The Aryl Ring Or Ring System And Amino Nitrogen Are Bonded Directly To The Same Acyclic Carbon, Which Carbon Additionally Has Only Hydrogen Or Acyclic Hydrocarbyl Substituents Bonded Directly Thereto Patents (Class 564/384)
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Patent number: 5504253Abstract: A method of making (R)-N- 1-(3-methoxyphenyl)ethyl!-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of (R)-3-methoxy-.alpha.-methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have the formula: ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl.Type: GrantFiled: July 15, 1994Date of Patent: April 2, 1996Assignee: NPS Pharmaceuticals, Inc.Inventors: Bradford C. VanWagenen, Thomas E. D'Ambra
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Patent number: 5407961Abstract: The present invention is concerned with antiretroviral (e.g. anti HIV-1) compounds having the formula ##STR1## Pharmaceutical compositions containing said compounds of formula (I-a) or (I-b), and processes of preparing said compounds and compositions.Type: GrantFiled: May 12, 1994Date of Patent: April 18, 1995Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Frans M. A. Van den Keybus, Karin J. M. M. Nuyens, Paul A. J. Janssen
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Patent number: 5359091Abstract: A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl; R.sup.21 is a group of the formula: ##STR2## wherein each of R.sup.3, R.sup.31, and R.sup.32 which may be the same or different, is hydrogen or lower alkyl, each of R.sup.4, R.sup.5, R.sup.41 and R.sup.51, which may be the same or different, is hydrogen, halogen, hydroxyl, lower alkyl or lower alkoxy, R.sup.42 is hydroxyl, halogen, R.sup.8 --O--, or R.sup.6 --X--Y-- wherein R.sup.6 is phenyl or thienyl which may have one or two substituents each of X and Y, which may be the same or different, is oxygen, sulfur, carbonyl, --CHR.sup.8 -- or --NR.sup.b, or X and Y together form a vinylene group or an ethynylene group, provided that when either one of X and Y is oxygen, sulfur or --NR.sup.b, the other is carbonyl or --CHR.sup.a, and R.sup.Type: GrantFiled: November 18, 1993Date of Patent: October 25, 1994Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
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Patent number: 5334628Abstract: Amine derivatives having the general formula (I): ##STR1## wherein X is selected from the group consisting of ##STR2## wherein Q is oxygen, sulfur or nitrogen atom, and ##STR3## wherein Q is as above; Y is selected from the group consisting of ##STR4## R.sup.1 is hydrogen atom or an alkyl group; R.sup.2 is hydrogen atom or an alkyl group; R.sup.3 is hydrogen atom, a halogen atom or an alkyl group; R.sup.4 hydrogen atom, an alkyl group, a cycloalkyl group, a halogenated alkyl group or a halogen atom; R.sup.5 is hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, nitro group or hydroxy group; R.sup.5 is attached to an arbitrary position of X, and R.sup.3 or R.sup.4 is attached to an arbitrary position of Y.The amine derivatives (I) are useful as fungicides.Type: GrantFiled: December 31, 1992Date of Patent: August 2, 1994Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Tetsuya Maeda, Toshiyuki Yamamoto, Mituo Takase, Kazuya Sasaki, Tadashi Arika, Mamoru Yokoo, Rieko Hashimoto, Kouji Amemiya, Sakae Koshikawa
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Patent number: 5306821Abstract: This invention relates to a novel process for the preparation of tertiary carbinamines by double addition of organolanthanide reagents, especially organocerium reagents, to nitriles. It further relates to the preparation of such amines by the addition of organolanthanide reagents to imines.Type: GrantFiled: January 10, 1992Date of Patent: April 26, 1994Assignee: The Du Pont Merck Pharmaceutical CompanyInventor: Engelbert Ciganek
