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)
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Publication number: 20120184514Abstract: An air-stable, high-melt 1a-hydroxy-vitamin D3 compound, methods for preparing an animal feed composition, methods of preparing 1?-hydroxy-vitamin D3, methods of enhancing phytate phosphorus and calcium utilization, and an animal feed regime are provided.Type: ApplicationFiled: June 29, 2010Publication date: July 19, 2012Applicant: Vitamin Derivatives Inc.Inventors: Hardy M. Edwards, George Majetich, Richard Hill, Dezhi Sha, George Yiannikouros
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Patent number: 8222235Abstract: 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: GrantFiled: November 18, 2005Date of Patent: July 17, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 8222236Abstract: This invention discloses 2-methylene-(20E)-20(22)-dehydro-19-nor-vitamin D analogs, and specifically 2-methylene-(20E)-20(22)-dehydro-19-nor-1?,25-dihydroxyvitamin D3, and pharmaceutical uses therefore. 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 lower activity in vivo on bone calcium mobilization and similar in vivo intestinal calcium transport activity compared to the native hormone 1?,25-dihydroxyvitamin D3, 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: GrantFiled: July 10, 2008Date of Patent: July 17, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Bulli Padmaja Tadi, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 8217023Abstract: 19-nor-vitamin D analogs having an additional cyclopentene ring connecting carbon 1 and carbon 2, or connecting carbon 3 and carbon-2 of the A-ring of the analog, and pharmaceutical uses therefore, are described. These compounds exhibit selective in vitro activities, making them therapeutic agents for the treatment or prophylaxis of some types of cancers, particularly leukemia, colon cancer, breast cancer, skin cancer or prostate cancer.Type: GrantFiled: September 30, 2010Date of Patent: July 10, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Agnieszka Glebocka, Lori A. Plum, Margaret Clagett-Dame, Rafal R. Sicinski
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Patent number: 8212059Abstract: There are provided a novel process for producing [{(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl}oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide, which process is characterized by irradiating a compound represented by the formula: with UV to ring-open the compound, and then isomerizing the resulting compound; an intermediate useful for carrying out the process; and a process for producing the intermediate.Type: GrantFiled: November 30, 2006Date of Patent: July 3, 2012Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Akira Kawase, Yasuharu Kato, Kazutomo Kinoshita, Yasushi Kitoh, Takuma Ikeda, Tsuyoshi Haneishi, Noriaki Maruyama, Mio Kobayashi
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Publication number: 20120165300Abstract: 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: ApplicationFiled: January 6, 2012Publication date: June 28, 2012Inventors: Hector F. DeLUCA, Agnieszka FLORES, Pawel GRZYWACZ, Lori A. PLUM, Margaret CLAGETT-DAME, James B. THODEN, Hazel M. HOLDEN
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Publication number: 20120157418Abstract: This invention discloses 2-methylene-19-nor-vitamin D analogs, and specifically (20S)-25-hydroxy-2-methylene-19-nor-vitamin D3 and (20R)-25-hydroxy-2-methylene-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 the monocyte thus evidencing use as an anti-cancer agent especially for the treatment or prevention of osteosarcoma, leukemia, colon cancer, breast cancer, skin cancer or prostate cancer. Although these compounds have relatively low calcemic activities they may also be useful in the treatment of bone diseases due to their ability to act as prodrugs in vivo.Type: ApplicationFiled: October 21, 2011Publication date: June 21, 2012Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: Hector F. DeLuca, Izabela Sibilska, Lori A. Plum, Margaret Clagett-Dame, Rafal R. Sicinski, Katarzyna M. Barycka, Katarzyna Plonska-Ocypa, Rafal Barycki
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Publication number: 20120149669Abstract: 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: ApplicationFiled: November 11, 2011Publication date: June 14, 2012Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: Hector F. DeLuca, Rafal Barycki, Lori A. Plum
