Patents by Inventor Heinrich K. Schnoes

Heinrich K. Schnoes 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).

  • Patent number: 5430196
    Abstract: A synthesis of 1.alpha.-hydroxy-19-nor-vitamin D compounds comprises (a) the construction of a 5,8-diol-6-yne intermediate by joining ring-A and ring-C/D portions of the desired end product via the condensation of an acetylenic derivative containing the C/D-ring portion of the desired end product with a cyclic dihydroxy ketone representing the A-ring of the desired end product; (b) the partial reduction of the 6,7 acetylenic triple bond linkage between the A and C/D ring potions to obtain a 5,8-diol-6-ene intermediate; and (c) the reductive removal of the 5,8-oxygen functions to generate the required 5,7-diene end product from which the desired 7-trans(7E)-isomer is purified directly, or after optional double bond isomerization of the 7-cis(7Z)-isomer employing a novel thiophenol-promoted isomerization step.
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: July 4, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Fariba Aria
  • Patent number: 5414098
    Abstract: The invention provides new 24, 26, and/or 27 homologated vitamin D.sub.2 compounds, such as 26,27-dihomo-1.alpha.-hydroxyvitamin D.sub.2, 26,27-dihomo-1.alpha.-hydroxy-24-epi-vitamin D.sub.2, 26,27-dihomo-1.alpha.,25-dihydroxy-24-epi-vitamin D.sub.2 and certain hydroxy-protected derivatives thereof. The new epi compounds in particular exhibit a distinctive activity pattern comprising high potency in stimulating intestinal calcium transport and little or no activity in inducing bone calcium mobilization or the differentiation of undifferentiated cells in culture, thereby evincing utility in the treatment of diseases characterized by loss of bone mass. In contrast, the natural form exhibits no activity in either mobilizing calcium from bone or stimulating intestinal calcium transport. A process for preparing such compounds is also disclosed.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: May 9, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5395830
    Abstract: A method of treating osteoporosis comprising the administration of an effective amount of 1.alpha.,24(R)-dihydroxy-22(E)-dehydro-vitamin D.sub.3.
    Type: Grant
    Filed: January 12, 1994
    Date of Patent: March 7, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. Deluca, Heinrich K. Schnoes
  • Patent number: 5393749
    Abstract: A method of treating osteoporosis comprising the administration of an effective amount of 1.alpha.,25-dihydroxy-22(E)-dehydro-vitamin D.sub.3.
    Type: Grant
    Filed: October 25, 1993
    Date of Patent: February 28, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes
  • Patent number: 5391755
    Abstract: A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.
    Type: Grant
    Filed: January 13, 1994
    Date of Patent: February 21, 1995
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5354744
    Abstract: This invention provides novel vitamin D-related compounds characterized by extended unsaturated side chain structures. Such compounds exhibit increased activity in arresting the proliferation and promoting the differentiation of malignant cells with only minimal calcemic activity and thus represents new therapeutic agents applicable and uniquely useful in differentiation therapy of malignant diseases. The activity characteristics of these compounds provide the basis of a method for the treatment of neoplastic diseases, specifically leukemoid diseases.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: October 11, 1994
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5342975
    Abstract: This invention provides a novel class of vitamin D-related compounds, namely the 1.alpha.-hydroxy-19-nor-vitamin D analogs, as well as a general method for their chemical synthesis. The compounds exhibit pronounced activity in arresting the proliferation of undifferentiated cells, including malignant cells, and in inducing their differentiation, and thus represent novel therapeutic agents for the treatment of malignant and other diseases characterized by the proliferative growth of undifferentiated cells. Formulations for therapeutic use and treatment methods are also provided.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: August 30, 1994
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rafal R. Sicinski, Jean M. Prahl
  • Patent number: 5281731
    Abstract: A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: January 25, 1994
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5260290
    Abstract: The invention provides new 24, 26, and/or 27 homologated vitamin D.sub.2 compounds, such as 26,27-dihomo-1.alpha.-hydroxyvitamin D.sub.2, 26,27-dihomo-1.alpha.-hydroxy-24-epi-vitamin D.sub.2, 26,27-dihomo-1.alpha.,25-dihydroxy-24-epi-vitamin D.sub.2 and certain hydroxy-protected derivatives thereof. The new epi compounds in particular exhibit a distinctive activity pattern comprising high potency in stimulating intestinal calcium transport and little or no activity in inducing bone calcium mobilization or the differentiation of undifferentiated cells in culture, thereby evincing utility in the treatment of diseases characterized by loss of bone mass. In contrast, the natural form exhibits no activity in either mobilizing calcium from bone or stimulating intestinal calcium transport. A process for preparing such compounds is also disclosed.
