Hydrogen Or Acyclic Hydrocarbyl Substituents Only Bonded Directly To The Part Of The Chain Between The Ether Oxygen And Amino Nitrogen Patents (Class 564/353)
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Patent number: 5637771Abstract: A method of lowering cholesterol which comprises administering to a host requiring such treatment an effective amount of a compound of the formula ##STR1## wherein one of R.sup.1 and R.sup.2 is C.sub.1-7 -alkyl and the other is C.sub.1-7 -alkyl or C.sub.2-6 -alkenyl-methyl;L is C.sub.1-11 -alkylene or C.sub.2-11 -alkenylene optionally bonded to the phenyl group via an O atom or L is 1,4-phenylene;n is 0 or, when L contains an O atom, n is 0 or 1;Q is C.sub.1-7 -alkyl, C.sub.2-10 -alkenyl or a group of formula ##STR2## wherein R is H, halogen, CF.sub.3, CN or NO.sub.2 ; R.sup.3 and R.sup.4 are H, C.sub.1-4 -alkyl or halogen; andR.sup.5 is H or, when R is H, R.sup.5 is H or halogen;or a pharmaceutically acceptable acid addition salt thereof, as well as certain compounds of formula I, are described.Type: GrantFiled: November 8, 1995Date of Patent: June 10, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Johannes Aebi, Philipe Guerry, Synese Jolidon, Olivier Morand
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Patent number: 5556864Abstract: Compounds of formula (I): ##STR1## [wherein: R.sup.1 is aryl; R.sup.2 is hydrogen, alkyl, alkoxy, halogen or cyano; R.sup.3 is a group of formula --B--NR.sup.4 R.sup.5, where R.sup.4 and R.sup.5 are independently hydrogen, alkyl or substituted alkyl or R.sup.4 and R.sup.5, together with the nitrogen to which they are attached, form a heterocycle, and B is alkylene or a group of formula --CH.sub.2 CH(OR.sup.6)CH.sub.2 --, where R.sup.6 is hydrogen, alkanoyl, substituted alkanoyl or arylcarbonyl, or a group of formula --D--R.sup.7, where D is a single bond or alkylene and R.sup.7 is a heterocycle; and A is alkylene; and pharmaceutically acceptable salts and esters thereof] are useful for the treatment and prevention of circulatory diseases and psychosis.Type: GrantFiled: January 5, 1995Date of Patent: September 17, 1996Assignee: Sankyo Company, LimitedInventors: Koichi Fujimoto, Naoki Tanaka, Fumitoshi Asai, Tomiyoshi Ito, Hiroyuki Koike
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Patent number: 5495048Abstract: A method of lowering cholesterol which comprises administering to a host requiring such treatment an effective amount of a compound of the formula ##STR1## wherein one of R.sup.1 and R.sup.2 is C.sub.1-7 -alkyl and the other is C.sub.1-7 -alkyl or C.sub.2-6 -alkenyl-methyl;L is C.sub.1-11 -alkylene or C.sub.2-11 -alkenylene optionally bonded to the phenyl group via an O atom or L is 1,4-phenylene;n is 0 or, when L contains an O atom, n is 0 or 1;Q is C.sub.1-7 -alkyl, C.sub.2-10 -alkenyl or a group of formula ##STR2## wherein R is H, halogen, CF.sub.3, CN or NO.sub.2 ; R.sup.3 and R.sup.4 are H, C.sub.1-4 -alkyl or halogen; andR.sup.5 is H or, when R is H, R.sup.5 is H or halogen;or a pharmaceutically acceptable acid addition salt thereof, as well as certain compounds of formula I, are described.Type: GrantFiled: June 17, 1994Date of Patent: February 27, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Johannes Aebi, Philipe Guerry, Synese Jolidon, Olivier Morand
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Patent number: 5430062Abstract: 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: GrantFiled: June 23, 1993Date of Patent: July 4, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Mark S. Cushman, Ernest Hamel
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Patent number: 5420352Abstract: 1-Methyl-2-phenoxy ethanol of the formula, ##STR1## [wherein R is hydrogen or an alkyl group having 1 to 6 carbon atoms, and n is an integer of 0 or 1 to 5]is allowed to react with ammonia in a solvent in the presence of a copper-chromium catalyst and hydrogen, whereby 1-phenoxy-2-aminopropane of the formula ##STR2## [wherein R and n are as defined above] can be obtained at high yields at high selectivity.Type: GrantFiled: May 31, 1994Date of Patent: May 30, 1995Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hidetoshi Koga, Izumi Terada
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Patent number: 5409957Abstract: 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: GrantFiled: March 23, 1993Date of Patent: April 25, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mitsunori Oda, Kazutoshi Kikkawa, Akinori Tanaka, Satoko Imaruoka, Shigeo Yoshinaka
