Additional Unsaturation In The Cyclopentanohydrophenanthrene Ring System Patents (Class 552/608)
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Publication number: 20140107089Abstract: Disclosed are compounds having the general formula: wherein R1-R4 and X are as defined herein, pharmaceutical compositions including such compounds, and a method of treating a patient involving antagonizing the endogenous progesterone, such as in inducing menses and treating endometriosis, dysmenorrhea, endocrine hormone-dependent tumors, meningiomas, uterine leiomyomas, or uterine fibroids, inhibiting uterine endometrial proliferation, inducing cervical ripening, inducing labor, and in contraception.Type: ApplicationFiled: September 10, 2013Publication date: April 17, 2014Applicant: The United States of America, as represented by the Secretary, Department of Health and Human ServInventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta, Anne Marie Simmons
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Patent number: 8586770Abstract: The invention relates to methods to manipulate stem cells in vivo and in vitro to treat, e.g., a condition where cell or tissue repair is needed.Type: GrantFiled: February 18, 2011Date of Patent: November 19, 2013Assignee: Harbor Therapeutics, Inc.Inventor: James M. Frincke
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Publication number: 20100120736Abstract: Compounds of the formula (I) are provided having a steroid skeleton and substitution characteristics in the A and B rings of the steroid skeleton effective for mineralocorticoid receptor antagonism, and rings C and D of the steroid skeleton having substituents thereon according to formula (I), wherein R1 is —OH or ?O; R2 is (C1-3)alkyl or (C2-3)alkenyl; R3 is selected from formulas (IIa), (IIb), (IIc). These compounds are useful in the treatment of inter alia aldosteronism, hypokalemia, hypertension, congestive heart failure, heart fibrosis, renal failure and restenosis.Type: ApplicationFiled: March 29, 2007Publication date: May 13, 2010Inventors: Bernardus Wijnand Machijs Marie Peeters, Marinus Bernard Groen, Ralf Plate
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Patent number: 6900193Abstract: The present invention relates, inter alia, to compounds having the general formula: in which: R1 is a member selected from the group consisting of —OCH3, —SCH3, —N(CH3)2, —NHCH3, —NC4H8, —NC5H10, —NC4H8O, —CHO, —CH(OH)CH3, —C(O)CH3, —O(CH2)2N(CH3)2, and —O(CH2)2NC5H10; R2 is a member selected from the group consisting of hydrogen, halogen, alkyl, acyl, hydroxy, alkoxy (e.g., methoxy, ethoxy, vinyloxy, ethynyloxy, cyclopropyloxy, etc.), acyloxy (e.g., acetoxy, glycinate, etc.), alkylcarbonate, cypionyloxy, S-alkyl, —SCN, S-acyl and —OC(O)R6, wherein R6 is a functional group including, but not limited to, alkyl (e.g., methyl, ethyl, etc.), alkoxy ester (e.g., —CH2OCH3) and alkoxy (—OCH3); R3 is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; R4 is a member selected from the group consisting of hydrogen and alkyl; and X is a member selected from the group consisting of ?O and ?N—OR5, wherein R5 is a member selected from the group consisting of hydrogen and alkyl.Type: GrantFiled: March 17, 2000Date of Patent: May 31, 2005Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta, Anne Marie Simmons
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Patent number: 6861415Abstract: A compound having the general formula: in which: R1 is a member selected from the group consisting of —OCH3, —SCH3, —N(CH3)2, —NHCH3, —CHO, —COCH3 and —CHOHCH3; R2 is a member selected from the group consisting of halogen, alkyl, acyl, hydroxy, alkoxy, acyloxy, alkyl carbonate, cypionyloxy, S-alkyl and S-acyl; R3 is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; R4 is a member selected from the group consisting of hydrogen and alkyl; and X is a member selected from the group consisting of ?O and ?N—OR5, wherein R5 is a member selected from the group consisting of hydrogen and alkyl.Type: GrantFiled: April 30, 1997Date of Patent: March 1, 2005Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Hyun K. Kim, Richard P. Blye, Pemmaraju N. Rao, James W. Cessac, Carmie K. Acosta
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Publication number: 20020002155Abstract: The subject of the invention is the products of formula (I): 1Type: ApplicationFiled: June 25, 2001Publication date: January 3, 2002Applicant: Hoechst Marion RousselInventors: Neerja Bhatnagar, Andre Claussner, Christian Marchandeau, Michele Resche Rigon, Jean-Georges Teutsch
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Patent number: 6310225Abstract: Steroid derivatives useful as intermediates for producing vitamin D derivates as well as processes for producing the steroid derivatives are provided. The steroid derivatives include halide compounds represented by the following formulae: wherein X, R1 and R2 are as defined by the specification.Type: GrantFiled: November 20, 2000Date of Patent: October 30, 2001Assignee: Kuraray Co., Ltd.Inventors: Yoshihisa Tsuji, Toshimichi Mitani
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Patent number: 6172052Abstract: The invention is directed to a novel class of 17&bgr;-acyl-17&bgr;-propynyl steroids which exhibit potent antiprogestational activity.Type: GrantFiled: December 4, 1998Date of Patent: January 9, 2001Assignee: Research Triangle InstituteInventors: C. Edgar Cook, John A. Kepler, Jill M. O'Reilly
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Patent number: 5994333Abstract: The invention relates to a method of altering hypothalamic function in an individual. The method comprises nasally administering a human vomeropherin, e.g. a pregnane or cholane steroid, or a pharmaceutical composition containing a vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers. Other embodiments of the invention include pharmaceutical compositions containing the steroids.Type: GrantFiled: August 3, 1995Date of Patent: November 30, 1999Assignee: Pherin CorporationInventors: Clive L. Jennings-White, David L. Berliner, Nathan William Adams
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Patent number: 5972922Abstract: Novel angiostatic .DELTA..sup.4,9(11) -steroids (I), ##STR1## C.sub.21 -oxygenated steroids (II) and other known steroidal compounds have been found to be useful in treating angiogenesis in mammals who have a need for the same. These steroids are useful in treating diseases of neovascularization such as cancer, diabetes and arthritis.Type: GrantFiled: December 21, 1995Date of Patent: October 26, 1999Assignee: Alcon Laboratories, Inc.Inventors: John W. Wilks, Thomas F. DeKoning, Paul A. Aristoff
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Patent number: 5827842Abstract: The invention describes 14,17-C.sub.2 -bridged steroids of general formula (I), ##STR1## wherein the various R groups are as defined in the specification, and wherein said steroids are, in contrast with the disclaimed compound 14,17-ethano-19-norpregn-4-ene-3,20-dione bioavailable even after peroral administration with high gestagenic action and are suitable for the production of pharmaceutical agents.Type: GrantFiled: December 26, 1995Date of Patent: October 27, 1998Assignee: Schering AktiengesellschaftInventors: Klaus Schollkopf, Wolfgang Halfbrodt, Joachim Kuhnke, Wolfgang Schwede, Karl-Heinrich Fritzemeier, Rolf Krattenmacher, Hans-Peter Muhn
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Patent number: 5739125Abstract: The invention relates to 11.beta.-aryl-gona-4,9-dienes of formula I ##STR1## wherein the variables are defined in the specification. The compounds are progesterone synthesis inhibitors and are suitable for inducing labor or an abortion, and for treating endometriosis, dysmenorrhea, and endocrine hormone-dependent tumors.Type: GrantFiled: February 21, 1995Date of Patent: April 14, 1998Assignee: Schering AktiengesellschaftInventors: Helmut Kasch, Gudrun Bertram, Kurt Ponsold, Gerd Schubert, Heidemarie Rohrig, Anatoli Kurischko, Bernd Menzenbach
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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: 5616743Abstract: A compound having the formulae selected from the group consisting of ##STR1## wherein R.sub.2 and R.sub.3 are hydrogen or R.sub.2 is fluorine and R.sub.3 is formyloxy or acetyloxy, the dotted line in 9(11) position indicates an optional double bond and the dotted line in position 16(17) indicates an optional double bond ##STR2## is a 3-keto-.DELTA..sup.4 -system or 3-keto-.DELTA..sup.1,4 -system or 3-OR.sub.4 -.DELTA..sup.5 -system, R.sub.4 is hydrogen or a protector group of hydroxy, R is --CH.sub.3, --CH.sub.2 OH or --CH.sub.2 --OR', R' is a hydroxy protector group and R'.sub.1 is selected from the group consisting of methyl, a branched alkyl of 5 to 8 carbon atoms not possessing hydrogen in the .beta.-position, aryl of up to 10 carbon atoms and benzyl, hetroaryl of up to 10 carbon atoms and at least one heteroatom selected from the group consisting of nitrogen, sulfur and oxygen, with the exception of the compounds of formula Vc in which R is methyl, R.sub.2 and R.sub.3 are hydrogen or R.sub.2 and R.sub.Type: GrantFiled: January 13, 1995Date of Patent: April 1, 1997Assignee: Roussel UCLAFInventors: Jean Boivin, Samir Zard, Christine Chauvet
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Patent number: 5352808Abstract: A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms optionally substituted by halogen or a nitrogen or oxygen function and alkenyl and alkynyl of 2 to 4 carbon atoms, R.sub.2 is alkyl of 1 to 4 carbon atoms and the A, B, C and D rings are optionally substituted by at least one member of the group consisting of optionally protected --OH or .dbd.0, halogen, alkyl and alkoxy of 1 to 4 carbon atoms and alkenyl and alkynyl of 2 to 4 carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.1 and R.sub.2 and the A, B, C and D rings are defined as above with an oxidizing agent in the presence of water and an at least partially water-miscible solvent to obtain a compound of the formula ##STR3## wherein R.sub.1 and R.sub.Type: GrantFiled: November 5, 1992Date of Patent: October 4, 1994Assignee: Roussel UclafInventors: Jean Buendia, Michel Vivat
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Patent number: 5273971Abstract: There are provided 13-alkyl-11beta-phenyl-gonanes of formula I ##STR1## wherein Z is an oxygen atom or N--OH;R.sup.2 is alpha- or beta-position methyl or ethyl;R.sup.1 is selected from heteroaryl radicals, cycloalkyl radicals, cycloalkenyl radicals, aryl radicals, alkenyl radicals, and alkyl radicals where R.sup.2 is in the alpha-position and an ethyl radical where R.sup.2 is in the beta-position; andR.sup.3 and R.sup.4 are selected from one of two different groups of substituent pairs, the group from which the selection is made being determined by the position of R.sup.2.Type: GrantFiled: July 3, 1989Date of Patent: December 28, 1993Assignee: Schering AktiengesellschaftInventors: Stefan Scholz, Eckhard Ottow, Guenter Neef, Walter Elger, Sybille Beier, Krzysztof Chwalisz
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Patent number: 5272140Abstract: The invention relates to 11-aryl steroid derivatives, having the structure ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as described in the specificationand to processes for their preparation and to pharmaceuticals comprising these compounds.These compounds exhibit a strong anti-progestinic activity and a weak or non-existent anti-glucocorticoid activity.Type: GrantFiled: February 27, 1990Date of Patent: December 21, 1993Assignee: Akzo N.V.Inventor: Hubert J. J. Loozen
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Patent number: 5140106Abstract: A process for the production of 3-deoxy-4-ene steroids of the general formula I ##STR1## is described, in which R.sub.1, R.sub.2 and R.sub.3 mean a hydrogen atom or a methyl group,R.sub.4 represents a lower alkyl group, a phenyl group or a free, esterified or etherified hydroxy group,R.sub.5 symbolizes a hydrogen atom, a vinyl group or the grouping --C.tbd.CR.sub.6 with R.sub.6 meaning a hydrogen atom, an alkyl group with a maximum of 4 carbon atoms or a halogen atom,X represents a methylene group, a fluoromethylene group, an ethylidene group or a vinylidene group,Y and U represent a methylene group or an ethylidene group andZ symbolizes a methylene group, an ethylidene group, a vinylidene group, a chloromethylene group or a hydroxymethylene group and in which the bonds represent three single bonds or one double bond and two single bonds or a conjugated double bond.Type: GrantFiled: January 17, 1991Date of Patent: August 18, 1992Assignee: Schering AktiengesellschaftInventors: Ekkehard Winterfeldt, Ulf Tilstamm, Helmut Hofmeister, Henry Laurent
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Patent number: 5086047Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl, alkylthio and haloalkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, optionally substituted arylthio of 6 to 10 carbon atoms, aryl of 6 to 12 carbon atoms, acyl of an organic carboxylic acid of 1 to 12 carbon atoms, --CN, cycloalkyl of 3 to 6 carbon atoms and --(CH.sub.2).sub.m --Re, m is an integer from 1 to 3, Re is --OH or --SH or --Salk, Alk is alkyl of 1 to 6 carbon atoms, X is selected from the group consisting of oxygen, N--O--R.sub.1, ##STR2## or =X is H.sub.2 or ##STR3## R.sub.A and R.sub.B are individually selected from the group consisting of hydrogen, halogen and alkyl of 1 to 6 carbon atoms, R.sub.1 is hydrogen or alkyl of 1 to 6 carbon, R' is hydrogen or acyl, the wavy lines indicate --or -position, Y is selected from the group consisting of oxygen, NOR, ##STR4## or =Y is ##STR5## H.sub.Type: GrantFiled: December 24, 1990Date of Patent: February 4, 1992Assignee: Roussel Uclaf, Department des BrevetsInventors: Jean-Francois Gourvest, Dominique Lesuisse
