Aminediols for the treatment of Alzheimer's disease
First Claim
Patent Images
1. A compound of the formula I:
-
or a pharmaceutical salt thereof, whereinR1 is aryl, or aryl (C1-C6)alkyl-, where the ring portions of each are optionally substituted with 1, 2, 3, or 4 groups independently selected from halogen, —
OH, —
SH, —
C≡
N, —
NO2, —
NR105R′
105, —
CO2R, —
N(R)COR′
, —
N(R)SO2R′
, —
C(═
O)—
(C1-C4)alkyl, —
SO2-amino, —
SO2-monoalkylamino, —
SO2-dialkylamino, —
C(═
O)-amino, —
C(═
O)-monoalkylamino, —
C(═
O)-dialkylamino, —
SO2—
(C1-C4)alkyl, C1-C6 alkoxy optionally substituted with 1, 2, or 3 groups which are independently selected from halogen, C3-C7 cycloalkyl optionally substituted with 1, 2, or 3 groups independently selected from halogen, —
OH, —
SH, —
C≡
N, —
CF3, C1-C3 alkoxy, amino, —
C1-C6 alkyl and mono- or dialkylamino, C1-C10 alkyl optionally substituted with 1, 2, or 3 groups independently selected from halogen, —
OH, —
SH, —
C≡
N, —
CF3, —
C1-C3 alkoxy, amino, mono- or dialkylamino and —
C1-C3 alkyl, and C2-C10 alkenyl or C2-C10 alkynyl each of which is optionally substituted with 1, 2, or 3 groups independently selected from halogen, —
OH, —
SH, —
C≡
N, —
CF3, C1-C3 alkoxy, amino, C1-C6 alkyl and mono- or dialkylamino;
R and R′
independently are hydrogen, C1-C10 alkyl, or C1-C10 alkylaryl;
R2 is H;
Rc is hydrogen, —
(CR245R250)0-4-aryl, —
(CR245R250)0-4-aryl-aryl, —
CH(aryl)2, —
(CH2)0-1—
CH((CH2)0-6—
OH)—
(CH2)0-1-aryl, —
CH(-aryl) —
CO—
O(C1-C4 alkyl), —
(C1-C6 alkyl)-O—
(C1-C6 alkyl) —
OH;
—
CH2—
NH—
CH2—
CH (—
O—
CH2—
CH3)2, —
(CH2)0-6—
C(═
NR235)(NR235R240), C1-C10 alkyl optionally substituted with 1, 2, or 3 groups independently selected from the group consisting of R110, R120 and R130, C2-C10 alkyl optionally substituted with 1, 2, or 3 groups independently selected from the group consisting of R205, R110, R120, R130, —
OC═
ONR235R240, —
S(═
O)0-2(C1-C6 alkyl), —
SH, and —
S(═
O)2NR235R240, C2-C10 alkenyl or C2-C10 alkynyl, each of which is optionally substituted with 1, 2, or 3 independently selected R205 groups, wherein each aryl is optionally substituted with 1, 2, or 3 R200;
R200 at each occurrence is independently selected from —
OH, —
NO2, halogen, —
CO2H, C≡
N, —
(CH2)0-4—
CO—
NR220R225, —
(CH2)0-4—
CO—
(C1-C12 alkyl), —
(CH2)0-4—
CO—
(C2-C12 alkenyl), —
(CH2)0-4—
CO—
(C2-C12 alkynyl), —
(CH2)0-4—
CO—
(C3-C7 cycloalkyl), —
(CH2)0-4—
CO-aryl, —
(CH2)0-4—
CO—
O—
R215, —
(CH2)0-4—
SO2—
NR220R225, —
(CH2)0-4—
SO—
(C1-C8 alkyl), —
(CH2)0-4—
SO2—
(C1-C12 alkyl), —
(CH2)0-4—
SO2—
(C3-C7 cycloalkyl), —
(CH2)0-4—
N(H or R215)—
CO—
O—
R215, —
(CH2)0-4—
N(H or R215)—
CO—
N(R215)2, —
(CH2)0-4—
N—
CS—
N(R215)2, —
(CH2)0-4—
N(—
H or R215)—
CO—
R220, —
(CH2)0-4—
NR220R225, —
(CH2)0-4—
O—
CO—
(C1-C6 alkyl), —
(CH2)0-4—
O—
P(O)—
(OR240)2, —
(CH2)0-4—
O—
CO—
N(R215)2, —
(CH2)0-4—
O—
CS—
N(R215)2, —
(CH2)0-4—
O—
(R215), —
(CH2)0-4—
O—
(R215)—
COOH, —
(CH2)0-4—
S—
(R215), —
(CH2)0-4—
O—
(C1-C6 alkyl optionally substituted with 1, 2, 3, or 5 —
F), C3-C7 cycloalkyl, —
(CH2)0-4—
N(H or R215)—
SO2—
R220, —
(CH2)0-4—
C3-C7 cycloalkyl, C1-C10 alkyl optionally substituted with 1, 2, or 3 independently selected R205 groups, C2-C10 alkenyl and C2-C10 alkynyl, each of which is optionally substituted with 1 or 2 independently selected R205 groups, wherein the aryl groups at each occurrence are optionally substituted with 1, 2, or 3 groups that are independently R205, R210, or C1-C6 alkyl substituted with 1, 2, or 3 groups that are independently R205 or R210;
R205 at each occurrence is independently selected from C1-C6 alkyl, halogen, —
OH, —
O-phenyl, —
SH, —
S—
C1-C6 alkyl, —
C≡
N, —
CF3, C1-C6 alkoxy, NH2, NH(C1-C6 alkyl) or N—
(C1-C6 alkyl)(C1-C6 alkyl);
R210 at each occurrence is independently selected from halogen, C1-C6 alkoxy, C1-C6 haloalkoxy, —
NR220R225, OH, C≡
N, —
CO—
(C1-C4 alkyl), —
SO2—
NR235R240, —
CO—
NR235R240, —
SO2—
(C1-C4 alkyl), ═
O, or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C7 cycloalkyl, each of which is optionally substituted with 1, 2, or 3 R205 groups;
R215 at each occurrence is independently selected from C1-C6 alkyl, —
(CH2)0-2-(aryl), C2-C6 alkenyl, C2-C6 alkynyl, and C3-C7 cycloalkyl, wherein the aryl group at each occurrence is optionally substituted with 1, 2, or 3 groups that are independently R205 or R210;
R220 and R225 at each occurrence are independently selected from —
H, —
C3-C7 cycloalkyl, —
(C1-C2 alkyl)-(C3-C7 cycloalkyl), —
(C1-C6 alkyl)-O—
(C1-C3 alkyl), —
C2-C6 alkenyl, —
C2-C6 alkynyl, —
C1-C6 alkyl chain with one double bond and one triple bond, -aryl, and —
C1-C10 alkyl optionally substituted with —
OH, —
NH2 or halogen, wherein the aryl, group at each occurrence is optionally substituted with 1, 2, or 3 independently selected R270 groups R235 and R240 at each occurrence are independently H, or C1-C6 alkyl;
