The Spiro Includes A Three- Or Four-membered Hetero Ring Patents (Class 549/332)
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Patent number: 5180738Abstract: The present invention is related to a compound of the formula ##STR1## wherein R.sup.1 is a 2-methyl-1-propenyl or isobutyl group which may be substituted and R.sup.2 is (1) a substituted alkanoyl group, (2) a substituted aroyl group having at least one substituent selected from the group consisting of C.sub.2-6 alkyl, amino, halogen, hydroxyl, lower alkoxy, cyano, carbamoyl and carboxyl, (3) an aromatic heterocycle-carbonyl, which may optionally be substituted, (4) a carbamoyl group, which may optionally be substituted, (5) an alkyl group, which may optionally be substituted, (6) a benzenesulfonyl group, which may optionally be substituted, (7) an alkylsulfonyl group, which may optionally be substituted, (8) a sulfamoyl group, which may optionally be substituted, (9) an alkoxycarbonyl group, which may optionally be substituted or (10) a phenoxycarbonyl group, which may optionally be substituted; or a salt thereof.The compound (I) has a strong angiogenesis inhibitory activity.Type: GrantFiled: June 13, 1991Date of Patent: January 19, 1993Assignee: Takeda Chemical IndustriesInventors: Shoji Kishimoto, Takeshi Fujita
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Patent number: 5171747Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group;D is an oxygen atom or a NOR group, wherein R.dbd.H or C.sub.1 -C.sub.4 alkyl;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group; andR'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain,useful as drugs.Type: GrantFiled: October 16, 1990Date of Patent: December 15, 1992Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5166172Abstract: The present invention is related to a compound of the formula ##STR1## wherein R.sup.1 is a 2-methyl-1-propenyl or isobutyl group which may be substituted and R.sup.2 is (1) a substituted alkanoyl group, (2) a substituted aroyl group having at least one substituent selected from the group consisting of C.sub.2-6 alkyl, amino, halogen, hydroxyl, lower alkoxy, cyano, carbamoyl and carboxyl, (3) an aromatic heterocycle-carbonyl, which may optionally be substituted, (4) a carbamoyl group, which may optionally be substituted, (5) an alkyl group, which may optionally be substituted, (6) a benzenesulfonyl group, which may optionally be substituted, (7) an alkylsulfonyl group, which may optionally be substituted, (8) a sulfamoyl group, which may optionally be substituted, (9) an alkoxycarbonyl group, which may optionally be substituted or (10) a phenoxycarbonyl group, which may optionally be substituted; or a salt thereof.The compound (I) has a strong angiogenesis inhibitory activity.Type: GrantFiled: February 28, 1991Date of Patent: November 24, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Shoji Kishimoto, Takeshi Fujita
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Patent number: 5164410Abstract: The present invention is related to a compound of the formula ##STR1## wherein R.sup.1 is a 2-methyl-1-propenyl or isobutyl group which may be substituted and R.sup.2 is (1) a substituted alkanoyl group, (2) a substituted aroyl group having at least one substituent selected from the group consisting of C.sub.2-6 alkyl, amino, halogen, hydroxyl, lower alkoxy, cyano, carbamoyl and carboxyl, (3) an aromatic heterocycle-carbonyl, which may optionally be substituted, (4) a carbamoyl group, which may optionally be substituted, (5) an alkyl group, which may optionally be substituted, (6) a benzenesulfonyl group, which may optionally be substituted, (7) an alkylsulfonyl group, which may optionally be substituted, (8) a sulfamoyl group, which may optionally be substituted, (9) an alkoxycarbonyl group, which may optionally be substituted or (10) a phenoxycarabonyl group, which may optionally be substituted; or a salt thereof.The compound (I) has a strong angiogenesis inhibitory activity.Type: GrantFiled: June 13, 1991Date of Patent: November 17, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Shoji Kishimoto, Takeshi Fujita
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Patent number: 5157131Abstract: Epoxides represented by the formula: ##STR1## in which A represents a methylene or oxirane group and a process for their preparation.Type: GrantFiled: October 24, 1991Date of Patent: October 20, 1992Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre Chabardes, Bernard Delmond, Claude Filliatre, Michel Pereyre, Dominique Serramedan
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Patent number: 5151352Abstract: A clerodane-type diterpene derivative, which has antibacterial and antitumor activities, as well as chemically equivalent tautomers thereof and a process for producing said derivative using a microorganism belonging to the genus Streptomyces.Type: GrantFiled: September 30, 1991Date of Patent: September 29, 1992Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hirofumi Nakano, Shozo Kawada, Yoichi Uosaki, Yutaka Saito, Katsushige Gomi, Toshiaki Iwazaki
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Patent number: 5125954Abstract: The present invention relates to novel bicyclo ether derivatives, to compositions containing them, and to their method of use especially to control the growth of undesired vegetation in rice.Type: GrantFiled: November 2, 1990Date of Patent: June 30, 1992Assignee: E.I. Du Pont de Nemours and CompanyInventors: James E. Powell, Richard B. Phillips
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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: 5089630Abstract: A dioxetane that includes a fluorescent chromophore spiro-bound at the 4-carbon of the dioxetane. The dioxetane has the formula ##STR1## where X is CR.sub.7 R.sub.8, O, S, or N-R (where each R.sub.7, R.sub.8, and R, independently, is H, alkyl, heteroalkyl, aryl, heteroaryl, cycloalkyl, cycloheteroalkyl, aralkyl, alkaryl, or an enzyme cleavable group), and each R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, andR.sub.6, independently, is H, an electron-withdrawing group, an electron-donating group, heteroaryl, or an enzyme cleavable group, or groups R.sub.1 -R.sub.6 together form a ring, and T is a substituted or unsubstituted aryl, polyaryl, cycloalkylidene or polycycloalkylidene group spiro-bound at the 3-carbon of the dioxetane.The dioxetane can be decomposed by direct cleavage of the dioxetane 0--0 bond or by cleavage of an enzyme cleavable group bonded to the dioxetane to form a luminescent substance that includes the coumarin portion of the dioxetane.Type: GrantFiled: April 13, 1990Date of Patent: February 18, 1992
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Patent number: 5081312Abstract: New 4,4,5,8-tetramethyl-1-oxaspiro[2,5]octane. A process for its preparation starting from 2,2,3,6-tetramethyl-1-cyclohexanone is described.4,4,5,8-Tetramethyl-1-oxaspiro[2,5]octane is a useful raw material for the preparation of 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde, a key intermediate for the synthesis of valuable fragrance ingredients.Type: GrantFiled: February 20, 1991Date of Patent: January 14, 1992Assignee: Firmenich SAInventors: Christian Chapuis, Christian Margot, Karl-Heinrich Schulte-Elte, Herve Pamingle
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Patent number: 5017711Abstract: New 4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane. A process for its preparation starting from 2,2,3,6-tetramethyl-1-cyclohexanone is described.4,4,5,8-Tetramethyl-1-oxaspiro[2.5]octane is a useful raw material for the preparation of 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde, a key intermediate for the synthetis of valuable fragrance ingredients.Type: GrantFiled: December 13, 1989Date of Patent: May 21, 1991Assignee: Firmenich S.A.Inventors: Christian Chapuis, Christian Margot, Karl-Heinrich Schulte-Elte, Herve Pamingle
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Patent number: 5015744Abstract: Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: ##STR1## wherein R.sub.1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R.sub.2 is hydrogen, ethoxyethyl, 2,2,2-trichloroethoxymethyl or other hydroxyl protecting group; and R.sub.3 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; the contacting of said alcohol and oxazinone being carried out in the presence of a sufficient amount of an activating agent under effective conditions to cause the oxazinone to react with the alcohol to form a .beta.-amido ester which is suitable for use as an intermediate in the synthesis of taxol.Type: GrantFiled: November 14, 1989Date of Patent: May 14, 1991Assignee: Florida State UniversityInventor: Robert A. Holton
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Patent number: 5013827Abstract: Triggerable dioxetanes with a fluorescent molecule containing group bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.Type: GrantFiled: November 13, 1989Date of Patent: May 7, 1991Assignee: Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
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Patent number: 5004815Abstract: .beta.-Lactones are synthesized from a thiol ester and a ketone by a method which efficiently produces .beta.-lactones in high yields. The method involves combining the thiol ester, a ketone or aldehyde, a base, and an organic solvent at subambient temperatures. The thiol ester and ketone form an adduct, which upon warming, spontaneously cyclizes to yield a .beta.-lactone. .beta.-Lactones formed by this method are then decarboxylated, generally by warming in the presence of an adsorbent in an organic solvent, to stereospecifically form the corresponding alkenes.Type: GrantFiled: April 26, 1989Date of Patent: April 2, 1991Assignee: Massachusetts Institute of TechnologyInventors: Rick L. Danheiser, James S. Nowick
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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: 4975380Abstract: Thermochemically induced luminescence is generated in a fluorescent labeled organic compound containing a covalently bonded fluorescent label which is a polycyclic aromatic radical having at least three linearly fused benzene rings and capable of being excited to a fluorescent electronic excited state by energy transfer from an energy donor molecule or radical having an electronic excited state, by a process comprising generating an energy donor radical or molecule by a thermochemical reaction in the presence of the fluorescent label. The energy donor radical may be generated by a chemical reaction in the presence of the fluorescent labeled organic compound or the fluorescent labeled compound itself may be additionally labeled with a radical capable of being excited to an electronic excited state by a thermochemical reaction, i.e., by a process initiated by adsorption of thermal energy.Type: GrantFiled: November 30, 1989Date of Patent: December 4, 1990Assignee: Rijksuniversiteit Te GroningenInventors: Jan C. Hummelen, Hans Wynberg
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Patent number: 4965257Abstract: Bicyclo-[2,2,1]-heptanes, bicyclo-[2,2,2]-octanes and bicyclo-[2,2,3]-nonanes, having 2 or 3 ring hetero atoms selected from O, S and N, substituted at the 1-position by a 4-alkynylphenyl group and at the 4-position and optionally at the 3 and/or 5-position are valuable pesticides, particularly insecticides and acaracides. The compounds may be prepared by reacting an alkyne with the corresponding 4-iodophenyl substituted compounds or by debromination of the corresponding 4-dibromomethylphenyl substituted compound.Type: GrantFiled: July 24, 1989Date of Patent: October 23, 1990Assignee: The Regents of the University of CaliforniaInventors: John E. Casida, Christopher J. Palmer, John P. Larkin, Ian H. Smith
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Patent number: 4956477Abstract: Compounds having the formula: ##STR1## wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C.sub.1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., m-phenylene), produced by reacting a compound having the formula: ##STR2## with an R-ylating agent (e.g., R.sub.2 SO.sub.4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: ##STR3## are produced by reacting a compound having the formula: ##STR4## wherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having the formula ##STR5## are produced by reacting a compound of the formula ##STR6## with a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups.Type: GrantFiled: September 22, 1989Date of Patent: September 11, 1990
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Patent number: 4952707Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.Type: GrantFiled: June 30, 1988Date of Patent: August 28, 1990
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Patent number: 4939275Abstract: Synthetically prepared periplanone A of the formula I ##STR1## its preparation and its use for controlling cockroaches.Type: GrantFiled: November 6, 1987Date of Patent: July 3, 1990Assignee: BASF AktiengesellschaftInventors: Peter Hofmeister, Wolfgang Krieg, Reinhard Neudert, Hagen Hauptmann
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Patent number: 4931569Abstract: Methods are disclosed for purifying chemiluminescent water-soluble 1,2-dioxetane derivatives suitable for use as reporter molecules in a variety of biological analytical systems, including enzyme-linked immunoassays, nucleic acid probe techniques, and structural determinations. The methods are based upon high pressure, medium pressure or low pressure liquid chromatography using as the stationary phase alkaline pH-stable compositions with the chromatographic characteristics of reversed-phase adsorbents, at alkaline pH values, and in the absence of acid-forming compounds or compounds with an unshared pair of electrons. Desalting of substantially pure water soluble 1,2-dioxetane derivatives may be accomplished by the same chromatographic systems or by molecular sieve chromatography systems, but in the absence of salt buffers. Under some circumstances, purification and desalting may be combined in a single chromatographic step.Type: GrantFiled: September 14, 1988Date of Patent: June 5, 1990
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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: 4912132Abstract: Novel physiologically active substances KS-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.Type: GrantFiled: April 14, 1988Date of Patent: March 27, 1990Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu
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Patent number: 4885246Abstract: New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octan-3-one , by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.Type: GrantFiled: December 19, 1988Date of Patent: December 5, 1989Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Kenji Mori, Masahiro Tsuji
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Patent number: 4880894Abstract: Novel quaternary ammonium salts of general formula (I) ##STR1## wherein: R is a saturated or unsaturated, linear or branched alkyl radical of C.sub.1 to C.sub.8.R' is a saturated or unsaturated, linear or branched alkyl radical of C.sub.1 to C.sub.12, or a benzyl radical.n is a number equal to 2 or 3.X.sup..theta. is a halogenide anion, such as Cl.sup..theta., Br.sup..theta., I.sup..theta., are used as phase transfer catalysts, in heterogeneous ionic reactions wherein the reagents are in different phase and have different polarity.Type: GrantFiled: September 26, 1988Date of Patent: November 14, 1989Assignee: Alter, S.A.Inventors: Carlos Sunkel, Miguel Fay de Casa Juana, Fernando Dorrego, Basilio Pando, Julio Alvarez-Builla, Juan J. Vaquero, Carlos Galera, Maria L. Vazquez
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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: 4868204Abstract: Mycalamide compounds are derived from marine sponges of the genus Mycale or prepared by synthetic methods. These compounds and pharmaceutical compositions containing them as active ingredients are useful as antitumor and antiviral agents.Type: GrantFiled: May 25, 1988Date of Patent: September 19, 1989Assignee: Harbor Branch Oceanographic Institution, Inc.Inventors: John W. Blunt, Murray H. G. Munro, Nigel B. Perry, Andrew M. Thompson
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Patent number: 4861703Abstract: Radiation-sensitive silver halide photographic elements are disclosed which are protected against fog by cyclic dichalcogenides. A new cyclic oxaspiro ditelluride is disclosed.Type: GrantFiled: August 15, 1988Date of Patent: August 29, 1989Assignee: Eastman Kodak CompanyInventors: Roger Lok, Wolfgang H. H. Gunther, John P. Freeman
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Patent number: 4857652Abstract: Novel light producing 1,2-dioxetanes are described of the formula ##STR1## wherein ArOX is an aryl ring substituted with an X oxy group and A are passive organic groups which allow the 1,2-dioxetane to produce light when triggered by removing X. X is a chemically labile group which is removed by an activating agent. The 1,2-dioxetane compounds can be triggered to produce light at room temperatures.Type: GrantFiled: August 23, 1988Date of Patent: August 15, 1989Assignee: Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
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Patent number: 4847390Abstract: Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopentanecarbonyl)-R-1,1-diaminoe thane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxymethylene, or --CH.sub.2 --O--.Type: GrantFiled: April 27, 1988Date of Patent: July 11, 1989Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shunichi Ikeda, Kentaro Tamaki
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Patent number: 4814468Abstract: New intermediate, an optically active (1S,5R)-7,7-alkylenedioxy-2-alkoxycarbonylbicyclo[3.3.0]octan-3-one which is useful for the synthesis of an optically active carbacyclin. This intermediate is prepared, as a non-reduced compound, from a racemic compound, (1SR,5RS)-7,7-alkylenedioxy-2-alkoxycarbonyl-cis-bicyclo[3.3.0]octane-3-on e, by treatment of the racemic compound with a microorganism. The microorganism has an ability of specifically reducing the keto group of the (1R,5S) epimer of the racemic compound.Type: GrantFiled: May 30, 1986Date of Patent: March 21, 1989Assignee: Nisshin Flour Milling Co., Ltd.Inventors: Kenji Mori, Masahiro Tsuji
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Patent number: 4792606Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.Type: GrantFiled: July 16, 1987Date of Patent: December 20, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hermann-Dieter Krall
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Patent number: 4731458Abstract: Compounds of the formula ##STR1## are described wherein X is a C.sup.2-11 -alkyl group, optionally substituted by a protected hydroxy, protected oxo or protected carboxy group.Type: GrantFiled: April 25, 1986Date of Patent: March 15, 1988Assignee: CBD CorporationInventor: Walter J. Kasha
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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: 4716241Abstract: Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopentanecarbonyl)-R-1,1-diaminoe thane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxy-methylene, or --CH.sub.2 --O--.Type: GrantFiled: February 28, 1986Date of Patent: December 29, 1987Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shunichi Ikeda, Kentaro Tamaki
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Patent number: 4713470Abstract: There is disclosed a process for the racemization of amino acids and derivatives thereof. The racemization process of the present invention uses an aromatic aldehyde-containing polymer made from the reaction of a hydroxy-aromatic aldehyde with a chloromethylated vinylbenzene polymer under reaction conditions to form an aromatic aldehyde-containing polymer wherein the aldehydic moiety is linked to the polymer through an ether linkage. There is also disclosed a process for the production of the racemization catalyst. Another embodiment of the invention comprises a process for the promotion of the racemization reaction wherein a tertiary amine-containing resin is used as a promoting agent.Type: GrantFiled: May 22, 1985Date of Patent: December 15, 1987Assignee: Stauffer Chemical CompanyInventor: Stanley B. Mirviss
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Patent number: 4684664Abstract: Disclosed herein are derivatives of .beta.-(4-isocyano-1,2,3,4-diepoxycyclopentyl)acrylic acid, the derivatives showing an antibacterial activity, an antifungal activity and an antimycoplasmal activity.Type: GrantFiled: January 16, 1985Date of Patent: August 4, 1987Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Katsuhisa Osugi, Isao Ichinose, Eisaku Takahashi, Masato Arahira
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Patent number: 4668698Abstract: The invention concerns novel [(4-phenyl-1,3-dioxan-cis-5-yl)alkyl]phenylalkanoic acids of the formula I wherein Ra and Rb are a variety of substituents including alkyl, alkenyl, halogenoalkyl, phenyl and benzyl, or together form polymethylene; Rc is hydroxy, alkoxy or alkanesulphonamido; A.sup.1 and A.sup.2 are polymethylene; X is oxygen, sulphur or a direct bond; and benzene ring A bears a variety of substituents; and, when Rc is hydroxy, the physiologically acceptable salts thereof. The compounds of formula I are thromboxane antagonists of value in treating a variety of disease conditions. The invention also provides processes for the manufacture of, and pharmaceutical compositions of, the compounds of formula I.Type: GrantFiled: November 9, 1984Date of Patent: May 26, 1987Assignee: Imperial Chemical Industries PLCInventor: Andrew G. Brewster
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Patent number: 4647579Abstract: Novel substituted 4-hydroxy-benzopyrans of the formula ##STR1## in which X is a single bond, ##STR2## and the other radicals can have various meanings, or pharmaceutically acceptable addition salts thereof, which are active on the circulation system.Type: GrantFiled: March 21, 1985Date of Patent: March 3, 1987Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Kabbe, Arno Widdig, Ulrich Niewohner, Andreas Knorr, Bernward Garthoff, Stanislav Kazda
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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: 4602934Abstract: Novel compounds of the formula ##STR1## wherein D is hydrogen, halogen, (halo)alkyl or (halo)alkoxy; R is alkyl or is cycloalkyl optionally 1-substituted by alkyl or halogen and R.sup.1 is the hydrocarbyl residue of a saturated oxygen-heterocyclic alcohol, are useful as herbicides.Type: GrantFiled: November 13, 1984Date of Patent: July 29, 1986Assignee: Shell Oil CompanyInventor: Kurt H. Pilgram
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Patent number: 4602933Abstract: Novel compounds of the formula ##STR1## wherein D is hydrogen, halogen, (halo)alkyl or (halo)alkoxy; R is hydrogen, alkyl or alkoxy and R.sup.1 is the hydrocarbyl residue of a saturated oxygen-heterocyclic alcohol, are useful as herbicides.Type: GrantFiled: November 13, 1984Date of Patent: July 29, 1986Assignee: Shell Oil CompanyInventor: Kurt H. Pilgram
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Patent number: 4591457Abstract: Azetidine compounds of the general formula I ##STR1## wherein Ar represents a para-tolyl group and X represents a hydrogen atom, a carboxyl group or a hydroxymethyl group; their preparation from pentaerythritol via compounds of formula ##STR2## wherein Hal represents chlorine, bromine or iodine, Y represents oxygen or ##STR3## and Z represents Hal or OH, together with their use as intermediates in the preparation of 3-carboxyazetidine; also the compounds of formula ##STR4## wherein R.sub.1 and R.sub.Type: GrantFiled: July 29, 1985Date of Patent: May 27, 1986Assignee: Shell Oil CompanyInventors: Gary Scholes, Robert van Helden
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Patent number: 4576961Abstract: This invention relates to antibiotic substances, in particular to an antibiotic complex for use in the human and veterinary clinical practice and as an additive in feeds.Type: GrantFiled: August 30, 1983Date of Patent: March 18, 1986Inventors: Henning O. B. Lorck, Poul R. Rasmussen
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Patent number: 4552971Abstract: Novel mono-, di- and triacylated derivatives of scirpentriol are provided for use as antitumor agents. Also provided are methods for the production of such derivatives.Type: GrantFiled: February 27, 1984Date of Patent: November 12, 1985Assignee: Bristol-Myers CompanyInventors: Henry Schmitz, Takushi Kaneko, John M. Essery, Terrence W. Doyle
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Patent number: 4525201Abstract: The present invention is directed to novel compounds of formulas I or II ##STR1## wherein R is an optionally substituted unsaturated group containing up to 4 carbon atoms, a cycloalkyl group containing 3 to 10 carbon atoms, a secondary alkyl group containing 3 to 10 carbon atoms, an aromatic group containing up to 14 carbon atoms or a heterocyclic group containing up to 14 carbon atoms; in formula I, m is 0, 1 or 2; n is 1, 2 or 3; R.sup.1 and R.sup.2 each independently is a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or a hydroxyalkyl or an alkoxymethyl group in which the alkyl portion contains 1 to 6 carbon atoms; X is CH.sub.2 when m is 0, 1 or 2; or X is oxygen when m is 1 or 2; or in formula II, n is 1, 2 or 3; m is 0 or 1; and R.sup.1 and R.sup.2 each independently is a hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or a hydroxyalkyl or an alkoxymethyl group in which the alkyl portion contains 1 to 6 carbon atoms.Type: GrantFiled: October 24, 1983Date of Patent: June 25, 1985Assignee: Shell Oil CompanyInventors: Willy D. Kollmeyer, Thomas L. Brown
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Patent number: 4523022Abstract: The present invention concerns the novel, sugar-ring expansion for synthesis of novel analogs of spectinomycin or C-6' analogs of spectinomycin from known aminomethyldihydrospectinomycin and analogs thereof. Additionally, the invention concerns the novel synthesis of novel 7 membered sugar-ring analogs of dihydrospectinomycin and C-6' analogs thereof from novel 7 membered sugar-ring spectinomycin and C-6' analogs thereof by treatment with NaBH.sub.4.Type: GrantFiled: July 7, 1983Date of Patent: June 11, 1985Assignee: The Upjohn CompanyInventor: Richard C. Thomas
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Patent number: 4499000Abstract: Certain spirocyclic ketals of the formula ##STR1## in which R.sup.1 in the case where R.sup.2 denotes hydrogen, represents a cyclohexyl radical optionally substituted by lower alkyl, lower alkoxy and/or cycloalkyl with 5 to 7 carbon atoms, or in whichR.sup.1 and R.sup.2 are linked through 4 methylene groups, which are optionally substituted by lower alkyl, lower alkoxy and/or cycloalkyl with 5 to 7 carbon atoms and form a further acyclic ring.R.sup.3, R.sup.4 and R.sup.5 are identical or different and denote hydrogen, lower alkyl, lower alkoxy or cycloalkyl with 5 to 7 carbon atoms, andZ denotes alkylene with 2 to 4 carbon atoms which is optionally substituted by lower alkyl and/or cycloalkyl with 5 to 7 carbon atoms,are disclosed together with their use in power transmission fluids.Type: GrantFiled: February 18, 1983Date of Patent: February 12, 1985Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Hentschel, Rolf Dhein, Hans Winter, Herbert Vojacek
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Patent number: 4496745Abstract: Compounds of formula (I): ##STR1## (in which: R.sup.1 and R.sup.2 are the same or different and each represents hydrogen or a hydroxy-protecting group:R.sup.3 represents an alkyl group having from 1 to 12 carbon atoms which is optionally substituted, an alkenyl group having from 2 to 12 carbon atoms, an alkynyl group having from 2 to 6 carbon atoms or a cycloalkyl group which is optionally substituted; andX represents an ethylene group, a trans-vinylene group or an ethynylene group) and salts and esters thereof are useful intermediates in the conversion of 5Z-carbacyclin derivatives to their 5E-isomers and in the preparation of certain other carbacyclin compounds.Type: GrantFiled: October 25, 1983Date of Patent: January 29, 1985Assignee: Sankyo Company, LimitedInventors: Shigeo Amemiya, Koichi Kojima
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Patent number: 4479007Abstract: Chroman-4-ones are prepared by reacting an o-hydroxyarylcarbonyl compound with a carbonyl compound in the presence of an amine.Type: GrantFiled: July 23, 1979Date of Patent: October 23, 1984Assignee: Bayer AktiengesellschaftInventor: Hans-Joachim Kabbe