Abstract: [1-Oxo-2-halo(or hydrogen)indanyloxy(or thio)]-alkanoic acid products and salts, esters and amide derivatives where the indanyl ring may be further substituted with from 2 to 5 nuclear substituents. The [1-oxo-2-haloindanyloxy-(or thio)]alkanoic acids are prepared (1) via the halogenation of a [1-oxoindanyloxy(or thio)]alkanoic acid or (2) via the addition of halogen to a [1-oxoindenyloxy(or thio)]-alkanoic acid. The [1-oxoindanyloxy(or thio)]alkanoic acids are prepared (1) via cyclialkylation of a (2-alkylideneacyl)-phenoxy(or thio)alkanoic acid or (2) via etherification of a hydroxy(or mercapto)-2-alkyl-1-indanone. The [1-oxo-2-halo(or hydrogen)indanyloxy(or thio)]alkanoic acids are diuretics and saluretics. In addition, some of these compounds are also able to maintain the uric acid concentration in the body at pretreatment level or to cause a decrease in uric acid concentration.
Type:
Grant
Filed:
May 5, 1976
Date of Patent:
January 24, 1978
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: Quaternary salts of 3,4-dihydrospiro-2H-1,3-benzoxazines are prepared by treating 3,4-dihydrospiro-2H-1,3-benzoxazines with an alkylating agent. The products are antihypertensive agents.
Type:
Grant
Filed:
August 16, 1976
Date of Patent:
January 10, 1978
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Gerald E. Stokker, Everett M. Schultz
Abstract: Certain substituted 2-aminomethyl-6-iodophenols and their pharmaceutically acceptable acid addition salts wherein the phenyl nucleus may be further substituted with 1 to 3 nuclear substituents are useful as antihypertensive, diuretic and saluretic agents. These products may be prepared by either iodinating a 2-aminomethyl-3,4,5-substituted phenol or hydrolyzing an appropriately substituted N-(2-hydroxy-3-iodo-4,5,6-substituted benzyl)carboxamide under either acidic or basic conditions.
Type:
Grant
Filed:
September 20, 1976
Date of Patent:
June 14, 1977
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Everett M. Schultz
Abstract: This application illustrates staging of injector type evaporative heat exchangers in such a way that the water to have heat extracted from it flows through the stages in series but comes into contact with a new volume of air at each stage. Dramatic reductions in size of unit required to deal with high loads is achieved without increase in horsepower requirements.
Abstract: A splash bar for a cooling tower fill assembly is of longitudinally Z-shaped configuration. The top and bottom of the bar are parallel and are connected by an essentially vertical surface. The entire bar has openings throughout.
Abstract: [1-Hydroxy-5-indanyloxy (or thio)]alkanoic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and hypouricemic activity. The acid products are prepared by several synthetic methods.
Type:
Grant
Filed:
June 10, 1975
Date of Patent:
March 15, 1977
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: [1,3-Dihydroxy-2-substituted and 2,2-disubstituted-indanyloxy(or thio)]alkanoic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a 1,3-dioxo-2-substituted or 2,2-disubstituted-indanyloxy(or thio)alkanoic acid with a reducing agent.
Type:
Grant
Filed:
July 31, 1974
Date of Patent:
February 1, 1977
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: (1-Oxo-7,8-disubstituted-1,2,3,4-tetrahydro-6-naphthyloxy)- and (3,4-disubstituted-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)ac etic acids, their carboxylate salts, and the amide and 5-tetrazole derivatives thereof are active as diuretic and saluretic agents, which also have uricosuric activity.
Type:
Grant
Filed:
October 12, 1973
Date of Patent:
January 18, 1977
Assignee:
Merck & Co., Inc.
Inventors:
Otto W. Woltersdorf, Jr., Edward J. Cragoe, Jr., Everett M. Schultz, Gerald E. Stokker
Abstract: A crossflow cooling tower, water flow control valve and diffuser which includes an open ended inner valve cylinder which moves from a closed to an open position by means of a screw mechanism and allows water to be evenly distributed over a 360.degree. range to all parts of a hot water basin located directly under the valve. The water leaving the valve is directed and proportioned by a series of baffles and a cone to effect a uniform distribution over the basin.
Abstract: 1-Oxo-2,2-disubstituted-5-indanyloxy(or thio)alkanoic acids and their salt, ester, anhydride, amide and 5-tetrazolyl derivatives are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a 2,2-disubstituted-5-hydroxy(or mercapto)-1-indanone with an haloalkanoic acid or ester thereof and, if the ester is employed, hydrolyzing the ester.
