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: 20090177002Abstract: Indene derivatives that are utilizable as intermediates in the synthesis of the vitamin D2 derivative paricalcitol, which is useful as pharmaceutical are efficiently prepared by subjecting a vitamin D2 derivative such as 25-hydroxyvitamin D2 to a two-steps oxidation reaction using an oxidizing agent such as potassium permanganates and sodium periodate in a suitable solvent such as methanol and ethanol.Type: ApplicationFiled: March 14, 2007Publication date: July 9, 2009Inventors: Asako Toyoda, Hazuki Nagai
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Publication number: 20090170819Abstract: This invention discloses (20R)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-vitamin D analogs, and specifically (20R)-23,23-difluoro-1 ?-hydroxy-2-methylene-19-nor-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: ApplicationFiled: December 24, 2008Publication date: July 2, 2009Inventors: Hector F. DeLuca, Lori A. Plum, Rafal Barycki, Margaret Clagett-Dame
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Publication number: 20090170820Abstract: 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: ApplicationFiled: December 24, 2008Publication date: July 2, 2009Inventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Grazia Chiellini, Pawel Grzywacz
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Publication number: 20090170821Abstract: This invention discloses 2-methylene-(20S,25S)-19,26-dinor-vitamin D analogs, and specifically 2-methylene-(20S,25S)-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: ApplicationFiled: December 24, 2008Publication date: July 2, 2009Inventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Grazia Chiellini, Pawel Grzywacz
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Publication number: 20090170818Abstract: This invention discloses (20S)-23,23-difluoro-2-methylene-19-nor-bishomopregnacalciferol-vitamin D analogs, and specifically (20S)-23,23-difluoro-1?-hydroxy-2-methylene-19-nor-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: ApplicationFiled: December 24, 2008Publication date: July 2, 2009Inventors: Hector F. DeLuca, Lori A. Plum, Rafal Barycki, Margaret Clagett-Dame
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Publication number: 20090170822Abstract: 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: ApplicationFiled: December 24, 2008Publication date: July 2, 2009Inventors: Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Agnieszka Glebocka, Rafal R. Sicinski
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Patent number: 7541348Abstract: 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: June 2, 2009Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7541349Abstract: Compounds of formula 1A and 1B 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 disorders.Type: GrantFiled: June 22, 2007Date of Patent: June 2, 2009Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame, Grazia Chiellini, Pawel Grzywacz
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Publication number: 20090137828Abstract: The invention provides a method of producing 20-methyl vitamin D3 compounds of formula (I). The method includes allylic and olefin oxidation, de-carbonylation, carbonyl reduction, fluoride substitution, epoxide deoxygenation, and Wittig-type couplings.Type: ApplicationFiled: August 18, 2006Publication date: May 28, 2009Applicant: BIOXELL S.P.A.Inventors: Milan R. Uskokovic, Stanislaw Marczak, Ralf Loo, Marcel Van Der Sluis, Pawel Jankowski, Hubert Maehr
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Patent number: 7538098Abstract: 19-nor-vitamin D analogs having an additional heterocyclic ring connecting the 3?-oxygen and carbon-2 or the 1?-oxygen and carbon-2 of the A-ring of the analog, and pharmaceutical uses therefore, are described. These compounds exhibit significant activity in mobilization of bone, making them therapeutic agents for the treatment or prophylaxis of osteoporosis, osteomalacia, osteopenia, renal osteodystrophy and hypoparathyroidism.Type: GrantFiled: April 6, 2007Date of Patent: May 26, 2009Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Rafal R. Sicinski, Agnieszka Glebocka, Lori A. Plum, Margaret Clagett-Dame
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Publication number: 20090131379Abstract: The invention relates to compounds that are vitamin D receptor activators, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.Type: ApplicationFiled: September 8, 2008Publication date: May 21, 2009Applicant: ABBOTT LABORATORIESInventors: Thomas W. Von Geldern, Jufang H. Barkalow, David M. Barnes, Anthony R. Haight, John E. Hengeveld, Xiaofeng Li, Maureen A. McLaughlin, William T. Noonan, Zhonghua Pei, Jinshyun Ruth Wu-Wong
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Patent number: 7534777Abstract: Des-C,D 2-methylene-19-norvitamin D3 analogs are provided including compounds of formula 1, in which R1 is a straight or branched chain alkyl or alkylene group having from 8 to 27 carbons and bearing an OY3 group; and Y1, Y2 and Y3 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: August 30, 2006Date of Patent: May 19, 2009Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Katarzyna Plonska-Ocypa, Rafal Sicinski, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
