The Part Of The Chain Between The Ether Oxygen And Amino Nitrogen Consists Of Two Unsubstituted Saturated Carbons Patents (Class 564/354)
  • Patent number: 5959103
    Abstract: The invention provides naphthofluorene compounds, intermediates, formulations, processes, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, cardiovascular-related pathological conditions, including hyperlipidemia, and estrogen-dependent cancer.
    Type: Grant
    Filed: September 30, 1998
    Date of Patent: September 28, 1999
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Jeffrey Alan Dodge, Charles Willis Lugar, III
  • Patent number: 5952350
    Abstract: The invention provides a compound of formula I: ##STR1## or a pharmaceutically acceptable salt or solvate thereof; pharmaceutical compositions containing a compound of formula I, and methods of using a compound of formula I for inhibiting bone loss or bone resorption, particularly osteoporosis, and cardiovascular-related pathological conditions including hyperlipidemia, and estrogen dependent cancer.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: September 14, 1999
    Assignee: Eli Lilly and Company
    Inventors: George Joseph Cullinan, Brian Stephen Muehl
  • Patent number: 5866611
    Abstract: Compounds of formula I, and their pharmaceutically acceptable salts, ##STR1## in which R.sup.1 and R.sup.2 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, phenylalkyl or alkenyl; or NR.sup.1 R.sup.2 is a heterocyclic group; A is trimethylene optionally substituted by alkyl and the phenyl ring is optionally substituted by substituents such as halogeno, alkenyl, amino, cyano, ureido, alkyl, carbamoylalkyl, alkanoylamino, alkoxycarbonyl, N-alkyl-alkanoylamino, alkanoyl and amines thereof; are inhibitors of squalene synthese and hence useful in treating diseases in which a lowering of cholesterol is desirable. As well as the use of these compounds in medicine, novel compounds, processes for their preparation and pharmaceutical compositions are also referred to.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: February 2, 1999
    Assignee: Zeneca Limited
    Inventors: George Robert Brown, Murdoch Allan Eakin, Peter John Harrison, deceased, Keith Blakeney Mallion
  • Patent number: 5792762
    Abstract: The invention provides dihydronaphthofluorene compounds, formulations, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, and cardiovascular-related pathological conditions.
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: August 11, 1998
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Thomas Alan Crowell, Charles David Jones
  • Patent number: 5736568
    Abstract: Compounds of the formula I ##STR1## including pharmaceutically acceptable salts thereof are disclosed in which R.sub.1, R.sub.2, R.sub.3, and R.sub.4 independently represent hydrogen, hydroxy, halo, halogenated alkyl, halogenated alkoxy, alkyl, alkoxy, cyano, a carbamoyl group, carbonyl group, or R.sub.1 and R.sub.2 together with the phenyl ring represent a naphthalene ring (optionally substituted); L.sub.1 represents C.sub.2-6 alkylene; R.sub.5 represents hydrogen or alkyl, R.sub.6 represents hydrogen or alkyl, phenylalkyl (optionally substituted) or R.sub.5 and R.sub.6 together with the nitrogen atom to which they are attached represent a saturated 3-7 membered heterocyclic ring; L.sub.2 represents a C.sub.1-6 alkylene chain; and R.sub.7 and R.sub.8 independently represent hydrogen or alkyl or R.sub.7 and R.sub.8 together with the nitrogen atom to which they are attached represent a saturated 3-7 membered heterocyclic ring.
    Type: Grant
    Filed: November 25, 1996
    Date of Patent: April 7, 1998
    Assignee: Knoll Aktiengesellschaft
    Inventors: Paul Rafferty, Gerald Bernard Tometzki
  • Patent number: 5674909
    Abstract: Compounds of formula ##STR1## wherein R, R', R", R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X, Y, m, n and p have the meanings reported in the description;and their pharmaceutically acceptable salts are described.The compounds of formula I are useful in the treatment of arterial hypertension and congestive heart failure, of renal failure, of peripheral arteriopathies, of cerebrovascular insufficiencies and of ischemic cardiopathy.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 7, 1997
    Assignee: Zambon Group
    Inventors: Stefania Montanari, Paolo Cavalleri, Cristina Fraire, Gian Carlo Grancini, Mauro Napoletano, Francesco Santangelo
  • Patent number: 5669939
    Abstract: Polyalkylphenoxyaminoalkanes having the formula: ##STR1## wherein R is a polyalkyl group having an average molecular weight in the range of about 600 to 5,000;R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; andA is amino, N-alkyl amino having about 1 to about 20 carbon atoms in the alkyl group, N,N-dialkyl amino having about 1 to about 20 carbon atoms in each alkyl group, or a polyamine moiety having about 2 to about 12 amine nitrogen atoms and about 2 to about 40 carbon atoms.The compounds of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: May 14, 1996
    Date of Patent: September 23, 1997
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5624961
    Abstract: Novel benzylaminoethoxybenzene derivatives of the formula (I) ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl, a lower hydroxyalkyl, a lower alkoxyalkyl, an allyl or a benzyl; R.sup.2 is a hydrogen atom, a lower alkyl, a lower acyl, an allyl or a benzyl; R.sup.3 is a hydrogen atom, a lower alkyl, a lower alkoxyalkyl, a lower dialkylaminoalkyl or a lower acyl; and R.sup.4 is a hydrogen atom, a halogen atom, a lower alkoxy, an amino, a lower acylamino, a hydroxy, a lower acyloxy, a lower acyl, a carboxy or a lower alkoxycarbonyl, salts thereof and solvates thereof. An .alpha..sub.1 -adrenoceptor blocker obtained from this compound has a strong .alpha..sub.1 -adrenoceptor blocking effect and causes less side effects such as orthostatic hypotension.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: April 29, 1997
    Assignee: Japan Tobacco Inc.
