Carbonyl Attached Directly Or Indirectly To Silicon By Nonionic Bonding Patents (Class 556/436)
- Silicon and the carbon of the -COO- group are bonded directly to the same hydrocarbon group (Class 556/438)
- Silicon and the oxy of the -COO- group are bonded directly to the same hydrocarbon group (Class 556/440)
- Carbocyclic ring having silicon as part of one substituent and the -COO- as part of another substituent (Class 556/441)
- Silicon is bonded directly to the oxy of the -COO- group (Class 556/442)
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Patent number: 5124467Abstract: The instant invention relates to polysiloxane polyoxyalkylene compounds containing at least one perfluoroalkyl terminated polyoxyalkylene group. These compounds are useful as surfactants and improve or impart properties such as wetting, penetration, spreading, levelling, foam stability, flow properties, dispersion properties and oil and water repellency.Type: GrantFiled: July 20, 1990Date of Patent: June 23, 1992Assignee: Ciba-Geigy CorporationInventors: Juliana Rodgers, Athanasios Karydas
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Patent number: 5124468Abstract: Silicon hydrides substituted with oxygen containing radicals such as alkoxy, can be silylformylated with alkynes and carbon monoxide in the presence of a rhodium catalyst to produce silyl alkenyl acetals. The silyl alkenyl acetals are useful as plasticizers for organosilicon copolymers.Type: GrantFiled: August 2, 1991Date of Patent: June 23, 1992Assignee: General Electric CompanyInventors: Terry E. Krafft, Jonathan D. Rich, Timothy B. Burnell
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Patent number: 5118839Abstract: A process for preparing nitro substituted polyarylketones of the formula: ##STR1## is disclosed. The process involves the condensation of ##STR2## where R.sub.A is hydrogen, --COOH, or C.sup.1 to C.sub.12 linear or branched alkyl, Y and Y' are the same or different and are a chemical bond ##STR3## or --Si(CH.sub.3).sub.2 -- and m is 0 or 1 and X is halo. These nitro groups of these compounds can be reduced to provide the corresponding amines, which are useful for the preparation of thermally stable high melting polyimides.Type: GrantFiled: September 4, 1990Date of Patent: June 2, 1992Assignee: Ethyl CorporationInventors: Allan A. Eisenbraun, Venkataraman Ramachandran
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Patent number: 5113003Abstract: The silicon-containing phenoxy ethers are of the formula III: ##STR1## wherein R.sup.1 and R.sup.2 which may be the same or different are selected from H, --R.sup.3 --X, aliphatic hydrocarbyl having 1-6 carbon atoms or aryl, or substituted derivatives thereof, provided that not more than one of R.sup.1 and R.sup.2 is H;R.sup.3 is a divalent C.sub.1 -C.sub.30 aliphatic and/or aromatic hydrocarbyl group which may optionally be substituted, or interrupted, by a hetero atom;R.sup.4 and R.sup.5 which may be the same or different are H, ##STR2## or an ortho para directing activating group for aromatic electrophilic substitution, other than an amine;and X is a reactive functional group capable of undergoing an acid-catalyzed electrophilic aromatic substitution reaction with a phenol, for example an aldehyde group. They can be polymerized to produce silicone-modified polymers of the phenol-aldehyde type without the use of free aldehyde.Type: GrantFiled: March 20, 1991Date of Patent: May 12, 1992Assignee: Loctite (Ireland) LimitedInventors: John G. Woods, Pauline Coakley
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Patent number: 5107010Abstract: The present invention related to novel compounds useful in the manufacture of astaxanthin and to processes for their preparation.The novel intermediates have the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are C.sub.1-6 -alkyl which may be branched or phenyl, and ##STR2## wherein R.sup.1 is alkyl, alkoxy, NO.sub.2, NH.sub.2 or halogen.Type: GrantFiled: December 12, 1990Date of Patent: April 21, 1992Assignee: NeuroSearch A/SInventor: Peter Moldt
