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)
  • Patent number: 5504253
    Abstract: 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: Grant
    Filed: July 15, 1994
    Date of Patent: April 2, 1996
    Assignee: NPS Pharmaceuticals, Inc.
    Inventors: Bradford C. VanWagenen, Thomas E. D'Ambra
  • Patent number: 5407961
    Abstract: 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: Grant
    Filed: May 12, 1994
    Date of Patent: April 18, 1995
    Assignee: 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
  • Patent number: 5359091
    Abstract: 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: Grant
    Filed: November 18, 1993
    Date of Patent: October 25, 1994
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5334628
    Abstract: 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: Grant
    Filed: December 31, 1992
    Date of Patent: August 2, 1994
    Assignee: Kaken Pharmaceutical Co., Ltd.
    Inventors: Tetsuya Maeda, Toshiyuki Yamamoto, Mituo Takase, Kazuya Sasaki, Tadashi Arika, Mamoru Yokoo, Rieko Hashimoto, Kouji Amemiya, Sakae Koshikawa
  • Patent number: 5306821
    Abstract: 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: Grant
    Filed: January 10, 1992
    Date of Patent: April 26, 1994
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventor: Engelbert Ciganek
  • Patent number: 5294638
    Abstract: 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: Grant
    Filed: January 19, 1993
    Date of Patent: March 15, 1994
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Insa Hell, Ulf Preuschoff, Hermann Kraehling, Samuel David, Ivan Ban, Marie-Odile Christen
  • Patent number: 5286753
    Abstract: 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: Grant
    Filed: April 16, 1993
    Date of Patent: February 15, 1994
    Assignee: Eli Lilly and Company
    Inventors: John M. Schaus, Craig S. Hoechstetter, Diane Huser, Charles J. Paget, Robert D. Titus
  • Patent number: 5274002
    Abstract: Novel trisubstituted phenyl analogs are now found to have activity as for the treatment of congestive heart failure.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: December 28, 1993
    Assignee: Warner-Lambert Company
    Inventor: Lynn D. Hawkins
  • Patent number: 5274106
    Abstract: 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: Grant
    Filed: December 30, 1991
    Date of Patent: December 28, 1993
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Thomas A. Antkowiak, Mark L. Stayer, Jr., John R. Schreffler, Hideki Komatsu
  • Patent number: 5248823
    Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: September 28, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5248826
    Abstract: 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: Grant
    Filed: July 29, 1992
    Date of Patent: September 28, 1993
    Assignee: Ricoh Company, Ltd.
    Inventors: Masaomi Sasaki, Tamotsu Aruga, Tomoyuki Shimada
  • Patent number: 5237100
    Abstract: 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: Grant
    Filed: April 23, 1992
    Date of Patent: August 17, 1993
    Assignee: Nihon Bayer Agrochem K.K.
    Inventors: Yasuo Yamada, Junichi Saito, Tatsuo Tamura, Shinji Sakawa
  • Patent number: 5234946
    Abstract: 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: Grant
    Filed: August 30, 1991
    Date of Patent: August 10, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
  • Patent number: 5206380
    Abstract: 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: Grant
    Filed: June 8, 1992
    Date of Patent: April 27, 1993
    Assignee: The Wiggins Teape Group Limited
    Inventor: Kenneth J. Shanton
  • Patent number: 5200561
    Abstract: 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: Grant
    Filed: October 7, 1991
    Date of Patent: April 6, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
  • Patent number: 5189065
    Abstract: 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: Grant
    Filed: October 17, 1991
    Date of Patent: February 23, 1993
    Assignee: Roussel Uclaf
    Inventors: Jorg Czech, Hans H. Sedlacek, Lucien Nedelec, Jacques Guillaume, Christian Marchandeau
  • Patent number: 5166439
    Abstract: 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: Grant
    Filed: November 24, 1989
    Date of Patent: November 24, 1992
    Assignee: Ethyl Petroleum Additives, Inc.
    Inventors: William Y. Lam, Christian S. Harstick
  • Patent number: 5166438
    Abstract: 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: Grant
    Filed: August 23, 1991
    Date of Patent: November 24, 1992
    Assignees: Ricoh Company, Ltd., Hodogaya Chemical Co., Ltd.
    Inventors: Mitsuru Hashimoto, Masaomi Sasaki, Tomoyuki Shimada, Nobuo Suzuki, Takayuki Sakai, Susumu Suzuka
  • Patent number: 5153235
    Abstract: 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: Grant
    Filed: January 24, 1992
    Date of Patent: October 6, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Becker, Guenther Matzke, Hans U. Schmidt, Willibald Schoenleben
  • Patent number: 5130454
    Abstract: 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: Grant
    Filed: December 19, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
  • Patent number: 5128479
    Abstract: 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: Grant
    Filed: January 29, 1990
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5126371
    Abstract: 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: Grant
    Filed: August 20, 1990
    Date of Patent: June 30, 1992
    Assignee: BASF Akteingesellschaft
    Inventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
  • Patent number: 5117061
    Abstract: 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: Grant
    Filed: May 12, 1986
    Date of Patent: May 26, 1992
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • Patent number: 5101032
    Abstract: 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: Grant
    Filed: October 22, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Dieter Martin, Bernhard Albert, Knut Kessel
  • Patent number: 5095039
    Abstract: 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: Grant
    Filed: June 5, 1990
    Date of Patent: March 10, 1992
    Assignee: Burroughs Wellcome Co.
