Acyclic -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Lactone Ring Patents (Class 549/291)
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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: 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: 5412110Abstract: Process to separate racemic mixtures of beta-hydroxy or beta-acyloxy-delta-valerolactones, which in position 2 and/or 5 of the lactone ring are substituted by hydrogen, alkyl groups having 4 to 20 C atoms, which are optionally penetrated by an oxygen atom, or by aralkyl groups, whereby not both positions are substituted by hydrogen, through reaction of the racemic mixture in the presence of a hydrolase with or without esterifying agent in a diluent and separation of the reaction mixture, which contains an enantiomerically pure beta-hydroxy-delta-valerolactone and an enantiomerically pure beta-acyloxy-delta-valerolactone, through conventional methods into the enantiomically pure compounds,a process for the manufacture of enantiomerically pure oxetanones using said separation process and enantiomerically pure beta-acyloxy-delta-valerolactones.Type: GrantFiled: August 28, 1992Date of Patent: May 2, 1995Assignee: Chemie Linz Gesellschaft m.b.H.Inventors: Peter Pochlauer, Marion Wagner
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Patent number: 5393729Abstract: The invention relates to 3-aryl-pyrone derivatives of the general formula (I) ##STR1## in which the substituents are as defined in the specification. The compounds are useful as pesticides, herbicides and fungicides.Type: GrantFiled: September 3, 1993Date of Patent: February 28, 1995Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Andreas Krebs, Folker Lieb, Michael Ruther, Jorg Stetter, Christoph Erdelen, Ulrike Wachendorff-Neumann, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
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Patent number: 5387689Abstract: The invention relates to chiral valerolactone derivatives of the formula I ##STR1## wherein R.sup.1 is C.sub.1-18 alkyl in which one or two non-adjacent --CH.sub.2 groups are optionally replaced by --O--, --CO--O--, --O--CO-- or --S--,A is --H.sub.2 --, --C--(CH.sub.3).sub.2 -- or --CH.sub.2 CH.sub.2,Sp is a spacer, which optionally contains a chiral carbon atom,Z.sup.0 is --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --C.tbd.C-- or --CH.tbd.CH--,MG is a mesogenic group, andn and p are each 0 or 1,and the use thereof as components of liquid-crystalline media for electrooptical displays.Type: GrantFiled: September 10, 1993Date of Patent: February 7, 1995Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Ulrich Finkenzeller
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Patent number: 5296613Abstract: Compounds of formula I: ##STR1## wherein: R1 is hydrogen or alkyl;R2 is alkyl optionally substituted by one or more alkoxy groups or halogen atoms;X is a group of formula --OR3 wherein R3 is alkyl, cycloalkyl, or arylalkyl; or X is a group of formula --NHCVR4 wherein V is oxygen or sulphur, R4 is hydrogen, alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted), alkenyl, aryl, arylalkyl, amino, mono- or di-alkylamino or a group of the formula --OR5 wherein R5 is optionally substituted alkyl, aryl or arylalkyl; or X is a group of formula --NHSO.sub.2 R4a wherein R4a is alkyl, aryl or a group of formula --CH.sub.2 COR4b wherein R4b is alkyl or aryl;Y is optionally substituted alkoxy, cycloalkoxy, arylalkoxy or a group of formula --NR6R7 wherein R6 is hydrogen or alkyl and R7 is alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted), aryl or arylalkyl or R7 is a group of formula --COOR8 wherein R8 is alkyl are useful intermediates in the synthesis of beta-lactam antibiotics.Type: GrantFiled: July 23, 1992Date of Patent: March 22, 1994Assignee: Imperial Chemical Industries plcInventors: Richard W. Bayles, Anthony P. Flynn, Ralph W. Turner
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Patent number: 5260426Abstract: The invention relates to antibacterial pseudo-primycin complexes of formula (I) ##STR1## to the components and acid addition salts thereof, as well as to the preparation of these compounds and to the pharmaceutical compositions containing said compounds as active ingredient.In the formula (I) R.sup.1 is butyl, pentyl or hexyl, R.sup.2 is hydrogen, hydroxyl or O-arabinose and X is organic or inorganic acid ion.Type: GrantFiled: March 24, 1992Date of Patent: November 9, 1993Assignee: Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T.Inventors: Gyula Dekany, Judit Frank, Istvan Pelczer, Gabor Kulcsar, Eniko Schreiner
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Patent number: 5185349Abstract: Novel lactone and lactam compounds which are useful to lower blood cholesterol levels in a patient, said compounds containing an arylcarboxamide or arylthiocarboxamide moiety.Type: GrantFiled: March 8, 1991Date of Patent: February 9, 1993Assignee: Warner-Lambert CompanyInventor: Corinne E. Augelli-Szafran
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Patent number: 5155236Abstract: Compounds of formula I: ##STR1## wherein: R1 is hydrogen or alkyl;R2 is alkyl optionally substituted by one or more alkoxy groups or halogen atoms;X is a group of formula --OR3 wherein R3 is alkyl, cycloalkyl, or arylalkyl; or X is a group of formula --NHCVR4 wherein V is oxygen or sulphur, R4 is hydrogen, alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted), alkenyl, aryl, arylalkyl, amino, mono- or di-alkylamino or a group of the formula --OR5 wherein R5 is optionally substituted alkyl, aryl or arylalkyl; or X is a group of formula --NHSO.sub.2 R4a wherein R4a is alkyl, aryl or a group of formula --CH.sub.2 COR4b wherein R4b is alkyl or aryl;Y is optionally substituted alkoxy, cycloalkoxy, arylalkoxy or a group of formula --NR6R7 wherein R6 is hydrogen or alkyl and R7 is alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted), aryl or arylalkyl or R7 is a group of formula --COOR8 wherein R8 is alkyl are useful intermediates in the synthesis of beta-lactam antibiotics.Type: GrantFiled: April 6, 1989Date of Patent: October 13, 1992Assignee: Imperial Chemical Industrial PLCInventors: Richard W. Bayles, Anthony P. Flynn, Ralph W. Turner
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Patent number: 5134231Abstract: An amino acid compound of the formula: ##STR1## wherein R is a lower alkyl group, R.sub.1 is a hydrogen atom or a protecting group for carboxyl, R.sub.2 is a hydrogen atom, a protecting group for amino, an optionally substituted allyl group of the formula: ##STR2## (wherein R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group or an aryl group), a beta-hydroxyethyl group in which the hydroxyl group is optionally protected, a formylmethyl group in which the formyl group is optionally protected, a carboxymethyl group in which the carboxyl group is protected or a 2-furylmethyl group and X is an optionally protected carboxyl group, a hydroxymethyl group in which the hydroxyl group is optionally protected or a substituted mercaptomethyl group of the formula:--CH.sub.2 SR.sub.5(wherein R.sub.5 is an aryl group or an ar(lower)alkyl group), which is a useful intermediate in the synthesis of 1-alkylcarbapenem compounds.Type: GrantFiled: January 17, 1991Date of Patent: July 28, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Yoshihito Nozaki, Akira Sasaki, Haruki Matsumura
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Patent number: 5114461Abstract: A 2-benzoylcyclic-1,3-dione derivative of the formula: ##STR1## wherein X represents methylene, oxygen, sulphur or --NR.sup.4 --, Y represents --C(R.sup.5) (R.sup.6)-- or oxygen, R.sup.1 represents hydrogen or alkyl optionally substituted by halogen or represents cycloalkyl, R.sup.2 represents hydrogen or R.sup.7 or R.sup.1 and R.sup.2 together represent alkylene, R.sup.3 represents halogen, hydroxy, carboxy, nitro, cyano or amino or carbamoyl (which may be substituted by one or two alkyl groups), alkoxycarbonyl, alkanoyl, or alkanoylamino, R, RO, RS, RSO or RSO.sub.2 in which R represents alkyl optionally substituted by halogen, R.sup.4 represents hydrogen or alkyl or alkoxycarbonyl, R.sup.5 represents hydrogen or alkyl or alkoxycarbonyl, R.sup.6 represents hydrogen or alkyl, R.sup.7 represents alkyl which may be substituted by halogen or alkylthio or by a group (R.sup.8).sub.n -phenyl-S-, or represents cycloalkyl or tetrahydrothiapyran-3-yl or represents a group (R.sup.8).sub.n -phenyl- in which R.sup.Type: GrantFiled: November 22, 1989Date of Patent: May 19, 1992Assignee: May & Baker LimitedInventors: Neil J. Geach, James Gilmour, Leslie R. Hatton, Philip H. G. Smith
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Patent number: 5104857Abstract: The invention relates to antibacterial pseudo-primycin complexes of formula (I) ##STR1## to the components and acid addition salts thereof, as well as to the preparation of these compounds and to the pharmaceutical compositions containing said compounds as active ingredient.In the formula (I) R.sup.1 is butyl, pentyl or hexyl, R.sup.2 is hydrogen, hydroxyl or O-arabinose and X is organic or inorganic acid ion.Type: GrantFiled: October 31, 1990Date of Patent: April 14, 1992Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.Inventors: Gyula Dekany, Judit Frank, Istvan Pelczer, Gabor Kulcsar, Eniko Schreiner
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Patent number: 5062880Abstract: This invention relates to 1-aryl-1,4-dihydro-4-oxo-5-carboxypyridazine derivatives which are not only useful as plant growth regulators and hybridizing agents for cereal crops but possess the additional utility of having an improved margin of safety as concerns plant injury and seed quality.Type: GrantFiled: December 19, 1989Date of Patent: November 5, 1991Assignee: Monsanto CompanyInventor: Dennis R. Patterson
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Patent number: 5011944Abstract: .alpha.-Pyrones of the formula I ##STR1## in which R.sup.1 is --CF.sub.3 or --COOR.sup.3 and R.sup.3 is the radical of a C.sub.1 -C.sub.18 alcohol diminished by a hydroxyl group, and R.sup.2 is --F, --Br, --Cl, --CN, --CF.sub.3, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.2 -C.sub.18 alkynyl, C.sub.1 -C.sub.18 alkoxy, C.sub.1 -C.sub.18 alkylthio, C.sub.1 -C.sub.18 alkylsulfonyl, C.sub.6 -C.sub.16 aryl, C.sub.7 -C.sub.24 alkaryl, C.sub.7 -C.sub.12 aralkyl, C.sub.8 -C.sub.24 alkaralkyl, C.sub.6 -C.sub.16 aryloxy, C.sub.6 -C.sub.16 arylthio, C.sub.6 -C.sub.16 arylsulfonyl, C.sub.7 -C.sub.24 alkaryloxy, C.sub.7 -C.sub.24 alkarylthio, C.sub.7 -C.sub.24 alkarylsulfonyl, C.sub.7 -C.sub.12 aralkyloxy, C.sub.7 -C.sub.12 aralkylthio, C.sub.7 -C.sub.12 aralkylsulfonyl, C.sub.8 -C.sub.24 alkaralyloxy, C.sub.8 -C.sub.24 alkaralylthio, C.sub.8 -C.sub.24 alkaralylsulfonyl, secondary amine having 2 to 24 C atoms or trialkylsilyl or trialkoxysilyl each of which has 3 to 18 C atoms.Type: GrantFiled: May 24, 1989Date of Patent: April 30, 1991Assignee: Ciba-Geigy CorporationInventors: Vratislav Kvita, Marcus Baumann, Walter Fischer, Carl W. Mayer, Thomas Allmendinger
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Patent number: 5001255Abstract: Compounds of the formula ##STR1## the use thereof for inhibiting cholesterol biosynthesis and lowering the blood cholesterol level and, therefore, in the treatment of hyperlipoproteinemia and atherosclerosis, pharmaceutical compositions comprising such compounds and processes for and intermediates in the synthesis of such compounds.Type: GrantFiled: July 1, 1988Date of Patent: March 19, 1991Assignee: Sandoz Pharm. Corp.Inventors: Faizulla G. Kathawala, Sompong Wattanasin
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Patent number: 4980342Abstract: A convenient process for the preparation of .gamma.-alkyl-substituted-.gamma.-butyrolactones and .delta.-valerolactones is provided. The process involves forming the .alpha.-alkylidene lactone by reacting essentially equimolar amounts of an .alpha.-acyl lactone, an aldehyde, and an alkali metal hydroxide in an inert diluent at an elevated temperature while removing water and hydrogenating the .alpha.-alkylidene lactone to obtain the corresponding .alpha.-alkyl lactone.Type: GrantFiled: September 1, 1989Date of Patent: December 25, 1990Assignee: Henkel CorporationInventors: Louis Rebrovic, Eugene G. Harris
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Patent number: 4970313Abstract: A process for the preparation of optically active 3-de-methylmevalonic acid derivatives, and intermediates A process for the preparation of optically active 3-de-methylmevalonic acid derivatives of the formula I ##STR1## (3,5-dihydroxy carboxylic acid derivatives) or of the formula II ##STR2## (.beta.-hydroxy lactones) in which R, R.sup.1 and Y have the indicated meanings, is described. The invention furthermore relates to aldehydes of the formula XII ##STR3## in which M represents the indicated protective groups. The 3-demethylmevalonic acid derivatives of this invention are useful for lowering cholesterol levels of a host.Type: GrantFiled: December 6, 1988Date of Patent: November 13, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Kurt Kesseler, Ekkehard Baader, Gerhard Beck
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Optically active .beta.-amino acid derivatives and their salts, and processes for producing the same
Patent number: 4837343Abstract: Optically active .beta.-amino acid derivatives and their salts of the following formula: ##STR1## wherein COOR.sup.1 is an esterified or unesterified carboxyl group; R.sup.2 is hydrogen or a C.sub.1-10 acyl or esterified carboxyl group and processes for producing the same. These compounds permit important intermediate for the synthesis of 1.beta.-methylcarbapenem derivatives to be produced in an efficient way.Type: GrantFiled: September 1, 1987Date of Patent: June 6, 1989Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventor: Minoru Hatanaka -
Patent number: 4818431Abstract: New tetrahydropyran derivatives of the formula I ##STR1## in which G is H.sub.2 or .dbd.O, R.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, it also being possible for one or two CH.sub.2 groups to be replaced by O atoms, or are F, Cl, Br or CN, R.sup.2 is also H, A.sup.1 and A.sup.2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by 1-4 F atoms, Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, or a single bond, m and n are each 0, 1, 2 or 3, but (m+n) is at least 1 and at most 3, it being possible, when m is 2 or 3, for the group A.sup.1 and, when n is 2 or 3, for the groups A.sup.2 each to be identical or different from one another, and the acid addition salts of those among these compounds which are basic, are suitable for use as components in liquid-crystal dielectrics.Type: GrantFiled: November 24, 1986Date of Patent: April 4, 1989Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Joachim Krause, Peter Fuss
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Patent number: 4780124Abstract: Compounds having the formula ##STR1## wherein X is sulfur;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together form a single bond; orR.sup.1 and R.sup.3 together are alkylene having 2-5 carbon atoms; orR.sup.2 and R.sup.4 together are alkylene having 2-5 carbon atoms; andR.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10)--NR.sup.Type: GrantFiled: December 21, 1987Date of Patent: October 25, 1988Assignee: Stauffer Chemical CompanyInventors: Christopher G. Knudsen, William J. Michaely, Donald R. James, Hsiao-Ling M. Chin
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Patent number: 4751306Abstract: Imide intermediates for the preparation of analgesic and/or antagonist octahydrobenzofuro[3,2-e]-isoquinolines and octahydro-4a,7-ethano- and ethenobenzofuro[3,2-e]isoquinolines and processes for their preparation are provided.Type: GrantFiled: September 9, 1985Date of Patent: June 14, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Engelbert Ciganek, Bet-key Wong
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Patent number: 4741755Abstract: Compounds having the formula ##STR1## wherein X is oxygen or sulfur;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together form a single bond; orR.sup.1 and R.sup.3 together are alkylene having 2-5 carbon atoms; orR.sup.2 and R.sup.4 together are alkylene having 2-5 carbon atoms; andR.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: June 9, 1986Date of Patent: May 3, 1988Assignee: Stauffer Chemical CompanyInventors: Christopher G. Knudsen, William J. Michaely, Donald R. James, Hsiao-Ling M. Chin
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Patent number: 4707181Abstract: This invention relates to 1-aryl-1,4-dihydro-4-oxo-3,5-dicarboxypyridazine derivatives which are not only useful as plant growth regulators and hybridizing agents for cereal grain crops but possess the additional utility of having an improved margin of safety as concerns plant injury and seed quality.Type: GrantFiled: August 30, 1982Date of Patent: November 17, 1987Assignee: Rohm and Haas CompanyInventor: Dennis R. Patterson
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Patent number: 4668803Abstract: Novel organic compound of the basic formula ##STR1## which have substantial luminescent emission characteristics and advantages.Type: GrantFiled: July 1, 1985Date of Patent: May 26, 1987Assignee: Atlantic Richfield CompanyInventors: Elliot Berman, Brian A. Zentner
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Patent number: 4634783Abstract: Amidine compounds of the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsin, anti-plasmin, anti-kallikrein and anti-thrombin agents. They are also useful as a powerful anti-complement agent.Type: GrantFiled: January 23, 1984Date of Patent: January 6, 1987Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Toyoo Nakayama, Shigeki Nunomura, Ryoji Matsui, Shin-ichi Watanabe, Kimio Sudo, Toshiyuki Okutome, Masateru Kurumi, Yojiro Sakurai, Takuo Aoyama
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Patent number: 4559406Abstract: The invention relates to a process for the preparation of the compound of the formula I, ##STR1## which comprises (a.sub.1) splitting off the ethylene ketal protecting group from the azetidinone derivative of the formula IVa, ##STR2## reducing the compound of the formula III thus obtained, ##STR3## treating the resulting compound of the formula II ##STR4## with concentrated aqueous hydrogen chloride solution; or (a.sub.2) reducing the compound of the formula III, treating the compound of the formula II thus obtained with concentrated aqueous hydrogen chloride solution; or (a.sub.3) treating the compound of the formula II with concentrated aqueous hydrogen chloride solution; and isolating the compound of the formula I thus obtained from the reaction mixture. The compound of the formula I is useful as an intermediate in the production of thienamycin, a highly potent antibiotic.Type: GrantFiled: June 27, 1983Date of Patent: December 17, 1985Assignee: Richter Gedeon Vegyeszeti Gyav R.T.Inventors: Karoly Lempert, Gabor Doleschall, Jozsef Fetter, Gyula Hornyak, Jozsef Nyitrai, Gyula Simig, Karoly Zauer
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Patent number: 4547579Abstract: There are described novel dyes of the formulae ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, and R.sub.1 and R.sub.2 together with the nitrogen atom, and optionally with the inclusion of further hetero atoms, can also form a 5- to 7-membered heterocycle, or one of the radicals R.sub.1 or R.sub.2 can be linked with the carbon atoms, in the o-position with respect to the amino group, of the ring A to form a fused-on, saturated, unsubstituted or substituted 5- or 6- membered ring,X is .dbd.NR.sub.3, .dbd.NCOR.sub.4, ##STR2## .dbd.NH or .dbd.O, wherein R.sub.3 is alkyl or unsubstituted or substituted phenyl,R.sub.4 is unsubstituted or substituted alkyl, aralkyl, aryl, vinyl, alkoxy, phenoxy or amino, andR.sub.5 is cyano, carbalkoxy, or unsubstituted or substituted carbonamide, andR.sub.Type: GrantFiled: September 30, 1982Date of Patent: October 15, 1985Assignee: Ciba-Geigy CorporationInventor: Peter Mockli
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Patent number: 4496747Abstract: A process for the preparation of dehydroacetic acid which comprises heating 2,2,6-trimethyl-4H-1,3-dioxin-4-one, preferably at a temperature of about 130.degree. C. to about 160.degree.C., the heating being carried out preferably in the presence of an inert solvent such as xylene and preferably dehydroacetic acid; the solvent being present in an amount of about 0.05 to about 2.0 moles per mole of the compound being heated, the process further comprising recovering dehydroacetic acid so produced.Type: GrantFiled: April 21, 1983Date of Patent: January 29, 1985Assignee: Eastman Kodak CompanyInventor: Robert J. Clemens
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Patent number: 4491659Abstract: Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II, III and IV to known lactone V which is known to be useful via acid VI in the total synthesis of thienamycin (VII): ##STR1## wherein R.sup.1 is hydrogen or a removable protecting group; R is a removable protecting group.Type: GrantFiled: May 26, 1983Date of Patent: January 1, 1985Assignee: Merck & Co., Inc.Inventor: Philippe L. Durette
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Patent number: 4482727Abstract: Compounds having the structural formula ##STR1## wherein R is hydrogen or halogen, R.sup.1 is halogen, R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl, and X is oxygen or methylene useful as post-emergent herbicides against annual and perennial grasses.Type: GrantFiled: July 1, 1983Date of Patent: November 13, 1984Assignee: Stauffer Chemical CompanyInventor: David L. Lee
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Patent number: 4415740Abstract: A method for preparing a lactone reaction product comprising reacting an alkenyl-succinic acid under substantially anhydrous conditions at elevated temperature ranging up to about 100.degree. in the presence of an .alpha. carbon halogen substituted acetic acid. The .alpha. carbon halogen substituted acetic acid may have from one to three halogen substituents and has a pKa of less than 3.Type: GrantFiled: June 14, 1982Date of Patent: November 15, 1983Assignee: Texaco Inc.Inventor: Benjamin J. Kaufman
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Patent number: 4360684Abstract: Disclosed is a process for preparing (2S)-tetrahydro-2.alpha.-methyl-6-oxo-4.beta.-amino-2H-pyran-3.alpha.-carb oxylic acid (I) which is useful in the synthesis of thienamycin. The process proceeds via a stereospecific reduction of the 2-acetyl-3-(R)-.alpha.-methylbenzylamino-2-pentenedioic acid diester (II). ##STR1## wherein R is, .alpha.-methylbenzyl, and R.sup.1 is lower alkyl having 1-6 carbon atoms or arylalkyl such as benzyl.Type: GrantFiled: April 8, 1981Date of Patent: November 23, 1982Assignee: Merck & Co., Inc.Inventors: Raymond J. Cvetovich, David G. Melillo, Kenneth M. Ryan, Meyer Sletzinger
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Patent number: 4349687Abstract: Disclosed is a process for the stereocontrolled total synthesis of thienamycin via intermediates II and IIa: ##STR1## wherein R is a readily removable carboxyl protecting group.Type: GrantFiled: April 8, 1981Date of Patent: September 14, 1982Assignee: Merck & Co., Inc.Inventors: Thomas M. H. Liu, David G. Melillo, Kenneth M. Ryan, Ichiro Shinkai, Meyer Sletzinger
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Patent number: 4344885Abstract: Disclosed is a process for the stereocontrolled total synthesis of thienamycin from acetone dicarboxylate via intermediate II: ##STR1## wherein R is a readily removable carboxyl protecting group.Type: GrantFiled: April 17, 1981Date of Patent: August 17, 1982Assignee: Merck & Co., Inc.Inventors: Thomas M. H. Liu, David G. Melillo, Kenneth M. Ryan, Ichiro Shinkai, Meyer Sletzinger