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Patent number: 8198263Abstract: The invention relates to vitamin D derivatives and their uses, particularly in the pharmaceutical industry. The invention discloses compounds having different interesting biological properties, including vitamin D nuclear receptor (VDR) agonist activity, as well as therapeutics methods by administering said compounds, in particular for treating cancer, psoriasis, autoimmune diseases, osteodistrophy and osteoporosis. It further relates to pharmaceutical compositions comprising said compounds and methods for preparing the same.Type: GrantFiled: September 26, 2006Date of Patent: June 12, 2012Assignees: Centre National de la Recherche Scientifique, Universite De Strasbourg, Universidad De Santiago De Compostela, Institut National de la Sante Et de la Recherche MedicaleInventors: Dino Moras, Antonio Mourino-Mosquera, Luis Cezar Rodrigues, Natacha Rochel, Jean-Marie Wurtz
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Patent number: 8193170Abstract: This invention discloses 2-methylene-19,26-dinor-(20R,22E,25R)-vitamin D analogs, and specifically 2-methylene-19,26-dinor-(20R,22E,25R)-1?,25-dihydroxyvitamin D3, and pharmaceutical uses therefor. This compound exhibits 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 very low activity in vivo on bone calcium mobilization and relatively high intestinal calcium transport activity compared to the native hormone 1?,25-dihydroxyvitamin D3, 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: GrantFiled: July 10, 2008Date of Patent: June 5, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Grazia Chiellini, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 8193169Abstract: This invention discloses (20R)-2?-methyl-19,26,27-trinor-vitamin D analogs, and specifically (20R)-2?-methyl-19,26,27-trinor-1?,25-dihydroxyvitamin D3, and pharmaceutical uses therefor. This compound exhibits 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 very low activity in vivo on bone calcium mobilization and intestinal calcium transport activity compared to the native hormone 1?,25-dihydroxyvitamin D3, 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: GrantFiled: July 10, 2008Date of Patent: June 5, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 8193171Abstract: 13,13-Dimethyl-des-C,D analogs of 1?,25-dihydroxy-19-nor-vitamin D3 compounds and topical composition dosage forms thereof, and methods of treating skin conditions thereof. Exemplary active pharmaceutical ingredients include (1R,3R)-5-[(E)-(S)-11?-hydroxy-5?,5?,7?,11?-tetramethyl-dodec-2?-enylidene]-2-methylene-cyclohexane-1,3-diol, (1R,3R)-5-[(Z)-(S)-11?-hydroxy-5?,5?,7?,11?-tetramethyl-dodec-2?-enylidene]-2-methylene-cyclohexane-1,3-diol, (1R,3R)-5-[(E)-(R)-11?-hydroxy-5?,5?,7?,11?-tetramethyl-dodec-2?-enylidene]-2-methylene-cyclohexane-1,3-diol, and (1R,3R)-5-[(Z)-(R)-11?-hydroxy-5?,5?,7?,11?-tetramethyl-dodec-2?-enylidene]-2-methylene-cyclohexane-1,3-diol.Type: GrantFiled: January 22, 2009Date of Patent: June 5, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Rafal R. Sicinski, Katarzyna Plonska-Ocypa, Nirca J. Nieves, Pawel Grzywacz
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Patent number: 8188064Abstract: Methods for treating and preventing obesity, inhibiting adipocyte differentiation, inhibiting increased SCD-1 gene transcription, and/or reducing body fat in a subject include administering at least one analog of 1?,25-dihydroxyvitamin D3 or 1?,25-dihydroxyvitamin D2 or a pharmaceutical composition that includes such an analog to a subject in need thereof. The analog may be a 19-nor vitamin D analog such as a compound of formula IA, a compound of formula IB, or a mixture thereof where the variables R1, R2, and R3 have the values described herein.Type: GrantFiled: November 24, 2004Date of Patent: May 29, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Margaret Clagett-Dame, Hector F. DeLuca, Jamie M. Ahrens, James M. Ntambi, Brian Thomson
