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Details for Patent: 5,585,377

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Details for Patent: 5,585,377

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), May; Jesse A. (Fort Worth, TX), Chen; Hwang-Hsing (Fort Worth, TX)
Assignee: Alcon Laboratories, Inc. (Fort Worth, TX)
Filing Date:Dec 23, 1994
Application Number:08/362,716
Claims:1. A compound of the formula ##STR28## or a pharmaceutically acceptable salt thereof wherein: R.sub.1 and R.sub.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 C.sub.1-8 alkyl substituted with C(.dbd.O)R.sub.7 ; or C.sub.2-8 alkyl substituted with OC(.dbd.O)R.sub.7, or NHC(.dbd.O)R.sub.7 ;

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 and R.sub.6 are the same or different and are H; C.sub.1-6 alkyl; C.sub.2-6 alkyl substituted optionally with OH, halogen, C.sub.1-4 alkoxy or C(.dbd.O)R.sub.7 ; hydroxy; 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, 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; 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 selected from the group consisting of R-(+)-6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-thia zine-2-butanoic acid 1,1-dioxide ethyl ester hydrochloride; R-(+)-6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-thia zine-2-butanoic acid 1,1-dioxide 1-methylethyl ester hydrochloride; R-(+)-6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-thia zine-2-propanoic acid 1,1-dioxide 1-methylethyl ester hydrochloride; R-(+)-6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-thia zine-2-propanoic acid 1,1-dioxide ethyl ester hydrochloride; R-(+)-4-Ethylamino-3,4-dihydro-2-(3-acetyloxypropyl)-2H-thieno[3,2-e]-1,2- thiazine-6-sulfonamide 1,1-dioxide hydrochloride; R-(+)-4-Ethylamino-3,4-dihydro-2-[3-(2-methyl-1-oxo-propoxy)propyl]-2H-thi eno[3,2-e]-1,2thiazine-6-sulfonamide 1,1-dioxide hydrochloride; R-(+)-2-(3-acetyloxypropyl)-3,4-dihydro-4-propylamino-2H-thieno[3,2-e]-1,2 -thiazine-6-sulfonamide 1,1-dioxide;R-(+)-4-Ethylamino-3,4-dihydro-2-[2-(2-methyl-1-oxo-propoxy)et hyl]-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide hydrochloride; R-(+)-4-Ethylamino-3,4-dihydro-2-(2-acetyloxyethyl)-2H-thieno[3,2-e]-1,2-t hiazine-6-sulfonamide 1,1-dioxide hydrochloride; R-(+)-2-[6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno 3,2-e]-1,2-thiazin-2-yl]ethylcyclopropane-carboxylate S.sup.1,S.sup.1 -dioxide hydrochloride; (R)-4-Ethylamino-3,4-dihydro-2-[4-methoxyphenylcarbonyloxy)propyl]-2H-thie no[3,2e]-1,2-thiazine-6-sulfonamide 1,1-dioxide; (R)-4-Ethylamino-3,4-dihydro-2-[(3-methoxy-1-oxo-propoxy)ethyl]-2H-thieno[ 3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide; (R)-4-Ethylamino-3,4-dihydro-2-[(3-hydoxy-1-oxo-propoxy)ethyl]-2H-thieno[3 ,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide; R-(+)-6-(Aminosulfonyl)-N-ethyl-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]- 1,2-thiazine-2-butanamide 1,1-dioxide; R-(+)-6-(Aminosulfonyl)-N-ethyl-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]- 1,2-thiazine-2-propanamide 1,1-dioxide hydrochloride; (R)-6-(Aminosulfonyl)-N-(2-methoxyethyl)-4-ethylamino-3,4-dihydro-2H-thien o[3,2-e]-1,2-thiazine-2-propanamide 1,1-dioxide; (R)-6-(Aminosulfonyl)-N-methyl-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1 ,2-thiazine-2-propanamide 1,1-dioxide; (R)-6-(Aminosulfonyl)-N-cyclopropyl-4-ethylamino-3,4-dihydro-2H-thieno[3,2 -e]-1,2-thiazine-2-propanamide 1,1-dioxide; (R)-N-[[[6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-t hiazin-2-yl]ethyl]carbonyl]-alanine ethyl ester S.sup.1,S.sup.1 -dioxide; (R)-N-[[6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-th iazin-2-yl]propyl]propanamide S.sup.1,S.sup.1 -dioxide; (R)-N-[[6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-th iazin-2-yl]propyl]acetamide S.sup.1,S.sup.1 -dioxide; (R)-N-[[6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-th iazin-2-yl]propyl]cyclopropyl-carboxamide S.sup.1,S.sup.1 -dioxide; (R)-N-[[6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-th iazin-2-yl]propyl]-3-methoxy propanamide S.sup.1,S.sup.1 -dioxide.

3. The compound of claim 2 which is R-(+)-6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-thia zine-2-butanoic acid 1,1-dioxide ethyl ester hydrochloride.

4. The compound of claim 2 which is R-(+)-6-(Aminosulfonyl)-4-ethylamino-3,4-dihydro-2H-thieno[3,2-e]-1,2-thia zine-2-butanoic acid 1,1-dioxide1-methyester hydrochloride.

5. A topical ophthalmic formulation for controlling intraocular pressure comprising a pharmaceutically effective amount of the compound of claim 1 in an inert carrier.

6. A method for controlling intraocular pressure by administering a pharmaceutically effective amount of the compound of claim 1 to a human eye.
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