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Patent number: 5294638Abstract: Pharmacologically active compounds corresponding to the general formula I: ##STR1## wherein m represents 1-4,n represents 2-5,R.sup.1 is hydrogen or lower alkyl,R.sup.2 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, andR.sup.3 is hydrogen, lower alkyl, lower alkoxy or halogen, orR.sup.2 and R.sup.3 are linked to adjacent carbon atoms and together form an alkylenedioxy group with 1-2 carbon atoms,R.sup.4 represents a saturated monocyclic or bicyclic hydrocarbon radical derived from terpenes and having 10 or 11 hydrocarbon atoms, andZ represents oxygen, an N--R.sup.5 group, wherein R.sup.5 is lower alkyl, or if R.sup.4 is a dihydronopyl radical, Z may also be sulfur,and their acid addition salts.Type: GrantFiled: January 19, 1993Date of Patent: March 15, 1994Assignee: Kali-Chemie Pharma GmbHInventors: Insa Hell, Ulf Preuschoff, Hermann Kraehling, Samuel David, Ivan Ban, Marie-Odile Christen
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Patent number: 5286753Abstract: The present invention provides novel ring-substituted 2-amino-1,2,3,4-tetrahydronaphthalenes, 3-aminochromanes, and 3-aminothiochromanes, including their corresponding sulfoxides and sulfones, which ring-substituted compounds exhibit agonist activity at the serotonin 1A receptor.Type: GrantFiled: April 16, 1993Date of Patent: February 15, 1994Assignee: Eli Lilly and CompanyInventors: John M. Schaus, Craig S. Hoechstetter, Diane Huser, Charles J. Paget, Robert D. Titus
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Patent number: 5274002Abstract: Novel trisubstituted phenyl analogs are now found to have activity as for the treatment of congestive heart failure.Type: GrantFiled: September 6, 1990Date of Patent: December 28, 1993Assignee: Warner-Lambert CompanyInventor: Lynn D. Hawkins
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Patent number: 5274106Abstract: A vulcanizable elastomeric compound and products such as pneumatic tires and the like, are formed from a functionalized polymer having a functional group derived from an anionic polymerization initiator. The anionic polymerization initiator comprises the general formula ##STR1## where R.sup.1 -R.sup.5 are the same or different and are selected from the group consisting of hydrogen; alkyls having from alkyls having from 1 to about 12 carbon atoms; aralkyls having from 7 to about 20 carbon atoms; dialkylaminos having from 2 to about 20 carbon atoms; and, dialkylaminoalkyls having from 3 to about 20 carbon atoms. At least one of R.sup.1 -R.sup.5 is selected from the group consisting of the dialkylaminos and the dialkylaminoalkyls. Methods of the present invention include preparing functionalized polymers and reducing the hysteresis of vulcanizable elastomeric compounds.Type: GrantFiled: December 30, 1991Date of Patent: December 28, 1993Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, Mark L. Stayer, Jr., John R. Schreffler, Hideki Komatsu
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Patent number: 5248823Abstract: 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: GrantFiled: December 4, 1992Date of Patent: September 28, 1993Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5248826Abstract: An electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed thereon comprising as an effective component at least one polyether compound represented by formula (I): ##STR1## wherein Ar represents a phenylene group or a biphenylene group; R.sup.1 and R.sup.2 each represent an alkyl group which may have a substituent, or an aryl group which may have a substituent; and n is an integer of 1 to 4. Furthermore, charge transporting material comprising the above polyether compound, polyether compounds having formula (II) for use in the electrophotographic photoconductor and a method of preparing the same are disclosed, ##STR2## wherein m is an integer of 1 or 2.Type: GrantFiled: July 29, 1992Date of Patent: September 28, 1993Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tamotsu Aruga, Tomoyuki Shimada
