Cyano Bonded Directly To The Hetero Ring Patents (Class 549/474)
  • Patent number: 6150397
    Abstract: The present invention relates to certain 5-aroylnaphthalene derivatives of formula (I): ##STR1## that are inhibitors of prostaglandin G/H synthase, pharmaceutical compositions containing them, methods for their use, and methods for preparing these compounds.
    Type: Grant
    Filed: June 21, 1999
    Date of Patent: November 21, 2000
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: David Mark Rotstein, Eric Brian Sjogren
  • Patent number: 6124344
    Abstract: The invention relates to the use of derivatives of F-type prostaglandins as ocular hypotensives. The compounds used in accordance with the invention are represented by the following formula I: ##STR1## wherein wavy line attachments indicate either the alpha (.alpha.) or beta (.beta.) configuration; hatched segments indicate a configuration; the solid triangle is used to indicate .beta. configuration; dashed bonds represent a double bond, or a single bond; R is a substituted heteroaryl radical having at least two pendant substituents selected from the group consisting of C.sub.1 to C.sub.6 alkyl; halogen; trifluoromethyl; COR.sup.1 ; COCF.sub.3 ; SO.sub.2 NR.sup.1 ; NO.sub.2 and CN or at least one cyano group; R.sup.1 is hydrogen or a lower alkyl radical having up to six carbon atoms, X is selected from the group consisting of --OR.sup.1 and --N(R.sup.1).sub.2 ; Y is .dbd.
    Type: Grant
    Filed: November 19, 1997
    Date of Patent: September 26, 2000
    Assignee: Allergan Sales, Inc.
    Inventor: Robert M. Burk
  • Patent number: 6063928
    Abstract: Novel compounds having the ability to inhibit 5-lipoxygenase enzyme and having the following formula I: ##STR1## and the pharmaceutically acceptable salts thereof, wherein Ar.sup.1 is a heterocyclic moiety which is selected from imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl, which is bonded to X.sup.1 through a ring nitrogen atom, and which may be optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C.sub.1-4 alkyl and the like; X.sup.1 is a direct bond or C.sub.1-4 alkylene; Ar.sup.2 is phenylene optionally substituted with halo, hydroxy, cyano, amino and the like; X.sup.2 is --A--X-- or --X--A-- wherein A is a direct bond or C.sub.1-4 alkylene and X is oxy, thio, sulfinyl or sulfonyl; Ar.sup.3 is phenylene, pyridylene, thienylene, furylene, oxazolylene or thiazolylene optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, C.sub.1-4 alkyl and the like; R.sup.1 and R.
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: May 16, 2000
    Assignee: Pfizer Inc
    Inventors: Rodney W. Stevens, Takashi Mano, Kazunari Nakao, Yoshiyuki Okumura
  • Patent number: 6057319
    Abstract: The invention encompasses the novel compound of formula (I) useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of formula (I).
    Type: Grant
    Filed: October 2, 1998
    Date of Patent: May 2, 2000
    Assignee: Merck Frosst Canada & Co.
    Inventors: Cameron Black, Serge Leger, Petpiboon Prasit, Zhaoyin Wang, Pierre Hamel, Yongxin Han, Gregory Hughes
  • Patent number: 6057342
    Abstract: The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula I: ##STR1## or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(.dbd.NH)NH.sub.2 and the other H, and J.sup.1 and J.sup.2 may be O or CH.sub.2, which are useful as inhibitors of factor Xa.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: May 2, 2000
    Assignee: Dupont Pharmaceutical Co.
    Inventors: John Matthew Fevig, Donald Joseph Phillip Pinto, Mimi Lifen Quan, Petrus Fredericus Wilhelmus Stouten
  • Patent number: 6005113
    Abstract: The invention relates to fluorescent dyes that are substituted or unsubstituted derivatives of 1-(isoindolyl)methylene-isoindole that are bound through both isoindole nitrogens to a boron difluoride moiety, forming a fluorescent dibenzopyrrometheneboron difluoride compound ##STR1## that is further substituted by bathochromic substituents that are aryl or heteroaryl moieties further substituted by an additional aryl or heteroaryl, that is itself optionally further substituted by an additional aryl or heteroaryl. These aryl and heteroaryl groups are separated by a covalent bond, or by an ethenyl, butadienyl or hexatrienyl linkage. The dyes of the invention are particularly useful as labels for carriers, particularly polymeric microparticles. The resulting microparticles have a long-wavelength fluorescence emission, and possess utility for tracing flow in biological systems, particularly in tracing blood flow.
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: December 21, 1999
    Assignee: Molecular Probes, Inc.
    Inventors: Yexin Wu, Dieter H. Klaubert, Hee Chol Kang, Yu-Zhong Zhang
  • Patent number: 5922767
    Abstract: Disclosed herein are substituted benzylurea derivatives represented by the following general formula (1): ##STR1## wherein R.sup.1 and R.sup.2 are independently H, a halogen atom, or an alkyl or alkoxyl group, R.sup.3 is a phenyl or heterocyclic group which may be substituted, n is an integer of 1-6, and R.sup.4 is a phenyl group which may be substituted, or salts thereof, and medicines comprising such a derivative as an active ingredient. The derivatives or salts thereof strongly inhibit only ACAT in macrophages and are hence useful as prophylactic and therapeutic agents for arteriosclerosis.
    Type: Grant
    Filed: October 7, 1997
    Date of Patent: July 13, 1999
    Assignee: SS Pharmaceutical Co., Ltd.
    Inventors: Yoshihiko Kanamaru, Hiroyuki Hirota, Akihiro Shibata, Teruo Komoto, Hiroyuki Naito, Koichi Tachibana, Mari Ohtsuka, Fumio Ishii, Susumu Sato
  • Patent number: 5883106
    Abstract: Novel compounds having the ability to inhibit 5-lipoxygenase enzyme and having the following formula I: ##STR1## and the pharmaceutically acceptable salts thereof, wherein Ar.sup.1 is a heterocyclic moiety which is selected from imidazolyl, pyrrolyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, indolyl, indazolyl and benzimidazolyl, which is bonded to X.sup.1 through a ring nitrogen atom, and which may be optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino, and C.sub.1-4 alkyl; X.sup.1 is a direct bond or C.sub.1-4 alkylene; Ar.sup.2 is phenylene optionally substituted with halo, hydroxy, cyano, and amino X.sup.2 is --A--X-- or --X--A-- wherein A is a direct bond or C.sub.1-4 alkylene and X is oxy, thio, sulfinyl or sulfonyl; Ar.sup.3 is phenylene, pyridylene, thienylene, furylene, oxazolylene or thiazolylene optionally substituted with one or two substituents selected from halo, hydroxy, cyano, amino and C.sub.1-4 alkyl; R.sup.1 and R.sup.2 are each C.sub.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: March 16, 1999
    Assignee: Pfizer Inc.
    Inventors: Rodney W. Stevens, Takashi Mano, Kazunari Nakao, Yoshiyuki Okumura
  • Patent number: 5824691
    Abstract: Guanidine derivatives of the formula: ##STR1## wherein Y is C--R.sup.1(in which R.sup.1 is hydrogen, lower alkyl, hydroxy, protected hydroxy, etc.,)R.sup.2 is pyrrolyl, tetrazolyl, pyrazolyl, etc.,R.sup.3 is hydrogen, lower alkoxy, hydroxy, protected hydroxy, etc.,Z is C--R.sup.4(in which R.sup.4 is hydrogen, carboxy, protected carboxy, nitro, halogen, hydroxy(lower)alkyl, etc.,), andW is R.sup.12(in which R.sup.12 is hydrogen, lower alkoxy, nitro, hydroxy or protected hydroxy)and pharmaceutically acceptable salts thereof which are useful as a medicament which are useful in inhibiting Na.sup.+ /H.sup.+ exchange in cells and in the prevention of cardiovascular diseases, cerebrovascular diseases, renal diseases, arteriosclerosis and shock.
    Type: Grant
    Filed: November 9, 1995
    Date of Patent: October 20, 1998
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Atsushi Kuno, Yoshikazu Inoue, Hisashi Takasugi, Hiroaki Mizuno, Kumi Yamasaki
  • Patent number: 5693667
    Abstract: A compound, composition, and method for controlling Take-all disease of plants by applying a fungicide of the formula: ##STR1## wherein Z.sub.1 and Z.sub.2 are carbons of a furan ring; A is selected from the group consisting of --C(X)-amine wherein the amine is substituted with a first and a second amine substituent or with an alkylaminocarbonyl and a hydrogen, --C(O)--SR.sub.3 ; --NH--C(X)R.sub.4, and --C(.dbd.NR.sub.3)--XR.sub.7 ;B is --W.sub.m --Q(R.sub.2).sub.3 or selected from o-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ; Q is C, Si, Ge, or Sn; W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W may also be selected from --N(R.sub.3).sub.m H.sub.(1-m) --, --S(O).sub.p --, and --O--; X is O or S; n is 0, 1, or 2; m is 0 or 1; p is 0, 1, or 2;wherein two R.sub.
