Chalcogen Bonded Directly To The Oxazine Ring Patents (Class 544/97)
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Patent number: 6028224Abstract: A synthesis of fluoxetine is disclosed. The process begins with a lower alkyl ester of 3-benzoylpropionic acid, which is reduced in the presence of a chiral ligand to produce the corresponding .gamma.-hydroxy ester, and the ester is cleaved. The free acid is then condensed with the alcohol to form a .gamma.-lactone, which is treated with ammonia to provide the .gamma.-hydroxy amide. The amide undergoes a Hoffman rearrangement to provide a 2-oxo-1,3 oxazine, which is reduced to 3-(methylamino)-1-phenyl-1-propanol. The alcohol is deprotonated and reacted with a 4-chloro- or 4-fluoro benzotrifluoride to provide fluoxetine free base.Type: GrantFiled: May 24, 1999Date of Patent: February 22, 2000Assignee: Sepracor Inc.Inventors: James Wallace Hilborn, Alex Roger Jurgens, Chris Hugh Senanayake
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Patent number: 6028032Abstract: 1,3-oxazin-4-ones of formula (I), ##STR1## wherein R.sup.1 represents phenyl optionally substituted; R.sup.2 represents: a straight- or branched-chain alkyl having from one to ten carbon atoms which is substituted by one or more groups R.sup.8 which may be the same or different; a straight- or branched-chain optionally halogenated alkenyl or alkynyl group having up to ten carbon atoms; or a group selected from cyano, --CHO, --COR.sup.7, --CO.sub.2 H, --CO.sub.2 R.sup.7, --COSR.sup.7, --CONR.sup.9 R.sup.10, --CH.dbd.NOH, --CH.dbd.NOR.sup.7, --CH.dbd.NOCOR.sup.7, --CH.dbd.NNR.sup.9 R.sup.10, --CH.sub.2 CN, --CH.sub.2 NO.sub.2 and oxiranyl; R.sup.3 represents phenyl optionally substituted or R.sup.3 represents a first five to seven membered heteroaromatic ring; said first ring being optionally fused and said first ring being linked to the nitrogen atom of the group NR.sup.6 via one of the ring carbon atoms; R.sup.4 and R.sup.5 independently represent lower alkyl; W represents --NR.sup.6 --; R.sup.Type: GrantFiled: April 13, 1998Date of Patent: February 22, 2000Assignee: Rhone-Poulenc Agriculture Ltd.Inventors: Michael Colin Cramp, Yoshihiro Usui, Keiichi Hayashizaki
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Patent number: 6004955Type: GrantFiled: August 12, 1998Date of Patent: December 21, 1999Assignee: DuPont Pharmaceuticals CompanyInventors: Fuqiang Jin, Pasquale Nicholas Confalone
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Patent number: 5977025Abstract: This invention provides 1,3-oxazin-4-one derivatives represented by following general formula (I): ##STR1## in which R.sup.1 represents a phenyl group which may be substituted; R.sup.2 represents a hydrogen atom or a lower alkyl group; R.sup.3 represents a hydrogen atom, a lower alkyl group, an aralkyl group or a phenyl group which may be substituted; R.sup.4 and R.sup.5 each independently represent a lower alkyl group; and W represents an oxygen atom or a group represented by the formula --N(R.sup.6)-- in which R.sup.6 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkynyl group. There are also provided herbicidal compositions containing the derivatives and intermediates for preparing them. The compounds according to the present invention exhibit strong herbicidal activities and thus they are useful as active ingredients of agricultural chemicals.Type: GrantFiled: June 20, 1996Date of Patent: November 2, 1999Assignee: Mitsubishi Chemical CorporationInventors: Keiichi Hayashizaki, Yoshihiro Usui, Koichi Araki, Norishige Toshima, Tetsuya Murata, Takako Aoki, Atsushi Go, Hideshi Mukaida, Rika Higurashi
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Patent number: 5977359Abstract: The invention relates to compounds of the formula ##STR1## in which: A is a divalent radical selected from:A.sub.1) --O--CO--A.sub.2) --CH.sub.2 --O--CO--A.sub.3) --O--CH.sub.2 --CO--A.sub.4) --O--CH.sub.2 --CH.sub.2 --A.sub.5) --N(R.sub.1)--CO--A.sub.6) --N(R.sub.1)--CO--CO--A.sub.7) --N(R.sub.1)--CH.sub.2 --CH.sub.2 --A.sub.8) --O--CH.sub.2 --in which:R.sub.1 is a hydrogen or a (C.sub.1 -C.sub.4)-alkyl; andAm is a nitrogen-containing heterocycle.Type: GrantFiled: October 20, 1998Date of Patent: November 2, 1999Assignee: SanofiInventors: Xavier Emonds-Alt, Isabelle Grossriether, Patrick Gueule, Vincenzo Proietto, Didier Van Broeck
