Hydroxy, Bonded Directly To Carbon, Or Ether Containing (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 564/443)
  • Patent number: 5703266
    Abstract: The invention concerns the use of a 3-substituted para-aminophenol as an oxidation dye precursor for dyeing keratinous fibres, in particular human hair. The 3-substituted para-aminophenol has formula: ##STR1## where R.sub.1 represents alkyl, alkenyl, mono- or polyhydroxyalkyl, nitrile, cyanoalkyl, halogenoalkyl, aminoalkyl or alkoxyalkyl and R.sub.2 represents hydrogen, alkyl or mono- or polyhydroxyalkyl, provided that when R.sub.2 is hydrogen R.sub.1 is not methyl or trifluoromethyl, and to addition salts thereof with an acid. The invention also concerns dye compositions containing compound (I). The invention further concerns novel 3-substituted para-aminophenols.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: December 30, 1997
    Assignee: L'Oreal
    Inventors: Alain Lagrange, Jean Jacques Vandenbosche, Jean Cotteret, Marie Pascale Audousset
  • Patent number: 5693863
    Abstract: The present invention relates to methods for the production of E-1-?4'-(2-dimethylaminoethoxy)-phenyl!-1-(3'-hydroxyphenyl)-2-phenyl-1-bu tene of formula (I) which comprises heating the compound of formula (II) in the presence of an organic solvent and HCl gas and cooling the reaction to obtain the compound of formula (IIIa), and then heating the isolated compound of formula (IIIa) in the presence of sulfuric acid or hydrochloric acid to obtain the compound according to formula (I).
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: December 2, 1997
    Assignee: Klinge Pharma GmbH
    Inventors: Helmut Grill, Axel Woschina
  • Patent number: 5686464
    Abstract: A 3,3-diphenylpropylamine of the formula I, or its physiologically acceptable acid salt thereof: ##STR1## wherein R.sup.1 represents hydrogen or methyl, R.sup.2 and R.sup.3 independently represent hydrogen, methyl, methoxy, hydroxy, carbamoyl, sulphamoyl or halogen, and X represents a tertiary amino group of formula II ##STR2## wherein R.sup.4 and R.sup.5 independently represent a hydroxy substituted or unsubstituted non-aromatic hydrocarbyl group which can join together to form a ring and which together contain at least three carbon atoms, wherein at least one of R.sup.4 and R.sup.5 is hydroxy substituted, is useful in treating acetylcholine-mediated disorders such as urinary incontinence.
    Type: Grant
    Filed: July 22, 1996
    Date of Patent: November 11, 1997
    Assignee: Pharmacia AB
    Inventors: Rolf Arne Johansson, Pinchas Moses, Lisbeth Nilvebrant, Bengt .ANG.ke Sparf
  • Patent number: 5685881
    Abstract: Aromatic allylaminonitro compounds corresponding to formula (I): ##STR1## in which R.sup.1 is hydrogen or an alkyl group containing 1 to 4 carbon atoms, R.sup.2 is hydrogen, an alkyl group containing 1 to 4 carbon atoms or an allyl group CH.sub.2 C(R.sup.5)=CH.sub.2, where R.sup.5 is hydrogen or an alkyl group containing 1 to 4 carbon atoms, R.sup.3 is carboxyl, hydroxy, nitro, halogen or a group NR.sup.6 R.sup.7, where R.sup.6 and R.sup.7 independently of one another represent hydrogen, an alkyl group containing 1 to 4 carbon atoms, a hydroxyalkyl or dihydroxyalkyl group containing 2 to 4 carbon atoms or an allyl group CH.sub.2 C(R.sup.8)=CH.sub.2, where R.sup.8 is hydrogen or an alkyl group containing 1 to 4 carbon atoms, and R.sup.4 is hydrogen or nitro, with the proviso that R.sup.3 and R.sup.4 are not both nitro. The compounds are useful for dyeing fibers, particularly human hair.
    Type: Grant
    Filed: June 30, 1995
    Date of Patent: November 11, 1997
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: David Rose, Horst Hoeffkes, Edgar Lieske, Iduna Matzik
  • Patent number: 5679859
    Abstract: The present invention concerns a process for producing crystals of 3-amino-2-hydroxyacetophenone salt having a high bulk density and improved flow properties, by treating 3-amino-2-hydroxyacetophenone of formula (1) ##STR1## or hydrogen halide salt thereof with sulfuric acid, in a solvent.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: October 21, 1997
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Hirokazu Murata, Hideki Ushio, Atsushi Furutani, Hiroaki Hibino, Etsuko Fukuda
  • Patent number: 5676706
    Abstract: Compounds of the formula (I) and their salts with inorganic and organic acids, ##STR1## in which R.sub.1 is a hydrogen atom or a trimethylsilyl group, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are, independently of each other, a hydrogen atom, a (C.sub.1 -C.sub.4) alkyl group, a hydroxy-(C.sub.2 -C.sub.3) alkyl group, an alkoxy-(C.sub.2 -C.sub.3) group, an amino-(C.sub.2 -C.sub.3) group, or a 2,3-dihydroxypropyl group, and in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are not simultaneously hydrogen atoms, and processes for their preparation and use as hair-coloring agents.
    Type: Grant
    Filed: October 25, 1995
    Date of Patent: October 14, 1997
    Inventors: Mustafa Akram, Wolfgang Wolff, Andreas Bittner, Uwe Kobs
  • Patent number: 5672759
    Abstract: The invention relates to a dye composition for keratinic fibers comprising an oxidation colorant precursor of the type ortho and/or para and a sulfured metaphenylenediamine having formula (I) ##STR1## wherein Z is alkyl, aralkyl, monohydroxyalkyl or polyhydroxyalkyl, aryl or aminoalkyl, as well as the acid salts thereof, with the condition that R.sub.1 and R.sub.2 do not represent simultaneously hydrogen when Z is alkyl or hydroxyalkyl, as well as the acid salts corresponding to the compounds of formula (I).
    Type: Grant
    Filed: January 19, 1996
    Date of Patent: September 30, 1997
    Assignee: L'Oreal
    Inventors: Alex Junino, Alain Genet, Alain Lagrange
  • Patent number: 5656619
    Abstract: Abstract of the Disclosure: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 12, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5645610
    Abstract: The new coupler compounds of the invention are 4-amino-2 -(2'-hydroxyethyl)-amino-5-methoxytoluene and/or 4-amino-2-(2'-hydroxyethyl)amino-5-chlorotoluene. The invention also includes an oxidation hair dye composition including an effective amount, advantageously from 0.01 to 5 percent by weight, of the above-mentioned new coupler compounds together with one or more known developer compounds and optionally certain direct dyes.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 8, 1997
    Inventors: Wolfgang R. Balzer, Anke Frank, Alexa Weinges
  • Patent number: 5639915
    Abstract: Industrial process for the efficient production of aniline derivatives which are important intermediates for the manufacture of oxazolidinedione derivatives and tetrahydrophthalimide derivatives which are useful as active ingredients of herbicides. The process starts from 2,4-dihalo-5-aminophenol or bis(2,4-dihalo-5-aminophenyl)carbonate and selectively cycloalkylates or alkynylates the hydroxy group without protecting the amino group, whereby aniline derivatives having the cycloalkyloxy group or alkynyloxy group can be produced in high yield.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: June 17, 1997
    Assignees: Sagami Chemical Research Center, Kaken Pharmaceutical Co., Ltd.
