The Cyclopentanohydrophenanthrene Ring System Is Fully Saturated (e.g., Androstandiols, Androsterones, Dihydrotestosterones, Etc.) Patents (Class 552/641)
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Patent number: 9314471Abstract: The invention provides and describes solid state 17?-ethynyl-5?-androstane-3?,17?-diol including amorphous and crystalline forms and specific polymorphic forms thereof. Anhydrates and solvates of 17?-ethynyl-5?-androstane-3?,17?-diol include Form III anhydrate and Form I solvate. The invention further relates to solid and suspension formulations containing 17?-ethynyl-5?-androstane-3?,17?-diol in a described solid state form and use of the formulations to treat cancers or precancers such as prostate cancer or breast cancer in subjects or human patients. The invention also relates to methods to make liquid formulations from solid state forms of 17?-ethynyl-5?-androstane-3?,17?-diol and uses of such formulations in treating the described conditions.Type: GrantFiled: June 17, 2013Date of Patent: April 19, 2016Assignee: NEURMEDIX, INC.Inventors: Steven K. White, Erin E. Jansen, Keith Lorimer, Brenton Skylar Wolfe
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Publication number: 20140121190Abstract: The invention relates to the field of male and/or female sexual dysfunction. The invention specifically relates to the use of 3-alpha-androstanediol, preferably in combination with a type 5 phosphodiesterase (PDE5) inhibitor.Type: ApplicationFiled: January 3, 2014Publication date: May 1, 2014Applicant: EMOTIONAL BRAIN B.V.Inventors: Jan Johan Adriaan TUITEN, Johannes Martinus Maria BLOEMERS, Robertus Petrus Johannes DE LANGE
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Publication number: 20140121189Abstract: The invention relates to the field of male and/or female sexual dysfunction. The invention specifically relates to the use of 3-alpha-androstanediol, preferably in combination with a 5-HT1A agonist. Optionally, said 3-alpha-androstanediol and said 5HT1a agonist are further combined with a type 5 phosphodiesterase (PDE5) inhibitor.Type: ApplicationFiled: January 3, 2014Publication date: May 1, 2014Applicant: EMOTIONAL BRAIN B.V.Inventors: Jan Johan Adriaan TUITEN, Johannes Martinus Maria BLOEMERS, Robertus Petrus Johannes DE LANGE
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Publication number: 20140107328Abstract: Chemoselective isolation of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds is accomplished via formation of polymeric siloxyl ethers. Chemoselective release of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds from polymeric siloxyl reagents is described.Type: ApplicationFiled: December 11, 2013Publication date: April 17, 2014Inventors: Erin E. CARLSON, Darci TRADER
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Publication number: 20140045697Abstract: The present invention relates to novel androstan derivatives, methods for their production, and their use for influencing plant growth.Type: ApplicationFiled: March 8, 2012Publication date: February 13, 2014Applicant: SYNGENTA PARTICIPATIONS AGInventors: Pierre Joseph Marcel Jung, Anna Elizabeth Louw-Gaume, Alain De Mesmaeker, Mathilde Denise Lachia
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Publication number: 20140017675Abstract: Provided is a ultra-high-sensitivity assay in which the assay can be made on a commonly used assay apparatus such as an absorptiometer and a plate reader or with naked eyes. The high-sensitivity assay in which the assay can be made on a commonly used assay apparatus or with naked eyes can be provided by combining an enzyme cycling method using thio-NAD(P) as a coenzyme, a labeling enzyme and a substrate for the labeling enzyme optimally, and by amplifying thio-NAD(P)H, which is a signaling substance, exponentially and then quantifying the thio-NAD(P)H colorimetrically.Type: ApplicationFiled: March 23, 2012Publication date: January 16, 2014Inventor: Etsuro Ito
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Publication number: 20140011785Abstract: The present invention relates to antiandrogenic compounds which may be administered for the treatment of androgen excess in the skin and by way of consequence, the treatment of acne, baldness or hirsuitism in subject or patient.Type: ApplicationFiled: September 6, 2013Publication date: January 9, 2014Applicant: Yale UniversityInventor: Richard Hochberg
