Polycyclo Ring System Patents (Class 564/308)
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Patent number: 7157604Abstract: The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer, in particular of the breast, uterus and prostate.Type: GrantFiled: August 9, 2002Date of Patent: January 2, 2007Assignee: Merck & Co., Inc.Inventors: Dongfang Meng, Dann LeRoy Parker, Jr., Robert R. Wilkening, Ronald W. Ratcliffe
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Patent number: 7154007Abstract: This invention provides: a compound represented by formula (I): R—Y—(—X-Phe-COCH2COCnF2n+1)m ??(I) wherein R denotes hydrogen, alkyl, phenyl, or a group capable of binding to a protein, peptide, amino acid, nucleic acid, or nucleotide; Y denotes CH2, a carbocyclic ring, or a heterocyclic ring; X denotes O, S, NH, CH2, OCH2, CONH, or NHCO; Phe denotes phenylene; n is an integer between 1 and 5; and m is 1, 2, or 3. This inventions also provides a luminous complex of such compound and a rare earth ion, a labeling reagent comprising such compound or luminous complex, and a process for labeling a protein, peptide, amino acid, nucleic acid, or nucleotide using such labeling reagent.Type: GrantFiled: October 10, 2002Date of Patent: December 26, 2006Assignee: Hitachi High-Technologies CorporationInventors: Michihiro Saito, Ernoe Pretsch
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Self-assembled calixarene-based guest-host assemblies for guest storage by van der Waals confinement
Patent number: 7132571Abstract: A guest-host assembly having a generally spheroidal host assembly formed of trimers of calixarene molecules in a hexagonal close-packed assembly and its preparation. The calixarene trimers are associated together predominantly by van der Waals forces to provide dilated channels having void volumes within the range of 100-200 ?3. A guest component, such as hydrogen, methane, or another hydrocarbon or halocarbon, is encapsulated within the dilated channels of the spheroidal host assembly and retained within the channels primarily by van der Waals forces. The guest-host assembly is stable at a temperature of 150° C. or higher. The temperature at which the onset of the release of the guest component occurs is within the range of 150-300° C.Type: GrantFiled: May 9, 2002Date of Patent: November 7, 2006Assignee: The Curators of the University of MissouriInventors: Jerry L. Atwood, Leonard J. Barbour, Agoston Jerga -
Patent number: 7115780Abstract: The invention concerns compounds of formula (I), wherein A is a group of formula (a) or (b), wherein: R represents a hydrogen or halogen atom, a —S(O)z(C1–C4)Alk wherein z is 0, 1 or 2, a —NHSO2(C1–C4)Alk, —SO2NH(C1–C4)Alk, —NHSO2—(C1–C4)Alk-phenyl or —NHSO2-phenyl group, said phenyl capable of bearing a halogen atom, a (C1–C4)Alk group or a (C1–C6)alkoxy group; R1 represents a hydrogen atom or a —(C1–C4)Alk, —CO(C1–C4)Alk, —(C1–C4)Alk-phenyl or —CO-phenyl group, said phenyl capable of bearing a halogen atom or a —(C1–C4)Alk or (C1–C6)alkoxy group; R2 is a hydrogen atom, a —SO2(C1–C4)Alk, —SO2—(C1–C4)Alk-phenyl, —SO2-phenyl group, or a —(C1–C4)Alk group; X completes a saturated or unsaturated cycle of 5 to 8 atoms, capable of bearing one or two —(C1–C4)Alk groups and/or two carbonyl groups; R3 and R?3 represent each independently a hydrogen or halogen atom, a —(C1–C6)Alk, hydroxy, —CN, —(C1–C6)alkoxy, —COR4 or Y—CR8R9—COR4 group; Y represents O or CH2; R4 represents a hydroxy, (C1–C6)alkoxy or —NR5R6 group; RType: GrantFiled: December 2, 2002Date of Patent: October 3, 2006Assignee: Sanofi-AventisInventors: Laura Barzaghi, Roberto Cecchi, Nunzia Viviani
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Patent number: 7105699Abstract: Treatment of CNS disorders with (1R,4S)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine; and (1S,4R)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine is disclosed. A process for preparing 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine is also disclosed. The process includes the preparation of all four isomers of N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]formamide, which are also useful.Type: GrantFiled: September 7, 2005Date of Patent: September 12, 2006Assignee: Sepracor Inc.Inventors: Thomas P. Jerussi, Qun Kevin Fang, Mark G. Currie
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Patent number: 7094930Abstract: The present invention is directed to certain pharmaceutically acceptable salts of the therapeutically potent selective serotonin reuptake inhibitor, sertraline: and pharmaceutical compositions thereof, wherein said salts are selected from the group consisting of the p-toluenesulfonic acid salt, the fumaric acid salt, the benzenesulfonic acid salt, the benzoic acid salt, the L-tartaric acid salt and the (?)-camphor-10-sulfonic acid salt.Type: GrantFiled: January 22, 2004Date of Patent: August 22, 2006Assignee: Pfizer IncInventors: George J. Quallich, Lewin T. Wint
