Nitrogen Attached Indirectly To The Hetero Ring By Acyclic Nonionic Bonding Patents (Class 549/366)
  • Patent number: 5126366
    Abstract: The compounds: ##STR1## wherein R.sup.1 and R.sup.2 are, independently, hydrogen, alkyl, alkoxy, aralkoxy, alkanoyloxy, hydroxy, halo, amino, mono- or dialkylamino, alkanamido, or sulfonamido, or R.sup.1 and R.sup.2 together form methylenedioxy, ethylenedioxy, or propylenedioxy; R.sup.3 is hydrogen or alkyl; n is one of the integers 2, 3 or 4; R.sup.4 and R.sup.5 are, independently, hydrogen, alkyl, cycloalkyl, alkanoyl, aroyl, alkylsulfonyl or arylsulfonyl, or R.sup.4 and R.sup.5 together form a 3-7 membered polymethylene ring; or a pharmaceutically acceptable salt thereof, are antipsychotic, antidepressant and anxiolytic agents useful in the treatment of multi-CNS disease states.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: June 30, 1992
    Assignee: American Home Products Corporation
    Inventors: Gary P. Stack, Magid A. Abou-Gharbia, Terrance H. Andree, Noreen T. Scherer
  • Patent number: 5126367
    Abstract: A compound of the formula: ##STR1## wherein the dotted line represents optional unsaturation; R.sup.1 is hydrogen, alkyl, alkoxy, alkanoyloxy, hydroxy, halo, nitro, amino, alkylamino, dialkylamino and alkanoylamino; X is O, S or CH.sub.2 ; n is an integer 2, 3 or 4; R.sup.2 is hydrogen or lower alkyl; R.sup.3 is hydrogen, lower alkyl, phenyl or benzyl; R.sup.4 is one of the structures ##STR2## in which m is one of the integers 0, 1 or 2; R.sup.5 is H or CH.sub.3 ; Z is H.sub.2 or O; Y is OCO, NHCO, NHCONH, CONH, and in addition, when R.sup.4 is II, Y may be NHSO.sub.2 CH.sub.2 ; or a pharmaceutically acceptable salt thereof are useful as antipsychotic/anxiolytic agents.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: June 30, 1992
    Assignee: American Home Products Corporation
    Inventors: Gary P. Stack, Magid A. Abou-Gharbia, Wayne E. Childers, Jr.
  • Patent number: 5120758
    Abstract: The invention relates to the compounds of the formula ##STR1## wherein each R independently represents hydrogen, lower alkyl, halogen, trifluoromethyl, lower alkoxy, carbocyclic or heterocyclic aryl, carbocyclic or heterocyclic aryloxy, carbocyclic or heterocyclic aryl-lower alkyloxy, carbocyclic or heterocyclic aryl-lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl-lower alkyloxy, or C.sub.3 -C.sub.7 -cycloalkyloxy; n represents 1, 2, 3 or 4; m represents 0, 1 or 2; A represents a direct bond or lower alkylene; X represents oxygen or sulfur; R.sub.1 represents hydrogen, acyl, lower alkoxycarbonyl, aminocarbonyl, mono- or di-lower alkylaminocarbonyl, lower alkenylaminocarbonyl, lower alkynylaminocarbonyl, carbocyclic or heterocyclic aryl-lower alkylaminocarbonyl, carbocyclic or heterocyclic arylaminocarbonyl, C.sub.3 -C.sub.7 -cycloalkylaminocarbonyl or C.sub.3 -C.sub.7 -cycloalkyl-lower alkylaminocarbonyl; R.sub.2 represents lower alkyl, lower alkoxycarbonyl-lower alkyl, C.sub.3 -C.sub.