    Inventors: Masakazu Ban, Kiyotaka Shinoda, Mitsuru Takahashi, Shuhei Deguchi, Hiroaki Taguchi, Takeo Katsushima
  • 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: 5420130
    Abstract: Compounds corresponding to the general formula (I) ##STR1## in which n represents 0 or 1, R.sub.1 represents a methyl group, in which case R.sub.2 represents a phenoxy(C.sub.1 -C.sub.4)alkyl group (in which the phenoxy group is optionally substituted), or else R.sub.1 and R.sub.2 together form, and with the nitrogen atom which carries them, a 4-(phenoxymethyl)piperid-1-yl group (in which the phenoxy group is optionally substituted) or a 4-phenylpiperazin-1-yl group (in which the phenyl group is optionally substituted), R.sub.3 represents a hydrogen atom or a methyl group, R.sub.4 represents a hydrogen atom and R.sub.5 represents a hydrogen atom or a group of general formula -CH.sub.2 -CH.sub.2 -NH-R.sub.6, R.sub.6 being a hydrogen atom or a tert-butyloxycarbonyl, 4-carbamoylpyrimidin-2-yl or 5-carbamoylpyrazin-2-yl group, are useful in the treatment of diseases and complaints involving hyperactivity of the .alpha.-adrenergic system at the level of the lower urinary apparatus.
    Type: Grant
    Filed: May 16, 1994
    Date of Patent: May 30, 1995
    Assignee: Synthelabo
    Inventors: Pascal George, Benoit Marabout, Jacques Froissant
  • Patent number: 5409957
    Abstract: Disclosed are a phenoxyalkylamine represented by the following general formula I and a salt of said phenoxyalkylamine represented by the following general formula II: ##STR1## wherein R represents a linear saturated hydrocarbon having 7 to 12 carbon atoms, n is an integer of from 1 to 5, m is an integer of from 2 to 4, and HX represents a mineral acid.These compounds have strong bacteriostatic and bactericidal actions for plants with no phytotoxicity. Therefore, these compounds are effectively used as the active ingredient of an agricultural and horticultural bactericide.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: April 25, 1995
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Mitsunori Oda, Kazutoshi Kikkawa, Akinori Tanaka, Satoko Imaruoka, Shigeo Yoshinaka
  • Patent number: 5407956
    Abstract: Derivatives of 2-amino-1,2,3,4-tetrahydronaphthalene and their use in therapeutic field are described.The compounds are particularly useful in the treatment of arterial hypertension, cardiac decompensation and renal failure, in the treatment of peripheral arteriopathies and in cerebrovascular insufficiency.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: April 18, 1995
    Assignee: Zambon Group S.p.A.
    Inventors: Francesco Santangelo, Giorgio Bertolini, Cesare Casagrande, Francesco Marchini, Stefania Montanari, Claudio Semeraro
  • Patent number: 5385892
    Abstract: The ethylamino phenyl ethers of the invention and compositions thereof are endowed with high activities as inhibitors of the growth of several species of pathogen fungi and are applied to plants or to plant parts and are effective in preventing the diseases caused by pathogen fungi, such as, e.g., those belonging to Erysiphe and Helminthosporium genera.
    Type: Grant
    Filed: January 4, 1993
    Date of Patent: January 31, 1995
    Assignee: Ministero Dell "Universita" E Dell Ricerca Scientifica E Tecnologica
    Inventors: Giovanni Camaggi, Lucio Filippini, Marilena Gusmeroli, Carlo Garavaglia, Luigi Mirenna
  • Patent number: 5358971
    Abstract: Optically active or racemic compounds are provided having the formula ##STR1## where R.sub.2, R.sub.3 and R.sub.4 are selected from the group consisting of H and OA with the provision that at least one of R.sub.2, R.sub.3 and R.sub.4 is H, that R.sub.2 and R.sub.4 are not both OA; A is H or is selected from the group consisting of hydrocarbyl radicals, said hydrocarbyl radicals being further optionally substituted with radicals selected from the group consisting of ##STR2## R.sub.5 is selected from the group consisting of alkyl and aromatic residues, preferably radicals having between 1 and 12 carbon atoms, including alkyl, alkyl substituted with aryl radicals, and aryl radicals substituted with alkyl radicals; n is an integer between 1 and 4; R.sub.6 is an alkyl chain comprising between 1 and 4 carbon atoms; X is oxygen; and R.sub.1 is selected from the group consisting of ##STR3## wherein Y is as defined in the specification, and a is an integer of from zero to 3.
