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Claims for Patent: 5,378,703

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Claims for Patent: 5,378,703

Title: Sulfonamides useful as carbonic anhydrase inhibitors
Abstract:Sulfonamides and pharmaceutical compositions containing the compounds useful in controlling intraocular pressure are disclosed. Methods for controlling intraocular pressure through administration of the compositions are also disclosed.
Inventor(s): Dean; Thomas R. (Weatherford, TX), Chen; Hwang-Hsing (Fort Worth, TX), May; Jesse A. (Fort Worth, TX)
Assignee: Alcon Laboratories, Inc. (Fort Worth, TX)
Application Number:08/019,011
Patent Claims: 1. A compound of the formula ##STR33## or a pharmaceutically acceptable salt thereof wherein: R.sup.1 and R.sup.3 are each saturated carbon atoms joined together to form a ring of 6 members in which said carbon atoms can be unsubstituted or substituted optionally with R.sub.4 ;

R.sub.2 is H; C.sub.1-8 alkyl; C.sub.2-8 alkyl substituted with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.2-4 alkoxyC.sub.1-4 alkoxy, OC(.dbd.O)R.sub.7, or C(.dbd.O)R.sub.7 ; C.sub.3-7 alkenyl unsubstituted or substituted optionally with OH, NR.sub.5 R.sub.6, or C.sub.1-4 alkoxy; C.sub.3-7 alkynyl unsubstituted or substituted optionally with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 halo alkyl, OH, NR.sub.5 R.sub.6, or C.sub.1-4 alkoxy; C.sub.1-3 alkyl substituted with phenyl or R.sub.10 either of which can be unsubstituted or substituted optionally with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 halo alkyl, OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2; C.sub.2-4 alkoxy substituted optionally with NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, or C(.dbd.O)R.sub.7 ; phenyl or R.sub.10 either of which can be unsubstituted or substituted optionally with OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2;

R.sub.4 is OH; C.sub.1-4 alkyl unsubstituted or substituted optionally with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.7 ; C.sub.1-4 alkoxy; C.sub.2-4 alkoxy substituted optionally with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.7 ; NR.sub.5 R.sub.6 ; phenyl or R.sub.10 either of which can be unsubstituted or substituted optionally with OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2;

R.sub.5 & R.sub.6 are the same or different and are H; C.sub.1-4 alkyl; C.sub.2-4 alkyl substituted optionally with OH, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.7 ; C.sub.1-4 alkoxy; C.sub.2-4 alkoxy substituted optionally with OH, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.7 ; C.sub.3-7 alkenyl unsubstituted or substituted optionally with OH, NR.sub.5 R.sub.6, or C.sub.1-4 alkoxy; C.sub.3-7 alkynyl unsubstituted or substituted optionally with OH, NR.sub.5 R.sub.6, or C.sub.1-4 alkoxy; C.sub.1-2 alkylC.sub.3-5 cycloalkyl; C(.dbd.0)R.sub.7 or R.sub.5 and R.sub.6 can be joined to form a ring selected from the group consisting of pyrrolidine, oxazolidine, thiomorpholine, thiomorpholine 1,1 dioxide, morpholine, piperazine, and thiazolidine 1,1-dioxide, which can be unsubstituted or substituted optionally on carbon with OH, (.dbd.O), halogen, C.sub.1-4 alkoxy, C(.dbd.O)R.sub.7, C.sub.1-6 alkyl, C.sub.1-6 alkyl substituted optionally with OH, halogen, C.sub.1-4 alkoxy, C(.dbd.O)R.sub.7 or on nitrogen with C.sub.1-4 alkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8, C.sub.1-6 alkyl or C.sub.2-6 alkyl substituted optionally with OH, halogen, C.sub.1-4 alkoxy, C(.dbd.O)R.sub.7 or on sulfur by (.dbd.O).sub.m, wherein m is 0-2;

R.sub.7 is C.sub.1-8 alkyl; substituted optionally with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.9 ; C.sub.1-4 alkoxy; C.sub.2-4 alkoxy substituted optionally with OH, NR.sub.5 R.sub.6, halogen or C.sub.1-4 alkoxy; NR.sub.5 R.sub.6 ; or phenyl or R.sub.10 either of which can be unsubstituted or substituted optionally with OH, halogen, C.sub.1-3 alkyl, C.sub.1-3 haloalkoxy, (CH.sub.2).sub.n NR.sub.5 R.sub.6, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein n is 0 or 1 and m is 0-2;

R.sub.8 is C.sub.1-4 alkyl; C.sub.2-4 alkyl substituted optionally with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.7 ;

R.sub.9 is C.sub.1-4 alkyl; C.sub.1-4 alkoxy; amino, C.sub.1-3 alkylamino, or di-C.sub.1-3 alkylamino;

R.sub.10 is a monocyclic ring system selected from the group consisting of furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, isothiazole, thiazole, thiadiazole, pyridine, pyrimidine, pyridazine, and pyrazine; and

G is SO.sub.2.