R245 and R250 at each occurrence are independently selected from —
H, C1-C4 alkyl, C1-C4 alkylaryl, C1-C4 hydroxyalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, —
(CH2)0-4—
C3-C7 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, and phenyl;
or R245 and R250 are taken together with the carbon to which they are attached to form a carbocycle of 3, 4, 5, 6, or 7 carbon atoms R270 at each occurrence is independently R205, halogen C1-C6 alkoxy, C1-C6 haloalkoxy, NR235R240, —
OH, —
C≡
N, —
CO—
(C1-C4 alkyl), —
SO2—
NR235R240, —
CO—
NR235R240, —
SO2—
(C1-C4 alkyl), ═
O, or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or —
(CH2)0-4—
C3-C7 cycloalkyl, each of which is optionally substituted with 1, 2, or 3 R205 groups;
RN is R′
100, —
SO2R′
100, —
(CRR′
)1-6R′
100, —
C(═
O)—
(CRR′
)0-6R100, —
C(═
O)—
(CRR′
)1-6—
O—
R′
100, —
C(═
O)—
(CRR′
)1-6—
S—
R′
100, —
C(═
O)—
(CRR′
)1-6—
C(═
O)—
R100, —
C(═
O)—
(CRR′
)1-6—
SO2—
R100 or —
C(═
O)—
(CRR′
)1-6—
NR100—
R′
100;
R100 and R′
100 independently represent aryl, -aryl-W-aryl, -aryl-W-heteroaryl, -aryl-W-heterocyclyl, -heteroaryl-W-aryl, -heterocyclyl-W-aryl, —
CH[(CH2)0-2—
O—
R150]—
(CH2)0-2-aryl, where the ring portions of each are optionally substituted with 1, 2, or 3 groups independently selected from —
OR, —
NO2, C1-C6 alkyl, halogen, —
C≡
N, —
OCF3, —
CF3, —
(CH2)0-4—
O—
P(═
O)(OR)(OR′
), —
(CH2)0-4—
CO—
NR105R′
105, —
(CH2)0-4—
O—
(CH2)0-4—
CONR102R102′
, —
(CH2)0-4—
CO—
(C1-C12 alkyl), —
(CH2)0-4—
CO—
(C2-C12 alkenyl), —
(CH2)0-4—
CO—
(C2-C12 alkynyl), —
(CH2)0-4—
CO—
(CH2)0-4(C3-C7 cycloalkyl), —
(CH2)0-4—
R110, —
(CH2)0-4—
R120, —
(CH2)0-4—
R130, —
(CH2)0-4—
CO—
R110, —
(CH2)0-4—
CO—
R120, —
(CH2)0-4—
CO—
R130, —
(CH2)0-4—
CO—
R140, —
(CH2)0-4—
CO—
O—
R150, —
(CH2)0-4—
SO2—
NR105R′
105, —
(CH2)0-4—
SO—
(C1-C8 alkyl), —
(CH2)0-4—
SO2—
(C1-C12 alkyl), —
(CH2)0-4—
SO2—
(CH2)0-4—
(C3-C7 cycloalkyl), —
(CH2)0-4—
N(R150)—
CO—
O—
R150, —
(CH2)0-4—
N(R150)—
CO—
N(R150)2, —
(CH2)0-4—
N(R150)—
CS—
N(R150)2, —
(CH2)0-4—
N(R150)—
CO—
R105, —
(CH2)0-4—
NR105R′
105, —
(CH2)0-4—
R140, —
(CH2)0-4—
O—
CO—
(C1-C6 alkyl), —
(CH2)0-4—
O—
P(O)—
(O—
R110)2, —
(CH2)0-4—
O—
CO—
N(R150)2, —
(CH2)0-4—
O—
CS—
N(R150)2, —
(CR2)0-4—
O—
(R150), —
(CH2)0-4—
O—
R150′
—
COCH, —
(CH2)0-4—
S—
(R150), —
(CR2)0-4—
N(R150)—
SO2—
R105, —
(CH2)0-4—
C3-C7 cycloalkyl, (C2-C10alkenyl, and (C2-C10)alkynyl, or R100 is C1-C10 alkyl optionally substituted with 1, 2, or 3 R115 groups, or R100 is —
(C1-C6 alkyl)—
O-C1-C6 alkyl) or —
(C1-C6 alkyl)—
S—
(C1-C6 alkyl), each of which is optionally substituted with 1, 2, or 3 R115 groups, or R100 is C3-C8 cycloalkyl optionally substituted with 1, 2, or 3 R115 groups;
W is —
(CH2)0-4—
, —
O—
, —
S(O)0-2—
, —
N(R135)—
, —
CR(OH)—
or —
C(O)—
;
R102 and R102′
independently are hydrogen, or C1-C10 alkyl optionally substituted with 1, 2, or 3 groups that are independently halogen, aryl or —
R110;
R105 and R′
105 independently represent —
H, —
R110, —
R120, C3-C7 cycloalkyl, —
(C1-C2 alkyl)-(C3-C7 cycloalkyl), —
(C1-C6 alkyl)-O—
(C1-C3 alkyl), C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkyl chain with one double bond and one triple bond, or C1-C6 alkyl optionally substituted with —
OH or —
NH2;
or, C1-C6 alkyl optionally substituted with 1, 2, or 3 groups independently selected from halogen, or R105 and R′
105 together with the atom to which they are attached form a 3 to 7 membered carbocylic ring, where one member is optionally a heteratom selected from —
O—
, —
S(O)0-2—
, —
N(R135)—
, the ring being optionally substituted with 1, 2 or 3 independently selected R140 groups;
R115 at each occurrence is independently halogen, —
OH, —
CO2R102, —
C1-C6 thioalkoxy, —
CO2-phenyl, —
NR105R′
135, —
SO2—
(C1-C8 alkyl), —
C(═
O)R150, R180, —
CONR105R′
105, —
SO2NR105R′
105, —
NH—
CO—
(C1-C6 alkyl), —
NH—
C(═
O)—
OH, —
NH—
C(═
O)—
OR, —
NH—
C(═
O)—
O-phenyl, —
O—
C(═
O)—
(C1-C6 alkyl), —
O—
C(═
O)-amino, —
O—
C(═
O)-mono- or dialkylamino, —
O—
C(═
O)-phenyl, —
O—
(C1-C6 alkyl)-CO2H, —
NH—
SO2—
(C1-C6 alkyl), C1-C6 alkoxy or C1-C6 haloalkoxy;
R135 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, —
(CH2)0-2-(aryl), —
(CH2)0-2-(heteroaryl), or —
(CH2)0-2-(heterocyclyl);
R140 is heterocyclyl optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxy, cyano, nitro, amino, mono(C1-C6 alkylamino, di(C1-C6)alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, amino(C1-C6alkyl, mono(C1-C6)alkylamino(C1-C6)alkyl, di(C1-C6)alkylamino(C1-C6)alkyl, and ═
O;
R145 is C1-C6 alkyl or CF3;
R150 is hydrogen, C3-C7 cycloalkyl, —
(C1-C2 alkyl)-(C3-C7 cycloalkyl), C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl with one double bond and one triple bond, —
R110, —
R120, or C1-C6 alkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from —
OH, —