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Patent number: 5087619Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or hydroxy, R.sub.5 is hydrogen, and A is --C.tbd.C--, ##STR2## or --CH.sub.2 --CH.sub.2 --, with the proviso that when A is --C.tbd.C--, R.sub.5 may also be deuterium, are described.The compounds of formula I are useful as agents for the treatment of hyperproliferative disorders of the skin such as psoriasis, as agents for the treatment of neoplastic diseases such as leukemia, and as agents for the treatment of sebaceous gland diseases such as acne or seborrheic dermatitis.Type: GrantFiled: March 23, 1990Date of Patent: February 11, 1992Assignee: Hoffman-La Roche Inc.Inventors: Enrico G. Baggiolini, deceased, Barbara J. Baggiolini, Bernard M. Hennessy, Shian-Jan Shiuey, Gary A. Truitt, Milan R. Uskokovic
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Patent number: 5087717Abstract: Organotrialkoxysilane stabilizers for inorganic silicate corrosion inhibitor additives in antifreezer/coolant formulations are described. The stabilizers have the following structure; ##STR1## wherein R is an alkyl group of 1-4 carbon atoms, R.sub.1 is either ##STR2## and R.sub.2 may be selected from ##STR3## and R.sub.3 is phenyl or ##STR4## These stabilizers help prevent the gelling of the corrosion inhibiting silicate additives in antifreezer/coolant formulations thereby increasing the useful lifetime of such formulations.Type: GrantFiled: September 10, 1990Date of Patent: February 11, 1992Assignee: Korea Advanced Institute of Science and TechnologyInventors: Il Nam Jung, Sang Yo Hwang, Hae Kyung Bae
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Patent number: 5086192Abstract: Disclosed are siloxanyl-substituted diaromatic iodonium salts such as 4-[3-1,1,3,3,5,5,5-heptamethyl siloxanyl propoxy]phenyl-phenyliodonium hexafluoroantimonate. These diaryl iodonium salts are useful as photoinitiators for epoxy containing compounds, especially epoxypolysiloxanes. Also disclosed is a process for the preparation of a siloxanyl-substituted diaromatic iodonium salt.Type: GrantFiled: December 14, 1990Date of Patent: February 4, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventors: Carl R. Kessel, Tracy R. Woodward
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Patent number: 5084577Abstract: Novel volatile silicon compounds are disclosed which are very suitable for use in cosmetic and household products.Type: GrantFiled: January 3, 1991Date of Patent: January 28, 1992Assignee: The Procter & Gamble CompanyInventor: Raymond E. Bolich, Jr.
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Patent number: 5064961Abstract: A process for the preparation of the optically active compound [IR-(1.alpha., 2.beta., 3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-6H-purin-6-one, represented by the formula: ##STR1## and novel intermediates are described.Type: GrantFiled: December 18, 1989Date of Patent: November 12, 1991Assignee: E. R. Squibb & Sons, Inc.Inventors: Gregory S. Bisacchi, Toomas Mitt
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Patent number: 5061817Abstract: The present invention relates to .beta.-lactam compound having the formula (I): ##STR1## wherein R.sup.1 is a trialkylsilyl group, dimethyl-1,1,2-trimethylpropylsilyl group, acetyl group, benzyloxycarbonyl group, O-nitrobenzyloxycarbonyl group, p-nitrobenzyloxycarbonyl group or t-butyl group, R.sup.2, R.sup.3 and R.sup.4 are a member selected from the group consisting of a lower alkyl group having 1 to 6 carbon atoms, phenyl group and an aralkyl group and a process for preparing the compound which comprises reacting enolsilylethers having the formula (III): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as above, with chlorosulfonylisocyanate and then reducing the obtained product. The .beta.-lactam compound of the present invention is a useful intermediate for preparing carbapenem .beta.-lactam compound.Type: GrantFiled: May 31, 1988Date of Patent: October 29, 1991Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Takeisa Ohashi, Kazunori Kan, Noboru Ueyama, Isao Sada, Akimasa Miyama, Kiyoshi Watanabe
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Patent number: 5055592Abstract: This invention relates to the novel processes for the preparation of a 16-methoxy-16-methyl prostaglandin E.sub.1 derivative and to the novel intermediates useful therefor.Type: GrantFiled: January 30, 1990Date of Patent: October 8, 1991Assignee: Merrell Dow PharmaceuticalsInventors: Michael Kolb, Luc Van Hijfte