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Patent number: 5073548Abstract: A 11.beta.-aryl-19-norprogesterone steroid of the formula: ##STR1## wherein (i) R.sup.1 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, OH, OC(O)CH.sub.3, or OC(O)R.sup.5 , wherein R.sup.5 is C.sub.2-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl or aryl, R.sub.2 is H, R.sup.3 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl, R.sup.4 is H, CH.sub.3, F or Cl, R.sup.6 is H, (CH.sub.3).sub.2 N, CH.sub.3 O, CH.sub.3 CO, CH.sub.3 S, CH.sub.3 SO, CH.sub.3 SO.sub.2, and X is O or NOCH.sub.3 ; or(ii) R.sup.1 and R.sup.2 taken together are a carbon-carbon bond and R.sup.3, R.sup.4, R.sup.6 and X are as defined above; or(iii) R.sup.1 and R.sup.3 taken together are --CH.sub.2 -- or --N.dbd.N--CH.sub.2 --, R.sup.2 is H and R.sup.4, R.sup.6 and X are as defined above; or(iv) R.sup.2 and R.sup.3 taken together are .dbd.CH.sub.2 and R.sup.1 , R.sup.4, R.sup.6 and X are as defined above.Type: GrantFiled: April 3, 1990Date of Patent: December 17, 1991Assignee: Research Triangle InstituteInventors: C. Edgar Cook, Mansukh C. Wani, Yun W. Lee, Jerry R. Reel, Douglas Rector
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Patent number: 5064822Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of naphthyl, phenylphenyl, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms optionally containing additional unsaturations, phenoxy, furyl, cycloalkyl of 3 to 6 carbon atoms, thienyl optionally substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of --OH, halogen, --CF.sub.3, alkyl and alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, phenoxy and alkylthio of 1 to 6 carbon atoms optionally oxidized to the sulfoxide or sulfone, R.sub.2 is selected from the group consisting of methyl and ethyl, R.sub.Type: GrantFiled: November 16, 1989Date of Patent: November 12, 1991Assignee: Roussel UclafInventors: Daniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
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Patent number: 4954490Abstract: A 11.beta.-aryl-19-norprogesterone steroid of the formula: ##STR1## wherein (i) R.sup.1 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, OH, OC(O)CH.sub.3, or OC(O)R.sup.5, wherein R.sup.5 is C.sub.2-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl or aryl, R.sub.2 is H, R.sup.3 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl, R.sup.4 is H, CH.sub.3, F or Cl, R.sup.6 is H, (CH.sub.3).sub.2 N, CH.sub.3 O, CH.sub.3 CO, CH.sub.3 S, CH.sub.3 SO, CH.sub.3 SO.sub.2, and X is O or NOCH.sub.3 ; or(ii) R.sup.1 and R.sup.2 taken together are a carbon-carbon bond and R.sup.3, R.sup.4, R.sup.6 and X are as defined above; or(iii) R.sup.1 and R.sup.3 taken together are --CH.sub.2 -- or --N.dbd.N--CH.sub.2 --, R.sup.2 is H and R.sup.4, R.sup.6 and X are as defined above; or(iv) R.sup.2 and R.sup.3 taken together are .dbd.CH.sub.2 and R.sup.1, R.sup.4, R.sup.6 and X are as defined above.Type: GrantFiled: June 23, 1988Date of Patent: September 4, 1990Assignee: Research Triangle InstituteInventors: C. Edgar Cook, Mansukh C. Wani, Y.-W Lee, Jerry R. Reel, Douglas Rector
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Patent number: 4921638Abstract: The invention is the compound 17.beta.-cyano-9.alpha., 17.alpha.-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17.alpha.-halo silyl ethers (II).Type: GrantFiled: October 3, 1988Date of Patent: May 1, 1990Assignee: The Upjohn CompanyInventors: Douglas A. Livingston, Bruce A. Pearlman, Scott Denmark, Joel E. Huber
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Patent number: 4913852Abstract: Compounds obtained from the associative synthesis of sulfur-containing or sulfur-free amino acids with derivatives of .DELTA.-4-pregnene-3,20-dione or with derivatives of .DELTA.-1,4-pregnadiene-3,20-dione of the general formulas (I), (II) and (III), having glucocorticoidal and anti-inflammatory properties have been prepared and tested. Pharmaceutical compositions, medicaments containing them as well as their applications are claimed, particularly in the cutaneous and ophthalmic fields.Type: GrantFiled: February 24, 1988Date of Patent: April 3, 1990Inventors: Catherine Milioni, Constantin Efthyimiopoulos, Bernard Koch, Louis Jung, Jean Jung