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Patent number: 8178517Abstract: This invention discloses 6-methylvitamin D3 analogs, and specifically 1?,25-dihydroxy-6-methylvitamin D3, and pharmaceutical uses therefor. This compound exhibits vitamin D receptor binding activity and transcription activity as well as 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. This compound also exhibits low in vivo calcemic activity, but because it binds the receptor with the same affinity as the native hormone calcitriol, it may act as an antagonist to inhibit development of hypercalcemia.Type: GrantFiled: September 30, 2010Date of Patent: May 15, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Katarzyna Sokolowska, Lori A. Plum, Margaret Clagett-Dame, Rafal R. Sicinski, Antonio Mouriño
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Publication number: 20120115824Abstract: Disclosed is a compound of Formula (I) in which R1, R2, R3, R4, R5, R6, X, and a are defined herein, or a pharmaceutically acceptable salt thereof. Also disclosed are a pharmaceutical composition comprising a compound or salt thereof of Formula (I) and a method of treating a disease which benefits from the modulation of the vitamin D receptor, such as a bone disorder, cardiovascular disease, a cardiovascular complication associated with renal disease, endothelial dysfunction, hyperparathyroidism, hypocalcemia, an immune disorder, left ventricular hypertrophy, a proliferative disease, proteinuria, renal disease, and thrombosis.Type: ApplicationFiled: April 12, 2010Publication date: May 10, 2012Applicant: VIDASYM, LLCInventor: Megumi Kawai
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Patent number: 8173824Abstract: There are provided a novel process for producing [{(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl}oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide, which process is shown in the following reaction scheme: an intermediate useful for carrying out the process, and a process for producing the intermediate.Type: GrantFiled: December 4, 2006Date of Patent: May 8, 2012Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Kunio Ogasawara, Takashi Emura, Akira Kawase, Koji Takano, Keisuke Yamamoto, Yoshiaki Kato
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Publication number: 20120108554Abstract: The present invention relates to a process for purifying Doxercalciferol, a synthetic vitamin D analog, also known as 1?-hydroxy vitamin D2, to the purity greater than 99.5% by crystallization from a mixed solvent of methanol and acetonitrile. Each of the individual impurities can be controlled no more than 0.1% which meets the individual unknown impurities specification requirement of International Conference on Harmonisation (ICH) guideline. The crystallization yield is more than 75% which is suitable for employed as a commercial process.Type: ApplicationFiled: October 28, 2010Publication date: May 3, 2012Applicant: FORMOSA LABORATORIES, INC.Inventors: Bang-I Liou, Ching-Peng Wei
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Publication number: 20120107255Abstract: A method of reducing photodegradation of cholecalciferol when exposed to UV radiation in a composition containing cholecalciferol comprising combining with cholecalciferol a compound of formula (I) in an amount effective to quench excited state energy from cholecalciferol and transfer the excited state energy from cholecalciferol to the compound of formula (I), wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, and the non-alkoxy R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical, thereby photostabilizing the cholecalciferol compound.Type: ApplicationFiled: January 5, 2012Publication date: May 3, 2012Applicant: HALLSTAR INNOVATIONS CORP.Inventors: Craig A. Bonda, Jean Zhang
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Publication number: 20120083614Abstract: A method of purifying (20R,25S)-2-methylene-19,26-dinor-1?,25-dihydroxyvitamin D3 to obtain (20R,25S)-2-methylene-19,26-dinor-1?,25-dihydroxyvitamin D3 in crystalline form. The method includes the steps of preparing a solvent of methanol and water, dissolving a product containing (20R,25S)-2-methylene-19,26-dinor-1?,25-dihydroxyvitamin D3 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 (20R,25S)-2-methylene-19,26-dinor-1?,25-dihydroxyvitamin D3 crystals, and recovering the (20R,25S)-2-methylene-19,26-dinor-1?,25-dihydroxyvitamin D3 crystals.Type: ApplicationFiled: September 28, 2011Publication date: April 5, 2012Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: Hector F. DeLuca, Pawel Grzywacz, James B. Thoden, Hazel Holden
