Abstract: This invention relates to 8.alpha.-3-hydroxyestra- 1,3,5( 10),9( 11 )tetraen-17-one (.DELTA.9( 11 )-dehydro-8-isoestrone) (VI), ##STR1## to the process for its preparation, to pharmaceutical compositions containing said 8.alpha.-3-hydroxyestra- 1,3,5(10), 9(11)tetraen-17-one (.DELTA.9(11)-dehydro-8-isoestrone) (VI) and to the use of said 8.alpha.-3-hydroxyestra-1,3,5(10),9(11 )tetraen-17-one (A9( 11 )-dehydro-8-isoestrone) (VI) for modifying the balance between bone production and bone resorption, and as an antioxidant in a host animal, including man.
Type:
Grant
Filed:
April 8, 1994
Date of Patent:
March 7, 1995
Assignee:
American Home Products Corporation
Inventors:
Frederick O. Gemmill, Jr., Chester E. Orzech, Steven J. Adelman
Abstract: The new intermediate products of general formula I ##STR1## in which R.sup.1 stands for a hydrogen atom or a straight-chain or branched alkyl group with 1 to 4 carbon atoms,R.sup.2 stands for a hydrogen atom or a methyl group,R.sup.3 stands for a hydrogen atom,R.sup.4 stands for an acyloxy group with 1 to 4 carbon atoms in the acyl radical orR.sup.3 and R.sup.4 together stand for a keto-oxygen atom, are suitable in an excellent way for introducing a .DELTA..sup.1 double bond in the steroid skelton with the simultaneous presence of a .DELTA..sup.4 double bond, as well as a saturated carbonyl group, by clevage of hydrogen iodide with a base in an amidic solvent at elevated temperature. If R.sup.2 stands for a hydrogen atom, the A-ring is aromatized after the hydrogen iodide cleavage. For the production of a new intermediate products, special iodization processes, which partially also allow a stereoselective control of the iodization, are used.
Type:
Grant
Filed:
January 11, 1993
Date of Patent:
February 21, 1995
Assignee:
Schering Aktiengesellschaft
Inventors:
Jurgen Westermann, Klaus Nickisch, Michael Harre, Ralph Rohde
Abstract: This invention presents alkali metal salts of 8,9-dehydroestrone, its sulfate ester, and stable compositions thereof, as well as processes for their production. The sulfate ester salts are useful in estrogen replacement therapy.
Type:
Grant
Filed:
December 3, 1992
Date of Patent:
February 22, 1994
Assignee:
American Home Products Corporation
Inventors:
Panolil C. Raveendranath, John A. Wichtowski
Abstract: 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.
Abstract: Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## and their non-toxic, pharmaceutically acceptable acid addition salts possessing a remarkable antiglucocorticoidal activity.
Type:
Grant
Filed:
September 10, 1991
Date of Patent:
January 26, 1993
Assignee:
Roussel Ulcaf
Inventors:
Daniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
Abstract: A process for the production of 3-hydroxy-1,3,5(10)-estratrien-17-one by pyrolysis of 1,4-androstadiene-3,17-dione in the presence of 1,2,3,4-tetrahydronaphthalene as hydrogen donor is described, by 1,2,3,4-tetrahydronaphthalene, preheated to a temperature of 450.degree.-850.degree. C., in a mixing zone being mixed with a solution, heated to a temperature of up to 300.degree. C., of 1,4-androstadiene-3,17-dione, in 1,2,3,4-tetrahydronaphthalene, the mixture being heated in a pyrolysis zone at a retention time of 0.001 to 60 seconds to temperatures of 450.degree.-700.degree. C. and the product leaving the pyrolysis zone being cooled off, which is characterized in that the pyrolysis is performed under a pressure of 3.5.times.10.sup.6 to 3.times.10.sup.8 Pa.
Type:
Grant
Filed:
July 22, 1991
Date of Patent:
September 29, 1992
Assignee:
Schering Aktiengesellschaft
Inventors:
Michael Buback, Josef Hader, Hans-Peter Voegele, ZaKarya Al-Massri
Abstract: Deacylating agent represented by the formula (I): ##STR1## wherein R represents an insoluble polymer substituent, and R' and R" each represents an alkyl group, and a deacylation method using the above deacylating agent.
Abstract: 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.
Abstract: The present invention relates to an estrogen complex which consists of an estrogen or an estrogen derivative complexed with an organometallic compound containing at least one free carbonyl ligand, the said estrogen complex containing at least one free hydroxyl radical and no free phenolic hydroxyl radical in the .alpha.-position to the site where the organometallic compound is attached.The complexes according to the invention are useful for the determination of hormone receptors.
Type:
Grant
Filed:
July 24, 1988
Date of Patent:
January 8, 1991
Assignee:
Centre National de la Recherche Scientifique
Inventors:
Gerard Jaouen, Anne Vessieres, Siden Top
Abstract: Disclosed herein are (1) a fluorescent substance represented by the formula (I), (2) a process for producing the fluorescent substance, and (3) a cell-discriminating agent containing the fluorescent substance as an active ingredient. ##STR1## (wherein n is an integer of 0, 1, 2 or 3 and R represents a residual radical of a fluorescent material.
Abstract: A process for the production of 17.alpha.-ethinyl-17.beta.-hydroxy-18-methyl-4,15-estradien-3-one is described comprising reacting a 17-enolester of formula II ##STR1## wherein R.sub.1 represents an alkyl radical with 1-3 carbon atoms andR.sub.2 represents an acyl or a trialkylsilyl group with 1-10 carbon atomsunder palladium catalysis, with compounds of formula II ##STR2## wherein R.sub.1 represents an alkyl radical with 1-3 carbon atoms, reducing the 17-keto group to the 17-hydroxy group in a manner known in the art, reducing the aromatic A-ring according to Birch, with liquid ammonia, to 3-methoxy-2,5(10),15-estratrien-17.beta.-ol, reoxidizing the 17-hydroxy group to the 17-keto group, ethinylating the 17-keto group and splitting off the 3-enolether to form 17.alpha.-ethinyl-17.beta.-hydroxy-18-methyl-4,15-estradiene-3-one.
Type:
Grant
Filed:
March 31, 1988
Date of Patent:
May 8, 1990
Assignee:
Schering Aktiengesellschaft
Inventors:
Rolf Bohlmann, Henry Laurent, Helmut Hofmeister, Rudolf Wiechert