Additional Amino Nitrogen Attached Directly Or Indirectly To The Acyclic Carbon Or Chain By Acyclic Nonionic Bonding Patents (Class 564/372)
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Patent number: 6288231Abstract: This invention relates to peptide-containing &agr;-ketoamide inhibitors of cysteine and serine proteases, methods for making these compounds, and methods for using the same.Type: GrantFiled: March 16, 2000Date of Patent: September 11, 2001Assignee: Cephalon, Inc.Inventors: Sankar Chatterjee, John P. Mallamo, Ron Bihovsky, Gregory J. Wells
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Patent number: 6057358Abstract: Novel amine derivatives of the following general formula (I): ##STR1## (wherein) A may denote --(CH.sub.2)--O--, --(CH.sub.2).sub.2 --O--, or --(CH.sub.2).sub.2 --NH--;B may denote --(CH.sub.2).sub.2 --;R.sub.1 may denote a hydrogen atom, a halogen atom, a nitro group, a 1-pyrrolyl group, an acetamido group, an amino group or a dimethylamino group;R.sub.2 may denote a hydrogen atom or a nitro group;R.sub.3 and R.sub.4 may denote a hydrogen atom;R.sub.8a and R.sub.8b which are the same may denote a chlorine atom or a methoxy group;R.sub.9 may denote a hydrogen atom or an amino group;R may denote a methyl group; andX may denote a methanesulfonamido group, a 1-imidazolyl group or a nitro group or a salts thereof are useful as antiarrhythmic drugs.Type: GrantFiled: May 27, 1997Date of Patent: May 2, 2000Assignee: C&C Research Labs.Inventors: You Sup Chung, Hak Yeop Kim, Kyung Yun Jung, Jae Ki Min, Shigeru Tanabe
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Patent number: 5973205Abstract: A process for preparing a compound of formula (I) or an addition salt thereof and/or a solvate thereof: ##STR1## wherein R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are each independently C.sub.1-4 alkoxy and R.sup.3 is C.sub.1-6 alkyl, which process comprises reacting an arylamine of formula (II): ##STR2## wherein R.sup.4 and R.sup.5 are as defined in relation to formula (I) with a .beta.-aminoaldehyde of formula (III): ##STR3## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in relation to formula (I); and thereafter reducing the intermediate so formed and, optionally, forming an addition salt of the compound of formula (I) and/or a solvate thereof.Type: GrantFiled: April 23, 1998Date of Patent: October 26, 1999Assignee: SmithKline Beecham plcInventors: Thomas Weir Ramsay, Robin Patrick Attrill
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Patent number: 5932766Abstract: The present invention discloses a process for the preparation of a compound having formula 4: ##STR1## The process comprises the step of reacting an enolate having the formula: ##STR2## with a Grignard reagent. The enolate salt is formed in situ from the reaction of a protected ester wherein M is an alkali metal. R.sub.6 and R.sub.7 are each hydrogen or are independently selected from ##STR3## wherein R.sub.a and R.sub.b are independently selected from hydrogen, lower alkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, lower alkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR4## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from lower alkyl, trifluoromethyl, alkoxy and halo. Alternatively, R.sub.6 is as defined above and R.sub.7 is R.sub.12 OC(O)-- wherein R.sub.12 is benzyl; or R.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded form ##STR5## wherein R.sub.Type: GrantFiled: May 30, 1997Date of Patent: August 3, 1999Assignee: Abbott LaboratoriesInventors: Anthony R. Haight, Timothy L. Stuk, Jerome A. Menzia
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Patent number: 5922744Abstract: The present invention provides a compound of formula: ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6a and R.sup.6b are defined herein or a pharmaceutically acceptable salt thereof, a process for its preparation, intermediates and its use as a tachykinin antagonist.Type: GrantFiled: January 12, 1998Date of Patent: July 13, 1999Assignee: Merck Sharp & Dohme LimitedInventors: Timothy Harrison, Andrew Pate Owens