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Publication number: 20090124819Abstract: The object of the present invention is to synthesize novel vitamin D derivatives. According to the present invention, there are provided vitamin D derivatives represented by the following general formula (1): wherein R1 and R2 may be the same or different, and each represents a straight chain or branched chain alkyl group optionally substituted by a hydroxyl group, and R3 represents a straight chain or branched chain alkyl group optionally substituted by a hydroxyl group.Type: ApplicationFiled: January 7, 2009Publication date: May 14, 2009Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: Hiroaki Takayama, Toshie Fujishima, Atsushi kittaka
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Patent number: 7531527Abstract: 2-propylidene-19-nor-vitamin D compounds are disclosed as well as pharmaceutical uses for these compounds and methods of synthesizing these compounds. These compounds are characterized by high bone calcium mobilization activity and high intestinal calcium transport activity. This results in novel therapeutic agents for the treatment and prophylaxis of diseases where bone formation is desired, particularly osteoporosis, as well as autoimmune diseases such as multiple sclerosis, diabetes mellitus and lupus. These compounds also 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. These compounds also increase both breaking strength and crushing strength of bones evidencing use in conjunction with bone replacement surgery such as hip and knee replacements.Type: GrantFiled: May 17, 2007Date of Patent: May 12, 2009Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Rafal R. Sicinski, Agnieszka Glebocka, Lori A. Plum
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Patent number: 7528122Abstract: Compounds of formula IA or IB are provided where X1, X2 and X3 are independently selected from H or hydroxy protecting groups and R1 is selected from straight or branched chain alkyl groups having from 1 to 8 carbon atoms; straight or branched chain alkenyl groups having from 2 to 8 carbon atoms; straight or branched chain hydroxy-substituted alkyl groups having from 1 to 8 carbon atoms; straight and branched chain hydroxy-substituted alkenyl groups having from 2 to 8 carbon atoms. Such compounds are used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.Type: GrantFiled: January 30, 2007Date of Patent: May 5, 2009Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Grazia Chiellini, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7524980Abstract: Compounds expressed by the following formula (1) or pharmaceutically permissible solvate thereof which is effective for treating Paget's disease of bone, hypercalcemia or osteoporosis. In the formula, R1 is a C2-C10 alkyl group, or a C7-C15 aralkyl group whose aromatic ring is optionally substituted with a C1-C6 alkyl group, a C1-C6 alkoxyl group, a hydroxyl group, a halogen atom or a trifluoromethyl group; and R2 is a C1-C10 alkyl group, or a C7-C15 aralkyl group whose aromatic ring is optionally substituted with a C1-C6 alkyl group, a C1-C6 alkoxyl group, a hydroxyl group, a halogen atom or a trifluoromethyl group.Type: GrantFiled: November 4, 2004Date of Patent: April 28, 2009Assignee: Teijin Pharma LimitedInventors: Kazuo Nagasawa, Yuichi Hashimoto, Yuko Kato
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Publication number: 20090099141Abstract: The present invention provides for: (a) an oral dosage of vitamin D3 for humans sufficient to maintain a serum level above a minimally sufficient level and below a toxic level when administered according to a schedule of at least one dosage a week up to at least one dosage a day, (b) methods for administering the oral dosages and (c) a kit involving a blister pack and a plurality of oral dosages with instructions for administering the dosages and a location on the blister pack for recording information related to the administration of each dosage, the name of the person receiving the dosages and additional relevant information.Type: ApplicationFiled: December 22, 2008Publication date: April 16, 2009Inventor: James Grote
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Publication number: 20090099140Abstract: The invention provides 20-alkyl Gemini vitamin D3 compounds, methods for using the compounds to treat vitamin D3 associated states and pharmaceutical compositions containing the compounds.Type: ApplicationFiled: March 23, 2006Publication date: April 16, 2009Applicant: BioXell S.p.A.Inventors: Pawel Jankowski, Milan R. Uskokovic, Luciano Adorini
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Patent number: 7511030Abstract: 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: GrantFiled: February 10, 2006Date of Patent: March 31, 2009Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame
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Publication number: 20090082317Abstract: 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: ApplicationFiled: April 25, 2006Publication date: March 26, 2009Applicants: CYTOCHROMA INC., JOHNS HOPKINS UNIVERSITYInventors: Uttam Saha, Gary H. Posner, Mehmet Kahraman
