Patents Examined by Kimberly J. Kestler
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Patent number: 5449795Abstract: A method for the preparation of a steroidal allylic tertiary alcohol is disclosed which involves the deprotonation of a sulfoxide with a strong base which is capable of deprotonating the methine proton which is .alpha. to the sulfoxide, in an inert solvent to give the anion; reaction of the anion with a steroidal spiro-2'-oxirane to give a steroidal .gamma.-hydroxysulfoxide; and thermolysis in the presence of a base other than calcium carbonate to give the steroidal allylic tertiary alcohol.Type: GrantFiled: February 14, 1994Date of Patent: September 12, 1995Assignee: CoCensys, Inc.Inventor: Derk J. Hogenkamp
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Patent number: 5447924Abstract: Vitamin D analogues of the formula: ##STR1## wherein X is hydrogen or hydroxy; R.sup.1 and R.sup.2 are each hydrogen or C.sub.1 -C.sub.6 hydrocarbyl or R.sup.1 and R.sup.2 together with the starred carbon form a C.sub.3 -C.sub.8 carbocyclic ring; Q is a single bond or a C.sub.1 -C.sub.8 hydrocarbylene diradical; and m is 0, 1 or 2. One of the m carbons designated by .degree. may be optionally substituted with deuterium, fluorine or C.sub.1 -C.sub.2 alkyl. R.sup.1, R.sup.2 and/or Q may also be substituted with deuterium or fluorine. The analogues show, for example, anti-inflammatory and immunomodulating effects.Type: GrantFiled: September 22, 1992Date of Patent: September 5, 1995Assignee: Leo Pharmaceutical Products Ltd.Inventor: Claus Aage S. Bretting
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Patent number: 5446036Abstract: 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: November 2, 1993Date of Patent: August 29, 1995Assignee: Schering AktiengesellschaftInventors: Stefan Scholz, Eckhard Ottow, Guenter Neef, Walter Elger, Sybille Beier, Krzysztof Chwalisz
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Patent number: 5446035Abstract: New 20-methyl-substituted vitamin D derivatives of general formula I ##STR1## are described in whichR.sup.1 means a hydrogen atom, a hydroxy group or an alkanoyloxy group with 1 to 12 carbon atoms or a benzoyloxy group,R.sup.2 means a hydrogen atom or an alkanoyl group with 1 to 12 carbon atoms or a benzoyl group andR.sup.3 means a saturated or unsaturated, straight-chain or branched hydrocarbon radical with up to 18 C atoms, which optionally contains carbocyclic structures, optionally substituted with one or more hydroxy, oxo, amino group(s) and/or one or more halogen atom(s) as well as optionally exhibits one or more oxygen, sulfur and/or nitrogen atom(s) as a bridging link or links in the hydrocarbon radical, and a process for their production.Relative to calcitriol, the new compounds exhibit a greatly improved induction of cell differentiation (HL-60) and are suitable for the production of pharmaceutical agents.Type: GrantFiled: September 16, 1994Date of Patent: August 29, 1995Assignee: Schering AktiengesellschaftInventors: Gunter Neef, Andreas Steinmeyer, Gerald Kirsch, Katica Schwarz, Ruth Thieroff-Ekerdt, Herbert Wiesinger, Martin Haberey
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Patent number: 5446034Abstract: The invention relates to compounds of formula I in which formula X is hydrogen or hydroxy; R.sup.1 and R.sup.2 stand for hydrogen or a C.sub.1 -C.sub.6 hydrocarbyl radical; or taken together with the carbon atom bearing the group X, can form a C.sub.3 -C.sub.8 carbocyclic ring; R.sup.3 stands for hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl radical or for YR.sup.4, in which Y stands for the radicals --CO--, --CO--O--, --CO--S--, --CS--, --CS--O--, --CS--S--, --SO-- or SO.sub.2 --, and R.sup.4 stands for hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl radical; Q is a single bond or a C.sub.1 -C.sub.8 hydrocarbylene diradical. R.sup.1,R.sup.2,R.sup.3 and/or Q may be optionally substituted with one or more deuterium or fluorine atoms. The compounds show an antiinflammatory and immunomodulating effect as well as stong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells.Type: GrantFiled: April 4, 1994Date of Patent: August 29, 1995Assignee: Leo Pharmaceuitcal Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktiesel SKAB)Inventors: Claus Aage S. Bretting, Gunnar Grue-Sorensen
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Patent number: 5443971Abstract: A process for the separation of at least one isomer from a mixture of isomers of a tetrahydropyran-2-one, having at least two chiral centers which comprises selective reaction of at least one isomer with a reagent catalyzed by a hydrolase enzyme whereby at least one isomer is preferentially converted into a distinct chemical species from the other isomers so that it is susceptible of separation by an appropriate chemical or physical separation process in which the tetrahydropyran-2-one is of Formula (1): ##STR1## wherein: Z is --H or a protecting group susceptible of reaction with the reagent under the influence of the enzyme; andY is formyl or protected formyl.Type: GrantFiled: September 17, 1992Date of Patent: August 22, 1995Assignee: Zeneca LimitedInventors: Andrew J. Blacker, John Crosby, John A. L. Herbert