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Patent number: 5849048Abstract: Substituted biphenyl poly(oxyalkylene) ethers having the formula: ##STR1## wherein R.sub.1 is hydrogen or hydroxyl; R.sub.2 is hydroxyl, cyano, nitro, amino, aminomethyl, N-alkylamino or N-alkylaminomethyl wherein the alkyl group contains 1 to about 6 carbon atoms, N,N-dialkylamino or N,N-dialkylaminomethyl wherein each alkyl group independently contains 1 to about 6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are ortho relative to each other and meta or para relative to the adjoining phenyl substitutent; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl having 1 to about 6 carbon atoms and each R.sub.3 and R.sub.4 is independently selected in each --OCHR.sub.3 --CHR.sub.4 -- unit; R.sub.5 is hydrogen, alkyl having 1 to about 100 carbon atoms, phenyl, aralkyl having about 7 to about 100 carbon atoms, alkaryl having about 7 to about 100 carbon atoms; or an acyl group having the formula: ##STR2## wherein R.sub.Type: GrantFiled: September 30, 1997Date of Patent: December 15, 1998Assignee: Chevron Chemical Company LLCInventor: Richard E. Cherpeck
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Patent number: 5837873Abstract: A retroviral protease inhibiting compound of the formula A--X--B is disclosed. Also disclosed are a composition and method for inhibiting a retroviral protease and for treating an HIV infection. Also disclosed are processes and intermediates useful for the preparation of the retroviral protease inhibitors.Type: GrantFiled: March 24, 1995Date of Patent: November 17, 1998Assignee: Abbott LaboratoriesInventors: Daniel W. Norbeck, Lynn M. Codacovi, Steven J. Wittenberger
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Patent number: 5830869Abstract: The present invention provides novel thiadiazole amide derivatives represented by formula I ##STR1## The compounds of the present invention inhibit various enzymes from the matrix metalloproteinase family, predominantly stromelysins, and hence are useful for the treatment of matrix metallo endoproteinase diseases such as osteoarthritis, rheumatoid arthritis, septic arthritis, osteopenias such as osteoporosis, tumor metastasis, periodontitis, gingivitis, corneal ulceration, dermal ulceration, gastric ulceration, inflammation and other diseases related to connective tissue degradation.Type: GrantFiled: June 18, 1997Date of Patent: November 3, 1998Inventors: Mark Allen Mitchell, Heinrich Josef Schostarez, Linda Louise Maggiora, Thomas J. Lindberg
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Patent number: 5616776Abstract: Intermediates and processes are disclosed which are useful for the preparation of a substantially pure compound of the formula: ##STR1## wherein R.sub.6 and R.sub.7 are each hydrogen or R.sub.6 and R.sub.7 are independently selected from ##STR2## wherein R.sub.a and R.sub.b are independently selected from hydrogen, loweralkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, loweralkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR3## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from loweralkyl, trifluoromethyl, alkoxy and halo; orR.sub.6 is as defined above and R.sub.7 is R.sub.7a OC(O)-- wherein R.sub.7a is loweralkyl or benzyl; orR.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded are ##STR4## wherein R.sub.f, R.sub.g, R.sub.h and R.sub.i are independently selected from hydrogen, loweralkyl, alkoxy, halogen and trifluoromethyl and R.sub.Type: GrantFiled: April 7, 1995Date of Patent: April 1, 1997Assignee: Abbott LaboratoriesInventors: Timothy L. Stuk, Anthony R. Haight, Francis A. J. Kerdesky, M. Robert Leanna, Howard E. Morton, Timothy A. Robbins, David Scarpetti, Jien-Heh J. Tien
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Patent number: 5550291Abstract: Disclosed herein is a stereospecific synthesis amenable to the large scale preparation of a hydrochloric acid addition salt of a chlorohydrin of the formula ##STR1## wherein R.sup.1 and R.sup.2 are amino protective groups and R.sup.3 is an amino acid side chain or a protected amino acid side chain. The synthesis involves reacting an aldehyde of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined hereinbefore with (chloromethyl)lithium at -20.degree. C. or below and contacting the resulting diastereoisomeric mixture of lithium alcoholates with aqueous hydrochloric acid to obtain a separable mixture of the hydrochloric acid addition salts of the chlorohydrin and its corresponding hydroxy diastereoisomer. The hydrochloric acid addition salt of the chlorohydrin is transformed readily into corresponding optionally amino-protected aminoepoxides; for example, 3(S)-(tert-butyloxycarbonylamino)-l,2(S)-epoxy-4-phenyl-butane.Type: GrantFiled: May 4, 1995Date of Patent: August 27, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.Inventors: Pierre L. Beaulieu, Yvan Guindon, Dominik M. Wernic