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Patent number: 7087785Abstract: Treatment of CNS disorders with (1R,4S)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine; and (1S,4R)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine is disclosed. A process for preparing 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine is also disclosed. The process includes the preparation of all four isomers of N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]formamide, which are also useful.Type: GrantFiled: September 16, 2003Date of Patent: August 8, 2006Assignee: Sepracor Inc.Inventors: Thomas P. Jerussi, Qun Kevin Fang, Mark G. Currie
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Patent number: 7081550Abstract: A novel arylamine compound represented by the following general formula (1): wherein R1 and R2 each independently represent an alkyl group, an alkoxyl group, an aryl group, an arylalkyl group or an aryloxyl group, Ar1 to Ar4 each independently represent an aryl group or a heterocyclic group, with provisos that at least two of Ar1 to Ar4 each represent m-biphenyl group or a biphenyl group substituted with aryl groups and the others of Ar1 to Ar4 each represent biphenyl group and that, when the biphenyl group substituted with aryl groups is a biphenyl group substituted with two aryl groups, the others of Ar1 to Ar4 each represent an aryl group; and an organic electroluminescence device comprising a layer of organic compounds which comprises the novel arylamine compound. The organic electroluminescence device has a high luminance, excellent heat resistance and a long life and emits light at a high efficiency.Type: GrantFiled: September 10, 2003Date of Patent: July 25, 2006Assignee: Idemitsu Kosan Co., Ltd.Inventors: Chishio Hosokawa, Masakazu Funahashi
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Patent number: 7067555Abstract: The present invention provides an essentially nonaqueous, liquid pharmaceutical concentrate composition for oral administration containing sertraline or a pharmaceutically acceptable salt thereof and one or more pharmaceutically acceptable excipients. The present invention also provides a use of this concentrate composition to prepare an aqueous solution of sertraline. In addition, the present invention provides a method of using this concentrate composition to treat or prevent a variety of diseases or conditions. Finally, the present invention provides the compound, (1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine methanesulfonate.Type: GrantFiled: February 3, 2004Date of Patent: June 27, 2006Assignee: Pfizer IncInventors: Nancy J. Harper, Gautam R. Ranade, Willard M. Welch
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Patent number: 7067700Abstract: Sertraline hydrochloride, (1Scis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphtalenaminehydrochloride, polymorph II is prepared by extracting or dissolving the sertraline base into ethyl acetate, adding isopropanol as a solvent, adding hydrogen chloride dissolved in ethyl acetate or in gaseous form, and finally isolating and drying sertraline hydrochloride polymorphic form II.Type: GrantFiled: May 30, 2002Date of Patent: June 27, 2006Assignee: Fermion OyInventor: Ilpo Laitinen
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Patent number: 7057071Abstract: The present invention relates to a process for producing 5-nitro-3,4-dihydro-1(2H)-naphthalinone, 1,5-naphthalenediamine and 1,5-naphthalene diisocyanate, in which 4-(2-nitrophenyl)-n-butyronitrile is converted to 4-(2-nitrophenyl)-n-butyric acid.Type: GrantFiled: May 28, 2003Date of Patent: June 6, 2006Assignee: Bayer MaterialScience AGInventors: Joachim Zechlin, Kai Verkerk, Dietmar Wastian, Katrin Joschek, Tim Loddenkemper, Wilfried Pinke, Michael Schelhaas, Georg Ronge
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Patent number: 7022881Abstract: The present invention is directed to forms II, III, V, VI, VII, VIII, IX and X of sertraline hydrochloride and novel methods for their preparation. According to the present invention, sertraline hydrochloride polymorph II may be produced by slurrying sertraline hydrochloride polymorph VI in aprotic organic solvent. Sertraline hydrochloride polymorphic form III may be produced by heating sertraline hydrochloride polymorphs V and VI. Sertraline hydrochloride forms V and VI may be produced from either sertraline hydrochloride or sertraline base by crystallization. Sertraline hydrochloride Form VII may be produced by suspending sertraline chloride polymorph V in water, followed by filtration. Sertraline hydrochloride Forms VIII and IX may be produced by suspending sertraline base in water followed by acidification and filtration. Sertraline hydrochloride Form X may be produced by suspending sertraline hydrochloride in benzyl alcohol with heating, followed by filtration.Type: GrantFiled: June 4, 2004Date of Patent: April 4, 2006Assignee: Teva Pharmaceutical Industries, Ltd.Inventors: Eduard Schwartz, Tamar Nidam, Anita Liberman, Marioara Mendelovici, Judith Aronhime, Claude Singer, Evgeni Valdman
