Bicyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/546)
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Patent number: 5426193Abstract: Disclosed are the improvements of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl (meth)acrylate and 3,4-epoxycyclohexyl methyl (meth)acrylate which is prepared by the improvements, including only minor amounts of polymers having a low molecular weight composed of 3,4-epoxycyclohexyl methyl (meth)acrylate itself.Furthermore, disclosed is a 3,4-epoxycyclohexyl methyl (meth)acrylate composition which has an excellent resistance to coloring, including a specified organic phosphorous compound.Type: GrantFiled: September 6, 1994Date of Patent: June 20, 1995Assignee: Daicel Chemical Industries, Inc.Inventors: Akihiro Kuwana, Kimihide Honda, Kunio Koga
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Patent number: 5424460Abstract: The present invention relates to new fluorinated hexane compounds corresponding to the following general formula (II): ##STR1## in which X'.sub.2, X'.sub.3 and X'.sub.4 are the same or different, and denote a halogen or a pseudohalogen, preferably a halogen, more preferably chlorine and fluorine, with the condition that, when R.sub.1 is hydroxyl, cyano, amido, imido, ethoxy, benzyloxy, cyclohexyloxy and tert-butoxy, not all the halogens can simultaneously be chlorine and R.sub.4, R.sub.3 and R.sub.5 are simultaneously equal to H;R.sub.1 denotes a hydrogen, a hydrocarbon chain such as an alkyl chain, alkoxy, cycloalkyl ether, an aromatic group, aromatic ether or an alkoxy, carbonyl, carboxyl or acyloxy, cyano, amido, imido or hydroxyl group;R.sub.Type: GrantFiled: October 21, 1993Date of Patent: June 13, 1995Assignee: Rhone-Poulenc ChimieInventors: Lucette Duhamel, Pierre Duhamel, Bertrand Leblond, Jean-Marie Poirier
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Patent number: 5422365Abstract: A compound selected from those of formula (I): ##STR1## wherein: R.sub.1, R'.sub.1 and R.sub.2 are each selected, independently of the others, from hydrogen and an alkyl radical, the two R.sub.2 groups being in the cis position in relation to the rings,and R, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R'a and R'b are as defined in the description,useful therapeutically in the regulation of the secretion of insulin.Type: GrantFiled: August 12, 1994Date of Patent: June 6, 1995Assignee: Adir et CompagnieInventors: David Billington, Francoise Perron-Sierra, Isabelle Picard, Jacques Duhault, Joseph Espinal
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Patent number: 5382676Abstract: Disclosed are the improvements of a process for the preparation of a purified 3,4-epoxycyclohexyl methyl(meth)acrylate and 3,4-epoxyeyclohexyl methyl(meth)acrylate which is prepared by the improvements, including only minor amounts of polymers having a low molecular weight composed of 3,4-epoxycyclohexyl methyl(meth)acrylate itself.Furthermore, disclosed is a 3,4-epoxycyclohexyl methyl(meth)acrylate composition which has an excellent resistance to coloring, including a specified organic phosphorous compound.Type: GrantFiled: August 19, 1993Date of Patent: January 17, 1995Assignee: Daicel Chemical Industries, Ltd.Inventors: Akihiro Kuwana, Kimihide Honda, Kunio Koga
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Patent number: 5367087Abstract: A process for producing an epoxide represented by the formula (2) which comprises reacting an olefin represented by the formula (1) with oxygen in the presence of an aldehyde and in the presence or absence of a proton source by using no catalyst or using an iron-containing or copper-containing catalyst.Type: GrantFiled: October 29, 1992Date of Patent: November 22, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Shun-Ichi Murahashi, Yoshiaki Oda
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Patent number: 5306748Abstract: Fluorine-modified thermosetting reins are available as phenolic or epoxy resins having trifluoromethyl groups and a naphthalene skeleton in a molecule. They are useful as components of resin compositions or resin modifiers and cure to products having low water pickup, low coefficient of thermal expansion, and adhesion as well as heat resistance and mechanical strength. Thermosetting resin compositions having such a thermosetting resin blended therein are useful in semiconductor element packaging.Type: GrantFiled: July 29, 1992Date of Patent: April 26, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshio Shiobara, Hisashi Shimizu, Manabu Narumi