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Patent number: 5521220Abstract: The present invention relates to novel acyclic ethylenediamine derivatives of nitrogen containing heterocyclic compounds, and specifically, to compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined as in the specification. It also relates to novel intermediates used in the synthesis of such derivatives.Compounds of the formula I and their pharmaceutically acceptable salts are useful in the treatment of inflammatory and central nervous system disorders, as well as other disorders.Type: GrantFiled: July 20, 1994Date of Patent: May 28, 1996Assignee: Pfizer Inc.Inventor: Brian T. O'Neill
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Patent number: 5491253Abstract: Intermediates and processes are disclosed which are useful for the preparation of a substantially pure compound of the formula: ##STR1## wherein R.sub.6 and R.sub.7 are each hydrogen or R.sub.6 and R.sub.7 are independently selected from ##STR2## wherein R.sub.a and R.sub.b are independently selected from hydrogen, loweralkyl and phenyl and R.sub.c, R.sub.d and R.sub.e are independently selected from hydrogen, loweralkyl, trifluoromethyl, alkoxy, halo and phenyl; and ##STR3## wherein the naphthyl ring is unsubstituted or substituted with one, two or three substitutents independently selected from loweralkyl, trifluoromethyl, alkoxy and halo; orR.sub.6 is as defined above and R.sub.7 is R.sub.7a OC(O)--wherein R.sub.7a is loweralkyl or benzyl; orR.sub.6 and R.sub.7 taken together with the nitrogen atom to which they are bonded are ##STR4## wherein R.sub.f, R.sub.g, R.sub.h and R.sub.i are independently selected from hydrogen, loweralkyl, alkoxy, halogen and trifluoromethyl and R.sub.Type: GrantFiled: July 27, 1994Date of Patent: February 13, 1996Assignee: Abbott LaboratoriesInventors: Timothy L. Stuk, Michael S. Allen, Anthony R. Haight, Francis A. Kerdesky, Denton C. Langridge, M. Robert Leanna, Linda M. Lijewski, Laura Melcher, Howard E. Morton, Daniel W. Norbeck, Daniel S. Reno, Timothy A. Robbins, David Scarpetti, Hing L. Sham, Thomas J. Sowin, Jien-Heh J. Tien, Chen Zhao
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Patent number: 5414127Abstract: Antidepressant agents having the formula ##STR1## wherein R.sup.1 is a polycycloalkyl group; R.sup.2 is methyl or ethyl, X is O or NH; and Y comprises a 5- or 6-membered heterocyclic ring having one or two nitrogens; or fused bicyclic heterocyclic rings having a total of three nitrogen atoms, one in each ring and one angular nitrogen.Type: GrantFiled: January 19, 1994Date of Patent: May 9, 1995Assignee: Pfizer Inc.Inventors: Nicholas A. Saccomano, Fredric J. Vinick
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Patent number: 5389630Abstract: Diamine compounds of formula (I) or an addition salt thereof are provided: ##STR1## These compounds have an excellent cerebral protective action, are very safe, and exhibit a strong action when orally administered, and therefore, medicines containing such compounds are effective for treating disorders caused by cerebral hemorrhage, cerebral infarction, subarachnoid hemorrhage, transient ischemic attack, cerebrovascular disorders and the like, or preventing progress of such disorders.Type: GrantFiled: January 22, 1993Date of Patent: February 14, 1995Assignee: Kowa Co., Ltd.Inventors: Seiichi Sato, Kiyoshi Kawamura, Yoshio Takahashi, Koichiro Watanabe, Sadahiro Shimizu, Tomio Ohta
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Patent number: 5380850Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.Type: GrantFiled: December 16, 1993Date of Patent: January 10, 1995Assignee: Merck Frosst Canada, Inc.Inventors: Petpiboon Prasit, Rejean Fortin, John H. Hutchinson, Michel L. Belley, Serge Leger, Richard Frenette, John Gillard