    Inventors: Kenji Hirai, Emiko Ejiri, Tomoyuki Yano, Kiyomi Aizawa
  • Patent number: 5637256
    Abstract: This invention provides chiral nonracemic compound of formula: ##STR1## wherein n and m are 0 or 1, but one of n or m must be 1; k=0 or 1; B=COO or OOC; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are either H, an electron donor or an electron acceptor where at least one of the groups X.sub.1, X.sub.2, X.sub.3 or X.sub.4 is an electron acceptor and at least one of these groups is an electron donor and when one of X.sub.1 or X.sub.3 is an electron donor, the other is an electro a acceptor and when one of X.sub.2 or X.sub.4 is an electron donor, the other is an electron acceptor; and R.sub.1 and R.sub.2 can be various substituted and unsubstituted alkanes and monoalkenes. Compounds provided include those where one of R.sub.1 or R.sub.2 is a chiral non-racemic tail group, particularly a group selected from --O--C.sup.* H(CH.sub.3)R.sub.c, --O--C.sup.* H(CH.sub.3)COOR.sub.d, and --O--CH.sub.2 C.sup.* HF--C.sup.* HF--R.sub.2 in which the .sup.* indicates an asymmetric carbon enriched in one stereoconfiguration where R.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: June 10, 1997
    Assignee: University Research Corporation
    Inventors: David M. Walba, Maria B. Ros, James A. Rego, Teresa Sierra
  • Patent number: 5633407
    Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: May 27, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5618979
    Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: April 8, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5596020
    Abstract: This invention relates to a class of novel amino bi- and tri-carbocyclic alkane compounds having bis-aryl substitution which exhibit squalene synthase inhibition properties. The bi- and tri-carbocyclic alkane ring contains an amino group and the ring is further linked or bridged to two mono- and/or bicyclic rings. Compounds of this invention reduce levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention.
    Type: Grant
    Filed: December 7, 1994
    Date of Patent: January 21, 1997
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Robert L. Morris, Kent W. Neuenschwander, Keith S. Learn, Anthony C. Scotese
  • Patent number: 5559269
    Abstract: The invention relates to 3,3-diphenylpropylamines of formula (I), wherein R.sup.1 signifies hydrogen or methyl, R.sup.2 and R.sup.3 independently signify hydrogen, methyl, methoxy, hydroxy, carbamoyl, sulphamoyl or halogen, and X represents a tertiary amino group of formula (II), wherein R.sup.4 and R.sup.5 signify non-aromatic hydrocarbyl groups, which may be the same or different and which together contain at least three carbon atoms, and wherein R.sup.4 and R.sup.5 may form a ring together with the amine nitrogen, their salts with physiologically acceptable acids and, when the compounds can be in the form of optical isomers, the racemic mixture and the individual enantiomers.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: September 24, 1996
    Assignee: Pharmacia AB
    Inventors: Rolf A. Johansson, Pinchas Moses, Lisbeth Nilvebrant, Bengt .ANG.. Sparf
  • Patent number: 5550291
    Abstract: Disclosed herein is a stereospecific synthesis amenable to the large scale preparation of a hydrochloric acid addition salt of a chlorohydrin of the formula ##STR1## wherein R.sup.1 and R.sup.2 are amino protective groups and R.sup.3 is an amino acid side chain or a protected amino acid side chain. The synthesis involves reacting an aldehyde of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined hereinbefore with (chloromethyl)lithium at -20.degree. C. or below and contacting the resulting diastereoisomeric mixture of lithium alcoholates with aqueous hydrochloric acid to obtain a separable mixture of the hydrochloric acid addition salts of the chlorohydrin and its corresponding hydroxy diastereoisomer. The hydrochloric acid addition salt of the chlorohydrin is transformed readily into corresponding optionally amino-protected aminoepoxides; for example, 3(S)-(tert-butyloxycarbonylamino)-l,2(S)-epoxy-4-phenyl-butane.
    Type: Grant
    Filed: May 4, 1995
    Date of Patent: August 27, 1996
    Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.
    Inventors: Pierre L. Beaulieu, Yvan Guindon, Dominik M. Wernic
  • Patent number: 5525632
    Abstract: A stilbene derivative of the following general formula (I) or a pharmaceutically acceptable acid addition salt thereof have low toxicity, but are water soluble and effective as carcinostatics: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each represent an alkyl group having 1 to 3 carbon atoms; X represents a hydrogen atom or a nitrile group; Y represents an alkyloxy group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a halogen atom.
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: June 11, 1996
    Assignee: Ajinomoto Co., Ltd.
    Inventors: Koji Obsumi, Takashi Tsuji, Yoshihiro Morinaga, Kazuo Ohishi
  • Patent number: 5512067
    Abstract: Compounds are described in which a polyamine moiety is linked to a phenolic moiety by a Mannich base linkage involving one of the amino groups of the polyamine moiety, and in which an aminoalkylene-poly(oxyalkylene) moiety is linked to the phenolic moiety by a Mannich base linkage involving an amino group of the alkylene-poly(oxyalkylene) moiety. Compounds of this type have been found to be highly effective in controlling the formation of intake valve deposits in internal combustion engines.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: April 30, 1996
    Assignee: Ethyl Corporation
    Inventor: John T. Loper
  • Patent number: 5493055
    Abstract: A process for the manufacture of para-phenetidine is described. The process comprises the following steps: (a) diazotizing para-phenetidine and coupling the resulting compound to phenol at a molar ratio of 1.3 to 1 phenol to the diazo compound;(b) ethylating the resulting compound at a temperature in the range of between 130.degree. C. to 200.degree. C., and (c) catalytically hydrogenating the ethylated compound, whereby two moles of para-phenetidine are produced, one of which being recycled as the starting reagent in the first step. The product obtained is of a high purity being substantially free from the undesired isomers.
    Type: Grant
    Filed: April 6, 1995
    Date of Patent: February 20, 1996
    Assignee: Tambour, Ltd.
    Inventor: Jacob Kalo
  • Patent number: 5466872
    Abstract: Fuel compositions containing a major amount of hydrocarbons boiling in the gasoline or diesel range and an effective deposit-controlling amount of a poly(oxyalkylene) aromatic ether having the formula: ##STR1## where A.sub.1 is nitro, amino, N-alkylamino wherein the alkyl group contains 1 to 6 carbon atoms, or N,N-dialkylamino wherein each alkyl group independently contains 1 to 6 carbon atoms; R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkyl, or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl and each R.sub.3 and R.sub.4 is independently selected in each --O--CHR.sub.3 --CHR.sub.4 -- unit; R.sub.5 is hydrogen, alkyl having 1 to 100 carbon atoms, phenyl, aralkyl having 7 to 100 carbon atoms or alkaryl having 7 to 100 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: November 14, 1995
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5453542
    Abstract: The present invention is a method of preparing a 4,6-bisarylazoresorcinol comprising reacting an aryldiazonium salt and resorcinol in the presence of a base and a reaction medium containing water and a water-miscible solvent at a temperature in the range of about -5.degree. C to about -60.degree. C. The present invention is also a method of preparing a 2-substituted 4,6-bisarylazoresorcinol comprising reacting an aryldiazonium salt with a 2-substituted resorcinol. The 4,6-bisarylazoresorcinol or 2-substituted 4,6-bisarylazoresorcinol can then be hydrogenated to a 4,6-diaminoresorcinol, which is a precursor to polybisbenzoxazoles (PBOs), polymers which are useful as insulators, solar arrays, and tear-resistant gloves.
    Type: Grant
    Filed: February 24, 1994
    Date of Patent: September 26, 1995
    Assignee: The Dow Chemical Company
    Inventors: Ted A. Morgan, Bassam S. Nader, Paul Vosejpka, Weshi Wu, Andrew S. Kende
  • Patent number: 5446186
    Abstract: The synthesis and compound of a new caged calcium which is an ortho-nitrophenyl derivative of EGTA and various intermediates. It is synthesized in ten steps and 24% overall yield. The photosensitive chelator, nitrophenyl-EGTA, has a K.sub.d for Ca.sup.2+ of 80 nM and for Mg.sup.2+ of 8.8 mM. Upon exposure to ultra-violet light (in the region of 350 nm), the chelator is cleaved, yielding iminodiacetic acid photoproducts with known low Ca-affinity (K.sub.d =1 mM). The quantum yield of photolysis of nitrophenyl-EGTA in the presence of Ca.sup.a+ is 0.23 and in the absence of Ca.sup.2+ is 0.20. In experiments with chemically skinned skeletal muscle fibers, a fully relaxed fiber equilibrated with nitrophenyl-EGTA:Ca.sup.2+ complex, in the presence of physiological [Mg.sup.2+ ] (i.e. 1.0 mM), produced maximal contraction after a single flash from a frequency doubled ruby laser (347 nm). Half-maximal tension was achieved in 18 ms at 15.degree. C.
    Type: Grant
    Filed: November 9, 1993
    Date of Patent: August 29, 1995
    Inventors: Graham C. R. Ellis-Davies, Jack H. Kaplan
  • Patent number: 5442121
    Abstract: A process for producing N,N-disubstituted aminophenol which comprises the steps of:obtaining a reaction mixture containing N-substituted aminophenol by reacting a dihydric phenol and an amine;subjecting said reaction mixture to heat treatment so as to thermally decompose quaternary ammonia salt contained in said reaction mixture into a dihydric phenol and an amine, and removing at least said amine by distillation;separating high-boiling impurities by distillation to separate N-substituted aminophenol; andsubjecting said separated N-substituted aminophenol to reduction alkylation using an aldehyde compound.According to the present invention, high-purity N,N-disubstituted aminophenol can be obtained in a high yield at high selectivity, and a reduction catalyst can be used repeatedly because its activity can be maintained at a high level and yet it can retain high activity for a long period of time.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: August 15, 1995
    Assignee: Mitsui Petrochemical Industries Ltd.
    Inventors: Shigeki Nagamatsu, Tomohiro Arase, Masaaki Yasuda
  • Patent number: 5434308
    Abstract: A method of dehydrogenating 3-amino-2-cyclohexene-1-one with a supported palladium or palladium-platinum catalyst in a solvent in the presence of base to produce 3-aminophenol and its use directly without purification to produce 3,4'-oxydianiline.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: July 18, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Stephen E. Jacobson
  • Patent number: 5430062
    Abstract: The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceutical compositions containing the compounds are disclosed. Three preferred compounds among those disclosed are (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, (Z)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, and 4-methyl-3',4',5'-trimethoxybenzylaniline hydrochloride.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: July 4, 1995
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Mark S. Cushman, Ernest Hamel
  • Patent number: 5430130
    Abstract: An photosensitive polyfunctional aromatic diazo compound having at least two groups of Formula (uD) in the molecule, and a photosensitive composition using the same. The diazo compound can be handled under visible light free from ultraviolet, is highly photosensitive, has good shelf life, and is adequate as a photosensitive agent for lithographic printing plates and screen printing plates: ##STR1## wherein G.sup.1 is a substituent derived from alcoholic hydroxyl group; R.sup.1 and R.sup.2 are hydrogen, or alkyl or alkyloxy of 1 to 8 carbon atoms;R.sup.3 is alkyl or substituted alkyl of 1 to 8 carbon atoms, aralkyl or substituted aralkyl of 7 to 14 carbon atoms, or --CH.sub.2 CHG.sup.2 --CH.sub.2 --;X.sup.- is an anion based on protonic acid from which a proton is removed.
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: July 4, 1995
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Noriaki Tochizawa, Yasuo Kuniyoshi, Masaharu Watanabe, Katsuyo Tokuda, Ichiro Hozumi
  • Patent number: 5420277
    Abstract: Antibacterial activity is exhibited by novel compounds having the formula ##STR1## where R.sub.1, R.sub.2, and M are as defined herein and X is --(CH.sub.2).sub.n -- wherein n is 0, 1, 2, 3 or 4 or CR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5 or R.sub.3 and R.sub.4 taken together with the carbon atom to which they are attached form a 3, 4, 5, 6 or 7-membered cycloalkyl ring. Also described are various intermediates for the preparation of compounds of formula 1.
    Type: Grant
    Filed: November 29, 1993
    Date of Patent: May 30, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: William H. Koster, Joseph E. Sundeen, Henner Straub, Peter Ermann, Uwe D. Treuner, Kent Amsberry, Michael Fakes, Sailesh A. Varia
  • Patent number: 5414129
    Abstract: A process for the improved purification and separation of trans 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol hydrochloride from a reaction mixture containing the trans isomer, the cis isomer and Grignard reaction side products, comprising combining the mixture with a solution of hydrochloric acid in a low molecular weight alcohol or with gaseous hydrogen chloride in the presence of an organic solvent selected from medium molecular weight alcohols, ketones, esters and ethers or aromatic ethers, to effect the selective precipitation of trans 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol hydrochloride.
    Type: Grant
    Filed: September 8, 1993
    Date of Patent: May 9, 1995
    Assignee: Chemagis, Ltd.
    Inventors: Stephen Cherkez, Ori Lerman, Michael Tennenbaum, Hasalia Avner, Tamar Kunyevski
  • Patent number: 5414125
    Abstract: A diamino-alpha-alkylstilbene useful as an epoxy resin curing agent is represented by the following Formula I: ##STR1## wherein R is independently hydrogen, a C.sub.1 -C.sub.10 hydrocarbyl(oxy) group or a halogen, nitro, nitrile, phenyl or --CO--R.sup.1 group wherein R.sup.1 is independently hydrogen or a C.sub.1 -C.sub.3 hydrocarbyl group; each R.sup.4 is independently hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl group; and Y is a ##STR2## group wherein n=0 or 1.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5409503
    Abstract: The composition for oxidative dyeing of hair contains 0.01 to 5.0 percent by weight of at least one 5-aminophenol compound of the formula ##STR1## wherein R is an alkyl group having 1 to 4 carbon atoms, X is fluorine or OR.sup.1 and R.sup.1 is an alkyl group having 2 to 4 carbon atoms, a monohydroxyalkyl group with 2 to 4 carbon atoms or a dihydroxyalkyl group with 3 and 4 carbon atoms, and physiologically tolerated water-soluble salts thereof as coupler substance; and 0.1 to 6.1 percent by weight of a total amount of the coupler substance and at least one developer substance. The developer substance can be 1,4-diaminobenzene, 2,5-diaminotoluene, 2,5-diaminobenzyl alcohol, 2-(2'-hydroxyethyl)-1,4-diaminobenzene, 4-aminophenol, 4-amino-3-methylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-ethoxy-methylphenol and tetraaminophyrimidine and physiologically tolerated water-soluble salts thereof.
    Type: Grant
    Filed: October 21, 1993
    Date of Patent: April 25, 1995
    Assignee: Wella Aktiengesellschaft
    Inventors: Thomas Clausen, Wolfgang R. Balzer, Helmut Keller
  • Patent number: 5407591
    Abstract: An oil soluble dispersant comprising the reaction products of:(1) oil soluble salts, amides, imides, oxazolines, esters, or mixtures thereof of long chain hydrocarbyl substituted mono- and dicarboxlic acids or their anhydrides, (ii) long chain hydrocarbon having a polyamine attached directly thereto, and (iii) Mannich condensation product formed by condensing a long chain hydrocarbyl substituted hydroxy aromatic compound with an aldehyde and a polyalkylene polyamine, said adduct containing at least one reactive group selected from reactive amino groups and reactive hydroxyl groups; and(2) at least one polyepoxide.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: April 18, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jacob Emert, Robert D. Lundberg
  • Patent number: 5399673
    Abstract: Compounds containing at least one alkenyl group, at least one maleimide group and at least one rodlike mesogenic moiety are prepared by reacting one or more aminophenols containing one or more rodlike mesogenic moieties with a stoichiometric quantity of a maleic anhydride per amine group of said aminophenol and then alkenylating the resulting phenolic functional maleimide.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: March 21, 1995
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 5395958
    Abstract: The cyclopropene derivatives of the present invention are useful as the intermediates for producing cyclopropenone derivatives exhibiting strong inhibition activity of thiol protease such as calpain, papain, cathepsin B, cathepsin H, cathepsin L and the like.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: March 7, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Yasuhiro Morinaka, Eiichi Nakamura
  • 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: 5387718
    Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: February 7, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunther Kohler, Peter Bickert
  • Patent number: 5371291
    Abstract: The invention is a new process for preparing 4,6-diaminoresorcinol, a precursor to polybisbenzoxazoles. The desired product is prepared from resorcinol by incorporating a halo group on the 2-position of resorcinol to form 2-haloresorcinol, then nitrating selectively at the 4- and 6-positions of the 2-haloresorcinol to form 2-halo-4,6-dinitroresorcinol, then hydrogenating the 2-halo-4,6-dinitroresorcinol. The selective incorporation of a halo group on the 2-position of resorcinol is accomplished by sulfonating resorcinol at the 4- and 6-positions.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: December 6, 1994
    Assignee: The Dow Chemical Company
    Inventor: Bassam S. Nader
  • Patent number: 5364413
    Abstract: 3-Substituted para-aminophenols, process for preparing them, their use for dyeing keratinous fibres and the intermediate compounds used in the process of preparation.3-Substituted para-aminophenols, of general formula: ##STR1## where X.dbd.H, halogen; Y.dbd.O--, --S--; R.dbd.alkyl, hydroxyalkyl, C.sub.1-4 aminoalkyl or C.sub.3 -C.sub.6 polyhydroxyalkyl;with the proviso that, when X.dbd.H, R is not methyl, and when X.dbd.H and Y.dbd.O, R is not ethyl;process #or preparing them, intermediate compounds of formula: ##STR2## where X.sup.1 .dbd.halogen, Y and R have the meaning stated above; with the proviso that, when Y.dbd.O, R is not methyl, and when R.dbd.aminoalkyl, X.sub.1 can also denote hydrogen;dyeing compositions containing one or more compounds of formula (I), and a process for dyeing human hair.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: November 15, 1994
    Assignee: L'Oreal
    Inventors: Alex Junino, Alain Genet, Gerard Lang
  • Patent number: 5362856
    Abstract: Oxidation of C--H bonds in organic chemical compounds to C--OH bonds is accomplished by utilizing, as a monooxygenase, a heme protein such as methemoglobin or metmyoglobin in the presence of sulfate ion, in an aqueous medium.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: November 8, 1994
    Assignee: University of Toronto Innovations Foundation
    Inventors: Ronald Kluger, Yonghong Song
  • Patent number: 5354891
    Abstract: Disclosed is a method for producing aromatic amine derivatives in a high yield at a low price, which comprises inducing an aromatic hydroxamic acid derivative to undergo a rearrangement reaction under a mild condition in the presence of a base and a nitrile or a nitrile equivalent.
    Type: Grant
    Filed: March 4, 1993
    Date of Patent: October 11, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Tatsuhiko Obayashi
  • Patent number: 5319142
    Abstract: An arylisonitrosoalkanone is hydrogenated in the presence of a noble metal catalyst and a weak carboxylic acid to form an arylalkanolamine which is then hydrogenated in the presence of a strong mineral acid and the transition metal catalyst to form an arylalkylamine. When the arylisonitrosoalkanone is an isonitrosoacetophenone, the isonitrosoacetophenone is prepared by one of two methods.In the first method, a substituted or an unsubstituted isonitrosoacetophenone is prepared from a corresponding substituted or unsubstituted acetophenone by oxidizing the acetophenone to form a substituted or an unsubstituted phenylglyoxalacetal in a reactor, hydrolyzing the phenylglyoxal acetal in the same reactor to form a corresponding substituted or unsubstituted phenylglyoxal, and condensing the phenylglyoxal with hydroxylamine or a salt thereof in the same reactor to form the substituted or unsubstituted isonitrosoacetophenone.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: June 7, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Joseph A. McDonough, Ahmed M. Tafesh, Olan S. Fruchey
  • Patent number: 5312999
    Abstract: Propoxybenzene derivatives represented by the following formula ##STR1## wherein Ra represents a nitro group, an amino group which may have a protecting group or an --NHCH.dbd.C(COO--C.sub.1-6 -Alkyl).sub.2 group, Rb represents a hydrogen atom, a protecting group for the hydroxyl group or a substituted sulfonyl group and Xa and Xb, which may be the same or different, each represents a halogen atom, and processes for preparation thereof are disclosed. These derivatives are useful in preparing antibacterial agents.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: May 17, 1994
    Assignee: Daiichi Seiyaku Co., Ltd.
    Inventors: Toshihiro Fujiwara, Tutomu Ebata
  • Patent number: 5308829
    Abstract: There are disclosed novel benzofuran derivatives of the formula: ##STR1## Also disclosed are a herbicidal composition containing the above benzofuran derivative as an active ingredient and a method for exterminating undesired weeds by the application of a herbicidally effective amount of the above benzofuran derivative to an area where the undesired weeds grow or will grow.