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Patent number: 5237100Abstract: Substituted benzylcycloalkenylurea derivatives of the formula (I) ##STR1## wherein X represents a halogen atom or a lower alkyl group, Y represents an oxygen atom or a sulfur atom,R.sup.1 represents a cycloalkenyl group andR.sup.2 represents a lower alkyl group, a cycloalkyl group, a benzyl group or a phenyl group optionally substituted by 1 to 5 substituents selected from the group consisting of a hydroxyl group or a lower alkoxy groupand their use as fungicides. They can be synthesized, for example, by reacting of a substituted benzyl-cycloalkenylamine with an isocyanate or by reacting of a carbamoyl halide with an amine. The starting material, the substituted benzyl-cycloalkenyl amines, are also new.Type: GrantFiled: April 23, 1992Date of Patent: August 17, 1993Assignee: Nihon Bayer Agrochem K.K.Inventors: Yasuo Yamada, Junichi Saito, Tatsuo Tamura, Shinji Sakawa
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Patent number: 5234946Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.Type: GrantFiled: August 30, 1991Date of Patent: August 10, 1993Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
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Patent number: 5206380Abstract: A chromogenic compound for use in pressure- or heatsensitive record material has the general formula (I):R.sub.1 --CH.dbd.CH--CR.sub.3 (OR.sub.4)--CH.dbd.CH--R.sub.2 (I)in which:R.sub.1 and R.sub.2 are the same or different and each is a group of one of the formulae (II): ##STR1## in which the benzene ring of the group of formula (IIa) is optionally further substituted, and in which:R.sub.10 and R.sub.11 are each independently hydrogen or an optionally-substituted alkyl, aryl or aralkyl group, orR.sub.10 and R.sub.11 together with the nitrogen atom to which they are attached form an optionally-substituted heterocyclic ring, which may include one or more further hetero atoms;R.sub.12, R.sub.13 and R.sub.14 are each independently hydrogen or an optionally-substituted alkyl, aryl or aralkyl group;R.sub.3 is an optionally-substituted aryl group; andR.sub.4 is hydrogen or an optionally-substituted alkyl, aryl or aralkyl group.Type: GrantFiled: June 8, 1992Date of Patent: April 27, 1993Assignee: The Wiggins Teape Group LimitedInventor: Kenneth J. Shanton
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Patent number: 5200561Abstract: Disclosed is a process for producing an optically active amine represented by the formula (IV) ##STR1## wherein R.sub.7 and R.sub.8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) ##STR2## wherein R.sub.1 denotes an alkyl group, aryl group or aralkyl group; R.sub.2 denotes a hydrogen atom, alkyl group or aralkyl group; R.sub.3 denotes an aryl group or a substituent represented by the formula (II) ##STR3## wherein R.sub.4 and R.sub.5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers ##STR4## wherein R.sub.Type: GrantFiled: October 7, 1991Date of Patent: April 6, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
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Patent number: 5189065Abstract: The use of products of formula (I) is described, wherein X and Y represent hydrogen, hydroxy or alkoxy; and R.sub.1 and R.sub.2 represent H, alkyl, alkenyl or alkynyl, arylalkyl, acyl or R.sub.1 and R.sub.2 together with nitrogen form a heterocycle for preparing an antitumoral drug.Type: GrantFiled: October 17, 1991Date of Patent: February 23, 1993Assignee: Roussel UclafInventors: Jorg Czech, Hans H. Sedlacek, Lucien Nedelec, Jacques Guillaume, Christian Marchandeau
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Patent number: 5166439Abstract: A sulfurized, phenolic antioxidant having a low chlorine content and good copper corrosion properties is prepared by reacting a partially sulfurized mixture of reactive, hindered phenols with formaldehyde or formaldehyde and an amine.Type: GrantFiled: November 24, 1989Date of Patent: November 24, 1992Assignee: Ethyl Petroleum Additives, Inc.Inventors: William Y. Lam, Christian S. Harstick