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Patent number: 5288909Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.Type: GrantFiled: August 19, 1992Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5270471Abstract: A branched chain polyalkylene polyamine ("PAPA") having plural amine groups, including a secondary amine group intermediate terminal primary amine groups one of which is hindered, and having at least two carbon atoms between each group, is selectively reductively alkylated with a ketone. The reaction provides a convenient method for selectively reductively alkylating a PAPA having a hindered primary amine group, the method comprising contacting the PAPA with hydrogen and the ketone in the presence of a catalytically effective amount of a Group VIII metal on a catalyst support, at a pressure in the range from about 500-1000 psi and a temperature in the range from about 50.degree. C. to about 200.degree. C. for a period of time sufficient to preferentially alkylate the unhindered amine primary terminal amine group. The alkylation proceeds essentially without alkylating either the sterically hindered terminal primary amine group or the intermediate unhindered secondary amine group.Type: GrantFiled: October 27, 1992Date of Patent: December 14, 1993Assignee: The B. F. Goodrich CompanyInventors: John T. Lai, Pyong-Nae Son
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Patent number: 5248748Abstract: Disclosed is a diacetylene compound comprising, as structural units, (a) at least one member selected from diacetylene group-containing organic groups of the formulae (I) and (II):R.sup.I --C.tbd.C--C.tbd.C--R.sup.II -- (I)and--R.sup.III --C.tbd.C--C.tbd.C--R.sup.IV -- (II)wherein R.sup.I is hydrogen or a (C1-16) monovalent organic group, and R.sup.II, R.sup.III and R.sup.IV are a (C1-13) divalent organic group,(b) at least one organic group having at least one carbon-to-carbon double bond, and (c) at least one connecting group connecting the units (a) and (b) , which connecting group is selected from amide, imide, ester, ether, amino, imino, urethane, sulfonyl and carbonyl bonds. A cured shaped article made of this compound exhibits isotropically a high elastic modulus and has excellent mechanical properties.Type: GrantFiled: December 19, 1990Date of Patent: September 28, 1993Assignee: Dir. General of Agency of Industrial Science and TechnologyInventors: Katsuyuki Nakamura, Satoru Yamazaki, Jinichiro Kato, Kensaku Tokushige
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Patent number: 5220000Abstract: Novel bifunctional bis-quinolinols are provided as well as their chelates and processes for their production. The quinolinols can be attached to organic substrates before or after chelation and are useful for diagnostic and therapeutic purposes.Type: GrantFiled: January 23, 1992Date of Patent: June 15, 1993Inventor: Spyros Theodoropulos
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Patent number: 5210306Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a condensation catalyst and a condensation catalyst promoter, wherein said condensation catalyst promoter is present in an amount sufficient to promote the condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).Type: GrantFiled: August 8, 1989Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck, Stephen W. King, George A. Skoler
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Patent number: 5210307Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxides, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.Type: GrantFiled: January 31, 1992Date of Patent: May 11, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5185465Abstract: Novel 4-phenyl-1,3-benzodiazepines and 2-amino-.alpha.-phenylphenethylamines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants. The 2-amino-.alpha.-phenylphenethylamines are useful as anticonvulsant and neuroprotective agents.Type: GrantFiled: October 16, 1990Date of Patent: February 9, 1993Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
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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: 5151438Abstract: Compounds are disclosed which are retroviral protease inhibitors. Also disclosed are methods of using the compounds and compositions for inhibiting a retroviral protease and for treating an HIV infection.Type: GrantFiled: March 27, 1991Date of Patent: September 29, 1992Assignee: Abbott LaboratoriesInventors: Hing L. Sham, Daniel W. Norbeck, Dale J. Kempf, Chen Zhao