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Patent number: 5443970Abstract: A process for the separation of at least one isomer from a mixture of isomers of a tetrahydropyran-2-one, having at least two chiral centres, which comprises selective reaction of at least one isomer with a reagent catalysed by a hydrolase enzyme whereby at least one isomer is preferentially converted into a distinct chemical species from the other isomers so that it is susceptible of separation by an appropriate chemical or physical separation process in which the tetrahydropyranone is of Formula (1): ##STR1## wherein: Z is --H or a protecting group susceptible of reaction with the reagent under the influence of the enzyme; andY is optionally substituted hydrocarbyl.Type: GrantFiled: September 17, 1992Date of Patent: August 22, 1995Assignee: Zeneca LimitedInventors: Andrew J. Blacker, John Crosby, John A. L. Herbert
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Patent number: 5442080Abstract: The invention concerns a process of preparation of the polyazido alcohols by reaction of a polysubstituted oxirane having in position .beta. a nucleofuge group with a metal nitride, characterized in that the reaction is performed in an aqueous medium.The oxirane formula is: ##STR1## in which X represents a nucleofuge substituent, R1 represents an atom of hydrogen, a lower alkyl group substituted or not by a halogen, an aryl group possibly substituted, R2 and R3 represent an atom of hydrogen, a lower alkyl radical possibly substituted, an aryl group possibly substituted, R4 represents an atom of hydrogen, a lower alkyl group possibly substituted, an aryl group possibly substituted by an alkoxy group. Application to the preparation of polyamino alcohols, ureas, polyazidothiols and binding compositions for propergols.Type: GrantFiled: November 23, 1992Date of Patent: August 15, 1995Assignee: Etat Francais represente par le Delegue General pour l'ArmementInventors: Paul Caubere, Herve Forconi
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Patent number: 5442059Abstract: The invention provides compounds of the formula: ##STR1## wherein R, and R.sup.1 and W are defined in the specification. These compounds are useful as antibiotic agents.Type: GrantFiled: August 13, 1992Date of Patent: August 15, 1995Assignee: American Cyanamid CompanyInventors: Phaik-Eng Sum, Ving J. Lee, Raymond T. Testa
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Patent number: 5438049Abstract: A method for the treatment of inflammation, its signs and symptoms, in a mammal which comprises the administration of an anti-inflammatory effective amount of 16-epiestriol without glycogenic related adverse side-effects.Type: GrantFiled: August 12, 1993Date of Patent: August 1, 1995Inventors: Neal S. Latman, Virmal Kishore, Brent C. Bruot, Harold H. Flanders
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Patent number: 5430208Abstract: The present invention relates to a method of synthesizing 1-chloro-1-iodoethane by reacting hydrogen iodide with vinyl chloride monomer in the presence of an iodine containing catalyst under certain specified conditions. The resulting product of the reaction is a high yield, high purity 1-chloro-1-iodoethane which is useful as a chain transfer agent in the polymerization of vinyl chloride monomer. The 1-chloro-1-iodoethane formed by the instant invention can be made separately in a conventional synthesis apparatus or the compound can be synthesized in situ in the reaction vessel used for polymerization of vinyl chloride.Type: GrantFiled: May 19, 1994Date of Patent: July 4, 1995Assignee: The Geon CompanyInventors: Philip I. Bak, Gregory P. Bidinger, Ross J. Cozens, Paul R. Klich
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Patent number: 5430162Abstract: The invention provides compounds of formula ##STR1## wherein X, R and R.sup.1 are defined in the specification. These compounds are useful as antibiotic agents.Type: GrantFiled: March 21, 1994Date of Patent: July 4, 1995Assignee: American Cyanamid CompanyInventors: Phaik-Eng Sum, Ving J. Lee, Joseph J. Hlavka, Raymond T. Testa
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Patent number: 5428151Abstract: A process for the production of medrogestone, in which, in an intermediate step, the solvate 3.beta.,5.alpha.,6.beta.-trihydroxy-6.alpha.,17.alpha.-dimethylpregnan-20- one monomethanolate is obtained as a solid, stable compound by displacing the organic solvent from a solution of of 3.beta.,5.alpha.,6.beta.-trihydroxy-6.alpha.,17.alpha.-dimethylpregnan-20- one with a lower alkanol, and a Diels-Alder adduct of 6-methylene-17.alpha.-methylpregn-4-ene-3,20-dione with maleic anhydride is used as an intermediate for production of the corresponding dicarboxylic acid salt for removal of 6-methylene-17.alpha.-methylpregn-4-ene-3,20-dione contamination of the desired product. Another intermediate, 6.beta.-hydroxy-6.alpha.,17.alpha.-dimethylpregn-4-ene-3,20-dione, has been found to prevent smooth muscle proliferation and is useful in the treatment of atherosclerosis and restinosis.Type: GrantFiled: May 5, 1994Date of Patent: June 27, 1995Assignee: American Home Products CorporationInventors: Michael W. Winkley, Robert D. Mitchell