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Patent number: 8143238Abstract: Methods of increasing the thickness of the epidermal layer in the skin of a human comprising topically administering a therapeutically effective dose of an active pharmaceutical ingredient comprising a vitamin D analog including 2-methylene-19-nor-20(S)-1?-hydroxy-bishomopregnacalciferol, 19-nor-26,27-dimethylene-20(S)-2-methylene-1?,25-dihydroxyvitamin D3, 2-methylene-19-nor-(24R)-1?,25-dihydroxyvitamin D2, 2-methylene-1?,25-dihydroxy-(17E)-17(20)-dehydro-19-nor-vitamin D3, 2-methylene-(20R,25S)-19,26-dinor-1?,25-dihydroxyvitamin D3, 2-methylene-18,19-dinor-(20S)-1?,25-dihydroxyvitamin D3, 2-methylene-19-nor-1?-hydroxy-pregnacalciferol, 1?-hydroxy-2-methylene-19-nor-homopregnacalciferol, (20R)-1?-hydroxy-2-methylene-19-nor-bishomopregnacalciferol, 2-methylene-(20S)-19-nor-1?-hydroxy-trishomopregnacalciferol, 2-methylene-(20R)-23,23-difluoro-1?-hydroxy-19-nor-bishomopregnacalciferol, 2-methylene-(20S)-23,23-difluoro-1?-hydroxy-19-nor-bishomopregnacalciferol, 2-(3?hydroxypropyl-1?,2?-idene)-19,23,24-trinor-(20Type: GrantFiled: March 6, 2009Date of Patent: March 27, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Nirca J. Nieves, Jamie Ahrens
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Publication number: 20120058977Abstract: A pharmaceutical composition for the treatment of a disease caused by a bacterium that belongs to the group of nocardioform actinomycetes, said composition comprising an effective amount of a compound selected from compound I, (+)-compound II, (?)-compound II, compound III, or mixtures thereof.Type: ApplicationFiled: February 23, 2010Publication date: March 8, 2012Applicant: Rijksuniversiteit GroningenInventors: Robert Van Der Geize, Lubbert Dijkhuizen, Martin Ostendorf, Peter Van Der Meijden
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Patent number: 8114859Abstract: This invention discloses 2-methylene-(20S,25S)-19,27-dinor-(22E)-vitamin D analogs, and specifically 2-methylene-(20S,25S)-19,27-dinor-(22E)-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: GrantFiled: September 25, 2007Date of Patent: February 14, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Grazia Chiellini, Pawel Grzywacz
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Patent number: 8106035Abstract: The present invention provides novel D-ring and side-chain analogs of 1?,25-dihydroxyvitamin D3, compositions comprising these compounds and methods of using these compounds as selective inhibitors of CYP24. In particular, the compounds of the invention are useful for treating diseases which benefit from a modulation of the levels of 1?,25-dihydroxyvitamin D3, for example, cell-proliferative disorders.Type: GrantFiled: December 18, 2003Date of Patent: January 31, 2012Assignee: Cytochroma Inc.Inventors: Gary H. Posner, Jae Kyoo Lee, Qiang Wang, Kenneth R. Crawford, Hong Woon Yang, Steven M. Silverman, Byung-Chul Suh, Jay A. White, Glenville Jones, Uttam Saha, Heung Bae Jeon
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Publication number: 20120015913Abstract: The present invention provides new formulations of 14-epi-analogues of vitamin D, such as inecalcitol, providing improved absorption profile.Type: ApplicationFiled: July 15, 2010Publication date: January 19, 2012Inventor: Rémi Delansorne
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Patent number: 8093232Abstract: This invention discloses 2?-methyl-19-nor-(20S)-vitamin D analogs, and specifically 2?-methyl-19-nor-(20S)-1?-hydroxy-bishomopregnacalciferol 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: GrantFiled: July 9, 2007Date of Patent: January 10, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Rafal R. Sicinski, Lori A. Plum, Margaret Clagett-Dame
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Publication number: 20110319644Abstract: A cyclovitamin D derivative produced from 25-hydroxyvitamin D is reacted with osmium tetraoxide or a permanganic acid salt to produce a 10,19-diolcyclovitamin D derivative. The 10,19-diolcyclovitamin D derivative is reacted with a perhalogenic acid salt or lead tetraacetate to produce a 10-oxocyclovitamin D derivative. A 1-hydroxycyclovitamin D derivative is produced from the 10-oxocyclovitamin D derivative via a cyclovitamin D derivative and a 1,10-olefincyclovitamin D derivative. The 1-hydrocyclovitamin D derivative is subjected to solvolysis, thereby producing a 1-hydroxy-19-norviatmin D derivative. Thus provided are a novel process for production of 1-hydroxy-19-norcyclovitamin D derivative that is utilizable as an intermediate in the synthesis of 1-hydroxy-19-norvitamin D derivative which is useful as a pharmaceutical agent; and an intermediate for the production.Type: ApplicationFiled: November 1, 2007Publication date: December 29, 2011Inventors: Asako Toyoda, Hazuki Nagai, Kaname Konuki, Toshio Tsuchida
