Oxy Or Halogen Containing Patents (Class 568/43)
  • Publication number: 20030055288
    Abstract: The present invention relates to a process for producing a bis(4-hydroxy-3-nitrophenyl) compounds, characterized by nitrating a bis(4-hydroxyphenyl) compound wherein two phenyl groups are bonded to each other directly or through an electron-donating bridging group, sulfoxide group, sulfone group or carbonyl group in an inert solvent using nitric acid under the condition of substantially free from any other acid. According to the process, the target compounds reduced in the content of trinitrates can be produced in high yield and further recrystallizing the compound easily gives in high yield a high-purity products suitable for use as a raw material of producing a heat-resistant polymer and so on because the content of a trinitro-substitued compound in that compound is low.
    Type: Application
    Filed: October 10, 2002
    Publication date: March 20, 2003
    Inventors: Eiichi Tanaka, Masaki Fujimoto
  • Patent number: 6525225
    Abstract: A process for preparing compounds of the formula: wherein R2 is lower alkyl; or phenyl optionally substituted by from one to five groups, the same or different, which are lower alkyl, lower haloalkyl, halogen or —SR4; R3 is halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, —S-alkyl, cycloalkyl having from 3 to 7 carbon atoms in the ring, alkenyl or alkynyl having from 3 to 7 carbon atoms, or —(CR5R6)—SR2 wherein q is one or two; R4 is lower alkyl; R5 and R6 independently represent hydrogen, lower alkyl or lower haloalkyl; and n is zero or an integer from one to three; intermediate compounds of the formula: and processes for preparing them.
    Type: Grant
    Filed: November 23, 2001
    Date of Patent: February 25, 2003
    Assignee: Rhone Poulenc Agrochimie
    Inventors: Virginie Pevere, Alain Gadras, Susan Mary Cramp, Charles Walter Ellwood
  • Publication number: 20020103389
    Abstract: The invention relates to compounds of formula I 1
    Type: Application
    Filed: December 4, 2001
    Publication date: August 1, 2002
    Inventors: Sabine Haag, Herbert Kogler, Ziyu Li, Laszlo Vertesy
  • Patent number: 6368769
    Abstract: Novel aromatic sulfonium compounds of general formula (I), photoacid generators comprising the same, and photopolymerizable compositions containing the same, capable of providing stereolithographic resin compositions which do not suffer from the hindrance to curing by oxygen, can easily give shaped articles having desired sizes by virtue of the high accuracy thereof in curing, and can attain a satisfactory curing depth owing to the high sensitivity thereof for radiant energy; and a stereolithographic process.
    Type: Grant
    Filed: July 6, 2000
    Date of Patent: April 9, 2002
    Assignee: Asahi Denki Kogyo Kabushiki Kaisha
    Inventors: Kazuo Ohkawa, Hiroyuki Tachikawa, Satoyuki Chikaoka
  • Patent number: 6350892
    Abstract: Selective inhibitors of the cPLA2 enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula where (R′), p, D, Y, Z, Ra, Rb and A are as defined in the specification.
    Type: Grant
    Filed: February 18, 2000
    Date of Patent: February 26, 2002
    Assignee: Bristol-Myers Squibb Company
    Inventors: Jacques Banville, Yonghua Gai, Graham Johnson, Fred Christopher Zusi, James R. Burke
  • Patent number: 6281391
    Abstract: This invention encompasses a novel process for synthesizing compounds represented by formula A: These compounds are intermediates useful in the preparation of certain agents that are selective COX-2 inhibitors.
    Type: Grant
    Filed: October 27, 1999
    Date of Patent: August 28, 2001
    Assignees: Merck & Co., Inc., Merck Frosst Canada & Co.