    Type: Grant
    Filed: February 13, 1991
    Date of Patent: November 9, 1993
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5250523
    Abstract: This invention provides novel vitamin D-related compounds characterized by extended unsaturated side chain structures. Such compounds exhibit increased activity in arresting the proliferation and promoting the differentiation of malignant cells with only minimal calcemic activity and thus represents new therapeutic agents applicable and uniquely useful in differentiation therapy of malignant diseases. The activity characteristics of these compounds provide the basis of a method for the treatment of neoplastic diseases, specifically leukemoid diseases.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: October 5, 1993
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5246925
    Abstract: This invention provides a novel class of vitamin D-related compounds, namely the 1.alpha.-hydroxy-19-nor-vitamin D analogs, as well as a general method for their chemical synthesis. The compounds exhibit pronounced activity in arresting the proliferation of undifferentiated cells, including malignant cells, and in inducing their differentiation, and thus represent novel therapeutic agents for the treatment of malignant and other diseases characterized by the proliferative growth of undifferentiated cells. Formulations for therapeutic use and treatment methods are also provided.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: September 21, 1993
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rafal R. Sicinski, Jean M. Prahl
  • Patent number: 5247104
    Abstract: A synthesis of 1.alpha.,24(R)- and 1.alpha.,24(S)-dihydroxy-22(E)-dehydrovitamin D.sub.3 compounds. This process involves two major operations, namely, (a) the attachment of the required side chain to an existing vitamin D-22-aldehyde derivative to obtain an enone derivative as an intermediate, and (b) the stereoselective reduction of the ketone group of said enone intermediate to obtain the desired 24(R)- and 24(S)-hydroxyvitamin D compounds. The vitamin D enone derivatives generated as intermediates in the process are also new compounds.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: September 21, 1993
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes
  • Patent number: 5237110
    Abstract: This invention provides a novel class of vitamin D-related compounds, namely the 1.alpha.-hydroxy-19-nor-vitamin D analogs, as well as a general method for their chemical synthesis. The compounds exhibit pronounced activity in arresting the proliferation of undifferentiated cells, including malignant cells, and in inducing their differentiation, and thus represent novel therapeutic agents for the treatment of malignant and other diseases characterized by the proliferative growth of undifferentiated cells. Formulations for therapeutic use and treatment methods are also provided.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: August 17, 1993
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rafal R. Sicinski, Jean M. Prahl
  • Patent number: 5089647
    Abstract: This invention provides a novel method for the preparation of optically active arylalykylsulfone derivatives, having a chiral center in the alkyl moiety in either the (R)- or the (S)-configuration. These optically active sulfones find use in the stereospecific synthesis of steroid or vitamin D compounds having chiral center at either carbon 24 or carbon 25 of the side chain. The method comprises the steps of reacting an optically active sulfinate ester having a chiral center at sulfur with a racemic alkyl Grignard reagent to obtain a mixture of diastereomeric sulfoxides, separating the mixture of diastereomeric sulfoxides, and oxidizing separately each of the diastereomers to obtain the desired optically active sulfone.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: February 18, 1992
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5089641
    Abstract: This invention provides a new method of making secosterol compounds, and in particular to the preparation of 1.alpha.-hydroxy-homopregnacalciferol which is a secosterol compound that is effective in inducing the differentiation of malignant cells and is therefore useful for the treatment of malignancies such as leukemia.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: February 18, 1992
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5086191
    Abstract: New intermediate compounds that can be used effectively for the synthesis of a broad range of 1.alpha.-hydroxy-19-nor-vitamin D compounds. These novel intermediates are characterized by a group selected from hydroxy methyl (--CH.sub.2 OH), carboxaldehyde (--CHO), and carboxy ester (--COOAlkyl) at the carbon 22 position of the side chain of a 19-nor-vitamin D nucleus. Intermediates of this type are useful for the introduction of side chain units and thus represent important synthons for the preparation of many different 19-nor-vitamin D compounds.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: February 4, 1992
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5061699
    Abstract: This invention provides novel side chain homologs of 1.alpha.,25-dihydroxyvitamin D.sub.3 which exhibit enhanced and highly selective activity in inducing differentiation of malignant cells. It also provides a general method of synthesis applicable to the preparation of a variety of vitamin D side chain analogs, and a method of treatment of neoplastic diseases which takes advantage of the selective differentiation activity of the new vitamin D homologs.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: October 29, 1991
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Andrzej Kutner
  • Patent number: 5036061
    Abstract: The present invention provides novel derivatives of vitamin D.sub.2 and more specifically 1 alpha,25-dihydroxylated compounds of the vitamin D series. A process for the preparation of such derivatives is also provided as are certain intermediates in such process.The derivatives of this invention find ready application as substitutes for vitamin D.sub.3 or D.sub.2 or various of the known vitamin metabolites of these vitamins in their various applications to the correction of disorders involving calcium metabolism and associated bone disease.
    Type: Grant
    Filed: November 22, 1989
    Date of Patent: July 30, 1991
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Rafal R. Sicinski, Yoko Tanaka
  • Patent number: 5030772
    Abstract: This invention relates to hydroxylated derivatives of vitamin D.sub.2 and a process for preparing such compounds. In particular, a process for preparing the 24-epimer of vitamin D.sub.2 and the corresponding 1.alpha.-hydroxylated derivative thereof is disclosed. The vitamin D.sub.2 derivatives would find application in the treatment of or prophylaxsis for various disease states characterized by calcium and phosphorous imbalances.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: July 9, 1991
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Shigeya Okada
  • Patent number: 4973584
    Abstract: The invention provides a new vitamin D.sub.2 compound, 1.alpha.-hydroxy-24-epi-vitamin D.sub.2 and certain hydroxy-protected derivatives thereof. The new compound exhibits a distinctive activity pattern comprising high potency in stimulating intestinal calcium transport and little or no activity in inducing bone calcium mobilization or the differentiation of undifferentiated cells in culture, thereby evincing utility in the treatment of diseases characterized by loss of bone mass.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: November 27, 1990
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman