9,10-seco-cyclopentanohydrophenanthrene Ring System Or 9,10-seco Cyclopentanohydrophenanthrene Ring System Having A Bond Between The 3- And 5-positions (e.g., Vitamin D Compounds, Cholecalciferols, Activated 7-dehydrocholesterols, Dihydrotachysterols, 3,5 Cyclovitamin D Compounds, Etc.) Patents (Class 552/653)
  • Patent number: 11926583
    Abstract: A stabilized 1,25-dihydroxyvitamin D2 composition which is particularly well suited for pharmaceutical formulations, pharmaceutical formulations of the 1,25-dihydroxyvitamin D2 composition, and a method of making the purified composition by purifying a crude 1,25-dihydroxyvitamin D2 from acetone/water, are disclosed.
    Type: Grant
    Filed: January 2, 2014
    Date of Patent: March 12, 2024
    Assignee: EIRGEN PHARMA LTD.
    Inventor: Uttam Saha
  • Patent number: 11903952
    Abstract: Disclosed herein are methods and compositions useful in reducing inflammation, reducing inflammatory exudates, enhancing epithelial tissue generation or regeneration, and/or reducing mean pulmonary artery pressure in the lungs of a subject in need thereof. In particular, the compositions comprise vitamin D, an analog, or metabolite thereof, and the methods include administering the composition to a subject in need thereof. In some embodiments, the subject is suffering from an infection, such as a viral infection, which affects the lungs. In some embodiments, the viral infection comprises SARS-CoV-2.
    Type: Grant
    Filed: May 26, 2021
    Date of Patent: February 20, 2024
    Assignees: Northwestern University, Case Western Reserve University, The Regents of the University of Colorado
    Inventors: Kurt Q. Lu, Livia A. Veress, Kevin D. Cooper, Amisha Wallia
  • Patent number: 11819507
    Abstract: Pharmaceutically acceptable cholecalciferol sulfate salts are used for combating vitamin D3 deficiency. New cholecalciferol sulfate salts as well as pharmaceutical compositions of the pharmaceutically acceptable cholecalciferol sulfate salts are described as well.
    Type: Grant
    Filed: July 12, 2016
    Date of Patent: November 21, 2023
    Inventors: Oyewole Taye Salami, Sigrid Obenland, Reinhard Caliebe
  • Patent number: 11697635
    Abstract: Disclosed are methods of purifying the compound (22E)-(24R)-2-methylene-22-dehydro-1?,24,25-trihydroxy-19-nor-vitamin D3 to obtain the compound in crystalline form. The methods typically include the steps of dissolving (22E)-(24R)-2-methylene-22-dehydro-1?,24,25-trihydroxy-19-nor-vitamin D3 in a solvent comprising ethyl acetate and hexane to form a solution, allowing crystals of (22E)-(24R)-2-methylene-22-dehydro-1?,24,25-trihydroxy-19-nor-vitamin D3 to form and precipitate from the solution, and recovering the crystals of (22E)-(24R)-2-methylene-22-dehydro-1?,24,25-trihydroxy-19-nor-vitamin D3 from the solution.
    Type: Grant
    Filed: October 16, 2018
    Date of Patent: July 11, 2023
    Assignee: WISCONSIN ALUMNI RESEARCH FOUNDATION
    Inventors: Hector F. Deluca, Margaret Clagett-Dame, Lori Plum, Agnieszka Flores, James Thoden, Hazel Holden
  • Patent number: 11584713
    Abstract: A 25-hydroxycholecalciferol monohydrate crystal, a preparation method thereof, and a microemulsion using the 25-hydroxycholecalciferol monohydrate crystal. The X-ray powder diffraction spectrum of the 25-hydroxycholecalciferol monohydrate crystal of the present disclosure shows characteristic peaks at 2? of 10.035°, 11.623°, 14.631°, 15.054°, 15.551°, 16.471°, 17.198°, 19.002°, 19.628°, 20.109°, 21.886°, 23.113°, 23.661°, 24.701°, 25.220°, 25.440°, and 28.527°. The 25-hydroxycholecalciferol monohydrate crystal can effectively enhance the stability of 25-hydroxycholecalciferol, and is more beneficial to the production and storage of related preparations, and thus biological characteristics of 25-hydroxycholecalciferol can be effectively utilized.
    Type: Grant
    Filed: August 6, 2020
    Date of Patent: February 21, 2023
    Assignees: SHANDONG HAINENG BIOENGINEERING CO., LTD., SHANDONG HAINENG PHARMACEUTICAL CO., LTD.
