Patents by Inventor Norman L. Wendler

Norman L. Wendler has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Chemical synthesis of flavipucine
    Patent number: 4094878
    Abstract: A method for the total chemical synthesis of flavipucine employs the condensation of 4-hydroxy-6-methyl-2-pyridone with isobutylglyoxal in alkali alkoxide. The resulting alkali salt is acylated in both the 1' and 4 positions. Treatment of the 1',4-diacyloxy derivative with excess alkaline peroxide yields flavipucine.
    Type: Grant
    Filed: May 19, 1977
    Date of Patent: June 13, 1978
    Assignee: Merck & Co., Inc.
    Inventors: Norman L. Wendler, Narindar N. Girotra, Zbigniew S. Zelawski, deceased
  • 3.beta.-[(Methoxalyl)oxy]-2.alpha.-(3-oxo-1-octeny l)-5-oxo-1.beta.-cyclopentaneheptanoic acid and process
    Patent number: 4005106
    Abstract: Racemic or optically-active prostaglandin E.sub.1 is synthesized from racemic or optically-active precursors in good yield at the various steps from 3.alpha.,6,7,7.alpha.-tetrahydro-4-methyl-2-oxo-1.beta.-indaneheptanoic acid methyl ester proceeding through 2.alpha.-(2-carboxyethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentaneheptan oic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-formylethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopent aneheptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-oxoetyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentaneh eptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, and 3.beta.-hydroxy-2.alpha.-(3-oxo-1-octenyl)-5-oxo-1.beta.-cyclopentanehepta noic acid methyl ester, 5-cyclic ethylene acetal.
    Type: Grant
    Filed: May 7, 1975
    Date of Patent: January 25, 1977
    Assignee: Merck & Co., Inc.
    Inventors: Norman L. Wendler, David Taub, Harry L. Slates, Zbigniew S. Zelawski
  • 2.alpha.-(2-Carboxy-2-formylethyl )-3.beta.-hydroxy-5-oxo-.beta.-cyclopentaneheptanoic acid and process
    Patent number: 3998849
    Abstract: Racemic or optically-active prostaglandin E.sub.1 is synthesized from racemic or optically-active precursors in good yield at the various steps from 3.alpha.,6,7,7.alpha.-tetrahydro-4-methyl-2-oxo-1.beta.-indaneheptanoic acid methyl ester proceeding through 2.alpha.-(2-carboxyethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentaneheptan oic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-formylethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopent aneheptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-oxoethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentane heptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, and 3.beta.-hydroxy-2.alpha.-(3-oxo-1-octenyl)-5-oxo-1.beta.-cyclopentanehepta noic acid methyl ester, 5-cyclic ethylene acetal.
    Type: Grant
    Filed: May 8, 1975
    Date of Patent: December 21, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Norman L. Wendler, David Taub, Harry L. Slates, Zbigniew S. Zelawski
  • 2.alpha.-(2-Carboxy-2-oxoethyl)-3.beta.-hydroxy-5-oxo-1.beta.-c yclopentaneheptanoic acid and process
    Patent number: 3992412
    Abstract: Racemic or optically-active prostaglandin E.sub.1 is synthesized from racemic or optically-active precursors in good yield at the various steps from 3.alpha., 6,7,7.alpha.-tetrahydro-4-methyl-2-oxo-1.beta.-indaneheptanoic acid methyl ester proceeding through 2.alpha.-(2-carboxyethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentaneheptan oic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-formylethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopent aneheptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-oxoethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentane heptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, and 3.beta.-hydroxy-2.alpha.-(3-oxo-1-octenyl)-5-oxo-1.beta.-cyclopentanehepta noic acid methyl ester, 5-cyclic ethylene acetal.
    Type: Grant
    Filed: May 8, 1975
    Date of Patent: November 16, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Norman L. Wendler, David Taub, Harry L. Slates, Zbigniew S. Zelawski
  • 2.alpha.-Formyl-3.beta.-[(methoxalyl)oxy]-5-oxo-1.beta.-cyclopentanehepta noic acid and process
    Patent number: 3992411
    Abstract: Racemic or optically-active prostaglandin E.sub.1 is synthesized from racemic or optically-active precursors in good yield at the various steps from 3.alpha., 6,7,7.alpha.-tetrahydro-4-methyl-2-oxo-1.beta.-indaneheptanoic acid methyl ester proceeding through 2.alpha.-(2-carboxyethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentaneheptan oic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-formylethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopent aneheptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-oxoethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentane heptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, and 3.beta.-hydroxy-2.alpha.-(3-oxo-1-octenyl)-5-oxo-1.beta.-cyclopentanehepta noic acid methyl ester, 5-cyclic ethylene acetal.
    Type: Grant
    Filed: May 8, 1975
    Date of Patent: November 16, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Norman L. Wendler, David Taub, Harry L. Slates, Zbigniew S. Zelawski
  • Intermediates in the synthesis of prostaglandins
    Patent number: 3992413
    Abstract: The invention relates to a new and novel synthesis of prostaglandin E.sub.2, and it particularly relates to a novel process starting with relatively inexpensive starting materials. The invention further relates to a synthesis which is readily adaptable for large scale processing because of the high yields in the individual reaction steps.The invention further relates to novel compounds formed as intermediates in the synthesis of prostaglandin E.sub.2. The invention still further relates to synthetic analogs and known metabolites of prostaglandin E.sub.2 and prostaglandin E.sub.1, useful as standards in certain biological assays for determining prostaglandin-like activity.
    Type: Grant
    Filed: July 25, 1975
    Date of Patent: November 16, 1976
    Assignee: Merck & Co., Inc.