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Patent number: 5118850Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxdies, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.Type: GrantFiled: November 9, 1990Date of Patent: June 2, 1992Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5118851Abstract: A process of preparing a mixture of polyalkylenepolyamines and alkanolpolyamines comprising contacting a difunctional aliphatic alcohol with a primary or secondary aliphatic amine in the presence of a metal silicate catalyst wherein the metal is selected from the group consisting of Groups IIA, IIIB, and the lanthanide and actinide metals. For example, monoethanolamine reacts with diethylenetriamine in the presence of magnesium silicate to yield a mixture of higher molecular weight linear and branched polyethylenepolyamines and their corresponding alkanolpolyamines. These product mixtures are useful in the formation of specialty polyurethanes.Type: GrantFiled: December 5, 1990Date of Patent: June 2, 1992Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5105014Abstract: The present invention relates to an improved method of forming vicinal diamines. The method according to the present invention has the advantage of being highly stereoselective, capable of forming a wide variety of diamines including racemic and enantiomeric forms, and employing readily available starting and reaction materials.In particular the present invention relates to a method of forming vicinal diamines from a bis-imine precursor using nucleophilic additions of organometallic reagents.Type: GrantFiled: August 6, 1991Date of Patent: April 14, 1992Assignee: Mallinckrodt Medical, Inc.Inventor: William L. Neumann
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Patent number: 5099069Abstract: New polysubstituted diethylenetriaminepentaacetic acid chelates and protein conjugates of the same are described together with the methods of preparing such compounds. A method of delivering radiolabelled compound of the present invention to a target site while minimizing the distribution of the compound to non-targeted organs or tissues is also disclosed.Type: GrantFiled: December 16, 1988Date of Patent: March 24, 1992Inventors: Otto A. Gansow, Martin W. Brechbiel
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Patent number: 5079248Abstract: A series of [N-alkyl-N-(nitro-, alkylsulphonamido, or amino-phenalkyl) amino]-alkyl, alkoxy or alkylthio phenyl derivatives having utility as anti-arrhythmic agents.Type: GrantFiled: June 20, 1990Date of Patent: January 7, 1992Assignee: Pfizer Inc.Inventors: Peter E. Cross, Geoffrey N. Thomas, John E. Arrowsmith
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Patent number: 5041143Abstract: The present invention relates to a process for preparing a N,N'-disubstituted nitro-para-phenylenediamine (I) according to the following scheme: ##STR1## X denoting a halogen and R a lower alkyl, lower mono- or polyhydroxyalkyl, lower alkoxyalkyl or lower aminoalkyl group, in which the amino group can be mono- or disubstituted with a lower alkyl or lower mono- or polyhydroxyalkyl group, the nitrogen atom of said amino group being able to form part of a heterocyclic system.The invention also relates to the intermediate oxazolidones of formulae (II) and (III), and the new nitro-para-phenylenediamines in which R denotes a lower alkoxyalkyl, lower polyhydroxyalkyl or lower aminoalkyl group, as well as the dyeing compositions for keratinous fibres containing these new nitro-para-phenylenediamines.Type: GrantFiled: December 20, 1989Date of Patent: August 20, 1991Assignee: L'OrealInventors: Gerard Lang, Alex Junino
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Patent number: 5011999Abstract: A process for the preparation of predominantly non-cyclic polyalkylenepolyamines comprising contacting a difunctional aliphatic alcohol with ammonia or a primary or secondary aliphatic amine in the presence of a catalyst selected from the group consisting of Group VB metal oxides, niobium phosphates, tantalum phosphates, and mixtures thereof. For example, monoethanolamine is aminated by ethylenediamine to predominantly linear and branched polyethylenepolyamines in the presence of a catalyst containing niobium oxide supported on boehmite alumina.Type: GrantFiled: February 23, 1989Date of Patent: April 30, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, George E. Hartwell, David C. Molzahn, Enrique G. Ramirez, John E. Lastovica, Jr.
