Abstract: The invention relates to a novel process and novel intermediates useful in the preparation of sympathomimetic amines. The pharmacologically useful final products, which are acyl derivatives of mono- and dihydroxy aromatic amines (e.g., catechol amines) can be prepared in optically active or racemic form by reacting the corresponding mono- or dihydroxy aromatic amine with a reagent capable of forming the N-tert-butoxycarbonyl derivative thereof; reacting the novel intermediate thus obtained with an acyloxymethyl chloride to afford the corresponding novel mono- or diacylated N-protected aromatic amine; and removing the N-protecting group therefrom.
Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.
Type:
Grant
Filed:
December 28, 1979
Date of Patent:
February 2, 1982
Assignee:
INTERx Research Corp.
Inventors:
Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
Abstract: Soft quaternary surface active agents having the formula: ##STR1## wherein ##STR2## represents a tertiary open chain or cyclic aliphatic amine; wherein ##STR3## represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.20 open chain or cyclo alkyl group, a C.sub.1 -C.sub.20 alkoxyalkyl group, a C.sub.1 -C.sub.20 acyloxyalkyl group, a C.sub.1 -C.sub.20 haloalkyl group, a C.sub.1 -C.sub.20 carboxyalkyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O--C.sub.1 -C.sub.4 alkyl group, an O--C.sub.1 -C.sub.8 acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 represents a C.sub.9 -C.sub.22 straight or branched alkyl group, a --(CH.sub.2).sub.n -- ##STR4## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each selected from the group consisting of a hydrogen atom, a methyl group or an ethyl group, a C.sub.0 -C.sub.
Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.
Type:
Grant
Filed:
January 22, 1980
Date of Patent:
January 19, 1982
Assignee:
INTERx Research Corporation
Inventors:
Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
Abstract: Novel substituted pyrazinyl-1,2,4-oxadiazoles and processes for preparing the same. The compounds are useful in the treatment of edema and hypertension.
Type:
Grant
Filed:
May 19, 1980
Date of Patent:
January 5, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Mark G. Bock, Edward J. Cragoe, Jr., Robert L. Smith
Abstract: Novel 4-(substituted thiazolyl)-3-hydroxy-3-pyrroline-2,5-diones are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate renal lithiasis.
Type:
Grant
Filed:
September 11, 1979
Date of Patent:
November 3, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
Abstract: 2,3-Dihydro-6,7-disubstituted-5-(acyl)benzofuran-2-carboxylic acids, the pharmaceutically acceptable 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:
January 27, 1978
Date of Patent:
October 20, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
Abstract: Novel 4-(substituted thiazolyl)-3-hydroxy-3-pyrroline-2,5-diones are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate renal lithiasis.
Type:
Grant
Filed:
September 11, 1979
Date of Patent:
October 20, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Clarence S. Rovny
Abstract: An apparatus for eliminating accidents on power machines such as brake presses which comprises in combination a safety pedal, proximity switch and metal plate.
Abstract: This invention relates to 3-amino-5-substituted-6-halo-N-(3,4-dihydro-6-substituted-1,3,5-triazin-2- yl)-2-pyrazinecarboxamides and processes for preparing same. The compounds are eukalemic/saluretic agents useful in the treatment of edema and hypertension.
Type:
Grant
Filed:
July 2, 1980
Date of Patent:
July 7, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Otto W. Woltersdorf, Edward J. Cragoe, Jr.
Abstract: This invention relates to 3-amino-5-substituted-6-halo-N-(4,4-disubstituted-6-substituted-1,3,5-tria zin-2-yl)-2-pyrazinecarboxamides and processes for preparing same. The compounds are eukalemic/saluretic agents useful in the treatment of edema and hypertension.
Type:
Grant
Filed:
July 2, 1980
Date of Patent:
June 9, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Otto W. Woltersdorf, Jr., S. Jane deSolms, Robert L. Smith
Abstract: An injector type cooling apparatus is disclosed wherein multiple flat liquid sprays are directed into a conduit of uniform cross-section to draw cooling air into and through the conduit for mixture with and heat transfer from the liquid. The discharge end of the conduit is fitted with mist eliminators, in addition, holes or slots fitted with mist eliminators are provided in the conduit roof or sides downstream of the liquid sprays. These holes or slots cause increased air flow which results in improved cooling apparatus performance.
Abstract: The invention is a unique combination of a pressure switch, a temperature switch, and a check valve which act to automatically control the on-off operation of a centrifugal pump in response to an external flow demand.
Abstract: Novel 4-substituted-3-hydroxy-3-pyrroline-2,5-diones are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate renal lithiasis.
Type:
Grant
Filed:
June 11, 1979
Date of Patent:
March 17, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
Abstract: Substituted 1-oxo-2,2-disubstituted-5-indanacetic 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.
Type:
Grant
Filed:
February 26, 1979
Date of Patent:
February 3, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Haydn W. R. Williams, Otto W. Woltersdorf, Jr.
Abstract: The case involves novel heterocyclic substituted pyrazinoylguanidines and a process for preparing same. The heterocyclic pyrazinoylguanidines are eukalemic agents possessing diuretic and natriuretic properties.
Type:
Grant
Filed:
March 27, 1979
Date of Patent:
January 20, 1981
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr., Susan J. DeSolms
Abstract: The invention relates to 2,3-dihydro-6,7-disubstituted-5-(substituted sulfonyl)benzofuran-2-carboxylic acids and derivatives thereof having diuretic-saluretic, uricosuric and antihypertensive pharmacological activity.
Type:
Grant
Filed:
June 21, 1979
Date of Patent:
December 2, 1980
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., William F. Hoffman
Abstract: This invention relates to 2,3-dihydro-2,6,7-trisubstituted-5-acylbenzofurans, derivatives thereof and processes for their preparation. The novel benzofurans described herein have diuretic-saluretic, uricosuric and antihypertensive pharmacological activity.
Type:
Grant
Filed:
June 21, 1979
Date of Patent:
December 2, 1980
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., William F. Hoffman
Abstract: Novel derivatives of glycolic and glyoxylic acid are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate urolithiasis (calcium oxalate kidney and bladder stone disease).
Type:
Grant
Filed:
May 3, 1979
Date of Patent:
November 11, 1980
Assignee:
Merck & Co., Inc.
Inventors:
Haydn W. R. Williams, Edward J. Cragoe, Jr., Clarence S. Rooney