Chalcogen Bonded Directly To The Oxazine Ring Patents (Class 544/97)
  • Patent number: 6028224
    Abstract: 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: Grant
    Filed: May 24, 1999
    Date of Patent: February 22, 2000
    Assignee: Sepracor Inc.
    Inventors: James Wallace Hilborn, Alex Roger Jurgens, Chris Hugh Senanayake
  • Patent number: 6028032
    Abstract: 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: Grant
    Filed: April 13, 1998
    Date of Patent: February 22, 2000
    Assignee: Rhone-Poulenc Agriculture Ltd.
    Inventors: Michael Colin Cramp, Yoshihiro Usui, Keiichi Hayashizaki
  • Patent number: 6004955
    Type: Grant
    Filed: August 12, 1998
    Date of Patent: December 21, 1999
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Fuqiang Jin, Pasquale Nicholas Confalone
  • Patent number: 5977025
    Abstract: 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: Grant
    Filed: June 20, 1996
    Date of Patent: November 2, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Keiichi Hayashizaki, Yoshihiro Usui, Koichi Araki, Norishige Toshima, Tetsuya Murata, Takako Aoki, Atsushi Go, Hideshi Mukaida, Rika Higurashi
  • Patent number: 5977359
    Abstract: 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: Grant
    Filed: October 20, 1998
    Date of Patent: November 2, 1999
    Assignee: Sanofi
    Inventors: Xavier Emonds-Alt, Isabelle Grossriether, Patrick Gueule, Vincenzo Proietto, Didier Van Broeck
  • Patent number: 5972237
    Abstract: 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: Grant
    Filed: November 17, 1997
    Date of Patent: October 26, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Muller, Thomas Wehlage, Wolfgang Trieselt, Alfred Oftring, Elisabeth Kappes, Gunter Oetter, Dieter Boeckh, Roland Ettl, Albert Hettche
  • Patent number: 5932521
    Abstract: 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: Grant
    Filed: July 22, 1997
    Date of Patent: August 3, 1999
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Atsushi Go, Rika Higurashi, Miki Komine, Yoshimi Tsutsumi, Yoshihiro Usui
  • Patent number: 5914332
    Abstract: 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: Grant
    Filed: November 21, 1996
    Date of Patent: June 22, 1999
    Assignee: Abbott Laboratories
    Inventors: Hing Leung Sham, Daniel W. Norbeck, Xiaoqi Chen, David A. Betebenner
  • Patent number: 5789404
    Abstract: 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: Grant
    Filed: August 12, 1996
    Date of Patent: August 4, 1998
    Assignee: H. Lundbeck A/S
    Inventors: Kim Andersen, Jens Kristian Perregaard
  • Patent number: 5777111
    Abstract: 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: Grant
    Filed: May 23, 1997
    Date of Patent: July 7, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Christian Schumacher, Michael Meier, Werner Hubert Russ
  • Patent number: 5708167
    Abstract: 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: Grant
    Filed: August 23, 1995
    Date of Patent: January 13, 1998
    Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.
    Inventors: Yoshihiro Honma, Shozo Tanaka, Mitsuyoshi Oshima, Soji Tanioka, Fumiaki Kawamoto
  • Patent number: 5703215
    Abstract: 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: Grant
    Filed: May 30, 1995
    Date of Patent: December 30, 1997
    Assignee: Zeneca Limited
    Inventors: Andrew Hunter Morris Renfrew, Andrew Paul Shawcross
  • Patent number: 5696054
    Abstract: 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: Grant
    Filed: March 14, 1995
    Date of Patent: December 9, 1997
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Atsushi Go, Rika Higurashi, Miki Komine, Yoshimi Tsutsumi, Yoshihiro Usui
  • Patent number: 5693310
    Abstract: 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: Grant
    Filed: November 19, 1990
    Date of Patent: December 2, 1997
    Assignee: Schering Aktiengesellschaft
    Inventors: Heinz Gries, Bernd Raduechel, Hans-Joachim Weinmann, Wolfgang Muetzel, Ulrich Speck
  • Patent number: 5608057
    Abstract: 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: Grant
    Filed: August 23, 1995
    Date of Patent: March 4, 1997
    Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.
    Inventors: Yoshihiro Honma, Shozo Tanaka, Mitsuyoshi Oshima, Soji Tanioka, Fumiaki Kawamoto
  • Patent number: 5593944
    Abstract: 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: Grant
    Filed: August 2, 1994
    Date of Patent: January 14, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Hans-Joachim Santel, Markus Dollinger
  • Patent number: 5591846
    Abstract: 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: Grant
    Filed: October 27, 1993
    Date of Patent: January 7, 1997
    Assignee: Bracco International B.V.
    Inventors: Ramachandran S. Ranganathan, Thangavel Arunchalam, Edmund R. Marinelli, Radhakrishna K. Pillai
  • Patent number: 5562865
    Abstract: 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: Grant
    Filed: May 18, 1995
    Date of Patent: October 8, 1996
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Mohammad A. Rahman, Shang-Ren Wu, Anthony Hung
  • Patent number: 5560872
    Abstract: 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: Grant
    Filed: May 18, 1995
    Date of Patent: October 1, 1996
    Assignee: Lever Brothers Company
    Inventors: Mohammad A. Rahman, Shang-Ren Wu, Anthony Hung
  • Patent number: 5532363
    Abstract: 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: Grant
    Filed: November 7, 1994
    Date of Patent: July 2, 1996
    Assignee: Florida State University
    Inventor: Robert A. Holton
  • Patent number: 5496943
    Abstract: 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: Grant
    Filed: March 13, 1992
    Date of Patent: March 5, 1996
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Otohiko Tsuge, Taizo Hatta, Satoshi Urano, Noriyuki Tsuboniwa, Ryuzo Mizuguchi
  • Patent number: 5491201
    Abstract: Novel cyclic imino ether compositions containing one or more mesogenic moieties, when polymerized, result in products having improved properties.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: February 13, 1996
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5436224
    Abstract: 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: Grant
    Filed: September 30, 1993
    Date of Patent: July 25, 1995
    Assignees: 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
  • Patent number: 5422349
    Abstract: 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: Grant
    Filed: August 14, 1992
    Date of Patent: June 6, 1995
    Assignee: G. D. Seale & Co.
    Inventors: Gunnar J. Hanson, Robert E. Manning
  • Patent number: 5420127
    Abstract: 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: Grant
    Filed: July 19, 1991
    Date of Patent: May 30, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran
  • Patent number: 5393754
    Abstract: 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: Grant
    Filed: September 9, 1993
    Date of Patent: February 28, 1995
    Assignee: Agro-Kanesho Co., Ltd.
    Inventors: Katsumi Nanjo, Akinori Kariya, Shinya Henmi, Hideyo Fujii, Syuichi Usui
  • Patent number: 5384399
    Abstract: 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: Grant
    Filed: June 15, 1992
    Date of Patent: January 24, 1995
    Assignee: Florida State University
    Inventor: Robert A. Holton
  • Patent number: 5384422
    Abstract: 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: Grant
    Filed: November 25, 1992
    Date of Patent: January 24, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Dietmar Colignon, Erich Dorra, Guenter Panthel, Wolfgang Schmidt, Norbert Wrede
  • Patent number: 5342937
    Abstract: 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: Grant
    Filed: October 7, 1991
    Date of Patent: August 30, 1994
    Assignees: Zeneca, Limited, Nerco, Inc.