    Type: Grant
    Filed: October 4, 1993
    Date of Patent: October 25, 1994
    Assignee: Whitby Research, Inc.
    Inventors: James V. Peck, Gevork Minaskanian
  • Patent number: 5347049
    Abstract: Di-amines endowed with chain extension activity for formulations such as polyureas and polyurethanes are disclosed, and which have the general formula: ##STR1## wherein n is 0-1000; R.sub.1, R.sub.2, R.sub.5, and R.sub.6 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH; R.sub.3 =R.sub.4, and R.sub.3 and R.sub.4 are from the group --CH.sub.2 CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3) H--CH.sub.2 --; and the diasteromeric salts thereof.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: September 13, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III
  • Patent number: 5331011
    Abstract: Disclosed is an N-benzyl-N-phenoxyethylamine selected from the group consisting of the N-benzyl-N-phenoxyethylamine represented by the following formula (I): ##STR1## and an agriculturally acceptable acid addition salt represented by the following formula (II): ##STR2## wherein m represents a number of 1 or 2 with a proviso that when m is 1 and a chlorine atom in the ring A is present at para(4)-position of the ring A, two chlorine atoms in the ring B are present at 2,3-, 2,5-, 2,6-, 3,4- or 3,5-positions of the ring B, and HX represents an acid.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: July 19, 1994
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Mitsunori Oda, Kazutoshi Kikkawa, Akinori Tanaka, Satoko Imaruoka, Shigeo Yoshinaka
  • Patent number: 5312990
    Abstract: Di-amines endowed with chain extension activity for formulations such as polyureas and polyurethanes are disclosed, and which have the general formula: ##STR1## wherein n is 0-1000; R.sub.1, R.sub.2, R.sub.5, and R.sub.6 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH; R.sub.3 .dbd.R.sub.4, and R.sub.3 and R.sub.4 are from the group --CH.sub.2 --CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3)H--CH.sub.2 --; and the diasteromeric salts thereof.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: May 17, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III
  • Patent number: 5276192
    Abstract: A process for preparing phenoxyethanamines from phenols and 2-oxazolines in quantitative yields was discovered. Phosphoric acid hydrolyzes the amide intermediate from the phenol/2-oxazoline reaction without cleaving the amide at the ether linkage and without undesired aromatic ring substitution. Thus, yield to the desired phenoxyethanamines is often 98% or better, requiring no subsequent purification. In contrast, sulfuric and hydrochloric acids give these undesired side reactions. Phenoxyethanamines are useful in thermosetting resins, pharmaceuticals and as surfactants.
    Type: Grant
    Filed: April 22, 1991
    Date of Patent: January 4, 1994
    Assignee: Texaco Chemical Company
    Inventors: Wei-Yang Su, George P. Speranza
  • Patent number: 5238959
    Abstract: The present invention provides 3-(4-substitutedphenoxy)-3-phenyl propanamines capable of inhibiting the uptake of serotonin. These compounds are useful for treating many pharmacological disorders, including depression and obesity. These compounds can also be used to reduce the desire to smoke and consume alcohol.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: August 24, 1993
    Assignee: Eli Lilly and Company
    Inventors: David W. Robertson, David T. Wong
  • Patent number: 5198587
    Abstract: Phenethylamine derivatives shown by the general formula ##STR1## wherein Ro represents a lower alkyl group; R.sub.1 represents a lower alkyl group or a lower alkoxy group; R.sub.2 represents hydrogen atom or a hydroxyl group; R.sub.3 and R.sub.4 each represents hydrogen atom or a lower alkyl group; R.sub.5 represents hydrogen atom or a lower alkoxy group; X represents oxygen atom or a methylene group; m is an integer of 1-3; and n is an integer of 0-2 and the acid addition salts thereof.These compounds exhibit a strong .alpha.-adrenergic blocking action and are useful as an antihypertensive agent.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: March 30, 1993
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kazuo Imai, Kunihiro Niigata, Takashi Fujikura, Shinichi Hashimoto, Toichi Takenaka, Kazuo Honda
  • Patent number: 5147880
    Abstract: Benzo[a]fluorenes having an aminoalkoxy group on a phenyl ring at the 11-position have estrogenic and anti-estrogenic activity.