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Patent number: 5166438Abstract: A charge transporting material comprising a 1,3-pentadiene derivative having formula (I):A--CH.dbd.CH--CH.dbd.CH--CH.sub.2 --A (I)wherein A represents a 9-anthryl group which may have a substituent, a N-substituted carbazolyl group which may have a substituent, a N-substituted phenothiazinyl group which may have a substituent or ##STR1## in which Ar represents an arylene group which may have a substituent, R.sup.1 and R.sup.2 each represent an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent; an electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed thereon, which comprises as an effective component at least one of the 1,3-pentadiene derivatives of the above formula (I); and novel 1,3-pentadiene derivatives of the formula (I), provided that in the formula (I), R.sup.1 and R.sup.2 cannot be a methyl group at the same time, are disclosed.Type: GrantFiled: August 23, 1991Date of Patent: November 24, 1992Assignees: Ricoh Company, Ltd., Hodogaya Chemical Co., Ltd.Inventors: Mitsuru Hashimoto, Masaomi Sasaki, Tomoyuki Shimada, Nobuo Suzuki, Takayuki Sakai, Susumu Suzuka
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Patent number: 5153235Abstract: The present invention relates to a process for the production of elastic, compact or cellular moldings based on elastomers containing N-benzylurea groups in bound form, by reactinga) one or more organic and/or modified organic polyisocyanates withb) N-benzylpolyoxyalkylene-polyamines or mixtures of N-benzylpolyoxyalkylene-polyamines and polyoxyalkylene-polyamines containing from 2 to 4 primary amino groups andc) one or more alkyl-substituted aromatic polyamines having a molecular weight of up to 500,in the presence or absence ofd) catalystsand, if desired,e) blowing agents,f) auxiliaries and/org) additives,and to the N-benzylpolyoxyalkylene-polyamines and mixtures of N-benzylpolyoxyalkylene-polyamines and polyoxyalkylene-polyamines containing from 2 to 4 primary amino groups which can be used for this purpose, and to the elastomers prepared.Type: GrantFiled: January 24, 1992Date of Patent: October 6, 1992Assignee: BASF AktiengesellschaftInventors: Johannes Becker, Guenther Matzke, Hans U. Schmidt, Willibald Schoenleben
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Patent number: 5130454Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.Type: GrantFiled: December 19, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
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Patent number: 5128479Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A 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: GrantFiled: January 29, 1990Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5126371Abstract: Novel diarylacetylenes of the formula I ##STR1## where A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the meanings stated in the description, are useful for the treatment of disorders.Type: GrantFiled: August 20, 1990Date of Patent: June 30, 1992Assignee: BASF AkteingesellschaftInventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
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Patent number: 5117061Abstract: Novel anilines of the 2,6-dialkyl-4-dialkylaminomethylaniline type are prepared by reacting a secondary amine and an aldehyde with a primary aniline reactant having a free para position and substituents in both ortho positions in the presence of an acid catalyst, the amounts of amine and acid employed being at least equimolar with respect to the amount of aldehyde, and the reaction being conducted by adding the primary aniline reactant to a preformed mixture of the secondary amine, aldehyde, and acid.Type: GrantFiled: May 12, 1986Date of Patent: May 26, 1992Assignee: Ethyl CorporationInventor: Kju H. Shin
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Patent number: 5101032Abstract: Cycloalkylidene dyes have the formula ##STR1## where m is 0 or 1,L is a chemical bond or C.sub.1 -C.sub.2 -alkylene, which may be substituted,R.sup.1 is hydrogen, C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl or C.sub.3 -C.sub.7 -cycloalkyl,Y is oxygen or two hydrogens,X.sup.1 is oxygen andX.sup.2 is C.sub.1 -C.sub.8 -alkanoyloxy, substituted or unsubstituted benzoyloxy, C.sub.1 -C.sub.6 -trialkylsilyloxy or a radical of the formula OR.sup.1 or NR.sup.2 R.sup.3, where R.sup.1 is as defined above and R.sup.2 and R.sup.3 are identical or different and each is independently of the other C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl, or C.sub.3 -C.sub.7 -cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom joining them are saturated heterocyclyl, or else one of R.sup.2 and R.sup.3 is hydrogen, or X.sup.1 and X.sup.Type: GrantFiled: October 22, 1990Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventors: Hans-Dieter Martin, Bernhard Albert, Knut Kessel