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Publication number: 20130345184Abstract: The invention provides and describes solid state 17?-ethynyl-5?-androstane-3?,17?-diol including amorphous and crystalline forms and specific polymorphic forms thereof. Anhydrates and solvates of 17?-ethynyl-5?-androstane-3?,17?-diol include Form III anhydrate and Form I solvate. The invention further relates to solid and suspension formulations containing 17?-ethynyl-5?-androstane-3?,17?-diol in a described solid state form and use of the formulations to treat cancers or precancers such as prostate cancer or breast cancer in subjects or human patients. The invention also relates to methods to make liquid formulations from solid state forms of 17?-ethynyl-5?-androstane-3?,17?-diol and uses of such formulations in treating the described conditions.Type: ApplicationFiled: June 17, 2013Publication date: December 26, 2013Inventors: Steven K. White, Erin E. Jansen, Keith Lorimer, Brenton Skylar Wolfe
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Publication number: 20130267721Abstract: Synthetic methods for preparing deoxycholic acid and intermediates thereof are provided.Type: ApplicationFiled: January 28, 2013Publication date: October 10, 2013Inventors: Achampeta Rathan Prasad, Roy A. Swaringen, JR., John Gregory Reid, Robert M. Moriarty, Akhila Kumar Sahoo
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Patent number: 8518922Abstract: The invention provides and describes solid state 17?-ethynyl-5?-androstane-3?,17?-diol including amorphous and crystalline forms and specific polymorphic forms thereof. Anhydrates and solvates of 17?-ethynyl-5?-androstane-3?,17?-diol include Form III anhydrate and Form I solvate. The invention further relates to solid and suspension formulations containing 17?-ethynyl-5?-androstane-3?,17?-diol in a described solid state form and use of the formulations to treat cancers or precancers such as prostate cancer or breast cancer in subjects or human patients. The invention also relates to methods to make liquid formulations from solid state forms of 17?-ethynyl-5?-androstane-3?,17?-diol and uses of such formulations in treating the described conditions.Type: GrantFiled: February 12, 2009Date of Patent: August 27, 2013Assignee: Harbor Therapeutics, Inc.Inventors: Steven White, Erin Olson, Keith Lorimer, Brenton Skylar Wolfe
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Publication number: 20100152145Abstract: The invention relates to the field of male and/or female sexual dysfunction. The invention specifically relates to the use of 3-alpha-androstanediol, preferably in combination with a type 5 phosphodiesterase (PDE5) inhibitor.Type: ApplicationFiled: November 2, 2007Publication date: June 17, 2010Inventors: Jan Johan Adriaan Tuiten, Johannes Martinus Maria Bloemers, Robertus Petrus Johannes De Lange
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Publication number: 20100093680Abstract: The invention relates to the field of male and/or female sexual dysfunction. The invention specifically relates to the use of 3-alpha-androstanediol, preferably in combination with a 5-HT1A agonist. Optionally, said 3-alpha-androstanediol and said 5HT1a agonist are further combined with a type 5 phosphodiesterase (PDE5) inhibitor.Type: ApplicationFiled: November 2, 2007Publication date: April 15, 2010Inventors: Jan Johan Adriaan Tuiten, Johannes Martinus Maria Bloemers, Robertus Petrus Johannes De Lange
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Publication number: 20090105202Abstract: The disclosure provides androsterone derivatives. The derivatives of the disclosure are useful in the treatment of androgen- and estrogen-associated diseases and disorders, including breast cancer.Type: ApplicationFiled: October 18, 2006Publication date: April 23, 2009Applicants: CALIFORNIA PACIFIC MEDICAL CENTER, CATHOLIC HEALTHCARE WESTInventor: Li-Xi Yang
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Patent number: 7196074Abstract: Methods of using 7?,11?-dimethyl-17?-hydroxyestra-4,14-dien-3-one (III) and 17 esters thereof for various hormonal therapies, oral and parenteral dosage forms comprising these actives, and processes for their preparation.Type: GrantFiled: October 28, 2002Date of Patent: March 27, 2007Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Richard P. Blye, Hyun K. Kim, Pemmaraju Narasimha Rao, Carmie Kirk Acosta
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Patent number: 7018993Abstract: A compound pf general formula (I): wherein, for example, X1 and X2 independently represent a hydrogen atom. Ra represents a hydrogen atom or a protecting group for a hydroxyl group. Rb and Rc form an optionally protected —(C?O)— together with the 3-position carbon atom attached to Rb and Rc, and the broken line forms a single bond or double bond together with the solid line, or a pharmaceutically acceptable salt of the compound or a prodrug thereof.Type: GrantFiled: July 2, 2001Date of Patent: March 28, 2006Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Masateru Ohta, Nobuaki Kato, Mitsuaki Nakamura, Kazutaka Tachibana
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Patent number: 6780854Abstract: Novel, orally active androgens are 7&agr;-substituted &Dgr;14-nandrolone derivatives. The compounds satisfy the general formula: wherein R1 is O, (H,H), (H,OR), NOR, with R being hydrogen, (C1-6) alkyl, or (C,1-6) acyl; R2 is selected from the group consisting of (C2-4) alkyl, (C2-4) alkenyl, or (C2-4) alkynyl, each optionally substituted by halogen; or R2 is cyclopropyl, or cyclopropenyl, each optionally substituted by (C1-2) alkyl, or halogen; R3 is hydrogen, (C1-2) alkyl, or ethenyl; R4 is (C1-2) alkyl; R5 is hydrogen, or (C1-15) acyl; and the dotted lines indicate optional bonds.Type: GrantFiled: October 24, 2002Date of Patent: August 24, 2004Assignee: Akzo Nobel NVInventors: Hubert Jan Jozef Loozen, Dirk Leysen, Jaap van der Louw
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Patent number: 6756366Abstract: Orally Active androgens are derivative of 7&agr;-methyl-19-nortestosterone. The compounds satisfy formula (I) wherein R1 is O, (H,H), (H,OR), NOR, with R being hydrogen, (C1-6)alkyl, or (C1-6)acyl; R2 is selected from the group consisting of (C2-3)alkyl, isopropyl, (C2-3)1-alkenyl, isopropenyl, 1,2-proandienyl, or (C2-3)1-alynyl, each optionally substituted by halogen; or R2 is cyclopropyl, or cyclopropenyl, each optionally substituted by (C1-2)alkyl, or halogen; R3 is hydrogen, (C1-2)alkyl, or ethenyl; R4 is (C1-2)alkyl; R5 is hydrogen, or (C1-15)acyl; and the dotted lines indicate optional bonds.Type: GrantFiled: September 24, 2001Date of Patent: June 29, 2004Assignee: Akzo Nobel N.V.Inventors: Jaap van der Louw, Dirk Leysen, Roberta Burma Bursi
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Patent number: 6541465Abstract: Novel, orally active androgens are 7&agr;-substituted &Dgr;14-nandrolone derivatives. The compounds satisfy the general formula: wherein R1 is O, (H,H), (H,OR), NOR, with R being hydrogen, (C1-6) alkyl, or (C1-6) acyl; R2 is selected from the group consisting of (C2-4) alkyl, (C2-4) alkenyl, or (C2-4) alkynyl, each optionally substituted by halogen; or R2 is cyclopropyl, or cyclopropenyl, each optionally substituted by (C1-2) alkyl, or halogen; R3 is hydrogen, (C1-2) alkyl, or ethenyl; R4 is (C1-2) alkyl; R5 is hydrogen, or (C1-15) acyl; and the dotted lines indicate optional bonds.Type: GrantFiled: July 31, 2001Date of Patent: April 1, 2003Assignee: Akzo Nobel N.V.Inventors: Hubert Jan Jozef Loozen, Dirk Leysen, Jaap van der Louw
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Patent number: 6468981Abstract: A water soluble delivery system for nucleic acids to cells having androgen receptors, preferably prostate cells, is provided comprising a steroid moiety capable of binding to said receptors, said steroid moiety being covalently linked to a polycationic material. This molecule may be complexed with therapeutic or diagnostic nucleic acids. Methods of diagnosis and therapy using these compositions are also provided, including gene therapy treatments for prostate cancer.Type: GrantFiled: July 29, 1994Date of Patent: October 22, 2002Assignee: Emory UniversityInventors: John Anthony Petros, Dennis C. Liotta
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Patent number: 6313108Abstract: Novel, orally active androgens are 7&agr;-substituted &Dgr;14-nandrolone derivatives. The compounds satisfy the general formula: wherein R1 is O, (H,H), (H,OR), NOR, with R being hydrogen, (C1-6) alkyl, or (C1-6) acyl; R2 is selected from the group consisting of (C2-4) alkyl, (C2-4) alkenyl, or (C2-4) alkynyl, each optionally substituted by halogen; or R2 is cyclopropyl, or cyclopropenyl, each optionally substituted by (C1-2) alkyl, or halogen; R3 is hydrogen, (C1-2) alkyl, or ethenyl; R4 is (C1-2) alkyl; R5 is hydrogen, or (C1-15) acyl; and the dotted lines indicate optional bonds.Type: GrantFiled: July 11, 2000Date of Patent: November 6, 2001Assignee: Akzo Nobel N.V.Inventors: Hubert Jan Jozef Loozen, Dirk Leysen, Jaap van der Louw
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Patent number: 5977096Abstract: Novel substituted steroid compounds are disclosed which are more effective than known radical-trapping agents in methods of prophylaxis and therapy of radical-mediated cell damage and of treatment of diseases due to radical-mediated cell damage. The novel substituted steroid compounds can be made from steroids having an estrane, androstane, pregnane or cholestane basic skeleton and have a radical-attracting aromatic substituent of the general formula --(CH.sub.2).sub.n X, or .dbd.CH--(CH.sub.2).sub.m X at the 17 or 6 position of the steroid nucleus, wherein X=Y, OY, SY, SeY or NHY; n=0 to 5; m=n-1 and Y is a phenyl group having five substituents A, B, C, D and E, wherein A to E is independently H, alkyl, Oalkyl, Oacyl, OH, or one of the substituents B, C or D is NR.sub.2 wherein R=alkyl and each of the other substituents is hydrogen. Pharmaceutical compositions containing the novel substituted steroid compounds and methods of making them are also part of the invention.Type: GrantFiled: February 20, 1999Date of Patent: November 2, 1999Assignee: Jenapharm GmbH & Co. KGInventors: Peter Droescher, Bernd Menzenbach, Kurt Ponsold, Bernd Undeutsch, Michael Oettel, Wolfgang Romer, Gunter Kaufmann, Jens Schroder
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Patent number: 5952319Abstract: An androgenic steroid compound of the formula: ##STR1## wherein: X, Y, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.5 and R.sup.6 are as defined herein.Type: GrantFiled: November 26, 1997Date of Patent: September 14, 1999Assignee: Research Triangle InstituteInventors: C. Edgar Cook, John A. Kepler, Yue-Wei Lee, Mansukh C. Wani
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Patent number: 5925630Abstract: The invention relates to 3.alpha.-hydroxy, 17-(un)substituted derivatives of the androstane series and 3.alpha.-hydroxy, 21-substituted derivatives of the pregnane series. These derivatives are capable of acting at a recently identified site on the GRC, thereby modulating brain excitability in a manner that will alleviate stress, anxiety, insomnia, mood disorders that are amenable to GRC-active agents (such as depression) and seizure activity. The steroid derivatives of this invention are those having the general structural Formula: ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are further defined herein and the dotted lines are single or double bonds. The structure includes androstanes, pregnanes (R.sub.4 =methyl), 19-norandrostanes, and norpregnanes (R.sub.4 =H).Type: GrantFiled: June 6, 1996Date of Patent: July 20, 1999Assignee: CoCensys, Inc.Inventors: Ravindra B. Upasani, David B. Fick, Derk J. Hogenkamp, Nancy C. Lan
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Patent number: 5914324Abstract: 6-hydroxy and 6-oxo-androstane derivatives of formula (I), active on the cardiovascular system. ##STR1## wherein: the symbol A represents CH--OR, C.dbd.N--OR, CH--CH.dbd.N--OR and C.dbd.CH--N--OR; and R.sup.1, R.sup.2 and R.sup.3 are as defined herein.Type: GrantFiled: July 10, 1997Date of Patent: June 22, 1999Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Sergio De Munari, Elena Folpini, Marco Frigerio, Piero Melloni, Fulvio Serra, Simona Sputore
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Patent number: 5908944Abstract: This invention describes a new methylation or ethylation agent containing trimethyl aluminum or dimethyl zinc or triethyl aluminum as methyl or ethyl source, which additionally contains catalytic amounts of one or more copper(I) and/or copper(II) compounds as well as a process for the 1,4-addition of a methyl or ethyl group to an .alpha.,.beta.-unsaturated or an .alpha.,.beta.-double unsaturated ketone or an .alpha.,.beta.-unsaturated aldehyde using the agent according to the invention.By using only catalytic amounts of copper and a CKW (chlorinatedhydrocarbon)-free reaction medium, the new methylation/ethylation agent/process is distinguished by its environmental compatibility and it is, for example, suitable for the production of initial products for the synthesis of biologically effective compounds.Type: GrantFiled: September 30, 1994Date of Patent: June 1, 1999Assignee: Schering AktiengesellschaftInventors: Jurgen Westermann, Klaus Nickisch
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Patent number: 5723455Abstract: Novel antiandrogenic agents are provided. An exemplary group of compounds has the structural formula (I) ##STR1## wherein R.sup.1 through R.sup.10, a and b are as defined herein. Pharmaceutical compositions and methods for using the compounds of formula (I) to treat androgen-related clinical conditions are provided, as are methods and compositions for using the compounds as contraceptive agents.Type: GrantFiled: March 11, 1997Date of Patent: March 3, 1998Assignee: SRI InternationalInventors: Masato Tanabe, Wan-Ru Chao, Wesley K. M. Chong, David F. Crowe
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Patent number: 5597701Abstract: A process and appropriate device are disclosed for determining the androstenone content of adipose tissues in clearly shorter times. The disclosed process has the following steps: (a) liquefying an adipose tissue sample by heating up to a predetermined temperature in the 45.degree. to 60.degree. C.Type: GrantFiled: March 7, 1995Date of Patent: January 28, 1997Assignee: Riedel-De Haen AktiengesellschaftInventors: Rolf P. Claus, Martin Dehnhard
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Patent number: 5424304Abstract: Cardioactive steroidal compounds of the formula I ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 have the meanings shown in the description, and pharmaceutical compositions containing them.Type: GrantFiled: January 15, 1993Date of Patent: June 13, 1995Inventors: Giorgio Bertolini, Cesare Casagrande, Gabriele Norcini, Francesco Santangelo
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Patent number: 5266712Abstract: A process for crystallizing a pharmaceutically active steroidal product, without mechanical procedure, to obtain a homogeneous granulometric class which may be prepared beforehand, wherein the product which is desired to be crystallized is dissolved in a ternary mixture made of a lipophilic solvent, a hydrophilic solvent and a surface active agent at a temperature close to the boiling point of the mixture of solvents and wherein the mixture of solvents is allowed to revert to a temperature where the crystallization initiates, then, the thus-formed crystals are recovered.Type: GrantFiled: August 14, 1992Date of Patent: November 30, 1993Assignee: Laboratoire Theramex S.A.Inventor: Michel Lanquetin
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Patent number: 5227375Abstract: Novel aromatase inhibitors are disclosed for use in therapeutic preparations for treatment of estrogen-dependent diseases. The compounds are specified 7.alpha.-substituted androstanedione and androstenedione derivatives which show a strong inhibitory activity towards aromatase. The invention includes synthesis and pharmaceutical compositions of said compounds.Type: GrantFiled: February 8, 1990Date of Patent: July 13, 1993Assignee: Endorecherche, Inc.Inventors: Fernand Labrie, Yves Merand
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Patent number: 5093490Abstract: The invention relates to a process for the production of (+)-bicyclo[3.3.0]octan-3-one-2 carboxylic acid steroid esters of formula I ##STR1## in which X means oxygen or the radicals --O--(CH.sub.2).sub.n --O-- or --O--CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --O--,n means 2 or 3R.sub.2 means hydrogen or methyl,Y means the radicals X or X.sub.1,X.sub.1 means the radicals OCH.sub.3 or OCOR.sub.3,R.sub.3 means methyl, ethyl, phenyl, benzyl or pivalyl and the radical ##STR2## the radicals ##STR3## and X and X.sub.1 have the meanings indicated above, characterized in that D,L-bicyclo[3.3.0]octan-3-one-2 carboxylic acid esters of formula II ##STR4## in which X has the meaning indicated above and R is an alkyl group with 1-4 carbon atoms, with optically active steroids with a free 17'beta hydroxy group of formula III ##STR5## in which R.sub.Type: GrantFiled: November 13, 1989Date of Patent: March 3, 1992Assignee: Schering AktiengesellschaftInventor: Helmut Vorbrueggen