Abstract: The present invention relates to steroid hormone products, such as oral contraceptive products, including at least one steroid active ingredient mixed with an excipient and having improved dissolution and release rate properties. The invention further relates to methods for making such steroid hormone products, wherein a mixture of the hormone and the excipient is subjected to sufficient mechanical energy to form a powder blend wherein the hormone is stabilized by the excipient in substantially non-crystalline form.
Type:
Grant
Filed:
December 13, 2001
Date of Patent:
January 11, 2011
Assignee:
Ortho-McNeil Pharmaceutical, Inc.
Inventors:
Thomas Schultz, Bradley A. Clark, Angela Falzone
Abstract: The use of benzophenones of the formula I in which R is hydrogen or C1-C4-alkyl and Hal is fluorine, chlorine or bromine for controlling Pseudocercosporella herpotrichoides in crop plants is described.
Type:
Grant
Filed:
July 11, 2003
Date of Patent:
December 7, 2010
Assignee:
BASF SE
Inventors:
Markus Gewehr, Ingo Rose, Bernd Müller, Eberhard Ammermann, Ann Orth, Henry Van Tuyl Cotter
Abstract: The present invention provides a compound represented by the formula: wherein Q represents a fused heterocyclic group, X and Y are the same or different and each represent an optionally halogenated lower alkyl group, an optionally halogenated lower alkoxy group, etc., or a salt thereof, as well as a herbicide comprising the compound or a salt thereof, which exhibits a significant effect for control of sulfonylurea herbicide-resistant weeds in paddy fields and can reduce the number of active ingredients in a combined preparation and a method of controlling sulfonylurea herbicide-resistant weeds which comprises using the same.
Abstract: 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:
Grant
Filed:
January 30, 2007
Date of Patent:
September 28, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. Deluca, Grazia Chiellini, Pawel Grzywacz, Lori A. Plum, Margaret Clagett-Dame
Abstract: Syntheses of steroids such as 3-hydroxy-7?-methyl-21-[2?-methoxy-4?-(diethylaminomethyl)-phenoxy]-19-norpregna-1,3,5(10)triene citrate (“SR 16234”) and analogs thereof are provided, wherein 21-hydroxy-19-norpregna-4-en-3-one serves as a starting material or intermediate. The latter compound may be readily prepared from estrone-3-methyl ether. Certain intermediates in these syntheses also have value as therapeutic agents, for example in the treatment of prostate disorders such as prostatic cancer.
Type:
Grant
Filed:
August 9, 2004
Date of Patent:
August 10, 2010
Assignee:
SRI International
Inventors:
Richard H. Peters, Jyanwei Liu, John G. Johansson, Kenneth J. Ryan, Wan-Ru Chao, Masato Tanabe
Abstract: Disclosed are 3-heterocyclyl substituted benzoic acid derivatives of general formula (I), in which the variables R1 to R8 and X have the meanings indicated in claim 1, and the use thereof as herbicides or for desiccating/defoliating plants.
Type:
Grant
Filed:
July 22, 2003
Date of Patent:
August 3, 2010
Assignee:
BASF Aktiengesellschaft
Inventors:
Michael Puhl, Gerhard Hamprecht, Robert Reinhard, Ingo Sagasser, Werner Seitz, Cyrill Zagar, Matthias Witschel, Andreas Landes
Abstract: A fungicidal compound of formula (1): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by groups R7, R8 and R9; R1 is hydrogen, optionally substituted (C1-4)alkylC(?O), optionally substituted (C1-4)alkylC(?O)O, optionally substituted (C1-4)alkoxy(C1-4)alkyl, optionally substituted allyl, optionally substituted propargyl or optionally substituted allenyl; R2, R3, R4and R5 are each, independently, hydrogen, halogen, optionally substituted (C1-4)alkoxy(C1-4)alkoxy or optionally substituted (C1-4)alkoxy(C1-4)alkyl; R6 is an organic group containing three to thirteen carbon atoms and at least one silicon atom and, optionally, one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, and is optionally substituted by one to four independently selected halogen atoms; R7, R8 and R9are each, independently, hydrogen, halogen, C1-3alkyl, C1-3haloalkyl, C1-3alkoxy(C
Type:
Grant
Filed:
March 21, 2003
Date of Patent:
August 3, 2010
Assignee:
Syngenta Crop Protection, Inc.
Inventors:
Josef Ehrenfreund, Pierre Joseph Marcel Jung, Hans Tobler, Harald Walter
Abstract: A method of minimizing or reducing the toxicity of a retinoid having a free carboxyl group and the resulting modified retinoids are described. The method comprises the step of esterifying the carboxyl group of the retinoid with a highly sterically hindered compound, which is preferably a secondary or tertiary alcohol. The resulting retinoid esters are rendered much less toxic than the starting or parent retinoid. This process provides a retinoid ester analog of reduced toxicity so that it may be administered orally with minimal side effects and with a much greater therapeutic window. The modified retinoid compounds are useful in the treatment and prophylaxis of all diseases and disorders where retinoid compounds have been shown effective.