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Patent number: 5095039Abstract: A halogen-substituted diphenylsulfide compound is disclosed which produce a large selective inhibition of serotonin uptake in brain. This compound is useful in the treatment of depression as well as anxiety, obsessive compulsive disorders and alcoholism.Type: GrantFiled: June 5, 1990Date of Patent: March 10, 1992Assignee: Burroughs Wellcome Co.Inventors: Nariman B. Mehta, Lawrence E. Brieaddy
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Patent number: 5057624Abstract: New process for the synthesis of the N-methyl-3,4-dimetoxyphenylethylamine of formula ##STR1## intermediate in the synthesis of the drug internationally known as verapamil. The process starts from the 3,4-dimethoxybenzaldehyde which, by means of a Darzens condensation, gives an epoxyester that, by alkaline hydrolysis and subsequent decarboxylation, gives the 3,4-dimethoxyphenylacetaldehyde. This aldehyde gives the amine of formula I by reaction with monomethylamine followed by reduction with sodium borohydride.Type: GrantFiled: March 30, 1990Date of Patent: October 15, 1991Assignee: ALFA Wassermann S.p.A.Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
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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: 5011998Abstract: A novel synthesis of aromatic tertiary amines involves reacting an aromatic anil and an aromatic ether in a molar ratio of 1:1; adjusting the ratio to 2:1 produces novel enamines and by employing a two step process for enamine production, various unsymmetrically substituted enamines can be obtained which are readily hydrolyzed to corresponding deoxybenzoins which in turn are readily oxidized to benzils, the aromatic tertiary amines may be used to produce charge transport layers in xerography, while the benzils may be used to produce a variety of desired polymers.Type: GrantFiled: January 6, 1990Date of Patent: April 30, 1991Inventors: Allan S. Hay, Martino Paventi
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Patent number: 5006561Abstract: 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: GrantFiled: April 17, 1990Date of Patent: April 9, 1991Assignee: Pfizer Inc.Inventors: John E. Arrowsmith, Peter E. Cross
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Patent number: 5006563Abstract: This invention relates to alkylamino and alkyl amino alkyl diarylketones of the formula ##STR1## where Ar is aryl of the formula ##STR2## where V is hydrogen, halogen, loweralkyl, loweralkoxy, CF.sub.3, No.sub.2 and u is an integer of 1 to 3; X and Y are independently CH.sub.2 --, --CH.sub.2 -- or --CHF--; Z and W are independently --CH.sub.2 --, --O--, --CHOH--, or --CHF--; m, n, p, q and t are integers which are independently 0 or 1; R.sub.1 is H or loweralkyl; R.sub.2 and R.sub.3 are loweralkyl; and the pharmaceutically acceptable acid addition salts thereof and where applicable the geometric and optical isomers and racemic mixtures thereof. The compounds of this invention display utility as analgesic agents and as agents for alleviating various memory dysfunctions, characterized by a decreased cholinergic function, such as Alzheimer's disease.Type: GrantFiled: July 31, 1990Date of Patent: April 9, 1991Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: R. Richard L. Hamer, Brian Freed, Richard C. Allen
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Patent number: 5004755Abstract: The present invention relates to a new laevorotatory basic derivative of 9,10-ethanoanthracene, namely R-(-)-.alpha.-[(methylamino)methyl]-9,10-ethanoanthracene-9(10H)-ethanol of the formula I ##STR1## and the acid addition salts thereof, to pharmaceutical compositions containing these new substances and to a method for treating dysphoric conditions, psychovegetative or psychosomatic disorders.Type: GrantFiled: August 28, 1987Date of Patent: April 2, 1991Assignee: Ciba-Geigy CorporationInventor: Angelo Storni