    Type: Grant
    Filed: July 22, 1991
    Date of Patent: September 15, 1992
    Assignee: Eli Lilly and Company
    Inventor: Charles D. Jones
  • Patent number: 5093526
    Abstract: N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine is prepared by reacting 2-phenoxy ethanol with thionyl chloride in the presence of a catalytic amount of tetra-alkyl ammonium halide optionally in the presence of a solvent to form 2-phenoxy ethyl chloride; reacting the 2-phenoxy ethyl chloride with n-propylamine at a temperature of from 50.degree. C. to 150.degree. C. optionally in the presence of a solvent to form N-n-propyl-N-2-phenoxy-ethyl amine; selectively chlorinating N-n-propyl-N-2-phenoxyethyl amine with chlorine in the presence of a solvent; and recovering the N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine formed.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: March 3, 1992
    Assignee: Makhteshim Chemical Works Ltd.
    Inventors: Joseph Sharvit, Abraham A. Pereferkovich
  • Patent number: 5091578
    Abstract: N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethylamine is prepared by selectively chlorinating 2-phenoxy ethanol by reacting it with chlorine either in the presence of hydrogen chloride at a temperature of from -10.degree. C. to 50.degree. C. or in the presence of urea at a temperature of from 20.degree. C. to 55.degree. C. in a water/carbon tetrachloride solvent mixture to form 2-(2,4,6-trichlorophenoxy)ethanol; reacting the 2-(2,4,6-trichlorophenoxy)ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium chloride, optionally in the presence of a solvent to form 2-(2,4,6-trichlorophenoxy)ethyl chloride; and reacting the 2-(2,4,6-trichlorophenoxy) ethyl chloride with n-propylamine at a temperature of from 20.degree. C. to 150.degree. C., optionally in the presence of water to form N-n-propyl-N-2-(2,4,6-trichlorophenoxy) ethyl amine.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: February 25, 1992
    Assignee: Makhteshim Chemical Works Ltd.
    Inventors: Joseph Sharvit, Abraham A. Pereferkovich, Daniel Shohat
  • Patent number: 5091577
    Abstract: N-n-propyl-N-(2,4,6-trichlorophenoxy)-ethyl amine is prepared by reacting 2-phenoxy ethanol with thionyl chloride in the presence of a catalytic amount of tetraalkyl ammonium halide optionally in the presence of a solvent to form 2-phenoxy ethyl chloride; selectively chlorinating the 2-phenoxy ethyl chloride with chlorine at a temperature from 0.degree. C. to 60.degree. C. in the presence of a catalytic amount if urea to form 2-(2,4,6-trichlorophenoxy)-ethyl chloride; reacting the 2-(2,4,6-trichlorophenoxy)-ethyl chloride with n-propyl amine at a temperature of from 20.degree. C. to 150.degree. C., optionally in the presence of water; and recovering the N-n-propyl-N-2-(2,4,6-trichlorophenoxy)-ethyl amine formed.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: February 25, 1992
    Assignee: Makhteshim Chemical Works Ltd.
    Inventors: Joseph Sharvit, Abraham A. Pereferkovich
  • Patent number: 5070106
    Abstract: Compounds of formula ##STR1## (wherein R, R.sub.1, R.sub.2, R.sub.3, n, m, and p have the meanings reported in the specification), their preparation and the compositions for pharmaceutical use containing them as active ingredient are described.The compounds of formula I have dopaminergic vasodilator activity and they may be used in pharmaceutical field.
    Type: Grant
    Filed: February 22, 1991
    Date of Patent: December 3, 1991
    Assignee: Simes Societa Italiana Medicinali e Sintetici S.p.A.
    Inventors: Cesare Casagrande, Gabriele Norcini, Francesco Santangelo, Claudio Semeraro
  • Patent number: 5063246
    Abstract: Phenethylamine derivatives shown by the general formula ##STR1## wherein Ro represents a lower alkyl group; R.sub.1 represents a lower alkyl group or a lower alkoxy group, R.sub.2 represents hydrogen atom or a hydroxyl group; R.sub.3 and R.sub.4 each represents hydrogen atom or a lower alkyl group; R.sub.5 represents hydrogen atom or a lower alkoxy group; X represents oxygen atom or a methylene group; m is an integer of 1-3; and n is an integer of 0-2and the acid addition salts thereof.These compounds exhibit a strong .alpha.-adrenergic blocking action and are useful as an antihypertensive agent.
