Nitrogen Attached Directly Or Indirectly To The Hetero Ring By Acyclic Nonionic Bonding Patents (Class 549/419)
  • Patent number: 5155240
    Abstract: A process for producing an optically active dihydropyran derivative represented by formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each represents a hydrogen atom, a lower alkyl group, a tri-lower alkylsilylmethyl group, a lower alkoxycarbonylamino group, or an --OR.sup.5 group, wherein R.sup.5 represents a lower alkyl group, a lower acyl group, a lower alkoxycarbonyl group, a di-lower alkylcarbamoyl group, or a tri-lower alkylsilyl group, or R.sup.1 and R.sup.2 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, or R.sup.2 and R.sup.3 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, provided that all of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 do not represent hydrogen atoms at the same time; and R.sup.6 represents a lower alkyl group, which comprises reacting a diene compound represented by formula (2): ##STR2## wherein R.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: October 13, 1992
    Assignee: Takasago International Corporation
    Inventors: Koichi Mikami, Masahiro Terada, Takeshi Nakai, Noboru Sayo
  • Patent number: 5130468
    Abstract: A process and intermediates useful for the preparation of (E)-alkene dipeptide isosteres are disclosed.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: July 14, 1992
    Assignee: Abbott Laboratories
    Inventor: Dale J. Kempf
  • Patent number: 5128489
    Abstract: A process for production of an optically active isomer of 2-(tetrahydropyran-2-yloxy)-1-propanol represented by formula (I): ##STR1## is disclosed, which comprises reacting an optically active isomer of a 1-acyloxy-2-propanol represented by formula (II): ##STR2## wherein R is a substituted or unsubstituted aryl group, with 3,4-dihydro-2H-pyran to obtain an optically active isomer of a 1-acyloxy-2-(tetrahydropyran-2-yloxy)propane represented by formula (III): ##STR3## wherein R is as defined above, and hydrolyzing the compound (III) to eliminate the acyl group. The optically active isomer of 2-(tetrahydropyran-2-yloxy)-1-propanol represented by formula (I) is an intermediate for synthesis of pyridobenzoxazine derivatives useful as a synthetic antibacterial agent, particularly an optically active isomer of ofloxacin.
    Type: Grant
    Filed: October 4, 1990
    Date of Patent: July 7, 1992
    Assignees: Takasago International Corporation, Daiichi Pharmaceutical Co., Ltd.
    Inventors: Hidenori Kumobayashi, Akio Tachikawa, Yoshiki Okeda, Toshihiro Fujiwara
  • Patent number: 5120746
    Abstract: This invention relates to amine derivatives and salts thereof. These compounds have an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such compound, a process for the preparation thereof and an anti-ulcer agent containing the same.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: June 9, 1992
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Shiro Hirai, Hiroshi Hirano, Hirotoshi Arai, Yasuo Kiba, Hisanari Shibata, Yoshikazu Kusayanag, Minako Yotsuji, Kazuhiko Hashiba, Kikuko Tanada
  • Patent number: 5117057
    Abstract: This invention relates to insecticidal compositions containing N'-substituted-N,N'-disubstitutedhydrazines, methods of using such compositions and N'-substituted-N, N'-disubstitutedhydrazines. Specifically, the invention relates to insect growth regulating compositions, and methods of using such compositions, which include compounds having a nucleus of the formula ##STR1## where A', B', D and J are independently any atom or group of atoms; where E is a tertiary carbon containing organic radical, a haloalkyl having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen, and is attached to the nitrogen shown in the formula by a carbon-to-nitrogen single bond; where one G.sub.1 is C, N, O and S, and both G.sub.2 's and the other G.sub.1 are carbon; or one G.sub.2 is S or P, and both G.sub.1 's and the other G.sub.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: May 26, 1992
    Assignee: Rohm and Haas Company
    Inventors: Adam C. Hsu, Harold E. Aller, Raymond A. Murphy, Dat P. Le, Donald W. Hamp, Barry Weinstein
  • Patent number: 5112953
    Abstract: Chelating compounds of specified structure are useful for radiolabeling targeting molecules such as antibodies. Cleavable linkers connect the radionuclide metal chelates to the antibodies. The radiolabeled antibodies have improved biodistribution properties, including reduced localization within the intestines and kidneys.