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Patent number: 6979566Abstract: A water soluble derivative of buckministerfullerene (C50) having antiviral and virucidal properties is used to inhibit human retroviral replication and infections. The derivatized fullerene is symmetrically substituted with polar organic moieties containing 1 to 20 carbon atoms and optionally further containing oxygen or nitrogen.Type: GrantFiled: February 1, 2003Date of Patent: December 27, 2005Assignee: The Regents of the University of CaliforniaInventors: Simon H. Friedman, Raymond F. Schinazi, Fred Wudl, Craig L. Hill, Diane L. DeCamp, Rintje P. Sijbesma, George L. Kenyon
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Patent number: 6946462Abstract: New compounds represented by the formula or pharmaceutically acceptable salts or prodrugs thereof, wherein X1 and X2 are each independently selected from a CH group or a nitrogen atom; and R is an optionally substituted five or six membered nonaromatic carbocyclic ring or a nonaromatic or aromatic heterocyclic ring, whereby the ring is optionally condensed with a 6-membered, optionally substituted carbocyclic aromatic ring.Type: GrantFiled: April 13, 2004Date of Patent: September 20, 2005Assignee: Hoffmann-La Roche Inc.Inventors: Rainer Haag, Ulrike Leser-Reiff, Anja Limberg, Michael Weidner, Gerd Zimmermann
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Patent number: 6939992Abstract: A crystalline form of sertraline hydrochloride was found, referred to hereinafter as polymorphic form CSC2 having a dissolution rate which surprisingly will increase rate of absorption of a drug. Furthermore, different crystalline forms of sertraline hydrochloride alcohol solvates, crystalline forms of sertraline hydrochloride hydrates, referred to hereinafter as polymorphic form CSC1, a process for the preparation of the amorphous form of sertraline hydrochloride, and different processes for the preparation of polymorphic forms I, II, V, and T1 are disclosed.Type: GrantFiled: December 15, 2003Date of Patent: September 6, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Adriaan Van Der Schaaf, Franz Schwarzenbach, Hans-Jörg Kirner, Martin Szelagiewicz, Claudia Marcolli, Andreas Burkhard
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Patent number: 6914074Abstract: This invention provides estrogen receptor modulators of formula I, having the structure wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10, are as defined in the specification, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: December 11, 2002Date of Patent: July 5, 2005Assignee: WyethInventors: Richard E. Mewshaw, Richard J. Edsall, Cuijian Yang, Heather A. Harris, James C. Keith, Jr., Leo M. Albert, Eric S. Manas
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Patent number: 6900355Abstract: The invention relates to a process for the cis-selective preparation of cyclic amines of the sertralin type by reductive alkylation of cyclic imines or their precursors and catalytic hydrogenation in the presence of copper-containing catalysts and in the presence of a protic solvent.Type: GrantFiled: March 5, 2004Date of Patent: May 31, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Heinz Steiner, Marc Thommen, Hans-Peter Jalett, Markus Benz
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Patent number: 6872853Abstract: A cystalline form of sertraline hydrochloride was found, referred to hereinafter as polymorphic form CSC2 having a dissolution rate which surprisingly will increase rate of absorption of a drug. Furthermore, different crystalline forms of sertraline hydrochloride alcohol solvates, crystalline forms of sertraline hydrochloride hydrates, referred to hereinafter as polymorphic form CSC1, a process for the preparation of the amorphous form of sertraline hydrochloride, and different processes for the preparation of polymorphic forms I, II, V, and T1 are disclosed.Type: GrantFiled: October 23, 2000Date of Patent: March 29, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Adriaan Van Der Schaaf, Franz Schwarzenbach, Hans-Jörg Kirner, Martin Szelagiewicz, Claudia Marcolli, Andreas Burkhard, Regine Peter
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Patent number: 6869953Abstract: New compounds represented by the formula or pharmaceutically acceptable salts or prodrugs thereof, wherein X1 and X2 are each independently selected from a CH group or a nitrogen atom; and R is an optionally substituted five or six membered nonaromatic carbocyclic ring or a nonaromatic or aromatic heterocyclic ring, whereby the ring is optionally condensed with a 6-membered, optionally substituted carbocyclic aromatic ring.Type: GrantFiled: August 6, 2002Date of Patent: March 22, 2005Assignee: Hoffman-La Roche Inc.Inventors: Rainer Haag, Ulrike Leser-Reiff, Anja Limberg, Michael Weidner, Gerd Zimmermann