    Type: Grant
    Filed: July 8, 1991
    Date of Patent: June 9, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Yoshitaka Satoh
  • Patent number: 5070210
    Abstract: A series of novel imidate insecticides distinguished by the general formula ##STR1## in which R.sub.1 is an optionally substituted aryl group in which the substituents are halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 -C.sub.6 cycloalkyl, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 carboalkoxy, C.sub.1 -C.sub.4 alkylthio, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkylsulfonyl; C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.4 alkylenedioxy, C.sub.1 -C.sub.3 halo-substituted alkylenedioxy, phenyl, mono-substituted phenyl, pyridyloxy, C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkenyl, and/or amido;R.sub.2 is C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.6 haloalkyl, cyclopropyl, cyclobutyl, mono- or poly- halo- or methyl-substituted cyclopropyl, cyano, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.6 haloalkenyl or C.sub.2 -C.sub.6 alkenyl; andR.sub.
    Type: Grant
    Filed: May 7, 1990
    Date of Patent: December 3, 1991
    Assignee: ICI Americas Inc.
    Inventors: Michael D. Broadhurst, Thomas H. Cormartie, Karl J. Fisher, William G. Haag, David B. Kanne, Michael R. Leadbetter
  • Patent number: 5047417
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydrogen or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: September 10, 1991
    Assignee: Eisai Co. Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5045566
    Abstract: A series of novel imidate insecticides distinguished by the general formula ##STR1## in which R.sub.1 is an optionally substituted aryl group in which the substituents are halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.3 -C.sub.6 cycloalkyl, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.5 carboalkoxy, C.sub.1 -C.sub.4 alkylthio, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.2 -C.sub.4 haloalkylsulfonyl; C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.4 alkyleneoxy, C.sub.1 -C.sub.2 perhaloalkyleneoxy; C.sub.1 -C.sub.4 alkylendioxy, C.sub.1 -C.sub.3 halo-substituted alkylenedioxy, phenyl, mono-substituted phenyl, pyridyloxy, C.sub.2 -C.sub.4 alkylene, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -haloalkenoxy; and/or amido;R.sub.2 is C.sub.1 -C.sub.7 alkyl, C.sub.1 -C.sub.6 haloalkyl, cyclopropyl, cyclobutyl, mono- or poly- halo- or methyl-substituted cyclopropyl, cyano, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.6 haloalkenyl or C.sub.2 -C.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: September 3, 1991
    Assignee: ICI Americas Inc.
    Inventors: Michael D. Broadhurst, Thomas H. Cromartie, Karl J. Fisher, William G. Haag
  • Patent number: 5036070
    Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each, independently, hydrogen, alkyl, or phenyl, or R.sup.1 and R.sup.2 taken together represent --(CH.sub.2).sub.4 -- or ##STR2## where the dotted line represents an optional double bond; R.sup.3 is hydrogen, alkyl, alkoxy, or halo;Z is oxygen, or --N(R.sup.6), where R.sup.6 is hydrogen or alkyl;m is 1-4;n is 0-2; ##STR3## wherein R.sup.7 is unsubstituted or substituted phenyl, 2-pyridinyl, 2-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, or diphenylmethyl, where the substituents are selected from the group of alkyl, alkoxy, halo, cyano, nitro and trifluoromethyl;R.sup.8 is hydrogen, hydroxy, cyano, alkyl, alkoxy, halo, or NHR.sup.9 where R.sup.9 is hydrogen, alkyl, phenyl, tolyl, xylyl, mesityl, methoxyphenyl, or halophenyl with the proviso when Z is oxygen, R.sup.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: July 30, 1991
    Assignee: American Home Products Corporation
    Inventor: Magid A. Abou-Gharbia
  • Patent number: 4977170
    Abstract: Novel isoprenoidamine compounds (I) which show antiulcer activity are provided.
    Type: Grant
    Filed: May 3, 1989
    Date of Patent: December 11, 1990
    Assignee: Shionogi & Co., Ltd.
    Inventors: Saichi Matsumoto, Masami Doteuchi, Takuji Mizui, Kentaro Hirai
  • Patent number: 4929738
    Abstract: Microbicidal substituted pyrazolin-5-ones of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylaminocarbonylalkyl or dialkylaminocarbonylalkyl, or represent in each case optionally substituted oxiranylalkyl, aralkyl, heterocyclyl or aryl andHet represents an optionally substituted heterocyclic radial.Intermediates therefor of the formula ##STR2## in which R is alkyl, are also new.