    Type: Grant
    Filed: December 28, 1994
    Date of Patent: December 2, 1997
    Assignee: Monsanto Company
    Inventors: Dennis Paul Phillion, Diane Susan Braccolino, Matthew James Graneto, Wendell Gary Phillips, Karey Alan Van Sant, Daniel Mark Walker, Sai Chi Wong
  • Patent number: 5665763
    Abstract: Compounds of the formula ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the specification,Y is alkylene of 3 to 9 carbon atoms,R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle chosen from benzoxazolyl, benzathiazolyl, thiadiazolyl, imidazolyl, dihydroimidazolyl, oxazolyl, thiazolyl, oxadiazolyl, pyrazolyl, oxazolinyl, isoxazolyl, isothiazolyl, furyl, triazolyl, thiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or any of the above substituted with alkyl, alkoxyalkyl, cycloalkyl, halo alkyl, hydroxyalkyl, alkoxy, hydroxy, halo, furyl, thienyl, fluoroalkyl;or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.
    Type: Grant
    Filed: August 30, 1996
    Date of Patent: September 9, 1997
    Assignee: Sanofi, S.A.
    Inventors: David J. Aldous, Thomas R. Bailey, Guy Dominic Diana, Theodore J. Nitz
  • Patent number: 5591833
    Abstract: Colorants and compositions useful as a fugitive or permanent colorant for a variety of substrates, or as intermediates for their manufacture, and having one or more improved properties of enhanced aqueous washability, compatibility with and non-extractibility from thermoplastic resins, or reactivity with resins having reactive functionality, said composition having the formula C(Z).sub.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: January 7, 1997
    Assignee: Milliken Research Corporation
    Inventors: John B. Hines, David J. Moody, Edward W. Kluger
  • Patent number: 5506243
    Abstract: Since sulfonamide derivatives of the present invention show strong inhibitory activity against cysteine protease such as calpain papain, cathepsin B, cathepsin H, cathepsin L, they can be used as remedies for muscular dystrophy, cataract, myocardial infarction, stroke, Alzheimer's disease, amyotrophia, osteoporosis, hypercalcemia or the like.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: April 9, 1996
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Toshiro Sakaki, Chizuko Takahashi, Yoshiyuki Fujimura
  • Patent number: 5416235
    Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: May 16, 1995
    Assignee: Octel Chemicals Limited
    Inventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
  • Patent number: 5387747
    Abstract: The present invention relates to the derivatives of the formula ##STR1## and their tautomeric forms, as well as their addition salts, and to their use in therapeutics, especially for the treatment and prevention of cardiovascular diseases and in particular for the treatment of hypertension, cardiac insufficiency and diseases of the arterial wall, especially atherosclerosis.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: February 7, 1995
    Assignee: Laboratoires Upsa
    Inventors: Nicole Bru-Magniez, Timur Gungor, Jean-Marie Teulon
  • Patent number: 5364869
    Abstract: Compounds are disclosed having the formula: ##STR1## wherein D is a substituted heterocycle, especially substituted pyridyl, E-G is a linking group, especially --N(R.sub.5)--CH.sub.2 --, and Q is a substituted phenyl or substituted heterocyclic group, especially substituted benzothiopene. The compounds of the invention are angiotensin II receptor antagonists.
    Type: Grant
    Filed: January 7, 1993
    Date of Patent: November 15, 1994
    Assignee: Abbott Laboratories
    Inventor: Biswanath De
  • Patent number: 5330965
    Abstract: Cyclohexenone oxime ethers of the formula I ##STR1## (R.sup.1 =C.sub.1 -C.sub.6 -alkyl; A=substituted or unsubstituted alkylene or alkenylene;Z=a 5-membered or 6-membered heteroaromatic structure;X=substituted or unsubstituted amino, nitro, cyano, halogen, 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 phenyl;n=0 to 3, or 1 to 4 where Z is halogen-substituted pyridyl; andR.sup.
    Type: Grant
    Filed: January 15, 1993
    Date of Patent: July 19, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Thomas Kuekenhoehner, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
  • Patent number: 5274072
    Abstract: Provided are certain novel substituted 2(5H)furanone compounds which are useful as ultraviolet/visible light absorbing compounds. Also provided are polyester compositions having such compounds copolymerized therein and shaped or formed articles comprised of such polyester compositions.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: December 28, 1993
    Assignee: Eastman Kodak Company
    Inventors: Max A. Weaver, James J. Krutak, Clarence A. Coates, Jr., William W. Parham, Wayne P. Pruett, Samuel D. Hilbert
  • Patent number: 5258357
    Abstract: Carboxamides of the formulae Ia to Ic ##STR1## where X is oxygen or sulfur;R.sup.1 is hydrogen or substituted or unsubstituted cycloalkyl or alkyl;R.sup.2 is hydroxy, alkoxy, cyanoalkyl, substituted or unsubstituted alkenyl, alkynyl, phenyl or naphthyl, a substituted or unsubstituted 5- to 6-membered heterocyclic structure or one of the groups stated for R.sup.1, orR.sup.1 and R.sup.2 together are a 4- to 7-membered chain which contains, in addition to methylene groups, one of the following groups as ring member: oxygen, sulfur, N-methyl or carbonyl;R.sup.3 and R.sup.4 are each nitro, cyano, halogen, substituted or unsubstituted amino, alkoxy, alkylthio, a substituted or unsubstituted 5- to 6 -membered heterocyclic structure, substituted or unsubstituted alkenyl, alkynyl, phenyl, phenoxy or phenylthio, or one of the groups stated for R.sup.1 ;R.sup.5 is formyl, 4,5-dihydrooxazol-2-yl or COYR.sup.6 (Y=O,S);R.sup.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: November 2, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Muenster, Gerd Steiner, Wolfgang Freund, Bruno Wuerzer, Karl-Otto Westphalen
  • 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: 5217991
    Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from cycloalkyl and cycloalkylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloalkylalkyl group contains one to about eight carbon atoms; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl: wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: June 8, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
  • Patent number: 5216013
    Abstract: Non-peptidyl compounds characterized generally as heterocyclic acyl aminodiol .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are compounds of the formula ##STR1## wherein R.sub.1 is selected from aryl and aralkyl groups represented by ##STR2## and wherein R.sub.1 may be further selected from heteroaryl and heteroaralkyl represented by ##STR3## wherein each of T and A is independently selected from N and CH; wherein n is a number selected from zero through five, inclusive; wherein X is selected from oxygen atom, methylamino and NH; wherein each of Y and Z is independently selected from chloro, fluoro, methoxy and dimethylamino; wherein Q is oxygen atom; and wherein each of T and A is independently selected from N and CH; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is selected from methyl and ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; wherein R.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: June 1, 1993
    Assignee: G. D. Searle & Co.
    Inventor: Gunnar J. Hanson
  • Patent number: 5190573
    Abstract: Cyclohexenone oxime ethers ##STR1## where R.sup.1 is alkyl;A is substituted or unsubstituted alkylene or alkenylene, where methylene is replaced by an oxygen atom, a sulfur atom, a sulfoxyl group, a sulfonyl group or --NR.sup.a --,Z is phenyl or a 5- or 6-membered heteroaromatic structure;X is substituted or unsubstituted amino, nitro, cyano, halogen, 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 benzyloxycarbony or phenyl;n is 0 to 3, or 1 to 5 where X is halogen;R.sup.
    Type: Grant
    Filed: May 8, 1991
    Date of Patent: March 2, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
  • Patent number: 5145975
    Abstract: The present invention relates to the treatment of diseases caused by invading organisms in a host by first identifying an enzymatic difference between the host and the invading organism and then administering to the host a pharmaceutically effective amount of a subversive substrate for the differing enzyme of the invading organism, whereby the action of the differing enzyme causes a result counter to the intended result and function of the enzyme that results in its debilitation or death. In particular, treatment of parasitic diseases caused by kinetoplastids including trypanosomes and leishmanias, e.g., African sleeping sickness, Chagas' disease, oriental sore and kala-azar is accomplished by administration of a pharmaceutically effective antiparasitic amount of a competitive toxigenic substrate for trypanothione reductase. Methods of treatment and compositions therefor contain a competitive toxigenic substrate for trypanothione reductase. Numerous compounds and corresponding compositions are disclosed.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: September 8, 1992
    Assignee: The Rockefeller University
    Inventors: Graeme B. Henderson, Peter C. Ulrich, Anthony Cerami
  • Patent number: 5102905
    Abstract: The invention concerns heterocyclic nitromethane derivatives of the formula 1 as defined hereinafter (and their non-toxic salts) wherein the heterocyclic moiety Q is thienyl, benzothienyl or dibenzothienyl and may bear a wide variety of optional substituents, together with pharmaceutical compositions containing them. The nitromethane derivatives are inhibitors of the enzyme aldose reductase and are of value in the treatment of certain complications of diabetes and galactosemia.
    Type: Grant
    Filed: April 28, 1989
    Date of Patent: April 7, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey Morris, John Preston
  • Patent number: 5055471
    Abstract: This invention relates to derivatives of propanoic acid of the formula ##STR1## Useful as fungicides, insecticides and miticides, to processes for preparing them, to compositions containing them, and to methods of using them to combat fungi, especially fungal infections of plants, and to kill or control insects and mites.
    Type: Grant
    Filed: November 15, 1989
    Date of Patent: October 8, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul J. de Fraine, Anne Martin
  • Patent number: 5039685
    Abstract: Novel O-alkylated oximes of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are optionally substituted aromatic or heteroaromatic rings, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is a nitrogen containing, substituted ring or an amino group carrying a substituted ring, and n and m independently are 0, 1 or 2, are potent inhibitors of GABA reuptake from the synaptic cleft.
    Type: Grant
    Filed: May 10, 1989
    Date of Patent: August 13, 1991
    Assignee: Novo Nordisk A/S
    Inventors: Lars J. S. Knutsen, Knud E. Andersen, Anker S. Jorgensen, Ursula Sonnewald
  • Patent number: 4942170
    Abstract: The present invention relates to the treatment of diseases caused by invading organisms in a host by first identifying an enzymatic difference between the host and the invading organism and then administering to the host a pharmaceutically effective amount of a subversive substrate for the differing enzyme of the invading organism, whereby the action of the differing enzyme causes a result counter to the intended result and function of the enzyme that results in its debilitation or death. In particular, treatment of parasitic diseases caused by kinetoplastids including trypanosomes and leishmanias, e.g., African sleeping sickness, Chagas' disease, oriental sore and kala-azar is accomplished by administration of a pharmaceutically effective antiparasitic amount of a competitive toxigenic substrate for trypanothione reductase. Methods of treatment and compositions therefor contain a competitive toxigenic substrate for trypanothione reductase. Numerous compounds and corresponding compositions are disclosed.
    Type: Grant
    Filed: May 27, 1988
    Date of Patent: July 17, 1990
    Assignee: The Rockefeller University
    Inventors: Graeme B. Henderson, Peter C. Ulrich, Anthony Cerami
  • Patent number: 4920231
    Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: April 24, 1990
    Assignee: Roussel Uclaf
    Inventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4908452
    Abstract: A facile and mild process for the preparation of nitriles from reagent sensitive primary carboxamides is described. The process utilizes a (carboxysulfamoyl)ammonium hydroxide compound as the dehydrating agent. It is useful for preparing nitriles which have present other groups which are sensitive to the more conventional methods of dehydration or to other methods of nitrile synthesis. Some novel nitriles prepared by the new method are also described.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: March 13, 1990
    Assignee: Merck & Co., Inc.
    Inventor: David A. Claremon
  • 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: 4798892
    Abstract: The present invention relates to compounds of the general formula ##STR1## wherein Ar represents a substituted or unsubstituted heterocyclic group; W represents alkylene of from 1 to about 10 carbon atoms; and B represents --NR.sub.2 COR.sub.1, --NR.sub.2 CONR.sub.1 R.sub.3, --NR.sub.2 SO.sub.2 R.sub.1, NR.sub.2 SO.sub.2 NR.sub.1 R.sub.3, or --NR.sub.2 COOR.sub.1, wherein R.sub.1, R.sub.2 and R.sub.3 may be alike or different and may be hydrogen, alkyl, alkoxyalkyl cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.1 is not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.1 or --NR.sub.2 COOR.sub.1, or R.sub.1 and R.sub.3 may together with N form a 5 to 7 membered heterocyclic group and the pharmaceutically acceptable salts thereof. The compounds exhibit beta-adrenergic blocking activity and are also useful in the treatment of glaucoma.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: January 17, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Sheung T. Kam, William L. Matier, Ghanshyam Patil, Khuong H. X. Mai
  • Patent number: 4792606
    Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: December 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Hermann-Dieter Krall
  • Patent number: 4791123
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: December 13, 1988
    Assignee: Schering Akt.
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
  • Patent number: 4785109
    Abstract: These is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.
    Type: Grant
    Filed: January 30, 1987
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Werner Fory, Werner Topfl
  • Patent number: 4701527
    Abstract: A method of synthesizing with improved reaction kinetics and improved effective yields salicylamide compounds of the formula: ##STR1## wherein R.sub.1 is a substituent selected from the group consisting of --H, --COC.sub.n H.sub.2n+1 and --C.sub.n H.sub.2n+1 wherein n is an integer with a value of from 1 through to about 15, R.sub.2 is a substituent selected from the group consisting of --H, --CN, --NO.sub.2, --F, --Cl, --Br, --I, --CF.sub.3, --CBr.sub.3, --CCl.sub.3, --CI.sub.3 and R.sub.1 and R.sub.3 is an R.sub.2 substituted heterocyclic compound selected (e.g.) from the group consisting of furan, thiazole, benzothiazole and purine which comprises reacting a phenyl salicylate ester bearing an R.sub.1 substituent on the benzene ring of the salicylic acid portion thereof with an R.sub.2 substituted aniline or a heterocyclic amine NH.sub.2 --R.sub.
    Type: Grant
    Filed: November 20, 1984
    Date of Patent: October 20, 1987
    Assignee: Lever Brothers Company
    Inventors: Gerald S. Koermer, Eddie N. Gutierrez, Maryfrances Prorok
  • Patent number: 4681952
    Abstract: A process for the preparation of 2,2-dimethyl-3-arylcyclopropanecarboxylic acid or ester of the formula ##STR1## in which Ar is naphthyl or the radical ##STR2## R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, Z is oxygen, sulphur, or 1,2-ethenediyl, andR.sup.2 represents hydrogen, halogen, cyano, nitro or trialkylsilyl or a radical, which is optionally substituted by halogen, from the series comprising alkyl, cycloalkyl, alkenyl, alkoxy, alkylenedioxy, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylamino, phenyl and phenoxy,comprising reacting a 1-aryl-1-halogeno-2,2-dimethyl-3-butanone of the formula ##STR3## in which X.sup.1 is chlorine or bromine, with a base in the presence of a diluent at a temperature between about -20.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-arylcyclobutanone of the formula ##STR4## and reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +50.degree. C.
    Type: Grant
    Filed: November 7, 1984
    Date of Patent: July 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
  • Patent number: 4663465
    Abstract: 2,2-Dimethyl-3-arylcyclopropanecarboxylic acids and esters, suitable as insecticide intermediates, of the formula ##STR1## in which Ar is naphthyl or substituted furyl, thienyl or phenyl, andR.sup.1 is hydrogen or alkyl, are produced by subjecting ##STR2## to radical polymerization to produce ##STR3## reacting that with chlorine or bromine to produce ##STR4## and reacting that with an alkali metal or alkaline earth metal hydroxide or carbonate. Various intermediates II and III are new.
    Type: Grant
    Filed: December 4, 1985
    Date of Patent: May 5, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
  • Patent number: 4643849
    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 compounds, a process for the preparation thereof and an anti-ulcer agent containing the same.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: February 17, 1987
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Shiro Hirai, Hiroshi Hirano, Hirotoshi Arai, Yasuo Kiba, Hisanari Shibata, Yoshikazu Kusayanagi, Minako Yotsuji, Kazuhiko Hashiba, Kikuko Tanada
  • Patent number: 4643758
    Abstract: N-(Substituted heterocyclic)-2-pyrrolidinone derivatives useful as herbicides both alone and in combination with other herbicides.
    Type: Grant
    Filed: November 8, 1984
    Date of Patent: February 17, 1987
    Assignee: Eli Lilly and Company
    Inventors: Kenneth W. Burow, Jr., James C. Williams, Jr.
  • Patent number: 4522950
    Abstract: 2,4,5-Trisubstituted-2,3-dihydrofurans useful for fungicidal applications are provided herein. The 2,3-dihydrofuran compounds correspond to the general formula ##STR1## where R is an ethyl or vinyl group, R.sub.1 is a C.sub.1-10 hydrocarbon radical and X is a nitrile, amide or sulfonyl group. The compounds of this invention are effective fungicides for the treatment of seeds and also find use in other agricultural fungicidal applications.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: June 11, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventors: Allen L. Hall, Richard G. Fayter, Jr.
  • Patent number: 4493936
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or alkyl; n is 0 or 1 and R is an unsaturated moiety, are useful as herbicides and plant growth regulators.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: January 15, 1985
    Assignee: Shell Oil Company
    Inventor: Willy D. Kollmeyer
  • Patent number: 4487946
    Abstract: A process is provided wherein cyclopropyl ketones are readily isomerized to 2,3-dihydrofurans. The process involves the thermal rearrangement of 1,1-disubstituted-2-alkylcyclopropanes or 1,1-disubstituted-2-alkenylcyclopropanes, wherein one of the substituents in the 1-position is an acyl group, to 2,4,5-trisubstituted-2,3-dihydrofurans employing an onium compound as the catalyst.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: December 11, 1984
    Assignee: National Distillers and Chemical Corporation
    Inventors: Allen L. Hall, Richard G. Fayter, Jr.
  • Patent number: 4439225
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are H or alkyl; n is 0 or 1 and R is an unsaturated moiety, are useful as herbicides and plant growth regulators.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: March 27, 1984
    Assignee: Shell Oil Company
    Inventor: Willy D. Kollmeyer
  • Patent number: 4412856
    Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: November 1, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
  • Patent number: 4388469
    Abstract: Diphenylalkanoether and diphenylalkanone oxime-ether derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each independently an aryl group optionally substituted with 1 to 3 substituents selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro, cyano, di(C.sub.1 -C.sub.4)alkylamino, amino, benzyloxy, hydroxyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkanoylamino, C.sub.1 -C.sub.4 alkylamino and N-(C.sub.1 -C.sub.4)alkyl-N-(C.sub.1 -C.sub.4)alkanoylamino, Z.sup.1 is a group of the formula: ##STR2## (wherein R.sup.3 and R.sup.4 are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or an ar(C.sub.1 -C.sub.
    Type: Grant
    Filed: April 2, 1980
    Date of Patent: June 14, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Hajime Kawakami, Junki Katsube
  • Patent number: 4372776
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.3 each is hydrogen or R.sup.1 and R.sup.3 together form a second carbon-to-nitrogen bond, R.sup.2 is hydrogen or cyano, R.sup.4 is alkyl and Ar is one of certain aromatic moieties.The compounds can be used as abscission agents for the loosening of fruit and/or leaves on plants.
    Type: Grant
    Filed: October 16, 1981
    Date of Patent: February 8, 1983
    Assignee: Shell Oil Company
    Inventors: Janet A. Day, Robert J. G. Searle
  • Patent number: 4366102
    Abstract: In a process for the preparation of an aromatic chloroformic acid ester by contacting a phenol and phosgene, the improvement wherein the reaction is carried out in a homogeneous liquid phase at a temperature of 60.degree. to 180.degree. C. in the presence of organic phosphorus compound of the formulaR.sup.1 R.sup.2 R.sup.3 PR.sup.4.sub.n X.sub.nin whichR.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, alkyl, alkenyl, aralkyl, aryl or halogen and two of the said radicals together with the phosphorus atom can form a 5-membered or 6-membered phosphorus-containing saturated or unsaturated heterocyclic radical,X represents OH, homopolar-bonded halogen or an inorganic or organic acid anion,R.sup.4 denotes hydrogen or alkyl or, if X denotes halogen, can also denote halogen and n denotes 0 or 1,and in which, furthermore,R.sup.4 and X together can represent oxygen or sulfur.
    Type: Grant
    Filed: May 6, 1981
    Date of Patent: December 28, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Rauchschwalbe, Heinz U. Blank, Karl Mannes, Dietmar Mayer