    Inventors: Richard D. Tillyer, Ian W. Davies, Robert D. Larsen, Xin Wang, Paul O'Shea, Anthony On-Ping King, Dalian Zhao, Cheng Y. Chen, Edward J. J. Grabowski
  • Publication number: 20010012907
    Abstract: A halogenated substituted cyclopentene derivative of formula (I): 1
    Type: Application
    Filed: February 1, 2001
    Publication date: August 9, 2001
    Applicant: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 6235942
    Abstract: A process for preparing compounds of the formula: wherein R2 is lower alkyl; or phenyl optionally substituted by from one to five groups, the same or different, which are lower alkyl, lower haloalkyl, halogen or —SR4; R3 is halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, —S-alkyl, cycloalkyl having from 3 to 7 carbon atoms in the ring, alkenyl or alkynyl having from 3 to 7 carbon atoms, or -(CR5R6)—SR2 wherein q is one or two; R4 is lower alkyl; R5 and R6 independently represent hydrogen, lower alkyl or lower haloalkyl; and n is zero or an integer from one to three; intermediate compounds of the formula: and processes for preparing them.
    Type: Grant
    Filed: October 28, 1998
    Date of Patent: May 22, 2001
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Virginie Pevere, Alain Gadras, Susan Mary Cramp, Charles Walter Ellwood
  • Patent number: 6229049
    Abstract: The invention relates to a process for preparing a difluoroacetophenone derivative (4) by alkylthionating a compound (1) into a compound (2) and reacting this compound with a compound (3). wherein X1 is Cl, Br or I, X2 and X3 are independently a halogen atom, H or perfluoroalkyl group, X4 is a halogen atom, R1 is an alkyl, aryl or aralkyl group, and R2 is methyl, ethyl or cyclopropyl group.
    Type: Grant
    Filed: January 21, 2000
    Date of Patent: May 8, 2001
    Assignee: SSP Co., Ltd.
    Inventors: Sunao Takeda, Yasushi Kaneko, Hiromichi Eto, Susumu Sato
  • Patent number: 6225505
    Abstract: The present invention lies in a process for producing a trifluoromethylthiomethylbenzene derivative represented by the following general formula (2): (wherein R is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group, a nitro group, or a benzoyl group which may be substituted with halogen atom, alkyl group, alkoxy group, aliphatic or aromatic acyl group, nitro group, cyano group or alkoxycarbonyl group; n is an integer of 1 to 5; when n is an integer of 2 or more, a plurality of R's may be the same of each independently different), which process comprises reacting, in acetonitrile, a benzyl halide derivative represented by the following general formula (1): (wherein R and n have the same definitions as given above; and X is a halogen atom, an alkylsulfonyloxy group or an arylsulfonyloxy group which may be substituted with alkyl group or halogen atom) with thiophosgene and potassium fluoride.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: May 1, 2001
    Assignees: Ihara Chemical Industry Co., LTD, Kumiai Chemical Industry Co., LTD
    Inventors: Yoshikazu Kimura, Hidetaka Hiyoshi, Keiji Toriyabe, Nobuhide Wada
  • Patent number: 6204415
    Abstract: Described is a triazole derivative represented by the formula (1): wherein R1 represents a hydrogen atom, a lower alkyl group or an aralkyl group, X1 and X2 are the same or different and each independently represents a hydrogen atom, a halogen atom or a halogenoalkyl and n stands for an integer of 0 to 2, or salt thereof; a preparation process of said compound and a pharmaceutical comprising said compound as an effective ingredient. The compound as described above has high antimycotic activity and is useful for the prevention and treatment of mammalian mycotic infections.
    Type: Grant
    Filed: April 18, 2000
    Date of Patent: March 20, 2001
    Assignee: SSP Co., Ltd.
    Inventors: Sunao Takeda, Yasushi Kaneko, Minoru Tokizawa, Hiromichi Eto, Kazuya Ishida, Kazunori Maebashi, Masaru Matsumoto, Takemitsu Asaoka, Susumu Sato
  • Patent number: 6172266
    Abstract: Described is a triazole derivative represented by the formula (1): wherein R1 represents a hydrogen atom, a lower alkyl group or an aralkyl group, X1 and X2 are the same or different and each independently represents a hydrogen atom, a halogen atom or a halogenoalkyl and n stands for an integer of 0 to 2, or salt thereof; a preparation process of said compound and a pharmaceutical comprising said compound as an effective ingredient. The compound as described above has high antimycotic activity and is useful for the prevention and treatment of mammalian mycotic infections.