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Patent number: 8058265Abstract: Disclosed are 1?-hydroxy-2-(3?-hydroxypropylidene)-19-nor-vitamin D compounds, pharmaceutical compositions, and methods of making and treatment thereof. The compounds are generally directed to biologically active 2-alkylidene-19-nor-vitamin D compounds and analogs thereof characterized by the presence of a 3?-hydroxypropylidene moiety at C-2 and the presence of an abbreviated alkyl side-chain free of any hydroxyl moiety.Type: GrantFiled: April 5, 2007Date of Patent: November 15, 2011Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. Deluca, Rafal R. Sicinski, Lori A. Plum, Margaret Clagett-Dame, Agnieszka Glebocka
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Publication number: 20110274743Abstract: The use of vitamin D3 for the manufacture of a medicament for the transdermal treatment of neurogenic inflammation and neuropathic pain (including peripheral neuropathic pain); also a method for the relief of neurogenic inflammation and neuropathic pain using this medicament.Type: ApplicationFiled: August 13, 2009Publication date: November 10, 2011Applicant: PHARMACEUTICAL COMPOUNDING NZ LIMITEDInventor: Jan Anne Lyftogt
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Patent number: 8030295Abstract: Compounds of formula 1 are provided where X1, X2, and X3 are independently selected from H or hydroxy protecting groups, and R1 and R2 have the definitions provided herein. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.Type: GrantFiled: May 31, 2007Date of Patent: October 4, 2011Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
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Publication number: 20110237557Abstract: 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: ApplicationFiled: March 22, 2011Publication date: September 29, 2011Inventors: Hector F. DeLuca, Agnieszka Flores, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame, James B. Thoden, Hazel M. Holden
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Publication number: 20110237556Abstract: 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: ApplicationFiled: March 22, 2011Publication date: September 29, 2011Inventors: Hector F. DeLuca, Agnieszka Flores, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 8026379Abstract: The present invention relates to a compound and a novel process for the preparation of Paricalcitol intermediates.Type: GrantFiled: June 20, 2008Date of Patent: September 27, 2011Assignee: Formosa Laboratories, Inc.Inventors: Chze-Siong Ng, Ching-Peng Wei
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Patent number: 8013176Abstract: Paricalcitol, a synthetic vitamin D analog, is purified to a purity greater than 99.7% by crystallization from solution in isopropyl acetate solvent, followed by filtration and vacuum drying. Isopropyl acetate appears to be unique among commonly available and pharmaceutically acceptable solvents in its ability to precipitate paricalcitol in this high purity, essentially free of isomers thereof. In addition, paricalcitol of purity of at least 99.9% has been shown to have exceptional storage stability.Type: GrantFiled: August 19, 2009Date of Patent: September 6, 2011Assignee: Alphora Research Inc.Inventors: Fabio Eduardo Silva e Souza, Ming Pan, Kathleen Da Silva Turcot
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Publication number: 20110213168Abstract: The invention relates to deuterated vitamin D compounds and the process for preparing and synthesizing a class of vitamin D compounds which can be isotopically substituted. These compounds can be used as internal standards in methods for the quantification of vitamin D, its metabolites and analogues by mass spectrometry. These compounds are described by means of general formula I.Type: ApplicationFiled: June 25, 2009Publication date: September 1, 2011Applicant: UNIVERSIDADE DE SANTIAGO DE COMPOSTELAInventors: Miguel A. Maestro Saavedra, Antonio Mourino Mosquera, Daniel Nicoletti, Rita Sigueiro Ponte
