Phenylethylamine analogs and their use for treating glaucoma
First Claim
Patent Images
1. A method for lowering and controlling normal or elevated IOP, which comprises administering a composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a compound of the formula:
- wherein R1 and R2 independently are H or C1-4alkyl;
R3 and R4 independently are H, C1-4 alkyl, or R3, R4 and the carbon atom to which they are attached can form a cyclopropyl ring;
Y is H, C1-4alkyl, or OR5;
R5 is H or C1-4 alkyl;
A and B independently are OH, C1-3alkoxy, OS(O)2W, OC(═
O)W, or OC(═
O)NW2W3;
W is C1-4alkyl;
W2 and W3 independently are H or C1-4alkyl;
X is CH(OH)R6, C(═
O)R6, (CH2)nZ, or (CH2)mZ′
;
R6 is C1-4 alkyl, (CH2)m2SR8, or (CH2)m2OR8;
n is 1-4;
m is 2-4;
m2 is 1-4;
Z is OCF3, CN, S(O)n2R6, C(O)NR7R6, C(C═
O)R6, CH(OH)R6, SO2NR7R8, NR6R9, CO2R6, S(O)n2CH2CH(OH)R6, S(O)n2CH2C(═
)O)R6, S(O)n2CH2CO2R6, S(O)n2CH2C(═
O)NR7R8, aryl, heterocyclyl, or heteroaryl;
Z′
is OH or OR6;
n is 0 or 1;
R7 is H, C1-4alkyl, OH, or OCH3; and
R8 and R9 independently are H or C1-4alkyl.
1 Assignment
0 Petitions
Accused Products
Abstract
Phenylethylamine analogs useful for treating glaucoma are disclosed.
-
Citations
8 Claims
-
1. A method for lowering and controlling normal or elevated IOP, which comprises administering a composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a compound of the formula:
-
wherein R1 and R2 independently are H or C1-4alkyl;
R3 and R4 independently are H, C1-4 alkyl, or R3, R4 and the carbon atom to which they are attached can form a cyclopropyl ring;
Y is H, C1-4alkyl, or OR5;
R5 is H or C1-4 alkyl;
A and B independently are OH, C1-3alkoxy, OS(O)2W, OC(═
O)W, or OC(═
O)NW2W3;
W is C1-4alkyl;
W2 and W3 independently are H or C1-4alkyl;
X is CH(OH)R6, C(═
O)R6, (CH2)nZ, or (CH2)mZ′
;
R6 is C1-4 alkyl, (CH2)m2SR8, or (CH2)m2OR8;
n is 1-4;
m is 2-4;
m2 is 1-4;
Z is OCF3, CN, S(O)n2R6, C(O)NR7R6, C(C═
O)R6, CH(OH)R6, SO2NR7R8, NR6R9, CO2R6, S(O)n2CH2CH(OH)R6, S(O)n2CH2C(═
)O)R6, S(O)n2CH2CO2R6, S(O)n2CH2C(═
O)NR7R8, aryl, heterocyclyl, or heteroaryl;
Z′
is OH or OR6;
n is 0 or 1;
R7 is H, C1-4alkyl, OH, or OCH3; and
R8 and R9 independently are H or C1-4alkyl. - View Dependent Claims (2, 3, 4)
R3 and R4 are independently H or C1alkyl;
Y is H or OR5;
R5 is H or C1alkyl;
A and B are independently OH, C1alkoxy, or OC(═
O)W;
W is C1-4alkyl;
X is (CH2)nZ or (CH2)mZ′
;
n is 1-4;
m is 2-4;
Z is OR6, OCF3, S(O)n2R6, aryl, heterocyclyl or heteroaryl;
Z′
is OR6;
R6 is C1-4 alkyl, (CH2)mSR, or (CH2)mOR;
heterocyclyl or heteroaryl is;
n2 is 0.
-
-
3. The method of claim 2 wherein the compound is selected from the group consisting of:
-
4. The method of claim 1 wherein the composition is a topically administered ophthalmic composition and the pharmaceutically effective amount of the compound is 0.1-2% (w/v).
-
5. A method for treating glaucoma, which comprises administering a composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a compound of the formula:
-
wherein R1 and R2 independently are H or C1-4alkyl;
R3 and R4 independently are H, C1-4 alkyl, or R3, R4 and the carbon atom to which they are attached can form a cyclopropyl ring;
Y is H, C1-4alkyl, or OR5;
R5 is H or C1-4 alkyl;
A and B independently are OH, C1-3alkoxy, OS(O)2W, OC(═
O)W, or OC(═
O)NW2W3;
W is C1-4alkyl;
W2 and W3 independently are H or C1-4alkyl;
X is CH(OH)R6, C(═
O)R6, (CH2)nZ, or (CH2)mZ′
;
R6 is C1-4 alkyl, (CH2)m2SR8, or (CH2)m2OR8;
n is 1-4;
m is 2-4;
m2 is 1-4;
Z is OCF3, CN, S(O)n2R6, C(O)NR7R8, C(C═
O)R6, CH(OH)R6, SO2NR7R8, NR6R9, CO2R6, S(O)n2CH2CH(OH)R6, S(O)n2CH2C(═
)O)R6, S(O)n2CH2CO2R6, S(O)n2CH2C(═
O)NR7R8, aryl, heterocyclyl, or heteroaryl;
Z′
is OH or OR6;
n2 is 0 or 1;
R7 is H, C1-4alkyl, OH, or OCH3; and
R8 and R9 independently are H or C1-4alkyl. - View Dependent Claims (6, 7, 8)
R3 and R4 are independently H or C1alkyl;
Y is H or OR5;
R5 is H or C1alkyl;
A and B are independently OH, C1alkoxy, or OC(═
O)W;
W is C1-4alkyl;
X is (CH2)nZ or (CH2)mZ′
;
n is 1-4;
m is 2-4;
Z is OR6, OCF3, S(O)n2R6, aryl, heterocyclyl or heteroaryl;
Z′
is OR6;
R6 is C1-4 alkyl, (CH2)mSR, or (CH2)mOR;
heterocyclyl or heteroaryl is;
n2 is 0.
-
-
7. The method of claim 6 wherein the compound is selected from the group consisting of:
-
8. The method of claim 5 wherein the composition is a topically administered ophthalmic composition and the pharmaceutically effective amount of the compound is 0.1-2% (w/v).
Specification