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Patent number: 4994619Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: June 16, 1988Date of Patent: February 19, 1991Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 4978792Abstract: A commercially advantageous process for producing m- or p-aminobenzylamine is provided, which is characterized by subjecting m- or p-nitrobenzaldehyde and ammonia to catalytic reduction in the presence of a reducing catalyst in an organic solvent; in the reduction, when nitrobenzaldehyde and ammonia are in advance made a mixed solution in an organic solvent, and this solution is added in divided manner, the yield being further improved.Type: GrantFiled: March 14, 1989Date of Patent: December 18, 1990Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Akihiro Tamaki, Katsuzi Watanabe, Akihiro Yamaguchi
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Patent number: 4962234Abstract: An antioxidant for lubricating oils comprising an amine compound selected from substituted benzylamines or a substituted 1-amino-1,2,3,4-tetrahydro-naphthalene. The preferred anti-oxidants are N-(alpha -methyl -p -octylbenzyl) aniline, N-(alpha-methylbenzyl)- p -nonylaniline or 1-( p -dodecylanilino)-1,2,3,4-tetrahydronaphthalene.Type: GrantFiled: June 1, 1988Date of Patent: October 9, 1990Assignee: Uniroyal Chemical Company, Inc.Inventors: Baldev K. Bandlish, Frederick C. Loveless, Walter Nudenberg
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Patent number: 4956055Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each Ar is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and the y bonds are attached to adjacent carbon atoms on the ring structures;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralyky, alkaryl, alkoxyalky, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 where Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatieves thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.Type: GrantFiled: July 24, 1989Date of Patent: September 11, 1990Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
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Patent number: 4954227Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each AR is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and the y bonds are attached to adjacent carbon atoms on the ring structures;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 were Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatives thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.Type: GrantFiled: July 24, 1989Date of Patent: September 4, 1990Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
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Patent number: 4948794Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is C.sub.1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C.sub.3-8 -cycloalkyl, aryl, aralkyl; and wherein R.sup.6 is, hydrogen, halogen, CN, CF.sub.3, NO.sub.2, or OR', wherein R' is C.sub.1-4 -alkyl and R.sup.5, R.sup.7 and R.sup.8 is hydrogen, provided R.sup.6 is not CF.sub.3, OCH.sub.3, NO.sub.2, C.sup.1 or Br when R.sup.1 is CH.sub.3 ; orR.sup.6 and R.sup.7 independently are NO.sub.2, halogen, CN, CF.sub.3, or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.8 are each hydrogen; orR.sup.5 and R.sup.6 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.7 and R.sup.8 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 -alkyl; orR.sup.7 and R.sup.Type: GrantFiled: November 8, 1988Date of Patent: August 14, 1990Assignee: A/S FerrosanInventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
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Patent number: 4914133Abstract: Amino compounds of the formula ##STR1## where R.sup.1 is alkyl, A is alkylene or alkenylene, and Ar is aryl, and their acid addition salts, and fungicides containing these compounds.Type: GrantFiled: April 14, 1988Date of Patent: April 3, 1990Assignee: BASF AktiengesellschaftInventors: Walter Himmele, Hubert Sauter, Hardo Siegel, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 4912258Abstract: Fluorinated aniline derivatives of the general formula I are described ##STR1## in which R.sup.1 represents H or (CH.sub.2).sub.n -X, n is a whole number from 1 to 3, X is H, OH, NH.sub.2, CH.sub.3 CONH, CH.sub.3 SO.sub.2 NH, SO.sub.3 H or ArSO.sub.3 H, Ar