Patents Represented by Attorney Raymond M. Speer

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  • Steroidal glycolipids as host resistance stimulators
    Patent number: 4652553
    Abstract: Described are derivatives of glycolipids with substituted steroids bridged via a medium length hydrocarbon chain to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses. These compounds protect an immunocompromised human or animal host against opportunistic infection by virtue of their immunostimulant properties.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: March 24, 1987
    Assignee: Merck & Co., Inc.
    Inventors: William K. Hagmann, Philippe L. Durette, Mitree M. Ponpipom
  • 6-(1-hydroxyethyl)-2-carbamimidoyl-pen-2-em-3-carboxylic acids
    Patent number: 4650794
    Abstract: Disclosed are 6-(1-hydroxyethyl)-2-carbamimidoyl-pen-2-em-3-carboxylic acids (I) having the representative structure: ##STR1## wherein: A is a direct, single bond connecting the indicated S and C atoms, or A is a cyclic or acyclic connecting group selected, inter alia, from alkyl, cycloalkyl, aryl, heteroaryl, heteroalkyl; R.sup.1 and R.sup.2, which define the carbamimidoyl function, are, inter alia, independently selected from hydrogen, alkyl, aryl, alkoxy, amino; additionally, said carbamimidoyl is characterized by cyclic structures achieved by the joinder of the two nitrogen atoms via their substituents and by their joinder to connecting group A; additionally, "carbamimidiums" are disclosed by quaternization of one of the nitrogen atoms of said carbamimidoyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics.
    Type: Grant
    Filed: April 29, 1982
    Date of Patent: March 17, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Frank P. DiNinno, William J. Leanza, Ronald W. Ratcliffe
  • 1-oxa-1-dethia-cephalosporin compounds and antibacterial agent comprising the same
    Patent number: 4645769
    Abstract: The subject invention includes a 1-oxa-1-dethia-cephalosporin compound represented by the general formula (1) ##STR1## wherein R.sup.1 is a group of the formula: ##STR2## where R.sup.5 is a methyl group, an ethyl group, a carboxymethyl group or a 2-carboxy isopropyl group, or R.sup.1 is a group of the formula: ##STR3## where R.sup.6 is a hydrogen atom, a 4-ethyl-2,3-dioxopiperazine-1-yl group, a 3,4-dihydroxy phenyl group or a 5- and 6-membered heterocyclic radical having 2 ring nitrogens as the sole hetero substituent in the ring and having at least one hetero group on the carbon adjacent to the ring nitrogens.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: February 24, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Seiji Shibahara, Tsuneo Okonogy, Yasushi Murai, Shunzo Fukatsu, Taro Niida, Burton G. Christensen, Tadashi Wakazawa
  • Renin inhibitory peptides having improved solubility
    Patent number: 4636491
    Abstract: Renin inhibitory peptides of the formula ##STR1## and analogs thereof inhibit renin and are useful for treating various forms of renin-associated hypertension and hyperaldosteronism.
    Type: Grant
    Filed: March 27, 1984
    Date of Patent: January 13, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Mark G. Bock, Robert M. DiPardo, Joshua S. Boger, Ben E. Evans, Roger Freidinger
  • Process for preparing substituted 2-thioxopenams and 2-substituted thiopenems
    Patent number: 4610823
    Abstract: Disclosed is a synthesis for preparing substituted 2-thioxopenams which are useful in the synthesis of penem antibiotics 7 which may be conducted in an enantiospecific manner; said process proceeds from azetidinone 1 via the azetidinone acetic ester 2, the 4-metallothiozetidinone 3, and the 4-dithiocarbonylazetidinone 4 to the substituted 2-thioxopenam 5: ##STR1## wherein: R.sup.6 and R.sup.7 are independently selected from: hydrogen; R.sup.6 NH-- (R.sup.6 is acyl or H); substituted and unsubstituted: alkyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, and cycloalkenyl; wherein said substituents are, inter alia: halo (chloro, bromo, fluoro, iodo), hydroxyl, cyano, carboxyl, amino, and the above-recited values for R.sup.6 and R.sup.7 ; in functional terms,R.sup.2 is a group which potentially forms a stable carbonium ion, for example: trityl (--C(C.sub.6 H.sub.5).sub.
    Type: Grant
    Filed: January 25, 1983
    Date of Patent: September 9, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Frank P. DiNinno, William J. Leanza, Ronald W. Ratcliffe
  • R-(Z)-4-amino-3-chloro-2-pentenedioic acid, novel antibacterial agent
    Patent number: 4600691
    Abstract: R-(Z)-4-amino-3-chloro-2-pentenedioic acid is a novel antibacterial and isolated from Streptomyces viridogenes MA5450, ATCC 39387.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: July 15, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Louis Chaiet, Richard L. Monaghan, Sheldon B. Zimmerman, Maria I. M. Fernandez
  • 1-, 6- and 2-substituted-1-carba-2-penem-3-carboxylic acids
    Patent number: 4600713
    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, R.sup.4 and R.sup.5 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, spirocycloalkyl, heterocyclyl, heteroaryl, 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 5, 1983
    Date of Patent: July 15, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • 6-(1-hydroxyethyl)-2-(2-amin oethylthio)-1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acids
    Patent number: 4582643
    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: July 13, 1982
    Date of Patent: April 15, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, David H. Shih
  • Process for the production of antibiotic 1-oxadethiacephalosporins, and intermediate
    Patent number: 4556513
    Abstract: Disclosed is a process for preparing antibiotic 1-oxadethiacephalosporins via diazo-species I: ##STR1## wherein: A is acyl; R.sup.1 is H or OCH.sub.3 ; and R.sup.2 is a protecting group.
    Type: Grant
    Filed: August 15, 1984
    Date of Patent: December 3, 1985
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Seiji Shibahara, Tsuneo Okonogi, Yasushi Murai, Shunzo Fukatsu, Taro Niida, Tadashi Wakazawa
  • Difficidin and derivative antibacterials
    Patent number: 4545991
    Abstract: Difficidin and derivative antibacterial compounds of the formula: ##STR1## where R.sub.a and R.sub.b are members independently selected from the group consisting of hydrogen; alkali metal and alkaline earth metal cations; ammonium; and substituted ammonium; and R.sup.1 is hydrogen or hydroxy.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: October 8, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Sheldon B. Zimmerman, Kenneth E. Wilson, Richard L. Monaghan, Sagrario M. Del Val, Maria I. M. Fernandez, Otto D. Hensens, James E. Flor, Cheryl Deriso
  • 1-Carba-2-penem-3-carboxylic acid
    Patent number: 4543257
    Abstract: Disclosed are 1-carba-2-penem-3-carboxylic acids of the following structure: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 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: January 4, 1980
    Date of Patent: September 24, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Lovji D. Cama, Burton G. Christensen
  • 4-Substituted-3-hydroxy-3-pyrroline-2,5-dione inhibitors of glycolic acid oxidase
    Patent number: 4537902
    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: August 27, 1985
    Assignees: Merck & Co., Inc., Merck Sharp & Dohme (I.A.) Corp.
    Inventors: Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
  • 1-Oxa-1-dethia-cephalosporin derivatives
    Patent number: 4534898
    Abstract: This invention relates to 1-oxa-1-dethia-cephalosporins which are useful as anti-biotics.
    Type: Grant
    Filed: July 20, 1983
    Date of Patent: August 13, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Seiji Shibahara, Tsuneo Okonogi, Yasushi Murai, Shunzo Fukatsu, Tadashi Wakazawa, Taro Niida, Burton G. Christensen
  • 6- And 6,6-disubstituted-3-substituted amino-1-azabicyclo-[3.2.0]hept-2-en-7-one-2-carboxylic acid
    Patent number: 4530841
    Abstract: Disclosed are 6- and 6,6-disubstituted-3-substituted amino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acids (I): ##STR1## wherein R.sup.1 and R.sup.2 are, inter alia, independently selected from the group consisting of hydrogen, substituted and unsubstituted: alkyl, aryl, and aralkyl; and R' and R" are independently selected from the group consisting of: H, substituted and unsubstituted alkyl and aralkyl, or together form a substituted or unsubstituted cyclic group.Such compounds and 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 compounds and compositions when an antibiotic effect is indicated.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: July 23, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ronald W. Ratcliffe
  • Substituted 1-azabicyclo(3.2.0)hept-6-en-2-one-7-carboxylic acids
    Patent number: 4529597
    Abstract: Disclosed are substituted 1-azabicyclo [3.2.0]-hept-6-en-2-one-7-carboxylic acids (I) and their pharmaceutically acceptable salts and esters which are useful as antibiotics. ##STR1## wherein R is hydrogen, and, inter alia, unsubstituted and substituted alkyl, aryl, aralkyl; R.sup.8 is, inter alia, unsubstituted and substituted alkyl, alkenyl, aryl, and aralkyl. 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: April 19, 1982
    Date of Patent: July 16, 1985
    Assignee: Merck & Co., Inc.