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Patent number: 6861560Abstract: A bis-o-aminophenol has a formula I These bis-o-aminophenols permit the preparation of polybenzoxazoles stabilized at high temperatures. The bis-o-aminophenols are preferably prepared from the corresponding diols, which are first nitrosated. The nitroso compound is then reduced to the amino compound by hydrogenation with Pd/C and H2.Type: GrantFiled: June 27, 2003Date of Patent: March 1, 2005Assignee: Infineon Technologies AGInventors: Andreas Walter, Ingo Gnüchtel, Anna Maltenberger, Recai Sezi, Horst Hartmann
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Patent number: 6858652Abstract: The present invention is directed to novel polymorphic Forms XI, XII, XIII, XIV, XV and XVI of sertraline hydrochloride, to processes for preparing them, methods of using them to treat disease, methods of using them to make other sertraline hydrochloride forms, and to pharmaceutical dosages containing the novel forms.Type: GrantFiled: September 13, 2002Date of Patent: February 22, 2005Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Judith Aronhime, Marioara Mendelovici, Tamar Nidam, Claude Singer
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Patent number: 6830834Abstract: A compound having a host moiety chemically bonded to at least one guest moiety according to the following general molecular structure: Ho—(L—G)n. Ho represents a host moiety that receives hole and/or electron recombination energy and transfers that energy to a guest moiety; G represents a guest moiety that contains a luminescent chromophore; L represents a chemical moiety that links the host and guest moiety and n is from 1 to 4. The compound can be used in the emissive layer of an OLED, or as a dopant dispersed in a host material that forms the emissive layer, wherein the host material has the same chemical structure as Ho.Type: GrantFiled: April 29, 2003Date of Patent: December 14, 2004Assignee: Canon Kabushiki KaishaInventors: Xiao-Chang Charles Li, Jian Ping Chen, Kazunori Ueno
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Patent number: 6828461Abstract: A process for producing 1,5-diaminonaphthalene without formation of 1,8-diaminonaphthalene and not through an unstable nitro imine and nitro enamine as intermediates, the process including the steps of dehydrogenating 5-substituted-1-tetralone to produce a naphtol compound and then aminating the hydroxyl group of the naphtol compound.Type: GrantFiled: January 12, 2004Date of Patent: December 7, 2004Assignee: Mitsui Chemicals, Inc.Inventors: Yukihiro Kumamoto, Masazumi Takaoka, Hideki Mizuta, Yoriaki Matsuzaki
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Patent number: 6809221Abstract: The present invention is directed to (+)-cis-sertraline hydrochloride and methods of preparation. The present invention also includes processes for making sertraline having a cis/trans ratio greater than 3:1, greater than or equal to 8:1, or between about 8:1 and about 12:1, from the Schiff base of sertralone, sertraline-1-imine.Type: GrantFiled: February 12, 2003Date of Patent: October 26, 2004Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Marioara Mendelovici, Tamar Nidam, Gideon Pilarsky, Neomi Gershon
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Patent number: 6806386Abstract: The present invention relates to a process for the preparation of compounds of formula (1), in which R1, R2 and R3 independently of one another are hydrogen, halogen , trifluoromethyl of or C1-C4alkoxy, wherein a compound of formula (2), in which R1, R2 and R3 are as defined in formula (1), is reacted with methlyamine in the presence of a non-alcoholic solvent and, if desired, in the presence of a sulfonic acid catalyst to give the compound of formula (2) and, if desired, is subject to purification by recrystallization.Type: GrantFiled: May 14, 2002Date of Patent: October 19, 2004Assignee: Ciba Specialty Chemicals CorporationInventors: Marc Thommen, Andreas Hafner, Frédëric Brunner, Hans-Jörg Kirner, Roman Kolly
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Publication number: 20040138313Abstract: The invention relates to compounds of the formula (I) 1Type: ApplicationFiled: July 25, 2003Publication date: July 15, 2004Applicant: Aventis Pharma Deutschland GmbHInventors: Claudia Eder, Herbert Kogler, Sabine Haag-Richter
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Patent number: 6753429Abstract: Compounds of formula I: wherein A, B, D, and R are as defined herein and their agriculturally acceptable salts are disclosed as effective insecticides. In addition, compositions comprising an insecticidally effective amount of a compound of Formula I in admixture with at least one agriculturally acceptable extender or adjuvant and methods of controlling insects comprising applying said compositions to locus on crops where control is desired are disclosed. It is emphasized that this abstract is provided to comply with the rules requiring an abstract that will allow a searcher or other reader to quickly ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the claims (see 37 C.F.R. 1.72(b)).Type: GrantFiled: August 29, 2001Date of Patent: June 22, 2004Assignee: FMC CorporationInventors: George Theodoridis, Edward Barron, Daniel H. Cohen, Ellen M. Crawford, Thomas G. Cullen, Hongyan Qi, Elizabeth Rowley, Syed F. Ali, Walter H. Yeager, Christina B. Duggan