    Type: Grant
    Filed: December 29, 1989
    Date of Patent: May 12, 1992
    Assignee: NeoRx Corporation
    Inventors: Linda M. Gustavson, Ananthachari Srinivasan, Sudhakar Kasina, John M. Reno, Jeffrey N. Fitzner, David S. Jones
  • Patent number: 5041567
    Type: Grant
    Filed: November 28, 1988
    Date of Patent: August 20, 1991
    Assignee: Beecham Group plc
    Inventors: Norman H. Rogers, Peter J. O'Hanlon, Graham Walker, Michael J. Crimmin
  • Patent number: 5022914
    Abstract: Cyclohexenone oxime ethers of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl,A is substituted or unsubstituted C.sub.4 -alkylene or C.sub.4 -alkenylene,X is nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl and/or phenyl,n is from 0 to 3 or from 1 to 5 when X is halogen,R.sup.2 is C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.
    Type: Grant
    Filed: October 31, 1989
    Date of Patent: June 11, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
  • Patent number: 5017693
    Abstract: The present invention provides cleavable conjugates whose linkers contain a labile bond that is cleavable under a variety of mild conditions, including weakly acidic. Since the agent may be bonded directly to the linker, cleavage can result in release of native agent. The invention also provides methods for producing cleavable conjugates. Preferred agents include drugs, toxins, biological response modifiers, radiodiagnostic compounds, radiotherapeutic compounds, and derivatives thereof. The targeting molecule employed in the invention may be an intact molecule, a fragment thereof, or a functional equivalent thereof. In a particularly preferred embodiment, the targeting molecule is a monoclonal antibody directed towards a tumor-associated antigen in man. The invention further provides methods for delivering to the cytoplasm of target cell an agent free of its targeting molecular carrier.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: May 21, 1991
    Assignee: NeoRx Corporation
    Inventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
  • Patent number: 4988723
    Abstract: Benzopyran derivatives of formula (I) wherein the substituents are as defined herein are provided. The compounds possess vasodilating activity and are useful in the treatment of hypertension. Pharmaceutical compositions and methods of treating hypertension are also provided.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: January 29, 1991
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Youichi Shiokawa, Koichi Takimoto, Kohei Takenaka, Takeshi Kato
  • Patent number: 4962209
    Abstract: This invention relates to compounds of the formula I ##STR1## wherein: R1 is alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted) aryl, arylalkyl or silyl (bearing alkyl, aryl or arylalkyl substituents);R2 is hydrogen or alkyl;R3 is hydrogen, alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted), alkenyl, aryl, arylalkyl, amino, mono--or di--alkylamino or a group of the formula --OR5 wherein R5 is optionally substituted alkyl, aryl or arylalkyl;R4 is alkyl optionally substituted by one or more alkoxy groups or halogen atoms;Y is optionally substituted alkoxy or cycloalkoxy, arylalkoxy or a group of formula --NR6R7 wherein R6 is hydrogen or alkyl and R7 is alkyl, cycloalkyl (which alkyl and cycloalkyl groups may be substituted), aryl or arylalkyl or R7 is a group of formula --COOR8 is alkyl or arylalkyl, which are useful as intermediates in the synthesis of beta-lactam antibiotics, particularly carbapenems, and to a process for the manufacture of the said compounds.
    Type: Grant
    Filed: March 2, 1987
    Date of Patent: October 9, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventor: Ralph W. Turner
  • Patent number: 4925590
    Abstract: Derivatives of 4-cyano-2,3-difluorophenol of the formula I ##STR1## wherein R.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by --O--, --CO--, --CO--O-- and/or --CH.dbd.CH--, no two 0 atoms being directly attached to one another,A.sup.1 and A.sup.2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or S atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, OCH.sub.2 --, --CH.sub.2 O, --C.tbd.C-- or a single bond,m is 0, 1 or 2 andQ is --CO-- or --CH.sub.2 --.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: May 15, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller
  • Patent number: 4902334
    Abstract: A plant metabolism regulating agent comprising as an active ingredient an alpha,beta or beta,gamma-un-saturated carboxylic acid or its derivative. It is useful for controlling the metabolism of a plant, facilitating the growth of a beneficial plant such as cereals by inhibiting the growth of undesirable plants or eradicating them, regulating the growth of a plant and dwarfing a plant.
