Patents Represented by Attorney James Arno

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  • Substituted benzenesulfonylazides
    Patent number: 4284575
    Abstract: Disclosed are substituted benzenesulfonylazides (I) which are useful as diazo transfer reagents. ##STR1## R.degree.=C.sub.12 H.sub.
    Type: Grant
    Filed: October 10, 1980
    Date of Patent: August 18, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Frederick W. Bollinger, George G. Hazen
  • Synthesis of thienamycin via esters of (3SR, 4RS)-3-[(SR)-1-hydroxyethyl]-.beta.,2-dioxo-4-azetidinebutanoic acid
    Patent number: 4282148
    Abstract: Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: ##STR1## wherein R.sup.3 is a readily removable carboxyl protecting group.
    Type: Grant
    Filed: January 14, 1980
    Date of Patent: August 4, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Thomas M. H. Liu, David G. Melillo, Kenneth M. Ryan, Ichiro Shinkai, Meyer Sletzinger
  • 3-(2-Aminoethylthio)-6-amido-7-oxo-1-azabicyc lo(3.2.0)-hept-2-ene-2-carboxylic acid
    Patent number: 4281002
    Abstract: Disclosed are 3-(2-aminoethylthio)-6-amido-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylic acids having the structure: ##STR1## wherein R.sup.1 is hydrogen or acyl. 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.
    Type: Grant
    Filed: October 3, 1979
    Date of Patent: July 28, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ravindra N. Guthikonda, David B. R. Johnston, Susan M. Schmitt
  • 3-Substituted thio-6-amido-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid s-oxides
    Patent number: 4277482
    Abstract: Disclosed are S-oxides of 3-substituted thio-6-amido-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acids having the structure: ##STR1## wherein: n is 1 or 2; R.sup.1 is hydrogen or acyl; and R.sup.8 is, inter alia, independently selected from the group consisting of 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.
    Type: Grant
    Filed: October 15, 1979
    Date of Patent: July 7, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ravindra N. Guthikonda, David B. R. Johnston, Susan M. Schmitt
  • Process for preparing 7-(1-hydroxyethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxy lic acid and intermediate therefor
    Patent number: 4275207
    Abstract: Disclosed is a process for preparing 7-(1-hydroxethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxylic acid and its pharmaceutically acceptable salts and esters (I) by total synthesis starting with L-aspartic acid and proceeding via intermediate II: ##STR1## R=blocking group
    Type: Grant
    Filed: August 17, 1979
    Date of Patent: June 23, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Ronald W. Ratcliffe, Thomas N. Salzmann
  • Process for the preparation of thienamycin and intermediates
    Patent number: 4273709
    Abstract: Disclosed is a process for the total synthesis of thienamycin from 4-allylazetidinone (IIIa) via ##STR1## L-aspartic acid (III): ##STR2## R.dbd.H, blocking group or salt cation.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: June 16, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ronald W. Ratcliffe, Thomas N. Salzmann
  • 7-N-Heterocyclyl-2-substituted 1-oxadethia-cephalosporins
    Patent number: 4271159
    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; R.sup.o is H or CH.sub.3 ; and R.sup.2 is H, or loweralkoxyl: 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.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: June 2, 1981
    Assignee: Merck & Co., Inc.
    Inventor: John Hannah
  • 2-, 5-, and 6-Substituted-1-carbadethiapen-2-em-3-carboxylic acids
    Patent number: 4269873
    Abstract: Disclosed are 2-, 5- and 6-substituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: ##STR1## wherein R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are, inter alia, independently selected from the group consisting of hydrogen, (R.sup.9 is not 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 and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: May 26, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David B. R. Johnston, Susan M. Schmitt
  • Synthesis of thienamycin via trans-3-carboxymethylene-4-carboxy-5-methyl-.DELTA..sup.2 -isoxazoline
    Patent number: 4269772
    Abstract: Disclosed is a process for the stereocontrolled total synthesis of thienamycin, which synthesis proceeds via intermediate II: ##STR1## wherein R.sup.5 and R.sup.6 are removable protecting groups.
    Type: Grant
    Filed: January 14, 1980
    Date of Patent: May 26, 1981
    Assignee: Merck & Co., Inc.