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Publication number: 20090075953Abstract: The present application describes deuterium-enriched ED-71, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.Type: ApplicationFiled: August 22, 2008Publication date: March 19, 2009Applicant: PROTIA, LLCInventor: Anthony W. Czarnik
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Patent number: 7491712Abstract: The invention relates to a novel process for the preparation of Paricalcitol and intermediates thereof.Type: GrantFiled: December 10, 2007Date of Patent: February 17, 2009Assignee: Formosa Laboratories, Inc.Inventors: Chze Siong Ng, Ching-Peng Wei
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Patent number: 7491711Abstract: The present invention provides a method for treating osteoporosis, hyperparathyroidism or an autoimmune disease in a patient by administering to the patient a 3-desoxy vitamin D3 analog of the formula: a prodrug or a salt thereof, where the dotted line, R1, R2, R3, R4 and L are those defined herein. The present invention also provides methods for producing 3-desoxy vitamin D3 analog of Formula I.Type: GrantFiled: September 18, 2002Date of Patent: February 17, 2009Assignee: Roche Palo Alto LLCInventor: Milan Radoje Uskokovic
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Publication number: 20080318911Abstract: The invention provides vitamin D3 analogs of cholecalciferol, substituted at carbon 20 with cycloalkyl, e.g., cyclopropyl, wherein carbon-16 is a double bond, and carbon-23 is a single, double, or triple bond. Various alkyl or haloalkyl substitutions are incorporated as carbon-25. The invention provides pharmaceutically acceptable esters, salts, and prodrugs thereof. Methods for using the compounds to treat vitamin D3 associated states, and pharmaceutical compositions containing the compounds are also disclosed.Type: ApplicationFiled: September 23, 2005Publication date: December 25, 2008Applicant: BIOXELL S.P.A.Inventors: Milan R. Uskokovic, Luciano Adorini, Guiseppe Penna, Enrico Colli, Stanislaw Marczak
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Publication number: 20080300223Abstract: 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: ApplicationFiled: July 10, 2008Publication date: December 4, 2008Inventors: Hector F. DeLuca, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
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Publication number: 20080280859Abstract: The invention provides Gemini vitamin D3 compounds, methods for using the compounds to treat vitamin D3 associated states and pharmaceutical compositions containing the compounds.Type: ApplicationFiled: October 19, 2005Publication date: November 13, 2008Applicant: BioXell S.p.A.Inventors: Luciano Adorini, Giuseppe Penna, Milan R. Uskokovic, Hubert Maehr
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Publication number: 20080255380Abstract: Preparation of sulfonyl derivatives of cholecalciferol of Formula 1, wherein R1 is a protective group, preferably a t-butyl(dimethyl)silyl, and R2 is a heterocyclic group, such as a 2-thiazolyl, a 2-benzothiazolyl, a 1-phenyl-1H-tetrazo-5-yl, a 2-pyridyl, a 2-pyrimidynyl, a 1-isochinolinyl, a 1-methyl-2-imidazyl, or a 4-alkyl-1,2,4-triazo-3-yl, comprises the conversion of the hydroxyl derivative of cholecalciferol into the corresponding sulfide followed by its oxidation to the respective sulfone characterized by the use of a hydroxyl derivative of cholecalciferol as a starting material, in which the triene system is protected as a Diels-Alder adduct, and in particular as an adduct with sulfur dioxide of the Formula 2a. Novel are also the derivatives of Formula 3a and 4a, isolated in the process provided by the invention.Type: ApplicationFiled: May 13, 2005Publication date: October 16, 2008Applicant: INSTYTUT FARMACEUTYCZNYInventors: Michal Chodynski, Malgorzata Krupa, Hanna Fitak, Jerzy Winiarski, Teresa Ryznar, Bartlomiej Gorecki, Wieslaw Szelejewski, Andrzej Kutner
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Patent number: 7402688Abstract: A novel 2,2-di-substituted 19-norvitamin D derivative. It is a compound represented by the general formula (I) wherein R1 and R2 are the same or different and each represents hydroxy and A represents hydrogen, or an unsubstituted linear or branched alkyl.Type: GrantFiled: October 10, 2003Date of Patent: July 22, 2008Assignee: Wisconsin Alumni Research FoundationInventors: Sachiko Yamada, Masato Shimizu, Yukiko Miyamoto
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Publication number: 20080171728Abstract: Disclosed herein are methods for preparing steroids and Vitamin D derivatives having the unnatural beta (usually S) configuration at C20, the methods comprising the use of compounds of the formula: wherein R is as defined herein. Also disclosed are steroids and Vitamin D derivatives made using the methods disclosed herein and pharmaceutical compositions comprising said steroids and Vitamin D derivatives.Type: ApplicationFiled: January 11, 2008Publication date: July 17, 2008Inventor: Alexander James Bridges
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Publication number: 20080161587Abstract: Provided is a crystallization method for reducing the level of impurities in calcipotriene in which a solution of a starting calcipotriene in a first process solvent, for example THF, is combined with second process solvent, for example methyl formate, and, after cooling, calcipotriene is isolated. The method can include a slurry step for reducing the level of residual first process solvent.Type: ApplicationFiled: March 7, 2008Publication date: July 3, 2008Inventors: Anchel Schwartz, Asher Maimon