    Type: Grant
    Filed: August 21, 1990
    Date of Patent: November 5, 1991
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kazuo Imai, Kunihiro Niigata, Takashi Fujikura, Shinichi Hashimoto, Toichi Takenaka, Kazuo Honda
  • Patent number: 5057623
    Abstract: An organic fluorine compound represented by the general formulaR.sub.f -(X).sub.h -R-Mwherein R.sub.f is a group selected from the following (a) and (b); ##STR1## X denotes a linking group selected from --O--, --S--, and --COO--, h denotes 0 or 1, R is a hydrocarbon chain comprising a phenylene group having an alkylene group with a total carbon number of 10 or more, or the derivative thereof, or an aliphatic alkylene group of a carbon number of 10 or more, and M is a group selected from --OH, --COOH, --SH, and --CONH.sub.2.The organic fluorine compound of the present invention greatly improves the dispersibility of magnetic powders in magnetic coating materials, has also an excellent rust prevention effect on metallic magnetic powders, and exhibits a marked dispersing effect even on fluorocarbon resin fine powders, which can be difficultly dispersed with conventional dispersing agents.
    Type: Grant
    Filed: October 13, 1989
    Date of Patent: October 15, 1991
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yoshiaki Kai, Takashi Suzuki
  • Patent number: 5047420
    Abstract: Novel 1,3-diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediate by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: September 10, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
  • Patent number: 5030755
    Abstract: Disclosed are a process for producing a substituted phenoxyacetaldehyde oxime of the formula: ##STR1## (wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification), which comprises allowing a substituted phenoxyacetaldehyde dialkylacetal of the formula: ##STR2## (wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification) to react with hydroxylamine; a process for producing a substituted phenoxyethylamine of the formula: ##STR3## (wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification), which comprises reducing a substituted phenoxyacetaldehyde oxime of the formula (II) with hydrogen in the presence of a Raney-nickel catalyst; and a substituted phenoxyacetaldehyde oxime of the formula: ##STR4## (wherein R.sup.1, R.sup.2 and R.sup.6 are as defned in the specification).
    Type: Grant
    Filed: October 26, 1990
    Date of Patent: July 9, 1991
    Assignees: Ube Industries Ltd., Sankyo Co., Ltd.
    Inventors: Kikuo Ataka, Koji Imaoka, Kiyotaka Yoshii, Kenji Hirotsu
  • Patent number: 5021429
    Abstract: Compounds of the general formula: ##STR1## and physiologically acceptable salts, and hydrates, N-oxides and bioprecursors of such compounds and such salts in whichR.sub.1 and R.sub.2, which may be the same or different, represent hydrogen or lower alkyl, cycloalkyl, aralkyl or lower alkenyl groups, or lower alkyl groups interrupted by an oxygen atom or a group ##STR2## in which R.sub.4 represents hydrogen or lower alkyl; or R.sub.1 and R.sub.2 may, together with the nitrogen atom to which they are attached form a heterocyclic ring which may contain the hetero functions --O-- and ##STR3## R.sub.3 represents hydrogen, lower alkyl, alkenyl or alkoxyalkyl; X represents --O--, --S-- or --CH.sub.2 -- or ##STR4## where R.sub.5 is hydrogen or lower alkyl; Y represents .dbd.S, .dbd.O, .dbd.NR.sub.6 or .dbd.CHR.sub.7 ;in which R.sub.6 represents hydrogen, nitro, cyano, lower alkyl, aryl, arylsulphonyl or lower alkylsulphonyl; R.sub.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: June 4, 1991
    Assignee: Allen & Hansburys Limited
    Inventor: Michael Martin-Smith
  • Patent number: 5006561
    Abstract: Novel 5-alkanesulphonamido-2-[N-(4-alkanesulphonamidophenoxyalkyl)-N-methylamino ]indane and 5-alkanesulphonamido-2-[N-(4-alkanesulphonamidophenyl-alkyl)-N-methylamino ]indane compounds have been prepared, including their pharmaceutically acceptable salts and various key novel intermediates therefor. These compounds are useful in therapy as anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrhythmias. The most preferred member compouned is 5-methanesulphonamido-2-[N-(4-methanesulphonamidophenethyl)-N-methylamino] indane. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: April 17, 1990
    Date of Patent: April 9, 1991
    Assignee: Pfizer Inc.
    Inventors: John E. Arrowsmith, Peter E. Cross
  • Patent number: 4992474
    Abstract: Phenethanolamine derivatives are disclosed of formula ##STR1## wherein m is 2 to 8; n is 1 to 7 provided that m+n is 4 to 12;Ar is phenyl or phenyl substituted by one or two halogen atoms, alkyl or alkoxy groups or by an alkylenedioxy group;R.sup.1 and R.sup.2 are hydrogen or alkyl provided that the sum total of carbon atoms in R.sup.1 and R.sup.2 is not more than 4;and the physiologically acceptable salts and solvates thereof.The compounds have a selective stimulant action at .beta..sub.2 -adrenoreceptors and may be used inter alia in the treatment of diseases associated with reversible airways obstructions such as asthma and chronic bronchitis. The compounds may be formulated in conventional manner as pharmaceutical compositions with physiologically acceptable carriers or excipients.The compounds may be prepared, for example by alkylation of an amine: ##STR2## where R.sup.3, R.sup.5 and R.sup.6 is hydrogen or a protecting group, followed by removal of any protecting group.