    Inventors: Nariman B. Mehta, Lawrence E. Brieaddy
  • Patent number: 5057624
    Abstract: 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: Grant
    Filed: March 30, 1990
    Date of Patent: October 15, 1991
    Assignee: ALFA Wassermann S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
  • 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: 5011998
    Abstract: 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: Grant
    Filed: January 6, 1990
    Date of Patent: April 30, 1991
    Inventors: Allan S. Hay, Martino Paventi
  • 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: 5006563
    Abstract: 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: Grant
    Filed: July 31, 1990
    Date of Patent: April 9, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: R. Richard L. Hamer, Brian Freed, Richard C. Allen
  • Patent number: 5004755
    Abstract: 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: Grant
    Filed: August 28, 1987
    Date of Patent: April 2, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Angelo Storni
  • Patent number: 4994619
    Abstract: 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: Grant
    Filed: June 16, 1988
    Date of Patent: February 19, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
  • Patent number: 4978792
    Abstract: 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: Grant
    Filed: March 14, 1989
    Date of Patent: December 18, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Teruyuki Nagata, Akihiro Tamaki, Katsuzi Watanabe, Akihiro Yamaguchi
  • Patent number: 4962234
    Abstract: 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: Grant
    Filed: June 1, 1988
    Date of Patent: October 9, 1990
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Baldev K. Bandlish, Frederick C. Loveless, Walter Nudenberg
  • Patent number: 4956055
    Abstract: 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: Grant
    Filed: July 24, 1989
    Date of Patent: September 11, 1990
    Assignee: Eastman Kodak Company
    Inventor: Thomas A. Puckette
  • Patent number: 4954227
    Abstract: 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: Grant
    Filed: July 24, 1989
    Date of Patent: September 4, 1990
    Assignee: Eastman Kodak Company
    Inventor: Thomas A. Puckette
  • Patent number: 4948794
    Abstract: 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: Grant
    Filed: November 8, 1988
    Date of Patent: August 14, 1990
    Assignee: A/S Ferrosan
    Inventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
  • Patent number: 4914133
    Abstract: 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: Grant
    Filed: April 14, 1988
    Date of Patent: April 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Himmele, Hubert Sauter, Hardo Siegel, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4912258
    Abstract: 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: Grant
    Filed: February 5, 1988
    Date of Patent: March 27, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans-Georg Batz, Rupert Herrmann
  • Patent number: 4898986
    Abstract: 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: Grant
    Filed: August 31, 1987
    Date of Patent: February 6, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Satoshi Horii, Hiroshi Fukase
  • Patent number: 4897425
    Abstract: 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: Grant
    Filed: November 16, 1987
    Date of Patent: January 30, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Zipperer, Ernst Buschmann, Norbert Goetz, Ulrich Schirmer, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4891424
    Abstract: 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: Grant
    Filed: April 1, 1988
    Date of Patent: January 2, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter
  • Patent number: 4879008
    Abstract: 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: Grant
    Filed: November 9, 1987
    Date of Patent: November 7, 1989
    Assignee: Eastman Kodak Company
    Inventor: Thomas A. Puckette
  • Patent number: 4879416
    Abstract: 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: Grant
    Filed: November 23, 1987
    Date of Patent: November 7, 1989
    Assignee: Eastman Kodak Company
    Inventors: Thomas A. Puckette, Thomas J. Devon, Gerald W. Phillips, Jerome L. Stavinoha
  • Patent number: 4857651
    Abstract: 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: Grant
    Filed: July 29, 1987
    Date of Patent: August 15, 1989
    Assignee: American Cyanamid Company
    Inventors: Dale G. Brown, Jack K. Siddens, Robert E. Diehl, Donald P. Wright, Jr.
  • Patent number: 4843160
    Abstract: Prepare novel .alpha.-aminoalkylphenols by contacting an .alpha.-alkenylphenol and an amine under reaction conditions.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: June 27, 1989
    Assignee: The Dow Chemical Company
    Inventor: Eric W. Otterbacher
  • Patent number: 4814507
    Abstract: 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: Grant
    Filed: September 14, 1987
    Date of Patent: March 21, 1989
    Assignee: Mitsubishi Chemical Industries, Limited
    Inventors: Akihiro Tobe, Shinichiro Fujimori, Tomoshi Yamazaki, Mamoru Sugano, Ryoji Kikumoto, Issei Nitta
  • Patent number: 4806688
    Abstract: Prepare diamino- or dialkylaminobenzenediols by hydrogenating benzoquinone compounds in the presence of a solvent and a catalyst.
    Type: Grant
    Filed: May 16, 1986
    Date of Patent: February 21, 1989
    Assignee: The Dow Chemical Company
    Inventors: Muthiah N. Inbasekaran, Robert M. Strom
  • Patent number: 4795627
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: January 3, 1989
    Assignee: University of Pittsburgh
    Inventors: Abraham Fisher, Israel Hanin, Donald J. Abraham
  • Patent number: 4777294
    Abstract: 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: Grant
    Filed: April 17, 1987
    Date of Patent: October 11, 1988
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Satoshi Horii, Yukihiko Kameda, Hiroshi Fukase