is optionally substituted arylene radical, R.sup.1 is alternatively also a --(CH.sub.2).sub.3 -- group, which is bonded to the free o-position next to the N-atom, Y is H, --O--, --NH--, --S-- or a C--C single bond, R.sup.2, in the event that Y=H, is the same as or different from R.sup.1 and means one of the radicals shown for R.sup.1, and in the event that Y is a C--C single bond or --O--, --NH-- or --S--, is an alkylene group having 1 to 3 carbon atoms linked with Y, and R.sup.3 =H, alkyl having 1 to 3 carbon atoms, OCH.sub.3, CH.sub.3 CONH, CO.sub.2 H or SO.sub.3 H.Type: GrantFiled: February 5, 1988Date of Patent: March 27, 1990Assignee: Boehringer Mannheim GmbHInventors: Hans-Georg Batz, Rupert Herrmann
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Patent number: 4898986Abstract: Disclosed is a novel inosose compound represented by the general formula: ##STR1## wherein X.sup.1 and X.sup.2 are both halogen; X.sup.1 is hydrogen and X.sup.2 is halogen; or X.sup.1 is --SQ.sup.1 and X.sup.2 is --SQ.sup.2 (each of Q.sup.1 and Q.sup.2 is lower alkyl or Q.sup.1 and Q.sup.2 may form lower alkylene), R.sup.1 is a protective group for hydroxyl and Y is .dbd.O, .dbd.N--Z (Z is hydroxyl which may be protected) or ##STR2## (A is hydrogen or an amine residue), particularly to the compound wherein the symbol Y is oxygen.The inosose compound is useful as intermediates for production of valiolamine and the N-substituted derivatives thereof, which have potent .alpha.-glucosidase inhibiting activities and are useful as preventives or therapeutics for symptoms of hyperglycemia and various diseases derived therefrom in human and animals, such as diabetes, obesity and hyperlipemia.Type: GrantFiled: August 31, 1987Date of Patent: February 6, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Satoshi Horii, Hiroshi Fukase
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Patent number: 4897425Abstract: Cyclohexylamines of the formula ##STR1## where X is a single bond or an alkylene chain, Y is hydrogen or an aryl, cyclohexyl, 4-cyclohexylcyclohexyl, perhydro-1- or 2-naphthyl or piperidyl radical, R.sup.1 and R.sup.2 are hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkenyl or arylalkyl, or R.sup.1 and R.sup.2 together form an alkylene group and, togehter with the N atom, form a ring, and acid addition salts thereof, with the exception of compounds in which X is a single bond, Y is cyclohexyl, R.sup.1 and R.sup.2 are hydrogen or methyl, and the compounds in which X is C.sub.6 -, C.sub.7 - and C.sub.8 -alkyl, Y is hydrogen and R.sup.1 and R.sup.2 together with the N atom whose substituents they are form a 2,6-dimethylmorpholine radical, and fungicides containing such cyclohexylamines.Type: GrantFiled: November 16, 1987Date of Patent: January 30, 1990Assignee: BASF AktiengesellschaftInventors: Bernhard Zipperer, Ernst Buschmann, Norbert Goetz, Ulrich Schirmer, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 4891424Abstract: 4-Aralkyl-2-nitro-2'-hydroxy-3',5'-dialkyl (or cumyl)-azobenzenes are made by coupling the corresponding diazotized 4-aralkyl-o-nitroaniline with the corresponding phenol. These azobenzene intermediates are used to prepare the corresponding 2H-benzotriazole UV absorber stabilizers substituted on the 5-position of the benzo ring by an aralkyl group, preferably alpha,alpha-dimethylbenzyl.Type: GrantFiled: April 1, 1988Date of Patent: January 2, 1990Assignee: Ciba-Geigy CorporationInventors: Raymond Seltzer, Roland A. E. Winter
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Patent number: 4879008Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each Ar is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and y bonds are attached to adjacent carbon atoms on the ring structure;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 were Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatives thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.Type: GrantFiled: November 9, 1987Date of Patent: November 7, 1989Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
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Patent number: 4879416Abstract: The process for preparing a bidentate ligand comprising the steps,(1) contacting with ozone under ozonolysis conditions a suspension in a hydroxylic reaction medium of phenanthrene or a phenanthrene derivative to form an ozonated intermediate,(2) contacting said ozonated intermediate with a reducing agent under conditions appropriate to form the corresponding diol,(3) contacting said diol with a latent displaceable functional group under conditions appropriate to convert the diol to the corresponding difunctional biaryl compound, and(4) contacting said difunctional biaryl compound, with an anion of N, P, As, Sb or Bi under conditions appropriate to form the desired bidentate ligand.Type: GrantFiled: November 23, 1987Date of Patent: November 7, 1989Assignee: Eastman Kodak CompanyInventors: Thomas A. Puckette, Thomas J. Devon, Gerald W. Phillips, Jerome L. Stavinoha
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Patent number: 4857651Abstract: This invention provides novel .alpha.-[2,2-di(C.sub.1 -C.sub.4 alkoxy)ethylamino]-.beta.-cyanostyrene and .alpha.-[2,2-di(C.sub.1 -C.sub.4 alkoxy)ethylamino]-.beta.-nitrostyrene compounds that are useful for the preparation of pesticidal arylpyrroles. The invention also provides a method for the preparation of the above-said .beta.-cyanostyrene and .beta.-nitrostyrene compounds.Type: GrantFiled: July 29, 1987Date of Patent: August 15, 1989Assignee: American Cyanamid CompanyInventors: Dale G. Brown, Jack K. Siddens, Robert E. Diehl, Donald P. Wright, Jr.
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Patent number: 4843160Abstract: Prepare novel .alpha.-aminoalkylphenols by contacting an .alpha.-alkenylphenol and an amine under reaction conditions.Type: GrantFiled: October 1, 1984Date of Patent: June 27, 1989Assignee: The Dow Chemical CompanyInventor: Eric W. Otterbacher
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Patent number: 4814507Abstract: A novel sulfone compound represented by the general formula (I) ##STR1## wherein R.sup.1 is cyclohexyl, phenyl; or a phenyl substituted with a group selected from nitro, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are respectively hydrogen, halogen, cyano or carbonyl, wherein R.sup.1 and R.sup.2 may form an o-phenylene or an o-phenylene substituted with at least one group selected from nitro C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; X is oxygen or methylkene; Y is -(CH.sub.2).sub.n --, wherein n is an integer of 0, 5 or 6, or ##STR2## wherein m is an integer 1-3; R.sup.6 is hydrogen, C.sub.1 -C.sub.3 alkyl, .omega.-alkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms, or .omega.-dialkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms; R.sup.7 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.6 and R.sup.7 may form a ring together with N, or ##STR3## wherein R.sup.8 is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: September 14, 1987Date of Patent: March 21, 1989Assignee: Mitsubishi Chemical Industries, LimitedInventors: Akihiro Tobe, Shinichiro Fujimori, Tomoshi Yamazaki, Mamoru Sugano, Ryoji Kikumoto, Issei Nitta
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Patent number: 4806688Abstract: Prepare diamino- or dialkylaminobenzenediols by hydrogenating benzoquinone compounds in the presence of a solvent and a catalyst.Type: GrantFiled: May 16, 1986Date of Patent: February 21, 1989Assignee: The Dow Chemical CompanyInventors: Muthiah N. Inbasekaran, Robert M. Strom
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Patent number: 4795627Abstract: The present invention describes novel tritium labelled nitrogen mustard type compounds, and their aziridinium type analog, and a process for the production of same. The compounds are of value in medical research and development and also as active ingredients of pharmaceutical compositions. The compounds can be used to develop analogs of human disease states and can also be used to evaluate the mechanism of neurotransmitter regulation and function, both in vitro and in vivo.Type: GrantFiled: October 18, 1984Date of Patent: January 3, 1989Assignee: University of PittsburghInventors: Abraham Fisher, Israel Hanin, Donald J. Abraham
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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