NH2, C1-C3 alkoxy, R110, and halogen;
R150′
is C3-C7 cycloalkyl, —
(C1-C3 alkyl)-(C3-C7 cycloalkyl), C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl with one double bond and one triple bond, —
R110, —
R120, or C1-C6 alkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from —
OH, —
NH2, C1-C3 alkoxy, R110, and halogen;
R155 is C3-C7 cycloalkyl, —
(C1-C2 alkyl)-(C3-C7 cycloalkyl), C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl with one double bond and one triple bond, —
R110, —
R120, or C1-C6 alkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from —
OH, —
NH2, C1-C3 alkoxy, and halogen;
R180 is selected from morpholinyl, thiomorpholinyl, piperazinyl, piperidinyl, homomorpholinyl, homothiomorpholinyl, homothiomorpholinyl S-oxide, homothiomorpholinyl S,S-dioxide-dioxide, pyrrolinyl and pyrrolidinyl, each of which is optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxy, cyano, nitro, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, amino(C1-C6) alkyl, mono (C1-C6)alkylamino(C1-C6)alkyl, di(C1-C6) alkylamino(C1-C6)alkyl, and ═
O;
R110 is aryl optionally substituted with 1 or 2 R125 groups;
R125 at each occurrence is independently halogen, amino, mono- or dialkylamino, —
OH, —
C≡
N, —
SO2—
NH2, —
SO2—
NH—
C1-C6 alkyl, —
SO2—
N(C1-C6 alkyl)2, —
SO2—
(C1-C4 alkyl), —
CO—
NH2, —
CO—
NH—
C1-C6 alkyl, or —
CO—
N(C1-C6 alkyl)2, or C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, each of which is optionally substituted with 1, 2, or 3 groups that are independently selected from C1-C3 alkyl, halogen, —
OH, —
SH, —
C≡
N, —
CF3, C1-C3 alkoxy, amino, and mono- and dialkylamino, or C1-C6 alkoxy optionally substituted with one, two or three of halogen;
R120 is heteroaryl, which is optionally substituted with 1 or 2 R125 groups; and
R130 is heterocyclyl optionally substituted with 1 or 2 R125 groups.
1 Assignment
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Abstract
The present invention relates to compounds of formula (I):
useful in treating Alzheimer'"'"'s disease and other similar diseases. These compounds include inhibitors of the beta-secretase enzyme that are useful in the treatment of Alzheimer'"'"'s disease and other diseases characterized by deposition of A beta peptide in a mammal. The compounds of the invention are useful in pharmaceutical compositions and methods of treatment to reduce A beta peptide formation.
52 Citations
9 Claims
-
1. A compound of the formula I:
-
or a pharmaceutical salt thereof, wherein R1 is aryl, or aryl (C1-C6)alkyl-, where the ring portions of each are optionally substituted with 1, 2, 3, or 4 groups independently selected from halogen, —
OH, —
SH, —
C≡
N, —
NO2, —
NR105R′
105, —
CO2R, —
N(R)COR′
, —
N(R)SO2R′
, —
C(═
O)—
(C1-C4)alkyl, —
SO2-amino, —
SO2-monoalkylamino, —
SO2-dialkylamino, —
C(═
O)-amino, —
C(═
O)-monoalkylamino, —
C(═
O)-dialkylamino, —
SO2—
(C1-C4)alkyl,C1-C6 alkoxy optionally substituted with 1, 2, or 3 groups which are independently selected from halogen, C3-C7 cycloalkyl optionally substituted with 1, 2, or 3 groups independently selected from halogen, —
OH, —
SH, —
C≡
N, —
CF3, C1-C3 alkoxy, amino, —
C1-C6 alkyl and mono- or dialkylamino,C1-C10 alkyl optionally substituted with 1, 2, or 3 groups independently selected from halogen, —
OH, —
SH, —
C≡
N, —
CF3, —
C1-C3 alkoxy, amino, mono- or dialkylamino and —
C1-C3 alkyl, andC2-C10 alkenyl or C2-C10 alkynyl each of which is optionally substituted with 1, 2, or 3 groups independently selected from halogen, —
OH, —
SH, —
C≡
N, —
CF3, C1-C3 alkoxy, amino, C1-C6 alkyl and mono- or dialkylamino;
R and R′
independently are hydrogen, C1-C10 alkyl, or C1-C10 alkylaryl;
R2 is H;
Rc is hydrogen, —
(CR245R250)0-4-aryl, —
(CR245R250)0-4-aryl-aryl, —
CH(aryl)2, —
(CH2)0-1—
CH((CH2)0-6—
OH)—
(CH2)0-1-aryl, —
CH(-aryl) —
CO—
O(C1-C4 alkyl), —
(C1-C6 alkyl)-O—
(C1-C6 alkyl) —
OH;
—
CH2—
NH—
CH2—
CH (—
O—
CH2—
CH3)2, —
(CH2)0-6—C(═
NR235)(NR235R240), C1-C10 alkyl optionally substituted with 1, 2, or 3 groups independently selected from the group consisting of R110, R120 and R130,C2-C10 alkyl optionally substituted with 1, 2, or 3 groups independently selected from the group consisting of R205, R110, R120, R130, —
OC═
ONR235R240, —
S(═
O)0-2(C1-C6 alkyl), —
SH, and —
S(═
O)2NR235R240,C2-C10 alkenyl or C2-C10 alkynyl, each of which is optionally substituted with 1, 2, or 3 independently selected R205 groups, wherein each aryl is optionally substituted with 1, 2, or 3 R200;
R200 at each occurrence is independently selected from —
OH, —
NO2, halogen, —
CO2H, C≡
N, —
(CH2)0-4—
CO—
NR220R225, —
(CH2)0-4—
CO—
(C1-C12 alkyl), —
(CH2)0-4—
CO—
(C2-C12 alkenyl), —
(CH2)0-4—
CO—
(C2-C12 alkynyl), —
(CH2)0-4—
CO—
(C3-C7 cycloalkyl), —
(CH2)0-4—
CO-aryl, —
(CH2)0-4—
CO—
O—
R215, —
(CH2)0-4—
SO2—
NR220R225, —
(CH2)0-4—
SO—
(C1-C8 alkyl), —
(CH2)0-4—
SO2—
(C1-C12 alkyl), —
(CH2)0-4—
SO2—
(C3-C7 cycloalkyl), —
(CH2)0-4—
N(H or R215)—
CO—
O—
R215, —
(CH2)0-4—
N(H or R215)—
CO—
N(R215)2, —
(CH2)0-4—
N—
CS—
N(R215)2, —
(CH2)0-4—
N(—
H or R215)—
CO—
R220, —
(CH2)0-4—
NR220R225, —
(CH2)0-4—
O—
CO—
(C1-C6 alkyl), —
(CH2)0-4—
O—
P(O)—
(OR240)2, —
(CH2)0-4—
O—
CO—
N(R215)2, —
(CH2)0-4—
O—
CS—
N(R215)2, —
(CH2)0-4—
O—
(R215), —
(CH2)0-4—
O—
(R215)—
COOH, —
(CH2)0-4—
S—
(R215), —
(CH2)0-4—
O—
(C1-C6 alkyl optionally substituted with 1, 2, 3, or 5 —
F), C3-C7 cycloalkyl, —
(CH2)0-4—
N(H or R215)—
SO2—
R220, —
(CH2)0-4—
C3-C7 cycloalkyl,C1-C10 alkyl optionally substituted with 1, 2, or 3 independently selected R205 groups, C2-C10 alkenyl and C2-C10 alkynyl, each of which is optionally substituted with 1 or 2 independently selected R205 groups, wherein the aryl groups at each occurrence are optionally substituted with 1, 2, or 3 groups that are independently R205, R210, or C1-C6 alkyl substituted with 1, 2, or 3 groups that are independently R205 or R210;
R205 at each occurrence is independently selected from C1-C6 alkyl, halogen, —
OH, —
O-phenyl, —
SH, —
S—
C1-C6 alkyl, —
C≡
N, —
CF3, C1-C6 alkoxy, NH2, NH(C1-C6 alkyl) or N—
(C1-C6 alkyl)(C1-C6 alkyl);
R210 at each occurrence is independently selected from halogen, C1-C6 alkoxy, C1-C6 haloalkoxy, —
NR220R225, OH, C≡
N, —
CO—
(C1-C4 alkyl), —
SO2—
NR235R240, —
CO—
NR235R240, —
SO2—
(C1-C4 alkyl), ═
O, orC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or C3-C7 cycloalkyl, each of which is optionally substituted with 1, 2, or 3 R205 groups;
R215 at each occurrence is independently selected from C1-C6 alkyl, —
(CH2)0-2-(aryl), C2-C6 alkenyl, C2-C6 alkynyl, and C3-C7 cycloalkyl, whereinthe aryl group at each occurrence is optionally substituted with 1, 2, or 3 groups that are independently R205 or R210;
R220 and R225 at each occurrence are independently selected from —
H, —
C3-C7 cycloalkyl, —
(C1-C2 alkyl)-(C3-C7 cycloalkyl), —
(C1-C6 alkyl)-O—
(C1-C3 alkyl), —
C2-C6 alkenyl, —
C2-C6 alkynyl, —
C1-C6 alkyl chain with one double bond and one triple bond, -aryl, and—
C1-C10 alkyl optionally substituted with —
OH, —
NH2 or halogen, whereinthe aryl, group at each occurrence is optionally substituted with 1, 2, or 3 independently selected R270 groups R235 and R240 at each occurrence are independently H, or C1-C6 alkyl;
R245 and R250 at each occurrence are independently selected from —
H, C1-C4 alkyl, C1-C4 alkylaryl, C1-C4 hydroxyalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, —
(CH2)0-4—
C3-C7 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, and phenyl;
orR245 and R250 are taken together with the carbon to which they are attached to form a carbocycle of 3, 4, 5, 6, or 7 carbon atoms R270 at each occurrence is independently R205, halogen C1-C6 alkoxy, C1-C6 haloalkoxy, NR235R240, —
OH, —
C≡
N, —
CO—
(C1-C4 alkyl), —
SO2—
NR235R240, —
CO—
NR235R240, —
SO2—
(C1-C4 alkyl), ═
O, orC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or —
(CH2)0-4—
C3-C7 cycloalkyl, each of which is optionally substituted with 1, 2, or 3 R205 groups;
RN is R′
100, —
SO2R′
100, —
(CRR′
)1-6R′
100, —
C(═
O)—
(CRR′
)0-6R100, —
C(═
O)—
(CRR′
)1-6—
O—
R′
100, —
C(═
O)—
(CRR′
)1-6—
S—
R′
100, —
C(═
O)—
(CRR′
)1-6—
C(═
O)—
R100, —
C(═
O)—
(CRR′
)1-6—
SO2—
R100 or —
C(═
O)—
(CRR′
)1-6—
NR100—
R′
100;
R100 and R′
100 independently represent aryl, -aryl-W-aryl, -aryl-W-heteroaryl, -aryl-W-heterocyclyl, -heteroaryl-W-aryl, -heterocyclyl-W-aryl, —
CH[(CH2)0-2—
O—
R150]—
(CH2)0-2-aryl, where the ring portions of each are optionally substituted with 1, 2, or 3 groups independently selected from—
OR, —
NO2, C1-C6 alkyl, halogen, —
C≡
N, —
OCF3, —
CF3, —
(CH2)0-4—
O—
P(═
O)(OR)(OR′
), —
(CH2)0-4—
CO—
NR105R′
105, —
(CH2)0-4—
O—
(CH2)0-4—
CONR102R102′
, —
(CH2)0-4—
CO—
(C1-C12 alkyl), —
(CH2)0-4—
CO—
(C2-C12 alkenyl), —
(CH2)0-4—
CO—
(C2-C12 alkynyl), —
(CH2)0-4—
CO—
(CH2)0-4(C3-C7 cycloalkyl), —
(CH2)0-4—
R110, —
(CH2)0-4—
R120, —
(CH2)0-4—
R130, —
(CH2)0-4—
CO—
R110, —
(CH2)0-4—
CO—
R120, —
(CH2)0-4—
CO—
R130, —
(CH2)0-4—
CO—
R140, —
(CH2)0-4—
CO—
O—
R150, —
(CH2)0-4—
SO2—
NR105R′
105, —
(CH2)0-4—
SO—
(C1-C8 alkyl), —
(CH2)0-4—
SO2—
(C1-C12 alkyl), —
(CH2)0-4—
SO2—
(CH2)0-4—
(C3-C7 cycloalkyl), —
(CH2)0-4—
N(R150)—
CO—
O—
R150, —
(CH2)0-4—
N(R150)—
CO—
N(R150)2, —
(CH2)0-4—
N(R150)—
CS—
N(R150)2, —
(CH2)0-4—
N(R150)—
CO—
R105, —
(CH2)0-4—
NR105R′
105, —
(CH2)0-4—
R140, —
(CH2)0-4—
O—
CO—
(C1-C6 alkyl), —
(CH2)0-4—
O—
P(O)—
(O—
R110)2, —
(CH2)0-4—
O—
CO—
N(R150)2, —
(CH2)0-4—
O—
CS—
N(R150)2, —
(CR2)0-4—
O—
(R150), —
(CH2)0-4—
O—
R150′
—
COCH, —
(CH2)0-4—
S—
(R150), —
(CR2)0-4—
N(R150)—
SO2—
R105, —
(CH2)0-4—
C3-C7 cycloalkyl, (C2-C10alkenyl, and (C2-C10)alkynyl, orR100 is C1-C10 alkyl optionally substituted with 1, 2, or 3 R115 groups, or R100 is —