Type:
Grant
Filed:
September 21, 1973
Date of Patent:
October 5, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: 6-Oxo-7,7-disubstituted-1,2,7,8-tetrahydro (and 7,8-dihydro)-6H-indeno-[5,4-b]furan (and thiophene)carboxylic acids, the salt, ester and amide derivatives thereof and combinations of these compounds with antikaluretic agents are disclosed having diuretic-saluretic, uricosuric and antihypertensive activity.
Type:
Grant
Filed:
February 24, 1975
Date of Patent:
October 5, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: A process for preparing (1-oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid comprising reacting 5-cyclopentyl-5-methyl-2-cyclopentenone with a 4-carbon conjugated (open or cyclic) diene bearing vicinal chlorines adjacent to an ether group; aromatizing the resulting adduct to yield the desired indanone.
Abstract: Process for preparing (1-oxo-2-phenyl, halophenyl or thienyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid, pharmaceutically acceptable salt, ester and amide derivatives thereof and intermediate 5-ether derivatives thereof comprising reacting under Friedel-Crafts conditions a 2-phenyl, halophenyl or thienyl-2-propionyl halide or an anhydride thereof with an ether derivative of 2,3-dichlorophenyl; and reacting the resulting propiophenone with formaldehyde in the presence of acid to yield the desired indanone.
Type:
Grant
Filed:
July 30, 1974
Date of Patent:
September 21, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Warren K. Russ, Jr., George G. Hazen, Earl M. Chamberlin
Abstract: This invention relates to a process and apparatus for applying a double edge to any flexible sheetlike material by bending over a portion of the sheet edge on each side of said sheetlike material. The sheetlike material must then be cured or made rigid by heating. The entire process and the apparatus also is handled as an integral operation with the forming and curing of the flexible sheet.
Abstract: [1-Oxo-2,3-hydrocarbylene-5-indanyloxy(or thio)] alkanoic acids, and the non-toxic pharmaceutically acceptable salts, esters and amides thereof are disclosed. The products display a polyfunctional pharmaceutical utility in that they exhibit diuretic, saluretic, uricosuric and antihypertensive activity. Also disclosed are processes for the preparation of such compounds, and methods of treatment comprising administering such compounds and compositions.
Type:
Grant
Filed:
September 21, 1973
Date of Patent:
August 24, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: [1,3-Dioxo-2-substituted and 2,2-disubstituted-indanyloxy(or thio)]alkanoic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a (2,2-di or 2-)substituted-6-hydroxy-(or mercapto)-1,3-indanedione with a haloalkanoic acid or ester thereof and if the ester is employed hydrolyzing the ester.
Type:
Grant
Filed:
October 12, 1973
Date of Patent:
August 24, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: [1-Hydroximino-2,2-disubstituted-5-indanyloxy-(or thio)]alkanoic acids and their salt, ester, anhydride, amide and 5-tetrazolyl derivatives are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a 1-oxo-2,2-disubstituted-5-indanyloxy(or thio)alkanoic acids or derivatives thereof with hydroxylamine in the presence of a base.
Type:
Grant
Filed:
May 22, 1974
Date of Patent:
August 10, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: [1,3-Dioxo-2-substituted and 2,2-disubstituted-indanyloxy(or thio)]alkanoic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a (2- or 2,2-di)substituted-6-hydroxy-(or mercapto)-1,3-indanedione with a haloalkanoic acid or ester thereof and if the ester is employed hydrolyzing the ester.
Type:
Grant
Filed:
July 31, 1974
Date of Patent:
June 29, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: An air pumping and scrubbing apparatus which is suitable for use in spray paint booths is described. This apparatus uses liquid sprays directed into a conduit to cause an air pumping action to inject air into the conduit and dis-discharge to atmosphere using water pressure to move the air so as to avoid the necessity for any moving parts or electrical corrections in and around the air stream. The liquid sprays impinge on mist eliminator strips and are recovered along with foreign material from the air while the air is exhausted downstream of the strips. A novel transfer plate arrangement is provided between the strips and a sump to minimize foreign material buildup on structual surfaces while allowing stratification in the sump; and novel baffle means are provided to cause a controlled air blowback across the sump to facilitate collection of the floating material therein.
Type:
Grant
Filed:
October 29, 1974
Date of Patent:
June 22, 1976
Assignee:
Baltimore Aircoil Company, Inc.
Inventors:
John Engalitcheff, Jr., Edward N. Schinner
Abstract: This invention relates to a spacer-turbulator for use in separating corrugated type fill sheets of a cross-flow cooling tower and for imparting turbulence to the air flowing through said fill in said cross flow cooling tower.