    Type: Grant
    Filed: December 23, 1999
    Date of Patent: January 9, 2001
    Assignee: SSP Co., Ltd.
    Inventors: Sunao Takeda, Yasushi Kaneko, Minoru Tokizawa, Hiromichi Eto, Kazuya Ishida, Kazunori Maebashi, Masaru Matsumoto, Takemitsu Asaoka, Susumu Sato
  • Patent number: 6100431
    Abstract: The preparation of aromatic ketones substituted with a thioether group at the ortho position is accomplished by the initial reaction of an aromatic nucleus substituted with a halide and an ortho nitro group with a nitroalkane in the presence of a hydroxide base. The resulting ortho-nitroalkyl nitroarene compound is converted to the corresponding ortho-nitroaryl ketone by an oxidative Nef reaction. The aromatic nitro group of the ortho-nitroaryl ketone is replaced with a thioether group by reaction with a thiolate anion, most preferably under phase-transfer conditions. Aromatic ketones may be used to prepare various pharmaceutical and herbicidal compounds.
    Type: Grant
    Filed: June 2, 1998
    Date of Patent: August 8, 2000
    Assignee: Eastman Chemical Company
    Inventor: Neil W. Boaz
  • Patent number: 6096930
    Abstract: The present invention relates to novel cyclohexane-1-3-dione derivatives of formula (1) useful as herbicides and plant-growth regulants, ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, nitro, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 sulfamoyl, and N, N-di(C.sub.1 -C.sub.6 alkyl)sulfamoyl group; (X)n represents the number of X substituents which may be substituted on benzene ring, wherein n is 1, 2 or 3. Also, cyclohexyl moiety, one of the substituents on benzofuran ring, is substituted at C-4, C-5, C-6 or C-7 position on benzene ring; R.sup.1 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl group; R.sup.2 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl and C.sub.2 -C.sub.6 alkynyl group; R.sup.3 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: August 1, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Eung Kul Ryu, Kyoung Mahn Kim, Jae Nyoung Kim, Jin Seog Kim
  • Patent number: 6080739
    Abstract: The present invention relates to colchicine and thiocolchicine derivatives which can be obtained from these molecules by functionalization of the C-7 to ketone or functionalization of the amino group. Said compounds have a marked antiblastic activity both on the normal cancer cells and on the chemoresistant phenotype. The compounds of the invention can be administered both by injection and orally.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: June 27, 2000
    Assignee: Indena S.p.A.
    Inventor: Ezio Bombardelli
  • Patent number: 6025328
    Abstract: The present invention provides illudin analogs of the general formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions comprising compounds of formula I, intermediates and processes useful for preparing compounds of formula I, and methods comprising inhibiting tumor growth or treating cancer by administering one or more compounds of formula I.
    Type: Grant
    Filed: February 20, 1998
    Date of Patent: February 15, 2000
    Assignee: The Regents of the University of California
    Inventors: Trevor C. McMorris, Michael J. Kelner
  • Patent number: 6013839
    Abstract: The invention relates to a process for preparing a 2-(thiosubstituted)-4-haloacetophenone such as those of formula (I), which comprises reacting a 2,4-dihaloacetophenone with a thiolating agent under substantially anhydrous conditions. In formula (I), R.sup.1 and R.sup.2 have the meanings given in the description and R.sup.3 is halogen. The compounds prepared are useful as intermediates in the preparation of herbicidally active compounds.
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: January 11, 2000
    Assignee: Rhone-Poulenc Agriculture Limited
    Inventor: Susan Mary Cramp
  • Patent number: 5998667
    Abstract: The invention relates to new substituted biphenyloxazolines of the formula (I) ##STR1## in which R.sup.1 represents C.sub.1 -C.sub.6 -halogenoalkylthio andR.sup.2 represents hydrogen, orR.sup.1 and R.sup.2 together with the carbon atoms to which they are bonded form a halogen-substituted 5- or 6-membered heterocyclic ring,X represents hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: December 7, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Albrecht Marhold, Christoph Erdelen
  • Patent number: 5986144
    Abstract: Described is a triazole derivative represented by the formula (1) or salt thereof, preparation process thereof, preparation intermediates represented by the formulas (2) and (3), and a pharmaceutical comprising the compound represented by the formula (1) or salt thereof. wherein n stands for 0, 1 or 2, X.sup.1 represents H or F and Y.sup.1 and Y.sup.2 each independently represents H, halogen or CF.sub.3.
