TOPICALLY ACTIVE CARBONIC-ANHYDRASE INHIBITORS .4. [(HYDROXYALKYL)SULFONYL]BENZENE AND [(HYDROXYALKYL)SULFONYL]THIOPHENESULFONAMIDES

被引：22

作者：

SHEPARD, KL ^{[1
]}

GRAHAM, SL ^{[1
]}

HUDCOSKY, RJ ^{[1
]}

MICHELSON, SR ^{[1
]}

SCHOLZ, TH ^{[1
]}

SCHWAM, H ^{[1
]}

SMITH, AM ^{[1
]}

SONDEY, JM ^{[1
]}

STROHMAIER, KM ^{[1
]}

SMITH, RL ^{[1
]}

SUGRUE, MF ^{[1
]}

机构：

[1] MERCK SHARP & DOHME LTD,DEPT OCULAR PHARM,W POINT,PA 19486

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1991年 / 34卷 / 10期

关键词：

D O I：

10.1021/jm00114a020

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

For several decades a tantalizing goal for the treatment of primary open-angle glaucoma has been the development of a topically active carbonic anhydrase inhibitor. Recent results from several research groups indicate that considerable progress has been made toward this objective. In this report, we present the design and synthesis of (hydroxyalkyl)sulfonyl-substituted benzene- and thiophenesulfonamides. These compounds exhibit inhibition of carbonic anhydrase II in the nanomolar range and lower intraocular pressure in the alpha-chymotrypsinized rabbit model of ocular hypertension after topical instillation.

引用

页码：3098 / 3105

页数：8

共 28 条

[1] LIPOPHILICITY MEASUREMENTS OF BENZENESULFONAMIDE INHIBITORS OF CARBONIC-ANHYDRASE BY REVERSED-PHASE HPLC [J].

ALTOMARE, C ;

CAROTTI, A ;

CELLAMARE, S ;

FERAPPI, M .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1989, 56 (03) :273-281

[2] THIENOTHIOPYRAN-2-SULFONAMIDES - NOVEL TOPICALLY ACTIVE CARBONIC-ANHYDRASE INHIBITORS FOR THE TREATMENT OF GLAUCOMA [J].

BALDWIN, JJ ;

PONTICELLO, GS ;

ANDERSON, PS ;

CHRISTY, ME ;

MURCKO, MA ;

RANDALL, WC ;

SCHWAM, H ;

SUGRUE, MF ;

SPRINGER, JP ;

GAUTHERON, P ;

GROVE, J ;

MALLORGA, P ;

VIADER, MP ;

MCKEEVER, BM ;

NAVIA, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (12) :2510-2513

[3] CEREBROVASODILATATION THROUGH SELECTIVE-INHIBITION OF THE ENZYME CARBONIC-ANHYDRASE .3. 5-(ARYLTHIO)-, 5-(ARYLSULFINYL)-, AND 5-(ARYLSULFONYL)THIOPHENE-2-SULFONAMIDES [J].

BARNISH, IT ;

CROSS, PE ;

DICKINSON, RP ;

PARRY, MJ ;

RANDALL, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (08) :959-964

[4] INHIBITION OF CARBONIC-ANHYDRASE BY SUBSTITUTED BENZENESULFONAMIDES - A REINVESTIGATION BY QSAR AND MOLECULAR GRAPHICS ANALYSIS [J].

CAROTTI, A ;

RAGUSEO, C ;

CAMPAGNA, F ;

LANGRIDGE, R ;

KLEIN, TE .

QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS, 1989, 8 (01) :1-10

[5] TOPICALLY ACTIVE CARBONIC-ANHYDRASE INHIBITORS .3. BENZOFURAN-SULFONAMIDE AND INDOLE-2-SULFONAMIDE [J].

GRAHAM, SL ;

HOFFMAN, JM ;

GAUTHERON, P ;

MICHELSON, SR ;

SCHOLZ, TH ;

SCHWAM, H ;

SHEPARD, KL ;

SMITH, AM ;

SMITH, RL ;

SONDEY, JM ;

SUGRUE, MF .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :749-754

[6] TOPICALLY ACTIVE CARBONIC-ANHYDRASE INHIBITORS .2. BENZO[B]THIOPHENESULFONAMIDE DERIVATIVES WITH OCULAR HYPOTENSIVE ACTIVITY [J].

GRAHAM, SL ;

SHEPARD, KL ;

ANDERSON, PS ;

BALDWIN, JJ ;

BEST, DB ;

CHRISTY, ME ;

FREEDMAN, MB ;

GAUTHERON, P ;

HABECKER, CN ;

HOFFMAN, JM ;

LYLE, PA ;

MICHELSON, SR ;

PONTICELLO, GS ;

ROBB, CM ;

SCHWAM, H ;

SMITH, AM ;

SMITH, RL ;

SONDEY, JM ;

STROHMAIER, KM ;

SUGRUE, MF ;

VARGA, SL .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (12) :2548-2554

[7] MOLECULAR GRAPHICS AND QSAR IN THE STUDY OF ENZYME LIGAND INTERACTIONS - ON THE DEFINITION OF BIORECEPTORS [J].

HANSCH, C ;

KLEIN, TE .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (12) :392-400

[8]

HANSCH C, 1985, MOL PHARMACOL, V27, P493

[9]

HENNEKES R, 1988, INVEST OPHTHALMOL S, P82

[10] Identification of organic compounds I Chlorosuffonic acid as a reagent for the identification of aryl halides [J].

Huntress, EH ;

Carten, FH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :511-514

← 1 2 3 →