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Patent number: 4990633Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.Type: GrantFiled: May 4, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
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Patent number: 4965394Abstract: The difunctional polyfluoroaromatic compounds represented by the formula ##STR1## wherein X and Y are identical and are selected from the class consisting of --COOR.sup.1, --CH.sub.2 NH.sub.2, --CH.sub.2 NCO and ##STR2## wherein R.sup.1 is --H, alkyl and R.sup.2 and R.sup.3 independently are either --H, X or alkyl and n is either 0 or 1 are disclosed. These compounds are derived from those wherein X and Y are --CN which are produced in a solvent specific reaction. The process comprises reacting pentafluorobenzonitrile with a Grignard reagent of the formula CH.sub.3 MgHal, wherein Hal is --Cl or --Br, in the presence of either tetrahydrofuran, 1,3-dioxolane, dimethoxyethane or diglyme. When the solvent employed is tetrahydrofuran, the cyano compound wherein n is 1 is obtained. When the solvent is 1,3-dioxolane, the cyano compound wherein n is 0 is obtained.Type: GrantFiled: May 23, 1989Date of Patent: October 23, 1990Assignee: ICI Americas Inc.Inventors: Ludwig A. Hartmann, John F. Stephen
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Patent number: 4922024Abstract: A process for preparing amines comprising contacting an alcohol with a reactant amine in the presence of hydrogen and a catalyst comprising at least one compound containing an element of Group VIB and at least one non-metallic element of Groups IIIA, IVA, and VA of the Periodic Table, the contacting occurring under conditions such that the hydroxyl moiety of the alcohol is replaced by the reactant amine to form an amine product.Type: GrantFiled: April 14, 1988Date of Patent: May 1, 1990Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, Marvin H. Tegen, George E. Hartwell
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Patent number: 4847303Abstract: The present invention involves compounds having the structure: ##STR1## wherein: (a) --A.sup.1 is selected from the group consisting of --OH, --H, and --O.sub.2 CR;(b) --A.sup.2 is selected from the group consisting of unsubstituted or substituted, saturated or unsaturated, straight, branched and cyclic alkyl having from 1 to about 10 carbon atoms;(c)--A.sup.3 is selected from --C(CH.sub.3).sub.3, --Si(CH.sub.3).sub.3, and --CF.sub.3 ; and(d) --Y is selected from certain low molecular weight alkyl chains which terminate in specific unsaturated functional groups: ##STR2## and aldehydes in the form of their acetals; pharmaceutical compositions comprising such compounds; and methods for treating inflammation by administering such compounds.Type: GrantFiled: November 23, 1987Date of Patent: July 11, 1989Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4708966Abstract: The present invention relates to novel specifically-substituted phenyl compounds, especially substituted di-tert-butyl phenol derivatives, which are effective as anti-inflammatory, analgesic and/or antipyretic agents. These phenyl compounds are substituted with a low molecular weight alkyl chain which terminates in a specific unsaturated functional group. These unsaturated functionalities are --C.tbd.CH, C.dbd.CH.sub.2, C.dbd.C.dbd.CH.sub.2, and aldehydes in the form of their acetals.The present invention further relates to pharmaceutical compositions which contain an anti-inflammatory agent of the present invention and a pharmaceutically-acceptable carrier.Finally, the present invention relates to methods for treating diseases characterized by inflammation, such as rheumatoid arthritis and osteoarthritis, in humans or lower animals.Type: GrantFiled: June 27, 1986Date of Patent: November 24, 1987Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4658062Abstract: Novel amine terminated polybutadiene compounds of the formula: ##STR1## wherein R is hydrogen, a straight or branched chain alkyl group containing from 1 to 10 carbon atoms or a substituted or unsubstituted aryl or aralkyl group containing one or more benzenoid rings which may be fused or joined by single valency bonds, and n is an integer of from about 5 to 1500 and a process for the preparation thereof.Type: GrantFiled: June 24, 1985Date of Patent: April 14, 1987Assignee: Atlantic Richfield CompanyInventors: Harry R. Hinney, Jamil Baghdadchi
