or two substituents wherein the substitutents are V or W,(e) phenyl-C1 -C6 -alkyl or naphthyl-C1 -C6 -alkyl in which the phenyl or naphthyl group is unsubstituted, mono- or disubstituted with V or W,(f) --OR4,(g) heteroaryl, or(h) --CON(R4)2 ;
V and W are independently;
(a) H,(b) C1 -C5 -alkoxy,(c) C1 -C5 -alkyl,(d) hydroxy,(e) C1 -C5 -alkyl-S(O)x --,(f) CN,(g) NO2,(h) N(R4)2,(i) CON(R4)2,(j) CO2 R4,(k) COR4,(l) CF3,(m) Cl, Br, I, or F,(n) hydroxy-C1 -C5 -alkyl,(o) C1 -C5 -alkylthio,(p) --SO2 NR9 R10,(q) C3 -C7 -cycloalkyl, or(r) C2 -C10 -alkenyl;
R8a and R8b are independently(a) H,(b) C1 -C8 -alkyl, C2 -C6 -alkenyl or C2 -C6 -alkynyl or substituted C1 -C8 -alkyl, C2 -C6 -alkenyl or C2 -C6 -alkynyl with a substituent selected from the group consisting of --OH, -guanidino, C1 -C4 -alkoxy, --N(R4)2, COOR4, --CON(R4)2, --O--COR4, -aryl, -heteroaryl, --S(O)x --R22, -tetrazol-5-yl, --CONHSO2 R22, --SO2 NH-heteroaryl, --SO2 NHCOR22, --PO(OR4)2, --PO(OR4)R9, --SO2 NH--CN, --NR10 COOR22, --(CH2)1-4 R4, Cl, Br, F, or I,(c) --CO-aryl,(d) --C3 -C7 -cycloalkyl,(e) Cl, Br, I, or F,(f) --OH,(g) --OR22,(h) --C1 -C4 -perfluoroalkyl,(i) --S(O)x --R22,(j) --COOR4,(k) --SO3 H,(l) --NR22a R22,(m) --NR4 COR22,(n) --NR4 COOR22,(o) --SO2 NR4 R9,(p) --NO2,(q) --N(R22a)SO2 R22,(r) --NR22a CONR4 R22, ##STR120## (t) -aryl or -heteroaryl, (u) --SO2 NH-heteroaryl,(v) --SO2 NHCOR22,(w) --CONHSO2 R22,(x) --PO(OR4)2,(y) --PO(OR4)R4,(z) -tetrazol-5-yl,(aa) --CONH(tetrazol-5-yl),(bb) --COR4,(cc) --SO2 NHCN(dd) --NR4 SO2 NR4 R22,(ee) --NR4 SO2 OR22,(ff) --CONR4 R22, ##STR121## R9 is H, C1 -C5 -alkyl, aryl or arylmethyl;
R10 is H, C1 -C4 -alkyl;
R11 is H, C1 -C6 -alkyl, C1 -C4 -alkenyl, C1 -C4 -alkoxy alkyl, or ##STR122## R12 is --CN, --NO2, --CF3 or --CO2 R4 ;
R13 is H, (C1 -C4 -alkyl)CO--, C1 -C6 -alkyl, allyl, C3 -C6 -cycloalkyl, aryl or arylmethyl;
R14 is H, C1 -C8 -alkyl, C1 -C8 -perfluoroalkyl, C3 -C6 -cycloalkyl, aryl or arylmethyl;
R15 is H, C1 -C6 -alkyl;
R16 is H, C1 -C6 -alkyl, C3 -C6 -cycloalkyl, aryl or arylmethyl;
R17 is --NR9 R10, --OR10, --NHCONH2, --NHCSNH2, ##STR123## R18 and R19 are independently C1 -C4 -alkyl or taken together are --(CH2)q -- where q is 2 or 3;
R20 is H, --NO2, --NH2, --OH or --OCH3 ;
R21 is(a) aryl,(b) heteroaryl, or(c) C1 -C4 -alkyl or substituted C1 -C4 -alkyl with a substituent selected from the group consisting of aryl, heteroaryl as defined above, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, --CO2 R4a, Cl, Br, F, I, or --CF3 ;