    Type: Grant
    Filed: May 10, 1989
    Date of Patent: May 29, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Jelich, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4914124
    Abstract: A method of combating endoparasites which comprises applying thereto or to an endoparasite habitat an endoparasiticidally effective amount of an N-organooxycarbamic acid ester of the formula ##STR1## in which R.sup.1 represents alkyl, cycloalkyl, alkenyl, alkinyl or aryl, which can optionally be substituted,R.sup.2 represents alkyl, alkenyl or alkinyl, which can optionally be substituted, andR.sup.3 represents alkyl, alkenyl or alkinyl, which can optionally be substituted.Those compounds wherein one of R.sup.2 and R.sup.3 is alkinyl are new.
    Type: Grant
    Filed: January 25, 1988
    Date of Patent: April 3, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Nikolaus Muller, Peter Andrews
  • Patent number: 4897415
    Abstract: There are described new 2-imino-1,3-dithietanes of general formula I ##STR1## in which R is the group ##STR2## in which A is CFHal, C(CH.sub.3)C.sub.1-4 -alkyl, C(CH.sub.3)CHal.sub.3, C(CH.sub.3)CF.sub.2 Cl, C(CH.sub.3)CFCl.sub.2, C.sub.2 H.sub.4, C.sub.2 H.sub.3 Hal, C.sub.2 H.sub.2 Hal.sub.2, C.sub.2 HHal.sub.3, C.sub.2 F.sub.2 Cl.sub.2, C.sub.2 F.sub.4 or C.sub.2 F.sub.3 Cl, in which Hal is F or Cl,Y is nitrogen or CH,R.sup.1 is fluoro-C.sub.1-12 -alkyl, fluoro-C.sub.2-12 -alkenyl, fluoro-C.sub.2-12 -alkynyl, fluorocyclopropyl or fluorocyclopropylmethyl;X is oxygen or sulphur,2 is defined in the specification andn is 0, 1 or 2,as well as their acid addition salts, a process for their preparation and their use as pesticides. The new compounds are especially useful as nematicides.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: January 30, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Dieter Hubl, Ernst-Albrecht Pieroh, Eberhard Richter, Reinhold Puttner
  • Patent number: 4883796
    Abstract: Oxime ethers of 2,6-dioxabicyclo[3.3.0]octanones of the formula I ##STR1## have pharmacological activity and are especially applicable as drugs for the prophylaxis and therapy of cardiac and circulatory diseases.
    Type: Grant
    Filed: February 2, 1988
    Date of Patent: November 28, 1989
    Assignee: Heinrich Mack Nachf.
    Inventors: Matyas Leitold, Peter Stoss
  • Patent number: 4853381
    Abstract: The invention provides compounds of the general formula (I) ##STR1## whereinAr represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms, or the groups C.sub.1-6 alkyl, C.sub.1-6 alkoxy, nitro, --(CH.sub.2).sub.q R [where R is hydroxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O--, or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl or --NR.sup.3 R.sup.4 group), --NR.sup.5 SO.sub.2 R.sup.7 (where R.sup.7 represents a C.sub.1-4 alkyl, phenyl or --NR.sup.3 R.sup.4 group), --COR.sup.8 (where R.sup.8 represents hydroxy, C.sub.1-4 alkoxy or --NR.sup.3 R.sup.4), --SR.sup.