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Patent number: 5428181Abstract: A compound represented by the general formula: ##STR1## wherein A-O-denotes a residue of a compound having an estrogenic activity; R.sub.1 denotes H or a C.sub.1 -C.sub.6 alkyl group; X denotes a single bond, a C.sub.1 -C.sub.10 alkylene group or a group of the formula ##STR2## wherein R.sub.2 denotes H or a C.sub.1 -C.sub.5 alkyl group; Z denotes a nitro group or a halogen; n is an integer of 3 to 12; k is an integer of 1 to 5; L is an integer of 0 to 5; and q is an integer of 1 to 3,and physiologically acceptable salts thereof are disclosed.The compounds have a high affinity to bone tissues, and the compounds per se and metabolites thereof show significant therapeutic effect on bone diseases such as osteoporosis, rheumatoid arthritis and osteoarthritis.Type: GrantFiled: December 24, 1992Date of Patent: June 27, 1995Assignee: Hoechst Japan LimitedInventors: Tatsuo Sugioka, Mizuho Inazu
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Patent number: 5428029Abstract: Compounds of the formula ##STR1## wherein R is hydrogen, hydroxy, or fluorine, X is H.sub.2 or .dbd.CH.sub.2, and the 23,24-double bond is E or Z, are useful as agents for the treatment of hyperproliferative disorders of the skin such as psoriasis, as agents for the treatment of tumors such as breast cancer, as agents for the treatment of neoplastic diseases such as leukemia, and as agents for the treatment of sebaceous gland diseases such as acne and seborrheic dermatitis.Type: GrantFiled: November 24, 1993Date of Patent: June 27, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Thomas I. Doran, Bernard M. Hennessy, John A. McLane, Giacomo Pizzolato, Farhad Sedarati, Milan R. Uskokovic
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Patent number: 5428182Abstract: Bile acid derivatives of the formula IZ(X--GS)nin which GS, X, Z and n have the meanings indicated in the specification, and a process for the preparation of these compounds are described. The compounds are pharmacologically active and can, therefore, be used as pharmaceuticals, in particular as a hypolipidemic.Type: GrantFiled: June 10, 1993Date of Patent: June 27, 1995Assignee: Hoechst AktiengesellschaftInventors: Alfons Enhsen, Heiner Glombik, Werner Kramer, Gunther Wess
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Patent number: 5426102Abstract: Novel compounds of the general formula I ##STR1## and the pharmacologically tolerable addition salts thereof with acids are described, in which eitherIa) R.sup.11 represents a hydrogen atom in the .beta.-configuration and each of R.sup.12 and R.sup.13 represents a hydrogen atom, orIb) R.sup.11 represents a hydrogen atom in the .beta.-configuration and R.sup.12 and R.sup.13 together represent a second bond, orIc) R.sup.11 and R.sup.12 together represent a second bond and R.sup.13 represents a hydrogen atom, orId) R.sup.11 represents a hydrogen atom in the .alpha.-configuration and R.sup.12 and R.sup.13 together represent a second bond,and in Ia), Ib), Ic) or Id)X represents an oxygen atom, the hydroxyimino grouping >N.about.OH or two hydrogen atoms,R.sup.1 represents a hydrogen atom or a methyl group,R.sup.2 represents a hydroxy group, a C.sub.1 -C.sub.10 -alkoxy group or a C.sub.1 -C.sub.10 -acyloxy group, andR.sup.3 and R.sup.Type: GrantFiled: June 22, 1993Date of Patent: June 20, 1995Assignee: Schering AktiengesellschaftInventors: Wolfgang Schwede, Eckhard Ottow, Gunter Neef, Arwed Cleve, Krzysztof Chwalisz, Horst Michna
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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: 5424457Abstract: A process is provided which allows the isolation of sterols and a tocopherol concentrate in high yields from a deodorizer distillate (DOD) mixture obtained from the processing of, for example, soybean oils. Treatment of DOD with methanol at preferably 200.degree.-220.degree. C. in the presence of a monoalkyl- or dialkyl-tin compound results in the conversion of fatty acids and fatty acid esters into fatty acid methyl esters (FAME) and the liberation of free sterols and glycerin without appreciable degradation of tocopherols or sterols. The process can also be carried out in two steps where glycerin is used in the initial step and the fatty acids are converted into glycerides allowing the water of reaction to be removed as it is formed. The FAME produced by both methods are removed by a stripping operation to give a concentrate that allows the isolation of sterols in high yield and high purity and the isolation of a tocopherol concentrate by molecular distillation.Type: GrantFiled: May 27, 1994Date of Patent: June 13, 1995Assignee: Eastman Chemical CompanyInventors: Charles E. Sumner, Jr., Scott D. Barnicki, Martin D. Dolfi
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Patent number: 5420120Abstract: Topically administrable C-21 thioether glucocorticoid steroid derivatives are disclosed as effective anti-inflammatory agents for the treatment of ophthalmic inflammatory disorders. These C-21 thioether derivatives do not cause a significant increase in intraocular pressure as a side effect.Type: GrantFiled: December 17, 1993Date of Patent: May 30, 1995Assignee: Alcon Laboratories, Inc.Inventor: John J. Boltralik