    Type: Grant
    Filed: August 23, 1989
    Date of Patent: February 12, 1991
    Assignee: Glaxo Group Ltd.
    Inventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor
  • Patent number: 4985596
    Abstract: A process for producing a substituted phenoxyacetaldehyde oxime of the formula: ##STR1## (wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification), which comprises reacting a substituted phenoxyacetaldehyde dialkylacetal of the formula: ##STR2## (wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification) with a hydroxylamine at a pH of from 0.1 to 1.0.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: January 15, 1991
    Assignees: UBE Industries, Ltd., Sankyo Co., Ltd.
    Inventors: Kikuo Ataka, Koji Imaoka, Kiyotaka Yoshii, Kenji Hirotsu
  • Patent number: 4959366
    Abstract: A series of [N-alkyl-N-(nitro-, alkylsulphonamido, or amino-phenalkyl)amino]-alkyl, alkoxy or alkylthio phenyl derivatives having utility as anti-arrhythmic agents.
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: September 25, 1990
    Assignee: Pfizer Inc.
    Inventors: Peter E. Cross, Geoffrey N. Thomas, John E. Arrowsmith
  • Patent number: 4931474
    Abstract: An ether derivative compound of the formula: ##STR1## wherein R.sup.1 is hydrogen, chloro, methyl or (C.sub.1 -C.sub.3)-alkoxy, R.sup.2 is (C.sub.1 -C.sub.6)-alkyl, R.sup.3 is hydrogen, chloro, bromo, fluoro, --CF.sub.3, nitro, (C.sub.1 -C.sub.4)-alkyl, methoxy, phenoxy or (C.sub.1 -C.sub.3)-alkylthio, R.sup.4 is hydrogen, chloro or methyl, Y is oxygen, sulfur, sulfinyl, sulfonyl, or imino, x is 0, 1 or 2, y is 0 or 1, a is 0 or 1, b is an integer of 0 to 6, c is 0 or 1, d is 0, 1 or 2, e is 0 or 1, except that all of a, b and c are zero.
    Type: Grant
    Filed: July 27, 1987
    Date of Patent: June 5, 1990
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Shoichi Kato, Tatsumi Hayaoka
  • Patent number: 4888447
    Abstract: A process is described for selectively preparing alkoxylated tertiary amine compounds, such as aminated ethoxylated amines, at ambient pressure by reacting an oxyalkylated alcohol with a secondary amine in the presence of a reductive amination catalyst at above ambient temperature using, as a reductive amination catalyst, a combination of Raney nickel and molybdenum.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: December 19, 1989
    Assignee: Ethyl Corporation
    Inventor: Kim R. Smith
  • Patent number: 4883804
    Abstract: There are described compounds of formula I, ##STR1## in which X represents a C2 to 8 alkylene chain optionally interrupted by a double bond or by S(O).sub.n, wherein n is 0, 1 or 2;Y represents O or NH,l and m each independently represent 2, 3 or 4,R.sub.10 represents phenyl substituted by one or more substituents R.sub.23, which may be the same or different; or R.sub.10 represents pyridyl, a saturated carbocyclic group, alkyl C 1 to 6 or hydrogen,R.sub.15 represents hydrogen or together with R.sub.23 forms a (CH.sub.2).sub.p chain, wherein p represents 0, 1 or 2;R.sub.20, R.sub.21, R.sub.22 and R.sub.23, which may be the same or different, independently represent hydrogen, alkyl C 1 to 6, NHR.sub.25, SH, NO.sub.2, halogen, CF.sub.3, SO.sub.2 R.sub.30, CH.sub.2 OH or OH, wherein R.sub.25 represents hydrogen, alkyl C 1 to 6, alkanoyl C 1 to 6 or SO.sub.2 alkyl C 1 to 6, and R.sub.30 represents alkyl C 1 to 6 or NH.sub.
    Type: Grant
    Filed: November 19, 1986
    Date of Patent: November 28, 1989
    Assignee: Fisons plc
    Inventors: Francis Ince, Brian Springthorpe, John Dixon
  • Patent number: 4861916
    Abstract: Compounds of the general formula I ##STR1## wherein Z is CR.sup.1 R.sup.2 (OR.sup.3) or phenyl,R.sup.1 being H, C.sub.1-6 -alkyl or phenyl,R.sup.2 being H, C.sub.1-6 -alkyl or C.sub.1-6 -alkoxy andR.sup.3 being H, C.sub.1-6 -alkyl or C.sub.1-6 -alkanoyl andZ' is Y--[(CH.sub.2).sub.m --X].sub.n --,X being CH.sub.2 or 0,Y being OH; COOH or SO.sub.3 H including the alkali metal, alkaline earth metal or ammonium salts thereof and also the salts thereof with organic nitrogen bases; or NRR' in which R and R' are in each case H, C.sub.1-20 -alkyl or C.sub.1-4 -hydroxyalkyl, if appropriate quaternized or in the form of the acid addition salts, andn and m each being the numbers 1-4,are excellently suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds, in particular in aqueous systems.