    Type: Grant
    Filed: October 31, 1984
    Date of Patent: February 20, 1990
    Assignee: Teijin Limited
    Inventors: Shizuo Azuma, Toshiyuki Hiramatsu, Teizo Yamaji, Yataro Ichikawa
  • Patent number: 4897382
    Abstract: Organic amide compounds of the formula ##STR1## wherein R.sub.1 --CO is a residue of a carboxylic acid with the proviso that the carboxylic acid is not a natural fatty acid normally bound to nitrogen of nitrogenous lipids, R.sub.2 is a hydrogen atom, a C.sub.1-7 alkyl group, or a C.sub.4-7 cycloalkyl group, and R.sub.3-N is a residue of a nitrogenous lipid. The compounds are useful in increasing or stimulating the in vivo biological activity of in vitro biologically active carboxylic acids.
    Type: Grant
    Filed: June 21, 1988
    Date of Patent: January 30, 1990
    Assignee: Fidia S.p.A.
    Inventors: Francesco della Valle, Aurelio Romeo
  • Patent number: 4892961
    Abstract: An amino acid derivative of the formula: ##STR1## wherein R.sup.1 is a protective group for hydroxyl, which is useful as an intermediate for production of antimicrobial agent.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: January 9, 1990
    Assignee: Sumitomo Pharmaceuticals Company, Limited
    Inventors: Shiro Terashima, Yoshikazu Kimura, Yoshio Ito, Kunikazu Sakai, Tamejiro Hiyama
  • Patent number: 4891363
    Abstract: Compounds of formula (I): ##STR1## (wherein: l is 2-4; A and B are oxygen or sulfur; one of R.sup.1 and R.sup.2 represents a long chain alkyl, alkylcarbamoyl or aliphatic acyl group and the other of R.sup.1 and R.sup.2 represents a group of formula (III) or (II.sub.f): ##STR2## in which E represents a single bond, a bivalent heterocyclic group or a group of formula --CO--, --COO-- or --CONR.sup.6 --, where R.sup.6 is hydrogen or an imino-protecting group; m is 0-3; n is 0-10; q is 0 or 1; R.sup.4 is optionally protected hydroxy, mercapto group or carboxy; Q is an amino or nitrogen-containing heterocyclic group;R.sub.f.sup.4 R.sub.f.sup.5 and R.sub.f.sup.6 are independently selected from the group consisting of hydrogen atoms and C.sub.1 -C.sub.6 alkyl groups, or R.sub.f.sup.4 and R.sub.f.sup.5 or R.sub.f.sup.4, R.sub.f.sup.5 and R.sub.f.sup.
    Type: Grant
    Filed: February 4, 1988
    Date of Patent: January 2, 1990
    Assignee: Sankyo Company Limited
    Inventors: Norio Nakamura, Nobuyuki Ookawa, Hiroyuki Koike, Toshio Sada, Takeshi Oshmia, Yoshio Iizuka, Hideki Miyazaki
  • Patent number: 4889873
    Abstract: Novel compounds and compositions which inhibit SRS-A in mammals are disclosed. Methods for preparing said compounds and compositions and methods for their use for treating allergic reactions, inflammation and for reducing the severity of myocardial infarction resulting from heart attack are disclosed.Useful intermediates for preparing said compounds are also disclosed.
    Type: Grant
    Filed: November 17, 1987
    Date of Patent: December 26, 1989
    Assignee: Schering Corporation
    Inventors: Anil K. Saksena, Jesse K. Wong, Pietro Mangiaracina
  • Patent number: 4886546
    Abstract: A compound of the formula (I) ##STR1## wherein (1) when R.sub.1 is a C.sub.2-11 alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aralkyl which may be substituted, a lower haloalkyl or a 5 or 6 membered heterocycle;R.sub.2, R.sub.3 and R.sub.4 are the same or different, hydrogen, a halogen, cyano, nitro, amino, a lower alkyl, a lower haloalkyl, hydroxy, a lower alkoxy, an aryloxy, carboxy, or a lower alkoxycarbonyl;R.sub.5 is hydrogen, a halogen, a C.sub.1-11 alkyl, an aryl which may be substituted, an aralkyl which may be substituted;R.sub.6 is a C.sub.1-11 alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aryl which may be substituted, an aralkyl which may be substituted, a lower haloalkyl, or a 5 or 6 membered heterocycle; or R.sub.5 and R.sub.6 may be combined to form a group of --(CH.sub.2).sub.m -- (m is 3 or 4);(2) when R.sub.1 is an aryl which may be substituted;R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the same meanings as defined above; R.