(C1-C6 alkyl)—
O-C1-C6 alkyl) or —
(C1-C6 alkyl)—
S—
(C1-C6 alkyl), each of which is optionally substituted with 1, 2, or 3 R115 groups, orR100 is C3-C8 cycloalkyl optionally substituted with 1, 2, or 3 R115 groups;
W is —
(CH2)0-4—
, —
O—
, —
S(O)0-2—
, —
N(R135)—
, —
CR(OH)—
or —
C(O)—
;
R102 and R102′
independently are hydrogen, orC1-C10 alkyl optionally substituted with 1, 2, or 3 groups that are independently halogen, aryl or —
R110;
R105 and R′
105 independently represent —
H, —
R110, —
R120, C3-C7 cycloalkyl, —
(C1-C2 alkyl)-(C3-C7 cycloalkyl), —
(C1-C6 alkyl)-O—
(C1-C3 alkyl), C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkyl chain with one double bond and one triple bond, or C1-C6 alkyl optionally substituted with —
OH or —
NH2;
or,C1-C6 alkyl optionally substituted with 1, 2, or 3 groups independently selected from halogen, or R105 and R′
105 together with the atom to which they are attached form a 3 to 7 membered carbocylic ring, where one member is optionally a heteratom selected from —
O—
, —
S(O)0-2—
, —
N(R135)—
, the ring being optionally substituted with 1, 2 or 3 independently selected R140 groups;
R115 at each occurrence is independently halogen, —
OH, —
CO2R102, —
C1-C6 thioalkoxy, —
CO2-phenyl, —
NR105R′
135, —
SO2—
(C1-C8 alkyl), —
C(═
O)R150, R180, —
CONR105R′
105, —
SO2NR105R′
105, —
NH—
CO—
(C1-C6 alkyl), —
NH—
C(═
O)—
OH, —
NH—
C(═
O)—
OR, —
NH—
C(═
O)—
O-phenyl, —
O—
C(═
O)—
(C1-C6 alkyl), —
O—
C(═
O)-amino, —
O—
C(═
O)-mono- or dialkylamino, —
O—
C(═
O)-phenyl, —
O—
(C1-C6 alkyl)-CO2H, —
NH—
SO2—
(C1-C6 alkyl), C1-C6 alkoxy or C1-C6 haloalkoxy;
R135 is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, —
(CH2)0-2-(aryl), —
(CH2)0-2-(heteroaryl), or —
(CH2)0-2-(heterocyclyl);
R140 is heterocyclyl optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxy, cyano, nitro, amino, mono(C1-C6 alkylamino, di(C1-C6)alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, amino(C1-C6alkyl, mono(C1-C6)alkylamino(C1-C6)alkyl, di(C1-C6)alkylamino(C1-C6)alkyl, and ═
O;
R145 is C1-C6 alkyl or CF3;
R150 is hydrogen, C3-C7 cycloalkyl, —
(C1-C2 alkyl)-(C3-C7 cycloalkyl), C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl with one double bond and one triple bond, —
R110, —
R120, orC1-C6 alkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from —
OH, —
NH2, C1-C3 alkoxy, R110, and halogen;
R150′
is C3-C7 cycloalkyl, —
(C1-C3 alkyl)-(C3-C7 cycloalkyl), C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl with one double bond and one triple bond, —
R110, —
R120, orC1-C6 alkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from —
OH, —
NH2, C1-C3 alkoxy, R110, and halogen;
R155 is C3-C7 cycloalkyl, —
(C1-C2 alkyl)-(C3-C7 cycloalkyl), C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl with one double bond and one triple bond, —
R110, —
R120, orC1-C6 alkyl optionally substituted with 1, 2, 3, or 4 groups independently selected from —
OH, —
NH2, C1-C3 alkoxy, and halogen;
R180 is selected from morpholinyl, thiomorpholinyl, piperazinyl, piperidinyl, homomorpholinyl, homothiomorpholinyl, homothiomorpholinyl S-oxide, homothiomorpholinyl S,S-dioxide-dioxide, pyrrolinyl and pyrrolidinyl, each of which is optionally substituted with 1, 2, 3, or 4 groups independently selected from C1-C6 alkyl, C1-C6 alkoxy, halogen, hydroxy, cyano, nitro, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, amino(C1-C6) alkyl, mono (C1-C6)alkylamino(C1-C6)alkyl, di(C1-C6) alkylamino(C1-C6)alkyl, and ═
O;
R110 is aryl optionally substituted with 1 or 2 R125 groups;
R125 at each occurrence is independently halogen, amino, mono- or dialkylamino, —
OH, —
C≡
N, —
SO2—
NH2, —
SO2—
NH—
C1-C6 alkyl, —
SO2—
N(C1-C6 alkyl)2, —
SO2—
(C1-C4 alkyl), —
CO—
NH2, —
CO—
NH—
C1-C6 alkyl, or —
CO—
N(C1-C6 alkyl)2, orC1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, each of which is optionally substituted with 1, 2, or 3 groups that are independently selected from C1-C3 alkyl, halogen, —
OH, —
SH, —
C≡
N, —
CF3, C1-C3 alkoxy, amino, and mono- and dialkylamino, orC1-C6 alkoxy optionally substituted with one, two or three of halogen;
R120 is heteroaryl, which is optionally substituted with 1 or 2 R125 groups; and
R130 is heterocyclyl optionally substituted with 1 or 2 R125 groups. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
-
-
3. A compound according to claim 2 wherein
RC is C1-C10 alkyl optionally substituted with 1, 2, or 3 groups independently selected from the group consisting of R110, R120 and R130, or C2-C10 alkyl optionally substituted with 1, 2, or 3 groups independently selected from the group consisting of R205, R110, R120, R130, — - OC═
ONR235R240, —
S(═
O)0-2(C1-C6 alkyl), —
SH, and —
S(═
O)2NR235R240, orC2-C10 alkenyl or C2-C10 alkynyl, each of which is optionally substituted with 1, 2, or 3 R205 groups.