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Patent number: 5385892Abstract: 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: GrantFiled: January 4, 1993Date of Patent: January 31, 1995Assignee: Ministero Dell "Universita" E Dell Ricerca Scientifica E TecnologicaInventors: Giovanni Camaggi, Lucio Filippini, Marilena Gusmeroli, Carlo Garavaglia, Luigi Mirenna
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Patent number: 5358971Abstract: 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: GrantFiled: October 4, 1993Date of Patent: October 25, 1994Assignee: Whitby Research, Inc.Inventors: James V. Peck, Gevork Minaskanian
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Patent number: 5347049Abstract: 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: GrantFiled: January 11, 1994Date of Patent: September 13, 1994Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III
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Patent number: 5344984Abstract: A method for preparing "twin-tailed" tertiary amines which have two moles of alkoxylated phenol bonded to each nitrogen function of a molecule of methylamine and represented by the formula: ##STR1## wherein x represents zero to about 30 which comprises alkylating a mole of methylamine with two moles of alkoxylated alkylphenol over a catalyst comprising:5 to 70% nickel;1 to 20% copper;0.1 to 10% chromium; and0.1 to 10% molybdenum on an alumina support.Type: GrantFiled: April 8, 1993Date of Patent: September 6, 1994Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Carter G. Naylor
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Patent number: 5331011Abstract: 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: GrantFiled: April 7, 1993Date of Patent: July 19, 1994Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Mitsunori Oda, Kazutoshi Kikkawa, Akinori Tanaka, Satoko Imaruoka, Shigeo Yoshinaka
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Patent number: 5320825Abstract: Disclosed are novel compounds for CNS neurotransmitter systems, especially for the neurotransmitter serotonin, which have the formula ##STR1## where each of U, V, W, X, Y and Z is independently selected from the group consisting of hydrogen; halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkyl substituted with one or more moieties selected from halogen atoms and hydroxy groups; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 alkoxy substituted with one or more moieties selected from halogen atoms and hydroxy groups; C.sub.1 -C.sub.6 heterocycles; C.sub.1 -C.sub.4 thioalkyl; NR.sub.3 R.sub.4 ; --R.sub.5 --A --R.sub.6 ; and --A--R.sub.7 ; CN; SO.sub.2 R.sub.8 ; --NHCONH.sub.2 ; and C(O)NR.sub.3 R.sub.4 ;each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl;each of R.sub.5 and R.sub.6 is independently a C.sub.1 -C.sub.6 alkyl;R.sub.7 is selected from the group consisting of H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.Type: GrantFiled: May 1, 1991Date of Patent: June 14, 1994Assignee: Trustees of the University of PennsylvaniaInventor: Hank F. Kung
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Patent number: 5312990Abstract: 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: GrantFiled: May 28, 1993Date of Patent: May 17, 1994Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III
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Patent number: 5310756Abstract: Novel aryloxyphenylpropylamines having the formula ##STR1## wherein X is H, cyano, halogen, halogenoalkyl, C.sub.1-6 -alkoxy, C.sub.1- -alkyl, C.sub.1-5 -alkanoyl, C.sub.3-5 -alkylene, aryloxy- or aralkoxy, andR is 3,4-methylenedioxy, aryl or heteroaryl which are optionally substituted with one or more cyano, halogeno, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, C.sub.1-6 -alkenyl, trifluoromethyl, C.sub.3-5 -alkylene, aryloxy or aralkoxy; andR.sup.1 and R.sup.2 independently is C.sub.1-10 -alkyl, C.sub.3-7 -cycloalkyl, C.sub.2-10 -alkenyl, C.sub.3-6 -cycloalkyl-C.sub.1-5 -alkyl, optionally substituted with C.sub.1-5 -alkoxy or cyano; orR.sup.1 and R.sup.2 may together form a carbocyclic ring and a salt thereof with a pharmaceutically acceptable acid,provided however that R.sup.1 is not C.sub.3-7 -cycloalkyl, C.sub.1-10 -alkyl, or alkenyl which may be straight, branched or cyclic, unsubstituted or substituted with C.sub.1-4 -alkoxy, aryloxy or cycloalkyl or cycloalkylalkyl, when X is H and R.sup.2 is a methyl group.Type: GrantFiled: June 12, 1992Date of Patent: May 10, 1994Assignee: Novo Nordisk A/SInventors: Palle Jakobsen, Jorgen Drejer