    Inventors: Fei Tang, Jindang Cao, Xin Li, Chao Zhang, Hao Luo, Qiangqiang Li, Zhi Cao, Liang Shu
  • Patent number: 10479764
    Abstract: This invention discloses 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-vitamin D analogs, and specifically 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1?-hydroxyvitamin D3, and pharmaceutical uses therefor. This compound exhibits relatively high transcription activity as well as pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also shows low activity in vivo on bone calcium mobilization, and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.
    Type: Grant
    Filed: June 26, 2012
    Date of Patent: November 19, 2019
    Assignee: WISCONSIN ALUMNI RESEARCH FOUNDATION
    Inventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Rafal Barycki
  • Patent number: 10336694
    Abstract: It is an object of the present invention to provide methods for producing vitamin D that gives improved yields and reduced side product contamination. In various aspects, these methods provide for production of vitamin-D2 using ergosterol as provitamin D2 or a dihydroxy derivative thereof as a starting material, or production of vitamin-D3 using 7-dehydrocholesterol as provitamin D3 or a dihydroxy derivative thereof as the starting material. The methods described herein comprise irradiating the starting material in a solution including an organic or inorganic base with light in the wavelength range 245-360 nanometers (nm) to obtain a product containing pre-vitamin-D2 or pre-vitamin-D3, and heating the product to convert the resulting pre-vitamin-D2 or pre-vitamin-D3 to vitamin D2 or vitamin D3. In various embodiments, these methods further comprise recovering vitamin D2 or vitamin D3 from this reaction as a purified product.
    Type: Grant
    Filed: December 18, 2015
    Date of Patent: July 2, 2019
    Assignee: NUCELIS LLC
    Inventor: Laszlo Treiber
  • Patent number: 9994598
    Abstract: Disclosed are a polyene compound, preparation method and use thereof. Provided in the present invention is the preparation method of a polyene compound I, comprising the following steps: under an action of a base and in an organic solvent, conducting a Witting reaction on a compound II and a compound III to obtain the polyene compound I. By the preparation method in the present invention, a coupling reaction results in good product purity without producing an obvious by-product and involves no heavy metal, thus facilitating a control over product quality and costs, having a simple operation and mild reaction condition, enabling high reaction conversion, a high yield, few by-products, high resultant product purity, low production costs and simple post-processing, and being suitable for industrial production.
    Type: Grant
    Filed: May 26, 2016
    Date of Patent: June 12, 2018
    Assignee: CHEMVON BIOTECHNOLOGY CO., LTD.
    Inventors: Meng Wang, Qinghua Ye, Fangdao Wang, Maojun Cai, Jie Zhou, Dong Wang
  • Patent number: 9834512
    Abstract: Cyclopropane-containing vitamin D analogs of formulas I and IV are provided. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.
    Type: Grant
    Filed: May 31, 2012
    Date of Patent: December 5, 2017
    Assignee: WISCONSIN ALUMNI RESEARCH FOUNDATION
    Inventors: Hector DeLuca, Rafal Barycki, Lori Plum, Margaret Clagett-Dame
  • Patent number: 9416102
    Abstract: Disclosed are (22E)-2-methylene-22-dehydro-1,24,25-trihydroxy-19-nor-vitamin D3 compounds, their biological activities, and various pharmaceutical uses for these compounds. Particularly disclosed are (22E)-(24R)-2-methylene-22-dehydro-1?,24,25-trihydroxy-19-nor-vitamin D3 and (22E)-(24S)-2-methylene-22-dehydro-1?,24,25-trihydroxy-19-nor-vitamin D3, their biological activities, and various pharmaceutical uses for these compounds.
    Type: Grant
    Filed: November 19, 2013
    Date of Patent: August 16, 2016
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Lori A. Plum, Rafal Barycki, Margaret Clagett-Dame
  • Patent number: 9290447
    Abstract: This invention discloses (20R) and (20S)-24-(p-toluenesulfonyloxy)-25,26,27-trinorvitamin D3 analogs, and especially (20R)-25,26,27-trinor-24-(p-methylphenylsulfonate)-vitamin D3, its biological activities, and pharmaceutical uses therefor. This compound exhibits relatively little calcemic activity and does not promote cellular differentiation of HL-60 leukemia cells, but rather kills the cells. This cell death activity is found in small cell lung carcinoma also, but not in prostate, bone or ovarian cancer cells. This compound thus causes specific cell death in the absence of changes in calcium levels and without general toxicity in an animal. Therefore it might serve as a useful therapy for treatment of some forms of cancer, such as leukemia and lung cancer.