    Inventor: James V. Heck
  • Antibiotics-859A and production thereof
    Patent number: 4521408
    Abstract: The mixture, Antibiotics-859A and the production thereof is described. The Antibiotics-859A are produced by the controlled aerobic cultivation of Streptomyces griseoruber, ATCC 39068 in an aqueous nutrient medium. The Antibiotics-859A exhibit activity both in vitro and in vivo against gram negative and gram positive organisms including the genera: Diplococcus, Staphylococcus, Streptococcus, Pseudomonas and Salmonella.
    Type: Grant
    Filed: April 14, 1982
    Date of Patent: June 4, 1985
    Assignee: Merck & Co., Inc.
    Inventor: Edward O. Stapley
  • 2-Amino-3-cyano-5-halo-6-(substituted)pyrazine
    Patent number: 4518599
    Abstract: Antimicrobial compounds of the formula: ##STR1## wherein: Hal is bromine or chlorine; andR is mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C.sub.1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; are useful in various agricultural and industrial areas.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 21, 1985
    Assignee: Merck & Co., Inc.
    Inventor: David B. R. Johnston
  • 2-Amino-3,5-dicyano-6-(substituted)pyrazine antimicrobial compounds
    Patent number: 4517186
    Abstract: Antimicrobial compounds of the formula: ##STR1## wherein: R is mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C.sub.1-8 alkylthio; mono- or di-substituted lower alkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; are useful in various agricultural and industrial areas.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 14, 1985
    Assignee: Merck & Co., Inc.
    Inventor: David B. R. Johnston
  • 3-Acyl-2-amino-5-halo-6-(substituted)pyrazine antimicrobial compounds
    Patent number: 4512991
    Abstract: Antimicrobial compounds of the formula: ##STR1## wherein: Hal is bromine or chlorine;R is chloro, but only when R.sup.1 is other than hydrogen; mono- or di-substituted mono- or diloweralkylamino wherein the loweralkyl substituents are hydroxy or loweralkanoyloxy; 4-morpholino; thiocyano; mercapto; straight or branched chain C.sub.1-8 alkylthio; mono- or di-substituted loweralkylthio wherein the substituents are hydroxy, amino, loweralkanoylamino, or loweralkoxycarbonyl; arylthio; loweralkylsulfoxy; or loweralkylsulfonyl; andR.sup.1 is hydrogen; straight or branched C.sub.1-8 alkyl; aryl; aryl substituted with up to two members selected from the group consisting of C.sub.1-3 alkyl, C.sub.1-3 alkoxy, halo, and mono- or di-C.sub.1-3 alkyl substituted amino; heteroaryl; formyl C.sub.2-4 alkenyl; or C.sub.2-4 alkenyl;are useful in various agricultural and industrial areas.
    Type: Grant
    Filed: December 27, 1982
    Date of Patent: April 23, 1985
    Assignee: Merck & Co., Inc.
    Inventor: David B. R. Johnston
  • Indacrinone having enhanced uricosuric
    Patent number: 4510322
    Abstract: The uricosuric and diuretic properties of indacrinone, [6,7-dichloro-2,3-dihydro-2-methyl-1-oxo-2-phenyl-1H-inden-5-yl)oxy]acetic acid, are carefully balanced for maximum therapeutic benefit by manipulation of the proportion of (+) and (-) enantiomers in the final product within critical limits.
    Type: Grant
    Filed: February 3, 1983
    Date of Patent: April 9, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Edward H. Blaine, Edward J. Cragoe, Jr., Ralph F. Hirschmann, John F. Nancarrow, deceased, by Elisabeth M. Nancarrow, executrix, Jonathan A. Tobert