    Type: Grant
    Filed: October 15, 1986
    Date of Patent: August 1, 1989
    Assignee: Glaxo Group Limited
    Inventors: Harry Finch, Lawrence H. C. Lunts, Alan Naylor, Ian F. Skidmore, Ian B. Campbell
  • Patent number: 4794118
    Abstract: 1,4-Benzodioxane derivatives represented by the following general formula: ##STR1## wherein p stands for an integer of 0-2, X and Y are same or different, and each represent a hydrogen atom; or a group represented by the formula --OR in which R denotes a hydrogen atom, a lower alkyl, lower alkoxycarbonyl or acyl group, or a group represented by the formula ##STR2## m being an integer of 1 or 2; cyano group; or carboxy group, n is an integer of 1-3, exclusive of the case wherein p=0 and X=Y=H, or a pharmacologically acceptable salt thereof. Their process for the preparation, their use as therpeutic and/or preventive compositions for ischemic heart diseases and heart failure and their application for the control of blood pressure during surgical operations are also described.
    Type: Grant
    Filed: July 18, 1986
    Date of Patent: December 27, 1988
    Assignee: Eisai Co., Ltd.
    Inventors: Toshinobu Kunii, Norio Minami, Fumihiro Ozaki, Nobuyuki Mori, Mikio Takeda, Hiroshi Katoh
  • Patent number: 4785089
    Abstract: The invention relates to novel sulfonic acid esters of formula I ##STR1## wherein R.sup.1 is C.sub.5 -C.sub.6 cycloalkyl which is unsubstituted or substituted by C.sub.1 -C.sub.7 alkyl, unsubstituted or substituted phenyl, R.sup.2 is C.sub.1 -C.sub.7 alkyl, R.sup.3 is phenyl which is substituted by halogen or nitro, and the asterisk denotes a carbon atom that is either present in the preponderant number of molecules in the S configuration or in the preponderant number of molecules in the R configuration.These compounds can be prepared by enantio-selective reduction of 4--R.sup.1 --substituted .alpha.-oxobutyric acid compounds and subsequent conversion of the resultant .alpha.-hydroxy group into the --OSO.sub.2 --R.sup.3 group. The compounds of formula I are suitable intermediates for the preparation of ACE inhibitors or precursors thereof.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Hans-Peter Jalett, Gottfried Sedelmeier
  • Patent number: 4709038
    Abstract: Herbicidal and fungicidal compounds of the formula ##STR1## wherein R.sup.1 is (a) a phenyl group optionally substituted by one or more halogen atoms, cyano groups, alkoxy groups, methylene- or ethylene-dioxy groups, alkyl groups, or haloalkyl groups (e.g. trifluoromethyl groups); or (b) a heteroaromatic group optionally substituted by one or more alkyl groups, haloalkyl groups or halogen atoms X is a 5-membered heteroaromatic radical linked by a ring nitrogen atom to the carbon atom bearing Y, and optionally substituted by one or more alkyl groups, and Y is a CN group; a --CSNH.sub.2 group; a --CO.sub.2 R.sup.4 group wherein R.sup.4 is an esterifying radical, for example an alkyl radical; or an amide group --CONR.sup.5 R.sup.6 wherein each of R.sup.5 and R.sup.6 may be a hydrogen atom or an alkyl radical (e.g. an alkyl radical of 1 to 6 carbon atoms).
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: November 24, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ian T. Kay, Robert A. Noon
  • Patent number: 4686233
    Abstract: Pesticidal water-soluble aminoacid sulfenylated carbamates useful as broad spectrum insecticides and miticides, particularly useful as systemic insecticides.
    Type: Grant
    Filed: May 1, 1986
    Date of Patent: August 11, 1987
    Assignee: Union Carbide Corporation
    Inventors: Chennupati K. Rao, Themistocles D. D'Silva
  • Patent number: 4684739
    Abstract: Alkylenedioxybenzene derivatives are prepared and found to be useful as pharmaceutical agents, particularly as hypotensives.
    Type: Grant
    Filed: December 1, 1981
    Date of Patent: August 4, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Ryoji Kikumoto, Harukazu Fukami, Kenichiro Nakao, Mamoru Sugano
  • Patent number: 4681955
    Abstract: New compounds of the formula ##STR1## a process for their preparation and their use as intermediates for insecticides.