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Patent number: 5972237Abstract: Heterocyclic compounds IR.sup.1 --X--L (I)whereL is a cyclic carbamate residue, a lactonoxy residue or a lactam residue,X is an oxygen-containing group ##STR1## where A is a linker, and R.sup.1 is an organic radical or a group L,are used as activators for inorganic peroxy compounds, in particular as cold bleach activators or optical brighteners in detergents, cleaners and bleaches and in disinfectants.Type: GrantFiled: November 17, 1997Date of Patent: October 26, 1999Assignee: BASF AktiengesellschaftInventors: Reinhard Muller, Thomas Wehlage, Wolfgang Trieselt, Alfred Oftring, Elisabeth Kappes, Gunter Oetter, Dieter Boeckh, Roland Ettl, Albert Hettche
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Patent number: 5932521Abstract: Novel 1,3-oxazin-4-one derivatives of the formula ##STR1## wherein R.sup.1 to R.sup.5 are hydrocarbyl radicals which are optionally substituted, and herbicidal compositions comprising the same as active ingredients and their use in controlling the growth of weeds. The compounds can be produced by reacting substituted 1,3-dioxin-4-one derivatives and N-methylene-alkylamine.Type: GrantFiled: July 22, 1997Date of Patent: August 3, 1999Assignee: Rhone-Poulenc AgrochimieInventors: Atsushi Go, Rika Higurashi, Miki Komine, Yoshimi Tsutsumi, Yoshihiro Usui
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Patent number: 5914332Abstract: A compound of the formula: ##STR1## is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.Type: GrantFiled: November 21, 1996Date of Patent: June 22, 1999Assignee: Abbott LaboratoriesInventors: Hing Leung Sham, Daniel W. Norbeck, Xiaoqi Chen, David A. Betebenner
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Patent number: 5789404Abstract: 3-Substituted 1-arylindole compounds are provided having general formula (I) ##STR1## wherein Ar is an optionally substituted aryl group; X represents a divalent hydrocarbon group, methyleneoxy or -thioxo; R.sup.1 -R.sup.4 are hydrogen or other substituents; R.sup.5 is hydrogen, alkyl, alkenyl, etc.; R.sup.6 and R.sup.7 are independently hydrogen, alkyl, alkenyl, etc.; R.sup.8 is alkyl, alkenyl or R.sup.8 represents a group of formula 1a or 1b; wherein n is an integer from 2-8; W is O or S; U is N or CH; Z is (CH.sub.2).sub.m, m being 2 or 3, 1,2-phenylene optionally substituted with halogen or trifluoromethyl, CH.dbd.CH, COCH.sub.2 or CSCH.sub.2 ; V is O, S, CH.sub.2 or NR.sup.10, wherein R.sup.10 is hydrogen, alkyl, alkenyl, cycloalkyl, etc.; U.sup.1 is O, S, CH.sub.2 or a group NR.sup.11, wherein R.sup.11 is hydrogen, alkyl, alkenyl, etc.; and V.sup.1 is NR.sup.12 R.sup.13, OR.sup.14, SR.sup.15 or CR.sup.16 R.sup.17 R.sup.18, where R.sup.12 -R.sup.18 are as the R.sup.10 substituents; R.sup.Type: GrantFiled: August 12, 1996Date of Patent: August 4, 1998Assignee: H. Lundbeck A/SInventors: Kim Andersen, Jens Kristian Perregaard
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Patent number: 5777111Abstract: A compound of the formula (2a) ##STR1## in which Ar.sup.1 is 2-sulfophenyl, 3-sulfophenyl, 4-sulfophenyl, 2,5-disulfophenyl, 3-sulfo-4-aminophenyl, 4-sulfo-3-aminophenyl, 3-methoxy-5-sulfophenyl, 3-sulfo-4-methylphenyl, 3-sulfo-4-methoxyphenyl, 2,5-disulfo-4-methylphenyl, 2,5-disulfo-4-methoxyphenyl, 2,5-disulfo-4-aminophenyl, 5,7-disulfo-naphth-2-yl, 4,8-disulfo-naphth-2-yl, 3,6,8-trisulfo-napth-2-yl, 4,6,8-trisulfo-naphth-2-yl, 8-sulfonaphth-1-yl, 6-sulfo-naphth-1-yl or 7-sulfo-naphth-1-yl.Type: GrantFiled: May 23, 1997Date of Patent: July 7, 1998Assignee: Hoechst AktiengesellschaftInventors: Christian Schumacher, Michael Meier, Werner Hubert Russ
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Patent number: 5708167Abstract: Proposed is a novel and very efficient method for the preparation of an N-vinyl compound such as N-vinyl-2-pyrrolidone and N-vinyl-N-ethyl acetamide by the thermal decomposition of an N-(.alpha.-acyloxyethyl) compound which is a novel compound obtained by the addition reaction between an NH group-containing compound such as 2-pyrrolidone and N-ethyl acetamide and a vinyl carboxylate, e.g., vinyl acetate, in the presence of an alkali, e.g. alkali metal hydroxide. The reaction mixture after completion of this addition reaction as such, i.e. without isolating the N-(.alpha.-acyloxyethyl) compound, such as N-(.alpha.-acetoxyethyl)-2-pyrrolidone and N-(.alpha.-acetoxyethyl)-N-ethyl acetamide, is heated to effect in situ formation of the desired N-vinyl compound which can then be isolated by distillation under reduced pressure in a very high overall yield.Type: GrantFiled: August 23, 1995Date of Patent: January 13, 1998Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.Inventors: Yoshihiro Honma, Shozo Tanaka, Mitsuyoshi Oshima, Soji Tanioka, Fumiaki Kawamoto