R22 is(a) aryl,(b) heteroaryl,(c) C3 -C7 -cycloalkyl,(d) C1 -C6 -alkyl or substituted C1 -C6 -alkyl with a substituent selected from the group consisting of aryl, heteroaryl, --OH, --SH, C1 -C4 -alkyl, --O(C1 -C4 -alkyl), --S(C1 -C4 -alkyl), --CF3, Cl, Br, F, I, --NO2, --CO2 H, CO2 --(C1 -C4 -alkyl), --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, --PO3 H2, --PO(OH) (O-C1 -C4 -alkyl), --PO(OR4)R9, morpholinyl or N--C1 -C4 alkyl piperazinyl, or(e) perfluoro-C1 -C4 -alkyl;
R22a is(a) hydrogen,(b) aryl,(c) heteroaryl,(d) C3 -C7 -cycloalkyl,(e) C1 -C6 -alkyl or substituted C1 -C6 -alkyl with a substituent selected from the group consisting of aryl, heteroaryl, --OH, --SH, C1 -C4 -alkyl, --O(C1 -C4 -alkyl), --S(C1 -C4 -alkyl), --CF3, Cl, Br, F, I, --NO2, --CO2 H, CO2 --(C1 -C4 -alkyl), --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, --PO3 H2, --PO(OH)(O--C1 -C4 -alkyl), --PO(OR4)R9, morpholinyl or N--(C1 -C4 -alkyl)piperazinyl, or(f) perfluoro-C1 -C4 -alkyl;
R23 is(a) aryl,(b) heteroaryl,(c) C3 -C4 -cycloalkyl,(d) C1 -C4 -alkyl or substituted C1 -C4 alkyl with a substituent that is a member selected from the group consisting of aryl, heteroaryl, --OH, --SH, --C1 -C4 -alkyl, --C3 -C7 -cycloalkyl, --O(C1 -C4 -alkyl), --S(O)x (C1 -C4 -alkyl), --CF3, Cl, Br, F, I, --NO2, --CO2 H, --CO2 -C1 -C4 -alkyl, --NH2, --NH(C1 -C4 -alkyl), --NHCOR4a, --N(C1 -C4 -alkyl)2, --PO(OH)(C1 -C4 -alkyl), --PO(OH)(aryl), or --PO(OH)(O-C1 -C4 -alkyl);
where x is 0 to 2, or(e) perfluoro-C1 -C4 -alkyl;
R24 is(a) H,(b) aryl as defined above, or(c) C1 -C6 -alkyl optionally substituted with aryl, F, Cl, Br, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, or CF3 ;
R25 is(a) aryl as defined above,(b) C1 -C6 -alkyl optionally substituted with aryl, F, Cl, Br, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, CF3, --COOR4, or CN,(c) --OCH(R4)--O--CO--R4a, or(d) --OH, --O--C1 -C6 -alkyl wherein alkyl is as defined in (b);
R26 is(a) H,(b) C1 -C6 -alkyl optionally substituted with aryl, F, Cl, Br, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, CF3, --COOR4, or CN, or(c) F, Cl, Br;
X is(a) a carbon-carbon single bond,(b) --CO--,(c) --O--,(d) --S--, ##STR124## (h) --OCH2 --, (i) --CH2 O--(j) --SCH2 --,(k) --CH2 S--,(l) --NHC(R9)(R10),(m) --NR9 SO2 --,(n) --SO2 NR9 --,(o) --C(R9)(R10)NH--,(p) --CH═
CH--,(q) --CF═
CF--,(r) --CH═
CF--,(s) --CF═
CH--,(t) --CH2 CH2 --,(u) --CF2 CF2 --, ##STR125## r is 1 or 2; and
a pharmaceutically acceptable salt thereof.