    Type: Grant
    Filed: August 6, 1985
    Date of Patent: July 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventor: Albrecht Marhold
  • Patent number: 4634701
    Abstract: Compounds of formula (I): ##STR1## wherein: A represents a CH-NO.sub.2 group or a N-CN group;B represents CH.sub.2, O, S or a direct bond;R represents a bicyclic or polycyclic residue, variously substituted and functionalized;R.sup.1 and R.sup.2, which may be the same or different, are hydrogen or C.sub.1 -C.sub.4 alkyl groups; andn and m, which may be the same or different, are 0, 1, 2, 3 or 4;are valuable pharmacological agents.
    Type: Grant
    Filed: May 28, 1985
    Date of Patent: January 6, 1987
    Assignee: Ausonia Farmaceutici s.r.l.
    Inventor: Leonardo De Vincentiis
  • Patent number: 4616035
    Abstract: Combating pests such as insects, arachnids and nematodes with novel N-oxalyl-N-methylcarbamic acid esters of the formula ##STR1## in which R represents alkyl, alkenyl, alkinyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenalkylthio, halogen, nitro, dialkylamino, alkylsulphinyl, alkylsulphonyl, cycloalkyl or a saturated, optionally substituted heterocyclic radical with one or more hetero-atoms from the group comprising O, S and N, or forms a ring which is fused onto the phenyl radical, optionally contains one or more hetero-atoms from the group comprising O, S and N and is optionally substituted.
    Type: Grant
    Filed: October 15, 1984
    Date of Patent: October 7, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Heywang, Engelbert Kuhle, Bernhard Homeyer
  • Patent number: 4613612
    Abstract: Insecticidally and acaricidally active novel compounds of the formula ##STR1## in which A is --CF.sub.2 --CF.sub.2 --, --CF.sub.2 --CHF-- or --CF.sub.2 --CFCl--,X is oxygen or sulphur,R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen, halogen or alkyl,R.sup.4 and R.sup.5 each independently is hydrogen, halogen, alkyl or halogenoalkyl, andR.sup.6 is hydrogen, halogen or alkyl.The benzodioxene intermediates therefor are also new.
    Type: Grant
    Filed: August 8, 1985
    Date of Patent: September 23, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Albrecht Marhold, Benedikt Becker
  • Patent number: 4612313
    Abstract: The present invention provides phenylacetonitrile derivatives of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5, which can be the same or different, are hydrogen or haolgen atoms or alkyl, alkoxy, nitro, amino or acylamino radicals and two adjacent substituents can together also form a methylenedioxy or ethylenedioxy radical, A is a radical of the general formula: ##STR2## in which R.sub.6 is a straight-chained, cyclic or branched, saturated or unsaturated alkyl radical containing 2 to 12 carbon atoms, R.sub.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: September 16, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Herbert Leinert, Wolfgang Kampe, Klaus Strein, Bernd Muller-Beckmann, Wolfgang Bartsch
  • Patent number: 4611003
    Abstract: Compounds of the formula ##STR1## in which R.sup.1 is hydrogen, halogen or alkyl,R.sup.2 is halogen, alkyl or alkylthio,X is oxygen or sulphur, andY is hydrogen, halogen, alkyl or halogenoalkyl,which possess pesticidal activity.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: September 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann, Benedikt Becker, Ingomar Krehan, Wilhelm Stendel
  • Patent number: 4596880
    Abstract: Benzyl esters of the formula ##STR1## in which n is 1,2,3,4, or 5,R.sup.2 is hydrogen, C.sub.1-4 -alkyl, cyano or ethynyl,R.sup.3 is the radical of a carboxylic acid customary in pyrethroids or pyrethroid-like compounds, andat least one R.sup.1 is fluoroalkoxy or fluoroalkylmercapto, or two together are fluoromethylene- or fluoroethylene-dioxy, and the others, if present, are hydrogen or various radicals,which possess arthropodicidal properties. Various alcohols, amines, aldehydes, halides, and the like, corresponding to the alcohol moieties of the esters are also synthesized.