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Patent number: 6749644Abstract: The object of the present invention are colorants for oxidative dyeing of keratin fibers, particularly hair, based on a developer-coupler combination containing as the developer at least one 2-hydroxy-5-amino-biphenyl derivative of general formula (I), and novel 2-hydroxy-5-aminobiphenyl derivatives.Type: GrantFiled: January 30, 2002Date of Patent: June 15, 2004Assignee: Wella AktiengesellschaftInventors: Laurent Chassot, Hans-Juergen Braun
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Publication number: 20040110984Abstract: Disclosed are highly efficient multiphoton absorbing compounds and methods of their use. The compounds generally include a bridge of pi-conjugated bonds connecting electron donating groups or electron accepting groups. The bridge may be substituted with a variety of substituents as well. Solubility, lipophilicity, absorption maxima and other characteristics of the compounds may be tailored by changing the electron donating groups or electron accepting groups, the substituents attached to or the length of the pi-conjugated bridge. Numerous photophysical and photochemical methods are enabled by converting these compounds to electronically excited states upon simultaneous absorption of at least two photons of radiation. The compounds have large two-photon or higher-order absorptivities such that upon absorption, one or more Lewis acidic species, Lewis basic species, radical species or ionic species are formed.Type: ApplicationFiled: May 20, 2003Publication date: June 10, 2004Applicant: California Institute of TechnologyInventors: Brian Cumpston, Matthew Lipson, Seth R. Marder, Joseph W. Perry
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Patent number: 6737548Abstract: In a process where an ortho-alkylnitrobenzene derivative and a vinyl compound as starting materials are used to prepare a 1,5-diaminonaphthalene derivative via a 4-(2-nitrobenzene)propane derivative and a 5-nitro-1-tetralone derivative, the ortho-alkylnitrobenzene derivative and a vinyl compound having an electron withdrawing group such as an acrylonitrile derivative and an acrylate may be reacted in the presence of a base to provide an aromatic nitro compound. An aromatic nitro compound such as 4-(2-nitrobenzene)butanonitrile thus obtained may be cyclized to safely, cost-effectively and selectively provide a 5-nitro-1-tetralone derivative without forming any isomer. Furthermore, from the 5-nitro-1-tetralone derivative, a 1,5-diaminonaphthalene derivative may be prepared without forming any isomer.Type: GrantFiled: January 2, 2003Date of Patent: May 18, 2004Assignee: Mitsui Chemicals, Inc.Inventors: Satoshi Inoki, Yoshio Motoyama
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Patent number: 6723878Abstract: (1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (sertraline) may be prepared by hydrogenating of N-[4-(3,4-dichlorophenyl)-3, 4-dihydro-1(2H)-naphthalenylidene]methanamine in the presence of a dehalogenation inhibitor, e.g., triphenylphosphite or trimethylphosphite and a catalyst.Type: GrantFiled: June 14, 2002Date of Patent: April 20, 2004Assignee: Orion Corporation FermionInventor: Ilpo Laitinen
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Patent number: 6720454Abstract: The invention relates to a process for the cis-selective preparation of cyclic amines of the sertralin type by reductive alkylation of cyclic imines or their precursors and catalytic hydrogenation in the presence of copper-containing catalysts and in the presence of a protic solvent.Type: GrantFiled: January 25, 2002Date of Patent: April 13, 2004Assignee: Ciba Specialty Chemicals CorporationInventors: Heinz Steiner, Marc Thommen, Hans-Peter Jalett, Markus Benz
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Patent number: 6696178Abstract: An organic light-emitting device comprising a light-emitting layer or a plurality of organic compound thin layers including a light-emitting layer formed between a pair of electrodes, wherein at least one layer comprises at least one kind of compound represented by the following formula (1): wherein R11, R12 and R13 each represents a group having a cyclocondensed polycyclic hydrocarbon structure in which three or more rings are cyclocondensed; and a novel cyclocondensed polycyclic hydrocarbon compound.Type: GrantFiled: January 8, 2001Date of Patent: February 24, 2004Assignee: Fuji Photo Film Co., Ltd.Inventor: Tatsuya Igarashi