2. The compound of Claim 1 wherein: R.sub.3 is in the 4-position and GNR.sub.1 R.sub.2 is in the 5-position.

3. The compound of Claim 2 wherein:

R.sub.2 is H; C.sub.1-8 alkyl; C.sub.2-8 alkyl substituted with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.2-4 alkoxyC.sub.1-4 alkoxy, OC(.dbd.O)R.sub.7, or C(.dbd.O)R.sub.7 ; C.sub.3-7 alkenyl unsubstituted or substituted optionally with OH, NR.sub.5 R.sub.6, or C.sub.1-4 alkoxy; C.sub.3-7 alkynyl unsubstituted or substituted optionally with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 halo alkyl, OH, NR.sub.5 R.sub.6, or C.sub.1-4 alkoxy; C.sub.1-3 alkyl substituted with phenyl or R.sub.10 either of which can be unsubstituted or substituted optionally with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 Halo alkyl, OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7 S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2; C.sub.2-4 alkoxy substituted optionally with NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, or C(.dbd.O)R.sub.7 ; phenyl or R.sub.10 either of which can be unsubstituted or substituted optionally with OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2.

4. The compound of Claim 3 wherein:

R.sub.2 is C.sub.1-8 alkyl; C.sub.2-8 alkyl substituted with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-2 alkoxy, C.sub.2-4 alkoxyC.sub.1-4 alkoxy, OC(.dbd.O)R.sub.7, or C(.dbd.O)R.sub.7 ; C.sub.3-7 alkenyl unsubstituted or substituted optionally with OH, NR.sub.5 R.sub.6, or C.sub.1-4 alkoxy; phenyl, or R.sub.10, unsubstituted or substituted optionally with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 halo alkyl, OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2; C.sub.1-3 alkyl substituted with phenyl or R.sub.10 either of which can be unsubstituted or substituted optionally with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 halo alkyl OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2.

5. The compound of Claim 4 wherein:

R.sub.4 is OH; C.sub.1-4 alkoxy; C.sub.2-4 alkoxy substituted optionally with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.7 ; or NR.sub.5 R.sub.6 ; phenyl, or R.sub.10 unsubstituted or substituted optionally with OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2.

6. The compound of Claim 1 wherein:

R.sub.4 is OH; C.sub.1-4 alkoxy; C.sub.2-4 alkoxy substituted optionally with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.7 ; or NR.sub.5 R.sub.6 ; phenyl, or R.sub.10, unsubstituted or substituted optionally with OH, (CH.sub.2).sub.n NR.sub.5 R.sub.6, halogen, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, C(.dbd.O)R.sub.7, S(.dbd.O).sub.m R.sub.8 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2.

7. A compound selected from the group consisting of:

R-(+)-4-Ethylamino-3,4-dihydro-2-(3-methoxy)propyl-2H-thieno 1,2-thiazine-6-sulfonamide-1,1-dioxide;

(R)-4-Ethylamino-3,4-dihydro-2-(3-methoxy-phenyl)-2H-thieno-1,2-thiazine-6- sulfonamide 1,1-dioxide;

(R)-4-Ethylamino-2-(4-hydroxy-phenyl)-3,4-dihydro-2H-thieno-1,2-thiazine-6- sulfonamide 1,1-dioxide;

(R)-4-Ethylamino-3,4-dihydro-2-(3-hydroxy-phenyl)-2H-thieno-1,2-thiazine-6- sulfonamide 1,1-dioxide;

(R)-4-Ethylamino-3,4-dihydro-2-(4-hydroxy-phenylmethyl)-2H-thieno-1,2-thiaz ine-6-sulfonamide 1,1-dioxide;

(R)-4-Ethylamino-3,4-dihydro-2-(3-methoxy-phenylmethyl)-2H-thieno-1,2-thiaz ine-6-sulfonamide 1,1-dioxide;