    Type: Grant
    Filed: March 18, 1993
    Date of Patent: May 3, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Susumu Takemura, Masayuki Enomoto, Toru Uekawa, Masaharu Sakaki, Ryo Sato, Eiki Nagano
  • Patent number: 5306315
    Abstract: Poly(alkylene ether) amines having the formula: ##STR1## wherein A is an amine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; and n is an integer from 5 to 99. The poly(vinyl ether) amines of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: April 26, 1994
    Assignee: Chevron Research and Technology Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5306316
    Abstract: Poly(alkylene ether) amines having the formula: ##STR1## wherein A is an amine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; n is an integer from 5 to 99; and W is a hydroxy(oxypropylene) group having the formula: ##STR2## or mixtures thereof. The poly(vinyl ether) amines of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: April 26, 1994
    Assignee: Chevron Research and Technology Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5290929
    Abstract: Antibacterial activity is exhibited by novel compounds having the formula ##STR1## where R.sub.1, R.sub.2, and M are as defined herein and X is --(CH.sub.2).sub.n -- wherein n is 0, 1, 2, 3 or 4 or CR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5 or R.sub.3 and R.sub.4 taken together with the carbon atom to which they are attached form a 3, 4, 5, 6 or 7-membered cycloalkyl ring.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: March 1, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: William H. Koster, Joseph E. Sundeen, Henner Straub, Peter Ermann, Uwe D. Treuner, Kent Amsberry, Michael Fakes, Sailesh A. Varia
  • Patent number: 5288909
    Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 5288910
    Abstract: 4-amino-2-buten-1-ol is formed by the regioselective addition of primary amines or ammonia to 3,4-epoxy-1-butene. A quantity of a the primary amine or ammonia is reacted with 3,4-epoxy-1-butene in a reaction medium in the presence of a catalyst. The reaction medium is a liquid which has an E.sub.T (30) no less than about 32. The catalyst is a complex of palladium and phosphine ligands.
    Type: Grant
    Filed: September 4, 1992
    Date of Patent: February 22, 1994
    Assignee: Eastman Kodak Company
    Inventor: Yann Hung
  • Patent number: 5279619
    Abstract: Process for dyeing keratinous fibres, especially human keratinous fibres such as the hair, characterised in that a composition containing, in a medium suitable for dyeing, at least 2,4-diamino-1,3-dimethoxybenzene as a coupler;an oxidation dye precursor; andan oxidising agent; is applied to these fibres,the pH of the composition applied to the fibres being less than 7.
    Type: Grant
    Filed: January 4, 1993
    Date of Patent: January 18, 1994
    Assignee: L'Oreal
    Inventors: Jean Cotteret, Marie P. Audousset
  • Patent number: 5276058
    Abstract: Novel 3,4-dihydroxychalcone derivatives useful as a pharmaceutical material, and novel anti-inflammatory preparations. The 3,4-dihydroxychalcone derivatives are compounds of the formula [I], ##STR1## wherein X is a substituted phenyl group represented, e.g., by the formula (i), ##STR2## in which R.sup.1 is a hydrogen atom or an alkyl group and R.sup.2 is an alkyl group, an alkoxy group or an --OH group (excluding an OH-group in the 4-position)or salts thereof. The anti-inflammatory preparations contain one of the above 3,4-dihydroxychalcone derivatives as an active ingredient.
    Type: Grant
    Filed: June 9, 1993
    Date of Patent: January 4, 1994
    Assignee: Nippon Hypox Laboratories Incorporated
    Inventors: Toshio Satoh, Hitoshi Matsumoto, Yasunori Niiro
  • Patent number: RE34745
    Abstract: High purity 4,6-dinitro-1,3-benzenediol is prepared by (a) contacting a 1,2,3-trihalobenzene with a nitrating agent and an acid under reaction conditions such that a 1,2,3-trihalo-4,6-dinitrobenzene is produced, (b) contacting the 1,2,3-trihalo-4,6-dinitrobenzene prepared in (a) with an alkanol and a base under reaction conditions such that as 4,6-dinitro-2-halo-1,3-benzendiol is produced, and (c) contacting the 4,6-dinitro-2-halo-1,3-benzenediol prepared in (b) with a hydrogenating agent in the presence of a solvent and a catalyst under reaction conditions such that a 4,6-diamino-1,3-benzendiol is produced. This 4,6-diamino-1,3-benzene diol is useful in the preparation of high molecular weight polybenzoxazoles.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: September 27, 1994
    Assignee: The Dow Chemical Company
    Inventor: Zenon Lysenko