    Type: Grant
    Filed: March 11, 1987
    Date of Patent: December 12, 1989
    Assignee: Daicel Chemical Industries Ltd.
    Inventors: Hiroshi Yagihara, Yukihisa Goto, Kazuhisa Masamoto, Yasuo Morishima, Hirokazu Osabe
  • Patent number: 4885367
    Abstract: Sulfonanilide compounds represented by the formula ##STR1## wherein R.sup.1 is a lower alkyl group or a trifluoromethyl group, R.sup.2 is a cycloalkylidenemethyl group, a group of the formula --A--R.sup.3 (wherein A is an oxygen atom, a sulfur atom, a sulfynyl group or a sulfinyl group and R.sup.3 is a cycloalkyl group having 5-8 carbon atoms; a cycloalkyl group having 5-8 carbon atoms substituted by one or two of a lower alkyl group, an oxo group, a hydroxyl group or a methanesulfonyloxy group, a tetrahydropyranyl group; a tetrahydrothiopyranyl group; or a 1-methyl-piperidyl group) or a group of the formula --B--R.sup.4 (wherein B is a carbonyl group, a hydroxymethylene group or a methylene group, R.sup.4 is a cycloalkyl group having 5-8 carbon atoms) and the pharmaceutically acceptable salts thereof have anti-inflammatory activity.
    Type: Grant
    Filed: November 16, 1988
    Date of Patent: December 5, 1989
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Kensei Yoshikawa, Yutaka Ohuchi, Kazuto Sekiuchi, Shiuji Saito, Katsuo Hatayama, Kaoru Sota
  • Patent number: 4873345
    Abstract: This invention relates to novel intermediates, and novel processes for their preparation, where said intermediates are useful in a novel preparation of 5'-Oxa, 5'-Thia and 5'-Aza derivatives (I) of lovastatin and analogs thereof at the 8'-acyl side chain and 6'-position of the polyhydronaphthyl ring. Said derivatives (I) are useful in treating hypercholesterolermia. ##STR1## A is O, S(O).sub.n or N-R.sub.13.
    Type: Grant
    Filed: September 29, 1988
    Date of Patent: October 10, 1989
    Assignee: Merck & Co., Inc.
    Inventor: Mark E. Duggan
  • Patent number: 4871761
    Abstract: Novel pesticides of the formula ##STR1## in which R.sup.1 represents in each case optionally substituted cycloalkyl, cycloalkenyl, tetrahydronaphthyl, decahydronaphthyl, phenyl, naphthyl or thienyl,R.sup.2 represents alkyl,R.sup.3 represents hydrogen alkyl, alkenyl, alkinyl, hydroxyalkyl, alkoxyalkyl, dialkoxyalkyl, hydroxyalkoxyalkyl, cyano or formyl, or in each case optionally substituted cycloaklyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, aralkyl, aryl, furanylmethyl or tetrahydrofuranylmethyl,R.sup.4 represents hydrogen or alkyl, andHet represents an optionally substituted heterocyclic ring of the formula ##STR2## and acid-addition salts thereof.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: October 3, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Detlef Wollweber, Stefan Dutzmann
  • Patent number: 4837345
    Abstract: A process for producing a tetrahydropyran-3-one derivative of the formula: ##STR1## wherein R is a hydrogen atom; a straight chained or branched C.sub.1 -C.sub.10 alkyl group which is unsubstituted or substituted by a halogen atom, a hydroxyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkylcarbonyloxy group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 mono- or dialkylamino group, a C.sub.3 -C.sub.6 cycloaklyl group, a C.sub.1 -C.sub.6 alkylaminocarbonyl group, a C.sub.1 -C.sub.6 alkylcarbonylamino group, a C.sub.1 -C.sub.6 alkylcarbonyl group or a phenyl or benzoyl group which is unsubstituted or substituted by a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkythio group or a C.sub.1 -C.sub.6 alkoxycarbonyl group; a C.sub.3 -C.sub.6 cycloalkyl group; or a phenyl or biphenyl group which is unsubstituted or substituted by a halogen atom, a C.sub.1 -C.sub.6 alkoxy group or C.sub.1 -C.sub.