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Patent number: 6693218Abstract: Described is a process for the preparation of compounds of formula (1a) which comprises reacting an isomeric mixture consisting of from 75 to 95% of compound of formula (2a) and from 5 to 25% of a compound of formula (2b) with methylamine, in a suitable solvent, to form a sertraline-imine isomeric mixture consisting of from 75 to 95% of formula (1a) and from 5 to 25% of formula (1b)(A1), or reacting an isomeric mixture consisting of from 75 to 95% of a compound of formula (2a) and from 5 to 25% of a compound of formula (2b) with methylamine, in a suitable solvent, using suitable methods of isolation to form an enriched sertraline-imine isomeric mixture, consisting of >99% of a compound of formula (1a) and <1% of a compound of formula (1b)(A2); and then subjecting the sertraline-imine isomeric mixture obtained according to reaction route (A1) or (A2), in a suitable solvent, to recrystallisation (B), in accordance with scheme (I) wherein in formula (1a), R1, R2 and R3 are each independently of the othersType: GrantFiled: September 20, 2002Date of Patent: February 17, 2004Assignee: Ciba Specialty Chemicals CorporationInventors: Marc Thommen, Andreas Hafner, Roman Kolly, Hans-Jörg Kirner, Frédéric Brunner
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Patent number: 6683220Abstract: A process for producing substantially optically pure sertraline utilizes chromatographic separation on a solid stationary chiral phase of spherical clay particles having an interlayer containing an optically pure metal-organic complex, and a liquid mobile phase preferably containing at least methyl acetate. The liquid mobile phase is preferably free of acetonitrile. The process is operable at temperatures above 40° C.Type: GrantFiled: September 18, 2002Date of Patent: January 27, 2004Assignee: Pfizer, Inc.Inventors: Laurent Berger, Raphael Duval, Philippe Taillasson, Ingo Weber, Alexander Wick
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Patent number: 6657084Abstract: A novel arylamine compound represented by the following general formula (1): wherein R1 and R2 each independently represent an alkyl group, an alkoxyl group, an aryl group, an arylalkyl group or an aryloxyl group, Ar1 to Ar4 each independently represent an aryl group or a heterocyclic group, with provisos that at least two of Ar1 to Ar4 each represent m-biphenyl group or a biphenyl group substituted with aryl groups and the others of Ar1 to Ar4 each represent biphenyl group and that, when the biphenyl group substituted with aryl groups is a biphenyl group substituted with two aryl groups, the others of Ar1 to Ar4 each represent an aryl group; and an organic electroluminescence device comprising a layer of organic compounds which comprises the novel arylamine compound. The organic electroluminescence device has a high luminance, excellent heat resistance and a long life and emits light at a high efficiency.Type: GrantFiled: July 12, 2002Date of Patent: December 2, 2003Assignee: Idemitsu Kosan Co., Ltd.Inventors: Chishio Hosokawa, Masakazu Funahashi
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Patent number: 6608228Abstract: Disclosed are highly efficient multiphoton absorbing compounds and methods of their use. The compounds generally include a bridge of pi-conjugated bonds connecting electron donating groups or electron accepting groups. The bridge may be substituted with a variety of substituents as well. Solubility, lipophilicity, absorption maxima and other characteristics of the compounds may be tailored by changing the electron donating groups or electron accepting groups, the substituents attached to or the length of the pi-conjugated bridge. Numerous photophysical and photochemical methods are enabled by converting these compounds to electronically excited states upon simultaneous absorption of at least two photons of radiation. The compounds have large two-photon or higher-order absorptivities such that upon absorption, one or more Lewis acidic species, Lewis basic species, radical species or ionic species are formed.Type: GrantFiled: April 15, 1999Date of Patent: August 19, 2003Assignee: California Institute of TechnologyInventors: Brian Cumpston, Matthew Lipson, Seth R. Marder, Joseph W. Perry
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Patent number: 6600073Abstract: Novel methods for the preparation of sertraline hydrochloride Forms III, V, VI, VII, VII, IX and X are disclosed. According to the present invention, sertraline hydrochloride Form III may be produced by heating sertraline hydrochloride Forms V and VI. Sertraline hydrochloride Forms V and VI may be produced from either sertraline hydrochloride or sertraline base by crystallization. Sertraline hydrochloride Form VII may be produced by suspending sertraline chloride polymorph V in water, followed by filtration. Sertraline hydrochloride Forms VIII and IX may be produced by suspending sertraline base in water followed by acidification and filtration. Sertraline hydrochloride Form X may be produced by suspending sertraline hydrochloride in benzyl alcohol with heating, followed by filtration.Type: GrantFiled: June 5, 2000Date of Patent: July 29, 2003Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Eduard Schwartz, Tamar Nidam, Anita Liberman, Marioara Mendelovici, Judith Aronhime, Claude Singer, Evgeni Valdman