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Abstract
Novel substituted fused pyrimidinones of formula (I) are useful as angiotensin II antagonists. ##STR1##
41 Citations
6 Claims
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1. A compound of the Formula (I) ##STR115## wherein:
- A--B--C together with the pyrimidinone to which it is attached form a member selected from the group;
##STR116## Y is O, or S;
R1 is(a) --SO2 N(R24)--OR24, (b) --SO2 NHSO2 R23, ##STR117## (e) --SO2 NHCN, (f) --SO2 NHCO2 R23, ##STR118## wherein Y1 is O or S; R2a and R2b are each independently (a) H, (b) Cl, Br, I, or F, (c) NO2, (d) NH2, (e) C1 -C4 -alkylamino, (f) di(C1 -C4 -alkyl)amino, (g) SO2 NHR9, (h) CF3, (i) C1 -C6 -alkyl, (j) C1 -C6 -alkoxy, (k) C1 -C6 -alkyl-S-, (l) C2 -C6 -alkenyl, (m) C2 -C6 -alkynyl, (n) aryl, (o) aryl(C1 -C4 -alkyl), or (p) C3 -C7 -cycloalkyl; R3a is (a) H, (b) Cl, Br, I, or F, (c) C1 -C6 -alkyl, (d) C1 -C6 -alkoxy, or (e) C1 -C6 -alkoxyalkyl; R3b is (a) H, (b) Cl, Br, I, or F, (c) NO2, (d) C1 -C6 -alkyl, (e) C1 -C6 -acyloxy, (f) C3 -C7 -cycloalkyl, (g) C1 -C6 -alkoxy, (h) --NHSO2 R4, (i) hydroxy(C1 -C4 -alkyl), (j) aryl(C1 -C4 -alkyl), (k) C1 -C4 -alkylthio, (l) C1 -C4 -alkyl sulfinyl, (m) C1 -C4 -alkyl sulfonyl, (n) NH2, (o) C1 -C4 -alkylamino, (p) di(C1 -C4 -alkyl)amino, (q) fluoro-C1 -C4 -alkyl-, (r) --SO2 --NHR9, (s) aryl, (t) furyl, (u) CF3, (v) C2 -C6 -alkenyl, or (w) C2 -C6 -alkynyl; wherein aryl is phenyl or naphthyl or substituted phenyl or naphthyl with one or two substituents selected from the group consisting of Cl, Br, I, F, N(R4)2, CO2 R4, C1 -C4 -alkyl, C1 -C4 -alkoxy, NO2, CF3, C1 -C4 -alkylthio, --SO2 NR9 R10, C3 -C7 -cycloalkyl, C3 -C10 -alkenyl, or OH; R4 is H, aryl as defined hereinabove, C1 -C6 alkyl, or substituted C1 -C6 alkyl with an aryl or heteroaryl substituent, wherein heteroaryl is an unsubstituted, monosubstituted or disubstituted heteroaromatic 5 or 6 membered cyclic which contains one to three heteratoms selected from the group consisting of N, O and S, and wherein the substituents are members selected from the group consisting of --OH, --SH, C1 -C4 -alkyl, C1 -C4 -alkoxy, --CF3, Cl, Br, I, F, and NO2 ; R4a is aryl, C1 -C6 alkyl, or aryl-C1 -C6 -alkyl;
##STR119## E is a single bond, --NR13 (CH2)s --, --S(O)x (CH2)s -- where x is 0 to 2 and s is 0 to 5, --CH(OH)--, --O--, CO--;R6 is (a) aryl, (b) C1 -C6 -alkyl, C2 -C5 -alkenyl or C2 -C5 -alkynyl or substituted C1 -C6 -alkyl, C2 -C5 -alkenyl or C2 -C5 -alkynyl substituted with a substituent selected from the group consisting of aryl, C3 -C7 -cycloalkyl, Cl, Br, I, F, CF3, CF2 CF3, --NH2, --NH(C1 -C4 -alkyl), --OR4 --N(C1 -C4 -alkyl)2, --NH--SO2 R4, --COOR4, or --SO2 NHR9, (c) heteroaryl as defined hereinabove, (d) C3 -C7 -cycloalkyl, (e) perfluoro-C1 -C4 -alkyl, or (f) H; R7 is; (a) H, (b) C1 -C6 -alkyl, C2 -C6 -alkenyl or C2 -C6 -alkynyl or substituted C1 -C6 -alkyl, C2 -C6 -alkenyl or C2 -C6 -alkynyl substituted with a substituent selected from the group consisting of C3 -C7 -cycloalkyl, Cl, Br, I, F, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 alkyl)2, --NHSO2 R4, --COOR4, C1 -C4 -alkoxyl, C1 -C4 -alkylthio, --CONH2, --COR4, or --SO2 R4, --NR4 COR22, --NR4 CO2 R22, --NR4 CONR4 R22, or --CO-heteroaryl, (c) --COR4, (d) phenyl or naphthyl or substituted phenyl or naphthyl with one or two substituents wherein the substitutents are V or W, (e) phenyl-C1 -C6 -alkyl or naphthyl-C1 -C6 -alkyl in which the phenyl or naphthyl group is unsubstituted, mono- or disubstituted with V or W, (f) --OR4, (g) heteroaryl, or (h) --CON(R4)2 ; V and W are independently; (a) H, (b) C1 -C5 -alkoxy, (c) C1 -C5 -alkyl, (d) hydroxy, (e) C1 -C5 -alkyl-S(O)x --, (f) CN, (g) NO2, (h) N(R4)2, (i) CON(R4)2, (j) CO2 R4, (k) COR4, (l) CF3, (m) Cl, Br, I, or F, (n) hydroxy-C1 -C5 -alkyl, (o) C1 -C5 -alkylthio, (p) --SO2 NR9 R10, (q) C3 -C7 -cycloalkyl, or (r) C2 -C10 -alkenyl; R8a and R8b are independently (a) H, (b) C1 -C8 -alkyl, C2 -C6 -alkenyl or C2 -C6 -alkynyl or substituted C1 -C8 -alkyl, C2 -C6 -alkenyl or C2 -C6 -alkynyl with a substituent selected from the group consisting of --OH, -guanidino, C1 -C4 -alkoxy, --N(R4)2, COOR4, --CON(R4)2, --O--COR4, -aryl, -heteroaryl, --S(O)x --R22, -tetrazol-5-yl, --CONHSO2 R22, --SO2 NH-heteroaryl, --SO2 NHCOR22, --PO(OR4)2, --PO(OR4)R9, --SO2 NH--CN, --NR10 COOR22, --(CH2)1-4 R4, Cl, Br, F, or I, (c) --CO-aryl, (d) --C3 -C7 -cycloalkyl, (e) Cl, Br, I, or F, (f) --OH, (g) --OR22, (h) --C1 -C4 -perfluoroalkyl, (i) --S(O)x --R22, (j) --COOR4, (k) --SO3 H, (l) --NR22a R22, (m) --NR4 COR22, (n) --NR4 COOR22, (o) --SO2 NR4 R9, (p) --NO2, (q) --N(R22a)SO2 R22, (r) --NR22a CONR4 R22, ##STR120## (t) -aryl or -heteroaryl, (u) --SO2 NH-heteroaryl, (v) --SO2 NHCOR22, (w) --CONHSO2 R22, (x) --PO(OR4)2, (y) --PO(OR4)R4, (z) -tetrazol-5-yl, (aa) --CONH(tetrazol-5-yl), (bb) --COR4, (cc) --SO2 NHCN (dd) --NR4 SO2 NR4 R22, (ee) --NR4 SO2 OR22, (ff) --CONR4 R22, ##STR121## R9 is H, C1 -C5 -alkyl, aryl or arylmethyl;
R10 is H, C1 -C4 -alkyl;R11 is H, C1 -C6 -alkyl, C1 -C4 -alkenyl, C1 -C4 -alkoxy alkyl, or ##STR122## R12 is --CN, --NO2, --CF3 or --CO2 R4 ;
R13 is H, (C1 -C4 -alkyl)CO--, C1 -C6 -alkyl, allyl, C3 -C6 -cycloalkyl, aryl or arylmethyl;R14 is H, C1 -C8 -alkyl, C1 -C8 -perfluoroalkyl, C3 -C6 -cycloalkyl, aryl or arylmethyl; R15 is H, C1 -C6 -alkyl; R16 is H, C1 -C6 -alkyl, C3 -C6 -cycloalkyl, aryl or arylmethyl; R17 is --NR9 R10, --OR10, --NHCONH2, --NHCSNH2, ##STR123## R18 and R19 are independently C1 -C4 -alkyl or taken together are --(CH2)q -- where q is 2 or 3; R20 is H, --NO2, --NH2, --OH or --OCH3 ; R21 is (a) aryl, (b) heteroaryl, or (c) C1 -C4 -alkyl or substituted C1 -C4 -alkyl with a substituent selected from the group consisting of aryl, heteroaryl as defined above, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, --CO2 R4a, Cl, Br, F, I, or --CF3 ; R22 is (a) aryl, (b) heteroaryl, (c) C3 -C7 -cycloalkyl, (d) C1 -C6 -alkyl or substituted C1 -C6 -alkyl with a substituent selected from the group consisting of aryl, heteroaryl, --OH, --SH, C1 -C4 -alkyl, --O(C1 -C4 -alkyl), --S(C1 -C4 -alkyl), --CF3, Cl, Br, F, I, --NO2, --CO2 H, CO2 --(C1 -C4 -alkyl), --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, --PO3 H2, --PO(OH) (O-C1 -C4 -alkyl), --PO(OR4)R9, morpholinyl or N--C1 -C4 alkyl piperazinyl, or (e) perfluoro-C1 -C4 -alkyl; R22a is (a) hydrogen, (b) aryl, (c) heteroaryl, (d) C3 -C7 -cycloalkyl, (e) C1 -C6 -alkyl or substituted C1 -C6 -alkyl with a substituent selected from the group consisting of aryl, heteroaryl, --OH, --SH, C1 -C4 -alkyl, --O(C1 -C4 -alkyl), --S(C1 -C4 -alkyl), --CF3, Cl, Br, F, I, --NO2, --CO2 H, CO2 --(C1 -C4 -alkyl), --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, --PO3 H2, --PO(OH)(O--C1 -C4 -alkyl), --PO(OR4)R9, morpholinyl or N--(C1 -C4 -alkyl)piperazinyl, or (f) perfluoro-C1 -C4 -alkyl; R23 is (a) aryl, (b) heteroaryl, (c) C3 -C4 -cycloalkyl, (d) C1 -C4 -alkyl or substituted C1 -C4 alkyl with a substituent that is a member selected from the group consisting of aryl, heteroaryl, --OH, --SH, --C1 -C4 -alkyl, --C3 -C7 -cycloalkyl, --O(C1 -C4 -alkyl), --S(O)x (C1 -C4 -alkyl), --CF3, Cl, Br, F, I, --NO2, --CO2 H, --CO2 -C1 -C4 -alkyl, --NH2, --NH(C1 -C4 -alkyl), --NHCOR4a, --N(C1 -C4 -alkyl)2, --PO(OH)(C1 -C4 -alkyl), --PO(OH)(aryl), or --PO(OH)(O-C1 -C4 -alkyl);
where x is 0 to 2, or(e) perfluoro-C1 -C4 -alkyl; R24 is (a) H, (b) aryl as defined above, or (c) C1 -C6 -alkyl optionally substituted with aryl, F, Cl, Br, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, or CF3 ; R25 is (a) aryl as defined above, (b) C1 -C6 -alkyl optionally substituted with aryl, F, Cl, Br, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, CF3, --COOR4, or CN, (c) --OCH(R4)--O--CO--R4a, or (d) --OH, --O--C1 -C6 -alkyl wherein alkyl is as defined in (b); R26 is (a) H, (b) C1 -C6 -alkyl optionally substituted with aryl, F, Cl, Br, --OH, --NH2, --NH(C1 -C4 -alkyl), --N(C1 -C4 -alkyl)2, CF3, --COOR4, or CN, or (c) F, Cl, Br; X is (a) a carbon-carbon single bond, (b) --CO--, (c) --O--, (d) --S--, ##STR124## (h) --OCH2 --, (i) --CH2 O-- (j) --SCH2 --, (k) --CH2 S--, (l) --NHC(R9)(R10), (m) --NR9 SO2 --, (n) --SO2 NR9 --, (o) --C(R9)(R10)NH--, (p) --CH═
CH--,(q) --CF═
CF--,(r) --CH═
CF--,(s) --CF═
CH--,(t) --CH2 CH2 --, (u) --CF2 CF2 --, ##STR125## r is 1 or 2; and
a pharmaceutically acceptable salt thereof. - View Dependent Claims (2, 3, 4, 5, 6)
- A--B--C together with the pyrimidinone to which it is attached form a member selected from the group;
Specification
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Current AssigneeMerck & Co., Inc.
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Original AssigneeMerck & Co., Inc.
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InventorsGreenlee, William J., Kim, Dooseop, Chakravarty, Prasun K., Patchett, Arthur A., Mantlo, Nathan B.
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Primary Examiner(s)Ford, John M.
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Assistant Examiner(s)GUPTA, YOGENDRA N
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Application NumberUS07/698,440Time in Patent Office781 DaysField of Search544/244, 544/262, 544/280, 544/284, 544/289, 544/255, 544/278, 544/2, 544/97, 514/258, 514/262US Class Current514/81CPC Class CodesA61P 43/00 Drugs for specific purposes...A61P 9/00 Drugs for disorders of the ...A61P 9/12 AntihypertensivesC07D 475/02 with an oxygen atom directl...C07D 475/04 with a nitrogen atom direct...C07D 487/04 Ortho-condensed systemsC07D 491/04 Ortho-condensed systemsC07D 495/04 Ortho-condensed systemsC07D 513/04 Ortho-condensed systemsC07F 9/6561 containing systems of two o...