    Type: Grant
    Filed: April 19, 2012
    Date of Patent: March 22, 2016
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Rafal Barycki
  • Patent number: 9079843
    Abstract: To provide a novel vitamin D3 derivative useful as a therapeutic agent for osteoporosis. Provided is a vitamin D3 derivative represented by the following formula (1) or a medicinally acceptable solvate thereof: wherein R1 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkylcarbonyloxyalkyl group with each alkyl having 1 to 6 carbon atoms, or an arylcarbonyloxyalkyl group with the aryl having 6 to 10 carbon atoms and the alkyl having 1 to 6 carbon atoms; R2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms or, together with the other R2 and the carbon atom to which they are bound to, may form a cyclic alkyl group having 3 to 6 carbon atoms; R3 represents an alkyl group having 1 to 6 carbon atoms or, together with the other R3 and the carbon atom to which they are bound to, may form a cyclic alkyl group having 3 to 6 carbon atoms; X represents an oxygen atom or a methylene group; and n represents an integer of 1 or 2.
    Type: Grant
    Filed: February 3, 2015
    Date of Patent: July 14, 2015
    Assignee: Teijin Pharma Limited
    Inventor: Hiroshi Saito
  • Patent number: 9073885
    Abstract: A compound represented by the following Formula (1) that is effective for the treatment of Paget's disease of bone or hypercalcemia or a medically acceptable solvate thereof; [wherein R1 refers to hydrogen atom, C1-C6 alkyl group optionally substituted with hydrogen group or C1-C6 alkoxy group optionally substituted with hydroxyl group, R2a and R2b refer to hydrogen atom, C1-C10 alkyl group optionally substituted with hydroxyl group, C6-C10 aryl group optionally substituted with hydroxyl group or C7-C12 aralkyl group optionally substituted with a hydroxyl group, or are combined to represent ethylene group. However, a compound in which R1 is a hydrogen atom or a methyl group and R2a and R2b are hydrogen atoms is excluded].
    Type: Grant
    Filed: January 29, 2004
    Date of Patent: July 7, 2015
    Assignee: Teijin Pharma Limited
    Inventors: Kazuya Takenouchi, Miyuki Anzai, Hiroshi Saito, Kazuhisa Okada, Seiichi Ishizuka, Daishiro Miura, Hiroaki Takayama, Atsushi Kittaka, Nozomi Saito, Toshie Fujishima
  • Publication number: 20150148552
    Abstract: To provide a novel vitamin D3 derivative useful as a therapeutic agent for osteoporosis. Provided is a vitamin D3 derivative represented by the following formula (1) or a medicinally acceptable solvate thereof: wherein R1 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkylcarbonyloxyalkyl group with each alkyl having 1 to 6 carbon atoms, or an arylcarbonyloxyalkyl group with the aryl having 6 to 10 carbon atoms and the alkyl having 1 to 6 carbon atoms; R2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms or, together with the other R2 and the carbon atom to which they are bound to, may form a cyclic alkyl group having 3 to 6 carbon atoms; R3 represents an alkyl group having 1 to 6 carbon atoms or, together with the other R3 and the carbon atom to which they are bound to, may form a cyclic alkyl group having 3 to 6 carbon atoms; X represents an oxygen atom or a methylene group; and n represents an integer of 1 or 2.
    Type: Application
    Filed: February 3, 2015
    Publication date: May 28, 2015
    Applicant: TEIJIN PHARMA LIMITED
    Inventor: Hiroshi SAITO
  • Patent number: 9040728
    Abstract: Disclosed are methods of purifying the compound (20R)-19-nor-24-difluoro-1?,25-dihydroxyvitamin D3 to obtain the compound in crystalline form. The methods typically include the steps of dissolving a product containing the compound in a solvent comprising hexane and 2-propanol, cooling the solvent and dissolved product below ambient temperature for a sufficient amount of time to form a precipitate of crystals, and recovering the crystals.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: May 26, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Agnieszka Flores, James B. Thoden, Hazel M. Holden
  • Publication number: 20150141385
    Abstract: Methods for diagnosing, treating, and preventing catabolism-related vitamin D deficiency and related disorders, related compositions, apparatus and kits, are disclosed. A method involves measuring CYP24 expression and/or activity, or a proxy thereof such as FGF23 level, in a patient and correlating abnormally elevated CYP24 expression and/or activity with catabolism-related vitamin D deficiency or with susceptibility for catabolism-related vitamin D deficiency. In response to abnormally elevated CYP24 expression and/or activity, the method further includes administering a CYP24 inhibitor to the vitamin D deficient or at-risk patient, and preferably avoiding activation of the vitamin D binding receptor, such as by avoiding administration of active vitamin D compounds to such patients. Optionally, a vitamin D prohormone or prohormone can be administered.
    Type: Application
    Filed: January 28, 2015
    Publication date: May 21, 2015
    Inventors: P. Martin Petkovich, Christian F. Helvig, Joel Z. Melnick
  • Patent number: 9018194
    Abstract: The present invention provides a compound which functions as a selective vitamin D receptor modulator and has action-selectivity or tissue-selectivity such that it does not induce hypercalcemia but causes other effects. There is provided a compound represented by formula (I), a solvate thereof or a prodrug thereof. wherein m and n each independently represent 1 or 0; R represents a hydrogen atom or an alkyl group; Y represents an ethane-1,1-diyl group or an ethyne-1,2-diyl group; and Z1 represents a hydrogen atom and Z2 represents a hydroxyalkoxy group, or Z1 and Z2 jointly form a methylene group.
    Type: Grant
    Filed: March 1, 2012
    Date of Patent: April 28, 2015
    Assignees: Nibon University
    Inventors: Makoto Makishima, Sachiko Yamada, Antonio Mourino, Hiroaki Tokiwa, Takeru Kudo, Yusuke Watarai, Kazuki Maekawa
  • Patent number: 9006220
    Abstract: To provide a novel vitamin D3 derivative useful as a therapeutic agent for osteoporosis. Provided is a vitamin D3 derivative represented by the following formula (1) or a medicinally acceptable solvate thereof: wherein R1 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkylcarbonyloxyalkyl group with each alkyl having 1 to 6 carbon atoms, or an arylcarbonyloxyalkyl group with the aryl having 6 to 10 carbon atoms and the alkyl having 1 to 6 carbon atoms; R2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms or, together with the other R2 and the carbon atom to which they are bound to, may form a cyclic alkyl group having 3 to 6 carbon atoms; R3 represents an alkyl group having 1 to 6 carbon atoms or, together with the other R3 and the carbon atom to which they are bound to, may form a cyclic alkyl group having 3 to 6 carbon atoms; X represents an oxygen atom or a methylene group; and n represents an integer of 1 or 2.
    Type: Grant
    Filed: October 24, 2011
    Date of Patent: April 14, 2015
    Assignee: Teijin Pharma Limited
    Inventors: Hiroshi Saito, Masato Komiyama, Eiji Ochiai, Kenichiro Takagi, Takayuki Chida, Mariko Fujita, Keiichiro Imaizumi, Toshiyuki Kaneko
  • Patent number: 8993547
    Abstract: This invention discloses 3-desoxy-2-methylene-19-nor-vitamin D analogs, and specifically (20S)-3-desoxy-2-methylene-1?,25-dihydroxy-19-nor-vitamin D3 and (20R)-3-desoxy-2-methylene-1?,25-dihydroxy-19-nor-vitamin D3 as well as pharmaceutical uses therefor. These compounds exhibit relatively high binding activity and pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to monocytes thus evidencing use as anti-cancer agents especially for the treatment or prevention of osteosarcoma, leukemia, colon cancer, breast cancer, skin cancer or prostate cancer. These compounds also exhibit relatively high calcemic activity evidencing use in the treatment of bone diseases.
    Type: Grant
    Filed: June 13, 2012
    Date of Patent: March 31, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Lori A. Plum, Rafal R. Sicinski, Izabela Sibilska, Margaret Clagett-Dame
  • Patent number: 8987235
    Abstract: This invention discloses N-cyclopropyl-(20R)-2-methylene-19,26,27-trinor-25-aza-vitamin D analogs, and specifically N-cyclopropyl-(20R)-2-methylene-19,26,27-trinor-25-aza-1?-hydroxyvitamin D3 and pharmaceutical uses therefor. This compound exhibits relatively high binding activity and pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent especially for the treatment or prevention of leukemia, colon cancer, breast cancer, skin cancer or prostate cancer.
    Type: Grant
    Filed: May 16, 2012
    Date of Patent: March 24, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Grazia Chiellini
  • Publication number: 20150079165
    Abstract: Methods and compositions for treating 25-hydroxyvitamin D insufficiency and deficiency in a patient are described herein. The method includes orally administering to the patient a delayed, sustained release formulation including a first ingredient selected from the group consisting of 25-hydroxyvitamin D2, 25-hydroxyvitamin D3, or a combination of 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3, or it includes gradually administering to the patient a sterile intravenous formulation including a first ingredient selected from the group consisting of 25-hydroxyvitamin D2, 25-hydroxyvitamin D3, or a combination of 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3.
    Type: Application
    Filed: November 19, 2014
    Publication date: March 19, 2015
    Inventors: Charles W. Bishop, Keith H. Crawford, Eric J. Messner
  • Patent number: 8940916
    Abstract: Disclosed are methods of purifying the compound (20R)-2-methylene-19-nor-24-difluoro-1?,25-dihydroxyvitamin D3 to obtain the compound in crystalline form. The methods typically include the steps of dissolving a product containing the compound in a solvent comprising hexane and 2-propanol, cooling the solvent and dissolved product below ambient temperature for a sufficient amount of time to form a precipitate of crystals, and recovering the crystals.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: January 27, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Agnieszka Flores, James B. Thoden, Hazel M. Holden
  • Patent number: 8906888
    Abstract: The present invention provides novel 16,23-diene 25-oxime ether analogs of 1,25-dihydroxy vitamin D3, compositions comprising these compounds and methods of using these compounds as inhibitors of CYP24. In particular, the novel compound of the invention are useful for treating diseases which benefit from a modulation of the levels of 1,25-dihydroxy vitamin D3, for example, cell-proliferative disorders.
    Type: Grant
    Filed: April 25, 2006
    Date of Patent: December 9, 2014
    Assignees: Cytochroma Inc., Johns Hopkins University
    Inventors: Uttam Saha, Gary H. Posner, Mehmet Kahraman
  • Patent number: 8906410
    Abstract: Methods and compositions for treating 25-hydroxyvitamin D insufficiency and deficiency in a patient are described herein. The method includes orally administering to the patient a delayed, sustained release formulation including a first ingredient selected from the group consisting of 25-hydroxyvitamin D2, 25-hydroxyvitamin D3, or a combination of 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3, or it includes gradually administering to the patient a sterile intravenous formulation including a first ingredient selected from the group consisting of 25-hydroxyvitamin D2, 25-hydroxyvitamin D3, or a combination of 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3.
    Type: Grant
    Filed: March 22, 2013
    Date of Patent: December 9, 2014
    Inventors: Charles W. Bishop, Keith H. Crawford, Eric J. Messner
  • Publication number: 20140349979
    Abstract: A stabilized formulation for controlled release of a vitamin D compound is disclosed. The formulation comprises one or both of 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3 and a cellulosic compound. The stabilized formulations exhibit a stable dissolution profile following exposure to storage conditions and demonstrate improved pharmacokinetic parameters compared to unstabilized formulations.
    Type: Application
    Filed: March 14, 2014
    Publication date: November 27, 2014
    Applicant: OPKO IP HOLDINGS II, INC.
    Inventors: Jay A. White, Samir P. Tabash, Sammy A. Agudoawu, Joel Z. Melnick
  • Patent number: 8884039
    Abstract: Disclosed are methods of purifying (20R) and (20S) analogs of 2-methylene-19-nor-22-dimethyl-1?,25-dihydroxyvitamin D3 to obtain the (20R) and (20S) analogs in crystalline form. The method includes the steps of preparing a solvent of either diethyl ether or a mixture of 2-propanol and hexane, dissolving a product containing the (20R) and (20S) analog to be purified in the solvent, cooling the solvent and dissolved product below ambient temperature for a sufficient amount of time to form a precipitate of crystals, and recovering the crystals.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: November 11, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Agnieszka Flores, James B. Thoden, Hazel M. Holden
  • Patent number: 8853188
    Abstract: Bromoacetoxycalcidiol (B3CD), which is structurally related to calcidiol, exhibits cytotoxic and apoptotic activity toward cancer cells, including highly aggressive neuroblastoma cells. A series of small molecules designed around the structure of B3CD is expected to have growth inhibitory and apoptogenic activities toward a wide range of malignancies. B3CD shows no apparent toxicity in vivo, indicating potential value as a chemotherapeutic agent which will be particularly useful in treating highly aggressive tumors.
    Type: Grant
    Filed: February 22, 2012
    Date of Patent: October 7, 2014
    Assignee: Women and Infants Hospital of RI, Inc.