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Publication number: 20080064668Abstract: The invention provides (1,3)di-acylated vitamin D3 analogs of cholecalciferol, substituted at carbon (20) with methyl or cyclopropyl wherein carbon (16) is a single or double bond, and carbon (23) is a single, double, or triple bond. Various alkyl or haloalkyl substitutions are incorporated at carbon (25). The invention provides pharmaceutically acceptable esters, salts, and pro-drugs thereof. Methods for using the compounds to treat vitamin D3 associated states, and pharmaceutical compositions containing the compounds are also disclosed.Type: ApplicationFiled: September 24, 2004Publication date: March 13, 2008Applicant: BioXell S.p.A.Inventors: Milan R. Uskokovic, Luciano Adorini, Giuseppe Penna, Enrico Colli
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Patent number: 7332482Abstract: The use of 1-alpha-fluoro-25-hydroxy-16,23E-diene-26,27-bishomo-20-epi-cholecalciferol, or a pharmaceutically acceptable salt or ester thereof, for the manufacture of a medicament for the prevention and/or treatment of benign prostatic hyperplasia (BPH) and associated symptoms.Type: GrantFiled: July 29, 2004Date of Patent: February 19, 2008Assignee: BioXell S.p.A.Inventors: Luciano Adorini, Enrico Colli
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Patent number: 7323580Abstract: A compound represented by formula (III):Type: GrantFiled: May 21, 2007Date of Patent: January 29, 2008Assignee: Chugai Seiyaku Kabushiki KaishaInventor: Tsuyoshi Yamauchi
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Publication number: 20070238706Abstract: Compounds of formula I are provided where X1, X2 and X3 are independently selected from H or hydroxy protecting groups. Such compounds are used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.Type: ApplicationFiled: April 6, 2007Publication date: October 11, 2007Inventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame, Rafal Barycki
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Publication number: 20070238702Abstract: Compounds of formula I are provided where X1 and X2 are independently selected from H or hydroxy protecting groups. Such compounds are used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.Type: ApplicationFiled: April 6, 2007Publication date: October 11, 2007Inventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame, Rafal Barycki
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Publication number: 20070238705Abstract: Compounds of formula I are provided where X1, X2 and X3 are independently selected from H or hydroxy protecting groups. Such compounds are used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.Type: ApplicationFiled: April 6, 2007Publication date: October 11, 2007Inventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame, Rafal Barycki
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Publication number: 20070238703Abstract: This invention discloses 1?-hydroxy-2-(3?-hydroxypropylidene)-19-nor-vitamin D compounds with a 1,1-dimethylpropyl side chain, 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: ApplicationFiled: April 6, 2007Publication date: October 11, 2007Inventors: Hector F. DeLuca, Agnieszka Glebocka, Rafal R. Sicinski, Lori A. Plum, Margaret Clagette-Dame
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Publication number: 20070191317Abstract: Compounds of formula IA or IB are provided where X1, X2 and X3 are independently selected from H or hydroxy protecting groups and R1 is selected from straight or branched chain alkyl groups having from 1 to 8 carbon atoms; straight or branched chain alkenyl groups having from 2 to 8 carbon atoms; straight or branched chain hydroxy-substituted alkyl groups having from 1 to 8 carbon atoms; straight and branched chain hydroxy-substituted alkenyl groups having from 2 to 8 carbon atoms. Such compounds are used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.Type: ApplicationFiled: January 30, 2007Publication date: August 16, 2007Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: Hector F. DELUCA, Grazia CHIELLINI, Pawel GRZYWACZ, Lori A. PLUM, Margaret CLAGETT-DAME
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Publication number: 20070191316Abstract: Compounds of formula IA or IB are provided where X1, X2 and X3 are independently selected from H or hydroxy protecting groups and R1 is selected from straight or branched chain alkyl groups having from 1 to 8 carbon atoms; straight or branched chain alkenyl groups having from 2 to 8 carbon atoms; straight or branched chain hydroxy-substituted alkyl groups having from 1 to 8 carbon atoms; straight and branched chain hydroxy-substituted alkenyl groups having from 2 to 8 carbon atoms. Such compounds are used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.Type: ApplicationFiled: January 30, 2007Publication date: August 16, 2007Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventors: Hector F. DELUCA, Grazia CHIELLINI, Pawel GRZYWACZ, Lori A. PLUM, Margaret CLAGETT-DAME