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Patent number: 5276192Abstract: 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: GrantFiled: April 22, 1991Date of Patent: January 4, 1994Assignee: Texaco Chemical CompanyInventors: Wei-Yang Su, George P. Speranza
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Patent number: 5238959Abstract: 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: GrantFiled: April 20, 1992Date of Patent: August 24, 1993Assignee: Eli Lilly and CompanyInventors: David W. Robertson, David T. Wong
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Patent number: 5214046Abstract: The compound of the formula ##STR1## wherein each of R.sup.1 and R.sup.2 individually is hydrogen, lower alkyl or lower alkenyl or together signify straight-chain alkylene with 2 to 4 carbon atoms, R.sup.3 is hydrogen, halogen or lower alkyl, Q is alkylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies or alkenylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies and each of Y and Y' individually is a direct bond or the group --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--, the group R.sup.1 R.sup.Type: GrantFiled: February 6, 1992Date of Patent: May 25, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Philippe Guerry, Synese Jolidon, Rene Zurfluh
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Patent number: 5198587Abstract: 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: GrantFiled: July 30, 1991Date of Patent: March 30, 1993Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kazuo Imai, Kunihiro Niigata, Takashi Fujikura, Shinichi Hashimoto, Toichi Takenaka, Kazuo Honda
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Patent number: 5192799Abstract: Amine represented by the following formula (1), or their acid addition salts or their quaternary ammonium salts. ##STR1## The amines of formula (1) or their pharmaceutically acceptable acid addition salts or quaternary ammonium salts are useful for the treatment and prevention of heart diseases of animals, particularly arrhythima, myocardial infarction, angina pectoris and heart failure and psychoneurological diseases.Type: GrantFiled: June 5, 1992Date of Patent: March 9, 1993Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Ikuo Tomino, Masaharu Ishiguro, Takumi Kitahara, Keiichi Yokoyama, Noriaki Kihara, Joji Kamiya, Kanji Yoshihara, Masaaki Ishii, Akira Mizuchi, Kazutoshi Horikomi, Akira Awaya, Takuo Nakano
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Patent number: 5147880Abstract: Benzo[a]fluorenes having an aminoalkoxy group on a phenyl ring at the 11-position have estrogenic and anti-estrogenic activity.Type: GrantFiled: July 22, 1991Date of Patent: September 15, 1992Assignee: Eli Lilly and CompanyInventor: Charles D. Jones
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Patent number: 5145870Abstract: Novel aryloxyphenylpropylamines having the formula ##STR1## wherein X is H, cyano, halogen, halogenoalkyl, C.sub.1-6 -alkoxy, C.sub.1-6 -alkyl, C.sub.1-5 -alkanoyl, C.sub.3-5 -alkylene, aryloxy or aralkoxy, andR is 3,4-methylenedioxy, aryl or heteroaryl which are optionally substituted with one or more cyano, halogeno, C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, C.sub.1-6 -alkenyl, trifluoromethyl, C.sub.3-5 -alkylene, aryloxy or aralkoxy; andR.sup.1 and R.sup.2 independently is C.sub.1-10 -alkyl, C.sub.3-7 -cycloalkyl, C.sub.2-10 -alkenyl, C.sub.3-6 -cycloalkyl-C.sub.1-5 -alkyl, optionally substituted with C.sub.1-5 -alkoxy or cyano;R.sup.1 and R.sup.2 may together form a carbocyclic ring and a salt thereof with a pharmaceutically acceptable acid,provided however that R.sup.1 is not C.sub.3-7 -cycloalkyl, C.sub.1-10 -alkyl, or alkenyl which may be straight, branched or cyclic, unsubstituted or substituted with C.sub.1-4 -alkoxy, aryloxy or cycloalkyl or cycloalkylalkyl, when X is H and R.sup.2 is a methyl group.Type: GrantFiled: May 24, 1990Date of Patent: September 8, 1992Assignee: Novo Nordisk A/SInventors: Palle Jakobsen, Jorgen Drejer
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Patent number: 5093526Abstract: 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: GrantFiled: June 14, 1990Date of Patent: March 3, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich
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Patent number: 5091578Abstract: 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: GrantFiled: June 14, 1990Date of Patent: February 25, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich, Daniel Shohat
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Patent number: 5091577Abstract: 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: GrantFiled: June 14, 1990Date of Patent: February 25, 1992Assignee: Makhteshim Chemical Works Ltd.Inventors: Joseph Sharvit, Abraham A. Pereferkovich
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Patent number: 5070106Abstract: 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: GrantFiled: February 22, 1991Date of Patent: December 3, 1991Assignee: Simes Societa Italiana Medicinali e Sintetici S.p.A.Inventors: Cesare Casagrande, Gabriele Norcini, Francesco Santangelo, Claudio Semeraro
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Patent number: 5057623Abstract: 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: GrantFiled: October 13, 1989Date of Patent: October 15, 1991Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Yoshiaki Kai, Takashi Suzuki
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Patent number: 5047420Abstract: 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: GrantFiled: August 21, 1989Date of Patent: September 10, 1991Assignee: 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
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Patent number: 5021429Abstract: 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: GrantFiled: December 22, 1986Date of Patent: June 4, 1991Assignee: Allen & Hansburys LimitedInventor: Michael Martin-Smith
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Patent number: 4994616Abstract: A novel herbicide of formula I ##STR1## wherein R.sub.1 represents a halogen atom or an alkyl, haloalkoxy, haloalkyl or alkoxycarbonyl group;R.sub.2 represents a hydrogen or halogen atom;each of R.sub.3 to R.sub.6 independently represents a hydrogen or halogen atom or a cyano, alkyl, haloalkyl, alkoxy or haloalkoxy group;R.sub.7 represents a hydrogen or halogen atom, or an alkyl, haloalkoxy, haloalkyl or alkoxycarbonyl group;and A represents a nitrogen atom or a --CH-- group, together with its formulation and use as a herbicide, and its preparation.Type: GrantFiled: April 12, 1988Date of Patent: February 19, 1991Assignee: Ube Industries, Ltd.Inventor: David Munro
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Patent number: 4992474Abstract: 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: GrantFiled: August 23, 1989Date of Patent: February 12, 1991Assignee: Glaxo Group Ltd.Inventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor
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Patent number: 4971995Abstract: Pharmaceutical or veterinary preparations containing (a) at least one compound with the formula: ##STR1## where:R.sub.o represents a C.sub.3 -C.sub.6 alkyl group or a benzyl group with the formula: ##STR2##in which R.sub.3 =H, a halogen, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2 or a CN group; andR.sub.2 represents:a C.sub.1 -C.sub.4 alkoxy group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (CHOH, H), (O, H), (CH.sub.2, H) or (CO, H);and OH group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (O, H) or (CH.sub.2, H), with the reservation that when (X, R.sub.1)=(O, OH), R.sub.o is different from a C.sub.3 -C.sub.6 alkyl or a benzyl group; ora CN or C.sub.1 -C.sub.4 alkyl-NH group, in which case the pair (X, R.sub.1)=(O, H) or (CH.sub.2, H), together with (b) a carrier or vehicle which is physiologically acceptable and appropriate for the compound used.Type: GrantFiled: January 26, 1989Date of Patent: November 20, 1990Assignee: Delande S.A.Inventors: Alain R. Schoofs, Michel Langlois, Christian R. Jeanpetit, Maryse F. Masson
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Patent number: 4931474Abstract: 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: GrantFiled: July 27, 1987Date of Patent: June 5, 1990Assignee: Nippon Kayaku Kabushiki KaishaInventors: Shoichi Kato, Tatsumi Hayaoka
