Abstract: 1-(Substituted-aminoalkoxyphenyl)-2-methylene-1-alkanones, a class of compounds possessing anti-allergic properties for use in the treatment of allergic conditions, such as asthma prepared by etherifying an alkanoylphenol with an aminoalkyl halide, converting the ether formed to a salt of Mannich base by reacting it with a salt of a secondary amine in the presence of formaldehyde or paraformaldehyde and treating the Mannich salt with a weak base to deaminate the same and form the final product.
Abstract: Disclosed are 6-amido-2-S-oxides of substituted 2-organothio-pen-2-em-3-carboxylic acids (I) which are useful as antibiotics and as intermediates in the synthesis of substituted pen-2-em-3-carboxylic acids: ##STR1## wherein: R.sup.1 is H or acyl; R.sup.2 is hydrogen or methoxyl; R.sup.3 is alkyl having from 1-6 carbon atoms; phenylalkyl having 7-12 carbon atoms; and cycloalkyl having 3-6 carbon atoms; and R.sup.4 is hydrogen, a removable protecting group or a pharmaceutically acceptable salt or ester moiety.
Type:
Grant
Filed:
March 1, 1982
Date of Patent:
June 14, 1983
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Frank P. DiNinno, David A. Muthard, Ronald W. Ratcliffe
Abstract: Disclosed are 6-(1'-hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein R is, inter alia, hydrogen, --OR, --SR, --NR.sub.2, alkyl, aryl, aralkyl, or heterocylcyl; n is 0 or 1; when n=1 R is as defined but not --SR. Such compounds and their pharmaceutically acceptable salt and ester derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
Type:
Grant
Filed:
November 12, 1981
Date of Patent:
May 31, 1983
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Frank P. DiNinno
Abstract: Renin inhibitory peptides of the formula:Leu--Stav--Val--Phe (I.)and analogs thereof inhibit renin and are useful for treating various forms of renin-associated hypertension and hyperaldosteronism.
Abstract: 4-(Substituted thiazolyl)-3-hydroxy-3-pyrroline-2,5-diones of the formula: ##STR1## are inhibitors of glycolic acid oxidase useful in treating or preventing calcium oxalate kidney or bladder stones.
Type:
Grant
Filed:
June 1, 1981
Date of Patent:
April 12, 1983
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
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.
Abstract: Immunologically active compounds of the formula: ##STR1## wherein: R.sub.1 is C.sub.1-7 alkyl; substituted C.sub.1-7 alkyl; phenyl; or substituted phenyl;R.sub.2 is hydrogen; C.sub.1-7 alkyl; substituted C.sub.1-7 alkyl; phenyl; substituted phenyl; phenyl C.sub.1-4 alkyl; or substituted phenyl C.sub.1-4 alkyl;R.sub.3 and R.sub.4 may be the same or different and are each independently hydrogen, provided that R.sub.3 and R.sub.4 may not both be hydrogen; or ##STR2## where X is --O--; --S--; or ##STR3## R.sub.10 is hydrogen; C.sub.1-30 alkyl; C.sub.2-30 alkenyl; C.sub.1-30 alkoxy; phenyl; C.sub.1-20 alkylsulfonyl; or cholesteryl;R.sub.11, R.sub.12, R.sub.13, R.sub.14, and R.sub.15 may be the same or different and are each independently hydrogen; C.sub.1-20 alkyl; C.sub.1-20 alkylcarbonyloxy; amino; benzyl; C.sub.1-20 alkoxymethyl; C.sub.1-20 alkylamido; or ##STR4## r is 0 or 1; s is 0 or 1; and t is 0 to 20; provided that s may only be 0 when both r and t are greater than 0 or when r is 0 and R.sub.
Type:
Grant
Filed:
April 17, 1980
Date of Patent:
January 11, 1983
Assignee:
Merck & Co., Inc.
Inventors:
Tsung-Ying Shen, Philippe L. Durette, Conrad P. Dorn, Jr., James B. Doherty, Richard T. Dean
Abstract: Antimicrobial compounds of the formulas: ##STR1## where R.sup.1 and R.sup.2 are hydrogen; halo; C.sub.1-4 alkyl; C.sub.1-4 alkoxy; hydroxy; nitro; cyano; or trifluoromethyl;m is 0 or 1; andn is 1 or 2.
Type:
Grant
Filed:
December 22, 1981
Date of Patent:
December 28, 1982
Assignee:
Merck & Co., Inc.
Inventors:
John E. Engelhart, Marshall R. Angeles, Michael J. D'Errico
Abstract: Novel pyrazinyl -1,2,4-oxadiazoles of the formulas: ##STR1## are useful in treating edema and hypertension, and particularly may be combined with kaliuretic diuretics such as hydrochlorothiazide and indacrinone.