    Type: Grant
    Filed: November 2, 1983
    Date of Patent: June 24, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Albrecht Marhold, Wolfgang Behrenz, Ingeborg Hammann
  • Patent number: 4575557
    Abstract: Benzamides of the formula (I): ##STR1## in which Ar is optionally substituted aryl; X is O, S or NH and R is optionally substituted alkyl or alkenyl when X is O or S, or is optionally substituted alkenoyl when X is NH, are prepared by(a) reacting a compound of the formula (II):ArCONHCH.sub.2 CN (II)with a brominating agent in a solvent which is substantially chemically inert to the reactants and in which compound (II) is soluble, to form a compound of the formula (III): ##STR2## and (b) reacting the compound (III) with a compound RXH.Preferably, bromination is carried out rapidly in dried ethyl acetate.The process avoids hydration of the CN group of the compound (III) to a carbamoyl group obviating a subsequent dehydration step later.The intermediate compound (III) is novel.The substituted benzamides are useful as herbicides and fungicides.
    Type: Grant
    Filed: July 30, 1984
    Date of Patent: March 11, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventors: John D. Jones, David Schofield
  • 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: 4539413
    Abstract: The present invention concerns a novel process for the production of new chemical compounds of the general formula: ##STR1## in which: R.sub.1 and R.sub.2 may be identical or different and represent a hydrogen or halogen atom or else a lower alkyl, lower alkoxy, nitro or acetyl group andR represents a lower alkyl or lower aralkyl group, such as benzyl.These compounds are useful in therapy for the treatment of hypertension and cardiac arrhythmia.The novel process involves reaction of a 2-hydroxymethyl-1,4-benzodioxan with epichlorohydrin to produce an intermediate glycidyl ether, which is then reacted with a primary amine to produce the final 3-amino-1-[(1,4-benzodioxan)-2-yl-methoxy]-2-propanol or an acid addition salt thereof.
    Type: Grant
    Filed: January 3, 1983
    Date of Patent: September 3, 1985
    Assignee: Pierre Fabre S.A.
    Inventors: Gilbert Mouzin, Henri Cousse, Pol Vilain
  • Patent number: 4536587
    Abstract: A compound of the formula ##STR1## in which R.sup.1 represents a hydrogen or halogen atom or an alkyl radical,R.sup.2 represents a hydrogen or halogen atom,X represents an oxygen or sulphur atom,Y represents a hydrogen or halogen atom or an alkyl or halogenoalkyl radical andA represents an alkylene radical which is substituted by fluorine and optionally additionally substituted by chlorine,which possesses insecticidal activity.
    Type: Grant
    Filed: May 12, 1983
    Date of Patent: August 20, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Albrecht Marhold, Ingeborg Hammann, Ingomar Krehan, Wilhelm Stendel
  • Patent number: 4486447
    Abstract: Bis-sulfenylated bis-carbamate compounds exhibit activity against insect and mite pests.
    Type: Grant
    Filed: June 24, 1983
    Date of Patent: December 4, 1984
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4471127
    Abstract: The novel 1-(2,3-dihydro-1,4-benzodioxin-2S-yl)-5-(2,3-dihydro-1,4-benzodioxin-2R-yl )-3-azapentane-1R,5S-diol, and pharmaceutically acceptable acid addition salts thereof, are efficacious antihypertensive and bradycardic agents. Pharmaceutical compositions, methods of preparation and novel intermediates are described.
    Type: Grant
    Filed: August 26, 1982
    Date of Patent: September 11, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Charles F. Huebner, Heinz W. Gschwend
  • Patent number: 4471128
    Abstract: The novel 1-(2,3-dihydro-1,4-benzodioxin-2S-yl)-5-(2,3-dihydro-1,4-benzodioxin-2R-yl )-3-azapentane-1R,5S-diol, and pharmaceutically acceptable acid addition salts thereof, are efficacious antihypertensive and bradycardic agents. Pharmaceutical compositions, methods of preparation and novel intermediates are described.