    Inventors: David Taub, Norman L. Wendler
  • 2.alpha.-(2-Loweralkanoyloxy-2-carboxyvinyl)-3.beta.-hydroxy-5-oxo-1.beta.- c
    Patent number: 3991083
    Abstract: Racemic or optically-active prostaglandin E.sub.1 is synthesized from racemic or optically-active precursors in good yield at the various steps from 3.alpha.,6,7,7.alpha.-tetrahydro-4-methyl-2-oxo-1.beta.-indaneheptanoic acid methyl ester proceeding through 2.alpha.-(2-carboxyethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentaneheptan oic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-formylethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopent aneheptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, 2.alpha.-(2-carboxy-2-oxoethyl)-3.beta.-hydroxy-5-oxo-1.beta.-cyclopentane heptanoic acid methyl ester, .delta.-lactone, 5-cyclic ethylene acetal, and 3.beta.-hydroxy-2.alpha.-(3-oxo-1-octenyl)-5-oxo-1.beta.-cyclopentanehepta noic acid methyl ester, 5-cyclic ethylene acetal.
    Type: Grant
    Filed: May 8, 1975
    Date of Patent: November 9, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Norman L. Wendler, David Taub, Harry L. Slates, Zbigniew S. Zelawski
  • Prostaglandin intermediate
    Patent number: 3987082
    Abstract: (.+-.)-Prostaglandin E.sub.1 is totally synthesized with a high degree of stereoselectivity and in good yield at the various steps from 6-methoxy-3-indanol by a sequence of reactions proceeding through 6-methoxy-3-indeneheptanoic acid ester, 2,6-dioxo-4,5,6,7-tetrahydro-7-methyl-3-indanheptanoic acid ester 2-cyclic ethylene acetal, cis-3,4,5,7a-tetrahydro-7-methyl-2-oxoindanheptanoic acid ester, trans-trans 3-acetyl-2-(2-carboxy-ethyl)-5-oxocyclopentane heptanoic acid ester 5-cyclic-ethylene acetal, 3-acetoxy-2-formyl-5-oxocyclopentaneheptanoic acid ester 5-cyclic ethylene acetal, and 15-dehydro (.+-.)-prostaglandin E.sub.1. The end compound has the biological activity of naturally occurring prostaglandin E.sub.1.
    Type: Grant
    Filed: December 16, 1974
    Date of Patent: October 19, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Norman L. Wendler, David Taub
  • Precursors for prostaglandin E.sub.1
    Patent number: 3978115
    Abstract: The disclosure relates to novel precursors for the synthesis of prostaglandin E.sub.1 and the production of said precursors.
    Type: Grant
    Filed: May 14, 1975
    Date of Patent: August 31, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Zbigniew S. Zelawski, Norman L. Wendler
  • Prostaglandin E.sub.1 intermediate 3-carboxymethyl-4-methyl-2-1-carboxy-7-(loweralkoxy or aralkoxycarbonyl)-heptyl]-4-hydroxybutyric acid, .gamma.-lactone, and processes of their preparation
    Patent number: 3965120
    Abstract: Disclosed is a novel stereospecific synthesis of Prostaglandin E.sub.1.
    Type: Grant
    Filed: February 11, 1975
    Date of Patent: June 22, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Chan-Hwa Kuo, David Taub, Norman L. Wendler
  • Prostaglandins and methods of making same
    Patent number: 3950359
    Abstract: (.+-.)-Prostaglandin E.sub.1 is totally synthesized with a high degree of stereoselectivity and in good yield at the various steps from 6-methoxy-3-indanol by a sequence of reactions proceeding through 6-methoxy-3-indeneheptanoic acid ester, 2,6-dioxo-4,5,6,7-tetrahydro-7-methyl-3-indanheptanoic acid ester 2-cyclic ethylene acetal, cis-3,4,5,7a-tetrahydro-7-methyl-2-oxoindanheptanoic acid ester, trans-trans 3-acetyl-2-(2-carboxy-ethyl)-5-oxocyclopentane heptanoic acid ester 5-cyclic-ethylene acetal, 3-acetoxy-2-formyl-5-oxocyclopentaneheptanoic acid ester 5-cyclic ethylene acetal, and 15-dehydro (.+-.)-prostaglandin E.sub.1. The end compound has the biological activity of naturally occurring prostaglandin E.sub.1.
    Type: Grant
    Filed: December 16, 1974
    Date of Patent: April 13, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Norman L. Wendler, David Taub
  • Prostaglandin E.sub.1 intermediate 6.alpha.-carboxy-5.alpha.(1-hydroxyethyl)-2-cyclohexene-1-heptanoic acid,.gamma.-lactone, and lower alkyl or aralkyl esters thereof
    Patent number: 3939182
    Abstract: 6 .alpha.-Carboxy-5.alpha. (1-hydroxyethyl)-2-cyclohexene-1-heptanoic acid, .gamma. - lactone, and lower alkyl and aralkyl esters thereof, are useful intermediates for the production of Prostaglandin E.sub.1.
    Type: Grant
    Filed: February 11, 1975
    Date of Patent: February 17, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Chan-Hwa Kuo, David Taub, Norman L. Wendler
  • Precursors for prostaglandin E.sub.1
    Patent number: 3933901
    Abstract: This case relates to the synthesis of novel precursors of prostaglandin E.sub.1, particularly the intermediate 4-hydroxy-3 .alpha.-methyl-1.alpha., 2.alpha.-dilower-alkanoyloxymethylcyclohexene.
    Type: Grant
    Filed: May 2, 1973
    Date of Patent: January 20, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Zbigniew S. Zelawski, Norman L. Wendler