    Type: Grant
    Filed: May 14, 1999
    Date of Patent: November 16, 1999
    Assignee: SS Pharmaceutical Co., Ltd.
    Inventors: Minoru Tokizawa, Sunao Takeda, Yasushi Kaneko, Hiromichi Eto, Kazuya Ishida, Kazunori Maebashi, Masaru Matsumoto, Takemitsu Asaoka, Susumu Sato, Hideaki Matsuda
  • Patent number: 5932707
    Abstract: Ligands for radiopharmaceutical use are capable of chelating radiometal species and of being bound to biological targeting molecules. The ligands have the formula (a) and (b), where A, A'=--SZ or Y, B=O or S, Y=(c), Z=H or a thiol protecting group, m=2 or 3, n=2 or 3, q=0 or 1, R=H or unsubstituted or substituted hydrocarbon and pharmaceutically acceptable salts, provided that at least one CR.sub.2 group represents CO and forms, together with an adjacent N atom; a --CONR-- amide group.
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: August 3, 1999
    Assignee: Nycomed Amersham plc
    Inventors: Colin Mill Archer, Gary Robert Bower, Harjit Kaur Gill, Anthony Leonard Mark Riley, Anthony Eamon Storey, Lewis Reuben Canning, David Vaughan Griffiths
  • Patent number: 5821388
    Abstract: The present invention provides processes for preparing .alpha.-halo(methylthio)acetophenone and .alpha.-halo (methylsulfonyl)acetophenone in an industrially simple and economically advantageous manner. In the invention, methylthioacetophenone is halogenated with a halogenating agent in the presence of an alcohol, giving .alpha.-halo(methylthio) acetophenone. Then the compound is oxidized with an oxidizing agent, giving .alpha.-halo(methylsulfonyl)acetophenone.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: October 13, 1998
    Assignee: Sumitomo Seika Chemical Co., Ltd.
    Inventors: Junichi Sakamoto, Hideaki Nishiguchi, Hiroshi Goda
  • Patent number: 5801120
    Abstract: Substituted aryl or heteroaryl in particular benzoyl bicycloalkanediones and related compounds, intermediates therefor, synthesis thereof, and the use of said diones for the control of weeds.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: September 1, 1998
    Assignee: Sandoz Ltd.
    Inventors: Shy-Fuh Lee, Takashi Nishizaka, Kenichi Komatsubara
  • Patent number: 5798396
    Abstract: The present invention is directed to sulfonium salt-containing compounds represented by a following general formula; ##STR1## wherein R.sub.1 is alkyl containing from 1 to 18 carbon atoms, hydroxy, alkoxy containing from 1 to 18 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or halogen, n is any of 0, 1, 2 or 3, however, each of R.sub.1 may be different from the others when n is 2 or more, R.sub.2 is alkyl containing from 1 to 6 carbon atoms, R.sub.3 and R.sub.4 are each independently hydrogen or alkyl containing from 1 to 6 carbon atoms, R.sub.5 and R.sub.6 are each independently hydrogen, alkyl containing from 1 to 6 carbon atoms, hydroxy, alkoxy containing from 1 to 6 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or aromatic carbonyloxy, and R.sub.7 is alkyl containing from 4 to 20 carbon atoms or a group represented by a following formula; ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 4, 1996
    Date of Patent: August 25, 1998
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Eiji Takahashi, Hiroo Muramoto
  • Patent number: 5696282
    Abstract: A process comprises contacting, in the presence of a catalyst, hydrogen sulfide or a mercaptan such as, for example, n-dodecyl mercaptan with an .alpha.,.beta.-unsaturated carbonyl or .alpha.,.beta.-unsaturated cyano compound such as, for example, methyl acrylate wherein the catalyst comprises a pyridine derivative such as, for example, 4-(dimethylamino)pyridine or an ion exchange resin such as, for example, "AMBERLYST A-21" to produce a 3-hydrocarbylthio derivative of the .alpha.,.beta.-unsaturated carbonyl or .alpha.,.beta.-unsaturated cyano compound such as, for example, methyl 3-(dodecylthio)propionate.
    Type: Grant
    Filed: March 26, 1996
    Date of Patent: December 9, 1997
    Assignee: Phillips Petroleum Company
    Inventors: James E. Shaw, Harry Porter
  • Patent number: 5559218
    Abstract: 2-Aroylcyclohexanediones I ##STR1## (A is C.sub.1 -C.sub.6 -alkylene; R.sup.1 is substituted phenyl or hetaryl which may furthermore carry a fused ring; R.sup.2 -R.sup.5 are each hydrogen or C.sub.1 -C.sub.4 -alkyl; R.sup.6 is H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxycarbonyl and R.sup.7 is C.sub.1 -C.sub.4 -alkyl,with the proviso that R.sup.1 is not mono- or dihalophenyl)and the agriculturally useful salts thereof and the esters of I with C.sub.1 -C.sub.10 -carboxylic acids or inorganic acids.The 2-aroylcyclohexanediones I are suitable as herbicides and plant growth regulators.
    Type: Grant
    Filed: February 6, 1995
    Date of Patent: September 24, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: J urgen Kast, Wolfgang von Deyn, Christoph N ubling, Helmut Walter, Matthias Gerber, Karl-Otto Westphalen
  • Patent number: 5536703
    Abstract: The invention relates to novel thioether derivatives of substituted benzoyl bicycloalkane diones, their use as herbicides and agricultural compositions comprising the same.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: July 16, 1996
    Assignee: Sandoz Ltd.
    Inventor: Shy-Fuh Lee
  • Patent number: 5534557
    Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3): ##STR2## where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 9, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5525580
    Abstract: Compounds represented by general formula (I), herbicides or selective herbicides for paddy field containing said compounds as active ingredients, method of controlling growth of undesirable plants by applying the herbicides on places where control is desired. ##STR1## wherein A represents a --S(O)nR.sup.1 in which n is 0 or 2 and R.sup.1 represents a (substituted) lower alkyl; a cycloalkyl; a (substituted) benzyl; a (substituted) phenyl; or a --OR.sup.2 in which R.sup.2 represents a (substituted) phenyl;B represents a halogen, a nitro, a lower alkyl, or a lower alkylsulfonyl;D represents a hydrogen, a lower alkyl, a lower alkoxy, a lower alkoxymethyl, or a lower alkoxycarbonyl;E represents a halogen, a (substituted) lower alkoxy, a lower alkylthio, a (substituted) lower alkylsulfonyl, or a lower alkylsulfonyloxy.The herbicides of the present invention can prevent a wide variety of noxious weeds and further selectively prevent weeds on paddy field with considerably reduced phytotoxicities on rice plant.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: June 11, 1996
    Assignee: SDS Biotech K.K.
    Inventors: Kenichi Komatsubara, Tadashi Sato, Kenji Mikami, Yuji Yamada
  • Patent number: 5492917
    Abstract: Novel compounds of the general structural formula I: ##STR1## have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: February 20, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Ralph A. Rivero, Peter D. Williams, Daniel F. Veber
  • Patent number: 5476876
    Abstract: The subject invention relates to compounds having the structure: ##STR1## wherein (a) X is selected from hydroxy, C.sub.1 to about C.sub.2 alkanoxy, thiol, C.sub.1 to about C.sub.2 alkanylthiol, and halo;(b) R and R' are each independently selected from C.sub.1 to about C.sub.3 straight or branched alkanyl, and C.sub.3 to about C.sub.4 cyclic alkanyl; or R and R' are bonded together to form a C.sub.3 to about C.sub.6 cyclic alkanyl ring, or a C.sub.3 to about C.sub.5 cyclic heteroalkanyl ring having one oxygen or sulfur atom in the ring, the heteroatom not being bonded to the carbon to which X is bonded; and R and R', or the ring formed by them when bonded together, are each, independently, unsubstituted or monosubstituted with a substituent selected from halo, hydroxy, thiol, C.sub.1 to about C.sub.2 alkanoxy, and C.sub.1 to about C.sub.2 alkanylthiol.The subject invention also relates to the pharmaceutical compositions comprising the above compounds, and methods of treating inflammation using the compounds.
    Type: Grant
    Filed: May 24, 1994
    Date of Patent: December 19, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Stanislaw Pikul, Joseph A. Miller, John M. Janusz, Theresa Rosario-Jansen
  • Patent number: 5463138
    Abstract: Difluoromethoxyarenes and difluoromethylthioarenes of the general formula (I),Ar--Q--CHF.sub.2 (I)in whichAr represents optionally substituted aryl, andQ represents oxygen or sulphur,(which can be used as intermediates for preparing biologically active products) are obtained in very good yields and in a high degree of purity by reacting hydroxyarenes or mercaptoarenes of the general formulaAr--Q--H (II)with chlorodifluoromethane (ClCHF.sub.2) in the presence of an aqueous alkali metal hydroxide or alkaline earth metal hydroxide at temperatures of between 20.degree. C. and 120.degree. C.
    Type: Grant
    Filed: May 18, 1994
    Date of Patent: October 31, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus-Helmut Muller
  • Patent number: 5393776
    Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5350878
    Abstract: This invention provides 1) novel reactive fluorinated compounds derived from a specified class of telomers or cotelomers of fluoroolefins; and 2) stable products and stable polymers thereof obtained by reaction or polycondensation of the novel reactive fluorinated compounds with specified classes of hydrogenated aliphatic, alicyclic, aromatic reactive compounds, telechelic oligomers and block polymers wherein said stable products and polymers contain hetero atoms such as oxygen, sulfur or nitrogen and are characterized by high thermal and chemical resistance.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: September 27, 1994
    Assignee: Dow Corning Corporation
    Inventor: Gerardo Caporiccio
  • Patent number: 5300654
    Abstract: .beta.-hydroxyketones are prepared by reacting an aldehyde with acetone in the presence of perhydroisoindole or pyrrolidine and water. The resulting .beta.-hydroxyketone is further reacted in the presence of a solvent mixture to produce .alpha.-.beta.-unsaturated ketones.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: April 5, 1994
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Masashi Nakajima, Tadashi Kyotani, Mikio Sawaki
  • Patent number: 5288742
    Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different, is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: February 22, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Philip N. Edwards, David Waterson
  • Patent number: 5272178
    Abstract: The present invention relates to compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl, phenyl, or hydrogen; R.sup.3 represents hydrogen or alkyl; X represents O, S or (CH.sub.2).sub.m wherein m is 1 or 2; A represents O or S(O).sub.n wherein n is 0, 1, or 2; p is an integer from 0 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl; or NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl, and R.sup.6 is hydrogen, alkyl, heterocyclealkyl, substituted heterocyclealkyl, cycloalkyl, substituted cycloalkyl, phenyl, substituted phenyl, phenylalkyl, or substituted phenylalkyl, or NR.sup.5 R.sup.6 together form a heterocyclic ring which may optionally be substituted; or (CH.sub.2).sub.t COOR.sup.7 wherein t is an integer from 1 to 4 and R.sup.7 is hydrogen or alkyl; and the pharmaceutically acceptable salts thereof. The compounds are inhibitors or stimulators of superoxide generation.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: December 21, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 5245041
    Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: September 14, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5216183
    Abstract: A 2,3-epoxycyclopentanone represented by the formula (IV): ##STR1## wherein the variables are as defined in the specification, which is used in the preparation of a 2-substituted-2-cyclopentanone compound suitable for use as an anticancer agent and a bone formation accelerator.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: June 1, 1993
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Toru Minoshima, Atsuo Hazato, Yoshinori Kato
  • Patent number: 5208388
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5200535