    Inventor: Narasimha Swamy
  • Publication number: 20140248707
    Abstract: A reagent composition for releasing vitamin D compounds bound to vitamin D-binding protein and an in vitro method for the detection of a vitamin D compound in which the vitamin D compound is released from vitamin D-binding protein by the use of this reagent composition as well as the reagent mixture obtained in this manner. Also disclosed is the use of the reagent compositions to release vitamin D compounds as well as a kit for detecting a vitamin D compound.
    Type: Application
    Filed: May 14, 2014
    Publication date: September 4, 2014
    Applicant: Roche Diagnostics Operations, Inc.
    Inventors: Sascha Antoni, Christian Vogl
  • Publication number: 20140221324
    Abstract: 25-hydroxyvitamin D3 has been found to reduce drip losses in swine carcasses. Feed containing about 25-75 ?g/kg 25-hydroxyvitamin D3 improves the water holding capacity of meats, including pork.
    Type: Application
    Filed: April 4, 2014
    Publication date: August 7, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Arturo PINON-QUINTANA, Carlos SIMOES-NUNES
  • Patent number: 8796246
    Abstract: A main object of the invention is to provide a novel useful vitamin D3 derivative, which has an excellent vitamin D3 activity and, as compared with conventional vitamin D3 derivatives, has a relatively small amount of influence on the systemic calcium metabolism. The invention includes a 9,10-secopregnane derivative of the following general formula [1] and a pharmaceutical composition containing it as active ingredient. In the general formula [1], the following partial structure between the 16-position and the 17-position means a single bond or a double bond: Y is a single bond, an alkylene, an alkenylene or phenylene; R1 and R2 are the same or different, each represents hydrogen, an alkyl or a cycloalkyl; or R1 and R2, taken together with the adjacent carbon atom, form a cycloalkyl; R3 is hydrogen or methyl; Z is hydrogen, hydroxy or —NR11R12.
    Type: Grant
    Filed: June 1, 2007
    Date of Patent: August 5, 2014
    Assignee: Nippon Shinyaku Co., Ltd.
    Inventors: Hiroki Fujieda, Hironori Otsu, Shoji Yasufuku, Masaaki Shirai
  • Publication number: 20140206655
    Abstract: Disclosed are (22E)-2-methylene-22-dehydro-1,24,25-trihydroxy-19-nor-vitamin D3 compounds, their biological activities, and various pharmaceutical uses for these compounds. Particularly disclosed are (22E)-(24R)-2-methylene-22-dehydro-1?,24,25-trihydroxy-19-nor-vitamin D3 and (22E)-(24S)-2-methylene-22-dehydro-1?,24,25-trihydroxy-19-nor-vitamin D3, their biological activities, and various pharmaceutical uses for these compounds.
    Type: Application
    Filed: November 19, 2013
    Publication date: July 24, 2014
    Applicant: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Lori A. Plum, Rafal Barycki, Margaret Clagett-Dame
  • Patent number: 8785422
    Abstract: Disclosed are 19-nor-vitamin D compounds, and specifically seco-A-2,19-dinor-1,25-dihydroxyvitamin D3 as well as pharmaceutical uses therefor. These compounds exhibit relatively high activity in vivo, specifically in intestinal tissues, but relatively low VDR binding activity, cell differentiation activity and gene transcription activity. There is thus potential for these compounds to have strong cell selectivity for use as therapeutic agents against some cancers, such as colon cancer or polyps, as well as hyperplastic intestinal disorders, such as Crohn's disease, ulcerative colitis and celiac disease. These compounds also have relatively high intestinal calcium transport activity evidencing potential in the treatment of bone diseases.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: July 22, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Agnieszka Glebocka
  • Patent number: 8759555
    Abstract: The present invention relates to intermediates useful for the synthesis of calcipotriol or calcipotriol monohydrate, to methods of producing said intermediates, and to methods of stereoselectively reducing said intermediates.
    Type: Grant
    Filed: June 26, 2012
    Date of Patent: June 24, 2014
    Assignee: Leo Pharma A/S
    Inventors: Thomas Peter Sabroe, Martin John Calverley
  • Patent number: 8754067
    Abstract: This invention discloses 22-haloacetoxy-homopregnacalciferol analogs and specifically 22-bromoacetoxy-homopregnacalciferol and pharmaceutical uses therefor. This compound exhibits relatively little calcemic activity and does not promote cellular differentiation off HL-60 leukemia cells, but rather kills the cells. This cell death activity is found in small cell lung carcinoma also, but not in prostate cancer cells. This compound thus causes specific cell death in the absence of changes in calcium levels and without general toxicity in an animal. Therefore it might serve as a useful therapy for treatment of some forms of cancer, such as leukemia and lung cancer.
