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Details for Patent: 5,679,670

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Details for Patent: 5,679,670

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 Robert (Weatherford, TX), Chen; Hwang-Hsing (Fort Worth, TX), May; Jesse Albert (Fort Worth, TX)
Assignee: Alcon Laboratories, Inc. (Fort Worth, TX)
Filing Date:Dec 15, 1994
Application Number:08/357,623
Claims:1. A compound of the formula ##STR32## or a pharmaceutically acceptable salt thereof wherein: R.sub.1 and R.sub.2 are joined to make a carbon bridge between the nitrogen atom attached to G and the thiophene ring, forming a 5- or 7-membered ring, the carbon atoms of said 5- or 7-membered ring optionally substituted 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 alkoxy C.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.O)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, or 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; 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 of 5 or 6 atoms composed of C, N, O, and/or S, 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 C(.dbd.O) or 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:

G is SO.sub.2 and

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.

4. A compound of the formula ##STR33## or a pharmaceutically acceptable salt thereof wherein: R.sub.1 and R.sub.3 are joined to make a carbon bridge between the nitrogen atom attached to G and the thiophene ring, forming a 5- or 7-membered ring, the carbon atoms of said 5- or 7-membered ring optionally substituted 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 ; 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.1-3 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.m 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 C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 halo alkyl, OH, (CH.sub.2).sub.m 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.m 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.O)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, or 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; 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 of 5 or 6 atoms composed of C, N, O, and/or S, 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.

5. The compound of claim 4 wherein:

R.sub.3 is in the 4-position and GNR.sub.1 R.sub.2 is in the 5-position.

6. The compound of claim 5 wherein:

R.sub.2 is H; C.sub.1-4 alkyl; C.sub.2-4 alkyl substituted with OH, NR.sub.5 R.sub.6, halogen, C.sub.1-2 alkoxy, C.sub.2-4 alkoxy C.sub.1-4 alkoxy, OC(.dbd.O)R.sub.7, or C(.dbd.O)R.sub.7 ; 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. -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.6 or SO.sub.2 NR.sub.5 R.sub.6, wherein m is 0-2 and n is 0-2.

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

8. A formulation for controlling intraocular pressure comprising a therapeutically effective amount of the compound of claim 2 in a pharmaceutically acceptable carrier.

9. A formulation for controlling intraocular pressure comprising a therapeutically effective amount of the compound of claim 4 in a pharmaceutically acceptable carrier.

10. The formulation of claim 7 wherein the compound concentration is between 0.1 and 10% by weight.

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

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

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

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

15. A method for controlling intraocular pressure which comprises topically administering to the affected eye a therapeutically effective amount of the compound of claim 2.

16. A method for controlling intraocular pressure which comprises topically administering to the affected eye a therapeutically effective amount of the compound of claim 4.
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