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Enzymatic method to produce 7-dehydropregnenolone, vitamin D3-like compounds and derivatives thereof
Patent number: 7253293Abstract: Provided herein are enzymatic methods of producing steroid compounds such as 7-dehydropregnenolone, hydroxy derivatives thereof and vitamin D2- and D3-like compounds and derivatives thereof. Also provided are the derivatives of the vitamin D3-like compounds so generated via the action of cytochrome P450scc enzyme on substrates 7-dehydrocholesterol, vitamin D2 or vitamin D3.Type: GrantFiled: January 6, 2005Date of Patent: August 7, 2007Inventors: Andrzej Slominski, Robert Tuckey, Jordan Zjawiony, D. Jeremy Stewart, Jacobo Wortsman -
Patent number: 7244719Abstract: This invention discloses 2-methylene-19,26,27-trinor-(20S)-vitamin D analogs, and specifically 2-methylene-19,26,27-trinor-(20S)-1?-hydroxyvitamin 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: November 18, 2005Date of Patent: July 17, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Lori A. Plum, Pawel K. Grzywacz, Margaret Clagett-Dame
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Patent number: 7241748Abstract: This invention discloses 17,20(Z)-dehydro vitamin D analogs, and specifically 17(Z)-1?,25-dihydroxy-17(20)-dehydro-2-methylene-19-nor-vitamin 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 may be used to treat autoimmune disorders and inflammatory diseases in humans as well as renal osteodystrophy and obesity. This compound also has significant calcemic activity making it a therapeutic agent for the treatment or prophylaxis of osteoporosis, osteomalacia, renal osteodystrophy and hypoparathyroidism.Type: GrantFiled: November 18, 2005Date of Patent: July 10, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Bulli Padmaja Tadi, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7241909Abstract: 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.Type: GrantFiled: May 2, 2006Date of Patent: July 10, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7241752Abstract: This invention discloses 17,20(E)-dehydro vitamin D analogs, and specifically 17(E)-1?,25-dihydroxy-17(20)-dehydro-2-methylene-19-nor-vitamin 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 and inflammatory diseases in humans as well as renal osteodystrophy and obesity.Type: GrantFiled: November 18, 2005Date of Patent: July 10, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Bulli Padmaja Tadi, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7241751Abstract: 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: November 18, 2005Date of Patent: July 10, 2007Assignee: Wisconsin Alumi Research FoundationInventors: Hector F. DeLuca, Rafal R. Sicinski, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7241749Abstract: 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: GrantFiled: November 18, 2005Date of Patent: July 10, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Lori A. Plum, Pawel K. Grzywacz, Margaret Clagett-Dame
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Patent number: 7241747Abstract: 2-propylidene-19-nor-vitamin D compounds are disclosed as well as pharmaceutical uses for these compounds and methods of synthesizing these compounds. These compounds are characterized by high bone calcium mobilization activity and high intestinal calcium transport activity. This results in novel therapeutic agents for the treatment and prophylaxis of diseases where bone formation is desired, particularly osteoporosis, as well as autoimmune diseases such as multiple sclerosis, diabetes mellitus and lupus. These compounds also 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. These compounds also increase both breaking strength and crushing strength of bones evidencing use in conjunction with bone replacement surgery such as hip and knee replacements.Type: GrantFiled: April 9, 2004Date of Patent: July 10, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Rafal R. Sicinski, Agnieszka Glebocka, Lori A. Plum
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Patent number: 7241750Abstract: This invention discloses 2-methylene-19-nor-17-ene vitamin D analogs, and specifically 2-methylene-19-nor-1?-hydroxy-17-ene-homopregnacalciferol 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 and inflammatory diseases in humans as well as renal osteodystrophy. This compound may also be used for the treatment or prevention of obesity.Type: GrantFiled: November 18, 2005Date of Patent: July 10, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Bulli Padmaja Tadi, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7238681Abstract: This invention discloses 2-methylene-18,19-dinor-vitamin D analogs, and specifically 2-methylene-18,19-dinor-1?-hydroxy-homopregnacalciferol 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: November 18, 2005Date of Patent: July 3, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Rafal Barycki, Lori A. Plum, Margaret Clagett-Dame
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Patent number: 7235680Abstract: Compounds of formula 1A and 1B are provided where X1 and X2 are independently selected from H or hydroxy protecting groups.Type: GrantFiled: March 28, 2006Date of Patent: June 26, 2007Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Lori A. Plum, Margaret Clagett-Dame, Grazia Chiellini, Pawel Grzywacz