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Publication number: 20110207952Abstract: A process for producing vegan vitamin D3 from an algal waste processing stream by saponifying the waste stream to separate out and removing unsaponifiable cholesterol and converting it to vitamin D3 by ultraviolet irradiation, while precipitating out the saponified fatty acids, triglycerides and polysaccharides.Type: ApplicationFiled: February 15, 2011Publication date: August 25, 2011Inventor: RAFAEL AVILA
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Publication number: 20110184199Abstract: The present invention is directed to novel processes for the preparation of paricalcitol to novel intermediates used in these processes, and to processes for preparation of the novel intermediates.Type: ApplicationFiled: July 22, 2009Publication date: July 28, 2011Inventors: Thomas Bader, Alfred Stutz, Hans-Ulrich Bichsel, Changchun Fu
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Publication number: 20110184198Abstract: The present invention concerns a process of isomerizing trans fused bicyclic derivatives into cis fused bicyclic derivatives and the preparation of vitamin D or analogs thereof comprising said isomerisation step.Type: ApplicationFiled: January 24, 2011Publication date: July 28, 2011Inventors: Jean-Luc MOUTOU, Florent Mouton, Gilles Pellegrino, Jean Lafay
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Patent number: 7985744Abstract: The object of the present invention is to provide vitamin D derivatives that have excellent physiological activities as medicines, particularly as therapeutic agents for skin diseases such as psoriasis, and that have a reduced hypercalcemic effect. The present invention provides a vitamin D derivative of Formula (1): wherein X represents an oxygen atom or a sulfur atom; m represents a number of 1 to 3; R1 and R2 each represent a hydrogen atom or an alkyl group; R4 and R5 each represent a hydrogen atom or a hydroxyl group, etc.; R3 represents —YR8, etc.; R6 represents a hydrogen atom, etc.; R7 represents a hydrogen atom, etc.Type: GrantFiled: June 14, 2001Date of Patent: July 26, 2011Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Kazumi Morikawa, Masayuki Ohmori, Kazuki Shimizu, Akira Kawase, Takashi Emura
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Publication number: 20110166111Abstract: 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: ApplicationFiled: June 9, 2009Publication date: July 7, 2011Inventors: Arturo Pinon-Quintana, Carlos Simoes-Nunes
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Publication number: 20110137058Abstract: This invention relates to a method for purifying Paricalcitol by reverse phase chromatography. This invention also relates to a purified Paricalcitol prepared by said method. This invention further relates to a method for purifying Paricalcitol by crystallization.Type: ApplicationFiled: February 15, 2011Publication date: June 9, 2011Applicant: FORMOSA LABORATORIES, INC.Inventors: CHZE-SIONG NG, CHING-PENG WEI
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Publication number: 20110118218Abstract: We disclose the use of optionally in combination with vitamin D3 (cholecalciferol), 25-hydroxyvitamin D3 (cal-cifediol), to treat hypertension. Forms and dosages of a pharmaceutical composition, as well as processes for manufacturing medicaments, are also disclosed.Type: ApplicationFiled: February 12, 2009Publication date: May 19, 2011Inventors: Neil Robert Buck, Wouter Claerhout, Bruno H. Leuenberger, Elisabeth Stoecklin, Kai Urban, Swen Wolfram
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Patent number: 7943601Abstract: This invention discloses 2-methylene-20-methyl-19,24,25,26,27-pentanor-vitamin D analogs, and specifically 2-methylene-20-methyl-1?-hydroxy-19,24,25,26,27-pentanor-vitamin D3, and pharmaceutical uses therefore. This compound exhibits 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: GrantFiled: December 24, 2008Date of Patent: May 17, 2011Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Agnieszka Glebocka, Rafal R. Sicinski
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Publication number: 20110073810Abstract: The present invention is directed to a method for the synthesis of deuterium labeled Vitamin D and related compounds with a high level of deuterium incorporation, which are particularly suitable for use as standards for mass spectroscopy.Type: ApplicationFiled: July 16, 2010Publication date: March 31, 2011Inventors: Scott White Landvatter, Edith Foris Landvatter, Richard Steven Tyburski