    Inventors: Peter W. Austin, Peter M. Quan, Peter A. Tasker, Derek Thorp
  • Patent number: 5268473
    Abstract: 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: Grant
    Filed: June 26, 1992
    Date of Patent: December 7, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Dean M. Moren, Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
  • Patent number: 5245040
    Abstract: 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: Grant
    Filed: October 16, 1991
    Date of Patent: September 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Odd Kristiansen, Laurenz Gsell
  • Patent number: 5223501
    Abstract: Novel substituted fused pyrimidinones of formula (I) are useful as angiotensin II antagonists.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: June 29, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Prasun K. Chakravarty, Nathan B. Mantlo, William J. Greenlee, Arthur A. Patchett, Dooseop Kim
  • Patent number: 5164498
    Abstract: 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: Grant
    Filed: June 7, 1991
    Date of Patent: November 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Franz Kunisch, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 5157040
    Abstract: 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: Grant
    Filed: April 5, 1991
    Date of Patent: October 20, 1992
    Assignee: Merck & Co., Inc.
    Inventors: William J. Greenlee, David B. R. Johnston, Malcolm MacCoss
  • Patent number: 5157108
    Abstract: 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: Grant
    Filed: December 12, 1989
    Date of Patent: October 20, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Larry R. Krepski, Steven M. Heilmann, Dean M. Moren, Jerald K. Rasmussen
  • Patent number: 5149806
    Abstract: 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: Grant
    Filed: March 28, 1990
    Date of Patent: September 22, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Dean M. Moren, Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen
  • Patent number: 5136060
    Abstract: 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: Grant
    Filed: October 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Florida State University
    Inventor: Robert A. Holton
  • Patent number: 5061310
    Abstract: 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: Grant
    Filed: October 16, 1989
    Date of Patent: October 29, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Franz Kunisch, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 5028693
    Abstract: 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: Grant
    Filed: July 13, 1989
    Date of Patent: July 2, 1991
    Assignee: Bioresearch, Inc.
    Inventors: William D. Fuller, Michael P. Cohen, Fred R. Naider, Murray Goodman
  • Patent number: 4977141
    Abstract: Non-peptidyl compounds characterized generally as aminoacyl aminodiol carbamates are useful as renin inhibitors for the treatment of hypertension.
    Type: Grant
    Filed: October 1, 1987
    Date of Patent: December 11, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran
  • Patent number: 4946942
    Abstract: 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: Grant
    Filed: March 11, 1988
    Date of Patent: August 7, 1990
    Assignee: Bioresearch, Inc.
    Inventors: William D. Fuller, Michael P. Cohen, Fred R. Naider, Murray Goodman
  • Patent number: 4837290
    Abstract: 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: Grant
    Filed: July 11, 1988
    Date of Patent: June 6, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
  • Patent number: 4783451
    Abstract: 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: Grant
    Filed: June 25, 1986
    Date of Patent: November 8, 1988
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Hiroshi Okada, Kiyomitsu Yoshida, Osamu Imai
  • Patent number: 4777276
    Abstract: 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: Grant
    Filed: October 29, 1981
    Date of Patent: October 11, 1988
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
  • Patent number: 4737500
    Abstract: Thiazoles or pharmaceutically acceptable acid addition salts thereof are useful as anxiolytic, psychogeriatric, antidepressant and antischizophrenic agents.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: April 12, 1988
    Assignee: Sandoz Pharm. Corp.
    Inventor: Dieter Sorg
  • Patent number: 4715984
    Abstract: 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: Grant
    Filed: January 22, 1986
    Date of Patent: December 29, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Krause, Wachtler, Bernhard Scheuble
  • Patent number: 4710500
    Abstract: 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: Grant
    Filed: April 1, 1986
    Date of Patent: December 1, 1987
    Assignee: H. Lundbeck A/S
    Inventor: Jens K. Perregaard
  • Patent number: 4684650
    Abstract: 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: Grant
    Filed: October 10, 1985
    Date of Patent: August 4, 1987
    Assignee: H. Lundbeck A/S
    Inventor: Klaus P. Bogeso
  • Patent number: 4680410
    Abstract: 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: Grant
    Filed: March 2, 1984
    Date of Patent: July 14, 1987
    Assignee: The Dow Chemical Company
    Inventor: Pen C. Wang
  • Patent number: RE34299
    Abstract: 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: Grant
    Filed: September 13, 1991
    Date of Patent: June 29, 1993
    Assignee: H. Lundbeck A/S
    Inventor: Jens K. Perregaard