R-(+)-3,4-Dihydro-2-(4-methoxybutyl)-4-propylamino-2H-thieno-1,2-thiazine-6 -sulfonamide 1,1-dioxide;

R-(+)-4-Ethylamino-3,4-dihydro-2-(4-methoxybutyl)-2H-thieno-1,2-thiazine-6- sulfonamide 1,1-dioxide;

R-(+)-4-Ethylamino-3,4-dihydro-2-(2-methylpropyl)-2H-thieno-1,2-thiazine-6- sulfonamide 1,1-dioxide;

R-(+)-4-Ethylamino-3,4-dihydro-2-(6-hydroxyhexyl)-2H-thieno-1,2-thiazine-6- sulfonamide 1,1-dioxide;

(R)-3,4-Dihydro-2-(3-hydroxypropyl)-4-(2-methylpropyl)amino-2H-thieno -1,2-thiazine-6-sulfonamide 1,1-dioxide;

(R)-4-Ethylamino-3,4-dihydro-2-(3-hydroxy-phenylmethyl)-2H-thieno-1,2-thiaz ine-6-sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(3-methoxy-phenyl)-4-(2-methylpropyl)amino-2H-thieno-1,2- thiazine-6-sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(4-hydroxy-phenyl)-4-(2-methylpropyl)amino-2H-thieno-1,2- thiazine-6-sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(3-methoxy-phenyl)-4-propylamino-2H-thieno-1,2-thiazine-6 -sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(3-hydroxy-phenyl)-4-propylamino-2H-thieno-1,2-thiazine-6 -sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(3-hydroxy-phenyl)-4-(2-methylpropyl)amino-2H-thieno-1,2- thiazine-6-sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(4-methoxybutyl)-4-(2-methylpropyl)amino-2H-thieno-1,2-th iazine-6-sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(3-methoxypropyl)-4-(2-methylpropyl)amino-2H-thieno-1,2-t hiazine-6-sulfonamide 1,1 dioxide;

(R)-4-Cyclopropylmethylamino-3,4-dihydro-2-(2-propenyl)-2H-thieno-1,2-thiaz ine-6-sulfonamide 1,1 dioxide;

(R)-4-Cyclopropylmethylamino-3,4-dihydro-2-(4-methoxybutyl)-2H-thieno-1,2-t hiazine-6-sulfonamide 1,1 dioxide;

(R)-4-Cyclopropylmethylamino-3,4-dihyro-2-(3-methoxypropyl)-2H-thieno-1,2-t hiazine-6-sulfonamide 1,1 dioxide;

(R)-4-Cyclopropylmethylamino-3,4-dihydro-2-propyl-2H-thieno-1,2-thiazine-6- sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(2-methylpropyl)-4-(2-methylpropyl)amino-2H-thieno-1,2-th iazine-6-sulfonamide 1,1 dioxide;

(R)-4-Cyclopropylmethylamino-3,4-dihydro-2-(2-methylpropyl)-2H-thieno-1,2-t hiazine-6-sulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-4-(2-methylpropyl)amino-2-propyl-2H-thieno-1,2-thiazine-6-s ulfonamide 1,1 dioxide;

(R)-3,4-Dihydro-2-(4-hydroxybutyl)-4-(2-methylpropyl)amino-2H-thieno-1,2-th iazine-6-sulfonamide 1,1-dioxide;

(R)-3,4-Dihydro-2-(4-hydroxybutyl)-4-propylamino-2H-thieno-1,2-thiazine-6-s ulfonamide 1,1-dioxide.

8. A formulation for controlling intraocular pressure comprising a therapeutically effective amount of the compound of Claim 1 in a pharmaceutically acceptable carrier.

9. A formulation for controlling intraocular pressure comprising a therapeutically effective amount of the compound of Claim 7 in a pharmaceutically acceptable carrier.

10. The formulation of Claim 8 wherein the compound concentration is between 0.1 and 10% by weight.

11. The formulation of Claim 9 wherein the compound concentration is between 0.1 and 10% by weight.

12. The formulation of Claim 10 wherein the compound concentration is between 0.1 and 10% by weight.

13. A method for controlling intraocular pressure which comprises topically administering to the affected eye a therapeutically effective amount of the compound of Claim 1.

14. A method for controlling intraocular pressure which comprises topically administering to the affected eye a therapeutically effective amount of the compound of Claim 7.
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