    Type: Grant
    Filed: November 11, 2011
    Date of Patent: June 17, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Rafal Barycki, Lori A. Plum
  • Publication number: 20140154700
    Abstract: Compounds include carbamate derivatives of vitamin D including vitamin D3 and vitamin D2. The compounds are useful in methods and kits for determining the presence and/or amount of vitamin D including vitamin D analogs and metabolites thereof in a sample suspected of containing the same.
    Type: Application
    Filed: November 30, 2012
    Publication date: June 5, 2014
    Inventors: Zhu Teng, Roland Janzen, Martin A. Drinan
  • Patent number: 8729054
    Abstract: This invention discloses 3-desoxy-2-methylene-vitamin D analogs, and specifically (20S)-3-desoxy-1?,25-dihydroxy-2-methylene-vitamin D3 and (20R)-3-desoxy-1?,25-dihydroxy-2-methylene-vitamin D3 as well as pharmaceutical uses therefor. These compounds exhibit relatively high binding activity and pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to monocytes thus evidencing use as anti-cancer agents especially for the treatment or prevention of osteosarcoma, leukemia, colon cancer, breast cancer, skin cancer or prostate cancer. These compounds also exhibit relatively high calcemic activity evidencing use in the treatment of bone diseases.
    Type: Grant
    Filed: October 3, 2012
    Date of Patent: May 20, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Lori A. Plum, Rafal R. Sicinski, Izabela Sibilska
  • Publication number: 20140113886
    Abstract: A stabilized 1,25-dihydroxyvitamin D2 composition which is particularly well suited for pharmaceutical formulations, pharmaceutical formulations of the 1,25-dihydroxyvitamin D2 composition, and a method of making the purified composition by purifying a crude 1,25-dihydroxyvitamin D2 from acetone/water, are disclosed.
    Type: Application
    Filed: January 2, 2014
    Publication date: April 24, 2014
    Applicant: CYTOCHROMA INC.
    Inventor: Uttam Saha
  • Publication number: 20140100419
    Abstract: The present invention relates to methods for improving the ability of spermatozoa to fertilize an egg in vitro and/or vivo, said method comprising providing a medium comprising active vitamin D (calcitriol) or analogs thereof, providing a sample of spermatozoa, and incubating said sample of spermatozoa with said medium. In addition, the invention relates to compositions comprising active vitamin D or analogs thereof for use in the treatment of infertility in a male or female subject.
    Type: Application
    Filed: January 31, 2012
    Publication date: April 10, 2014
    Applicant: RIGSHOSPITALET COPENHAGEN UNIVERSITY HOSPITAL
    Inventor: Martin Blomberg Jensen
  • Patent number: 8664206
    Abstract: Compounds of formula I are provided where X1, X2, and X3 are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.
    Type: Grant
    Filed: January 6, 2012
    Date of Patent: March 4, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Agnieszka Flores, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame, James B. Thoden, Hazel M. Holden
  • Publication number: 20140051875
    Abstract: The present invention relates to maxacalcitol hydrate, a new crystalline form of maxacalcitol, with superior technical properties e.g. in the manufacture of crystal suspension formulations, and with superior stability properties.
    Type: Application
    Filed: August 16, 2013
    Publication date: February 20, 2014
    Applicant: FORMOSA LABORATORIES INC.
    Inventors: CHING-PENG WEI, PEI-CHEN HUANG
  • Publication number: 20140038925
    Abstract: The present invention provides a compound which functions as a selective vitamin D receptor modulator and has action-selectivity or tissue-selectivity such that it does not induce hypercalcemia but causes other effects. There is provided a compound represented by formula (I), a solvate thereof or a prodrug thereof. wherein m and n each independently represent 1 or 0; R represents a hydrogen atom or an alkyl group; Y represents an ethane-1,1-diyl group or an ethyne-1,2-diyl group; and Z1 represents a hydrogen atom and Z2 represents a hydroxyalkoxy group, or Z1 and Z2 jointly form a methylene group.
    Type: Application
    Filed: March 1, 2012
    Publication date: February 6, 2014
    Inventors: Makoto Makishima, Sachiko Yamada, Antonio Mourino, Hiroaki Tokiwa, Takeru Kudo, Yusuke Watarai, Kazuki Maekawa
  • Patent number: 8642579
    Abstract: This invention discloses 1-desoxy-2-methylene-19-nor-vitamin D analogs, and specifically (20S)-25-hydroxy-1-desoxy-2-methylene-19-nor-vitamin D3 and pharmaceutical uses therefor. This compound exhibits relatively high binding activity and pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent especially for the treatment or prevention of leukemia, colon cancer, breast cancer, skin cancer or prostate cancer.