- OC═
-
4. compound according to claim 3 wherein
RN is — - C(═
O)—
(CRR′
)0-6R100; and
R100 represents aryl, which is optionally substituted with 1, 2, or 3 groups independently selected from —
OR, —
NO2, C1-C6 alkyl, halogen, —
C≡
N, —
OCF3, —
CF3, —
(CH2)0-4—
O—
P(═
O)(OR)(OR′
), —
(CH2)0-4—
CO—
NR105R′
105, —
(CH2)0-4—
O—
(CH2)0-4—
CONR102R102′
, —
(CH2)0-4—
CO—
(C1-C12 alkyl), —
(CH2)0-4—
CO—
(C2-C12 alkenyl), —
(CH2)0-4—
CO—
(C2-C12 alkynyl), —
(CH2)0-4—
CO—
(CH2)0-4(C3-C7 cycloalkyl), —
(CH2)0-4—
R110, —
(CH2)0-4—
R120, —
(CH2)0-4—
R130, —
(CH2)0-4—
CO—
R110, —
(CH2)0-4—
CO—
R120, —
(CH2)0-4—
CO—
R130, —
(CH2)0-4—
CO—
R140, —
(CH2)0-4—
CO—
O—
R150, —
(CH2)0-4—
SO2—
NR105R′
105, —
(CH2)0-4—
SO—
(C1-C8 alkyl), —
(CH2)0-4—
SO2—
(C1-C12 alkyl), —
(CH2)0-4—
SO2—
(CH2)0-4—
(C3-C7 cycloalkyl), —
(CH2)0-4—
N(R150)—
CO—
O—
R150, —
(CH2)0-4—
N(R150)—
CO—
N(R150)2, —
(CH2)0-4—
N(R150)—
CS—
N(R150)2, —
(CH2)0-4—
N(R150)—
CO—
R105, —
(CH2)0-4—
NR105R′
105, —
(CH2)0-4—
R140, —
(CH2)0-4—
O—
CO—
(C1-C6 alkyl), —
(CH2)0-4—
O—
P(O)—
(O—
R110)2, —
(CH2)0-4—
O—
CO—
N(R150)2, —
(CH2)0-4—
O—
CS—
N(R150)2, —
(CH2)0-4—
O—
(R150), —
(CH2)0-4—
O—
R150′
—
COOH, —
(CH2)0-4—
S—
(R150), —
(CH2)0-4—
N(R150)—
SO2—
R105, —
(CH2)0-4—
C3-C7 cycloalkyl, (C2-C10)alkenyl, or (C2-C10)alkynyl.
- C(═
-
5. A compound according to claim 4 wherein
RN is — - C(═
O)—
R100; and
R100 represents aryl, which is optionally substituted with 1, 2, or 3 groups independently selected from —
OR, —
NO2, C1-C6 alkyl, halogen, —
C≡
N, —
OCF3, —
CF3, —
(CH2)0-4—
O—
P(═
O)(OR)(OR′
), —
(CH2)0-4—
CO—
NR105R′
105, —
(CH2)0-4—
O—
(CH2)0-4—
CONR102R102′
, —
(CH2)0-4—
CO—
(C1-C12 alkyl), —
(CH2)0-4—
CO—
(C2-C12 alkenyl), —
(CH2)0-4—
CO—
(C2-C12 alkynyl), —
(CH2)0-4—
CO—
(CH2)0-4(C3-C7 cycloalkyl), —
(CH2)0-4—
R110, —
(CH2)0-4—
R120, —
(CH2)0-4—
R130, —
(CH2)0-4—
CO—
R110, —
(CH2)0-4—
CO—
R120, —
(CH2)0-4—
CO—
R130, —
(CH2)0-4—
CO—
R140, —
(CH2)0-4—
CO—
O—
R150, —
(CH2)0-4—
SO2—
NR105R′
105, —
(CH2)0-4—
SO—
(C1-C8 alkyl), —
(CH2)0-4—
SO2—
(C1-C12 alkyl), —
(CH2)0-4—
SO2—
(CH2)0-4—
(C3-C7 cycloalkyl), —
(CH2)0-4—
N(R150)—
CO—
O—
R150, —
(CH2)0-4—
N(R150)—
CO—
N(R150)2, —
(CH2)0-4—
N(R150)—
CS—
N(R150)2, —
(CH2)0-4—
N(R150)—
CO—
R105, —
(CH2)0-4—
NR105R′
105, —
(CH2)0-4—
R140, —
(CH2)0-4—
O—
CO—
(C1-C6 alkyl), —
(CH2)0-4—
O—
P(O)—
(O—
R110)2, —
(CH2)0-4—
O—
CO—
N(R150)2, —
(CH2)0-4—
O—
CS—
N(R150)2, —
(CH2)0-4—
O—
(R150), —
(CH2)0-4—
O—
R150′
—
COOH, —
(CH2)0-4—
S—
(R150), —
(CH2)0-4—
N(R150)—
SO2—
R105, —
(CH2)0-4—
C3-C7 cycloalkyl, (C2-C10)alkenyl, and (C2-C10)alkynyl.