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Patent number: 7915242Abstract: Various compounds such as those having the formula I and XIV where the variables have the values described herein antagonize the vitamin D receptor and are useful in treating conditions such as asthma and in preparing medicaments for use in antagonizing the vitamin D receptor or treating conditions such as asthmaType: GrantFiled: February 16, 2005Date of Patent: March 29, 2011Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Rafal Barycki, Moisés A. Rivera-Bermúdez, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7915241Abstract: Disclosed is a process for the preparation of 24-alkyl analogs of cholecalcyferol of Formula 1 having a (5E) or (5Z) configuration, wherein X represents a hydrogen atom, a hydroxy group or an OR1 group, where R1, R2 and R3 may be the same or different and represent groups suitable for hydroxyl protection, and R4 is a C1-6 alkyl chain or a C1-6 cykloalkyl group, optionally substituted with C1-3 alkyl groups, especially for calcipotriol. The invention also provides new intermediates and non-racemic compounds being valuable synthones for the synthesis of pharmacologically active substances.Type: GrantFiled: October 8, 2004Date of Patent: March 29, 2011Assignee: Instytut FarmaceutycznyInventors: Andrzej Kutner, Jacek Martynow, Michal Chodynski, Wieslaw Szelejewski, Hanna Fitek, Malgorzata Krupa
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Patent number: 7906495Abstract: New vitamin D derivative compounds containing a monohalovinyl moiety at position C-20 are described. A process for obtaining the new compounds, consisting of reacting an aldehyde precursor with a haloform in the presence of Cr2+ salts, is also described.Type: GrantFiled: November 17, 2004Date of Patent: March 15, 2011Assignee: Laboratorios Vinas S.A.Inventors: Antonio Buxadé Viñas, Antonio Conchillo Teruel, Carlos Mola Soler
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Publication number: 20110059926Abstract: The present invention relates to compounds and methods for reducing intraocular pressure and treating ocular hypertension in a subject.Type: ApplicationFiled: March 10, 2009Publication date: March 10, 2011Inventors: Hector F. DeLuca, Galina D. Kutuzova, Paul L. Kaufman, B'Ann True Gabelt
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Patent number: 7893043Abstract: This invention discloses 2-methylene-(17Z)-17(20)-dehydro-19,21-dinor-vitamin D analogs, and specifically 2-methylene-(17Z)-17(20)-dehydro-19,21-dinor-1?, 25-dihydroxyvitamin 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 has significant calcemic activity in vivo having about the same bone calcium mobilization activity and intestinal calcium transport activity as the native hormone 1?,25-dihydroxyvitamin D3, 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: GrantFiled: July 10, 2008Date of Patent: February 22, 2011Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Bulli Padmaja Tadi, Lori A. Plum, Margaret Ciagett-Dame
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Publication number: 20110039811Abstract: We disclose treating hyperglycemia in a human with 25-hydroxyvitamin D3 (calcifediol). Blood glucose is reduced to a level which is closer to normal than baseline. Vitamin D3 (cholecalciferol) may optionally be used together with 25-hydroxy vitamin D3. Forms and dosages of a pharmaceutical composition, as well as processes for manufacturing medicaments, are also disclosed.Type: ApplicationFiled: February 12, 2009Publication date: February 17, 2011Inventors: Neil Robert Buck, Wouter Claerhout, Bruno H. Leuenberger, Elizabeth Stoecklin, Kai Urban, Swen Wolfram
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Publication number: 20110039810Abstract: We disclose the use of 25-OH D3 (calcifediol) to increase muscle strength, muscle function, or both. Vitamin D3 (cholecalciferol) may optionally be used together with 25-OH D3. Forms and dosages of a pharmaceutical composition, as well as processes for manufacturing medicaments, are also disclosed.Type: ApplicationFiled: February 12, 2009Publication date: February 17, 2011Inventors: Neil Robert Buck, Wouter Claerhout, Bruno H. Leuenberger, Elizabeth Stoecklin, Kai Urban, Swen Wolfram