    Type: Grant
    Filed: December 31, 1987
    Date of Patent: June 6, 1989
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Tatsuo Numata, Masataka Hatanaka, Junichi Watanabe
  • Patent number: 4818431
    Abstract: New tetrahydropyran derivatives of the formula I ##STR1## in which G is H.sub.2 or .dbd.O, R.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, it also being possible for one or two CH.sub.2 groups to be replaced by O atoms, or are F, Cl, Br or CN, R.sup.2 is also H, A.sup.1 and A.sup.2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by 1-4 F atoms, Z.sup.1 and Z.sup.2 are each --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, or a single bond, m and n are each 0, 1, 2 or 3, but (m+n) is at least 1 and at most 3, it being possible, when m is 2 or 3, for the group A.sup.1 and, when n is 2 or 3, for the groups A.sup.2 each to be identical or different from one another, and the acid addition salts of those among these compounds which are basic, are suitable for use as components in liquid-crystal dielectrics.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: April 4, 1989
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Joachim Krause, Peter Fuss
  • Patent number: 4812160
    Abstract: Cyclohexenone derivative of the formula ##STR1## where A is oxygen or NOR.sup.8, where R.sup.8 is alkyl, alkenyl, alkynyl, haloalkyl or haloalkenyl, chlorothienyl or alkoxyalkylB is O, S, SO or SO.sub.2,X is hydrogen or methoxycarbonyl,R.sup.1 is hydrogen, carbonylalkyl, benzoyl or a cation,R.sup.2 is alkyl,R.sup.3 and R.sup.4 are hydroxyl, chlorine, bromine, thioalkylcarboxyl, thiocarbonylalkyl, alkylcarbonyloxy, alkoxy, or alkylthio, or R.sup.3 and R.sup.4 together epoxy,R.sup.5 and R.sup.6 are hydrogen or methyl or R.sup.5 and R.sup.6 are together methyleneoxyethylene, andR.sup.7 is hydrogen or methyl,and herbicides containing these compounds.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: March 14, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer, Johann Jung, Wilhelm Rademacher
  • Patent number: 4788300
    Abstract: A process for preparing compounds (1) ##STR1## where Y is NR.sup.1 R.sup.2 or OR, R.sup.1 and R.sup.2 are hydrogen or C.sub.1-3 alkyl, and R is C.sub.1-3 alkyl, which comprises protecting the hydroxy group of a compound (2) ##STR2## cyclizing the product under basic conditions and removing the protecting group.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: November 29, 1988
    Assignee: I.S.F. Societa per Azioni
    Inventors: Mario Pinza, Ugo C. Pfeiffer
  • Patent number: 4761172
    Abstract: Cyclohexenol derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, X and A have the meanings stated in the description, are used for controlling undesirable plant growth.
    Type: Grant
    Filed: October 5, 1984
    Date of Patent: August 2, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Rainer Becker, Michael Keil, Ulrich Schirmer, Winfried Richarz, Bruno Wuerzer, Norbert Meyer
  • Patent number: 4758594
    Abstract: Novel compounds and compositions which inhibit SRS-A in mammals are disclosed. Methods for preparing said compounds and compositions and methods for their use for treating allergic reactions, inflammation and for reducing the severity of myocardial infarction resulting from heart attack are disclosed.Useful intermediates for preparing said compounds are also disclosed.
    Type: Grant
    Filed: May 19, 1986
    Date of Patent: July 19, 1988
    Assignee: Schering Corporation
    Inventors: Anil K. Saksena, Jesse K. Wong, Pietro Mangiaracina
  • Patent number: 4739083
    Abstract: A new process for preparing a pyrone-3-carboxamide compound of the formula (IV): ##STR1## wherein R.sub.1 is aryl or heterocyclic group optionally substituted, R.sub.2 is alkyl, aralkyl or like group, comprising reacting a compound of the formula (I) or (I'): ##STR2## wherein R.sub.3 is dialkylamino group and n is 0 to 6, and R.sub.1 and R.sub.2 are as above,with a compound of the formula (II): ##STR3## wherein R.sub.4 and R.sub.5 are hydrogen atom, alkyl or like group, or reacting a compound of the formula (III): ##STR4## wherein R.sub.6 is alkyl, aryl or like group, and R.sub.1 and R.sub.2 are as above,with a compound of the formula (II) or diketene in the presence of a tertiary organic base.