Type:
Grant
Filed:
April 2, 2008
Date of Patent:
July 27, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Margaret Clagett-Dame, Sumithra Gowlugari
Abstract: 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:
Grant
Filed:
April 6, 2007
Date of Patent:
July 27, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Agnieszka Glebocka, Rafal R. Sicinski, Lori A. Plum, Margaret Clagett-Dame
Abstract: The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.
Type:
Grant
Filed:
August 18, 2003
Date of Patent:
July 13, 2010
Assignee:
Bayer CropScience AG
Inventors:
Reiner Fischer, Thomas Bretschneider, Christoph Erdelen, Angelika Lubos-Erdelen, legal representative, Jörg Konze, Peter Lösel, Mark Wilhelm Drewes, Dieter Feucht, Karl-Heinz Kuck, Ulrike Wachendorff-Neumann
Abstract: A method of minimizing or reducing the toxicity of a retinoid having a free carboxyl group and the resulting modified retinoids are described. The method comprises the step of esterifying the carboxyl group of the retinoid with a highly sterically hindered compound, which is preferably a secondary or tertiary alcohol. The resulting retinoid esters are rendered much less toxic than the starting or parent retinoid. This process provides a retinoid ester analog of reduced toxicity so that it may be administered orally with minimal side effects and with a much greater therapeutic window. The modified retinoid compounds are useful in the treatment and prophylaxis of all diseases and disorders where retinoid compounds have been shown effective.
Type:
Grant
Filed:
April 2, 2008
Date of Patent:
July 6, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Margaret Clagett-Dame, Sumithra Gowlugari
Abstract: This invention discloses 2-methylene-(20R,25S)-19,27-dinor-(22E)-vitamin D analogs, and specifically 2-methylene-(20R,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:
Grant
Filed:
September 25, 2007
Date of Patent:
June 22, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Grazia Chiellini, Pawel Grzywacz
Abstract: 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:
Grant
Filed:
July 9, 2007
Date of Patent:
June 22, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Bulli Padmaja Tadi, Lori A. Plum, Margaret Clagett-Dame
Abstract: In the production of 2,2,3,3-tetrafluorooxethane by reaction of tetrafluoroethylene with a compound of formaldehyde generation source in anhydrous hydrogen fluoride, the reaction is carried out in the presence of polyfluoroalkylcarboxylic acid or polyfluoroalkyl ester thereof, represented by the following general formula RfCOORf? (where Rf is a polyfluoroalkyl group having 1-5 carbon atoms, and Rf? is a hydrogen atom or a polyfluoroalkyl group having 1-5 carbon atoms), preferably CF3COOH, CF3COOCH2CF2CF3, or CF3COOCH2CF3, whereby a high reaction yield can be attained.
Abstract: The invention relates to compounds of the formula I: and to the pharmaceutically acceptable salts thereof, to processes for the preparation of them and to pharmaceutical compositions comprising them, which are useful especially for the treatment and prevention of dyslipidaemia, atherosclerosis and diabetes.
Type:
Grant
Filed:
August 11, 2003
Date of Patent:
June 15, 2010
Assignee:
Merck Patent GmbH
Inventors:
Michel Brunet, Jean-Jacques Zeiller, Gérard Ferrand, Yves Bonhomme
Abstract: The invention provides compounds of the formula: wherein X, Y, and Z are as defined in the specification. The compounds are effective anti-tumor agents. The invention also provides pharmaceutical compositions comprising a compound of the above formula or a salt thereof, intermediates useful for preparing a compound of the above formula, and therapeutic methods comprising administering a compound of the above formula or a salt thereof to a mammal in need thereof.
Type:
Grant
Filed:
October 29, 2008
Date of Patent:
June 1, 2010
Assignee:
Wayne State University
Inventors:
Jerome P. Horwitz, Thomas H. Corbett, Eduardo Palomino, Lisa Polin, Stuart T. Hazeldine
Abstract: 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:
Grant
Filed:
December 24, 2008
Date of Patent:
May 18, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Rafal Barycki
Abstract: This invention provides pharmaceutical uses for 2-methylene-19-nor-20(S)-1?,25-dihydroxyvitamin D3. Administration of this compound increases the life expectancy of human beings, especially elderly human beings. In particular, it increases the survival rate of females lacking estrogen, especially post-menopausal females, and reduces mortality resulting from spontaneous development of malignant tumors in both males and females.
Type:
Grant
Filed:
June 21, 2006
Date of Patent:
May 18, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Lori A. Plum, Margaret Clagette-Dame
Abstract: 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:
Grant
Filed:
December 24, 2008
Date of Patent:
May 18, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Margaret Clagett-Dame, Lori A. Plum, Rafal Barycki
Abstract: This invention discloses 2-methylene-(22E)-25-(1-methylene-hexyl)-26,27-cyclo-22-dehydro-19-nor-vitamin D analogs, and specifically 2-methylene-(22E)-25-(1-methylene-hexyl)-26,27-cyclo-22-dehydro-19-nor-1?,24(R)-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 shows lower 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.
Type:
Grant
Filed:
July 10, 2008
Date of Patent:
May 11, 2010
Assignee:
Wisconsin Alumni Research Foundation
Inventors:
Hector F. DeLuca, Rafal Barycki, Lori A. Plum, Margaret Clagett-Dame