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Patent number: 6593012Abstract: An organic electroluminescent device of the type comprises an organic layer 5, 5a or 5b having a luminescent region and provided between an anode 2 and a cathode 3. The organic layer contains a distyryl compound represented by the following general formula (1). General Formula (1): wherein R1, R2, R3 and R4 are, respectively, groups which may be the same or different and independently represent an aryl group of the following general formula (2). General Formula (2): in which R9, R10, R11, R12 and R13 may be the same or different and, respectively, represent a hydrogen atom provided that at least one of them is a saturated or unsaturated alkoxyl group or an alkyl group, and R5, R6, R7 and R8 may be the same or different and, respectively, represent a hydrogen atom provided that at least one of them represents a cyano group, a nitro group or a halogen atom.Type: GrantFiled: August 8, 2001Date of Patent: July 15, 2003Assignee: Sony CorporationInventors: Tadashi Ishibashi, Mari Ichimura, Shinichiro Tamura
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Patent number: 6593496Abstract: This invention relates to a novel improved process for preparing the (+) enantiomer of N-[4(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine by reacting the (+) enantiomer of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone with monomethylamine and titanium chloride or molecular sieves.Type: GrantFiled: May 30, 2000Date of Patent: July 15, 2003Assignee: Pfizer IncInventor: George H. Quallich
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Patent number: 6552227Abstract: The present invention is directed to (+)-cis-sertraline hydrochloride and methods of preparation. The present invention also includes processes for making sertraline having a cis/trans ratio greater than 3:1, greater than or equal to 8:1, or between about 8:1 and about 12:1, from the Schiff base of sertralone, sertraline-1-imine.Type: GrantFiled: March 14, 2001Date of Patent: April 22, 2003Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Marioara Mendelovici, Tamar Nidam, Gideon Pilarsky, Neomi Gershon
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Patent number: 6552088Abstract: Biphenyl substituted amides with activity as antagonists of the neurokinin 1 (NK-1, substance P) receptor.Type: GrantFiled: June 21, 2001Date of Patent: April 22, 2003Assignee: Hoffmann-La Roche Inc.Inventors: Michael Bös, Guido Galley, Thierry Godel, Torsten Hoffmann, Walter Hunkeler, Patrick Schnider, Heinz Stadler
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Patent number: 6541129Abstract: The invention is to provide an organic EL device having a long life time that can reduce the driving voltage of the organic EL device, and to provide a material having a small ionization potential and exhibiting a large hole mobility by using as a layer or a zone. The organic electroluminescence device comprises a pair of electrodes and an organic light emitting layer sandwiched in the electrodes, characterized in that a hole transporting zone provided between the electrodes comprises the phenylenediamine derivative represented by the specific structural formulae, and the phenylenediamine derivative has a hole mobility of 10−4 cm2/V·s or more upon using as a layer or a zone, with the organic light emitting layer containing a charge injection auxiliary.Type: GrantFiled: May 9, 2000Date of Patent: April 1, 2003Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hisayuki Kawamura, Chishio Hosokawa
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Patent number: 6515182Abstract: A novel arylamine compound represented by the following general formula (1): wherein R1 and R2 each independently represent an alkyl group, an alkoxyl group, an aryl group, an arylalkyl group or an aryloxyl group, Ar1 to Ar4 each independently represent an aryl group or a heterocyclic group, with provisos that at least two of Ar1 to Ar4 each represent m-biphenyl group or a biphenyl group substituted with aryl groups and the others of Ar1 to Ar4 each represent biphenyl group and that, when the biphenyl group substituted with aryl groups is a biphenyl group substituted with two aryl groups, the others of Ar1 to Ar4 each represent an aryl group; and an organic electroluminescence device comprising a layer of organic compounds which comprises the novel arylamine compound. The organic electroluminescence device has a high luminance, excellent heat resistance and a long life and emits light at a high efficiency.Type: GrantFiled: September 5, 2001Date of Patent: February 4, 2003Assignee: Idemitsu Kosan Co., Ltd.Inventors: Chishio Hosokawa, Masakazu Funahashi