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Patent number: 4913891Abstract: This invention involves a new strategy for imaging and mapping enzyme activity in the living human and animal body using positron emitter-labeled suicide enzyme inactivators or inhibitors which become covalently bound to the enzyme as a result of enzymatic catalysis. Two such suicide inactivators for monoamine oxidase have been labeled with carbon-11 and used to map the enzyme subtypes in the living human and animal body using PET. By using positron emission tomography to image the distribution of radioactivity produced by the body penetrating radiation emitted by carbon-11, a map of functionally active monoamine oxidase activity is obtained. Clorgyline and L-deprenyl are suicide enzyme inhibitors and irreversibly inhibit monoamine oxidase. When these inhibitors are labeled with carbon-11 they provide selective probes for monoamine oxidase localization and reactivity in vivo using positron emission tomography.Type: GrantFiled: May 22, 1987Date of Patent: April 3, 1990Assignee: The United States of America as represented by the United States Department of EnergyInventors: Joanna S. Fowler, Robert R. MacGregor, Alfred P. Wolf, Bengt Langstrom
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Patent number: 4888447Abstract: 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: GrantFiled: June 30, 1988Date of Patent: December 19, 1989Assignee: Ethyl CorporationInventor: Kim R. Smith
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Patent number: 4861916Abstract: 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: GrantFiled: December 3, 1986Date of Patent: August 29, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Manfred Kohler, Jorg Ohngemach, Gregor Wehner, Jurgen Gehlhaus
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Patent number: 4845292Abstract: There are disclosed compounds of the formula ##STR1## R is --CH.sub.2 OH or --CO.sub.2 R.sup.3 ; R.sup.1 is hydrogen, lower alkyl, lower alkoxy or hydroxybenzyl;R.sup.2 is hydroxyloweralkyl or diloweralkoxyalkyl;R.sup.3 is hydrogen or lower alkyl;R.sup.4 is alkyl of 10-20 carbons atoms, phenylalkyl of 11-18 carbon atoms or phenoxyalkyl of 11-18 carbon atoms; orn is 1-3;or a pharmaceutically acceptable salt thereof, and their use in the prevention and/or treatment of conditions such as allergic rhinitis, allergic bronchial asthma and other naso-bronchial obstructive air-passageway conditions, other immediate hypersensitivity reactions such as allergic conjunctivitis and various inflammatory conditions.Type: GrantFiled: January 13, 1988Date of Patent: July 4, 1989Assignee: American Home Products CorporationInventors: William H. McGregor, Lisa A. Marshall, John H. Musser
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Patent number: 4838894Abstract: 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: GrantFiled: December 21, 1987Date of Patent: June 13, 1989Assignee: Clairol IncorporatedInventors: James E. Kijek, Keith C. Brown, Bryan P. Murphy
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Patent number: 4831051Abstract: 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: GrantFiled: January 22, 1988Date of Patent: May 16, 1989Assignee: Delande S.A.Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
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Patent number: 4818772Abstract: 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: GrantFiled: April 9, 1982Date of Patent: April 4, 1989Assignee: Societe Cortial S.A.Inventors: Henri Pontagnier, Christian Courtiol, Marie-Helene Creuzet, Claude Feniou, Gisele Prat
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Patent number: 4803225Abstract: There are provided compounds of formula I, ##STR1## and pharmaceutically acceptable derivatives thereof. There are also described the use of the compounds of formula I as pharmaceuticals, methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.Type: GrantFiled: December 2, 1987Date of Patent: February 7, 1989Assignee: Fisons, plcInventors: John Dixon, Francis Ince
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Patent number: 4792570Abstract: Compounds useful for treating inflammation, swelling and associated pain, represented by the formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: a is an integer of 0-3;b is an integer of 0-2;n is an integer of 3-12;each X and each Y are independently -halo, --R.sup.1, -alkoxy, or -phenyl; andB is selected from the group consisting of:--NR.sup.1 R.sup.2, --NR.sup.1 (CH.sub.2 CH.sub.2 OH), ##STR2## in which R.sup.1 and R.sup.2 are independently H, alkyl or cycloalkyl;R.sup.3 is H, alkyl or --CH.sub.2 CH.sub.2 OH; andm is an integer of 3-8.Novel compounds are those wherein n is at least 6 if both a and b are 0.Type: GrantFiled: April 6, 1984Date of Patent: December 20, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Peter H. Nelson, James P. Dunn, Stefan H. Unger, Thomas R. Thieme