    Type: Grant
    Filed: January 2, 1986
    Date of Patent: April 19, 1988
    Assignee: Daicel Chemical Industries Ltd.
    Inventors: Yoichiro Ueda, Yukihisa Goto, Kazuhisa Masamoto
  • Patent number: 4739068
    Abstract: N-Phenylsulfonyl-N'-pyrimidinylureas and --N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: April 19, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Karl Gass, Werner Fory, Willy Meyer, Werner Topfl
  • Patent number: 4730061
    Abstract: A pyrone-3-carboxamide compound of the formula (I): ##STR1## in which R.sub.1 is an alkyl group, and R.sub.2 is an alkyl group or a halogen atom, which is useful as a medicine and an agricultural chemical or an intermediate thereof.
    Type: Grant
    Filed: December 31, 1985
    Date of Patent: March 8, 1988
    Assignee: Daicel Chemical Industries Ltd.
    Inventors: Yoichiro Ueda, Yukihisa Goto, Kazuhisa Masamoto, Yoshiyuki Hirako, Hiroshi Yagihara, Yasuo Morishima, Hirokazu Osabe
  • Patent number: 4730058
    Abstract: This invention provides a novel compound expressed by the following formula (1): ##STR1## [wherein R.sup.1 denotes a hydrogen atom or CH.sub.3 CO--, R.sup.2 denotes --COOR.sup.4 (R.sup.4 denotes Na or a methyl group) or ##STR2## (R.sup.5 denotes a hydrogen atom, --COC.sub.6 H.sub.5 or --Si(C.sub.6 H.sub.5).sub.2 C(CH.sub.3).sub.3 and R.sup.3 denotes ##STR3## (R.sup.5 denotes a hydrogen atom, --COC.sub.6 H.sub.5 or --Si(C.sub.6 H.sub.5).sub.2 C(CH.sub.3).sub.3) when R.sup.2 is --COOR.sup.4 (R.sup.4 denotes Na or a methyl group) or denotes --COOR.sup.4 when R.sup.2 is ##STR4## and a method of preparation thereof. The above novel compounds of present invention are useful as a tumor maker, a molecular marker for cells having the ability of differential induction, or an intermediate of the synthesis thereof.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: March 8, 1988
    Assignee: Mect Corporation
    Inventors: Tomoya Ogawa, Mamoru Sugimoto, Masaaki Numata, Yoshiyasu Shitori, Masayoshi Ito
  • Patent number: 4728746
    Abstract: .beta.-Aminothiol ester having the general formula (I): ##STR1## which is useful as an intermediate in the preparation of carbapenen beta-lactam antiobiotics, wherein R.sup.1 is alkyl or aryl and R.sup.2 and R.sup.3 are protective groups. The .beta.-Aminothiol ester of formula (I) is prepared by reacting a .beta.-hydroxythiol ester having the general formula (III): ##STR2## wherein R.sup.1 is as above, with a boron compound having the general formula (IV): ##STR3## wherein each of R and R' is alkyl or cycloalkyl, or R and R' taken together, form a ring including the boron atom in the presence of a tertiary amine, the obtained reaction mixture being reacted with an imine having the general formula (V): ##STR4## Wherein R.sup.2 and R.sup.3 are protective groups, followed by treating the resultant product with hydrogen peroxide.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: March 1, 1988
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Shibasaki, Takamasa Iimori
  • Patent number: 4680388
    Abstract: Antibacterial activity is exhibited by compounds having the formula and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: July 14, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
  • Patent number: 4665092
    Abstract: Alkenes of the formula (I) and epoxides (II) used to make them are useful as anti-inflammatory and antiallergic pharmaceuticals: ##STR1## wherein R.sup.1 =H or CH.sub.3 ; R.sup.2 =phenyl, substituted phenyl, benzyl or a cysteinyl moiety; R.sup.4 and R.sup.5 =alkyl; n=O or 1; and R.sup.3 is as described.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: May 12, 1987
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Michael P. Ferro, Michael P. Wachter
  • Patent number: 4659818
    Abstract: 2,4-Diamino-5-benzylpyrimidines of the formula ##STR1## wherein R.sup.1, R.sup.2, A, Z and n are as hereinafter set forth, are described. The 2,4-diamino-5-benzylpyrimidines of the invention have useful antibacterial activity. More particularly, they inhibit bacterial dihydrofolate reductase and potentiate the antibacterial activity of sulfonamides.