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Patent number: 5703215Abstract: A process for the coloration of a substrate, especially a textile, comprising the steps of:(a) applying to the substrate a mixture comprising an aqueous solvent and a water-soluble dye comprising molecules which contain a nucleophilic group and an electrophilic group; and(b) heating or basifying or heating and basifying the dye thereby causing molecules of the dye to join together.Also claimed are dyes, polymers and oligomers.Type: GrantFiled: May 30, 1995Date of Patent: December 30, 1997Assignee: Zeneca LimitedInventors: Andrew Hunter Morris Renfrew, Andrew Paul Shawcross
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Patent number: 5696054Abstract: Novel 1,3-oxazin-4-one derivatives of the formula ##STR1## wherein R.sup.1 to R.sup.5 are hydrocarbyl radicals which are optionally substituted, and herbicidal compositions comprising the same as active ingredients and their use in controlling the growth of weeds. The compounds can be produced by reacting substituted 1,3-dioxin-4-one derivatives and N-methylene-alkylamine.Type: GrantFiled: March 14, 1995Date of Patent: December 9, 1997Assignee: Rhone-Poulenc AgrochimieInventors: Atsushi Go, Rika Higurashi, Miki Komine, Yoshimi Tsutsumi, Yoshihiro Usui
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Patent number: 5693310Abstract: Compounds of general Formula I ##STR1## wherein R.sup.3 is a saturated, unsaturated, straight- or branched-chain or cyclic aliphatic hydrocarbon residue of up to 16 carbon atoms or, if R.sup.4 is a hydrogen atom, a cycloalkyl group or an aryl or aralkyl group optionally substituted by one or several C.sub.1 -C.sub.6 -dialkylamino groups or by one or several C.sub.1 -C.sub.6 -alkoxy groups,R.sup.4 is a hydrogen atom, a saturated, unsaturated, straight- or branched-chain or cyclic hydrocarbon residue of up to 16 carbon atoms, orR.sup.3 and R.sup.4 jointly mean a saturated or unsaturated 5- or 6-membered ring optionally substituted or containing an O, S, N atom or oxo substituent, and Y is COOX or CONR.sub.3 R.sub.4,are valuable complexing agents, complexes or complex salts, e.g., for use as NMR or X-ray diagnostic image-enhancement agents or radioactive diagnostic agents.Type: GrantFiled: November 19, 1990Date of Patent: December 2, 1997Assignee: Schering AktiengesellschaftInventors: Heinz Gries, Bernd Raduechel, Hans-Joachim Weinmann, Wolfgang Muetzel, Ulrich Speck
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Patent number: 5608057Abstract: Proposed are an N-(.alpha.-acyloxyethyl) compound, e.g., (N-(.alpha.-acetoxyethyl)-2-pyrrolidone, which is a novel compound and can be converted into an industrially very important N-vinyl compound, e.g., N-vinyl-2-pyrrolidone, by a thermal decomposition reaction under relatively mild conditions as well as a method for the preparation of such an N-(.alpha.-acyloxyethyl) compound. The N-(.alpha.-acyloxyethyl) compound can be synthesized in a high yield by the addition reaction of an NH group-containing compound, e.g., 2-pyrrolidone, with a vinyl carboxylate, e.g., vinyl acetate, in the presence of an alkaline compound such as alkali metal hydroxides.Type: GrantFiled: August 23, 1995Date of Patent: March 4, 1997Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.Inventors: Yoshihiro Honma, Shozo Tanaka, Mitsuyoshi Oshima, Soji Tanioka, Fumiaki Kawamoto
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Patent number: 5593944Abstract: The invention relates to new aminoaryl-1,3-oxazine-2,4-diones of the general formula (I) ##STR1## in which A, Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 have the meanings given in the description, to processes for their preparation, to new intermediates, and to their use as herbicides.Type: GrantFiled: August 2, 1994Date of Patent: January 14, 1997Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Hans-Joachim Santel, Markus Dollinger
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Patent number: 5591846Abstract: New nonionic radiographic contrast agents having the formula ##STR1## wherein Y is a single bond, ##STR2## R.sub.1, R.sub.1 ' and R.sub.2 are the same or different and are hydrogen, alkyl or hydroxyalkyl.Hydroxyalkyl refers to such alkyl groups having 1 or more hydroxy groups. Preferred hydroxyalkyl groups include: ##STR3## R.sub.3 and R.sub.4 are the same or different and are hydrogen, methyl or --CH.sub.2 CH.sub.2 OH; R.sub.5 is hydrogen, alkyl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 OH or OH and R.sub.6 is alkyl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 OH, OH or hydrogen and may be the same or different than R.sub.5 and m is zero or one, with the proviso that no methylene or methine carbon atom of the heterocyclic ring is attached to both a nitrogen and an oxygen atom with the additional proviso that when Y is a single bond, m is not zero. These new contrast agents are water soluble and have desirable low osmolality and anticoagulant properties.Type: GrantFiled: October 27, 1993Date of Patent: January 7, 1997Assignee: Bracco International B.V.Inventors: Ramachandran S. Ranganathan, Thangavel Arunchalam, Edmund R. Marinelli, Radhakrishna K. Pillai
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Patent number: 5562865Abstract: The present invention relating to novel oxazolidine and tetrahydrooxazine amide surfactants and to processes for making the surfactants. These are cyclic surfactants having good solubility and which are readily biodegradable.Type: GrantFiled: May 18, 1995Date of Patent: October 8, 1996Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Mohammad A. Rahman, Shang-Ren Wu, Anthony Hung
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Patent number: 5560872Abstract: The present invention relating to compositions comprising novel oxazolidine and tetrahydrooxazine amide surfactants and to processes for making the surfactants. These are cyclic surfactants having good solubility and which are readily biodegradable.Type: GrantFiled: May 18, 1995Date of Patent: October 1, 1996Assignee: Lever Brothers CompanyInventors: Mohammad A. Rahman, Shang-Ren Wu, Anthony Hung
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Patent number: 5532363Abstract: 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, heteroaryl, alkyl, alkenyl, alkynyl or OR.sub.7 wherein R.sub.7 is alkyl, alkenyl, alkynyl, aryl or heteroaryl; R.sub.2 and R.sub.5 are independently selected from hydrogen, alkyl alkenyl, alkynyl, aryl, heteroaryl, and OR.sub.8 wherein R.sub.8 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxyl protecting group; and R.sub.3 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl.Type: GrantFiled: November 7, 1994Date of Patent: July 2, 1996Assignee: Florida State UniversityInventor: Robert A. Holton
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Patent number: 5496943Abstract: Disclosed is a novel heterocyclic compound selected from the group consisting of the compounds [IV] to [VII], [IX] and [X]. The heterocyclic compound is useful for reactive materials in chemical industry. A process for producing the heterocyclic compound is also disclosed.Type: GrantFiled: March 13, 1992Date of Patent: March 5, 1996Assignee: Nippon Paint Co., Ltd.Inventors: Otohiko Tsuge, Taizo Hatta, Satoshi Urano, Noriyuki Tsuboniwa, Ryuzo Mizuguchi
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Patent number: 5491201Abstract: Novel cyclic imino ether compositions containing one or more mesogenic moieties, when polymerized, result in products having improved properties.Type: GrantFiled: February 16, 1995Date of Patent: February 13, 1996Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5436224Abstract: 1,3-Oxazin-4-one derivatives represented by general formula (I) ##STR1## wherein R.sup.1 is a lower alkyl group, a lower alkenyl group, an aryl group which may be substituted, or an aralkyl group which may be substituted;R.sup.2 is a hydrogen atom or a lower alkyl group;R.sup.3 is a lower alkyl group, an aryl group which may be substituted, or an aralkyl group which may be substituted; andR.sup.4 and R.sup.5, independently, each is a lower alkyl group, or R.sup.4 and R.sup.5, taken together with the carbon atom to which they are bonded, combine to form a 3- to 8-membered carbocyclic group which may have a branch of a lower alkyl group. These compounds have broad herbicidal spectra and potent herbicidal activities and in addition high safety to useful crops, so that they are useful as herbicides.Type: GrantFiled: September 30, 1993Date of Patent: July 25, 1995Assignees: Mitsubishi Petrochemical Co., Ltd., Daicel Chemical Industries, Ltd.Inventors: Takeshi Hamatani, Hirokazu Hasebe, Keiichi Hayashizaki, Yoshihiro Usui, Chiharu Yasumoto, Atsushi Go, Mitsuru Hikido, Kumiko Tamura, Kazuo Jikihara
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Patent number: 5422349Abstract: Compounds characterized generally as morpholino/oxazinyl-terminated alkylamino ethynyl alanine amino diol derivatives are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 ; wherein X is selected from oxygen atom and methylene; wherein B is selected from morpholino, oxo-substituted-morpholino and 1,3-oxazinyl groups; wherein R.sub.1 is selected from hydrido, methyl, ethyl, isopropyl and n-propyl; wherein R.sub.2 is phenylmethyl; wherein each of R.sub.3 and R.sub.5 is hydrido; wherein R.sub.4 is selected from--(CH.sub.2).sub.q --C.tbd.C--Vwherein V is selected from hydrido and methyl; wherein R.sub.6 is cyclohexylmethyl; wherein R.sub.7 is selected from isobutyl, cyclopropyl and cyclopropylmethyl; wherein q is a number selected from zero through three, inclusive; and wherein n is a number selected from zero through three, inclusive; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: August 14, 1992Date of Patent: June 6, 1995Assignee: G. D. Seale & Co.Inventors: Gunnar J. Hanson, Robert E. Manning
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Patent number: 5420127Abstract: Non-peptidyl compounds characterized generally as .alpha.-succinamidoacyl aminodiols having a morpholino-type group at the N-terminus are useful as renin inhibitors for the treatment of hypertension.Type: GrantFiled: July 19, 1991Date of Patent: May 30, 1995Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran
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Patent number: 5393754Abstract: Insecticidal, acaricidal or nematocidal compositions which comprise a series of organophosphorus compounds represented by the following representative structural formulae: ##STR1## show excellent effect for controlling harmful insects, mites and nematodes, do not give off a bad or irritating smell and exhibit very low toxicity to warm-blooded animals.Type: GrantFiled: September 9, 1993Date of Patent: February 28, 1995Assignee: Agro-Kanesho Co., Ltd.Inventors: Katsumi Nanjo, Akinori Kariya, Shinya Henmi, Hideyo Fujii, Syuichi Usui
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Patent number: 5384399Abstract: 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, heteroaryl, alkyl, alkenyl, alkynyl or OR.sub.7 wherein R.sub.7 is alkyl, alkenyl, alkynyl, aryl or heteroaryl; R.sub.2 and R.sub.5 are independently selected from hydrogen, alkyl alkenyl, alkynyl, aryl, heteroaryl, and OR.sub.8 wherein R.sub.8 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxyl protecting group; and R.sub.3 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl.Type: GrantFiled: June 15, 1992Date of Patent: January 24, 1995Assignee: Florida State UniversityInventor: Robert A. Holton
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Patent number: 5384422Abstract: In the production of .alpha.-sulfofatty acid alkyl ester alkali metal salt pastes by reaction of fatty acid alkyl esters with gaseous SO.sub.3, subsequent after-reaction in liquid phase and neutralization with aqueous alkali metal hydroxide solutions, the crude sulfonation product is fed to an at least two-stage cascade of stirred tanks equipped with heating and cooling systems in which it is subjected with mechanical agitation to a temperature-controlled after-reaction until a degree of sulfonation of at least 90% is reached, after which the aged sulfonation product is further processed in known manner to .alpha.-sulfofatty acid alkyl ester alkali metal salt pastes.Type: GrantFiled: November 25, 1992Date of Patent: January 24, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Dietmar Colignon, Erich Dorra, Guenter Panthel, Wolfgang Schmidt, Norbert Wrede
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Patent number: 5342937Abstract: A solvent soluble heterocyclic o-hydroxy thione carrying a lipophilic group and the process for the selective extraction of gallium, and certain other related metals, especially from solutions containing excess aluminium.Type: GrantFiled: October 7, 1991Date of Patent: August 30, 1994Assignees: Zeneca, Limited, Nerco, Inc.Inventors: Peter W. Austin, Peter M. Quan, Peter A. Tasker, Derek Thorp
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Patent number: 5268473Abstract: Azlactone-functional Michael adducts are disclosed which are the Michael reaction products of 2-alkenyl azlactones and Michael donors selected from carbon and nitrogen nucleophiles. Reaction products which contain a plurality of azlactone groups are useful as step growth monomers in adhesives, sealants, and coatings.Type: GrantFiled: June 26, 1992Date of Patent: December 7, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Dean M. Moren, Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
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Patent number: 5245040Abstract: A process for the preparation of 1,3-disubstituted 2-nitroguanidines of the formula I ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or a radical --CH.sub.2 B; A is an unsubstituted or mono- to tetrasubstituted aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical, which may contain one or two substituents from the group comprising C.sub.1 -C.sub.3 haloalkyl having 1 to 7 halogen atoms, cyclopropyl, halocyclopropyl having 1 to 3 halogen atoms, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.2 -C.sub.3 haloalkenyl and C.sub.2 -C.sub.3 haloalkynyl having 1 to 4 halogen atoms, C.sub.1 -C.sub.3 haloalkoxy having 1 to 7 halogen atoms, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio having 1 to 7 halogen atoms, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro and one to four substituents from the group comprising C.sub.1 -C.sub.3 alkyl, C.sub.Type: GrantFiled: October 16, 1991Date of Patent: September 14, 1993Assignee: Ciba-Geigy CorporationInventors: Peter Maienfisch, Odd Kristiansen, Laurenz Gsell
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Patent number: 5223501Abstract: Novel substituted fused pyrimidinones of formula (I) are useful as angiotensin II antagonists.Type: GrantFiled: May 10, 1991Date of Patent: June 29, 1993Assignee: Merck & Co., Inc.Inventors: Prasun K. Chakravarty, Nathan B. Mantlo, William J. Greenlee, Arthur A. Patchett, Dooseop Kim
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Patent number: 5164498Abstract: Combating unwanted vegetation with N-phenyl-substituted oxazinediones of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 can each be hydrogen or an organic radical or R.sup.2 and R.sup.3 and/or R.sup.6 and R.sup.7 can form a ring, andQ is oxygen or sulphur.Those compounds are new wherein at least three of the radicals R.sup.1 to R.sup.5 are other than hydrogen or the two radicals R.sup.2 and R.sup.3 together represent --O--CH.sub.2 --O--CH.sub.2 -- or the group --X--(CO).sub.n --A--Y--.Type: GrantFiled: June 7, 1991Date of Patent: November 17, 1992Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Franz Kunisch, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5157040Abstract: Substituted quinolines of the formula (I), are angiotensin II antagonists, ##STR1## and useful in the treatment of hypertension, ocular hypertension and certain CNS disorders.Type: GrantFiled: April 5, 1991Date of Patent: October 20, 1992Assignee: Merck & Co., Inc.Inventors: William J. Greenlee, David B. R. Johnston, Malcolm MacCoss
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Patent number: 5157108Abstract: Compounds containing alpha-amidoacetyle linkages are described that are thermally labile and yield nucleophilic and azlactone products. Nucleophiles are useful as curing agents for epoxy resin sealants and adhesives and azlactones are useful in crosslinking systems for polymers.Type: GrantFiled: December 12, 1989Date of Patent: October 20, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventors: Larry R. Krepski, Steven M. Heilmann, Dean M. Moren, Jerald K. Rasmussen
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Patent number: 5149806Abstract: Azlactone-functional Michael adducts are disclosed which are the Michael reaction products of 2-alkenyl azlactones and Michael donors selected from carbon and nitrogen nucleophiles. Reaction products which contain a plurality of azlactone groups are useful as step growth monomers in adhesives, sealants, and coatings.Type: GrantFiled: March 28, 1990Date of Patent: September 22, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventors: Dean M. Moren, Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
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Patent number: 5136060Abstract: 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, heteroaryl, alkyl, alkenyl, alkynyl or OR.sub.7 wherein R.sub.7 is alkyl, alkenyl, alkynyl, aryl or heteroaryl; R.sub.2 and R.sub.5 are independently selected from hydrogen, alkyl alkenyl, alkynyl, aryl, heteroaryl, and OR.sub.8 wherein R.sub.8 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, or hydroxyl protecting group; and R.sub.3 and R.sub.6 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl and heteroaryl.Type: GrantFiled: October 30, 1990Date of Patent: August 4, 1992Assignee: Florida State UniversityInventor: Robert A. Holton
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Patent number: 5061310Abstract: Combating unwanted vegetation with N-phenyl-substituted oxazinediones of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 can each be hydrogen or an organic radical or R.sup.2 and R.sup.3 and/or R.sup.6 and R.sup.7 can form a ring, andQ is oxygen or sulphur.Those compounds are new wherein at least three of the radicals R.sup.1 to R.sup.5 are other than hydrogen or the two radicals R.sup.2 and R.sup.3 together represent --O--CH.sub.2 --O--CH.sub.2 -- or the group --X--(CO).sub.n --A--Y--.Type: GrantFiled: October 16, 1989Date of Patent: October 29, 1991Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Franz Kunisch, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5028693Abstract: Urethane-protected NCAs and MTAs are prepared by reacting an NCA or NTA with a haloformate in an inert diluent, under anhydrous conditions and in the presence of a tertiary nitrogen-containing base having an atom or functional group sufficiently electron rich and positioned relative to the nitrogen of said base so as to render said atom or group capable of complexing with the H--N< group of said N-carboxyanhydride or N-thiocarboxyanhydride but able to generate N-carboxyanhydride or N-thiocarboxyanhydride anionic complexes capable of reacting with the haloformate.Type: GrantFiled: July 13, 1989Date of Patent: July 2, 1991Assignee: Bioresearch, Inc.Inventors: William D. Fuller, Michael P. Cohen, Fred R. Naider, Murray Goodman
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Patent number: 4977141Abstract: Non-peptidyl compounds characterized generally as aminoacyl aminodiol carbamates are useful as renin inhibitors for the treatment of hypertension.Type: GrantFiled: October 1, 1987Date of Patent: December 11, 1990Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran
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Patent number: 4946942Abstract: The invention relates to urethane-protected amino acid-N-carboxyanhydride and N-thiocarboxyanhydride compounds which are useful in peptide, polypeptide and protein synthesis. Disclosed herein is the preparation and use of these novel compounds.Type: GrantFiled: March 11, 1988Date of Patent: August 7, 1990Assignee: Bioresearch, Inc.Inventors: William D. Fuller, Michael P. Cohen, Fred R. Naider, Murray Goodman
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Patent number: 4837290Abstract: A composition of matter comprising an acrylamido-acyl or methacrylamido-acyl oligomer derived from at least one nucleophilic oligomer having at least one amino-, hydroxyl-, or thiol-substituted polyoxyalkylene, polyalkyleneimine, polyester, polyolefin, polyacrylate, or polysiloxane oligomer, said nucleophilic oligomer having a molecular weight in the range of 200 to 20,000 is disclosed. Also disclosed are free radically polymerizable monomer-containing compositions containing said oligomers as well as acrylamido- and methacrylamido-acylated polymers which are thermal or photocured products of said oligomers. In addition, a process is disclosed for providing said acrylamido- and methacrylamido-acylated oligomers which are useful, for example, in coatings, films, printing inks, adhesives, and saturants.Type: GrantFiled: July 11, 1988Date of Patent: June 6, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
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Patent number: 4783451Abstract: An organophosphorus compound having the formula: ##STR1## wherein X is ##STR2## Z is an oxygen atom or a sulfur atom, and each of R.sub.1 and R.sub.2 is an alkyl group which may be substituted by halogen, alkoxy or alkylthio. The compound is useful as an insecticide, miticide, nematicide or soil pesticide.Type: GrantFiled: June 25, 1986Date of Patent: November 8, 1988Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Hiroshi Okada, Kiyomitsu Yoshida, Osamu Imai
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Patent number: 4777276Abstract: A composition of matter comprising an acrylamido-acyl or methacrylamido-acyl oligomer derived from at least one nucleophilic oligomer having at least one amino-, hydroxyl-, or thiol-substituted polyoxyalkylene, polyalkyleneimine, polyester, polyolefin, polyacrylate, or polysiloxane oligomer, said nucleophilic oliogmer having a molecular weight in the range of 200 to 20,000 is disclosed. Also disclosed are free radically polymerizable monomer-containing compositions containing said oligomers as well as acrylamido- and methacrylamido-acylated polymers which are the thermal or photocured products of said oligomers. In addition, a process is disclosed for providing said acrylamido- and methacrylamido-acylated oligomers which are useful, for example, in coatings, films, printing inks, adhesives, and saturants.Type: GrantFiled: October 29, 1981Date of Patent: October 11, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
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Patent number: 4737500Abstract: Thiazoles or pharmaceutically acceptable acid addition salts thereof are useful as anxiolytic, psychogeriatric, antidepressant and antischizophrenic agents.Type: GrantFiled: June 20, 1986Date of Patent: April 12, 1988Assignee: Sandoz Pharm. Corp.Inventor: Dieter Sorg