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Patent number: 6506940Abstract: A process for converting the cis (1R, 4R), trans (1S, 4R), and trans (1R, 4S) stereoisomers of sertraline into sertraline comprises, starting with an initial reaction mixture which contains at least one of these stereoisomers, converting the sertraline stereoisomers into an imine form of sertraline. The imine form of sertraline is then reduced so that sertraline and at least one sertraline stereoisomer byproduct is produced in the reaction mixture. The sertraline is then recovered from the reaction mixture, e.g., by fractional crystallization (followed by resolution of sertraline from the cis (1R, 4R) stereoisomer, if necessary). The reaction mixture is then recycled through the same steps so that sertraline is produced from its stereoisomers in an asymptotic yield.Type: GrantFiled: November 10, 2000Date of Patent: January 14, 2003Assignee: Sun Pharmaceuticals Industries Ltd.Inventors: Kanaksinh J. Jadav, Trinadha Rao Chitturi, Rajamannar Thennati
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Patent number: 6500987Abstract: The present invention is directed to forms II, III, V, VI, VII, VIII, IX and X of sertraline hydrochloride and novel methods for their preparation. According to the present invention, sertraline hydrochloride polymorph II may be produced by slurrying sertraline hydrochloride polymorph VI in aprotic organic solvent. Sertraline hydrochloride polymorphic form III may be produced by heating sertraline hydrochloride polymorphs V and VI. Sertraline hydrochloride forms V and VI may be produced from either sertraline hydrochloride or sertraline base by crystallization. Sertraline hydrochloride Form VII may be produced by suspending sertraline chloride polymorph V in water, followed by filtration. Sertraline hydrochloride Forms VIII and IX may be produced by suspending sertraline base in water followed by acidification and filtration. Sertraline hydrochloride Form X may be produced by suspending sertraline hydrochloride in benzyl alcohol with heating, followed by filtration.Type: GrantFiled: November 24, 1999Date of Patent: December 31, 2002Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Eduard Schwartz, Tamar Nidam, Anita Liberman, Marioara Mendelovici, Judith Aronhime, Claude Singer, Evgeni Valdman
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Patent number: 6495721Abstract: The present invention is directed to Form II of sertraline hydrochloride and novel methods for its preparation. According to the present invention, sertraline hydrochloride Form II may be produced directly form sertraline base or sertraline mandelate. It may also be produced from sertraline hydrochloride solvate and hydrate forms, and crystallized from new solvent systems. Pharmaceutical compositions containing sertraline hydrochloride Form II and methods of treatment using such pharmaceutical compositions are also disclosed.Type: GrantFiled: May 22, 2000Date of Patent: December 17, 2002Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Eduard Schwartz, Tamar Nidam, Anita Liberman, Marioara Mendelovici, Judith Aronhime
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Patent number: 6495546Abstract: Propanolamine derivatives represented by the following formula (I): These derivatives may be &bgr;3 agonists and exert sympathomimetic, anti-ulcerous, anti-pancreatitis, lipolytic and anti-urinary incontinence and anti-pollakiuria activities. Pharmaceutical compositions containing such propanolamine derivatives, methods for the prevention and/or treatment diseases using these propanolamine derivatives, and processes for their preparation are also described.Type: GrantFiled: November 22, 2000Date of Patent: December 17, 2002Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Kiyoshi Taniguchi, Minoru Sakurai, Naoaki Fujii, Kumi Hosoi, Yasuyo Tomishima, Hisashi Takasugi, Hajime Sogabe, Hirofumi Ishikawa, Naomi Hanioka
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Patent number: 6479702Abstract: The present invention relates to a compound which is expected to be a synthetic intermediate for medicines and pesticides or a separating agent for chromatography or a enantiomerically resolving agent for racemic bodies. That is, it provides 3-amino-1-indanol represented by the formula (I), a process for synthesizing it, an enantiomerically active compound of 3-amino-1-indanol and a process for enantiomerically resolving 3-amino-1-indanol, and a separating agent for enantiomeric isomers comprising enantiomerically active compound thereof as an effective ingredient. In the formula, the configuration between OH group and NH2 group are cis-configuration or trans-configuration and the compound may be a racemic body or an enantiomerically active compound.Type: GrantFiled: April 15, 2002Date of Patent: November 12, 2002Assignee: Daicel Chemical Industries, Ltd.Inventors: Kazuhiko Saigo, Kazushi Kinbara, Yoshiyuki Katsumata
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Patent number: 6476265Abstract: In a process for preparing aryl oligoamines, an amine is reacted with an activated aromatic and a base in a temperature range from 0 to 150° C. in the presence of a palladium component and a phosphine ligand. The aryl oligoamines are obtained simply and in good yields.Type: GrantFiled: May 10, 2000Date of Patent: November 5, 2002Assignee: Covion Organic Semiconductors GmbHInventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Ute Neumann