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Patent number: 5041587Abstract: A process for preparing an organic silicon compound is here disclosed which comprises the step of reacting a halogenated hydrocarbon selected from the group consisting ##STR1## wherein each of X.sup.1 to X.sup.16 is selected from the group consisting of hydrogen, an alkyl group, alkenyl group, phenyl group, naphthyl group, alkoxy group, acyl group, alkylamino group and dialkylamino group having 1 to 20 carbon atoms which are unsubstituted or substituted and a halogen atom; and each of at least one of X.sup.1 to X.sup.4, at least one of X.sup.8 to X.sup.10 and at least one of X.sup.11 to X.sup.16 is a halogen atom,with a silane selected from the group consisting of SiH.sub.4, Si.sub.2 H.sub.6 and Si.sub.3 H.sub.8.Type: GrantFiled: February 12, 1990Date of Patent: August 20, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Masayoshi Itoh, Kenji Iwata, Noriyuki Yanagawa, Tetsura Utsumi, Mineo Kobayashi, Ryo Takeuchi, Tomohiro Abe
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Patent number: 5037855Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom. R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.Type: GrantFiled: November 17, 1989Date of Patent: August 6, 1991Assignee: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 5025053Abstract: Linear and cyclic diorganopolysiloxanes containing dibenzoylmethane functional groups are well suited for the coating of optical fibers and for lubricating plastics, e.g., PVC.Type: GrantFiled: August 4, 1989Date of Patent: June 18, 1991Assignee: Rhone-Poulenc ChimieInventors: Edith Canivenc, Serge Forestier, Michel Gay, Gerard Lang, Herve Richard
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Patent number: 5021601Abstract: Novel linear or branched O.sub.2 -curable polyorganosiloxanes containing propanaldehyde functional groups and at least three recurring siloxyl units per molecule, at least one unit of which corresponds to the general formula: ##EQU1## in which X is the radical --CH.sub.2 --CH.sub.2 CHO or the radical ##STR1## and R is a monovalent hydrocarbon residue containing from 1 to 12 carbon atoms, are prepared by hydroformylation of the corresponding polyorganosiloxane in an organic phase by means of a catalyst system which is soluble in the organic phase but insoluble in aqueous phase, such catalyst system including a rhodium/sulfonated or carboxylated triarylphospine salt complex.Type: GrantFiled: September 5, 1989Date of Patent: June 4, 1991Assignee: Rhone-Poulenc ChimieInventors: Jean-Marc Frances, Francois Metz
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Patent number: 5019590Abstract: A process for synthesizing oxygen-containing polyoxatetracycle compounds and in particular analogs of the antimalarial agent known as qinghaosu or artemisinin is disclosed. The process employs as a reactant an olefinically unsaturated bicyclic bridging ketone having nonenolizable bridgehead moieties for both of its alpha positions. This ketone is converted to a vinylsilane that is subjected to ozonolytic cleavage of its olefinic bond to yield a member of a family of unique carboxyl/carbonyl-substituted vinylsilanes which may in turn optionally be subjected to a wide range of reactions prior to a final ozonolysis/acidification step which closes the oxygen-containing ring structure. The various intermediates are claimed as aspects of this invention as are novel tetracycles and their use as antimalarials.Type: GrantFiled: September 27, 1989Date of Patent: May 28, 1991Assignee: SRI InternationalInventors: Mitchell A. Avery, Wesley K. M. Chong
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Patent number: 5017718Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.Type: GrantFiled: January 26, 1984Date of Patent: May 21, 1991Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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Patent number: 5008425Abstract: A process which comprises reacting under substantially anhydrous conditions a perfluoroalkyltrihydrocarbylsilane and a carbonyl compound in the presence of a catalyst such that the carbonyl compound is perfluoroalkylated.Type: GrantFiled: April 12, 1989Date of Patent: April 16, 1991Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4992584Abstract: A process is disclosed for the preparation of .beta.-ketocarboximides of .alpha.,.beta.-unsaturated amides from 1,3-dioxin-4-ones and .alpha.,.beta.-unsaturated amides using an inert solvent system capable of maintaining both reactants substantially in homogeneous solution throughout the reaction. This process provides greatly improved yields of .alpha.,.beta.-ketocarboximides of .alpha.,.beta.-unsaturated amides as well as a simple method of recovering same since such products can readily be precipitated from the reaction mixture.Type: GrantFiled: August 12, 1988Date of Patent: February 12, 1991Assignee: Eastman Kodak CompanyInventor: Robert J. Clemens
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Patent number: 4982006Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.Type: GrantFiled: May 1, 1989Date of Patent: January 1, 1991Assignee: Norwich Eaton Pharmaceuticals, Inc.Inventor: Thomas T. Hudec
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Patent number: 4963683Abstract: A process for synthesizing polyoxa tetracyclics which involves the ozonolysis of a single-ring-structure vinyl silane with resulting direct formation of the desired multiple ring matrial. The polyoxa tetracyclic compounds have the formula ##STR1## The vinyl silanes have the structure ##STR2## The vinyl silanes are new chemical compounds as are corresponding primary ozonide and dioxetane intermediates. In a preferred embodiment, this invention provides a total synthesis of the antimalarial artemisinin.Type: GrantFiled: February 15, 1989Date of Patent: October 16, 1990Assignee: SRI InternationalInventors: Mitchell A. Avery, Clive Jennings-White
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Patent number: 4956484Abstract: A process for producing a silane or siloxane compound containing at least one cycloalkyl ring by hydrogenation of a corresponding derivative containing at least one aromatic ring in the presence of a Raney nickel catalyst modified with chromium.Type: GrantFiled: March 3, 1988Date of Patent: September 11, 1990Assignee: Instituto Guido Donegani S.p.A.Inventors: Francesco Gementi, Loris Sogli, Raffaele Ungarelli
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Patent number: 4940813Abstract: A process is described for the preparation of an optically active carboxylic acid or ester derivative thereof from a ketene and an optically active .alpha.-hydroxyester or an .alpha.-hydroxy amide.Type: GrantFiled: March 31, 1989Date of Patent: July 10, 1990Assignee: Merck & Co., Inc.Inventors: Edward G. Corley, Robert D. Larsen, Edward J. J. Grabowski, Paul Reider
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Patent number: 4940765Abstract: 3-Benzylidenecamphor-substituted diorganopolysiloxanes, well adopted for incorporation into coating and lubricant compositions (notably as a lubricant for PVC), have the structural formulae (1) and (2) ##STR1## wherein A and/or B is a 3-benzylidenecamphor moiety.Type: GrantFiled: December 29, 1988Date of Patent: July 10, 1990Assignee: Rhone-Poulenc ChimieInventors: Edith Canivenc, Serge Forestier, Michel Gay, Gerard Lang, Herve Richard
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Patent number: 4929740Abstract: Compounds of the formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or an ether-forming group and X is hydrogen, halo, trifluoromethyl, lower alkyl, or lower akoxy, are useful intermediates for making PGE and PGF derivatives having an allenic function.Type: GrantFiled: July 11, 1988Date of Patent: May 29, 1990Assignee: Syntex (U.S.A.) Inc.Inventor: Gary F. Cooper
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Patent number: 4925956Abstract: The invention relates to a process for manufacturing optically active carbacyclin intermediate products from racemic cis-bicyclo[3.3.0]octane-2-carboxylic acids. This process makes it possible in an advantageous way to produce important intermediates for the synthesis of stable and pharmacologically active carbacyclin derivatives.Type: GrantFiled: July 13, 1988Date of Patent: May 15, 1990Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Helmut Dahl
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Patent number: 4918197Abstract: A method is provided for silylating aromatic acylhalide by effecting reaction between an aromatic acylhalide and halogenated polysilane in the presence of an effective amount of a supported transition metal catalyst, such as a transition metal catalyst supported by an organic or inorganic substrate.Type: GrantFiled: August 15, 1988Date of Patent: April 17, 1990Assignee: General Electric CompanyInventors: Jonathan D. Rich, Terry E. Krafft, Philip J. McDermott
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Patent number: 4914221Abstract: The invention relates to dimethylsilyl-substituted benzoyl chlorides and a process for preparing the same, which comprises reacting a dihaloaromatic compound with dimethylchlorosilane and magnesium by the Grignard method to form halophenyldimethylsilanes, then reacting the halophenyldimethylsilanes with magnesium in the presence of carbon dioxide to form the corresponding dimethylsilyl-substituted benzoic acids, and thereafter reacting the dimethylsilyl-substituted benzoic acids with a halogenating agent, such as thionyl chloride, to form dimethylsilyl-substituted benzoyl chlorides.Type: GrantFiled: August 8, 1988Date of Patent: April 3, 1990Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Peter-Paul Winkler, Franz-Heinrich Kreuzer
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Patent number: 4914220Abstract: A process is described for the synthesis of E-2-methyl-.alpha.,.beta.-unsaturated aldehydes, which are useful as intermediates in the synthesis of the macrolide structure of the immunosuppressant FK-506. These compounds are also useful as ultraviolet radiation absorbers.Type: GrantFiled: February 27, 1989Date of Patent: April 3, 1990Assignee: Merck & Co., Inc.Inventors: Richard Desmond, Sander G. Mills, Ralph P. Volante, Ichiro Shinkai
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Patent number: 4898855Abstract: The invention is directed to deuterated vitamin D analogs, and processes and intermediates for their preparation. The end products, that is the deuterated vitamin D analogs, are useful for the treatment osteoporosis and cutaneous inflammations such as psoriasis, and contact dermatitis.Type: GrantFiled: September 14, 1987Date of Patent: February 6, 1990Assignee: Hoffman-La Roche Inc.Inventors: Enrico G. Baggiolini, Bernard M. Hennessy, Milan R. Uskokovic
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Patent number: 4880705Abstract: A method of combining a siloxy group (--SiO--) with a ketene-reactive compound to form a siloxy-containing product comprises:(a) subjecting a silyl diketone to photolysis under conditions effective for generating a siloxy ketene intermediate therefrom, said silyl diketone having the formula ##STR1## wherein Si is silicon, R.sub.1 and R.sub.4 are hydrocarbon groups containing from 1 to 18 carbons, and R.sub.2 and R.sub.Type: GrantFiled: December 22, 1988Date of Patent: November 14, 1989Assignee: Minnesota Mining & Manufacturing CompanyInventor: Bradford B. Wright
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Patent number: 4876399Abstract: The present invention is directed to novel taxols useful as a chemotherapeutic agent. Moreover, the present invention is directed to the process of preparing taxols and various intermediates in said process. A key intermediate is this process is 2,5-dihydroxy-2-patchoulenes. Therefore the present invention is also related to said intermediate and the process for its preparation.Type: GrantFiled: November 2, 1987Date of Patent: October 24, 1989Assignee: Research Corporation Technologies, Inc.Inventors: Robert A. Holton, Rouh-Rong Juo, Richard Lowenthal
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Patent number: 4871869Abstract: New intermediate, an optically active (1R,5S,6S,7R)-6-tert-butyldiphenylsilyloxmethyl-7-hydroxy-bicyclo[3.3.0]oc tan-3-one (I) having high optical purity which is useful for the synthesis of an optically active carbacyclin and an optically active pentalenolactone E methyl ester. The compound (I) is also an intermediate compound serving for the purpose of improving the optical purity of (1R,5S,6S,7R)-3,3-ethylenedioxy-6-hydroxymethyl-7-(2'-tetrahydropyranyloxy )bicyclo[3.3.0]octane. The compound (I) is prepared by reacting (1R,5S,6S,7R)-3,3-ethylenedioxy-6-hydroxymethyl-7-(2'-tetrahydropyranyloxy )bicyclo[3.3.0]octane with tert-butylchlorodiphenylsilane in the presence of a base and removing the ethylenedioxy and tetrahydropyranyl groups of the resultant compound under an acid condition.Type: GrantFiled: January 4, 1989Date of Patent: October 3, 1989Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Kenji Mori, Masahiro Tsuji
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Patent number: 4845258Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using quaternary ammonium bifluorides, quaternary phosphonium bifluorides or alkali metal bifluorides as catalysts. The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.Type: GrantFiled: April 4, 1988Date of Patent: July 4, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4827004Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.Type: GrantFiled: August 24, 1987Date of Patent: May 2, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
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Patent number: 4820829Abstract: There are disclosed novel substituted o-phthalaldehydes of formula I ##STR1## wherein at least one of the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 is Q(alkyl).sub.3, --CH.sub.2 --Q(alkyl).sub.3, --O--Q(alkyl).sub.3, --Q(aryl).sub.3 or --Q(alkylenearyl).sub.3, wherein Q is Si, Sn or Ge, the alkyl moieties contain 1 to 12 carbon atoms, the aryl groups contain 6 or 12 ring carbon atoms and the alkylene radicals contain 1 to 4 carbon atoms, and each of the remaining substituents R.sub.1 to R.sub.4 is a hydrogen or halogen atom or a cyano, nitro, carboxyl or hydroxyl group, a C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or an alkoxycarbonyl group containing 1 to 4 carbon atoms in the alkoxy moiety.The novel o-phthalaldehydes can be polymerized to give polymers that can be used as photoresists.Type: GrantFiled: January 8, 1987Date of Patent: April 11, 1989Assignee: Ciba-Geigy CorporationInventor: Alfred Steinmann
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Patent number: 4812214Abstract: A method of combining a siloxy group (--SiO--) with a ketene-reactive compound to form a siloxy-containing product comprises:(a) subjecting a silyl diketone to photolysis under conditions effective for generating a siloxy ketene intermediate therefrom, said silyl diketone having the formula ##STR1## wherein Si is silicon, R.sub.1 and R.sub.4 are hydrocarbon groups containing from 1 to 18 carbons, and R.sub.2 and R.sub.Type: GrantFiled: September 28, 1987Date of Patent: March 14, 1989Assignee: Minnesota Mining & Manufacturing CompanyInventor: Bradford B. Wright
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Patent number: 4806668Abstract: The invention relates to a process for the production of (5-chloro-3-hydroxycyclopentyl) acetaldehydes of formula II ##STR1## in which R signifies a benzyl radical, a tert-butyldimethylsilyl radical or a tert-butyldiphenylsilyl radical, characterized in that a compound of formula I ##STR2## in which R has the meanings already mentioned, is reduced in the presence of a reduction agent.Type: GrantFiled: August 7, 1987Date of Patent: February 21, 1989Assignee: Schering AktiengesellschaftInventors: Bernd Raduechel, Werner Skuballa, Helmut Vorbrueggen
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Patent number: 4804772Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts devoid of fluorine (e.g., LiN.sub.3, NaN.sub.3, KN.sub.3, NaCN KCN, CsCN, NaOH, KOH, K.sub.2 CO.sub.3, and Cs.sub.2 CO.sub.3). The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.Type: GrantFiled: April 4, 1988Date of Patent: February 14, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4804773Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using an aminopyridine as catalyst. The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsilyloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.Type: GrantFiled: April 4, 1988Date of Patent: February 14, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4804774Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using trialkylphosphites or hexahydrocarbylphosphorous triamides, or both as catalysts. The reaction --which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.Type: GrantFiled: April 4, 1988Date of Patent: February 14, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4778904Abstract: Compounds of the formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or an ether-forming group and X is hydrogen, halo, trifluoromethyl, lower alkyl, or lower alkoxy, are useful intermediates for making PGE and PGF derivatives having an allenic function.Type: GrantFiled: January 9, 1987Date of Patent: October 18, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Gary F. Cooper