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Patent number: 4715984Abstract: Dihydroazines of the formula IR.sub.1 --A.sup.1 --Z.sub.1 --A.sub.2 --R.sup.2 Iwherein R.sup.1, R.sup.2, A.sup.1, A.sup.2 and Z.sub.1 have the meanings specified herein may be used as components of liquid crystalline phases.Type: GrantFiled: January 22, 1986Date of Patent: December 29, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Krause, Wachtler, Bernhard Scheuble
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Patent number: 4710500Abstract: The present invention relates to novel indole derivatives which have interesting pharmacodynamic effects indicating pronounced activity in the treatment of psychic disorders, especially psychoses and, at the same time, a low degree of undesired side effects.Moreover, the invention relates to methods for the preparation of said indole derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, especially psychoses, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.The novel indole derivatives of the present invention are represented by the following formula: ##STR1## wherein R is phenyl, optionally substituted with halogen, lower alkyl or trifluoromethyl, or a hetero aromatic group, such as 2-thienyl, 3-thienyl, 2-furoyl, 3-furoyl, 2-thiazol, 2-oxazol, 2-imidazole, 2-pyridyl, 3-pyridyl or 4-pyridyl; R.sup.Type: GrantFiled: April 1, 1986Date of Patent: December 1, 1987Assignee: H. Lundbeck A/SInventor: Jens K. Perregaard
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Patent number: 4684650Abstract: The present invention relates to indane derivatives with the following formula: ##STR1## wherein R.sub.1 is H, Halogen, an alkyl group having from one to three carbon atoms inclusive, methoxy, a methylthio-group, or a trifluoromethyl group,n is 2-4X is O or S,Y is O, CH.sub.2 or N--R.sub.2, where R.sub.2 is hydrogen or an (1-6 C) alkyl, (2-6 C) alkenyl or cycloalkyl-methyl group having from three to six carbon atoms,Z is --(CH.sub.2).sub.n --, n is 2 or 3 or Z is 1,2-phenylene optionally substituted with halogen or trifluoromethyl or Z=1,2--C.sub.6 H.sub.4 CO-- (to form a quinazolidinone or -thione ring system). U=N or C.Each compound exists as geometric isomers and each of these as a pair of optical isomers; and the separation and isolation of these are also within the scope of the invention.Moreover, pharmaceutically acceptable acid addition salts of the compounds of Formula I are within the scope of the present invention.Type: GrantFiled: October 10, 1985Date of Patent: August 4, 1987Assignee: H. Lundbeck A/SInventor: Klaus P. Bogeso
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Patent number: 4680410Abstract: The invention is a process for the preparation of a N- or S-1,2-ethylenically unsaturated organic compound which comprises(a) contacting a N- or S-silylated organic compound with an aldehyde, wherein the aldehyde has a hydrogen atom bonded to the carbon adjacent to the carbonyl moiety, at elevated temperatures under conditions such that a N- or S-1-siloxyalkyl-substituted organic compound is prepared; and(b) pyrolyzing the N- or S-1-siloxyalkyl-substituted organic compound under conditions such that the siloxy moiety is elminated to prepare a N- or S-1,2-ethylenically unsaturated compound.Type: GrantFiled: March 2, 1984Date of Patent: July 14, 1987Assignee: The Dow Chemical CompanyInventor: Pen C. Wang
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Patent number: RE34299Abstract: The present invention relates to novel indole derivatives which have interesting pharmacodynamic effects indicating pronounced activity in the treatment of psychic disorders, especially psychoses and, at the same time, a low degree of undesired side effects.Moreover, the invention relates to methods for the preparation of said indole derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, especially psychoses, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.The novel indole derivatives of the present invention are represented by the following formula; ##STR1## wherein R is phenyl, optionally substituted with halogen.[., lower alkyl or trifluoromethyl,.]. or a hetero aromatic group, such as 2-thienyl, 3-thienyl, .[.2-furoyl, 3-furoyl, 2-thiazol, 2-oxazol, 2-imidazole, 2-pyridyl, 3-pyridyl.]. .Iadd.2-oxazolyl, 2-imidazolyl, 2-pyridyl 3-pyridyl.Iaddend.or 4-pyridyl; R.sup.Type: GrantFiled: September 13, 1991Date of Patent: June 29, 1993Assignee: H. Lundbeck A/SInventor: Jens K. Perregaard