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Patent number: 4777294Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against .alpha.-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.Type: GrantFiled: April 17, 1987Date of Patent: October 11, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
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Patent number: 4732896Abstract: 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: GrantFiled: June 26, 1985Date of Patent: March 22, 1988Assignee: Delalande S.A.Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
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Patent number: 4720586Abstract: There are provided compounds of formula I, ##STR1## in which R.sub.1 represents OH,R.sub.2 and R.sub.3, which may be the same or different, each independently represent hydrogen, fluorine, chlorine, bromine, alkyl C1 to 6, nitro, nitrile, (CH.sub.2).sub.p R.sub.9 or SR.sub.9,W represents a single bond, a 1,2; 1,3; or 1,4-disubstituted benzene ring; a --CH.dbd.CH--group or a 1,4-cyclohexanediyl group;X respresents NH, O, S, SO.sub.2, CO, CH.sub.2, CONH or --COO;Y represents (CH.sub.2)q, CO, CS, SO.sub.2 and R.sub.20 represents hydrogen,or Y represents CR.sub.15 R.sub.16 CR.sub.17 R.sub.18,wherein the carbon atom bearing R.sub.15 and R.sub.16 is adjacent to X and in whichR.sub.15 and R.sub.18, together with the carbon atom to which they are attached form a carbonyl group, and R.sub.15, R.sub.16 and R.sub.20 each represent hydrogen, orR.sub.15 and R.sub.20 together form a chain --CH.sub.2 --, and R.sub.16, R.sub.17 and R.sub.18 each represent hydrogen, orR.sub.15, R.sub.16, R.sub.17 and R.sub.Type: GrantFiled: October 18, 1984Date of Patent: January 19, 1988Assignee: Fisons, plcInventors: John Dixon, Francis Ince
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Patent number: 4701559Abstract: A compound of the formula: ##STR1## wherein A is a chain hydrocarbon group having 1 to 10 carbon atoms optionally substituted by hydroxyl, phenoxy, thienyl, furyl, pyridyl, cyclohexyl or an optionally substituted phenyl group, or a cyclic hydrocarbon group having 3 to 7 carbon atoms optionally substituted by hydroxyl, B is hydrogen or hydroxyl, and their production and use.These compounds exhibit excellent inhibitory activity against .alpha.-glucoside hydrolase, thus are useful for hyperglycemic symptoms and various disorders caused by hyperglycemia.Type: GrantFiled: December 28, 1981Date of Patent: October 20, 1987Assignee: Takeda Chemical Industries, Inc.Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase
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Patent number: 4699928Abstract: Fluoroallylamine derivatives of the following Formula I are novel MAO-inhibitors and at low dose levels selectively inhibit MAO-B: ##STR1## wherein: R.sub.1 and R.sub.2 independently represent hydrogen, chlorine or fluroine;R.sub.3 represents hydrogen or (C.sub.1 -C.sub.4)alkyl; andX represents oxygen or sulfur.They are useful for the treatment of depression and, co-administered with L-dopa, in the treatment of Parkinsonism.Type: GrantFiled: November 6, 1986Date of Patent: October 13, 1987Assignee: Merrell Dow Pharmaceuticals Inc.Inventor: Ian A. McDonald
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Patent number: 4692465Abstract: 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: GrantFiled: August 15, 1984Date of Patent: September 8, 1987Assignee: Beecham Group PLCInventors: Richard M. Hindley, John Berge
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Patent number: 4661297Abstract: 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: GrantFiled: September 14, 1982Date of Patent: April 28, 1987Assignee: SPOFA, spojene podniky pro zdravotnickou vyrobuInventors: Jiri Krepelka, Iva Vancurova, Karel Rezabek, Milan Melka, Vojtech Pujman, Stanislava Pokorna, Ruzena Reichlova, Slavjanka Cernochova
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Patent number: 4526973Abstract: 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: GrantFiled: June 9, 1982Date of Patent: July 2, 1985Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw
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Patent number: 4522943Abstract: 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: GrantFiled: April 21, 1982Date of Patent: June 11, 1985Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw