Patents Represented by Attorney Howard W. Bremer
  • Patent number: 4031129
    Abstract: Racemic 15-deoxy, 11,15-deoxy and other prostaglandins and methods for preparing the same. The initial reactant is lithium cyclopentadiene which is reacted with ethyl-7-bromoheptanoate to give the alkylated diene which in turn is oxygenated to a mixture of hydroxycyclopentenones. 2-(6'-carboethoxyhexyl)-4-hydroxy-cyclopenten-1-one is chromatographically recovered from the mixture and reacted with dihydropyran to give the tetrahydropyranyl ether which is then reacted with 1-lithium-1-trans-octene in the presence of tri-n-butylphosphine-copper iodide to produce racemic 15-deoxy-prostaglandin E.sub.1 ethyl ester which is chromatographically recovered. The ester is converted to the corresponding prostaglandin by the action of an esterase-producing microorganism.
    Type: Grant
    Filed: January 26, 1972
    Date of Patent: June 21, 1977
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: Charles J. Sih
  • Patent number: 4022768
    Abstract: 1.alpha.,25-dihydroxycholecalciferol is prepared by reacting 1,5,7-trien-3.beta.,25-diol with a 1,2,4-triazoline-dione derivative represented by the formula: ##STR1## wherein R represents an alkyl group or an aryl or substituted-aryl group; reacting the resulting 1,4-cyclic adduct represented by the general formula ##STR2## wherein R is as defined above, with a peroxide to form a 1.alpha.,2.alpha.-epoxide compound represented by the general formula ##STR3## wherein R is as defined above, reducing the so formed compound with a metal hydride to form cholesta-5,7-diene-1.alpha.,3.beta.,25-triol, irradiating the so formed compound with ultraviolet rays to form 1.alpha.,25-dihydroxyprevitamin D.sub.3, isomerizing the so formed previtamin D.sub.3, and recovering 1.alpha.,25-dihydroxycholecalciferol.
    Type: Grant
    Filed: February 12, 1976
    Date of Patent: May 10, 1977
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Isao Matsunaga, Kiyoshige Ochi, Hiroyuki Nagano, Minoru Shindo, Masayuki Ishikawa, Chikara Kaneko, Hector F. DeLuca
  • Patent number: 4021338
    Abstract: A method for correcting and preventing the failure of septic tank effluent seepage beds or similar installations which comprises treating such beds with a solution of an oxidizing agent, preferably hydrogen peroxide.
    Type: Grant
    Filed: November 8, 1976
    Date of Patent: May 3, 1977
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: John M. Harkin
  • Patent number: 4021568
    Abstract: A rodenticide suitable for the control of rat populations containing anticoagulant rodenticide-resistant rats comprising as the active rodenticidal ingredients 2-chloro-3-phytyl-1,4-naphthaquinone and a 3-substituted-4-hydroxycoumarin anticoagulant or a 2-substituted 1,3 indandione.
    Type: Grant
    Filed: May 12, 1975
    Date of Patent: May 3, 1977
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: John W. Suttie
  • Patent number: 3972916
    Abstract: A process for preparing dl-strigol, a potent seed germination agent, which comprises preparing the 2-bromomethyl-substituted methyl ester of 2,6,6-trimethylcyclohex-1-en-3-one-1-carboxylic acid, alkylating and cyclizing the said compound with an excess of dimethyl sodiomalonate to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-carboxylate and its enol, subjecting the said keto and enol forms of the compound, in admixture, to alkylation with methyl bromoacetate followed by acidic hydrolysis and spontaneous decarboxylation to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid, reducing the said acetic with a hydride reducing agent and recovering and separating the resulting 1,4-cis and trans-dihydroxy-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid lactones, formylating each of the cis and trans .gamma.
    Type: Grant
    Filed: December 13, 1974
    Date of Patent: August 3, 1976
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: Charles J. Sih
  • Patent number: 3968141
    Abstract: A method for stereospecifically preparing chiral 2-substituted-4-hydroxy-2-cyclopenten-1-one which comprises asymmetrically reducing 2-substituted cyclopentane-1,3,4-trione to the corresponding 2-substituted-4(R)-hydroxy-cyclopentane-1,3-dione, enolizing the said dione to obtain the enol ester or enol ether configuration, reducing the enol ester or ether and recovering the desired compound. The chiral 2-substituted-4-hydroxy-2-cyclopenten-1-one are key intermediates in the preparation of prostaglandins.
    Type: Grant
    Filed: June 12, 1974
    Date of Patent: July 6, 1976
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Charles J. Sih, James B. Heather
  • Patent number: 3962353
    Abstract: Compounds of the formula: ##SPC1##WhereR is hydrogen, methyl or ethyl;R' is hydrogen, a saturated hydrocarbon chain containing from 1 to about 9 carbon atoms, pentene, hexene, cyclohexyl, or benzylX is hydrogen, pyranoxy, OR" where R" is a hydrocarbon chain containing from 1 to about 5 carbon atoms or benzyl, ##EQU1## where R'" is a hydrocarbon chain containing from 1 to about 8 carbon atoms or benzyl, or ##SPC2##Where R.sub.1 and R.sub.2 are each a hydrocarbon chain containing from 1 to about 5 carbon atoms, andn is an integer from 0 to 5These compounds are key intermediates in the production of prostaglandins and exhibit antibacterial properties.
    Type: Grant
    Filed: September 9, 1974
    Date of Patent: June 8, 1976
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: Charles J. Sih
  • Patent number: 3962351
    Abstract: Compounds of the formula: ##SPC1##WhereR is hydrogen, methyl or ethyl;R' is hydrogen, a saturated hydrocarbon chain containing from 1 to about 9 carbon atoms, pentene, hexene, cyclohexyl, or benzylX is hydrogen, pyranoxy, OR" where R" is a hydrocarbon chain containing from 1 to about 5 carbon atoms or benzyl, ##EQU1## where R"' is a hydrocarbon chain containing from 1 to about 8 carbon atoms or benzyl, or ##EQU2## where R.sub.1 and R.sub.2 are each a hydrocarbon chain containing from 1 to about 5 carbon atoms, andn is an integer from 0 to 5These compounds are key intermediates in the production of prostaglandins and exhibit antibacterial properties.
    Type: Grant
    Filed: September 9, 1974
    Date of Patent: June 8, 1976
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: Charles J. Sih
  • Patent number: 3962352
    Abstract: Compounds of the formula: ##SPC1##WhereR is hydrogen, methyl or ethyl;R' is hydrogen, a saturated hydrocarbon chain containing from 1 to about 9 carbon atoms, pentene, hexene, cyclohexyl, or benzylX is hydrogen, pyranoxy, OR" where R" is a hydrocarbon chain containing from 1 to about 5 carbon atoms or benzyl, ##EQU1## where R'" is a hydrocarbon chain containing from 1 to about 8 carbon atoms or benzyl, or ##SPC2##Where R.sub.1 and R.sub.2 are each a hydrocarbon chain containing from 1 to about 5 carbon atoms, andn is an integer from 0 to 5These compounds are key intermediates in the production of prostaglandins and exhibit antibacterial properties.
    Type: Grant
    Filed: September 9, 1974
    Date of Patent: June 8, 1976
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: Charles J. Sih
  • Patent number: 3954806
    Abstract: A process for preparing dl-strigol, a potent seed germination agent, which comprises preparing the 2-bromomethyl-substituted methyl ester of 2,6,6-trimethylcyclohex-1-en-3-one-1-carboxylic acid, alkylating and cyclizing the said compound with an excess of dimethyl sodiomalonate to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-carboxylate and its enol, subjecting the said keto and enol forms of the compound, in admixture, to alkylation with methyl bromoacetate followed by acidic hydrolysis and spontaneous decarboxylation to obtain methyl 1,4-diketo-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid, reducing the said acetic acid with a hydride reducing agent and recovering and separating the resulting 1,4-cis and trans-dihydroxy-7,7-dimethyl-4,5,6,7-tetrahydroindane-2-acetic acid lactones, formylating each of the cis and trans .gamma.
    Type: Grant
    Filed: December 13, 1974
    Date of Patent: May 4, 1976
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: Charles J. Sih