- C(═
-
6. A compound according to claim 5 wherein
R1 is — - CH2-phenyl where the ring portion is optionally substituted with 1, 2, 3, or 4 groups independently selected from halogen, C1-C4 alkoxy, hydroxy, and C1-C4 alkyl optionally substituted with 1, 2, or 3 substituents halogen, OH, SH, NH2, NH(C1-C6 alkyl), N—
(C1-C6 alkyl)(C1-C6 alkyl), C≡
N, CF3; and
Rc is C2-C10 alkyl, C2-C10 alkenyl or C2-C10 alkynyl, each of which is optionally substituted with with 1, 2, or 3 groups independently selected from the group consisting of halogen, —
OH, phenyl, —
O-phenyl, —
SH, —
S—
C1-C6 alkyl, —
C≡
N, —
CF3, C1-C6 alkoxy, NH2, NH(C1-C6 alkyl) or N—
(C1-C6 alkyl)(C1-C6 alkyl).
- CH2-phenyl where the ring portion is optionally substituted with 1, 2, 3, or 4 groups independently selected from halogen, C1-C4 alkoxy, hydroxy, and C1-C4 alkyl optionally substituted with 1, 2, or 3 substituents halogen, OH, SH, NH2, NH(C1-C6 alkyl), N—
-
7. A compound according to claim 5 of the formula I-7:
-
wherein X is CH; and
A3 and A4 are independently hydrogen, halogen, C1-C4 alkoxy, hydroxy, and C1-C4 alkyl optionally substituted with 1, 2, or 3 substituents halogen, OH, SH, NH2, NH(C1-C6 alkyl), N—
(C1-C6 alkyl)(C1-C6 alkyl), C≡
N, CF3.
-
-
8. A compound according to claim 7 of the formula I-7-a:
-
wherein A1 and A2 are independently —
OR, —
NO2, C1-C6 alkyl, halogen, —
C≡
N, —
OCF3, —
CF3, —
(CH2)0-4—
O—
P(═
O)(OR)(OR′
), —
(CH2)0-4—
CO—
NR105, R′
105, —
(CH2)0-4—
O—
(CH2)0-4—
CONR102R102′
, —
(CH2)0-4—
CO—
(C1-C12 alkyl), —
(CH2)0-4—
CO—
(C2-C12 alkenyl), —
(CH2)0-4—
CO—
(C2-C12 alkynyl), —
(CH2)0-4—
CO—
(CH2)0-4(C3-C7 cycloalkyl), —
(CH2)0-4—
R110, —
(CH2)0-4—
R120, —
(CH2)0-4—
R130, —
(CH2)0-4—
CO—
R110, —
(CH2)0-4—
CO—
R120, —
(CH2)0-4—
CO—
R130, —
(CH2)0-4—
CO—
R140, —
(CH2)0-4—
CO—
O—
R150, —
(CH2)0-4—
SO2—
NR105R′
105, —
(CH2)0-4—
SO—
(C1-C8 alkyl), —
(CH2)0-4—
SO2—
(C1-C12 alkyl), —
(CH2)0-4—
SO2—
(CH2)0-4—
(C3-C7 cycloalkyl), —
(CH2)0-4—
N(R150)—
CO—
O—
R150, —
(CH2)0-4—
N(R150)—
CO—
N(R150)2, —
(CH2)0-4—
N(R150)—
CS—
N(R150)2, —
(CH2)0-4—
N(R150)—
CO—
R105, —
(CH2)0-4—
NR105R′
105, —
(CH2)0-4—
R140, —
(CH2)0-4—
O—
CO—
(C1-C6 alkyl), —
(CH2)0-4—
O—
P(O)—
(O—
R110)2, —
(CH2)0-4—
O—
CO—
N(R150)2, —
(CH2)0-4—
O—
CS—
N(R150)2, —
(CH2)0-4—
O—
(R150), —
(CH2)0-4—
O—
R150′
—
COOH, —
(CH2)0-4—
S—
(R150), —
(CH2)0-4—
N(R150)—
SO2—
R105, —
(CH2)0-4—
C3-C7 cycloalkyl, (C2-C10)alkenyl, or (C2-C10)alkynyl.
-
-
9. A compound according to claim 7 selected from the group consisting of
5-Bromo-N-[(1S,2R,3R)-1-(3,5-difluoro-benzyl)-2,3-dihydroxy-heptyl]-N′ - ,N′
-dipropyl-isophthalamide,N-[(1S,2R,3R)-1-(3,5-Difluoro-benzyl)-2,3-dihydroxy-heptyl]-5-methyl-N′
,N′
-dipropyl-isophthalamide,5-Carboxamido-N-[(1S,2R,3R)-1-(3,5-difluoro-benzyl)-2,3-dihydroxy-heptyl]-N′
,N′
-dipropyl-isophthalamide,N-[(1S,2R,3S)-1-benzyl-2,3-dihydroxy-heptyl]-5-methyl-N′
,N′
-dipropyl-isophthalamide,N-[(1S,2R,3S)-1-(3,5-difluorobenzyl)-2,3-dihydroxy-heptyl]-5-methyl-N′
,N′
-dipropyl-isophthalamide,5-Carboxamido-N-[(1S,2R,3S)-1-(3,5-difluoro-benzyl)-2,3-dihydroxy-heptyl]-N′
,N′
-dipropyl-isophthalamide,2-({3-bromo-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-6-S-methyl-1-phenyl-6-thio-D-xylo-hexitol, N1-[(1S,2R,3R)-1-benzyl-2,3-dihydroxy-6-phenylhexyl]-N3,N3-dipropylbenzene-1,3,5-tricarboxamide, N′
-[1-(3,5-difluorobenzyl)-2,3-dihydroxyheptyl]-5-methyl-N,N-dipropylisophthalamide,N′
-[1-(3,5-difluorobenzyl)-2,3-dihydroxyoctyl]-5-methyl-N,N-dipropylisophthalamide,1,2,5-trideoxy-1-(3,5-difluorophenyl)-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-6-O-methylhexitol, 1,2,5-trideoxy-1-(3,5-difluorophenyl)-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-6-S-methyl-6-thiohexitol, N′
-[1-(3,5-difluorobenzyl)-2,3-dihydroxyoct-7-ynyl]-5-methyl-N,N-dipropylisophthalamide,1,2,5,6-tetradeoxy-1-(3,5-difluorophenyl)-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-7-S-methyl-7-thioheptitol, N′
-[6-cyano-1-(3,5-difluorobenzyl)-2,3-dihydroxyhexyl]-5-methyl-N,N-dipropylisophthalamide,N′
-[5-cyano-1-(3,5-difluorobenzyl)-2,3-dihydroxypentyl]-5-methyl-N,N-dipropylisophthalamide,N′
-[4-cyano-1-(3,5-difluorobenzyl)-2,3-dihydroxybutyl]-5-methyl-N,N-dipropylisophthalamide,1,2-dideoxy-1-(3,5-difluorophenyl)-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-5-O-methylpentitol, N3-[1-(3,5-difluorobenzyl)-2,3-dihydroxyheptyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-[1-(3,5-difluorobenzyl)-2,3-dihydroxyoctyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-1-(3,5-difluorophenyl)-6-O-methylhexitol, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-1-(3,5-difluorophenyl)-6-S-methyl-6-thiohexitol, N3-[1-(3,5-difluorobenzyl)-2,3-dihydroxyoct-7-ynyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5,6-tetradeoxy-1-(3,5-difluorophenyl)-7-S-methyl-7-thioheptitol, N3-[6-cyano-1-(3,5-difluorobenzyl)-2,3-dihydroxyhexyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-[5-cyano-1-(3,5-difluorobenzyl)-2,3-dihydroxypentyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-[4-cyano-1-(3,5-difluorobenzyl)-2,3-dihydroxybutyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2-dideoxy-1-(3,5-difluorophenyl)-5-O-methylpentitol, N′