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Patent number: 4590288Abstract: A polydentate binucleating ligand having at least four donor sites selected from N, O and S, complexed with two atoms of the same metal, forms a coordination complex useful in homogeneous catalysis. Most preferably, all the metal cations are Cu cations and the ligand has a meta-xylyl functionality.Type: GrantFiled: June 29, 1983Date of Patent: May 20, 1986Assignee: Exxon Research and Engineering Co.Inventor: Lawrence P. Klemann
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Patent number: 4564707Abstract: This invention relates to the following compounds: ##STR1## Process for their preparation and uses thereof, where R.sub.1 and R.sub.2 are substituted groups, and R.sub.6, R.sub.5, R.sub.4 and R.sub.3 are hydrogen or substituted groups.Type: GrantFiled: March 19, 1981Date of Patent: January 14, 1986Assignee: Petrolite CorporationInventor: Bernardus A. Oude Alink
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Patent number: 4562249Abstract: There are described novel yellow to red azo compounds of the formula I ##STR1## wherein each D independently of the other is the radical of an aromatic or heterocyclic diazo component, each Z independently of the other is hydrogen or a C.sub.1 -C.sub.4 -alkyl group or an acylamino group, Y is hydrogen or an unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group, X is either the direct bond or C.sub.1 -C.sub.6 -alkylene, ##STR2## and n is a number from 2 to 6, preferably 2; and the substituent Y, in the case of an unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group, can also be bonded to the o-position relative to the N atom of the phenylene group to form a six-membered ring, or both Y substituents can be linked together to form a C.sub.1 -C.sub.Type: GrantFiled: March 5, 1985Date of Patent: December 31, 1985Assignee: Ciba-Geigy CorporationInventors: Hansrudolf Schwander, Rudolf Hurter
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Patent number: 4521627Abstract: The disclosure is of a method of preparing alkaline metal salts of organic diamines. The method comprises, in brief, reacting the alkaline metal with a molar excess of the diamine in the presence of a catalytic proportion of a transition metal compound, at a temperature of from about 20.degree. C. to reflux temperature for the reaction mixture.Type: GrantFiled: February 6, 1984Date of Patent: June 4, 1985Assignee: Union Camp CorporationInventor: Peter W. D. Mitchell
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Patent number: 4435425Abstract: Fluorinated diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: R.sub.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl, or phenyl-(C.sub.1 -C.sub.4 alkyl);R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.4 alkyl), or R.sub.4, where R.sub.4 is as defined below;R.sub.3 represents hydrogen, or, except when R.sub.2 represents R.sub.4, R.sub.4, where R.sub.4 is as defined below;each R.sub.4, independently, represents C.sub.2 -C.sub.5 alkylcarbonyl, phenylcarbonyl, phenyl-(C.sub.1 -C.sub.4 alkyl) carbonyl, or an aminocarboxylic acid residue derived by removal of an hydroxy group from the carboxy moiety of an L-aminocarboxylic acid; andp represents 1 or 2,and pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: April 9, 1982Date of Patent: March 6, 1984Assignee: Merrell Toraude et CompagnieInventors: Albert Sjoerdsma, Philippe Bey, Michel Jung, Fritz Gerhart, Daniel Schirlin
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Patent number: 4429158Abstract: Disclosed ar novel polyamine compounds having the general formula ##STR1## wherein R, R.sup.1, R.sup.2 and R.sup.3 are each independently selected from hydrogen and alkyl groups which may be substituted, the preparation of such compounds and their use as curing agents for epoxy resins.Type: GrantFiled: September 14, 1981Date of Patent: January 31, 1984Assignee: Eastman Kodak CompanyInventors: Raymond H. Good, Paul McBride
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Patent number: 4370500Abstract: There is provided a new compound: d-N-(2-amino-2-phenethyl-2-methoxyethylamine useful in the direct synthesis of levamisole. The compound is prepared by slurrying the racemic N-(2-amino-2-phenethyl)-2-methoxyethylamine with dibenzoyl-d-tartaric acid as the resolving agent in an aqueous acidic menstruum containing ammonium chloride, heating the resultant mixture, preferably under reflux, cooling and filtering the resultant mixture to recover crystals rich in the desired d-amine compound, hereinabove noted.Type: GrantFiled: November 6, 1978Date of Patent: January 25, 1983Assignee: American Cyanamid CompanyInventor: Nancy S. Kurose