Type:
Grant
Filed:
March 16, 1981
Date of Patent:
December 7, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Mark G. Bock, Edward J. Cragoe, Jr., Robert L. Smith
Abstract: 2,4-Disubstituted-1,2,5-thiadiazol-3(2H)-one antimicrobials have broad spectrum antibacterial and antifungal activity. They are found to be especially useful in agriculture to protect plants against diseases such as leaf, stem, and fruit spotting, internal discoloration and decay of fruits and vegetables. These compounds are particularly active against diseases caused by the genera Pseudomonas, Xanthomonas, Erwinia, and Corynebacterium.
Type:
Grant
Filed:
April 21, 1980
Date of Patent:
December 7, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Richard A. Dybas, Bruce E. Witzel, Nathaniel Grier
Abstract: Mercaptoalkylpyridines carrying an ethenyl or ethynyl substituent are prepared from known pyridine compounds, principally pyridoxine, by known chemical procedures, and are useful in the treatment of rheumatoid arthritis and related inflammatory diseases.
Type:
Grant
Filed:
July 25, 1980
Date of Patent:
October 19, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Tsung-Ying Shen, Howard Jones, Conrad P. Dorn
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 kidney stone formation. A novel process for their preparation is also disclosed.
Type:
Grant
Filed:
November 5, 1979
Date of Patent:
September 14, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
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 kidney stone formation. A novel process for their preparation is also disclosed.
Type:
Grant
Filed:
November 5, 1979
Date of Patent:
August 3, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
Abstract: Antimicrobial agents suitable for use in aqueous systems for their prservation against biodeterioration include substitutedpiperidinomethylpropenenitriles and propanenitriles. The unsaturated compounds are prepared by reaction of a suitable piperidine with cyano acetic acid and formaledehyde: the propane derivatives therefrom by nucleophilic addition.
Type:
Grant
Filed:
October 6, 1980
Date of Patent:
August 3, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Nathaniel Grier, Richard A. Dybas, Bruce E. Witzel
Abstract: 1-(Substituted-aminoalkoxyphenyl)-2-methylene-1-alkanones, a class of compounds possessing antiallergic propertiesfor use in the treatment of allergic conditions, such as asthma prepared by etherifying an alkanoylphenol with an aminoalkyl halide, converting the ether formed to a salt of Mannich base by reacting it with a salt of a secondary amine in the presence of formaldehyde or paraformaldehyde and treating the Mannich salt with a weak base todeaminate the same and form the final product.
Abstract: Antimicrobial agents suitable for use in aqueous systems for their preservation against biodeterioration include substitutedpiperidinomethyl-propenenitriles and propanenitriles. The unsaturated compounds are prepared by reaction of a suitable piperidine with cyano acetic acid and formaldehyde: the propane derivatives therefrom by nucleophilic addition.
Type:
Grant
Filed:
January 26, 1981
Date of Patent:
August 3, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Nathaniel Grier, Richard A. Dybas, Bruce E. Witzel
Abstract: Novel amino derivatives of 2-hydroxy-6,9-methano-11-amino-5,6,7,8,9,10-hexahydro-benzocyclooctenes, methods for their preparation, and their use as effective analgesic agents is described.
Abstract: 4-Amino- and 2,4-diaminopyrimidines with a quaternized ring nitrogen and an oxygen bearing substituent such as hydroxyalkyl, alkoxyalkyl, or alkanoyl on one of the exo- or endocyclic nitrogens and a C.sub.6-18 alkyl on another, are highly active antimicrobial agents with a relatively low acute mammalian toxicity.
Type:
Grant
Filed:
July 23, 1979
Date of Patent:
July 13, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Nathaniel Grier, Elbert E. Harris, Henry Joshua, Arthur A. Patchett, Bruce E. Witzel, Richard A. Dybas
Abstract: The invention relates to 1-[4-(4-sulfanilyl)phenyl] urea and derivatives thereof in pharmaceutical compositions and in methods of treating rheumatoid arthritis and immune complex diseases such as dermatitis herpetiformis.
Type:
Grant
Filed:
February 29, 1980
Date of Patent:
July 6, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Norman P. Jensen, David P. Jacobus, Howard Jones
Abstract: 2,4-Dioxo-4-substituted-1-butanoic acid derivatives of the formula: ##STR1## where R is hydrogen or C.sub.1-4 alkyl; andL is a lipophilic group consisting essentially of(1) ##STR2## where R' is (a) hydrogen; (b) C.sub.1-3 alkyl; (c) benzyl; (d) pyridyl C.sub.1-3 alkyl; or (e) (3,4-dihydro-3-hydroxy-2H-1,5-benzodioxepin-3-yl) methyl; provided that positions 2 and 6 of the substituted phenyl moiety may not be substituted; or(2) ##STR3## where R' has the same meaning as above; or a pharmaceutically acceptable salt thereof; useful in treating urinary tract, especially renal calcium oxalate lithiasis.
Type:
Grant
Filed:
December 29, 1980
Date of Patent:
June 29, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Clarence S. Rooney, Haydn W. R. Williams, Edward J. Cragoe, Jr., Arthur A. Patchett