    Abstract: The invention provides cyclohexanone derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group; R.sup.6 and R.sup.7 together represent a single carbon-carbon bond or an epoxy group; and R.sup.8 represents a hydrogen atom or a hydroxyl group; with the proviso that when R.sup.6 and R.sup.7 together represent an epoxy group then R.sup.8 represents a hydrogen atom; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: April 6, 1993
    Assignee: Shell Research Limited
    Inventor: Paul H. Briner
  • Patent number: 5189165
    Abstract: A process for preparing a compound I ##STR1## with A=t-butyl, aryl andR=alkyl, alkenyl, alkynyl, alkenynyl, cycloalkyl(alkyl), aryl, arylalkyl, alkyl-S-(-O)-arylby reacting a compound III ##STR2## with a compound IV ##STR3## under the conditions of a phase-transfer reaction, is described. The process gives excellent yields and is not associated with the unpleasant odor of mercaptans.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 23, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Burdinski, Reinhard Kirsch, Hariolf Kottmann
  • Patent number: 5154753
    Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, Y and Z have the meanings given in the disclosure, processes for their manufacture, herbicidal and growth-regulating agents containing the novel active ingredients, and processes for combating unwanted plant growth and for regulating plant growth.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: October 13, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Meyer, Johann Jung, Wilhelm Rademacher, Dieter Kolassa, Rainer Becker, Dieter Jahn, Michael Keil, Ulrich Schirmer, Bruno Wuerzer
  • Patent number: 5152826
    Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5142095
    Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: August 25, 1992
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Daniel L. Flynn
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5118856
    Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: June 2, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5116869
    Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: May 26, 1992
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
  • Patent number: 5113019
    Abstract: The invention relates to the preparation of alkylthiophenols by reaction of a dialkyl disulphide with a phenol.In the process according to the invention, the reaction is carried out in the presence of aluminum chloride or of ferric chloride in a solvent of the alkylbenzene type or, soley in the case of methylthiolation, in an excess of dimethyl disulphide.This process makes it possible, in particular to obtain, with a selectivity and in a yield which are excellent, 2-alkylthiophenols which may then be converted into 4-acyl-2-alkylthiophenols by means of a reaction at a temperature ranging from 40.degree. to 100.degree. C. with a complex BF.sub.3 :2RCOOH where R denotes an alkyl or propenyl radical, in a proportion of 10 to 15 moles of complex per mole of 2-alkylthiophenol.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: May 12, 1992
    Assignee: Societe Nationale Elf Aquitaine (Production)
    Inventors: Catherine Vottero, Yves Labat, Jean-Marie Poirier
  • Patent number: 5110343
    Abstract: The invention relates to a herbicidal composition having an inert carrier and an effective amount of a compound having the formula ##STR1## wherein X is the same or different substituent selected from the group consisting of halogen, nitro, C.sub.1-6 alkyl, halo C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio and C.sub.1-6 alkylsulfonyl;n is 1, 2, 3 or 4;R.sup.1 is C.sub.1-6 alkyl which is substituted by cyano, halogen, hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfonyl or tetrahydropyranyloxy; C.sub.1-6 alkylthio, phenylthio, pyridyl or tetrahydropyranyl;R.sup.2 is C.sub.1-6 alkyl;l is 0, 1 or 2.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: May 5, 1992
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Akiyoshi Ueda, Haruhito Ohishi, Toshio Aihara, Hisao Ishikawa, Kazuyuki Tomida, Hideo Hosaka
  • Patent number: 5101076
    Abstract: Compounds of the present invention are represented by the formula, ##STR1## wherein X represents a lower alkyl, lower alkoxy, lower haloalkyl or lower haloalkoxy group or a halogen atom, and R.sup.1 and R.sup.2, which may be the same or different, represent a hydrogen atom or a methyl group. They are useful intermediates for preparing herbicidal compounds.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: March 31, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsunori Hiratsuka, Masao Shiroshita, Susumu Ohtsuka, Kenji Arai, Naonori Hirata