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Patent number: 4339603Abstract: There is provided a process for racemizing an undesirable, optically active compound for conversion to levamisole, namely, l-N-(2-amino-2-phenethyl)-2-methoxyethylamine, by converting the latter to optically active l-(2-methoxyethyl)-4-phenyl-2-imidazolidone, which is next converted to the corresponding optically inactive imidazolidone derivative, which derivative is hydrolyzed to the optically inactive racemate, dl-N-(2-amino-2-phenethyl)-2-methoxyethylamine. The latter can be resolved to obtain the d and l components of the racemate, the d component being utilized directly in levamisole synthesis and the l component being again subjected to the above procedure.Type: GrantFiled: January 8, 1979Date of Patent: July 13, 1982Assignee: American Cyanamid CompanyInventors: Sivaraman Raghu, Arnold Zweig
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Patent number: 4316038Abstract: Processes for reacting aryl vinyl compounds, nitriles, and halogens to provide imidoyl halides; processes for preparing amidine hydrohalides from the imidoyl compounds; processes for producing novel imidazolines from the amidine hydrohalides; processes for preparing novel amidoamines from the imidazolines; processes for preparing novel diamines from the amidoamines, together with novel nitrogen-containing products so produced, such products being useful for the production of various imidazothiazoles including tetramisole.Type: GrantFiled: May 21, 1980Date of Patent: February 16, 1982Assignee: American Cyanamid CompanyInventor: Sivaraman Raghu
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Patent number: 4313005Abstract: This invention relates to a process for reducing amidine formation during reduction of organonitriles. The process comprises including a boron compound in the reaction medium in sufficient amount to complex the amidine compound as it is formed.Type: GrantFiled: April 3, 1980Date of Patent: January 26, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Randall J. Daughenbaugh
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Patent number: 4288625Abstract: Unsaturated dinitriles are reacted with an aromatic compound such as benzene in the presence of a Lewis acid such as aluminum chloride to yield novel aralkylenedinitriles, such as 5-methyl-5-phenylnonanedinitrile and isomers thereof. The aralkylenedinitriles can be reduced to novel aralkylenediamines or novel cycloalkylalkylenediamines. Polymerization of the aralkylenediamines or cycloalkylalkylenediamines with polycarboxylic acids provides novel polyamides of tough, clear, colorless character.Type: GrantFiled: August 23, 1976Date of Patent: September 8, 1981Assignee: Phillips Petroleum Co.Inventors: Charles A. Drake, Stanley D. Turk
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Patent number: 4279834Abstract: New dinitriles are prepared by reacting an alpha, beta saturated nitrile with an alpha, beta unsaturated nitrile. For this preparation subzero temperatures are preferred. Higher diamines can be prepared by hydrogenating the dinitriles thus obtained, such diamines being reacted with a dicarboxylic acid or a salt, ester or chloride of such an acid to prepare polyamides having an amorphous character, i.e. transparent polyamides.Type: GrantFiled: January 17, 1980Date of Patent: July 21, 1981Assignee: Anic S.p.A.Inventors: Aldo Prevedello, Maurizio Brunelli, Edoardo Platone
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Patent number: 4275237Abstract: Heavy reaction product after separation as by distillation of light reaction product or diadduct from a reaction mixture obtained by reaction of olefinically unsaturated nitriles with monoolefinic hydrocarbons containing an allylic hydrogen atom is hydrogenated to produce a polyamine mixture useful as an epoxy resin hardener yielding cured resins exhibiting low water absorption.Type: GrantFiled: August 6, 1979Date of Patent: June 23, 1981Assignee: Philips Petroleum CompanyInventors: Charles A. Drake, Ralph P. Williams