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Patent number: 5302745Abstract: Process for the preparation of alkyl 3-oxo-2-pentyl-1-cyclopentene acetates starting from an epoxy-ester of formula ##STR1## wherein R designates a lower linear or branched alkyl radical of C.sub.1 -C.sub.6 and wherein the wavy line stands for a C--C bond of cis or trans configuration via an isomerization process.Type: GrantFiled: June 16, 1993Date of Patent: April 12, 1994Assignee: Firmenich S.A.Inventor: Beat Winter
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Patent number: 5254694Abstract: An optically active epoxycyclohexane derivative represented by the general formula: ##STR1## wherein R represents a 4-oxycarbonyl-1-hydroxy-3-methyl-3(Z)-buten-1-yl or 4-hydroxycarbonyl-3-methyl-1(E),3(Z)-butadien-1-yl group; and R.sup.1 and R.sup.2 each represent a lower alkoxy group or together form a 1,3-dioxolane ring together with the carbon atom to which they are bonded,and an enantiometer thereof.An optically active epoxycyclohexanone derivative represented by the general formula: ##STR2## wherein R.sup.3 represents a hydrogen atom or a lower alkyl, allyl, aralkyl or aryl group,and an enantiomer thereof.Further, the process for preparing these compounds, is also disclosed.Type: GrantFiled: February 12, 1992Date of Patent: October 19, 1993Assignee: Sagami Chemical Research CenterInventors: Kunikazu Sakai, Kyoko Takahashi
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Patent number: 5241104Abstract: Optically active mono-esters of dicarboxylic acid of the formula III: ##STR1## being useful as intermediates for preparing optically active natural products or medicines; asymmetric synthesis process for preparing thereof being characterized by the reaction of an acid anhydride with an (R)- or (S)-arylacetic acid derivative; and the key substances therefor are also claimed.Type: GrantFiled: June 23, 1992Date of Patent: August 31, 1993Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Takaharu Matsuura
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Patent number: 5223602Abstract: This invention relates to naphthol aralkyl resins of the general formula (I) ##STR1## in which A is a naphthalene nucleus, R is hydrogen or methyl, and n is an integer from 0 to 15 and cured products thereof, which are highly heat- and moisture-resistant, possess excellent impact strength and other mechanical properties, and are useful for such applications as lamination, molding, casting, and adhesion.Type: GrantFiled: January 24, 1992Date of Patent: June 29, 1993Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Masashi Kaji, Takanori Aramaki, Norito Nakahara, Yasuharu Yamada
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Patent number: 5216183Abstract: A 2,3-epoxycyclopentanone represented by the formula (IV): ##STR1## wherein the variables are as defined in the specification, which is used in the preparation of a 2-substituted-2-cyclopentanone compound suitable for use as an anticancer agent and a bone formation accelerator.Type: GrantFiled: February 18, 1992Date of Patent: June 1, 1993Assignee: Teijin LimitedInventors: Satoshi Sugiura, Toru Minoshima, Atsuo Hazato, Yoshinori Kato
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Patent number: 5214165Abstract: 6-Fluoroshikimic acid derivatives of the formula (I): ##STR1## wherein R.sup.1 is hydroxy or a moiety biotransformable thereto and R.sup.2 is hydrogen or --P(O)(OH).sub.2 have antibacterial, antifungal and herbicidal activity. Their preparation and use are described as are pharmaceutical compositions containing them.Type: GrantFiled: August 24, 1992Date of Patent: May 25, 1993Assignee: Imperial Chemical Industries PLCInventors: James K. Sutherland, William J. Watkins, George A. Snow, Gareth M. Davies
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Patent number: 5214169Abstract: The present invention as directed to a new class of N-(2,3-epoxycyclopentyl) carbamate derivatives as described by Formula V below, that are useful as chemical intermediates in the production of a new class of anti-hypertensives: ##STR1##Type: GrantFiled: April 30, 1992Date of Patent: May 25, 1993Assignee: Merrell Dow Pharmaceuticals Inc.Inventor: Theophilus F. Leapheart
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Patent number: 5200535Abstract: The invention provides cyclohexanone derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group; R.sup.6 and R.sup.7 together represent a single carbon-carbon bond or an epoxy group; and R.sup.8 represents a hydrogen atom or a hydroxyl group; with the proviso that when R.sup.6 and R.sup.7 together represent an epoxy group then R.sup.8 represents a hydrogen atom; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: August 19, 1991Date of Patent: April 6, 1993Assignee: Shell Research LimitedInventor: Paul H. Briner
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Patent number: 5169426Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and A have the meanings stated in the description, herbicides which contain these compounds as active ingredients, and a method for controlling undesirable plant growth.Type: GrantFiled: August 30, 1990Date of Patent: December 8, 1992Assignee: BASF AktiengesellschaftInventors: Dieter Jahn, Rainer Becker, Michael Keil, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer
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Patent number: 5155233Abstract: Compositions are provided containing epoxysilanes and diphenylamine in an amount at least sufficient to inhibit degradation. Methods for producing such compositions are also provided.Type: GrantFiled: December 24, 1991Date of Patent: October 13, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Shiu-Chin Su, Frederick D. Osterholtz
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Patent number: 5155243Abstract: The present invention provides a composition represented by the formula ##STR1## (wherein x is an integer of 3 to 7, y is an integer of 0 to 50, and R.sub.a and R.sub.b are H, methyl group, or propyl group and each of the R.sub.a and R.sub.b groups may be replaced with any of the other groups simultaneously)and useful as a raw material or modifier for resins for use in coating compositions, adhesives, epoxy resins, and the like, and further provides a process for producing a composition comprising compounds represented by the above formula (I) which process is characterized in that a compound represented by the formula ##STR2## is reacted with a lactone at 30.degree. to 20.degree. C. or compounds represented by the formula ##STR3## (wherein x, y, R.sub.a, and R.sub.b have the meanings as defined above) are epoxidized at 0.degree. to 80.degree. C. using a peroxide.Type: GrantFiled: October 15, 1991Date of Patent: October 13, 1992Assignee: Daicel Chemical Industries, Ltd.Inventors: Takaaki Fujiwa, Tomohisa Isobe
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Patent number: 5147873Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, or a pharmaceutically acceptable cation;Y is cyclopropyl, ethyl or p-fluorophenyl, and X is hydrogen or fluoro, or X and Y taken together form a group ##STR2## wherein R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; or a pharmaceutically acceptable salt thereof. Also disclosed are antibacterial pharmaceutical compositions comprising the foregoing compounds, methods of using the compounds in treating bacterial infections, and intermediates for the preparation of the compounds.Type: GrantFiled: February 15, 1991Date of Patent: September 15, 1992Assignee: Pfizer Inc.Inventor: Edward F. Kleinman
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Patent number: 5137921Abstract: There is provided an inhibitory agent of an increase in blood sugar level, comprising conduritol A of the formula(I): ##STR1## or a derivative thereof, as an active component.Type: GrantFiled: July 26, 1991Date of Patent: August 11, 1992Assignee: Dai-Nippon Sugar Mfg. Co., Ltd.Inventors: Ituo Kensho, Fumio Yamashita, Toshikazu Nagai, Tadashi Fujimoto, Yoshihisa Nakano, Hideki Tukimura
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Patent number: 5126128Abstract: Periplanone-B analogue of (4E, 8R, 9R, 10R)-8,9-epoxy-5-methyl-10,10-methylene-oxy-4-cyclodecen-1-one, suitable as cockroach attractant can be prepared by reacting 6-methyl-2,6-cyclodecadien-1-one with a silylating reagent under the presence of a basic catalyst to form a silyldienol ether, reacting the resultant ether with an organic peracid to obtain (2Z, 6E)-10-hydroxy-6-methyl-2,6-cyclodecadien-1-one, reacting the resultant product with a peroxide under the presence of a basic catalyst after protecting hydroxy groups thereof with protection groups to obtain an epoxide, reacting the epoxide with chloromethyl lithium or dimethyl sulfonium methylide thereby introducing a spiroepoxy group and then removing the protection groups, to obtain (1S, 4E, 8R, 9R, 10S)-8,9-epoxy-5-methyl-10,10-methyleneoxy-4-cyclodecen-1-ol and, further, oxidizing the resultant product with a chromic acid type or dimethyl sulfoxide type oxidizing agents.Type: GrantFiled: October 16, 1990Date of Patent: June 30, 1992Assignee: Japan Tobacco Inc.Inventors: Masataka Mori, Kentaro Okada, Kazuko Shimazaki, Tatsuji Chuman
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Patent number: 5118865Abstract: Novel compounds of formula ##STR1## wherein the dotted lines indicate the location of a single or double bond, symbol R.sup.1 stands for a hydrogen atom or a methyl radical, symbol R.sup.2 represents a linear or branched, saturated or unsaturated, C.sub.1 to C.sub.4 alkyl radical, provided that R.sup.1 is not hydrogen when R.sup.2 represents a methyl or n-propyl radical and the ring is saturated. Compounds (Ia) are useful as perfuming ingredients.A process for their preparation is disclosed.Type: GrantFiled: March 11, 1991Date of Patent: June 2, 1992Assignee: Firmenich SAInventors: Christian Chapuis, Karl-Heinrich Schulte-Elte, Herve Pamingle, Christian Margot
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Patent number: 5117057Abstract: This invention relates to insecticidal compositions containing N'-substituted-N,N'-disubstitutedhydrazines, methods of using such compositions and N'-substituted-N, N'-disubstitutedhydrazines. Specifically, the invention relates to insect growth regulating compositions, and methods of using such compositions, which include compounds having a nucleus of the formula ##STR1## where A', B', D and J are independently any atom or group of atoms; where E is a tertiary carbon containing organic radical, a haloalkyl having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen, and is attached to the nitrogen shown in the formula by a carbon-to-nitrogen single bond; where one G.sub.1 is C, N, O and S, and both G.sub.2 's and the other G.sub.1 are carbon; or one G.sub.2 is S or P, and both G.sub.1 's and the other G.sub.Type: GrantFiled: June 14, 1991Date of Patent: May 26, 1992Assignee: Rohm and Haas CompanyInventors: Adam C. Hsu, Harold E. Aller, Raymond A. Murphy, Dat P. Le, Donald W. Hamp, Barry Weinstein
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Patent number: 5114967Abstract: Alisamycin, a compound of the formula I ##STR1## has an antibiotic, antitumor and antiparasitic action.Type: GrantFiled: January 10, 1991Date of Patent: May 19, 1992Assignee: Hoechst AktiengesellschaftInventors: Christopher M. M. Franco, Erra K. S. Vijayakumar, Sugata Chatterjee, Bimal N. Ganguli, Jurgen Blumbach, Herbert Kogler, Hans-Wolfram Fehlhaber
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Patent number: 5106868Abstract: Compounds UCF1 and derivatives thereof exhibit anti-bacterial and anti-tumor activities and may be used for the preparation of anti-bacterial and anti-tumor agents.Compounds UCF1 may be produced by fermentation of a microorganism of the genus Streptomyces capable of producing compounds UCF1, preferably Streptomyces sp. UOF1 (FERM BP-2844) and recovering the desired compounds from the cultured broth.The compounds UCF1 have the formula ##STR1## wherein R represents either ##STR2## The compounds may be oxidized to obtain derivatives of formula ##STR3## which exhibit similar pharmacological activities.Type: GrantFiled: May 7, 1991Date of Patent: April 21, 1992Assignee: Kyowa Hakko Kogyo Kabushiki KaishaInventors: Hirofumi Nakano, Mitsunobu Hara, Yutaka Saito, Yoji Ikuina, Toshimitsu Takiguchi, Masami Okabe
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Patent number: 5076829Abstract: 2-substituted 2,3-epoxy-5-cyclohexenone derivatives of the formula I ##STR1## where W is C.dbd.O or CHOR.sup.1, R.sup.1 is hydrogen, alkyl, alkenyl, alkynyl or alkoxycarbonyl, R is a substituted or unsubstituted hydrocarbon chain, or phenyl or phenylalkyl whose phenyl radical is substituted or unsubstituted and whose alkyl radical may be interrupted by O or S and fungicides and herbicides containing these compounds.Type: GrantFiled: April 20, 1990Date of Patent: December 31, 1991Assignee: BASF AktiengesellschaftInventors: Ulrich Wriede, John-Bryan Speakman, Rudolf Karl, Ernst-Heinrich Pommer, Eberhard Ammermann, Bruno Wuerzer
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Patent number: 5068293Abstract: The invention relates to naphthol-based epoxy resins of the general formula (I) ##STR1## in which A is a naphthalene nucleus, R is hydrogen or methyl, and n is an integer from 0 to 15, naphthol aralkyl resins which are intermediates for said epoxy resins, a process for the preparation of said naphthol aralkyl resins, and epoxy resin compositions containing said naphthol-based epoxy resins which are highly heat- and moisture-resistant, possess excellent impact strength and other mechanical properties, and are useful for such applications as lamination, molding, casting, and adhesion.Type: GrantFiled: August 30, 1990Date of Patent: November 26, 1991Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Masashi Kaji, Takanori Aramaki, Norito Nakahara, Yasuharu Yamada
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Patent number: 5043456Abstract: There are provided compounds of the formula: ##STR1## wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.5 alkyl; R.sub.2 is an C.sub.1 -C.sub.10 alkyl, aryl, aralkyl, or pyridyl, where the aryl, aralkyl, or pyridyl are unsubstituted or are substituted by C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro, hydroxy, carboxy, amino, C.sub.1 -C.sub.5 alkylamino, C.sub.1 -C.sub.5 dialkyamino whose two alkyl groups may be different from each other, C.sub.2 -C.sub.3 alkanoylamino, or halogen and X is an C.sub.1 -C.sub.7 alkylene, C.sub.2 -C.sub.7 alkenylene, --CH(F)CH.dbd.CH(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 --S--(CH.sub.2).sub.2 --, --(CH.sub.2).sub.2 --S--(CH.sub.2).sub.3 --, --C.sub.6 H.sub.4 -O--CH.sub.2 -- or --CH.sub.2 CH.dbd.CH--m--C.sub.6 H.sub.4 --, or their pharmaceutically accepatble salts. The compounds are useful as antithrombotic, anti-vasconstricting and anti-bronchoconstricting drugs.Type: GrantFiled: April 27, 1990Date of Patent: August 27, 1991Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Fumihiko Watanabe, Susumu Kamata, Nobuhiro Haga, Tatsuo Tsuri, Tadahiko Tsushima, Kenji Kawada
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Patent number: 5006552Abstract: The invention provides cyclopentane derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5, each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group, R.sup.1 and R.sup.2 independently represent a hydrogen atom or an alkyl group, and R.sup.5 represents a hydrogen atom or an alkyl or cycloalkyl group; a process for their preparation; compositions containing such compounds and their use as fungicides. Compounds of formula I are also useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: August 23, 1989Date of Patent: April 9, 1991Assignee: Shell Internationale Research Maatschappij B.V.Inventor: Paul H. Briner
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Patent number: 4981981Abstract: The novel sesquiterpene epoxides trans-(Z)-1-methyl-4-(1,5-dimethyl-1,4-hexadienyl)-1,2-epoxycyclohexane and cis-(z)-1-methyl-4-(1,5-dimethyl-1,4-hexadienyl)-1,2-expoxycyclohexane have been isolated from N. viridula adult males, and have been successfully synthesized. The compounds are useful for the production of synthetic sex attractants for N. viridula and its parasitoids.Type: GrantFiled: March 14, 1988Date of Patent: January 1, 1991Assignees: The United States of America as represented by the Secretary of Agriculture, The Trustees of the University of PennsylvaniaInventors: Jeffrey R. Aldrich, James E. Oliver, Kyriacos C. Nicolaou, Brian E. Marron
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Patent number: 4980485Abstract: Optically active periplanone-B is manufactured through oxidizing (1RS, 4S, 5E)-isopropyl-7-methylene-5-cyclodecene-1-ol. The oxidized product is regioselectively enolized and then sulfenylated. The sulfenylated product is oxidized and then subjected to decomposition of the sulfoxide. The decomposed product is epoxidated, and the epoxidated product is converted into an enolate which is then oxidized. The oxidized product is oxidized and then regio- and stereoselectively epoxidated to obtain optically active periplanone-B.Type: GrantFiled: September 26, 1989Date of Patent: December 25, 1990Assignee: Japan Tobacco Inc.Inventors: Kenji Mori, Takeshi Kitahara, Koshi Koseki
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Patent number: 4918075Abstract: Antiviral activity is exhibited by compounds having the formula ##STR1## its pharmaceutically acceptable salts thereof wherein R.sub.2 and R.sub.3 are independently hydrogen, --PO.sub.3 H.sub.2 or ##STR2## and R.sub.1 is either a purine, pyrimidine or an analog thereof.Type: GrantFiled: December 20, 1988Date of Patent: April 17, 1990Assignee: E. R. Squibb & Sons, Inc.Inventors: Robert Zahler, Glenn A. Jacobs
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Patent number: 4882445Abstract: This invention relates to antitumor cyclohexanone compositions and derivatives thereof, a process of producing the compositions and a method for inhibiting tumors utilizing the compositions. More particularly, the compositions are cyclohexanone and derivatives thereof which are derived from marine organisms, i.e., the acord worm, Ptychodera sp.Type: GrantFiled: December 30, 1987Date of Patent: November 21, 1989Assignee: Harbor Branch Oceanographic Institution, Inc.Inventors: Tatsuo Higa, Paul J. Scheuer
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Patent number: 4864041Abstract: A novel process for the homogenous oxidation of organic substrates is disclosed. This process uses a transition metal-substituted polyoxometalate catalyst, which in the presence of an oxygen donor, catalyses the carbon-hydrogen bond (e.g., alkane) hydroxylation reaction and/or epoxidation reaction of the organic substrate.Type: GrantFiled: February 4, 1987Date of Patent: September 5, 1989Assignee: Emory UniversityInventor: Craig L. Hill
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Patent number: 4861913Abstract: Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted aryl, aralkyl or heterocycle; R.sub.3 is a hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms an may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkenylene, oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.Type: GrantFiled: November 5, 1986Date of Patent: August 29, 1989Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Sanji Hagishita, Kaoru Seno, Susumu Kamata, Nobuhiro Haga, Tatsuo Tsuri, Tadahiko Tsushima, Kenji Kawada
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Patent number: 4855466Abstract: Disclosed are compounds having the formula ##STR1## wherein Prot is a hydroxyl protecting group. The compounds are useful as intermediates in the preparation of compounds of the formula ##STR2## which in turn are useful as antiviral agents.Type: GrantFiled: December 28, 1987Date of Patent: August 8, 1989Assignee: E. R. Squibb & Sons, Inc.Inventors: Robert Zahler, Glenn A. Jacobs
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Patent number: 4841081Abstract: A method of optically resolving a racemate, or a diastereomeric mixture, of a substituted or unsubstituted glycidyl ester or ether compound having at least one glycidylic structure represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, independently from each other, represent H or CH.sub.3, and 1 to 3 asymmetric carbon atoms in the molecule, or a racemate of a beta-dihalohydrin ester compound, which comprises contacting said racemate or diastereomeric mixture with an optically active form of a compound having the following formula (I) ##STR2## wherein X represents a halogen atom, to form an inclusion complex compound having the optically active compound of formula (I) as a host, and separating the resulting complex compound.Type: GrantFiled: October 14, 1986Date of Patent: June 20, 1989Assignee: Osaka Soda Co., Ltd.Inventors: Fumio Toda, Koichi Tanaka, Tetsuya Nakata
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Patent number: 4766107Abstract: The compound 16-oxa-bicyclo-[13.1.0]-hexadec-7-ene, and a process for its production, having the structural formula: ##STR1## is disclosed. 16-oxa-bicyclo-[13.1.0]-hexadec-7-ene is useful as a fragrance and may be produced by reacting cyclopentadeca-1,8-diene in the presence of an organic peracid.Type: GrantFiled: April 24, 1986Date of Patent: August 23, 1988Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Hans-Jurgen Eberle, Helmut Gebauer
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Patent number: 4723038Abstract: Processes for preparing compounds which exhibit seed germinating activity are disclosed. An ester of acetoacetic acid is condensed with a ketone to produce a substituted cyclohexenone which is reacted with a thiol to get a dithioketal which is then desulfurized to produce an ester of a substituted cyclohex-2-ene-1-carboxylic acid which exhibits seed germinating activity. The same compound can be produced by a different process which reacts the substituted cyclohexenone with a reducing agent. An exemplary reducing agent would be an organosilane and a Lewis acid.Type: GrantFiled: December 31, 1985Date of Patent: February 2, 1988Assignee: The United States of America as represented by the Secretary of AgricultureInventor: Oliver D. Dailey, Jr.
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Patent number: 4721798Abstract: The invention provides a process for epoxidizing an olefinic double bond in an olefinically-unsaturated compound by contact of a liquid phase mixture containing the olefinically-unsaturated compound, an aldehyde having at least two carbon atoms and a suitable solvent with molecular oxygen in the presence of a catalyst which is soluble in the reaction mixture and which comprises a praseodymium compound. The process has particularly advantageous application to oxidation of aldrin to dieldrin.Type: GrantFiled: February 18, 1986Date of Patent: January 26, 1988Assignee: Shell Oil CompanyInventor: Albertus J. Mulder
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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: 4642361Abstract: A novel process for the manufacture of quinone derivatives which are suitable as intermediates for the manufacture of (2RS,4'R,8'R)-tocopherol is described.Type: GrantFiled: September 18, 1985Date of Patent: February 10, 1987Assignee: Hoffmann-La Roche Inc.Inventor: August Ruttimann
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Patent number: 4639532Abstract: Disclosed is an improved process for synthesizing periplanone-B, the sex attractant and sex excitant pheromone of the American cockroach, Periplaneta americana.Type: GrantFiled: June 18, 1984Date of Patent: January 27, 1987Assignee: Yale UniversityInventor: Stuart L. Schreiber
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Patent number: 4595770Abstract: Novel antibiotic U-56,407 producible in a fermentation under controlled conditions using a biologically pure culture of the microorganism Streptomyces hagronensis strain 360, NRRL 15064. This antibiotic is active against various Gram-positive bacteria, for example, Staphylococcus aureus, Streptococcus pyogenes and Streptococcus pneumoniae. Thus, antibiotic U-56,407 can be used in various environments to eradicate or control such bacteria.Type: GrantFiled: June 21, 1982Date of Patent: June 17, 1986Assignee: The Upjohn CompanyInventors: Thomas F. Brodasky, David W. Stroman
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Patent number: 4567283Abstract: Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1;Y is (--CR.sub.5 R.sub.6 --).sub.n in which n is 0, 1 or 2;Z is (--CR.sub.7 R.sub.7 --).sub.p in which p is 1, 2 or 3;the sum of m+n+p is an integer of 2 to 5, inclusive;R.sub.2 and R.sub.3 each is H or alkyl, and the like;R.sub.1 is H or alkyl; andW is an unsaturated moiety, are useful as plant growth regulators and herbicides.Type: GrantFiled: June 25, 1984Date of Patent: January 28, 1986Assignee: Shell Oil CompanyInventors: George B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
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Patent number: 4533713Abstract: Compounds containing (a) a fluoroaliphaticsulfonamido moiety, and (b) a moiety containing (1) at least two oxirane groups, (2) at least two non-terminal N-.beta.-hydroxyalkylene groups, or (3) at least one oxirane group and at least one non-terminal N-.beta.-hydroxyalkylene group. The compound is capable of being cured with a curing agent to give a cured product having excellent water resistance and oil resistance.Type: GrantFiled: May 6, 1983Date of Patent: August 6, 1985Assignee: Minnesota Mining and Manufacturing CompanyInventor: Richard D. Howells
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Patent number: 4503062Abstract: This invention relates to novel alicyclic alcohol compounds of the formula ##STR1## wherein Az is imidazole or 1,2,4-triazole, R.sup.6 is optionally substituted phenyl and A is an alicyclic ring optionally benzo-fused, which compounds possess pharmaceutical, veterinary, agricultural and horticultural antifungal properties; together with a process for their manufacture, compositions containing them, and a method of combatting plant fungal diseases.Type: GrantFiled: March 28, 1983Date of Patent: March 5, 1985Assignee: Imperial Chemical Industries PLCInventor: Michael B. Gravestock
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Patent number: 4442299Abstract: New bromoepoxy-cyclohexenes and their derivatives, which are starting compounds for units used to synthesize natural compounds, e.g. cyclitols or aminocyclitols.Type: GrantFiled: April 22, 1982Date of Patent: April 10, 1984Assignee: BASF AktiengesellschaftInventors: Horst Prinzbach, Reinhard Schwesinger, Reinhold Keller
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Patent number: 4414418Abstract: Process for the production of dimedone from isophorone. The isophorone is converted in the presence of a solvent with ozone into an ozone-addition product. An alcohol corresponding to the ester radical is added at the latest after the formation of the ozone-addition product for the formation of the intermediate product, 3,3-dimethyl-5-oxo-hexanoic acid ester. The ozone addition product is heated in the presence of acids to a temperature of 20.degree. to 150.degree. C. The 3,3-dimethyl-5-oxo-hexanoic acid ester is isolated thereby. The ester is then converted in a further step into dimedone by treatment of the ester with an alkali alcoholate in an anhydrous milieu.Type: GrantFiled: May 19, 1982Date of Patent: November 8, 1983Assignee: Lonza Ltd.Inventor: Pavel Lehky
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Patent number: 4389529Abstract: A mixture of tetrachloroacetone and hydrogen peroxide has been found effective for epoxidizing olefinically unsaturated organic material dissolved in various aromatic or halogenated aliphatic organic solvents.Type: GrantFiled: April 22, 1982Date of Patent: June 21, 1983Assignee: General Electric CompanyInventor: Charles J. Stark
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Patent number: 4384127Abstract: The invention comprises a multi-step synthesis of l(-) prostaglandin E.sub.2. The special features of the synthesis include: (1) a triply-convergent conjugate-addition and alkylation reaction involving the 1,4-addition of a chiral vinyl lithium reagent to a chiral vinylsulfone to produce a sulfone-stabilized anion. This anion is alkylated in situ to produce the basic prostaglandin skeleton structure, which is then subjected to (2) an efficient peracid oxidation of a secondary amine to a .beta.-silyloxy oxime; and (3) an alkali-catalyzed 1,4-elimination of an .alpha.-sulfonyl oxime to produce a vinyl nitroso intermediate. This intermediate is treated with borohydride to give a stereospecific 1,4-reduction which yields the bis-silyloxy oxime of l(-)PGE.sub.2. Hydrolysis of the oxime, with concurrent cleavage of the silyloxy protecting groups, affords l(-)PGE.sub.2.Type: GrantFiled: April 8, 1981Date of Patent: May 17, 1983Assignee: Purdue Research FoundationInventor: Phillip L. Fuchs