    Type: Grant
    Filed: December 3, 1986
    Date of Patent: August 29, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Manfred Kohler, Jorg Ohngemach, Gregor Wehner, Jurgen Gehlhaus
  • Patent number: 4838894
    Abstract: A substituted m-aminophenol coupler useful in hair dyeing having the formula ##STR1## and acid addition salts thereof wherein x and y are selected from the group consisting of halogen and the groups OR of which R is the same or different alkyl, aminoalkyl or hydroxyalkyl groups, at least one of x or y being a group OR and a process for preparing these compounds.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: June 13, 1989
    Assignee: Clairol Incorporated
    Inventors: James E. Kijek, Keith C. Brown, Bryan P. Murphy
  • Patent number: 4831051
    Abstract: New aromatic derivatives having an activity antagonistic to calcium and corresponding to formula: ##STR1## in which: A represents a chain having any one of the following structures: ##STR2## Ar represents a group of structure: ##STR3## n takes the value 1 or 2 when R is different from H; m takes the value 2 or 3.
    Type: Grant
    Filed: January 22, 1988
    Date of Patent: May 16, 1989
    Assignee: Delande S.A.
    Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
  • Patent number: 4818772
    Abstract: A compound with alpha 1-blocking activity having the formula: ##STR1## wherein R.sub.1 is --H, --CH.sub.3 or --COCH.sub.3 ; R.sub.2 is --H or CH.sub.3 ; and R.sub.3 is ##STR2## wherein .SIGMA. is --H or one or more substituents selected from the group consisting of halogen, --OH and --OCH.sub.3 ; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: April 9, 1982
    Date of Patent: April 4, 1989
    Assignee: Societe Cortial S.A.
    Inventors: Henri Pontagnier, Christian Courtiol, Marie-Helene Creuzet, Claude Feniou, Gisele Prat
  • Patent number: 4764533
    Abstract: Erythro-1,2,3-triphenyl-1-pentanones of Formula 1 ##STR1## wherein R.sup.1 may be a dimethylamino, diethylamino, piperidin-1-yl- or pyrrolidin-1-yl group and R.sup.2 represents a hydrogen atom, a methoxy or hydroxy group, and their pharmacologically acceptable salts, have a pronounced antiestrogenic effect and are suitable for the treatment of hormone-dependent tumors.They may be prepared by reacting 1,2-diphenyl-ethanone of Formula 2 ##STR2## wherein R.sup.1 is as set forth in Formula 1 and R.sup.2 represents a hydrogen atom or a methoxy group, with sodium hydride in anhydrous dimethyl-formamide, isolating after conversion with 1-chloro-1-phenylpropane, the erythro form from the reaction product and possibly releasing the hydroxy group from the methoxy group by selective cleavage with hydrobromic acid.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: August 16, 1988
    Assignee: Klinge Pharma GmbH
    Inventors: Helmut Schickaneder, Roland Loser
  • Patent number: 4732896
    Abstract: New aromatic derivatives having an activity antagonistic to calcium and corresponding to formula: ##STR1## in which: A represents a chain having any one of the following structures: ##STR2## Ar represents a group of structure: ##STR3## n takes the value 1 or 2 when R is different from H; m takes the value 2 or 3.
    Type: Grant
    Filed: June 26, 1985
    Date of Patent: March 22, 1988
    Assignee: Delalande S.A.
    Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
  • Patent number: 4692465
    Abstract: Compounds of formula (I): ##STR1## or a pharmaceutically acceptable salt, ester or amide thereof, wherein: Ar is benzofuran-2-yl, or phenyl optionally substituted by groups R.sup.1 and/or R.sup.2 wherein R.sup.1 is halogen, trifluoromethyl or hydroxy and R.sup.2 is halogen;R.sup.3 is hydrogen or methyl;X is --O(CH.sub.2).sub.a CO.sub.2 H, --O(CH.sub.2)bM or --CO.sub.2 Hin whicha is an integer from 1 to 6,b is an integer from 2 to 7,M is hydroxy, C.sub.1-6 alkoxy, phenyl C.sub.1-6 alkoxy, or --NR.sup.4 R.sup.5 in which R.sup.4 and R.sup.5 are each hydrogen or C.sub.1-6 alkyl or together form a five or six membered heterocyclic ring;Y is C.sub.2-6 straight or branched alkylene, with at least two carbon atoms between the --O-- and --OH;and n is 1 or 2,having anti-obesity and/or anti-hyperglycaemic activity, processes for their preparation and their pharmaceutical use.