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Patent number: 4762936Abstract: There are disclosed a bicyclo[3.3.0]octene derivatives having the following formula: ##STR1## wherein R.sup.1 : a straight, branched or cyclic alkyl group or alkenyl group each having 5 to 10 carbon atoms;R.sup.2 and R.sup.3 : each represent a hydrogen atom or a protective group of a hydroxy group; andR.sup.4 : --CH.dbd.CH--(CH.sub.2).sub.2 --COOR.sup.5 or --CH.sub.2 R.sup.6 ; whereR.sup.5 : a hydrogen atom or an alkyl group; andR.sup.6 : a hydroxy group, an acetyloxy group or a butenyl group,and process for producing the same. These compounds and the process for producing them are available for producing a 9(0)-methano-.DELTA..sup.6 (9.alpha.)-PGI.sub.1.Type: GrantFiled: December 11, 1986Date of Patent: August 9, 1988Assignee: Sagami Chemical Research CenterInventors: Masakatsu Shibasaki, Toshiaki Mase, Mikiko Sodeoka, Yuji Ogawa
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Patent number: 4742144Abstract: An improvement is provided in the compression molding of lignocellulosic composite articles, such as particle or flake board, in which polyisocyanate binder systems are employed, the improvement being the provision of a novel copolymeric reaction product of a functional polysiloxane and a monocarboxylic acid or metal salt thereof as release agent on the mold surfaces to give multiple release. Optionally organopolysiloxane fluid may be employed along with the copolymer as diluent.Type: GrantFiled: May 15, 1987Date of Patent: May 3, 1988Assignee: ARCO Chemical CompanyInventors: Tinh Nguyen, James M. Gaul
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Patent number: 4739089Abstract: A method for making certain silylaryl ketones is provided by acylating a silarylene with an arylacyl halide in the presence of a Friedel-Crafts catalyst. Silicon containing arylketones are also provided.Type: GrantFiled: February 24, 1987Date of Patent: April 19, 1988Assignee: General Electric CompanyInventor: Peter P. Policastro
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Patent number: 4709054Abstract: A method is provided for silylating organic substrates, utilizing a halogenated polysilane, such as 1,1,2,2-tetrachloro dimethyldisilane and an aromatic acyl halide, for example, trimellitic anhydride acid chloride in the presence of a transition metal catalyst.Type: GrantFiled: August 13, 1985Date of Patent: November 24, 1987Assignee: General Electric CompanyInventor: Jonathan D. Rich
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Patent number: 4703127Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sup.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight- or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y and R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.Type: GrantFiled: September 2, 1983Date of Patent: October 27, 1987Assignee: The Australian National UniversityInventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
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Patent number: 4701536Abstract: Disclosed are a compound of Formula I: ##STR1## wherein R.sub.1 represents a hydrogen atom or a protective group for a hydroxyl group; and Z represents a direct bond (2,3-cis-5R*, 8S*) or an oxygen atom which forms an oxirane ring having a configuration of (2R*, 3R*, 5R*, 8S*),and a process for preparing the same.By use of the above compound as an intermediate, there can be synthesized periplanone-B which is a sex pheromone of periplaneta.Type: GrantFiled: July 7, 1986Date of Patent: October 20, 1987Assignee: UBE Industries, Ltd.Inventors: Jiro Tsuji, Takashi Takahashi
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Patent number: 4681951Abstract: There are disclosed bicyclo[3.3.0]octene derivatives having the following formula: ##STR1## wherein R.sup.1 is a straight, branched or cyclic alkyl group or alkenyl group each having 5 to 10 carbon atoms; andR.sup.2 and R.sup.3 are each separately a hydrogen atom or a protective group of a hydroxy group,and process for producing the same. These compounds and the process for producing them are available for producing a 9(0)-methano-.DELTA.6(9.alpha.)-PGI.sub.1.Type: GrantFiled: August 17, 1984Date of Patent: July 21, 1987Assignee: Sagami Chemical Research CenterInventors: Masakatsu Shibasaki, Toshiaki Mase, Mikiko Sodeoka, Yuji Ogawa