    Inventors: David G. Melillo, Kenneth M. Ryan
  • 5-Substituted-1-carba-pen-2-em-3-carboxylic acid
    Patent number: 4267188
    Abstract: Disclosed are 1-carba-pen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, inter alia, independently selected from the group consisting of hydrogen (R.sup.4 is not hydrogen), alkyl, 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.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: May 12, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Lovji D. Cama, Burton G. Christensen
  • 5-Substituted-3 -(2-aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-en e-2-carboxylic acid
    Patent number: 4264621
    Abstract: Antibiotic 5-substituted-3-(2-aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3 .2.0]hept-2-ene-2-carboxylic acids (I) are disclosed: ##STR1## wherein R is alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl or heteroaryl.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: April 28, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David B. R. Johnston, Susan M. Schmitt
  • 3-N-Pyridinium nocardicin and antibiotic composition thereof
    Patent number: 4263306
    Abstract: This invention relates to a new class of antibiotics (I): ##STR1## wherein the stylized radical (hereafter referred to as R'): ##STR2## attached to the 3-amino nitrogen of nocardicin represents a mono- or polycyclic N-containing heterocyclic group; R is, inter alia, hydrogen, substituted and unsubstituted: alkyl, aryl, alkenyl, heterocyclylalkyl, heterocyclylalkenyl, aralkenyl, aralkyl, --NR.sub.2, COOR, CONR.sub.2, --OR, or CN.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: April 21, 1981
    Assignee: Merck & Co., Inc.
    Inventor: John Hannah
  • 6- And 1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acid
    Patent number: 4262009
    Abstract: Disclosed are 6- and 1-substituted-1-carbadethiapen-2-em-3-carboxylic acids I of the following structure: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, inter alia, independently selected from the group consisting of alkyl, 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.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: April 14, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • 1-1-Disubstituted-pen-2-em-3-carboxylic acids
    Patent number: 4262011
    Abstract: Disclosed are 1-substituted-pen-2-em-3-carboxylic acids (I) and their pharmaceutically acceptable salts and esters which are useful as antibiotics; such compounds are prepared by total synthesis. ##STR1## wherein R.sup.1 and R.sup.2 are, inter alia, substituted and unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, and spirocycloalkyl.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: April 14, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • 6-(1-Hydroxyethyl)-2-(2-aminoethylthio)-1,1-disubstituted-1-carbadet hiapen-2-em-3-carboxylic acids
    Patent number: 4262010
    Abstract: Disclosed are 1-substituted-6-(1-hydroxyethyl)-2-(2-aminoethylthio)-1-carbadethiapen-2-e m-3-carboxylic acids (I) and their pharmaceutically acceptable salts and esters which are useful as antibiotics; such compounds are prepared by total synthesis. ##STR1## wherein R.sup.1 and R.sup.2 are, inter alia, substituted and unsubstituted alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl and the spiro substituent formed by the joinder of R.sup.1 and R.sup.2.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: April 14, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • Crystalline N-formimidoyl thienamycin
    Patent number: 4260543
    Abstract: Disclosed is crystalline N-formimidoyl thienamycin and a process for its preparation.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: April 7, 1981
    Assignee: Merck & Co., Inc.
    Inventor: Thomas W. Miller
  • 6-(1'-Hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acid
    Patent number: 4260618
    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: October 10, 1978
    Date of Patent: April 7, 1981
    Assignee: Merck & Co., Inc.
    Inventor: Burton G. Christensen
  • 1-, 6- And 2-substituted-1-carba-2-penem-3-carboxylic acids
    Patent number: 4260627
    Abstract: Disclosed are 1-, 6- and 2-substituted-1-carba-2-penem-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, 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.
    Type: Grant
    Filed: October 24, 1978
    Date of Patent: April 7, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • Process for preparing 6-substituted amino-2-substituted-pen-2-em-3-carboxylic acid
    Patent number: 4255330
    Abstract: Disclosed are 6-substituted amino-2-substituted-pen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1 is hydrogen or acyl, R.sup.2 is hydrogen or methoxyl, and R.sup.3 is, inter alia, hydrogen, --R, --OR, --SR, --NR.sub.2 ; R is alkyl, aryl, aralkyl, heterocyclyl or heterocyclylalkyl; n is 0 or 1; when n=1, R.sup.3 is 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: December 31, 1979
    Date of Patent: March 10, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Frank P. DiNinno
  • 7-N-Heterocyclyl 1-oxa, 1-aza, and 1-carbadethiacephalosporins
    Patent number: 4255424
    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 loweralkoxyl; X is O, CH.sub.2, or NR.sup.7 (R.sup.7 is, inter alia, hydrogen, alkyl or aralkyl. 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.
    Type: Grant
    Filed: April 27, 1979
    Date of Patent: March 10, 1981
    Assignee: Merck & Co., Inc.
    Inventor: John Hannah