    Type: Grant
    Filed: August 15, 1984
    Date of Patent: September 8, 1987
    Assignee: Beecham Group PLC
    Inventors: Richard M. Hindley, John Berge
  • Patent number: 4661297
    Abstract: Basic ethers of 7-oxo-7H-benzo(c) fluorene have been shown to evidence a pronounced antineoplastic and immunosuppressive effect in mammals suffering from leukemia. The technique for preparing the described ethers and the addition salts thereof with pharmaceutically acceptable organic and inorganic acids involves the aminoalkylation of 5-hydroxy-7-oxo-7H-benzo(c) fluorene and its corresponding nuclear substituted derivatives on the hydroxylic oxygen atom.
    Type: Grant
    Filed: September 14, 1982
    Date of Patent: April 28, 1987
    Assignee: SPOFA, spojene podniky pro zdravotnickou vyrobu
    Inventors: Jiri Krepelka, Iva Vancurova, Karel Rezabek, Milan Melka, Vojtech Pujman, Stanislava Pokorna, Ruzena Reichlova, Slavjanka Cernochova
  • Patent number: 4526973
    Abstract: Certain 1-(substituted amino)-2-(amino or substituted amino)cyclobutene-3,4-diones of the general formula ##STR1## are potent histamine H.sub.2 -antagonists useful in the treatment of peptic ulcers. A preferred compound, 1-amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione, is prepared by treating an intermediate, 1-methoxy-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dion e, with ammonia.
    Type: Grant
    Filed: June 9, 1982
    Date of Patent: July 2, 1985
    Assignee: Bristol-Myers Company
    Inventors: Aldo A. Algieri, Ronnie R. Crenshaw
  • Patent number: 4522943
    Abstract: Compounds of the formula ##STR1## wherein R.sup.12 is a leaving group, Z is S, O or CH.sub.2 and A is a phenyl, furyl, thienyl or pyridyl ring substituted by a ##STR2## moiety, in which R.sup.8 and R.sup.9 are various substituents or, when taken together with the nitrogen, may be a specified heterocyclic ring, are intermediates in the preparation of histamine H.sub.2 -antagonist anti-ulcer agents of the formula ##STR3## in which R.sup.1 and R.sup.2 are any of several specified substituents.
    Type: Grant
    Filed: April 21, 1982
    Date of Patent: June 11, 1985
    Assignee: Bristol-Myers Company
    Inventors: Aldo A. Algieri, Ronnie R. Crenshaw
  • Patent number: 4417896
    Abstract: Novel compounds of the general formula ##STR1## wherein Z represents a substituted lower alkyl radical; each of R.sub.1 and R.sub.2 is hydrogen atom, a lower alkyl or a substituted lower alkyl identical with or different from Z and the functional groups NO.sub.2 and NR.sub.1 R.sub.2 can occupy all ring positions in relation to OZ, with the exception that if Z is .beta.-hydroxyethyl, --NO.sub.2 is in the 4 position and --N(R.sub.1)(R.sub.2) is in the 2 position then either R.sub.1 or R.sub.2 is other than hydrogen.The novel compounds are for dyeing human hair in a variety of yellow shades. The compounds of formula (I) may be used as aqueous or water-alcohol solutions to form dye compositions for dyeing human hair.
    Type: Grant
    Filed: April 6, 1982
    Date of Patent: November 29, 1983
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Andree Bugaut, Patrick Andrillon
  • Patent number: 4342782
    Abstract: 1-(Substituted-aminoalkoxyphenyl)-2-methylene-1-alkanones, a class of compounds possessing antiallergic propertiesfor use in the treatment of allergic conditions, such as asthma prepared by etherifying an alkanoylphenol with an aminoalkyl halide, converting the ether formed to a salt of Mannich base by reacting it with a salt of a secondary amine in the presence of formaldehyde or paraformaldehyde and treating the Mannich salt with a weak base todeaminate the same and form the final product.
    Type: Grant
    Filed: November 16, 1978
    Date of Patent: August 3, 1982
    Assignee: Merck & Co., Inc.
    Inventor: Edward J. Cragoe, Jr.
  • Patent number: 4339393
    Abstract: The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1--3 --alkylene--CON(R.sub.4)--, --CON(R.sub.4)--,--O--C.sub.1--3 --alkylene--COO--, OCO or --COO--, with the proviso that if n+n'=O, X and X' may not be --CON(R.sub.4)--or O--C.sub.1--3 --alkylene--CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)--or --COO--, A.crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1--20 --alkylene, R.sub.1 and R.sub.1' independently of one another are unsubstituted or substituted C.sub.1--8 --alkyl or C.sub.3--4 --alkenyl, or R.sub.1 together with R.sub.2, or R.sub.1' together with R.sub.2', is a heterocyclic ring, R.sub.2 and R.sub.2' independently of one another are unsubstituted or substituted C.sub.1--8 --alkyl or C.sub.3--4 -- alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2' together with R.sub.1', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1' and R.
    Type: Grant
    Filed: April 4, 1980
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Christian Luthi, Hans R. Meyer, Kurt Weber