    Type: Grant
    Filed: September 30, 2010
    Date of Patent: February 4, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Katarzyna M. Barycka, Izabela Sibilska, Lori A. Plum, Margaret Clagett-Dame, Rafal Barycki, Rafal R. Sicinski, Katarzyna Plonska-Ocypa
  • Publication number: 20140018332
    Abstract: Oral and topical pharmaceutical compositions, kits and methods of treatment thereof for treating various skin disorder including acne, psoriasis, ichthyosis, photoaging, photodamaged skin, and, skin cancer.
    Type: Application
    Filed: September 23, 2013
    Publication date: January 16, 2014
    Applicant: Wisconsin Alumni Research Foundation
    Inventors: Margaret Clagett-Dame, Hector F. DeLuca, Nircaq J. Nieves, Lori A. Plum, Mary E. Kaiser
  • Publication number: 20140011778
    Abstract: Compounds of Formula I are provided where R1 and R2 are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.
    Type: Application
    Filed: September 12, 2013
    Publication date: January 9, 2014
    Applicant: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLUCA, Margaret Clagett-Dame, Lori A. Plum, Agnieszka Glebocka, Rafal Sicinski
  • Patent number: 8614202
    Abstract: This invention discloses 2?-methyl and 2?-methyl analogs of 19,26,27-trinor-(20S)-1?-hydroxyvitamin D3 and pharmaceutical uses therefor. These compounds exhibit pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. These compounds also have little, if any, calcemic activity and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. These compounds may also be used for the treatment or prevention of obesity.
    Type: Grant
    Filed: September 18, 2012
    Date of Patent: December 24, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Lori A. Plum, Pawel K. Grzywacz, Margaret Clagett-Dame
  • Patent number: 8609643
    Abstract: This invention discloses 2-methylene-(20S,25R)-19,26-dinor-vitamin D analogs, and specifically 2-methylene-(20S,25R)-19,26-dinor-1?,25-dihydroxyvitamin D3, and pharmaceutical uses therefor. This compound exhibits pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also has little, if any, calcemic activity and therefore may be used to treat autoimmune disorders or inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.
    Type: Grant
    Filed: December 24, 2008
    Date of Patent: December 17, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Grazia Chiellini, Pawel Grzywacz
  • Patent number: 8604008
    Abstract: Compounds of formula I are provided where X1 and X2 are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.
    Type: Grant
    Filed: November 18, 2005
    Date of Patent: December 10, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame
  • Patent number: 8604009
    Abstract: Compounds of formula I are provided where X1, X2 and X3 are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.
    Type: Grant
    Filed: March 22, 2011
    Date of Patent: December 10, 2013
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Agnieszka Flores, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
  • Publication number: 20130324752
    Abstract: Disclosed are methods of purifying the compound (20R,22R)-2-methylene-19-nor-22-methyl-1?,25-dihydroxyvitamin D3 to obtain the compound in crystalline form. The methods typically include the steps of dissolving a product containing the compound in a solvent comprising hexane and 2-propanol, cooling the solvent and dissolved product below ambient temperature for a sufficient amount of time to form a precipitate of crystals, and recovering the crystals. Certain diol precursors formed during the synthesis of the compound and its diasteromers also may be obtained in crystalline form using ethyl acetate as a solvent.
    Type: Application
    Filed: March 14, 2013
    Publication date: December 5, 2013
    Inventors: Hector F. DeLuca, Pawel Grzywacz, Lori A. Plum, Agnieszka Flores, James B. Thoden, Hazel M. Holden
  • Publication number: 20130324749
    Abstract: Disclosed are methods of purifying (20R) and (20S) analogs of 2-methylene-19-nor-22-dimethyl-1?,25-dihydroxyvitamin D3 to obtain the (20R) and (20S) analogs in crystalline form. The method includes the steps of preparing a solvent of either diethyl ether or a mixture of 2-propanol and hexane, dissolving a product containing the (20R) and (20S) analog to be purified in the solvent, cooling the solvent and dissolved product below ambient temperature for a sufficient amount of time to form a precipitate of crystals, and recovering the crystals.
    Type: Application
    Filed: March 14, 2013
    Publication date: December 5, 2013
    Applicant: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Agnieszka Flores, James B. Thoden, Hazel M. Holden