    Type: Grant
    Filed: February 27, 1985
    Date of Patent: April 21, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ivan Kompis, Gerald Rey-Bellet, Guido Zanetti
  • Patent number: 4659844
    Abstract: The invention relates to new cyclic ethers which are substituted in the .alpha.-position by an isocyanide-dichloride group, of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n have the meaning indicated in the description, and to a process for their preparation.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Tillmann Hassel, Hanns P. Muller, Horst Boshagen
  • Patent number: 4639535
    Abstract: Disclosed are trisubstituted benzene derivatives of the formula ##STR1## wherein B is selected from the group consisting of --NHCOC(CH.sub.3).sub.3, 1,3-oxazolinyl and --CONHR, wherein R is methyl, phenyl, or t-butyl; Y is selected from the group consisting of CO.sub.2 H, CHO, CO.sub.2 R' and COR', wherein R' is a lower alkyl having from 1 to 4 carbon atoms; and A is H or tetrahydropyran. Said compounds are valuable intermediates in the preparation of certain anti-allergic chromone or thiochromone-5-oxamic acid derivatives.
    Type: Grant
    Filed: October 30, 1985
    Date of Patent: January 27, 1987
    Assignee: Miles Laboratories, Inc.
    Inventors: Trevor S. Abram, Peter Norman, Brian T. Warren
  • Patent number: 4638060
    Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: April 29, 1985
    Date of Patent: January 20, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
  • Patent number: 4623660
    Abstract: The disclosure relates to 1-p-aminoalkoxy phenyl-1-p-hydroxyphenyl-2-phenylalk-1-ene derivatives, processes for their manufacture and pharmaceutical compositions containing them. The compounds possess anti-oestrogenic activity and are useful in the treatment of anovulatory infertility and the breast tumors. Representative of the compounds disclosed is 1-(p-.beta.-dimethylaminoethoxyphenyl)-trans-1-p-hydroxyphenyl-2-p-tolylbu t-1-ene.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: November 18, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventor: Dora N. Richardson
  • Patent number: 4611067
    Abstract: This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-cyano-3(R)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: September 9, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Ralph P. Volante, Thomas R. Verhoeven, Meyer Sletzinger, James M. McNamara, Thomas M. H. Liu, Edward G. Corley
  • Patent number: 4608385
    Abstract: Use of an N-phenylcarbamate of the formula: ##STR1## as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole thiophanate fungicides and/or cyclic imide fungicides.
    Type: Grant
    Filed: October 22, 1982
    Date of Patent: August 26, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Noguchi, Toshiro Kato, Junya Takahashi, Yukio Ishiguri, Shigeo Yamamoto, Katsuzo Kamoshita
  • Patent number: 4602935
    Abstract: Cyclohexane-1,3-dione derivatives of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or halogen-substituted alkenyl or alkynyl, X is a saturated or unsaturated five-membered or six-membered heterocyclic structure which carries one or more substituents, and Z is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, and salts of these compounds are used for controlling undesirable plant growth.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: July 29, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Dieter Jahn, Michael Keil, Walter Himmele, Bruno Wuerzer
  • Patent number: 4556649
    Abstract: Insecticidally active novel substituted malonic acid diamide insecticides of the formula ##STR1## wherein R.sup.1 represents aryl or heteroaryl, each of which can optionally be substituted,R.sup.2 represents hydrogen or trialkylsilyl, and represents alkyl, cycloalkyl, alkenyl, alkinyl, aralkyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphenyl, arylsulphenyl, alkylsulphonyl, arylsulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, arylaminosulphonyl or arylalkylaminosulphonyl, each of which can optionally be substituted, and represents radicals of the formula--CO--NR.sup.5 R.sup.6whereinR.sup.5 and R.sup.6 independently of one another represent hydrogen, alkyl, cycloalkyl, aryl, alkylaminocarbonyl, arylaminocarbonyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphonyl or arylsulphonyl, it being possible for these radicals to be optionally substituted,R.sup.3 represents hydrogen or the radical R.sup.4,R.sup.7 and R.sup.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: December 3, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Salzburg, Rudolf Fauss, Kurt Findeisen, Bernhard Homeyer
  • Patent number: 4551472
    Abstract: Unsymmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: November 5, 1985
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4539148
    Abstract: Useful intermediates, 7.alpha.-acylamino-3-(oxo or exomethylene)-1-dethia-1-oxacepham-4.alpha.-carboxylates, are produced by the intramolecular carbenoid insertion of a 2-diazo-3-(oxo or exomethylene)-4-(3.alpha.-acylamino-2-oxoazetidin-4.beta.-yl)oxybutyrate prepared in several steps from the corresponding oxazolinoazetidinone and diketone.
