Abstract: A complex of polyriboinosinic-polyribocytidylic acid (poly I:C) with poly-L-lysine hydrobromide ([lysine.HBr].sub.n) having a defined molecular weight is prepared which is about 5-15 times as resistant to hydrolysis by pancreatic ribonuclease as the parent poly I:C. A pharmaceutical solution, containing a relatively high concentration of the complex, prepared as described, induces significant antiviral levels of serum interferon in monkeys under conditions in which poly I:C itself induces little or no interferon. An important feature of this invention is that the product is a soluble material requiring no special solubilizing agent, thereby facilitating the preparation of solutions having the desired concentration. The product will hereinafter be designated as poly I:C/poly-L-lysine.
Type:
Grant
Filed:
February 8, 1982
Date of Patent:
June 14, 1983
Assignee:
Merck & Co., Inc.
Inventors:
A. Kirk Field, Alfred A. Tytell, George P. Lampson
Abstract: A vesicular, immunogenic, non-pyrogenic complex is obtained from isolates of N. gonorrhoeae by cultivating N. gonorrhoeae on a suitable nutrient medium; harvesting and centrifuging the cells; extracting the cell pellet with TRITON X-100 at alkaline pH; suspending the solids remaining after extraction in aqueous medium and precipitating in the cold with ethanol.
Type:
Grant
Filed:
August 20, 1981
Date of Patent:
May 31, 1983
Assignee:
Merck & Co., Inc.
Inventors:
Edward C. O'Rourke, W. Wardle Fullerton
Abstract: Disclosed are antibiotic cephalosporins (I) of the formula: ##STR1## Wherein the stylized radical attached to the 7-amino nitrogen of the cephalosporin moiety represents a nitrogen-containing heterocyclic group (mono- or polycyclic); R is, inter alia, hydrogen, alkyl, heterocyclylalkyl, aryl, alkenyl, aralkyl, --NR.sub.2, --OR, COOR, CONR.sub.2 or CN; A is conventionally known in the cephalosporin art; and R.sup.2 is H, or lower alkoxyl. Also disclosed are the pharmaceutically acceptable salt and ester derivatives of I; 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.
Abstract: Disclosed is a process for the stereocontrolled total synthesis of thienamycin via intermediates II and IIa: ##STR1## wherein R is a readily removable carboxyl protecting group.
Type:
Grant
Filed:
April 8, 1981
Date of Patent:
September 14, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Thomas M. H. Liu, David G. Melillo, Kenneth M. Ryan, Ichiro Shinkai, Meyer Sletzinger
Abstract: Disclosed is methyl 3-azido-4-C-cyano-2,3,4,6-tetradeoxy-.alpha.-D-arabino-hexopyranoside and processes for its preparation from methyl 3-azido-2,3,6-trideoxy-.alpha.-D-arabino-hexopyranoside via the 4-bromo-4-deoxy intermediate; wherein the two inversions of configuration at C-4 result in a net retention of the .alpha.-D-arabino stereochemistry.
Abstract: Disclosed is a process for the stereocontrolled total synthesis of thienamycin from acetone dicarboxylate via intermediate II: ##STR1## wherein R is a readily removable carboxyl protecting group.
Type:
Grant
Filed:
April 17, 1981
Date of Patent:
August 17, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Thomas M. H. Liu, David G. Melillo, Kenneth M. Ryan, Ichiro Shinkai, Meyer Sletzinger
Abstract: Process and intermediate products useful in the preparation of cephalosporin compounds having a substituent at the 7-position in place of hydrogen are provided. The new cephalosporin compounds are active against various gram-negative and gram-positive organisms.
Type:
Grant
Filed:
April 30, 1980
Date of Patent:
August 10, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Sandor Karady, Lovji D. Cama, Meyer Sletzinger
Abstract: Process and intermediate products useful in the preparation of cephalosporin compounds having a substituent at the 7-position in place of hydrogen are provided. The new cephalosporin compounds are active against various gram-negative and gram-positive organisms.
Type:
Grant
Filed:
April 30, 1980
Date of Patent:
August 3, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Sandor Karady, Lovji D. Cama, Meyer Sletzinger
Abstract: Process and intermediate products useful in the preparation of cephalosporin compounds having a substituent at the 7-position in place of hydrogen are provided. The new cephalosporin compounds are active against various gram-negative and gram-positive organisms.
Type:
Grant
Filed:
April 30, 1980
Date of Patent:
August 3, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Sandor Karady, Lovji D. Cama, Meyer Sletzinger
Abstract: Disclosed is a process for the synthesis of carbapenem antibiotics I and their pharmaceutically acceptable salts and esters from 1: ##STR1## wherein: R.sup.7, R.sup.6, R.sup.1, R.sup.2 and R.sup.8 are selected from hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, spirocycloalkyl, cycloalkylalkyl, alkylcycloalkyl, aryl, aralkyl, aralkenyl, aralkynyl, heteroalkyl, heteroaralkyl, heterocyclyl and heterocyclyalkyl.
Abstract: Disclosed are S-oxides of 6-, 2- and 1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: ##STR1## wherein: n is 1 or 2; and R.sup.1, R.sup.2, R.sup.6, R.sup.7 and R.sup.8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide 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.
Abstract: Certain glucans modify the biosynthetic route of extracellular polysaccharides involved in dental plaque development causing critical loss of adhesiveness. They interfere with the biosynthesis of cell-bound polysaccharides reducing and preventing agglutination of cells. They thus aid in the prevention of dental plaque formation or concomitant dental caries and periodontal disease.
Abstract: Process and intermediate products useful in the preparation of cephalosporin compounds having a substituent at the 7-position in place of hydrogen are provided. The new cephalosporin compounds are active against various gram-negative and gram-positive organisms.
Type:
Grant
Filed:
April 30, 1980
Date of Patent:
July 6, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Sandor Karady, Lovji D. Cama, Meyer Sletzinger
Abstract: Process and intermediate products useful in the preparation of cephalosporin compounds having a substituent at the 7-position in place of hydrogen are provided. The new cephalosporin compounds are active against various gram-negative and gram-positive organisms.
Type:
Grant
Filed:
April 30, 1980
Date of Patent:
July 6, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Sandor Karady, Lovji D. Cama, Meyer Sletzinger
Abstract: Disclosed is a fermentation process for preparing and isolating the antibiotic, (5R,6S,8S)-3-(2-aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2. 0]hept-2-ene-2-carboxylic acid in substantially pure form.
Abstract: Enzymes called cariogenanases, elaborated by microorganisms are isolated and characterized as polysaccharases capable of degrading cariogenan, a newly discovered glucan of dental plaque composed of .alpha.-(1.fwdarw.3) and .alpha.-(1.fwdarw.2) linkages. The enzymes are isolable from culture broths of various organisms by protein precipitation methods, and have utility as an anti-dental plaque agent, either as the sole enzymatic agent or in combination with dextranases and/or plaque dispersing proteases.
Abstract: The antibiotic Tunicamycin is produced by fermenting a Tunicamycin-producing strain of Streptomyces (Streptomyces griseus ATCC 31591) under controlled conditions in a suitable nutrient medium and isolating the antibiotic so produced from the fermentation medium.
Type:
Grant
Filed:
December 3, 1980
Date of Patent:
May 18, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Enrique Tejera, Sara A. Currie, James E. Flor, Richard L. Monaghan
Abstract: Process and intermediate products useful in the preparation of cephalosporin compounds having a substituent at the 7-position in place of hydrogen are provided. The new cephalosporin compounds are active against various gram-negative and gram-positive organisms.
Type:
Grant
Filed:
April 30, 1980
Date of Patent:
April 13, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Burton G. Christensen, Sandor Karady, Lovji D. Cama, Meyer Sletzinger
Abstract: Disclosed is a chiral, total synthesis of thienamycin from D-glucose, which proceeds via intermediates I, II, and III and joins aldehyde IV or acid V, which are known to be useful in the total synthesis of thienamycin (VI): ##STR1## wherein R.sup.1 is hydrogen or a removable protecting group;R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms.
Abstract: Antibiotic 1-carba-6-(1-hydroxyethyl-2-carbonyl-penem-3-carboxylic acid is prepared by total chemical synthesis from 4-iodomethyl-1-(t-butyldimethylsilyl)-2-azetidinone.
Type:
Grant
Filed:
December 24, 1980
Date of Patent:
March 23, 1982
Assignee:
Merck & Co., Inc.
Inventors:
Lovji D. Cama, Ravindra Guthikonda, Burton G. Christensen