-(1-benzyl-2,3-dihydroxyheptyl)-5-methyl-N,N-dipropylisophthalamide,N′
-(1-benzyl-2,3-dihydroxyoctyl)-5-methyl-N,N-dipropylisophthalamide,1,2,5-trideoxy-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-6-O-methyl-1-phenylhexitol, 1,2,5-trideoxy-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-6-S-methyl-1-phenyl-6-thiohexitol, N′
-(1-benzyl-2,3-dihydroxyoct-7-ynyl)-5-methyl-N,N-dipropylisophthalamide,1,2,5,6-tetradeoxy-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-7-S-methyl-1-phenyl-7-thioheptitol, N′
-(1-benzyl-6-cyano-2,3-dihydroxyhexyl)-5-methyl-N,N-dipropylisophthalamide,N′
-(1-benzyl-5-cyano-2,3-dihydroxypentyl)-5-methyl-N,N-dipropylisophthalamide,N′
-(1-benzyl-4-cyano-2,3-dihydroxybutyl)-5-methyl-N,N-dipropylisophthalamide,1,2-dideoxy-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-5-O-methyl-1-phenylpentitol, N3-(1-benzyl-2,3-dihydroxyheptyl)-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-(1-benzyl-2,3-dihydroxyoctyl)-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-6-O-methyl-1-phenylhexitol, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-6-S-methyl-1-phenyl-6-thiohexitol, N3-(1-benzyl-2,3-dihydroxyoct-7-ynyl)-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5,6-tetradeoxy-7-S-methyl-1-phenyl-7-thioheptitol, N3-(1-benzyl-6-cyano-2,3-dihydroxyhexyl)-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-(1-benzyl-5-cyano-2,3-dihydroxypentyl)-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-(1-benzyl-4-cyano-2,3-dihydroxybutyl)-N1,N1dipropylbenzene-1,3,5-tricarboxamide, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2-dideoxy-5-O-methyl-1-phenylpentitol, N′
-[2,3-dihydroxy-1-(4-hydroxybenzyl)heptyl]-5-methyl-N,N-dipropylisophthalamide,N′
-[2,3-dihydroxy-1-(4-hydroxybenzyl)octyl]-5-methyl-N,N-dipropylisophthalamide,1,2,5-trideoxy-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-1-(4-hydroxyphenyl)-6-O-methylhexitol, 1,2,5-trideoxy-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-1-(4-hydroxyphenyl)-6-S-methyl-6-thiohexitol, N′
-[2,3-dihydroxy-1-(4-hydroxybenzyl)oct-7-ynyl]-5-methyl-N,N-dipropylisophthalamide,1,2,5,6-tetradeoxy-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-1-(4-hydroxyphenyl)-7-S-methyl-7-thioheptitol, N′
-[6-cyano-2,3-dihydroxy-1-(4-hydroxybenzyl)hexyl]-5-methyl-N,N-dipropylisophthalamide,N′
-[5-cyano-2,3-dihydroxy-1-(4-hydroxybenzyl)pentyl]-5-methyl-N,N-dipropylisophthalamide,N′
-[4-cyano-2,3-dihydroxy-1-(4-hydroxybenzyl)butyl]-5-methyl-N,N-dipropylisophthalamide,1,2-dideoxy-2-({3-[(dipropylamino)carbonyl]-5-methylbenzoyl}amino)-1-(4-hydroxyphenyl)-5-O-methylpentitol, N3-[2,3-dihydroxy-1-(4-hydroxybenzyl)heptyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-[2,3-dihydroxy-1-(4-hydroxybenzyl)octyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-1-(4-hydroxyphenyl)-6-O-methylhexitol, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5-trideoxy-1-(4-hydroxyphenyl)-6-S-methyl-6-thiohexitol, N3-[2,3-dihydroxy-1-(4-hydroxybenzyl)oct-7-ynyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2,5,6-tetradeoxy-1-(4-hydroxyphenyl)-7-S-methyl-7-thioheptitol, N3-[6-cyano-2,3-dihydroxy-1-(4-hydroxybenzyl)hexyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-[5-cyano-2,3-dihydroxy-1-(4-hydroxybenzyl)pentyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, N3-[4-cyano-2,3-dihydroxy-1-(4-hydroxybenzyl)butyl]-N1,N1-dipropylbenzene-1,3,5-tricarboxamide, and 2-({3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoyl}amino)-1,2-dideoxy-1-(4-hydroxyphenyl)-5-O-methylpentitol.
- ,N′
Specification
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Current AssigneePharmacia & Upjohn Company (Pfizer Inc.)
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Original AssigneePharmacia & Upjohn Company (Pfizer Inc.)
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InventorsSchostarez, Heinrich Josef, Chrusciel, Robert Alan
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Primary Examiner(s)Chang, Ceila
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Assistant Examiner(s)Coppins, Janet L.
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Application NumberUS10/171,343Publication NumberTime in Patent Office1,097 DaysField of Search564/297, 564/300, 564/306, 514/615, 514/645, 514/649US Class Current514/649CPC Class CodesA61P 25/00 Drugs for disorders of the ...A61P 25/16 Anti-Parkinson drugsA61P 25/28 for treating neurodegenerat...A61P 43/00 Drugs for specific purposes...C07C 215/28 and containing six-membered...C07C 235/84 with the carbon atom of at ...C07C 255/44 at least one of the singly-...C07C 323/42 Y being a carbon atom of a ...C07D 263/48 Nitrogen atoms not forming ...C07D 277/52 to sulfur atoms, e.g. sulfo...C07D 413/12 linked by a chain containin...C07D 417/12 linked by a chain containin...