    Type: Grant
    Filed: August 26, 1982
    Date of Patent: September 11, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Charles F. Huebner, Heinz W. Gschwend
  • Patent number: 4456614
    Abstract: The present invention concerns chemical compounds of the general formula: ##STR1## in which: R.sub.1 and R.sub.2 may be identical or different and represent a hydrogen or halogen atom or else a lower alkyl, lower alkoxy, nitro or acetyl group andR represents a lower alkyl or lower aralkyl group, such as benzyl.These compounds are useful in therapy for the treatment of hypertension and cardiac arrhythmia.
    Type: Grant
    Filed: April 2, 1981
    Date of Patent: June 26, 1984
    Assignee: Pierre Fabre S.A.
    Inventors: Gilbert Mouzin, Henri Cousse, Pol Vilain
  • Patent number: 4438131
    Abstract: .omega.-Cyano-1,.omega.-diphenyl-azaalkane derivatives of the formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, m and n have the meanings given in the description, and salts thereof with physiologically tolerated acids, are useful in treating cardiovascular disorders.
    Type: Grant
    Filed: March 30, 1982
    Date of Patent: March 20, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Oskar Ehrmann, Manfred Raschack, Josef Gries, Rolf Kretzschmar, Hans D. Lehmann, Ludwig Friedrich, Dirk Wuppermann, Frank Zimmermann, Werner Seitz, Hans J. Treiber, Ferdinand Dengel, Wolfram Frank, Hans-Georg Kurbjuweit, Claus D. Mueller
  • Patent number: 4436914
    Abstract: Compounds of the formula ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein:n is an integer equal to 0, 1, 2 or 3;R.sup.1 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenyl lower alkyl;each R is independently hydrogen, lower alkyl, optionally substituted phenyl, or optionally substituted phenyl lower alkyl;are .alpha..sub.2 blockers, and, therefore, are useful in treating essential hypertension and depression, and in inhibiting platelet aggregation.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: March 13, 1984
    Inventors: Arthur F. Kluge, Arthur M. Strosberg, Roger L. Whiting, George A. Christie
  • Patent number: 4423237
    Abstract: Novel compounds are disclosed having the formula ##STR1## in which R is selected from the group consisting of alkoxy having from 1 to 6 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, alkyl having from 1 to 6 carbon atoms, thioalkyl having from 1 to 6 carbon atoms, chloroalkyl having from 1 to 6 carbon atoms, alkynyl having from 2 to 6 carbon atoms and ##STR2## wherein R.sub.2 is alkyl having from 1 to 6 carbon atoms or alkoxy having from 1 to 6 carbon atoms, and R.sub.3 is hydrogen or alkyl having from 1 to 6 carbon atoms.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: December 27, 1983
    Assignee: Stauffer Chemical Company
    Inventor: Don R. Baker
  • Patent number: 4405639
    Abstract: Fluorine-containing phenylacetic acid esters of the formula ##STR1## in which R represents the radical of an alcohol customary in the case of pyrethroids,R.sup.1 represents C.sub.2-4 -alkyl, C.sub.2-4 -alkenyl or cyclopropyl,X represents H, halogen, alkyl, alkoxy, OCHF.sub.2, SCHF.sub.2, SCClF.sub.2 or SCF.sub.3 andX.sup.1 can vary widely or form a fused ring with X,the overall compound necessarily containing a fluorine atom, which compounds possess arthropodicidal properties. Intermediates therefor and an overall synthesis from an alcohol of the formula ROH and a toluene of the formula ##STR2## are also shown.
    Type: Grant
    Filed: May 3, 1982
    Date of Patent: September 20, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Erich Klauke, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel, Reinhard Lantzsch, Albrecht Marhold
  • Patent number: 4400389
    Abstract: Bis-sulfenylated bis-carbamate compounds exhibit activity against insect and mite pests.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: August 23, 1983
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4388322
    Abstract: Substituted 3-(1,2-dibromo-alkyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is halogen or optionally substituted phenyl or optionally substituted alkyl,R.sup.2 is hydrogen, halogen or optionally substituted alkyl, andY is the radical of an alcohol customary in pyrethroids, with the proviso that Y is a benzyloxy radical which is substituted by halogen and optionally substituted by at least one additional radical if R.sup.1 is halogen or methyl,which possess pesticidal properties. The acid moieties of such esters wherein R.sup.1 is optionally substituted phenyl are new compounds.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: June 14, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Wilhelm Stendel
  • Patent number: 4381398
    Abstract: New amino-alcohol derivatives and processes for production thereof are disclosed. These compounds exhibit .alpha. and .beta.-adrenergic receptor blocking activity or they act to increase the flow of blood of certain organs.
    Type: Grant
    Filed: March 18, 1980
    Date of Patent: April 26, 1983
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hiroshi Takizawa, Yoshimasa Oiji, Kazuhiro Kubo
  • Patent number: 4380653
    Abstract: The novel 1-(2,3-dihydro-1,4-benzodioxin-2S-yl)-5-(2,3-dihydro-1,4-benzodioxin-2R-yl )-3-azapentane-1R,5S-diol, and pharmaceutically acceptable acid addition salts thereof, are efficacious antihypertensive and bradycardic agents. Pharmaceutical compositions, methods of preparation and novel intermediates are described.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: April 19, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Charles F. Huebner, Heinz W. Gschwend
  • Patent number: 4360464
    Abstract: A process for the preparation of 1-aryloxy-3-aminopropane derivatives and acid addition salts thereof and such products per se the process comprising ring opening of tertiary azetidinol derivatives. They possess .beta.-adrenergic blocking activity and an activity of controlling secretion of gastric juice and are therefore useful antiulcerative medicines for peptic ulcer and duodenal ulcer.
    Type: Grant
    Filed: June 6, 1978
    Date of Patent: November 23, 1982
    Assignee: Teikoku Hormone Mfg. Co. Ltd.
    Inventors: Kunio Tsukamoto, Yasushi Suzuki, Akihiro Izumi, Yoshio Hiramatsu
  • Patent number: 4360690
    Abstract: 1-Aryl-cyclopropane-1-carboxylic acid esters of the formula ##STR1## in which R.sup.1 represents a hydrogen atom, a cyano radical or an alkyl, alkenyl or alkinyl radical within each case up to 7 carbon atoms, andR.sup.2 represents a phenyl radical which is substituted by halogen and/or optionally halogen-substituted phenoxy, with the proviso that the radical R.sup.2 in total contains at least one fluorine substituent,R.sup.3 and R.sup.4, which can be identical or different, represents a fluorine, chlorine or bromine atom or a methyl radical,R.sup.5 represents a hydrogen or halogen atom or a methyl or methoxy radical, andR.sup.6 represents a hydrogen or halogen atom, a cyano nitro or amino radical or an optionally halogen-substituted radical selected from C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy and C.sub.1 to C.sub.4 alkylthio,or whereinthe two radicals R.sup.5 and R.sup.6 together represent an optionally halogen-substituted C.sub.1 or C.sub.
    Type: Grant
    Filed: June 12, 1981
    Date of Patent: November 23, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
  • Patent number: 4348323
    Abstract: Fluorine-containing phenylacetic acid esters of the formula ##STR1## in which R represents the radical of an alcohol customary in the case of pyrethroids,R.sup.1 represents C.sub.2-4 -alkyl, C.sub.2-4 -alkenyl or cyclopropyl,X represents H, halogen, alkyl, alkoxy, OCHF.sub.2, SCHF.sub.2, SCClF.sub.2 or SCF.sub.3 andX.sup.1 can vary widely or form a fused ring with X, the overall compound necessarily containing a fluorine atom, which compounds possess arthropodicidal properties. Intermediates therefor and an overall synthesis from an alcohol of the formula ROH and a toluene of the formula ##STR2## are also shown.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: September 7, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Erich Klauke, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm St-Noel, Reinhard Lantzsch, Albrecht Harhold