    Type: Grant
    Filed: August 16, 1983
    Date of Patent: September 3, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Sadao Yamamoto, Hikaru Itani, Hiromi Takahashi, Teruji Tsuji, Wataru Nagata
  • Patent number: 4482495
    Abstract: N-acetyl-para-aminophenyl N'-acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenol. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: November 13, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Margetts, Roderic S. Andrews, Jean Legros
  • Patent number: 4416889
    Abstract: N-allenyl-acetanilides of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or halogen,R.sup.2 represents hydrogen or alkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen or alkyl andR.sup.6 represents furyl, tetrahydrofuryl, thiophenyl or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by alkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted by cyano or thiocyano; dihalogenoalkyl; or the grouping ##STR2## wherein R.sup.7 represents an optionally substituted alkyl, alkenyl, alkynyl or alkoxyalkyl radical andAz represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl.which possess fungicidal properties.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: November 22, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Winfried Lunkenheimer, Wilhelm Brandes
  • Patent number: 4413006
    Abstract: A piperazine derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl (C.sub.1-8), alkyl (C.sub.1-4)-sulfonyl or an acyl group of the formula: R.sup.3 CO--(wherein R.sup.3 is hydrogen, alkyl (C.sub.1-7), halogenoalkyl (C.sub.1-4), alkoxy (C.sub.1-4)-carbonyl-alkyl (C.sub.1-4), cycloalkyl (C.sub.3-6), alkenyl (C.sub.2-5), alkoxy (C.sub.1-4), amino, alkyl (C.sub.1-4)-amino or anilino), R.sup.2 is hydrogen, alkyl (C.sub.1-4), alkoxy (C.sub.1-4)-carbonyl-alkyl (C.sub.1-4), carboxy-alkyl (C.sub.1-4), alkenyl (C.sub.2-5) or alkyl (C.sub.1-4)-sulfonyl, or R.sup.1 and R.sup.2 are combined together to form succinyl group, Ring A is phenyl, alkyl (C.sub.1-4)-phenyl or halogenophenyl, and n is an integer of 2 to 6, or a pharmaceutically acceptable acid addition salt thereof. The piperazine derivative (I) has an intracranial pressure-lowering activity. Said derivative also has a depressing effect on central nervous system.
    Type: Grant
    Filed: May 3, 1982
    Date of Patent: November 1, 1983
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Takeshi Kanno, Mitsunori Gaino, Michio Yamamura, Ryuichi Ishida, Keiichi Shintomi
  • Patent number: 4405333
    Abstract: The cetane number of diesel fuel is increased by the addition of a tetrahydropyranol nitrate ester, e.g. tetrahydro-2H-pyran-3-ol nitrate.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: September 20, 1983
    Assignee: Ethyl Corporation
    Inventor: Paul D. Seemuth
  • Patent number: 4405640
    Abstract: Insecticides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each selected from methyl, halomethyl, and halo; X is oxygen, sulphur, sulphonyl or a group NR.sup.4 where R.sup.4 represents hydrogen, lower alkyl or lower carboxylic acyl; R.sup.3 is lower alkyl, lower alkenyl or benzyl; m has the value zero or one, and n has a value from one to four.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: September 20, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: Nazim Punja